data_I-c_dark _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.795(2) _cell_length_b 8.071(2) _cell_length_c 13.457(3) _cell_angle_alpha 85.12(2) _cell_angle_beta 75.70(2) _cell_angle_gamma 81.12(2) _cell_volume 809.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6417 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6417 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 24.67 _reflns_number_total 2727 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2727 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35407(15) 1.08115(15) 0.23560(9) 0.0449(3) Uani 1 1 d . . . H1 H 0.4216 1.0313 0.2697 0.054 Uiso 1 1 calc R . . C1 C 0.0394(2) 0.9980(2) 0.44778(13) 0.0449(5) Uani 1 1 d . . . C2 C 0.1068(2) 0.9953(2) 0.35823(13) 0.0438(5) Uani 1 1 d . . . C3 C 0.2032(2) 0.9953(2) 0.24839(12) 0.0369(4) Uani 1 1 d . . . C4 C 0.0854(2) 1.0886(2) 0.18004(13) 0.0380(4) Uani 1 1 d . . . C5 C -0.0984(2) 1.1138(3) 0.21170(16) 0.0564(6) Uani 1 1 d . . . H5 H -0.1540 1.0794 0.2780 0.068 Uiso 1 1 calc R . . C6 C -0.2013(3) 1.1903(3) 0.14540(19) 0.0731(7) Uani 1 1 d . . . H6 H -0.3252 1.2061 0.1675 0.088 Uiso 1 1 calc R . . C7 C -0.1220(3) 1.2424(3) 0.04827(18) 0.0679(6) Uani 1 1 d . . . H7 H -0.1914 1.2945 0.0044 0.082 Uiso 1 1 calc R . . C8 C 0.0611(3) 1.2175(3) 0.01543(16) 0.0636(6) Uani 1 1 d . . . H8 H 0.1159 1.2523 -0.0510 0.076 Uiso 1 1 calc R . . C9 C 0.1638(2) 1.1409(3) 0.08096(14) 0.0502(5) Uani 1 1 d . . . H9 H 0.2877 1.1243 0.0581 0.060 Uiso 1 1 calc R . . C10 C 0.2604(2) 0.8143(2) 0.21458(12) 0.0370(4) Uani 1 1 d . . . C11 C 0.4294(2) 0.7658(3) 0.15379(14) 0.0489(5) Uani 1 1 d . . . H11 H 0.5100 0.8432 0.1344 0.059 Uiso 1 1 calc R . . C12 C 0.4793(3) 0.6035(3) 0.12169(15) 0.0590(6) Uani 1 1 d . . . H12 H 0.5939 0.5717 0.0820 0.071 Uiso 1 1 calc R . . C13 C 0.3606(3) 0.4894(3) 0.14817(16) 0.0603(6) Uani 1 1 d . . . H13 H 0.3946 0.3804 0.1263 0.072 Uiso 1 1 calc R . . C14 C 0.1914(3) 0.5357(3) 0.20702(16) 0.0617(6) Uani 1 1 d . . . H14 H 0.1104 0.4585 0.2246 0.074 Uiso 1 1 calc R . . C15 C 0.1421(3) 0.6977(2) 0.23999(15) 0.0509(5) Uani 1 1 d . . . H15 H 0.0275 0.7287 0.2799 0.061 Uiso 1 1 calc R . . O2 O 0.4607(2) 0.0686(2) 0.62512(11) 0.0745(5) Uani 1 1 d . . . N1A N 0.3802(2) 0.2162(2) 0.48970(13) 0.0644(5) Uani 1 1 d . . . H1NA H 0.4192 0.1281 0.4547 0.077 Uiso 1 1 calc R . . C16A C 0.3945(3) 0.2066(3) 0.58837(17) 0.0587(6) Uani 1 1 d . . . C17A C 0.3291(3) 0.3555(4) 0.64156(19) 0.0748(7) Uani 1 1 d . . . H17A H 0.3350 0.3574 0.7096 0.090 Uiso 1 1 calc R . . C18 C 0.2578(3) 0.4957(3) 0.5950(2) 0.0822(8) Uani 1 1 d . . . H18A H 0.2163 0.5927 0.6313 0.099 Uiso 1 1 calc R . . C19 C 0.2462(3) 0.4960(4) 0.4932(2) 0.0828(8) Uani 1 1 d . . . H19A H 0.1962 0.5917 0.4614 0.099 Uiso 1 1 calc R . . C20A C 0.3086(3) 0.3555(3) 0.4424(2) 0.0814(8) Uani 1 1 d . . . H20A H 0.3028 0.3533 0.3743 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0487(7) 0.0466(8) 0.0430(7) 0.0005(6) -0.0150(5) -0.0126(5) C1 0.0511(10) 0.0478(12) 0.0332(10) -0.0038(9) -0.0065(8) -0.0031(8) C2 0.0531(10) 0.0424(11) 0.0336(11) -0.0048(8) -0.0072(8) -0.0032(8) C3 0.0400(9) 0.0413(11) 0.0283(9) -0.0014(8) -0.0042(7) -0.0088(7) C4 0.0476(10) 0.0327(10) 0.0327(10) -0.0034(8) -0.0089(7) -0.0026(7) C5 0.0473(11) 0.0629(14) 0.0502(12) 0.0052(10) -0.0050(9) 0.0040(9) C6 0.0525(12) 0.0821(18) 0.0774(17) 0.0102(14) -0.0176(11) 0.0086(11) C7 0.0757(15) 0.0659(16) 0.0655(15) 0.0044(12) -0.0363(12) 0.0077(11) C8 0.0797(15) 0.0706(16) 0.0399(12) 0.0090(11) -0.0207(10) -0.0044(11) C9 0.0528(11) 0.0579(13) 0.0368(11) 0.0038(9) -0.0088(8) -0.0048(9) C10 0.0448(9) 0.0388(10) 0.0265(9) -0.0010(8) -0.0096(7) -0.0020(7) C11 0.0476(10) 0.0527(13) 0.0441(11) -0.0102(9) -0.0065(8) -0.0029(8) C12 0.0615(13) 0.0589(14) 0.0528(13) -0.0176(11) -0.0128(10) 0.0102(11) C13 0.0887(16) 0.0419(13) 0.0502(13) -0.0086(10) -0.0263(11) 0.0108(11) C14 0.0842(15) 0.0402(13) 0.0618(14) 0.0018(11) -0.0166(11) -0.0158(11) C15 0.0575(11) 0.0430(12) 0.0474(12) -0.0011(9) -0.0027(9) -0.0083(9) O2 0.0834(10) 0.0854(13) 0.0609(10) 0.0064(9) -0.0355(8) -0.0062(9) N1A 0.0753(12) 0.0651(13) 0.0592(12) 0.0056(10) -0.0300(9) -0.0112(9) C16A 0.0515(11) 0.0749(17) 0.0563(14) 0.0063(12) -0.0241(10) -0.0161(10) C17A 0.0712(15) 0.090(2) 0.0680(16) -0.0124(15) -0.0228(12) -0.0116(13) C18 0.0688(15) 0.0742(19) 0.103(2) -0.0125(16) -0.0176(14) -0.0082(13) C19 0.0857(18) 0.072(2) 0.092(2) 0.0088(16) -0.0310(15) -0.0071(14) C20A 0.0961(18) 0.077(2) 0.0751(18) 0.0135(15) -0.0385(14) -0.0051(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4229(19) . ? O1 H1 0.8200 . ? C1 C2 1.190(2) . ? C1 C1 1.389(3) 2_576 ? C2 C3 1.483(2) . ? C3 C4 1.530(2) . ? C3 C10 1.534(2) . ? C4 C5 1.378(2) . ? C4 C9 1.382(2) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.362(3) . ? C6 H6 0.9300 . ? C7 C8 1.374(3) . ? C7 H7 0.9300 . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.382(2) . ? C10 C11 1.386(2) . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.370(3) . ? C12 H12 0.9300 . ? C13 C14 1.374(3) . ? C13 H13 0.9300 . ? C14 C15 1.383(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.267(3) . ? N1A C16A 1.354(3) . ? N1A C20A 1.357(3) . ? N1A H1NA 0.8600 . ? C16A C17A 1.412(3) . ? C17A C18 1.356(3) . ? C17A H17A 0.9300 . ? C18 C19 1.395(4) . ? C18 H18A 0.9300 . ? C19 C20A 1.336(4) . ? C19 H19A 0.9300 . ? C20A H20A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.7(3) . 2_576 ? C1 C2 C3 175.68(19) . . ? O1 C3 C2 108.49(14) . . ? O1 C3 C4 107.52(13) . . ? C2 C3 C4 111.38(14) . . ? O1 C3 C10 111.05(13) . . ? C2 C3 C10 109.89(14) . . ? C4 C3 C10 108.49(14) . . ? C5 C4 C9 118.33(17) . . ? C5 C4 C3 122.14(15) . . ? C9 C4 C3 119.42(15) . . ? C4 C5 C6 120.50(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.48(19) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.7(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 119.99(19) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C4 C9 C8 121.00(18) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C15 C10 C11 118.38(17) . . ? C15 C10 C3 120.84(15) . . ? C11 C10 C3 120.72(16) . . ? C12 C11 C10 120.61(18) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.17(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 121.04(18) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C16A N1A C20A 124.4(2) . . ? C16A N1A H1NA 117.8 . . ? C20A N1A H1NA 117.8 . . ? O2 C16A N1A 118.9(2) . . ? O2 C16A C17A 126.0(2) . . ? N1A C16A C17A 115.1(2) . . ? C18 C17A C16A 121.1(2) . . ? C18 C17A H17A 119.5 . . ? C16A C17A H17A 119.5 . . ? C17A C18 C19 120.7(3) . . ? C17A C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20A C19 C18 118.5(3) . . ? C20A C19 H19A 120.8 . . ? C18 C19 H19A 120.8 . . ? C19 C20A N1A 120.3(3) . . ? C19 C20A H20A 119.8 . . ? N1A C20A H20A 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 72(54) 2_576 . . . ? C1 C2 C3 O1 -16(3) . . . . ? C1 C2 C3 C4 -134(3) . . . . ? C1 C2 C3 C10 105(3) . . . . ? O1 C3 C4 C5 -140.00(17) . . . . ? C2 C3 C4 C5 -21.3(2) . . . . ? C10 C3 C4 C5 99.82(19) . . . . ? O1 C3 C4 C9 44.0(2) . . . . ? C2 C3 C4 C9 162.70(16) . . . . ? C10 C3 C4 C9 -76.2(2) . . . . ? C9 C4 C5 C6 -0.1(3) . . . . ? C3 C4 C5 C6 -176.2(2) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C5 C4 C9 C8 0.4(3) . . . . ? C3 C4 C9 C8 176.58(18) . . . . ? C7 C8 C9 C4 -0.1(3) . . . . ? O1 C3 C10 C15 166.22(15) . . . . ? C2 C3 C10 C15 46.2(2) . . . . ? C4 C3 C10 C15 -75.82(19) . . . . ? O1 C3 C10 C11 -16.8(2) . . . . ? C2 C3 C10 C11 -136.82(16) . . . . ? C4 C3 C10 C11 101.18(17) . . . . ? C15 C10 C11 C12 -1.6(3) . . . . ? C3 C10 C11 C12 -178.66(16) . . . . ? C10 C11 C12 C13 1.2(3) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C11 C10 C15 C14 0.9(3) . . . . ? C3 C10 C15 C14 178.02(17) . . . . ? C13 C14 C15 C10 0.1(3) . . . . ? C20A N1A C16A O2 178.6(2) . . . . ? C20A N1A C16A C17A -0.3(3) . . . . ? O2 C16A C17A C18 -178.8(2) . . . . ? N1A C16A C17A C18 0.1(3) . . . . ? C16A C17A C18 C19 0.5(4) . . . . ? C17A C18 C19 C20A -0.7(4) . . . . ? C18 C19 C20A N1A 0.4(4) . . . . ? C16A N1A C20A C19 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.67 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.170 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.031 data_1-c_1hr _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8000(10) _cell_length_b 8.0810(10) _cell_length_c 13.476(2) _cell_angle_alpha 85.03(2) _cell_angle_beta 75.62(2) _cell_angle_gamma 81.09(2) _cell_volume 811.85(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6455 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6455 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 24.65 _reflns_number_total 2720 _reflns_number_gt 1713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2720 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35450(15) 1.08079(16) 0.23534(9) 0.0427(4) Uani 1 1 d . . . H1 H 0.4218 1.0309 0.2695 0.051 Uiso 1 1 calc R . . C1 C 0.0395(2) 0.9981(2) 0.44773(14) 0.0421(5) Uani 1 1 d . . . C2 C 0.1071(2) 0.9950(2) 0.35827(14) 0.0411(5) Uani 1 1 d . . . C3 C 0.2032(2) 0.9953(2) 0.24823(12) 0.0335(4) Uani 1 1 d . . . C4 C 0.0854(2) 1.0884(2) 0.17988(13) 0.0355(4) Uani 1 1 d . . . C5 C -0.0981(2) 1.1141(3) 0.21198(16) 0.0535(6) Uani 1 1 d . . . H5 H -0.1536 1.0802 0.2784 0.064 Uiso 1 1 calc R . . C6 C -0.2011(3) 1.1908(3) 0.14514(19) 0.0699(7) Uani 1 1 d . . . H6 H -0.3250 1.2071 0.1674 0.084 Uiso 1 1 calc R . . C7 C -0.1225(3) 1.2422(3) 0.04790(19) 0.0652(7) Uani 1 1 d . . . H7 H -0.1918 1.2937 0.0039 0.078 Uiso 1 1 calc R . . C8 C 0.0609(3) 1.2169(3) 0.01547(16) 0.0602(6) Uani 1 1 d . . . H8 H 0.1159 1.2517 -0.0509 0.072 Uiso 1 1 calc R . . C9 C 0.1639(2) 1.1403(3) 0.08087(14) 0.0474(5) Uani 1 1 d . . . H9 H 0.2877 1.1235 0.0579 0.057 Uiso 1 1 calc R . . C10 C 0.2605(2) 0.8139(2) 0.21449(12) 0.0341(4) Uani 1 1 d . . . C11 C 0.4297(2) 0.7658(3) 0.15392(14) 0.0463(5) Uani 1 1 d . . . H11 H 0.5105 0.8428 0.1347 0.056 Uiso 1 1 calc R . . C12 C 0.4786(3) 0.6030(3) 0.12186(16) 0.0558(6) Uani 1 1 d . . . H12 H 0.5928 0.5712 0.0819 0.067 Uiso 1 1 calc R . . C13 C 0.3607(3) 0.4889(3) 0.14842(16) 0.0579(6) Uani 1 1 d . . . H13 H 0.3950 0.3799 0.1270 0.069 Uiso 1 1 calc R . . C14 C 0.1912(3) 0.5357(3) 0.20695(16) 0.0588(6) Uani 1 1 d . . . H14 H 0.1102 0.4587 0.2242 0.071 Uiso 1 1 calc R . . C15 C 0.1412(3) 0.6979(2) 0.24019(15) 0.0483(5) Uani 1 1 d . . . H15 H 0.0266 0.7289 0.2800 0.058 Uiso 1 1 calc R . . O2 O 0.4607(2) 0.0689(2) 0.62506(12) 0.0735(5) Uani 1 1 d . . . N1A N 0.3804(2) 0.2158(2) 0.48954(14) 0.0635(6) Uani 1 1 d . . . H1NA H 0.4195 0.1278 0.4547 0.076 Uiso 1 1 calc R . . C16A C 0.3942(3) 0.2071(3) 0.58816(18) 0.0578(6) Uani 1 1 d . . . C17A C 0.3296(3) 0.3555(4) 0.6413(2) 0.0730(7) Uani 1 1 d . . . H17A H 0.3361 0.3572 0.7092 0.088 Uiso 1 1 calc R . . C18 C 0.2580(3) 0.4960(4) 0.5951(2) 0.0804(8) Uani 1 1 d . . . H18A H 0.2163 0.5927 0.6314 0.097 Uiso 1 1 calc R . . C19 C 0.2465(3) 0.4965(4) 0.4936(2) 0.0819(8) Uani 1 1 d . . . H19A H 0.1969 0.5924 0.4619 0.098 Uiso 1 1 calc R . . C20A C 0.3085(3) 0.3555(4) 0.4425(2) 0.0795(8) Uani 1 1 d . . . H20A H 0.3022 0.3535 0.3746 0.095 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0455(7) 0.0438(9) 0.0426(8) 0.0021(6) -0.0154(6) -0.0119(6) C1 0.0489(11) 0.0430(12) 0.0309(10) -0.0042(9) -0.0046(8) -0.0028(9) C2 0.0487(11) 0.0385(12) 0.0345(11) -0.0022(9) -0.0084(8) -0.0030(8) C3 0.0362(9) 0.0361(11) 0.0272(10) -0.0013(8) -0.0040(7) -0.0076(7) C4 0.0419(10) 0.0306(11) 0.0326(10) -0.0042(8) -0.0074(7) -0.0020(8) C5 0.0439(11) 0.0589(15) 0.0488(13) 0.0072(11) -0.0045(9) 0.0037(9) C6 0.0485(13) 0.0815(19) 0.0729(17) 0.0089(14) -0.0173(11) 0.0096(12) C7 0.0707(15) 0.0627(17) 0.0643(16) 0.0056(13) -0.0346(12) 0.0092(12) C8 0.0747(15) 0.0667(17) 0.0387(12) 0.0093(11) -0.0206(10) -0.0037(11) C9 0.0488(11) 0.0545(14) 0.0358(11) 0.0021(10) -0.0081(8) -0.0035(9) C10 0.0409(10) 0.0359(11) 0.0253(9) -0.0017(8) -0.0095(7) -0.0019(8) C11 0.0452(11) 0.0492(14) 0.0422(12) -0.0086(10) -0.0064(9) -0.0022(9) C12 0.0558(13) 0.0553(15) 0.0531(14) -0.0187(11) -0.0135(10) 0.0118(11) C13 0.0846(16) 0.0377(13) 0.0503(14) -0.0098(10) -0.0234(12) 0.0110(12) C14 0.0829(15) 0.0380(14) 0.0554(14) 0.0025(11) -0.0146(12) -0.0142(11) C15 0.0531(11) 0.0393(13) 0.0475(12) -0.0019(10) -0.0034(9) -0.0055(9) O2 0.0811(11) 0.0848(14) 0.0609(11) 0.0041(9) -0.0359(8) -0.0038(9) N1A 0.0733(12) 0.0660(14) 0.0577(13) 0.0039(10) -0.0310(10) -0.0079(10) C16A 0.0485(12) 0.0741(18) 0.0565(15) 0.0043(13) -0.0230(10) -0.0133(11) C17A 0.0695(15) 0.088(2) 0.0653(17) -0.0131(15) -0.0217(12) -0.0095(14) C18 0.0699(16) 0.075(2) 0.096(2) -0.0114(17) -0.0179(14) -0.0088(13) C19 0.0824(18) 0.067(2) 0.097(2) 0.0086(17) -0.0310(16) -0.0026(14) C20A 0.0896(18) 0.078(2) 0.0765(19) 0.0130(16) -0.0393(15) -0.0072(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.425(2) . ? O1 H1 0.8200 . ? C1 C2 1.191(2) . ? C1 C1 1.391(4) 2_576 ? C2 C3 1.486(2) . ? C3 C4 1.531(2) . ? C3 C10 1.539(2) . ? C4 C5 1.376(2) . ? C4 C9 1.381(2) . ? C5 C6 1.396(3) . ? C5 H5 0.9300 . ? C6 C7 1.360(3) . ? C6 H6 0.9300 . ? C7 C8 1.376(3) . ? C7 H7 0.9300 . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.385(3) . ? C10 C11 1.385(2) . ? C11 C12 1.387(3) . ? C11 H11 0.9300 . ? C12 C13 1.365(3) . ? C12 H12 0.9300 . ? C13 C14 1.376(3) . ? C13 H13 0.9300 . ? C14 C15 1.388(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.271(3) . ? N1A C16A 1.355(3) . ? N1A C20A 1.359(3) . ? N1A H1NA 0.8600 . ? C16A C17A 1.411(3) . ? C17A C18 1.358(4) . ? C17A H17A 0.9300 . ? C18 C19 1.392(4) . ? C18 H18A 0.9300 . ? C19 C20A 1.344(4) . ? C19 H19A 0.9300 . ? C20A H20A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.9(3) . 2_576 ? C1 C2 C3 175.77(19) . . ? O1 C3 C2 108.42(14) . . ? O1 C3 C4 107.68(14) . . ? C2 C3 C4 111.55(14) . . ? O1 C3 C10 110.94(13) . . ? C2 C3 C10 109.80(14) . . ? C4 C3 C10 108.44(14) . . ? C5 C4 C9 118.53(17) . . ? C5 C4 C3 122.00(16) . . ? C9 C4 C3 119.37(15) . . ? C4 C5 C6 120.19(19) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.84(19) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.2(2) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.87(18) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C15 C10 C11 118.85(18) . . ? C15 C10 C3 120.55(15) . . ? C11 C10 C3 120.54(16) . . ? C12 C11 C10 120.09(19) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.68(19) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.52(18) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C16A N1A C20A 123.9(2) . . ? C16A N1A H1NA 118.1 . . ? C20A N1A H1NA 118.1 . . ? O2 C16A N1A 118.6(2) . . ? O2 C16A C17A 125.8(2) . . ? N1A C16A C17A 115.6(2) . . ? C18 C17A C16A 121.1(3) . . ? C18 C17A H17A 119.5 . . ? C16A C17A H17A 119.5 . . ? C17A C18 C19 120.5(3) . . ? C17A C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20A C19 C18 118.7(3) . . ? C20A C19 H19A 120.7 . . ? C18 C19 H19A 120.7 . . ? C19 C20A N1A 120.3(3) . . ? C19 C20A H20A 119.9 . . ? N1A C20A H20A 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 55(100) 2_576 . . . ? C1 C2 C3 O1 -13(3) . . . . ? C1 C2 C3 C4 -131(3) . . . . ? C1 C2 C3 C10 109(3) . . . . ? O1 C3 C4 C5 -139.74(18) . . . . ? C2 C3 C4 C5 -20.9(3) . . . . ? C10 C3 C4 C5 100.1(2) . . . . ? O1 C3 C4 C9 44.0(2) . . . . ? C2 C3 C4 C9 162.81(17) . . . . ? C10 C3 C4 C9 -76.1(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C6 -176.2(2) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C5 C4 C9 C8 0.2(3) . . . . ? C3 C4 C9 C8 176.67(19) . . . . ? C7 C8 C9 C4 -0.3(3) . . . . ? O1 C3 C10 C15 166.26(15) . . . . ? C2 C3 C10 C15 46.4(2) . . . . ? C4 C3 C10 C15 -75.68(19) . . . . ? O1 C3 C10 C11 -16.7(2) . . . . ? C2 C3 C10 C11 -136.56(17) . . . . ? C4 C3 C10 C11 101.32(18) . . . . ? C15 C10 C11 C12 -1.4(3) . . . . ? C3 C10 C11 C12 -178.45(16) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C11 C10 C15 C14 0.9(3) . . . . ? C3 C10 C15 C14 177.93(17) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C20A N1A C16A O2 178.7(2) . . . . ? C20A N1A C16A C17A -0.6(3) . . . . ? O2 C16A C17A C18 -178.8(2) . . . . ? N1A C16A C17A C18 0.4(3) . . . . ? C16A C17A C18 C19 0.1(4) . . . . ? C17A C18 C19 C20A -0.3(4) . . . . ? C18 C19 C20A N1A 0.1(4) . . . . ? C16A N1A C20A C19 0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.65 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.153 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.036 data_I-c_2hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7870(10) _cell_length_b 8.0650(10) _cell_length_c 13.452(2) _cell_angle_alpha 85.02(2) _cell_angle_beta 75.61(2) _cell_angle_gamma 81.18(2) _cell_volume 807.59(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6468 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6601 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 24.96 _reflns_number_total 2805 _reflns_number_gt 1929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0578P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2805 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35455(15) 1.08027(15) 0.23536(9) 0.0410(3) Uani 1 1 d . . . H1 H 0.4218 1.0302 0.2696 0.049 Uiso 1 1 calc R . . C1 C 0.0392(2) 0.9979(2) 0.44778(12) 0.0407(4) Uani 1 1 d . . . C2 C 0.1069(2) 0.9948(2) 0.35823(13) 0.0387(4) Uani 1 1 d . . . C3 C 0.2032(2) 0.9947(2) 0.24794(11) 0.0323(4) Uani 1 1 d . . . C4 C 0.0852(2) 1.0883(2) 0.17991(12) 0.0332(4) Uani 1 1 d . . . C5 C -0.0984(2) 1.1141(3) 0.21188(15) 0.0514(5) Uani 1 1 d . . . H5 H -0.1541 1.0798 0.2783 0.062 Uiso 1 1 calc R . . C6 C -0.2009(3) 1.1911(3) 0.14568(19) 0.0686(7) Uani 1 1 d . . . H6 H -0.3250 1.2078 0.1681 0.082 Uiso 1 1 calc R . . C7 C -0.1217(3) 1.2426(3) 0.04796(17) 0.0630(6) Uani 1 1 d . . . H7 H -0.1912 1.2947 0.0040 0.076 Uiso 1 1 calc R . . C8 C 0.0609(3) 1.2169(3) 0.01530(15) 0.0586(6) Uani 1 1 d . . . H8 H 0.1157 1.2515 -0.0513 0.070 Uiso 1 1 calc R . . C9 C 0.1645(2) 1.1398(3) 0.08065(13) 0.0461(5) Uani 1 1 d . . . H9 H 0.2885 1.1225 0.0576 0.055 Uiso 1 1 calc R . . C10 C 0.2597(2) 0.8133(2) 0.21448(11) 0.0325(4) Uani 1 1 d . . . C11 C 0.4291(2) 0.7647(2) 0.15397(14) 0.0443(5) Uani 1 1 d . . . H11 H 0.5103 0.8418 0.1349 0.053 Uiso 1 1 calc R . . C12 C 0.4779(3) 0.6026(3) 0.12189(15) 0.0536(5) Uani 1 1 d . . . H12 H 0.5923 0.5708 0.0818 0.064 Uiso 1 1 calc R . . C13 C 0.3597(3) 0.4885(3) 0.14843(15) 0.0551(6) Uani 1 1 d . . . H13 H 0.3941 0.3791 0.1271 0.066 Uiso 1 1 calc R . . C14 C 0.1895(3) 0.5352(2) 0.20681(15) 0.0560(6) Uani 1 1 d . . . H14 H 0.1077 0.4584 0.2238 0.067 Uiso 1 1 calc R . . C15 C 0.1409(3) 0.6972(2) 0.23996(14) 0.0464(5) Uani 1 1 d . . . H15 H 0.0264 0.7283 0.2800 0.056 Uiso 1 1 calc R . . O2 O 0.4611(2) 0.0700(2) 0.62458(12) 0.0747(5) Uani 1 1 d . . . N1A N 0.3797(3) 0.2146(3) 0.48949(15) 0.0589(7) Uani 0.934(5) 1 d P . . H1NA H 0.4196 0.1264 0.4548 0.071 Uiso 0.934(5) 1 d PR . . C16A C 0.3943(3) 0.2056(4) 0.58819(18) 0.0522(7) Uani 0.934(5) 1 d P . . C17A C 0.3292(4) 0.3542(4) 0.6412(2) 0.0672(8) Uani 0.934(5) 1 d P . . H17A H 0.3368 0.3571 0.7088 0.081 Uiso 0.934(5) 1 d PR . . C18 C 0.2590(3) 0.4963(4) 0.5939(2) 0.0801(8) Uani 1 1 d . . . H18A H 0.2179 0.5937 0.6296 0.096 Uiso 0.934(5) 1 d PR . . C19 C 0.2469(3) 0.4965(4) 0.4922(2) 0.0830(8) Uani 1 1 d . . . H19A H 0.1974 0.5911 0.4592 0.100 Uiso 0.934(5) 1 d PR . . C20A C 0.3077(4) 0.3541(4) 0.4427(2) 0.0739(9) Uani 0.934(5) 1 d P . . H20A H 0.2997 0.3494 0.3753 0.089 Uiso 0.934(5) 1 d PR . . N1B N 0.450(8) 0.287(8) 0.466(4) 0.125(19) Uiso 0.066(5) 1 d P . . H1NB H 0.4692 0.1977 0.4318 0.150 Uiso 0.066(5) 1 d PR . . C16B C 0.456(7) 0.280(7) 0.573(4) 0.081(15) Uiso 0.066(5) 1 d P . . C17B C 0.404(7) 0.419(6) 0.618(4) 0.077(14) Uiso 0.066(5) 1 d P . . H17B H 0.3757 0.3962 0.6927 0.092 Uiso 0.066(5) 1 d PR . . C20B C 0.427(7) 0.459(8) 0.409(5) 0.12(2) Uiso 0.066(5) 1 d P . . H20B H 0.3960 0.4413 0.3451 0.145 Uiso 0.066(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.145 Uiso 0.07 1 d P . . H19B H 0.1382 0.5198 0.4735 0.145 Uiso 0.07 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0460(7) 0.0436(8) 0.0370(7) 0.0005(6) -0.0142(5) -0.0116(5) C1 0.0477(10) 0.0451(11) 0.0263(9) -0.0048(8) -0.0048(7) -0.0024(8) C2 0.0477(10) 0.0378(10) 0.0276(9) -0.0054(8) -0.0049(7) -0.0016(8) C3 0.0382(9) 0.0351(10) 0.0218(8) -0.0018(7) -0.0041(6) -0.0046(7) C4 0.0445(9) 0.0278(9) 0.0268(9) -0.0052(7) -0.0078(7) -0.0022(7) C5 0.0448(11) 0.0568(13) 0.0435(11) 0.0066(10) -0.0042(8) 0.0054(9) C6 0.0475(12) 0.0814(18) 0.0709(16) 0.0064(13) -0.0182(10) 0.0107(11) C7 0.0730(15) 0.0614(15) 0.0563(14) 0.0087(11) -0.0326(11) 0.0078(11) C8 0.0730(14) 0.0657(15) 0.0365(11) 0.0083(10) -0.0189(9) -0.0041(11) C9 0.0486(10) 0.0562(13) 0.0304(10) 0.0027(9) -0.0075(8) -0.0033(8) C10 0.0425(9) 0.0342(10) 0.0205(8) -0.0016(7) -0.0096(6) -0.0004(7) C11 0.0445(10) 0.0490(12) 0.0366(10) -0.0096(9) -0.0051(8) -0.0008(8) C12 0.0583(12) 0.0531(13) 0.0455(12) -0.0180(10) -0.0125(9) 0.0133(10) C13 0.0845(15) 0.0361(12) 0.0446(12) -0.0093(9) -0.0242(10) 0.0112(10) C14 0.0814(14) 0.0368(12) 0.0507(12) 0.0017(10) -0.0146(11) -0.0153(10) C15 0.0539(11) 0.0402(11) 0.0416(11) -0.0020(9) -0.0038(8) -0.0081(8) O2 0.0827(11) 0.0919(13) 0.0549(10) 0.0027(9) -0.0351(8) -0.0012(9) N1A 0.0669(13) 0.0667(15) 0.0492(12) 0.0040(10) -0.0285(10) -0.0078(11) C16A 0.0444(13) 0.0666(17) 0.0509(14) 0.0064(13) -0.0218(10) -0.0124(12) C17A 0.0630(17) 0.084(2) 0.0587(16) -0.0113(15) -0.0187(13) -0.0107(15) C18 0.0638(15) 0.0792(19) 0.097(2) -0.0133(16) -0.0164(13) -0.0088(13) C19 0.0804(18) 0.082(2) 0.089(2) 0.0103(17) -0.0336(15) -0.0047(15) C20A 0.0839(19) 0.075(2) 0.0681(17) 0.0144(15) -0.0385(14) -0.0049(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4225(19) . ? O1 H1 0.8200 . ? C1 C2 1.190(2) . ? C1 C1 1.387(3) 2_576 ? C2 C3 1.487(2) . ? C3 C4 1.529(2) . ? C3 C10 1.534(2) . ? C4 C5 1.375(2) . ? C4 C9 1.382(2) . ? C5 C6 1.386(3) . ? C5 H5 0.9300 . ? C6 C7 1.365(3) . ? C6 H6 0.9300 . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 C9 1.384(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.379(2) . ? C10 C11 1.385(2) . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.364(3) . ? C12 H12 0.9300 . ? C13 C14 1.377(3) . ? C13 H13 0.9300 . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.252(3) . ? O2 C16B 1.77(6) . ? N1A N1B 0.85(6) . ? N1A C16A 1.355(3) . ? N1A C20A 1.355(3) . ? N1A C16B 1.56(5) . ? N1A H1NA 0.8591 . ? N1A H1NB 0.9089 . ? C16A C16B 0.80(6) . ? C16A C17A 1.408(4) . ? C16A N1B 1.69(6) . ? C16A C17B 1.82(5) . ? C17A C17B 0.83(5) . ? C17A C16B 1.28(5) . ? C17A C18 1.367(4) . ? C17A H17A 0.9287 . ? C17A H17B 0.9642 . ? C18 C17B 1.31(5) . ? C18 C19 1.394(4) . ? C18 H18A 0.9291 . ? C18 H18B 0.9076 . ? C19 C20A 1.340(4) . ? C19 C20B 1.57(6) . ? C19 H19A 0.9291 . ? C19 H19B 0.9295 . ? C20A C20B 1.32(6) . ? C20A N1B 1.26(6) . ? C20A H20A 0.9287 . ? C20A H20B 1.4938 . ? N1B C16B 1.45(6) . ? N1B C20B 1.53(7) . ? N1B H1NA 1.3756 . ? N1B H1NB 0.8595 . ? C16B C17B 1.28(6) . ? C17B C20B 1.71(9) 2_666 ? C17B H17A 1.2923 . ? C17B H17B 0.9795 . ? C20B C17B 1.71(9) 2_666 ? C20B H20A 1.5928 . ? C20B H20B 0.9788 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.7(3) . 2_576 ? C1 C2 C3 175.85(18) . . ? O1 C3 C2 108.14(13) . . ? O1 C3 C4 107.74(13) . . ? C2 C3 C4 111.30(13) . . ? O1 C3 C10 111.19(13) . . ? C2 C3 C10 109.81(13) . . ? C4 C3 C10 108.66(13) . . ? C5 C4 C9 118.62(16) . . ? C5 C4 C3 122.23(15) . . ? C9 C4 C3 119.03(15) . . ? C4 C5 C6 120.39(18) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.68(19) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.36(19) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 120.43(19) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.52(17) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C15 C10 C11 118.53(17) . . ? C15 C10 C3 120.89(14) . . ? C11 C10 C3 120.52(15) . . ? C12 C11 C10 120.35(18) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.56(18) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.99(18) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.53(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 121.02(17) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C16A O2 C16B 23.8(17) . . ? N1B N1A C16A 98(4) . . ? N1B N1A C20A 65(4) . . ? C16A N1A C20A 123.9(2) . . ? N1B N1A C16B 67(4) . . ? C16A N1A C16B 31(2) . . ? C20A N1A C16B 105.3(19) . . ? N1B N1A H1NA 107.6 . . ? C16A N1A H1NA 117.6 . . ? C20A N1A H1NA 118.5 . . ? C16B N1A H1NA 128.3 . . ? N1B N1A H1NB 58.5 . . ? C16A N1A H1NB 127.7 . . ? C20A N1A H1NB 89.7 . . ? C16B N1A H1NB 108.8 . . ? H1NA N1A H1NB 49.6 . . ? C16B C16A O2 117(3) . . ? C16B C16A N1A 88(4) . . ? O2 C16A N1A 118.9(2) . . ? C16B C16A C17A 64(4) . . ? O2 C16A C17A 125.8(2) . . ? N1A C16A C17A 115.3(2) . . ? C16B C16A N1B 59(4) . . ? O2 C16A N1B 127.5(19) . . ? N1A C16A N1B 30(2) . . ? C17A C16A N1B 100(2) . . ? C16B C16A C17B 38(4) . . ? O2 C16A C17B 128.7(15) . . ? N1A C16A C17B 106.1(15) . . ? C17A C16A C17B 26.0(15) . . ? N1B C16A C17B 82(3) . . ? C17B C17A C16B 71(4) . . ? C17B C17A C18 68(3) . . ? C16B C17A C18 107(2) . . ? C17B C17A C16A 106(3) . . ? C16B C17A C16A 34(3) . . ? C18 C17A C16A 121.1(2) . . ? C17B C17A H17A 94.5 . . ? C16B C17A H17A 122.1 . . ? C18 C17A H17A 119.2 . . ? C16A C17A H17A 119.7 . . ? C17B C17A H17B 65.7 . . ? C16B C17A H17B 110.8 . . ? C18 C17A H17B 103.9 . . ? C16A C17A H17B 127.5 . . ? H17A C17A H17B 28.8 . . ? C17B C18 C17A 36(2) . . ? C17B C18 C19 118(2) . . ? C17A C18 C19 120.7(3) . . ? C17B C18 H18A 110.3 . . ? C17A C18 H18A 120.1 . . ? C19 C18 H18A 119.3 . . ? C17B C18 H18B 122.4 . . ? C17A C18 H18B 103.8 . . ? C19 C18 H18B 118.7 . . ? H18A C18 H18B 43.0 . . ? C20A C19 C18 117.8(3) . . ? C20A C19 C20B 53(2) . . ? C18 C19 C20B 117(2) . . ? C20A C19 H19A 120.3 . . ? C18 C19 H19A 121.9 . . ? C20B C19 H19A 98.1 . . ? C20A C19 H19B 97.4 . . ? C18 C19 H19B 122.3 . . ? C20B C19 H19B 120.9 . . ? H19A C19 H19B 49.2 . . ? C20B C20A N1B 73(4) . . ? C20B C20A C19 72(3) . . ? N1B C20A C19 109(3) . . ? C20B C20A N1A 110(3) . . ? N1B C20A N1A 38(3) . . ? C19 C20A N1A 121.3(3) . . ? C20B C20A H20A 88.2 . . ? N1B C20A H20A 118.0 . . ? C19 C20A H20A 120.0 . . ? N1A C20A H20A 118.7 . . ? C20B C20A H20B 40.1 . . ? N1B C20A H20B 96.1 . . ? C19 C20A H20B 94.1 . . ? N1A C20A H20B 126.3 . . ? H20A C20A H20B 48.2 . . ? N1A N1B C20A 78(4) . . ? N1A N1B C16B 81(4) . . ? C20A N1B C16B 118(4) . . ? N1A N1B C20B 133(6) . . ? C20A N1B C20B 56(3) . . ? C16B N1B C20B 119(5) . . ? N1A N1B C16A 53(3) . . ? C20A N1B C16A 108(4) . . ? C16B N1B C16A 28(2) . . ? C20B N1B C16A 137(5) . . ? N1A N1B H1NA 36.5 . . ? C20A N1B H1NA 93.5 . . ? C16B N1B H1NA 102.1 . . ? C20B N1B H1NA 136.5 . . ? C16A N1B H1NA 76.4 . . ? N1A N1B H1NB 64.4 . . ? C20A N1B H1NB 98.8 . . ? C16B N1B H1NB 122.3 . . ? C20B N1B H1NB 118.7 . . ? C16A N1B H1NB 101.4 . . ? H1NA N1B H1NB 28.5 . . ? C16A C16B C17A 82(4) . . ? C16A C16B N1B 93(5) . . ? C17A C16B N1B 122(4) . . ? C16A C16B C17B 120(5) . . ? C17A C16B C17B 38(3) . . ? N1B C16B C17B 116(5) . . ? C16A C16B N1A 60(3) . . ? C17A C16B N1A 111(3) . . ? N1B C16B N1A 32(3) . . ? C17B C16B N1A 128(4) . . ? C16A C16B O2 39(3) . . ? C17A C16B O2 101(3) . . ? N1B C16B O2 110(4) . . ? C17B C16B O2 130(4) . . ? N1A C16B O2 85(3) . . ? C17A C17B C18 76(4) . . ? C17A C17B C16B 71(4) . . ? C18 C17B C16B 110(4) . . ? C17A C17B C20B 169(5) . 2_666 ? C18 C17B C20B 112(4) . 2_666 ? C16B C17B C20B 111(4) . 2_666 ? C17A C17B C16A 48(3) . . ? C18 C17B C16A 100(3) . . ? C16B C17B C16A 23(3) . . ? C20B C17B C16A 133(3) 2_666 . ? C17A C17B H17A 45.8 . . ? C18 C17B H17A 100.2 . . ? C16B C17B H17A 97.6 . . ? C20B C17B H17A 124.3 2_666 . ? C16A C17B H17A 79.7 . . ? C17A C17B H17B 63.8 . . ? C18 C17B H17B 107.5 . . ? C16B C17B H17B 109.4 . . ? C20B C17B H17B 106.5 2_666 . ? C16A C17B H17B 94.8 . . ? H17A C17B H17B 18.1 . . ? C20A C20B C19 54(2) . . ? C20A C20B N1B 52(3) . . ? C19 C20B N1B 86(4) . . ? C20A C20B C17B 171(5) . 2_666 ? C19 C20B C17B 125(4) . 2_666 ? N1B C20B C17B 120(5) . 2_666 ? C20A C20B H20A 35.6 . . ? C19 C20B H20A 77.3 . . ? N1B C20B H20A 73.9 . . ? C17B C20B H20A 151.9 2_666 . ? C20A C20B H20B 79.4 . . ? C19 C20B H20B 106.9 . . ? N1B C20B H20B 107.4 . . ? C17B C20B H20B 108.6 2_666 . ? H20A C20B H20B 43.