# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef 'A.cif' _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_address ; Department of chemistry Zhengzhou University Zhengzhou 450052 China ; _publ_contact_author_email niuyy@zzu.edu.cn _publ_contact_author_fax '86 371 67767627' _publ_contact_author_phone '86 371 67767627' _publ_contact_author_name 'Professor. Niu, Yun-Yin' loop_ _publ_author_name 'Yong-Zhen Qiao' 'Jun-Ming Yue' 'Xiu-Cun Liu' 'Yunyin Niu' data_a _database_code_depnum_ccdc_archive 'CCDC 818364' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 Cu N3 S2' _chemical_formula_weight 286.85 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.3892(4) _cell_length_b 10.6944(4) _cell_length_c 20.3245(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2258.18(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 3.0007 _cell_measurement_theta_max 26.3146 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 2.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5688 _exptl_absorpt_correction_T_max 0.6721 _exptl_absorpt_process_details sadabs _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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6262 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2311 _reflns_number_gt 1190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.0277P)^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 2311 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0611 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 0.761 _refine_ls_restrained_S_all 0.761 _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 Cu1 Cu 0.14779(4) 0.12048(3) 0.08694(2) 0.05489(15) Uani 1 1 d . . . S1 S -0.09778(7) 0.10805(8) 0.10689(4) 0.0483(2) Uani 1 1 d . . . S2 S 0.24373(8) 0.00895(8) 0.17748(4) 0.0542(2) Uani 1 1 d . . . N1 N 0.5625(2) 0.1852(3) 0.13828(13) 0.0443(7) Uani 1 1 d . . . N2 N -0.1602(2) -0.0294(2) -0.00644(13) 0.0459(7) Uani 1 1 d . . . N3 N 0.3106(2) -0.2101(2) 0.11206(14) 0.0488(7) Uani 1 1 d . . . C1 C 0.5895(3) 0.0620(3) 0.13922(16) 0.0450(8) Uani 1 1 d . . . H1 H 0.6253 0.0266 0.1768 0.054 Uiso 1 1 calc R . . C2 C 0.5651(2) -0.0110(3) 0.08618(15) 0.0413(7) Uani 1 1 d . . . H2 H 0.5844 -0.0958 0.0880 0.050 Uiso 1 1 calc R . . C3 C 0.5118(2) 0.0383(3) 0.02934(15) 0.0356(7) Uani 1 1 d . . . C4 C 0.4826(3) 0.1656(3) 0.02996(17) 0.0514(9) Uani 1 1 d . . . H4 H 0.4456 0.2030 -0.0068 0.062 Uiso 1 1 calc R . . C5 C 0.5084(3) 0.2349(3) 0.08446(18) 0.0539(9) Uani 1 1 d . . . H5 H 0.4878 0.3195 0.0844 0.065 Uiso 1 1 calc R . . C6 C 0.5912(3) 0.2637(3) 0.19697(16) 0.0617(9) Uani 1 1 d . . . H6A H 0.6716 0.2365 0.2166 0.074 Uiso 1 1 calc R . . H6B H 0.6013 0.3502 0.1835 0.074 Uiso 1 1 calc R . . C7 C 0.4870(3) 0.2546(4) 0.24598(16) 0.0681(10) Uani 1 1 d . . . H7A H 0.4082 0.2849 0.2271 0.102 Uiso 1 1 calc R . . H7B H 0.5085 0.3039 0.2839 0.102 Uiso 1 1 calc R . . H7C H 0.4762 0.1688 0.2589 0.102 Uiso 1 1 calc R . . C8 C -0.1365(2) 0.0289(3) 0.03979(15) 0.0372(7) Uani 1 1 d . . . C9 C 0.2818(3) -0.1207(3) 0.13889(15) 0.0374(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0708(3) 0.0383(2) 0.0556(3) -0.0135(2) -0.0048(2) 0.0007(2) S1 0.0441(4) 0.0561(5) 0.0446(5) -0.0151(5) 0.0070(3) -0.0071(4) S2 0.0723(5) 0.0414(5) 0.0488(5) -0.0096(5) -0.0014(4) 0.0134(4) N1 0.0415(15) 0.0502(19) 0.0412(17) -0.0031(17) 0.0085(13) -0.0074(14) N2 0.0400(15) 0.0495(17) 