# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tian673 #TrackingRef 'CCDC 729228.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 N2 O2' _chemical_formula_weight 428.56 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 Tetragonal _symmetry_space_group_name_H-M 'I4(1)/a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-y+3/4, x+1/4, z+1/4' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-y+5/4, x+3/4, z+3/4' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'x, y-1/2, -z' 'y-3/4, -x-1/4, -z-1/4' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 27.908(5) _cell_length_b 27.908(5) _cell_length_c 6.521(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 5079(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1015 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 15.90 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9657 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11340 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.0939 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2238 _reflns_number_gt 1040 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1000P)^2^+0.3000P] 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 0.0011(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2238 _refine_ls_number_parameters 147 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1679 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.2462 _refine_ls_wR_factor_gt 0.1921 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.225 _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 C10 C 0.48592(14) 0.95961(15) 0.3895(6) 0.0566(12) Uani 1 1 d . . . C6 C 0.40155(15) 1.02051(14) 0.9017(6) 0.0567(12) Uani 1 1 d . . . H6 H 0.3853 0.9994 0.8159 0.068 Uiso 1 1 calc R . . O1 O 0.47592(11) 0.91908(11) 0.2770(5) 0.0846(12) Uani 1 1 d . . . C8 C 0.47350(14) 1.01439(14) 0.6753(6) 0.0524(11) Uani 1 1 d . . . C7 C 0.44654(15) 1.03061(14) 0.8559(6) 0.0562(12) Uani 1 1 d . . . H7 H 0.4629 1.0501 0.9479 0.067 Uiso 1 1 calc R . . C9 C 0.46028(14) 0.97387(14) 0.5611(6) 0.0569(12) Uani 1 1 d . . . H13 H 0.4337 0.9562 0.6016 0.068 Uiso 1 1 calc R . . C1 C 0.39788(16) 1.05751(14) 1.2525(7) 0.0603(12) Uani 1 1 d . . . H2 H 0.4311 1.0560 1.2638 0.072 Uiso 1 1 calc R . . N1 N 0.32323(16) 1.08113(14) 1.4070(6) 0.0762(12) Uani 1 1 d . . . C5 C 0.37523(14) 1.04003(13) 1.0775(6) 0.0508(11) Uani 1 1 d . . . C2 C 0.37067(19) 1.07724(15) 1.4106(7) 0.0683(13) Uani 1 1 d . . . H1 H 0.3868 1.0884 1.5260 0.082 Uiso 1 1 calc R . . C4 C 0.32537(16) 1.04330(16) 1.0749(7) 0.0672(13) Uani 1 1 d . . . H4 H 0.3081 1.0315 0.9638 0.081 Uiso 1 1 calc R . . C3 C 0.30165(17) 1.06429(17) 1.2391(9) 0.0781(15) Uani 1 1 d . . . H5 H 0.2685 1.0668 1.2316 0.094 Uiso 1 1 calc R . . C11 C 0.42910(17) 0.90028(18) 0.2775(8) 0.0861(17) Uani 1 1 d . . . H14A H 0.4067 0.9243 0.2294 0.103 Uiso 1 1 calc R . . H14B H 0.4201 0.8912 0.4158 0.103 Uiso 1 1 calc R . . C13 C 0.4493(3) 0.8550(3) -0.0477(11) 0.156(3) Uani 1 1 d DU . . H15A H 0.4830 0.8613 -0.0248 0.187 Uiso 1 1 calc R . . H15B H 0.4370 0.8816 -0.1279 0.187 Uiso 1 1 calc R . . C12 C 0.4273(2) 0.8570(3) 0.1389(10) 0.132(3) Uani 1 1 d DU . . H16A H 0.4398 0.8303 0.2181 0.159 Uiso 1 1 calc R . . H16B H 0.3937 0.8503 0.1150 0.159 Uiso 1 1 calc R . . C14 C 0.4462(2) 0.8120(2) -0.1784(9) 0.133(2) Uani 1 1 d U . . H17A H 0.4665 0.7873 -0.1234 0.199 Uiso 1 1 calc R . . H17B H 0.4564 0.8198 -0.3149 0.199 Uiso 1 1 calc R . . H17C H 0.4137 0.8008 -0.1819 0.199 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C10 0.049(2) 0.061(3) 0.059(3) -0.016(2) 0.005(2) -0.002(2) C6 0.054(3) 0.060(3) 0.056(3) -0.011(2) -0.003(2) -0.001(2) O1 0.065(2) 0.087(2) 0.101(3) -0.044(2) 0.0215(18) -0.0229(16) C8 0.051(2) 0.058(3) 0.048(3) -0.009(2) 0.000(2) 0.007(2) C7 0.054(3) 0.063(3) 0.052(3) -0.006(2) -0.002(2) 0.000(2) C9 0.051(2) 0.062(3) 0.057(3) -0.005(2) 0.006(2) -0.004(2) C1 0.064(3) 0.059(3) 0.057(3) -0.002(2) 0.005(2) 0.008(2) N1 0.085(3) 0.078(3) 0.066(3) -0.005(2) 0.013(2) 0.019(2) C5 0.058(3) 0.045(2) 0.050(3) 0.000(2) 0.001(2) 0.0017(19) C2 0.086(4) 0.062(3) 0.057(3) -0.004(2) -0.005(3) 0.006(2) C4 0.060(3) 0.077(3) 0.064(3) -0.009(3) 0.005(2) 0.002(2) C3 0.060(3) 0.088(4) 0.086(4) -0.002(3) 0.011(3) 0.013(3) C11 0.075(3) 0.083(4) 0.100(4) -0.033(3) 0.015(3) -0.026(3) C13 0.143(6) 0.171(6) 0.155(6) -0.082(5) 0.023(5) -0.041(5) C12 0.122(5) 0.159(6) 0.116(5) -0.058(4) 0.032(4) -0.071(4) C14 0.150(5) 0.121(5) 0.128(5) -0.054(4) 0.009(4) 0.003(4) _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 C10 O1 1.377(4) . ? C10 C9 1.387(5) . ? C10 C8 1.410(5) 9_676 ? C6 C7 1.321(5) . ? C6 C5 1.467(5) . ? C6 H6 0.9300 . ? O1 C11 1.408(5) . ? C8 C9 1.403(5) . ? C8 C10 1.410(5) 9_676 ? C8 C7 1.469(5) . ? C7 H7 0.9300 . ? C9 H13 0.9300 . ? C1 C5 1.393(6) . ? C1 C2 1.394(6) . ? C1 H2 0.9300 . ? N1 C2 1.329(6) . ? N1 C3 1.335(6) . ? C5 C4 1.395(5) . ? C2 H1 0.9300 . ? C4 C3 1.389(6) . ? C4 H4 0.9300 . ? C3 H5 0.9300 . ? C11 C12 1.509(7) . ? C11 H14A 0.9700 . ? C11 H14B 0.9700 . ? C13 C12 1.364(6) . ? C13 C14 1.476(7) . ? C13 H15A 0.9700 . ? C13 H15B 0.9700 . ? C12 H16A 0.9700 . ? C12 H16B 0.9700 . ? C14 H17A 0.9600 . ? C14 H17B 0.9600 . ? C14 H17C 0.9600 . ? 