# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yao-Yu Wang' _publ_contact_author_address ; Xian 710069 ; _publ_contact_author_email wyaoyu@nwu.edu.cn loop_ _publ_author_name 'Yao-Yu Wang.' 'Lei Hou.' 'Wen-Juan Shi.' 'Bo Liu.' 'Qizhen Shi.' # Attachment '- cif.cif' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 775861' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 Cu5 N9 S4' _chemical_formula_weight 916.46 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 Cc 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' _cell_length_a 16.824(3) _cell_length_b 13.646(2) _cell_length_c 15.090(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.192(3) _cell_angle_gamma 90.00 _cell_volume 3230.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 23.20 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 3.533 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5688 _exptl_absorpt_correction_T_max 0.7189 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8691 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4985 _reflns_number_gt 4387 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.35(2) _refine_ls_number_reflns 4985 _refine_ls_number_parameters 407 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.54963(6) 0.14877(7) 0.12035(6) 0.0398(2) Uani 1 1 d . . . Cu2 Cu 0.46774(7) 0.20025(7) 0.22937(9) 0.0547(3) Uani 1 1 d . . . Cu3 Cu 0.25634(6) 0.23713(8) -0.07464(8) 0.0455(3) Uani 1 1 d . . . Cu4 Cu 1.34834(6) -0.11553(7) 0.25945(7) 0.0432(3) Uani 1 1 d . . . Cu5 Cu -0.54068(6) 0.44796(7) -0.22373(7) 0.0440(3) Uani 1 1 d . . . S1 S 0.79317(14) -0.0256(2) -0.09952(17) 0.0587(7) Uani 1 1 d . . . S2 S 0.96286(13) 0.05545(17) 0.02044(18) 0.0542(6) Uani 1 1 d . . . S3 S 0.01991(15) 0.4204(2) 0.15144(16) 0.0547(6) Uani 1 1 d . . . S4 S -0.14528(14) 0.32577(17) 0.03837(17) 0.0500(6) Uani 1 1 d . . . N1 N 0.6280(4) 0.0995(5) 0.0540(4) 0.0365(15) Uani 1 1 d . . . N2 N 1.2288(4) -0.0612(5) 0.1835(4) 0.0387(16) Uani 1 1 d . . . N3 N 0.1831(4) 0.2647(6) 0.0127(5) 0.0447(17) Uani 1 1 d . . . N4 N -0.4120(4) 0.4126(5) -0.1535(5) 0.0459(18) Uani 1 1 d . . . N5 N 0.3679(5) 0.1935(5) -0.0054(5) 0.0481(18) Uani 1 1 d . . . N6 N 0.6702(4) 0.2282(6) 0.3070(5) 0.0490(18) Uani 1 1 d . . . N7 N 1.4085(4) 0.0087(6) 0.2840(5) 0.0488(18) Uani 1 1 d . . . N8 N -0.5487(5) 0.6622(5) -0.2683(5) 0.0463(17) Uani 1 1 d . . . N9 N -0.5944(4) 0.3257(5) -0.2233(5) 0.0441(17) Uani 1 1 d . . . C1 C 0.7118(5) 0.0923(6) 0.0978(6) 0.0383(19) Uani 1 1 d . . . H1 H 0.7351 0.1146 0.1601 0.046 Uiso 1 1 calc