0.0480(16) -0.0139(16) 0.0045(12) -0.0018(13) N3 0.0520(16) 0.0298(14) 0.0646(19) -0.0028(15) 0.0000(13) 0.0057(13) C1 0.0440(18) 0.048(2) 0.043(2) 0.007(2) 0.0015(15) -0.0004(17) C2 0.0387(17) 0.0400(18) 0.045(2) 0.004(2) 0.0067(15) 0.0040(15) C3 0.0333(16) 0.037(2) 0.0359(18) 0.0030(16) 0.0129(15) 0.0012(15) C4 0.075(2) 0.0424(19) 0.036(2) 0.0026(19) 0.0007(16) 0.0029(19) C5 0.070(2) 0.0345(18) 0.057(2) 0.001(2) 0.0088(19) 0.0007(18) C6 0.069(2) 0.057(2) 0.059(2) -0.013(2) -0.0045(18) -0.015(2) C7 0.075(2) 0.086(3) 0.043(2) -0.016(2) -0.0058(17) 0.007(2) C8 0.0261(16) 0.0383(18) 0.0472(19) 0.0041(17) 0.0087(14) -0.0026(15) C9 0.0346(17) 0.0324(17) 0.0450(19) 0.0038(19) -0.0027(13) 0.0010(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.908(3) 5 ? Cu1 N3 1.931(3) 8_665 ? Cu1 S2 2.4088(10) . ? Cu1 S1 2.5867(8) . ? S1 C8 1.655(3) . ? S2 C9 1.641(3) . ? N1 C5 1.340(4) . ? N1 C1 1.347(4) . ? N1 C6 1.489(4) . ? N2 C8 1.155(3) . ? N2 Cu1 1.908(3) 5 ? N3 C9 1.141(3) . ? N3 Cu1 1.931(3) 8_655 ? C1 C2 1.355(4) . ? C1 H1 0.9300 . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.395(4) . ? C3 C3 1.467(6) 5_655 ? C4 C5 1.359(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.475(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 N2 Cu1 N3 133.64(11) 5 8_665 ? N2 Cu1 S2 111.98(8) 5 . ? N3 Cu1 S2 99.79(8) 8_665 . ? N2 Cu1 S1 100.08(7) 5 . ? N3 Cu1 S1 103.15(8) 8_665 . ? S2 Cu1 S1 105.25(3) . . ? C8 S1 Cu1 97.85(9) . . ? C9 S2 Cu1 98.80(10) . . ? C5 N1 C1 119.1(3) . . ? C5 N1 C6 121.0(3) . . ? C1 N1 C6 119.9(3) . . ? C8 N2 Cu1 163.5(2) . 5 ? C9 N3 Cu1 166.3(3) . 8_655 ? N1 C1 C2 120.9(3) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 121.3(3) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C2 C3 C4 116.8(3) . . ? C2 C3 C3 122.2(3) . 5_655 ? C4 C3 C3 121.0(4) . 5_655 ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 122.1(3) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C7 C6 N1 110.8(2) . . ? C7 C6 H6A 109.5 . . ? N1 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 S1 177.6(3) . . ? N3 C9 S2 178.7(3) . . ? 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 N2 Cu1 S1 C8 -1.22(12) 5 . . . ? N3 Cu1 S1 C8 138.37(13) 8_665 . . . ? S2 Cu1 S1 C8 -117.47(10) . . . . ? N2 Cu1 S2 C9 -3.90(12) 5 . . . ? N3 Cu1 S2 C9 -149.47(13) 8_665 . . . ? S1 Cu1 S2 C9 103.90(10) . . . . ? C5 N1 C1 C2 1.4(4) . . . . ? C6 N1 C1 C2 -179.4(2) . . . . ? N1 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C1 C2 C3 C3 178.1(3) . . . 5_655 ? C2 C3 C4 C5 0.9(4) . . . . ? C3 C3 C4 C5 -178.4(3) 5_655 . . . ? C1 N1 C5 C4 -1.6(4) . . . . ? C6 N1 C5 C4 179.2(3) . . . . ? C3 C4 C5 N1 0.5(4) . . . . ? C5 N1 C6 C7 96.2(3) . . . . ? C1 N1 C6 C7 -83.0(4) . . . . ? Cu1 N2 C8 S1 -55(7) 5 . . . ? Cu1 S1 C8 N2 53(6) . . . . ? Cu1 N3 C9 S2 106(12) 8_655 . . . ? Cu1 S2 C9 N3 105(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.269 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.062 # Attachment 'B.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 818365' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 Ag2 Br2 N6 S3' _chemical_formula_weight 829.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 9.7369(12) _cell_length_b 9.0907(11) _cell_length_c 31.145(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.6590(10) _cell_angle_gamma 90.00 _cell_volume 2755.