data_I-b_290K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 6-Methyl-2(1H)-Pyridinone ; _chemical_name_common 'Tetraphenylhexadiynediol and Methylpyridone' _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C6 H7 N O)' _chemical_formula_sum 'C42 H36 N2 O4' _chemical_formula_weight 632.73 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.454(10) _cell_length_b 10.833(12) _cell_length_c 11.37(2) _cell_angle_alpha 63.86(4) _cell_angle_beta 79.73(5) _cell_angle_gamma 68.44(3) _cell_volume 869(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7693 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.03 _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.078 _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 7693 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3042 _reflns_number_gt 1872 _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^)+(0.0796P)^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 SHELXL _refine_ls_extinction_coef 0.047(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3042 _refine_ls_number_parameters 235 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.992 _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 0.15685(14) 0.77642(14) 0.66441(13) 0.0657(4) Uani 1 1 d . . . H1O1 H 0.2332 0.7012 0.6689 0.099 Uiso 1 1 calc R . . C1 C 0.0277(2) 0.55678(19) 0.95761(19) 0.0524(5) Uani 1 1 d . . . C2 C 0.07828(19) 0.65442(19) 0.88476(18) 0.0506(5) Uani 1 1 d . . . C3 C 0.12868(19) 0.78147(18) 0.79032(17) 0.0488(5) Uani 1 1 d . . . C4 C 0.2869(2) 0.78611(19) 0.8331(2) 0.0556(5) Uani 1 1 d . . . C5 C 0.3473(3) 0.8999(2) 0.7531(3) 0.0866(8) Uani 1 1 d . . . H5 H 0.2923 0.9698 0.6756 0.104 Uiso 1 1 calc R . . C6 C 0.4892(4) 0.9094(4) 0.7883(4) 0.1198(12) Uani 1 1 d . . . H6 H 0.5286 0.9867 0.7348 0.144 Uiso 1 1 calc R . . C7 C 0.5725(3) 0.8059(4) 0.9014(4) 0.1225(13) Uani 1 1 d . . . H7 H 0.6692 0.8118 0.9238 0.147 Uiso 1 1 calc R . . C8 C 0.5134(3) 0.6949(3) 0.9806(3) 0.0951(9) Uani 1 1 d . . . H8 H 0.5691 0.6253 1.0578 0.114 Uiso 1 1 calc R . . C9 C 0.3708(2) 0.6844(2) 0.9473(2) 0.0656(6) Uani 1 1 d . . . H9 H 0.3311 0.6078 1.0026 0.079 Uiso 1 1 calc R . . C10 C -0.02089(19) 0.91906(18) 0.78093(18) 0.0479(5) Uani 1 1 d . . . C11 C -0.1006(2) 1.0199(2) 0.6649(2) 0.0659(6) Uani 1 1 d . . . H11 H -0.0674 1.0040 0.5889 0.079 Uiso 1 1 calc R . . C12 C -0.2308(2) 1.1455(2) 0.6616(2) 0.0747(6) Uani 1 1 d . . . H12 H -0.2828 1.2140 0.5825 0.090 Uiso 1 1 calc R . . C13 C -0.2832(2) 1.1696(2) 0.7716(3) 0.0724(6) Uani 1 1 d . . . H13 H -0.3701 1.2542 0.7681 0.087 Uiso 1 1 calc R . . C14 C -0.2065(2) 1.0677(2) 0.8889(2) 0.0727(6) Uani 1 1 d . . . H14 H -0.2431 1.0826 0.9652 0.087 Uiso 1 1 calc R . . C15 C -0.0754(2) 0.9438(2) 0.8929(2) 0.0621(5) Uani 1 1 d . . . H15 H -0.0231 0.8760 0.9720 0.074 Uiso 1 1 calc R . . O2A O 0.4610(2) 0.55229(17) 0.63375(16) 0.0665(5) Uani 0.849(3) 1 d P . . N1 N 0.65719(18) 0.59205(17) 0.47068(18) 0.0649(5) Uani 1 1 d D . . H1NA H 0.6166 0.5539 0.4360 0.078 Uiso 0.849(3) 1 d PR . . C16A C 0.5880(3) 0.5945(2) 0.5869(3) 0.0598(7) Uani 0.849(3) 1 d P . . C17A C 0.6724(3) 0.6445(3) 0.6477(3) 0.0884(7) Uani 1 1 d . . . H17A H 0.6369 0.6433 0.7303 0.106 Uiso 0.849(3) 1 d PR . . C18A C 0.8015(3) 0.6934(3) 0.5850(4) 0.0947(10) Uani 0.849(3) 1 d P . . H18A H 0.8538 0.7271 0.6245 0.114 Uiso 0.849(3) 1 d PR . . C19 C 0.8614(3) 0.6945(3) 0.4583(3) 0.0910(8) Uani 1 1 d D . . H19A H 0.9508 0.7290 0.4154 0.109 Uiso 0.849(3) 1 d PR . . C20A C 0.7856(3) 0.6449(3) 0.4037(3) 0.0736(8) Uani 0.849(3) 1 d P . . C22A C 0.8335(3) 0.6373(4) 0.2746(3) 0.1123(10) Uani 1 1 d . . . H22A H 0.9359 0.6614 0.2423 0.135 Uiso 0.849(3) 1 d PR . . H22B H 0.7435 0.7051 0.2141 0.135 Uiso 0.849(3) 1 d PR . . H22C H 0.8520 0.5406 0.2837 0.135 Uiso 0.849(3) 1 d PR . . H1NB H 0.5572 0.5902 0.5022 0.135 Uiso 0.15 1 d P . . H22D H 0.5976 0.5878 0.6852 0.135 Uiso 0.15 1 d P . . H22E H 0.6077 0.7456 0.6265 0.135 Uiso 0.15 1 d P . . H22F H 0.7579 0.6130 0.7095 0.135 Uiso 0.15 1 d P . . H19B H 0.9019 0.7461 0.4859 0.135 Uiso 0.15 1 d P . . H17B H 0.8500 0.6539 0.1867 0.135 Uiso 0.15 1 d P . . O2B O 0.6222(14) 0.4810(10) 0.3608(10) 0.071(3) Uiso 0.151(3) 1 d PD . . C16B C 0.7059(15) 0.5500(14) 0.3722(11) 0.067(4) Uiso 0.151(3) 1 d PD . . C18B C 0.907(2) 0.679(2) 0.3325(12) 0.104(6) Uiso 0.151(3) 1 d PD . . H18B H 1.0027 0.7041 0.2900 0.125 Uiso 0.151(3) 1 d PR . . C20B C 0.7515(19) 0.629(2) 0.5297(11) 0.106(6) Uiso 0.151(3) 1 d PD . . 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 0.0655(8) 0.0630(9) 0.0607(9) -0.0286(7) 0.0057(6) -0.0115(6) C1 0.0443(9) 0.0463(10) 0.0673(13) -0.0242(9) 0.0009(8) -0.0151(8) C2 0.0429(9) 0.0453(10) 0.0630(12) -0.0230(9) -0.0030(8) -0.0117(8) C3 0.0454(9) 0.0449(10) 0.0539(12) -0.0197(9) 0.0046(8) -0.0156(8) C4 0.0396(9) 0.0457(10) 0.0840(15) -0.0317(10) 0.0062(9) -0.0136(8) C5 0.0627(12) 0.0642(14) 0.132(2) -0.0365(14) 0.0146(12) -0.0319(11) C6 0.0692(17) 0.094(2) 0.228(4) -0.089(3) 0.033(2) -0.0484(16) C7 0.0466(13) 0.126(3) 0.252(4) -0.136(3) 0.0035(19) -0.0197(16) C8 0.0521(12) 0.0981(19) 0.164(3) -0.0930(19) -0.0254(14) 0.0038(12) C9 0.0470(10) 0.0591(12) 0.0980(17) -0.0446(12) -0.0097(10) -0.0061(9) C10 0.0409(8) 0.0437(10) 0.0562(12) -0.0175(9) 0.0037(8) -0.0164(7) C11 0.0551(10) 0.0651(13) 0.0575(13) -0.0173(11) 0.0035(9) -0.0101(10) C12 0.0567(11) 0.0598(13) 0.0749(16) -0.0088(12) -0.0037(10) -0.0063(10) C13 0.0513(10) 0.0537(13) 0.1005(19) -0.0309(13) -0.0028(11) -0.0050(9) C14 0.0617(11) 0.0728(15) 0.0902(17) -0.0495(14) -0.0042(11) -0.0079(11) C15 0.0555(10) 0.0588(12) 0.0686(14) -0.0301(11) -0.0094(9) -0.0064(9) O2A 0.0554(10) 0.0688(11) 0.0810(13) -0.0388(9) 0.0058(8) -0.0196(8) N1 0.0534(9) 0.0627(11) 0.0845(13) -0.0362(10) 0.0023(8) -0.0194(8) C16A 0.0483(12) 0.0534(14) 0.0751(18) -0.0301(12) -0.0035(11) -0.0083(10) C17A 0.0789(15) 0.0955(18) 0.112(2) -0.0635(17) -0.0037(13) -0.0239(13) C18A 0.0736(18) 0.089(2) 0.148(3) -0.066(2) -0.0117(18) -0.0292(15) C19 0.0712(14) 0.0809(17) 0.126(2) -0.0418(17) 0.0050(14) -0.0344(12) C20A 0.0565(14) 0.0654(16) 0.090(2) -0.0252(15) 0.0034(13) -0.0205(12) C22A 0.0910(17) 0.140(3) 0.100(2) -0.047(2) 0.0210(15) -0.0455(17) _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 1.431(4) . ? O1 H1O1 0.8200 . ? C1 C2 1.192(3) . ? C1 C1 1.371(4) 2_567 ? C2 C3 1.481(3) . ? C3 C4 1.527(3) . ? C3 C10 1.535(3) . ? C4 C9 1.377(4) . ? C4 C5 1.384(3) . ? C5 C6 1.382(4) . ? C5 H5 0.9300 . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 C8 1.353(4) . ? C7 H7 0.9300 . ? C8 C9 1.383(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 C15 1.381(4) . ? C11 C12 1.390(3) . ? C11 H11 0.9300 . ? C12 C13 1.355(4) . ? C12 H12 0.9300 . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 C15 1.380(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A O2B 0.883(10) 2_666 ? O2A C16A 1.261(3) . ? N1 C16A 1.354(4) . ? N1 C16B 1.333(8) . ? N1 C20A 1.365(3) . ? N1 C20B 1.381(9) . ? N1 H1NA 0.8600 . ? N1 H1NB 0.8611 . ? C16A C17A 1.439(4) . ? C16A C20B 1.522(10) . ? C16A H1NB 1.0655 . ? C16A H22D 1.1037 . ? C17A C18A 1.340(4) . ? C17A C20B 1.439(12) . ? C17A H17A 0.9300 . ? C17A H22D 0.9576 . ? C17A H22E 0.9650 . ? C17A H22F 0.9596 . ? C18A C20B 1.326(10) . ? C18A C19 1.435(5) . ? C18A H18A 0.9300 . ? C18A H22E 1.5828 . ? C18A H22F 1.3647 . ? C18A H19B 1.3283 . ? C19 C20B 1.317(9) . ? C19 C20A 1.332(4) . ? C19 C18B 1.478(9) . ? C19 H19A 0.9300 . ? C19 H19B 0.9286 . ? C20A C18B 1.253(14) . ? C20A C20B 1.355(11) . ? C20A C22A 1.482(5) . ? C20A C16B 1.600(9) . ? C22A C18B 1.284(14) . ? C22A C16B 1.640(11) . ? C22A H22A 0.9600 . ? C22A H22B 0.9600 . ? C22A H22C 0.9600 . ? C22A H17B 0.9281 . ? O2B O2A 0.883(10) 2_666 ? O2B C16B 1.257(9) . ? O2B H1NA 1.3824 . ? C16B H1NA 0.9521 . ? C16B H22C 1.4512 . ? C18B H19A 1.4251 . ? C18B H22A 1.0963 . ? C18B H18B 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 H1O1 109.5 . . ? C2 C1 C1 179.0(3) . 2_567 ? C1 C2 C3 175.88(17) . . ? O1 C3 C2 108.69(17) . . ? O1 C3 C4 110.57(15) . . ? C2 C3 C4 112.15(17) . . ? O1 C3 C10 108.41(15) . . ? C2 C3 C10 107.54(16) . . ? C4 C3 C10 109.36(16) . . ? C9 C4 C5 118.7(2) . . ? C9 C4 C3 123.46(17) . . ? C5 C4 C3 117.9(2) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 120.6(2) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C11 C10 C15 118.8(2) . . ? C11 C10 C3 122.56(19) . . ? C15 C10 C3 118.60(18) . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.5(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 120.8(2) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O2B O2A C16A 158.8(7) 2_666 . ? C16A N1 C16B 159.9(5) . . ? C16A N1 C20A 125.7(2) . . ? C16B N1 C20A 72.7(5) . . ? C16A N1 C20B 67.6(5) . . ? C16B N1 C20B 127.5(7) . . ? C20A N1 C20B 59.1(5) . . ? C16A N1 H1NA 117.1 . . ? C16B N1 H1NA 45.4 . . ? C20A N1 H1NA 117.2 . . ? C20B N1 H1NA 168.4 . . ? C16A N1 H1NB 51.9 . . ? C16B N1 H1NB 114.1 . . ? C20A N1 H1NB 160.3 . . ? C20B N1 H1NB 118.3 . . ? H1NA N1 H1NB 69.1 . . ? O2A C16A N1 119.5(2) . . ? O2A C16A C17A 125.6(3) . . ? N1 C16A C17A 114.9(2) . . ? O2A C16A C20B 173.6(7) . . ? N1 C16A C20B 57.0(4) . . ? C17A C16A C20B 58.1(4) . . ? O2A C16A H1NB 81.8 . . ? N1 C16A H1NB 39.5 . . ? C17A C16A H1NB 150.9 . . ? C20B C16A H1NB 95.8 . . ? O2A C16A H22D 85.5 . . ? N1 C16A H22D 151.8 . . ? C17A C16A H22D 41.7 . . ? C20B C16A H22D 96.7 . . ? H1NB C16A H22D 167.2 . . ? C18A C17A C16A 120.0(3) . . ? C18A C17A C20B 56.9(4) . . ? C16A C17A C20B 63.9(4) . . ? C18A C17A H17A 120.1 . . ? C16A C17A H17A 119.9 . . ? C20B C17A H17A 171.0 . . ? C18A C17A H22D 163.9 . . ? C16A C17A H22D 50.1 . . ? C20B C17A H22D 109.9 . . ? H17A C17A H22D 71.4 . . ? C18A C17A H22E 85.1 . . ? C16A C17A H22E 106.4 . . ? C20B C17A H22E 108.9 . . ? H17A C17A H22E 78.4 . . ? H22D C17A H22E 109.3 . . ? C18A C17A H22F 70.6 . . ? C16A C17A H22F 143.7 . . ? C20B C17A H22F 109.9 . . ? H17A C17A H22F 61.9 . . ? H22D C17A H22F 109.7 . . ? H22E C17A H22F 109.1 . . ? C17A C18A C20B 65.3(5) . . ? C17A C18A C19 121.5(3) . . ? C20B C18A C19 56.8(5) . . ? C17A C18A H18A 119.2 . . ? C20B C18A H18A 170.7 . . ? C19 C18A H18A 119.2 . . ? C17A C18A H22E 37.4 . . ? C20B C18A H22E 85.1 . . ? C19 C18A H22E 124.8 . . ? H18A C18A H22E 103.3 . . ? C17A C18A H22F 41.5 . . ? C20B C18A H22F 94.9 . . ? C19 C18A H22F 145.7 . . ? H18A C18A H22F 85.4 . . ? H22E C18A H22F 63.8 . . ? C17A C18A H19B 158.6 . . ? C20B C18A H19B 95.8 . . ? C19 C18A H19B 39.0 . . ? H18A C18A H19B 80.9 . . ? H22E C18A H19B 136.6 . . ? H22F C18A H19B 157.8 . . ? C20B C19 C20A 61.6(5) . . ? C20B C19 C18A 57.4(5) . . ? C20A C19 C18A 118.3(2) . . ? C20B C19 C18B 113.2(7) . . ? C20A C19 C18B 52.7(6) . . ? C18A C19 C18B 170.6(6) . . ? C20B C19 H19A 171.8 . . ? C20A C19 H19A 120.8 . . ? C18A C19 H19A 120.9 . . ? C18B C19 H19A 68.2 . . ? C20B C19 H19B 121.6 . . ? C20A C19 H19B 169.3 . . ? C18A C19 H19B 64.2 . . ? C18B C19 H19B 125.1 . . ? H19A C19 H19B 57.7 . . ? C18B C20A C19 69.7(6) . . ? C18B C20A C20B 127.1(7) . . ? C19 C20A C20B 58.7(4) . . ? C18B C20A N1 170.1(7) . . ? C19 C20A N1 119.3(3) . . ? C20B C20A N1 61.0(4) . . ? C18B C20A C22A 55.2(6) . . ? C19 C20A C22A 124.9(3) . . ? C20B C20A C22A 171.1(8) . . ? N1 C20A C22A 115.8(2) . . ? C18B C20A C16B 117.5(7) . . ? C19 C20A C16B 165.6(5) . . ? C20B C20A C16B 110.7(5) . . ? N1 C20A C16B 52.7(4) . . ? C22A C20A C16B 64.1(4) . . ? C18B C22A C20A 53.3(5) . . ? C18B C22A C16B 113.0(7) . . ? C20A C22A C16B 61.4(3) . . ? C18B C22A H22A 56.3 . . ? C20A C22A H22A 109.4 . . ? C16B C22A H22A 159.2 . . ? C18B C22A H22B 121.4 . . ? C20A C22A H22B 109.4 . . ? C16B C22A H22B 91.4 . . ? H22A C22A H22B 109.5 . . ? C18B C22A H22C 129.2 . . ? C20A C22A H22C 109.6 . . ? C16B C22A H22C 61.