Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal SOciety of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prof. Dan Li' _publ_contact_author_email DLI@STU.EDU.CN _publ_author_name 'Dan Li' data_1 _database_code_depnum_ccdc_archive 'CCDC 670247' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Cu I N4 S2' _chemical_formula_weight 426.75 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' I I -0.4742 1.8119 '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 11.7889(7) _cell_length_b 14.2524(9) _cell_length_c 16.3910(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.416(1) _cell_angle_gamma 90.00 _cell_volume 2716.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5009 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.67 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 4.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3152 _exptl_absorpt_correction_T_max 0.6132 _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 'Bruker APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _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 11630 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3193 _reflns_number_gt 2855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0326P)^2^+3.4087P] 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 3193 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 I1 I 0.896282(16) 0.197417(15) 0.582317(12) 0.04206(8) Uani 1 1 d . . . Cu1 Cu 0.67439(3) 0.23758(3) 0.56937(2) 0.04228(11) Uani 1 1 d . . . S1 S 0.72188(8) 0.22144(6) 0.76750(5) 0.04569(19) Uani 1 1 d . . . N1 N 0.6652(2) 0.34638(16) 0.65154(15) 0.0357(5) Uani 1 1 d . . . C1 C 0.6843(2) 0.3361(2) 0.73416(18) 0.0346(6) Uani 1 1 d . . . N2 N 0.6766(2) 0.40261(19) 0.78930(16) 0.0451(6) Uani 1 1 d . . . C3 C 0.6223(3) 0.5055(2) 0.6759(2) 0.0500(8) Uani 1 1 d . . . H3 H 0.6000 0.5649 0.6558 0.060 Uiso 1 1 calc R . . C2 C 0.6449(3) 0.4874(2) 0.7586(2) 0.0513(8) Uani 1 1 d . . . H2 H 0.6379 0.5360 0.7953 0.062 Uiso 1 1 calc R . . C4 C 0.6339(3) 0.4323(2) 0.6237(2) 0.0444(7) Uani 1 1 d . . . H4 H 0.6196 0.4428 0.5669 0.053 Uiso 1 1 calc R . . N3 N 0.5744(2) 0.12381(16) 0.58811(14) 0.0356(5) Uani 1 1 d . . . C8 C 0.6164(3) 0.0360(2) 0.5941(2) 0.0465(7) Uani 1 1 d . . . H8 H 0.6916 0.0260 0.5857 0.056 Uiso 1 1 calc R . . N4 N 0.3959(2) 0.0632(2) 0.6167(2) 0.0535(7) Uani 1 1 d . . . C5 C 0.4646(2) 0.1322(2) 0.59995(18) 0.0378(6) Uani 1 1 d . . . C6 C 0.4427(3) -0.0215(3) 0.6232(3) 0.0643(11) Uani 1 1 d . . . H6 H 0.3982 -0.0716 0.6361 0.077 Uiso 1 1 calc R . . C7 C 0.5528(3) -0.0388(2) 0.6119(3) 0.0616(10) Uani 1 1 d . . . H7 H 0.5832 -0.0991 0.6162 0.074 Uiso 1 1 calc R . . C9 C 0.7259(2) 0.2332(2) 0.87716(18) 0.0408(7) Uani 1 1 d . . . H9A H 0.7735 0.2869 0.8963 0.049 Uiso 1 1 calc R . . H9B H 0.7629 0.1780 0.9041 0.049 Uiso 1 1 calc R . . S2 S 0.41165(7) 0.24749(6) 0.59027(5) 0.04394(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 I1 0.04056(12) 0.04902(13) 0.03834(12) 0.01374(8) 0.01168(8) 0.00880(8) Cu1 0.0480(2) 0.0370(2) 0.0427(2) 0.00197(15) 0.01014(17) 0.00472(16) S1 0.0653(5) 0.0378(4) 0.0364(4) 0.0038(3) 0.0158(4) 0.0090(4) N1 0.0378(12) 0.0322(12) 0.0380(12) -0.0010(10) 0.0089(10) 0.0024(10) C1 0.0317(13) 0.0327(14) 0.0407(15) -0.0030(11) 0.0092(12) -0.0014(11) N2 0.0472(15) 0.0418(14) 0.0462(15) -0.0098(12) 0.0074(12) -0.0004(12) C3 0.0470(18) 0.0290(15) 0.072(2) -0.0010(15) 0.0038(17) 0.0024(14) C2 0.0502(19) 0.0359(17) 0.068(2) -0.0180(16) 0.0099(17) -0.0015(14) C4 0.0467(17) 0.0360(15) 0.0510(18) 0.0056(13) 0.0090(14) 0.0035(13) N3 0.0357(12) 0.0362(12) 0.0356(12) -0.0001(10) 0.0074(10) 0.0031(10) C8 0.0361(15) 0.0397(17) 0.062(2) -0.0025(14) 0.0043(14) 0.0042(13) N4 0.0444(15) 0.0428(15) 0.076(2) 0.0018(14) 0.0174(14) -0.0023(12) C5 0.0380(15) 0.0382(15) 0.0377(15) -0.0015(12) 0.0075(12) 0.0038(12) C6 0.051(2) 0.0415(19) 0.102(3) 0.0037(19) 0.018(2) -0.0043(16) C7 0.052(2) 0.0355(18) 0.096(3) 0.0018(18) 0.009(2) 0.0042(15) C9 0.0353(15) 0.0504(17) 