# 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_b363 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N8 S2' _chemical_formula_weight 438.58 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 5.512(2) _cell_length_b 25.524(10) _cell_length_c 7.743(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.287(9) _cell_angle_gamma 90.00 _cell_volume 1028.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1343 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 23.25 _exptl_crystal_description Thin_Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9044 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details 'Sadabs. (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 '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 7055 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2342 _reflns_number_gt 1798 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0818P)^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 2342 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 S1 S 0.25447(11) 0.29700(2) 0.74990(8) 0.0417(2) Uani 1 1 d . . . N1 N -0.1774(4) 0.41843(8) 0.6798(3) 0.0358(5) Uani 1 1 d . . . N2 N -0.0887(4) 0.46657(7) 0.7094(3) 0.0346(5) Uani 1 1 d . . . N3 N 0.1492(3) 0.46598(7) 0.6988(2) 0.0271(4) Uani 1 1 d . . . N4 N 0.3785(4) 0.19959(8) 0.7869(3) 0.0410(5) Uani 1 1 d . . . C1 C 0.3415(6) 0.14841(11) 0.7632(4) 0.0480(7) Uani 1 1 d . . . H1 H 0.4816 0.1262 0.8186 0.058 Uiso 1 1 calc R . . C2 C 0.1118(5) 0.12566(10) 0.6628(4) 0.0467(7) Uani 1 1 d . . . H2 H 0.0958 0.0891 0.6498 0.056 Uiso 1 1 calc R . . C3 C -0.0934(5) 0.15808(10) 0.5823(4) 0.0443(6) Uani 1 1 d . . . H3 H -0.2531 0.1438 0.5127 0.053 Uiso 1 1 calc R . . C4 C -0.0647(5) 0.21137(9) 0.6037(3) 0.0391(6) Uani 1 1 d . . . H4 H -0.2032 0.2342 0.5508 0.047 Uiso 1 1 calc R . . C5 C 0.1774(5) 0.23054(9) 0.7068(3) 0.0320(5) Uani 1 1 d . . . C6 C -0.0383(4) 0.33017(9) 0.6174(3) 0.0350(5) Uani 1 1 d . . . H6A H -0.0785 0.3224 0.4869 0.042 Uiso 1 1 calc R . . H6B H -0.1823 0.3184 0.6553 0.042 Uiso 1 1 calc R . . C7 C 0.0040(4) 0.38740(9) 0.6507(3) 0.0293(5) Uani 1 1 d . . . C8 C 0.2146(4) 0.41776(8) 0.6621(3) 0.0306(5) Uani 1 1 d . . . H8 H 0.3698 0.4071 0.6474 0.037 Uiso 1 1 calc R . . C9 C 0.3093(4) 0.51300(9) 0.7430(3) 0.0310(5) Uani 1 1 d . . . H9A H 0.2071 0.5434 0.6836 0.037 Uiso 1 1 calc R . . H9B H 0.4524 0.5093 0.6953 0.037 Uiso 1 1 calc R . . C10 C 0.4146(4) 0.52204(8) 0.9482(3) 0.0311(5) Uani 1 1 d . . . H10A H 0.5132 0.5548 0.9722 0.037 Uiso 1 1 calc R . . H10B H 0.2704 0.5262 0.9946 0.037 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 S1 0.0286(4) 0.0337(4) 0.0503(4) -0.0041(3) -0.0036(3) -0.0014(2) N1 0.0249(10) 0.0403(11) 0.0407(11) -0.0011(9) 0.0087(9) 0.0000(8) N2 0.0241(10) 0.0385(11) 0.0412(11) -0.0029(8) 0.0107(8) 0.0027(8) N3 0.0233(9) 0.0315(10) 0.0239(8) -0.0009(7) 0.0042(7) 0.0007(7) N4 0.0340(12) 0.0370(12) 0.0446(12) -0.0010(9) 0.0029(9) 0.0026(9) C1 0.0407(15) 0.0418(16) 0.0538(16) 0.0020(12) 0.0051(12) 0.0072(11) C2 0.0485(16) 0.0322(13) 0.0576(16) -0.0015(11) 0.0150(13) -0.0025(11) C3 0.0364(14) 0.0400(14) 0.0520(15) -0.0044(11) 0.0085(12) -0.0091(11) C4 0.0288(13) 0.0373(13) 0.0459(13) -0.0020(11) 0.0051(10) -0.0005(10) C5 0.0292(12) 0.0361(13) 0.0281(11) -0.0028(9) 0.0058(9) -0.0019(9) C6 0.0265(12) 0.0336(12) 0.0368(12) -0.0002(9) -0.0004(10) -0.0006(9) C7 0.0232(11) 0.0336(12) 0.0268(10) -0.0003(9) 0.0023(9) 0.0009(9) C8 0.0229(11) 0.0368(12) 0.0319(11) -0.0045(9) 0.0088(9) 0.0029(9) C9 0.0296(11) 0.0301(12) 0.0301(11) 0.0024(9) 0.0054(9) -0.0023(9) C10 0.0326(12) 0.0263(11) 0.0287(11) -0.0027(9) 0.0025(9) 0.0008(9) _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 S1 C5 1.754(2) . ? S1 C6 1.811(2) . ? N1 N2 1.314(3) . ? N1 C7 1.352(3) . ? N2 N3 1.341(3) . ? N3 C8 1.339(3) . ? N3 C9 1.462(3) . ? N4 C1 1.326(3) . ? N4 C5 1.335(3) . ? C1 C2 1.376(4) . ? C2 C3 1.374(4) . ? C3 C4 1.373(3) . ? C4 C5 1.398(3) . ? C6 C7 1.488(3) . ? C7 C8 1.374(3) . ? C9 C10 1.519(3) . ? C10 C10 1.515(4) 3_667 ? 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 C5 S1 C6 103.29(11) . . ? N2 N1 C7 108.90(19) . . ? N1 N2 N3 107.09(17) . . ? C8 N3 N2 111.13(18) . . ? C8 N3 C9 128.34(19) . . ? N2 N3 C9 120.24(18) . . ? C1 N4 C5 116.9(2) . . ? N4 C1 C2 124.4(3) . . ? C3 C2 C1 117.9(2) . . ? C4 C3 C2 119.8(2) . . ? C3 C4 C5 117.8(2) . . ? N4 C5 C4 123.2(2) . . ? N4 C5 S1 111.84(17) . . ? C4 C5 S1 124.94(19) . . ? C7 C6 S1 107.54(15) . . ? N1 C7 C8 108.3(2) . . ? N1 C7 C6 121.4(2) . . ? C8 C7 C6 130.2(2) . . ? N3 C8 C7 104.5(2) . . ? N3 C9 C10 111.24(17) . . ? C10 C10 C9 113.4(2) 3_667 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.521 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.265 _database_code_depnum_ccdc_archive 'CCDC 938526' ####################################################################### # # 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_c386a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Cl4 N8 S2 Zn2' _chemical_formula_weight 683.06 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.584(3) _cell_length_b 7.9537(15) _cell_length_c 12.942(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.153(4) _cell_angle_gamma 90.00 _cell_volume 1265.