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C18B C22A H17B 124.1 . . ? C20A C22A H17B 167.5 . . ? C16B C22A H17B 122.9 . . ? H22A C22A H17B 70.5 . . ? H22B C22A H17B 60.3 . . ? H22C C22A H17B 81.5 . . ? O2A O2B C16B 161.7(12) 2_666 . ? O2A O2B H1NA 120.4 2_666 . ? C16B O2B H1NA 41.9 . . ? O2B C16B N1 115.7(9) . . ? O2B C16B C22A 134.3(8) . . ? N1 C16B C22A 108.1(6) . . ? O2B C16B C20A 169.9(9) . . ? N1 C16B C20A 54.6(3) . . ? C22A C16B C20A 54.4(4) . . ? O2B C16B H1NA 76.1 . . ? N1 C16B H1NA 40.0 . . ? C22A C16B H1NA 143.5 . . ? C20A C16B H1NA 93.9 . . ? O2B C16B H22C 107.4 . . ? N1 C16B H22C 136.0 . . ? C22A C16B H22C 35.5 . . ? C20A C16B H22C 82.7 . . ? H1NA C16B H22C 175.0 . . ? C20A C18B C22A 71.5(9) . . ? C20A C18B C19 57.7(4) . . ? C22A C18B C19 129.1(11) . . ? C20A C18B H19A 94.9 . . ? C22A C18B H19A 165.8 . . ? C19 C18B H19A 37.3 . . ? C20A C18B H22A 118.0 . . ? C22A C18B H22A 46.7 . . ? C19 C18B H22A 175.4 . . ? H19A C18B H22A 147.0 . . ? C20A C18B H18B 172.1 . . ? C22A C18B H18B 116.1 . . ? C19 C18B H18B 114.8 . . ? H19A C18B H18B 77.7 . . ? H22A C18B H18B 69.4 . . ? C19 C20B C20A 59.8(5) . . ? C19 C20B C18A 65.8(4) . . ? C20A C20B C18A 124.8(7) . . ? C19 C20B N1 119.2(8) . . ? C20A C20B N1 59.8(4) . . ? C18A C20B N1 164.1(16) . . ? C19 C20B C17A 122.9(8) . . ? C20A C20B C17A 164.0(15) . . ? C18A C20B C17A 57.8(5) . . ? N1 C20B C17A 113.2(7) . . ? C19 C20B C16A 163.3(15) . . ? C20A C20B C16A 114.3(6) . . ? C18A C20B C16A 115.2(9) . . ? N1 C20B C16A 55.3(3) . . ? C17A C20B C16A 58.1(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 -177(100) 2_567 . . . ? C1 C2 C3 O1 -79(3) . . . . ? C1 C2 C3 C4 159(3) . . . . ? C1 C2 C3 C10 38(3) . . . . ? O1 C3 C4 C9 -122.2(2) . . . . ? C2 C3 C4 C9 -0.7(2) . . . . ? C10 C3 C4 C9 118.5(2) . . . . ? O1 C3 C4 C5 58.5(2) . . . . ? C2 C3 C4 C5 -179.99(17) . . . . ? C10 C3 C4 C5 -60.8(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -1.2(4) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 C4 0.2(3) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? C3 C4 C9 C8 -179.91(17) . . . . ? O1 C3 C10 C11 -3.7(2) . . . . ? C2 C3 C10 C11 -121.03(19) . . . . ? C4 C3 C10 C11 117.0(2) . . . . ? O1 C3 C10 C15 177.53(14) . . . . ? C2 C3 C10 C15 60.2(2) . . . . ? C4 C3 C10 C15 -61.8(2) . . . . ? C15 C10 C11 C12 1.5(3) . . . . ? C3 C10 C11 C12 -177.30(16) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C10 -0.9(3) . . . . ? C11 C10 C15 C14 -0.5(3) . . . . ? C3 C10 C15 C14 178.33(16) . . . . ? O2B O2A C16A N1 -1.7(19) 2_666 . . . ? O2B O2A C16A C17A 179.5(18) 2_666 . . . ? O2B O2A C16A C20B -57(5) 2_666 . . . ? C16B N1 C16A O2A -31.6(17) . . . . ? C20A N1 C16A O2A 174.5(2) . . . . ? C20B N1 C16A O2A -173.7(9) . . . . ? C16B N1 C16A C17A 147.2(17) . . . . ? C20A N1 C16A C17A -6.6(3) . . . . ? C20B N1 C16A C17A 5.1(9) . . . . ? C16B N1 C16A C20B 142.1(18) . . . . ? C20A N1 C16A C20B -11.7(9) . . . . ? O2A C16A C17A C18A -176.8(2) . . . . ? N1 C16A C17A C18A 4.5(3) . . . . ? C20B C16A C17A C18A 9.6(8) . . . . ? O2A C16A C17A C20B 173.7(9) . . . . ? N1 C16A C17A C20B -5.1(9) . . . . ? C16A C17A C18A C20B -10.3(9) . . . . ? C16A C17A C18A C19 -1.4(4) . . . . ? C20B C17A C18A C19 8.9(9) . . . . ? C17A C18A C19 C20B -9.7(10) . . . . ? C17A C18A C19 C20A -0.2(4) . . . . ? C20B C18A C19 C20A 9.4(10) . . . . ? C17A C18A C19 C18B -15(5) . . . . ? C20B C18A C19 C18B -6(5) . . . . ? C20B C19 C20A C18B -167.9(14) . . . . ? C18A C19 C20A C18B -176.9(10) . . . . ? C18A C19 C20A C20B -9.0(10) . . . . ? C18B C19 C20A C20B 167.9(14) . . . . ? C20B C19 C20A N1 7.6(10) . . . . ? C18A C19 C20A N1 -1.5(4) . . . . ? C18B C19 C20A N1 175.4(10) . . . . ? C20B C19 C20A C22A -170.3(10) . . . . ? C18A C19 C20A C22A -179.3(3) . . . . ? C18B C19 C20A C22A -2.4(10) . . . . ? C20B C19 C20A C16B -45(2) . . . . ? C18A C19 C20A C16B -54.2(18) . . . . ? C18B C19 C20A C16B 123(2) . . . . ? C16A N1 C20A C18B 160(5) . . . . ? C16B N1 C20A C18B -11(5) . . . . ? C20B N1 C20A C18B 147(5) . . . . ? C16A N1 C20A C19 5.3(3) . . . . ? C16B N1 C20A C19 -165.6(6) . . . . ? C20B N1 C20A C19 -7.4(9) . . . . ? C16A N1 C20A C20B 12.7(10) . . . . ? C16B N1 C20A C20B -158.2(11) . . . . ? C16A N1 C20A C22A -176.7(2) . . . . ? C16B N1 C20A C22A 12.4(6) . . . . ? C20B N1 C20A C22A 170.6(10) . . . . ? C16A N1 C20A C16B 170.9(7) . . . . ? C20B N1 C20A C16B 158.2(11) . . . . ? C19 C20A C22A C18B 2.7(11) . . . . ? C20B C20A C22A C18B -108(3) . . . . ? N1 C20A C22A C18B -175.2(11) . . . . ? C16B C20A C22A C18B -164.2(12) . . . . ? C18B C20A C22A C16B 164.2(12) . . . . ? C19 C20A C22A C16B 166.9(6) . . . . ? C20B C20A C22A C16B 56(3) . . . . ? N1 C20A C22A C16B -11.0(6) . . . . ? O2A O2B C16B N1 24(5) 2_666 . . . ? O2A O2B C16B C22A -138(3) 2_666 . . . ? O2A O2B C16B C20A 10(10) 2_666 . . . ? C16A N1 C16B O2B 25(3) . . . . ? C20A N1 C16B O2B -177.1(12) . . . . ? C20B N1 C16B O2B 159.2(12) . . . . ? C16A N1 C16B C22A -168.6(10) . . . . ? C20A N1 C16B C22A -10.6(5) . . . . ? C20B N1 C16B C22A -34.3(14) . . . . ? C16A N1 C16B C20A -158.0(14) . . . . ? C20B N1 C16B C20A -23.7(11) . . . . ? C18B C22A C16B O2B -172.8(15) . . . . ? C20A C22A C16B O2B 173.5(17) . . . . ? C18B C22A C16B N1 24.4(13) . . . . ? C20A C22A C16B N1 10.6(5) . . . . ? C18B C22A C16B C20A 13.7(10) . . . . ? C18B C20A C16B O2B -167(7) . . . . ? C19 C20A C16B O2B 76(7) . . . . ? C20B C20A C16B O2B 36(7) . . . . ? N1 C20A C16B O2B 15(6) . . . . ? C22A C20A C16B O2B -152(7) . . . . ? C18B C20A C16B N1 177.8(10) . . . . ? C19 C20A C16B N1 60.7(19) . . . . ? C20B C20A C16B N1 20.3(10) . . . . ? C22A C20A C16B N1 -167.6(6) . . . . ? C18B C20A C16B C22A -14.6(11) . . . . ? C19 C20A C16B C22A -131.8(16) . . . . ? C20B C20A C16B C22A -172.1(9) . . . . ? N1 C20A C16B C22A 167.6(6) . . . . ? C19 C20A C18B C22A -177.6(10) . . . . ? C20B C20A C18B C22A 169.4(11) . . . . ? N1 C20A C18B C22A 26(6) . . . . ? C16B C20A C18B C22A 16.0(12) . . . . ? C20B C20A C18B C19 -13.0(14) . . . . ? N1 C20A C18B C19 -156(5) . . . . ? C22A C20A C18B C19 177.6(10) . . . . ? C16B C20A C18B C19 -166.3(6) . . . . ? C16B C22A C18B C20A -15.1(11) . . . . ? C20A C22A C18B C19 -2.6(10) . . . . ? C16B C22A C18B C19 -18(2) . . . . ? C20B C19 C18B C20A 11.6(13) . . . . ? C18A C19 C18B C20A 17(5) . . . . ? C20B C19 C18B C22A 14(2) . . . . ? C20A C19 C18B C22A 2.9(12) . . . . ? C18A C19 C18B C22A 20(6) . . . . ? C18A C19 C20B C20A 170.6(10) . . . . ? C18B C19 C20B C20A -10.5(12) . . . . ? C20A C19 C20B C18A -170.6(10) . . . . ? C18B C19 C20B C18A 179.0(9) . . . . ? C20A C19 C20B N1 -7.5(9) . . . . ? C18A C19 C20B N1 163.1(19) . . . . ? C18B C19 C20B N1 -18(2) . . . . ? C20A C19 C20B C17A -161.4(19) . . . . ? C18A C19 C20B C17A 9.1(9) . . . . ? C18B C19 C20B C17A -171.9(13) . . . . ? C20A C19 C20B C16A -73(3) . . . . ? C18A C19 C20B C16A 97(4) . . . . ? C18B C19 C20B C16A -84(4) . . . . ? C18B C20A C20B C19 14.3(16) . . . . ? N1 C20A C20B C19 -172.5(10) . . . . ? C22A C20A C20B C19 116(3) . . . . ? C16B C20A C20B C19 169.1(6) . . . . ? C18B C20A C20B C18A 25(2) . . . . ? C19 C20A C20B C18A 10.5(11) . . . . ? N1 C20A C20B C18A -162(2) . . . . ? C22A C20A C20B C18A 127(2) . . . . ? C16B C20A C20B C18A 179.6(14) . . . . ? C18B C20A C20B N1 -173.2(11) . . . . ? C19 C20A C20B N1 172.5(10) . . . . ? C22A C20A C20B N1 -71(3) . . . . ? C16B C20A C20B N1 -18.4(9) . . . . ? C18B C20A C20B C17A 119(3) . . . . ? C19 C20A C20B C17A 104(3) . . . . ? N1 C20A C20B C17A -68(3) . . . . ? C22A C20A C20B C17A -139(4) . . . . ? C16B C20A C20B C17A -86(3) . . . . ? C18B C20A C20B C16A 176.7(12) . . . . ? C19 C20A C20B C16A 162.5(16) . . . . ? N1 C20A C20B C16A -10.0(7) . . . . ? C22A C20A C20B C16A -81(4) . . . . ? C16B C20A C20B C16A -28.4(15) . . . . ? C17A C18A C20B C19 170.9(9) . . . . ? C17A C18A C20B C20A 161.0(19) . . . . ? C19 C18A C20B C20A -9.9(10) . . . . ? C17A C18A C20B N1 59(3) . . . . ? C19 C18A C20B N1 -112(4) . . . . ? C19 C18A C20B C17A -170.9(9) . . . . ? C17A C18A C20B C16A 9.3(8) . . . . ? C19 C18A C20B C16A -161.7(17) . . . . ? C16A N1 C20B C19 -161.4(17) . . . . ? C16B N1 C20B C19 34(2) . . . . ? C20A N1 C20B C19 7.5(9) . . . . ? C16A N1 C20B C20A -168.9(8) . . . . ? C16B N1 C20B C20A 26.6(13) . . . . ? C16A N1 C20B C18A -57(3) . . . . ? C16B N1 C20B C18A 138(3) . . . . ? C20A N1 C20B C18A 112(4) . . . . ? C16A N1 C20B C17A -5.1(8) . . . . ? C16B N1 C20B C17A -169.6(10) . . . . ? C20A N1 C20B C17A 163.8(16) . . . . ? C16B N1 C20B C16A -164.6(8) . . . . ? C20A N1 C20B C16A 168.9(8) . . . . ? C18A C17A C20B C19 -9.8(10) . . . . ? C16A C17A C20B C19 160.3(18) . . . . ? C18A C17A C20B C20A -104(3) . . . . ? C16A C17A C20B C20A 66(3) . . . . ? C16A C17A C20B C18A 170.1(9) . . . . ? C18A C17A C20B N1 -165.2(17) . . . . ? C16A C17A C20B N1 4.9(8) . . . . ? C18A C17A C20B C16A -170.1(9) . . . . ? O2A C16A C20B C19 135(5) . . . . ? N1 C16A C20B C19 76(3) . . . . ? C17A C16A C20B C19 -99(3) . . . . ? O2A C16A C20B C20A 69(5) . . . . ? N1 C16A C20B C20A 10.5(8) . . . . ? C17A C16A C20B C20A -164.0(17) . . . . ? O2A C16A C20B C18A -136(4) . . . . ? N1 C16A C20B C18A 165.3(17) . . . . ? C17A C16A C20B C18A -9.2(8) . . . . ? O2A C16A C20B N1 59(5) . . . . ? C17A C16A C20B N1 -174.5(9) . . . . ? O2A C16A C20B C17A -127(4) . . . . ? N1 C16A C20B C17A 174.