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 17(74) 2_576 . . . ? C1 C2 C3 O1 -14(3) . . . . ? C1 C2 C3 C4 -132(3) . . . . ? C1 C2 C3 C10 107(3) . . . . ? O1 C3 C4 C5 -139.62(17) . . . . ? C2 C3 C4 C5 -21.2(2) . . . . ? C10 C3 C4 C5 99.81(19) . . . . ? O1 C3 C4 C9 44.5(2) . . . . ? C2 C3 C4 C9 162.86(16) . . . . ? C10 C3 C4 C9 -76.10(19) . . . . ? C9 C4 C5 C6 -0.3(3) . . . . ? C3 C4 C5 C6 -176.3(2) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? C5 C4 C9 C8 0.5(3) . . . . ? C3 C4 C9 C8 176.58(18) . . . . ? C7 C8 C9 C4 -0.3(3) . . . . ? O1 C3 C10 C15 166.11(14) . . . . ? C2 C3 C10 C15 46.5(2) . . . . ? C4 C3 C10 C15 -75.48(18) . . . . ? O1 C3 C10 C11 -16.8(2) . . . . ? C2 C3 C10 C11 -136.47(16) . . . . ? C4 C3 C10 C11 101.59(17) . . . . ? C15 C10 C11 C12 -1.2(3) . . . . ? C3 C10 C11 C12 -178.38(16) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C11 C10 C15 C14 0.6(3) . . . . ? C3 C10 C15 C14 177.69(16) . . . . ? C13 C14 C15 C10 0.7(3) . . . . ? C16B O2 C16A N1A 104(4) . . . . ? C16B O2 C16A C17A -76(4) . . . . ? C16B O2 C16A N1B 70(5) . . . . ? C16B O2 C16A C17B -43(4) . . . . ? N1B N1A C16A C16B 5(5) . . . . ? C20A N1A C16A C16B -60(3) . . . . ? N1B N1A C16A O2 -116(4) . . . . ? C20A N1A C16A O2 179.2(2) . . . . ? C16B N1A C16A O2 -121(3) . . . . ? N1B N1A C16A C17A 65(4) . . . . ? C20A N1A C16A C17A -0.3(4) . . . . ? C16B N1A C16A C17A 60(3) . . . . ? C20A N1A C16A N1B -65(4) . . . . ? C16B N1A C16A N1B -5(5) . . . . ? N1B N1A C16A C17B 39(4) . . . . ? C20A N1A C16A C17B -26.4(17) . . . . ? C16B N1A C16A C17B 34(4) . . . . ? C16B C16A C17A C17B 0(5) . . . . ? O2 C16A C17A C17B 106(3) . . . . ? N1A C16A C17A C17B -74(3) . . . . ? N1B C16A C17A C17B -47(4) . . . . ? O2 C16A C17A C16B 106(4) . . . . ? N1A C16A C17A C16B -75(4) . . . . ? N1B C16A C17A C16B -47(4) . . . . ? C17B C16A C17A C16B 0(5) . . . . ? C16B C16A C17A C18 74(4) . . . . ? O2 C16A C17A C18 179.8(3) . . . . ? N1A C16A C17A C18 -0.8(4) . . . . ? N1B C16A C17A C18 26(2) . . . . ? C17B C16A C17A C18 73(3) . . . . ? C16B C17A C18 C17B -61(4) . . . . ? C16A C17A C18 C17B -96(4) . . . . ? C17B C17A C18 C19 97(4) . . . . ? C16B C17A C18 C19 36(3) . . . . ? C16A C17A C18 C19 1.3(4) . . . . ? C17B C18 C19 C20A 41(3) . . . . ? C17A C18 C19 C20A -0.6(4) . . . . ? C17B C18 C19 C20B -20(4) . . . . ? C17A C18 C19 C20B -61(3) . . . . ? C18 C19 C20A C20B -104(3) . . . . ? C18 C19 C20A N1B -40(3) . . . . ? C20B C19 C20A N1B 64(4) . . . . ? C18 C19 C20A N1A -0.4(4) . . . . ? C20B C19 C20A N1A 104(3) . . . . ? N1B N1A C20A C20B 0(5) . . . . ? C16A N1A C20A C20B 82(3) . . . . ? C16B N1A C20A C20B 54(4) . . . . ? C16A N1A C20A N1B 82(4) . . . . ? C16B N1A C20A N1B 54(5) . . . . ? N1B N1A C20A C19 -81(4) . . . . ? C16A N1A C20A C19 0.9(4) . . . . ? C16B N1A C20A C19 -27(2) . . . . ? C16A N1A N1B C20A -123.9(16) . . . . ? C16B N1A N1B C20A -121(4) . . . . ? C16A N1A N1B C16B -3(3) . . . . ? C20A N1A N1B C16B 121(4) . . . . ? C16A N1A N1B C20B -124(7) . . . . ? C20A N1A N1B C20B 0(6) . . . . ? C16B N1A N1B C20B -121(9) . . . . ? C20A N1A N1B C16A 123.9(16) . . . . ? C16B N1A N1B C16A 3(3) . . . . ? C20B C20A N1B N1A 180(5) . . . . ? C19 C20A N1B N1A 116(3) . . . . ? C20B C20A N1B C16B 107(6) . . . . ? C19 C20A N1B C16B 44(5) . . . . ? N1A C20A N1B C16B -73(5) . . . . ? C19 C20A N1B C20B -63(3) . . . . ? N1A C20A N1B C20B -180(5) . . . . ? C20B C20A N1B C16A 136(5) . . . . ? C19 C20A N1B C16A 73(4) . . . . ? N1A C20A N1B C16A -44(2) . . . . ? C16B C16A N1B N1A -174(6) . . . . ? O2 C16A N1B N1A 83(4) . . . . ? C17A C16A N1B N1A -124(3) . . . . ? C17B C16A N1B N1A -143(4) . . . . ? C16B C16A N1B C20A -116(6) . . . . ? O2 C16A N1B C20A 141(3) . . . . ? N1A C16A N1B C20A 58(4) . . . . ? C17A C16A N1B C20A -66(4) . . . . ? C17B C16A N1B C20A -85(4) . . . . ? O2 C16A N1B C16B -102(5) . . . . ? N1A C16A N1B C16B 174(6) . . . . ? C17A C16A N1B C16B 51(4) . . . . ? C17B C16A N1B C16B 32(4) . . . . ? C16B C16A N1B C20B -59(7) . . . . ? O2 C16A N1B C20B -161(5) . . . . ? N1A C16A N1B C20B 116(8) . . . . ? C17A C16A N1B C20B -8(7) . . . . ? C17B C16A N1B C20B -27(7) . . . . ? O2 C16A C16B C17A -118.7(18) . . . . ? N1A C16A C16B C17A 119.3(17) . . . . ? N1B C16A C16B C17A 122(4) . . . . ? C17B C16A C16B C17A 0(4) . . . . ? O2 C16A C16B N1B 119(3) . . . . ? N1A C16A C16B N1B -3(3) . . . . ? C17A C16A C16B N1B -122(4) . . . . ? C17B C16A C16B N1B -122(7) . . . . ? O2 C16A C16B C17B -119(5) . . . . ? N1A C16A C16B C17B 119(5) . . . . ? C17A C16A C16B C17B 0(4) . . . . ? N1B C16A C16B C17B 122(7) . . . . ? O2 C16A C16B N1A 122.0(19) . . . . ? C17A C16A C16B N1A -119.3(17) . . . . ? N1B C16A C16B N1A 3(3) . . . . ? C17B C16A C16B N1A -119(5) . . . . ? N1A C16A C16B O2 -122.0(19) . . . . ? C17A C16A C16B O2 118.7(18) . . . . ? N1B C16A C16B O2 -119(3) . . . . ? C17B C16A C16B O2 119(5) . . . . ? C17B C17A C16B C16A -180(5) . . . . ? C18 C17A C16B C16A -121(3) . . . . ? C17B C17A C16B N1B -92(6) . . . . ? C18 C17A C16B N1B -33(5) . . . . ? C16A C17A C16B N1B 88(6) . . . . ? C18 C17A C16B C17B 59(4) . . . . ? C16A C17A C16B C17B 180(5) . . . . ? C17B C17A C16B N1A -126(5) . . . . ? C18 C17A C16B N1A -67(4) . . . . ? C16A C17A C16B N1A 54(3) . . . . ? C17B C17A C16B O2 146(4) . . . . ? C18 C17A C16B O2 -154.9(15) . . . . ? C16A C17A C16B O2 -34(2) . . . . ? N1A N1B C16B C16A 4(5) . . . . ? C20A N1B C16B C16A 75(6) . . . . ? C20B N1B C16B C16A 139(5) . . . . ? N1A N1B C16B C17A -78(6) . . . . ? C20A N1B C16B C17A -7(8) . . . . ? C20B N1B C16B C17A 57(7) . . . . ? C16A N1B C16B C17A -82(5) . . . . ? N1A N1B C16B C17B -120(5) . . . . ? C20A N1B C16B C17B -50(7) . . . . ? C20B N1B C16B C17B 14(8) . . . . ? C16A N1B C16B C17B -125(7) . . . . ? C20A N1B C16B N1A 71(5) . . . . ? C20B N1B C16B N1A 134(7) . . . . ? C16A N1B C16B N1A -4(5) . . . . ? N1A N1B C16B O2 40(5) . . . . ? C20A N1B C16B O2 111(5) . . . . ? C20B N1B C16B O2 175(4) . . . . ? C16A N1B C16B O2 36(2) . . . . ? N1B N1A C16B C16A -175(6) . . . . ? C20A N1A C16B C16A 132(3) . . . . ? N1B N1A C16B C17A 118(6) . . . . ? C16A N1A C16B C17A -67(4) . . . . ? C20A N1A C16B C17A 65(4) . . . . ? C16A N1A C16B N1B 175(6) . . . . ? C20A N1A C16B N1B -53(4) . . . . ? N1B N1A C16B C17B 79(7) . . . . ? C16A N1A C16B C17B -106(7) . . . . ? C20A N1A C16B C17B 25(6) . . . . ? N1B N1A C16B O2 -143(5) . . . . ? C16A N1A C16B O2 32(2) . . . . ? C20A N1A C16B O2 164.0(10) . . . . ? C16A O2 C16B C17A 62(3) . . . . ? C16A O2 C16B N1B -68(4) . . . . ? C16A O2 C16B C17B 89(6) . . . . ? C16A O2 C16B N1A -48(3) . . . . ? C16B C17A C17B C18 118(3) . . . . ? C16A C17A C17B C18 117.7(12) . . . . ? C18 C17A C17B C16B -118(3) . . . . ? C16A C17A C17B C16B 0(3) . . . . ? C16B C17A C17B C20B -100(28) . . . 2_666 ? C18 C17A C17B C20B 142(29) . . . 2_666 ? C16A C17A C17B C20B -100(28) . . . 2_666 ? C16B C17A C17B C16A 0(3) . . . . ? C18 C17A C17B C16A -117.7(12) . . . . ? C19 C18 C17B C17A -104(3) . . . . ? C17A C18 C17B C16B 63(4) . . . . ? C19 C18 C17B C16B -41(5) . . . . ? C17A C18 C17B C20B -173(6) . . . 2_666 ? C19 C18 C17B C20B 83(4) . . . 2_666 ? C17A C18 C17B C16A 42(2) . . . . ? C19 C18 C17B C16A -62(3) . . . . ? C16A C16B C17B C17A 0(6) . . . . ? N1B C16B C17B C17A 110(5) . . . . ? N1A C16B C17B C17A 74(6) . . . . ? O2 C16B C17B C17A -46(5) . . . . ? C16A C16B C17B C18 -66(7) . . . . ? C17A C16B C17B C18 -66(4) . . . . ? N1B C16B C17B C18 44(6) . . . . ? N1A C16B C17B C18 8(7) . . . . ? O2 C16B C17B C18 -112(5) . . . . ? C16A C16B C17B C20B 169(5) . . . 2_666 ? C17A C16B C17B C20B 169(6) . . . 2_666 ? N1B C16B C17B C20B -81(5) . . . 2_666 ? N1A C16B C17B C20B -117(5) . . . 2_666 ? O2 C16B C17B C20B 123(5) . . . 2_666 ? C17A C16B C17B C16A 0(6) . . . . ? N1B C16B C17B C16A 110(8) . . . . ? N1A C16B C17B C16A 74(6) . . . . ? O2 C16B C17B C16A -46(4) . . . . ? C16B C16A C17B C17A -180(8) . . . . ? O2 C16A C17B C17A -94(3) . . . . ? N1A C16A C17B C17A 115(3) . . . . ? N1B C16A C17B C17A 133(4) . . . . ? C16B C16A C17B C18 120(7) . . . . ? O2 C16A C17B C18 -154.6(15) . . . . ? N1A C16A C17B C18 54(3) . . . . ? C17A C16A C17B C18 -61(3) . . . . ? N1B C16A C17B C18 72(3) . . . . ? O2 C16A C17B C16B 86(6) . . . . ? N1A C16A C17B C16B -65(6) . . . . ? C17A C16A C17B C16B 180(8) . . . . ? N1B C16A C17B C16B -47(6) . . . . ? C16B C16A C17B C20B -14(7) . . . 2_666 ? O2 C16A C17B C20B 72(5) . . . 2_666 ? N1A C16A C17B C20B -79(5) . . . 2_666 ? C17A C16A C17B C20B 166(7) . . . 2_666 ? N1B C16A C17B C20B -61(5) . . . 2_666 ? N1B C20A C20B C19 -118(3) . . . . ? N1A C20A C20B C19 -117.5(9) . . . . ? C19 C20A C20B N1B 118(3) . . . . ? N1A C20A C20B N1B 0(3) . . . . ? N1B C20A C20B C17B -30(30) . . . 2_666 ? C19 C20A C20B C17B 88(31) . . . 2_666 ? N1A C20A C20B C17B -30(31) . . . 2_666 ? C18 C19 C20B C20A 106.0(18) . . . . ? C20A C19 C20B N1B -44(3) . . . . ? C18 C19 C20B N1B 62(4) . . . . ? C20A C19 C20B C17B -169(6) . . . 2_666 ? C18 C19 C20B C17B -63(5) . . . 2_666 ? N1A N1B C20B C20A 0(7) . . . . ? C16B N1B C20B C20A -106(5) . . . . ? C16A N1B C20B C20A -78(6) . . . . ? N1A N1B C20B C19 46(8) . . . . ? C20A N1B C20B C19 46(2) . . . . ? C16B N1B C20B C19 -59(5) . . . . ? C16A N1B C20B C19 -32(7) . . . . ? N1A N1B C20B C17B 175(6) . . . 2_666 ? C20A N1B C20B C17B 175(6) . . . 2_666 ? C16B N1B C20B C17B 69(6) . . . 2_666 ? C16A N1B C20B C17B 97(7) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.175 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.037 data_I-c_3hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7800(10) _cell_length_b 8.0590(10) _cell_length_c 13.452(2) _cell_angle_alpha 84.98(2) _cell_angle_beta 75.61(2) _cell_angle_gamma 81.22(2) _cell_volume 806.30(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8170 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8170 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2840 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.1483P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2840 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35456(15) 1.08016(15) 0.23511(8) 0.0431(3) Uani 1 1 d . . . H1 H 0.4221 1.0303 0.2693 0.052 Uiso 1 1 calc R . . C1 C 0.0391(2) 0.9976(2) 0.44790(13) 0.0433(4) Uani 1 1 d . . . C2 C 0.1069(2) 0.9944(2) 0.35805(12) 0.0416(4) Uani 1 1 d . . . C3 C 0.2030(2) 0.9942(2) 0.24820(11) 0.0349(4) Uani 1 1 d . . . C4 C 0.0853(2) 1.0884(2) 0.17959(12) 0.0352(4) Uani 1 1 d . . . C5 C -0.0981(2) 1.1146(3) 0.21194(15) 0.0541(5) Uani 1 1 d . . . H5 H -0.1538 1.0806 0.2785 0.065 Uiso 1 1 calc R . . C6 C -0.2008(3) 1.1919(3) 0.14558(18) 0.0708(7) Uani 1 1 d . . . H6 H -0.3249 1.2090 0.1681 0.085 Uiso 1 1 calc R . . C7 C -0.1220(3) 1.2427(3) 0.04825(17) 0.0643(6) Uani 1 1 d . . . H7 H -0.1915 1.2947 0.0043 0.077 Uiso 1 1 calc R . . C8 C 0.0608(3) 1.2168(3) 0.01536(15) 0.0604(6) Uani 1 1 d . . . H8 H 0.1155 1.2518 -0.0512 0.072 Uiso 1 1 calc R . . C9 C 0.1648(3) 1.1391(2) 0.08033(13) 0.0476(5) Uani 1 1 d . . . H9 H 0.2888 1.1208 0.0570 0.057 Uiso 1 1 calc R . . C10 C 0.2593(2) 0.8130(2) 0.21452(11) 0.0346(4) Uani 1 1 d . . . C11 C 0.4286(2) 0.7645(2) 0.15431(13) 0.0466(5) Uani 1 1 d . . . H11 H 0.5101 0.8415 0.1353 0.056 Uiso 1 1 calc R . . C12 C 0.4772(3) 0.6022(3) 0.12217(15) 0.0562(5) Uani 1 1 d . . . H12 H 0.5919 0.5704 0.0824 0.067 Uiso 1 1 calc R . . C13 C 0.3588(3) 0.4883(3) 0.14826(15) 0.0575(6) Uani 1 1 d . . . H13 H 0.3928 0.3790 0.1266 0.069 Uiso 1 1 calc R . . C14 C 0.1890(3) 0.5352(2) 0.20669(15) 0.0583(6) Uani 1 1 d . . . H14 H 0.1073 0.4582 0.2239 0.070 Uiso 1 1 calc R . . C15 C 0.1398(3) 0.6974(2) 0.23990(14) 0.0483(5) Uani 1 1 d . . . H15 H 0.0250 0.7286 0.2797 0.058 Uiso 1 1 calc R . . O2 O 0.4619(2) 0.0702(2) 0.62443(12) 0.0819(5) Uani 1 1 d . . . N1A N 0.3794(3) 0.2133(3) 0.48961(15) 0.0624(7) Uani 0.910(5) 1 d P . . H1NA H 0.4193 0.1251 0.4549 0.075 Uiso 0.910(5) 1 d PR . . C16A C 0.3948(3) 0.2047(4) 0.58797(19) 0.0564(7) Uani 0.910(5) 1 d P . . C17A C 0.3307(4) 0.3535(4) 0.6403(2) 0.0700(9) Uani 0.910(5) 1 d P . . H17A H 0.3382 0.3564 0.7079 0.084 Uiso 0.910(5) 1 d PR . . C18 C 0.2590(3) 0.4966(4) 0.5931(2) 0.0842(8) Uani 1 1 d . . . H18A H 0.2179 0.5940 0.6288 0.101 Uiso 0.910(5) 1 d PR . . C19 C 0.2474(3) 0.4963(4) 0.4920(2) 0.0863(8) Uani 1 1 d . . . H19A H 0.1980 0.5909 0.4590 0.104 Uiso 0.910(5) 1 d PR . . C20A C 0.3081(4) 0.3522(4) 0.4421(2) 0.0769(9) Uani 0.910(5) 1 d P . . H20A H 0.3001 0.3475 0.3747 0.092 Uiso 0.910(5) 1 d PR . . N1B N 0.452(4) 0.283(4) 0.466(2) 0.081(8) Uiso 0.090(5) 1 d P . . H1NB H 0.4713 0.1943 0.4318 0.097 Uiso 0.090(5) 1 d PR . . C16B C 0.454(5) 0.279(5) 0.568(3) 0.080(10) Uiso 0.090(5) 1 d P . . C17B C 0.407(4) 0.437(4) 0.616(2) 0.075(9) Uiso 0.090(5) 1 d P . . H17B H 0.3787 0.4144 0.6901 0.090 Uiso 0.090(5) 1 d PR . . C20B C 0.419(4) 0.456(4) 0.416(2) 0.083(10) Uiso 0.090(5) 1 d P . . H20B H 0.3877 0.4381 0.3517 0.099 Uiso 0.090(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.099 Uiso 0.09 1 d P . . H19B H 0.1382 0.5198 0.4735 0.099 Uiso 0.09 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0457(7) 0.0435(8) 0.0440(7) -0.0002(5) -0.0159(5) -0.0108(5) C1 0.0520(10) 0.0431(11) 0.0324(9) -0.0056(8) -0.0075(7) -0.0010(8) C2 0.0506(10) 0.0390(11) 0.0327(9) -0.0054(8) -0.0072(7) -0.0007(8) C3 0.0391(9) 0.0366(10) 0.0277(8) -0.0020(7) -0.0052(7) -0.0053(7) C4 0.0443(9) 0.0281(9) 0.0327(9) -0.0044(7) -0.0093(7) -0.0017(7) C5 0.0476(11) 0.0563(13) 0.0502(11) 0.0070(10) -0.0063(8) 0.0038(9) C6 0.0486(12) 0.0802(18) 0.0770(16) 0.0109(13) -0.0186(11) 0.0096(11) C7 0.0710(15) 0.0617(15) 0.0627(14) 0.0057(11) -0.0331(11) 0.0062(11) C8 0.0775(15) 0.0639(15) 0.0397(11) 0.0080(10) -0.0200(10) -0.0053(11) C9 0.0514(11) 0.0530(12) 0.0351(10) 0.0028(8) -0.0083(8) -0.0033(9) C10 0.0452(9) 0.0335(10) 0.0248(8) -0.0004(7) -0.0105(7) -0.0012(7) C11 0.0465(10) 0.0481(12) 0.0429(10) -0.0099(9) -0.0069(8) -0.0008(8) C12 0.0592(12) 0.0543(14) 0.0511(12) -0.0172(10) -0.0123(9) 0.0116(10) C13 0.0859(15) 0.0366(12) 0.0500(12) -0.0085(9) -0.0253(11) 0.0099(10) C14 0.0825(15) 0.0375(12) 0.0555(12) 0.0035(9) -0.0157(11) -0.0151(10) C15 0.0554(11) 0.0381(11) 0.0475(11) -0.0009(8) -0.0049(8) -0.0074(8) O2 0.0846(11) 0.1043(15) 0.0619(10) 0.0007(9) -0.0369(8) 0.0002(10) N1A 0.0685(14) 0.0684(15) 0.0564(13) 0.0051(11) -0.0290(10) -0.0100(12) C16A 0.0500(14) 0.0703(19) 0.0538(14) 0.0075(13) -0.0220(11) -0.0128(13) C17A 0.0647(17) 0.087(2) 0.0628(16) -0.0102(15) -0.0199(13) -0.0118(15) C18 0.0676(16) 0.085(2) 0.099(2) -0.0133(16) -0.0157(14) -0.0100(13) C19 0.0816(18) 0.082(2) 0.097(2) 0.0102(16) -0.0336(15) -0.0037(15) C20A 0.086(2) 0.079(2) 0.0712(17) 0.0151(16) -0.0377(15) -0.0071(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4238(19) . ? O1 H1 0.8200 . ? C1 C2 1.193(2) . ? C1 C1 1.384(3) 2_576 ? C2 C3 1.481(2) . ? C3 C4 1.533(2) . ? C3 C10 1.534(2) . ? C4 C5 1.373(2) . ? C4 C9 1.380(2) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.357(3) . ? C6 H6 0.9300 . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.379(2) . ? C10 C11 1.382(2) . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.362(3) . ? C12 H12 0.9300 . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.244(3) . ? O2 C16B 1.78(4) . ? N1A N1B 0.84(3) . ? N1A C20A 1.353(3) . ? N1A C16A 1.353(3) . ? N1A C16B 1.49(3) . ? N1A H1NA 0.8591 . ? N1A H1NB 0.9220 . ? C16A C16B 0.80(4) . ? C16A C17A 1.404(4) . ? C16A N1B 1.68(3) . ? C16A C17B 1.96(3) . ? C17A C17B 0.95(4) . ? C17A C16B 1.30(3) . ? C17A C18 1.377(4) . ? C17A H17A 0.9287 . ? C17A H17B 1.0337 . ? C18 C17B 1.28(3) . ? C18 C19 1.386(4) . ? C18 H18A 0.9291 . ? C18 H18B 0.9124 . ? C19 C20A 1.354(4) . ? C19 C20B 1.48(3) . ? C19 H19A 0.9285 . ? C19 H19B 0.9313 . ? C20A N1B 1.28(3) . ? C20A C20B 1.26(3) . ? C20A H20A 0.9287 . ? C20A H20B 1.3975 . ? N1B C16B 1.37(4) . ? N1B C20B 1.51(4) . ? N1B H1NA 1.3642 . ? N1B H1NB 0.8594 . ? C16B C17B 1.44(5) . ? C17B C20B 1.66(5) 2_666 ? C17B H17A 1.3747 . ? C17B H17B 0.9793 . ? C20B C17B 1.66(5) 2_666 ? C20B H20A 1.5820 . ? C20B H20B 0.9788 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.6(3) . 2_576 ? C1 C2 C3 175.77(18) . . ? O1 C3 C2 108.33(13) . . ? O1 C3 C4 107.32(13) . . ? C2 C3 C4 111.49(13) . . ? O1 C3 C10 111.16(13) . . ? C2 C3 C10 110.02(14) . . ? C4 C3 C10 108.52(12) . . ? C5 C4 C9 118.89(16) . . ? C5 C4 C3 121.84(15) . . ? C9 C4 C3 119.15(15) . . ? C4 C5 C6 120.19(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.43(19) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 120.50(18) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 120.24(18) . . ? C4 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C15 C10 C11 118.71(16) . . ? C15 C10 C3 120.66(15) . . ? C11 C10 C3 120.57(15) . . ? C12 C11 C10 120.33(18) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.60(18) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.81(19) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 119.89(19) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C10 C15 C14 120.64(18) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C16A O2 C16B 22.9(11) . . ? N1B N1A C20A 66.3(19) . . ? N1B N1A C16A 97.1(19) . . ? C20A N1A C16A 124.3(3) . . ? N1B N1A C16B 65(2) . . ? C20A N1A C16B 104.8(15) . . ? C16A N1A C16B 32.1(15) . . ? N1B N1A H1NA 106.4 . . ? C20A N1A H1NA 118.1 . . ? C16A N1A H1NA 117.6 . . ? C16B N1A H1NA 128.5 . . ? N1B N1A H1NB 58.0 . . ? C20A N1A H1NB 90.5 . . ? C16A N1A H1NB 126.6 . . ? C16B N1A H1NB 107.5 . . ? H1NA N1A H1NB 48.9 . . ? C16B C16A O2 120(3) . . ? C16B C16A N1A 83(2) . . ? O2 C16A N1A 119.1(2) . . ? C16B C16A C17A 66(3) . . ? O2 C16A C17A 125.8(2) . . ? N1A C16A C17A 115.1(2) . . ? C16B C16A N1B 54(3) . . ? O2 C16A N1B 126.9(10) . . ? N1A C16A N1B 29.9(11) . . ? C17A C16A N1B 100.6(10) . . ? C16B C16A C17B 39(3) . . ? O2 C16A C17B 129.7(9) . . ? N1A C16A C17B 104.5(9) . . ? C17A C16A C17B 26.8(9) . . ? N1B C16A C17B 81.1(15) . . ? C17B C17A C16B 77(3) . . ? C17B C17A C18 63.5(19) . . ? C16B C17A C18 105.3(16) . . ? C17B C17A C16A 111.4(18) . . ? C16B C17A C16A 34.0(18) . . ? C18 C17A C16A 121.5(2) . . ? C17B C17A H17A 93.9 . . ? C16B C17A H17A 124.9 . . ? C18 C17A H17A 119.0 . . ? C16A C17A H17A 119.5 . . ? C17B C17A H17B 58.9 . . ? C16B C17A H17B 114.5 . . ? C18 C17A H17B 96.3 . . ? C16A C17A H17B 132.8 . . ? H17A C17A H17B 35.2 . . ? C17B C18 C17A 41.8(16) . . ? C17B C18 C19 118.6(14) . . ? C17A C18 C19 120.2(3) . . ? C17B C18 H18A 105.8 . . ? C17A C18 H18A 120.2 . . ? C19 C18 H18A 119.5 . . ? C17B C18 H18B 121.8 . . ? C17A C18 H18B 103.7 . . ? C19 C18 H18B 119.5 . . ? H18A C18 H18B 43.0 . . ? C20A C19 C18 118.0(3) . . ? C20A C19 C20B 52.5(13) . . ? C18 C19 C20B 115.8(12) . . ? C20A C19 H19A 120.3 . . ? C18 C19 H19A 121.7 . . ? C20B C19 H19A 100.0 . . ? C20A C19 H19B 97.4 . . ? C18 C19 H19B 121.9 . . ? C20B C19 H19B 122.3 . . ? H19A C19 H19B 49.2 . . ? N1B C20A C20B 73(2) . . ? N1B C20A N1A 37.3(15) . . ? C20B C20A N1A 110.2(14) . . ? N1B C20A C19 109.3(14) . . ? C20B C20A C19 68.9(14) . . ? N1A C20A C19 120.8(3) . . ? N1B C20A H20A 118.0 . . ? C20B C20A H20A 91.5 . . ? N1A C20A H20A 119.1 . . ? C19 C20A H20A 120.0 . . ? N1B C20A H20B 97.4 . . ? C20B C20A H20B 42.9 . . ? N1A C20A H20B 128.1 . . ? C19 C20A H20B 92.4 . . ? H20A C20A H20B 48.7 . . ? N1A N1B C20A 76(2) . . ? N1A N1B C16B 81(2) . . ? C20A N1B C16B 117(2) . . ? N1A N1B C20B 129(3) . . ? C20A N1B C20B 53.0(16) . . ? C16B N1B C20B 116(3) . . ? N1A N1B C16A 53.0(15) . . ? C20A N1B C16A 107.2(19) . . ? C16B N1B C16A 28.0(17) . . ? C20B N1B C16A 133(2) . . ? N1A N1B H1NA 37.2 . . ? C20A N1B H1NA 92.9 . . ? C16B N1B H1NA 102.6 . . ? C20B N1B H1NA 136.7 . . ? C16A N1B H1NA 76.9 . . ? N1A N1B H1NB 65.5 . . ? C20A N1B H1NB 98.9 . . ? C16B N1B H1NB 123.0 . . ? C20B N1B H1NB 121.2 . . ? C16A N1B H1NB 102.0 . . ? H1NA N1B H1NB 28.9 . . ? C16A C16B C17A 80(3) . . ? C16A C16B N1B 98(3) . . ? C17A C16B N1B 126(3) . . ? C16A C16B N1A 64(2) . . ? C17A C16B N1A 113(2) . . ? N1B C16B N1A 34.0(15) . . ? C16A C16B C17B 120(4) . . ? C17A C16B C17B 40.3(17) . . ? N1B C16B C17B 116(3) . . ? N1A C16B C17B 130(3) . . ? C16A C16B O2 37.3(19) . . ? C17A C16B O2 99(2) . . ? N1B C16B O2 112(3) . . ? N1A C16B O2 85.9(19) . . ? C17B C16B O2 130(3) . . ? C17A C17B C18 75(2) . . ? C17A C17B C16B 62(2) . . ? C18 C17B C16B 103(2) . . ? C17A C17B C20B 164(3) . 2_666 ? C18 C17B C20B 121(3) . 2_666 ? C16B C17B C20B 110(3) . 2_666 ? C17A C17B C16A 41.8(14) . . ? C18 C17B C16A 95(2) . . ? C16B C17B C16A 20.5(16) . . ? C20B C17B C16A 129(2) 2_666 . ? C17A C17B H17A 42.4 . . ? C18 C17B H17A 97.8 . . ? C16B C17B H17A 89.9 . . ? C20B C17B H17A 128.6 2_666 . ? C16A C17B H17A 72.5 . . ? C17A C17B H17B 64.7 . . ? C18 C17B H17B 105.9 . . ? C16B C17B H17B 107.8 . . ? C20B C17B H17B 108.1 2_666 . ? C16A C17B H17B 93.0 . . ? H17A C17B H17B 22.6 . . ? C20A C20B C19 58.7(13) . . ? C20A C20B N1B 54.0(16) . . ? C19 C20B N1B 91.9(19) . . ? C20A C20B C17B 170(3) . 2_666 ? C19 C20B C17B 128(2) . 2_666 ? N1B C20B C17B 116(2) . 2_666 ? C20A C20B H20A 35.9 . . ? C19 C20B H20A 81.0 . . ? N1B C20B H20A 75.8 . . ? C17B C20B H20A 145.7 2_666 . ? C20A C20B H20B 76.2 . . ? C19 C20B H20B 106.1 . . ? N1B C20B H20B 105.9 . . ? C17B C20B H20B 106.9 2_666 . ? H20A C20B H20B 40.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 50(48) 2_576 . . . ? C1 C2 C3 O1 -15(3) . . . . ? C1 C2 C3 C4 -133(3) . . . . ? C1 C2 C3 C10 107(3) . . . . ? O1 C3 C4 C5 -139.50(17) . . . . ? C2 C3 C4 C5 -21.0(2) . . . . ? C10 C3 C4 C5 100.29(19) . . . . ? O1 C3 C4 C9 44.6(2) . . . . ? C2 C3 C4 C9 163.09(15) . . . . ? C10 C3 C4 C9 -75.60(19) . . . . ? C9 C4 C5 C6 -0.4(3) . . . . ? C3 C4 C5 C6 -176.28(19) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 0.2(4) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C5 C4 C9 C8 0.8(3) . . . . ? C3 C4 C9 C8 176.81(17) . . . . ? C7 C8 C9 C4 -0.7(3) . . . . ? O1 C3 C10 C15 166.58(14) . . . . ? C2 C3 C10 C15 46.6(2) . . . . ? C4 C3 C10 C15 -75.63(18) . . . . ? O1 C3 C10 C11 -16.3(2) . . . . ? C2 C3 C10 C11 -136.27(16) . . . . ? C4 C3 C10 C11 101.51(17) . . . . ? C15 C10 C11 C12 -1.3(2) . . . . ? C3 C10 C11 C12 -178.47(15) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C11 C10 C15 C14 0.7(3) . . . . ? C3 C10 C15 C14 177.93(16) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C16B O2 C16A N1A 100(3) . . . . ? C16B O2 C16A C17A -80(3) . . . . ? C16B O2 C16A N1B 65(3) . . . . ? C16B O2 C16A C17B -47(3) . . . . ? N1B N1A C16A C16B 6(3) . . . . ? C20A N1A C16A C16B -60(3) . . . . ? N1B N1A C16A O2 -114(2) . . . . ? C20A N1A C16A O2 179.7(3) . . . . ? C16B N1A C16A O2 -121(3) . . . . ? N1B N1A C16A C17A 66(2) . . . . ? C20A N1A C16A C17A -0.1(4) . . . . ? C16B N1A C16A C17A 60(3) . . . . ? C20A N1A C16A N1B -66.1(19) . . . . ? C16B N1A C16A N1B -6(3) . . . . ? N1B N1A C16A C17B 40(2) . . . . ? C20A N1A C16A C17B -26.4(10) . . . . ? C16B N1A C16A C17B 33(3) . . . . ? C16B C16A C17A C17B -2(3) . . . . ? O2 C16A C17A C17B 109(2) . . . . ? N1A C16A C17A C17B -72(2) . . . . ? N1B C16A C17A C17B -44(2) . . . . ? O2 C16A C17A C16B 110(3) . . . . ? N1A C16A C17A C16B -70(3) . . . . ? N1B C16A C17A C16B -42(3) . . . . ? C17B C16A C17A C16B 2(3) . . . . ? C16B C16A C17A C18 69(3) . . . . ? O2 C16A C17A C18 179.8(3) . . . . ? N1A C16A C17A C18 -0.4(4) . . . . ? N1B C16A C17A C18 27.2(11) . . . . ? C17B C16A C17A C18 71(2) . . . . ? C16B C17A C18 C17B -67(3) . . . . ? C16A C17A C18 C17B -100(2) . . . . ? C17B C17A C18 C19 100(2) . . . . ? C16B C17A C18 C19 33.3(18) . . . . ? C16A C17A C18 C19 0.5(4) . . . . ? C17B C18 C19 C20A 48.5(19) . . . . ? C17A C18 C19 C20A 0.1(4) . . . . ? C17B C18 C19 C20B -11(2) . . . . ? C17A C18 C19 C20B -59.3(14) . . . . ? C16A N1A C20A N1B 82(2) . . . . ? C16B N1A C20A N1B 54(2) . . . . ? N1B N1A C20A C20B -5(3) . . . . ? C16A N1A C20A C20B 77.5(16) . . . . ? C16B N1A C20A C20B 49(2) . . . . ? N1B N1A C20A C19 -82(2) . . . . ? C16A N1A C20A C19 0.7(4) . . . . ? C16B N1A C20A C19 -27.7(15) . . . . ? C18 C19 C20A N1B -40.1(15) . . . . ? C20B C19 C20A N1B 62(2) . . . . ? C18 C19 C20A C20B -102.2(15) . . . . ? C18 C19 C20A N1A -0.6(4) . . . . ? C20B C19 C20A N1A 101.6(15) . . . . ? C16A N1A N1B C20A -124.4(7) . . . . ? C16B N1A N1B C20A -121(2) . . . . ? C20A N1A N1B C16B 121(2) . . . . ? C16A N1A N1B C16B -3.8(19) . . . . ? C20A N1A N1B C20B 5(3) . . . . ? C16A N1A N1B C20B -120(3) . . . . ? C16B N1A N1B C20B -116(4) . . . . ? C20A N1A N1B C16A 124.4(7) . . . . ? C16B N1A N1B C16A 3.8(19) . . . . ? C20B C20A N1B N1A 175(3) . . . . ? C19 C20A N1B N1A 115.8(16) . . . . ? C20B C20A N1B C16B 103(3) . . . . ? N1A C20A N1B C16B -72(3) . . . . ? C19 C20A N1B C16B 44(3) . . . . ? N1A C20A N1B C20B -175(3) . . . . ? C19 C20A N1B C20B -59.6(16) . . . . ? C20B C20A N1B C16A 132(2) . . . . ? N1A C20A N1B C16A -43.6(13) . . . . ? C19 C20A N1B C16A 72.2(19) . . . . ? C16B C16A N1B N1A -172(4) . . . . ? O2 C16A N1B N1A 85.1(19) . . . . ? C17A C16A N1B N1A -122.7(17) . . . . ? C17B C16A N1B N1A -141(2) . . . . ? C16B C16A N1B C20A -115(4) . . . . ? O2 C16A N1B C20A 142.2(13) . . . . ? N1A C16A N1B C20A 57.1(18) . . . . ? C17A C16A N1B C20A -66(2) . . . . ? C17B C16A N1B C20A -84(2) . . . . ? O2 C16A N1B C16B -103(3) . . . . ? N1A C16A N1B C16B 172(4) . . . . ? C17A C16A N1B C16B 49(3) . . . . ? C17B C16A N1B C16B 31(3) . . . . ? C16B C16A N1B C20B -60(4) . . . . ? O2 C16A N1B C20B -163(2) . . . . ? N1A C16A N1B C20B 112(4) . . . . ? C17A C16A N1B C20B -11(3) . . . . ? C17B C16A N1B C20B -29(3) . . . . ? O2 C16A C16B C17A -118.8(14) . . . . ? N1A C16A C16B C17A 121.3(12) . . . . ? N1B C16A C16B C17A 125(3) . . . . ? C17B C16A C16B C17A -1(2) . . . . ? O2 C16A C16B N1B 116(2) . . . . ? N1A C16A C16B N1B -4(2) . . . . ? C17A C16A C16B N1B -125(3) . . . . ? C17B C16A C16B N1B -127(5) . . . . ? O2 C16A C16B N1A 119.9(14) . . . . ? C17A C16A C16B N1A -121.3(12) . . . . ? N1B C16A C16B N1A 4(2) . . . . ? C17B C16A C16B N1A -123(3) . . . . ? O2 C16A C16B C17B -117(3) . . . . ? N1A C16A C16B C17B 123(3) . . . . ? C17A C16A C16B C17B 1(2) . . . . ? N1B C16A C16B C17B 127(5) . . . . ? N1A C16A C16B O2 -119.9(14) . . . . ? C17A C16A C16B O2 118.8(14) . . . . ? N1B C16A C16B O2 -116(2) . . . . ? C17B C16A C16B O2 117(3) . . . . ? C17B C17A C16B C16A 178(3) . . . . ? C18 C17A C16B C16A -124(2) . . . . ? C17B C17A C16B N1B -89(4) . . . . ? C18 C17A C16B N1B -31(4) . . . . ? C16A C17A C16B N1B 93(4) . . . . ? C17B C17A C16B N1A -125(3) . . . . ? C18 C17A C16B N1A -68(3) . . . . ? C16A C17A C16B N1A 57(2) . . . . ? C18 C17A C16B C17B 58(2) . . . . ? C16A C17A C16B C17B -178(3) . . . . ? C17B C17A C16B O2 146(2) . . . . ? C18 C17A C16B O2 -156.7(10) . . . . ? C16A C17A C16B O2 -32.5(15) . . . . ? N1A N1B C16B C16A 6(3) . . . . ? C20A N1B C16B C16A 76(4) . . . . ? C20B N1B C16B C16A 136(3) . . . . ? N1A N1B C16B C17A -77(4) . . . . ? C20A N1B C16B C17A -8(5) . . . . ? C20B N1B C16B C17A 52(5) . . . . ? C16A N1B C16B C17A -84(4) . . . . ? C20A N1B C16B N1A 70(2) . . . . ? C20B N1B C16B N1A 129(3) . . . . ? C16A N1B C16B N1A -6(3) . . . . ? N1A N1B C16B C17B -123(3) . . . . ? C20A N1B C16B C17B -54(4) . . . . ? C20B N1B C16B C17B 6(4) . . . . ? C16A N1B C16B C17B -130(5) . . . . ? N1A N1B C16B O2 42(3) . . . . ? C20A N1B C16B O2 112(3) . . . . ? C20B N1B C16B O2 172(2) . . . . ? C16A N1B C16B O2 36.0(19) . . . . ? N1B N1A C16B C16A -173(4) . . . . ? C20A N1A C16B C16A 132(2) . . . . ? N1B N1A C16B C17A 121(4) . . . . ? C20A N1A C16B C17A 67(3) . . . . ? C16A N1A C16B C17A -66(3) . . . . ? C20A N1A C16B N1B -55(2) . . . . ? C16A N1A C16B N1B 173(4) . . . . ? N1B N1A C16B C17B 78(4) . . . . ? C20A N1A C16B C17B 23(4) . . . . ? C16A N1A C16B C17B -109(5) . . . . ? N1B N1A C16B O2 -141(3) . . . . ? C20A N1A C16B O2 164.2(7) . . . . ? C16A N1A C16B O2 31.8(15) . . . . ? C16A O2 C16B C17A 61(2) . . . . ? C16A O2 C16B N1B -74(3) . . . . ? C16A O2 C16B N1A -52(2) . . . . ? C16A O2 C16B C17B 89(4) . . . . ? C16B C17A C17B C18 114.5(19) . . . . ? C16A C17A C17B C18 115.6(9) . . . . ? C18 C17A C17B C16B -114.5(19) . . . . ? C16A C17A C17B C16B 1.1(19) . . . . ? C16B C17A C17B C20B -63(11) . . . 2_666 ? C18 C17A C17B C20B -178(12) . . . 2_666 ? C16A C17A C17B C20B -62(11) . . . 2_666 ? C16B C17A C17B C16A -1.1(19) . . . . ? C18 C17A C17B C16A -115.6(9) . . . . ? C19 C18 C17B C17A -104.5(16) . . . . ? C17A C18 C17B C16B 56(2) . . . . ? C19 C18 C17B C16B -49(3) . . . . ? C17A C18 C17B C20B 179(4) . . . 2_666 ? C19 C18 C17B C20B 75(3) . . . 2_666 ? C17A C18 C17B C16A 37.1(11) . . . . ? C19 C18 C17B C16A -67.5(17) . . . . ? C16A C16B C17B C17A -2(4) . . . . ? N1B C16B C17B C17A 116(3) . . . . ? N1A C16B C17B C17A 78(4) . . . . ? O2 C16B C17B C17A -47(3) . . . . ? C16A C16B C17B C18 -67(4) . . . . ? C17A C16B C17B C18 -64(2) . . . . ? N1B C16B C17B C18 51(4) . . . . ? N1A C16B C17B C18 14(5) . . . . ? O2 C16B C17B C18 -111(3) . . . . ? C16A C16B C17B C20B 163(4) . . . 2_666 ? C17A C16B C17B C20B 165(3) . . . 2_666 ? N1B C16B C17B C20B -79(3) . . . 2_666 ? N1A C16B C17B C20B -116(3) . . . 2_666 ? O2 C16B C17B C20B 118(3) . . . 2_666 ? C17A C16B C17B C16A 2(4) . . . . ? N1B C16B C17B C16A 118(5) . . . . ? N1A C16B C17B C16A 81(4) . . . . ? O2 C16B C17B C16A -45(3) . . . . ? C16B C16A C17B C17A 177(5) . . . . ? O2 C16A C17B C17A -92(2) . . . . ? N1A C16A C17B C17A 117.4(18) . . . . ? N1B C16A C17B C17A 136(2) . . . . ? C16B C16A C17B C18 116(4) . . . . ? O2 C16A C17B C18 -153.3(9) . . . . ? N1A C16A C17B C18 56.7(17) . . . . ? C17A C16A C17B C18 -60.8(18) . . . . ? N1B C16A C17B C18 75.5(19) . . . . ? O2 C16A C17B C16B 90(4) . . . . ? N1A C16A C17B C16B -60(4) . . . . ? C17A C16A C17B C16B -177(5) . . . . ? N1B C16A C17B C16B -41(4) . . . . ? C16B C16A C17B C20B -21(4) . . . 2_666 ? O2 C16A C17B C20B 69(3) . . . 2_666 ? N1A C16A C17B C20B -81(3) . . . 2_666 ? C17A C16A C17B C20B 162(4) . . . 2_666 ? N1B C16A C17B C20B -62(3) . . . 2_666 ? N1B C20A C20B C19 -119.3(16) . . . . ? N1A C20A C20B C19 -116.3(6) . . . . ? N1A C20A C20B N1B 3.0(16) . . . . ? C19 C20A C20B N1B 119.3(16) . . . . ? N1B C20A C20B C17B 13(15) . . . 2_666 ? N1A C20A C20B C17B 16(15) . . . 2_666 ? C19 C20A C20B C17B 132(15) . . . 2_666 ? C18 C19 C20B C20A 106.7(10) . . . . ? C20A C19 C20B N1B -44.9(14) . . . . ? C18 C19 C20B N1B 62(2) . . . . ? C20A C19 C20B C17B -170(4) . . . 2_666 ? C18 C19 C20B C17B -63(3) . . . 2_666 ? N1A N1B C20B C20A -6(3) . . . . ? C16B N1B C20B C20A -105(3) . . . . ? C16A N1B C20B C20A -78(3) . . . . ? N1A N1B C20B C19 42(4) . . . . ? C20A N1B C20B C19 48.2(12) . . . . ? C16B N1B C20B C19 -57(3) . . . . ? C16A N1B C20B C19 -30(3) . . . . ? N1A N1B C20B C17B 177(3) . . . 2_666 ? C20A N1B C20B C17B -177(3) . . . 2_666 ? C16B N1B C20B C17B 77(3) . . . 2_666 ? C16A N1B C20B C17B 104(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.141 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.034 data_I-c_4hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7750(10) _cell_length_b 8.0580(10) _cell_length_c 13.462(2) _cell_angle_alpha 84.97(2) _cell_angle_beta 75.54(2) _cell_angle_gamma 81.31(2) _cell_volume 806.23(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8754 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8754 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2842 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.1943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2842 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35460(15) 1.07985(16) 0.23506(9) 0.0408(3) Uani 1 1 d . . . H1 H 0.4219 1.0299 0.2693 0.049 Uiso 1 1 calc R . . C1 C 0.0390(2) 0.9982(2) 0.44781(13) 0.0399(4) Uani 1 1 d . . . C2 C 0.1061(2) 0.9942(2) 0.35818(13) 0.0385(4) Uani 1 1 d . . . C3 C 0.2031(2) 0.9945(2) 0.24814(12) 0.0319(4) Uani 1 1 d . . . C4 C 0.0851(2) 1.0880(2) 0.17986(12) 0.0319(4) Uani 1 1 d . . . C5 C -0.0988(3) 1.1149(3) 0.21198(15) 0.0501(5) Uani 1 1 d . . . H5 H -0.1548 1.0811 0.2785 0.060 Uiso 1 1 calc R . . C6 C -0.2013(3) 1.1921(3) 0.14593(19) 0.0685(7) Uani 1 1 d . . . H6 H -0.3256 1.2097 0.1686 0.082 Uiso 1 1 calc R . . C7 C -0.1218(3) 1.2425(3) 0.04817(17) 0.0614(6) Uani 1 1 d . . . H7 H -0.1912 1.2945 0.0042 0.074 Uiso 1 1 calc R . . C8 C 0.0610(3) 1.2161(3) 0.01518(16) 0.0572(6) Uani 1 1 d . . . H8 H 0.1159 1.2505 -0.0515 0.069 Uiso 1 1 calc R . . C9 C 0.1645(3) 1.1387(2) 0.08042(13) 0.0440(5) Uani 1 1 d . . . H9 H 0.2886 1.1206 0.0571 0.053 Uiso 1 1 calc R . . C10 C 0.2594(2) 0.8129(2) 0.21454(11) 0.0314(4) Uani 1 1 d . . . C11 C 0.4290(2) 0.7644(2) 0.15424(14) 0.0429(5) Uani 1 1 d . . . H11 H 0.5108 0.8414 0.1352 0.052 Uiso 1 1 calc R . . C12 C 0.4772(3) 0.6020(3) 0.12218(15) 0.0526(5) Uani 1 1 d . . . H12 H 0.5920 0.5702 0.0824 0.063 Uiso 1 1 calc R . . C13 C 0.3582(3) 0.4879(3) 0.14823(15) 0.0542(6) Uani 1 1 d . . . H13 H 0.3919 0.3787 0.1267 0.065 Uiso 1 1 calc R . . C14 C 0.1882(3) 0.5352(2) 0.20651(16) 0.0557(6) Uani 1 1 d . . . H14 H 0.1061 0.4584 0.2236 0.067 Uiso 1 1 calc R . . C15 C 0.1393(3) 0.6972(2) 0.23977(14) 0.0451(5) Uani 1 1 d . . . H15 H 0.0243 0.7284 0.2795 0.054 Uiso 1 1 calc R . . O2 O 0.4619(2) 0.0707(3) 0.62422(12) 0.0809(6) Uani 1 1 d . . . N1A N 0.3794(3) 0.2124(3) 0.48920(16) 0.0592(7) Uani 0.895(5) 1 d P . . H1NA H 0.4193 0.1242 0.4545 0.071 Uiso 0.895(5) 1 d PR . . C16A C 0.3950(3) 0.2043(4) 0.5876(2) 0.0547(7) Uani 0.895(5) 1 d P . . C17A C 0.3312(4) 0.3544(4) 0.6398(2) 0.0681(9) Uani 0.895(5) 1 d P . . H17A H 0.3388 0.3573 0.7074 0.082 Uiso 0.895(5) 1 d PR . . C18 C 0.2599(3) 0.4970(4) 0.5922(2) 0.0817(8) Uani 1 1 d . . . H18A H 0.2188 0.5945 0.6279 0.098 Uiso 0.895(5) 1 d PR . . C19 C 0.2474(4) 0.4962(4) 0.4914(2) 0.0850(8) Uani 1 1 d . . . H19A H 0.1979 0.5908 0.4584 0.102 Uiso 0.895(5) 1 d PR . . C20A C 0.3084(4) 0.3514(4) 0.4419(2) 0.0734(9) Uani 0.895(5) 1 d P . . H20A H 0.3004 0.3467 0.3745 0.088 Uiso 0.895(5) 1 d PR . . N1B N 0.451(3) 0.288(3) 0.4668(18) 0.078(7) Uiso 0.105(5) 1 d P . . H1NB H 0.4700 0.1993 0.4326 0.094 Uiso 0.105(5) 1 d PR . . C16B C 0.457(4) 0.279(4) 0.566(2) 0.064(7) Uiso 0.105(5) 1 d P . . C17B C 0.416(3) 0.441(3) 0.6160(19) 0.066(7) Uiso 0.105(5) 1 d P . . H17B H 0.3871 0.4186 0.6905 0.079 Uiso 0.105(5) 1 d PR . . C20B C 0.416(3) 0.457(3) 0.4155(19) 0.072(8) Uiso 0.105(5) 1 d P . . H20B H 0.3849 0.4399 0.3514 0.086 Uiso 0.105(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.086 Uiso 0.11 1 d P . . H19B H 0.1382 0.5198 0.4735 0.086 Uiso 0.11 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0428(7) 0.0421(8) 0.0411(7) 0.0006(6) -0.0153(5) -0.0102(5) C1 0.0486(10) 0.0396(11) 0.0289(9) -0.0046(8) -0.0069(8) -0.0004(8) C2 0.0480(10) 0.0358(10) 0.0299(10) -0.0042(8) -0.0081(8) -0.0005(8) C3 0.0362(9) 0.0344(10) 0.0236(8) -0.0011(7) -0.0051(7) -0.0041(7) C4 0.0425(10) 0.0243(9) 0.0286(9) -0.0040(7) -0.0093(7) -0.0010(7) C5 0.0430(11) 0.0518(13) 0.0467(11) 0.0083(9) -0.0048(9) 0.0042(9) C6 0.0465(12) 0.0802(18) 0.0723(16) 0.0095(13) -0.0190(11) 0.0119(11) C7 0.0692(15) 0.0588(15) 0.0580(14) 0.0070(11) -0.0313(12) 0.0070(11) C8 0.0751(15) 0.0589(14) 0.0373(11) 0.0094(10) -0.0197(10) -0.0045(11) C9 0.0487(11) 0.0501(12) 0.0311(10) 0.0042(8) -0.0088(8) -0.0046(9) C10 0.0421(9) 0.0300(9) 0.0214(8) 0.0014(7) -0.0105(7) 0.0005(7) C11 0.0429(10) 0.0460(12) 0.0376(10) -0.0071(8) -0.0068(8) -0.0008(8) C12 0.0568(12) 0.0499(13) 0.0470(12) -0.0154(10) -0.0135(9) 0.0146(10) C13 0.0839(15) 0.0323(11) 0.0470(12) -0.0073(9) -0.0254(11) 0.0098(10) C14 0.0796(15) 0.0326(11) 0.0558(13) 0.0025(10) -0.0157(11) -0.0141(10) C15 0.0518(11) 0.0365(11) 0.0424(11) 0.0004(8) -0.0037(8) -0.0062(9) O2 0.0826(12) 0.1085(15) 0.0566(10) 0.0021(10) -0.0360(9) 0.0005(10) N1A 0.0670(14) 0.0650(15) 0.0518(13) 0.0073(11) -0.0293(11) -0.0091(12) C16A 0.0450(14) 0.0697(19) 0.0554(15) 0.0105(14) -0.0240(11) -0.0141(14) C17A 0.0634(17) 0.085(2) 0.0610(17) -0.0092(15) -0.0212(13) -0.0116(16) C18 0.0625(16) 0.087(2) 0.094(2) -0.0133(17) -0.0139(14) -0.0106(14) C19 0.0774(19) 0.090(2) 0.089(2) 0.0121(17) -0.0329(16) -0.0054(16) C20A 0.085(2) 0.077(2) 0.0642(18) 0.0149(16) -0.0368(15) -0.0083(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.418(2) . ? O1 H1 0.8200 . ? C1 C2 1.190(2) . ? C1 C1 1.386(3) 2_576 ? C2 C3 1.485(2) . ? C3 C10 1.536(2) . ? C3 C4 1.531(2) . ? C4 C5 1.376(3) . ? C4 C9 1.381(2) . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 C7 1.362(3) . ? C6 H6 0.9300 . ? C7 C8 1.368(3) . ? C7 H7 0.9300 . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.381(2) . ? C10 C11 1.384(2) . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.365(3) . ? C12 H12 0.9300 . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.241(3) . ? O2 C16B 1.79(3) . ? N1A N1B 0.87(3) . ? N1A C16A 1.355(3) . ? N1A C20A 1.352(3) . ? N1A C16B 1.49(3) . ? N1A H1NA 0.8595 . ? N1A H1NB 0.9014 . ? C16A C16B 0.82(3) . ? C16A C17A 1.413(4) . ? C16A N1B 1.68(3) . ? C16A C17B 2.02(3) . ? C17A C17B 1.01(3) . ? C17A C16B 1.32(3) . ? C17A C18 1.376(4) . ? C17A H17A 0.9294 . ? C17A H17B 1.0962 . ? C18 C17B 1.33(2) . ? C18 C19 1.385(4) . ? C18 H18A 0.9295 . ? C18 H18B 0.9222 . ? C19 C20A 1.357(4) . ? C19 C20B 1.46(2) . ? C19 H19A 0.9291 . ? C19 H19B 0.9275 . ? C20A N1B 1.26(2) . ? C20A C20B 1.25(3) . ? C20A H20A 0.9294 . ? C20A H20B 1.3999 . ? N1B C16B 1.34(3) . ? N1B C20B 1.49(3) . ? N1B H1NA 1.4104 . ? N1B H1NB 0.8597 . ? C16B C17B 1.48(4) . ? C17B C20B 1.59(4) 2_666 ? C17B H17A 1.3931 . ? C17B H17B 0.9796 . ? C20B C17B 1.59(4) 2_666 ? C20B H20B 0.9795 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.7(3) . 2_576 ? C1 C2 C3 175.17(18) . . ? O1 C3 C2 108.57(13) . . ? O1 C3 C10 111.06(13) . . ? C2 C3 C10 109.82(14) . . ? O1 C3 C4 107.64(14) . . ? C2 C3 C4 111.27(14) . . ? C10 C3 C4 108.46(12) . . ? C5 C4 C9 118.47(16) . . ? C5 C4 C3 122.28(15) . . ? C9 C4 C3 119.13(15) . . ? C4 C5 C6 120.51(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.57(18) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C15 C10 C11 118.68(16) . . ? C15 C10 C3 120.67(15) . . ? C11 C10 C3 120.58(15) . . ? C12 C11 C10 120.28(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.69(19) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.67(18) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.02(19) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.65(18) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C16A O2 C16B 23.4(8) . . ? N1B N1A C16A 95.8(16) . . ? N1B N1A C20A 64.7(16) . . ? C16A N1A C20A 124.0(3) . . ? N1B N1A C16B 62.9(19) . . ? C16A N1A C16B 32.9(12) . . ? C20A N1A C16B 104.3(11) . . ? N1B N1A H1NA 109.2 . . ? C16A N1A H1NA 117.8 . . ? C20A N1A H1NA 118.2 . . ? C16B N1A H1NA 128.3 . . ? N1B N1A H1NB 58.0 . . ? C16A N1A H1NB 126.4 . . ? C20A N1A H1NB 88.5 . . ? C16B N1A H1NB 105.1 . . ? H1NA N1A H1NB 51.7 . . ? C16B C16A O2 119.5(18) . . ? C16B C16A N1A 82.7(18) . . ? O2 C16A N1A 119.2(3) . . ? C16B C16A C17A 66.8(18) . . ? O2 C16A C17A 125.6(2) . . ? N1A C16A C17A 115.1(3) . . ? C16B C16A N1B 52(2) . . ? O2 C16A N1B 128.4(8) . . ? N1A C16A N1B 31.0(9) . . ? C17A C16A N1B 98.8(9) . . ? C16B C16A C17B 39.3(19) . . ? O2 C16A C17B 128.1(7) . . ? N1A C16A C17B 105.3(7) . . ? C17A C16A C17B 27.7(7) . . ? N1B C16A C17B 79.7(12) . . ? C17B C17A C16B 77.4(19) . . ? C17B C17A C18 65.8(14) . . ? C16B C17A C18 104.8(12) . . ? C17B C17A C16A 111.8(14) . . ? C16B C17A C16A 34.5(13) . . ? C18 C17A C16A 121.4(3) . . ? C17B C17A H17A 91.7 . . ? C16B C17A H17A 125.1 . . ? C18 C17A H17A 119.3 . . ? C16A C17A H17A 119.3 . . ? C17B C17A H17B 55.2 . . ? C16B C17A H17B 112.5 . . ? C18 C17A H17B 96.7 . . ? C16A C17A H17B 131.5 . . ? H17A C17A H17B 36.6 . . ? C17B C18 C17A 43.8(12) . . ? C17B C18 C19 119.5(11) . . ? C17A C18 C19 120.5(3) . . ? C17B C18 H18A 103.8 . . ? C17A C18 H18A 119.9 . . ? C19 C18 H18A 119.6 . . ? C17B C18 H18B 120.8 . . ? C17A C18 H18B 102.9 . . ? C19 C18 H18B 119.6 . . ? H18A C18 H18B 43.2 . . ? C20A C19 C18 117.8(3) . . ? C20A C19 C20B 52.8(10) . . ? C18 C19 C20B 115.9(10) . . ? C20A C19 H19A 120.5 . . ? C18 C19 H19A 121.6 . . ? C20B C19 H19A 99.5 . . ? C20A C19 H19B 97.9 . . ? C18 C19 H19B 121.8 . . ? C20B C19 H19B 122.3 . . ? H19A C19 H19B 49.2 . . ? N1B C20A C20B 72.9(17) . . ? N1B C20A N1A 38.8(13) . . ? C20B C20A N1A 111.6(12) . . ? N1B C20A C19 107.5(12) . . ? C20B C20A C19 67.8(11) . . ? N1A C20A C19 121.2(3) . . ? N1B C20A H20A 119.3 . . ? C20B C20A H20A 91.3 . . ? N1A C20A H20A 119.1 . . ? C19 C20A H20A 119.8 . . ? N1B C20A H20B 98.2 . . ? C20B C20A H20B 42.9 . . ? N1A C20A H20B 129.4 . . ? C19 C20A H20B 91.4 . . ? H20A C20A H20B 48.5 . . ? N1A N1B C20A 76.5(19) . . ? N1A N1B C16B 82(2) . . ? C20A N1B C16B 120(2) . . ? N1A N1B C20B 130(3) . . ? C20A N1B C20B 53.5(14) . . ? C16B N1B C20B 119(2) . . ? N1A N1B C16A 53.2(13) . . ? C20A N1B C16A 107.9(17) . . ? C16B N1B C16A 28.6(13) . . ? C20B N1B C16A 135.5(19) . . ? N1A N1B H1NA 35.1 . . ? C20A N1B H1NA 91.5 . . ? C16B N1B H1NA 101.6 . . ? C20B N1B H1NA 135.6 . . ? C16A N1B H1NA 75.8 . . ? N1A N1B H1NB 62.8 . . ? C20A N1B H1NB 96.9 . . ? C16B N1B H1NB 121.3 . . ? C20B N1B H1NB 120.2 . . ? C16A N1B H1NB 100.5 . . ? H1NA N1B H1NB 28.2 . . ? C16A C16B C17A 79(2) . . ? C16A C16B N1B 100(3) . . ? C17A C16B N1B 124(2) . . ? C16A C16B C17B 120(3) . . ? C17A C16B C17B 41.8(13) . . ? N1B C16B C17B 115(2) . . ? C16A C16B N1A 64.4(17) . . ? C17A C16B N1A 112.1(18) . . ? N1B C16B N1A 35.3(13) . . ? C17B C16B N1A 132(2) . . ? C16A C16B O2 37.1(14) . . ? C17A C16B O2 97.6(17) . . ? N1B C16B O2 114(2) . . ? C17B C16B O2 129(2) . . ? N1A C16B O2 85.6(14) . . ? C17A C17B C18 70.4(16) . . ? C17A C17B C16B 60.8(17) . . ? C18 C17B C16B 98.9(18) . . ? C17A C17B C20B 166(2) . 2_666 ? C18 C17B C20B 123(2) . 2_666 ? C16B C17B C20B 111(2) . 2_666 ? C17A C17B C16A 40.5(10) . . ? C18 C17B C16A 90.7(14) . . ? C16B C17B C16A 20.4(12) . . ? C20B C17B C16A 130.0(16) 2_666 . ? C17A C17B H17A 41.8 . . ? C18 C17B H17A 94.5 . . ? C16B C17B H17A 88.6 . . ? C20B C17B H17A 132.0 2_666 . ? C16A C17B H17A 70.6 . . ? C17A C17B H17B 66.8 . . ? C18 C17B H17B 105.9 . . ? C16B C17B H17B 108.4 . . ? C20B C17B H17B 108.7 2_666 . ? C16A C17B H17B 93.1 . . ? H17A C17B H17B 25.2 . . ? C20A C20B C19 59.5(11) . . ? C20A C20B N1B 53.7(14) . . ? C19 C20B N1B 91.3(17) . . ? C20A C20B C17B 168(2) . 2_666 ? C19 C20B C17B 128.9(19) . 2_666 ? N1B C20B C17B 115(2) . 2_666 ? C20A C20B H20B 76.5 . . ? C19 C20B H20B 106.5 . . ? N1B C20B H20B 107.1 . . ? C17B C20B H20B 106.3 2_666 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -113(44) 2_576 . . . ? C1 C2 C3 O1 -11(2) . . . . ? C1 C2 C3 C10 111(2) . . . . ? C1 C2 C3 C4 -129(2) . . . . ? O1 C3 C4 C5 -139.32(17) . . . . ? C2 C3 C4 C5 -20.5(2) . . . . ? C10 C3 C4 C5 100.43(19) . . . . ? O1 C3 C4 C9 44.6(2) . . . . ? C2 C3 C4 C9 163.44(15) . . . . ? C10 C3 C4 C9 -75.66(19) . . . . ? C9 C4 C5 C6 -0.4(3) . . . . ? C3 C4 C5 C6 -176.49(19) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C5 C4 C9 C8 0.6(3) . . . . ? C3 C4 C9 C8 176.84(17) . . . . ? C7 C8 C9 C4 -0.5(3) . . . . ? O1 C3 C10 C15 166.71(14) . . . . ? C2 C3 C10 C15 46.6(2) . . . . ? C4 C3 C10 C15 -75.20(19) . . . . ? O1 C3 C10 C11 -16.4(2) . . . . ? C2 C3 C10 C11 -136.51(16) . . . . ? C4 C3 C10 C11 101.69(17) . . . . ? C15 C10 C11 C12 -1.4(3) . . . . ? C3 C10 C11 C12 -178.38(16) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C11 C10 C15 C14 0.8(3) . . . . ? C3 C10 C15 C14 177.78(17) . . . . ? C13 C14 C15 C10 0.4(3) . . . . ? C16B O2 C16A N1A 99(2) . . . . ? C16B O2 C16A C17A -81(2) . . . . ? C16B O2 C16A N1B 63(2) . . . . ? C16B O2 C16A C17B -47(2) . . . . ? N1B N1A C16A C16B 3(3) . . . . ? C20A N1A C16A C16B -60.2(19) . . . . ? N1B N1A C16A O2 -116.8(16) . . . . ? C20A N1A C16A O2 179.9(3) . . . . ? C16B N1A C16A O2 -119.8(19) . . . . ? N1B N1A C16A C17A 63.1(16) . . . . ? C20A N1A C16A C17A -0.2(4) . . . . ? C16B N1A C16A C17A 60.1(18) . . . . ? C20A N1A C16A N1B -63.3(16) . . . . ? C16B N1A C16A N1B -3(3) . . . . ? N1B N1A C16A C17B 35.5(18) . . . . ? C20A N1A C16A C17B -27.8(8) . . . . ? C16B N1A C16A C17B 32.4(19) . . . . ? C16B C16A C17A C17B -5(2) . . . . ? O2 C16A C17A C17B 105.5(16) . . . . ? N1A C16A C17A C17B -74.5(16) . . . . ? N1B C16A C17A C17B -46.8(18) . . . . ? O2 C16A C17A C16B 111(2) . . . . ? N1A C16A C17A C16B -69(2) . . . . ? N1B C16A C17A C16B -42(2) . . . . ? C17B C16A C17A C16B 5(2) . . . . ? C16B C16A C17A C18 69(2) . . . . ? O2 C16A C17A C18 179.6(3) . . . . ? N1A C16A C17A C18 -0.3(4) . . . . ? N1B C16A C17A C18 27.4(10) . . . . ? C17B C16A C17A C18 74.1(16) . . . . ? C16B C17A C18 C17B -68.5(19) . . . . ? C16A C17A C18 C17B -101.7(15) . . . . ? C17B C17A C18 C19 102.3(15) . . . . ? C16B C17A C18 C19 33.8(13) . . . . ? C16A C17A C18 C19 0.6(4) . . . . ? C17B C18 C19 C20A 50.6(15) . . . . ? C17A C18 C19 C20A -0.4(4) . . . . ? C17B C18 C19 C20B -9.1(18) . . . . ? C17A C18 C19 C20B -60.1(12) . . . . ? C16A N1A C20A N1B 79.3(17) . . . . ? C16B N1A C20A N1B 50(2) . . . . ? N1B N1A C20A C20B -3(2) . . . . ? C16A N1A C20A C20B 76.7(13) . . . . ? C16B N1A C20A C20B 47.6(17) . . . . ? N1B N1A C20A C19 -79.0(17) . . . . ? C16A N1A C20A C19 0.4(4) . . . . ? C16B N1A C20A C19 -28.7(12) . . . . ? C18 C19 C20A N1B -40.2(13) . . . . ? C20B C19 C20A N1B 62.4(17) . . . . ? C18 C19 C20A C20B -102.6(13) . . . . ? C18 C19 C20A N1A -0.1(4) . . . . ? C20B C19 C20A N1A 102.5(13) . . . . ? C16A N1A N1B C20A -125.1(7) . . . . ? C16B N1A N1B C20A -123.2(18) . . . . ? C16A N1A N1B C16B -1.8(15) . . . . ? C20A N1A N1B C16B 123.2(18) . . . . ? C16A N1A N1B C20B -122(3) . . . . ? C20A N1A N1B C20B 3(2) . . . . ? C16B N1A N1B C20B -121(3) . . . . ? C20A N1A N1B C16A 125.1(7) . . . . ? C16B N1A N1B C16A 1.8(15) . . . . ? C20B C20A N1B N1A 177(2) . . . . ? C19 C20A N1B N1A 118.3(13) . . . . ? C20B C20A N1B C16B 105(3) . . . . ? N1A C20A N1B C16B -72(2) . . . . ? C19 C20A N1B C16B 46(3) . . . . ? N1A C20A N1B C20B -177(2) . . . . ? C19 C20A N1B C20B -59.2(13) . . . . ? C20B C20A N1B C16A 134(2) . . . . ? N1A C20A N1B C16A -43.6(11) . . . . ? C19 C20A N1B C16A 74.7(16) . . . . ? C16B C16A N1B N1A -176(3) . . . . ? O2 C16A N1B N1A 83.7(16) . . . . ? C17A C16A N1B N1A -125.2(14) . . . . ? C17B C16A N1B N1A -145.3(17) . . . . ? C16B C16A N1B C20A -119(3) . . . . ? O2 C16A N1B C20A 140.5(11) . . . . ? N1A C16A N1B C20A 56.8(15) . . . . ? C17A C16A N1B C20A -68.4(17) . . . . ? C17B C16A N1B C20A -88.5(18) . . . . ? O2 C16A N1B C16B -100(3) . . . . ? N1A C16A N1B C16B 176(3) . . . . ? C17A C16A N1B C16B 51(2) . . . . ? C17B C16A N1B C16B 31(2) . . . . ? C16B C16A N1B C20B -64(4) . . . . ? O2 C16A N1B C20B -164(2) . . . . ? N1A C16A N1B C20B 113(3) . . . . ? C17A C16A N1B C20B -13(3) . . . . ? C17B C16A N1B C20B -33(3) . . . . ? O2 C16A C16B C17A -119.1(10) . . . . ? N1A C16A C16B C17A 121.4(9) . . . . ? N1B C16A C16B C17A 123(2) . . . . ? C17B C16A C16B C17A -3.8(18) . . . . ? O2 C16A C16B N1B 117.6(17) . . . . ? N1A C16A C16B N1B -2.0(16) . . . . ? C17A C16A C16B N1B -123(2) . . . . ? C17B C16A C16B N1B -127(4) . . . . ? O2 C16A C16B C17B -115(2) . . . . ? N1A C16A C16B C17B 125(3) . . . . ? C17A C16A C16B C17B 3.8(18) . . . . ? N1B C16A C16B C17B 127(4) . . . . ? O2 C16A C16B N1A 119.6(10) . . . . ? C17A C16A C16B N1A -121.4(9) . . . . ? N1B C16A C16B N1A 2.0(16) . . . . ? C17B C16A C16B N1A -125(3) . . . . ? N1A C16A C16B O2 -119.6(10) . . . . ? C17A C16A C16B O2 119.1(10) . . . . ? N1B C16A C16B O2 -117.6(17) . . . . ? C17B C16A C16B O2 115(2) . . . . ? C17B C17A C16B C16A 175(2) . . . . ? C18 C17A C16B C16A -124.5(15) . . . . ? C17B C17A C16B N1B -91(3) . . . . ? C18 C17A C16B N1B -30(3) . . . . ? C16A C17A C16B N1B 94(3) . . . . ? C18 C17A C16B C17B 60.4(15) . . . . ? C16A C17A C16B C17B -175(2) . . . . ? C17B C17A C16B N1A -129(2) . . . . ? C18 C17A C16B N1A -68(2) . . . . ? C16A C17A C16B N1A 56.2(17) . . . . ? C17B C17A C16B O2 143.0(18) . . . . ? C18 C17A C16B O2 -156.6(8) . . . . ? C16A C17A C16B O2 -32.1(11) . . . . ? N1A N1B C16B C16A 3(3) . . . . ? C20A N1B C16B C16A 72(3) . . . . ? C20B N1B C16B C16A 134(3) . . . . ? N1A N1B C16B C17A -80(3) . . . . ? C20A N1B C16B C17A -10(4) . . . . ? C20B N1B C16B C17A 51(4) . . . . ? C16A N1B C16B C17A -83(3) . . . . ? N1A N1B C16B C17B -127(2) . . . . ? C20A N1B C16B C17B -58(3) . . . . ? C20B N1B C16B C17B 4(4) . . . . ? C16A N1B C16B C17B -130(4) . . . . ? C20A N1B C16B N1A 69(2) . . . . ? C20B N1B C16B N1A 131(3) . . . . ? C16A N1B C16B N1A -3(3) . . . . ? N1A N1B C16B O2 39(2) . . . . ? C20A N1B C16B O2 108(3) . . . . ? C20B N1B C16B O2 170.2(19) . . . . ? C16A N1B C16B O2 35.9(14) . . . . ? N1B N1A C16B C16A -177(3) . . . . ? C20A N1A C16B C16A 132.1(14) . . . . ? N1B N1A C16B C17A 119(3) . . . . ? C16A N1A C16B C17A -65(2) . . . . ? C20A N1A C16B C17A 67(2) . . . . ? C16A N1A C16B N1B 177(3) . . . . ? C20A N1A C16B N1B -51.3(19) . . . . ? N1B N1A C16B C17B 75(3) . . . . ? C16A N1A C16B C17B -109(4) . . . . ? C20A N1A C16B C17B 23(3) . . . . ? N1B N1A C16B O2 -145(2) . . . . ? C16A N1A C16B O2 31.8(11) . . . . ? C20A N1A C16B O2 163.8(6) . . . . ? C16A O2 C16B C17A 59.9(18) . . . . ? C16A O2 C16B N1B -73(2) . . . . ? C16A O2 C16B C17B 91(3) . . . . ? C16A O2 C16B N1A -51.9(16) . . . . ? C16B C17A C17B C18 112.8(14) . . . . ? C16A C17A C17B C18 115.8(7) . . . . ? C18 C17A C17B C16B -112.8(14) . . . . ? C16A C17A C17B C16B 3.0(14) . . . . ? C16B C17A C17B C20B -55(10) . . . 2_666 ? C18 C17A C17B C20B -168(10) . . . 2_666 ? C16A C17A C17B C20B -52(10) . . . 2_666 ? C16B C17A C17B C16A -3.0(14) . . . . ? C18 C17A C17B C16A -115.8(7) . . . . ? C19 C18 C17B C17A -104.5(12) . . . . ? C17A C18 C17B C16B 54.6(16) . . . . ? C19 C18 C17B C16B -50(2) . . . . ? C17A C18 C17B C20B 177(3) . . . 2_666 ? C19 C18 C17B C20B 72(2) . . . 2_666 ? C17A C18 C17B C16A 35.8(7) . . . . ? C19 C18 C17B C16A -68.7(13) . . . . ? C16A C16B C17B C17A -6(3) . . . . ? N1B C16B C17B C17A 114(3) . . . . ? N1A C16B C17B C17A 76(3) . . . . ? O2 C16B C17B C17A -50(2) . . . . ? C16A C16B C17B C18 -67(3) . . . . ? C17A C16B C17B C18 -61.6(15) . . . . ? N1B C16B C17B C18 52(3) . . . . ? N1A C16B C17B C18 14(3) . . . . ? O2 C16B C17B C18 -111(2) . . . . ? C16A C16B C17B C20B 162(3) . . . 2_666 ? C17A C16B C17B C20B 168(3) . . . 2_666 ? N1B C16B C17B C20B -78(3) . . . 2_666 ? N1A C16B C17B C20B -116(3) . . . 2_666 ? O2 C16B C17B C20B 118(2) . . . 2_666 ? C17A C16B C17B C16A 6(3) . . . . ? N1B C16B C17B C16A 120(4) . . . . ? N1A C16B C17B C16A 81(3) . . . . ? O2 C16B C17B C16A -44(2) . . . . ? C16B C16A C17B C17A 173(4) . . . . ? O2 C16A C17B C17A -95.8(15) . . . . ? N1A C16A C17B C17A 115.3(13) . . . . ? N1B C16A C17B C17A 133.0(17) . . . . ? C16B C16A C17B C18 114(3) . . . . ? O2 C16A C17B C18 -153.8(7) . . . . ? N1A C16A C17B C18 57.2(13) . . . . ? C17A C16A C17B C18 -58.1(13) . . . . ? N1B C16A C17B C18 74.9(15) . . . . ? O2 C16A C17B C16B 92(3) . . . . ? N1A C16A C17B C16B -57(3) . . . . ? C17A C16A C17B C16B -173(4) . . . . ? N1B C16A C17B C16B -40(3) . . . . ? C16B C16A C17B C20B -22(3) . . . 2_666 ? O2 C16A C17B C20B 70(2) . . . 2_666 ? N1A C16A C17B C20B -79(2) . . . 2_666 ? C17A C16A C17B C20B 166(3) . . . 2_666 ? N1B C16A C17B C20B -61(2) . . . 2_666 ? N1B C20A C20B C19 -117.8(13) . . . . ? N1A C20A C20B C19 -116.1(6) . . . . ? N1A C20A C20B N1B 1.7(14) . . . . ? C19 C20A C20B N1B 117.8(13) . . . . ? N1B C20A C20B C17B 19(10) . . . 2_666 ? N1A C20A C20B C17B 20(11) . . . 2_666 ? C19 C20A C20B C17B 137(11) . . . 2_666 ? C18 C19 C20B C20A 106.4(8) . . . . ? C20A C19 C20B N1B -45.5(12) . . . . ? C18 C19 C20B N1B 61.0(17) . . . . ? C20A C19 C20B C17B -169(3) . . . 2_666 ? C18 C19 C20B C17B -63(3) . . . 2_666 ? N1A N1B C20B C20A -3(3) . . . . ? C16B N1B C20B C20A -107(2) . . . . ? C16A N1B C20B C20A -78(3) . . . . ? N1A N1B C20B C19 46(3) . . . . ? C20A N1B C20B C19 49.7(10) . . . . ? C16B N1B C20B C19 -58(3) . . . . ? C16A N1B C20B C19 -28(3) . . . . ? N1A N1B C20B C17B -179(3) . . . 2_666 ? C20A N1B C20B C17B -176(2) . . . 2_666 ? C16B N1B C20B C17B 77(3) . . . 2_666 ? C16A N1B C20B C17B 106(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.202 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.033 data_I-c_5hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7690(10) _cell_length_b 8.0540(10) _cell_length_c 13.456(2) _cell_angle_alpha 84.98(2) _cell_angle_beta 75.56(2) _cell_angle_gamma 81.35(2) _cell_volume 805.01(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8470 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8470 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2837 _reflns_number_gt 1863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+0.1907P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2837 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35479(17) 1.07986(17) 0.23490(9) 0.0432(4) Uani 1 1 d . . . H1 H 0.4223 1.0300 0.2691 0.052 Uiso 1 1 calc R . . C1 C 0.0390(3) 0.9980(3) 0.44804(14) 0.0428(5) Uani 1 1 d . . . C2 C 0.1062(3) 0.9940(3) 0.35808(14) 0.0410(5) Uani 1 1 d . . . C3 C 0.2028(2) 0.9940(2) 0.24817(13) 0.0341(4) Uani 1 1 d . . . C4 C 0.0850(2) 1.0883(2) 0.17969(13) 0.0350(4) Uani 1 1 d . . . C5 C -0.0990(3) 1.1152(3) 0.21233(16) 0.0535(6) Uani 1 1 d . . . H5 H -0.1549 1.0817 0.2790 0.064 Uiso 1 1 calc R . . C6 C -0.2012(3) 1.1922(3) 0.1458(2) 0.0691(7) Uani 1 1 d . . . H6 H -0.3255 1.2093 0.1683 0.083 Uiso 1 1 calc R . . C7 C -0.1221(3) 1.2429(3) 0.04840(19) 0.0647(7) Uani 1 1 d . . . H7 H -0.1915 1.2957 0.0046 0.078 Uiso 1 1 calc R . . C8 C 0.0608(3) 1.2156(3) 0.01516(17) 0.0596(6) Uani 1 1 d . . . H8 H 0.1156 1.2491 -0.0517 0.072 Uiso 1 1 calc R . . C9 C 0.1644(3) 1.1385(3) 0.08031(14) 0.0468(5) Uani 1 1 d . . . H9 H 0.2886 1.1203 0.0570 0.056 Uiso 1 1 calc R . . C10 C 0.2590(2) 0.8130(2) 0.21453(12) 0.0338(4) Uani 1 1 d . . . C11 C 0.4288(3) 0.7644(3) 0.15428(15) 0.0457(5) Uani 1 1 d . . . H11 H 0.5108 0.8414 0.1355 0.055 Uiso 1 1 calc R . . C12 C 0.4768(3) 0.6020(3) 0.12196(16) 0.0556(6) Uani 1 1 d . . . H12 H 0.5914 0.5703 0.0819 0.067 Uiso 1 1 calc R . . C13 C 0.3577(3) 0.4879(3) 0.14824(16) 0.0562(6) Uani 1 1 d . . . H13 H 0.3918 0.3785 0.1269 0.067 Uiso 1 1 calc R . . C14 C 0.1874(3) 0.5347(3) 0.20629(17) 0.0575(6) Uani 1 1 d . . . H14 H 0.1052 0.4579 0.2232 0.069 Uiso 1 1 calc R . . C15 C 0.1389(3) 0.6969(3) 0.23945(16) 0.0471(5) Uani 1 1 d . . . H15 H 0.0238 0.7282 0.2791 0.057 Uiso 1 1 calc R . . O2 O 0.4624(3) 0.0712(3) 0.62406(14) 0.0880(6) Uani 1 1 d . . . N1A N 0.3793(3) 0.2111(4) 0.48904(18) 0.0622(8) Uani 0.867(5) 1 d P . . H1NA H 0.4192 0.1229 0.4543 0.075 Uiso 0.867(5) 1 d PR . . C16A C 0.3952(4) 0.2040(5) 0.5871(2) 0.0569(8) Uani 0.867(5) 1 d P . . C17A C 0.3316(4) 0.3535(5) 0.6399(2) 0.0691(10) Uani 0.867(5) 1 d P . . H17A H 0.3391 0.3564 0.7075 0.083 Uiso 0.867(5) 1 d PR . . C18 C 0.2600(4) 0.4975(4) 0.5919(3) 0.0851(9) Uani 1 1 d . . . H18A H 0.2189 0.5949 0.6277 0.102 Uiso 0.867(5) 1 d PR . . C19 C 0.2477(4) 0.4963(5) 0.4910(3) 0.0891(9) Uani 1 1 d . . . H19A H 0.1982 0.5909 0.4580 0.107 Uiso 0.867(5) 1 d PR . . C20A C 0.3085(4) 0.3497(5) 0.4415(3) 0.0760(11) Uani 0.867(5) 1 d P . . H20A H 0.3005 0.3450 0.3741 0.091 Uiso 0.867(5) 1 d PR . . N1B N 0.451(3) 0.285(3) 0.4653(17) 0.092(7) Uiso 0.133(5) 1 d P . . H1NB H 0.4708 0.1965 0.4310 0.111 Uiso 0.133(5) 1 d PR . . C16B C 0.453(4) 0.280(4) 0.568(2) 0.079(8) Uiso 0.133(5) 1 d P . . C17B C 0.412(3) 0.446(3) 0.6140(17) 0.076(7) Uiso 0.133(5) 1 d P . . H17B H 0.3835 0.4230 0.6886 0.091 Uiso 0.133(5) 1 d PR . . C20B C 0.417(3) 0.458(3) 0.4148(17) 0.078(7) Uiso 0.133(5) 1 d P . . H20B H 0.3861 0.4410 0.3507 0.094 Uiso 0.133(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.094 Uiso 0.13 1 d P . . H19B H 0.1382 0.5198 0.4735 0.094 Uiso 0.13 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0453(8) 0.0452(9) 0.0429(8) -0.0010(6) -0.0153(6) -0.0106(6) C1 0.0499(11) 0.0435(13) 0.0322(10) -0.0053(9) -0.0072(8) 0.0002(9) C2 0.0500(11) 0.0386(12) 0.0329(11) -0.0057(8) -0.0093(8) -0.0001(9) C3 0.0381(10) 0.0357(11) 0.0274(9) -0.0033(8) -0.0056(7) -0.0049(8) C4 0.0428(10) 0.0301(11) 0.0316(10) -0.0039(8) -0.0093(8) -0.0012(8) C5 0.0452(12) 0.0579(15) 0.0474(12) 0.0063(11) -0.0039(9) 0.0066(10) C6 0.0488(13) 0.0777(19) 0.0741(17) 0.0088(14) -0.0178(12) 0.0108(12) C7 0.0720(16) 0.0622(17) 0.0619(15) 0.0059(12) -0.0336(13) 0.0092(12) C8 0.0746(16) 0.0632(17) 0.0407(12) 0.0071(11) -0.0200(11) -0.0031(12) C9 0.0502(12) 0.0524(14) 0.0352(11) 0.0013(9) -0.0095(9) -0.0024(9) C10 0.0432(10) 0.0339(11) 0.0235(9) -0.0007(8) -0.0097(7) -0.0006(8) C11 0.0450(11) 0.0486(14) 0.0409(11) -0.0086(9) -0.0068(9) -0.0007(9) C12 0.0582(13) 0.0538(15) 0.0505(13) -0.0173(11) -0.0123(10) 0.0134(11) C13 0.0859(17) 0.0327(13) 0.0489(13) -0.0068(10) -0.0237(12) 0.0111(11) C14 0.0798(16) 0.0356(13) 0.0579(14) 0.0022(11) -0.0160(12) -0.0136(11) C15 0.0529(12) 0.0379(13) 0.0462(12) -0.0004(9) -0.0046(9) -0.0055(9) O2 0.0847(13) 0.1214(19) 0.0626(11) -0.0022(11) -0.0373(10) 0.0034(12) N1A 0.0672(16) 0.0711(18) 0.0556(15) 0.0044(13) -0.0311(12) -0.0092(14) C16A 0.0456(15) 0.074(2) 0.0572(17) 0.0109(16) -0.0253(13) -0.0127(16) C17A 0.0627(19) 0.088(3) 0.0605(18) -0.0113(17) -0.0185(14) -0.0118(18) C18 0.0641(17) 0.092(2) 0.099(2) -0.0143(19) -0.0153(15) -0.0111(15) C19 0.076(2) 0.099(3) 0.093(2) 0.0084(19) -0.0324(17) -0.0048(17) C20A 0.083(2) 0.081(3) 0.069(2) 0.0120(18) -0.0362(17) -0.0070(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.423(2) . ? O1 H1 0.8200 . ? C1 C2 1.194(2) . ? C1 C1 1.380(4) 2_576 ? C2 C3 1.482(2) . ? C3 C4 1.534(3) . ? C3 C10 1.532(3) . ? C4 C5 1.376(3) . ? C4 C9 1.379(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.358(3) . ? C6 H6 0.9300 . ? C7 C8 1.368(3) . ? C7 H7 0.9300 . ? C8 C9 1.382(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.381(3) . ? C10 C11 1.384(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.365(3) . ? C12 H12 0.9300 . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.238(4) . ? O2 C16B 1.78(3) . ? N1A N1B 0.87(3) . ? N1A C20A 1.350(4) . ? N1A C16A 1.352(3) . ? N1A C16B 1.51(3) . ? N1A H1NA 0.8592 . ? N1A H1NB 0.9181 . ? C16A C16B 0.80(3) . ? C16A C17A 1.412(5) . ? C16A N1B 1.69(2) . ? C16A C17B 2.04(3) . ? C17A C17B 1.03(3) . ? C17A C16B 1.29(3) . ? C17A C18 1.387(5) . ? C17A H17A 0.9290 . ? C17A H17B 1.0813 . ? C18 C17B 1.29(2) . ? C18 C19 1.386(4) . ? C18 H18A 0.9292 . ? C18 H18B 0.9230 . ? C19 C20A 1.369(4) . ? C19 C20B 1.46(2) . ? C19 H19A 0.9289 . ? C19 H19B 0.9266 . ? C20A N1B 1.26(2) . ? C20A C20B 1.28(2) . ? C20A H20A 0.9290 . ? C20A H1NB 1.6145 . ? C20A H20B 1.4166 . ? N1B C16B 1.38(3) . ? N1B C20B 1.51(3) . ? N1B H1NA 1.3953 . ? N1B H1NB 0.8593 . ? C16B C17B 1.48(3) . ? C17B C20B 1.58(4) 2_666 ? C17B H17A 1.4262 . ? C17B H17B 0.9793 . ? C20B C17B 1.58(4) 2_666 ? C20B H20A 1.5952 . ? C20B H20B 0.9789 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.8(3) . 2_576 ? C1 C2 C3 175.2(2) . . ? O1 C3 C2 108.52(14) . . ? O1 C3 C4 107.31(15) . . ? C2 C3 C4 111.38(15) . . ? O1 C3 C10 111.04(14) . . ? C2 C3 C10 109.97(15) . . ? C4 C3 C10 108.61(14) . . ? C5 C4 C9 118.82(18) . . ? C5 C4 C3 121.88(16) . . ? C9 C4 C3 119.18(16) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.9(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.4(2) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.43(19) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C15 C10 C11 118.56(18) . . ? C15 C10 C3 120.76(16) . . ? C11 C10 C3 120.61(17) . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 120.94(19) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C16A O2 C16B 22.9(8) . . ? N1B N1A C20A 64.9(16) . . ? N1B N1A C16A 96.6(15) . . ? C20A N1A C16A 124.0(3) . . ? N1B N1A C16B 64.7(18) . . ? C20A N1A C16B 103.9(11) . . ? C16A N1A C16B 32.1(11) . . ? N1B N1A H1NA 107.8 . . ? C20A N1A H1NA 118.0 . . ? C16A N1A H1NA 118.0 . . ? C16B N1A H1NA 129.4 . . ? N1B N1A H1NB 57.5 . . ? C20A N1A H1NB 88.6 . . ? C16A N1A H1NB 126.8 . . ? C16B N1A H1NB 107.1 . . ? H1NA N1A H1NB 50.9 . . ? C16B C16A O2 120.3(19) . . ? C16B C16A N1A 84.5(19) . . ? O2 C16A N1A 119.3(3) . . ? C16B C16A C17A 64.5(19) . . ? O2 C16A C17A 125.0(3) . . ? N1A C16A C17A 115.7(3) . . ? C16B C16A N1B 54(2) . . ? O2 C16A N1B 127.9(8) . . ? N1A C16A N1B 30.7(9) . . ? C17A C16A N1B 100.0(9) . . ? C16B C16A C17B 37(2) . . ? O2 C16A C17B 129.0(7) . . ? N1A C16A C17B 104.6(7) . . ? C17A C16A C17B 27.6(7) . . ? N1B C16A C17B 79.8(11) . . ? C17B C17A C16B 78.5(18) . . ? C17B C17A C18 62.5(13) . . ? C16B C17A C18 104.6(12) . . ? C17B C17A C16A 112.8(13) . . ? C16B C17A C16A 34.2(13) . . ? C18 C17A C16A 121.1(3) . . ? C17B C17A H17A 93.6 . . ? C16B C17A H17A 125.3 . . ? C18 C17A H17A 119.2 . . ? C16A C17A H17A 119.7 . . ? C17B C17A H17B 55.3 . . ? C16B C17A H17B 113.9 . . ? C18 C17A H17B 93.6 . . ? C16A C17A H17B 134.2 . . ? H17A C17A H17B 38.5 . . ? C17B C18 C19 119.0(10) . . ? C17B C18 C17A 44.9(12) . . ? C19 C18 C17A 120.3(3) . . ? C17B C18 H18A 103.5 . . ? C19 C18 H18A 119.7 . . ? C17A C18 H18A 120.0 . . ? C17B C18 H18B 121.1 . . ? C19 C18 H18B 119.9 . . ? C17A C18 H18B 102.6 . . ? H18A C18 H18B 43.4 . . ? C18 C19 C20A 117.8(3) . . ? C18 C19 C20B 116.0(9) . . ? C20A C19 C20B 53.4(9) . . ? C18 C19 H19A 121.5 . . ? C20A C19 H19A 120.7 . . ? C20B C19 H19A 99.2 . . ? C18 C19 H19B 121.4 . . ? C20A C19 H19B 98.0 . . ? C20B C19 H19B 122.6 . . ? H19A C19 H19B 49.3 . . ? N1B C20A C20B 73.3(15) . . ? N1B C20A N1A 38.6(12) . . ? C20B C20A N1A 111.9(10) . . ? N1B C20A C19 108.2(12) . . ? C20B C20A C19 67.1(10) . . ? N1A C20A C19 121.2(3) . . ? N1B C20A H20A 118.5 . . ? C20B C20A H20A 91.3 . . ? N1A C20A H20A 119.3 . . ? C19 C20A H20A 119.6 . . ? N1B C20A H1NB 31.8 . . ? C20B C20A H1NB 91.9 . . ? N1A C20A H1NB 34.6 . . ? C19 C20A H1NB 140.1 . . ? H20A C20A H1NB 93.2 . . ? N1B C20A H20B 97.8 . . ? C20B C20A H20B 42.2 . . ? N1A C20A H20B 129.7 . . ? C19 C20A H20B 90.4 . . ? H20A C20A H20B 49.1 . . ? H1NB C20A H20B 95.8 . . ? N1A N1B C20A 76.5(18) . . ? N1A N1B C16B 81(2) . . ? C20A N1B C16B 117(2) . . ? N1A N1B C20B 130(2) . . ? C20A N1B C20B 53.9(13) . . ? C16B N1B C20B 116(2) . . ? N1A N1B C16A 52.7(12) . . ? C20A N1B C16A 107.3(15) . . ? C16B N1B C16A 28.1(13) . . ? C20B N1B C16A 134.0(18) . . ? N1A N1B H1NA 35.9 . . ? C20A N1B H1NA 92.0 . . ? C16B N1B H1NA 102.0 . . ? C20B N1B H1NA 137.0 . . ? C16A N1B H1NA 76.0 . . ? N1A N1B H1NB 64.2 . . ? C20A N1B H1NB 97.6 . . ? C16B N1B H1NB 122.8 . . ? C20B N1B H1NB 121.1 . . ? C16A N1B H1NB 101.3 . . ? H1NA N1B H1NB 28.9 . . ? C16A C16B C17A 81(2) . . ? C16A C16B N1B 98(2) . . ? C17A C16B N1B 126(2) . . ? C16A C16B N1A 63.4(18) . . ? C17A C16B N1A 113.6(18) . . ? N1B C16B N1A 34.7(12) . . ? C16A C16B C17B 124(3) . . ? C17A C16B C17B 42.8(13) . . ? N1B C16B C17B 115(2) . . ? N1A C16B C17B 131(2) . . ? C16A C16B O2 36.8(14) . . ? C17A C16B O2 98.6(17) . . ? N1B C16B O2 112(2) . . ? N1A C16B O2 85.2(14) . . ? C17B C16B O2 131.7(19) . . ? C17A C17B C18 72.6(15) . . ? C17A C17B C16B 58.6(16) . . ? C18 C17B C16B 99.6(18) . . ? C17A C17B C20B 161(2) . 2_666 ? C18 C17B C20B 126(2) . 2_666 ? C16B C17B C20B 110.6(19) . 2_666 ? C17A C17B C16A 39.6(9) . . ? C18 C17B C16A 91.2(14) . . ? C16B C17B C16A 19.0(11) . . ? C20B C17B C16A 128.4(15) 2_666 . ? C17A C17B H17A 40.6 . . ? C18 C17B H17A 95.5 . . ? C16B C17B H17A 85.7 . . ? C20B C17B H17A 129.1 2_666 . ? C16A C17B H17A 69.4 . . ? C17A C17B H17B 65.2 . . ? C18 C17B H17B 105.2 . . ? C16B C17B H17B 106.3 . . ? C20B C17B H17B 107.3 2_666 . ? C16A C17B H17B 92.4 . . ? H17A C17B H17B 24.9 . . ? C20A C20B C19 59.5(9) . . ? C20A C20B N1B 52.8(12) . . ? C19 C20B N1B 91.3(15) . . ? C20A C20B C17B 166(2) . 2_666 ? C19 C20B C17B 129.6(18) . 2_666 ? N1B C20B C17B 113.2(19) . 2_666 ? C20A C20B H20A 35.6 . . ? C19 C20B H20A 81.5 . . ? N1B C20B H20A 74.7 . . ? C17B C20B H20A 145.7 2_666 . ? C20A C20B H20B 76.6 . . ? C19 C20B H20B 106.4 . . ? N1B C20B H20B 106.1 . . ? C17B C20B H20B 107.6 2_666 . ? H20A C20B H20B 41.