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 941 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.33 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 2.508 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5962 _exptl_absorpt_correction_T_max 0.7699 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 8760 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2912 _reflns_number_gt 2460 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.2442P] 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 2912 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 Zn1 Zn 0.26283(3) 0.74880(3) 0.22357(3) 0.01570(13) Uani 1 1 d . . . Cl1 Cl 0.14346(5) 0.61676(8) 0.26890(6) 0.02068(17) Uani 1 1 d . . . Cl2 Cl 0.40230(6) 0.87404(9) 0.36816(6) 0.02651(19) Uani 1 1 d . . . S1 S 0.14335(6) 0.75434(8) -0.07681(6) 0.02024(18) Uani 1 1 d . . . N1 N 0.32561(18) 0.5777(3) 0.15271(19) 0.0163(5) Uani 1 1 d . . . N2 N 0.36977(18) 0.4404(3) 0.2111(2) 0.0193(5) Uani 1 1 d . . . N3 N 0.40500(18) 0.3532(3) 0.1461(2) 0.0187(5) Uani 1 1 d . . . N4 N 0.19206(18) 0.9454(3) 0.11229(19) 0.0170(5) Uani 1 1 d . . . C1 C 0.4652(2) 0.1948(4) 0.1868(2) 0.0231(6) Uani 1 1 d . . . H1A H 0.5119 0.1757 0.1465 0.028 Uiso 1 1 calc R . . H1B H 0.4127 0.1007 0.1675 0.028 Uiso 1 1 calc R . . C2 C 0.3844(2) 0.4324(4) 0.0469(2) 0.0210(6) Uani 1 1 d . . . H2 H 0.4023 0.3954 -0.0128 0.025 Uiso 1 1 calc R . . C3 C 0.3320(2) 0.5778(3) 0.0509(2) 0.0178(5) Uani 1 1 d . . . C4 C 0.2885(2) 0.7159(4) -0.0337(2) 0.0205(6) Uani 1 1 d . . . H4A H 0.3002 0.6875 -0.1021 0.025 Uiso 1 1 calc R . . H4B H 0.3295 0.8202 -0.0004 0.025 Uiso 1 1 calc R . . C5 C 0.1452(2) 0.9432(3) -0.0030(2) 0.0176(5) Uani 1 1 d . . . C6 C 0.0919(2) 1.0828(4) -0.0660(2) 0.0211(6) Uani 1 1 d . . . H6 H 0.0600 1.0783 -0.1471 0.025 Uiso 1 1 calc R . . C7 C 0.0852(3) 1.2286(3) -0.0112(3) 0.0240(6) Uani 1 1 d . . . H7 H 0.0490 1.3250 -0.0537 0.029 Uiso 1 1 calc R . . C8 C 0.1326(3) 1.2311(3) 0.1079(3) 0.0222(6) Uani 1 1 d . . . H8 H 0.1281 1.3283 0.1483 0.027 Uiso 1 1 calc R . . C9 C 0.1861(2) 1.0892(4) 0.1654(2) 0.0222(6) Uani 1 1 d . . . H9 H 0.2206 1.0923 0.2465 0.027 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 0.0202(2) 0.0131(2) 0.01442(19) -0.00023(10) 0.00797(15) 0.00028(11) Cl1 0.0239(3) 0.0196(3) 0.0233(3) -0.0003(3) 0.0146(3) -0.0007(3) Cl2 0.0315(4) 0.0214(4) 0.0188(3) 0.0026(3) 0.0031(3) -0.0100(3) S1 0.0237(4) 0.0192(4) 0.0154(3) -0.0031(2) 0.0060(3) 0.0021(2) N1 0.0173(11) 0.0157(11) 0.0174(11) 0.0005(8) 0.0088(9) 0.0013(8) N2 0.0183(11) 0.0163(11) 0.0235(12) -0.0007(9) 0.0091(10) 0.0008(9) N3 0.0175(11) 0.0145(11) 0.0230(11) -0.0041(9) 0.0076(10) -0.0001(9) N4 0.0195(11) 0.0137(11) 0.0177(11) -0.0007(9) 0.0078(9) -0.0015(9) C1 0.0232(15) 0.0135(13) 0.0310(17) -0.0014(11) 0.0100(13) 0.0036(11) C2 0.0212(14) 0.0193(14) 0.0224(14) -0.0033(11) 0.0092(12) -0.0017(11) C3 0.0160(13) 0.0192(14) 0.0182(13) -0.0043(10) 0.0072(11) -0.0026(10) C4 0.0232(15) 0.0219(14) 0.0190(14) -0.0005(11) 0.0115(12) 0.0011(11) C5 0.0197(13) 0.0165(13) 0.0193(13) -0.0011(10) 0.0107(11) -0.0005(10) C6 0.0243(14) 0.0237(15) 0.0157(12) 0.0050(10) 0.0087(11) 0.0023(11) C7 0.0264(16) 0.0187(15) 0.0270(16) 0.0057(11) 0.0113(13) 0.0037(11) C8 0.0230(15) 0.0134(14) 0.0297(16) -0.0028(11) 0.0106(13) -0.0008(10) C9 0.0254(15) 0.0199(14) 0.0193(13) -0.0022(11) 0.0075(12) -0.0004(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 Zn1 N1 2.021(2) . ? Zn1 N4 2.066(2) . ? Zn1 Cl1 2.2102(7) . ? Zn1 Cl2 2.2516(8) . ? S1 C5 1.774(3) . ? S1 C4 1.832(3) . ? N1 N2 1.318(3) . ? N1 C3 1.358(3) . ? N2 N3 1.326(3) . ? N3 C2 1.348(4) . ? N3 C1 1.472(4) . ? N4 C5 1.351(3) . ? N4 C9 1.354(3) . ? C1 C1 1.503(6) 2_655 ? C2 C3 1.370(4) . ? C3 C4 1.484(4) . ? C5 C6 1.386(4) . ? C6 C7 1.383(4) . ? C7 C8 1.395(4) . ? C8 C9 1.377(4) . ? 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 N1 Zn1 N4 110.77(9) . . ? N1 Zn1 Cl1 107.40(7) . . ? N4 Zn1 Cl1 111.60(7) . . ? N1 Zn1 Cl2 107.86(7) . . ? N4 Zn1 Cl2 102.85(7) . . ? Cl1 Zn1 Cl2 116.28(3) . . ? C5 S1 C4 102.14(13) . . ? N2 N1 C3 110.8(2) . . ? N2 N1 Zn1 118.36(17) . . ? C3 N1 Zn1 130.80(18) . . ? N1 N2 N3 105.6(2) . . ? N2 N3 C2 112.0(2) . . ? N2 N3 C1 121.1(2) . . ? C2 N3 C1 126.8(2) . . ? C5 N4 C9 118.1(2) . . ? C5 N4 Zn1 128.41(18) . . ? C9 N4 Zn1 113.31(18) . . ? N3 C1 C1 112.73(17) . 