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4567 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 26.19 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1604 _exptl_absorpt_coefficient_mu 4.571 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3000 _exptl_absorpt_correction_T_max 0.4329 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 12735 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5093 _reflns_number_gt 4020 _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^)+(0.0292P)^2^+1.5887P] 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 5093 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 Ag1 Ag 0.70569(3) 0.51300(4) 0.130156(10) 0.05124(10) Uani 1 1 d . . . Ag2 Ag 0.66056(4) 0.98195(4) 0.021975(11) 0.05736(11) Uani 1 1 d . . . Br1 Br 0.72928(4) 0.75776(4) 0.078002(13) 0.04714(11) Uani 1 1 d . . . Br2 Br 0.42742(4) 1.09308(5) 0.057742(13) 0.05173(12) Uani 1 1 d . . . S1 S 0.80732(12) 0.59207(15) 0.20257(3) 0.0596(3) Uani 1 1 d . . . S2 S 0.45696(11) 0.44806(13) 0.14599(4) 0.0575(3) Uani 1 1 d . . . S3 S 0.87613(11) 1.14063(12) 0.02478(4) 0.0531(3) Uani 1 1 d . . . N1 N 0.3344(3) 0.5611(4) 0.02337(12) 0.0514(9) Uani 1 1 d . . . N2 N 0.5778(3) 0.5891(3) 0.33328(10) 0.0392(7) Uani 1 1 d . . . N3 N 0.9562(3) 0.5287(3) 0.32274(9) 0.0364(7) Uani 1 1 d . . . N4 N 1.0616(4) 0.6965(5) 0.17623(12) 0.0701(11) Uani 1 1 d . . . N5 N 0.4706(5) 0.5026(5) 0.23496(15) 0.0779(13) Uani 1 1 d . . . N6 N 0.8014(3) 1.3398(4) 0.08871(12) 0.0536(9) Uani 1 1 d . . . C1 C 0.3325(5) 0.6680(5) 0.05248(14) 0.0559(11) Uani 1 1 d . . . H1 H 0.4059 0.7331 0.0553 0.067 Uiso 1 1 calc R . . C2 C 0.2218(5) 0.6814(6) 0.07829(15) 0.0688(14) Uani 1 1 d . . . H2 H 0.2190 0.7569 0.0984 0.083 Uiso 1 1 calc R . . C3 C 0.1170(5) 0.5852(7) 0.07457(16) 0.0709(14) Uani 1 1 d . . . H3 H 0.0415 0.5945 0.0920 0.085 Uiso 1 1 calc R . . C4 C 0.1217(5) 0.4760(6) 0.04573(17) 0.0667(13) Uani 1 1 d . . . H4 H 0.0492 0.4096 0.0431 0.080 Uiso 1 1 calc R . . C5 C 0.2316(5) 0.4618(5) 0.02032(16) 0.0642(13) Uani 1 1 d . . . H5 H 0.2361 0.3842 0.0009 0.077 Uiso 1 1 calc R . . C6 C 0.4504(5) 0.5516(5) -0.00916(16) 0.0652(13) Uani 1 1 d . . . H6A H 0.4150 0.5165 -0.0367 0.078 Uiso 1 1 calc R . . H6B H 0.4922 0.6472 -0.0131 0.078 Uiso 1 1 calc R . . C7 C 1.0052(4) 0.3974(4) 0.33594(13) 0.0473(10) Uani 1 1 d . . . H7 H 0.9578 0.3432 0.3561 0.057 Uiso 1 1 calc R . . C8 C 1.1244(4) 0.3431(5) 0.31993(14) 0.0514(10) Uani 1 1 d . . . H8 H 1.1569 0.2514 0.3287 0.062 Uiso 1 1 calc R . . C9 C 1.1954(4) 0.4243(5) 0.29110(13) 0.0482(10) Uani 1 1 d . . . H9 H 1.2783 0.3901 0.2809 0.058 Uiso 1 1 calc R . . C10 C 1.1428(4) 0.5573(5) 0.27735(13) 0.0476(10) Uani 1 1 d . . . H10 H 1.1890 0.6126 0.2572 0.057 Uiso 1 1 calc R . . C11 C 1.0230(4) 0.6075(4) 0.29340(12) 0.0421(9) Uani 1 1 d . . . H11 H 0.9871 0.6970 0.2840 0.051 Uiso 1 1 calc R . . C12 C 0.8277(4) 0.5850(5) 0.34101(13) 0.0475(10) Uani 1 1 d . . . H12A H 0.8265 0.6916 0.3394 0.057 Uiso 1 1 calc R . . H12B H 0.8242 0.5572 0.3710 0.057 Uiso 1 1 calc R . . C13 C 0.7044(4) 0.5238(5) 0.31692(13) 0.0476(10) Uani 1 1 d . . . H13A H 0.7111 0.5455 0.2866 0.057 Uiso 1 1 calc R . . H13B H 0.7017 0.4178 0.3204 0.057 Uiso 1 1 calc R . . C14 C 0.5174(4) 0.5259(4) 0.36659(13) 0.0449(9) Uani 1 1 d . . . H14 H 0.5542 0.4404 0.3786 0.054 Uiso 1 1 calc R . . C15 C 0.4010(4) 0.5869(5) 0.38321(14) 0.0532(11) Uani 1 1 d . . . H15 H 0.3596 0.5429 0.4065 