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 O1 C10 C9 124.1(4) . . ? O1 C10 C8 115.2(4) . 9_676 ? C9 C10 C8 120.6(4) . 9_676 ? C7 C6 C5 125.0(4) . . ? C7 C6 H6 117.5 . . ? C5 C6 H6 117.5 . . ? C10 O1 C11 119.6(3) . . ? C9 C8 C10 117.8(4) . 9_676 ? C9 C8 C7 122.6(4) . . ? C10 C8 C7 119.6(4) 9_676 . ? C6 C7 C8 127.0(4) . . ? C6 C7 H7 116.5 . . ? C8 C7 H7 116.5 . . ? C10 C9 C8 121.6(4) . . ? C10 C9 H13 119.2 . . ? C8 C9 H13 119.2 . . ? C5 C1 C2 119.8(4) . . ? C5 C1 H2 120.1 . . ? C2 C1 H2 120.1 . . ? C2 N1 C3 115.8(4) . . ? C1 C5 C4 116.1(4) . . ? C1 C5 C6 122.9(4) . . ? C4 C5 C6 120.9(4) . . ? N1 C2 C1 124.2(4) . . ? N1 C2 H1 117.9 . . ? C1 C2 H1 117.9 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C3 C4 124.5(4) . . ? N1 C3 H5 117.8 . . ? C4 C3 H5 117.8 . . ? O1 C11 C12 109.1(4) . . ? O1 C11 H14A 109.9 . . ? C12 C11 H14A 109.9 . . ? O1 C11 H14B 109.9 . . ? C12 C11 H14B 109.9 . . ? H14A C11 H14B 108.3 . . ? C12 C13 C14 121.4(7) . . ? C12 C13 H15A 107.0 . . ? C14 C13 H15A 107.0 . . ? C12 C13 H15B 107.0 . . ? C14 C13 H15B 107.0 . . ? H15A C13 H15B 106.7 . . ? C13 C12 C11 123.5(6) . . ? C13 C12 H16A 106.5 . . ? C11 C12 H16A 106.5 . . ? C13 C12 H16B 106.5 . . ? C11 C12 H16B 106.5 . . ? H16A C12 H16B 106.5 . . ? C13 C14 H17A 109.5 . . ? C13 C14 H17B 109.5 . . ? H17A C14 H17B 109.5 . . ? C13 C14 H17C 109.5 . . ? H17A C14 H17C 109.5 . . ? H17B C14 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C10 O1 C11 25.4(7) . . . . ? C8 C10 O1 C11 -157.6(4) 9_676 . . . ? C5 C6 C7 C8 -176.0(4) . . . . ? C9 C8 C7 C6 -21.3(6) . . . . ? C10 C8 C7 C6 158.0(4) 9_676 . . . ? O1 C10 C9 C8 177.0(4) . . . . ? C8 C10 C9 C8 0.2(7) 9_676 . . . ? C10 C8 C9 C10 -0.2(7) 9_676 . . . ? C7 C8 C9 C10 179.1(4) . . . . ? C2 C1 C5 C4 -0.6(6) . . . . ? C2 C1 C5 C6 177.5(4) . . . . ? C7 C6 C5 C1 -23.1(6) . . . . ? C7 C6 C5 C4 155.0(4) . . . . ? C3 N1 C2 C1 0.5(7) . . . . ? C5 C1 C2 N1 -0.5(7) . . . . ? C1 C5 C4 C3 1.6(6) . . . . ? C6 C5 C4 C3 -176.6(4) . . . . ? C2 N1 C3 C4 0.6(7) . . . . ? C5 C4 C3 N1 -1.7(7) . . . . ? C10 O1 C11 C12 178.5(5) . . . . ? C14 C13 C12 C11 -179.5(7) . . . . ? O1 C11 C12 C13 -42.1(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.415 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 729228' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tian_727 #TrackingRef 'tian 727.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 N2 O2' _chemical_formula_weight 428.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5234(15) _cell_length_b 10.7419(19) _cell_length_c 14.505(3) _cell_angle_alpha 73.507(2) _cell_angle_beta 83.091(2) _cell_angle_gamma 76.901(2) _cell_volume 1238.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1313 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9893 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8796 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4301 _reflns_number_gt 1922 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1595P)^2^+0.2327P] 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 0.041(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4301 _refine_ls_number_parameters 292 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1809 _refine_ls_R_factor_gt 0.0943 _refine_ls_wR_factor_ref 0.3201 _refine_ls_wR_factor_gt 0.2441 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.006 _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 0.9978(4) 0.1378(3) 0.1345(2) 0.0862(10) Uani 1 1 d . . . C9 C 0.9988(5) 0.0719(5) 0.0670(3) 0.0716(12) Uani 1 1 d . . . C8 C 0.9354(5) -0.0434(5) 0.0956(3) 0.0744(13) Uani 1 1 d . . . C11 C 1.0665(5) 0.2517(5) 0.1090(3) 0.0826(13) Uani 1 1 d . . . H11A H 1.0081 0.3194 0.0582 0.099 Uiso 1 1 calc R . . H11B H 1.1780 0.2298 0.0856 0.099 Uiso 1 1 calc R . . C12 C 1.0580(6) 0.3026(5) 0.1965(3) 0.0850(14) Uani 1 1 d . . . H12A H 1.1225 0.2362 0.2452 0.102 Uiso 1 1 calc R . . H12B H 0.9471 0.3163 0.2227 0.102 Uiso 1 1 calc R . . C10 C 1.0609(5) 0.1136(5) -0.0275(3) 0.0749(12) Uani 1 1 d . . . H10 H 1.1014 0.1911 -0.0459 0.090 Uiso 1 1 calc R . . C14 C 1.1028(7) 0.4900(6) 0.2597(4) 0.1214(19) Uani 1 1 d . . . H14A H 0.9915 0.5092 0.2819 0.182 Uiso 1 1 calc R . . H14B H 1.1439 0.5703 0.2402 0.182 Uiso 1 1 calc R . . H14C H 1.1639 0.4277 0.3108 0.182 Uiso 1 1 calc R . . C13 C 1.1172(6) 0.4312(5) 0.1745(3) 0.0939(15) Uani 1 1 d . . . H13A