2_655 ? N3 C2 C3 105.1(2) . . ? N1 C3 C2 106.5(2) . . ? N1 C3 C4 123.1(2) . . ? C2 C3 C4 130.4(2) . . ? C3 C4 S1 112.83(19) . . ? N4 C5 C6 121.5(2) . . ? N4 C5 S1 119.9(2) . . ? C6 C5 S1 118.5(2) . . ? C7 C6 C5 120.1(3) . . ? C6 C7 C8 118.6(3) . . ? C9 C8 C7 118.4(3) . . ? N4 C9 C8 123.3(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.637 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.160 _database_code_depnum_ccdc_archive 'CCDC 938527' ####################################################################### # # 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_d108 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl4 N8 S2 Zn2' _chemical_formula_weight 711.12 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.4605(18) _cell_length_b 11.6501(10) _cell_length_c 14.0409(13) _cell_angle_alpha 90.00 _cell_angle_beta 121.981(2) _cell_angle_gamma 90.00 _cell_volume 2700.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1396 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.96 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 2.355 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6018 _exptl_absorpt_correction_T_max 0.8340 _exptl_absorpt_process_details 'Sadabs. (Sheldrick 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 9371 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3106 _reflns_number_gt 2511 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0573P)^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 3106 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Zn1 Zn 0.22158(2) 0.24405(3) 0.21664(3) 0.01340(14) Uani 1 1 d . . . Cl1 Cl 0.21172(6) 0.41837(7) 0.14460(7) 0.0221(2) Uani 1 1 d . . . Cl2 Cl 0.14398(5) 0.23673(7) 0.29252(7) 0.0175(2) Uani 1 1 d . . . S1 S 0.36723(5) 0.18719(8) 0.17978(7) 0.0206(2) Uani 1 1 d . . . N1 N 0.33677(17) 0.2035(2) 0.3442(2) 0.0135(6) Uani 1 1 d . . . N2 N 0.18814(17) 0.1140(2) 0.1033(2) 0.0178(6) Uani 1 1 d . . . N3 N 0.10998(18) 0.0910(3) 0.0385(2) 0.0226(7) Uani 1 1 d . . . N4 N 0.10423(18) 0.0082(3) -0.0313(2) 0.0234(7) Uani 1 1 d . . . C1 C 0.3562(2) 0.1974(3) 0.4511(3) 0.0166(7) Uani 1 1 d . . . H1 H 0.3154 0.2125 0.4672 0.020 Uiso 1 1 calc R . . C2 C 0.4335(2) 0.1701(3) 0.5391(3) 0.0212(8) Uani 1 1 d . . . H2 H 0.4453 0.1668 0.6139 0.025 Uiso 1 1 calc R . . C3 C 0.4926(2) 0.1479(3) 0.5165(3) 0.0214(8) Uani 1 1 d . . . H3 H 0.5462 0.1302 0.5756 0.026 Uiso 1 1 calc R . . C4 C 0.4732(2) 0.1517(3) 0.4061(3) 0.0211(8) Uani 1 1 d . . . H4 H 0.5131 0.1356 0.3884 0.025 Uiso 1 1 calc R . . C5 C 0.3949(2) 0.1793(3) 0.3225(3) 0.0159(7) Uani 1 1 d . . . C6 C 0.3210(2) 0.0468(3) 0.1311(3) 0.0209(8) Uani 1 1 d . . . H6A H 0.3357 0.0164 0.0784 0.025 Uiso 1 1 calc R . . H6B H 0.3438 -0.0060 0.1962 0.025 Uiso 1 1 calc R . . C7 C 0.2317(2) 0.0468(3) 0.0745(3) 0.0179(7) Uani 1 1 d . . . C8 C 0.1775(2) -0.0202(3) -0.0134(3) 0.0214(8) Uani 1 1 d . . . H8 H 0.1889 -0.0751 -0.0533 0.026 Uiso 1 1 calc R . . C9 C 0.0238(2) -0.0313(4) -0.1197(3) 0.0328(10) Uani 1 1 d . . . H9A H -0.0098 -0.0461 -0.0873 0.039 Uiso 1 1 calc R . . H9B H 0.0289 -0.1041 -0.1518 0.039 Uiso 1 1 calc R . . C10 C -0.0166(2) 0.0570(4) -0.2106(4) 0.0391(12) Uani 1 1 d . . . H10A H -0.0082 0.1338 -0.1760 0.047 Uiso 1 1 calc R . . H10B H -0.0756 0.0419 -0.2554 0.047 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 0.0130(2) 0.0167(2) 0.0119(2) 0.00008(15) 0.00744(18) -0.00016(15) Cl1 0.0274(5) 0.0198(4) 0.0239(5) 0.0058(4) 0.0169(4) 0.0027(4) Cl2 0.0185(4) 0.0208(4) 0.0183(4) 0.0039(3) 0.0133(4) 0.0032(3) S1 0.0189(5) 0.0291(5) 0.0183(4) 0.0020(4) 0.0130(4) -0.0015(4) N1 0.0127(14) 0.0141(14) 0.0145(14) 0.0006(11) 0.0078(12) -0.0017(11) N2 0.0167(15) 0.0233(16) 0.0121(14) -0.0031(12) 0.0068(12) -0.0064(12) N3 0.0193(16) 0.0325(18) 0.0194(15) -0.0100(14) 0.0126(14) -0.0078(13) N4 0.0238(17) 0.0297(18) 0.0190(15) -0.0105(14) 0.0128(14) -0.0099(14) C1 0.0163(18) 0.0178(17) 0.0160(17) -0.0035(14) 0.0088(15) -0.0039(14) C2 0.023(2) 0.0242(19) 0.0146(17) -0.0051(15) 0.0084(16) -0.0035(15) C3 0.0112(18) 0.0232(19) 0.0202(18) -0.0031(15) 0.0018(15) -0.0028(14) C4 0.0109(17) 0.028(2) 0.0258(19) -0.0009(16) 0.0109(16) -0.0022(14) C5 0.0142(17) 0.0166(17) 0.0179(17) -0.0022(14) 0.0092(15) -0.0014(13) C6 0.024(2) 0.0237(19) 0.0157(17) -0.0028(15) 0.0108(16) 0.0025(15) C7 0.027(2) 0.0134(17) 0.0187(17) 0.0011(14) 0.0154(16) -0.0004(14) C8 0.027(2) 0.0213(18) 0.0236(19) -0.0009(15) 0.0190(17) 0.0002(16) C9 0.027(2) 0.050(3) 0.033(2) -0.021(2) 0.0227(19) -0.0205(19) C10 0.017(2) 0.035(2) 0.044(3) -0.023(2) 0.0014(19) 0.0038(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 Zn1 N2 2.038(3) . ? Zn1 N1 2.050(3) . ? Zn1 Cl1 2.2312(9) . ? Zn1 Cl2 2.2644(9) . ? S1 C5 1.781(3) . ? S1 C6 1.817(4) . ? N1 C1 1.342(4) . ? N1 C5 1.348(4) . ? N2 N3 1.322(4) . ? N2 C7 1.363(4) . ? N3 N4 1.336(4) . ? N4 C8 1.351(4) . ? N4 C9 1.465(4) . ? C1 C2 1.385(5) . ? C2 C3 1.371(5) . ? C3 C4 1.388(5) . ? C4 C5 1.382(5) . ? C6 C7 1.479(5) . ? C7 C8 1.366(5) . ? C9 C10 1.497(6) . ? C10 C10 1.549(9) 2_554 ? 