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.125 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.030 data_I-b-313K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 6-Methyl-2(1H)-Pyridinone ; _chemical_name_common 'Tetraphenylhexadiynediol and Methylpyridone' _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C6 H7 N O)' _chemical_formula_sum 'C42 H36 N2 O4' _chemical_formula_weight 632.73 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.46(2) _cell_length_b 10.84(3) _cell_length_c 11.35(3) _cell_angle_alpha 64.31(11) _cell_angle_beta 80.49(8) _cell_angle_gamma 68.68(6) _cell_volume 874(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10382 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.65 _exptl_crystal_description Blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.077 _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 10382 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 24.65 _reflns_number_total 2930 _reflns_number_gt 1572 _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^)+(0.1290P)^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 2930 _refine_ls_number_parameters 234 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1822 _refine_ls_wR_factor_gt 0.1643 _refine_ls_goodness_of_fit_ref 0.814 _refine_ls_restrained_S_all 0.816 _refine_ls_shift/su_max 0.003 _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 0.1557(2) 0.77448(19) 0.66584(17) 0.0682(6) Uani 1 1 d . . . H1O1 H 0.2319 0.6994 0.6706 0.102 Uiso 1 1 calc R . . C1 C 0.0277(3) 0.5565(3) 0.9580(3) 0.0529(6) Uani 1 1 d . . . C2 C 0.0775(3) 0.6541(3) 0.8850(2) 0.0525(6) Uani 1 1 d . . . C3 C 0.1278(3) 0.7798(2) 0.7914(2) 0.0497(6) Uani 1 1 d . . . C4 C 0.2859(3) 0.7849(3) 0.8356(3) 0.0574(7) Uani 1 1 d . . . C5 C 0.3476(4) 0.8973(3) 0.7579(4) 0.0885(10) Uani 1 1 d . . . H5 H 0.2930 0.9669 0.6802 0.106 Uiso 1 1 calc R . . C6 C 0.4876(5) 0.9078(5) 0.7932(6) 0.1243(17) Uani 1 1 d . . . H6 H 0.5263 0.9849 0.7406 0.149 Uiso 1 1 calc R . . C7 C 0.5708(4) 0.8039(6) 0.9070(6) 0.1255(18) Uani 1 1 d . . . H7 H 0.6674 0.8097 0.9304 0.151 Uiso 1 1 calc R . . C8 C 0.5123(4) 0.6933(4) 0.9849(4) 0.0964(12) Uani 1 1 d . . . H8 H 0.5676 0.6241 1.0624 0.116 Uiso 1 1 calc R . . C9 C 0.3708(3) 0.6830(3) 0.9494(3) 0.0675(8) Uani 1 1 d . . . H9 H 0.3322 0.6061 1.0030 0.081 Uiso 1 1 calc R . . C10 C -0.0221(3) 0.9180(2) 0.7804(2) 0.0485(6) Uani 1 1 d . . . C11 C -0.1007(3) 1.0171(3) 0.6648(3) 0.0679(8) Uani 1 1 d . . . H11 H -0.0665 1.0008 0.5891 0.081 Uiso 1 1 calc R . . C12 C -0.2329(3) 1.1437(3) 0.6597(3) 0.0788(9) Uani 1 1 d . . . H12 H -0.2858 1.2107 0.5806 0.095 Uiso 1 1 calc R . . C13 C -0.2840(3) 1.1689(3) 0.7691(4) 0.0749(9) Uani 1 1 d . . . H13 H -0.3709 1.2532 0.7652 0.090 Uiso 1 1 calc R . . C14 C -0.2057(3) 1.0680(3) 0.8868(3) 0.0767(9) Uani 1 1 d . . . H14 H -0.2405 1.0842 0.9625 0.092 Uiso 1 1 calc R . . C15 C -0.0762(3) 0.9437(3) 0.8919(3) 0.0627(7) Uani 1 1 d . . . H15 H -0.0245 0.8763 0.9713 0.075 Uiso 1 1 calc R . . O2A O 0.4613(3) 0.5518(3) 0.6342(2) 0.0707(8) Uani 0.777(4) 1 d P . . N1 N 0.6578(3) 0.5906(2) 0.4749(2) 0.0692(7) Uani 1 1 d D . . H1NA H 0.6171 0.5525 0.4402 0.083 Uiso 0.777(4) 1 d PR . . C16A C 0.5866(4) 0.5944(4) 0.5892(4) 0.0628(10) Uani 0.777(4) 1 d P . . C17A C 0.6722(4) 0.6448(4) 0.6518(4) 0.0946(11) Uani 1 1 d . . . H17A H 0.6366 0.6436 0.7345 0.114 Uiso 0.777(4) 1 d PR . . C18A C 0.7963(5) 0.6955(5) 0.5890(6) 0.1023(16) Uani 0.777(4) 1 d P . . H18A H 0.8486 0.7292 0.6285 0.123 Uiso 0.777(4) 1 d PR . . C19 C 0.8596(4) 0.6950(4) 0.4602(4) 0.0957(11) Uani 1 1 d D . . H19A H 0.9490 0.7295 0.4173 0.115 Uiso 0.777(4) 1 d PR . . C20A C 0.7834(4) 0.6458(4) 0.4074(4) 0.0777(13) Uani 0.777(4) 1 d P . . C22A C 0.8305(4) 0.6349(5) 0.2795(4) 0.1136(13) Uani 1 1 d . . . H22A H 0.9330 0.6591 0.2472 0.136 Uiso 0.777(4) 1 d PR . . H22B H 0.7406 0.7028 0.2190 0.136 Uiso 0.777(4) 1 d PR . . H22C H 0.8491 0.5383 0.2886 0.136 Uiso 0.777(4) 1 d PR . . H1NB H 0.5572 0.5902 0.5022 0.136 Uiso 0.22 1 d P . . H22D H 0.5976 0.5878 0.6852 0.136 Uiso 0.22 1 d P . . H22E H 0.6077 0.7456 0.6265 0.136 Uiso 0.22 1 d P . . H22F H 0.7579 0.6130 0.7095 0.136 Uiso 0.22 1 d P . . H19B H 0.9019 0.7461 0.4859 0.136 Uiso 0.22 1 d P . . H17B H 0.8500 0.6539 0.1867 0.136 Uiso 0.22 1 d P . . O2B O 0.6203(12) 0.4819(9) 0.3591(8) 0.063(3) Uiso 0.223(4) 1 d PD . . C16B C 0.7016(13) 0.5496(12) 0.3756(9) 0.060(3) Uiso 0.223(4) 1 d PD . . C18B C 0.897(2) 0.6812(17) 0.3337(11) 0.098(5) Uiso 0.223(4) 1 d PD . . H18B H 0.9930 0.7060 0.2911 0.118 Uiso 0.223(4) 1 d PR . . C20B C 0.7461(14) 0.6345(14) 0.5321(10) 0.080(4) Uiso 0.223(4) 1 d PD . . 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 0.0710(11) 0.0636(12) 0.0605(12) -0.0278(10) 0.0086(9) -0.0125(9) C1 0.0471(12) 0.0455(14) 0.0657(16) -0.0221(12) 0.0011(11) -0.0160(11) C2 0.0448(13) 0.0465(15) 0.0641(16) -0.0221(13) -0.0022(11) -0.0126(11) C3 0.0466(12) 0.0433(14) 0.0550(15) -0.0179(12) 0.0049(10) -0.0149(11) C4 0.0453(13) 0.0450(15) 0.0855(19) -0.0339(14) 0.0115(12) -0.0148(11) C5 0.0667(18) 0.0658(19) 0.132(3) -0.0357(19) 0.0173(17) -0.0334(15) C6 0.068(2) 0.097(3) 0.240(6) -0.093(4) 0.038(3) -0.049(2) C7 0.0472(19) 0.124(4) 0.263(6) -0.140(4) 0.010(3) -0.020(2) C8 0.0554(17) 0.099(3) 0.164(3) -0.092(3) -0.0234(19) 0.0003(17) C9 0.0462(14) 0.0593(17) 0.104(2) -0.0458(17) -0.0088(14) -0.0054(12) C10 0.0397(11) 0.0441(14) 0.0567(16) -0.0160(12) 0.0033(10) -0.0154(10) C11 0.0582(15) 0.0652(19) 0.0578(17) -0.0149(14) 0.0053(12) -0.0107(14) C12 0.0617(16) 0.0601(19) 0.075(2) -0.0048(16) -0.0007(14) -0.0045(14) C13 0.0529(15) 0.0530(18) 0.105(3) -0.0292(18) -0.0041(16) -0.0045(13) C14 0.0674(17) 0.072(2) 0.100(2) -0.0541(19) -0.0025(16) -0.0092(16) C15 0.0540(14) 0.0571(17) 0.0722(19) -0.0292(14) -0.0096(12) -0.0055(12) O2A 0.0555(16) 0.0731(18) 0.0875(19) -0.0398(14) 0.0063(12) -0.0198(13) N1 0.0588(13) 0.0682(16) 0.0900(18) -0.0406(14) 0.0044(12) -0.0229(11) C16A 0.0532(19) 0.057(2) 0.073(3) -0.0295(18) -0.0016(17) -0.0077(16) C17A 0.088(2) 0.104(3) 0.117(3) -0.068(2) -0.002(2) -0.030(2) C18A 0.089(3) 0.092(3) 0.151(5) -0.064(3) -0.016(3) -0.033(3) C19 0.081(2) 0.082(2) 0.130(3) -0.043(2) 0.005(2) -0.0362(19) C20A 0.056(2) 0.068(3) 0.100(3) -0.027(2) 0.005(2) -0.0201(18) C22A 0.087(2) 0.143(4) 0.094(3) -0.041(3) 0.017(2) -0.036(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 1.429(4) . ? O1 H1O1 0.8200 . ? C1 C2 1.197(4) . ? C1 C1 1.374(6) 2_567 ? C2 C3 1.478(5) . ? C3 C4 1.530(5) . ? C3 C10 1.541(5) . ? C4 C9 1.377(5) . ? C4 C5 1.383(5) . ? C5 C6 1.368(6) . ? C5 H5 0.9300 . ? C6 C7 1.377(7) . ? C6 H6 0.9300 . ? C7 C8 1.354(6) . ? C7 H7 0.9300 . ? C8 C9 1.379(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.365(5) . ? C10 C15 1.383(5) . ? C11 C12 1.405(5) . ? C11 H11 0.9300 . ? C12 C13 1.354(5) . ? C12 H12 0.9300 . ? C13 C14 1.386(5) . ? C13 H13 0.9300 . ? C14 C15 1.378(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A O2B 0.870(8) 2_666 ? O2A C16A 1.252(5) . ? N1 C16B 1.335(8) . ? N1 C16A 1.348(5) . ? N1 C20B 1.376(8) . ? N1 C20A 1.367(5) . ? N1 H1NA 0.8558 . ? N1 H1NB 0.8565 . ? C16A C17A 1.458(5) . ? C16A C20B 1.524(9) . ? C16A H1NB 1.0800 . ? C16A H22D 1.0786 . ? C17A C18A 1.322(6) . ? C17A C20B 1.432(11) . ? C17A H17A 0.9324 . ? C17A H22D 0.9613 . ? C17A H22E 0.9593 . ? C17A H22F 0.9229 . ? C18A C20B 1.304(10) . ? C18A C19 1.473(7) . ? C18A H18A 0.9251 . ? C18A H22F 1.3344 . ? C18A H19B 1.3861 . ? C19 C20A 1.310(6) . ? C19 C20B 1.324(8) . ? C19 C18B 1.479(9) . ? C19 H19A 0.9355 . ? C19 H19B 0.9161 . ? C20A C18B 1.226(13) . ? C20A C20B 1.360(11) . ? C20A C22A 1.484(7) . ? C20A C16B 1.621(10) . ? C22A C18B 1.241(13) . ? C22A C16B 1.643(11) . ? C22A H22A 0.9644 . ? C22A H22B 0.9586 . ? C22A H22C 0.9622 . ? C22A H17B 0.9792 . ? O2B O2A 0.870(8) 2_666 ? O2B C16B 1.255(9) . ? O2B H1NA 1.4216 . ? C16B H1NA 0.9382 . ? C16B H22C 1.4607 . ? C18B H19A 1.4487 . ? C18B H22A 1.0799 . ? C18B H18B 0.9356 . ? 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 H1O1 109.5 . . ? C2 C1 C1 179.4(3) . 2_567 ? C1 C2 C3 176.3(2) . . ? O1 C3 C2 109.0(3) . . ? O1 C3 C4 110.6(2) . . ? C2 C3 C4 112.2(2) . . ? O1 C3 C10 108.0(2) . . ? C2 C3 C10 107.6(3) . . ? C4 C3 C10 109.4(3) . . ? C9 C4 C5 117.9(3) . . ? C9 C4 C3 123.4(3) . . ? C5 C4 C3 118.7(3) . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C7 C6 C5 119.8(4) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.1(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 121.0(3) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C15 118.9(3) . . ? C11 C10 C3 122.7(3) . . ? C15 C10 C3 118.4(2) . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.4(3) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 120.8(3) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? O2B O2A C16A 160.5(7) 2_666 . ? C16B N1 C16A 158.9(5) . . ? C16B N1 C20B 130.0(6) . . ? C16A N1 C20B 68.0(5) . . ? C16B N1 C20A 73.7(5) . . ? C16A N1 C20A 126.6(3) . . ? C20B N1 C20A 59.4(5) . . ? C16B N1 H1NA 44.3 . . ? C16A N1 H1NA 116.2 . . ? C20B N1 H1NA 171.1 . . ? C20A N1 H1NA 117.2 . . ? C16B N1 H1NB 110.8 . . ? C16A N1 H1NB 53.2 . . ? C20B N1 H1NB 119.2 . . ? C20A N1 H1NB 158.0 . . ? H1NA N1 H1NB 67.3 . . ? O2A C16A N1 119.8(3) . . ? O2A C16A C17A 126.0(4) . . ? N1 C16A C17A 114.2(3) . . ? O2A C16A C20B 175.1(6) . . ? N1 C16A C20B 56.8(4) . . ? C17A C16A C20B 57.4(4) . . ? O2A C16A H1NB 82.4 . . ? N1 C16A H1NB 39.4 . . ? C17A C16A H1NB 150.0 . . ? C20B C16A H1NB 95.0 . . ? O2A C16A H22D 86.4 . . ? N1 C16A H22D 150.3 . . ? C17A C16A H22D 41.3 . . ? C20B C16A H22D 96.0 . . ? H1NB C16A H22D 168.7 . . ? C18A C17A C16A 119.4(4) . . ? C18A C17A C20B 56.3(4) . . ? C16A C17A C20B 63.7(4) . . ? C18A C17A H17A 120.8 . . ? C16A C17A H17A 119.8 . . ? C20B C17A H17A 173.0 . . ? C18A C17A H22D 162.6 . . ? C16A C17A H22D 47.7 . . ? C20B C17A H22D 108.1 . . ? H17A C17A H22D 73.6 . . ? C18A C17A H22E 83.2 . . ? C16A C17A H22E 104.4 . . ? C20B C17A H22E 104.3 . . ? H17A C17A H22E 81.1 . . ? H22D C17A H22E 110.1 . . ? C18A C17A H22F 70.4 . . ? C16A C17A H22F 142.5 . . ? C20B C17A H22F 108.9 . . ? H17A C17A H22F 64.5 . . ? H22D C17A H22F 112.2 . . ? H22E C17A H22F 112.9 . . ? C20B C18A C17A 66.1(5) . . ? C20B C18A C19 56.5(5) . . ? C17A C18A C19 122.4(4) . . ? C20B C18A H18A 171.1 . . ? C17A C18A H18A 119.0 . . ? C19 C18A H18A 118.6 . . ? C20B C18A H22F 94.6 . . ? C17A C18A H22F 40.7 . . ? C19 C18A H22F 143.4 . . ? H18A C18A H22F 86.5 . . ? C20B C18A H19B 93.7 . . ? C17A C18A H19B 158.6 . . ? C19 C18A H19B 37.2 . . ? H18A C18A H19B 82.0 . . ? H22F C18A H19B 156.2 . . ? C20A C19 C20B 62.2(5) . . ? C20A C19 C18A 116.9(4) . . ? C20B C19 C18A 55.3(5) . . ? C20A C19 C18B 51.7(6) . . ? C20B C19 C18B 113.5(7) . . ? C18A C19 C18B 168.7(6) . . ? C20A C19 H19A 121.4 . . ? C20B C19 H19A 173.2 . . ? C18A C19 H19A 121.7 . . ? C18B C19 H19A 69.6 . . ? C20A C19 H19B 169.3 . . ? C20B C19 H19B 121.4 . . ? C18A C19 H19B 66.2 . . ? C18B C19 H19B 125.0 . . ? H19A C19 H19B 56.4 . . ? C18B C20A C19 71.2(6) . . ? C18B C20A C20B 130.0(7) . . ? C19 C20A C20B 59.4(4) . . ? C18B C20A N1 168.2(7) . . ? C19 C20A N1 119.9(4) . . ? C20B C20A N1 60.6(4) . . ? C18B C20A C22A 53.5(6) . . ? C19 C20A C22A 124.7(4) . . ? C20B C20A C22A 171.7(6) . . ? N1 C20A C22A 115.2(4) . . ? C18B C20A C16B 116.0(7) . . ? C19 C20A C16B 165.8(5) . . ? C20B C20A C16B 110.7(5) . . ? N1 C20A C16B 52.2(3) . . ? C22A C20A C16B 63.7(4) . . ? C18B C22A C20A 52.6(6) . . ? C18B C22A C16B 113.7(7) . . ? C20A C22A C16B 62.2(3) . . ? C18B C22A H22A 57.0 . . ? C20A C22A H22A 109.2 . . ? C16B C22A H22A 160.0 . . ? C18B C22A H22B 118.4 . . ? C20A C22A H22B 108.7 . . ? C16B C22A H22B 90.9 . . ? H22A C22A H22B 109.1 . . ? C18B C22A H22C 131.6 . . ? C20A C22A H22C 110.5 . . ? C16B C22A H22C 61.8 . . ? H22A C22A H22C 109.4 . . ? H22B C22A H22C 110.0 . . ? C18B C22A H17B 121.6 . . ? C20A C22A H17B 165.8 . . ? C16B C22A H17B 124.7 . . ? H22A C22A H17B 68.3 . . ? H22B C22A H17B 61.1 . . ? H22C C22A H17B 83.0 . . ? O2A O2B C16B 159.4(11) 2_666 . ? O2A O2B H1NA 119.3 2_666 . ? C16B O2B H1NA 40.4 . . ? O2B C16B N1 118.7(8) . . ? O2B C16B C20A 172.1(8) . . ? N1 C16B C20A 54.1(4) . . ? O2B C16B C22A 132.2(7) . . ? N1 C16B C22A 107.5(6) . . ? C20A C16B C22A 54.1(4) . . ? O2B C16B H1NA 79.4 . . ? N1 C16B H1NA 39.6 . . ? C20A C16B H1NA 93.1 . . ? C22A C16B H1NA 143.4 . . ? O2B C16B H22C 105.4 . . ? N1 C16B H22C 134.7 . . ? C20A C16B H22C 82.3 . . ? C22A C16B H22C 35.5 . . ? H1NA C16B H22C 172.4 . . ? C20A C18B C22A 74.0(9) . . ? C20A C18B C19 57.0(5) . . ? C22A C18B C19 131.0(10) . . ? C20A C18B H19A 94.3 . . ? C22A C18B H19A 168.2 . . ? C19 C18B H19A 37.3 . . ? C20A C18B H22A 122.0 . . ? C22A C18B H22A 48.5 . . ? C19 C18B H22A 173.8 . . ? H19A C18B H22A 143.2 . . ? C20A C18B H18B 169.6 . . ? C22A C18B H18B 115.6 . . ? C19 C18B H18B 113.3 . . ? H19A C18B H18B 76.2 . . ? H22A C18B H18B 67.2 . . ? C18A C20B C19 68.2(5) . . ? C18A C20B C20A 126.0(7) . . ? C19 C20B C20A 58.4(4) . . ? C18A C20B N1 167.2(11) . . ? C19 C20B N1 118.3(7) . . ? C20A C20B N1 60.0(4) . . ? C18A C20B C17A 57.5(5) . . ? C19 C20B C17A 125.4(7) . . ? C20A C20B C17A 167.6(11) . . ? N1 C20B C17A 114.1(6) . . ? C18A C20B C16A 115.9(8) . . ? C19 C20B C16A 166.3(10) . . ? C20A C20B C16A 114.4(6) . . ? N1 C20B C16A 55.1(4) . . ? C17A C20B C16A 59.0(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 156(33) 2_567 . . . ? C1 C2 C3 O1 -81(4) . . . . ? C1 C2 C3 C4 157(4) . . . . ? C1 C2 C3 C10 36(4) . . . . ? O1 C3 C4 C9 -121.6(3) . . . . ? C2 C3 C4 C9 0.3(3) . . . . ? C10 C3 C4 C9 119.6(3) . . . . ? O1 C3 C4 C5 58.4(3) . . . . ? C2 C3 C4 C5 -179.7(2) . . . . ? C10 C3 C4 C5 -60.4(3) . . . . ? C9 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 C6 179.4(3) . . . . ? C4 C5 C6 C7 1.1(6) . . . . ? C5 C6 C7 C8 -1.3(6) . . . . ? C6 C7 C8 C9 1.1(6) . . . . ? C5 C4 C9 C8 0.4(4) . . . . ? C3 C4 C9 C8 -179.6(2) . . . . ? C7 C8 C9 C4 -0.6(5) . . . . ? O1 C3 C10 C11 -3.7(3) . . . . ? C2 C3 C10 C11 -121.2(3) . . . . ? C4 C3 C10 C11 116.7(3) . . . . ? O1 C3 C10 C15 177.88(19) . . . . ? C2 C3 C10 C15 60.4(3) . . . . ? C4 C3 C10 C15 -61.7(3) . . . . ? C15 C10 C11 C12 0.7(4) . . . . ? C3 C10 C11 C12 -177.8(2) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C11 C10 C15 C14 -0.8(4) . . . . ? C3 C10 C15 C14 177.7(2) . . . . ? C13 C14 C15 C10 0.2(4) . . . . ? O2B O2A C16A N1 -2(2) 2_666 . . . ? O2B O2A C16A C17A -179.0(19) 2_666 . . . ? O2B O2A C16A C20B -47(7) 2_666 . . . ? C16B N1 C16A O2A -24.1(16) . . . . ? C20B N1 C16A O2A -175.8(7) . . . . ? C20A N1 C16A O2A 173.3(3) . . . . ? C16B N1 C16A C17A 153.6(14) . . . . ? C20B N1 C16A C17A 1.9(7) . . . . ? C20A N1 C16A C17A -9.1(5) . . . . ? C16B N1 C16A C20B 151.7(16) . . . . ? C20A N1 C16A C20B -11.0(7) . . . . ? O2A C16A C17A C18A -175.6(3) . . . . ? N1 C16A C17A C18A 6.8(5) . . . . ? C20B C16A C17A C18A 8.7(7) . . . . ? O2A C16A C17A C20B 175.6(7) . . . . ? N1 C16A C17A C20B -1.9(7) . . . . ? C16A C17A C18A C20B -9.4(7) . . . . ? C16A C17A C18A C19 -3.9(6) . . . . ? C20B C17A C18A C19 5.6(7) . . . . ? C20B C18A C19 C20A 8.2(8) . . . . ? C17A C18A C19 C20A 2.1(6) . . . . ? C17A C18A C19 C20B -6.1(8) . . . . ? C20B C18A C19 C18B 6(4) . . . . ? C17A C18A C19 C18B 0(4) . . . . ? C20B C19 C20A C18B -171.8(11) . . . . ? C18A C19 C20A C18B -179.5(9) . . . . ? C18A C19 C20A C20B -7.6(8) . . . . ? C18B C19 C20A C20B 171.8(11) . . . . ? C20B C19 C20A N1 4.1(7) . . . . ? C18A C19 C20A N1 -3.6(5) . . . . ? C18B C19 C20A N1 175.9(9) . . . . ? C20B C19 C20A C22A -171.5(8) . . . . ? C18A C19 C20A C22A -179.1(4) . . . . ? C18B C19 C20A C22A 0.3(9) . . . . ? C20B C19 C20A C16B -48(2) . . . . ? C18A C19 C20A C16B -56(2) . . . . ? C18B C19 C20A C16B 123(2) . . . . ? C16B N1 C20A C18B -5(4) . . . . ? C16A N1 C20A C18B 168(4) . . . . ? C20B N1 C20A C18B 157(4) . . . . ? C16B N1 C20A C19 -165.8(6) . . . . ? C16A N1 C20A C19 7.8(5) . . . . ? C20B N1 C20A C19 -4.0(7) . . . . ? C16B N1 C20A C20B -161.8(9) . . . . ? C16A N1 C20A C20B 11.8(7) . . . . ? C16B N1 C20A C22A 10.2(6) . . . . ? C16A N1 C20A C22A -176.2(3) . . . . ? C20B N1 C20A C22A 171.9(8) . . . . ? C16A N1 C20A C16B 173.6(6) . . . . ? C20B N1 C20A C16B 161.8(9) . . . . ? C19 C20A C22A C18B -0.4(11) . . . . ? C20B C20A C22A C18B -118(4) . . . . ? N1 C20A C22A C18B -176.1(10) . . . . ? C16B C20A C22A C18B -167.2(11) . . . . ? C18B C20A C22A C16B 167.2(11) . . . . ? C19 C20A C22A C16B 166.8(6) . . . . ? C20B C20A C22A C16B 49(3) . . . . ? N1 C20A C22A C16B -9.0(5) . . . . ? O2A O2B C16B N1 18(4) 2_666 . . . ? O2A O2B C16B C20A -6(10) 2_666 . . . ? O2A O2B C16B C22A -146(2) 2_666 . . . ? C16A N1 C16B O2B 18(2) . . . . ? C20B N1 C16B O2B 163.3(10) . . . . ? C20A N1 C16B O2B -176.1(11) . . . . ? C16A N1 C16B C20A -165.6(13) . . . . ? C20B N1 C16B C20A -20.6(9) . . . . ? C16A N1 C16B C22A -174.3(9) . . . . ? C20B N1 C16B C22A -29.3(12) . . . . ? C20A N1 C16B C22A -8.7(5) . . . . ? C18B C20A C16B O2B -156(7) . . . . ? C19 C20A C16B O2B 86(8) . . . . ? C20B C20A C16B O2B 43(7) . . . . ? N1 C20A C16B O2B 26(7) . . . . ? C22A C20A C16B O2B -144(7) . . . . ? C18B C20A C16B N1 178.8(9) . . . . ? C19 C20A C16B N1 60(2) . . . . ? C20B C20A C16B N1 16.9(8) . . . . ? C22A C20A C16B N1 -169.7(6) . . . . ? C18B C20A C16B C22A -11.5(10) . . . . ? C19 C20A C16B C22A -129.8(19) . . . . ? C20B C20A C16B C22A -173.3(7) . . . . ? N1 C20A C16B C22A 169.7(6) . . . . ? C18B C22A C16B O2B -175.2(13) . . . . ? C20A C22A C16B O2B 173.7(14) . . . . ? C18B C22A C16B N1 19.8(13) . . . . ? C20A C22A C16B N1 8.7(5) . . . . ? C18B C22A C16B C20A 11.1(10) . . . . ? C19 C20A C18B C22A 179.7(9) . . . . ? C20B C20A C18B C22A 170.5(9) . . . . ? N1 C20A C18B C22A 17(5) . . . . ? C16B C20A C18B C22A 12.8(11) . . . . ? C20B C20A C18B C19 -9.2(12) . . . . ? N1 C20A C18B C19 -162(4) . . . . ? C22A C20A C18B C19 -179.7(9) . . . . ? C16B C20A C18B C19 -166.9(6) . . . . ? C16B C22A C18B C20A -12.4(11) . . . . ? C20A C22A C18B C19 0.4(10) . . . . ? C16B C22A C18B C19 -12(2) . . . . ? C20B C19 C18B C20A 7.9(10) . . . . ? C18A C19 C18B C20A 2(4) . . . . ? C20A C19 C18B C22A -0.4(12) . . . . ? C20B C19 C18B C22A 7(2) . . . . ? C18A C19 C18B C22A 2(5) . . . . ? C17A C18A C20B C19 174.4(7) . . . . ? C17A C18A C20B C20A 165.7(14) . . . . ? C19 C18A C20B C20A -8.7(9) . . . . ? C17A C18A C20B N1 52(4) . . . . ? C19 C18A C20B N1 -123(4) . . . . ? C19 C18A C20B C17A -174.4(7) . . . . ? C17A C18A C20B C16A 8.7(7) . . . . ? C19 C18A C20B C16A -165.7(13) . . . . ? C20A C19 C20B C18A -171.7(8) . . . . ? C18B C19 C20B C18A -178.7(8) . . . . ? C18A C19 C20B C20A 171.7(8) . . . . ? C18B C19 C20B C20A -7.0(9) . . . . ? C20A C19 C20B N1 -4.0(7) . . . . ? C18A C19 C20B N1 167.7(14) . . . . ? C18B C19 C20B N1 -11.0(15) . . . . ? C20A C19 C20B C17A -165.9(14) . . . . ? C18A C19 C20B C17A 5.8(7) . . . . ? C18B C19 C20B C17A -172.9(11) . . . . ? C20A C19 C20B C16A -62(4) . . . . ? C18A C19 C20B C16A 110(4) . . . . ? C18B C19 C20B C16A -69(4) . . . . ? C18B C20A C20B C18A 20(2) . . . . ? C19 C20A C20B C18A 9.5(9) . . . . ? N1 C20A C20B C18A -166.4(15) . . . . ? C22A C20A C20B C18A 132(3) . . . . ? C16B C20A C20B C18A 178.2(11) . . . . ? C18B C20A C20B C19 10.1(13) . . . . ? N1 C20A C20B C19 -176.0(7) . . . . ? C22A C20A C20B C19 122(3) . . . . ? C16B C20A C20B C19 168.7(6) . . . . ? C18B C20A C20B N1 -173.9(11) . . . . ? C19 C20A C20B N1 176.0(7) . . . . ? C22A C20A C20B N1 -62(4) . . . . ? C16B C20A C20B N1 -15.3(7) . . . . ? C18B C20A C20B C17A 122(3) . . . . ? C19 C20A C20B C17A 112(4) . . . . ? N1 C20A C20B C17A -64(3) . . . . ? C22A C20A C20B C17A -126(5) . . . . ? C16B C20A C20B C17A -79(4) . . . . ? C18B C20A C20B C16A 176.9(11) . . . . ? C19 C20A C20B C16A 166.8(12) . . . . ? N1 C20A C20B C16A -9.2(5) . . . . ? C22A C20A C20B C16A -71(4) . . . . ? C16B C20A C20B C16A -24.5(12) . . . . ? C16B N1 C20B C18A 144(4) . . . . ? C16A N1 C20B C18A -48(4) . . . . ? C20A N1 C20B C18A 121(4) . . . . ? C16B N1 C20B C19 27.0(16) . . . . ? C16A N1 C20B C19 -165.9(12) . . . . ? C20A N1 C20B C19 3.9(7) . . . . ? C16B N1 C20B C20A 23.1(10) . . . . ? C16A N1 C20B C20A -169.8(6) . . . . ? C16B N1 C20B C17A -169.1(8) . . . . ? C16A N1 C20B C17A -1.9(7) . . . . ? C20A N1 C20B C17A 167.8(12) . . . . ? C16B N1 C20B C16A -167.2(8) . . . . ? C20A N1 C20B C16A 169.8(6) . . . . ? C16A C17A C20B C18A 170.9(7) . . . . ? C18A C17A C20B C19 -6.4(8) . . . . ? C16A C17A C20B C19 164.4(14) . . . . ? C18A C17A C20B C20A -111(4) . . . . ? C16A C17A C20B C20A 60(3) . . . . ? C18A C17A C20B N1 -169.0(13) . . . . ? C16A C17A C20B N1 1.9(7) . . . . ? C18A C17A C20B C16A -170.9(7) . . . . ? O2A C16A C20B C18A -143(5) . . . . ? N1 C16A C20B C18A 169.4(13) . . . . ? C17A C16A C20B C18A -8.6(7) . . . . ? O2A C16A C20B C19 113(7) . . . . ? N1 C16A C20B C19 65(4) . . . . ? C17A C16A C20B C19 -113(4) . . . . ? O2A C16A C20B C20A 58(7) . . . . ? N1 C16A C20B C20A 9.7(6) . . . . ? C17A C16A C20B C20A -168.2(12) . . . . ? O2A C16A C20B N1 48(6) . . . . ? C17A C16A C20B N1 -177.9(7) . . . . ? O2A C16A C20B C17A -134(6) . . . . ? N1 C16A C20B C17A 177.