H 1.2295 0.4158 0.1511 0.113 Uiso 1 1 calc R . . H13B H 1.0564 0.4956 0.1231 0.113 Uiso 1 1 calc R . . C7 C 0.8644(6) -0.0984(6) 0.1929(3) 0.1017(18) Uani 1 1 d D . . H7 H 0.8406 -0.1808 0.1988 0.122 Uiso 1 1 calc R . . C3 C 0.6618(7) -0.3139(6) 0.4761(4) 0.1092(18) Uani 1 1 d . . . H3 H 0.6388 -0.3983 0.4919 0.131 Uiso 1 1 calc R . . C1 C 0.7577(6) -0.1361(8) 0.3580(4) 0.111(2) Uani 1 1 d . . . N1 N 0.6355(6) -0.2491(5) 0.5425(3) 0.1055(15) Uani 1 1 d . . . C6 C 0.8307(7) -0.0665(7) 0.2634(5) 0.132(2) Uani 1 1 d DU . . H6 H 0.8521 0.0155 0.2612 0.158 Uiso 1 1 calc R . . C4 C 0.6694(8) -0.1325(7) 0.5143(4) 0.117(2) Uani 1 1 d . . . H4 H 0.6502 -0.0835 0.5595 0.141 Uiso 1 1 calc R . . C5 C 0.7290(8) -0.0748(7) 0.4274(5) 0.126(2) Uani 1 1 d . . . H5 H 0.7506 0.0096 0.4154 0.151 Uiso 1 1 calc R . . C2 C 0.7236(6) -0.2611(7) 0.3812(4) 0.1059(18) Uani 1 1 d . . . H2 H 0.7407 -0.3097 0.3358 0.127 Uiso 1 1 calc R . . C23 C 0.4420(5) -0.0185(5) 0.0967(4) 0.0785(13) Uani 1 1 d . . . C16 C 0.6627(5) 0.4858(4) 0.0889(3) 0.0751(12) Uani 1 1 d . . . H16 H 0.6929 0.5018 0.0235 0.090 Uiso 1 1 calc R . . C22 C 0.5163(5) 0.0865(4) 0.0520(4) 0.0785(13) Uani 1 1 d . . . C21 C 0.5346(5) 0.1784(5) 0.1100(4) 0.0857(14) Uani 1 1 d . . . H21 H 0.4952 0.1587 0.1740 0.103 Uiso 1 1 calc R . . O2 O 0.3861(4) -0.0292(3) 0.1906(3) 0.0935(10) Uani 1 1 d . . . C15 C 0.6092(5) 0.3730(4) 0.1363(3) 0.0667(11) Uani 1 1 d . . . C20 C 0.5972(5) 0.2786(5) 0.0808(3) 0.0849(14) Uani 1 1 d . . . H20 H 0.6410 0.2958 0.0177 0.102 Uiso 1 1 calc R . . N2 N 0.6356(5) 0.5617(4) 0.2297(3) 0.0892(12) Uani 1 1 d . . . C24 C 0.4264(5) -0.1042(4) 0.0434(4) 0.0833(14) Uani 1 1 d . . . H24 H 0.3761 -0.1752 0.0726 0.100 Uiso 1 1 calc R . . C19 C 0.5678(5) 0.3547(4) 0.2342(3) 0.0785(13) Uani 1 1 d . . . H19 H 0.5303 0.2797 0.2707 0.094 Uiso 1 1 calc R . . C25 C 0.3224(6) -0.1416(5) 0.2414(4) 0.0912(14) Uani 1 1 d . . . H25A H 0.4037 -0.2216 0.2429 0.109 Uiso 1 1 calc R . . H25B H 0.2308 -0.1458 0.2095 0.109 Uiso 1 1 calc R . . C26 C 0.2715(6) -0.1316(5) 0.3409(4) 0.0992(16) Uani 1 1 d . . . H26A H 0.1861 -0.0539 0.3384 0.119 Uiso 1 1 calc R . . H26B H 0.3620 -0.1200 0.3700 0.119 Uiso 1 1 calc R . . C18 C 0.5842(6) 0.4518(5) 0.2752(3) 0.0909(15) Uani 1 1 d . . . H18 H 0.5566 0.4387 0.3408 0.109 Uiso 1 1 calc R . . C27 C 0.2115(8) -0.2536(6) 0.4036(4) 0.1166(19) Uani 1 1 d . . . H27A H 0.1209 -0.2648 0.3744 0.140 Uiso 1 1 calc R . . H27B H 0.2968 -0.3312 0.4054 0.140 Uiso 1 1 calc R . . C17 C 0.6723(6) 0.5752(5) 0.1373(4) 0.0887(14) Uani 1 1 d . . . H17 H 0.7075 0.6519 0.1022 0.106 Uiso 1 1 calc R . . C28 C 0.1609(9) -0.2462(8) 0.5035(5) 0.162(3) Uani 1 1 d . . . H28A H 0.2516 -0.2404 0.5343 0.243 Uiso 1 1 calc R . . H28B H 0.1211 -0.3242 0.5386 0.243 Uiso 1 1 calc R . . H28C H 0.0772 -0.1692 0.5025 0.243 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.088(2) 0.102(2) 0.0647(19) -0.0149(17) 0.0053(15) -0.0241(18) C9 0.057(3) 0.093(3) 0.052(2) -0.009(2) 0.0017(18) -0.005(2) C8 0.055(3) 0.095(3) 0.055(2) 0.002(2) 0.0005(19) -0.009(2) C11 0.070(3) 0.094(3) 0.071(3) -0.016(2) 0.000(2) -0.001(3) C12 0.077(3) 0.091(3) 0.078(3) -0.016(3) -0.005(2) -0.008(3) C10 0.064(3) 0.088(3) 0.062(3) -0.005(2) -0.001(2) -0.015(2) C14 0.120(5) 0.131(5) 0.122(5) -0.053(4) -0.011(4) -0.017(4) C13 0.078(3) 0.116(4) 0.084(3) -0.029(3) -0.002(2) -0.012(3) C7 0.073(3) 0.156(5) 0.055(3) -0.021(3) -0.003(2) 0.011(3) C3 0.131(5) 0.105(4) 0.091(4) -0.024(3) 0.017(3) -0.037(3) C1 0.072(3) 0.149(6) 0.069(3) 0.021(4) 0.005(3) -0.006(3) N1 0.129(4) 0.119(4) 0.061(3) -0.015(3) 0.017(2) -0.031(3) C6 0.096(4) 0.162(5) 0.102(4) -0.008(4) -0.002(3) 0.006(4) C4 0.144(5) 0.119(5) 0.089(4) -0.038(4) 0.024(4) -0.030(4) C5 0.133(5) 0.120(5) 0.104(5) -0.008(4) 0.029(4) -0.032(4) C2 0.095(4) 0.153(5) 0.079(4) -0.058(4) 0.004(3) -0.014(4) C23 0.068(3) 0.069(3) 0.098(4) -0.023(3) -0.016(2) -0.004(2) C16 0.080(3) 0.075(3) 0.063(3) -0.009(2) -0.001(2) -0.016(2) C22 0.069(3) 0.071(3) 0.102(4) -0.043(3) -0.027(3) 0.008(2) C21 0.074(3) 0.078(3) 0.090(3) -0.007(3) -0.007(2) -0.004(3) O2 0.099(2) 0.086(2) 0.099(3) -0.0346(19) -0.0077(19) -0.0124(19) C15 0.056(2) 0.077(3) 0.074(3) -0.035(2) -0.013(2) -0.003(2) C20 0.074(3) 0.085(3) 0.083(3) -0.005(3) -0.001(2) -0.013(3) N2 0.097(3) 0.085(3) 0.097(3) -0.041(2) -0.007(2) -0.018(2) C24 0.073(3) 0.066(3) 0.116(4) -0.035(3) -0.017(3) -0.005(2) C19 0.081(3) 0.074(3) 0.079(3) -0.016(2) 0.004(2) -0.024(2) C25 0.088(3) 0.079(3) 0.104(4) -0.024(3) -0.016(3) -0.008(3) C26 0.086(4) 0.107(4) 0.106(4) -0.040(3) -0.019(3) -0.001(3) C18 0.104(4) 0.101(4) 0.068(3) -0.028(3) 0.010(3) -0.021(3) C27 0.121(5) 0.117(4) 0.102(4) -0.009(3) -0.009(3) -0.028(4) C17 0.087(3) 0.071(3) 0.107(4) -0.018(3) -0.007(3) -0.019(3) C28 0.162(7) 