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 N2 Zn1 N1 105.07(11) . . ? N2 Zn1 Cl1 114.04(8) . . ? N1 Zn1 Cl1 113.43(8) . . ? N2 Zn1 Cl2 108.82(9) . . ? N1 Zn1 Cl2 105.85(8) . . ? Cl1 Zn1 Cl2 109.21(3) . . ? C5 S1 C6 99.83(16) . . ? C1 N1 C5 118.0(3) . . ? C1 N1 Zn1 121.3(2) . . ? C5 N1 Zn1 120.7(2) . . ? N3 N2 C7 110.4(3) . . ? N3 N2 Zn1 117.6(2) . . ? C7 N2 Zn1 131.8(2) . . ? N2 N3 N4 105.7(3) . . ? N3 N4 C8 111.7(3) . . ? N3 N4 C9 119.0(3) . . ? C8 N4 C9 129.0(3) . . ? N1 C1 C2 122.6(3) . . ? C3 C2 C1 119.0(3) . . ? C2 C3 C4 119.2(3) . . ? C5 C4 C3 118.7(3) . . ? N1 C5 C4 122.4(3) . . ? N1 C5 S1 117.0(2) . . ? C4 C5 S1 120.5(3) . . ? C7 C6 S1 114.1(2) . . ? N2 C7 C8 107.0(3) . . ? N2 C7 C6 125.4(3) . . ? C8 C7 C6 127.7(3) . . ? N4 C8 C7 105.2(3) . . ? N4 C9 C10 110.4(3) . . ? C9 C10 C10 112.3(3) . 2_554 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.063 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 938528' ####################################################################### # # 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_c329 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H48 Cl4 N16 S4 Zn2' _chemical_formula_weight 1177.74 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1507(15) _cell_length_b 16.620(2) _cell_length_c 14.0288(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.922(3) _cell_angle_gamma 90.00 _cell_volume 2473.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 906 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.37 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.406 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7027 _exptl_absorpt_correction_T_max 0.8275 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 17259 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5675 _reflns_number_gt 4835 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0490P)^2^+0.4539P] 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 5675 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.84956(2) 1.094491(13) 0.265194(18) 0.01478(8) Uani 1 1 d . . . Cl1 Cl 0.97985(5) 1.18628(3) 0.35688(4) 0.02089(12) Uani 1 1 d . . . Cl2 Cl 0.82471(5) 1.09168(3) 0.10225(4) 0.02094(12) Uani 1 1 d . . . S1 S 1.17923(5) 1.00733(3) 0.30605(4) 0.01804(12) Uani 1 1 d . . . S2 S 0.51571(5) 0.88171(4) 0.96763(4) 0.02219(12) Uani 1 1 d . . . N1 N 0.88876(15) 0.98244(10) 0.32820(12) 0.0158(3) Uani 1 1 d . . . N2 N 0.79168(16) 0.93278(10) 0.31390(13) 0.0177(4) Uani 1 1 d . . . N3 N 0.83971(16) 0.86426(10) 0.35888(13) 0.0172(4) Uani 1 1 d . . . N4 N 1.20350(16) 0.84778(10) 0.33001(13) 0.0188(4) Uani 1 1 d . . . N5 N 0.44373(16) 0.85872(10) 0.62549(13) 0.0176(4) Uani 1 1 d . . . N6 N 0.32365(15) 0.85659(11) 0.62404(13) 0.0183(4) Uani 1 1 d . . . N7 N 0.32145(16) 0.89013(10) 0.70929(13) 0.0165(3) Uani 1 1 d . . . N8 N 0.73308(17) 0.91542(10) 0.92955(14) 0.0193(4) Uani 1 1 d . . . C1 C 0.96536(19) 0.86886(12) 0.40145(16) 0.0186(4) Uani 1 1 d . . . H1 H 1.0203 0.8279 0.4374 0.022 Uiso 1 1 calc R . . C2 C 0.99689(18) 0.94516(12) 0.38181(15) 0.0161(4) Uani 1 1 d . . . C3 C 1.12210(18) 0.98568(12) 0.41123(15) 0.0180(4) Uani 1 1 d . . . H3A H 1.1841 0.9509 0.4593 0.022 Uiso 1 1 calc R . . H3B H 1.1160 1.0367 0.4459 0.022 Uiso 1 1 calc R . . C4 C 1.21919(18) 0.90970(12) 0.27468(16) 0.0159(4) Uani 1 1 d . . . C5 C 1.26467(19) 0.90228(13) 0.19288(16) 0.0189(4) Uani 1 1 d . . . H5 H 1.2738 0.9482 0.1553 0.023 Uiso 1 1 calc R . . C6 C 1.29603(19) 0.82668(13) 0.16802(16) 0.0215(4) Uani 1 1 d . . . H6 H 1.3286 0.8195 0.1135 0.026 Uiso 1 1 calc R . . C7 C 1.27924(19) 0.76125(13) 0.22399(17) 0.0229(5) Uani 1 1 d . . . H7 H 1.2990 0.7084 0.2080 0.027 Uiso 1 1 calc R . . C8 C 1.2334(2) 0.77449(13) 0.30333(17) 0.0220(4) Uani 1 1 d . . . H8 H 1.2222 0.7294 0.3413 0.026 Uiso 1 1 calc R . . C9 C 0.7568(2) 0.79624(12) 0.36317(16) 0.0200(4) Uani 1 1 d . . . H9A H 0.8081 0.7466 0.3808 0.024 Uiso 1 1 calc R . . H9B H 0.6948 0.7882 0.2962 0.024 Uiso 1 1 calc R . . C10 C 0.68671(19) 0.80992(12) 0.43983(15) 0.0176(4) Uani 1 1 d . . . H10A H 0.6572 0.7574 0.4573 0.021 Uiso 1 1 calc R . . H10B H 0.7461 0.8327 0.5016 0.021 Uiso 1 1 calc R . . C11 C 0.57405(19) 0.86610(13) 0.40280(16) 0.0195(4) Uani 1 1 d . . . H11A H 0.5061 0.8378 0.3513 0.023 Uiso 1 1 calc R . . H11B H 0.5992 0.9134 0.3705 0.023 Uiso 1 1 calc R . . C12 C 0.5225(2) 0.89509(12) 0.48568(16) 0.0191(4) Uani 1 1 d . . . H12A H 0.5885 0.9268 0.5347 0.023 Uiso 1 1 calc R . . H12B H 0.4501 0.9313 0.4562 0.023 Uiso 1 1 calc R . . C13 C 0.48036(19) 0.82706(13) 0.54052(15) 0.0182(4) Uani 1 1 d . . . H13A H 0.4079 0.7987 0.4937 0.022 Uiso 1 1 calc R . . H13B H 0.5499 0.7879 0.5652 0.022 Uiso 1 1 calc R . . C14 C 0.51845(19) 0.89328(12) 0.70979(16) 0.0193(4) Uani 1 1 d . . . H14 H 0.6068 0.9018 0.7276 0.023 Uiso 1 1 calc R . . C15 C 0.43976(19) 0.91356(12) 0.76458(16) 0.0173(4) Uani 1 1 d . . . C16 C 0.46595(19) 0.95221(13) 0.86335(16) 0.0198(4) Uani 1 1 d . . . H16A H 