0.064 Uiso 1 1 calc R . . C16 C 0.3469(4) 0.7111(5) 0.36562(16) 0.0578(12) Uani 1 1 d . . . H16 H 0.2676 0.7522 0.3765 0.069 Uiso 1 1 calc R . . C17 C 0.4099(5) 0.7752(5) 0.33189(17) 0.0668(14) Uani 1 1 d . . . H17 H 0.3744 0.8612 0.3198 0.080 Uiso 1 1 calc R . . C18 C 0.5258(5) 0.7124(5) 0.31573(15) 0.0582(11) Uani 1 1 d . . . H18 H 0.5684 0.7557 0.2926 0.070 Uiso 1 1 calc R . . C19 C 0.9573(4) 0.6531(5) 0.18667(12) 0.0453(10) Uani 1 1 d . . . C20 C 0.4646(4) 0.4822(4) 0.19817(17) 0.0515(11) Uani 1 1 d . . . C21 C 0.8290(4) 1.2572(4) 0.06234(13) 0.0401(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0535(2) 0.0552(2) 0.04527(19) -0.00200(15) 0.00549(14) -0.01060(15) Ag2 0.0630(2) 0.0524(2) 0.0565(2) -0.00150(16) -0.00193(17) -0.01034(16) Br1 0.0633(3) 0.0371(2) 0.0410(2) 0.00319(17) 0.00365(18) -0.00502(19) Br2 0.0498(2) 0.0617(3) 0.0438(2) -0.0041(2) 0.00396(19) -0.0034(2) S1 0.0536(6) 0.0884(9) 0.0368(6) -0.0010(6) 0.0029(5) -0.0221(6) S2 0.0423(6) 0.0681(8) 0.0618(7) 0.0020(6) -0.0018(5) -0.0149(5) S3 0.0540(6) 0.0558(7) 0.0499(7) -0.0081(5) 0.0069(5) -0.0107(5) N1 0.0400(19) 0.053(2) 0.062(2) -0.0123(18) 0.0141(17) -0.0113(16) N2 0.0321(16) 0.0442(19) 0.0414(19) -0.0058(15) 0.0009(14) 0.0025(14) N3 0.0335(16) 0.0395(18) 0.0364(17) -0.0049(14) 0.0026(13) 0.0013(13) N4 0.060(3) 0.087(3) 0.063(3) -0.006(2) 0.005(2) -0.022(2) N5 0.076(3) 0.093(3) 0.065(3) -0.003(3) 0.023(2) -0.015(2) N6 0.048(2) 0.052(2) 0.062(2) -0.0020(19) 0.0073(18) -0.0011(17) C1 0.055(3) 0.049(3) 0.063(3) -0.011(2) -0.010(2) -0.009(2) C2 0.076(4) 0.077(3) 0.053(3) -0.019(2) -0.004(3) 0.023(3) C3 0.052(3) 0.107(4) 0.054(3) 0.003(3) 0.017(2) 0.010(3) C4 0.046(3) 0.078(3) 0.076(3) 0.004(3) 0.013(2) -0.020(2) C5 0.052(3) 0.061(3) 0.080(3) -0.028(2) 0.017(2) -0.018(2) C6 0.065(3) 0.064(3) 0.067(3) 0.021(2) -0.008(2) -0.011(2) C7 0.047(2) 0.046(2) 0.050(3) 0.0073(19) 0.0104(19) -0.001(2) C8 0.049(2) 0.043(2) 0.062(3) 0.003(2) 0.005(2) 0.0103(19) C9 0.035(2) 0.057(3) 0.052(3) -0.006(2) 0.0060(19) 0.0046(19) C10 0.041(2) 0.060(3) 0.043(2) 0.0062(19) 0.0049(18) -0.010(2) C11 0.044(2) 0.038(2) 0.044(2) 0.0022(17) -0.0066(18) -0.0032(18) C12 0.039(2) 0.054(2) 0.050(2) -0.014(2) 0.0090(18) 0.0080(19) C13 0.038(2) 0.061(3) 0.044(2) -0.012(2) 0.0080(18) 0.0011(19) C14 0.039(2) 0.043(2) 0.053(3) -0.0011(19) 0.0026(19) 0.0018(18) C15 0.034(2) 0.069(3) 0.057(3) -0.008(2) 0.0091(19) -0.002(2) C16 0.036(2) 0.066(3) 0.071(3) -0.019(2) -0.006(2) 0.011(2) C17 0.060(3) 0.050(3) 0.089(4) 0.002(3) -0.022(3) 0.017(2) C18 0.057(3) 0.059(3) 0.058(3) 0.011(2) -0.001(2) 0.000(2) C19 0.048(2) 0.055(3) 0.033(2) -0.0014(18) -0.0021(19) -0.006(2) C20 0.038(2) 0.045(3) 0.072(3) 0.007(2) 0.012(2) -0.0025(19) C21 0.036(2) 0.040(2) 0.044(2) 0.0109(19) 0.0020(17) -0.0085(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N6 2.255(4) 1_545 ? Ag1 S1 2.5402(11) . ? Ag1 S2 2.5547(11) . ? Ag1 Br1 2.7684(5) . ? Ag2 S3 2.5462(11) . ? Ag2 Br2 2.6907(6) 3_675 ? Ag2 Br2 2.7498(6) . ? Ag2 Br1 2.7529(6) . ? Br2 Ag2 2.6907(6) 3_675 ? S1 C19 1.651(5) . ? S2 C20 1.654(5) . ? S3 C21 1.653(5) . ? N1 C1 1.329(5) . ? N1 C5 1.349(5) . ? N1 C6 1.542(6) . ? N2 C14 1.337(5) . ? N2 C18 1.340(5) . ? N2 C13 1.473(5) . ? N3 C11 1.343(5) . ? N3 C7 1.346(5) . ? N3 C12 1.481(4) . ? N4 C19 1.146(5) . ? N5 C20 1.160(6) . ? N6 C21 1.150(5) . ? N6 Ag1 2.255(4) 1_565 ? C1 C2 1.369(6) . ? C1 H1 0.9300 . ? C2 C3 1.347(7) . ? C2 H2 0.9300 . ? C3 C4 1.341(7) . ? C3 H3 0.9300 . ? C4 C5 1.355(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C6 1.451(9) 3_665 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.368(5) . ? C7 H7 0.9300 . ? C8 C9 1.366(6) . ? C8 H8 0.9300 . ? C9 C10 1.376(6) . ? C9 H9 0.9300 . ? C10 C11 1.362(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.504(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.376(5) . ? C14 H14 0.9300 . ? C15 C16 1.355(6) . ? C15 H15 0.9300 . ? C16 C17 1.362(7) . ? C16 H16 0.9300 . ? C17 C18 1.374(7) . ? C17 H17 0.9300 . ? C18 H18 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 N6 Ag1 S1 123.30(10) 1_545 . ? N6 Ag1 S2 111.04(9) 1_545 . ? S1 Ag1 S2 103.95(4) . . ? N6 Ag1 Br1 100.53(9) 1_545 . ? S1 Ag1 Br1 104.87(3) . . ? S2 Ag1 Br1 113.22(3) . . ? S3 Ag2 Br2 114.54(3) . 3_675 ? S3 Ag2 Br2 117.86(3) . . ? Br2 Ag2 Br2 102.848(17) 3_675 . ? S3 Ag2 Br1 102.28(3) . . ? Br2 Ag2 Br1 117.535(19) 3_675 . ? Br2 Ag2 Br1 101.745(18) . . ? Ag2 Br1 Ag1 160.76(2) . . ? Ag2 Br2 Ag2 77.152(17) 3_675 . ? C19 S1 Ag1 98.86(14) . . ? C20 S2 Ag1 97.50(15) . . ? C21 S3 Ag2 98.15(13) . . ? C1 N1 C5 120.9(4) . . ? C1 N1 C6 120.9(4) . . ? C5 N1 C6 118.2(4) . . ? C14 N2 C18 120.5(4) . . ? C14 N2 C13 119.1(3) . . ? C18 N2 C13 120.4(4) . . ? C11 N3 C7 120.4(3) . . ? C11 N3 C12 120.5(3) . . ? C7 N3 C12 119.0(3) . . ? C21 N6 Ag1 166.8(3) . 1_565 ? N1 C1 C2 119.5(4) . . ? N1 C1 H1 120.3 . . ? C2 C1 H1 120.3 . . ? C3 C2 C1 120.0(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 119.4(4) . . ? N1 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C6 C6 N1 105.7(5) 3_665 . ? C6 C6 H6A 110.6 3_665 . ? N1 C6 H6A 110.6 . . ? C6 C6 H6B 110.6 3_665 . ? N1 C6 H6B 110.6 . . ? H6A C6 H6B 108.7 . . ? N3 C7 C8 120.3(4) . . ? N3 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 119.3(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N3 C11 C10 120.5(4) . . ? N3 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? N3 C12 C13 110.6(3) . . ? N3 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N2 C13 C12 110.1(3) . . ? N2 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? N2 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? N2 C14 C15 120.3(4) . . ? N2 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 119.9(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? N2 C18 C17 120.2(4) . . ? N2 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? N4 C19 S1 178.9(4) . . ? N5 C20 S2 178.4(4) . . ? N6 C21 S3 177.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S3 Ag2 Br1 Ag1 169.72(6) . . . . ? Br2 Ag2 Br1 Ag1 -63.92(6) 3_675 . . . ? Br2 Ag2 Br1 Ag1 47.46(6) . . . . ? N6 Ag1 Br1 Ag2 104.03(11) 1_545 . . . ? S1 Ag1 Br1 Ag2 -127.13(6) . . . . ? S2 Ag1 Br1 Ag2 -14.46(7) . . . . ? S3 Ag2 Br2 Ag2 127.05(4) . . . 3_675 ? Br2 Ag2 Br2 Ag2 0.0 3_675 . . 3_675 ? Br1 Ag2 Br2 Ag2 -122.122(19) . . . 3_675 ? N6 Ag1 S1 C19 60.60(19) 1_545 . . . ? S2 Ag1 S1 C19 -172.12(15) . . . . ? Br1 Ag1 S1 C19 -53.02(16) . . . . ? N6 Ag1 S2 C20 133.67(18) 1_545 . . . ? S1 Ag1 S2 C20 -0.89(16) . . . . ? Br1 Ag1 S2 C20 -114.12(15) . . . . ? Br2 Ag2 S3 C21 137.98(13) 3_675 . . . ? Br2 Ag2 S3 C21 16.79(14) . . . . ? Br1 Ag2 S3 C21 -93.74(14) . . . . ? C5 N1 C1 C2 -3.1(7) . . . . ? C6 N1 C1 C2 174.0(4) . . . . ? N1 C1 C2 C3 1.2(7) . . . . ? C1 C2 C3 C4 0.3(8) . . . . ? C2 C3 C4 C5 0.1(8) . . . . ? C1 N1 C5 C4 3.6(7) . . . . ? C6 N1 C5 C4 -173.7(4) . . . . ? C3 C4 C5 N1 -2.0(8) . . . . ? C1 N1 C6 C6 96.0(6) . . . 