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.65 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.157 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.046 data_I-b_353K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 6-Methyl-2(1H)-Pyridinone ; _chemical_name_common 'Tetraphenylhexadiynediol and Methylpyridone' _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C6 H7 N O)' _chemical_formula_sum 'C42 H36 N2 O4' _chemical_formula_weight 632.73 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.465(20) _cell_length_b 10.85(3) _cell_length_c 11.36(2) _cell_angle_alpha 64.56(10) _cell_angle_beta 80.82(7) _cell_angle_gamma 68.92(6) _cell_volume 879(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10498 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 24.71 _exptl_crystal_description Blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.077 _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 10498 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2974 _reflns_number_gt 1569 _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^)+(0.1094P)^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 SHELXL _refine_ls_extinction_coef 0.074(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2974 _refine_ls_number_parameters 235 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.891 _refine_ls_shift/su_max 0.012 _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 0.15533(19) 0.77252(18) 0.66741(16) 0.0804(6) Uani 1 1 d . . . H1O1 H 0.2313 0.6976 0.6725 0.121 Uiso 1 1 calc R . . C1 C 0.0279(3) 0.5559(3) 0.9583(2) 0.0627(6) Uani 1 1 d . . . C2 C 0.0767(2) 0.6536(2) 0.8855(2) 0.0619(6) Uani 1 1 d . . . C3 C 0.1270(2) 0.7785(2) 0.7926(2) 0.0588(6) Uani 1 1 d . . . C4 C 0.2844(3) 0.7844(3) 0.8368(3) 0.0675(7) Uani 1 1 d . . . C5 C 0.3453(3) 0.8959(3) 0.7598(4) 0.1039(10) Uani 1 1 d . . . H5 H 0.2909 0.9651 0.6821 0.125 Uiso 1 1 calc R . . C6 C 0.4853(5) 0.9064(5) 0.7962(5) 0.1411(17) Uani 1 1 d . . . H6 H 0.5235 0.9837 0.7444 0.169 Uiso 1 1 calc R . . C7 C 0.5693(4) 0.8030(6) 0.9089(6) 0.1424(19) Uani 1 1 d . . . H7 H 0.6663 0.8086 0.9320 0.171 Uiso 1 1 calc R . . C8 C 0.5109(4) 0.6934(4) 0.9861(4) 0.1119(12) Uani 1 1 d . . . H8 H 0.5661 0.6248 1.0635 0.134 Uiso 1 1 calc R . . C9 C 0.3688(3) 0.6828(3) 0.9503(3) 0.0793(8) Uani 1 1 d . . . H9 H 0.3300 0.6062 1.0037 0.095 Uiso 1 1 calc R . . C10 C -0.0221(2) 0.9165(2) 0.7802(2) 0.0581(6) Uani 1 1 d . . . C11 C -0.1006(3) 1.0136(3) 0.6651(3) 0.0813(8) Uani 1 1 d . . . H11 H -0.0672 0.9960 0.5901 0.098 Uiso 1 1 calc R . . C12 C -0.2313(3) 1.1400(3) 0.6589(3) 0.0939(10) Uani 1 1 d . . . H12 H -0.2840 1.2061 0.5798 0.113 Uiso 1 1 calc R . . C13 C -0.2813(3) 1.1665(3) 0.7668(4) 0.0900(9) Uani 1 1 d . . . H13 H -0.3672 1.2512 0.7621 0.108 Uiso 1 1 calc R . . C14 C -0.2046(3) 1.0675(3) 0.8842(3) 0.0893(9) Uani 1 1 d . . . H14 H -0.2400 1.0845 0.9592 0.107 Uiso 1 1 calc R . . C15 C -0.0765(3) 0.9442(3) 0.8904(3) 0.0740(7) Uani 1 1 d . . . H15 H -0.0252 0.8779 0.9700 0.089 Uiso 1 1 calc R . . O2A O 0.4630(4) 0.5510(3) 0.6343(2) 0.0820(9) Uani 0.711(4) 1 d P . . N1 N 0.6593(2) 0.5894(2) 0.4763(2) 0.0810(7) Uani 1 1 d D . . H1NA H 0.6187 0.5513 0.4417 0.097 Uiso 0.711(4) 1 d PR . . C16A C 0.5874(4) 0.5940(4) 0.5895(4) 0.0717(11) Uani 0.711(4) 1 d P . . C17A C 0.6764(4) 0.6447(4) 0.6520(4) 0.1130(11) Uani 1 1 d . . . H17A H 0.6408 0.6435 0.7347 0.136 Uiso 0.711(4) 1 d PR . . C18A C 0.7961(6) 0.6959(5) 0.5899(6) 0.1161(18) Uani 0.711(4) 1 d P . . H18A H 0.8484 0.7296 0.6295 0.139 Uiso 0.711(4) 1 d PR . . C19 C 0.8595(4) 0.6955(4) 0.4597(4) 0.1142(11) Uani 1 1 d D . . H19A H 0.9490 0.7300 0.4168 0.137 Uiso 0.711(4) 1 d PR . . C20A C 0.7832(4) 0.6459(4) 0.4088(4) 0.0871(14) Uani 0.711(4) 1 d P . . C22A C 0.8298(4) 0.6329(5) 0.2816(4) 0.1313(14) Uani 1 1 d . . . H22A H 0.9323 0.6571 0.2493 0.158 Uiso 0.711(4) 1 d PR . . H22B H 0.7399 0.7008 0.2211 0.158 Uiso 0.711(4) 1 d PR . . H22C H 0.8484 0.5363 0.2906 0.158 Uiso 0.711(4) 1 d PR . . H1NB H 0.5572 0.5902 0.5022 0.158 Uiso 0.29 1 d P . . H22D H 0.5976 0.5878 0.6852 0.158 Uiso 0.29 1 d P . . H22E H 0.6077 0.7456 0.6265 0.158 Uiso 0.29 1 d P . . H22F H 0.7579 0.6130 0.7095 0.158 Uiso 0.29 1 d P . . H19B H 0.9019 0.7461 0.4859 0.158 Uiso 0.29 1 d P . . H17B H 0.8500 0.6539 0.1867 0.158 Uiso 0.29 1 d P . . O2B O 0.6205(10) 0.4814(7) 0.3602(6) 0.082(2) Uiso 0.289(4) 1 d PD . . C16B C 0.7028(10) 0.5492(9) 0.3767(7) 0.075(3) Uiso 0.289(4) 1 d PD . . C18B C 0.9015(16) 0.6794(14) 0.3332(9) 0.118(4) Uiso 0.289(4) 1 d PD . . H18B H 0.9970 0.7042 0.2906 0.142 Uiso 0.289(4) 1 d PR . . C20B C 0.7486(12) 0.6359(11) 0.5307(9) 0.098(3) Uiso 0.289(4) 1 d PD . . 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 0.0854(11) 0.0746(12) 0.0729(12) -0.0333(9) 0.0099(9) -0.0170(9) C1 0.0570(12) 0.0546(14) 0.0754(16) -0.0260(12) 0.0031(10) -0.0188(10) C2 0.0543(12) 0.0545(14) 0.0745(16) -0.0258(12) -0.0008(10) -0.0153(11) C3 0.0572(12) 0.0519(13) 0.0643(15) -0.0221(11) 0.0055(10) -0.0185(10) C4 0.0534(12) 0.0544(14) 0.1002(19) -0.0387(14) 0.0126(12) -0.0197(11) C5 0.0768(18) 0.082(2) 0.152(3) -0.0420(19) 0.0212(17) -0.0419(15) C6 0.087(2) 0.111(3) 0.256(6) -0.095(4) 0.044(3) -0.059(2) C7 0.063(2) 0.136(4) 0.289(6) -0.147(4) 0.015(3) -0.031(2) C8 0.0677(17) 0.113(3) 0.185(4) -0.102(3) -0.0271(19) 0.0003(18) C9 0.0546(14) 0.0720(17) 0.119(2) -0.0518(17) -0.0098(13) -0.0088(12) C10 0.0503(11) 0.0515(13) 0.0674(15) -0.0181(12) 0.0029(10) -0.0195(10) C11 0.0719(15) 0.0758(18) 0.0683(17) -0.0146(14) 0.0055(13) -0.0136(14) C12 0.0690(16) 0.0748(19) 0.091(2) -0.0060(17) -0.0013(14) -0.0055(14) C13 0.0632(15) 0.0660(19) 0.126(3) -0.0366(19) -0.0019(17) -0.0073(13) C14 0.0763(16) 0.084(2) 0.115(2) -0.0610(19) -0.0025(16) -0.0081(15) C15 0.0653(14) 0.0683(17) 0.0839(18) -0.0361(14) -0.0095(12) -0.0064(12) O2A 0.0657(16) 0.0881(19) 0.102(2) -0.0488(15) 0.0070(13) -0.0259(14) N1 0.0685(12) 0.0818(16) 0.1041(18) -0.0484(13) 0.0035(12) -0.0252(11) C16A 0.063(2) 0.067(2) 0.083(3) -0.037(2) -0.0016(18) -0.0103(17) C17A 0.107(2) 0.127(3) 0.136(3) -0.082(2) -0.002(2) -0.036(2) C18A 0.089(3) 0.109(4) 0.183(5) -0.077(4) -0.014(3) -0.040(3) C19 0.098(2) 0.099(2) 0.156(3) -0.053(2) 0.003(2) -0.0430(19) C20A 0.060(2) 0.081(3) 0.109(4) -0.030(2) 0.005(2) -0.0243(19) C22A 0.102(2) 0.167(4) 0.110(3) -0.051(3) 0.019(2) -0.040(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 1.430(4) . ? O1 H1O1 0.8200 . ? C1 C2 1.196(4) . ? C1 C1 1.369(5) 2_567 ? C2 C3 1.474(4) . ? C3 C4 1.527(4) . ? C3 C10 1.539(4) . ? C4 C9 1.377(4) . ? C4 C5 1.375(4) . ? C5 C6 1.372(6) . ? C5 H5 0.9300 . ? C6 C7 1.373(6) . ? C6 H6 0.9300 . ? C7 C8 1.346(6) . ? C7 H7 0.9300 . ? C8 C9 1.386(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.360(4) . ? C10 C15 1.382(4) . ? C11 C12 1.399(5) . ? C11 H11 0.9300 . ? C12 C13 1.347(5) . ? C12 H12 0.9300 . ? C13 C14 1.377(5) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A O2B 0.878(7) 2_666 ? O2A C16A 1.251(5) . ? N1 C16B 1.335(7) . ? N1 C16A 1.345(5) . ? N1 C20A 1.366(5) . ? N1 C20B 1.378(8) . ? N1 H1NA 0.8541 . ? N1 H1NB 0.8655 . ? C16A C17A 1.476(5) . ? C16A C20B 1.552(9) . ? C16A H1NB 1.0834 . ? C16A H22D 1.0755 . ? C17A C18A 1.294(6) . ? C17A C20B 1.443(10) . ? C17A H17A 0.9348 . ? C17A H22D 0.9912 . ? C17A H22E 0.9713 . ? C17A H22F 0.8946 . ? C18A C20B 1.299(9) . ? C18A C19 1.492(7) . ? C18A H18A 0.9231 . ? C18A H22E 1.5389 . ? C18A H22F 1.3331 . ? C18A H19B 1.3983 . ? C19 C20A 1.296(6) . ? C19 C20B 1.303(8) . ? C19 C18B 1.493(9) . ? C19 H19A 0.9381 . ? C19 H19B 0.9136 . ? C20A C18B 1.261(11) . ? C20A C20B 1.335(10) . ? C20A C22A 1.489(6) . ? C20A C16B 1.617(9) . ? C22A C18B 1.246(11) . ? C22A C16B 1.624(9) . ? C22A H22A 0.9666 . ? C22A H22B 0.9604 . ? C22A H22C 0.9635 . ? C22A H17B 1.0005 . ? O2B O2A 0.878(7) 2_666 ? O2B C16B 1.262(8) . ? O2B H1NA 1.4219 . ? C16B H1NA 0.9419 . ? C16B H22C 1.4505 . ? C18B H19A 1.4470 . ? C18B H22A 1.0532 . ? C18B H18B 0.9385 . ? 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 H1O1 109.5 . . ? C2 C1 C1 180.0(4) . 2_567 ? C1 C2 C3 176.8(2) . . ? O1 C3 C2 109.0(2) . . ? O1 C3 C4 110.34(19) . . ? C2 C3 C4 112.4(2) . . ? O1 C3 C10 107.7(2) . . ? C2 C3 C10 107.9(2) . . ? C4 C3 C10 109.4(2) . . ? C9 C4 C5 118.2(3) . . ? C9 C4 C3 123.1(2) . . ? C5 C4 C3 118.7(3) . . ? C6 C5 C4 120.7(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.2(4) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 119.9(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 120.7(3) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C11 C10 C15 118.6(3) . . ? C11 C10 C3 122.9(3) . . ? C15 C10 C3 118.5(2) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.6(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O2B O2A C16A 160.2(6) 2_666 . ? C16B N1 C16A 159.2(4) . . ? C16B N1 C20A 73.6(4) . . ? C16A N1 C20A 126.7(3) . . ? C16B N1 C20B 128.8(5) . . ? C16A N1 C20B 69.5(4) . . ? C20A N1 C20B 58.2(4) . . ? C16B N1 H1NA 44.6 . . ? C16A N1 H1NA 115.9 . . ? C20A N1 H1NA 117.3 . . ? C20B N1 H1NA 171.2 . . ? C16B N1 H1NB 110.5 . . ? C16A N1 H1NB 53.5 . . ? C20A N1 H1NB 156.5 . . ? C20B N1 H1NB 120.5 . . ? H1NA N1 H1NB 66.9 . . ? O2A C16A N1 120.1(3) . . ? O2A C16A C17A 126.7(4) . . ? N1 C16A C17A 113.1(3) . . ? O2A C16A C20B 175.0(5) . . ? N1 C16A C20B 56.3(4) . . ? C17A C16A C20B 56.9(4) . . ? O2A C16A H1NB 82.5 . . ? N1 C16A H1NB 40.0 . . ? C17A C16A H1NB 149.4 . . ? C20B C16A H1NB 94.7 . . ? O2A C16A H22D 85.9 . . ? N1 C16A H22D 150.3 . . ? C17A C16A H22D 42.2 . . ? C20B C16A H22D 96.8 . . ? H1NB C16A H22D 168.3 . . ? C18A C17A C20B 56.3(4) . . ? C18A C17A C16A 119.9(4) . . ? C20B C17A C16A 64.2(4) . . ? C18A C17A H17A 121.1 . . ? C20B C17A H17A 173.8 . . ? C16A C17A H17A 118.9 . . ? C18A C17A H22D 163.4 . . ? C20B C17A H22D 108.2 . . ? C16A C17A H22D 46.8 . . ? H17A C17A H22D 73.5 . . ? C18A C17A H22E 84.3 . . ? C20B C17A H22E 103.8 . . ? C16A C17A H22E 102.3 . . ? H17A C17A H22E 81.0 . . ? H22D C17A H22E 107.0 . . ? C18A C17A H22F 72.5 . . ? C20B C17A H22F 110.6 . . ? C16A C17A H22F 142.2 . . ? H17A C17A H22F 63.5 . . ? H22D C17A H22F 111.8 . . ? H22E C17A H22F 114.9 . . ? C20B C18A C17A 67.6(5) . . ? C20B C18A C19 55.1(4) . . ? C17A C18A C19 122.6(4) . . ? C20B C18A H18A 170.2 . . ? C17A C18A H18A 118.8 . . ? C19 C18A H18A 118.5 . . ? C20B C18A H22E 84.9 . . ? C17A C18A H22E 38.9 . . ? C19 C18A H22E 124.4 . . ? H18A C18A H22E 104.7 . . ? C20B C18A H22F 95.4 . . ? C17A C18A H22F 39.8 . . ? C19 C18A H22F 143.0 . . ? H18A C18A H22F 87.0 . . ? H22E C18A H22F 66.0 . . ? C20B C18A H19B 91.8 . . ? C17A C18A H19B 158.4 . . ? C19 C18A H19B 36.7 . . ? H18A C18A H19B 82.5 . . ? H22E C18A H19B 137.3 . . ? H22F C18A H19B 156.4 . . ? C20A C19 C20B 61.8(5) . . ? C20A C19 C18A 116.2(4) . . ? C20B C19 C18A 54.9(4) . . ? C20A C19 C18B 53.2(5) . . ? C20B C19 C18B 114.4(7) . . ? C18A C19 C18B 169.3(6) . . ? C20A C19 H19A 121.9 . . ? C20B C19 H19A 172.9 . . ? C18A C19 H19A 121.9 . . ? C18B