0.0370(15) 0.0022(13) 0.0067(12) -0.0065(13) S2 0.0432(4) 0.0407(4) 0.0512(5) 0.0064(3) 0.0173(4) 0.0085(3) _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 I1 Cu1 2.6521(5) . ? I1 Cu1 2.6564(4) 7_656 ? Cu1 N3 2.057(2) . ? Cu1 N1 2.069(2) . ? Cu1 I1 2.6564(4) 7_656 ? S1 C1 1.757(3) . ? S1 C9 1.798(3) . ? N1 C4 1.338(4) . ? N1 C1 1.344(4) . ? C1 N2 1.323(4) . ? N2 C2 1.339(4) . ? C3 C2 1.363(5) . ? C3 C4 1.370(4) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C4 H4 0.9300 . ? N3 C8 1.343(4) . ? N3 C5 1.345(4) . ? C8 C7 1.363(5) . ? C8 H8 0.9300 . ? N4 C6 1.323(5) . ? N4 C5 1.332(4) . ? C5 S2 1.756(3) . ? C6 C7 1.364(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 S2 1.800(3) 2_656 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? S2 C9 1.800(3) 2_656 ? 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 Cu1 I1 Cu1 72.279(14) . 7_656 ? N3 Cu1 N1 113.66(10) . . ? N3 Cu1 I1 113.56(7) . . ? N1 Cu1 I1 105.43(7) . . ? N3 Cu1 I1 108.36(7) . 7_656 ? N1 Cu1 I1 107.82(7) . 7_656 ? I1 Cu1 I1 107.721(14) . 7_656 ? C1 S1 C9 100.86(15) . . ? C4 N1 C1 115.8(3) . . ? C4 N1 Cu1 120.4(2) . . ? C1 N1 Cu1 123.83(19) . . ? N2 C1 N1 126.3(3) . . ? N2 C1 S1 119.7(2) . . ? N1 C1 S1 114.0(2) . . ? C1 N2 C2 115.9(3) . . ? C2 C3 C4 117.0(3) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? N2 C2 C3 122.8(3) . . ? N2 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? N1 C4 C3 122.3(3) . . ? N1 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C8 N3 C5 115.1(3) . . ? C8 N3 Cu1 122.1(2) . . ? C5 N3 Cu1 122.67(19) . . ? N3 C8 C7 122.4(3) . . ? N3 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C6 N4 C5 115.5(3) . . ? N4 C5 N3 126.6(3) . . ? N4 C5 S2 119.4(2) . . ? N3 C5 S2 114.0(2) . . ? N4 C6 C7 123.2(3) . . ? N4 C6 H6 118.4 . . ? C7 C6 H6 118.4 . . ? C8 C7 C6 117.2(3) . . ? C8 C7 H7 121.4 . . ? C6 C7 H7 121.4 . . ? S1 C9 S2 115.42(16) . 2_656 ? S1 C9 H9A 108.4 . . ? S2 C9 H9A 108.4 2_656 . ? S1 C9 H9B 108.4 . . ? S2 C9 H9B 108.4 2_656 . ? H9A C9 H9B 107.5 . . ? C5 S2 C9 101.05(15) . 2_656 ? 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 Cu1 I1 Cu1 N3 120.01(7) 7_656 . . . ? Cu1 I1 Cu1 N1 -114.93(7) 7_656 . . . ? Cu1 I1 Cu1 I1 0.0 7_656 . . 7_656 ? N3 Cu1 N1 C4 -123.6(2) . . . . ? I1 Cu1 N1 C4 111.4(2) . . . . ? I1 Cu1 N1 C4 -3.5(2) 7_656 . . . ? N3 Cu1 N1 C1 53.4(2) . . . . ? I1 Cu1 N1 C1 -71.6(2) . . . . ? I1 Cu1 N1 C1 173.5(2) 7_656 . . . ? C4 N1 C1 N2 -1.0(4) . . . . ? Cu1 N1 C1 N2 -178.1(2) . . . . ? C4 N1 C1 S1 178.6(2) . . . . ? Cu1 N1 C1 S1 1.5(3) . . . . ? C9 S1 C1 N2 5.1(3) . . . . ? C9 S1 C1 N1 -174.6(2) . . . . ? N1 C1 N2 C2 1.2(5) . . . . ? S1 C1 N2 C2 -178.5(2) . . . . ? C1 N2 C2 C3 -0.5(5) . . . . ? C4 C3 C2 N2 -0.3(5) . . . . ? C1 N1 C4 C3 0.1(4) . . . . ? Cu1 N1 C4 C3 177.4(2) . . . . ? C2 C3 C4 N1 0.5(5) . . . . ? N1 Cu1 N3 C8 -129.7(2) . . . . ? I1 Cu1 N3 C8 -9.2(3) . . . . ? I1 Cu1 N3 C8 110.5(2) 7_656 . . . ? N1 Cu1 N3 C5 46.4(2) . . . . ? I1 Cu1 N3 C5 166.9(2) . . . . ? I1 Cu1 N3 C5 -73.4(2) 7_656 . . . ? C5 N3 C8 C7 -0.8(5) . . . . ? Cu1 N3 C8 C7 175.5(3) . . . . ? C6 N4 C5 N3 1.0(5) . . . . ? C6 N4 C5 S2 -179.8(3) . . . . ? C8 N3 C5 N4 0.1(5) . . . . ? Cu1 N3 C5 N4 -176.3(3) . . . . ? C8 N3 C5 S2 -179.1(2) . . . . ? Cu1 N3 C5 S2 4.5(3) . . . . ? C5 N4 C6 C7 -1.4(6) . . . . ? N3 C8 C7 C6 0.4(6) . . . . ? N4 C6 C7 C8 0.8(7) . . . . ? C1 S1 C9 S2 71.1(2) . . . 2_656 ? N4 C5 S2 C9 7.9(3) . . . 2_656 ? N3 C5 S2 C9 -172.9(2) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.070 _refine_diff_density_min -1.058 _refine_diff_density_rms 0.117 data_2 _database_code_depnum_ccdc_archive 'CCDC 670248' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Cu N5 S2' _chemical_formula_weight 325.87 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 8.4287(5) _cell_length_b 8.8723(6) _cell_length_c 16.1154(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.731(1) _cell_angle_gamma 90.00 _cell_volume 1203.77(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3898 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 2.