0.197(7) 0.111(5) -0.013(5) -0.002(5) -0.043(6) _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 C9 1.360(5) . ? O1 C11 1.412(5) . ? C9 C10 1.395(6) . ? C9 C8 1.399(6) . ? C8 C10 1.397(6) 2_755 ? C8 C7 1.480(6) . ? C11 C12 1.506(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.513(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C10 C8 1.397(6) 2_755 ? C10 H10 0.9300 . ? C14 C13 1.522(6) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C7 C6 1.152(7) . ? C7 H7 0.9300 . ? C3 N1 1.312(6) . ? C3 C2 1.418(7) . ? C3 H3 0.9300 . ? C1 C5 1.324(8) . ? C1 C2 1.377(8) . ? C1 C6 1.501(8) . ? N1 C4 1.290(7) . ? C6 H6 0.9300 . ? C4 C5 1.333(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? C23 O2 1.370(6) . ? C23 C22 1.379(6) . ? C23 C24 1.396(6) . ? C16 C17 1.362(6) . ? C16 C15 1.360(6) . ? C16 H16 0.9300 . ? C22 C24 1.385(7) 2_655 ? C22 C21 1.511(6) . ? C21 C20 1.253(6) . ? C21 H21 0.9300 . ? O2 C25 1.411(6) . ? C15 C19 1.390(6) . ? C15 C20 1.489(6) . ? C20 H20 0.9300 . ? N2 C17 1.313(6) . ? N2 C18 1.321(6) . ? C24 C22 1.385(7) 2_655 ? C24 H24 0.9300 . ? C19 C18 1.378(6) . ? C19 H19 0.9300 . ? C25 C26 1.483(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.524(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C18 H18 0.9300 . ? C27 C28 1.481(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C17 H17 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 C9 O1 C11 118.8(3) . . ? O1 C9 C10 123.0(4) . . ? O1 C9 C8 117.4(4) . . ? C10 C9 C8 119.6(4) . . ? C10 C8 C9 118.0(4) 2_755 . ? C10 C8 C7 116.7(5) 2_755 . ? C9 C8 C7 125.4(5) . . ? O1 C11 C12 108.8(4) . . ? O1 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O1 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? C11 C12 C13 112.7(4) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C9 C10 C8 122.5(4) . 2_755 ? C9 C10 H10 118.8 . . ? C8 C10 H10 118.8 2_755 . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C14 C13 C12 114.6(4) . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C6 C7 C8 137.0(7) . . ? C6 C7 H7 111.5 . . ? C8 C7 H7 111.5 . . ? N1 C3 C2 123.0(5) . . ? N1 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C5 C1 C2 116.3(5) . . ? C5 C1 C6 117.5(7) . . ? C2 C1 C6 126.1(7) . . ? C4 N1 C3 114.5(5) . . ? C7 C6 C1 130.2(8) . . ? C7 C6 H6 114.9 . . ? C1 C6 H6 114.9 . . ? N1 C4 C5 127.0(6) . . ? N1 C4 H4 116.5 . . ? C5 C4 H4 116.5 . . ? C1 C5 C4 120.8(6) . . ? C1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C2 C3 118.4(5) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? O2 C23 C22 116.8(4) . . ? O2 C23 C24 124.8(5) . . ? C22 C23 C24 118.4(5) . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C23 C22 C24 119.9(4) . 2_655 ? C23 C22 C21 118.3(5) . . ? C24 C22 C21 121.8(5) 2_655 . ? C20 C21 C22 126.7(5) . . ? C20 C21 H21 116.6 . . ? C22 C21 H21 116.6 . . ? C23 O2 C25 118.5(4) . . ? C16 C15 C19 117.0(4) . . ? C16 C15 C20 118.6(4) . . ? C19 C15 C20 124.4(4) . . ? C21 C20 C15 127.0(5) . . ? C21 C20 H20 116.5 . . ? C15 C20 H20 116.5 . . ? C17 N2 C18 114.5(4) . . ? C22 C24 C23 121.8(5) 2_655 . ? C22 C24 H24 119.1 2_655 . ? C23 C24 H24 119.1 . . ? C18 C19 C15 117.6(4) . . ? C18 C19 H19 121.2 . . ? C15 C19 H19 121.2 . . ? O2 C25 C26 108.6(4) . . ? O2 C25 H25A 110.0 . . ? C26 C25 H25A 110.0 . . ? O2 C25 H25B 110.0 . . ? C26 C25 H25B 110.0 . . ? H25A C25 H25B 108.3 . . ? C25 C26 C27 112.5(5) . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? N2 C18 C19 125.8(4) . . ? N2 C18 H18 117.1 . . ? C19 C18 H18 117.1 . . ? C28 C27 C26 113.5(6) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? N2 C17 C16 125.1(5) . . ? N2 C17 H17 117.4 . . ? C16 C17 H17 117.4 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.879 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.160 _database_code_depnum_ccdc_archive 'CCDC 771894' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tian691 #TrackingRef 'CCDC 737794.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H40 Cl2 N7 O9 Zn' _chemical_formula_weight 1019.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.976(5) _cell_length_b 12.928(5) _cell_length_c 18.049(5) _cell_angle_alpha 90.231(5) _cell_angle_beta 92.082(5) _cell_angle_gamma 113.369(5) _cell_volume 2349.0(15) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3565 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 19.79 _exptl_crystal_description red _exptl_crystal_colour block _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1050 _exptl_absorpt_coefficient_mu 0.702 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7204 _exptl_absorpt_correction_T_max 0.8723 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22046 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8187 _reflns_number_gt 5156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1000P)^2^+0.4766P] 