C19 H19A 68.7 . . ? C20A C19 H19B 169.9 . . ? C20B C19 H19B 120.9 . . ? C18A C19 H19B 66.1 . . ? C18B C19 H19B 124.6 . . ? H19A C19 H19B 56.7 . . ? C18B C20A C19 71.5(5) . . ? C18B C20A C20B 130.0(7) . . ? C19 C20A C20B 59.3(4) . . ? C18B C20A N1 166.8(7) . . ? C19 C20A N1 120.6(4) . . ? C20B C20A N1 61.4(4) . . ? C18B C20A C22A 53.1(5) . . ? C19 C20A C22A 124.6(4) . . ? C20B C20A C22A 171.4(6) . . ? N1 C20A C22A 114.6(4) . . ? C18B C20A C16B 114.7(7) . . ? C19 C20A C16B 166.2(5) . . ? C20B C20A C16B 111.6(5) . . ? N1 C20A C16B 52.3(3) . . ? C22A C20A C16B 62.9(4) . . ? C18B C22A C20A 54.1(5) . . ? C18B C22A C16B 115.1(6) . . ? C20A C22A C16B 62.4(3) . . ? C18B C22A H22A 55.1 . . ? C20A C22A H22A 108.9 . . ? C16B C22A H22A 159.9 . . ? C18B C22A H22B 118.6 . . ? C20A C22A H22B 108.3 . . ? C16B C22A H22B 91.1 . . ? H22A C22A H22B 108.9 . . ? C18B C22A H22C 131.2 . . ? C20A C22A H22C 111.2 . . ? C16B C22A H22C 62.2 . . ? H22A C22A H22C 109.2 . . ? H22B C22A H22C 110.3 . . ? C18B C22A H17B 118.7 . . ? C20A C22A H17B 164.2 . . ? C16B C22A H17B 126.1 . . ? H22A C22A H17B 67.3 . . ? H22B C22A H17B 61.1 . . ? H22C C22A H17B 84.2 . . ? O2A O2B C16B 159.3(8) 2_666 . ? O2A O2B H1NA 119.4 2_666 . ? C16B O2B H1NA 40.5 . . ? O2B C16B N1 118.2(7) . . ? O2B C16B C20A 171.4(7) . . ? N1 C16B C20A 54.1(3) . . ? O2B C16B C22A 132.0(6) . . ? N1 C16B C22A 108.3(5) . . ? C20A C16B C22A 54.7(3) . . ? O2B C16B H1NA 78.9 . . ? N1 C16B H1NA 39.5 . . ? C20A C16B H1NA 93.1 . . ? C22A C16B H1NA 144.2 . . ? O2B C16B H22C 104.9 . . ? N1 C16B H22C 135.5 . . ? C20A C16B H22C 83.4 . . ? C22A C16B H22C 36.0 . . ? H1NA C16B H22C 172.4 . . ? C20A C18B C22A 72.8(8) . . ? C20A C18B C19 55.4(4) . . ? C22A C18B C19 128.2(9) . . ? C20A C18B H19A 92.5 . . ? C22A C18B H19A 165.2 . . ? C19 C18B H19A 37.2 . . ? C20A C18B H22A 121.4 . . ? C22A C18B H22A 48.8 . . ? C19 C18B H22A 174.3 . . ? H19A C18B H22A 145.9 . . ? C20A C18B H18B 169.2 . . ? C22A C18B H18B 117.5 . . ? C19 C18B H18B 114.3 . . ? H19A C18B H18B 77.3 . . ? H22A C18B H18B 68.7 . . ? C18A C20B C19 70.0(5) . . ? C18A C20B C20A 128.2(7) . . ? C19 C20B C20A 58.8(4) . . ? C18A C20B N1 166.0(9) . . ? C19 C20B N1 119.2(7) . . ? C20A C20B N1 60.4(4) . . ? C18A C20B C17A 56.0(5) . . ? C19 C20B C17A 125.8(7) . . ? C20A C20B C17A 168.0(9) . . ? N1 C20B C17A 113.1(6) . . ? C18A C20B C16A 114.3(7) . . ? C19 C20B C16A 166.5(8) . . ? C20A C20B C16A 113.9(6) . . ? N1 C20B C16A 54.2(3) . . ? C17A C20B C16A 58.9(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 -27(100) 2_567 . . . ? C1 C2 C3 O1 -80(5) . . . . ? C1 C2 C3 C4 158(5) . . . . ? C1 C2 C3 C10 37(5) . . . . ? O1 C3 C4 C9 -121.4(3) . . . . ? C2 C3 C4 C9 0.4(3) . . . . ? C10 C3 C4 C9 120.2(3) . . . . ? O1 C3 C4 C5 58.5(3) . . . . ? C2 C3 C4 C5 -179.6(2) . . . . ? C10 C3 C4 C5 -59.9(3) . . . . ? C9 C4 C5 C6 -0.7(4) . . . . ? C3 C4 C5 C6 179.3(3) . . . . ? C4 C5 C6 C7 1.6(6) . . . . ? C5 C6 C7 C8 -2.1(6) . . . . ? C6 C7 C8 C9 1.6(5) . . . . ? C7 C8 C9 C4 -0.7(4) . . . . ? C5 C4 C9 C8 0.3(4) . . . . ? C3 C4 C9 C8 -179.8(2) . . . . ? O1 C3 C10 C11 -2.9(3) . . . . ? C2 C3 C10 C11 -120.4(3) . . . . ? C4 C3 C10 C11 117.1(3) . . . . ? O1 C3 C10 C15 178.30(18) . . . . ? C2 C3 C10 C15 60.8(3) . . . . ? C4 C3 C10 C15 -61.7(3) . . . . ? C15 C10 C11 C12 1.2(3) . . . . ? C3 C10 C11 C12 -177.6(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 -0.9(4) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? C13 C14 C15 C10 -0.1(4) . . . . ? C11 C10 C15 C14 -1.0(3) . . . . ? C3 C10 C15 C14 177.8(2) . . . . ? O2B O2A C16A N1 -6.1(18) 2_666 . . . ? O2B O2A C16A C17A 177.7(16) 2_666 . . . ? O2B O2A C16A C20B -48(6) 2_666 . . . ? C16B N1 C16A O2A -21.8(13) . . . . ? C20A N1 C16A O2A 172.6(3) . . . . ? C20B N1 C16A O2A -176.0(6) . . . . ? C16B N1 C16A C17A 154.9(12) . . . . ? C20A N1 C16A C17A -10.7(4) . . . . ? C20B N1 C16A C17A 0.6(5) . . . . ? C16B N1 C16A C20B 154.2(13) . . . . ? C20A N1 C16A C20B -11.3(5) . . . . ? O2A C16A C17A C18A -175.1(4) . . . . ? N1 C16A C17A C18A 8.5(5) . . . . ? C20B C16A C17A C18A 9.1(6) . . . . ? O2A C16A C17A C20B 175.8(6) . . . . ? N1 C16A C17A C20B -0.6(5) . . . . ? C16A C17A C18A C20B -9.9(6) . . . . ? C20B C17A C18A C19 4.8(6) . . . . ? C16A C17A C18A C19 -5.1(6) . . . . ? C20B C18A C19 C20A 8.1(7) . . . . ? C17A C18A C19 C20A 2.7(6) . . . . ? C17A C18A C19 C20B -5.4(7) . . . . ? C20B C18A C19 C18B 0(3) . . . . ? C17A C18A C19 C18B -6(3) . . . . ? C20B C19 C20A C18B -170.5(9) . . . . ? C18A C19 C20A C18B -178.1(7) . . . . ? C18A C19 C20A C20B -7.5(6) . . . . ? C18B C19 C20A C20B 170.5(9) . . . . ? C20B C19 C20A N1 3.5(6) . . . . ? C18A C19 C20A N1 -4.0(5) . . . . ? C18B C19 C20A N1 174.0(7) . . . . ? C20B C19 C20A C22A -170.9(7) . . . . ? C18A C19 C20A C22A -178.4(4) . . . . ? C18B C19 C20A C22A -0.4(7) . . . . ? C20B C19 C20A C16B -51.8(19) . . . . ? C18A C19 C20A C16B -59.4(19) . . . . ? C18B C19 C20A C16B 119(2) . . . . ? C16B N1 C20A C18B -11(3) . . . . ? C16A N1 C20A C18B 164(3) . . . . ? C20B N1 C20A C18B 151(3) . . . . ? C16B N1 C20A C19 -165.7(5) . . . . ? C16A N1 C20A C19 9.0(5) . . . . ? C20B N1 C20A C19 -3.4(6) . . . . ? C16B N1 C20A C20B -162.2(7) . . . . ? C16A N1 C20A C20B 12.5(6) . . . . ? C16B N1 C20A C22A 9.3(5) . . . . ? C16A N1 C20A C22A -176.0(3) . . . . ? C20B N1 C20A C22A 171.5(6) . . . . ? C16A N1 C20A C16B 174.7(5) . . . . ? C20B N1 C20A C16B 162.2(7) . . . . ? C19 C20A C22A C18B 0.4(9) . . . . ? C20B C20A C22A C18B -114(3) . . . . ? N1 C20A C22A C18B -174.3(8) . . . . ? C16B C20A C22A C18B -166.0(9) . . . . ? C18B C20A C22A C16B 166.0(9) . . . . ? C19 C20A C22A C16B 166.5(5) . . . . ? C20B C20A C22A C16B 52(3) . . . . ? N1 C20A C22A C16B -8.2(4) . . . . ? O2A O2B C16B N1 21(3) 2_666 . . . ? O2A O2B C16B C20A -4(7) 2_666 . . . ? O2A O2B C16B C22A -143(2) 2_666 . . . ? C16A N1 C16B O2B 16.5(18) . . . . ? C20A N1 C16B O2B -175.6(8) . . . . ? C20B N1 C16B O2B 165.0(8) . . . . ? C16A N1 C16B C20A -168.0(11) . . . . ? C20B N1 C16B C20A -19.5(7) . . . . ? C16A N1 C16B C22A -176.1(8) . . . . ? C20A N1 C16B C22A -8.1(4) . . . . ? C20B N1 C16B C22A -27.6(10) . . . . ? C18B C20A C16B O2B -156(5) . . . . ? C19 C20A C16B O2B 91(5) . . . . ? C20B C20A C16B O2B 44(5) . . . . ? N1 C20A C16B O2B 27(5) . . . . ? C22A C20A C16B O2B -143(5) . . . . ? C18B C20A C16B N1 177.2(7) . . . . ? C19 C20A C16B N1 63.4(19) . . . . ? C20B C20A C16B N1 16.8(6) . . . . ? C22A C20A C16B N1 -170.5(5) . . . . ? C18B C20A C16B C22A -12.3(8) . . . . ? C19 C20A C16B C22A -126.0(18) . . . . ? C20B C20A C16B C22A -172.7(6) . . . . ? N1 C20A C16B C22A 170.5(5) . . . . ? C18B C22A C16B O2B -174.4(10) . . . . ? C20A C22A C16B O2B 173.1(11) . . . . ? C18B C22A C16B N1 20.5(10) . . . . ? C20A C22A C16B N1 8.1(4) . . . . ? C18B C22A C16B C20A 12.5(8) . . . . ? C19 C20A C18B C22A -179.6(7) . . . . ? C20B C20A C18B C22A 169.7(8) . . . . ? N1 C20A C18B C22A 23(3) . . . . ? C16B C20A C18B C22A 13.7(9) . . . . ? C20B C20A C18B C19 -10.6(10) . . . . ? N1 C20A C18B C19 -157(3) . . . . ? C22A C20A C18B C19 179.6(7) . . . . ? C16B C20A C18B C19 -166.7(5) . . . . ? C16B C22A C18B C20A -13.7(8) . . . . ? C20A C22A C18B C19 -0.4(8) . . . . ? C16B C22A C18B C19 -14.1(15) . . . . ? C20B C19 C18B C20A 9.2(8) . . . . ? C18A C19 C18B C20A 9(3) . . . . ? C20A C19 C18B C22A 0.5(9) . . . . ? C20B C19 C18B C22A 9.6(16) . . . . ? C18A C19 C18B C22A 10(4) . . . . ? C17A C18A C20B C19 175.1(6) . . . . ? C17A C18A C20B C20A 166.1(12) . . . . ? C19 C18A C20B C20A -9.0(8) . . . . ? C17A C18A C20B N1 42(3) . . . . ? C19 C18A C20B N1 -133(4) . . . . ? C19 C18A C20B C17A -175.1(6) . . . . ? C17A C18A C20B C16A 8.9(6) . . . . ? C19 C18A C20B C16A -166.1(10) . . . . ? C20A C19 C20B C18A -171.7(7) . . . . ? C18B C19 C20B C18A 179.9(7) . . . . ? C18A C19 C20B C20A 171.7(7) . . . . ? C18B C19 C20B C20A -8.3(8) . . . . ? C20A C19 C20B N1 -3.4(6) . . . . ? C18A C19 C20B N1 168.3(12) . . . . ? C18B C19 C20B N1 -11.7(12) . . . . ? C20A C19 C20B C17A -166.7(12) . . . . ? C18A C19 C20B C17A 5.0(6) . . . . ? C18B C19 C20B C17A -175.0(9) . . . . ? C20A C19 C20B C16A -61(3) . . . . ? C18A C19 C20B C16A 111(4) . . . . ? C18B C19 C20B C16A -69(4) . . . . ? C18B C20A C20B C18A 21.6(17) . . . . ? C19 C20A C20B C18A 9.9(8) . . . . ? N1 C20A C20B C18A -166.7(13) . . . . ? C22A C20A C20B C18A 129(3) . . . . ? C16B C20A C20B C18A 178.2(9) . . . . ? C18B C20A C20B C19 11.7(11) . . . . ? N1 C20A C20B C19 -176.6(6) . . . . ? C22A C20A C20B C19 119(3) . . . . ? C16B C20A C20B C19 168.4(5) . . . . ? C18B C20A C20B N1 -171.7(9) . . . . ? C19 C20A C20B N1 176.6(6) . . . . ? C22A C20A C20B N1 -64(3) . . . . ? C16B C20A C20B N1 -15.1(6) . . . . ? C18B C20A C20B C17A 128(3) . . . . ? C19 C20A C20B C17A 116(4) . . . . ? N1 C20A C20B C17A -60(3) . . . . ? C22A C20A C20B C17A -124(4) . . . . ? C16B C20A C20B C17A -75(4) . . . . ? C18B C20A C20B C16A 178.8(8) . . . . ? C19 C20A C20B C16A 167.1(9) . . . . ? N1 C20A C20B C16A -9.5(4) . . . . ? C22A C20A C20B C16A -73(3) . . . . ? C16B C20A C20B C16A -24.5(9) . . . . ? C16B N1 C20B C18A 154(3) . . . . ? C16A N1 C20B C18A -38(3) . . . . ? C20A N1 C20B C18A 132(4) . . . . ? C16B N1 C20B C19 25.5(13) . . . . ? C16A N1 C20B C19 -166.0(10) . . . . ? C20A N1 C20B C19 3.4(6) . . . . ? C16B N1 C20B C20A 22.1(8) . . . . ? C16A N1 C20B C20A -169.3(5) . . . . ? C16B N1 C20B C17A -169.2(6) . . . . ? C16A N1 C20B C17A -0.6(6) . . . . ? C20A N1 C20B C17A 168.7(10) . . . . ? C16B N1 C20B C16A -168.6(6) . . . . ? C20A N1 C20B C16A 169.3(5) . . . . ? C16A C17A C20B C18A 170.5(6) . . . . ? C18A C17A C20B C19 -5.7(7) . . . . ? C16A C17A C20B C19 164.8(11) . . . . ? C18A C17A C20B C20A -115(4) . . . . ? C16A C17A C20B C20A 56(3) . . . . ? C18A C17A C20B N1 -169.9(10) . . . . ? C16A C17A C20B N1 0.6(5) . . . . ? C18A C17A C20B C16A -170.5(6) . . . . ? O2A C16A C20B C18A -146(5) . . . . ? N1 C16A C20B C18A 170.6(10) . . . . ? C17A C16A C20B C18A -8.7(5) . . . . ? O2A C16A C20B C19 109(6) . . . . ? N1 C16A C20B C19 65(3) . . . . ? C17A C16A C20B C19 -114(4) . . . . ? O2A C16A C20B C20A 54(6) . . . . ? N1 C16A C20B C20A 10.1(5) . . . . ? C17A C16A C20B C20A -169.2(10) . . . . ? O2A C16A C20B N1 44(6) . . . . ? C17A C16A C20B N1 -179.3(6) . . . . ? O2A C16A C20B C17A -137(5) . . . . ? N1 C16A C20B C17A 179.