R . . C2 C 0.7663(4) 0.0547(6) 0.0583(5) 0.0358(18) Uani 1 1 d . . . H2 H 0.8245 0.0516 0.0935 0.043 Uiso 1 1 calc R . . C3 C 0.7352(5) 0.0219(6) -0.0330(6) 0.0377(18) Uani 1 1 d . . . C4 C 0.6455(5) 0.0275(6) -0.0814(5) 0.0387(19) Uani 1 1 d . . . H4 H 0.6207 0.0050 -0.1435 0.046 Uiso 1 1 calc R . . C5 C 0.5969(5) 0.0660(6) -0.0361(5) 0.041(2) Uani 1 1 d . . . H5 H 0.5384 0.0696 -0.0690 0.049 Uiso 1 1 calc R . . C6 C 0.8961(5) -0.0530(6) -0.0124(6) 0.043(2) Uani 1 1 d . . . H6A H 0.9239 -0.1020 -0.0377 0.052 Uiso 1 1 calc R . . H6B H 0.8891 -0.0801 0.0438 0.052 Uiso 1 1 calc R . . C7 C 1.0635(5) 0.0057(6) 0.0836(6) 0.038(2) Uani 1 1 d . . . C8 C 1.1264(5) 0.0689(6) 0.1343(6) 0.043(2) Uani 1 1 d . . . H8 H 1.1151 0.1353 0.1365 0.052 Uiso 1 1 calc R . . C9 C 1.2083(5) 0.0319(6) 0.1829(6) 0.046(2) Uani 1 1 d . . . H9 H 1.2508 0.0757 0.2167 0.055 Uiso 1 1 calc R . . C10 C 1.1674(5) -0.1219(6) 0.1327(6) 0.044(2) Uani 1 1 d . . . H10A H 1.1804 -0.1879 0.1311 0.053 Uiso 1 1 calc R . . C11 C 1.0856(6) -0.0916(6) 0.0825(7) 0.049(2) Uani 1 1 d . . . H11 H 1.0450 -0.1367 0.0476 0.059 Uiso 1 1 calc R . . C12 C 0.0983(5) 0.2682(6) -0.0298(6) 0.046(2) Uani 1 1 d . . . H12 H 0.0739 0.2385 -0.0889 0.055 Uiso 1 1 calc R . . C13 C 0.0455(5) 0.3124(6) 0.0082(5) 0.040(2) Uani 1 1 d . . . H13 H -0.0131 0.3124 -0.0250 0.048 Uiso 1 1 calc R . . C14 C 0.0789(5) 0.3574(6) 0.0958(6) 0.0377(19) Uani 1 1 d . . . C15 C 0.1665(5) 0.3509(7) 0.1432(6) 0.048(2) Uani 1 1 d . . . H15 H 0.1917 0.3772 0.2038 0.058 Uiso 1 1 calc R . . C16 C 0.2165(5) 0.3045(7) 0.0991(6) 0.047(2) Uani 1 1 d . . . H16 H 0.2752 0.3012 0.1312 0.056 Uiso 1 1 calc R . . C17 C -0.0822(5) 0.4359(6) 0.0604(6) 0.044(2) Uani 1 1 d . . . H17A H -0.0747 0.4558 0.0022 0.053 Uiso 1 1 calc R . . H17B H -0.1125 0.4879 0.0786 0.053 Uiso 1 1 calc R . . C18 C -0.2444(5) 0.3660(6) -0.0398(6) 0.040(2) Uani 1 1 d . . . C19 C -0.3051(5) 0.2936(6) -0.0815(7) 0.051(2) Uani 1 1 d . . . H19 H -0.2900 0.2278 -0.0725 0.061 Uiso 1 1 calc R . . C20 C -0.3849(6) 0.3191(6) -0.1342(7) 0.054(2) Uani 1 1 d . . . H20 H -0.4244 0.2692 -0.1593 0.065 Uiso 1 1 calc R . . C21 C -0.3533(6) 0.4791(7) -0.1177(7) 0.055(3) Uani 1 1 d . . . H21 H -0.3694 0.5441 -0.1320 0.067 Uiso 1 1 calc R . . C22 C -0.2697(5) 0.4619(6) -0.0605(7) 0.048(2) Uani 1 1 d . . . H22 H -0.2316 0.5133 -0.0367 0.058 Uiso 1 1 calc R . . C23 C 0.4355(5) 0.1723(5) 0.0399(5) 0.0290(16) Uani 1 1 d . . . C24 C 0.6174(5) 0.1946(6) 0.2426(6) 0.0373(18) Uani 1 1 d . . . C25 C 1.4340(5) 0.0821(6) 0.2694(6) 0.0405(19) Uani 1 