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 refined _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8187 _refine_ls_number_parameters 624 _refine_ls_number_restraints 414 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2326 _refine_ls_wR_factor_gt 0.2088 _refine_ls_goodness_of_fit_ref 1.325 _refine_ls_restrained_S_all 1.382 _refine_ls_shift/su_max 0.017 _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 Zn1 Zn 0.47662(6) 0.24427(5) 0.78958(4) 0.0467(3) Uani 1 1 d U . . Cl2 Cl 0.2296(2) 0.30056(16) 0.07085(12) 0.0799(6) Uani 1 1 d U . . Cl1 Cl 0.2692(2) 0.77307(16) 0.68257(11) 0.0774(6) Uani 1 1 d U . . N6 N 0.2727(5) 0.1339(4) 0.8154(3) 0.0516(12) Uani 1 1 d U . . N1 N 0.5499(4) 0.1133(4) 0.8083(3) 0.0469(12) Uani 1 1 d U . . N3 N 0.6609(5) 0.3706(4) 0.7524(3) 0.0539(13) Uani 1 1 d U . . O9 O 0.7026(4) 0.6595(4) 0.5837(2) 0.0663(12) Uani 1 1 d U . . C42 C 0.6385(6) 0.0287(5) 0.9045(4) 0.0538(16) Uani 1 1 d U . . N5 N 0.3773(5) 0.3596(4) 0.7964(3) 0.0498(12) Uani 1 1 d U . . N2 N 0.5394(5) 0.2690(4) 0.9060(3) 0.0475(12) Uani 1 1 d U . . C32 C 0.7904(10) 0.4187(8) 0.5634(5) 0.091(3) Uani 1 1 d U . . H108 H 0.8658 0.4632 0.5387 0.109 Uiso 1 1 calc R . . N4 N 0.4566(5) 0.2209(4) 0.6720(3) 0.0550(13) Uani 1 1 d U . . C10 C 0.4782(6) 0.5184(5) 0.5714(4) 0.0566(16) Uani 1 1 d U . . H113 H 0.4641 0.5308 0.6205 0.068 Uiso 1 1 calc R . . C50 C 0.5918(5) 0.1096(5) 0.8799(3) 0.0453(14) Uani 1 1 d U . . C49 C 0.5892(5) 0.1938(4) 0.9316(3) 0.0437(13) Uani 1 1 d U . . C7 C 0.7510(6) 0.6206(5) 0.4352(4) 0.0585(16) Uani 1 1 d U . . H109 H 0.7481 0.6090 0.3842 0.070 Uiso 1 1 calc R . . C45 C 0.6318(6) 0.1945(5) 1.0053(3) 0.0546(16) Uani 1 1 d U . . C25 C 0.1996(6) 0.1919(6) 0.8333(3) 0.0562(16) Uani 1 1 d U . . C5 C 0.9925(6) 0.7440(5) 0.4273(4) 0.0572(16) Uani 1 1 d U . . C9 C 0.6001(6) 0.5795(5) 0.5440(3) 0.0528(15) Uani 1 1 d U . . C18 C 0.1761(7) 0.3756(7) 0.8318(4) 0.0687(19) Uani 1 1 d U . . C26 C 0.2536(6) 0.3109(5) 0.8203(3) 0.0514(15) Uani 1 1 d U . . C38 C 0.5645(7) 0.2856(5) 0.6354(3) 0.0553(16) Uani 1 1 d U . . C41 C 0.6398(6) -0.0513(5) 0.8528(4) 0.0615(17) Uani 1 1 d U . . H105 H 0.6693 -0.1068 0.8669 0.074 Uiso 1 1 calc R . . C15 C 0.4254(7) 0.4693(5) 0.7819(3) 0.0562(16) Uani 1 1 d U . . H103 H 0.5126 0.5032 0.7672 0.067 Uiso 1 1 calc R . . C30 C 0.5765(8) 0.2778(6) 0.5598(4) 0.0684(19) Uani 1 1 d U . . C8 C 0.6261(6) 0.5615(5) 0.4706(3) 0.0525(15) Uani 1 1 d U . . C44 C 0.6791(7) 0.1111(6) 1.0279(4) 0.069(2) Uani 1 1 d U . . H28 H 0.7088 0.1114 1.0769 0.083 Uiso 1 1 calc R . . C4 C 1.0097(7) 0.7375(6) 0.3527(4) 0.0716(19) Uani 1 1 d U . . H29 H 0.9390 0.6925 0.3216 0.086 Uiso 1 1 calc R . . O6 O 0.2266(7) 0.2025(5) 0.0361(4) 0.125(2) Uani 1 1 d U . . C37 C 0.6738(6) 0.3649(5) 0.6789(4) 0.0557(16) Uani 1 1 d U . . C40 C 0.5975(7) -0.0474(6) 0.7813(4) 0.0689(19) Uani 1 1 d U . . H32 H 0.5982 -0.1004 0.7466 0.083 Uiso 1 1 calc R . . C39 C 0.5524(6) 0.0369(5) 0.7598(4) 0.0547(15) Uani 1 1 d U . . H33 H 0.5241 0.0388 0.7108 0.066 Uiso 1 1 calc R . . C43 C 0.6818(6) 0.0321(6) 0.9802(4) 0.0648(18) Uani 1 1 d U . . H34 H 0.7126 -0.0215 0.9969 0.078 Uiso 1 1 calc R . . C6 C 0.8681(7) 0.6883(6) 0.4639(4) 0.0653(18) Uani 1 1 d U . . H35 H 0.8714 0.7022 0.5147 0.078 Uiso 1 1 calc R . . C1 C 1.1043(7) 0.8114(6) 0.4681(4) 0.0686(19) Uani 1 1 d U . . H36 H 1.1003 0.8206 0.5190 0.082 Uiso 1 1 calc R . . C21 C 0.0721(6) 0.1394(6) 0.8624(4) 0.0694(19) Uani 1 1 d U . . N106 N 1.2369(6) 0.8594(5) 0.3630(4) 0.0807(18) Uani 1 1 d U . . C46 C 0.6258(7) 0.2754(6) 1.0527(4) 0.0669(18) Uani 1 1 d U . . H39 H 0.6554 0.2788 1.1019 0.080 Uiso 1 1 calc R . . C47 C 0.5765(8) 0.3509(6) 1.0274(4) 0.076(2) Uani 1 1 d U . . H40 H 0.5700 0.4053 1.0591 0.091 Uiso 1 1 calc R . . O8 O 0.2842(7) 0.3905(5) 0.0243(4) 0.128(2) Uani 1 1 d U . . C48 C 0.5358(7) 0.3442(6) 0.9523(4) 0.0625(17) Uani 1 1 d U . . H42 H 0.5043 0.3969 0.9348 0.075 Uiso 1 1 calc R . . C27 C 0.3546(8) 0.1479(6) 0.6318(4) 0.0720(19) Uani 1 1 d U . . H43 H 0.2781 0.1032 0.6555 0.086 Uiso 1 1 calc R . . C33 C 0.7892(7) 0.4340(6) 0.6424(5) 0.072(2) Uani 1 1 d U . . C24 C 0.2219(6) 0.0254(6) 0.8248(4) 0.0672(19) Uani 1 1 d U . . H45 H 0.2699 -0.0163 0.8110 0.081 Uiso 1 1 calc R . . C31 C 0.6926(10) 0.3467(8) 0.5258(5) 0.089(2) Uani 1 1 d U . . H46 H 0.6987 0.3400 0.4749 0.106 Uiso 1 1 calc R . . C12 C 0.8130(7) 0.7850(6) 0.6833(4) 0.073(2) Uani 1 1 d U . . H47A H 0.8041 0.8055 0.7339 0.087 Uiso 1 1 calc R . . H47B H 0.8844 0.7587 0.6833 0.087 Uiso 1 1 calc R . . C16 C 0.3541(8) 0.5349(6) 0.7873(4) 0.0670(18) Uani 1 1 d U . . H48 H 0.3905 0.6102 0.7739 0.080 Uiso 1 1 calc R . . C28 C 0.3587(10) 0.1363(7) 0.5551(5) 0.090(2) Uani 1 1 d U . . H49 H 0.2858 0.0853 0.5281 0.108 Uiso 1 1 calc R . . O3 O 0.2634(8) 0.7682(7) 0.7591(4) 0.139(3) Uani 1 1 d U . . C2 C 1.2219(8) 0.8650(6) 0.4337(5) 0.079(2) Uani 1 1 d U . . H51 H 1.2962 0.9085 0.4632 0.095 Uiso 1 1 calc R . . C17 C 0.2309(8) 0.4886(7) 0.8121(4) 0.077(2) Uani 1 1 d U . . H52 H 0.1813 0.5322 0.8162 0.093 Uiso 1 1 calc R . . O2 O 0.1717(9) 0.6913(8) 0.6415(5) 0.187(4) Uani 1 1 d U . . C36 C 0.7602(6) 0.4459(6) 0.7928(4) 0.0713(19) Uani 1 1 d U . . H54 H 0.7512 0.4501 0.8437 0.086 Uiso 1 1 calc R . . C23 C 0.0970(7) -0.0310(6) 0.8551(4) 0.080(2) Uani 1 1 d U . . H55 H 0.0649 -0.1084 0.8619 0.095 Uiso 1 1 calc R . . O4 O 0.3908(8) 0.7661(8) 0.6652(5) 0.160(3) Uani 1 1 d U . . C35 C 0.8782(7) 0.5194(6) 0.7620(6) 0.087(2) Uani 1 1 d U . . H57 H 0.9462 0.5718 0.7914 0.105 Uiso 1 1 calc R . . O7 O 0.0989(7) 0.2890(6) 0.0893(5) 0.149(3) Uani 1 1 d U . . C34 C 0.8899(8) 0.5113(7) 0.6881(6) 0.091(3) Uani 1 1 d U . . H59 H 0.9678 0.5590 0.6669 0.110 Uiso 1 1 calc R . . C29 C 0.4706(11) 0.2004(8) 0.5209(5) 0.091(2) Uani 1 1 d U . . H60 H 0.4754 0.1916 0.4701 0.109 Uiso 1 1 calc R . . C22 C 0.0253(8) 0.0250(8) 0.8739(5) 0.087(2) Uani 1 1 d U . . H61 H -0.0566 -0.0123 0.8947 0.104 Uiso 1 1 calc R . . C3 C 1.1314(8) 0.7973(7) 0.3243(5) 0.082(2) Uani 1 1 d U . . H63 H 1.1386 0.7930 0.2733 0.098 Uiso 1 1 calc R . . C11 C 0.6856(7) 0.6900(6) 0.6569(4) 0.0700(19) Uani 1 1 d U . . H64A H 0.6660 0.6260 0.6892 0.084 Uiso 1 1 calc R . . H64B H 0.6124 0.7141 0.6576 0.084 Uiso 1 1 calc R . . C19 C 0.0466(8) 0.3197(8) 0.8619(5) 0.092(3) Uani 1 1 d U . . H65 H -0.0051 0.3602 0.8708 0.110 Uiso 1 1 calc R . . C20 C -0.0009(8) 0.2063(8) 0.8776(5) 0.094(3) Uani 1 1 d U . . H66 H -0.0831 0.1726 0.8987 0.113 Uiso 1 1 calc R . . O5 O 0.3140(8) 0.3189(7) 0.1357(4) 0.151(3) Uani 1 1 d U . . O1 O 0.2848(11) 0.8775(7) 0.6597(5) 0.188(4) Uani 1 1 d U . . C13 C 0.8494(8) 0.8864(6) 0.6372(5) 0.089(2) Uani 1 1 d U . . H69A H 0.7854 0.9198 0.6436 0.106 Uiso 1 1 calc R . . H69B H 0.8443 0.8639 0.5855 0.106 Uiso 1 1 calc R . . C14 C 0.9868(10) 0.9738(8) 0.6559(6) 0.122(3) Uani 1 1 d U . . H70A H 0.9918 0.9986 0.7066 0.182 Uiso 1 1 calc R . . H70B H 1.0050 1.0370 0.6239 0.182 Uiso 1 1 calc R . . H70C H 1.0510 0.9417 0.6492 0.182 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0460(4) 0.0493(4) 0.0440(4) 0.0079(3) 0.0049(3) 0.0178(3) Cl2 0.0859(13) 0.0606(11) 0.0964(15) 0.0133(10) 0.0134(11) 0.0315(10) Cl1 0.0759(12) 0.0708(12) 0.0765(13) 0.0035(10) -0.0024(10) 0.0200(10) N6 0.046(3) 0.053(3) 0.056(3) 0.012(2) 0.000(2) 0.019(2) N1 0.046(3) 0.049(3) 0.046(3) 0.003(2) 0.004(2) 0.019(2) N3 0.045(3) 0.051(3) 0.064(3) 0.008(2) 0.006(2) 0.016(2) O9 0.061(3) 0.072(3) 0.056(3) -0.009(2) 0.010(2) 0.016(2) C42 0.041(3) 0.055(4) 0.062(4) 0.012(3) 0.002(3) 0.017(3) N5 0.053(3) 0.055(3) 0.044(3) 0.005(2) 0.003(2) 0.024(2) N2 0.055(3) 0.046(3) 0.047(3) 0.001(2) 0.002(2) 0.026(2) C32 0.106(6) 0.090(5) 0.101(6) 0.049(5) 0.065(5) 0.059(5) N4 0.059(3) 0.055(3) 0.053(3) 0.002(2) -0.003(2) 0.025(3) C10 0.060(4) 0.059(4) 0.049(3) -0.001(3) 0.008(3) 0.021(3) C50 0.036(3) 0.047(3) 0.050(3) 0.007(3) 0.005(2) 0.012(2) C49 0.041(3) 0.042(3) 0.044(3) 0.006(3) 0.004(2) 0.012(2) C7 0.057(4) 0.062(4) 0.055(4) 0.007(3) 0.007(3) 0.022(3) C45 0.061(4) 0.056(4) 0.044(3) 0.006(3) -0.003(3) 0.021(3) C25 0.044(3) 0.073(4) 0.046(3) 0.005(3) -0.003(3) 0.019(3) C5 0.059(4) 0.052(3) 0.064(4) 0.005(3) 0.009(3) 0.026(3) C9 0.052(3) 0.053(3) 0.054(4) -0.002(3) 0.003(3) 0.021(3) C18 0.061(4) 0.087(5) 0.065(4) -0.011(4) -0.004(3) 0.038(4) C26 0.051(3) 0.069(4) 0.041(3) -0.004(3) -0.003(3) 0.032(3) C38 0.069(4) 0.057(4) 0.053(4) 0.018(3) 0.013(3) 0.039(3) C41 0.060(4) 0.053(4) 0.077(4) -0.003(3) 0.000(3) 0.028(3) C15 0.065(4) 0.056(4) 0.048(3) 0.003(3) 0.003(3) 0.025(3) C30 0.097(5) 0.073(4) 0.057(4) 0.014(3) 0.017(4) 0.054(4) C8 0.051(3) 0.056(3) 0.053(4) 0.005(3) 0.007(3) 0.023(3) C44 0.070(4) 0.070(4) 0.067(4) 0.015(4) -0.013(3) 0.027(3) C4 0.065(4) 0.080(5) 0.072(5) -0.002(4) 0.007(3) 0.031(4) O6 0.142(5) 0.094(4) 0.150(5) -0.017(4) -0.019(4) 0.063(4) C37 0.060(4) 0.055(4) 0.063(4) 0.021(3) 0.024(3) 0.034(3) C40 0.071(4) 0.062(4) 0.080(5) -0.016(3) 0.011(4) 0.032(3) C39 0.053(3) 0.059(4) 0.055(4) -0.003(3) 0.005(3) 0.025(3) C43 0.065(4) 0.062(4) 0.072(4) 0.014(4) -0.003(3) 0.031(3) C6 0.070(4) 0.065(4) 0.058(4) 0.004(3) 0.011(3) 0.023(3) C1 0.064(4) 0.070(4) 0.074(4) 0.001(4) 0.009(3) 0.027(3) C21 0.050(4) 0.083(5) 0.070(4) 0.002(4) 0.001(3) 0.021(3) N106 0.067(4) 0.080(4) 0.096(5) 0.012(4) 0.022(4) 0.028(3) C46 0.086(5) 0.073(4) 0.045(4) -0.001(3) -0.008(3) 0.036(4) C47 0.098(5) 0.078(5) 0.053(4) -0.011(3) -0.003(4) 0.037(4) O8 0.121(5) 0.098(4) 0.170(6) 0.059(4) 0.035(4) 0.044(4) C48 0.082(4) 0.057(4) 0.057(4) 0.000(3) -0.003(3) 0.036(3) C27 0.079(5) 0.071(4) 