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -149(100) 2_576 . . . ? C1 C2 C3 O1 -12(3) . . . . ? C1 C2 C3 C4 -130(3) . . . . ? C1 C2 C3 C10 110(3) . . . . ? O1 C3 C4 C5 -139.32(19) . . . . ? C2 C3 C4 C5 -20.7(3) . . . . ? C10 C3 C4 C5 100.6(2) . . . . ? O1 C3 C4 C9 44.9(2) . . . . ? C2 C3 C4 C9 163.49(17) . . . . ? C10 C3 C4 C9 -75.3(2) . . . . ? C9 C4 C5 C6 -0.3(3) . . . . ? C3 C4 C5 C6 -176.1(2) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C6 C7 C8 C9 -0.6(4) . . . . ? C5 C4 C9 C8 0.5(3) . . . . ? C3 C4 C9 C8 176.50(19) . . . . ? C7 C8 C9 C4 -0.1(4) . . . . ? O1 C3 C10 C15 166.94(16) . . . . ? C2 C3 C10 C15 46.8(2) . . . . ? C4 C3 C10 C15 -75.3(2) . . . . ? O1 C3 C10 C11 -16.2(2) . . . . ? C2 C3 C10 C11 -136.30(17) . . . . ? C4 C3 C10 C11 101.58(18) . . . . ? C15 C10 C11 C12 -1.3(3) . . . . ? C3 C10 C11 C12 -178.26(17) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C11 C10 C15 C14 0.9(3) . . . . ? C3 C10 C15 C14 177.84(18) . . . . ? C13 C14 C15 C10 0.4(3) . . . . ? C16B O2 C16A N1A 102(2) . . . . ? C16B O2 C16A C17A -78(2) . . . . ? C16B O2 C16A N1B 66(2) . . . . ? C16B O2 C16A C17B -44(2) . . . . ? N1B N1A C16A C16B 6(3) . . . . ? C20A N1A C16A C16B -58(2) . . . . ? N1B N1A C16A O2 -115.8(16) . . . . ? C20A N1A C16A O2 -179.8(3) . . . . ? C16B N1A C16A O2 -122(2) . . . . ? N1B N1A C16A C17A 64.3(16) . . . . ? C20A N1A C16A C17A 0.2(4) . . . . ? C16B N1A C16A C17A 58.2(19) . . . . ? C20A N1A C16A N1B -64.0(16) . . . . ? C16B N1A C16A N1B -6(3) . . . . ? N1B N1A C16A C17B 37.3(17) . . . . ? C20A N1A C16A C17B -26.8(8) . . . . ? C16B N1A C16A C17B 31(2) . . . . ? C16B C16A C17A C17B -2(2) . . . . ? O2 C16A C17A C17B 108.6(15) . . . . ? N1A C16A C17A C17B -71.4(15) . . . . ? N1B C16A C17A C17B -43.6(17) . . . . ? O2 C16A C17A C16B 110(2) . . . . ? N1A C16A C17A C16B -70(2) . . . . ? N1B C16A C17A C16B -42(2) . . . . ? C17B C16A C17A C16B 2(2) . . . . ? C16B C16A C17A C18 69(2) . . . . ? O2 C16A C17A C18 179.2(3) . . . . ? N1A C16A C17A C18 -0.8(4) . . . . ? N1B C16A C17A C18 27.0(9) . . . . ? C17B C16A C17A C18 70.6(15) . . . . ? C16B C17A C18 C17B -68.4(19) . . . . ? C16A C17A C18 C17B -101.3(14) . . . . ? C17B C17A C18 C19 102.1(14) . . . . ? C16B C17A C18 C19 33.6(14) . . . . ? C16A C17A C18 C19 0.8(5) . . . . ? C17B C18 C19 C20A 52.0(14) . . . . ? C17A C18 C19 C20A -0.1(4) . . . . ? C17B C18 C19 C20B -8.5(17) . . . . ? C17A C18 C19 C20B -60.6(11) . . . . ? C16A N1A C20A N1B 80.6(17) . . . . ? C16B N1A C20A N1B 52.9(19) . . . . ? N1B N1A C20A C20B -4(2) . . . . ? C16A N1A C20A C20B 76.1(12) . . . . ? C16B N1A C20A C20B 48.5(16) . . . . ? N1B N1A C20A C19 -80.1(17) . . . . ? C16A N1A C20A C19 0.5(5) . . . . ? C16B N1A C20A C19 -27.2(11) . . . . ? C18 C19 C20A N1B -40.9(13) . . . . ? C20B C19 C20A N1B 62.2(16) . . . . ? C18 C19 C20A C20B -103.0(11) . . . . ? C18 C19 C20A N1A -0.5(5) . . . . ? C20B C19 C20A N1A 102.5(11) . . . . ? C16A N1A N1B C20A -124.6(7) . . . . ? C16B N1A N1B C20A -121.0(17) . . . . ? C20A N1A N1B C16B 121.0(17) . . . . ? C16A N1A N1B C16B -3.6(15) . . . . ? C20A N1A N1B C20B 5(2) . . . . ? C16A N1A N1B C20B -120(3) . . . . ? C16B N1A N1B C20B -116(3) . . . . ? C20A N1A N1B C16A 124.6(7) . . . . ? C16B N1A N1B C16A 3.6(15) . . . . ? C20B C20A N1B N1A 176(2) . . . . ? C19 C20A N1B N1A 117.4(13) . . . . ? C20B C20A N1B C16B 104(3) . . . . ? N1A C20A N1B C16B -72(2) . . . . ? C19 C20A N1B C16B 46(2) . . . . ? N1A C20A N1B C20B -176(2) . . . . ? C19 C20A N1B C20B -58.2(12) . . . . ? C20B C20A N1B C16A 132.3(19) . . . . ? N1A C20A N1B C16A -43.3(10) . . . . ? C19 C20A N1B C16A 74.1(15) . . . . ? C16B C16A N1B N1A -173(3) . . . . ? O2 C16A N1B N1A 84.4(16) . . . . ? C17A C16A N1B N1A -124.5(14) . . . . ? C17B C16A N1B N1A -143.5(16) . . . . ? C16B C16A N1B C20A -116(3) . . . . ? O2 C16A N1B C20A 141.4(11) . . . . ? N1A C16A N1B C20A 57.0(15) . . . . ? C17A C16A N1B C20A -67.5(16) . . . . ? C17B C16A N1B C20A -86.5(17) . . . . ? O2 C16A N1B C16B -103(3) . . . . ? N1A C16A N1B C16B 173(3) . . . . ? C17A C16A N1B C16B 48(2) . . . . ? C17B C16A N1B C16B 29(2) . . . . ? C16B C16A N1B C20B -59(3) . . . . ? O2 C16A N1B C20B -162.4(19) . . . . ? N1A C16A N1B C20B 113(3) . . . . ? C17A C16A N1B C20B -11(3) . . . . ? C17B C16A N1B C20B -30(3) . . . . ? O2 C16A C16B C17A -117.2(11) . . . . ? N1A C16A C16B C17A 121.9(10) . . . . ? N1B C16A C16B C17A 126(2) . . . . ? C17B C16A C16B C17A -1.4(19) . . . . ? O2 C16A C16B N1B 117.1(17) . . . . ? N1A C16A C16B N1B -3.8(16) . . . . ? C17A C16A C16B N1B -126(2) . . . . ? C17B C16A C16B N1B -127(4) . . . . ? O2 C16A C16B N1A 120.9(11) . . . . ? C17A C16A C16B N1A -121.9(10) . . . . ? N1B C16A C16B N1A 3.8(16) . . . . ? C17B C16A C16B N1A -123(3) . . . . ? O2 C16A C16B C17B -116(2) . . . . ? N1A C16A C16B C17B 123(3) . . . . ? C17A C16A C16B C17B 1.4(19) . . . . ? N1B C16A C16B C17B 127(4) . . . . ? N1A C16A C16B O2 -120.9(11) . . . . ? C17A C16A C16B O2 117.2(11) . . . . ? N1B C16A C16B O2 -117.1(17) . . . . ? C17B C16A C16B O2 116(2) . . . . ? C17B C17A C16B C16A 178(2) . . . . ? C18 C17A C16B C16A -124.4(16) . . . . ? C17B C17A C16B N1B -88(3) . . . . ? C18 C17A C16B N1B -31(3) . . . . ? C16A C17A C16B N1B 93(3) . . . . ? C17B C17A C16B N1A -126(2) . . . . ? C18 C17A C16B N1A -69(2) . . . . ? C16A C17A C16B N1A 55.9(18) . . . . ? C18 C17A C16B C17B 57.3(14) . . . . ? C16A C17A C16B C17B -178(2) . . . . ? C17B C17A C16B O2 145.7(18) . . . . ? C18 C17A C16B O2 -157.0(8) . . . . ? C16A C17A C16B O2 -32.6(11) . . . . ? N1A N1B C16B C16A 6(3) . . . . ? C20A N1B C16B C16A 75(3) . . . . ? C20B N1B C16B C16A 136(2) . . . . ? N1A N1B C16B C17A -79(3) . . . . ? C20A N1B C16B C17A -9(4) . . . . ? C20B N1B C16B C17A 51(4) . . . . ? C16A N1B C16B C17A -85(3) . . . . ? C20A N1B C16B N1A 69(2) . . . . ? C20B N1B C16B N1A 130(3) . . . . ? C16A N1B C16B N1A -6(3) . . . . ? N1A N1B C16B C17B -127(2) . . . . ? C20A N1B C16B C17B -58(3) . . . . ? C20B N1B C16B C17B 3(3) . . . . ? C16A N1B C16B C17B -133(3) . . . . ? N1A N1B C16B O2 41(2) . . . . ? C20A N1B C16B O2 111(2) . . . . ? C20B N1B C16B O2 171.6(17) . . . . ? C16A N1B C16B O2 35.2(14) . . . . ? N1B N1A C16B C16A -173(3) . . . . ? C20A N1A C16B C16A 133.6(15) . . . . ? N1B N1A C16B C17A 120(3) . . . . ? C20A N1A C16B C17A 67(2) . . . . ? C16A N1A C16B C17A -66(2) . . . . ? C20A N1A C16B N1B -53.1(19) . . . . ? C16A N1A C16B N1B 173(3) . . . . ? N1B N1A C16B C17B 73(3) . . . . ? C20A N1A C16B C17B 20(3) . . . . ? C16A N1A C16B C17B -113(4) . . . . ? N1B N1A C16B O2 -142(2) . . . . ? C20A N1A C16B O2 164.6(6) . . . . ? C16A N1A C16B O2 31.1(11) . . . . ? C16A O2 C16B C17A 62.8(19) . . . . ? C16A O2 C16B N1B -72(2) . . . . ? C16A O2 C16B N1A -50.4(17) . . . . ? C16A O2 C16B C17B 94(3) . . . . ? C16B C17A C17B C18 113.4(14) . . . . ? C16A C17A C17B C18 114.4(7) . . . . ? C18 C17A C17B C16B -113.4(14) . . . . ? C16A C17A C17B C16B 1.0(14) . . . . ? C16B C17A C17B C20B -60(7) . . . 2_666 ? C18 C17A C17B C20B -173(7) . . . 2_666 ? C16A C17A C17B C20B -59(7) . . . 2_666 ? C16B C17A C17B C16A -1.0(14) . . . . ? C18 C17A C17B C16A -114.4(7) . . . . ? C19 C18 C17B C17A -105.1(11) . . . . ? C19 C18 C17B C16B -52(2) . . . . ? C17A C18 C17B C16B 52.7(15) . . . . ? C19 C18 C17B C20B 72(2) . . . 2_666 ? C17A C18 C17B C20B 177(3) . . . 2_666 ? C19 C18 C17B C16A -69.6(12) . . . . ? C17A C18 C17B C16A 35.5(7) . . . . ? C16A C16B C17B C17A -2(3) . . . . ? N1B C16B C17B C17A 118(2) . . . . ? N1A C16B C17B C17A 81(3) . . . . ? O2 C16B C17B C17A -48(2) . . . . ? C16A C16B C17B C18 -65(3) . . . . ? C17A C16B C17B C18 -62.7(15) . . . . ? N1B C16B C17B C18 55(3) . . . . ? N1A C16B C17B C18 18(3) . . . . ? O2 C16B C17B C18 -111(2) . . . . ? C16A C16B C17B C20B 161(3) . . . 2_666 ? C17A C16B C17B C20B 163(2) . . . 2_666 ? N1B C16B C17B C20B -80(3) . . . 2_666 ? N1A C16B C17B C20B -117(3) . . . 2_666 ? O2 C16B C17B C20B 114(2) . . . 2_666 ? C17A C16B C17B C16A 2(3) . . . . ? N1B C16B C17B C16A 120(4) . . . . ? N1A C16B C17B C16A 83(4) . . . . ? O2 C16B C17B C16A -46(2) . . . . ? C16B C16A C17B C17A 177(4) . . . . ? O2 C16A C17B C17A -92.5(14) . . . . ? N1A C16A C17B C17A 118.1(13) . . . . ? N1B C16A C17B C17A 136.4(16) . . . . ? C16B C16A C17B C18 117(3) . . . . ? O2 C16A C17B C18 -152.9(7) . . . . ? N1A C16A C17B C18 57.7(12) . . . . ? C17A C16A C17B C18 -60.4(12) . . . . ? N1B C16A C17B C18 76.0(14) . . . . ? O2 C16A C17B C16B 90(3) . . . . ? N1A C16A C17B C16B -59(3) . . . . ? C17A C16A C17B C16B -177(4) . . . . ? N1B C16A C17B C16B -41(3) . . . . ? C16B C16A C17B C20B -23(3) . . . 2_666 ? O2 C16A C17B C20B 67(2) . . . 2_666 ? N1A C16A C17B C20B -82.7(19) . . . 2_666 ? C17A C16A C17B C20B 159(3) . . . 2_666 ? N1B C16A C17B C20B -64(2) . . . 2_666 ? N1B C20A C20B C19 -118.8(13) . . . . ? N1A C20A C20B C19 -115.8(6) . . . . ? N1A C20A C20B N1B 2.9(13) . . . . ? C19 C20A C20B N1B 118.8(13) . . . . ? N1B C20A C20B C17B 14(8) . . . 2_666 ? N1A C20A C20B C17B 17(8) . . . 2_666 ? C19 C20A C20B C17B 133(8) . . . 2_666 ? C18 C19 C20B C20A 106.5(8) . . . . ? C18 C19 C20B N1B 62.2(15) . . . . ? C20A C19 C20B N1B -44.3(11) . . . . ? C18 C19 C20B C17B -60(2) . . . 2_666 ? C20A C19 C20B C17B -166(3) . . . 2_666 ? N1A N1B C20B C20A -6(3) . . . . ? C16B N1B C20B C20A -106(2) . . . . ? C16A N1B C20B C20A -79(2) . . . . ? N1A N1B C20B C19 44(3) . . . . ? C20A N1B C20B C19 49.1(10) . . . . ? C16B N1B C20B C19 -57(2) . . . . ? C16A N1B C20B C19 -30(3) . . . . ? N1A N1B C20B C17B 178(3) . . . 2_666 ? C20A N1B C20B C17B -176(2) . . . 2_666 ? C16B N1B C20B C17B 78(3) . . . 2_666 ? C16A N1B C20B C17B 105(2) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.178 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.036 data_I-c_6hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7730(10) _cell_length_b 8.0570(10) _cell_length_c 13.470(2) _cell_angle_alpha 84.97(2) _cell_angle_beta 75.51(2) _cell_angle_gamma 81.44(2) _cell_volume 806.53(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8558 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8558 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2841 _reflns_number_gt 1838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.1277P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2841 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35461(17) 1.07981(17) 0.23481(10) 0.0443(4) Uani 1 1 d . . . H1 H 0.4219 1.0299 0.2690 0.053 Uiso 1 1 calc R . . C1 C 0.0388(3) 0.9977(3) 0.44796(14) 0.0440(5) Uani 1 1 d . . . C2 C 0.1059(3) 0.9937(3) 0.35805(14) 0.0424(5) Uani 1 1 d . . . C3 C 0.2026(2) 0.9941(2) 0.24809(13) 0.0353(5) Uani 1 1 d . . . C4 C 0.0850(2) 1.0878(2) 0.17976(13) 0.0355(4) Uani 1 1 d . . . C5 C -0.0990(3) 1.1156(3) 0.21252(17) 0.0545(6) Uani 1 1 d . . . H5 H -0.1549 1.0827 0.2793 0.065 Uiso 1 1 calc R . . C6 C -0.2009(3) 1.1923(3) 0.1463(2) 0.0705(7) Uani 1 1 d . . . H6 H -0.3251 1.2092 0.1690 0.085 Uiso 1 1 calc R . . C7 C -0.1225(3) 1.2434(3) 0.04859(19) 0.0655(7) Uani 1 1 d . . . H7 H -0.1921 1.2964 0.0050 0.079 Uiso 1 1 calc R . . C8 C 0.0607(3) 1.2154(3) 0.01528(17) 0.0604(6) Uani 1 1 d . . . H8 H 0.1157 1.2487 -0.0516 0.073 Uiso 1 1 calc R . . C9 C 0.1643(3) 1.1381(3) 0.08032(14) 0.0473(5) Uani 1 1 d . . . H9 H 0.2883 1.1199 0.0569 0.057 Uiso 1 1 calc R . . C10 C 0.2589(2) 0.8125(2) 0.21455(13) 0.0347(4) Uani 1 1 d . . . C11 C 0.4285(3) 0.7640(3) 0.15465(15) 0.0460(5) Uani 1 1 d . . . H11 H 0.5106 0.8409 0.1361 0.055 Uiso 1 1 calc R . . C12 C 0.4767(3) 0.6019(3) 0.12214(16) 0.0567(6) Uani 1 1 d . . . H12 H 0.5914 0.5704 0.0823 0.068 Uiso 1 1 calc R . . C13 C 0.3574(3) 0.4877(3) 0.14811(17) 0.0578(6) Uani 1 1 d . . . H13 H 0.3911 0.3786 0.1265 0.069 Uiso 1 1 calc R . . C14 C 0.1869(3) 0.5345(3) 0.20636(17) 0.0596(6) Uani 1 1 d . . . H14 H 0.1047 0.4576 0.2233 0.072 Uiso 1 1 calc R . . C15 C 0.1385(3) 0.6966(3) 0.23965(16) 0.0480(5) Uani 1 1 d . . . H15 H 0.0236 0.7278 0.2794 0.058 Uiso 1 1 calc R . . O2 O 0.4633(3) 0.0715(3) 0.62359(14) 0.0935(7) Uani 1 1 d . . . N1A N 0.3800(4) 0.2109(4) 0.48870(18) 0.0651(8) Uani 0.855(5) 1 d P . . H1NA H 0.4200 0.1227 0.4540 0.078 Uiso 0.855(5) 1 d PR . . C16A C 0.3956(4) 0.2037(5) 0.5871(2) 0.0596(9) Uani 0.855(5) 1 d P . . C17A C 0.3322(4) 0.3529(5) 0.6392(2) 0.0736(11) Uani 0.855(5) 1 d P . . H17A H 0.3398 0.3558 0.7069 0.088 Uiso 0.855(5) 1 d PR . . C18 C 0.2604(4) 0.4977(5) 0.5912(3) 0.0886(9) Uani 1 1 d . . . H18A H 0.2194 0.5951 0.6270 0.106 Uiso 0.855(5) 1 d PR . . C19 C 0.2482(4) 0.4969(5) 0.4909(3) 0.0922(10) Uani 1 1 d . . . H19A H 0.1988 0.5915 0.4579 0.111 Uiso 0.855(5) 1 d PR . . C20A C 0.3086(5) 0.3486(5) 0.4413(3) 0.0796(11) Uani 0.855(5) 1 d P . . H20A H 0.3007 0.3439 0.3739 0.095 Uiso 0.855(5) 1 d PR . . N1B N 0.453(3) 0.291(3) 0.4651(14) 0.084(6) Uiso 0.145(5) 1 d P . . H1NB H 0.4719 0.2022 0.4308 0.100 Uiso 0.145(5) 1 d PR . . C16B C 0.458(3) 0.276(3) 0.5664(17) 0.073(6) Uiso 0.145(5) 1 d P . . C17B C 0.415(3) 0.446(2) 0.6156(14) 0.063(5) Uiso 0.145(5) 1 d P . . H17B H 0.3867 0.4229 0.6902 0.075 Uiso 0.145(5) 1 d PR . . C20B C 0.414(2) 0.458(2) 0.4149(14) 0.068(6) Uiso 0.145(5) 1 d P . . H20B H 0.3825 0.4407 0.3508 0.081 Uiso 0.145(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.081 Uiso 0.14 1 d P . . H19B H 0.1382 0.5198 0.4735 0.081 Uiso 0.14 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0474(8) 0.0461(9) 0.0436(8) -0.0018(6) -0.0160(6) -0.0109(6) C1 0.0514(12) 0.0456(13) 0.0319(10) -0.0042(9) -0.0073(8) 0.0002(9) C2 0.0514(11) 0.0409(13) 0.0329(11) -0.0053(9) -0.0092(9) 0.0002(9) C3 0.0383(10) 0.0391(12) 0.0275(9) -0.0034(8) -0.0054(7) -0.0049(8) C4 0.0453(11) 0.0304(11) 0.0306(10) -0.0041(8) -0.0100(8) -0.0019(8) C5 0.0474(12) 0.0589(16) 0.0483(13) 0.0065(11) -0.0057(10) 0.0053(10) C6 0.0502(13) 0.080(2) 0.0745(17) 0.0106(15) -0.0188(12) 0.0098(12) C7 0.0713(16) 0.0645(18) 0.0638(16) 0.0053(13) -0.0335(13) 0.0055(13) C8 0.0781(16) 0.0639(17) 0.0388(12) 0.0086(11) -0.0192(11) -0.0054(12) C9 0.0518(12) 0.0530(14) 0.0346(11) 0.0012(9) -0.0093(9) -0.0023(10) C10 0.0440(10) 0.0356(11) 0.0238(9) -0.0008(8) -0.0106(8) 0.0001(8) C11 0.0462(11) 0.0486(14) 0.0398(11) -0.0083(10) -0.0055(9) -0.0003(9) C12 0.0614(14) 0.0556(16) 0.0485(13) -0.0158(11) -0.0134(10) 0.0141(12) C13 0.0868(17) 0.0370(14) 0.0492(13) -0.0075(10) -0.0254(12) 0.0119(12) C14 0.0817(17) 0.0391(14) 0.0580(15) 0.0009(11) -0.0148(12) -0.0136(12) C15 0.0538(12) 0.0419(13) 0.0437(12) -0.0015(10) -0.0038(9) -0.0059(10) O2 0.0876(13) 0.134(2) 0.0632(12) -0.0035(12) -0.0377(10) 0.0036(13) N1A 0.0718(17) 0.075(2) 0.0558(15) 0.0053(13) -0.0313(13) -0.0102(15) C16A 0.0458(16) 0.080(3) 0.0583(18) 0.0120(18) -0.0248(14) -0.0132(17) C17A 0.066(2) 0.096(3) 0.064(2) -0.0133(19) -0.0212(16) -0.0129(19) C18 0.0669(18) 0.101(3) 0.097(2) -0.016(2) -0.0135(16) -0.0113(16) C19 0.079(2) 0.107(3) 0.093(2) 0.004(2) -0.0327(17) -0.0049(18) C20A 0.086(2) 0.089(3) 0.070(2) 0.014(2) -0.0382(18) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.422(2) . ? O1 H1 0.8200 . ? C1 C2 1.194(3) . ? C1 C1 1.382(4) 2_576 ? C2 C3 1.484(2) . ? C3 C4 1.531(3) . ? C3 C10 1.537(3) . ? C4 C5 1.377(3) . ? C4 C9 1.380(3) . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 C7 1.361(3) . ? C6 H6 0.9300 . ? C7 C8 1.372(3) . ? C7 H7 0.9300 . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.381(3) . ? C10 C11 1.383(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 H12 0.9300 . ? C13 C14 1.377(3) . ? C13 H13 0.9300 . ? C14 C15 1.386(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.234(4) . ? O2 C16B 1.76(3) . ? N1A N1B 0.91(2) . ? N1A C20A 1.348(4) . ? N1A C16A 1.356(4) . ? N1A C16B 1.50(2) . ? N1A H1NA 0.8600 . ? N1A H1NB 0.9161 . ? C16A C16B 0.80(2) . ? C16A C17A 1.407(5) . ? C16A N1B 1.71(2) . ? C16A C17B 2.06(2) . ? C17A C17B 1.04(2) . ? C17A C16B 1.32(2) . ? C17A C18 1.394(5) . ? C17A H17A 0.9300 . ? C17A H17B 1.1193 . ? C18 C17B 1.325(19) . ? C18 C19 1.379(4) . ? C18 H18A 0.9300 . ? C18 H18B 0.9304 . ? C19 C20A 1.382(5) . ? C19 C20B 1.442(18) . ? C19 H19A 0.9300 . ? C19 H19B 0.9305 . ? C20A C20B 1.261(18) . ? C20A N1B 1.253(19) . ? C20A H20A 0.9300 . ? C20A H20B 1.4088 . ? N1B C16B 1.37(3) . ? N1B C20B 1.48(3) . ? N1B H1NA 1.4432 . ? N1B H1NB 0.8600 . ? C16B C17B 1.53(3) . ? C17B C20B 1.58(3) 2_666 ? C17B H17A 1.4109 . ? C17B H17B 0.9800 . ? C20B C17B 1.58(3) 2_666 ? C20B H20A 1.5808 . ? C20B H20B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.9(3) . 2_576 ? C1 C2 C3 175.2(2) . . ? O1 C3 C2 108.54(14) . . ? O1 C3 C4 107.47(15) . . ? C2 C3 C4 111.45(15) . . ? O1 C3 C10 110.98(14) . . ? C2 C3 C10 109.82(15) . . ? C4 C3 C10 108.57(14) . . ? C5 C4 C9 118.61(18) . . ? C5 C4 C3 122.01(17) . . ? C9 C4 C3 119.28(16) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 119.0(2) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 120.5(2) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C15 C10 C11 118.65(19) . . ? C15 C10 C3 120.68(16) . . ? C11 C10 C3 120.61(17) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C10 C15 C14 120.81(19) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C16A O2 C16B 23.9(7) . . ? N1B N1A C20A 64.1(13) . . ? N1B N1A C16A 96.1(12) . . ? C20A N1A C16A 124.1(3) . . ? N1B N1A C16B 63.9(15) . . ? C20A N1A C16B 105.3(10) . . ? C16A N1A C16B 32.2(9) . . ? N1B N1A H1NA 109.7 . . ? C20A N1A H1NA 117.9 . . ? C16A N1A H1NA 118.0 . . ? C16B N1A H1NA 127.8 . . ? N1B N1A H1NB 56.4 . . ? C20A N1A H1NB 86.8 . . ? C16A N1A H1NB 126.7 . . ? C16B N1A H1NB 104.5 . . ? H1NA N1A H1NB 53.9 . . ? C16B C16A O2 117.7(17) . . ? C16B C16A N1A 83.9(16) . . ? O2 C16A N1A 119.2(3) . . ? C16B C16A C17A 67.2(17) . . ? O2 C16A C17A 125.3(3) . . ? N1A C16A C17A 115.5(3) . . ? C16B C16A N1B 52.1(17) . . ? O2 C16A N1B 128.7(7) . . ? N1A C16A N1B 31.8(7) . . ? C17A C16A N1B 98.3(7) . . ? C16B C16A C17B 39.7(17) . . ? O2 C16A C17B 128.0(6) . . ? N1A C16A C17B 105.3(6) . . ? C17A C16A C17B 27.6(5) . . ? N1B C16A C17B 78.9(9) . . ? C17B C17A C16B 79.6(15) . . ? C17B C17A C18 64.1(11) . . ? C16B C17A C18 105.6(11) . . ? C17B C17A C16A 113.6(10) . . ? C16B C17A C16A 34.0(11) . . ? C18 C17A C16A 121.4(3) . . ? C17B C17A H17A 91.4 . . ? C16B C17A H17A 124.4 . . ? C18 C17A H17A 119.1 . . ? C16A C17A H17A 119.4 . . ? C17B C17A H17B 53.9 . . ? C16B C17A H17B 113.3 . . ? C18 C17A H17B 94.5 . . ? C16A C17A H17B 133.4 . . ? H17A C17A H17B 37.8 . . ? C17B C18 C19 120.1(8) . . ? C17B C18 C17A 44.8(9) . . ? C19 C18 C17A 120.3(3) . . ? C17B C18 H18A 102.7 . . ? C19 C18 H18A 119.6 . . ? C17A C18 H18A 120.1 . . ? C17B C18 H18B 119.7 . . ? C19 C18 H18B 120.2 . . ? C17A C18 H18B 102.4 . . ? H18A C18 H18B 43.4 . . ? C20A C19 C18 117.5(3) . . ? C20A C19 C20B 53.0(8) . . ? C18 C19 C20B 116.7(8) . . ? C20A C19 H19A 120.8 . . ? C18 C19 H19A 121.6 . . ? C20B C19 H19A 99.2 . . ? C20A C19 H19B 97.7 . . ? C18 C19 H19B 121.3 . . ? C20B C19 H19B 122.0 . . ? H19A C19 H19B 49.6 . . ? C20B C20A N1B 72.0(13) . . ? C20B C20A N1A 112.5(9) . . ? N1B C20A N1A 40.5(10) . . ? C20B C20A C19 66.0(9) . . ? N1B C20A C19 106.0(10) . . ? N1A C20A C19 121.2(3) . . ? C20B C20A H20A 91.1 . . ? N1B C20A H20A 119.2 . . ? N1A C20A H20A 119.4 . . ? C19 C20A H20A 119.4 . . ? C20B C20A H20B 42.6 . . ? N1B C20A H20B 97.6 . . ? N1A C20A H20B 130.5 . . ? C19 C20A H20B 89.8 . . ? H20A C20A H20B 48.6 . . ? N1A N1B C20A 75.4(14) . . ? N1A N1B C16B 79.7(16) . . ? C20A N1B C16B 119.5(17) . . ? N1A N1B C20B 130(2) . . ? C20A N1B C20B 54.3(11) . . ? C16B N1B C20B 120.4(19) . . ? N1A N1B C16A 52.1(10) . . ? C20A N1B C16A 106.5(13) . . ? C16B N1B C16A 27.6(11) . . ? C20B N1B C16A 135.4(15) . . ? N1A N1B H1NA 34.1 . . ? C20A N1B H1NA 89.8 . . ? C16B N1B H1NA 98.9 . . ? C20B N1B H1NA 135.5 . . ? C16A N1B H1NA 74.4 . . ? N1A N1B H1NB 62.5 . . ? C20A N1B H1NB 95.5 . . ? C16B N1B H1NB 119.5 . . ? C20B N1B H1NB 120.1 . . ? C16A N1B H1NB 99.9 . . ? H1NA N1B H1NB 28.9 . . ? C16A C16B C17A 78.8(18) . . ? C16A C16B N1B 100(2) . . ? C17A C16B N1B 122.9(19) . . ? C16A C16B N1A 64.0(15) . . ? C17A C16B N1A 111.6(15) . . ? N1B C16B N1A 36.4(10) . . ? C16A C16B C17B 121(2) . . ? C17A C16B C17B 42.0(10) . . ? N1B C16B C17B 112(2) . . ? N1A C16B C17B 130.2(16) . . ? C16A C16B O2 38.4(12) . . ? C17A C16B O2 98.3(15) . . ? N1B C16B O2 116.0(17) . . ? N1A C16B O2 86.2(12) . . ? C17B C16B O2 130.1(16) . . ? C17A C17B C18 71.2(12) . . ? C17A C17B C16B 58.5(13) . . ? C18 C17B C16B 98.6(14) . . ? C17A C17B C20B 162.6(18) . 2_666 ? C18 C17B C20B 125.5(16) . 2_666 ? C16B C17B C20B 109.9(15) . 2_666 ? C17A C17B C16A 38.9(7) . . ? C18 C17B C16A 89.9(11) . . ? C16B C17B C16A 19.6(9) . . ? C20B C17B C16A 128.5(12) 2_666 . ? C17A C17B H17A 41.2 . . ? C18 C17B H17A 95.0 . . ? C16B C17B H17A 85.8 . . ? C20B C17B H17A 131.4 2_666 . ? C16A C17B H17A 68.9 . . ? C17A C17B H17B 67.3 . . ? C18 C17B H17B 106.2 . . ? C16B C17B H17B 107.2 . . ? C20B C17B H17B 108.1 2_666 . ? C16A C17B H17B 93.0 . . ? H17A C17B H17B 26.3 . . ? C20A C20B C19 61.1(8) . . ? C20A C20B N1B 53.8(11) . . ? C19 C20B N1B 92.3(13) . . ? C20A C20B C17B 164.7(17) . 2_666 ? C19 C20B C17B 129.2(15) . 2_666 ? N1B C20B C17B 111.6(16) . 2_666 ? C20A C20B H20A 36.0 . . ? C19 C20B H20A 83.2 . . ? N1B C20B H20A 76.2 . . ? C17B C20B H20A 144.3 2_666 . ? C20A C20B H20B 76.8 . . ? C19 C20B H20B 107.3 . . ? N1B C20B H20B 107.6 . . ? C17B C20B H20B 106.8 2_666 . ? H20A C20B H20B 40.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 11(100) 2_576 . . . ? C1 C2 C3 O1 -11(3) . . . . ? C1 C2 C3 C4 -129(3) . . . . ? C1 C2 C3 C10 111(3) . . . . ? O1 C3 C4 C5 -138.87(19) . . . . ? C2 C3 C4 C5 -20.1(3) . . . . ? C10 C3 C4 C5 101.0(2) . . . . ? O1 C3 C4 C9 44.8(2) . . . . ? C2 C3 C4 C9 163.56(17) . . . . ? C10 C3 C4 C9 -75.4(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C6 -176.3(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C5 C4 C9 C8 0.3(3) . . . . ? C3 C4 C9 C8 176.76(19) . . . . ? C7 C8 C9 C4 0.0(4) . . . . ? O1 C3 C10 C15 166.88(16) . . . . ? C2 C3 C10 C15 46.9(2) . . . . ? C4 C3 C10 C15 -75.2(2) . . . . ? O1 C3 C10 C11 -16.1(2) . . . . ? C2 C3 C10 C11 -136.12(18) . . . . ? C4 C3 C10 C11 101.79(19) . . . . ? C15 C10 C11 C12 -1.0(3) . . . . ? C3 C10 C11 C12 -178.08(17) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C11 C10 C15 C14 0.6(3) . . . . ? C3 C10 C15 C14 177.65(18) . . . . ? C13 C14 C15 C10 0.4(3) . . . . ? C16B O2 C16A N1A 98.9(19) . . . . ? C16B O2 C16A C17A -80.5(19) . . . . ? C16B O2 C16A N1B 62(2) . . . . ? C16B O2 C16A C17B -46.1(19) . . . . ? N1B N1A C16A C16B 1(2) . . . . ? C20A N1A C16A C16B -61.5(17) . . . . ? N1B N1A C16A O2 -117.2(13) . . . . ? C20A N1A C16A O2 -179.9(3) . . . . ? C16B N1A C16A O2 -118.4(17) . . . . ? N1B N1A C16A C17A 62.3(13) . . . . ? C20A N1A C16A C17A -0.4(5) . . . . ? C16B N1A C16A C17A 61.1(17) . . . . ? C20A N1A C16A N1B -62.7(13) . . . . ? C16B N1A C16A N1B -1(2) . . . . ? N1B N1A C16A C17B 34.9(14) . . . . ? C20A N1A C16A C17B -27.8(7) . . . . ? C16B N1A C16A C17B 33.7(17) . . . . ? C16B C16A C17A C17B -3(2) . . . . ? O2 C16A C17A C17B 105.8(12) . . . . ? N1A C16A C17A C17B -73.6(12) . . . . ? N1B C16A C17A C17B -45.5(13) . . . . ? O2 C16A C17A C16B 108.6(18) . . . . ? N1A C16A C17A C16B -70.8(17) . . . . ? N1B C16A C17A C16B -42.7(18) . . . . ? C17B C16A C17A C16B 3(2) . . . . ? C16B C16A C17A C18 70.2(18) . . . . ? O2 C16A C17A C18 178.8(3) . . . . ? N1A C16A C17A C18 -0.6(5) . . . . ? N1B C16A C17A C18 27.5(8) . . . . ? C17B C16A C17A C18 73.0(12) . . . . ? C16B C17A C18 C17B -69.8(15) . . . . ? C16A C17A C18 C17B -102.9(12) . . . . ? C17B C17A C18 C19 103.7(11) . . . . ? C16B C17A C18 C19 33.9(12) . . . . ? C16A C17A C18 C19 0.7(5) . . . . ? C17B C18 C19 C20A 52.6(11) . . . . ? C17A C18 C19 C20A 0.2(5) . . . . ? C17B C18 C19 C20B -7.6(14) . . . . ? C17A C18 C19 C20B -59.9(10) . . . . ? N1B N1A C20A C20B -3.2(17) . . . . ? C16A N1A C20A C20B 76.1(10) . . . . ? C16B N1A C20A C20B 47.0(14) . . . . ? C16A N1A C20A N1B 79.3(14) . . . . ? C16B N1A C20A N1B 50.2(16) . . . . ? N1B N1A C20A C19 -77.8(14) . . . . ? C16A N1A C20A C19 1.4(5) . . . . ? C16B N1A C20A C19 -27.6(10) . . . . ? C18 C19 C20A C20B -103.9(10) . . . . ? C18 C19 C20A N1B -42.7(11) . . . . ? C20B C19 C20A N1B 61.3(13) . . . . ? C18 C19 C20A N1A -1.3(5) . . . . ? C20B C19 C20A N1A 102.7(10) . . . . ? C16A N1A N1B C20A -125.1(6) . . . . ? C16B N1A N1B C20A -124.4(14) . . . . ? C20A N1A N1B C16B 124.4(14) . . . . ? C16A N1A N1B C16B -0.7(13) . . . . ? C20A N1A N1B C20B 3.3(17) . . . . ? C16A N1A N1B C20B -122(2) . . . . ? C16B N1A N1B C20B -121(3) . . . . ? C20A N1A N1B C16A 125.1(6) . . . . ? C16B N1A N1B C16A 0.7(13) . . . . ? C20B C20A N1B N1A 176.9(16) . . . . ? C19 C20A N1B N1A 119.5(10) . . . . ? C20B C20A N1B C16B 108(2) . . . . ? N1A C20A N1B C16B -68.9(19) . . . . ? C19 C20A N1B C16B 51(2) . . . . ? N1A C20A N1B C20B -176.9(16) . . . . ? C19 C20A N1B C20B -57.4(10) . . . . ? C20B C20A N1B C16A 134.5(16) . . . . ? N1A C20A N1B C16A -42.4(8) . . . . ? C19 C20A N1B C16A 77.2(12) . . . . ? C16B C16A N1B N1A -179(3) . . . . ? O2 C16A N1B N1A 83.9(13) . . . . ? C17A C16A N1B N1A -126.2(11) . . . . ? C17B C16A N1B N1A -145.8(13) . . . . ? C16B C16A N1B C20A -123(3) . . . . ? O2 C16A N1B C20A 139.6(9) . . . . ? N1A C16A N1B C20A 55.7(12) . . . . ? C17A C16A N1B C20A -70.5(13) . . . . ? C17B C16A N1B C20A -90.1(14) . . . . ? O2 C16A N1B C16B -98(2) . . . . ? N1A C16A N1B C16B 179(3) . . . . ? C17A C16A N1B C16B 52(2) . . . . ? C17B C16A N1B C16B 33(2) . . . . ? C16B C16A N1B C20B -67(3) . . . . ? O2 C16A N1B C20B -164.9(17) . . . . ? N1A C16A N1B C20B 111(3) . . . . ? C17A C16A N1B C20B -15(2) . . . . ? C17B C16A N1B C20B -35(2) . . . . ? O2 C16A C16B C17A -119.2(9) . . . . ? N1A C16A C16B C17A 121.0(8) . . . . ? N1B C16A C16B C17A 121.8(19) . . . . ? C17B C16A C16B C17A -2.0(15) . . . . ? O2 C16A C16B N1B 119.1(14) . . . . ? N1A C16A C16B N1B -0.8(15) . . . . ? C17A C16A C16B N1B -121.8(19) . . . . ? C17B C16A C16B N1B -124(3) . . . . ? O2 C16A C16B N1A 119.8(9) . . . . ? C17A C16A C16B N1A -121.0(8) . . . . ? N1B C16A C16B N1A 0.8(15) . . . . ? C17B C16A C16B N1A -123(2) . . . . ? O2 C16A C16B C17B -117.1(19) . . . . ? N1A C16A C16B C17B 123(2) . . . . ? C17A C16A C16B C17B 2.0(15) . . . . ? N1B C16A C16B C17B 124(3) . . . . ? N1A C16A C16B O2 -119.8(9) . . . . ? C17A C16A C16B O2 119.2(9) . . . . ? N1B C16A C16B O2 -119.1(14) . . . . ? C17B C16A C16B O2 117.1(19) . . . . ? C17B C17A C16B C16A 177.4(19) . . . . ? C18 C17A C16B C16A -123.5(14) . . . . ? C17B C17A C16B N1B -87(2) . . . . ? C18 C17A C16B N1B -28(2) . . . . ? C16A C17A C16B N1B 95(3) . . . . ? C17B C17A C16B N1A -126.7(19) . . . . ? C18 C17A C16B N1A -67.6(17) . . . . ? C16A C17A C16B N1A 56.0(15) . . . . ? C18 C17A C16B C17B 59.1(11) . . . . ? C16A C17A C16B C17B -177.4(19) . . . . ? C17B C17A C16B O2 144.1(14) . . . . ? C18 C17A C16B O2 -156.8(7) . . . . ? C16A C17A C16B O2 -33.3(10) . . . . ? N1A N1B C16B C16A 1(2) . . . . ? C20A N1B C16B C16A 68(3) . . . . ? C20B N1B C16B C16A 131(2) . . . . ? N1A N1B C16B C17A -82(2) . . . . ? C20A N1B C16B C17A -15(3) . . . . ? C20B N1B C16B C17A 48(3) . . . . ? C16A N1B C16B C17A -83(3) . . . . ? C20A N1B C16B N1A 66.6(17) . . . . ? C20B N1B C16B N1A 130(2) . . . . ? C16A N1B C16B N1A -1(2) . . . . ? N1A N1B C16B C17B -128.3(18) . . . . ? C20A N1B C16B C17B -62(3) . . . . ? C20B N1B C16B C17B 2(3) . . . . ? C16A N1B C16B C17B -129(3) . . . . ? N1A N1B C16B O2 38.4(19) . . . . ? C20A N1B C16B O2 105(2) . . . . ? C20B N1B C16B O2 168.4(15) . . . . ? C16A N1B C16B O2 37.2(13) . . . . ? N1B N1A C16B C16A -179(2) . . . . ? C20A N1A C16B C16A 131.0(13) . . . . ? N1B N1A C16B C17A 117(2) . . . . ? C20A N1A C16B C17A 66.2(17) . . . . ? C16A N1A C16B C17A -64.7(17) . . . . ? C20A N1A C16B N1B -50.3(15) . . . . ? C16A N1A C16B N1B 179(2) . . . . ? N1B N1A C16B C17B 72(3) . . . . ? C20A N1A C16B C17B 22(2) . . . . ? C16A N1A C16B C17B -109(3) . . . . ? N1B N1A C16B O2 -146.0(18) . . . . ? C20A N1A C16B O2 163.7(5) . . . . ? C16A N1A C16B O2 32.7(10) . . . . ? C16A O2 C16B C17A 59.9(16) . . . . ? C16A O2 C16B N1B -73(2) . . . . ? C16A O2 C16B N1A -51.4(14) . . . . ? C16A O2 C16B C17B 91(3) . . . . ? C16B C17A C17B C18 113.2(11) . . . . ? C16A C17A C17B C18 114.8(6) . . . . ? C18 C17A C17B C16B -113.2(11) . . . . ? C16A C17A C17B C16B 1.6(12) . . . . ? C16B C17A C17B C20B -51(6) . . . 2_666 ? C18 C17A C17B C20B -165(6) . . . 2_666 ? C16A C17A C17B C20B -50(6) . . . 2_666 ? C16B C17A C17B C16A -1.6(12) . . . . ? C18 C17A C17B C16A -114.8(6) . . . . ? C19 C18 C17B C17A -104.1(9) . . . . ? C19 C18 C17B C16B -51.7(16) . . . . ? C17A C18 C17B C16B 52.4(12) . . . . ? C19 C18 C17B C20B 70.4(18) . . . 2_666 ? C17A C18 C17B C20B 174(2) . . . 2_666 ? C19 C18 C17B C16A -69.4(10) . . . . ? C17A C18 C17B C16A 34.7(5) . . . . ? C16A C16B C17B C17A -3(2) . . . . ? N1B C16B C17B C17A 115(2) . . . . ? N1A C16B C17B C17A 77(2) . . . . ? O2 C16B C17B C17A -49.3(19) . . . . ? C16A C16B C17B C18 -65(3) . . . . ? C17A C16B C17B C18 -61.6(11) . . . . ? N1B C16B C17B C18 53(2) . . . . ? N1A C16B C17B C18 16(3) . . . . ? O2 C16B C17B C18 -110.9(19) . . . . ? C16A C16B C17B C20B 163(2) . . . 2_666 ? C17A C16B C17B C20B 165.6(19) . . . 2_666 ? N1B C16B C17B C20B -79(2) . . . 2_666 ? N1A C16B C17B C20B -117(2) . . . 2_666 ? O2 C16B C17B C20B 116(2) . . . 2_666 ? C17A C16B C17B C16A 3(2) . . . . ? N1B C16B C17B C16A 118(3) . . . . ? N1A C16B C17B C16A 80(3) . . . . ? O2 C16B C17B C16A -46.3(19) . . . . ? C16B C16A C17B C17A 176(3) . . . . ? O2 C16A C17B C17A -95.1(11) . . . . ? N1A C16A C17B C17A 116.2(10) . . . . ? N1B C16A C17B C17A 134.0(13) . . . . ? C16B C16A C17B C18 117(3) . . . . ? O2 C16A C17B C18 -154.3(6) . . . . ? N1A C16A C17B C18 57.0(9) . . . . ? C17A C16A C17B C18 -59.2(10) . . . . ? N1B C16A C17B C18 74.8(11) . . . . ? O2 C16A C17B C16B 89(3) . . . . ? N1A C16A C17B C16B -60(3) . . . . ? C17A C16A C17B C16B -176(3) . . . . ? N1B C16A C17B C16B -42(3) . . . . ? C16B C16A C17B C20B -21(3) . . . 2_666 ? O2 C16A C17B C20B 67.9(17) . . . 2_666 ? N1A C16A C17B C20B -80.8(16) . . . 2_666 ? C17A C16A C17B C20B 163(2) . . . 2_666 ? N1B C16A C17B C20B -62.9(16) . . . 2_666 ? N1B C20A C20B C19 -117.6(11) . . . . ? N1A C20A C20B C19 -115.4(5) . . . . ? N1A C20A C20B N1B 2.2(11) . . . . ? C19 C20A C20B N1B 117.6(11) . . . . ? N1B C20A C20B C17B 18(6) . . . 2_666 ? N1A C20A C20B C17B 21(7) . . . 2_666 ? C19 C20A C20B C17B 136(6) . . . 2_666 ? C18 C19 C20B C20A 105.6(7) . . . . ? C20A C19 C20B N1B -45.7(10) . . . . ? C18 C19 C20B N1B 59.9(13) . . . . ? C20A C19 C20B C17B -166(2) . . . 2_666 ? C18 C19 C20B C17B -61(2) . . . 2_666 ? N1A N1B C20B C20A -4(2) . . . . ? C16B N1B C20B C20A -106(2) . . . . ? C16A N1B C20B C20A -77(2) . . . . ? N1A N1B C20B C19 47(3) . . . . ? C20A N1B C20B C19 50.9(8) . . . . ? C16B N1B C20B C19 -55(2) . . . . ? C16A N1B C20B C19 -26(2) . . . . ? N1A N1B C20B C17B -179(2) . . . 2_666 ? C20A N1B C20B C17B -174.9(17) . . . 2_666 ? C16B N1B C20B C17B 79(2) . . . 