0.3890 0.9804 0.8664 0.024 Uiso 1 1 calc R . . H16B H 0.5327 0.9931 0.8708 0.024 Uiso 1 1 calc R . . C17 C 0.6818(2) 0.88267(13) 0.99431(16) 0.0195(4) Uani 1 1 d . . . C18 C 0.7520(2) 0.84902(14) 1.08523(17) 0.0255(5) Uani 1 1 d . . . H18 H 0.7117 0.8253 1.1289 0.031 Uiso 1 1 calc R . . C19 C 0.8821(2) 0.85106(14) 1.11030(17) 0.0285(5) Uani 1 1 d . . . H19 H 0.9328 0.8294 1.1722 0.034 Uiso 1 1 calc R . . C20 C 0.9375(2) 0.88504(14) 1.04414(17) 0.0253(5) Uani 1 1 d . . . H20 H 1.0266 0.8872 1.0596 0.030 Uiso 1 1 calc R . . C21 C 0.8599(2) 0.91559(13) 0.95540(17) 0.0218(5) Uani 1 1 d . . . H21 H 0.8980 0.9382 0.9096 0.026 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 0.01376(12) 0.01532(13) 0.01710(14) 0.00112(8) 0.00747(9) -0.00019(8) Cl1 0.0184(2) 0.0212(3) 0.0233(3) -0.0021(2) 0.00680(19) -0.00414(19) Cl2 0.0261(3) 0.0213(3) 0.0186(3) 0.00109(19) 0.0116(2) 0.00150(19) S1 0.0169(2) 0.0160(2) 0.0237(3) 0.00086(19) 0.0099(2) -0.00114(18) S2 0.0204(3) 0.0305(3) 0.0172(3) -0.0030(2) 0.0081(2) -0.0064(2) N1 0.0163(8) 0.0165(8) 0.0172(9) 0.0002(7) 0.0091(7) -0.0018(6) N2 0.0191(8) 0.0157(8) 0.0215(9) 0.0006(7) 0.0112(7) -0.0014(7) N3 0.0217(9) 0.0144(8) 0.0194(9) 0.0002(7) 0.0122(7) -0.0003(7) N4 0.0179(8) 0.0191(9) 0.0200(9) 0.0014(7) 0.0070(7) -0.0008(7) N5 0.0150(8) 0.0221(9) 0.0174(9) -0.0003(7) 0.0077(7) 0.0001(7) N6 0.0154(8) 0.0229(9) 0.0186(9) -0.0002(7) 0.0079(7) 0.0015(7) N7 0.0161(8) 0.0197(9) 0.0143(8) -0.0013(7) 0.0052(7) -0.0005(6) N8 0.0200(9) 0.0189(9) 0.0195(9) -0.0016(7) 0.0067(7) -0.0025(7) C1 0.0207(10) 0.0195(10) 0.0188(10) 0.0013(8) 0.0110(8) 0.0028(8) C2 0.0167(9) 0.0195(10) 0.0146(10) -0.0011(8) 0.0086(8) 0.0010(8) C3 0.0171(9) 0.0200(10) 0.0185(10) -0.0022(8) 0.0080(8) 0.0002(8) C4 0.0117(9) 0.0184(10) 0.0173(10) -0.0003(8) 0.0041(8) -0.0001(7) C5 0.0156(9) 0.0238(11) 0.0170(11) 0.0034(8) 0.0047(8) 0.0006(8) C6 0.0164(10) 0.0296(12) 0.0190(11) -0.0010(9) 0.0061(8) 0.0016(8) C7 0.0192(10) 0.0191(10) 0.0304(12) -0.0059(9) 0.0076(9) 0.0012(8) C8 0.0214(10) 0.0183(10) 0.0270(12) 0.0023(9) 0.0087(9) -0.0008(8) C9 0.0253(11) 0.0144(10) 0.0259(11) -0.0020(8) 0.0159(9) -0.0033(8) C10 0.0198(10) 0.0169(10) 0.0190(10) 0.0013(8) 0.0104(8) -0.0014(8) C11 0.0173(10) 0.0239(11) 0.0184(10) 0.0030(8) 0.0067(8) -0.0015(8) C12 0.0179(10) 0.0193(10) 0.0218(11) 0.0027(8) 0.0088(8) 0.0013(8) C13 0.0191(10) 0.0202(10) 0.0175(10) -0.0025(8) 0.0091(8) 0.0000(8) C14 0.0156(10) 0.0208(10) 0.0226(11) -0.0021(8) 0.0077(8) -0.0010(8) C15 0.0151(9) 0.0175(10) 0.0195(11) 0.0017(8) 0.0054(8) -0.0003(7) C16 0.0160(9) 0.0202(10) 0.0248(11) -0.0021(9) 0.0086(8) -0.0007(8) C17 0.0222(10) 0.0203(10) 0.0163(10) -0.0066(8) 0.0066(8) -0.0030(8) C18 0.0311(12) 0.0267(12) 0.0204(11) 0.0022(9) 0.0104(9) 0.0004(9) C19 0.0333(13) 0.0286(12) 0.0199(12) 0.0030(9) 0.0026(9) 0.0060(10) C20 0.0208(11) 0.0257(11) 0.0270(12) -0.0034(9) 0.0037(9) 0.0015(9) C21 0.0208(10) 0.0204(11) 0.0249(12) -0.0002(8) 0.0081(9) -0.0009(8) _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 N1 2.0501(17) . ? Zn1 N7 2.0615(17) 3_676 ? Zn1 Cl2 2.2169(6) . ? Zn1 Cl1 2.2231(6) . ? S1 C4 1.774(2) . ? S1 C3 1.814(2) . ? S2 C17 1.773(2) . ? S2 C16 1.822(2) . ? N1 N2 1.326(2) . ? N1 C2 1.358(3) . ? N2 N3 1.332(2) . ? N3 C1 1.346(3) . ? N3 C9 1.473(3) . ? N4 C4 1.333(3) . ? N4 C8 1.346(3) . ? N5 N6 1.333(2) . ? N5 C14 1.348(3) . ? N5 C13 1.471(2) . ? N6 N7 1.327(2) . ? N7 C15 1.365(3) . ? N7 Zn1 2.0615(17) 3_676 ? N8 C17 1.330(3) . ? N8 C21 1.347(3) . ? C1 C2 1.366(3) . ? C2 C3 1.489(3) . ? C4 C5 1.396(3) . ? C5 C6 1.378(3) . ? C6 C7 1.387(3) . ? C7 C8 1.378(3) . ? C9 C10 1.529(3) . ? C10 C11 1.523(3) . ? C11 C12 1.525(3) . ? C12 C13 1.521(3) . ? C14 C15 1.374(3) . ? C15 C16 1.473(3) . ? C17 C18 1.392(3) . ? C18 C19 1.384(3) . ? C19 C20 1.384(3) . ? C20 C21 1.376(3) . ? 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 N1 Zn1 N7 97.10(7) . 3_676 ? N1 Zn1 Cl2 111.58(5) . . ? N7 Zn1 Cl2 110.66(5) 3_676 . ? N1 Zn1 Cl1 111.05(5) . . ? N7 Zn1 Cl1 106.81(5) 3_676 . ? Cl2 Zn1 Cl1 117.59(2) . . ? C4 S1 C3 101.43(10) . . ? C17 S2 C16 101.76(10) . . ? N2 N1 C2 110.12(16) . . ? N2 N1 Zn1 116.38(12) . . ? C2 N1 Zn1 133.49(14) . . ? N1 N2 N3 105.66(16) . . ? N2 N3 C1 111.94(17) . . ? N2 N3 C9 120.65(17) . . ? C1 N3 C9 127.31(18) . . ? C4 N4 C8 116.67(19) . . ? N6 N5 C14 111.80(17) . . ? N6 N5 C13 120.41(16) . . ? C14 N5 C13 127.78(17) . . ? N7 N6 N5 105.80(16) . . ? N6 N7 C15 110.45(17) . . ? N6 N7 Zn1 118.91(12) . 3_676 ? C15 N7 Zn1 130.52(14) . 