############################################################################ # # # # # ### # # ### ### # ### # # ### # # ### # ### # # # # # # # # # # # # # ## ## # ## # # # # # # # # # # ### # # ### ### # ### # # # ### # ## # ### ### # # # # # # # # # # # # # # # # # # ## # # # ### ### # # ### ### # # ### # # # # # # # # # # # # # # # # # ### ### ### # # # # # ## ## # # # # # # # # # # # # # # # ### # ### ### # ### # # # # # # # # # ## # # # # # # # # # # # ### # # # # # ### # # # # # ############################################################################ ############################################################################ # # # This Supplementary Material is written in the Crystallographic # # Information File (CIF) format. For further details see: S.R. Hall, # # F.H. Allen and I.D. Brown, Acta Cryst. (1991) A47, 655-685. # # # ############################################################################ data_5759 ############################################################################ # # _publ_requested_journal 'test' #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _publ_section_title ; ? ; loop_ _publ_author_name _publ_author_address 'Aissa' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'F/"urstner' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Rust' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; # # ############################################################################ _audit_creation_date 2007-01-26 _audit_block_code 'AIS-CE-079-01' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source 'methanole' _chemical_formula_moiety 'C17 H13 Cl2 N' _chemical_formula_sum 'C17 H13 Cl2 N' _chemical_formula_weight 302.18 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8433(3) _cell_length_b 14.5296(4) _cell_length_c 7.6465(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.8060(10) _cell_angle_gamma 90.00 _cell_volume 1406.05(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5516 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 33.14 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method none _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.449 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'XPREP, Siemens (1994)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.3 mm focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 29441 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 33.13 _reflns_number_total 5351 _reflns_number_gt 4088 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect software (Nonius, 1998)' _computing_cell_refinement 'Denzo / Scalepack (Otwinowski 1997)' _computing_data_reduction 'Denzo / Scalepack (Otwinowski 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0458P)^2^+0.5016P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 5351 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _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 C1 C 0.52760(10) 0.12019(9) 0.79968(17) 0.0162(2) Uani 1 1 d . . . C2 C 0.47674(9) 