2_666 ? C16A N1B C20B C17B 108(2) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.262 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.035 data_I-c_7hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7700(10) _cell_length_b 8.0550(10) _cell_length_c 13.474(2) _cell_angle_alpha 84.99(2) _cell_angle_beta 75.45(2) _cell_angle_gamma 81.50(2) _cell_volume 806.18(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7936 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7936 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2836 _reflns_number_gt 1952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.3286P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2836 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35452(17) 1.08028(17) 0.23474(10) 0.0454(4) Uani 1 1 d . . . H1 H 0.4218 1.0305 0.2689 0.054 Uiso 1 1 calc R . . C1 C 0.0389(3) 0.9978(3) 0.44795(14) 0.0452(5) Uani 1 1 d . . . C2 C 0.1057(3) 0.9939(3) 0.35821(14) 0.0426(5) Uani 1 1 d . . . C3 C 0.2026(2) 0.9943(2) 0.24794(13) 0.0355(4) Uani 1 1 d . . . C4 C 0.0846(2) 1.0882(2) 0.17984(13) 0.0356(4) Uani 1 1 d . . . C5 C -0.0993(3) 1.1157(3) 0.21256(17) 0.0540(6) Uani 1 1 d . . . H5 H -0.1552 1.0825 0.2793 0.065 Uiso 1 1 calc R . . C6 C -0.2018(3) 1.1926(3) 0.1465(2) 0.0716(7) Uani 1 1 d . . . H6 H -0.3261 1.2098 0.1693 0.086 Uiso 1 1 calc R . . C7 C -0.1226(3) 1.2430(3) 0.04868(19) 0.0650(7) Uani 1 1 d . . . H7 H -0.1919 1.2957 0.0050 0.078 Uiso 1 1 calc R . . C8 C 0.0605(3) 1.2152(3) 0.01538(17) 0.0600(6) Uani 1 1 d . . . H8 H 0.1157 1.2488 -0.0514 0.072 Uiso 1 1 calc R . . C9 C 0.1638(3) 1.1378(3) 0.08030(15) 0.0482(5) Uani 1 1 d . . . H9 H 0.2879 1.1190 0.0567 0.058 Uiso 1 1 calc R . . C10 C 0.2582(2) 0.8130(2) 0.21463(13) 0.0354(4) Uani 1 1 d . . . C11 C 0.4284(3) 0.7646(3) 0.15465(15) 0.0468(5) Uani 1 1 d . . . H11 H 0.5106 0.8417 0.1361 0.056 Uiso 1 1 calc R . . C12 C 0.4767(3) 0.6024(3) 0.12222(17) 0.0570(6) Uani 1 1 d . . . H12 H 0.5916 0.5708 0.0825 0.068 Uiso 1 1 calc R . . C13 C 0.3572(4) 0.4881(3) 0.14795(17) 0.0581(6) Uani 1 1 d . . . H13 H 0.3910 0.3789 0.1264 0.070 Uiso 1 1 calc R . . C14 C 0.1872(4) 0.5349(3) 0.20576(18) 0.0609(6) Uani 1 1 d . . . H14 H 0.1047 0.4580 0.2224 0.073 Uiso 1 1 calc R . . C15 C 0.1381(3) 0.6970(3) 0.23942(16) 0.0486(5) Uani 1 1 d . . . H15 H 0.0230 0.7277 0.2791 0.058 Uiso 1 1 calc R . . O2 O 0.4634(3) 0.0716(3) 0.62355(15) 0.0983(7) Uani 1 1 d . . . N1A N 0.3803(4) 0.2101(4) 0.48835(19) 0.0668(8) Uani 0.835(5) 1 d P . . H1NA H 0.4202 0.1220 0.4536 0.080 Uiso 0.835(5) 1 d PR . . C16A C 0.3961(4) 0.2028(5) 0.5868(2) 0.0610(9) Uani 0.835(5) 1 d P . . C17A C 0.3325(4) 0.3529(5) 0.6391(3) 0.0737(11) Uani 0.835(5) 1 d P . . H17A H 0.3401 0.3558 0.7067 0.088 Uiso 0.835(5) 1 d PR . . C18 C 0.2601(4) 0.4983(5) 0.5908(3) 0.0914(10) Uani 1 1 d . . . H18A H 0.2190 0.5957 0.6266 0.110 Uiso 0.835(5) 1 d PR . . C19 C 0.2484(4) 0.4962(5) 0.4910(3) 0.0943(10) Uani 1 1 d . . . H19A H 0.1990 0.5907 0.4580 0.113 Uiso 0.835(5) 1 d PR . . C20A C 0.3084(5) 0.3475(5) 0.4415(3) 0.0803(12) Uani 0.835(5) 1 d P . . H20A H 0.3005 0.3428 0.3741 0.096 Uiso 0.835(5) 1 d PR . . N1B N 0.453(2) 0.291(2) 0.4628(13) 0.083(5) Uiso 0.165(5) 1 d P . . H1NB H 0.4720 0.2024 0.4285 0.100 Uiso 0.165(5) 1 d PR . . C16B C 0.454(2) 0.282(2) 0.5645(13) 0.062(5) Uiso 0.165(5) 1 d P . . C17B C 0.415(2) 0.443(2) 0.6146(13) 0.068(5) Uiso 0.165(5) 1 d P . . H17B H 0.3869 0.4201 0.6892 0.082 Uiso 0.165(5) 1 d PR . . C20B C 0.412(2) 0.458(2) 0.4145(12) 0.067(5) Uiso 0.165(5) 1 d P . . H20B H 0.3807 0.4410 0.3505 0.081 Uiso 0.165(5) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.081 Uiso 0.16 1 d P . . H19B H 0.1382 0.5198 0.4735 0.081 Uiso 0.16 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0477(8) 0.0484(9) 0.0437(8) -0.0020(6) -0.0155(6) -0.0111(6) C1 0.0519(12) 0.0483(12) 0.0326(10) -0.0057(9) -0.0082(8) 0.0008(9) C2 0.0514(11) 0.0433(12) 0.0307(10) -0.0056(8) -0.0078(8) 0.0002(9) C3 0.0398(10) 0.0390(11) 0.0263(9) -0.0027(8) -0.0061(7) -0.0036(8) C4 0.0456(11) 0.0300(10) 0.0307(9) -0.0051(8) -0.0090(8) -0.0018(8) C5 0.0450(12) 0.0596(14) 0.0491(13) 0.0064(10) -0.0060(9) 0.0049(10) C6 0.0498(14) 0.0808(19) 0.0783(18) 0.0088(14) -0.0198(12) 0.0103(12) C7 0.0736(17) 0.0614(16) 0.0629(16) 0.0062(12) -0.0343(13) 0.0070(12) C8 0.0760(16) 0.0636(16) 0.0397(12) 0.0062(11) -0.0179(11) -0.0054(12) C9 0.0519(12) 0.0551(14) 0.0356(11) 0.0033(9) -0.0107(9) -0.0041(10) C10 0.0447(10) 0.0357(10) 0.0251(9) -0.0004(8) -0.0106(7) -0.0002(8) C11 0.0454(11) 0.0518(13) 0.0408(11) -0.0080(9) -0.0069(9) -0.0017(9) C12 0.0592(14) 0.0576(15) 0.0499(13) -0.0168(11) -0.0136(10) 0.0154(11) C13 0.0853(17) 0.0393(13) 0.0494(13) -0.0076(10) -0.0248(12) 0.0103(12) C14 0.0833(17) 0.0400(13) 0.0604(15) 0.0015(11) -0.0177(13) -0.0132(12) C15 0.0556(12) 0.0418(12) 0.0437(11) -0.0009(9) -0.0038(9) -0.0066(10) O2 0.0906(14) 0.145(2) 0.0644(12) -0.0027(13) -0.0389(11) 0.0013(14) N1A 0.0708(17) 0.077(2) 0.0597(16) 0.0067(14) -0.0333(13) -0.0081(15) C16A 0.0487(16) 0.080(2) 0.0607(19) 0.0144(18) -0.0267(14) -0.0164(17) C17A 0.066(2) 0.097(3) 0.064(2) -0.0141(19) -0.0205(16) -0.0144(19) C18 0.0664(18) 0.109(3) 0.097(2) -0.015(2) -0.0117(16) -0.0129(17) C19 0.082(2) 0.110(3) 0.092(2) 0.006(2) -0.0326(18) -0.0048(19) C20A 0.087(3) 0.090(3) 0.071(2) 0.015(2) -0.0392(19) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.421(2) . ? O1 H1 0.8200 . ? C1 C2 1.191(3) . ? C1 C1 1.382(4) 2_576 ? C2 C3 1.487(2) . ? C3 C4 1.533(2) . ? C3 C10 1.534(3) . ? C4 C5 1.376(3) . ? C4 C9 1.379(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.362(3) . ? C6 H6 0.9300 . ? C7 C8 1.370(3) . ? C7 H7 0.9300 . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.379(3) . ? C10 C11 1.385(3) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 H12 0.9300 . ? C13 C14 1.372(3) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.230(4) . ? O2 C16B 1.81(2) . ? N1A N1B 0.913(19) . ? N1A C20A 1.344(4) . ? N1A C16A 1.358(4) . ? N1A C16B 1.487(17) . ? N1A H1NA 0.8599 . ? N1A H1NB 0.9327 . ? C16A C16B 0.83(2) . ? C16A C17A 1.414(5) . ? C16A N1B 1.734(18) . ? C16A C17B 2.036(19) . ? C17A C17B 1.020(19) . ? C17A C16B 1.299(17) . ? C17A C18 1.403(5) . ? C17A H17A 0.9303 . ? C17A H17B 1.0959 . ? C18 C17B 1.330(17) . ? C18 C19 1.372(4) . ? C18 H18A 0.9299 . ? C18 H18B 0.9302 . ? C19 C20A 1.383(5) . ? C19 C20B 1.433(16) . ? C19 H19A 0.9305 . ? C19 H19B 0.9329 . ? C20A N1B 1.238(17) . ? C20A C20B 1.260(16) . ? C20A H20A 0.9303 . ? C20A H1NB 1.5803 . ? C20A H20B 1.4161 . ? N1B C16B 1.37(2) . ? N1B C20B 1.47(2) . ? N1B H1NA 1.4437 . ? N1B H1NB 0.8599 . ? C16B C17B 1.47(2) . ? C17B C20B 1.61(3) 2_666 ? C17B H17A 1.4076 . ? C17B H17B 0.9801 . ? C20B C17B 1.61(3) 2_666 ? C20B H20A 1.5748 . ? C20B H20B 0.9803 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.9(3) . 2_576 ? C1 C2 C3 175.1(2) . . ? O1 C3 C2 108.45(14) . . ? O1 C3 C4 107.51(15) . . ? C2 C3 C4 111.33(15) . . ? O1 C3 C10 111.23(14) . . ? C2 C3 C10 109.69(15) . . ? C4 C3 C10 108.63(14) . . ? C5 C4 C9 118.57(18) . . ? C5 C4 C3 122.15(17) . . ? C9 C4 C3 119.16(16) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.2(2) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.6(2) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C15 C10 C11 118.59(18) . . ? C15 C10 C3 120.99(17) . . ? C11 C10 C3 120.35(17) . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.7(2) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C16A O2 C16B 22.8(5) . . ? N1B N1A C20A 63.2(11) . . ? N1B N1A C16A 97.7(11) . . ? C20A N1A C16A 124.0(3) . . ? N1B N1A C16B 64.4(13) . . ? C20A N1A C16B 102.9(8) . . ? C16A N1A C16B 33.3(7) . . ? N1B N1A H1NA 109.0 . . ? C20A N1A H1NA 118.1 . . ? C16A N1A H1NA 117.9 . . ? C16B N1A H1NA 130.0 . . ? N1B N1A H1NB 55.5 . . ? C20A N1A H1NB 85.9 . . ? C16A N1A H1NB 127.8 . . ? C16B N1A H1NB 105.9 . . ? H1NA N1A H1NB 54.0 . . ? C16B C16A O2 122.0(12) . . ? C16B C16A N1A 81.9(12) . . ? O2 C16A N1A 119.6(3) . . ? C16B C16A C17A 64.8(12) . . ? O2 C16A C17A 125.0(3) . . ? N1A C16A C17A 115.4(3) . . ? C16B C16A N1B 50.6(13) . . ? O2 C16A N1B 129.1(6) . . ? N1A C16A N1B 31.5(6) . . ? C17A C16A N1B 98.3(6) . . ? C16B C16A C17B 37.5(13) . . ? O2 C16A C17B 127.9(5) . . ? N1A C16A C17B 105.1(5) . . ? C17A C16A C17B 27.6(5) . . ? N1B C16A C17B 78.9(8) . . ? C17B C17A C16B 77.7(13) . . ? C17B C17A C18 64.3(10) . . ? C16B C17A C18 103.2(9) . . ? C17B C17A C16A 112.6(10) . . ? C16B C17A C16A 35.1(9) . . ? C18 C17A C16A 121.4(3) . . ? C17B C17A H17A 92.3 . . ? C16B C17A H17A 126.7 . . ? C18 C17A H17A 119.2 . . ? C16A C17A H17A 119.4 . . ? C17B C17A H17B 55.0 . . ? C16B C17A H17B 113.9 . . ? C18 C17A H17B 95.2 . . ? C16A C17A H17B 132.8 . . ? H17A C17A H17B 37.4 . . ? C17B C18 C19 119.3(8) . . ? C17B C18 C17A 43.7(8) . . ? C19 C18 C17A 119.9(3) . . ? C17B C18 H18A 103.8 . . ? C19 C18 H18A 120.0 . . ? C17A C18 H18A 120.1 . . ? C17B C18 H18B 119.8 . . ? C19 C18 H18B 120.8 . . ? C17A C18 H18B 101.9 . . ? H18A C18 H18B 43.6 . . ? C20A C19 C18 117.9(3) . . ? C20A C19 C20B 53.1(7) . . ? C18 C19 C20B 117.5(7) . . ? C20A C19 H19A 120.9 . . ? C18 C19 H19A 121.2 . . ? C20B C19 H19A 98.7 . . ? C20A C19 H19B 97.9 . . ? C18 C19 H19B 121.2 . . ? C20B C19 H19B 121.3 . . ? H19A C19 H19B 49.2 . . ? N1B C20A C20B 72.1(12) . . ? N1B C20A N1A 41.2(9) . . ? C20B C20A N1A 113.1(8) . . ? N1B C20A C19 106.5(9) . . ? C20B C20A C19 65.4(8) . . ? N1A C20A C19 121.4(3) . . ? N1B C20A H20A 117.9 . . ? C20B C20A H20A 90.7 . . ? N1A C20A H20A 119.2 . . ? C19 C20A H20A 119.4 . . ? N1B C20A H1NB 32.8 . . ? C20B C20A H1NB 91.6 . . ? N1A C20A H1NB 36.1 . . ? C19 C20A H1NB 139.3 . . ? H20A C20A H1NB 92.5 . . ? N1B C20A H20B 97.0 . . ? C20B C20A H20B 42.5 . . ? N1A C20A H20B 130.9 . . ? C19 C20A H20B 89.3 . . ? H20A C20A H20B 48.3 . . ? H1NB C20A H20B 95.3 . . ? N1A N1B C20A 75.7(13) . . ? N1A N1B C16B 78.5(14) . . ? C20A N1B C16B 116.4(15) . . ? N1A N1B C20B 130.2(18) . . ? C20A N1B C20B 54.7(9) . . ? C16B N1B C20B 117.6(16) . . ? N1A N1B C16A 50.9(9) . . ? C20A N1B C16A 105.5(12) . . ? C16B N1B C16A 27.8(9) . . ? C20B N1B C16A 134.4(13) . . ? N1A N1B H1NA 34.3 . . ? C20A N1B H1NA 90.3 . . ? C16B N1B H1NA 99.3 . . ? C20B N1B H1NA 136.9 . . ? C16A N1B H1NA 73.6 . . ? N1A N1B H1NB 63.4 . . ? C20A N1B H1NB 96.1 . . ? C16B N1B H1NB 121.4 . . ? C20B N1B H1NB 120.9 . . ? C16A N1B H1NB 100.0 . . ? H1NA N1B H1NB 29.7 . . ? C16A C16B C17A 80.1(15) . . ? C16A C16B N1B 101.6(17) . . ? C17A C16B N1B 127.3(15) . . ? C16A C16B N1A 64.7(12) . . ? C17A C16B N1A 114.3(13) . . ? N1B C16B N1A 37.0(9) . . ? C16A C16B C17B 122.5(19) . . ? C17A C16B C17B 42.7(9) . . ? N1B C16B C17B 116.0(16) . . ? N1A C16B C17B 134.3(14) . . ? C16A C16B O2 35.2(9) . . ? C17A C16B O2 96.7(12) . . ? N1B C16B O2 114.7(13) . . ? N1A C16B O2 84.9(10) . . ? C17B C16B O2 128.4(13) . . ? C17A C17B C18 71.9(11) . . ? C17A C17B C16B 59.7(12) . . ? C18 C17B C16B 98.2(13) . . ? C17A C17B C20B 163.1(17) . 2_666 ? C18 C17B C20B 124.8(15) . 2_666 ? C16B C17B C20B 111.0(14) . 2_666 ? C17A C17B C16A 39.9(7) . . ? C18 C17B C16A 91.3(10) . . ? C16B C17B C16A 20.0(8) . . ? C20B C17B C16A 129.1(11) 2_666 . ? C17A C17B H17A 41.3 . . ? C18 C17B H17A 95.5 . . ? C16B C17B H17A 88.0 . . ? C20B C17B H17A 130.0 2_666 . ? C16A C17B H17A 69.9 . . ? C17A C17B H17B 66.4 . . ? C18 C17B H17B 106.1 . . ? C16B C17B H17B 108.6 . . ? C20B C17B H17B 107.2 2_666 . ? C16A C17B H17B 92.9 . . ? H17A C17B H17B 25.3 . . ? C20A C20B C19 61.4(7) . . ? C20A C20B N1B 53.3(10) . . ? C19 C20B N1B 92.8(11) . . ? C20A C20B C17B 164.1(15) . 2_666 ? C19 C20B C17B 128.2(13) . 2_666 ? N1B C20B C17B 111.2(14) . 2_666 ? C20A C20B H20A 36.2 . . ? C19 C20B H20A 83.8 . . ? N1B C20B H20A 75.4 . . ? C17B C20B H20A 145.3 2_666 . ? C20A C20B H20B 77.3 . . ? C19 C20B H20B 107.8 . . ? N1B C20B H20B 107.0 . . ? C17B C20B H20B 107.6 2_666 . ? H20A C20B H20B 41.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 163(100) 2_576 . . . ? C1 C2 C3 O1 -11(3) . . . . ? C1 C2 C3 C4 -130(2) . . . . ? C1 C2 C3 C10 110(2) . . . . ? O1 C3 C4 C5 -138.87(19) . . . . ? C2 C3 C4 C5 -20.2(3) . . . . ? C10 C3 C4 C5 100.7(2) . . . . ? O1 C3 C4 C9 45.2(2) . . . . ? C2 C3 C4 C9 163.88(17) . . . . ? C10 C3 C4 C9 -75.2(2) . . . . ? C9 C4 C5 C6 -0.3(3) . . . . ? C3 C4 C5 C6 -176.3(2) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C5 C4 C9 C8 0.8(3) . . . . ? C3 C4 C9 C8 176.81(19) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? O1 C3 C10 C15 166.96(16) . . . . ? C2 C3 C10 C15 47.0(2) . . . . ? C4 C3 C10 C15 -74.9(2) . . . . ? O1 C3 C10 C11 -16.1(2) . . . . ? C2 C3 C10 C11 -136.06(18) . . . . ? C4 C3 C10 C11 102.05(19) . . . . ? C15 C10 C11 C12 -1.1(3) . . . . ? C3 C10 C11 C12 -178.16(17) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C11 C10 C15 C14 0.5(3) . . . . ? C3 C10 C15 C14 177.54(18) . . . . ? C13 C14 C15 C10 0.6(3) . . . . ? C16B O2 C16A N1A 99.5(15) . . . . ? C16B O2 C16A C17A -80.0(15) . . . . ? C16B O2 C16A N1B 62.9(16) . . . . ? C16B O2 C16A C17B -45.7(16) . . . . ? N1B N1A C16A C16B 4.9(17) . . . . ? C20A N1A C16A C16B -57.8(13) . . . . ? N1B N1A C16A O2 -117.5(12) . . . . ? C20A N1A C16A O2 179.9(3) . . . . ? C16B N1A C16A O2 -122.4(13) . . . . ? N1B N1A C16A C17A 62.1(12) . . . . ? C20A N1A C16A C17A -0.6(5) . . . . ? C16B N1A C16A C17A 57.1(12) . . . . ? C20A N1A C16A N1B -62.7(11) . . . . ? C16B N1A C16A N1B -4.9(17) . . . . ? N1B N1A C16A C17B 34.8(12) . . . . ? C20A N1A C16A C17B -27.9(6) . . . . ? C16B N1A C16A C17B 29.8(13) . . . . ? C16B C16A C17A C17B -6.6(17) . . . . ? O2 C16A C17A C17B 106.2(11) . . . . ? N1A C16A C17A C17B -73.3(11) . . . . ? N1B C16A C17A C17B -45.6(12) . . . . ? O2 C16A C17A C16B 112.7(14) . . . . ? N1A C16A C17A C16B -66.8(13) . . . . ? N1B C16A C17A C16B -39.0(14) . . . . ? C17B C16A C17A C16B 6.6(17) . . . . ? C16B C16A C17A C18 66.2(13) . . . . ? O2 C16A C17A C18 178.9(3) . . . . ? N1A C16A C17A C18 -0.6(5) . . . . ? N1B C16A C17A C18 27.2(7) . . . . ? C17B C16A C17A C18 72.8(11) . . . . ? C16B C17A C18 C17B -69.1(14) . . . . ? C16A C17A C18 C17B -101.9(11) . . . . ? C17B C17A C18 C19 102.4(11) . . . . ? C16B C17A C18 C19 33.3(9) . . . . ? C16A C17A C18 C19 0.6(5) . . . . ? C17B C18 C19 C20A 51.2(11) . . . . ? C17A C18 C19 C20A 0.5(5) . . . . ? C17B C18 C19 C20B -9.5(13) . . . . ? C17A C18 C19 C20B -60.2(9) . . . . ? C16A N1A C20A N1B 80.7(12) . . . . ? C16B N1A C20A N1B 52.3(14) . . . . ? N1B N1A C20A C20B -4.6(15) . . . . ? C16A N1A C20A C20B 76.2(9) . . . . ? C16B N1A C20A C20B 47.7(11) . . . . ? N1B N1A C20A C19 -79.0(12) . . . . ? C16A N1A C20A C19 1.8(5) . . . . ? C16B N1A C20A C19 -26.7(8) . . . . ? C18 C19 C20A N1B -44.0(10) . . . . ? C20B C19 C20A N1B 60.8(12) . . . . ? C18 C19 C20A C20B -104.8(9) . . . . ? C18 C19 C20A N1A -1.6(5) . . . . ? C20B C19 C20A N1A 103.1(9) . . . . ? C16A N1A N1B C20A -124.3(5) . . . . ? C16B N1A N1B C20A -121.3(12) . . . . ? C20A N1A N1B C16B 121.3(12) . . . . ? C16A N1A N1B C16B -3.0(10) . . . . ? C20A N1A N1B C20B 4.7(15) . . . . ? C16A N1A N1B C20B -119.6(19) . . . . ? C16B N1A N1B C20B -117(2) . . . . ? C20A N1A N1B C16A 124.3(5) . . . . ? C16B N1A N1B C16A 3.0(10) . . . . ? C20B C20A N1B N1A 175.6(14) . . . . ? C19 C20A N1B N1A 119.1(9) . . . . ? C20B C20A N1B C16B 106.4(19) . . . . ? N1A C20A N1B C16B -69.2(16) . . . . ? C19 C20A N1B C16B 49.9(18) . . . . ? N1A C20A N1B C20B -175.6(14) . . . . ? C19 C20A N1B C20B -56.5(9) . . . . ? C20B C20A N1B C16A 133.9(14) . . . . ? N1A C20A N1B C16A -41.7(7) . . . . ? C19 C20A N1B C16A 77.4(11) . . . . ? C16B C16A N1B N1A -174(2) . . . . ? O2 C16A N1B N1A 83.8(12) . . . . ? C17A C16A N1B N1A -126.2(10) . . . . ? C17B C16A N1B N1A -145.9(12) . . . . ? C16B C16A N1B C20A -118(2) . . . . ? O2 C16A N1B C20A 139.9(8) . . . . ? N1A C16A N1B C20A 56.2(11) . . . . ? C17A C16A N1B C20A -70.1(12) . . . . ? C17B C16A N1B C20A -89.7(12) . . . . ? O2 C16A N1B C16B -102.6(17) . . . . ? N1A C16A N1B C16B 174(2) . . . . ? C17A C16A N1B C16B 47.5(16) . . . . ? C17B C16A N1B C16B 27.8(17) . . . . ? C16B C16A N1B C20B -62(2) . . . . ? O2 C16A N1B C20B -164.7(15) . . . . ? N1A C16A N1B C20B 112(2) . . . . ? C17A C16A N1B C20B -15(2) . . . . ? C17B C16A N1B C20B -34.4(19) . . . . ? O2 C16A C16B C17A -117.0(8) . . . . ? N1A C16A C16B C17A 123.0(7) . . . . ? N1B C16A C16B C17A 126.4(16) . . . . ? C17B C16A C16B C17A -5.0(13) . . . . ? O2 C16A C16B N1B 116.7(12) . . . . ? N1A C16A C16B N1B -3.3(12) . . . . ? C17A C16A C16B N1B -126.4(16) . . . . ? C17B C16A C16B N1B -131(3) . . . . ? O2 C16A C16B N1A 120.0(8) . . . . ? C17A C16A C16B N1A -123.0(7) . . . . ? N1B C16A C16B N1A 3.3(12) . . . . ? C17B C16A C16B N1A -128.0(18) . . . . ? O2 C16A C16B C17B -112.0(17) . . . . ? N1A C16A C16B C17B 128.0(18) . . . . ? C17A C16A C16B C17B 5.0(13) . . . . ? N1B C16A C16B C17B 131(3) . . . . ? N1A C16A C16B O2 -120.0(8) . . . . ? C17A C16A C16B O2 117.0(8) . . . . ? N1B C16A C16B O2 -116.7(12) . . . . ? C17B C16A C16B O2 112.0(17) . . . . ? C17B C17A C16B C16A 173.8(16) . . . . ? C18 C17A C16B C16A -126.6(10) . . . . ? C17B C17A C16B N1B -89(2) . . . . ? C18 C17A C16B N1B -30(2) . . . . ? C16A C17A C16B N1B 97(2) . . . . ? C17B C17A C16B N1A -129.9(17) . . . . ? C18 C17A C16B N1A -70.4(14) . . . . ? C16A C17A C16B N1A 56.3(12) . . . . ? C18 C17A C16B C17B 59.6(10) . . . . ? C16A C17A C16B C17B -173.8(16) . . . . ? C17B C17A C16B O2 142.7(12) . . . . ? C18 C17A C16B O2 -157.8(5) . . . . ? C16A C17A C16B O2 -31.1(7) . . . . ? N1A N1B C16B C16A 5.0(17) . . . . ? C20A N1B C16B C16A 73(2) . . . . ? C20B N1B C16B C16A 134.5(18) . . . . ? N1A N1B C16B C17A -81(2) . . . . ? C20A N1B C16B C17A -14(3) . . . . ? C20B N1B C16B C17A 48(3) . . . . ? C16A N1B C16B C17A -86(2) . . . . ? C20A N1B C16B N1A 67.5(15) . . . . ? C20B N1B C16B N1A 130(2) . . . . ? C16A N1B C16B N1A -5.0(17) . . . . ? N1A N1B C16B C17B -130.2(16) . . . . ? C20A N1B C16B C17B -63(2) . . . . ? C20B N1B C16B C17B -1(2) . . . . ? C16A N1B C16B C17B -135(2) . . . . ? N1A N1B C16B O2 39.5(15) . . . . ? C20A N1B C16B O2 107.1(17) . . . . ? C20B N1B C16B O2 169.1(13) . . . . ? C16A N1B C16B O2 34.5(9) . . . . ? N1B N1A C16B C16A -174.6(19) . . . . ? C20A N1A C16B C16A 134.0(10) . . . . ? N1B N1A C16B C17A 120(2) . . . . ? C20A N1A C16B C17A 69.0(14) . . . . ? C16A N1A C16B C17A -65.0(14) . . . . ? C20A N1A C16B N1B -51.4(13) . . . . ? C16A N1A C16B N1B 174.6(19) . . . . ? N1B N1A C16B C17B 74(2) . . . . ? C20A N1A C16B C17B 22(2) . . . . ? C16A N1A C16B C17B -112(3) . . . . ? N1B N1A C16B O2 -144.5(15) . . . . ? C20A N1A C16B O2 164.1(4) . . . . ? C16A N1A C16B O2 30.1(7) . . . . ? C16A O2 C16B C17A 62.1(13) . . . . ? C16A O2 C16B N1B -74.5(17) . . . . ? C16A O2 C16B N1A -51.8(11) . . . . ? C16A O2 C16B C17B 94(2) . . . . ? C16B C17A C17B C18 111.4(9) . . . . ? C16A C17A C17B C18 115.2(6) . . . . ? C18 C17A C17B C16B -111.4(9) . . . . ? C16A C17A C17B C16B 3.9(10) . . . . ? C16B C17A C17B C20B -60(6) . . . 2_666 ? C18 C17A C17B C20B -172(6) . . . 2_666 ? C16A C17A C17B C20B -57(6) . . . 2_666 ? C16B C17A C17B C16A -3.9(10) . . . . ? C18 C17A C17B C16A -115.2(6) . . . . ? C19 C18 C17B C17A -103.9(9) . . . . ? C19 C18 C17B C16B -49.6(15) . . . . ? C17A C18 C17B C16B 54.3(11) . . . . ? C19 C18 C17B C20B 73.2(16) . . . 2_666 ? C17A C18 C17B C20B 177(2) . . . 2_666 ? C19 C18 C17B C16A -68.4(9) . . . . ? C17A C18 C17B C16A 35.5(5) . . . . ? C16A C16B C17B C17A -7.2(19) . . . . ? N1B C16B C17B C17A 117.8(17) . . . . ? N1A C16B C17B C17A 78(2) . . . . ? O2 C16B C17B C17A -50.2(16) . . . . ? C16A C16B C17B C18 -71(2) . . . . ? C17A C16B C17B C18 -63.5(11) . . . . ? N1B C16B C17B C18 54.4(19) . . . . ? N1A C16B C17B C18 14(2) . . . . ? O2 C16B C17B C18 -113.7(15) . . . . ? C16A C16B C17B C20B 157.0(18) . . . 2_666 ? C17A C16B C17B C20B 164.3(18) . . . 2_666 ? N1B C16B C17B C20B -77.9(19) . . . 2_666 ? N1A C16B C17B C20B -118(2) . . . 2_666 ? O2 C16B C17B C20B 114.0(16) . . . 2_666 ? C17A C16B C17B C16A 7.2(19) . . . . ? N1B C16B C17B C16A 125(3) . . . . ? N1A C16B C17B C16A 85(3) . . . . ? O2 C16B C17B C16A -43.0(14) . . . . ? C16B C16A C17B C17A 170(2) . . . . ? O2 C16A C17B C17A -94.6(11) . . . . ? N1A C16A C17B C17A 116.3(10) . . . . ? N1B C16A C17B C17A 134.0(12) . . . . ? C16B C16A C17B C18 111(2) . . . . ? O2 C16A C17B C18 -153.9(6) . . . . ? N1A C16A C17B C18 57.0(9) . . . . ? C17A C16A C17B C18 -59.4(10) . . . . ? N1B C16A C17B C18 74.6(10) . . . . ? O2 C16A C17B C16B 95(2) . . . . ? N1A C16A C17B C16B -54(2) . . . . ? C17A C16A C17B C16B -170(2) . . . . ? N1B C16A C17B C16B -36(2) . . . . ? C16B C16A C17B C20B -28(2) . . . 2_666 ? O2 C16A C17B C20B 67.2(16) . . . 2_666 ? N1A C16A C17B C20B -81.9(14) . . . 2_666 ? C17A C16A C17B C20B 162(2) . . . 2_666 ? N1B C16A C17B C20B -64.3(15) . . . 2_666 ? N1B C20A C20B C19 -118.5(10) . . . . ? N1A C20A C20B C19 -115.3(5) . . . . ? N1A C20A C20B N1B 3.2(10) . . . . ? C19 C20A C20B N1B 118.5(10) . . . . ? N1B C20A C20B C17B 13(5) . . . 2_666 ? N1A C20A C20B C17B 16(6) . . . 2_666 ? C19 C20A C20B C17B 131(5) . . . 2_666 ? C18 C19 C20B C20A 105.6(7) . . . . ? C20A C19 C20B N1B -44.8(9) . . . . ? C18 C19 C20B N1B 60.8(12) . . . . ? C20A C19 C20B C17B -164.8(19) . . . 2_666 ? C18 C19 C20B C17B -59.2(17) . . . 2_666 ? N1A N1B C20B C20A -5.6(18) . . . . ? C16B N1B C20B C20A -104.1(17) . . . . ? C16A N1B C20B C20A -76.4(18) . . . . ? N1A N1B C20B C19 45(2) . . . . ? C20A N1B C20B C19 50.6(8) . . . . ? C16B N1B C20B C19 -53.5(18) . . . . ? C16A N1B C20B C19 -26(2) . . . . ? N1A N1B C20B C17B 178.1(19) . . . 2_666 ? C20A N1B C20B C17B -176.3(15) . . . 2_666 ? C16B N1B C20B C17B 79.6(19) . . . 2_666 ? C16A N1B C20B C17B 107.4(19) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.304 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.035 data_I-c_17hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7440(10) _cell_length_b 7.992(2) _cell_length_c 13.534(3) _cell_angle_alpha 85.40(2) _cell_angle_beta 75.41(2) _cell_angle_gamma 82.78(2) _cell_volume 803.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8467 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8467 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2822 _reflns_number_gt 1617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1347P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2822 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2161 _refine_ls_wR_factor_gt 0.1838 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3515(2) 1.0876(3) 0.23463(14) 0.0605(6) Uani 1 1 d . . . H1 H 0.4192 1.0392 0.2682 0.073 Uiso 1 1 calc R . . C1 C 0.0377(4) 0.9985(4) 0.4478(2) 0.0563(8) Uani 1 1 d . . . C2 C 0.1032(4) 0.9949(4) 0.3585(2) 0.0548(7) Uani 1 1 d . . . C3 C 0.1984(3) 0.9978(3) 0.24858(17) 0.0454(7) Uani 1 1 d . . . C4 C 0.0794(3) 1.0896(3) 0.18117(18) 0.0427(6) Uani 1 1 d . . . C5 C -0.1022(4) 1.1189(4) 0.2154(2) 0.0631(8) Uani 1 1 d . . . H5 H -0.1573 1.0874 0.2825 0.076 Uiso 1 1 calc R . . C6 C -0.2061(4) 1.1959(5) 0.1503(3) 0.0803(10) Uani 1 1 d . . . H6 H -0.3302 1.2145 0.1740 0.096 Uiso 1 1 calc R . . C7 C -0.1266(4) 1.2439(4) 0.0521(3) 0.0725(9) Uani 1 1 d . . . H7 H -0.1959 1.2969 0.0092 0.087 Uiso 1 1 calc R . . C8 C 0.0549(4) 1.2138(4) 0.0170(2) 0.0662(9) Uani 1 1 d . . . H8 H 0.1094 1.2457 -0.0501 0.079 Uiso 1 1 calc R . . C9 C 0.1591(4) 1.1356(4) 0.0810(2) 0.0561(8) Uani 1 1 d . . . H9 H 0.2828 1.1142 0.0563 0.067 Uiso 1 1 calc R . . C10 C 0.2566(3) 0.8167(3) 0.21434(17) 0.0421(6) Uani 1 1 d . . . C11 C 0.4290(3) 0.7712(4) 0.1562(2) 0.0568(8) Uani 1 1 d . . . H11 H 0.5119 0.8499 0.1395 0.068 Uiso 1 1 calc R . . C12 C 0.4776(4) 0.6082(4) 0.1230(2) 0.0640(9) Uani 1 1 d . . . H12 H 0.5937 0.5781 0.0848 0.077 Uiso 1 1 calc R . . C13 C 0.3572(5) 0.4915(4) 0.1457(2) 0.0666(9) Uani 1 1 d . . . H13 H 0.3909 0.3829 0.1225 0.080 Uiso 1 1 calc R . . C14 C 0.1859(4) 0.5351(4) 0.2029(2) 0.0664(9) Uani 1 1 d . . . H14 H 0.1036 0.4557 0.2187 0.080 Uiso 1 1 calc R . . C15 C 0.1354(4) 0.6975(4) 0.2372(2) 0.0565(8) Uani 1 1 d . . . H15 H 0.0194 0.7263 0.2758 0.068 Uiso 1 1 calc R . . O2A1 O 0.4871(18) -0.001(2) 0.6178(9) 0.084(5) Uiso 0.260(13) 1 d P . . O2A2 O 0.5386(16) -0.1549(18) 0.6046(10) 0.108(6) Uiso 0.258(11) 1 d P . . N1A N 0.3826(10) 0.1856(13) 0.4879(6) 0.081(2) Uani 0.462(9) 1 d P . . H1NA H 0.4226 0.0974 0.4532 0.098 Uiso 0.462(9) 1 d PR . . C16A C 0.4034(14) 0.1738(18) 0.5863(10) 0.100(5) Uani 0.462(9) 1 d P . . C17A C 0.3347(13) 0.3375(18) 0.6379(8) 0.095(4) Uani 0.462(9) 1 d P . . H17A H 0.3423 0.3404 0.7055 0.114 Uiso 0.462(9) 1 d PR . . C18 C 0.2618(6) 0.5071(9) 0.5859(5) 0.133(2) Uani 1 1 d . . . H18A H 0.2207 0.6045 0.6217 0.159 Uiso 0.462(9) 1 d PR . . C19 C 0.2576(7) 0.5060(10) 0.4893(5) 0.154(3) Uani 1 1 d . . . H19A H 0.2081 0.6006 0.4564 0.185 Uiso 0.462(9) 1 d PR . . C20A C 0.3127(13) 0.3247(12) 0.4379(7) 0.084(3) Uani 0.462(9) 1 d P . . H20A H 0.3047 0.3201 0.3705 0.101 Uiso 0.462(9) 1 d PR . . O2B O 0.4668(8) 0.1067(17) 0.6207(5) 0.119(3) Uani 0.538(9) 1 d P . . N1B N 0.4463(13) 0.2853(14) 0.4612(6) 0.107(3) Uani 0.538(9) 1 d P . . H1NB H 0.4656 0.1964 0.4270 0.128 Uiso 0.538(9) 1 d PR . . C16B C 0.4498(13) 0.2701(16) 0.5599(7) 0.095(3) Uani 0.538(9) 1 d P . . C17B C 0.4078(16) 0.4356(16) 0.6147(6) 0.109(4) Uani 0.538(9) 1 d P . . H17B H 0.3793 0.4127 0.6892 0.131 Uiso 0.538(9) 1 d PR . . C20B C 0.4123(13) 0.4516(14) 0.4159(6) 0.112(4) Uani 0.538(9) 1 d P . . H20B H 0.3810 0.4341 0.3519 0.134 Uiso 0.538(9) 1 d PR . . H18B H 0.1606 0.5365 0.6419 0.134 Uiso 0.54 1 d P . . H19B H 0.1382 0.5198 0.4735 0.134 Uiso 0.54 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0599(11) 0.0736(14) 0.0540(12) -0.0111(10) -0.0176(9) -0.0176(10) C1 0.0626(17) 0.0643(19) 0.0392(15) -0.0091(13) -0.0103(12) 0.0033(14) C2 0.0624(17) 0.0598(19) 0.0403(16) -0.0098(13) -0.0112(13) 0.0018(14) C3 0.0473(14) 0.0561(17) 0.0326(13) -0.0072(12) -0.0072(11) -0.0076(12) C4 0.0507(15) 0.0397(15) 0.0365(14) -0.0056(11) -0.0074(11) -0.0043(11) C5 0.0550(17) 0.069(2) 0.0568(18) 0.0043(15) -0.0055(14) 0.0034(14) C6 0.0618(19) 0.091(3) 0.081(3) 0.011(2) -0.0180(17) 0.0108(17) C7 0.082(2) 0.065(2) 0.073(2) 0.0049(17) -0.0325(18) 0.0071(17) C8 0.084(2) 0.070(2) 0.0443(17) 0.0057(14) -0.0197(15) -0.0066(17) C9 0.0587(17) 0.065(2) 0.0420(16) -0.0032(13) -0.0075(13) -0.0070(14) C10 0.0473(14) 0.0493(16) 0.0275(13) 0.0007(11) -0.0080(10) -0.0009(11) C11 0.0512(16) 0.070(2) 0.0461(16) -0.0054(14) -0.0078(12) -0.0002(14) C12 0.0631(19) 0.070(2) 0.0522(18) -0.0128(15) -0.0100(14) 0.0148(16) C13 0.087(2) 0.055(2) 0.0554(19) -0.0075(15) -0.0209(16) 0.0149(17) C14 0.083(2) 0.0487(19) 0.065(2) 0.0015(15) -0.0126(16) -0.0100(16) C15 0.0573(16) 0.0562(19) 0.0501(17) -0.0024(13) -0.0044(13) -0.0020(14) N1A 0.081(5) 0.093(6) 0.079(5) 0.014(4) -0.035(4) -0.024(4) C16A 0.076(6) 0.132(10) 0.110(9) 0.092(9) -0.062(6) -0.060(7) C17A 0.086(6) 0.136(11) 0.074(6) -0.010(6) -0.016(5) -0.064(7) C18 0.070(3) 0.205(7) 0.113(4) -0.015(4) 0.007(3) -0.031(3) C19 0.092(4) 0.274(9) 0.105(4) -0.019(5) -0.040(3) -0.016(4) C20A 0.081(6) 0.097(7) 0.090(6) 0.007(5) -0.049(5) -0.021(5) O2B 0.107(4) 0.180(9) 0.071(4) -0.029(4) -0.049(3) 0.055(5) N1B 0.115(7) 0.104(7) 0.096(6) 0.017(5) -0.028(5) 0.001(5) C16B 0.098(6) 0.123(9) 0.062(6) 0.010(5) -0.038(5) 0.022(6) C17B 0.128(8) 0.143(9) 0.043(4) 0.010(5) -0.011(4) 0.007(7) C20B 0.116(7) 0.158(10) 0.075(5) -0.012(6) -0.054(5) 0.000(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.427(3) . ? O1 H1 0.8200 . ? C1 C2 1.189(4) . ? C1 C1 1.387(5) 2_576 ? C2 C3 1.484(3) . ? C3 C10 1.533(4) . ? C3 C4 1.538(4) . ? C4 C5 1.361(4) . ? C4 C9 1.383(4) . ? C5 C6 1.396(4) . ? C5 H5 0.9300 . ? C6 C7 1.364(5) . ? C6 H6 0.9300 . ? C7 C8 1.362(4) . ? C7 H7 0.9300 . ? C8 C9 1.388(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.384(4) . ? C10 C11 1.388(3) . ? C11 C12 1.388(4) . ? C11 H11 0.9300 . ? C12 C13 1.365(4) . ? C12 H12 0.9300 . ? C13 C14 1.375(4) . ? C13 H13 0.9300 . ? C14 C15 1.390(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A1 O2B 0.858(12) . ? O2A1 O2A2 1.256(18) . ? O2A1 C16A 1.540(18) . ? O2A2 N1A 1.275(14) 2_656 ? O2A2 N1B 1.399(16) 2_656 ? O2A2 C20A 1.702(17) 2_656 ? N1A N1B 0.986(9) . ? N1A O2A2 1.275(14) 2_656 ? N1A C20A 1.379(13) . ? N1A C16A 1.375(14) . ? N1A C16B 1.458(12) . ? N1A H1NA 0.8591 . ? N1A H1NB 0.9148 . ? C16A O2B 0.868(10) . ? C16A C16B 0.900(12) . ? C16A C17A 1.506(17) . ? C16A N1B 1.821(12) . ? C17A C17B 1.008(12) . ? C17A C16B 1.303(13) . ? C17A C18 1.583(15) . ? C17A H17A 0.9341 . ? C17A H17B 1.0963 . ? C18 C17B 1.334(11) . ? C18 C19 1.316(7) . ? C18 H18A 0.9287 . ? C18 H18B 0.9624 . ? C19 C20B 1.397(10) . ? C19 C20A 1.619(11) . ? C19 H19A 0.9363 . ? C19 H19B 0.9916 . ? C20A N1B 1.156(10) . ? C20A C20B 1.320(12) . ? C20A O2A2 1.702(17) 2_656 ? C20A H20A 0.9340 . ? C20A H1NB 1.4515 . ? C20A H20B 1.4292 . ? O2B C16B 1.496(14) . ? N1B C16B 1.338(11) . ? N1B O2A2 1.399(16) 2_656 ? N1B C20B 1.440(13) . ? N1B H1NB 0.8563 . ? C16B C17B 1.527(15) . ? C17B C20B 1.700(19) 2_666 ? C17B H17A 1.4076 . ? C17B H17B 0.9844 . ? C20B C17B 1.700(19) 2_666 ? C20B H20B 0.9818 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.5(4) . 2_576 ? C1 C2 C3 174.8(3) . . ? O1 C3 C2 108.64(19) . . ? O1 C3 C10 110.2(2) . . ? C2 C3 C10 109.8(2) . . ? O1 C3 C4 107.5(2) . . ? C2 C3 C4 111.8(2) . . ? C10 C3 C4 108.86(18) . . ? C5 C4 C9 119.2(2) . . ? C5 C4 C3 122.1(2) . . ? C9 C4 C3 118.6(2) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.2(3) . . ? C4 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C15 C10 C11 118.8(3) . . ? C15 C10 C3 120.4(2) . . ? C11 C10 C3 120.8(2) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.5(3) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O2B O2A1 O2A2 171.5(18) . . ? O2B O2A1 C16A 27.0(9) . . ? O2A2 O2A1 C16A 152.8(12) . . ? O2A1 O2A2 N1A 113.4(13) . 2_656 ? O2A1 O2A2 N1B 144.1(13) . 2_656 ? N1A O2A2 N1B 42.9(6) 2_656 2_656 ? O2A1 O2A2 C20A 155.8(12) . 2_656 ? N1A O2A2 C20A 52.8(7) 2_656 2_656 ? N1B O2A2 C20A 42.4(6) 2_656 2_656 ? N1B N1A O2A2 75.3(10) . 2_656 ? N1B N1A C20A 55.6(8) . . ? O2A2 N1A C20A 79.7(9) 2_656 . ? N1B N1A C16A 99.7(9) . . ? O2A2 N1A C16A 144.1(10) 2_656 . ? C20A N1A C16A 127.3(10) . . ? N1B N1A C16B 62.9(8) . . ? O2A2 N1A C16B 127.5(9) 2_656 . ? C20A N1A C16B 99.6(8) . . ? C16A N1A C16B 36.9(5) . . ? N1B N1A H1NA 114.3 . . ? O2A2 N1A H1NA 43.4 2_656 . ? C20A N1A H1NA 116.8 . . ? C16A N1A H1NA 115.8 . . ? C16B N1A H1NA 133.3 . . ? N1B N1A H1NB 53.4 . . ? O2A2 N1A H1NB 23.6 2_656 . ? C20A N1A H1NB 75.5 . . ? C16A N1A H1NB 130.1 . . ? C16B N1A H1NB 104.7 . . ? H1NA N1A H1NB 61.5 . . ? O2B C16A C16B 115.6(14) . . ? O2B C16A N1A 135.8(17) . . ? C16B C16A N1A 76.5(10) . . ? O2B C16A C17A 111.5(15) . . ? C16B C16A C17A 59.4(11) . . ? N1A C16A C17A 110.9(10) . . ? O2B C16A O2A1 26.7(9) . . ? C16B C16A O2A1 133.2(12) . . ? N1A C16A O2A1 113.7(12) . . ? C17A C16A O2A1 135.4(11) . . ? O2B C16A N1B 135.9(13) . . ? C16B C16A N1B 44.5(9) . . ? N1A C16A N1B 32.2(4) . . ? C17A C16A N1B 90.8(8) . . ? O2A1 C16A N1B 128.8(11) . . ? C17B C17A C16B 81.7(11) . . ? C17B C17A C16A 117.4(12) . . ? C16B C17A C16A 36.5(6) . . ? C17B C17A C18 56.9(10) . . ? C16B C17A C18 101.0(9) . . ? C16A C17A C18 125.8(9) . . ? C17B C17A H17A 92.8 . . ? C16B C17A H17A 129.9 . . ? C16A C17A H17A 116.7 . . ? C18 C17A H17A 117.4 . . ? C17B C17A H17B 55.6 . . ? C16B C17A H17B 120.4 . . ? C16A C17A H17B 135.5 . . ? C18 C17A H17B 89.1 . . ? H17A C17A H17B 37.7 . . ? C17B C18 C19 119.1(6) . . ? C17B C18 C17A 39.3(6) . . ? C19 C18 C17A 117.8(6) . . ? C17B C18 H18A 107.6 . . ? C19 C18 H18A 120.1 . . ? C17A C18 H18A 122.1 . . ? C17B C18 H18B 114.1 . . ? C19 C18 H18B 125.7 . . ? C17A C18 H18B 96.7 . . ? H18A C18 H18B 46.7 . . ? C18 C19 C20B 120.2(5) . . ? C18 C19 C20A 115.9(7) . . ? C20B C19 C20A 51.3(6) . . ? C18 C19 H19A 121.2 . . ? C20B C19 H19A 102.9 . . ? C20A C19 H19A 122.2 . . ? C18 C19 H19B 117.6 . . ? C20B C19 H19B 120.8 . . ? C20A C19 H19B 92.6 . . ? H19A C19 H19B 53.9 . . ? N1B C20A C20B 70.8(8) . . ? N1B C20A N1A 44.7(6) . . ? C20B C20A N1A 115.3(8) . . ? N1B C20A C19 99.4(8) . . ? C20B C20A C19 55.6(6) . . ? N1A C20A C19 121.7(7) . . ? N1B C20A O2A2 54.7(8) . 2_656 ? C20B C20A O2A2 103.2(8) . 2_656 ? N1A C20A O2A2 47.5(6) . 2_656 ? C19 C20A O2A2 152.9(7) . 