3_676 ? C17 N8 C21 116.96(19) . . ? N3 C1 C2 105.11(18) . . ? N1 C2 C1 107.17(17) . . ? N1 C2 C3 122.94(18) . . ? C1 C2 C3 129.88(19) . . ? C2 C3 S1 113.46(14) . . ? N4 C4 C5 123.84(19) . . ? N4 C4 S1 118.30(16) . . ? C5 C4 S1 117.87(16) . . ? C6 C5 C4 118.3(2) . . ? C5 C6 C7 118.9(2) . . ? C8 C7 C6 118.7(2) . . ? N4 C8 C7 123.7(2) . . ? N3 C9 C10 112.19(16) . . ? C11 C10 C9 113.46(17) . . ? C10 C11 C12 113.48(17) . . ? C13 C12 C11 113.48(17) . . ? N5 C13 C12 110.49(17) . . ? N5 C14 C15 105.46(18) . . ? N7 C15 C14 106.49(18) . . ? N7 C15 C16 122.42(18) . . ? C14 C15 C16 131.09(19) . . ? C15 C16 S2 113.46(15) . . ? N8 C17 C18 123.5(2) . . ? N8 C17 S2 120.03(16) . . ? C18 C17 S2 116.51(17) . . ? C19 C18 C17 118.2(2) . . ? C20 C19 C18 119.3(2) . . ? C21 C20 C19 118.1(2) . . ? N8 C21 C20 124.0(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.578 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 938529' ####################################################################### # # 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_c158 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 Cl2 N5 S Zn' _chemical_formula_weight 419.62 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.1365(10) _cell_length_b 13.0198(15) _cell_length_c 13.8696(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.449(2) _cell_angle_gamma 90.00 _cell_volume 1648.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3021 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.62 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.945 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6201 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11495 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3776 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0477P)^2^+0.3830P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3776 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Zn1 Zn 0.32835(3) 0.14427(2) 0.17624(2) 0.01610(10) Uani 1 1 d . . . Cl1 Cl 0.30640(8) 0.06255(5) 0.03543(5) 0.03055(18) Uani 1 1 d . . . Cl2 Cl 0.24240(7) 0.05598(5) 0.29967(5) 0.02473(16) Uani 1 1 d . . . S1 S -0.02373(7) 0.19021(5) -0.00906(5) 0.01971(15) Uani 1 1 d . . . N1 N 0.2283(2) 0.28545(16) 0.17088(15) 0.0170(4) Uani 1 1 d . . . N2 N 0.2294(2) 0.33740(16) 0.25198(16) 0.0187(5) Uani 1 1 d . . . N3 N 0.1399(2) 0.41750(15) 0.23479(15) 0.0147(4) Uani 1 1 d . . . N4 N 0.4517(2) 0.66732(16) 0.30182(15) 0.0157(4) Uani 1 1 d . . . N5 N -0.1749(2) 0.36700(17) -0.01647(17) 0.0220(5) Uani 1 1 d . . . C1 C 0.0809(3) 0.41561(18) 0.14392(18) 0.0161(5) Uani 1 1 d . . . H1 H 0.0154 0.4624 0.1155 0.019 Uiso 1 1 calc R . . C2 C 0.1386(3) 0.32984(19) 0.10257(19) 0.0170(5) Uani 1 1 d . . . C3 C 0.1198(3) 0.49507(19) 0.31056(18) 0.0170(5) Uani 1 1 d . . . H3A H 0.1456 0.4652 0.3731 0.020 Uiso 1 1 calc R . . H3B H 0.0174 0.5149 0.3103 0.020 Uiso 1 1 calc R . . C4 C 0.3636(3) 0.58509(18) 0.31180(17) 0.0152(5) Uani 1 1 d . . . H4 H 0.4058 0.5227 0.3302 0.018 Uiso 1 1 calc R . . C5 C 0.2128(3) 0.58950(19) 0.29583(17) 0.0155(5) Uani 1 1 d . . . C6 C 0.1513(3) 0.6830(2) 0.26922(18) 0.0181(5) Uani 1 1 d . . . H6 H 0.0509 0.6883 0.2562 0.022 Uiso 1 1 calc R . . C7 C 0.2402(3) 0.76840(19) 0.26215(19) 0.0202(5) Uani 1 1 d . . . H7 H 0.2002 0.8324 0.2469 0.024 Uiso 1 1 calc R . . C8 C 0.3893(3) 0.75679(19) 0.27812(18) 0.0197(5) Uani 1 1 d . . . H8 H 0.4490 0.8141 0.2721 0.024 Uiso 1 1 calc R . . C9 C 0.1159(3) 0.2890(2) 0.00221(19) 0.0196(5) Uani 1 1 d . . . H9A H 0.2078 0.2611 -0.0186 0.024 Uiso 1 1 calc R . . H9B H 0.0887 0.3454 -0.0406 0.024 Uiso 1 1 calc R . . C10 C -0.1853(3) 0.2652(2) -0.01724(17) 0.0185(5) Uani 1 1 d . . . C11 C -0.3176(3) 0.2115(2) -0.02750(19) 0.0237(6) Uani 1 1 d . . . H11 H -0.3196 0.1401 -0.0254 0.028 Uiso 1 1 calc R . . C12 C -0.4449(3) 0.2674(2) -0.0408(2) 0.0298(7) Uani 1 1 d . . . H12 H -0.5348 0.2343 -0.0486 0.036 Uiso 1 1 calc R . . C13 C -0.4373(3) 0.3732(2) -0.0422(2) 0.0308(7) Uani 1 1 d . . . H13 H -0.5213 0.4127 -0.0524 0.037 Uiso 1 1 calc R . . C14 C -0.3024(3) 0.4188(2) -0.0283(2) 0.0280(6) Uani 1 1 d . . . H14 H -0.2987 0.4902 -0.0268 0.034 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 0.01270(16) 0.01307(16) 0.02221(18) -0.00151(11) -0.00297(12) 0.00256(10) Cl1 0.0350(4) 0.0248(4) 0.0309(4) -0.0124(3) -0.0094(3) 0.0081(3) Cl2 0.0201(3) 0.0243(3) 0.0296(4) 0.0040(3) -0.0005(3) -0.0054(2) S1 0.0197(3) 0.0174(3) 0.0219(3) -0.0041(2) -0.0021(2) 0.0021(2) N1 0.0145(10) 0.0160(10) 0.0201(11) -0.0002(8) -0.0026(8) 0.0024(8) N2 0.0169(11) 0.0143(10) 0.0244(12) -0.0013(9) -0.0035(9) 0.0014(8) N3 0.0123(10) 0.0115(10) 0.0202(10) 0.0002(8) -0.0001(8) -0.0003(7) N4 0.0159(11) 0.0155(10) 0.0156(10) -0.0009(8) 0.0001(8) 0.0020(8) N5 0.0198(12) 0.0218(12) 0.0243(12) 0.0011(9) 0.0002(9) 0.0037(9) C1 0.0138(12) 0.0155(12) 0.0187(12) 0.0016(10) -0.0030(9) -0.0010(9) C2 0.0127(12) 0.0146(12) 0.0237(13) 0.0019(10) 0.0009(10) -0.0016(9) C3 0.0138(12) 0.0172(13) 0.0200(13) -0.0042(10) 0.0010(10) -0.0003(9) C4 0.0147(12) 0.0147(12) 0.0160(12) 0.0008(9) -0.0013(9) -0.0005(9) C5 0.0182(13) 0.0154(12) 0.0128(11) -0.0036(9) -0.0013(9) 0.0004(9) C6 0.0182(13) 0.0184(13) 0.0176(12) -0.0021(10) 0.0010(10) 0.0051(10) C7 0.0249(14) 0.0155(12) 0.0202(13) 0.0022(10) 0.0016(11) 0.0041(10) C8 