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5847 _exptl_absorpt_correction_T_max 0.6158 _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 'Bruker APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _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 6578 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2349 _reflns_number_gt 2176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0369P)^2^+0.7229P] 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 2349 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Cu1 Cu 0.62351(3) 0.52545(3) 1.224823(17) 0.03396(11) Uani 1 1 d . . . S1 S 0.80644(7) 0.71449(6) 1.07406(3) 0.03451(14) Uani 1 1 d . . . S2 S 0.78721(6) 0.86686(7) 0.90966(3) 0.03447(14) Uani 1 1 d . . . N1 N 0.6623(2) 0.4576(2) 1.09181(10) 0.0287(4) Uani 1 1 d . . . N2 N 0.7769(2) 0.4948(2) 0.96043(11) 0.0356(4) Uani 1 1 d . . . N3 N 1.0819(2) 0.9182(2) 0.86424(11) 0.0339(4) Uani 1 1 d . . . N4 N 0.8686(2) 0.9917(2) 0.77009(10) 0.0290(4) Uani 1 1 d . . . N5 N 0.5322(2) 0.3319(2) 1.25863(11) 0.0336(4) Uani 1 1 d . . . C1 C 0.7426(2) 0.5372(2) 1.03669(12) 0.0272(4) Uani 1 1 d . . . C2 C 0.6064(3) 0.3245(3) 1.06464(14) 0.0346(5) Uani 1 1 d . . . H2 H 0.5485 0.2657 1.1002 0.042 Uiso 1 1 calc R . . C3 C 0.6314(3) 0.2712(3) 0.98586(14) 0.0395(5) Uani 1 1 d . . . H3 H 0.5903 0.1792 0.9674 0.047 Uiso 1 1 calc R . . C4 C 0.7197(3) 0.3605(3) 0.93619(14) 0.0395(5) Uani 1 1 d . . . H4 H 0.7407 0.3262 0.8833 0.047 Uiso 1 1 calc R . . C5 C 0.9186(3) 0.7824(3) 0.98930(12) 0.0321(5) Uani 1 1 d . . . H5A H 0.9762 0.6994 0.9656 0.039 Uiso 1 1 calc R . . H5B H 0.9954 0.8566 1.0098 0.039 Uiso 1 1 calc R . . C6 C 0.9288(2) 0.9314(2) 0.84117(12) 0.0253(4) Uani 1 1 d . . . C7 C 1.1842(3) 0.9743(3) 0.81193(14) 0.0365(5) Uani 1 1 d . . . H7 H 1.2923 0.9659 0.8256 0.044 Uiso 1 1 calc R . . C8 C 1.1374(3) 1.0438(3) 0.73892(14) 0.0371(5) Uani 1 1 d . . . H8 H 1.2104 1.0849 0.7038 0.045 Uiso 1 1 calc R . . C9 C 0.9764(3) 1.0494(3) 0.72037(13) 0.0366(5) Uani 1 1 d . . . H9 H 0.9407 1.0953 0.6711 0.044 Uiso 1 1 calc R . . C10 C 0.5280(2) 0.7178(2) 1.23298(12) 0.0276(4) 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 0.03568(17) 0.02290(16) 0.04375(18) -0.00194(11) 0.00641(12) 0.00047(10) S1 0.0505(3) 0.0310(3) 0.0225(3) -0.0009(2) 0.0069(2) -0.0092(2) S2 0.0281(3) 0.0447(3) 0.0310(3) 0.0110(2) 0.0059(2) -0.0005(2) N1 0.0331(9) 0.0282(9) 0.0251(8) -0.0007(7) 0.0031(7) -0.0002(7) N2 0.0441(11) 0.0395(11) 0.0235(9) -0.0040(7) 0.0032(8) 0.0000(8) N3 0.0282(9) 0.0410(11) 0.0325(9) 0.0067(8) 0.0032(7) 0.0009(8) N4 0.0288(9) 0.0297(9) 0.0284(9) 0.0042(7) 0.0006(7) -0.0034(7) N5 0.0355(10) 0.0292(10) 0.0366(10) 0.0040(8) 0.0062(7) -0.0021(8) C1 0.0312(10) 0.0274(10) 0.0229(9) -0.0004(8) -0.0006(8) 0.0017(8) C2 0.0364(11) 0.0311(11) 0.0364(11) -0.0009(9) 0.0013(9) -0.0042(9) C3 0.0437(13) 0.0339(12) 0.0403(12) -0.0105(10) -0.0053(10) -0.0022(10) C4 0.0449(13) 0.0440(14) 0.0294(11) -0.0106(10) 0.0006(9) 0.0039(11) C5 0.0345(11) 0.0349(12) 0.0269(10) 0.0059(9) 0.0016(8) -0.0043(9) C6 0.0295(10) 0.0230(10) 0.0237(9) -0.0003(7) 0.0039(7) -0.0003(8) C7 0.0281(10) 0.0430(13) 0.0385(12) -0.0007(10) 0.0036(9) -0.0018(9) C8 0.0364(12) 0.0455(14) 0.0302(11) 0.0003(10) 0.0092(9) -0.0130(10) C9 0.0422(12) 0.0403(13) 0.0269(10) 0.0075(9) -0.0016(9) -0.0117(10) C10 0.0277(9) 0.0286(11) 0.0268(10) -0.0030(8) 0.0038(8) -0.0030(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 Cu1 C10 1.894(2) . ? Cu1 N5 1.9690(19) . ? Cu1 N4 2.1635(17) 4_576 ? Cu1 N1 2.2651(17) . ? S1 C1 1.760(2) . ? S1 C5 1.802(2) . ? S2 C6 1.760(2) . ? S2 C5 1.817(2) . ? N1 C2 1.338(3) . ? N1 C1 1.342(3) . ? N2 C1 1.330(3) . ? N2 C4 1.337(3) . ? N3 C6 1.331(3) . ? N3 C7 1.331(3) . ? N4 C9 1.341(3) . ? N4 C6 1.342(3) . ? N4 Cu1 2.1635(17) 4_575 ? N5 C10 1.144(3) 2_647 ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.371(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 C9 1.377(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N5 1.144(3) 2_657 ? 