1 d . . . C26 C -0.5501(5) 0.5803(6) -0.2535(5) 0.0358(18) Uani 1 1 d . . . C27 C -0.6182(5) 0.2468(6) -0.2267(5) 0.0385(19) 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 0.0236(5) 0.0489(6) 0.0393(5) -0.0055(5) 0.0023(4) 0.0013(4) Cu2 0.0613(7) 0.0301(6) 0.0664(7) -0.0024(5) 0.0156(6) -0.0038(5) Cu3 0.0251(5) 0.0516(7) 0.0483(6) 0.0045(5) -0.0006(4) 0.0070(5) Cu4 0.0396(6) 0.0319(5) 0.0554(7) 0.0077(5) 0.0140(5) 0.0082(5) Cu5 0.0430(6) 0.0301(5) 0.0501(6) 0.0047(5) 0.0061(5) -0.0038(5) S1 0.0337(12) 0.095(2) 0.0442(14) -0.0201(13) 0.0107(11) 0.0043(13) S2 0.0271(11) 0.0430(13) 0.0832(18) 0.0119(12) 0.0087(11) 0.0027(10) S3 0.0392(13) 0.0757(17) 0.0429(14) -0.0168(12) 0.0073(10) 0.0028(12) S4 0.0321(11) 0.0443(13) 0.0674(15) 0.0149(11) 0.0106(11) 0.0018(10) N1 0.027(3) 0.039(4) 0.039(4) 0.000(3) 0.006(3) 0.009(3) N2 0.032(4) 0.029(4) 0.046(4) 0.003(3) 0.004(3) 0.006(3) N3 0.026(4) 0.061(5) 0.042(4) -0.003(3) 0.008(3) -0.003(3) N4 0.037(4) 0.032(4) 0.061(5) 0.009(3) 0.008(4) -0.009(3) N5 0.047(5) 0.052(5) 0.045(4) 0.000(3) 0.015(4) 0.001(4) N6 0.024(4) 0.073(5) 0.045(4) -0.005(4) 0.007(3) -0.007(4) N7 0.039(4) 0.047(5) 0.053(5) 0.007(4) 0.008(4) -0.001(4) N8 0.044(4) 0.035(4) 0.054(4) 0.003(3) 0.011(3) -0.002(3) N9 0.034(4) 0.039(4) 0.056(5) 0.005(3) 0.011(3) -0.005(3) C1 0.028(4) 0.045(5) 0.031(4) -0.005(4) -0.002(3) 0.000(4) C2 0.017(4) 0.049(5) 0.033(4) 0.002(3) -0.002(3) 0.001(3) C3 0.028(4) 0.040(5) 0.044(5) 0.003(4) 0.012(4) -0.005(4) C4 0.037(5) 0.046(5) 0.026(4) -0.002(3) 0.004(4) -0.004(4) C5 0.023(4) 0.057(6) 0.031(5) -0.001(4) -0.006(3) 0.003(4) C6 0.033(4) 0.046(5) 0.048(5) -0.015(4) 0.011(4) -0.004(4) C7 0.032(4) 0.040(5) 0.046(5) 0.014(4) 0.018(4) 0.007(4) C8 0.030(4) 0.031(4) 0.063(6) 0.000(4) 0.008(4) 0.004(4) C9 0.038(5) 0.041(5) 0.050(5) 0.002(4) 0.006(4) -0.001(4) C10 0.040(5) 0.027(4) 0.068(6) 0.008(4) 0.024(5) 0.011(4) C11 0.041(5) 0.031(5) 0.070(6) 0.002(4) 0.014(5) -0.008(4) C12 0.030(5) 0.064(6) 0.035(5) -0.009(4) 0.002(4) -0.006(4) C13 0.027(4) 0.056(5) 0.034(5) -0.007(4) 0.007(4) -0.007(4) C14 0.025(4) 0.039(5) 0.046(5) 0.000(4) 0.009(4) -0.005(4) C15 0.034(5) 0.059(6) 0.041(5) -0.005(4) 0.001(4) -0.008(4) C16 0.026(4) 0.058(6) 0.048(5) 0.013(4) 0.002(4) -0.005(4) C17 0.036(5) 0.049(5) 0.047(5) -0.007(4) 0.015(4) 0.001(4) C18 0.030(4) 0.033(5) 0.055(5) 0.010(4) 0.014(4) 0.005(4) C19 0.040(5) 0.028(5) 0.076(7) 0.013(4) 0.009(5) 0.003(4) C20 0.042(6) 0.035(5) 0.080(7) 0.002(4) 0.017(5) -0.013(4) C21 0.049(6) 0.028(5) 0.077(7) 0.009(4) 0.009(5) -0.004(4) C22 