0.0225(13) 0.0155(12) 0.0212(13) 0.0007(10) 0.0018(10) -0.0050(10) C9 0.0159(13) 0.0215(13) 0.0214(13) -0.0010(10) 0.0008(10) 0.0016(10) C10 0.0201(13) 0.0248(14) 0.0105(12) 0.0011(10) -0.0005(9) 0.0024(10) C11 0.0250(15) 0.0244(14) 0.0216(14) -0.0009(11) 0.0014(11) -0.0024(11) C12 0.0196(14) 0.0423(18) 0.0275(15) -0.0039(13) 0.0008(12) -0.0059(12) C13 0.0204(14) 0.0393(18) 0.0325(16) 0.0016(13) 0.0001(12) 0.0080(12) C14 0.0245(15) 0.0253(15) 0.0345(16) 0.0040(12) 0.0041(12) 0.0045(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 Zn1 N4 2.042(2) 2_645 ? Zn1 N1 2.053(2) . ? Zn1 Cl1 2.2256(8) . ? Zn1 Cl2 2.2324(7) . ? S1 C10 1.769(3) . ? S1 C9 1.814(3) . ? N1 N2 1.312(3) . ? N1 C2 1.355(3) . ? N2 N3 1.341(3) . ? N3 C1 1.350(3) . ? N3 C3 1.475(3) . ? N4 C8 1.332(3) . ? N4 C4 1.350(3) . ? N4 Zn1 2.042(2) 2_655 ? N5 C10 1.329(3) . ? N5 C14 1.350(4) . ? C1 C2 1.371(3) . ? C1 H1 0.9300 . ? C2 C9 1.496(4) . ? C3 C5 1.513(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C6 C7 1.383(4) . ? C6 H6 0.9300 . ? C7 C8 1.379(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.398(4) . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.379(4) . ? C12 H12 0.9300 . ? C13 C14 1.374(4) . ? C13 H13 0.9300 . ? C14 H14 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 N4 Zn1 N1 107.92(8) 2_645 . ? N4 Zn1 Cl1 104.61(6) 2_645 . ? N1 Zn1 Cl1 111.90(6) . . ? N4 Zn1 Cl2 109.73(6) 2_645 . ? N1 Zn1 Cl2 108.55(6) . . ? Cl1 Zn1 Cl2 113.91(3) . . ? C10 S1 C9 101.31(12) . . ? N2 N1 C2 111.2(2) . . ? N2 N1 Zn1 116.32(16) . . ? C2 N1 Zn1 131.46(17) . . ? N1 N2 N3 105.44(19) . . ? N2 N3 C1 111.6(2) . . ? N2 N3 C3 120.0(2) . . ? C1 N3 C3 128.4(2) . . ? C8 N4 C4 117.9(2) . . ? C8 N4 Zn1 125.02(17) . 2_655 ? C4 N4 Zn1 117.10(17) . 2_655 ? C10 N5 C14 115.9(2) . . ? N3 C1 C2 105.1(2) . . ? N3 C1 H1 127.5 . . ? C2 C1 H1 127.5 . . ? N1 C2 C1 106.7(2) . . ? N1 C2 C9 123.7(2) . . ? C1 C2 C9 129.7(2) . . ? N3 C3 C5 111.87(19) . . ? N3 C3 H3A 109.2 . . ? C5 C3 H3A 109.2 . . ? N3 C3 H3B 109.2 . . ? C5 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N4 C4 C5 122.9(2) . . ? N4 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C6 C5 C4 117.9(2) . . ? C6 C5 C3 121.8(2) . . ? C4 C5 C3 120.3(2) . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 118.6(2) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? N4 C8 C7 123.0(2) . . ? N4 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? C2 C9 S1 113.64(18) . . ? C2 C9 H9A 108.8 . . ? S1 C9 H9A 108.8 . . ? C2 C9 H9B 108.8 . . ? S1 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N5 C10 C11 124.1(2) . . ? N5 C10 S1 119.4(2) . . ? C11 C10 S1 116.5(2) . . ? C12 C11 C10 118.0(3) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C11 C12 C13 119.1(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 118.4(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? N5 C14 C13 124.4(3) . . ? N5 C14 H14 117.8 . . ? C13 C14 H14 117.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.747 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 938530' ####################################################################### # # 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_9571 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Cl4 N10 S2 Zn2' _chemical_formula_weight 839.25 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' S S 0.1246 0.1234 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9397(5) _cell_length_b 17.7137(9) _cell_length_c 10.9396(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.9140(10) _cell_angle_gamma 90.00 _cell_volume 1701.01(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6905 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.51 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.885 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3521 _exptl_absorpt_correction_T_max 0.7043 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 11963 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3905 _reflns_number_gt 3603 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0304P)^2^+1.1292P] 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 3905 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Zn1 Zn 0.23274(2) -0.002044(10) 0.790934(17) 0.01529(7) Uani 1 1 d . . . Cl1 Cl 0.18277(5) -0.12354(2) 0.80995(4) 0.02128(10) Uani 1 1 d . . . Cl2 Cl 0.10619(5) 0.08194(2) 0.88294(4) 0.01988(10) Uani 1 1 d . . . S1 S 0.41909(5) 0.19764(2) 0.80337(4) 0.02110(10) Uani 1 1 d . . . N1 N 0.46491(17) 0.00936(8) 0.83388(13) 0.0156(3) Uani 1 1 d . . . N2 N 0.54360(16) -0.04628(8) 0.79546(13) 0.0164(3) Uani 1 1 d . . . N3 N 0.68930(16) -0.02600(8) 0.82676(13) 0.0150(3) Uani 1 1 d . . . N4 N 0.80085(17) -0.02141(9) 0.39582(13) 0.0182(3) Uani 1 1 d . . . N5 N 0.71571(18) 0.20978(9) 0.79532(15) 0.0243(3) Uani 1 1 d . . . C1 C 0.56077(19) 0.06489(9) 0.88767(15) 0.0156(3) Uani 1 1 d . . . C2 C 0.70644(19) 0.04179(9) 