3_665 ? C5 N1 C6 C6 -86.8(6) . . . 3_665 ? C11 N3 C7 C8 0.6(6) . . . . ? C12 N3 C7 C8 -179.4(4) . . . . ? N3 C7 C8 C9 1.4(6) . . . . ? C7 C8 C9 C10 -2.5(6) . . . . ? C8 C9 C10 C11 1.5(6) . . . . ? C7 N3 C11 C10 -1.6(5) . . . . ? C12 N3 C11 C10 178.5(3) . . . . ? C9 C10 C11 N3 0.5(6) . . . . ? C11 N3 C12 C13 95.3(4) . . . . ? C7 N3 C12 C13 -84.7(4) . . . . ? C14 N2 C13 C12 -87.7(4) . . . . ? C18 N2 C13 C12 90.5(4) . . . . ? N3 C12 C13 N2 -175.8(3) . . . . ? C18 N2 C14 C15 0.1(6) . . . . ? C13 N2 C14 C15 178.3(3) . . . . ? N2 C14 C15 C16 0.3(6) . . . . ? C14 C15 C16 C17 -0.8(6) . . . . ? C15 C16 C17 C18 0.9(7) . . . . ? C14 N2 C18 C17 0.0(6) . . . . ? C13 N2 C18 C17 -178.2(4) . . . . ? C16 C17 C18 N2 -0.5(7) . . . . ? Ag1 S1 C19 N4 163(27) . . . . ? Ag1 S2 C20 N5 -94(15) . . . . ? Ag1 N6 C21 S3 140(7) 1_565 . . . ? Ag2 S3 C21 N6 162(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.754 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.073 # Attachment 't.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 818366' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Cu2 N6 S4' _chemical_formula_weight 657.86 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' Cu Cu 0.3201 1.2651 '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 12.9290(12) _cell_length_b 10.5303(9) _cell_length_c 10.7521(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.796(2) _cell_angle_gamma 90.00 _cell_volume 1456.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5136 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 24.74 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 1.772 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 14351 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2709 _reflns_number_gt 2064 _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^)+(0.0693P)^2^+0.2907P] 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 2709 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 Cu1 Cu 0.13483(4) 0.14827(5) 0.89906(4) 0.0779(2) Uani 1 1 d . . . S1 S 0.17198(7) -0.09905(9) 0.90963(8) 0.0741(3) Uani 1 1 d . . . S2 S 0.27459(7) 0.24033(10) 1.02888(8) 0.0769(3) Uani 1 1 d . . . C1 C 0.1355(2) 0.5619(3) 1.0207(3) 0.0628(8) Uani 1 1 d . . . H1 H 0.1408 0.5828 1.1052 0.075 Uiso 1 1 calc R . . C2 C 0.2171(3) 0.5830(4) 0.9525(4) 0.0801(10) Uani 1 1 d . . . H2 H 0.2771 0.6209 0.9907 0.096 Uiso 1 1 calc R . . C3 C 0.0461(2) 0.5100(3) 0.9650(3) 0.0520(7) Uani 1 1 d . . . C4 C 0.0445(3) 0.4766(4) 0.8400(3) 0.0757(10) Uani 1 1 d . . . H4 H -0.0149 0.4398 0.7992 0.091 Uiso 1 1 calc R . . C5 C 0.1285(3) 0.4971(4) 0.7763(3) 0.0759(10) Uani 1 1 d . . . H5 H 0.1263 0.4732 0.6928 0.091 Uiso 1 1 calc R . . N3 N 0.1734(2) 0.1848(3) 0.7338(2) 0.0707(7) Uani 1 1 d . . . N1 N 0.2128(2) 0.5504(3) 0.8317(3) 0.0742(8) Uani 1 1 d . . . C6 C 0.3010(4) 0.5887(6) 0.7569(5) 0.1198(17) Uani 1 1 d . A . H6A H 0.2807 0.5726 0.6690 0.144 Uiso 1 1 calc R . . H6B H 0.3133 0.6792 0.7670 0.144 Uiso 1 1 calc R . . C7 C 0.3921(4) 0.5246(6) 0.7926(5) 0.1149(15) Uani 1 1 d . . . H7A H 0.3846 0.4358 0.7692 0.138 Uiso 0.56(4) 1 calc PR A 1 H7B H 0.4080 0.5294 0.8826 0.138 Uiso 0.56(4) 1 calc PR A 1 H7C H 0.3739 0.4371 0.8087 0.138 Uiso 0.44(4) 1 d PR A 2 H7D H 0.4196 0.5606 0.8721 0.138 Uiso 0.44(4) 1 d PR A 2 C8 