0.028(5) 0.040(5) 0.067(6) 0.006(4) 0.006(4) -0.007(4) C23 0.018(4) 0.028(4) 0.030(4) 0.007(3) -0.005(3) 0.011(3) C24 0.021(4) 0.044(5) 0.040(5) -0.001(4) 0.002(3) -0.003(3) C25 0.031(4) 0.039(5) 0.048(5) -0.006(4) 0.010(4) 0.000(4) C26 0.030(4) 0.033(4) 0.042(5) 0.001(3) 0.009(4) -0.007(3) C27 0.034(4) 0.045(5) 0.036(5) 0.002(4) 0.011(4) 0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C24 1.890(8) . ? Cu1 C23 1.892(7) . ? Cu1 N1 2.036(6) . ? Cu1 Cu2 2.5955(15) . ? Cu2 C25 1.880(9) 1_455 ? Cu2 N8 1.899(7) 2_665 ? Cu2 C24 2.455(8) . ? Cu3 N5 1.885(7) . ? Cu3 N6 1.909(7) 4_454 ? Cu3 N3 2.138(7) . ? Cu4 C27 1.866(9) 2_755 ? Cu4 N7 1.940(8) . ? Cu4 N2 2.060(6) . ? Cu5 C26 1.853(8) . ? Cu5 N9 1.899(7) . ? Cu5 N4 2.093(7) . ? S1 C3 1.757(8) . ? S1 C6 1.794(8) . ? S2 C7 1.751(8) . ? S2 C6 1.816(8) . ? S3 C14 1.741(8) . ? S3 C17 1.782(8) . ? S4 C18 1.747(8) . ? S4 C17 1.801(8) . ? N1 C1 1.327(9) . ? N1 C5 1.349(9) . ? N2 C9 1.315(10) . ? N2 C10 1.330(10) . ? N3 C16 1.335(10) . ? N3 C12 1.337(10) . ? N4 C21 1.306(11) . ? N4 C20 1.351(11) . ? N5 C23 1.132(8) . ? N6 C24 1.149(9) . ? N6 Cu3 1.909(7) 4 ? N7 C25 1.142(10) . ? N8 C26 1.142(9) . ? N8 Cu2 1.899(7) 2_464 ? N9 C27 1.143(10) . ? C1 C2 1.361(10) . ? C1 H1 0.9300 . ? C2 C3 1.361(11) . ? C2 H2 0.9300 . ? C3 C4 1.420(11) . ? C4 C5 1.346(11) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.366(12) . ? C7 C11 1.380(12) . ? C8 C9 1.400(11) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.373(12) . ? C10 H10A 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.360(11) . ? C12 H12 0.9300 . ? C13 C14 1.380(10) . ? C13 H13 0.9300 . ? C14 C15 1.389(11) . ? C15 C16 1.398(12) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C22 1.376(11) . ? C18 C19 1.396(11) . ? C19 C20 1.337(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.379(12) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C25 Cu2 1.880(9) 1_655 ? C27 Cu4 1.866(9) 2_354 ? 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 C24 Cu1 C23 133.2(3) . . ? C24 Cu1 N1 108.6(3) . . ? C23 Cu1 N1 115.3(3) . . ? C24 Cu1 Cu2 64.1(2) . . ? C23 Cu1 Cu2 73.3(2) . . ? N1 Cu1 Cu2 170.86(18) . . ? C25 Cu2 N8 141.1(3) 1_455 2_665 ? C25 Cu2 C24 111.5(3) 1_455 . ? N8 Cu2 C24 100.5(3) 2_665 . ? C25 Cu2 Cu1 105.2(2) 1_455 . ? N8 Cu2 Cu1 113.2(2) 2_665 . ? C24 Cu2 Cu1 43.85(19) . . ? N5 Cu3 N6 149.8(3) . 