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 C10 Cu1 N5 126.40(8) . . ? C10 Cu1 N4 116.25(8) . 4_576 ? N5 Cu1 N4 103.00(7) . 4_576 ? C10 Cu1 N1 112.71(7) . . ? N5 Cu1 N1 96.09(7) . . ? N4 Cu1 N1 97.00(6) 4_576 . ? C1 S1 C5 101.68(10) . . ? C6 S2 C5 99.70(9) . . ? C2 N1 C1 115.37(18) . . ? C2 N1 Cu1 118.67(14) . . ? C1 N1 Cu1 125.92(13) . . ? C1 N2 C4 115.5(2) . . ? C6 N3 C7 116.05(18) . . ? C9 N4 C6 115.03(17) . . ? C9 N4 Cu1 119.23(14) . 4_575 ? C6 N4 Cu1 125.17(13) . 4_575 ? C10 N5 Cu1 170.53(18) 2_647 . ? N2 C1 N1 126.99(19) . . ? N2 C1 S1 119.49(16) . . ? N1 C1 S1 113.52(14) . . ? N1 C2 C3 122.5(2) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 C2 116.7(2) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 121.6 . . ? N2 C4 C3 122.9(2) . . ? N2 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? S1 C5 S2 110.45(11) . . ? S1 C5 H5A 109.6 . . ? S2 C5 H5A 109.6 . . ? S1 C5 H5B 109.6 . . ? S2 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? N3 C6 N4 126.56(18) . . ? N3 C6 S2 118.28(15) . . ? N4 C6 S2 115.16(14) . . ? N3 C7 C8 122.9(2) . . ? N3 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C7 C8 C9 116.3(2) . . ? C7 C8 H8 121.8 . . ? C9 C8 H8 121.8 . . ? N4 C9 C8 123.0(2) . . ? N4 C9 H9 118.5 . . ? C8 C9 H9 118.5 . . ? N5 C10 Cu1 176.83(18) 2_657 . ? 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 C10 Cu1 N1 C2 -127.14(16) . . . . ? N5 Cu1 N1 C2 6.61(16) . . . . ? N4 Cu1 N1 C2 110.56(16) 4_576 . . . ? C10 Cu1 N1 C1 55.33(18) . . . . ? N5 Cu1 N1 C1 -170.91(17) . . . . ? N4 Cu1 N1 C1 -66.96(17) 4_576 . . . ? C10 Cu1 N5 C10 95.2(11) . . . 2_647 ? N4 Cu1 N5 C10 -127.6(11) 4_576 . . 2_647 ? N1 Cu1 N5 C10 -29.0(11) . . . 2_647 ? C4 N2 C1 N1 2.5(3) . . . . ? C4 N2 C1 S1 -178.05(16) . . . . ? C2 N1 C1 N2 -2.9(3) . . . . ? Cu1 N1 C1 N2 174.65(16) . . . . ? C2 N1 C1 S1 177.53(15) . . . . ? Cu1 N1 C1 S1 -4.9(2) . . . . ? C5 S1 C1 N2 -3.4(2) . . . . ? C5 S1 C1 N1 176.18(15) . . . . ? C1 N1 C2 C3 1.0(3) . . . . ? Cu1 N1 C2 C3 -176.80(17) . . . . ? N1 C2 C3 C4 1.1(3) . . . . ? C1 N2 C4 C3 0.0(3) . . . . ? C2 C3 C4 N2 -1.7(3) . . . . ? C1 S1 C5 S2 83.12(13) . . . . ? C6 S2 C5 S1 176.31(12) . . . . ? C7 N3 C6 N4 1.8(3) . . . . ? C7 N3 C6 S2 -177.32(17) . . . . ? C9 N4 C6 N3 -3.1(3) . . . . ? Cu1 N4 C6 N3 168.13(16) 4_575 . . . ? C9 N4 C6 S2 175.98(16) . . . . ? Cu1 N4 C6 S2 -12.8(2) 4_575 . . . ? C5 S2 C6 N3 -5.67(19) . . . . ? C5 S2 C6 N4 175.14(16) . . . . ? C6 N3 C7 C8 0.9(3) . . . . ? N3 C7 C8 C9 -1.9(4) . . . . ? C6 N4 C9 C8 1.9(3) . . . . ? Cu1 N4 C9 C8 -169.89(18) 4_575 . . . ? C7 C8 C9 N4 0.4(4) . . . . ? N5 Cu1 C10 N5 39(3) . . . 2_657 ? N4 Cu1 C10 N5 -93(3) 4_576 . . 2_657 ? N1 Cu1 C10 N5 156(3) . . . 2_657 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.287 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.067 data_3 _database_code_depnum_ccdc_archive 'CCDC 670249' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cu I N6 S3' _chemical_formula_weight 565.95 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8050(10) _cell_length_b 9.0434(10) _cell_length_c 12.5826(14) _cell_angle_alpha 87.137(2) _cell_angle_beta 85.596(2) _cell_angle_gamma 88.277(2) _cell_volume 997.37(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3278 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.10 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 2.969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4695 _exptl_absorpt_correction_T_max 0.5882 _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 'Bruker APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _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 9624 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4825 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0575P)^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 4825 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 I1 I 0.69219(3) 