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.138 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.037 data_I-b_393K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 6-Methyl-2(1H)-Pyridinone ; _chemical_name_common 'Tetraphenylhexadiynediol and Methylpyridone' _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 O2, 2(C6 H7 N O)' _chemical_formula_sum 'C42 H36 N2 O4' _chemical_formula_weight 632.73 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4750(5) _cell_length_b 10.8530(6) _cell_length_c 11.3600(10) _cell_angle_alpha 64.798(3) _cell_angle_beta 81.182(2) _cell_angle_gamma 69.185(7) _cell_volume 883.72(11) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9264 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 25.16 _exptl_crystal_description Blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 0.076 _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 9264 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.16 _reflns_number_total 2986 _reflns_number_gt 1327 _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^)+(0.0996P)^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 SHELXL _refine_ls_extinction_coef 0.031(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2986 _refine_ls_number_parameters 235 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1374 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1825 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.915 _refine_ls_shift/su_max 0.004 _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 0.1547(2) 0.7705(2) 0.66872(19) 0.0884(7) Uani 1 1 d . . . H1O1 H 0.2303 0.6957 0.6743 0.133 Uiso 1 1 calc R . . C1 C 0.0277(3) 0.5560(3) 0.9583(3) 0.0688(8) Uani 1 1 d . . . C2 C 0.0758(3) 0.6536(3) 0.8855(3) 0.0667(8) Uani 1 1 d . . . C3 C 0.1262(3) 0.7777(3) 0.7933(3) 0.0624(7) Uani 1 1 d . . . C4 C 0.2826(3) 0.7836(3) 0.8377(3) 0.0736(8) Uani 1 1 d . . . C5 C 0.3438(4) 0.8947(4) 0.7620(4) 0.1110(12) Uani 1 1 d . . . H5 H 0.2898 0.9638 0.6844 0.133 Uiso 1 1 calc R . . C6 C 0.4848(6) 0.9050(6) 0.7996(6) 0.148(2) Uani 1 1 d . . . H6 H 0.5234 0.9821 0.7489 0.178 Uiso 1 1 calc R . . C7 C 0.5657(5) 0.8026(7) 0.9102(7) 0.151(2) Uani 1 1 d . . . H7 H 0.6630 0.8079 0.9332 0.181 Uiso 1 1 calc R . . C8 C 0.5087(4) 0.6923(5) 0.9884(5) 0.1205(15) Uani 1 1 d . . . H8 H 0.5638 0.6241 1.0658 0.145 Uiso 1 1 calc R . . C9 C 0.3664(3) 0.6829(4) 0.9510(4) 0.0871(10) Uani 1 1 d . . . H9 H 0.3271 0.6068 1.0037 0.105 Uiso 1 1 calc R . . C10 C -0.0223(3) 0.9157(3) 0.7801(3) 0.0628(7) Uani 1 1 d . . . C11 C -0.1013(4) 1.0109(3) 0.6648(3) 0.0874(10) Uani 1 1 d . . . H11 H -0.0691 0.9917 0.5907 0.105 Uiso 1 1 calc R . . C12 C -0.2298(4) 1.1365(4) 0.6578(4) 0.1027(12) Uani 1 1 d . . . H12 H -0.2823 1.2019 0.5786 0.123 Uiso 1 1 calc R . . C13 C -0.2788(4) 1.1641(4) 0.7648(5) 0.0997(11) Uani 1 1 d . . . H13 H -0.3640 1.2489 0.7593 0.120 Uiso 1 1 calc R . . C14 C -0.2034(4) 1.0673(4) 0.8822(4) 0.0978(11) Uani 1 1 d . . . H14 H -0.2391 1.0852 0.9567 0.117 Uiso 1 1 calc R . . C15 C -0.0751(3) 0.9441(3) 0.8891(3) 0.0813(9) Uani 1 1 d . . . H15 H -0.0233 0.8790 0.9685 0.098 Uiso 1 1 calc R . . O2A O 0.4647(5) 0.5500(4) 0.6344(3) 0.0870(12) Uani 0.627(5) 1 d P . . N1 N 0.6596(3) 0.5881(3) 0.4784(3) 0.0869(8) Uani 1 1 d D . . H1NA H 0.6189 0.5500 0.4437 0.104 Uiso 0.627(5) 1 d PR . . C16A C 0.5884(6) 0.5939(5) 0.5895(5) 0.0757(16) Uani 0.627(5) 1 d P . . C17A C 0.6775(6) 0.6462(5) 0.6526(4) 0.1291(14) Uani 1 1 d . . . H17A H 0.6419 0.6450 0.7352 0.155 Uiso 0.627(5) 1 d PR . . C18A C 0.7974(8) 0.6970(7) 0.5899(8) 0.122(3) Uani 0.627(5) 1 d P . . H18A H 0.8497 0.7307 0.6294 0.146 Uiso 0.627(5) 1 d PR . . C19 C 0.8591(5) 0.6958(5) 0.4597(5) 0.1224(14) Uani 1 1 d D . . H19A H 0.9485 0.7303 0.4168 0.147 Uiso 0.627(5) 1 d PR . . C20A C 0.7822(6) 0.6466(6) 0.4121(6) 0.0945(19) Uani 0.627(5) 1 d P . . C22A C 0.8275(5) 0.6296(6) 0.2850(4) 0.1426(16) Uani 1 1 d . . . H22A H 0.9299 0.6538 0.2527 0.171 Uiso 0.627(5) 1 d PR . . H22B H 0.7375 0.6975 0.2245 0.171 Uiso 0.627(5) 1 d PR . . H22C H 0.8460 0.5330 0.2941 0.171 Uiso 0.627(5) 1 d PR . . H1NB H 0.5572 0.5902 0.5022 0.171 Uiso 0.37 1 d P . . H22D H 0.5976 0.5878 0.6852 0.171 Uiso 0.37 1 d P . . H22E H 0.6077 0.7456 0.6265 0.171 Uiso 0.37 1 d P . . H22F H 0.7579 0.6130 0.7095 0.171 Uiso 0.37 1 d P . . H19B H 0.9019 0.7461 0.4859 0.171 Uiso 0.37 1 d P . . H17B H 0.8500 0.6539 0.1867 0.171 Uiso 0.37 1 d P . . O2B O 0.6213(10) 0.4805(8) 0.3610(6) 0.099(2) Uiso 0.373(5) 1 d PD . . C16B C 0.6992(10) 0.5516(9) 0.3771(7) 0.089(3) Uiso 0.373(5) 1 d PD . . C18B C 0.8954(15) 0.6821(13) 0.3329(9) 0.132(4) Uiso 0.373(5) 1 d PD . . H18B H 0.9910 0.7069 0.2903 0.159 Uiso 0.373(5) 1 d PR . . C20B C 0.7466(11) 0.6380(11) 0.5312(9) 0.108(4) Uiso 0.373(5) 1 d PD . . 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 0.0980(14) 0.0817(15) 0.0796(15) -0.0357(12) 0.0130(11) -0.0238(11) C1 0.0640(15) 0.0582(18) 0.084(2) -0.0274(16) 0.0032(13) -0.0218(13) C2 0.0606(16) 0.0592(18) 0.078(2) -0.0267(16) 0.0014(13) -0.0179(14) C3 0.0631(15) 0.0567(17) 0.0650(19) -0.0227(14) 0.0099(12) -0.0231(13) C4 0.0561(16) 0.0583(18) 0.108(2) -0.0381(18) 0.0113(16) -0.0198(14) C5 0.083(2) 0.085(2) 0.162(3) -0.039(2) 0.025(2) -0.0459(19) C6 0.091(3) 0.111(4) 0.270(7) -0.092(4) 0.045(3) -0.062(3) C7 0.066(2) 0.137(5) 0.303(8) -0.145(5) 0.010(3) -0.028(3) C8 0.074(2) 0.112(3) 0.202(5) -0.103(3) -0.030(2) 0.002(2) C9 0.0622(18) 0.075(2) 0.131(3) -0.053(2) -0.0095(18) -0.0118(16) C10 0.0513(14) 0.0554(17) 0.076(2) -0.0219(17) 0.0049(14) -0.0194(13) C11 0.0795(19) 0.085(2) 0.067(2) -0.0130(19) 0.0054(16) -0.0169(19) C12 0.079(2) 0.075(2) 0.099(3) -0.002(2) -0.0030(19) -0.0036(19) C13 0.0709(19) 0.070(2) 0.141(4) -0.038(3) -0.001(2) -0.0088(17) C14 0.085(2) 0.093(3) 0.121(3) -0.063(3) -0.007(2) -0.008(2) C15 0.0735(18) 0.074(2) 0.089(2) -0.0388(18) -0.0083(16) -0.0049(16) O2A 0.080(3) 0.089(3) 0.102(3) -0.049(2) 0.0072(19) -0.029(2) N1 0.0742(16) 0.089(2) 0.111(2) -0.0514(17) 0.0049(15) -0.0298(14) C16A 0.059(3) 0.075(3) 0.091(4) -0.038(3) 0.001(3) -0.014(2) C17A 0.129(3) 0.148(4) 0.148(4) -0.095(3) -0.004(3) -0.042(3) C18A 0.102(5) 0.113(5) 0.189(8) -0.076(5) -0.013(4) -0.054(4) C19 0.103(3) 0.111(3) 0.165(4) -0.059(3) 0.003(3) -0.044(2) C20A 0.075(4) 0.090(4) 0.107(5) -0.030(4) 0.008(3) -0.029(3) C22A 0.119(3) 0.176(5) 0.116(4) -0.051(3) 0.020(3) -0.046(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 1.430(3) . ? O1 H1O1 0.8200 . ? C1 C2 1.195(3) . ? C1 C1 1.372(6) 2_567 ? C2 C3 1.472(4) . ? C3 C4 1.519(4) . ? C3 C10 1.541(4) . ? C4 C5 1.373(4) . ? C4 C9 1.373(4) . ? C5 C6 1.385(6) . ? C5 H5 0.9300 . ? C6 C7 1.348(7) . ? C6 H6 0.9300 . ? C7 C8 1.353(6) . ? C7 H7 0.9300 . ? C8 C9 1.388(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.362(4) . ? C10 C15 1.373(4) . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 C13 1.344(5) . ? C12 H12 0.9300 . ? C13 C14 1.371(5) . ? C13 H13 0.9300 . ? C14 C15 1.371(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O2A O2B 0.888(7) 2_666 ? O2A C16A 1.253(6) . ? N1 C16B 1.329(7) . ? N1 C16A 1.330(5) . ? N1 C20A 1.368(6) . ? N1 C20B 1.377(7) . ? N1 H1NA 0.8521 . ? N1 H1NB 0.8634 . ? C16A C17A 1.490(6) . ? C16A C20B 1.543(9) . ? C16A H1NB 1.0850 . ? C16A H22D 1.0737 . ? C17A C18A 1.299(7) . ? C17A C20B 1.440(10) . ? C17A H17A 0.9368 . ? C17A H22D 1.0125 . ? C17A H22E 0.9638 . ? C17A H22F 0.8800 . ? C18A C20B 1.299(10) . ? C18A C19 1.495(8) . ? C18A H18A 0.9209 . ? C18A H22E 1.5538 . ? C18A H22F 1.3462 . ? C18A H19B 1.3935 . ? C19 C20A 1.266(7) . ? C19 C20B 1.310(7) . ? C19 C18B 1.485(8) . ? C19 H19A 0.9409 . ? C19 H19B 0.9111 . ? C20A C18B 1.258(11) . ? C20A C20B 1.310(10) . ? C20A C22A 1.508(7) . ? C20A C16B 1.633(10) . ? C22A C18B 1.243(11) . ? C22A C16B 1.596(9) . ? C22A H22A 0.9690 . ? C22A H22B 0.9623 . ? C22A H22C 0.9652 . ? C22A H17B 1.0357 . ? O2B O2A 0.888(7) 2_666 ? O2B C16B 1.259(7) . ? O2B H1NA 1.4277 . ? C16B H1NA 0.9348 . ? C16B H22C 1.4506 . ? C18B H19A 1.4524 . ? C18B H22A 1.0504 . ? C18B H18B 0.9415 . ? 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 H1O1 109.5 . . ? C2 C1 C1 179.9(6) . 2_567 ? C1 C2 C3 177.1(3) . . ? O1 C3 C2 108.7(2) . . ? O1 C3 C4 110.38(19) . . ? C2 C3 C4 112.3(2) . . ? O1 C3 C10 107.8(2) . . ? C2 C3 C10 107.98(19) . . ? C4 C3 C10 109.5(2) . . ? C5 C4 C9 118.0(3) . . ? C5 C4 C3 119.0(3) . . ? C9 C4 C3 123.1(2) . . ? C6 C5 C4 120.8(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 119.5(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 118.8(4) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C4 C9 C8 121.3(3) . . ? C4 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C11 C10 C15 118.9(3) . . ? C11 C10 C3 122.7(3) . . ? C15 C10 C3 118.4(3) . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.6(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C10 120.8(3) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O2B O2A C16A 160.3(6) 2_666 . ? C16B N1 C16A 159.8(5) . . ? C16B N1 C20A 74.5(5) . . ? C16A N1 C20A 125.5(4) . . ? C16B N1 C20B 129.4(5) . . ? C16A N1 C20B 69.5(4) . . ? C20A N1 C20B 57.0(5) . . ? C16B N1 H1NA 44.4 . . ? C16A N1 H1NA 116.1 . . ? C20A N1 H1NA 118.3 . . ? C20B N1 H1NA 172.1 . . ? C16B N1 H1NB 109.2 . . ? C16A N1 H1NB 54.4 . . ? C20A N1 H1NB 154.8 . . ? C20B N1 H1NB 120.7 . . ? H1NA N1 H1NB 66.5 . . ? O2A C16A N1 119.9(4) . . ? O2A C16A C17A 126.6(5) . . ? N1 C16A C17A 113.3(4) . . ? O2A C16A C20B 175.5(6) . . ? N1 C16A C20B 56.7(4) . . ? C17A C16A C20B 56.7(4) . . ? O2A C16A H1NB 82.3 . . ? N1 C16A H1NB 40.3 . . ? C17A C16A H1NB 149.5 . . ? C20B C16A H1NB 95.1 . . ? O2A C16A H22D 85.2 . . ? N1 C16A H22D 150.7 . . ? C17A C16A H22D 42.8 . . ? C20B C16A H22D 97.3 . . ? H1NB C16A H22D 167.5 . . ? C18A C17A C20B 56.4(5) . . ? C18A C17A C16A 119.3(5) . . ? C20B C17A C16A 63.5(4) . . ? C18A C17A H17A 121.9 . . ? C20B C17A H17A 174.6 . . ? C16A C17A H17A 118.8 . . ? C18A C17A H22D 162.2 . . ? C20B C17A H22D 107.0 . . ? C16A C17A H22D 46.1 . . ? H17A C17A H22D 74.0 . . ? C18A C17A H22E 85.4 . . ? C20B C17A H22E 103.1 . . ? C16A C17A H22E 101.4 . . ? H17A C17A H22E 81.4 . . ? H22D C17A H22E 106.2 . . ? C18A C17A H22F 73.5 . . ? C20B C17A H22F 111.1 . . ? C16A C17A H22F 140.3 . . ? H17A C17A H22F 63.9 . . ? H22D C17A H22F 111.0 . . ? H22E C17A H22F 117.6 . . ? C20B C18A C17A 67.3(5) . . ? C20B C18A C19 55.4(5) . . ? C17A C18A C19 122.5(5) . . ? C20B C18A H18A 171.3 . . ? C17A C18A H18A 118.3 . . ? C19 C18A H18A 119.1 . . ? C20B C18A H22E 83.3 . . ? C17A C18A H22E 38.2 . . ? C19 C18A H22E 123.9 . . ? H18A C18A H22E 105.2 . . ? C20B C18A H22F 94.2 . . ? C17A C18A H22F 38.8 . . ? C19 C18A H22F 142.1 . . ? H18A C18A H22F 87.8 . . ? H22E C18A H22F 65.5 . . ? C20B C18A H19B 91.9 . . ? C17A C18A H19B 158.3 . . ? C19 C18A H19B 36.6 . . ? H18A C18A H19B 83.1 . . ? H22E C18A H19B 137.5 . . ? H22F C18A H19B 156.9 . . ? C20A C19 C20B 61.1(5) . . ? C20A C19 C18B 53.7(5) . . ? C20B