C 0.484(2) 0.588(3) 0.725(4) 0.139(8) Uani 0.56(4) 1 d P A 1 H8 H 0.5071 0.6618 0.7749 0.166 Uiso 0.56(4) 1 calc PR A 1 C9 C 0.4603(17) 0.633(2) 0.593(3) 0.150(7) Uani 0.56(4) 1 d P A 1 H9A H 0.5236 0.6360 0.5538 0.225 Uiso 0.56(4) 1 calc PR A 1 H9B H 0.4301 0.7161 0.5936 0.225 Uiso 0.56(4) 1 calc PR A 1 H9C H 0.4124 0.5755 0.5485 0.225 Uiso 0.56(4) 1 calc PR A 1 C10 C 0.574(3) 0.499(4) 0.729(3) 0.153(9) Uani 0.56(4) 1 d P A 1 H10A H 0.5521 0.4211 0.6877 0.229 Uiso 0.56(4) 1 calc PR A 1 H10B H 0.5983 0.4815 0.8146 0.229 Uiso 0.56(4) 1 calc PR A 1 H10C H 0.6282 0.5370 0.6877 0.229 Uiso 0.56(4) 1 calc PR A 1 C8' C 0.481(2) 0.529(4) 0.708(4) 0.112(8) Uani 0.44(4) 1 d P A 2 H8' H 0.4626 0.4766 0.6338 0.135 Uiso 0.44(4) 1 calc PR A 2 C9' C 0.579(3) 0.474(4) 0.784(4) 0.127(9) Uani 0.44(4) 1 d P A 2 H9D H 0.5920 0.5198 0.8615 0.191 Uiso 0.44(4) 1 calc PR A 2 H9E H 0.6374 0.4820 0.7368 0.191 Uiso 0.44(4) 1 calc PR A 2 H9F H 0.5675 0.3859 0.8019 0.191 Uiso 0.44(4) 1 calc PR A 2 C10' C 0.500(3) 0.663(3) 0.669(4) 0.163(11) Uani 0.44(4) 1 d P A 2 H10D H 0.4451 0.6887 0.6071 0.244 Uiso 0.44(4) 1 calc PR A 2 H10F H 0.5653 0.6675 0.6347 0.244 Uiso 0.44(4) 1 calc PR A 2 H10E H 0.5008 0.7177 0.7404 0.244 Uiso 0.44(4) 1 calc PR A 2 N2 N 0.0047(2) 0.1571(2) 0.9715(3) 0.0658(7) Uani 1 1 d . . . C11 C -0.0670(3) 0.1352(3) 1.0216(3) 0.0556(7) Uani 1 1 d . . . C12 C 0.2151(3) 0.2166(3) 0.6500(3) 0.0608(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0861(4) 0.0993(4) 0.0534(3) 0.0052(2) 0.0318(2) 0.0065(2) S1 0.0644(5) 0.0958(6) 0.0620(6) 0.0049(4) 0.0037(4) 0.0009(4) S2 0.0755(6) 0.0965(7) 0.0632(5) 0.0189(4) 0.0287(4) 0.0024(5) C1 0.0647(19) 0.072(2) 0.0527(17) -0.0039(15) 0.0118(15) -0.0016(15) C2 0.066(2) 0.101(3) 0.074(2) -0.012(2) 0.0135(18) -0.0164(19) C3 0.0557(16) 0.0535(16) 0.0474(15) 0.0055(13) 0.0081(13) 0.0098(13) C4 0.0577(18) 0.118(3) 0.0518(18) -0.0074(18) 0.0088(14) -0.0038(19) C5 0.073(2) 0.107(3) 0.0496(18) -0.0010(18) 0.0132(16) 0.007(2) N3 0.091(2) 0.0786(18) 0.0455(14) 0.0046(13) 0.0231(14) 0.0035(15) N1 0.0665(18) 0.094(2) 0.0657(18) 0.0027(15) 0.0234(14) -0.0030(16) C6 0.091(3) 0.178(5) 0.097(3) 0.011(3) 0.037(3) -0.002(3) C7 0.101(4) 0.135(4) 0.112(4) -0.010(3) 0.032(3) 0.003(3) C8 0.126(12) 0.14(2) 0.158(19) -0.005(16) 0.067(11) -0.002(15) C9 0.114(11) 0.208(16) 0.136(16) -0.013(12) 0.046(10) -0.021(9) C10 0.129(13) 0.179(18) 0.15(2) 0.006(16) 0.029(16) -0.005(11) C8' 0.078(9) 0.13(2) 0.143(14) -0.024(15) 0.058(8) -0.012(12) C9' 0.088(11) 0.16(2) 0.14(2) -0.018(17) 0.040(14) -0.019(12) C10' 0.142(18) 0.19(2) 0.16(3) 0.011(18) 0.042(19) -0.034(16) N2 0.0718(17) 0.0626(16) 0.0664(17) 0.0044(12) 0.0243(14) 0.0084(13) C11 0.0647(19) 0.0526(17) 0.0503(16) 0.0016(12) 0.0097(15) 0.0107(13) C12 0.076(2) 0.0613(18) 0.0467(16) 0.0001(14) 0.0125(15) -0.0005(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.926(3) . ? Cu1 N3 1.932(3) . ? Cu1 S2 2.3757(11) . ? Cu1 S1 2.6486(10) . ? S1 C11 1.655(3) 3_557 ? S2 C12 1.642(3) 4_566 ? C1 C3 1.361(4) . ? C1 C2 1.363(5) . ? C1 H1 0.9300 . ? C2 N1 1.339(5) . ? C2 H2 0.9300 . ? C3 C4 1.387(4) . ? C3 C3 1.489(6) 3_567 ? C4 C5 1.358(5) . ? C4 H4 0.9300 . ? C5 N1 1.315(5) . ? C5 H5 0.9300 . ? N3 C12 1.145(4) . ? N1 C6 1.515(5) . ? C6 C7 1.377(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8' 1.53(3) . ? C7 C8 1.59(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C7 H7D 0.9700 . ? C8 C10 1.49(4) . ? C8 C9 1.49(5) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C8' C10' 1.50(6) . ? C8' C9' 1.55(5) . ? C8' H8' 0.9800 . ? C9' H9D 0.9600 . ? C9' H9E 0.9600 . ? C9' H9F 0.9600 . ? C10' H10D 0.9600 . ? C10' H10F 0.9600 . ? C10' H10E 0.9600 . ? N2 C11 1.141(4) . ? C11 S1 1.655(3) 3_557 ? C12 S2 1.642(3) 4_565 ? 