4_454 ? N5 Cu3 N3 113.2(3) . . ? N6 Cu3 N3 97.0(3) 4_454 . ? C27 Cu4 N7 134.5(3) 2_755 . ? C27 Cu4 N2 127.0(3) 2_755 . ? N7 Cu4 N2 97.4(3) . . ? C26 Cu5 N9 149.1(3) . . ? C26 Cu5 N4 109.2(3) . . ? N9 Cu5 N4 101.7(3) . . ? C3 S1 C6 104.3(4) . . ? C7 S2 C6 102.3(4) . . ? C14 S3 C17 104.2(4) . . ? C18 S4 C17 102.6(4) . . ? C1 N1 C5 115.6(7) . . ? C1 N1 Cu1 122.7(6) . . ? C5 N1 Cu1 121.6(5) . . ? C9 N2 C10 116.8(7) . . ? C9 N2 Cu4 123.5(6) . . ? C10 N2 Cu4 119.7(5) . . ? C16 N3 C12 116.9(7) . . ? C16 N3 Cu3 122.8(5) . . ? C12 N3 Cu3 117.6(6) . . ? C21 N4 C20 114.9(7) . . ? C21 N4 Cu5 122.6(6) . . ? C20 N4 Cu5 122.2(6) . . ? C23 N5 Cu3 175.6(7) . . ? C24 N6 Cu3 169.7(7) . 4 ? C25 N7 Cu4 159.3(7) . . ? C26 N8 Cu2 169.8(7) . 2_464 ? C27 N9 Cu5 170.6(7) . . ? N1 C1 C2 124.9(7) . . ? N1 C1 H1 117.5 . . ? C2 C1 H1 117.5 . . ? C1 C2 C3 119.6(7) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 116.8(7) . . ? C2 C3 S1 127.6(6) . . ? C4 C3 S1 115.7(6) . . ? C5 C4 C3 119.2(7) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 N1 123.9(7) . . ? C4 C5 H5 118.0 . . ? N1 C5 H5 118.0 . . ? S1 C6 S2 111.6(5) . . ? S1 C6 H6A 109.3 . . ? S2 C6 H6A 109.3 . . ? S1 C6 H6B 109.3 . . ? S2 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C11 117.1(7) . . ? C8 C7 S2 117.5(6) . . ? C11 C7 S2 125.4(7) . . ? C7 C8 C9 118.9(8) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? N2 C9 C8 123.9(8) . . ? N2 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? N2 C10 C11 123.0(8) . . ? N2 C10 H10A 118.5 . . ? C11 C10 H10A 118.5 . . ? C10 C11 C7 120.3(8) . . ? C10 C11 H11 119.9 . . ? C7 C11 H11 119.9 . . ? N3 C12 C13 124.1(8) . . ? N3 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 120.0(7) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 117.0(7) . . ? C13 C14 S3 125.2(6) . . ? C15 C14 S3 117.8(6) . . ? C14 C15 C16 119.5(8) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N3 C16 C15 122.4(8) . . ? N3 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? S3 C17 S4 112.5(5) . . ? S3 C17 H17A 109.1 . . ? S4 C17 H17A 109.1 . . ? S3 C17 H17B 109.1 . . ? S4 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C22 C18 C19 117.0(8) . . ? C22 C18 S4 126.4(7) . . ? C19 C18 S4 116.5(6) . . ? C20 C19 C18 119.9(8) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 N4 124.2(8) . . ? C19 C20 H20 117.9 . . ? N4 C20 H20 117.9 . . ? N4 C21 C22 126.0(8) . . ? N4 C21 H21 117.0 . . ? C22 C21 H21 117.0 . . ? C18 C22 C21 117.8(8) . . ? C18 C22 H22 121.1 . . ? C21 C22 H22 121.1 . . ? N5 C23 Cu1 174.7(7) . . ? N6 C24 Cu1 165.2(7) . . ? N6 C24 Cu2 120.8(6) . . ? Cu1 C24 Cu2 72.0(2) . . ? N7 C25 Cu2 172.9(8) . 1_655 ? N8 C26 Cu5 174.4(7) . . ? N9 C27 Cu4 174.4(7) . 