0.88378(15) 0.0158(3) Uani 1 1 d . . . H2 H 0.7988 0.0678 0.9145 0.019 Uiso 1 1 calc R . . C3 C 0.5063(2) 0.13721(9) 0.93196(15) 0.0181(3) Uani 1 1 d . . . H3A H 0.5933 0.1641 0.9831 0.022 Uiso 1 1 calc R . . H3B H 0.4310 0.1265 0.9854 0.022 Uiso 1 1 calc R . . C4 C 0.5753(2) 0.21171(9) 0.72686(17) 0.0197(3) Uani 1 1 d . . . C5 C 0.5448(2) 0.22442(11) 0.59878(18) 0.0266(4) Uani 1 1 d . . . H5 H 0.4430 0.2263 0.5536 0.032 Uiso 1 1 calc R . . C6 C 0.6668(3) 0.23421(12) 0.53930(19) 0.0318(4) Uani 1 1 d . . . H6 H 0.6503 0.2432 0.4522 0.038 Uiso 1 1 calc R . . C7 C 0.8136(2) 0.23079(11) 0.6084(2) 0.0322(5) Uani 1 1 d . . . H7 H 0.8994 0.2365 0.5696 0.039 Uiso 1 1 calc R . . C8 C 0.8319(2) 0.21889(11) 0.7347(2) 0.0291(4) Uani 1 1 d . . . H8 H 0.9327 0.2170 0.7818 0.035 Uiso 1 1 calc R . . C9 C 0.80481(19) -0.07096(10) 0.78136(15) 0.0174(3) Uani 1 1 d . . . H9A H 0.7834 -0.1253 0.7899 0.021 Uiso 1 1 calc R . . H9B H 0.9065 -0.0600 0.8320 0.021 Uiso 1 1 calc R . . C10 C 0.7591(3) 0.03080(11) 0.47113(17) 0.0280(4) Uani 1 1 d . . . H10 H 0.7280 0.0791 0.4378 0.034 Uiso 1 1 calc R . . C11 C 0.7595(3) 0.01729(11) 0.59541(18) 0.0281(4) Uani 1 1 d . . . H11 H 0.7289 0.0558 0.6460 0.034 Uiso 1 1 calc R . . C12 C 0.80462(18) -0.05270(10) 0.64613(15) 0.0164(3) Uani 1 1 d . . . C13 C 0.8506(2) -0.10613(10) 0.56865(16) 0.0228(4) Uani 1 1 d . . . H13 H 0.8846 -0.1544 0.6001 0.027 Uiso 1 1 calc R . . C14 C 0.8467(2) -0.08843(11) 0.44483(16) 0.0233(4) Uani 1 1 d . . . H14 H 0.8779 -0.1256 0.3924 0.028 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 0.01349(11) 0.01870(11) 0.01390(11) 0.00017(7) 0.00319(7) 0.00084(7) Cl1 0.0187(2) 0.0188(2) 0.0249(2) -0.00058(15) 0.00056(15) -0.00225(15) Cl2 0.01772(19) 0.0224(2) 0.0205(2) -0.00078(15) 0.00621(15) 0.00340(15) S1 0.0196(2) 0.0212(2) 0.0232(2) 0.00570(16) 0.00587(16) 0.00493(16) N1 0.0168(7) 0.0156(7) 0.0148(6) 0.0017(5) 0.0043(5) 0.0017(5) N2 0.0155(6) 0.0179(7) 0.0165(7) 0.0011(5) 0.0045(5) 0.0016(5) N3 0.0143(6) 0.0185(7) 0.0125(6) 0.0026(5) 0.0035(5) 0.0012(5) N4 0.0179(7) 0.0226(7) 0.0142(7) -0.0010(6) 0.0032(5) 0.0006(6) N5 0.0226(8) 0.0209(8) 0.0291(8) 0.0041(6) 0.0045(6) 0.0003(6) C1 0.0182(8) 0.0178(8) 0.0111(7) 0.0027(6) 0.0036(6) 0.0004(6) C2 0.0164(8) 0.0185(8) 0.0123(7) 0.0014(6) 0.0025(6) -0.0010(6) C3 0.0213(8) 0.0184(8) 0.0149(7) 0.0006(6) 0.0045(6) 0.0013(7) C4 0.0217(8) 0.0137(8) 0.0248(9) 0.0023(6) 0.0074(7) 0.0015(6) C5 0.0287(10) 0.0261(10) 0.0250(9) 0.0043(7) 0.0054(7) 0.0041(8) C6 0.0419(12) 0.0280(10) 0.0284(10) 0.0103(8) 0.0145(9) 0.0067(9) C7 0.0316(10) 0.0233(10) 0.0466(12) 0.0118(9) 0.0202(9) 0.0057(8) C8 0.0210(9) 0.0234(9) 0.0433(12) 0.0087(8) 0.0072(8) 0.0006(7) C9 0.0170(8) 0.0202(8) 0.0161(8) 0.0018(6) 0.0057(6) 0.0056(6) C10 0.0449(12) 0.0200(9) 0.0208(9) 0.0031(7) 0.0105(8) 0.0080(8) C11 0.0436(12) 0.0227(9) 0.0209(9) -0.0005(7) 0.0132(8) 0.0080(8) C12 0.0132(7) 0.0212(8) 0.0150(8) 0.0005(6) 0.0034(6) -0.0002(6) C13 0.0273(9) 0.0214(9) 0.0194(8) 0.0018(7) 0.0036(7) 0.0091(7) C14 0.0272(9) 0.0243(9) 0.0185(8) -0.0025(7) 0.0047(7) 0.0074(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.0494(15) . ? Zn1 N4 2.0504(14) 3_656 ? Zn1 Cl1 2.2158(5) . ? Zn1 Cl2 2.2220(4) . ? S1 C4 1.7766(18) . ? S1 C3 1.8215(17) . ? N1 N2 1.3246(19) . ? N1 C1 1.363(2) . ? N2 N3 1.3319(19) . ? N3 C2 1.349(2) . ? N3 C9 1.463(2) . ? N4 C14 1.335(2) . ? N4 C10 1.338(2) . ? N4 Zn1 2.0504(14) 3_656 ? N5 C4 1.335(2) . ? N5 C8 1.344(2) . ? C1 C2 1.373(2) . ? C1 C3 1.484(2) . ? C4 C5 1.394(3) . ? C5 C6 1.383(3) . ? C6 C7 1.386(3) . ? C7 C8 1.376(3) . ? C9 C12 1.514(2) . ? C10 C11 1.380(3) . ? C11 C12 1.387(3) . ? C12 C13 1.384(2) . ? C13 C14 1.384(2) . ? 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 N1 Zn1 N4 99.17(6) . 3_656 ? N1 Zn1 Cl1 106.71(4) . . ? N4 Zn1 Cl1 107.23(4) 3_656 . ? N1 Zn1 Cl2 114.24(4) . . ? N4 Zn1 Cl2 108.94(4) 3_656 . ? Cl1 Zn1 Cl2 118.608(18) . . ? C4 S1 C3 100.74(8) . . ? N2 N1 C1 110.23(14) . . ? N2 N1 Zn1 115.44(11) . . ? C1 N1 Zn1 134.17(11) . . ? N1 N2 N3 105.67(13) . . ? N2 N3 C2 112.27(14) . . ? N2 N3 C9 118.98(14) . . ? C2 N3 C9 128.02(14) . . ? C14 N4 C10 117.89(15) . . ? C14 N4 Zn1 123.80(12) . 3_656 ? C10 N4 Zn1 117.92(12) . 3_656 ? C4 N5 C8 116.91(17) . . ? N1 C1 C2 107.10(14) . . ? N1 C1 C3 123.08(15) . . ? C2 C1 C3 129.71(16) . . ? N3 C2 C1 104.73(14) . . ? C1 C3 S1 111.96(11) . . ? N5 C4 C5 123.54(17) . . ? N5 C4 S1 118.15(13) . . ? C5 C4 S1 118.32(14) . . ? C6 C5 C4 118.13(19) . . ? C5 C6 C7 119.15(19) . . ? C8 C7 C6 118.37(18) . . ? N5 C8 C7 123.87(19) . . ? N3 C9 C12 110.18(13) . . ? N4 C10 C11 122.54(17) . . ? C10 C11 C12 119.70(17) . . ? C13 C12 C11 117.66(16) . . ? C13 C12 C9 120.45(15) . . ? C11 C12 C9 121.89(15) . . ? C12 C13 C14 119.26(16) . . ? N4 C14 C13 122.93(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.507 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 938531'