0.51009(3) -0.108048(19) 0.05053(11) Uani 1 1 d . . . Cu1 Cu 0.59196(5) 0.58697(5) 0.08591(4) 0.04433(13) Uani 1 1 d . . . S2 S 0.55193(11) 0.60691(10) 0.33997(7) 0.0476(2) Uani 1 1 d . . . S1 S 0.87348(10) 0.80342(10) 0.06441(9) 0.0481(2) Uani 1 1 d . . . S3 S 0.31019(16) 1.11249(13) 0.42109(12) 0.0766(4) Uani 1 1 d . . . C8 C 0.9392(4) 0.3189(4) 0.2314(4) 0.0552(10) Uani 1 1 d . . . H8 H 1.0234 0.2615 0.2080 0.066 Uiso 1 1 calc R . . N3 N 0.7291(3) 0.4800(3) 0.1935(2) 0.0391(6) Uani 1 1 d . . . N1 N 0.5795(3) 0.8120(3) 0.1070(2) 0.0356(6) Uani 1 1 d . . . C6 C 0.7019(4) 0.4855(4) 0.2996(3) 0.0390(7) Uani 1 1 d . . . N6 N 0.2587(4) 0.8262(4) 0.3994(3) 0.0553(8) Uani 1 1 d . . . N5 N 0.0630(4) 1.0043(4) 0.3661(4) 0.0670(10) Uani 1 1 d . . . N4 N 0.7798(4) 0.4128(4) 0.3738(3) 0.0542(8) Uani 1 1 d . . . C1 C 0.7017(4) 0.8976(4) 0.0993(3) 0.0371(7) Uani 1 1 d . . . N2 N 0.7017(4) 1.0423(3) 0.1156(3) 0.0485(8) Uani 1 1 d . . . C11 C 0.2015(4) 0.9617(4) 0.3930(3) 0.0492(9) Uani 1 1 d . . . C4 C 0.4456(4) 0.8809(4) 0.1329(3) 0.0429(8) Uani 1 1 d . . . H4 H 0.3576 0.8258 0.1398 0.052 Uiso 1 1 calc R . . C5 C 1.0062(4) 0.9530(4) 0.0503(3) 0.0495(9) Uani 1 1 d . . . H5A H 0.9882 1.0150 0.1110 0.059 Uiso 1 1 calc R . . H5B H 1.1091 0.9118 0.0513 0.059 Uiso 1 1 calc R . . C2 C 0.5659(5) 1.1058(4) 0.1399(3) 0.0532(10) Uani 1 1 d . . . H2 H 0.5610 1.2068 0.1509 0.064 Uiso 1 1 calc R . . C9 C 0.8515(4) 0.3960(4) 0.1606(3) 0.0501(9) Uani 1 1 d . . . H9 H 0.8773 0.3902 0.0878 0.060 Uiso 1 1 calc R . . C3 C 0.4337(4) 1.0297(4) 0.1496(3) 0.0492(9) Uani 1 1 d . . . H3 H 0.3401 1.0764 0.1666 0.059 Uiso 1 1 calc R . . C14 C 0.1667(6) 0.7218(5) 0.3731(4) 0.0652(12) Uani 1 1 d . . . H14 H 0.2019 0.6238 0.3754 0.078 Uiso 1 1 calc R . . C7 C 0.8980(5) 0.3298(5) 0.3369(4) 0.0609(11) Uani 1 1 d . . . H7 H 0.9551 0.2769 0.3859 0.073 Uiso 1 1 calc R . . C13 C 0.0241(6) 0.7520(6) 0.3433(4) 0.0710(13) Uani 1 1 d . . . H13 H -0.0384 0.6776 0.3251 0.085 Uiso 1 1 calc R . . C12 C -0.0231(6) 0.8961(6) 0.3413(4) 0.0742(14) Uani 1 1 d . . . H12 H -0.1208 0.9199 0.3214 0.089 Uiso 1 1 calc R . . C18 C 0.4969(6) 1.0266(5) 0.4434(4) 0.0704(13) Uani 1 1 d . . . H18A H 0.5158 0.9440 0.3975 0.084 Uiso 1 1 calc R . . H18B H 0.5757 1.0982 0.4252 0.084 Uiso 1 1 calc R . . C10 C 0.5366(4) 0.5722(4) 0.4833(3) 0.0411(8) Uani 1 1 d . . . H10A H 0.6376 0.5719 0.5091 0.049 Uiso 1 1 calc R . . H10B H 0.4771 0.6521 0.5161 0.049 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 I1 0.04188(15) 0.06184(18) 0.04840(17) -0.01791(12) 0.00918(11) -0.01705(12) Cu1 0.0425(2) 0.0406(3) 0.0490(3) -0.00231(19) 0.0022(2) -0.00071(18) S2 0.0577(6) 0.0442(5) 0.0385(5) 0.0008(4) 0.0006(4) 0.0223(4) S1 0.0344(4) 0.0397(5) 0.0698(7) -0.0048(4) 0.0014(4) -0.0061(4) S3 0.0807(8) 0.0437(6) 0.1108(11) -0.0208(6) -0.0347(8) 0.0093(6) C8 0.043(2) 0.046(2) 0.075(3) -0.002(2) 0.0052(19) 0.0125(17) N3 0.0363(14) 0.0332(14) 0.0464(17) -0.0043(12) 0.0055(12) 0.0035(11) N1 0.0342(14) 0.0363(14) 0.0358(15) 0.0011(11) -0.0008(11) -0.0035(11) C6 0.0410(18) 0.0292(16) 0.046(2) -0.0003(14) -0.0005(15) 0.0030(13) N6 0.0538(19) 0.0392(17) 0.075(2) -0.0069(16) -0.0161(17) 0.0060(15) N5 0.062(2) 0.058(2) 0.083(3) -0.005(2) -0.025(2) 0.0162(18) N4 0.057(2) 0.0500(19) 0.055(2) 0.0050(15) -0.0050(16) 0.0141(16) C1 0.0382(17) 0.0379(18) 0.0354(17) -0.0017(14) -0.0026(14) -0.0045(14) N2 0.0497(18) 0.0360(16) 0.060(2) -0.0070(14) -0.0007(15) -0.0057(13) C11 0.051(2) 0.047(2) 0.051(2) -0.0078(17) -0.0093(18) 0.0106(17) C4 0.0356(17) 0.044(2) 0.048(2) 0.0013(16) 0.0019(15) 0.0000(15) C5 0.0372(18) 0.049(2) 0.064(2) -0.0025(18) -0.0066(17) -0.0161(16) C2 0.063(3) 0.0363(19) 0.060(2) -0.0083(17) -0.004(2) 0.0039(18) C9 0.046(2) 0.043(2) 0.059(2) -0.0041(17) 0.0105(18) 0.0030(16) C3 0.047(2) 0.050(2) 0.049(2) -0.0031(17) 0.0050(17) 0.0085(17) C14 0.073(3) 0.045(2) 0.080(3) -0.002(2) -0.021(2) 0.000(2) C7 0.054(2) 0.058(3) 0.069(3) 0.005(2) -0.010(2) 0.021(2) C13 0.064(3) 0.066(3) 