0.068(4) -0.001(4) -0.011(4) 0.033(4) C33 0.070(4) 0.064(4) 0.098(5) 0.027(4) 0.028(4) 0.040(4) C24 0.058(4) 0.064(4) 0.073(4) 0.021(3) -0.003(3) 0.018(3) C31 0.129(6) 0.095(5) 0.070(5) 0.024(4) 0.037(5) 0.071(5) C12 0.078(4) 0.071(4) 0.061(4) -0.002(3) -0.004(3) 0.023(4) C16 0.085(5) 0.058(4) 0.065(4) -0.007(3) -0.007(4) 0.037(4) C28 0.116(6) 0.088(5) 0.072(5) -0.016(4) -0.033(5) 0.049(5) O3 0.178(6) 0.168(6) 0.088(4) 0.007(4) 0.017(4) 0.086(5) C2 0.065(4) 0.069(4) 0.101(6) -0.004(4) 0.002(4) 0.023(4) C17 0.089(5) 0.073(5) 0.083(5) -0.021(4) -0.016(4) 0.048(4) O2 0.141(6) 0.182(7) 0.151(6) -0.024(5) 0.022(5) -0.029(5) C36 0.054(4) 0.066(4) 0.084(5) 0.009(4) -0.002(3) 0.014(3) C23 0.063(4) 0.069(4) 0.087(5) 0.027(4) -0.010(4) 0.007(4) O4 0.117(5) 0.216(7) 0.151(6) -0.029(5) 0.003(5) 0.071(5) C35 0.062(4) 0.066(4) 0.125(6) 0.008(4) -0.006(4) 0.017(4) O7 0.107(5) 0.144(6) 0.198(7) 0.042(5) 0.048(5) 0.049(4) C34 0.072(5) 0.076(5) 0.138(7) 0.039(5) 0.036(5) 0.038(4) C29 0.135(7) 0.093(5) 0.069(5) 0.009(4) 0.010(5) 0.070(5) C22 0.054(4) 0.100(5) 0.096(5) 0.027(4) 0.010(4) 0.019(4) C3 0.078(5) 0.093(5) 0.070(5) 0.009(4) 0.019(4) 0.029(4) C11 0.068(4) 0.072(4) 0.066(4) 0.002(3) 0.011(3) 0.024(3) C19 0.068(5) 0.115(6) 0.100(6) -0.020(5) -0.001(4) 0.045(4) C20 0.052(4) 0.121(6) 0.103(6) -0.007(5) 0.012(4) 0.027(4) O5 0.160(6) 0.193(7) 0.112(5) -0.024(5) -0.018(5) 0.084(5) O1 0.236(8) 0.130(6) 0.204(7) 0.039(5) -0.028(6) 0.084(6) C13 0.086(5) 0.072(5) 0.102(5) -0.003(4) -0.013(4) 0.028(4) C14 0.106(6) 0.108(6) 0.138(7) 0.024(5) -0.019(5) 0.030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.133(5) . ? Zn1 N1 2.167(5) . ? Zn1 N3 2.167(5) . ? Zn1 N2 2.170(5) . ? Zn1 N5 2.174(5) . ? Zn1 N6 2.193(5) . ? Cl2 O8 1.382(6) . ? Cl2 O6 1.401(6) . ? Cl2 O5 1.425(8) . ? Cl2 O7 1.433(7) . ? Cl1 O2 1.360(8) . ? Cl1 O1 1.359(8) . ? Cl1 O3 1.385(7) . ? Cl1 O4 1.419(8) . ? N6 C24 1.303(8) . ? N6 C25 1.343(8) . ? N1 C39 1.327(7) . ? N1 C50 1.362(7) . ? N3 C36 1.328(8) . ? N3 C37 1.343(8) . ? O9 C9 1.365(7) . ? O9 C11 1.418(8) . ? C42 C41 1.395(9) . ? C42 C50 1.403(8) . ? C42 C43 1.425(9) . ? N5 C15 1.332(7) . ? N5 C26 1.339(7) . ? N2 C48 1.293(8) . ? N2 C49 1.364(7) . ? C32 C31 1.276(12) . ? C32 C33 1.440(12) . ? C32 H108 0.9300 . ? N4 C27 1.329(8) . ? N4 C38 1.348(8) . ? C10 C9 1.368(8) . ? C10 C8 1.394(8) 2_666 ? C10 H113 0.9300 . ? C50 C49 1.441(8) . ? C49 C45 1.392(8) . ? C7 C6 1.319(9) . ? C7 C8 1.452(8) . ? C7 H109 0.9300 . ? C45 C46 1.372(9) . ? C45 C44 1.425(9) . ? C25 C21 1.414(9) . ? C25 C26 1.437(9) . ? C5 C4 1.373(9) . ? C5 C1 1.374(9) . ? C5 C6 1.453(9) . ? C9 C8 1.402(8) . ? C18 C17 1.395(10) . ? C18 C26 1.429(9) . ? C18 C19 1.443(10) . ? C38 C30 1.382(9) . ? C38 C37 1.434(9) . ? C41 C40 1.362(9) . ? C41 H105 0.9300 . ? C15 C16 1.369(9) . ? C15 H103 0.9300 . ? C30 C29 1.362(11) . ? C30 C31 1.398(11) . ? C8 C10 1.394(8) 2_666 ? C44 C43 1.344(10) . ? C44 H28 0.9300 . ? C4 C3 1.371(10) . ? C4 H29 0.9300 . ? C37 C33 1.416(9) . ? C40 C39 1.413(9) . ? C40 H32 0.9300 . ? C39 H33 0.9300 . ? C43 H34 0.9300 . ? C6 H35 0.9300 . ? C1 C2 1.373(10) . ? C1 H36 0.9300 . ? C21 C22 1.379(11) . ? C21 C20 1.424(11) . ? N106 C3 1.293(9) . ? N106 C2 1.298(10) . ? C46 C47 1.363(10) . ? C46 H39 0.9300 . ? C47 C48 1.403(9) . ? C47 H40 0.9300 . ? C48 H42 0.9300 . ? C27 C28 1.396(10) . ? C27 H43 0.9300 . ? C33 C34 1.396(11) . ? C24 C23 1.404(9) . ? C24 H45 0.9300 . ? C31 H46 0.9300 . ? C12 C13 1.478(10) . ? C12 C11 1.508(9) . ? C12 H47A 0.9700 . ? C12 H47B 0.9700 . ? C16 C17 1.339(10) . ? C16 H48 0.9300 . ? C28 C29 1.353(12) . ? C28 H49 0.9300 . ? C2 H51 0.9300 . ? C17 H52 0.9300 . ? C36 C35 1.404(10) . ? C36 H54 0.9300 . ? C23 C22 1.315(11) . ? C23 H55 0.9300 . ? C35 C34 1.352(12) . ? C35 H57 0.9300 . ? C34 H59 0.9300 . ? C29 H60 0.9300 . ? C22 H61 0.9300 . ? C3 H63 0.9300 . ? C11 H64A 0.9700 . ? C11 H64B 0.9700 . ? C19 C20 1.381(12) . ? C19 H65 0.9300 . ? C20 H66 0.9300 . ? C13 C14 1.508(11) . ? C13 H69A 0.9700 . ? C13 H69B 0.9700 . ? C14 H70A 0.9600 . ? C14 H70B 0.9600 . ? C14 H70C 0.9600 . ? 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 N4 Zn1 N1 94.76(18) . . ? N4 Zn1 N3 77.1(2) . . ? N1 Zn1 N3 96.60(18) . . ? N4 Zn1 N2 167.65(19) . . ? N1 Zn1 N2 77.34(18) . . ? N3 Zn1 N2 94.26(19) . . ? N4 Zn1 N5 96.71(18) . . ? N1 Zn1 N5 165.52(17) . . ? N3 Zn1 N5 94.56(18) . . ? N2 Zn1 N5 92.68(18) . . ? N4 Zn1 N6 97.86(19) . . ? N1 Zn1 N6 93.08(18) . . ? N3 Zn1 N6 169.39(18) . . ? N2 Zn1 N6 92.09(18) . . ? N5 Zn1 N6 76.63(19) . . ? O8 Cl2 O6 109.3(5) . . ? O8 Cl2 O5 108.9(5) . . ? O6 Cl2 O5 106.5(5) . . ? O8 Cl2 O7 109.8(4) . . ? O6 Cl2 O7 111.2(5) . . ? O5 Cl2 O7 111.1(5) . . ? O2 Cl1 O1 111.2(7) . . ? O2 Cl1 O3 118.0(5) . . ? O1 Cl1 O3 110.0(6) . . ? O2 Cl1 O4 106.8(6) . . ? O1 Cl1 O4 103.5(6) . . ? O3 Cl1 O4 106.2(5) . . ? C24 N6 C25 117.8(5) . . ? C24 N6 Zn1 128.9(5) . . ? C25 N6 Zn1 112.5(4) . . ? C39 N1 C50 118.9(5) . . ? C39 N1 Zn1 127.6(4) . . ? C50 N1 Zn1 113.5(4) . . ? C36 N3 C37 118.6(6) . . ? C36 N3 Zn1 128.4(5) . . ? C37 N3 Zn1 112.9(4) . . ? C9 O9 C11 120.8(5) . . ? C41 C42 C50 117.5(6) . . ? C41 C42 C43 123.5(6) . . ? C50 C42 C43 119.0(6) . . ? C15 N5 C26 118.5(5) . . ? C15 N5 Zn1 128.3(4) . . ? C26 N5 Zn1 113.2(4) . . ? C48 N2 C49 117.7(5) . . ? C48 N2 Zn1 128.6(4) . . ? C49 N2 Zn1 113.6(4) . . ? C31 C32 C33 122.9(8) . . ? C31 C32 H108 118.6 . . ? C33 C32 H108 118.6 . . ? C27 N4 C38 117.1(6) . . ? C27 N4 Zn1 128.2(5) . . ? C38 N4 Zn1 114.6(4) . . ? C9 C10 C8 123.4(6) . 