2_656 ? N1B C20A H20A 121.4 . . ? C20B C20A H20A 93.3 . . ? N1A C20A H20A 120.8 . . ? C19 C20A H20A 117.3 . . ? O2A2 C20A H20A 77.1 2_656 . ? N1B C20A H1NB 36.1 . . ? C20B C20A H1NB 94.1 . . ? N1A C20A H1NB 37.6 . . ? C19 C20A H1NB 135.4 . . ? O2A2 C20A H1NB 18.8 2_656 . ? H20A C20A H1NB 93.9 . . ? N1B C20A H20B 97.4 . . ? C20B C20A H20B 41.6 . . ? N1A C20A H20B 135.5 . . ? C19 C20A H20B 79.8 . . ? O2A2 C20A H20B 94.7 2_656 . ? H20A C20A H20B 51.9 . . ? H1NB C20A H20B 98.8 . . ? O2A1 O2B C16A 126.3(17) . . ? O2A1 O2B C16B 145.0(12) . . ? C16A O2B C16B 32.8(8) . . ? N1A N1B C20A 79.7(11) . . ? N1A N1B C16B 76.0(9) . . ? C20A N1B C16B 120.5(9) . . ? N1A N1B O2A2 61.8(9) . 2_656 ? C20A N1B O2A2 83.0(10) . 2_656 ? C16B N1B O2A2 127.3(11) . 2_656 ? N1A N1B C20B 139.4(11) . . ? C20A N1B C20B 60.0(7) . . ? C16B N1B C20B 118.6(9) . . ? O2A2 N1B C20B 113.9(9) 2_656 . ? N1A N1B C16A 48.1(7) . . ? C20A N1B C16A 110.0(9) . . ? C16B N1B C16A 28.1(7) . . ? O2A2 N1B C16A 102.3(10) 2_656 . ? C20B N1B C16A 139.6(8) . . ? N1A N1B H1NB 59.1 . . ? C20A N1B H1NB 91.1 . . ? C16B N1B H1NB 119.2 . . ? O2A2 N1B H1NB 9.2 2_656 . ? C20B N1B H1NB 122.2 . . ? C16A N1B H1NB 95.5 . . ? C16A C16B C17A 84.2(13) . . ? C16A C16B N1B 107.4(14) . . ? C17A C16B N1B 128.7(9) . . ? C16A C16B N1A 66.6(12) . . ? C17A C16B N1A 118.5(9) . . ? N1B C16B N1A 41.0(5) . . ? C16A C16B O2B 31.5(8) . . ? C17A C16B O2B 90.6(9) . . ? N1B C16B O2B 125.3(10) . . ? N1A C16B O2B 89.9(8) . . ? C16A C16B C17B 124.0(15) . . ? C17A C16B C17B 40.8(6) . . ? N1B C16B C17B 114.9(9) . . ? N1A C16B C17B 138.4(7) . . ? O2B C16B C17B 119.3(7) . . ? C17A C17B C18 83.8(13) . . ? C17A C17B C16B 57.6(10) . . ? C18 C17B C16B 102.4(9) . . ? C17A C17B C20B 159.9(13) . 2_666 ? C18 C17B C20B 115.9(9) . 2_666 ? C16B C17B C20B 111.0(8) . 2_666 ? C17A C17B H17A 41.5 . . ? C18 C17B H17A 105.1 . . ? C16B C17B H17A 87.5 . . ? C20B C17B H17A 128.6 2_666 . ? C17A C17B H17B 66.8 . . ? C18 C17B H17B 110.1 . . ? C16B C17B H17B 110.3 . . ? C20B C17B H17B 107.1 2_666 . ? H17A C17B H17B 25.7 . . ? C20A C20B C19 73.1(7) . . ? C20A C20B N1B 49.3(6) . . ? C19 C20B N1B 97.8(7) . . ? C20A C20B C17B 162.1(9) . 2_666 ? C19 C20B C17B 120.8(8) . 2_666 ? N1B C20B C17B 114.4(8) . 2_666 ? C20A C20B H20B 75.1 . . ? C19 C20B H20B 109.8 . . ? N1B C20B H20B 105.7 . . ? C17B C20B H20B 107.2 2_666 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -79(58) 2_576 . . . ? C1 C2 C3 O1 -5(4) . . . . ? C1 C2 C3 C10 115(3) . . . . ? C1 C2 C3 C4 -124(3) . . . . ? O1 C3 C4 C5 -136.6(3) . . . . ? C2 C3 C4 C5 -17.5(3) . . . . ? C10 C3 C4 C5 104.0(3) . . . . ? O1 C3 C4 C9 46.9(3) . . . . ? C2 C3 C4 C9 166.0(2) . . . . ? C10 C3 C4 C9 -72.5(3) . . . . ? C9 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C6 -177.1(3) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C8 1.1(5) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C5 C4 C9 C8 1.3(4) . . . . ? C3 C4 C9 C8 177.9(2) . . . . ? C7 C8 C9 C4 -0.8(4) . . . . ? O1 C3 C10 C15 168.6(2) . . . . ? C2 C3 C10 C15 48.9(3) . . . . ? C4 C3 C10 C15 -73.7(3) . . . . ? O1 C3 C10 C11 -14.2(3) . . . . ? C2 C3 C10 C11 -133.9(2) . . . . ? C4 C3 C10 C11 103.5(3) . . . . ? C15 C10 C11 C12 -0.6(4) . . . . ? C3 C10 C11 C12 -177.9(2) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C11 C12 C13 C14 -0.6(5) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C11 C10 C15 C14 0.3(4) . . . . ? C3 C10 C15 C14 177.5(2) . . . . ? C13 C14 C15 C10 -0.1(4) . . . . ? O2B O2A1 O2A2 N1A -40(12) . . . 2_656 ? C16A O2A1 O2A2 N1A 41(3) . . . 2_656 ? O2B O2A1 O2A2 N1B -80(12) . . . 2_656 ? C16A O2A1 O2A2 N1B 0(4) . . . 2_656 ? O2B O2A1 O2A2 C20A 10(13) . . . 2_656 ? C16A O2A1 O2A2 C20A 91(4) . . . 2_656 ? N1B N1A C16A O2B -107.5(17) . . . . ? O2A2 N1A C16A O2B -29(3) 2_656 . . . ? C20A N1A C16A O2B -161.2(14) . . . . ? C16B N1A C16A O2B -113(2) . . . . ? N1B N1A C16A C16B 5.6(14) . . . . ? O2A2 N1A C16A C16B 84(2) 2_656 . . . ? C20A N1A C16A C16B -48.2(15) . . . . ? N1B N1A C16A C17A 54.9(11) . . . . ? O2A2 N1A C16A C17A 133.0(18) 2_656 . . . ? C20A N1A C16A C17A 1.1(13) . . . . ? C16B N1A C16A C17A 49.3(9) . . . . ? N1B N1A C16A O2A1 -126.0(10) . . . . ? O2A2 N1A C16A O2A1 -48(2) 2_656 . . . ? C20A N1A C16A O2A1 -179.8(9) . . . . ? C16B N1A C16A O2A1 -131.6(14) . . . . ? O2A2 N1A C16A N1B 78.2(18) 2_656 . . . ? C20A N1A C16A N1B -53.7(9) . . . . ? C16B N1A C16A N1B -5.6(14) . . . . ? O2A2 O2A1 C16A O2B -161(4) . . . . ? O2B O2A1 C16A C16B 57(2) . . . . ? O2A2 O2A1 C16A C16B -105(3) . . . . ? O2B O2A1 C16A N1A 150(2) . . . . ? O2A2 O2A1 C16A N1A -11(3) . . . . ? O2B O2A1 C16A C17A -31(2) . . . . ? O2A2 O2A1 C16A C17A 168(2) . . . . ? O2B O2A1 C16A N1B 117(2) . . . . ? O2A2 O2A1 C16A N1B -45(3) . . . . ? O2B C16A C17A C17B 94.9(17) . . . . ? C16B C16A C17A C17B -13.0(15) . . . . ? N1A C16A C17A C17B -72.0(14) . . . . ? O2A1 C16A C17A C17B 109.2(16) . . . . ? N1B C16A C17A C17B -46.1(13) . . . . ? O2B C16A C17A C16B 107.9(14) . . . . ? N1A C16A C17A C16B -59.0(9) . . . . ? O2A1 C16A C17A C16B 122.2(15) . . . . ? N1B C16A C17A C16B -33.1(8) . . . . ? O2B C16A C17A C18 162.3(10) . . . . ? C16B C16A C17A C18 54.4(12) . . . . ? N1A C16A C17A C18 -4.6(12) . . . . ? O2A1 C16A C17A C18 176.6(9) . . . . ? N1B C16A C17A C18 21.3(10) . . . . ? C16B C17A C18 C17B -72.4(10) . . . . ? C16A C17A C18 C17B -101.9(13) . . . . ? C17B C17A C18 C19 103.0(8) . . . . ? C16B C17A C18 C19 30.6(9) . . . . ? C16A C17A C18 C19 1.1(11) . . . . ? C17B C18 C19 C20B -8.6(13) . . . . ? C17A C18 C19 C20B -53.6(10) . . . . ? C17B C18 C19 C20A 49.9(11) . . . . ? C17A C18 C19 C20A 5.0(8) . . . . ? O2A2 N1A C20A N1B -79.1(10) 2_656 . . . ? C16A N1A C20A N1B 74.5(11) . . . . ? C16B N1A C20A N1B 47.5(8) . . . . ? N1B N1A C20A C20B -5.7(10) . . . . ? O2A2 N1A C20A C20B -84.8(10) 2_656 . . . ? C16A N1A C20A C20B 68.8(13) . . . . ? C16B N1A C20A C20B 41.8(11) . . . . ? N1B N1A C20A C19 -69.5(10) . . . . ? O2A2 N1A C20A C19 -148.6(9) 2_656 . . . ? C16A N1A C20A C19 5.1(14) . . . . ? C16B N1A C20A C19 -21.9(10) . . . . ? N1B N1A C20A O2A2 79.1(10) . . . 2_656 ? C16A N1A C20A O2A2 153.7(12) . . . 2_656 ? C16B N1A C20A O2A2 126.7(9) . . . 2_656 ? C18 C19 C20A N1B -50.3(9) . . . . ? C20B C19 C20A N1B 58.8(7) . . . . ? C18 C19 C20A C20B -109.1(7) . . . . ? C18 C19 C20A N1A -8.4(11) . . . . ? C20B C19 C20A N1A 100.7(10) . . . . ? C18 C19 C20A O2A2 -66.0(19) . . . 2_656 ? C20B C19 C20A O2A2 43.1(16) . . . 2_656 ? O2A2 O2A1 O2B C16A 97(11) . . . . ? O2A2 O2A1 O2B C16B 58(12) . . . . ? C16A O2A1 O2B C16B -39.7(16) . . . . ? C16B C16A O2B O2A1 -137(2) . . . . ? N1A C16A O2B O2A1 -40(3) . . . . ? C17A C16A O2B O2A1 157.3(15) . . . . ? N1B C16A O2B O2A1 -87(2) . . . . ? N1A C16A O2B C16B 97(2) . . . . ? C17A C16A O2B C16B -65.3(16) . . . . ? O2A1 C16A O2B C16B 137(2) . . . . ? N1B C16A O2B C16B 50.1(13) . . . . ? O2A2 N1A N1B C20A 87.5(9) 2_656 . . . ? C16A N1A N1B C20A -129.0(10) . . . . ? C16B N1A N1B C20A -125.2(8) . . . . ? O2A2 N1A N1B C16B -147.3(8) 2_656 . . . ? C20A N1A N1B C16B 125.2(8) . . . . ? C16A N1A N1B C16B -3.7(9) . . . . ? C20A N1A N1B O2A2 -87.5(9) . . . 2_656 ? C16A N1A N1B O2A2 143.6(11) . . . 2_656 ? C16B N1A N1B O2A2 147.3(8) . . . 2_656 ? O2A2 N1A N1B C20B 94.7(16) 2_656 . . . ? C20A N1A N1B C20B 7.3(13) . . . . ? C16A N1A N1B C20B -121.7(15) . . . . ? C16B N1A N1B C20B -118.0(15) . . . . ? O2A2 N1A N1B C16A -143.6(11) 2_656 . . . ? C20A N1A N1B C16A 129.0(10) . . . . ? C16B N1A N1B C16A 3.7(9) . . . . ? C20B C20A N1B N1A 174.5(10) . . . . ? C19 C20A N1B N1A 126.2(9) . . . . ? O2A2 C20A N1B N1A -62.5(9) 2_656 . . . ? C20B C20A N1B C16B 107.6(12) . . . . ? N1A C20A N1B C16B -67.0(11) . . . . ? C19 C20A N1B C16B 59.2(13) . . . . ? O2A2 C20A N1B C16B -129.5(15) 2_656 . . . ? C20B C20A N1B O2A2 -122.9(9) . . . 2_656 ? N1A C20A N1B O2A2 62.5(9) . . . 2_656 ? C19 C20A N1B O2A2 -171.3(8) . . . 2_656 ? N1A C20A N1B C20B -174.5(10) . . . . ? C19 C20A N1B C20B -48.4(6) . . . . ? O2A2 C20A N1B C20B 122.9(9) 2_656 . . . ? C20B C20A N1B C16A 136.5(9) . . . . ? N1A C20A N1B C16A -38.0(8) . . . . ? C19 C20A N1B C16A 88.2(9) . . . . ? O2A2 C20A N1B C16A -100.5(11) 2_656 . . . ? O2B C16A N1B N1A 107(2) . . . . ? C16B C16A N1B N1A -172.3(19) . . . . ? C17A C16A N1B N1A -130.2(12) . . . . ? O2A1 C16A N1B N1A 71.9(13) . . . . ? O2B C16A N1B C20A 161.6(18) . . . . ? C16B C16A N1B C20A -117.8(15) . . . . ? N1A C16A N1B C20A 54.5(12) . . . . ? C17A C16A N1B C20A -75.7(10) . . . . ? O2A1 C16A N1B C20A 126.4(10) . . . . ? O2B C16A N1B C16B -80.6(19) . . . . ? N1A C16A N1B C16B 172.3(19) . . . . ? C17A C16A N1B C16B 42.1(12) . . . . ? O2A1 C16A N1B C16B -115.8(15) . . . . ? O2B C16A N1B O2A2 75(2) . . . 2_656 ? C16B C16A N1B O2A2 155.4(15) . . . 2_656 ? N1A C16A N1B O2A2 -32.4(10) . . . 2_656 ? C17A C16A N1B O2A2 -162.5(8) . . . 2_656 ? O2A1 C16A N1B O2A2 39.6(12) . . . 2_656 ? O2B C16A N1B C20B -132(2) . . . . ? C16B C16A N1B C20B -51.0(17) . . . . ? N1A C16A N1B C20B 121.2(17) . . . . ? C17A C16A N1B C20B -8.9(13) . . . . ? O2A1 C16A N1B C20B -166.8(12) . . . . ? O2B C16A C16B C17A -100.8(19) . . . . ? N1A C16A C16B C17A 124.6(8) . . . . ? O2A1 C16A C16B C17A -125.4(19) . . . . ? N1B C16A C16B C17A 128.8(10) . . . . ? O2B C16A C16B N1B 130.4(16) . . . . ? N1A C16A C16B N1B -4.2(10) . . . . ? C17A C16A C16B N1B -128.8(10) . . . . ? O2A1 C16A C16B N1B 105.7(18) . . . . ? O2B C16A C16B N1A 135(2) . . . . ? C17A C16A C16B N1A -124.6(8) . . . . ? O2A1 C16A C16B N1A 110(2) . . . . ? N1B C16A C16B N1A 4.2(10) . . . . ? N1A C16A C16B O2B -135(2) . . . . ? C17A C16A C16B O2B 100.8(19) . . . . ? O2A1 C16A C16B O2B -24.6(10) . . . . ? N1B C16A C16B O2B -130.4(16) . . . . ? O2B C16A C16B C17B -92(2) . . . . ? N1A C16A C16B C17B 133.7(10) . . . . ? C17A C16A C16B C17B 9.1(10) . . . . ? O2A1 C16A C16B C17B -116.3(19) . . . . ? N1B C16A C16B C17B 138.0(15) . . . . ? C17B C17A C16B C16A 168.4(13) . . . . ? C18 C17A C16B C16A -137.8(9) . . . . ? C17B C17A C16B N1B -84.0(16) . . . . ? C16A C17A C16B N1B 107.6(19) . . . . ? C18 C17A C16B N1B -30.2(17) . . . . ? C17B C17A C16B N1A -132.4(12) . . . . ? C16A C17A C16B N1A 59.3(14) . . . . ? C18 C17A C16B N1A -78.5(12) . . . . ? C17B C17A C16B O2B 137.4(11) . . . . ? C16A C17A C16B O2B -30.9(7) . . . . ? C18 C17A C16B O2B -168.7(6) . . . . ? C16A C17A C16B C17B -168.4(13) . . . . ? C18 C17A C16B C17B 53.8(10) . . . . ? N1A N1B C16B C16A 5.9(15) . . . . ? C20A N1B C16B C16A 74.9(17) . . . . ? O2A2 N1B C16B C16A -30.8(18) 2_656 . . . ? C20B N1B C16B C16A 145.0(13) . . . . ? N1A N1B C16B C17A -90.6(16) . . . . ? C20A N1B C16B C17A -22(2) . . . . ? O2A2 N1B C16B C17A -127.4(15) 2_656 . . . ? C20B N1B C16B C17A 48.4(19) . . . . ? C16A N1B C16B C17A -96.6(19) . . . . ? C20A N1B C16B N1A 68.9(13) . . . . ? O2A2 N1B C16B N1A -36.7(10) 2_656 . . . ? C20B N1B C16B N1A 139.0(13) . . . . ? C16A N1B C16B N1A -5.9(15) . . . . ? N1A N1B C16B O2B 35.2(12) . . . . ? C20A N1B C16B O2B 104.1(12) . . . . ? O2A2 N1B C16B O2B -1.6(17) 2_656 . . . ? C20B N1B C16B O2B 174.2(8) . . . . ? C16A N1B C16B O2B 29.2(11) . . . . ? N1A N1B C16B C17B -136.3(10) . . . . ? C20A N1B C16B C17B -67.4(16) . . . . ? O2A2 N1B C16B C17B -173.1(11) 2_656 . . . ? C20B N1B C16B C17B 2.7(14) . . . . ? C16A N1B C16B C17B -142.3(17) . . . . ? N1B N1A C16B C16A -173.8(15) . . . . ? O2A2 N1A C16B C16A -132.7(17) 2_656 . . . ? C20A N1A C16B C16A 143.1(13) . . . . ? N1B N1A C16B C17A 117.4(14) . . . . ? O2A2 N1A C16B C17A 158.6(14) 2_656 . . . ? C20A N1A C16B C17A 74.3(14) . . . . ? C16A N1A C16B C17A -68.8(15) . . . . ? O2A2 N1A C16B N1B 41.2(12) 2_656 . . . ? C20A N1A C16B N1B -43.1(7) . . . . ? C16A N1A C16B N1B 173.8(15) . . . . ? N1B N1A C16B O2B -152.0(9) . . . . ? O2A2 N1A C16B O2B -110.8(13) 2_656 . . . ? C20A N1A C16B O2B 164.9(7) . . . . ? C16A N1A C16B O2B 21.9(10) . . . . ? N1B N1A C16B C17B 70.7(16) . . . . ? O2A2 N1A C16B C17B 111.9(16) 2_656 . . . ? C20A N1A C16B C17B 27.6(17) . . . . ? C16A N1A C16B C17B -115(2) . . . . ? O2A1 O2B C16B C16A 72(3) . . . . ? O2A1 O2B C16B C17A 150(2) . . . . ? C16A O2B C16B C17A 78(2) . . . . ? O2A1 O2B C16B N1B 9(3) . . . . ? C16A O2B C16B N1B -63(2) . . . . ? O2A1 O2B C16B N1A 31(2) . . . . ? C16A O2B C16B N1A -41(2) . . . . ? O2A1 O2B C16B C17B -180(2) . . . . ? C16A O2B C16B C17B 108(2) . . . . ? C16B C17A C17B C18 109.0(7) . . . . ? C16A C17A C17B C18 116.7(11) . . . . ? C16A C17A C17B C16B 7.8(8) . . . . ? C18 C17A C17B C16B -109.0(7) . . . . ? C16B C17A C17B C20B -60(3) . . . 2_666 ? C16A C17A C17B C20B -52(3) . . . 2_666 ? C18 C17A C17B C20B -169(3) . . . 2_666 ? C19 C18 C17B C17A -99.3(9) . . . . ? C19 C18 C17B C16B -44.5(11) . . . . ? C17A C18 C17B C16B 54.8(10) . . . . ? C19 C18 C17B C20B 76.5(11) . . . 2_666 ? C17A C18 C17B C20B 175.8(12) . . . 2_666 ? C16A C16B C17B C17A -14.0(16) . . . . ? N1B C16B C17B C17A 121.2(12) . . . . ? N1A C16B C17B C17A 78.1(16) . . . . ? O2B C16B C17B C17A -50.8(13) . . . . ? C16A C16B C17B C18 -88.3(13) . . . . ? C17A C16B C17B C18 -74.3(13) . . . . ? N1B C16B C17B C18 46.9(12) . . . . ? N1A C16B C17B C18 3.8(18) . . . . ? O2B C16B C17B C18 -125.1(8) . . . . ? C16A C16B C17B C20B 147.4(12) . . . 2_666 ? C17A C16B C17B C20B 161.4(13) . . . 2_666 ? N1B C16B C17B C20B -77.4(10) . . . 2_666 ? N1A C16B C17B C20B -120.5(14) . . . 2_666 ? O2B C16B C17B C20B 110.5(9) . . . 2_666 ? N1B C20A C20B C19 -116.7(7) . . . . ? N1A C20A C20B C19 -112.4(9) . . . . ? O2A2 C20A C20B C19 -161.4(7) 2_656 . . . ? N1A C20A C20B N1B 4.2(8) . . . . ? C19 C20A C20B N1B 116.7(7) . . . . ? O2A2 C20A C20B N1B -44.7(7) 2_656 . . . ? N1B C20A C20B C17B 27(3) . . . 2_666 ? N1A C20A C20B C17B 31(3) . . . 2_666 ? C19 C20A C20B C17B 143(2) . . . 2_666 ? O2A2 C20A C20B C17B -18(3) 2_656 . . 2_666 ? C18 C19 C20B C20A 100.5(9) . . . . ? C18 C19 C20B N1B 57.4(10) . . . . ? C20A C19 C20B N1B -43.1(6) . . . . ? C18 C19 C20B C17B -67.2(11) . . . 2_666 ? C20A C19 C20B C17B -167.7(10) . . . 2_666 ? N1A N1B C20B C20A -8.3(15) . . . . ? C16B N1B C20B C20A -110.6(11) . . . . ? O2A2 N1B C20B C20A 65.7(11) 2_656 . . . ? C16A N1B C20B C20A -86.0(13) . . . . ? N1A N1B C20B C19 51.4(17) . . . . ? C20A N1B C20B C19 59.7(8) . . . . ? C16B N1B C20B C19 -51.0(10) . . . . ? O2A2 N1B C20B C19 125.3(9) 2_656 . . . ? C16A N1B C20B C19 -26.3(14) . . . . ? N1A N1B C20B C17B -179.5(14) . . . 2_666 ? C20A N1B C20B C17B -171.3(9) . . . 2_666 ? C16B N1B C20B C17B 78.1(10) . . . 2_666 ? O2A2 N1B C20B C17B -105.6(10) 2_656 . . 2_666 ? C16A N1B C20B C17B 102.8(12) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.244 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.037 data_I-c_27hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8090(10) _cell_length_b 7.861(2) _cell_length_c 13.539(3) _cell_angle_alpha 87.33(2) _cell_angle_beta 75.75(2) _cell_angle_gamma 84.88(2) _cell_volume 802.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8031 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8031 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2790 _reflns_number_gt 1488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1073P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2790 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1302 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1919 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3281(3) 1.1300(3) 0.23534(14) 0.0590(6) Uani 1 1 d . . . H1 H 0.3996 1.0886 0.2669 0.22(3) Uiso 1 1 calc R . . C1 C 0.0345(4) 1.0050(4) 0.4482(2) 0.0563(8) Uani 1 1 d . . . C2 C 0.0949(4) 1.0132(4) 0.3577(2) 0.0544(8) Uani 1 1 d . . . C3 C 0.1861(3) 1.0225(3) 0.24852(18) 0.0452(7) Uani 1 1 d . . . C4 C 0.0644(3) 1.1016(3) 0.18288(19) 0.0443(6) Uani 1 1 d . . . C5 C -0.1168(4) 1.1270(4) 0.2196(2) 0.0645(9) Uani 1 1 d . . . H5 H -0.1693 1.0964 0.2867 0.070(9) Uiso 1 1 calc R . . C6 C -0.2211(4) 1.1988(5) 0.1557(3) 0.0786(10) Uani 1 1 d . . . H6 H -0.3434 1.2152 0.1806 0.122(14) Uiso 1 1 calc R . . C7 C -0.1466(4) 1.2449(4) 0.0578(3) 0.0725(9) Uani 1 1 d . . . H7 H -0.2171 1.2941 0.0162 0.112(13) Uiso 1 1 calc R . . C8 C 0.0340(4) 1.2185(4) 0.0204(2) 0.0655(9) Uani 1 1 d . . . H8 H 0.0857 1.2491 -0.0468 0.078(10) Uiso 1 1 calc R . . C9 C 0.1383(4) 1.1466(4) 0.0828(2) 0.0555(8) Uani 1 1 d . . . H9 H 0.2602 1.1284 0.0569 0.088(11) Uiso 1 1 calc R . . C10 C 0.2547(3) 0.8413(3) 0.21235(18) 0.0441(7) Uani 1 1 d . . . C11 C 0.4283(4) 0.8056(4) 0.1576(2) 0.0580(8) Uani 1 1 d . . . H11 H 0.5066 0.8911 0.1443 0.071(9) Uiso 1 1 calc R . . C12 C 0.4851(4) 0.6410(4) 0.1225(2) 0.0648(9) Uani 1 1 d . . . H12 H 0.6015 0.6178 0.0856 0.067(9) Uiso 1 1 calc R . . C13 C 0.3729(4) 0.5137(4) 0.1414(2) 0.0627(8) Uani 1 1 d . . . H13 H 0.4127 0.4042 0.1183 0.090(11) Uiso 1 1 calc R . . C14 C 0.1996(4) 0.5490(4) 0.1954(2) 0.0631(8) Uani 1 1 d . . . H14 H 0.1218 0.4631 0.2080 0.082(10) Uiso 1 1 calc R . . C15 C 0.1413(4) 0.7112(4) 0.2305(2) 0.0560(8) Uani 1 1 d . . . H15 H 0.0244 0.7335 0.2669 0.082(10) Uiso 1 1 calc R . . O2 O 0.4683(5) 0.1366(6) 0.3971(2) 0.1304(16) Uani 1 1 d . . . N1B N 0.4834(17) 0.2754(12) 0.5442(6) 0.117(3) Uani 0.605(14) 1 d P . . H1NB H 0.5300 0.1813 0.5662 0.140 Uiso 0.605(14) 1 d PR . . C16B C 0.4506(13) 0.2865(15) 0.4524(5) 0.076(3) Uani 0.605(14) 1 d P . . C17B C 0.3975(15) 0.4659(18) 0.4196(7) 0.113(3) Uani 0.605(14) 1 d P . . H17B H 0.3462 0.4569 0.3603 0.136 Uiso 0.605(14) 1 d PR . . C18B C 0.2555(8) 0.5117(10) 0.5101(7) 0.168(3) Uani 1 1 d . . . H18B H 0.1475 0.5589 0.4985 0.202 Uiso 0.605(14) 1 d PR . . C19B C 0.2748(10) 0.4971(11) 0.6002(7) 0.163(3) Uani 1 1 d . . . H19B H 0.1876 0.5408 0.6554 0.196 Uiso 0.605(14) 1 d PR . . C20B C 0.4367(19) 0.4282(13) 0.6089(5) 0.125(4) Uani 0.605(14) 1 d P . . H20B H 0.4233 0.3902 0.6805 0.149 Uiso 0.605(14) 1 d PR . . N1A N 0.4233(15) 0.174(3) 0.5605(10) 0.109(5) Uani 0.395(14) 1 d P . . H1NA H 0.4886 0.0869 0.5764 0.131 Uiso 0.395(14) 1 d PR . . C16A C 0.401(2) 0.191(3) 0.4657(15) 0.095(5) Uani 0.395(14) 1 d P . . C17A C 0.314(2) 0.361(3) 0.4458(12) 0.110(6) Uani 0.395(14) 1 d P . . H17A H 0.3108 0.3846 0.3779 0.131 Uiso 0.395(14) 1 d PR . . C20A C 0.355(2) 0.295(4) 0.6373(10) 0.179(12) Uani 0.395(14) 1 d P . . H20A H 0.3390 0.2676 0.7067 0.214 Uiso 0.395(14) 1 d PR . . H18A H 0.1902 0.6145 0.4904 0.214 Uiso 0.40 1 d P . . H19A H 0.2501 0.6033 0.6404 0.214 Uiso 0.40 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0628(12) 0.0623(14) 0.0557(12) 0.0010(10) -0.0193(10) -0.0138(10) C1 0.0678(18) 0.060(2) 0.0376(15) -0.0011(13) -0.0104(13) 0.0077(14) C2 0.0639(18) 0.0515(18) 0.0461(19) -0.0035(13) -0.0137(14) 0.0056(14) C3 0.0515(15) 0.0483(17) 0.0338(14) 0.0011(12) -0.0073(11) -0.0028(13) C4 0.0507(15) 0.0394(16) 0.0420(15) -0.0018(12) -0.0112(12) 0.0010(12) C5 0.0513(18) 0.077(2) 0.056(2) 0.0067(16) -0.0029(15) 0.0079(15) C6 0.054(2) 0.093(3) 0.085(3) 0.013(2) -0.0175(17) 0.0144(17) C7 0.073(2) 0.079(2) 0.069(2) 0.0051(18) -0.0303(19) 0.0059(18) C8 0.073(2) 0.073(2) 0.0507(19) 0.0121(16) -0.0191(16) -0.0040(17) C9 0.0531(18) 0.067(2) 0.0449(17) 0.0036(14) -0.0103(13) -0.0001(14) C10 0.0475(15) 0.0498(17) 0.0328(14) 0.0027(12) -0.0090(11) 0.0040(12) C11 0.0507(17) 0.064(2) 0.0534(18) -0.0011(15) -0.0042(13) 0.0022(15) C12 0.0566(19) 0.071(2) 0.0581(19) -0.0047(17) -0.0047(15) 0.0183(17) C13 0.077(2) 0.052(2) 0.0546(19) -0.0018(15) -0.0148(16) 0.0128(17) C14 0.073(2) 0.048(2) 0.065(2) 0.0012(15) -0.0127(16) -0.0023(16) C15 0.0533(18) 0.0495(19) 0.0591(18) 0.0002(14) -0.0039(14) 0.0000(14) O2 0.094(2) 0.237(5) 0.066(2) 0.003(2) -0.0351(17) -0.006(2) N1B 0.196(9) 0.101(6) 0.079(5) 0.005(4) -0.080(5) -0.022(6) C16B 0.090(6) 0.106(7) 0.042(4) -0.009(4) -0.031(4) -0.007(5) C17B 0.114(7) 0.158(10) 0.090(6) 0.012(6) -0.069(6) -0.010(7) C18B 0.097(4) 0.239(8) 0.185(7) -0.091(7) -0.063(5) 0.017(4) C19B 0.097(5) 0.201(8) 0.167(7) -0.061(6) 0.036(4) -0.047(5) C20B 0.191(12) 0.149(9) 0.035(4) 0.013(5) -0.029(5) -0.025(8) N1A 0.088(7) 0.166(15) 0.079(8) -0.029(9) -0.029(6) -0.007(7) C16A 0.075(9) 0.102(12) 0.117(13) 0.006(10) -0.042(8) -0.005(8) C17A 0.096(11) 0.136(15) 0.102(10) -0.022(9) -0.044(8) 0.029(10) C20A 0.140(12) 0.37(4) 0.051(7) 0.002(13) -0.018(8) -0.147(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.425(3) . ? O1 H1 0.8200 . ? C1 C2 1.201(4) . ? C1 C1 1.375(6) 2_576 ? C2 C3 1.476(4) . ? C3 C4 1.529(3) . ? C3 C10 1.535(4) . ? C4 C5 1.379(4) . ? C4 C9 1.379(4) . ? C5 C6 1.397(4) . ? C5 H5 0.9300 . ? C6 C7 1.356(5) . ? C6 H6 0.9300 . ? C7 C8 1.376(4) . ? C7 H7 0.9300 . ? C8 C9 1.381(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.386(4) . ? C10 C11 1.387(4) . ? C11 C12 1.396(4) . ? C11 H11 0.9300 . ? C12 C13 1.362(4) . ? C12 H12 0.9300 . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 C15 1.381(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 1.040(18) . ? O2 C16B 1.404(11) . ? N1B N1A 0.951(14) . ? N1B C16B 1.326(9) . ? N1B C20A 1.410(17) . ? N1B C20B 1.485(12) . ? N1B C16A 1.571(19) . ? N1B H1NB 0.8675 . ? C16B C16A 0.868(14) . ? C16B C17A 1.191(14) . ? C16B C17B 1.512(15) . ? C16B N1A 1.652(17) . ? C17B C17A 1.085(16) . ? C17B C18B 1.471(12) . ? C17B C20B 1.56(2) 2_666 ? C17B H17B 0.9892 . ? C17B H17A 1.2182 . ? C18B C19B 1.264(10) . ? C18B C17A 1.472(16) . ? C18B H18B 0.9367 . ? C18B H18A 0.9784 . ? C19B C20B 1.361(14) . ? C19B C20A 1.75(3) . ? C19B H19B 0.9338 . ? C19B H19A 0.9965 . ? C20B C20A 1.27(2) . ? C20B C17B 1.56(2) 2_666 ? C20B H20B 0.9842 . ? N1A C16A 1.34(2) . ? N1A C20A 1.41(3) . ? N1A H1NB 0.8625 . ? N1A H1NA 0.8670 . ? C16A C17A 1.49(2) . ? C17A H17B 1.3325 . ? C17A H17A 0.9348 . ? C20A H20B 1.2094 . ? C20A H20A 0.9339 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.8(5) . 2_576 ? C1 C2 C3 174.5(3) . . ? O1 C3 C2 108.9(2) . . ? O1 C3 C4 106.6(2) . . ? C2 C3 C4 112.4(2) . . ? O1 C3 C10 111.1(2) . . ? C2 C3 C10 108.8(2) . . ? C4 C3 C10 109.06(19) . . ? C5 C4 C9 118.8(3) . . ? C5 C4 C3 122.4(2) . . ? C9 C4 C3 118.8(2) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C4 C9 C8 120.9(3) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C15 C10 C11 118.7(3) . . ? C15 C10 C3 120.3(2) . . ? C11 C10 C3 121.0(2) . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.3(3) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 120.9(3) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C16A O2 C16B 38.1(10) . . ? N1A N1B C16B 91.5(11) . . ? N1A N1B C20A 70.4(15) . . ? C16B N1B C20A 125.3(12) . . ? N1A N1B C20B 122.5(15) . . ? C16B N1B C20B 118.2(8) . . ? C20A N1B C20B 52.1(11) . . ? N1A N1B C16A 58.0(11) . . ? C16B N1B C16A 33.5(6) . . ? C20A N1B C16A 109.0(11) . . ? C20B N1B C16A 135.7(10) . . ? N1A N1B H1NB 56.4 . . ? C16B N1B H1NB 121.1 . . ? C20A N1B H1NB 91.6 . . ? C20B N1B H1NB 120.8 . . ? C16A N1B H1NB 96.5 . . ? C16A C16B C17A 91.2(17) . . ? C16A C16B N1B 88.9(16) . . ? C17A C16B N1B 116.8(11) . . ? C16A C16B O2 47.6(14) . . ? C17A C16B O2 106.5(9) . . ? N1B C16B O2 118.6(9) . . ? C16A C16B C17B 136.1(16) . . ? C17A C16B C17B 45.4(9) . . ? N1B C16B C17B 114.1(8) . . ? O2 C16B C17B 127.3(6) . . ? C16A C16B N1A 53.8(15) . . ? C17A C16B N1A 110.5(11) . . ? N1B C16B N1A 35.1(4) . . ? O2 C16B N1A 90.8(8) . . ? C17B C16B N1A 136.7(8) . . ? C17A C17B C18B 68.4(11) . . ? C17A C17B C16B 51.5(10) . . ? C18B C17B C16B 98.8(8) . . ? C17A C17B C20B 161.1(14) . 2_666 ? C18B C17B C20B 119.0(9) . 2_666 ? C16B C17B C20B 109.7(8) . 2_666 ? C17A C17B H17B 79.8 . . ? C18B C17B H17B 109.7 . . ? C16B C17B H17B 107.5 . . ? C20B C17B H17B 111.0 2_666 . ? C17A C17B H17A 47.5 . . ? C18B C17B H17A 97.2 . . ? C16B C17B H17A 79.9 . . ? C20B C17B H17A 139.3 2_666 . ? H17B C17B H17A 32.9 . . ? C19B C18B C17B 123.6(7) . . ? C19B C18B C17A 116.7(10) . . ? C17B C18B C17A 43.3(6) . . ? C19B C18B H18B 119.6 . . ? C17B C18B H18B 116.7 . . ? C17A C18B H18B 108.1 . . ? C19B C18B H18A 118.7 . . ? C17B C18B H18A 105.9 . . ? C17A C18B H18A 124.1 . . ? H18B C18B H18A 34.2 . . ? C18B C19B C20B 115.1(6) . . ? C18B C19B C20A 116.1(8) . . ? C20B C19B C20A 46.2(6) . . ? C18B C19B H19B 121.7 . . ? C20B C19B H19B 123.0 . . ? C20A C19B H19B 107.6 . . ? C18B C19B H19A 116.4 . . ? C20B C19B H19A 106.0 . . ? C20A C19B H19A 127.4 . . ? H19B C19B H19A 43.1 . . ? C20A C20B C19B 83.4(16) . . ? C20A C20B N1B 60.9(11) . . ? C19B C20B N1B 107.5(8) . . ? C20A C20B C17B 155.2(17) . 2_666 ? C19B C20B C17B 121.3(9) . 2_666 ? N1B C20B C17B 105.7(9) . 2_666 ? C20A C20B H20B 63.2 . . ? C19B C20B H20B 106.8 . . ? N1B C20B H20B 108.3 . . ? C17B C20B H20B 106.6 2_666 . ? N1B N1A C16A 84.9(15) . . ? N1B N1A C20A 70.2(14) . . ? C16A N1A C20A 124.1(16) . . ? N1B N1A C16B 53.4(10) . . ? C16A N1A C16B 31.6(7) . . ? C20A N1A C16B 104.8(14) . . ? N1B N1A H1NB 56.9 . . ? C16A N1A H1NB 115.6 . . ? C20A N1A H1NB 91.7 . . ? C16B N1A H1NB 94.5 . . ? N1B N1A H1NA 113.9 . . ? C16A N1A H1NA 119.4 . . ? C20A N1A H1NA 116.4 . . ? C16B N1A H1NA 128.9 . . ? H1NB N1A H1NA 57.2 . . ? C16B C16A O2 94(2) . . ? C16B C16A N1A 94.6(18) . . ? O2 C16A N1A 133.0(15) . . ? C16B C16A C17A 53.2(13) . . ? O2 C16A C17A 109.7(16) . . ? N1A C16A C17A 112.5(15) . . ? C16B C16A N1B 57.6(13) . . ? O2 C16A N1B 127.0(13) . . ? N1A C16A N1B 37.1(8) . . ? C17A C16A N1B 89.0(12) . . ? C17B C17A C16B 83.1(14) . . ? C17B C17A C18B 68.3(12) . . ? C16B C17A C18B 116.0(12) . . ? C17B C17A C16A 118.4(16) . . ? C16B C17A C16A 35.7(7) . . ? C18B C17A C16A 131.6(14) . . ? C17B C17A H17B 46.9 . . ? C16B C17A H17B 107.8 . . ? C18B C17A H17B 92.6 . . ? C16A C17A H17B 128.3 . . ? C17B C17A H17A 73.8 . . ? C16B C17A H17A 112.0 . . ? C18B C17A H17A 112.5 . . ? C16A C17A H17A 115.2 . . ? H17B C17A H17A 27.5 . . ? C20B C20A N1B 66.9(8) . . ? C20B C20A N1A 106.3(13) . . ? N1B C20A N1A 39.4(8) . . ? C20B C20A C19B 50.4(14) . . ? N1B C20A C19B 92.4(12) . . ? N1A C20A C19B 117.8(12) . . ? C20B C20A H20B 46.6 . . ? N1B C20A H20B 100.8 . . ? N1A C20A H20B 133.0 . . ? C19B C20A H20B 77.1 . . ? C20B C20A H20A 113.6 . . ? N1B C20A H20A 140.5 . . ? N1A C20A H20A 122.9 . . ? C19B C20A H20A 119.0 . . ? H20B C20A H20A 67.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -75(100) 2_576 . . . ? C1 C2 C3 O1 -40(3) . . . . ? C1 C2 C3 C4 -158(3) . . . . ? C1 C2 C3 C10 81(3) . . . . ? O1 C3 C4 C5 -131.8(3) . . . . ? C2 C3 C4 C5 -12.5(4) . . . . ? C10 C3 C4 C5 108.2(3) . . . . ? O1 C3 C4 C9 49.3(3) . . . . ? C2 C3 C4 C9 168.5(2) . . . . ? C10 C3 C4 C9 -70.8(3) . . . . ? C9 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 C6 -179.6(3) . . . . ? C4 C5 C6 C7 -0.3(5) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C5 C4 C9 C8 1.0(4) . . . . ? C3 C4 C9 C8 -180.0(3) . . . . ? C7 C8 C9 C4 -0.5(5) . . . . ? O1 C3 C10 C15 171.7(2) . . . . ? C2 C3 C10 C15 51.7(3) . . . . ? C4 C3 C10 C15 -71.2(3) . . . . ? O1 C3 C10 C11 -10.9(3) . . . . ? C2 C3 C10 C11 -130.8(3) . . . . ? C4 C3 C10 C11 106.3(3) . . . . ? C15 C10 C11 C12 -0.2(4) . . . . ? C3 C10 C11 C12 -177.7(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 C15 -0.6(5) . . . . ? C13 C14 C15 C10 0.2(4) . . . . ? C11 C10 C15 C14 0.3(4) . . . . ? C3 C10 C15 C14 177.7(2) . . . . ? N1A N1B C16B C16A -2.8(19) . . . . ? C20A N1B C16B C16A -70(2) . . . . ? C20B N1B C16B C16A -131.4(16) . . . . ? N1A N1B C16B C17A 87.9(17) . . . . ? C20A N1B C16B C17A 21(2) . . . . ? C20B N1B C16B C17A -40.7(18) . . . . ? C16A N1B C16B C17A 90.7(19) . . . . ? N1A N1B C16B O2 -41.6(15) . . . . ? C20A N1B C16B O2 -108.5(17) . . . . ? C20B N1B C16B O2 -170.3(9) . . . . ? C16A N1B C16B O2 -38.8(12) . . . . ? N1A N1B C16B C17B 138.5(13) . . . . ? C20A N1B C16B C17B 71.6(18) . . . . ? C20B N1B C16B C17B 9.9(15) . . . . ? C16A N1B C16B C17B 141.3(19) . . . . ? C20A N1B C16B N1A -66.9(19) . . . . ? C20B N1B C16B N1A -128.6(19) . . . . ? C16A N1B C16B N1A 2.8(19) . . . . ? C16A O2 C16B C17A -76.0(19) . . . . ? C16A O2 C16B N1B 58.1(16) . . . . ? C16A O2 C16B C17B -122(2) . . . . ? C16A O2 C16B N1A 35.6(15) . . . . ? C16A C16B C17B C17A 11(3) . . . . ? N1B C16B C17B C17A -104.6(14) . . . . ? O2 C16B C17B C17A 75.6(14) . . . . ? N1A C16B C17B C17A -70.8(16) . . . . ? C16A C16B C17B C18B 64(2) . . . . ? C17A C16B C17B C18B 53.3(11) . . . . ? N1B C16B C17B C18B -51.3(11) . . . . ? O2 C16B C17B C18B 128.8(10) . . . . ? N1A C16B C17B C18B -17.6(14) . . . . ? C16A C16B C17B C20B -170(2) . . . 2_666 ? C17A C16B C17B C20B 178.4(15) . . . 2_666 ? N1B C16B C17B C20B 73.8(10) . . . 2_666 ? O2 C16B C17B C20B -106.0(9) . . . 2_666 ? N1A C16B C17B C20B 107.6(12) . . . 2_666 ? C17A C17B C18B C19B 94.6(14) . . . . ? C16B C17B C18B C19B 52.2(11) . . . . ? C20B C17B C18B C19B -66.2(13) 2_666 . . . ? C16B C17B C18B C17A -42.4(10) . . . . ? C20B C17B C18B C17A -160.8(15) 2_666 . . . ? C17B C18B C19B C20B -2.6(14) . . . . ? C17A C18B C19B C20B 47.2(13) . . . . ? C17B C18B C19B C20A -54.2(13) . . . . ? C17A C18B C19B C20A -4.3(14) . . . . ? C18B C19B C20B C20A -102.9(10) . . . . ? C18B C19B C20B N1B -46.2(11) . . . . ? C20A C19B C20B N1B 56.7(9) . . . . ? C18B C19B C20B C17B 75.5(10) . . . 2_666 ? C20A C19B C20B C17B 178.4(11) . . . 2_666 ? N1A N1B C20B C20A 2.4(18) . . . . ? C16B N1B C20B C20A 114.5(16) . . . . ? C16A N1B C20B C20A 78.1(18) . . . . ? N1A N1B C20B C19B -69.4(17) . . . . ? C16B N1B C20B C19B 42.7(13) . . . . ? C20A N1B C20B C19B -71.8(14) . . . . ? C16A N1B C20B C19B 6.4(17) . . . . ? N1A N1B C20B C17B 159.7(15) . . . 2_666 ? C16B N1B C20B C17B -88.2(11) . . . 2_666 ? C20A N1B C20B C17B 157.3(15) . . . 2_666 ? C16A N1B C20B C17B -124.6(14) . . . 