2_354 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.615 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.096 data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 775862' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 Cu3 N5 S2' _chemical_formula_weight 517.04 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 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 14.474(3) _cell_length_b 6.9490(12) _cell_length_c 17.450(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.255(4) _cell_angle_gamma 90.00 _cell_volume 1744.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1212 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 26.79 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 3.871 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6133 _exptl_absorpt_correction_T_max 0.7734 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4598 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1710 _reflns_number_gt 1451 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+3.8321P] 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 1710 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.61252(6) 1.03735(15) 0.22940(6) 0.0291(3) Uani 1 1 d . . . Cu2 Cu 1.0000 1.21396(11) 0.7500 0.0383(2) Uani 1 2 d S . . Cu1 Cu 0.94203(4) 0.83829(8) 0.50882(3) 0.0402(2) Uani 1 1 d . . . N1 N 0.8230(2) 0.9053(5) 0.4360(2) 0.0325(8) Uani 1 1 d . . . N2 N 0.9691(3) 1.0941(5) 0.6499(2) 0.0416(9) Uani 1 1 d . . . C1 C 0.7691(3) 0.7674(6) 0.4032(2) 0.0308(9) Uani 1 1 d . . . H1 H 0.7774 0.6429 0.4222 0.037 Uiso 1 1 calc R . . C2 C 0.7015(3) 0.7977(6) 0.3426(2) 0.0304(9) Uani 1 1 d . . . H2 H 0.6657 0.6957 0.3214 0.036 Uiso 1 1 calc R . . C3 C 0.6875(2) 0.9819(6) 0.3137(2) 0.0272(8) Uani 1 1 d . . . C4 C 0.7405(3) 1.1289(6) 0.3491(3) 0.0377(10) Uani 1 1 d . . . H4 H 0.7315 1.2555 0.3326 0.045 Uiso 1 1 calc R . . C5 C 0.8066(3) 1.0852(7) 0.4090(3) 0.0406(11) Uani 1 1 d . . . H5 H 0.8421 1.1852 0.4322 0.049 Uiso 1 1 calc R . . C6 C 0.5338(3) 0.8349(5) 0.2200(2) 0.0300(9) Uani 1 1 d . . . H6 H 0.4993 0.8374 0.1691 0.036 Uiso 1 1 calc R . . H6A H 0.5696 0.7167 0.2244 0.036 Uiso 1 1 calc R . . C7 C 0.9594(3) 1.0178(6) 0.5931(2) 0.0269(8) Uani 1 1 d . . . C8 C 0.9863(3) 0.5678(6) 0.5013(2) 0.0392(10) Uani 0.50 1 d P . . N3 N 0.9863(3) 0.5678(6) 0.5013(2) 0.0392(10) Uani 0.50 1 d P . . 