0.086(4) -0.009(3) -0.021(3) -0.012(2) C12 0.058(3) 0.085(4) 0.083(4) -0.006(3) -0.033(3) 0.009(3) C18 0.077(3) 0.062(3) 0.075(3) -0.026(2) -0.006(3) -0.009(2) C10 0.054(2) 0.0339(17) 0.0356(17) -0.0080(14) -0.0038(15) 0.0091(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 I1 Cu1 2.6495(6) . ? I1 Cu1 2.6661(6) 2_665 ? Cu1 N1 2.064(3) . ? Cu1 N3 2.068(3) . ? Cu1 I1 2.6661(6) 2_665 ? S2 C6 1.753(3) . ? S2 C10 1.810(4) . ? S1 C1 1.750(3) . ? S1 C5 1.807(4) . ? S3 C11 1.755(4) . ? S3 C18 1.832(5) . ? C8 C7 1.357(6) . ? C8 C9 1.374(6) . ? N3 C6 1.341(4) . ? N3 C9 1.350(4) . ? N1 C1 1.338(4) . ? N1 C4 1.343(4) . ? C6 N4 1.336(5) . ? N6 C11 1.312(5) . ? N6 C14 1.333(5) . ? N5 C12 1.320(6) . ? N5 C11 1.331(5) . ? N4 C7 1.332(5) . ? C1 N2 1.335(4) . ? N2 C2 1.332(5) . ? C4 C3 1.372(5) . ? C5 C5 1.499(8) 2_775 ? C2 C3 1.364(6) . ? C14 C13 1.354(6) . ? C13 C12 1.355(7) . ? C18 C18 1.485(10) 2_676 ? C10 C10 1.501(7) 2_666 ? 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 Cu1 I1 Cu1 76.378(17) . 2_665 ? N1 Cu1 N3 110.95(11) . . ? N1 Cu1 I1 115.13(8) . . ? N3 Cu1 I1 107.85(8) . . ? N1 Cu1 I1 107.18(8) . 2_665 ? N3 Cu1 I1 111.96(8) . 2_665 ? I1 Cu1 I1 103.622(17) . 2_665 ? C6 S2 C10 102.03(17) . . ? C1 S1 C5 101.74(18) . . ? C11 S3 C18 103.1(2) . . ? C7 C8 C9 117.4(4) . . ? C6 N3 C9 115.4(3) . . ? C6 N3 Cu1 123.1(2) . . ? C9 N3 Cu1 121.5(3) . . ? C1 N1 C4 115.7(3) . . ? C1 N1 Cu1 123.3(2) . . ? C4 N1 Cu1 120.9(2) . . ? N4 C6 N3 126.5(3) . . ? N4 C6 S2 119.1(3) . . ? N3 C6 S2 114.3(2) . . ? C11 N6 C14 114.9(3) . . ? C12 N5 C11 114.9(4) . . ? C7 N4 C6 115.6(4) . . ? N2 C1 N1 126.1(3) . . ? N2 C1 S1 119.7(3) . . ? N1 C1 S1 114.2(2) . . ? C2 N2 C1 115.8(3) . . ? N6 C11 N5 127.4(4) . . ? N6 C11 S3 120.6(3) . . ? N5 C11 S3 112.0(3) . . ? N1 C4 C3 122.4(3) . . ? C5 C5 S1 113.2(3) 2_775 . ? N2 C2 C3 123.1(4) . . ? N3 C9 C8 121.9(4) . . ? C2 C3 C4 116.8(3) . . ? N6 C14 C13 122.9(4) . . ? N4 C7 C8 123.2(4) . . ? C14 C13 C12 116.7(5) . . ? N5 C12 C13 123.1(4) . . ? C18 C18 S3 110.6(5) 2_676 . ? C10 C10 S2 112.7(3) 2_666 . ? 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 Cu1 I1 Cu1 N1 -116.70(9) 2_665 . . . ? Cu1 I1 Cu1 N3 118.83(8) 2_665 . . . ? Cu1 I1 Cu1 I1 0.0 2_665 . . 2_665 ? N1 Cu1 N3 C6 58.6(3) . . . . ? I1 Cu1 N3 C6 -174.5(2) . . . . ? I1 Cu1 N3 C6 -61.1(3) 2_665 . . . ? N1 Cu1 N3 C9 -123.1(3) . . . . ? I1 Cu1 N3 C9 3.9(3) . . . . ? I1 Cu1 N3 C9 117.2(3) 2_665 . . . ? N3 Cu1 N1 C1 58.8(3) . . . . ? I1 Cu1 N1 C1 -64.0(3) . . . . ? I1 Cu1 N1 C1 -178.7(2) 2_665 . . . ? N3 Cu1 N1 C4 -119.2(3) . . . . ? I1 Cu1 N1 C4 118.0(2) . . . . ? I1 Cu1 N1 C4 3.3(3) 2_665 . . . ? C9 N3 C6 N4 -2.6(5) . . . . ? Cu1 N3 C6 N4 175.9(3) . . . . ? C9 N3 C6 S2 175.1(3) . . . . ? Cu1 N3 C6 S2 -6.5(4) . . . . ? C10 S2 C6 N4 -7.5(3) . . . . ? C10 S2 C6 N3 174.7(2) . . . . ? N3 C6 N4 C7 1.6(6) . . . . ? S2 C6 N4 C7 -175.9(3) . . . . ? C4 N1 C1 N2 0.5(5) . . . . ? Cu1 N1 C1 N2 -177.6(3) . . . . ? C4 N1 C1 S1 -179.5(2) . . . . ? Cu1 N1 C1 S1 2.4(4) . . . . ? C5 S1 C1 N2 -4.8(3) . . . . ? C5 S1 C1 N1 175.2(3) . . . . ? N1 C1 N2 C2 -1.2(6) . . . . ? S1 C1 N2 C2 178.8(3) . . . . ? C14 N6 C11 N5 1.7(7) . . . . ? C14 N6 C11 S3 -178.1(3) . . . . ? C12 N5 C11 N6 -1.6(7) . . . . ? C12 N5 C11 S3 178.3(4) . . . . ? C18 S3 C11 N6 4.7(4) . . . . ? C18 S3 C11 N5 -175.2(4) . . . . ? C1 N1 C4 C3 0.6(5) . . . . ? Cu1 N1 C4 C3 178.7(3) . . . . ? C1 S1 C5 C5 -75.0(4) . . . 2_775 ? C1 N2 C2 C3 0.9(6) . . . . ? C6 N3 C9 C8 1.6(5) . . . . ? Cu1 N3 C9 C8 -176.9(3) . . . . ? C7 C8 C9 N3 0.1(6) . . . . ? N2 C2 C3 C4 0.1(6) . . . . ? N1 C4 C3 C2 -0.8(6) . . . . ? C11 N6 C14 C13 -0.8(7) . . . . ? C6 N4 C7 C8 0.3(7) . . . . ? C9 C8 C7 N4 -1.1(7) . . . . ? N6 C14 C13 C12 -0.2(8) . . . . ? C11 N5 C12 C13 0.4(8) . . . . ? C14 C13 C12 N5 0.3(9) . . . . ? C11 S3 C18 C18 -87.0(5) . . . 