0.13820(9) 0.62758(17) 0.0168(2) Uani 1 1 d . . . C3 C 0.53543(10) 0.14215(9) 0.49119(16) 0.0175(2) Uani 1 1 d . . . C4 C 0.64488(9) 0.12795(8) 0.52045(16) 0.0146(2) Uani 1 1 d . . . C5 C 0.69779(10) 0.13846(9) 0.36514(16) 0.0178(2) Uani 1 1 d . . . C6 C 0.79574(10) 0.11700(9) 0.33925(16) 0.0180(2) Uani 1 1 d . . . C7 C 0.88435(10) 0.06922(9) 0.45730(16) 0.0171(2) Uani 1 1 d . . . C8 C 0.85513(9) 0.02592(9) 0.62430(16) 0.0150(2) Uani 1 1 d . . . C9 C 0.81234(9) 0.09603(8) 0.73903(15) 0.0129(2) Uani 1 1 d . . . C10 C 0.69643(9) 0.11091(8) 0.69669(15) 0.0134(2) Uani 1 1 d . . . C11 C 0.63654(9) 0.10659(9) 0.83329(16) 0.0156(2) Uani 1 1 d . . . C12 C 0.86922(9) 0.14446(8) 0.87286(15) 0.0129(2) Uani 1 1 d . . . C13 C 0.98287(9) 0.14198(8) 0.94501(15) 0.0123(2) Uani 1 1 d . . . C14 C 1.01961(9) 0.19471(9) 1.09675(16) 0.0153(2) Uani 1 1 d . . . C15 C 1.12613(10) 0.19392(9) 1.16956(16) 0.0177(2) Uani 1 1 d . . . C16 C 1.19425(9) 0.14042(9) 1.08875(17) 0.0167(2) Uani 1 1 d . . . C17 C 1.15211(9) 0.09121(9) 0.93751(16) 0.0162(2) Uani 1 1 d . . . H3 H 0.5012(14) 0.1571(12) 0.371(2) 0.028(5) Uiso 1 1 d . . . H5 H 0.6516(13) 0.1685(12) 0.265(2) 0.022(4) Uiso 1 1 d . . . H6 H 0.8088(14) 0.1337(12) 0.222(2) 0.028(5) Uiso 1 1 d . . . H7A H 0.9111(13) 0.0209(12) 0.389(2) 0.024(4) Uiso 1 1 d . . . H7B H 0.9412(13) 0.1144(11) 0.489(2) 0.020(4) Uiso 1 1 d . . . H8A H 0.9176(12) -0.0038(11) 0.692(2) 0.013(4) Uiso 1 1 d . . . H8B H 0.8021(12) -0.0221(11) 0.591(2) 0.015(4) Uiso 1 1 d . . . H11 H 0.6718(12) 0.0938(11) 0.952(2) 0.017(4) Uiso 1 1 d . . . H12 H 0.8314(11) 0.1895(11) 0.9302(19) 0.014(4) Uiso 1 1 d . . . H14 H 0.9698(13) 0.2309(12) 1.146(2) 0.025(4) Uiso 1 1 d . . . H15 H 1.1519(12) 0.2319(12) 1.272(2) 0.019(4) Uiso 1 1 d . . . H16 H 1.2676(13) 0.1371(12) 1.135(2) 0.020(4) Uiso 1 1 d . . . H17 H 1.1977(13) 0.0570(11) 0.876(2) 0.019(4) Uiso 1 1 d . . . N1 N 1.04944(8) 0.09113(7) 0.86448(13) 0.01515(19) Uani 1 1 d . . . Cl1 Cl 0.45715(2) 0.11511(3) 0.97349(4) 0.02318(8) Uani 1 1 d . . . Cl2 Cl 0.34200(2) 0.15692(3) 0.58169(5) 0.02402(9) Uani 1 1 d . . . 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 C1 0.0133(5) 0.0185(6) 0.0181(5) -0.0016(4) 0.0063(4) -0.0002(4) C2 0.0093(5) 0.0190(6) 0.0213(6) -0.0024(4) 0.0005(4) 0.0004(4) C3 0.0139(5) 0.0217(6) 0.0160(5) -0.0010(4) -0.0003(4) 0.0021(4) C4 0.0134(5) 0.0174(6) 0.0127(5) -0.0003(4) 0.0016(4) 0.0004(4) C5 0.0185(6) 0.0218(6) 0.0129(5) 0.0004(4) 0.0022(4) -0.0002(5) C6 0.0191(6) 0.0234(6) 0.0121(5) -0.0016(4) 0.0042(4) -0.0023(5) C7 0.0145(5) 0.0230(6) 0.0148(5) -0.0046(4) 0.0054(4) -0.0011(4) C8 0.0131(5) 0.0156(5) 0.0164(5) -0.0026(4) 0.0028(4) 0.0000(4) C9 0.0119(5) 0.0156(5) 0.0117(5) 0.0016(4) 0.0031(4) 0.0005(4) C10 0.0115(5) 0.0153(5) 0.0135(5) -0.0018(4) 0.0022(4) -0.0002(4) C11 0.0129(5) 0.0203(6) 0.0139(5) -0.0002(4) 0.0030(4) 0.0009(4) C12 0.0115(5) 0.0160(5) 0.0116(5) 0.0003(4) 0.0032(4) 0.0020(4) C13 0.0125(5) 0.0135(5) 0.0109(5) 0.0006(4) 0.0019(4) 0.0006(4) C14 0.0159(5) 0.0161(5) 