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 0.0267(5) 0.0305(6) 0.0291(5) 0.0023(4) -0.0020(4) 0.0008(4) Cu2 0.0535(5) 0.0279(4) 0.0312(4) 0.000 -0.0061(3) 0.000 Cu1 0.0415(3) 0.0418(4) 0.0339(3) -0.0048(2) -0.0116(2) 0.0038(2) N1 0.0279(17) 0.035(2) 0.0333(19) -0.0028(15) -0.0051(14) 0.0002(15) N2 0.043(2) 0.0250(19) 0.056(3) 0.0116(19) 0.0038(19) -0.0020(16) C1 0.031(2) 0.031(2) 0.030(2) 0.0000(17) 0.0035(17) 0.0006(17) C2 0.0263(19) 0.028(2) 0.036(2) -0.0004(18) -0.0035(17) -0.0065(16) C3 0.0188(17) 0.031(2) 0.031(2) -0.0002(17) -0.0009(15) -0.0002(15) C4 0.033(2) 0.025(2) 0.051(3) 0.0016(19) -0.010(2) -0.0018(17) C5 0.034(2) 0.033(2) 0.052(3) -0.011(2) -0.013(2) -0.0017(19) C6 0.031(2) 0.025(2) 0.032(2) -0.0029(17) -0.0111(17) 0.0026(16) C7 0.032(2) 0.028(2) 0.0183(19) 0.0008(17) -0.0084(16) -0.0009(16) C8 0.046(3) 0.049(3) 0.0198(17) -0.001(2) -0.0082(17) -0.015(2) N3 0.046(3) 0.049(3) 0.0198(17) -0.001(2) -0.0082(17) -0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.773(4) . ? S1 C6 1.806(4) . ? S1 Cu2 2.4281(11) 7_676 ? Cu2 N2 1.942(4) . ? Cu2 N2 1.942(4) 2_756 ? Cu2 S1 2.4281(12) 8_576 ? Cu2 S1 2.4281(11) 7_676 ? Cu1 C7 1.924(4) . ? Cu1 C8 1.995(4) . ? Cu1 N1 2.078(3) . ? Cu1 Cu1 2.8416(12) 5_776 ? N1 C1 1.327(5) . ? N1 C5 1.348(6) . ? N2 C7 1.119(5) . ? C1 C2 1.376(6) . ? C1 H1 0.9300 . ? C2 C3 1.383(6) . ? C2 H2 0.9300 . ? C3 C4 1.383(6) . ? C4 C5 1.372(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C6 1.510(8) 2_655 ? C6 H6 0.9700 . ? C6 H6A 0.9700 . ? C8 N3 1.026(8) 5_766 ? C8 C8 1.026(8) 5_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C6 103.25(19) . . ? C3 S1 Cu2 113.07(13) . 7_676 ? C6 S1 Cu2 98.13(13) . 7_676 ? N2 Cu2 N2 129.2(2) . 2_756 ? N2 Cu2 S1 105.33(11) . 8_576 ? N2 Cu2 S1 110.24(11) 2_756 8_576 ? N2 Cu2 S1 110.24(11) . 7_676 ? N2 Cu2 S1 105.33(11) 2_756 7_676 ? S1 Cu2 S1 89.25(5) 8_576 7_676 ? C7 Cu1 C8 130.18(17) . . ? C7 Cu1 N1 110.63(15) . . ? C8 Cu1 N1 114.93(16) . . ? C7 Cu1 Cu1 62.66(12) . 5_776 ? C8 Cu1 Cu1 122.72(13) . 5_776 ? N1 Cu1 Cu1 102.50(10) . 5_776 ? C1 N1 C5 116.5(4) . . ? C1 N1 Cu1 120.8(3) . . ? C5 N1 Cu1 121.6(3) . . ? C7 N2 Cu2 173.5(4) . . ? N1 C1 C2 123.9(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 118.0(4) . . ? C2 C3 S1 123.8(3) . . ? C4 C3 S1 118.0(3) . . ? C5 C4 C3 118.9(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 123.6(4) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C6 C6 S1 112.8(2) 2_655 . ? C6 C6 H6 109.0 2_655 . ? S1 C6 H6 109.0 . . ? C6 C6 H6A 109.0 2_655 . ? S1 C6 H6A 109.0 . . ? H6 C6 H6A 107.8 . . ? N2 C7 Cu1 167.8(4) . . ? N3 C8 C8 0.0(5) 5_766 5_766 ? N3 C8 Cu1 175.9(6) 5_766 . ? C8 C8 Cu1 175.9(6) 5_766 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.619 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.100