2_676 ? C6 S2 C10 C10 -74.6(4) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.983 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.167 data_4 _database_code_depnum_ccdc_archive 'CCDC 670250' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Cu N5 S2' _chemical_formula_weight 339.90 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 8.3584(8) _cell_length_b 9.1892(9) _cell_length_c 17.7463(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.063(2) _cell_angle_gamma 90.00 _cell_volume 1352.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2468 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.57 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.915 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6359 _exptl_absorpt_correction_T_max 0.7493 _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 'Bruker APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _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 6954 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2585 _reflns_number_gt 2303 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0389P)^2^+0.7810P] 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 2585 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.11249(4) 0.33000(4) 0.24045(2) 0.04134(13) Uani 1 1 d . . . S1 S 0.31905(8) 0.46305(9) 0.40009(4) 0.04159(19) Uani 1 1 d . . . S2 S 0.36585(10) 0.48583(10) 0.09970(5) 0.0539(2) Uani 1 1 d . . . C1 C 0.0215(3) 0.5175(3) 0.24465(14) 0.0311(5) Uani 1 1 d . . . C2 C 0.4442(3) 0.3809(3) 0.33981(14) 0.0306(5) Uani 1 1 d . . . C3 C 0.6898(3) 0.3294(4) 0.30676(17) 0.0465(7) Uani 1 1 d . . . H3 H 0.8014 0.3386 0.3142 0.056 Uiso 1 1 calc R . . C4 C 0.6214(3) 0.2493(4) 0.24691(16) 0.0519(8) Uani 1 1 d . . . H4 H 0.6841 0.2022 0.2146 0.062 Uiso 1 1 calc R . . C5 C 0.4573(3) 0.2405(3) 0.23608(16) 0.0446(7) Uani 1 1 d . . . H5 H 0.4080 0.1851 0.1959 0.054 Uiso 1 1 calc R . . C6 C 0.4633(3) 0.5515(3) 0.46988(15) 0.0387(6) Uani 1 1 d . . . H6A H 0.5483 0.5940 0.4444 0.046 Uiso 1 1 calc R . . H6B H 0.4099 0.6297 0.4937 0.046 Uiso 1 1 calc R . . C7 C 0.2047(3) 0.3814(3) 0.05562(15) 0.0379(6) Uani 1 1 d . . . C8 C 0.0449(4) 0.3087(4) -0.04850(17) 0.0536(8) Uani 1 1 d . . . H8 H 0.0141 0.3122 -0.1006 0.064 Uiso 1 1 calc R . . C9 C -0.0367(4) 0.2180(4) -0.00536(17) 0.0558(8) Uani 1 1 d . . . H9 H -0.1210 0.1598 -0.0271 0.067 Uiso 1 1 calc R . . C10 C 0.0112(4) 0.2169(4) 0.07124(17) 0.0530(8) Uani 1 1 d . . . H10 H -0.0424 0.1563 0.1018 0.064 Uiso 1 1 calc R . . C11 C 0.4526(4) 0.5566(3) 0.01897(18) 0.0500(8) Uani 1 1 d . . . H11A H 0.3670 0.5938 -0.0178 0.060 Uiso 1 1 calc R . . H11B H 0.5234 0.6372 0.0354 0.060 Uiso 1 1 calc R . . N1 N 0.0309(2) 0.1327(3) 0.25126(12) 0.0354(5) Uani 1 1 d . . . N2 N 0.3649(2) 0.3089(2) 0.28131(12) 0.0344(5) Uani 1 1 d . . . N3 N 0.6039(2) 0.3952(3) 0.35524(12) 0.0387(5) Uani 1 1 d . . . N4 N 0.1323(3) 0.2998(3) 0.10385(13) 0.0443(6) Uani 1 1 d . . . N5 N 0.1662(3) 0.3915(3) -0.01877(14) 0.0470(6) 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 0.0385(2) 0.0268(2) 0.0584(3) -0.00480(15) 0.00494(15) 0.00085(13) S1 0.0319(3) 0.0552(5) 0.0374(4) -0.0114(3) 0.0033(3) 0.0046(3) S2 0.0618(5) 0.0524(5) 0.0469(5) -0.0043(4) 0.0041(4) -0.0210(4) C1 0.0303(12) 0.0322(16) 0.0304(13) -0.0009(11) 0.0031(10) -0.0044(11) C2 0.0330(13) 0.0295(14) 0.0294(13) 0.0021(10) 0.0038(10) 0.0018(10) C3 0.0331(14) 0.064(2) 0.0435(16) 0.0062(14) 0.0074(12) 0.0065(13) C4 0.0476(17) 0.069(2) 0.0402(16) 0.0006(15) 0.0087(13) 0.0247(15) C5 0.0517(17) 0.0419(18) 0.0382(16) -0.0094(13) -0.0028(12) 0.0145(13) C6 0.0474(15) 0.0345(16) 0.0337(14) -0.0074(12) 0.0027(11) 0.0009(12) C7 0.0393(14) 0.0375(16) 0.0369(15) -0.0018(12) 0.0042(11) -0.0007(12) C8 0.0534(18) 0.071(2) 0.0349(16) -0.0039(15) 0.0001(13) -0.0010(16) C9 0.0451(17) 0.077(2) 0.0446(17) -0.0090(16) 0.0023(13) -0.0184(16) C10 0.0505(17) 0.069(2) 0.0399(16) 0.0008(15) 0.0064(13) -0.0203(16) C11 0.0594(19) 0.0310(18) 0.061(2) 0.0039(14) 0.0120(14) -0.0086(13) N1 0.0351(12) 0.0319(14) 0.0394(12) 0.0005(10) 0.0052(9) -0.0009(10) N2 0.0338(11) 0.0313(13) 0.0367(12) -0.0053(10) -0.0004(9) 0.0037(9) N3 0.0296(11) 0.0490(15) 