0.0139(5) -0.0019(4) 0.0027(4) 0.0006(4) C15 0.0162(5) 0.0205(6) 0.0152(5) -0.0026(4) -0.0004(4) -0.0022(4) C16 0.0116(5) 0.0207(6) 0.0173(5) 0.0009(4) 0.0009(4) -0.0014(4) C17 0.0128(5) 0.0196(6) 0.0164(5) -0.0005(4) 0.0032(4) 0.0010(4) N1 0.0126(4) 0.0188(5) 0.0142(5) -0.0021(4) 0.0028(3) 0.0009(4) Cl1 0.01536(14) 0.03398(19) 0.02246(15) -0.00209(13) 0.00968(11) 0.00053(12) Cl2 0.01037(13) 0.03026(18) 0.03028(17) -0.00183(13) 0.00014(11) 0.00160(11) _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 C1 C2 1.3907(18) . ? C1 C11 1.3929(17) . ? C1 Cl1 1.7322(12) . ? C2 C3 1.3881(18) . ? C2 Cl2 1.7278(12) . ? C3 C4 1.4005(17) . ? C3 H3 0.970(18) . ? C4 C10 1.4184(16) . ? C4 C5 1.4732(17) . ? C5 C6 1.3431(18) . ? C5 H5 0.989(17) . ? C6 C7 1.4973(18) . ? C6 H6 0.973(18) . ? C7 C8 1.5265(17) . ? C7 H7A 0.972(17) . ? C7 H7B 0.981(17) . ? C8 C9 1.5078(16) . ? C8 H8A 0.977(15) . ? C8 H8B 0.979(16) . ? C9 C12 1.3496(16) . ? C9 C10 1.4844(16) . ? C10 C11 1.4001(16) . ? C11 H11 0.959(16) . ? C12 C13 1.4704(16) . ? C12 H12 0.964(15) . ? C13 N1 1.3548(15) . ? C13 C14 1.4033(16) . ? C14 C15 1.3864(16) . ? C14 H14 0.954(17) . ? C15 C16 1.3913(18) . ? C15 H15 0.971(17) . ? C16 C17 1.3886(18) . ? C16 H16 0.949(16) . ? C17 N1 1.3416(15) . ? C17 H17 0.951(16) . ? 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 C2 C1 C11 119.77(11) . . ? C2 C1 Cl1 120.76(9) . . ? C11 C1 Cl1 119.47(10) . . ? C3 C2 C1 119.41(11) . . ? C3 C2 Cl2 119.62(10) . . ? C1 C2 Cl2 120.97(10) . . ? C2 C3 C4 122.18(11) . . ? C2 C3 H3 120.1(10) . . ? C4 C3 H3 117.7(10) . . ? C3 C4 C10 118.09(11) . . ? C3 C4 C5 116.37(11) . . ? C10 C4 C5 125.39(11) . . ? C6 C5 C4 131.84(12) . . ? C6 C5 H5 116.2(9) . . ? C4 C5 H5 112.0(9) . . ? C5 C6 C7 130.81(11) . . ? C5 C6 H6 113.1(11) . . ? C7 C6 H6 116.1(11) . . ? C6 C7 C8 115.18(10) . . ? C6 C7 H7A 108.2(10) . . ? C8 C7 H7A 108.2(10) . . ? C6 C7 H7B 107.2(10) . . ? C8 C7 H7B 110.4(10) . . ? H7A C7 H7B 107.4(13) . . ? C9 C8 C7 111.98(10) . . ? C9 C8 H8A 109.9(9) . . ? C7 C8 H8A 109.0(9) . . ? C9 C8 H8B 109.1(9) . . ? C7 C8 H8B 109.5(9) . . ? H8A C8 H8B 107.2(13) . . ? C12 C9 C10 118.86(10) . . ? C12 C9 C8 126.13(10) . . ? C10 C9 C8 115.02(10) . . ? C11 C10 C4 119.32(11) . . ? C11 C10 C9 119.26(10) . . ? C4 C10 C9 121.41(10) . . ? C1 C11 C10 121.21(11) . . ? C1 C11 H11 120.0(9) . . ? C10 C11 H11 118.8(9) . . ? C9 C12 C13 130.26(11) . . ? C9 C12 H12 116.7(9) . . ? C13 C12 H12 113.0(9) . . ? N1 C13 C14 121.61(10) . . ? N1 C13 C12 120.39(10) . . ? C14 C13 C12 117.99(10) . . ? C15 C14 C13 119.82(11) . . ? C15 C14 H14 121.9(10) . . ? C13 C14 H14 118.3(10) . . ? C14 C15 C16 118.59(11) . . ? C14 C15 H15 119.8(9) . . ? C16 C15 H15 121.5(9) . . ? C17 C16 C15 118.17(11) . . ? C17 C16 H16 120.3(10) . . ? C15 C16 H16 121.5(10) . . ? N1 C17 C16 124.28(11) . . ? N1 C17 H17 116.0(10) . . ? C16 C17 H17 119.6(10) . . ? C17 N1 C13 117.51(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.460 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.064