2_666 ? C9 C10 H113 118.3 . . ? C8 C10 H113 118.3 2_666 . ? N1 C50 C42 122.8(6) . . ? N1 C50 C49 118.0(5) . . ? C42 C50 C49 119.2(5) . . ? N2 C49 C45 122.1(6) . . ? N2 C49 C50 117.4(5) . . ? C45 C49 C50 120.4(5) . . ? C6 C7 C8 130.3(6) . . ? C6 C7 H109 114.8 . . ? C8 C7 H109 114.8 . . ? C46 C45 C49 118.3(6) . . ? C46 C45 C44 123.1(6) . . ? C49 C45 C44 118.6(6) . . ? N6 C25 C21 122.3(6) . . ? N6 C25 C26 117.8(5) . . ? C21 C25 C26 119.9(6) . . ? C4 C5 C1 115.0(6) . . ? C4 C5 C6 125.3(6) . . ? C1 C5 C6 119.7(6) . . ? O9 C9 C10 124.3(6) . . ? O9 C9 C8 115.7(5) . . ? C10 C9 C8 120.0(6) . . ? C17 C18 C26 117.3(7) . . ? C17 C18 C19 124.6(7) . . ? C26 C18 C19 118.1(7) . . ? N5 C26 C18 120.8(6) . . ? N5 C26 C25 118.7(5) . . ? C18 C26 C25 120.6(6) . . ? N4 C38 C30 124.1(7) . . ? N4 C38 C37 116.9(5) . . ? C30 C38 C37 119.1(6) . . ? C40 C41 C42 119.4(6) . . ? C40 C41 H105 120.3 . . ? C42 C41 H105 120.3 . . ? N5 C15 C16 123.9(6) . . ? N5 C15 H103 118.0 . . ? C16 C15 H103 118.0 . . ? C38 C30 C29 116.9(7) . . ? C38 C30 C31 120.8(8) . . ? C29 C30 C31 122.3(8) . . ? C10 C8 C9 116.6(5) 2_666 . ? C10 C8 C7 118.2(6) 2_666 . ? C9 C8 C7 125.2(6) . . ? C43 C44 C45 121.5(6) . . ? C43 C44 H28 119.2 . . ? C45 C44 H28 119.2 . . ? C3 C4 C5 119.9(7) . . ? C3 C4 H29 120.1 . . ? C5 C4 H29 120.1 . . ? N3 C37 C33 123.2(7) . . ? N3 C37 C38 118.2(5) . . ? C33 C37 C38 118.5(6) . . ? C41 C40 C39 120.3(6) . . ? C41 C40 H32 119.8 . . ? C39 C40 H32 119.8 . . ? N1 C39 C40 121.1(6) . . ? N1 C39 H33 119.5 . . ? C40 C39 H33 119.5 . . ? C44 C43 C42 121.3(6) . . ? C44 C43 H34 119.3 . . ? C42 C43 H34 119.3 . . ? C7 C6 C5 129.1(7) . . ? C7 C6 H35 115.5 . . ? C5 C6 H35 115.4 . . ? C2 C1 C5 119.9(7) . . ? C2 C1 H36 120.0 . . ? C5 C1 H36 120.0 . . ? C22 C21 C25 117.4(7) . . ? C22 C21 C20 123.8(7) . . ? C25 C21 C20 118.8(7) . . ? C3 N106 C2 115.6(7) . . ? C47 C46 C45 119.8(6) . . ? C47 C46 H39 120.1 . . ? C45 C46 H39 120.1 . . ? C46 C47 C48 118.1(7) . . ? C46 C47 H40 121.0 . . ? C48 C47 H40 121.0 . . ? N2 C48 C47 123.9(6) . . ? N2 C48 H42 118.1 . . ? C47 C48 H42 118.1 . . ? N4 C27 C28 122.0(8) . . ? N4 C27 H43 119.0 . . ? C28 C27 H43 119.0 . . ? C34 C33 C37 115.3(7) . . ? C34 C33 C32 127.1(8) . . ? C37 C33 C32 117.6(8) . . ? N6 C24 C23 122.4(7) . . ? N6 C24 H45 118.8 . . ? C23 C24 H45 118.8 . . ? C32 C31 C30 121.2(8) . . ? C32 C31 H46 119.4 . . ? C30 C31 H46 119.4 . . ? C13 C12 C11 113.5(6) . . ? C13 C12 H47A 108.9 . . ? C11 C12 H47A 108.9 . . ? C13 C12 H47B 108.9 . . ? C11 C12 H47B 108.9 . . ? H47A C12 H47B 107.7 . . ? C17 C16 C15 118.7(7) . . ? C17 C16 H48 120.7 . . ? C15 C16 H48 120.7 . . ? C29 C28 C27 118.9(8) . . ? C29 C28 H49 120.5 . . ? C27 C28 H49 120.6 . . ? N106 C2 C1 124.6(8) . . ? N106 C2 H51 117.7 . . ? C1 C2 H51 117.7 . . ? C16 C17 C18 120.6(7) . . ? C16 C17 H52 119.7 . . ? C18 C17 H52 119.7 . . ? N3 C36 C35 122.6(7) . . ? N3 C36 H54 118.7 . . ? C35 C36 H54 118.7 . . ? C22 C23 C24 120.4(7) . . ? C22 C23 H55 119.8 . . ? C24 C23 H55 119.8 . . ? C34 C35 C36 117.8(8) . . ? C34 C35 H57 121.1 . . ? C36 C35 H57 121.1 . . ? C35 C34 C33 122.4(7) . . ? C35 C34 H59 118.8 . . ? C33 C34 H59 118.8 . . ? C28 C29 C30 121.0(8) . . ? C28 C29 H60 119.5 . . ? C30 C29 H60 119.5 . . ? C23 C22 C21 119.7(7) . . ? C23 C22 H61 120.2 . . ? C21 C22 H61 120.2 . . ? N106 C3 C4 125.0(8) . . ? N106 C3 H63 117.5 . . ? C4 C3 H63 117.5 . . ? O9 C11 C12 107.7(6) . . ? O9 C11 H64A 110.2 . . ? C12 C11 H64A 110.2 . . ? O9 C11 H64B 110.2 . . ? C12 C11 H64B 110.2 . . ? H64A C11 H64B 108.5 . . ? C20 C19 C18 120.4(8) . . ? C20 C19 H65 119.8 . . ? C18 C19 H65 119.8 . . ? C19 C20 C21 122.1(7) . . ? C19 C20 H66 118.9 . . ? C21 C20 H66 118.9 . . ? C12 C13 C14 113.4(7) . . ? C12 C13 H69A 108.9 . . ? C14 C13 H69A 108.9 . . ? C12 C13 H69B 108.9 . . ? C14 C13 H69B 108.9 . . ? H69A C13 H69B 107.7 . . ? C13 C14 H70A 109.5 . . ? C13 C14 H70B 109.5 . . ? H70A C14 H70B 109.5 . . ? C13 C14 H70C 109.5 . . ? H70A C14 H70C 109.5 . . ? H70B C14 H70C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.663 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 737794'