2_666 ? C16B N1B N1A C16A 1.8(13) . . . . ? C20A N1B N1A C16A 129.1(13) . . . . ? C20B N1B N1A C16A 127.0(12) . . . . ? C16B N1B N1A C20A -127.2(12) . . . . ? C20B N1B N1A C20A -2.0(15) . . . . ? C16A N1B N1A C20A -129.1(13) . . . . ? C20A N1B N1A C16B 127.2(12) . . . . ? C20B N1B N1A C16B 125.2(15) . . . . ? C16A N1B N1A C16B -1.8(13) . . . . ? C16A C16B N1A N1B 177(2) . . . . ? C17A C16B N1A N1B -107.7(15) . . . . ? O2 C16B N1A N1B 144.3(14) . . . . ? C17B C16B N1A N1B -61.8(16) . . . . ? C17A C16B N1A C16A 75.7(19) . . . . ? N1B C16B N1A C16A -177(2) . . . . ? O2 C16B N1A C16A -32.2(15) . . . . ? C17B C16B N1A C16A 122(2) . . . . ? C16A C16B N1A C20A -132.7(19) . . . . ? C17A C16B N1A C20A -56.9(15) . . . . ? N1B C16B N1A C20A 50.8(15) . . . . ? O2 C16B N1A C20A -164.9(9) . . . . ? C17B C16B N1A C20A -11.0(16) . . . . ? C17A C16B C16A O2 111.5(12) . . . . ? N1B C16B C16A O2 -131.8(10) . . . . ? C17B C16B C16A O2 103.6(19) . . . . ? N1A C16B C16A O2 -133.8(16) . . . . ? C17A C16B C16A N1A -114.7(12) . . . . ? N1B C16B C16A N1A 2.0(14) . . . . ? O2 C16B C16A N1A 133.8(16) . . . . ? C17B C16B C16A N1A -122.6(16) . . . . ? N1B C16B C16A C17A 116.7(11) . . . . ? O2 C16B C16A C17A -111.5(12) . . . . ? C17B C16B C16A C17A -7.9(19) . . . . ? N1A C16B C16A C17A 114.7(12) . . . . ? C17A C16B C16A N1B -116.7(11) . . . . ? O2 C16B C16A N1B 131.8(10) . . . . ? C17B C16B C16A N1B -125(2) . . . . ? N1A C16B C16A N1B -2.0(14) . . . . ? C16B O2 C16A N1A -100(3) . . . . ? C16B O2 C16A C17A 52.3(14) . . . . ? C16B O2 C16A N1B -52.0(16) . . . . ? N1B N1A C16A C16B -2.8(19) . . . . ? C20A N1A C16A C16B 59(2) . . . . ? N1B N1A C16A O2 98(2) . . . . ? C20A N1A C16A O2 159(2) . . . . ? C16B N1A C16A O2 100(3) . . . . ? N1B N1A C16A C17A -54.7(17) . . . . ? C20A N1A C16A C17A 7(2) . . . . ? C16B N1A C16A C17A -51.9(14) . . . . ? C20A N1A C16A N1B 61.9(18) . . . . ? C16B N1A C16A N1B 2.8(19) . . . . ? N1A N1B C16A C16B 177(2) . . . . ? C20A N1B C16A C16B 126(2) . . . . ? C20B N1B C16A C16B 71(2) . . . . ? N1A N1B C16A O2 -115(2) . . . . ? C16B N1B C16A O2 69(2) . . . . ? C20A N1B C16A O2 -165(2) . . . . ? C20B N1B C16A O2 139.7(19) . . . . ? C16B N1B C16A N1A -177(2) . . . . ? C20A N1B C16A N1A -50.7(17) . . . . ? C20B N1B C16A N1A -106(2) . . . . ? N1A N1B C16A C17A 131.1(17) . . . . ? C16B N1B C16A C17A -45.6(13) . . . . ? C20A N1B C16A C17A 80.4(18) . . . . ? C20B N1B C16A C17A 25.6(19) . . . . ? C18B C17B C17A C16B -121.6(9) . . . . ? C20B C17B C17A C16B -5(4) 2_666 . . . ? C16B C17B C17A C18B 121.6(9) . . . . ? C20B C17B C17A C18B 117(4) 2_666 . . . ? C18B C17B C17A C16A -126.7(16) . . . . ? C16B C17B C17A C16A -5.1(12) . . . . ? C20B C17B C17A C16A -10(5) 2_666 . . . ? C16A C16B C17A C17B -172.3(18) . . . . ? N1B C16B C17A C17B 98.4(14) . . . . ? O2 C16B C17A C17B -126.5(10) . . . . ? N1A C16B C17A C17B 136.2(12) . . . . ? C16A C16B C17A C18B 126(2) . . . . ? N1B C16B C17A C18B 37(2) . . . . ? O2 C16B C17A C18B 171.7(14) . . . . ? C17B C16B C17A C18B -61.7(14) . . . . ? N1A C16B C17A C18B 74.5(19) . . . . ? N1B C16B C17A C16A -89.3(18) . . . . ? O2 C16B C17A C16A 45.8(14) . . . . ? C17B C16B C17A C16A 172.3(18) . . . . ? N1A C16B C17A C16A -51.5(16) . . . . ? C19B C18B C17A C17B -111.7(11) . . . . ? C19B C18B C17A C16B -42(2) . . . . ? C17B C18B C17A C16B 70.2(15) . . . . ? C19B C18B C17A C16A -2(2) . . . . ? C17B C18B C17A C16A 109(2) . . . . ? C16B C16A C17A C17B 9(2) . . . . ? O2 C16A C17A C17B -72(2) . . . . ? N1A C16A C17A C17B 87.1(19) . . . . ? N1B C16A C17A C17B 57.6(17) . . . . ? O2 C16A C17A C16B -80.3(18) . . . . ? N1A C16A C17A C16B 78.4(17) . . . . ? N1B C16A C17A C16B 48.9(11) . . . . ? C16B C16A C17A C18B -77(2) . . . . ? O2 C16A C17A C18B -157(2) . . . . ? N1A C16A C17A C18B 2(3) . . . . ? N1B C16A C17A C18B -28(2) . . . . ? C19B C20B C20A N1B 114.3(8) . . . . ? C17B C20B C20A N1B -62(2) 2_666 . . . ? C19B C20B C20A N1A 112.8(13) . . . . ? N1B C20B C20A N1A -1.4(11) . . . . ? C17B C20B C20A N1A -64(2) 2_666 . . . ? N1B C20B C20A C19B -114.3(7) . . . . ? C17B C20B C20A C19B -177(2) 2_666 . . . ? N1A N1B C20A C20B -177.8(16) . . . . ? C16B N1B C20A C20B -100.5(12) . . . . ? C16A N1B C20A C20B -133.7(10) . . . . ? C16B N1B C20A N1A 77.4(17) . . . . ? C20B N1B C20A N1A 177.8(16) . . . . ? C16A N1B C20A N1A 44.1(13) . . . . ? N1A N1B C20A C19B -133.2(13) . . . . ? C16B N1B C20A C19B -55.8(16) . . . . ? C20B N1B C20A C19B 44.7(11) . . . . ? C16A N1B C20A C19B -89.1(13) . . . . ? N1B N1A C20A C20B 2.1(16) . . . . ? C16A N1A C20A C20B -67(2) . . . . ? C16B N1A C20A C20B -39.3(17) . . . . ? C16A N1A C20A N1B -69.1(18) . . . . ? C16B N1A C20A N1B -41.4(11) . . . . ? N1B N1A C20A C19B 55.4(14) . . . . ? C16A N1A C20A C19B -14(2) . . . . ? C16B N1A C20A C19B 14.1(13) . . . . ? C18B C19B C20A C20B 100.6(8) . . . . ? C18B C19B C20A N1B 43.6(11) . . . . ? C20B C19B C20A N1B -57.1(8) . . . . ? C18B C19B C20A N1A 12.0(14) . . . . ? C20B C19B C20A N1A -88.6(13) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.229 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.047 data_I-c_40hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7430(10) _cell_length_b 7.751(2) _cell_length_c 13.459(3) _cell_angle_alpha 87.69(2) _cell_angle_beta 76.13(2) _cell_angle_gamma 85.27(2) _cell_volume 781.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7220 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7220 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2660 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+0.0389P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2660 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.2059 _refine_ls_wR_factor_gt 0.1826 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3265(2) 1.1355(2) 0.23679(14) 0.0517(6) Uani 1 1 d . . . H1 H 0.3993 1.0949 0.2684 0.15(2) Uiso 1 1 calc R . . C1 C 0.0346(4) 1.0050(4) 0.4483(2) 0.0515(7) Uani 1 1 d . . . C2 C 0.0946(4) 1.0154(3) 0.3583(2) 0.0485(7) Uani 1 1 d . . . C3 C 0.1862(3) 1.0247(3) 0.24934(18) 0.0409(6) Uani 1 1 d . . . C4 C 0.0631(3) 1.1028(3) 0.18325(18) 0.0398(6) Uani 1 1 d . . . C5 C -0.1178(4) 1.1292(4) 0.2196(2) 0.0573(8) Uani 1 1 d . . . H5 H -0.1702 1.0994 0.2871 0.043(7) Uiso 1 1 calc R . . C6 C -0.2222(4) 1.2000(5) 0.1564(3) 0.0704(10) Uani 1 1 d . . . H6 H -0.3452 1.2161 0.1811 0.077(10) Uiso 1 1 calc R . . C7 C -0.1472(4) 1.2460(4) 0.0589(3) 0.0649(9) Uani 1 1 d . . . H7 H -0.2179 1.2970 0.0171 0.081(10) Uiso 1 1 calc R . . C8 C 0.0333(4) 1.2176(4) 0.0213(2) 0.0579(8) Uani 1 1 d . . . H8 H 0.0851 1.2470 -0.0463 0.079(10) Uiso 1 1 calc R . . C9 C 0.1368(4) 1.1463(4) 0.08333(19) 0.0484(7) Uani 1 1 d . . . H9 H 0.2592 1.1269 0.0575 0.063(9) Uiso 1 1 calc R . . C10 C 0.2551(3) 0.8444(3) 0.21246(17) 0.0393(6) Uani 1 1 d . . . C11 C 0.4285(3) 0.8094(4) 0.1592(2) 0.0507(7) Uani 1 1 d . . . H11 H 0.5071 0.8965 0.1472 0.065(9) Uiso 1 1 calc R . . C12 C 0.4863(4) 0.6455(4) 0.1236(2) 0.0574(8) Uani 1 1 d . . . H12 H 0.6037 0.6229 0.0870 0.079(10) Uiso 1 1 calc R . . C13 C 0.3735(4) 0.5167(4) 0.1413(2) 0.0567(8) Uani 1 1 d . . . H13 H 0.4137 0.4060 0.1176 0.073(10) Uiso 1 1 calc R . . C14 C 0.2003(4) 0.5504(4) 0.1943(2) 0.0574(8) Uani 1 1 d . . . H14 H 0.1222 0.4628 0.2060 0.066(9) Uiso 1 1 calc R . . C15 C 0.1423(4) 0.7114(4) 0.2296(2) 0.0497(7) Uani 1 1 d . . . H15 H 0.0247 0.7327 0.2660 0.080(10) Uiso 1 1 calc R . . O2 O 0.4753(4) 0.1408(5) 0.3971(2) 0.0984(11) Uani 1 1 d . . . N1B N 0.4828(13) 0.2743(9) 0.5457(5) 0.098(2) Uani 0.707(13) 1 d P . . H1NB H 0.5294 0.1802 0.5676 0.118 Uiso 0.707(13) 1 d PR . . C16B C 0.4531(9) 0.2822(12) 0.4533(4) 0.0642(19) Uani 0.707(13) 1 d P . . C17B C 0.3942(13) 0.4565(12) 0.4196(6) 0.090(2) Uani 0.707(13) 1 d P . . H17B H 0.3428 0.4475 0.3603 0.108 Uiso 0.707(13) 1 d PR . . C18B C 0.2570(7) 0.5161(10) 0.5073(7) 0.161(3) Uani 1 1 d . . . H18B H 0.1490 0.5633 0.4957 0.194 Uiso 0.707(13) 1 d PR . . C19B C 0.2740(9) 0.5049(10) 0.5976(7) 0.143(3) Uani 1 1 d . . . H19B H 0.1869 0.5486 0.6529 0.172 Uiso 0.707(13) 1 d PR . . C20B C 0.4377(14) 0.4258(9) 0.6088(4) 0.109(4) Uani 0.707(13) 1 d P . . H20B H 0.4243 0.3878 0.6804 0.131 Uiso 0.707(13) 1 d PR . . N1A N 0.4245(19) 0.179(4) 0.5594(12) 0.100(6) Uani 0.293(13) 1 d P . . H1NA H 0.4898 0.0922 0.5752 0.120 Uiso 0.293(13) 1 d PR . . C16A C 0.407(3) 0.193(3) 0.4585(19) 0.085(6) Uani 0.293(13) 1 d P . . C17A C 0.317(3) 0.369(3) 0.4463(17) 0.101(7) Uani 0.293(13) 1 d P . . H17A H 0.3137 0.3921 0.3785 0.122 Uiso 0.293(13) 1 d PR . . C20A C 0.343(3) 0.301(5) 0.6392(15) 0.183(17) Uani 0.293(13) 1 d P . . H20A H 0.3276 0.2744 0.7086 0.220 Uiso 0.293(13) 1 d PR . . H18A H 0.1902 0.6145 0.4904 0.220 Uiso 0.29 1 d P . . H19A H 0.2501 0.6033 0.6404 0.220 Uiso 0.29 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0594(12) 0.0478(12) 0.0518(11) 0.0035(9) -0.0202(9) -0.0090(9) C1 0.0627(18) 0.0491(17) 0.0400(14) -0.0017(12) -0.0108(13) 0.0078(13) C2 0.0606(17) 0.0420(17) 0.0421(16) -0.0011(12) -0.0137(13) 0.0050(12) C3 0.0494(15) 0.0357(15) 0.0372(14) 0.0011(11) -0.0103(11) -0.0016(11) C4 0.0494(15) 0.0303(14) 0.0399(14) -0.0028(10) -0.0119(11) 0.0010(10) C5 0.0518(17) 0.063(2) 0.0517(18) 0.0055(14) -0.0048(13) 0.0040(14) C6 0.0481(19) 0.084(3) 0.078(2) 0.0060(19) -0.0194(15) 0.0139(15) C7 0.070(2) 0.062(2) 0.070(2) 0.0081(16) -0.0368(17) 0.0063(15) C8 0.069(2) 0.061(2) 0.0458(17) 0.0098(14) -0.0201(14) -0.0034(15) C9 0.0490(16) 0.0545(18) 0.0401(15) 0.0020(13) -0.0092(12) 0.0008(12) C10 0.0476(14) 0.0369(15) 0.0327(13) 0.0022(10) -0.0114(11) 0.0044(11) C11 0.0459(15) 0.0498(19) 0.0521(16) 0.0007(13) -0.0048(12) 0.0001(13) C12 0.0571(18) 0.054(2) 0.0547(17) -0.0015(14) -0.0068(14) 0.0148(15) C13 0.077(2) 0.0404(18) 0.0499(17) -0.0018(13) -0.0165(14) 0.0145(15) C14 0.074(2) 0.0371(18) 0.0595(18) 0.0060(13) -0.0138(15) -0.0033(15) C15 0.0512(16) 0.0407(17) 0.0531(16) 0.0002(13) -0.0064(13) 0.0016(13) O2 0.089(2) 0.149(3) 0.0610(18) -0.0070(18) -0.0325(15) 0.0111(19) N1B 0.158(6) 0.091(4) 0.062(3) 0.011(3) -0.058(4) -0.018(4) C16B 0.068(4) 0.088(5) 0.045(3) -0.006(3) -0.026(2) -0.014(4) C17B 0.102(6) 0.106(6) 0.075(4) 0.004(4) -0.053(4) 0.008(4) C18B 0.082(4) 0.208(8) 0.212(8) -0.090(7) -0.067(5) 0.019(4) C19B 0.085(4) 0.161(6) 0.160(6) -0.060(5) 0.035(4) -0.036(4) C20B 0.203(10) 0.096(5) 0.032(3) 0.004(3) -0.033(4) -0.019(6) N1A 0.071(8) 0.16(2) 0.068(9) -0.038(11) -0.016(6) 0.011(9) C16A 0.056(10) 0.087(15) 0.120(18) -0.020(13) -0.040(10) 0.006(9) C17A 0.085(13) 0.118(19) 0.101(13) -0.010(12) -0.033(10) 0.029(12) C20A 0.156(19) 0.34(4) 0.071(11) -0.017(18) -0.006(11) -0.17(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.414(3) . ? O1 H1 0.8200 . ? C1 C2 1.191(3) . ? C1 C1 1.367(5) 2_576 ? C2 C3 1.470(4) . ? C3 C10 1.513(3) . ? C3 C4 1.528(3) . ? C4 C9 1.370(3) . ? C4 C5 1.369(4) . ? C5 C6 1.377(4) . ? C5 H5 0.9300 . ? C6 C7 1.349(4) . ? C6 H6 0.9300 . ? C7 C8 1.370(4) . ? C7 H7 0.9300 . ? C8 C9 1.362(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.373(4) . ? C10 C15 1.383(4) . ? C11 C12 1.377(4) . ? C11 H11 0.9300 . ? C12 C13 1.357(4) . ? C12 H12 0.9300 . ? C13 C14 1.369(4) . ? C13 H13 0.9300 . ? C14 C15 1.355(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 0.95(2) . ? O2 C16B 1.333(9) . ? N1B N1A 0.89(2) . ? N1B C16B 1.315(8) . ? N1B C20B 1.447(9) . ? N1B C20A 1.46(2) . ? N1B C16A 1.60(2) . ? N1B H1NB 0.8600 . ? N1B H1NA 1.4511 . ? C16B C16A 0.79(2) . ? C16B C17A 1.223(19) . ? C16B C17B 1.479(11) . ? C16B N1A 1.58(2) . ? C17B C17A 0.94(2) . ? C17B C18B 1.448(11) . ? C17B C20B 1.613(16) 2_666 ? C17B H17B 0.9800 . ? C17B H17A 1.0875 . ? C18B C19B 1.253(9) . ? C18B C17A 1.41(2) . ? C18B H18B 0.9300 . ? C18B H18A 0.9370 . ? C19B C20B 1.400(11) . ? C19B C20A 1.74(4) . ? C19B H19B 0.9300 . ? C19B H19A 0.9536 . ? C20B C20A 1.26(3) . ? C20B C17B 1.613(16) 2_666 ? C20B H20B 0.9800 . ? N1A C16A 1.40(3) . ? N1A C20A 1.45(3) . ? N1A H1NB 0.8462 . ? N1A H1NA 0.8600 . ? C16A C17A 1.50(3) . ? C17A H17B 1.2660 . ? C17A H17A 0.9300 . ? C20A H20B 1.1902 . ? C20A H20A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.4(4) . 2_576 ? C1 C2 C3 174.3(3) . . ? O1 C3 C2 108.9(2) . . ? O1 C3 C10 111.5(2) . . ? C2 C3 C10 109.3(2) . . ? O1 C3 C4 106.30(19) . . ? C2 C3 C4 112.2(2) . . ? C10 C3 C4 108.64(19) . . ? C9 C4 C5 118.8(2) . . ? C9 C4 C3 118.5(2) . . ? C5 C4 C3 122.7(2) . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.9(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 120.9(3) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? C11 C10 C15 118.3(2) . . ? C11 C10 C3 121.3(2) . . ? C15 C10 C3 120.4(2) . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 121.2(3) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? C16A O2 C16B 36.0(15) . . ? N1A N1B C16B 89.9(13) . . ? N1A N1B C20B 123.0(15) . . ? C16B N1B C20B 119.2(6) . . ? N1A N1B C20A 71.8(16) . . ? C16B N1B C20A 123.8(13) . . ? C20B N1B C20A 51.2(13) . . ? N1A N1B C16A 60.4(14) . . ? C16B N1B C16A 29.6(8) . . ? C20B N1B C16A 136.0(9) . . ? C20A N1B C16A 111.2(11) . . ? N1A N1B H1NB 57.9 . . ? C16B N1B H1NB 120.0 . . ? C20B N1B H1NB 120.8 . . ? C20A N1B H1NB 94.6 . . ? C16A N1B H1NB 98.4 . . ? N1A N1B H1NA 33.2 . . ? C16B N1B H1NA 106.2 . . ? C20B N1B H1NA 129.8 . . ? C20A N1B H1NA 86.8 . . ? C16A N1B H1NA 79.2 . . ? H1NB N1B H1NA 25.0 . . ? C16A C16B C17A 93(2) . . ? C16A C16B N1B 96(2) . . ? C17A C16B N1B 114.5(12) . . ? C16A C16B O2 45.0(18) . . ? C17A C16B O2 110.5(11) . . ? N1B C16B O2 120.9(7) . . ? C16A C16B C17B 130.6(17) . . ? C17A C16B C17B 39.4(11) . . ? N1B C16B C17B 114.8(7) . . ? O2 C16B C17B 124.3(5) . . ? C16A C16B N1A 62(2) . . ? C17A C16B N1A 111.0(13) . . ? N1B C16B N1A 34.0(6) . . ? O2 C16B N1A 94.7(8) . . ? C17B C16B N1A 135.1(9) . . ? C17A C17B C18B 68.7(16) . . ? C17A C17B C16B 55.5(14) . . ? C18B C17B C16B 102.9(7) . . ? C17A C17B C20B 163.6(17) . 2_666 ? C18B C17B C20B 113.7(7) . 2_666 ? C16B C17B C20B 109.2(6) . 2_666 ? C17A C17B H17B 82.3 . . ? C18B C17B H17B 110.1 . . ? C16B C17B H17B 110.0 . . ? C20B C17B H17B 110.5 2_666 . ? C17A C17B H17A 53.9 . . ? C18B C17B H17A 99.9 . . ? C16B C17B H17A 87.1 . . ? C20B C17B H17A 137.0 2_666 . ? H17B C17B H17A 28.8 . . ? C19B C18B C17B 124.0(6) . . ? C19B C18B C17A 116.7(12) . . ? C17B C18B C17A 38.5(9) . . ? C19B C18B H18B 118.3 . . ? C17B C18B H18B 117.8 . . ? C17A C18B H18B 109.8 . . ? C19B C18B H18A 116.2 . . ? C17B C18B H18A 111.2 . . ? C17A C18B H18A 126.4 . . ? H18B C18B H18A 32.5 . . ? C18B C19B C20B 114.6(5) . . ? C18B C19B C20A 116.2(9) . . ? C20B C19B C20A 45.6(7) . . ? C18B C19B H19B 123.0 . . ? C20B C19B H19B 122.4 . . ? C20A C19B H19B 104.7 . . ? C18B C19B H19A 121.2 . . ? C20B C19B H19A 106.0 . . ? C20A C19B H19A 122.6 . . ? H19B C19B H19A 41.1 . . ? C20A C20B C19B 81.6(18) . . ? C20A C20B N1B 64.9(13) . . ? C19B C20B N1B 109.1(6) . . ? C20A C20B C17B 161.8(19) . 2_666 ? C19B C20B C17B 116.5(6) . 2_666 ? N1B C20B C17B 107.5(7) . 2_666 ? C20A C20B H20B 62.9 . . ? C19B C20B H20B 108.3 . . ? N1B C20B H20B 108.1 . . ? C17B C20B H20B 107.0 2_666 . ? N1B N1A C16A 86.0(18) . . ? N1B N1A C20A 72.7(17) . . ? C16A N1A C20A 125(2) . . ? N1B N1A C16B 56.1(14) . . ? C16A N1A C16B 30.1(9) . . ? C20A N1A C16B 107.4(19) . . ? N1B N1A H1NB 59.5 . . ? C16A N1A H1NB 116.1 . . ? C20A N1A H1NB 95.8 . . ? C16B N1A H1NB 98.0 . . ? N1B N1A H1NA 112.4 . . ? C16A N1A H1NA 117.5 . . ? C20A N1A H1NA 117.5 . . ? C16B N1A H1NA 127.3 . . ? H1NB N1A H1NA 53.2 . . ? C16B C16A O2 99(3) . . ? C16B C16A N1A 88(2) . . ? O2 C16A N1A 131.9(18) . . ? C16B C16A N1B 54.8(15) . . ? O2 C16A N1B 126.9(16) . . ? N1A C16A N1B 33.5(10) . . ? C16B C16A C17A 54.6(16) . . ? O2 C16A C17A 116(2) . . ? N1A C16A C17A 106.7(19) . . ? N1B C16A C17A 87.0(15) . . ? C17B C17A C16B 85.1(18) . . ? C17B C17A C18B 72.8(19) . . ? C16B C17A C18B 120.5(17) . . ? C17B C17A C16A 115(2) . . ? C16B C17A C16A 32.0(10) . . ? C18B C17A C16A 137(2) . . ? C17B C17A H17B 50.1 . . ? C16B C17A H17B 109.7 . . ? C18B C17A H17B 97.0 . . ? C16A C17A H17B 121.3 . . ? C17B C17A H17A 71.0 . . ? C16B C17A H17A 111.9 . . ? C18B C17A H17A 111.4 . . ? C16A C17A H17A 111.1 . . ? H17B C17A H17A 21.4 . . ? C20B C20A N1B 63.9(9) . . ? C20B C20A N1A 99.4(16) . . ? N1B C20A N1A 35.4(10) . . ? C20B C20A C19B 52.8(17) . . ? N1B C20A C19B 92.5(15) . . ? N1A C20A C19B 115.8(16) . . ? C20B C20A H20B 47.2 . . ? N1B C20A H20B 96.5 . . ? N1A C20A H20B 124.5 . . ? C19B C20A H20B 80.9 . . ? C20B C20A H20A 114.3 . . ? N1B C20A H20A 137.4 . . ? N1A C20A H20A 123.2 . . ? C19B C20A H20A 121.0 . . ? H20B C20A H20A 67.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 107(36) 2_576 . . . ? C1 C2 C3 O1 -49(3) . . . . ? C1 C2 C3 C10 73(3) . . . . ? C1 C2 C3 C4 -167(3) . . . . ? O1 C3 C4 C9 50.2(3) . . . . ? C2 C3 C4 C9 169.2(2) . . . . ? C10 C3 C4 C9 -69.8(3) . . . . ? O1 C3 C4 C5 -130.5(3) . . . . ? C2 C3 C4 C5 -11.5(3) . . . . ? C10 C3 C4 C5 109.5(3) . . . . ? C9 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C6 -179.9(3) . . . . ? C4 C5 C6 C7 -1.0(5) . . . . ? C5 C6 C7 C8 1.9(5) . . . . ? C6 C7 C8 C9 -1.4(5) . . . . ? C7 C8 C9 C4 -0.2(4) . . . . ? C5 C4 C9 C8 1.2(4) . . . . ? C3 C4 C9 C8 -179.5(2) . . . . ? O1 C3 C10 C11 -9.6(3) . . . . ? C2 C3 C10 C11 -130.2(3) . . . . ? C4 C3 C10 C11 107.1(3) . . . . ? O1 C3 C10 C15 172.0(2) . . . . ? C2 C3 C10 C15 51.5(3) . . . . ? C4 C3 C10 C15 -71.2(3) . . . . ? C15 C10 C11 C12 0.5(4) . . . . ? C3 C10 C11 C12 -177.9(2) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C13 C14 C15 C10 0.5(4) . . . . ? C11 C10 C15 C14 -0.5(4) . . . . ? C3 C10 C15 C14 177.9(2) . . . . ? N1A N1B C16B C16A -5(2) . . . . ? C20B N1B C16B C16A -133.3(17) . . . . ? C20A N1B C16B C16A -73(3) . . . . ? N1A N1B C16B C17A 91.7(18) . . . . ? C20B N1B C16B C17A -36.8(18) . . . . ? C20A N1B C16B C17A 24(2) . . . . ? C16A N1B C16B C17A 96(2) . . . . ? N1A N1B C16B O2 -44.5(16) . . . . ? C20B N1B C16B O2 -172.9(7) . . . . ? C20A N1B C16B O2 -112.3(18) . . . . ? C16A N1B C16B O2 -39.7(15) . . . . ? N1A N1B C16B C17B 135.3(14) . . . . ? C20B N1B C16B C17B 6.8(11) . . . . ? C20A N1B C16B C17B 67.4(19) . . . . ? C16A N1B C16B C17B 140(2) . . . . ? C20B N1B C16B N1A -128.5(19) . . . . ? C20A N1B C16B N1A -68(2) . . . . ? C16A N1B C16B N1A 5(2) . . . . ? C16A O2 C16B C17A -74(2) . . . . ? C16A O2 C16B N1B 64(2) . . . . ? C16A O2 C16B C17B -116(2) . . . . ? C16A O2 C16B N1A 41(2) . . . . ? C16A C16B C17B C17A 24(3) . . . . ? N1B C16B C17B C17A -99.1(18) . . . . ? O2 C16B C17B C17A 80.6(19) . . . . ? N1A C16B C17B C17A -65(2) . . . . ? C16A C16B C17B C18B 76(3) . . . . ? C17A C16B C17B C18B 52.4(17) . . . . ? N1B C16B C17B C18B -46.6(9) . . . . ? O2 C16B C17B C18B 133.1(7) . . . . ? N1A C16B C17B C18B -12.7(14) . . . . ? C16A C16B C17B C20B -163(3) . . . 2_666 ? C17A C16B C17B C20B 174(2) . . . 2_666 ? N1B C16B C17B C20B 74.5(8) . . . 2_666 ? O2 C16B C17B C20B -105.8(7) . . . 2_666 ? N1A C16B C17B C20B 108.4(12) . . . 2_666 ? C17A C17B C18B C19B 91.4(18) . . . . ? C16B C17B C18B C19B 46.9(11) . . . . ? C20B C17B C18B C19B -71.1(11) 2_666 . . . ? C16B C17B C18B C17A -44.5(14) . . . . ? C20B C17B C18B C17A -162.5(18) 2_666 . . . ? C17B C18B C19B C20B -1.2(12) . . . . ? C17A C18B C19B C20B 43.0(15) . . . . ? C17B C18B C19B C20A -51.9(13) . . . . ? C17A C18B C19B C20A -7.8(16) . . . . ? C18B C19B C20B C20A -103.3(11) . . . . ? C18B C19B C20B N1B -43.6(9) . . . . ? C20A C19B C20B N1B 59.7(10) . . . . ? C18B C19B C20B C17B 78.3(8) . . . 2_666 ? C20A C19B C20B C17B -178.4(11) . . . 2_666 ? N1A N1B C20B C20A 1(2) . . . . ? C16B N1B C20B C20A 111.7(19) . . . . ? C16A N1B C20B C20A 81(2) . . . . ? N1A N1B C20B C19B -70.0(19) . . . . ? C16B N1B C20B C19B 41.1(10) . . . . ? C20A N1B C20B C19B -70.6(17) . . . . ? C16A N1B C20B C19B 9.9(17) . . . . ? N1A N1B C20B C17B 162.8(18) . . . 2_666 ? C16B N1B C20B C17B -86.1(8) . . . 2_666 ? C20A N1B C20B C17B 162.2(18) . . . 2_666 ? C16A N1B C20B C17B -117.3(15) . . . 2_666 ? C16B N1B N1A C16A 2.7(13) . . . . ? C20B N1B N1A C16A 128.1(12) . . . . ? C20A N1B N1A C16A 128.6(16) . . . . ? C16B N1B N1A C20A -125.9(14) . . . . ? C20B N1B N1A C20A -0.5(19) . . . . ? C16A N1B N1A C20A -128.6(16) . . . . ? C20B N1B N1A C16B 125.4(15) . . . . ? C20A N1B N1A C16B 125.9(14) . . . . ? C16A N1B N1A C16B -2.7(13) . . . . ? C16A C16B N1A N1B 175(3) . . . . ? C17A C16B N1A N1B -103.0(17) . . . . ? O2 C16B N1A N1B 142.9(14) . . . . ? C17B C16B N1A N1B -64.9(16) . . . . ? C17A C16B N1A C16A 82(2) . . . . ? N1B C16B N1A C16A -175(3) . . . . ? O2 C16B N1A C16A -31.7(17) . . . . ? C17B C16B N1A C16A 121(2) . . . . ? C16A C16B N1A C20A -131(2) . . . . ? C17A C16B N1A C20A -49(2) . . . . ? N1B C16B N1A C20A 54.1(17) . . . . ? O2 C16B N1A C20A -163.0(12) . . . . ? C17B C16B N1A C20A -10.7(19) . . . . ? C17A C16B C16A O2 115.8(17) . . . . ? N1B C16B C16A O2 -129.1(14) . . . . ? C17B C16B C16A O2 101(2) . . . . ? N1A C16B C16A O2 -132.2(19) . . . . ? C17A C16B C16A N1A -112.0(14) . . . . ? N1B C16B C16A N1A 3.0(14) . . . . ? O2 C16B C16A N1A 132.2(19) . . . . ? C17B C16B C16A N1A -126.8(17) . . . . ? C17A C16B C16A N1B -115.1(13) . . . . ? O2 C16B C16A N1B 129.1(14) . . . . ? C17B C16B C16A N1B -130(2) . . . . ? N1A C16B C16A N1B -3.0(14) . . . . ? N1B C16B C16A C17A 115.1(13) . . . . ? O2 C16B C16A C17A -115.8(17) . . . . ? C17B C16B C16A C17A -15(2) . . . . ? N1A C16B C16A C17A 112.0(14) . . . . ? C16B O2 C16A N1A -96(3) . . . . ? C16B O2 C16A N1B -52(2) . . . . ? C16B O2 C16A C17A 55(2) . . . . ? N1B N1A C16A C16B -4(2) . . . . ? C20A N1A C16A C16B 61(3) . . . . ? N1B N1A C16A O2 96(3) . . . . ? C20A N1A C16A O2 162(3) . . . . ? C16B N1A C16A O2 101(4) . . . . ? C20A N1A C16A N1B 66(2) . . . . ? C16B N1A C16A N1B 4(2) . . . . ? N1B N1A C16A C17A -56.5(19) . . . . ? C20A N1A C16A C17A 9(3) . . . . ? C16B N1A C16A C17A -52.0(16) . . . . ? N1A N1B C16A C16B 175(3) . . . . ? C20B N1B C16A C16B 66(2) . . . . ? C20A N1B C16A C16B 122(2) . . . . ? N1A N1B C16A O2 -112(3) . . . . ? C16B N1B C16A O2 73(3) . . . . ? C20B N1B C16A O2 139(2) . . . . ? C20A N1B C16A O2 -165(3) . . . . ? C16B N1B C16A N1A -175(3) . . . . ? C20B N1B C16A N1A -108(2) . . . . ? C20A N1B C16A N1A -53(2) . . . . ? N1A N1B C16A C17A 127(2) . . . . ? C16B N1B C16A C17A -47.6(15) . . . . ? C20B N1B C16A C17A 19(2) . . . . ? C20A N1B C16A C17A 74(2) . . . . ? C18B C17B C17A C16B -124.0(12) . . . . ? C20B C17B C17A C16B -22(7) 2_666 . . . ? C16B C17B C17A C18B 124.0(12) . . . . ? C20B C17B C17A C18B 102(6) 2_666 . . . ? C18B C17B C17A C16A -134(2) . . . . ? C16B C17B C17A C16A -10.3(14) . . . . ? C20B C17B C17A C16A -32(8) 2_666 . . . ? C16A C16B C17A C17B -162(3) . . . . ? N1B C16B C17A C17B 99.9(16) . . . . ? O2 C16B C17A C17B -119.5(14) . . . . ? N1A C16B C17A C17B 136.7(16) . . . . ? C16A C16B C17A C18B 131(3) . . . . ? N1B C16B C17A C18B 33(3) . . . . ? O2 C16B C17A C18B 173.7(18) . . . . ? C17B C16B C17A C18B -67(2) . . . . ? N1A C16B C17A C18B 70(3) . . . . ? N1B C16B C17A C16A -98(2) . . . . ? O2 C16B C17A C16A 42.8(19) . . . . ? C17B C16B C17A C16A 162(3) . . . . ? N1A C16B C17A C16A -61(2) . . . . ? C19B C18B C17A C17B -111.8(15) . . . . ? C19B C18B C17A C16B -38(3) . . . . ? C17B C18B C17A C16B 73(2) . . . . ? C19B C18B C17A C16A -3(3) . . . . ? C17B C18B C17A C16A 109(3) . . . . ? C16B C16A C17A C17B 20(3) . . . . ? O2 C16A C17A C17B -63(3) . . . . ? N1A C16A C17A C17B 95(3) . . . . ? N1B C16A C17A C17B 67(2) . . . . ? O2 C16A C17A C16B -82(3) . . . . ? N1A C16A C17A C16B 75.3(19) . . . . ? N1B C16A C17A C16B 47.8(14) . . . . ? C16B C16A C17A C18B -72(3) . . . . ? O2 C16A C17A C18B -154(3) . . . . ? N1A C16A C17A C18B 3(3) . . . . ? N1B C16A C17A C18B -24(3) . . . . ? C19B C20B C20A N1B 115.7(8) . . . . ? C17B C20B C20A N1B -69(3) 2_666 . . . ? C19B C20B C20A N1A 115.4(16) . . . . ? N1B C20B C20A N1A -0.3(12) . . . . ? C17B C20B C20A N1A -69(3) 2_666 . . . ? N1B C20B C20A C19B -115.7(8) . . . . ? C17B C20B C20A C19B 175(3) 2_666 . . . ? N1A N1B C20A C20B -179(2) . . . . ? C16B N1B C20A C20B -102.3(10) . . . . ? C16A N1B C20A C20B -132.7(11) . . . . ? C16B N1B C20A N1A 77.1(19) . . . . ? C20B N1B C20A N1A 179(2) . . . . ? C16A N1B C20A N1A 46.8(18) . . . . ? N1A N1B C20A C19B -133.5(16) . . . . ? C16B N1B C20A C19B -56.4(15) . . . . ? C20B N1B C20A C19B 45.9(12) . . . . ? C16A N1B C20A C19B -86.8(14) . . . . ? N1B N1A C20A C20B 0.5(18) . . . . ? C16A N1A C20A C20B -72(3) . . . . ? C16B N1A C20A C20B -44(2) . . . . ? C16A N1A C20A N1B -72(2) . . . . ? C16B N1A C20A N1B -44.8(15) . . . . ? N1B N1A C20A C19B 53.5(16) . . . . ? C16A N1A C20A C19B -19(2) . . . . ? C16B N1A C20A C19B 8.8(16) . . . . ? C18B C19B C20A C20B 99.7(9) . . . . ? C18B C19B C20A N1B 45.6(11) . . . . ? C20B C19B C20A N1B -54.1(8) . . . . ? C18B C19B C20A N1A 17.7(16) . . . . ? C20B C19B C20A N1A -81.9(14) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.328 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044 data_I-c_60hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7400(10) _cell_length_b 7.780(2) _cell_length_c 13.527(3) _cell_angle_alpha 87.86(2) _cell_angle_beta 76.29(2) _cell_angle_gamma 85.79(2) _cell_volume 789.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7650 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7650 _diffrn_reflns_av_R_equivalents 0.086 _diffrn_reflns_av_sigmaI/netI 0.0913 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2767 _reflns_number_gt 1428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2767 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 0.764 _refine_ls_restrained_S_all 0.764 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3268(2) 1.1373(2) 0.23755(12) 0.0551(5) Uani 1 1 d . . . H1 H 0.3996 1.0971 0.2689 0.18(2) Uiso 1 1 calc R . . C1 C 0.0344(3) 1.0048(3) 0.44792(19) 0.0536(6) Uani 1 1 d . . . C2 C 0.0952(3) 1.0157(3) 0.35867(19) 0.0530(6) Uani 1 1 d . . . C3 C 0.1864(3) 1.0263(3) 0.24971(16) 0.0438(6) Uani 1 1 d . . . C4 C 0.0628(3) 1.1023(3) 0.18397(17) 0.0427(6) Uani 1 1 d . . . C5 C -0.1175(3) 1.1296(3) 0.2199(2) 0.0593(7) Uani 1 1 d . . . H5 H -0.1703 1.1001 0.2870 0.045(6) Uiso 1 1 calc R . . C6 C -0.2219(4) 1.2013(4) 0.1563(2) 0.0743(9) Uani 1 1 d . . . H6 H -0.3445 1.2183 0.1810 0.092(10) Uiso 1 1 calc R . . C7 C -0.1472(4) 1.2468(4) 0.0586(2) 0.0679(8) Uani 1 1 d . . . H7 H -0.2178 1.2973 0.0171 0.080(8) Uiso 1 1 calc R . . C8 C 0.0324(4) 1.2181(4) 0.0214(2) 0.0621(7) Uani 1 1 d . . . H8 H 0.0845 1.2473 -0.0458 0.072(8) Uiso 1 1 calc R . . C9 C 0.1360(3) 1.1455(3) 0.08409(17) 0.0524(6) Uani 1 1 d . . . H9 H 0.2580 1.1253 0.0582 0.063(8) Uiso 1 1 calc R . . C10 C 0.2556(3) 0.8442(3) 0.21322(16) 0.0422(6) Uani 1 1 d . . . C11 C 0.4288(3) 0.8109(3) 0.15991(18) 0.0552(7) Uani 1 1 d . . . H11 H 0.5074 0.8984 0.1478 0.052(7) Uiso 1 1 calc R . . C12 C 0.4866(3) 0.6464(4) 0.12417(19) 0.0608(7) Uani 1 1 d . . . H12 H 0.6040 0.6245 0.0883 0.080(9) Uiso 1 1 calc R . . C13 C 0.3734(4) 0.5171(4) 0.14105(19) 0.0591(7) Uani 1 1 d . . . H13 H 0.4132 0.4073 0.1169 0.082(9) Uiso 1 1 calc R . . C14 C 0.1998(4) 0.5496(3) 0.1940(2) 0.0602(7) Uani 1 1 d . . . H14 H 0.1216 0.4618 0.2061 0.067(8) Uiso 1 1 calc R . . C15 C 0.1421(3) 0.7124(3) 0.22903(19) 0.0543(7) Uani 1 1 d . . . H15 H 0.0241 0.7340 0.2641 0.070(8) Uiso 1 1 calc R . . O2 O 0.4775(3) 0.1421(4) 0.39765(17) 0.0949(8) Uani 1 1 d . . . N1B N 0.4793(6) 0.2726(6) 0.5462(3) 0.0999(16) Uani 0.796(7) 1 d P . . H1NB H 0.5259 0.1786 0.5682 0.120 Uiso 0.796(7) 1 d PR . . C16B C 0.4541(6) 0.2801(7) 0.4527(3) 0.0682(13) Uani 0.796(7) 1 d P . . C17B C 0.3908(7) 0.4514(8) 0.4198(4) 0.0928(17) Uani 0.796(7) 1 d P . . H17B H 0.3395 0.4424 0.3605 0.111 Uiso 0.796(7) 1 d PR . . C18B C 0.2595(7) 0.5191(8) 0.5033(6) 0.163(2) Uani 1 1 d . . . H18B H 0.1515 0.5662 0.4917 0.195 Uiso 0.796(7) 1 d PR . . C19B C 0.2709(7) 0.5085(8) 0.5945(5) 0.141(2) Uani 1 1 d . . . H19B H 0.1837 0.5522 0.6497 0.170 Uiso 0.796(7) 1 d PR . . C20B C 0.4341(12) 0.4262(7) 0.6096(3) 0.130(3) Uani 0.796(7) 1 d P . . H20B H 0.4207 0.3882 0.6812 0.156 Uiso 0.796(7) 1 d PR . . N1A N 0.4192(19) 0.159(3) 0.5632(11) 0.095(5) Uiso 0.204(7) 1 d P . . H1NA H 0.4845 0.0721 0.5791 0.114 Uiso 0.204(7) 1 d PR . . C16A C 0.401(2) 0.190(3) 0.4596(16) 0.073(6) Uiso 0.204(7) 1 d P . . C17A C 0.316(3) 0.356(3) 0.4490(16) 0.091(6) Uiso 0.204(7) 1 d P . . H17A H 0.3121 0.3793 0.3812 0.110 Uiso 0.204(7) 1 d PR . . C20A C 0.350(3) 0.301(3) 0.6383(19) 0.115(8) Uiso 0.204(7) 1 d P . . H20A H 0.3342 0.2744 0.7077 0.138 Uiso 0.204(7) 1 d PR . . H18A H 0.1902 0.6145 0.4904 0.138 Uiso 0.20 1 d P . . H19A H 0.2501 0.6033 0.6404 0.138 Uiso 0.20 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0620(10) 0.0493(11) 0.0580(11) 0.0011(8) -0.0204(9) -0.0100(8) C1 0.0632(16) 0.0503(16) 0.0453(14) -0.0017(12) -0.0111(12) 0.0052(12) C2 0.0675(16) 0.0444(15) 0.0467(16) -0.0011(12) -0.0150(13) 0.0047(12) C3 0.0521(13) 0.0399(14) 0.0384(13) -0.0007(10) -0.0094(10) 0.0000(11) C4 0.0512(14) 0.0328(14) 0.0443(14) -0.0049(10) -0.0119(11) 0.0014(10) C5 0.0564(16) 0.0641(19) 0.0513(17) 0.0032(14) -0.0049(13) 0.0076(12) C6 0.0534(18) 0.084(2) 0.083(2) 0.0029(18) -0.0178(15) 0.0138(14) C7 0.0705(19) 0.067(2) 0.072(2) 0.0053(15) -0.0332(16) 0.0082(14) C8 0.0712(18) 0.0664(19) 0.0526(17) 0.0089(14) -0.0240(14) -0.0032(14) C9 0.0521(15) 0.0547(17) 0.0497(16) -0.0009(12) -0.0118(12) 0.0001(12) C10 0.0518(14) 0.0395(14) 0.0352(12) 0.0022(10) -0.0123(10) 0.0035(11) C11 0.0553(15) 0.0513(17) 0.0556(16) -0.0003(13) -0.0071(12) -0.0009(13) C12 0.0569(17) 0.0580(19) 0.0603(17) -0.0021(14) -0.0048(13) 0.0147(14) C13 0.0782(19) 0.0449(18) 0.0528(16) -0.0029(13) -0.0175(14) 0.0126(14) C14 0.0744(18) 0.0406(17) 0.0639(17) 0.0026(13) -0.0139(14) -0.0037(14) C15 0.0545(16) 0.0450(17) 0.0602(16) -0.0008(13) -0.0082(12) 0.0001(12) O2 0.0895(16) 0.139(2) 0.0621(14) -0.0096(15) -0.0315(13) 0.0043(14) N1B 0.159(4) 0.095(3) 0.058(2) 0.005(2) -0.052(2) -0.001(3) C16B 0.068(3) 0.089(3) 0.054(2) -0.011(2) -0.0238(18) -0.008(3) C17B 0.104(4) 0.105(4) 0.084(3) -0.005(3) -0.059(3) 0.019(4) C18B 0.105(4) 0.192(6) 0.212(6) -0.095(5) -0.077(4) 0.028(3) C19B 0.088(3) 0.164(5) 0.150(5) -0.059(4) 0.032(3) -0.035(3) C20B 0.262(8) 0.096(4) 0.041(3) 0.002(3) -0.052(4) -0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.413(3) . ? O1 H1 0.8200 . ? C1 C2 1.190(3) . ? C1 C1 1.384(5) 2_576 ? C2 C3 1.478(3) . ? C3 C10 1.534(3) . ? C3 C4 1.528(3) . ? C4 C5 1.368(3) . ? C4 C9 1.375(3) . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? C6 C7 1.356(4) . ? C6 H6 0.9300 . ? C7 C8 1.366(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.375(3) . ? C10 C15 1.377(3) . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.359(4) . ? C12 H12 0.9300 . ? C13 C14 1.375(4) . ? C13 H13 0.9300 . ? C14 C15 1.375(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 0.97(2) . ? O2 C16B 1.306(5) . ? N1B N1A 1.022(16) . ? N1B C16B 1.323(5) . ? N1B C20B 1.469(6) . ? N1B C20A 1.42(2) . ? N1B C16A 1.61(2) . ? N1B H1NB 0.8659 . ? N1B H1NA 1.6068 . ? C16B C16A 0.83(2) . ? C16B C17A 1.20(2) . ? C16B C17B 1.476(7) . ? C16B N1A 1.714(17) . ? C17B C17A 0.99(2) . ? C17B C18B 1.417(7) . ? C17B C20B 1.675(11) 2_666 ? C17B H17B 0.9823 . ? C17B H17A 1.0872 . ? C18B C19B 1.257(7) . ? C18B C17A 1.47(2) . ? C18B H18B 0.9332 . ? C18B H18A 0.9198 . ? C19B C20B 1.429(8) . ? C19B C20A 1.81(3) . ? C19B H19B 0.9356 . ? C19B H19A 0.9618 . ? C20B C20A 1.21(2) . ? C20B C17B 1.675(11) 2_666 ? C20B H20B 0.9858 . ? N1A C16A 1.45(2) . ? N1A C20A 1.51(3) . ? N1A H1NB 0.8688 . ? N1A H1NA 0.8659 . ? C16A C17A 1.43(3) . ? C17A H17B 1.3309 . ? C17A H17A 0.9351 . ? C20A H20B 1.1530 . ? C20A H20A 0.9354 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 178.8(4) . 2_576 ? C1 C2 C3 175.0(2) . . ? O1 C3 C2 108.90(18) . . ? O1 C3 C10 111.49(18) . . ? C2 C3 C10 108.67(18) . . ? O1 C3 C4 106.71(17) . . ? C2 C3 C4 112.37(18) . . ? C10 C3 C4 108.72(17) . . ? C5 C4 C9 118.4(2) . . ? C5 C4 C3 123.0(2) . . ? C9 C4 C3 118.56(19) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.6(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C4 121.4(2) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? C11 C10 C15 118.6(2) . . ? C11 C10 C3 121.0(2) . . ? C15 C10 C3 120.3(2) . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.6(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 121.3(2) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? C16A O2 C16B 39.4(12) . . ? N1A N1B C16B 93.0(9) . . ? N1A N1B C20B 124.3(10) . . ? C16B N1B C20B 119.5(4) . . ? N1A N1B C20A 74.7(13) . . ? C16B N1B C20A 127.5(9) . . ? C20B N1B C20A 49.6(10) . . ? N1A N1B C16A 62.1(11) . . ? C16B N1B C16A 30.9(7) . . ? C20B N1B C16A 135.8(8) . . ? C20A N1B C16A 113.3(11) . . ? N1A N1B H1NB 54.0 . . ? C16B N1B H1NB 119.4 . . ? C20B N1B H1NB 121.1 . . ? C20A N1B H1NB 94.2 . . ? C16A N1B H1NB 98.1 . . ? N1A N1B H1NA 28.9 . . ? C16B N1B H1NA 106.3 . . ? C20B N1B H1NA 129.8 . . ? C20A N1B H1NA 87.0 . . ? C16A N1B H1NA 78.6 . . ? H1NB N1B H1NA 25.4 . . ? C16A C16B C17A 87.7(17) . . ? C16A C16B N1B 94.2(16) . . ? C17A C16B N1B 111.8(11) . . ? C16A C16B O2 47.9(16) . . ? C17A C16B O2 109.7(11) . . ? N1B C16B O2 121.0(4) . . ? C16A C16B C17B 127.4(14) . . ? C17A C16B C17B 41.8(10) . . ? N1B C16B C17B 114.8(4) . . ? O2 C16B C17B 124.2(3) . . ? C16A C16B N1A 57.7(16) . . ? C17A C16B N1A 107.6(12) . . ? N1B C16B N1A 36.6(5) . . ? O2 C16B N1A 91.6(7) . . ? C17B C16B N1A 136.5(7) . . ? C17A C17B C18B 73.1(13) . . ? C17A C17B C16B 53.8(13) . . ? C18B C17B C16B 106.7(5) . . ? C17A C17B C20B 160.4(14) . 