C19 C18B 114.4(7) . . ? C20A C19 C18A 115.4(4) . . ? C20B C19 C18A 54.7(5) . . ? C18B C19 C18A 169.1(6) . . ? C20A C19 H19A 123.1 . . ? C20B C19 H19A 173.3 . . ? C18B C19 H19A 69.4 . . ? C18A C19 H19A 121.5 . . ? C20A C19 H19B 170.3 . . ? C20B C19 H19B 120.3 . . ? C18B C19 H19B 125.1 . . ? C18A C19 H19B 65.7 . . ? H19A C19 H19B 56.6 . . ? C18B C20A C19 72.1(6) . . ? C18B C20A C20B 132.7(8) . . ? C19 C20A C20B 61.1(5) . . ? C18B C20A N1 164.3(8) . . ? C19 C20A N1 122.9(6) . . ? C20B C20A N1 61.8(4) . . ? C18B C20A C22A 52.5(5) . . ? C19 C20A C22A 124.5(5) . . ? C20B C20A C22A 170.3(7) . . ? N1 C20A C22A 112.2(5) . . ? C18B C20A C16B 112.7(7) . . ? C19 C20A C16B 168.0(6) . . ? C20B C20A C16B 112.0(5) . . ? N1 C20A C16B 51.6(3) . . ? C22A C20A C16B 60.9(4) . . ? C18B C22A C20A 53.4(6) . . ? C18B C22A C16B 116.1(6) . . ? C20A C22A C16B 63.4(4) . . ? C18B C22A H22A 55.0 . . ? C20A C22A H22A 107.8 . . ? C16B C22A H22A 161.1 . . ? C18B C22A H22B 115.6 . . ? C20A C22A H22B 107.8 . . ? C16B C22A H22B 90.0 . . ? H22A C22A H22B 108.8 . . ? C18B C22A H22C 133.8 . . ? C20A C22A H22C 112.6 . . ? C16B C22A H22C 63.5 . . ? H22A C22A H22C 109.0 . . ? H22B C22A H22C 110.6 . . ? C18B C22A H17B 115.2 . . ? C20A C22A H17B 161.3 . . ? C16B C22A H17B 128.2 . . ? H22A C22A H17B 65.4 . . ? H22B C22A H17B 61.4 . . ? H22C C22A H17B 86.0 . . ? O2A O2B C16B 156.9(9) 2_666 . ? O2A O2B H1NA 118.2 2_666 . ? C16B O2B H1NA 40.1 . . ? O2B C16B N1 119.0(7) . . ? O2B C16B C20A 172.7(7) . . ? N1 C16B C20A 53.9(4) . . ? O2B C16B C22A 131.2(7) . . ? N1 C16B C22A 109.2(5) . . ? C20A C16B C22A 55.7(4) . . ? O2B C16B H1NA 79.7 . . ? N1 C16B H1NA 39.6 . . ? C20A C16B H1NA 93.0 . . ? C22A C16B H1NA 146.4 . . ? O2B C16B H22C 102.6 . . ? N1 C16B H22C 135.5 . . ? C20A C16B H22C 84.6 . . ? C22A C16B H22C 36.6 . . ? H1NA C16B H22C 168.9 . . ? C22A C18B C20A 74.2(8) . . ? C22A C18B C19 128.3(9) . . ? C20A C18B C19 54.2(5) . . ? C22A C18B H19A 165.6 . . ? C20A C18B H19A 91.6 . . ? C19 C18B H19A 37.3 . . ? C22A C18B H22A 49.1 . . ? C20A C18B H22A 122.6 . . ? C19 C18B H22A 170.4 . . ? H19A C18B H22A 144.4 . . ? C22A C18B H18B 117.8 . . ? C20A C18B H18B 166.9 . . ? C19 C18B H18B 113.4 . . ? H19A C18B H18B 76.3 . . ? H22A C18B H18B 68.8 . . ? C18A C20B C19 69.9(5) . . ? C18A C20B C20A 127.2(7) . . ? C19 C20B C20A 57.8(5) . . ? C18A C20B N1 167.8(9) . . ? C19 C20B N1 119.0(7) . . ? C20A C20B N1 61.2(5) . . ? C18A C20B C17A 56.3(5) . . ? C19 C20B C17A 126.1(7) . . ? C20A C20B C17A 169.5(9) . . ? N1 C20B C17A 113.7(6) . . ? C18A C20B C16A 115.7(8) . . ? C19 C20B C16A 167.4(8) . . ? C20A C20B C16A 114.3(6) . . ? N1 C20B C16A 53.9(3) . . ? C17A C20B C16A 59.8(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 -6(100) 2_567 . . . ? C1 C2 C3 O1 -81(6) . . . . ? C1 C2 C3 C4 156(6) . . . . ? C1 C2 C3 C10 35(6) . . . . ? O1 C3 C4 C5 59.2(3) . . . . ? C2 C3 C4 C5 -179.4(3) . . . . ? C10 C3 C4 C5 -59.4(3) . . . . ? O1 C3 C4 C9 -121.0(3) . . . . ? C2 C3 C4 C9 0.4(4) . . . . ? C10 C3 C4 C9 120.4(3) . . . . ? C9 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 C6 179.3(3) . . . . ? C4 C5 C6 C7 1.8(7) . . . . ? C5 C6 C7 C8 -2.6(8) . . . . ? C6 C7 C8 C9 2.0(7) . . . . ? C5 C4 C9 C8 0.0(5) . . . . ? C3 C4 C9 C8 -179.8(3) . . . . ? C7 C8 C9 C4 -0.7(5) . . . . ? O1 C3 C10 C11 -2.2(3) . . . . ? C2 C3 C10 C11 -119.4(3) . . . . ? C4 C3 C10 C11 118.0(3) . . . . ? O1 C3 C10 C15 178.6(2) . . . . ? C2 C3 C10 C15 61.4(3) . . . . ? C4 C3 C10 C15 -61.2(3) . . . . ? C15 C10 C11 C12 1.9(4) . . . . ? C3 C10 C11 C12 -177.3(2) . . . . ? C10 C11 C12 C13 -1.0(5) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C12 C13 C14 C15 1.6(5) . . . . ? C13 C14 C15 C10 -0.6(5) . . . . ? C11 C10 C15 C14 -1.1(4) . . . . ? C3 C10 C15 C14 178.1(3) . . . . ? O2B O2A C16A N1 -12(2) 2_666 . . . ? O2B O2A C16A C17A 172.2(17) 2_666 . . . ? O2B O2A C16A C20B -52(8) 2_666 . . . ? C16B N1 C16A O2A -15.4(15) . . . . ? C20A N1 C16A O2A 172.4(4) . . . . ? C20B N1 C16A O2A -176.6(6) . . . . ? C16B N1 C16A C17A 160.8(13) . . . . ? C20A N1 C16A C17A -11.4(6) . . . . ? C20B N1 C16A C17A -0.4(6) . . . . ? C16B N1 C16A C20B 161.2(14) . . . . ? C20A N1 C16A C20B -11.0(6) . . . . ? O2A C16A C17A C18A -175.7(5) . . . . ? N1 C16A C17A C18A 8.5(6) . . . . ? C20B C16A C17A C18A 8.0(6) . . . . ? O2A C16A C17A C20B 176.3(7) . . . . ? N1 C16A C17A C20B 0.4(6) . . . . ? C16A C17A C18A C20B -8.6(7) . . . . ? C20B C17A C18A C19 4.2(6) . . . . ? C16A C17A C18A C19 -4.5(8) . . . . ? C20B C18A C19 C20A 7.2(7) . . . . ? C17A C18A C19 C20A 2.5(8) . . . . ? C17A C18A C19 C20B -4.7(7) . . . . ? C20B C18A C19 C18B 6(3) . . . . ? C17A C18A C19 C18B 1(4) . . . . ? C20B C19 C20A C18B -173.1(9) . . . . ? C18A C19 C20A C18B -179.7(7) . . . . ? C18B C19 C20A C20B 173.1(9) . . . . ? C18A C19 C20A C20B -6.7(7) . . . . ? C20B C19 C20A N1 1.9(6) . . . . ? C18B C19 C20A N1 174.9(8) . . . . ? C18A C19 C20A N1 -4.8(7) . . . . ? C20B C19 C20A C22A -170.7(8) . . . . ? C18B C19 C20A C22A 2.3(7) . . . . ? C18A C19 C20A C22A -177.4(5) . . . . ? C20B C19 C20A C16B -57(3) . . . . ? C18B C19 C20A C16B 116(3) . . . . ? C18A C19 C20A C16B -64(3) . . . . ? C16B N1 C20A C18B -5(3) . . . . ? C16A N1 C20A C18B 172(3) . . . . ? C20B N1 C20A C18B 160(3) . . . . ? C16B N1 C20A C19 -166.8(7) . . . . ? C16A N1 C20A C19 10.4(7) . . . . ? C20B N1 C20A C19 -1.9(6) . . . . ? C16B N1 C20A C20B -164.9(7) . . . . ? C16A N1 C20A C20B 12.3(6) . . . . ? C16B N1 C20A C22A 6.6(5) . . . . ? C16A N1 C20A C22A -176.1(4) . . . . ? C20B N1 C20A C22A 171.6(7) . . . . ? C16A N1 C20A C16B 177.2(5) . . . . ? C20B N1 C20A C16B 164.9(7) . . . . ? C19 C20A C22A C18B -2.8(9) . . . . ? C20B C20A C22A C18B -126(4) . . . . ? N1 C20A C22A C18B -176.1(8) . . . . ? C16B C20A C22A C18B -170.1(9) . . . . ? C18B C20A C22A C16B 170.1(9) . . . . ? C19 C20A C22A C16B 167.3(7) . . . . ? C20B C20A C22A C16B 44(3) . . . . ? N1 C20A C22A C16B -6.0(5) . . . . ? O2A O2B C16B N1 29(3) 2_666 . . . ? O2A O2B C16B C20A 19(8) 2_666 . . . ? O2A O2B C16B C22A -140.9(19) 2_666 . . . ? C16A N1 C16B O2B 8.2(19) . . . . ? C20A N1 C16B O2B -178.3(9) . . . . ? C20B N1 C16B O2B 165.3(8) . . . . ? C16A N1 C16B C20A -173.4(13) . . . . ? C20B N1 C16B C20A -16.4(7) . . . . ? C16A N1 C16B C22A -179.6(10) . . . . ? C20A N1 C16B C22A -6.2(5) . . . . ? C20B N1 C16B C22A -22.5(10) . . . . ? C18B C20A C16B O2B -170(6) . . . . ? C19 C20A C16B O2B 78(7) . . . . ? C20B C20A C16B O2B 26(6) . . . . ? N1 C20A C16B O2B 12(6) . . . . ? C22A C20A C16B O2B -161(6) . . . . ? C18B C20A C16B N1 178.6(8) . . . . ? C19 C20A C16B N1 67(3) . . . . ? C20B C20A C16B N1 14.3(6) . . . . ? C22A C20A C16B N1 -173.0(5) . . . . ? C18B C20A C16B C22A -8.5(8) . . . . ? C19 C20A C16B C22A -120(3) . . . . ? C20B C20A C16B C22A -172.7(7) . . . . ? N1 C20A C16B C22A 173.0(5) . . . . ? C18B C22A C16B O2B -174.3(10) . . . . ? C20A C22A C16B O2B 176.9(11) . . . . ? C18B C22A C16B N1 14.8(10) . . . . ? C20A C22A C16B N1 6.0(5) . . . . ? C18B C22A C16B C20A 8.8(8) . . . . ? C16B C22A C18B C20A -9.8(9) . . . . ? C20A C22A C18B C19 2.5(8) . . . . ? C16B C22A C18B C19 -7.3(15) . . . . ? C19 C20A C18B C22A 177.6(8) . . . . ? C20B C20A C18B C22A 169.3(9) . . . . ? N1 C20A C18B C22A 14(3) . . . . ? C16B C20A C18B C22A 9.3(8) . . . . ? C20B C20A C18B C19 -8.3(10) . . . . ? N1 C20A C18B C19 -164(3) . . . . ? C22A C20A C18B C19 -177.6(8) . . . . ? C16B C20A C18B C19 -168.2(6) . . . . ? C20A C19 C18B C22A -3.0(9) . . . . ? C20B C19 C18B C22A 3.7(15) . . . . ? C18A C19 C18B C22A -2(4) . . . . ? C20B C19 C18B C20A 6.7(8) . . . . ? C18A C19 C18B C20A 1(3) . . . . ? C17A C18A C20B C19 175.7(6) . . . . ? C17A C18A C20B C20A 167.9(12) . . . . ? C19 C18A C20B C20A -7.9(8) . . . . ? C17A C18A C20B N1 37(4) . . . . ? C19 C18A C20B N1 -139(4) . . . . ? C19 C18A C20B C17A -175.7(6) . . . . ? C17A C18A C20B C16A 8.1(6) . . . . ? C19 C18A C20B C16A -167.7(10) . . . . ? C20A C19 C20B C18A -172.6(8) . . . . ? C18B C19 C20B C18A -178.7(7) . . . . ? C18B C19 C20B C20A -6.1(8) . . . . ? C18A C19 C20B C20A 172.6(8) . . . . ? C20A C19 C20B N1 -1.8(6) . . . . ? C18B C19 C20B N1 -7.9(12) . . . . ? C18A C19 C20B N1 170.8(11) . . . . ? C20A C19 C20B C17A -168.2(11) . . . . ? C18B C19 C20B C17A -174.4(8) . . . . ? C18A C19 C20B C17A 4.4(6) . . . . ? C20A C19 C20B C16A -54(4) . . . . ? C18B C19 C20B C16A -60(4) . . . . ? C18A C19 C20B C16A 118(4) . . . . ? C18B C20A C20B C18A 17.7(18) . . . . ? C19 C20A C20B C18A 8.7(9) . . . . ? N1 C20A C20B C18A -169.5(12) . . . . ? C22A C20A C20B C18A 137(3) . . . . ? C16B C20A C20B C18A 177.8(9) . . . . ? C18B C20A C20B C19 9.0(11) . . . . ? N1 C20A C20B C19 -178.2(6) . . . . ? C22A C20A C20B C19 128(3) . . . . ? C16B C20A C20B C19 169.1(6) . . . . ? C18B C20A C20B N1 -172.8(10) . . . . ? C19 C20A C20B N1 178.2(6) . . . . ? C22A C20A C20B N1 -54(3) . . . . ? C16B C20A C20B N1 -12.7(6) . . . . ? C18B C20A C20B C17A 124(4) . . . . ? C19 C20A C20B C17A 115(4) . . . . ? N1 C20A C20B C17A -63(4) . . . . ? C22A C20A C20B C17A -117(5) . . . . ? C16B C20A C20B C17A -76(4) . . . . ? C18B C20A C20B C16A 177.8(9) . . . . ? C19 C20A C20B C16A 168.8(9) . . . . ? N1 C20A C20B C16A -9.4(5) . . . . ? C22A C20A C20B C16A -63(4) . . . . ? C16B C20A C20B C16A -22.1(10) . . . . ? C16B N1 C20B C18A 155(4) . . . . ? C16A N1 C20B C18A -33(4) . . . . ? C20A N1 C20B C18A 137(4) . . . . ? C16B N1 C20B C19 20.7(13) . . . . ? C16A N1 C20B C19 -167.6(9) . . . . ? C20A N1 C20B C19 1.7(6) . . . . ? C16B N1 C20B C20A 18.9(9) . . . . ? C16A N1 C20B C20A -169.3(6) . . . . ? C16B N1 C20B C17A -171.3(6) . . . . ? C16A N1 C20B C17A 0.4(6) . . . . ? C20A N1 C20B C17A 169.8(10) . . . . ? C16B N1 C20B C16A -171.7(7) . . . . ? C20A N1 C20B C16A 169.3(6) . . . . ? C16A C17A C20B C18A 171.6(7) . . . . ? C18A C17A C20B C19 -5.0(7) . . . . ? C16A C17A C20B C19 166.6(11) . . . . ? C18A C17A C20B C20A -113(4) . . . . ? C16A C17A C20B C20A 58(4) . . . . ? C18A C17A C20B N1 -172.0(10) . . . . ? C16A C17A C20B N1 -0.4(5) . . . . ? C18A C17A C20B C16A -171.6(7) . . . . ? O2A C16A C20B C18A -146(7) . . . . ? N1 C16A C20B C18A 172.7(10) . . . . ? C17A C16A C20B C18A -7.8(6) . . . . ? O2A C16A C20B C19 100(8) . . . . ? N1 C16A C20B C19 59(4) . . . . ? C17A C16A C20B C19 -121(4) . . . . ? O2A C16A C20B C20A 51(8) . . . . ? N1 C16A C20B C20A 10.2(5) . . . . ? C17A C16A C20B C20A -170.2(10) . . . . ? O2A C16A C20B N1 41(7) . . . . ? C17A C16A C20B N1 179.5(6) . . . . ? O2A C16A C20B C17A -138(7) . . . . ? N1 C16A C20B C17A -179.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.128 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.033 #END