0.0372(12) -0.0005(11) 0.0026(9) -0.0010(10) N4 0.0478(14) 0.0500(16) 0.0345(12) 0.0012(11) 0.0032(10) -0.0090(11) N5 0.0513(14) 0.0502(16) 0.0400(14) 0.0023(11) 0.0082(11) -0.0054(12) _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 C1 1.888(3) . ? Cu1 N1 1.955(2) . ? Cu1 N2 2.153(2) . ? Cu1 N4 2.466(2) . ? S1 C2 1.756(2) . ? S1 C6 1.811(3) . ? S2 C7 1.757(3) . ? S2 C11 1.805(3) . ? C1 N1 1.151(3) 2 ? C2 N3 1.336(3) . ? C2 N2 1.336(3) . ? C3 N3 1.332(4) . ? C3 C4 1.359(4) . ? C3 H3 0.9300 . ? C4 C5 1.364(4) . ? C4 H4 0.9300 . ? C5 N2 1.337(3) . ? C5 H5 0.9300 . ? C6 C6 1.501(5) 3_666 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N5 1.323(4) . ? C7 N4 1.337(4) . ? C8 N5 1.324(4) . ? C8 C9 1.369(4) . ? C8 H8 0.9300 . ? C9 C10 1.369(4) . ? C9 H9 0.9300 . ? C10 N4 1.340(4) . ? C10 H10 0.9300 . ? C11 C11 1.514(6) 3_665 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N1 C1 1.151(3) 2_545 ? 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 C1 Cu1 N1 134.05(10) . . ? C1 Cu1 N2 116.83(9) . . ? N1 Cu1 N2 102.87(9) . . ? C1 Cu1 N4 102.57(10) . . ? N1 Cu1 N4 93.36(9) . . ? N2 Cu1 N4 98.02(8) . . ? C2 S1 C6 102.31(12) . . ? C7 S2 C11 101.79(14) . . ? N1 C1 Cu1 178.2(2) 2 . ? N3 C2 N2 126.6(2) . . ? N3 C2 S1 119.20(19) . . ? N2 C2 S1 114.23(18) . . ? N3 C3 C4 122.8(3) . . ? N3 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C3 C4 C5 117.5(3) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N2 C5 C4 122.2(3) . . ? N2 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C6 C6 S1 112.6(3) 3_666 . ? C6 C6 H6A 109.1 3_666 . ? S1 C6 H6A 109.1 . . ? C6 C6 H6B 109.1 3_666 . ? S1 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N5 C7 N4 127.2(3) . . ? N5 C7 S2 119.0(2) . . ? N4 C7 S2 113.8(2) . . ? N5 C8 C9 122.5(3) . . ? N5 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C8 C9 C10 117.1(3) . . ? C8 C9 H9 121.5 . . ? C10 C9 H9 121.5 . . ? N4 C10 C9 122.5(3) . . ? N4 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C11 C11 S2 112.9(3) 3_665 . ? C11 C11 H11A 109.0 3_665 . ? S2 C11 H11A 109.0 . . ? C11 C11 H11B 109.0 3_665 . ? S2 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C1 N1 Cu1 177.4(2) 2_545 . ? C2 N2 C5 115.5(2) . . ? C2 N2 Cu1 126.09(17) . . ? C5 N2 Cu1 117.01(17) . . ? C3 N3 C2 115.3(2) . . ? C7 N4 C10 114.8(2) . . ? C7 N4 Cu1 131.05(19) . . ? C10 N4 Cu1 110.47(18) . . ? C7 N5 C8 116.0(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 N1 Cu1 C1 N1 121(8) . . . 2 ? N2 Cu1 C1 N1 -25(8) . . . 2 ? N4 Cu1 C1 N1 -131(8) . . . 2 ? C6 S1 C2 N3 0.8(2) . . . . ? C6 S1 C2 N2 -178.9(2) . . . . ? N3 C3 C4 C5 1.7(5) . . . . ? C3 C4 C5 N2 0.9(5) . . . . ? C2 S1 C6 C6 -81.0(3) . . . 3_666 ? C11 S2 C7 N5 -9.6(3) . . . . ? C11 S2 C7 N4 171.3(2) . . . . ? N5 C8 C9 C10 0.6(5) . . . . ? C8 C9 C10 N4 0.0(5) . . . . ? C7 S2 C11 C11 -74.7(3) . . . 3_665 ? C1 Cu1 N1 C1 60(5) . . . 2_545 ? N2 Cu1 N1 C1 -151(5) . . . 2_545 ? N4 Cu1 N1 C1 -52(5) . . . 2_545 ? N3 C2 N2 C5 2.8(4) . . . . ? S1 C2 N2 C5 -177.5(2) . . . . ? N3 C2 N2 Cu1 -163.4(2) . . . . ? S1 C2 N2 Cu1 16.3(3) . . . . ? C4 C5 N2 C2 -2.9(4) . . . . ? C4 C5 N2 Cu1 164.6(2) . . . . ? C1 Cu1 N2 C2 35.9(3) . . . . ? N1 Cu1 N2 C2 -120.3(2) . . . . ? N4 Cu1 N2 C2 144.4(2) . . . . ? C1 Cu1 N2 C5 -130.2(2) . . . . ? N1 Cu1 N2 C5 73.7(2) . . . . ? N4 Cu1 N2 C5 -21.7(2) . . . . ? C4 C3 N3 C2 -1.9(4) . . . . ? N2 C2 N3 C3 -0.4(4) . . . . ? S1 C2 N3 C3 179.9(2) . . . . ? N5 C7 N4 C10 2.3(5) . . . . ? S2 C7 N4 C10 -178.7(2) . . . . ? N5 C7 N4 Cu1 -153.7(2) . . . . ? S2 C7 N4 Cu1 25.3(3) . . . . ? C9 C10 N4 C7 -1.3(5) . . . . ? C9 C10 N4 Cu1 159.6(3) . . . . ? C1 Cu1 N4 C7 55.9(3) . . . . ? N1 Cu1 N4 C7 -167.5(3) . . . . ? N2 Cu1 N4 C7 -64.0(3) . . . . ? C1 Cu1 N4 C10 -100.9(2) . . . . ? N1 Cu1 N4 C10 35.7(2) . . . . ? N2 Cu1 N4 C10 139.2(2) . . . . ? N4 C7 N5 C8 -1.8(5) . . . . ? S2 C7 N5 C8 179.2(2) . . . . ? C9 C8 N5 C7 0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.550 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.060