2_666 ? C18B C17B C20B 111.0(5) . 2_666 ? C16B C17B C20B 107.6(4) . 2_666 ? C17A C17B H17B 85.0 . . ? C18B C17B H17B 110.2 . . ? C16B C17B H17B 110.9 . . ? C20B C17B H17B 110.2 2_666 . ? C17A C17B H17A 53.3 . . ? C18B C17B H17A 102.0 . . ? C16B C17B H17A 84.7 . . ? C20B C17B H17A 138.8 2_666 . ? H17B C17B H17A 32.3 . . ? C19B C18B C17A 112.9(10) . . ? C19B C18B C17B 124.9(5) . . ? C17A C18B C17B 39.9(8) . . ? C19B C18B H18B 116.3 . . ? C17A C18B H18B 111.2 . . ? C17B C18B H18B 118.6 . . ? C19B C18B H18A 112.4 . . ? C17A C18B H18A 132.1 . . ? C17B C18B H18A 116.9 . . ? H18B C18B H18A 31.0 . . ? C18B C19B C20B 114.6(5) . . ? C18B C19B C20A 116.5(9) . . ? C20B C19B C20A 41.8(7) . . ? C18B C19B H19B 124.9 . . ? C20B C19B H19B 120.5 . . ? C20A C19B H19B 105.3 . . ? C18B C19B H19A 125.1 . . ? C20B C19B H19A 102.8 . . ? C20A C19B H19A 118.1 . . ? H19B C19B H19A 40.6 . . ? C20A C20B C19B 86.2(12) . . ? C20A C20B N1B 62.9(11) . . ? C19B C20B N1B 108.8(5) . . ? C20A C20B C17B 158.9(12) . 2_666 ? C19B C20B C17B 114.9(4) . 2_666 ? N1B C20B C17B 107.5(5) . 2_666 ? C20A C20B H20B 62.4 . . ? C19B C20B H20B 110.5 . . ? N1B C20B H20B 107.9 . . ? C17B C20B H20B 107.0 2_666 . ? N1B N1A C16A 79.3(13) . . ? N1B N1A C20A 64.6(13) . . ? C16A N1A C20A 117.4(17) . . ? N1B N1A C16B 50.4(8) . . ? C16A N1A C16B 28.9(9) . . ? C20A N1A C16B 99.0(14) . . ? N1B N1A H1NB 53.8 . . ? C16A N1A H1NB 110.5 . . ? C20A N1A H1NB 87.7 . . ? C16B N1A H1NB 88.7 . . ? N1B N1A H1NA 116.4 . . ? C16A N1A H1NA 121.4 . . ? C20A N1A H1NA 120.2 . . ? C16B N1A H1NA 128.3 . . ? H1NB N1A H1NA 62.9 . . ? C16B C16A O2 92.7(19) . . ? C16B C16A N1A 93(2) . . ? O2 C16A N1A 127.7(18) . . ? C16B C16A C17A 56.8(15) . . ? O2 C16A C17A 115.8(18) . . ? N1A C16A C17A 111(2) . . ? C16B C16A N1B 54.9(14) . . ? O2 C16A N1B 122.7(16) . . ? N1A C16A N1B 38.5(9) . . ? C17A C16A N1B 86.5(16) . . ? C17B C17A C16B 84.4(16) . . ? C17B C17A C18B 66.9(14) . . ? C16B C17A C18B 120.4(16) . . ? C17B C17A C16A 118(2) . . ? C16B C17A C16A 35.5(10) . . ? C18B C17A C16A 141.5(19) . . ? C17B C17A H17B 47.3 . . ? C16B C17A H17B 107.8 . . ? C18B C17A H17B 89.9 . . ? C16A C17A H17B 122.5 . . ? C17B C17A H17A 68.8 . . ? C16B C17A H17A 109.8 . . ? C18B C17A H17A 106.5 . . ? C16A C17A H17A 110.7 . . ? H17B C17A H17A 22.2 . . ? C20B C20A N1A 108.3(18) . . ? C20B C20A N1B 67.5(12) . . ? N1A C20A N1B 40.7(9) . . ? C20B C20A C19B 52.0(11) . . ? N1A C20A C19B 119.9(16) . . ? N1B C20A C19B 93.0(14) . . ? C20B C20A H20B 49.2 . . ? N1A C20A H20B 132.1 . . ? N1B C20A H20B 102.2 . . ? C19B C20A H20B 81.6 . . ? C20B C20A H20A 114.6 . . ? N1A C20A H20A 118.1 . . ? N1B C20A H20A 138.8 . . ? C19B C20A H20A 121.4 . . ? H20B C20A H20A 65.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 63(18) 2_576 . . . ? C1 C2 C3 O1 -49(3) . . . . ? C1 C2 C3 C10 73(3) . . . . ? C1 C2 C3 C4 -167(3) . . . . ? O1 C3 C4 C5 -129.5(2) . . . . ? C2 C3 C4 C5 -10.2(3) . . . . ? C10 C3 C4 C5 110.1(2) . . . . ? O1 C3 C4 C9 50.4(3) . . . . ? C2 C3 C4 C9 169.7(2) . . . . ? C10 C3 C4 C9 -70.0(2) . . . . ? C9 C4 C5 C6 -0.8(4) . . . . ? C3 C4 C5 C6 179.1(2) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C5 C6 C7 C8 1.6(5) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C4 -0.6(4) . . . . ? C5 C4 C9 C8 1.4(4) . . . . ? C3 C4 C9 C8 -178.5(2) . . . . ? O1 C3 C10 C11 -10.4(3) . . . . ? C2 C3 C10 C11 -130.4(2) . . . . ? C4 C3 C10 C11 107.0(2) . . . . ? O1 C3 C10 C15 172.82(19) . . . . ? C2 C3 C10 C15 52.8(3) . . . . ? C4 C3 C10 C15 -69.8(3) . . . . ? C15 C10 C11 C12 -0.7(3) . . . . ? C3 C10 C11 C12 -177.5(2) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 0.1(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C10 -0.7(4) . . . . ? C11 C10 C15 C14 1.0(3) . . . . ? C3 C10 C15 C14 177.8(2) . . . . ? N1A N1B C16B C16A 1.2(18) . . . . ? C20B N1B C16B C16A -131.4(16) . . . . ? C20A N1B C16B C16A -72(2) . . . . ? N1A N1B C16B C17A 90.5(15) . . . . ? C20B N1B C16B C17A -42.1(14) . . . . ? C20A N1B C16B C17A 17.5(18) . . . . ? C16A N1B C16B C17A 89(2) . . . . ? N1A N1B C16B O2 -41.1(11) . . . . ? C20B N1B C16B O2 -173.7(5) . . . . ? C20A N1B C16B O2 -114.1(14) . . . . ? C16A N1B C16B O2 -42.4(14) . . . . ? N1A N1B C16B C17B 136.1(10) . . . . ? C20B N1B C16B C17B 3.5(7) . . . . ? C20A N1B C16B C17B 63.1(14) . . . . ? C16A N1B C16B C17B 134.8(17) . . . . ? C20B N1B C16B N1A -132.6(12) . . . . ? C20A N1B C16B N1A -72.9(16) . . . . ? C16A N1B C16B N1A -1.2(18) . . . . ? C16A O2 C16B C17A -68(2) . . . . ? C16A O2 C16B N1B 64.8(18) . . . . ? C16A O2 C16B C17B -112.1(18) . . . . ? C16A O2 C16B N1A 41.7(18) . . . . ? C16A C16B C17B C17A 21(3) . . . . ? N1B C16B C17B C17A -95.6(16) . . . . ? O2 C16B C17B C17A 81.5(16) . . . . ? N1A C16B C17B C17A -58.7(18) . . . . ? C16A C16B C17B C18B 75(2) . . . . ? C17A C16B C17B C18B 53.5(15) . . . . ? N1B C16B C17B C18B -42.2(6) . . . . ? O2 C16B C17B C18B 134.9(5) . . . . ? N1A C16B C17B C18B -5.2(10) . . . . ? C16A C16B C17B C20B -166(2) . . . 2_666 ? C17A C16B C17B C20B 172.7(16) . . . 2_666 ? N1B C16B C17B C20B 77.1(5) . . . 2_666 ? O2 C16B C17B C20B -105.8(5) . . . 2_666 ? N1A C16B C17B C20B 114.0(9) . . . 2_666 ? C17A C17B C18B C19B 84.6(15) . . . . ? C16B C17B C18B C19B 41.9(8) . . . . ? C20B C17B C18B C19B -75.1(8) 2_666 . . . ? C16B C17B C18B C17A -42.7(13) . . . . ? C20B C17B C18B C17A -159.7(15) 2_666 . . . ? C17A C18B C19B C20B 46.2(11) . . . . ? C17B C18B C19B C20B 2.3(10) . . . . ? C17A C18B C19B C20A -0.4(13) . . . . ? C17B C18B C19B C20A -44.3(11) . . . . ? C18B C19B C20B C20A -103.1(13) . . . . ? C18B C19B C20B N1B -43.4(7) . . . . ? C20A C19B C20B N1B 59.7(12) . . . . ? C18B C19B C20B C17B 77.1(7) . . . 2_666 ? C20A C19B C20B C17B -179.8(13) . . . 2_666 ? N1A N1B C20B C20A -1.2(16) . . . . ? C16B N1B C20B C20A 116.0(13) . . . . ? C16A N1B C20B C20A 82.4(15) . . . . ? N1A N1B C20B C19B -76.6(12) . . . . ? C16B N1B C20B C19B 40.6(7) . . . . ? C20A N1B C20B C19B -75.4(13) . . . . ? C16A N1B C20B C19B 7.0(13) . . . . ? N1A N1B C20B C17B 158.4(11) . . . 2_666 ? C16B N1B C20B C17B -84.4(6) . . . 2_666 ? C20A N1B C20B C17B 159.6(13) . . . 2_666 ? C16A N1B C20B C17B -117.9(11) . . . 2_666 ? C16B N1B N1A C16A -0.7(11) . . . . ? C20B N1B N1A C16A 128.4(10) . . . . ? C20A N1B N1A C16A 127.5(13) . . . . ? C16B N1B N1A C20A -128.2(10) . . . . ? C20B N1B N1A C20A 1.0(13) . . . . ? C16A N1B N1A C20A -127.5(13) . . . . ? C20B N1B N1A C16B 129.1(9) . . . . ? C20A N1B N1A C16B 128.2(10) . . . . ? C16A N1B N1A C16B 0.7(11) . . . . ? C16A C16B N1A N1B -179(2) . . . . ? C17A C16B N1A N1B -103.1(14) . . . . ? O2 C16B N1A N1B 145.6(9) . . . . ? C17B C16B N1A N1B -66.4(12) . . . . ? C17A C16B N1A C16A 76(2) . . . . ? N1B C16B N1A C16A 179(2) . . . . ? O2 C16B N1A C16A -35.8(17) . . . . ? C17B C16B N1A C16A 112(2) . . . . ? C16A C16B N1A C20A -133(2) . . . . ? C17A C16B N1A C20A -57.1(16) . . . . ? N1B C16B N1A C20A 46.0(10) . . . . ? O2 C16B N1A C20A -168.4(10) . . . . ? C17B C16B N1A C20A -20.4(14) . . . . ? C17A C16B C16A O2 119.4(15) . . . . ? N1B C16B C16A O2 -128.9(11) . . . . ? C17B C16B C16A O2 105.3(16) . . . . ? N1A C16B C16A O2 -128.1(19) . . . . ? C17A C16B C16A N1A -112.6(15) . . . . ? N1B C16B C16A N1A -0.9(13) . . . . ? O2 C16B C16A N1A 128.1(19) . . . . ? C17B C16B C16A N1A -126.7(12) . . . . ? N1B C16B C16A C17A 111.7(11) . . . . ? O2 C16B C16A C17A -119.4(15) . . . . ? C17B C16B C16A C17A -14.1(17) . . . . ? N1A C16B C16A C17A 112.6(15) . . . . ? C17A C16B C16A N1B -111.7(11) . . . . ? O2 C16B C16A N1B 128.9(11) . . . . ? C17B C16B C16A N1B -125.8(16) . . . . ? N1A C16B C16A N1B 0.9(13) . . . . ? C16B O2 C16A N1A -96(3) . . . . ? C16B O2 C16A C17A 54.1(17) . . . . ? C16B O2 C16A N1B -49.2(15) . . . . ? N1B N1A C16A C16B 1.1(17) . . . . ? C20A N1A C16A C16B 55(2) . . . . ? N1B N1A C16A O2 97(3) . . . . ? C20A N1A C16A O2 151(2) . . . . ? C16B N1A C16A O2 96(3) . . . . ? N1B N1A C16A C17A -54.6(17) . . . . ? C20A N1A C16A C17A -1(2) . . . . ? C16B N1A C16A C17A -55.7(18) . . . . ? C20A N1A C16A N1B 53.9(14) . . . . ? C16B N1A C16A N1B -1.1(17) . . . . ? N1A N1B C16A C16B -179(2) . . . . ? C20B N1B C16A C16B 69.7(18) . . . . ? C20A N1B C16A C16B 124.9(17) . . . . ? N1A N1B C16A O2 -111(2) . . . . ? C16B N1B C16A O2 67.5(19) . . . . ? C20B N1B C16A O2 137.2(16) . . . . ? C20A N1B C16A O2 -167.6(19) . . . . ? C16B N1B C16A N1A 179(2) . . . . ? C20B N1B C16A N1A -111.7(14) . . . . ? C20A N1B C16A N1A -56.4(16) . . . . ? N1A N1B C16A C17A 130.2(17) . . . . ? C16B N1B C16A C17A -51.2(13) . . . . ? C20B N1B C16A C17A 18.5(17) . . . . ? C20A N1B C16A C17A 73.8(16) . . . . ? C18B C17B C17A C16B -126.5(12) . . . . ? C20B C17B C17A C16B -21(5) 2_666 . . . ? C16B C17B C17A C18B 126.5(12) . . . . ? C20B C17B C17A C18B 105(4) 2_666 . . . ? C18B C17B C17A C16A -137(2) . . . . ? C16B C17B C17A C16A -11.0(14) . . . . ? C20B C17B C17A C16A -32(5) 2_666 . . . ? C16A C16B C17A C17B -163(2) . . . . ? N1B C16B C17A C17B 103.2(12) . . . . ? O2 C16B C17A C17B -119.7(11) . . . . ? N1A C16B C17A C17B 141.9(12) . . . . ? C16A C16B C17A C18B 138(2) . . . . ? N1B C16B C17A C18B 44(2) . . . . ? O2 C16B C17A C18B -178.8(14) . . . . ? C17B C16B C17A C18B -59.1(16) . . . . ? N1A C16B C17A C18B 83(2) . . . . ? N1B C16B C17A C16A -93.6(18) . . . . ? O2 C16B C17A C16A 43.4(15) . . . . ? C17B C16B C17A C16A 163(2) . . . . ? N1A C16B C17A C16A -54.9(18) . . . . ? C19B C18B C17A C17B -117.6(11) . . . . ? C19B C18B C17A C16B -49(2) . . . . ? C17B C18B C17A C16B 68.1(17) . . . . ? C19B C18B C17A C16A -11(3) . . . . ? C17B C18B C17A C16A 107(3) . . . . ? C16B C16A C17A C17B 19(2) . . . . ? O2 C16A C17A C17B -56(3) . . . . ? N1A C16A C17A C17B 99(2) . . . . ? N1B C16A C17A C17B 69(2) . . . . ? O2 C16A C17A C16B -75(2) . . . . ? N1A C16A C17A C16B 80(2) . . . . ? N1B C16A C17A C16B 49.6(12) . . . . ? C16B C16A C17A C18B -69(3) . . . . ? O2 C16A C17A C18B -144(3) . . . . ? N1A C16A C17A C18B 12(4) . . . . ? N1B C16A C17A C18B -19(3) . . . . ? C19B C20B C20A N1A 114.1(14) . . . . ? N1B C20B C20A N1A 0.7(10) . . . . ? C17B C20B C20A N1A -66(4) 2_666 . . . ? C19B C20B C20A N1B 113.4(7) . . . . ? C17B C20B C20A N1B -67(3) 2_666 . . . ? N1B C20B C20A C19B -113.4(7) . . . . ? C17B C20B C20A C19B 180(3) 2_666 . . . ? N1B N1A C20A C20B -1.0(14) . . . . ? C16A N1A C20A C20B -63(2) . . . . ? C16B N1A C20A C20B -38.9(16) . . . . ? C16A N1A C20A N1B -61.5(14) . . . . ? C16B N1A C20A N1B -37.9(7) . . . . ? N1B N1A C20A C19B 55.0(15) . . . . ? C16A N1A C20A C19B -6(2) . . . . ? C16B N1A C20A C19B 17.1(16) . . . . ? N1A N1B C20A C20B 178.9(14) . . . . ? C16B N1B C20A C20B -99.2(11) . . . . ? C16A N1B C20A C20B -131.3(10) . . . . ? C16B N1B C20A N1A 81.8(14) . . . . ? C20B N1B C20A N1A -178.9(14) . . . . ? C16A N1B C20A N1A 49.8(13) . . . . ? N1A N1B C20A C19B -134.7(13) . . . . ? C16B N1B C20A C19B -52.8(15) . . . . ? C20B N1B C20A C19B 46.4(8) . . . . ? C16A N1B C20A C19B -84.9(13) . . . . ? C18B C19B C20A C20B 98.0(10) . . . . ? C18B C19B C20A N1A 7.5(18) . . . . ? C20B C19B C20A N1A -90.5(18) . . . . ? C18B C19B C20A N1B 39.8(13) . . . . ? C20B C19B C20A N1B -58.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.217 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.040 data_I-c_80hrs _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C5 H5 N O)' _chemical_formula_sum 'C40 H32 N2 O4' _chemical_formula_weight 604.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7810(10) _cell_length_b 7.803(2) _cell_length_c 13.491(3) _cell_angle_alpha 87.76(2) _cell_angle_beta 76.74(2) _cell_angle_gamma 86.24(2) _cell_volume 795.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7657 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7657 _diffrn_reflns_av_R_equivalents 0.083 _diffrn_reflns_av_sigmaI/netI 0.0979 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2784 _reflns_number_gt 1433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2784 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 0.837 _refine_ls_restrained_S_all 0.837 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3271(2) 1.1379(2) 0.23790(12) 0.0596(5) Uani 1 1 d . . . H1 H 0.3996 1.0976 0.2693 0.19(2) Uiso 1 1 calc R . . C1 C 0.0344(3) 1.0050(3) 0.44813(18) 0.0573(6) Uani 1 1 d . . . C2 C 0.0952(3) 1.0154(3) 0.35879(19) 0.0561(6) Uani 1 1 d . . . C3 C 0.1859(3) 1.0264(3) 0.25000(15) 0.0483(6) Uani 1 1 d . . . C4 C 0.0637(3) 1.1030(3) 0.18356(16) 0.0462(6) Uani 1 1 d . . . C5 C -0.1176(3) 1.1303(3) 0.21966(19) 0.0647(7) Uani 1 1 d . . . H5 H -0.1697 1.1003 0.2867 0.052(6) Uiso 1 1 calc R . . C6 C -0.2213(4) 1.2019(4) 0.1561(2) 0.0796(8) Uani 1 1 d . . . H6 H -0.3427 1.2192 0.1807 0.103(10) Uiso 1 1 calc R . . C7 C -0.1478(4) 1.2468(4) 0.0589(2) 0.0726(8) Uani 1 1 d . . . H7 H -0.2179 1.2970 0.0170 0.092(9) Uiso 1 1 calc R . . C8 C 0.0329(4) 1.2180(4) 0.0214(2) 0.0678(7) Uani 1 1 d . . . H8 H 0.0843 1.2476 -0.0458 0.064(7) Uiso 1 1 calc R . . C9 C 0.1360(3) 1.1452(3) 0.08418(17) 0.0567(6) Uani 1 1 d . . . H9 H 0.2569 1.1245 0.0585 0.050(6) Uiso 1 1 calc R . . C10 C 0.2562(3) 0.8445(3) 0.21343(15) 0.0465(6) Uani 1 1 d . . . C11 C 0.4289(3) 0.8116(3) 0.16034(18) 0.0592(7) Uani 1 1 d . . . H11 H 0.5069 0.8994 0.1484 0.055(6) Uiso 1 1 calc R . . C12 C 0.4868(3) 0.6474(4) 0.12448(19) 0.0661(7) Uani 1 1 d . . . H12 H 0.6035 0.6263 0.0893 0.094(9) Uiso 1 1 calc R . . C13 C 0.3730(4) 0.5176(3) 0.14088(18) 0.0640(7) Uani 1 1 d . . . H13 H 0.4117 0.4083 0.1170 0.065(7) Uiso 1 1 calc R . . C14 C 0.1995(3) 0.5504(3) 0.19340(18) 0.0650(7) Uani 1 1 d . . . H14 H 0.1213 0.4627 0.2046 0.061(7) Uiso 1 1 calc R . . C15 C 0.1419(3) 0.7126(3) 0.22918(18) 0.0570(6) Uani 1 1 d . . . H15 H 0.0251 0.7333 0.2642 0.074(8) Uiso 1 1 calc R . . O2 O 0.4793(3) 0.1436(4) 0.39737(17) 0.0981(8) Uani 1 1 d . . . N1B N 0.4795(6) 0.2731(6) 0.5463(3) 0.1021(15) Uani 0.801(7) 1 d P . . H1NB H 0.5261 0.1790 0.5682 0.122 Uiso 0.801(7) 1 d PR . . C16B C 0.4546(5) 0.2790(7) 0.4530(3) 0.0709(13) Uani 0.801(7) 1 d P . . C17B C 0.3906(7) 0.4497(8) 0.4201(4) 0.0968(16) Uani 0.801(7) 1 d P . . H17B H 0.3393 0.4407 0.3609 0.116 Uiso 0.801(7) 1 d PR . . C18B C 0.2608(6) 0.5227(8) 0.5012(6) 0.172(3) Uani 1 1 d . . . H18B H 0.1528 0.5698 0.4897 0.207 Uiso 0.801(7) 1 d PR . . C19B C 0.2702(6) 0.5094(7) 0.5934(5) 0.143(2) Uani 1 1 d . . . H19B H 0.1830 0.5530 0.6486 0.172 Uiso 0.801(7) 1 d PR . . C20B C 0.4322(11) 0.4271(7) 0.6095(3) 0.130(2) Uani 0.801(7) 1 d P . . H20B H 0.4188 0.3891 0.6811 0.157 Uiso 0.801(7) 1 d PR . . N1A N 0.419(2) 0.165(3) 0.5655(12) 0.109(6) Uiso 0.199(7) 1 d P . . H1NA H 0.4847 0.0780 0.5814 0.131 Uiso 0.199(7) 1 d PR . . C16A C 0.408(3) 0.178(4) 0.4552(19) 0.099(8) Uiso 0.199(7) 1 d P . . C17A C 0.319(3) 0.362(3) 0.4464(17) 0.105(7) Uiso 0.199(7) 1 d P . . H17A H 0.3159 0.3854 0.3786 0.125 Uiso 0.199(7) 1 d PR . . C20A C 0.347(3) 0.303(4) 0.6397(19) 0.128(8) Uiso 0.199(7) 1 d P . . H20A H 0.3312 0.2761 0.7091 0.154 Uiso 0.199(7) 1 d PR . . H18A H 0.1902 0.6145 0.4904 0.154 Uiso 0.20 1 d P . . H19A H 0.2501 0.6033 0.6404 0.154 Uiso 0.20 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0680(10) 0.0516(11) 0.0638(10) 0.0038(8) -0.0228(8) -0.0118(8) C1 0.0721(16) 0.0494(16) 0.0497(14) -0.0037(12) -0.0149(12) 0.0065(11) C2 0.0728(15) 0.0440(15) 0.0520(16) -0.0014(11) -0.0174(12) 0.0050(11) C3 0.0578(13) 0.0402(14) 0.0465(13) -0.0003(10) -0.0117(10) -0.0014(11) C4 0.0588(14) 0.0306(13) 0.0494(14) -0.0044(10) -0.0125(11) -0.0003(10) C5 0.0651(16) 0.0663(19) 0.0580(17) 0.0047(13) -0.0077(13) 0.0041(13) C6 0.0611(19) 0.088(2) 0.088(2) 0.0062(18) -0.0184(15) 0.0118(14) C7 0.0794(19) 0.068(2) 0.077(2) 0.0033(15) -0.0363(16) 0.0078(14) C8 0.0815(19) 0.0692(19) 0.0570(17) 0.0087(13) -0.0258(14) -0.0056(14) C9 0.0574(15) 0.0578(17) 0.0548(15) 0.0007(12) -0.0138(12) -0.0002(11) C10 0.0564(14) 0.0430(14) 0.0403(12) 0.0030(10) -0.0124(10) 0.0003(11) C11 0.0631(15) 0.0500(17) 0.0627(15) -0.0030(12) -0.0106(12) -0.0014(13) C12 0.0644(17) 0.062(2) 0.0669(17) -0.0043(14) -0.0089(13) 0.0111(14) C13 0.0886(19) 0.0417(17) 0.0616(16) -0.0048(12) -0.0212(14) 0.0139(14) C14 0.0815(18) 0.0443(17) 0.0694(17) 0.0042(13) -0.0169(14) -0.0078(14) C15 0.0590(15) 0.0447(16) 0.0635(15) -0.0022(12) -0.0072(12) 0.0007(12) O2 0.0931(15) 0.139(2) 0.0680(14) -0.0047(14) -0.0317(12) 0.0016(14) N1B 0.159(3) 0.093(3) 0.063(2) 0.009(2) -0.047(2) -0.004(3) C16B 0.076(3) 0.088(3) 0.056(2) -0.015(2) -0.0277(17) -0.003(2) C17B 0.113(4) 0.106(4) 0.088(3) -0.006(3) -0.062(3) 0.016(4) C18B 0.122(4) 0.197(6) 0.222(6) -0.102(6) -0.084(4) 0.034(3) C19B 0.090(3) 0.152(5) 0.165(5) -0.057(4) 0.033(3) -0.034(3) C20B 0.260(8) 0.095(4) 0.044(2) 0.002(2) -0.048(3) -0.018(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.422(2) . ? O1 H1 0.8200 . ? C1 C2 1.191(3) . ? C1 C1 1.380(5) 2_576 ? C2 C3 1.477(3) . ? C3 C4 1.530(3) . ? C3 C10 1.545(3) . ? C4 C9 1.366(3) . ? C4 C5 1.388(3) . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 C7 1.348(4) . ? C6 H6 0.9300 . ? C7 C8 1.387(4) . ? C7 H7 0.9300 . ? C8 C9 1.377(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.382(3) . ? C10 C11 1.383(3) . ? C11 C12 1.397(3) . ? C11 H11 0.9300 . ? C12 C13 1.367(3) . ? C12 H12 0.9300 . ? C13 C14 1.386(3) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2 C16A 0.89(2) . ? O2 C16B 1.298(5) . ? N1B N1A 0.989(18) . ? N1B C16B 1.315(4) . ? N1B C20A 1.45(2) . ? N1B C20B 1.478(6) . ? N1B C16A 1.67(3) . ? N1B H1NB 0.8692 . ? C16B C16A 0.88(3) . ? C16B C17A 1.22(2) . ? C16B C17B 1.479(7) . ? C16B N1A 1.705(19) . ? C17B C17A 0.92(2) . ? C17B C18B 1.417(7) . ? C17B C20B 1.696(11) 2_666 ? C17B H17B 0.9791 . ? C17B H17A 1.0550 . ? C18B C19B 1.262(7) . ? C18B C17A 1.47(2) . ? C18B H18B 0.9388 . ? C18B H18A 0.9023 . ? C19B C20B 1.434(7) . ? C19B C20A 1.82(3) . ? C19B H19B 0.9429 . ? C19B H19A 0.9701 . ? C20B C20A 1.21(3) . ? C20B C17B 1.696(11) 2_666 ? C20B H20B 0.9835 . ? N1A C20A 1.49(3) . ? N1A C16A 1.51(3) . ? N1A H1NB 0.8539 . ? N1A H1NA 0.8705 . ? C16A C17A 1.56(4) . ? C17A H17B 1.2676 . ? C17A H17A 0.9324 . ? C20A H20B 1.1397 . ? C20A H20A 0.9334 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C2 C1 C1 179.1(3) . 2_576 ? C1 C2 C3 175.0(2) . . ? O1 C3 C2 109.15(17) . . ? O1 C3 C4 106.39(17) . . ? C2 C3 C4 112.27(18) . . ? O1 C3 C10 110.72(17) . . ? C2 C3 C10 108.95(18) . . ? C4 C3 C10 109.35(16) . . ? C9 C4 C5 118.6(2) . . ? C9 C4 C3 118.57(19) . . ? C5 C4 C3 122.83(19) . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C4 C9 C8 121.1(2) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C15 C10 C11 118.8(2) . . ? C15 C10 C3 119.5(2) . . ? C11 C10 C3 121.6(2) . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.4(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C10 C15 C14 120.7(2) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C16A O2 C16B 42.8(17) . . ? N1A N1B C16B 94.4(10) . . ? N1A N1B C20A 72.6(13) . . ? C16B N1B C20A 127.1(9) . . ? N1A N1B C20B 121.6(11) . . ? C16B N1B C20B 119.4(4) . . ? C20A N1B C20B 49.0(10) . . ? N1A N1B C16A 63.0(12) . . ? C16B N1B C16A 31.6(8) . . ? C20A N1B C16A 114.9(12) . . ? C20B N1B C16A 138.3(9) . . ? N1A N1B H1NB 54.3 . . ? C16B N1B H1NB 118.6 . . ? C20A N1B H1NB 95.3 . . ? C20B N1B H1NB 122.0 . . ? C16A N1B H1NB 95.0 . . ? C16A C16B C17A 94.8(19) . . ? C16A C16B O2 43.0(16) . . ? C17A C16B O2 111.5(11) . . ? C16A C16B N1B 97.3(18) . . ? C17A C16B N1B 112.3(11) . . ? O2 C16B N1B 121.9(4) . . ? C16A C16B C17B 129.8(16) . . ? C17A C16B C17B 38.2(11) . . ? O2 C16B C17B 124.0(3) . . ? N1B C16B C17B 114.1(4) . . ? C16A C16B N1A 62.2(18) . . ? C17A C16B N1A 109.5(13) . . ? O2 C16B N1A 94.3(7) . . ? N1B C16B N1A 35.3(6) . . ? C17B C16B N1A 134.5(7) . . ? C17A C17B C18B 74.8(16) . . ? C17A C17B C16B 55.4(16) . . ? C18B C17B C16B 109.4(5) . . ? C17A C17B C20B 161.3(18) . 2_666 ? C18B C17B C20B 110.0(4) . 2_666 ? C16B C17B C20B 106.9(4) . 2_666 ? C17A C17B H17B 83.9 . . ? C18B C17B H17B 109.3 . . ? C16B C17B H17B 111.0 . . ? C20B C17B H17B 110.3 2_666 . ? C17A C17B H17A 55.9 . . ? C18B C17B H17A 103.5 . . ? C16B C17B H17A 87.8 . . ? C20B C17B H17A 135.6 2_666 . ? H17B C17B H17A 28.6 . . ? C19B C18B C17B 123.6(5) . . ? C19B C18B C17A 112.3(11) . . ? C17B C18B C17A 36.9(8) . . ? C19B C18B H18B 115.5 . . ? C17B C18B H18B 120.2 . . ? C17A C18B H18B 112.3 . . ? C19B C18B H18A 111.3 . . ? C17B C18B H18A 121.0 . . ? C17A C18B H18A 133.2 . . ? H18B C18B H18A 29.5 . . ? C18B C19B C20B 114.4(4) . . ? C18B C19B C20A 118.0(9) . . ? C20B C19B C20A 41.8(7) . . ? C18B C19B H19B 124.9 . . ? C20B C19B H19B 120.7 . . ? C20A C19B H19B 104.8 . . ? C18B C19B H19A 125.2 . . ? C20B C19B H19A 102.3 . . ? C20A C19B H19A 116.6 . . ? H19B C19B H19A 40.4 . . ? C20A C20B C19B 86.3(12) . . ? C20A C20B N1B 64.3(11) . . ? C19B C20B N1B 109.8(4) . . ? C20A C20B C17B 158.7(12) . 2_666 ? C19B C20B C17B 115.0(4) . 2_666 ? N1B C20B C17B 106.5(5) . 2_666 ? C20A C20B H20B 61.4 . . ? C19B C20B H20B 110.6 . . ? N1B C20B H20B 107.5 . . ? C17B C20B H20B 107.2 2_666 . ? N1B N1A C20A 68.1(14) . . ? N1B N1A C16A 81.3(15) . . ? C20A N1A C16A 122.9(19) . . ? N1B N1A C16B 50.2(9) . . ? C20A N1A C16B 101.3(15) . . ? C16A N1A C16B 31.2(10) . . ? N1B N1A H1NB 55.7 . . ? C20A N1A H1NB 93.1 . . ? C16A N1A H1NB 108.1 . . ? C16B N1A H1NB 88.9 . . ? N1B N1A H1NA 115.9 . . ? C20A N1A H1NA 121.1 . . ? C16A N1A H1NA 115.3 . . ? C16B N1A H1NA 126.7 . . ? H1NB N1A H1NA 60.4 . . ? O2 C16A C16B 94(2) . . ? O2 C16A N1A 134(2) . . ? C16B C16A N1A 87(2) . . ? O2 C16A C17A 113(2) . . ? C16B C16A C17A 50.9(16) . . ? N1A C16A C17A 103(2) . . ? O2 C16A N1B 123(2) . . ? C16B C16A N1B 51.1(15) . . ? N1A C16A N1B 35.7(9) . . ? C17A C16A N1B 81.0(17) . . ? C17B C17A C16B 86.5(18) . . ? C17B C17A C18B 68.3(17) . . ? C16B C17A C18B 122.6(18) . . ? C17B C17A C16A 118(2) . . ? C16B C17A C16A 34.3(11) . . ? C18B C17A C16A 144(2) . . ? C17B C17A H17B 50.2 . . ? C16B C17A H17B 110.7 . . ? C18B C17A H17B 91.7 . . ? C16A C17A H17B 120.5 . . ? C17B C17A H17A 69.6 . . ? C16B C17A H17A 111.2 . . ? C18B C17A H17A 106.7 . . ? C16A C17A H17A 108.8 . . ? H17B C17A H17A 20.2 . . ? C20B C20A N1B 66.7(12) . . ? C20B C20A N1A 105.9(17) . . ? N1B C20A N1A 39.2(9) . . ? C20B C20A C19B 51.9(11) . . ? N1B C20A C19B 92.9(14) . . ? N1A C20A C19B 119.2(17) . . ? C20B C20A H20B 49.3 . . ? N1B C20A H20B 100.9 . . ? N1A C20A H20B 129.8 . . ? C19B C20A H20B 81.8 . . ? C20B C20A H20A 115.6 . . ? N1B C20A H20A 138.3 . . ? N1A C20A H20A 118.3 . . ? C19B C20A H20A 122.1 . . ? H20B C20A H20A 66.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 52(26) 2_576 . . . ? C1 C2 C3 O1 -45(3) . . . . ? C1 C2 C3 C4 -163(3) . . . . ? C1 C2 C3 C10 76(3) . . . . ? O1 C3 C4 C9 50.8(2) . . . . ? C2 C3 C4 C9 170.1(2) . . . . ? C10 C3 C4 C9 -68.8(2) . . . . ? O1 C3 C4 C5 -129.7(2) . . . . ? C2 C3 C4 C5 -10.4(3) . . . . ? C10 C3 C4 C5 110.6(2) . . . . ? C9 C4 C5 C6 -1.2(4) . . . . ? C3 C4 C5 C6 179.3(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C6 C7 C8 C9 -0.6(4) . . . . ? C5 C4 C9 C8 1.9(3) . . . . ? C3 C4 C9 C8 -178.6(2) . . . . ? C7 C8 C9 C4 -1.0(4) . . . . ? O1 C3 C10 C15 172.99(19) . . . . ? C2 C3 C10 C15 52.9(3) . . . . ? C4 C3 C10 C15 -70.1(2) . . . . ? O1 C3 C10 C11 -10.5(3) . . . . ? C2 C3 C10 C11 -130.5(2) . . . . ? C4 C3 C10 C11 106.4(2) . . . . ? C15 C10 C11 C12 -0.8(3) . . . . ? C3 C10 C11 C12 -177.3(2) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C11 C10 C15 C14 0.6(3) . . . . ? C3 C10 C15 C14 177.2(2) . . . . ? C13 C14 C15 C10 -0.1(4) . . . . ? C16A O2 C16B C17A -73(3) . . . . ? C16A O2 C16B N1B 63(2) . . . . ? C16A O2 C16B C17B -114(2) . . . . ? C16A O2 C16B N1A 40(2) . . . . ? N1A N1B C16B C16A -6(2) . . . . ? C20A N1B C16B C16A -77(2) . . . . ? C20B N1B C16B C16A -136.0(17) . . . . ? N1A N1B C16B C17A 92.5(16) . . . . ? C20A N1B C16B C17A 21.0(18) . . . . ? C20B N1B C16B C17A -37.8(14) . . . . ? C16A N1B C16B C17A 98(2) . . . . ? N1A N1B C16B O2 -43.6(12) . . . . ? C20A N1B C16B O2 -115.2(14) . . . . ? C20B N1B C16B O2 -173.9(5) . . . . ? C16A N1B C16B O2 -37.9(15) . . . . ? N1A N1B C16B C17B 134.2(11) . . . . ? C20A N1B C16B C17B 62.6(14) . . . . ? C20B N1B C16B C17B 3.9(7) . . . . ? C16A N1B C16B C17B 139.9(18) . . . . ? C20A N1B C16B N1A -71.6(16) . . . . ? C20B N1B C16B N1A -130.3(12) . . . . ? C16A N1B C16B N1A 6(2) . . . . ? C16A C16B C17B C17A 28(3) . . . . ? O2 C16B C17B C17A 81.8(19) . . . . ? N1B C16B C17B C17A -96.0(18) . . . . ? N1A C16B C17B C17A -60(2) . . . . ? C16A C16B C17B C18B 82(2) . . . . ? C17A C16B C17B C18B 54.4(18) . . . . ? O2 C16B C17B C18B 136.2(5) . . . . ? N1B C16B C17B C18B -41.5(6) . . . . ? N1A C16B C17B C18B -6.0(11) . . . . ? C16A C16B C17B C20B -159(2) . . . 2_666 ? C17A C16B C17B C20B 173.5(19) . . . 2_666 ? O2 C16B C17B C20B -104.7(5) . . . 2_666 ? N1B C16B C17B C20B 77.5(5) . . . 2_666 ? N1A C16B C17B C20B 113.1(9) . . . 2_666 ? C17A C17B C18B C19B 82.8(18) . . . . ? C16B C17B C18B C19B 38.8(8) . . . . ? C20B C17B C18B C19B -78.3(8) 2_666 . . . ? C16B C17B C18B C17A -43.9(17) . . . . ? C20B C17B C18B C17A -161.0(18) 2_666 . . . ? C17B C18B C19B C20B 5.5(9) . . . . ? C17A C18B C19B C20B 45.6(11) . . . . ? C17B C18B C19B C20A -41.2(11) . . . . ? C17A C18B C19B C20A -1.1(14) . . . . ? C18B C19B C20B C20A -105.3(12) . . . . ? C18B C19B C20B N1B -44.4(7) . . . . ? C20A C19B C20B N1B 61.0(11) . . . . ? C18B C19B C20B C17B 75.6(6) . . . 2_666 ? C20A C19B C20B C17B -179.0(12) . . . 2_666 ? N1A N1B C20B C20A -1.5(17) . . . . ? C16B N1B C20B C20A 115.3(13) . . . . ? C16A N1B C20B C20A 82.2(17) . . . . ? N1A N1B C20B C19B -77.0(14) . . . . ? C16B N1B C20B C19B 39.8(7) . . . . ? C20A N1B C20B C19B -75.5(13) . . . . ? C16A N1B C20B C19B 6.7(14) . . . . ? N1A N1B C20B C17B 157.9(13) . . . 2_666 ? C16B N1B C20B C17B -85.3(5) . . . 2_666 ? C20A N1B C20B C17B 159.4(13) . . . 2_666 ? C16A N1B C20B C17B -118.4(13) . . . 2_666 ? C16B N1B N1A C20A -127.5(10) . . . . ? C20B N1B N1A C20A 1.2(14) . . . . ? C16A N1B N1A C20A -130.9(15) . . . . ? C16B N1B N1A C16A 3.4(12) . . . . ? C20A N1B N1A C16A 130.9(15) . . . . ? C20B N1B N1A C16A 132.1(11) . . . . ? C20A N1B N1A C16B 127.5(10) . . . . ? C20B N1B N1A C16B 128.7(9) . . . . ? C16A N1B N1A C16B -3.4(12) . . . . ? C16A C16B N1A N1B 174(2) . . . . ? C17A C16B N1A N1B -101.4(15) . . . . ? O2 C16B N1A N1B 144.0(9) . . . . ? C17B C16B N1A N1B -66.6(12) . . . . ? C16A C16B N1A C20A -138(2) . . . . ? C17A C16B N1A C20A -52.8(17) . . . . ? O2 C16B N1A C20A -167.4(10) . . . . ? N1B C16B N1A C20A 48.6(11) . . . . ? C17B C16B N1A C20A -18.0(15) . . . . ? C17A C16B N1A C16A 85(2) . . . . ? O2 C16B N1A C16A -29.6(17) . . . . ? N1B C16B N1A C16A -174(2) . . . . ? C17B C16B N1A C16A 120(2) . . . . ? C16B O2 C16A N1A -89(4) . . . . ? C16B O2 C16A C17A 49.0(18) . . . . ? C16B O2 C16A N1B -45.3(17) . . . . ? C17A C16B C16A O2 116.7(19) . . . . ? N1B C16B C16A O2 -130.0(15) . . . . ? C17B C16B C16A O2 100(2) . . . . ? N1A C16B C16A O2 -134(2) . . . . ? C17A C16B C16A N1A -109.5(15) . . . . ? O2 C16B C16A N1A 134(2) . . . . ? N1B C16B C16A N1A 3.7(13) . . . . ? C17B C16B C16A N1A -126.3(14) . . . . ? O2 C16B C16A C17A -116.7(19) . . . . ? N1B C16B C16A C17A 113.3(12) . . . . ? C17B C16B C16A C17A -16.7(18) . . . . ? N1A C16B C16A C17A 109.5(15) . . . . ? C17A C16B C16A N1B -113.3(12) . . . . ? O2 C16B C16A N1B 130.0(15) . . . . ? C17B C16B C16A N1B -130.0(18) . . . . ? N1A C16B C16A N1B -3.7(13) . . . . ? N1B N1A C16A O2 88(4) . . . . ? C20A N1A C16A O2 144(3) . . . . ? C16B N1A C16A O2 93(4) . . . . ? N1B N1A C16A C16B -5.0(17) . . . . ? C20A N1A C16A C16B 52(2) . . . . ? N1B N1A C16A C17A -53.6(17) . . . . ? C20A N1A C16A C17A 3(2) . . . . ? C16B N1A C16A C17A -48.6(16) . . . . ? C20A N1A C16A N1B 56.7(16) . . . . ? C16B N1A C16A N1B 5.0(17) . . . . ? N1A N1B C16A O2 -121(3) . . . . ? C16B N1B C16A O2 66(2) . . . . ? C20A N1B C16A O2 -173(2) . . . . ? C20B N1B C16A O2 131(2) . . . . ? N1A N1B C16A C16B 174(2) . . . . ? C20A N1B C16A C16B 120.9(18) . . . . ? C20B N1B C16A C16B 65.4(19) . . . . ? C16B N1B C16A N1A -174(2) . . . . ? C20A N1B C16A N1A -52.7(17) . . . . ? C20B N1B C16A N1A -108.2(16) . . . . ? N1A N1B C16A C17A 127.4(17) . . . . ? C16B N1B C16A C17A -46.2(14) . . . . ? C20A N1B C16A C17A 74.6(17) . . . . ? C20B N1B C16A C17A 19.1(18) . . . . ? C18B C17B C17A C16B -127.3(13) . . . . ? C20B C17B C17A C16B -20(6) 2_666 . . . ? C16B C17B C17A C18B 127.3(13) . . . . ? C20B C17B C17A C18B 108(5) 2_666 . . . ? C18B C17B C17A C16A -141(2) . . . . ? C16B C17B C17A C16A -13.2(15) . . . . ? C20B C17B C17A C16A -33(6) 2_666 . . . ? C16A C16B C17A C17B -159(2) . . . . ? O2 C16B C17A C17B -118.1(14) . . . . ? N1B C16B C17A C17B 101.1(15) . . . . ? N1A C16B C17A C17B 138.8(14) . . . . ? C16A C16B C17A C18B 140(3) . . . . ? O2 C16B C17A C18B -179.5(15) . . . . ? N1B C16B C17A C18B 40(2) . . . . ? C17B C16B C17A C18B -61.4(19) . . . . ? N1A C16B C17A C18B 77(2) . . . . ? O2 C16B C17A C16A 40.9(17) . . . . ? N1B C16B C17A C16A -100(2) . . . . ? C17B C16B C17A C16A 159(2) . . . . ? N1A C16B C17A C16A -62.1(19) . . . . ? C19B C18B C17A C17B -116.8(14) . . . . ? C19B C18B C17A C16B -46(2) . . . . ? C17B C18B C17A C16B 70.5(19) . . . . ? C19B C18B C17A C16A -8(3) . . . . ? C17B C18B C17A C16A 109(4) . . . . ? O2 C16A C17A C17B -52(4) . . . . ? C16B C16A C17A C17B 24(3) . . . . ? N1A C16A C17A C17B 99(2) . . . . ? N1B C16A C17A C17B 70(2) . . . . ? O2 C16A C17A C16B -76(2) . . . . ? N1A C16A C17A C16B 75(2) . . . . ? N1B C16A C17A C16B 46.4(13) . . . . ? O2 C16A C17A C18B -143(3) . . . . ? C16B C16A C17A C18B -68(3) . . . . ? N1A C16A C17A C18B 7(4) . . . . ? N1B C16A C17A C18B -21(3) . . . . ? C19B C20B C20A N1B 114.1(6) . . . . ? C17B C20B C20A N1B -68(3) 2_666 . . . ? C19B C20B C20A N1A 114.9(14) . . . . ? N1B C20B C20A N1A 0.9(10) . . . . ? C17B C20B C20A N1A -67(4) 2_666 . . . ? N1B C20B C20A C19B -114.1(6) . . . . ? C17B C20B C20A C19B 178(3) 2_666 . . . ? N1A N1B C20A C20B 178.7(15) . . . . ? C16B N1B C20A C20B -99.0(11) . . . . ? C16A N1B C20A C20B -133.3(12) . . . . ? C16B N1B C20A N1A 82.3(15) . . . . ? C20B N1B C20A N1A -178.7(15) . . . . ? C16A N1B C20A N1A 48.0(16) . . . . ? N1A N1B C20A C19B -135.3(14) . . . . ? C16B N1B C20A C19B -53.0(15) . . . . ? C20B N1B C20A C19B 46.0(8) . . . . ? C16A N1B C20A C19B -87.3(15) . . . . ? N1B N1A C20A C20B -1.3(15) . . . . ? C16A N1A C20A C20B -64(2) . . . . ? C16B N1A C20A C20B -39.7(17) . . . . ? C16A N1A C20A N1B -62.9(17) . . . . ? C16B N1A C20A N1B -38.4(8) . . . . ? N1B N1A C20A C19B 53.6(16) . . . . ? C16A N1A C20A C19B -9(2) . . . . ? C16B N1A C20A C19B 15.2(17) . . . . ? C18B C19B C20A C20B 96.2(10) . . . . ? C18B C19B C20A N1B 39.1(13) . . . . ? C20B C19B C20A N1B -57.1(9) . . . . ? C18B C19B C20A N1A 8.5(19) . . . . ? C20B C19B C20A N1A -87.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.216 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.038 #END