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 Cu1 N3 132.80(13) . . ? N2 Cu1 S2 112.74(9) . . ? N3 Cu1 S2 101.97(10) . . ? N2 Cu1 S1 101.07(8) . . ? N3 Cu1 S1 99.94(9) . . ? S2 Cu1 S1 104.61(4) . . ? C11 S1 Cu1 95.28(10) 3_557 . ? C12 S2 Cu1 100.90(12) 4_566 . ? C3 C1 C2 119.8(3) . . ? C3 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? N1 C2 C1 121.4(3) . . ? N1 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C1 C3 C4 117.2(3) . . ? C1 C3 C3 121.4(3) . 3_567 ? C4 C3 C3 121.3(3) . 3_567 ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? N1 C5 C4 120.5(3) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C12 N3 Cu1 165.3(3) . . ? C5 N1 C2 120.0(3) . . ? C5 N1 C6 120.5(3) . . ? C2 N1 C6 119.1(3) . . ? C7 C6 N1 112.9(4) . . ? C7 C6 H6A 109.0 . . ? N1 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? N1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8' 119.2(16) . . ? C6 C7 C8 108.8(13) . . ? C6 C7 H7A 109.9 . . ? C8' C7 H7A 86.4 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8' C7 H7B 119.6 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C6 C7 H7C 107.4 . . ? C8' C7 H7C 110.2 . . ? C8 C7 H7C 132.9 . . ? H7B C7 H7C 84.4 . . ? C6 C7 H7D 106.3 . . ? C8' C7 H7D 106.3 . . ? C8 C7 H7D 90.9 . . ? H7A C7 H7D 128.6 . . ? H7C C7 H7D 106.7 . . ? C10 C8 C9 108(3) . . ? C10 C8 C7 110(2) . . ? C9 C8 C7 119(3) . . ? C10 C8 H8 106.6 . . ? C9 C8 H8 106.6 . . ? C7 C8 H8 106.6 . . ? C7 C8' C9' 107(3) . . ? C10' C8' H8' 109.5 . . ? C7 C8' H8' 109.5 . . ? C9' C8' H8' 109.5 . . ? C8' C9' H9D 109.5 . . ? C8' C9' H9E 109.5 . . ? H9D C9' H9E 109.5 . . ? C8' C9' H9F 109.5 . . ? H9D C9' H9F 109.5 . . ? H9E C9' H9F 109.5 . . ? C8' C10' H10D 109.5 . . ? C8' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? C8' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? H10F C10' H10E 109.5 . . ? C11 N2 Cu1 164.8(2) . . ? N2 C11 S1 177.8(3) . 3_557 ? N3 C12 S2 179.0(3) . 4_565 ? 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 N2 Cu1 S1 C11 -1.55(14) . . . 3_557 ? N3 Cu1 S1 C11 -139.03(15) . . . 3_557 ? S2 Cu1 S1 C11 115.71(11) . . . 3_557 ? N2 Cu1 S2 C12 1.32(15) . . . 4_566 ? N3 Cu1 S2 C12 148.65(15) . . . 4_566 ? S1 Cu1 S2 C12 -107.61(12) . . . 4_566 ? C3 C1 C2 N1 -2.0(6) . . . . ? C2 C1 C3 C4 2.3(5) . . . . ? C2 C1 C3 C3 -177.6(4) . . . 3_567 ? C1 C3 C4 C5 -1.0(5) . . . . ? C3 C3 C4 C5 178.9(4) 3_567 . . . ? C3 C4 C5 N1 -0.8(6) . . . . ? N2 Cu1 N3 C12 141.6(11) . . . . ? S2 Cu1 N3 C12 4.3(12) . . . . ? S1 Cu1 N3 C12 -103.1(11) . . . . ? C4 C5 N1 C2 1.2(6) . . . . ? C4 C5 N1 C6 -172.1(4) . . . . ? C1 C2 N1 C5 0.2(6) . . . . ? C1 C2 N1 C6 173.6(4) . . . . ? C5 N1 C6 C7 -117.4(5) . . . . ? C2 N1 C6 C7 69.3(6) . . . . ? N1 C6 C7 C8' 166.2(16) . . . . ? N1 C6 C7 C8 -170.7(16) . . . . ? C8 C7 C8' C10' -21(6) . . . . ? C6 C7 C8' C9' 168.2(19) . . . . ? N3 Cu1 N2 C11 127.1(11) . . . . ? S2 Cu1 N2 C11 -98.9(11) . . . . ? S1 Cu1 N2 C11 12.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.570 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.061