# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_081110c_0m _database_code_depnum_ccdc_archive 'CCDC 799036' #TrackingRef '36.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H44 Cl2 Cu4 N14 O18 S4' _chemical_formula_weight 1462.19 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 13.9583(13) _cell_length_b 25.467(2) _cell_length_c 15.4276(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.572(6) _cell_angle_gamma 90.00 _cell_volume 5330.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2960 _exptl_absorpt_coefficient_mu 1.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7751 _exptl_absorpt_correction_T_max 0.8936 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 13995 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.63 _reflns_number_total 6138 _reflns_number_gt 4536 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0619P)^2^+4.3082P] 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 6138 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 C1 C 0.1522(2) 0.28854(13) -0.1905(2) 0.0427(7) Uani 1 1 d . . . C2 C 0.1348(2) 0.23396(12) -0.16264(19) 0.0362(6) Uani 1 1 d . . . C3 C 0.1141(2) 0.21904(12) -0.0811(2) 0.0363(7) Uani 1 1 d . . . C4 C 0.0921(2) 0.16640(13) -0.0681(2) 0.0449(7) Uani 1 1 d . . . H4 H 0.0747 0.1566 -0.0158 0.054 Uiso 1 1 calc R . . C5 C 0.0960(3) 0.12895(14) -0.1317(2) 0.0531(9) Uani 1 1 d . . . H5 H 0.0813 0.0941 -0.1220 0.064 Uiso 1 1 calc R . . C6 C 0.1216(3) 0.14297(15) -0.2100(2) 0.0527(9) Uani 1 1 d . . . H6 H 0.1270 0.1176 -0.2519 0.063 Uiso 1 1 calc R . . C7 C 0.1389(2) 0.19428(14) -0.2249(2) 0.0458(8) Uani 1 1 d . . . H7 H 0.1539 0.2035 -0.2785 0.055 Uiso 1 1 calc R . . C8 C 0.1207(2) 0.24555(12) 0.06983(19) 0.0337(6) Uani 1 1 d . . . C9 C 0.1198(2) 0.29231(12) 0.1306(2) 0.0357(6) Uani 1 1 d . . . C10 C 0.1182(3) 0.38390(13) 0.1511(2) 0.0514(8) Uani 1 1 d . . . H10A H 0.1649 0.3777 0.2075 0.062 Uiso 1 1 calc R . . H10B H 0.0540 0.3900 0.1633 0.062 Uiso 1 1 calc R . . C11 C 0.1492(3) 0.43197(14) 0.1067(3) 0.0587(10) Uani 1 1 d . . . H11A H 0.1559 0.4615 0.1473 0.070 Uiso 1 1 calc R . . H11B H 0.2130 0.4256 0.0940 0.070 Uiso 1 1 calc R . . C12 C 0.0764(3) 0.44547(13) 0.0219(2) 0.0534(9) Uani 1 1 d . . . H12A H 0.0104 0.4427 0.0316 0.064 Uiso 1 1 calc R . . H12B H 0.0865 0.4817 0.0067 0.064 Uiso 1 1 calc R . . C13 C 0.0001(3) 0.42029(15) -0.1310(2) 0.0612(10) Uani 1 1 d . . . H13A H 0.0150 0.4048 -0.1837 0.073 Uiso 1 1 calc R . . H13B H -0.0086 0.4577 -0.1414 0.073 Uiso 1 1 calc R . . C14 C -0.0935(3) 0.39756(15) -0.1177(3) 0.0661(11) Uani 1 1 d . . . H14A H -0.1156 0.4174 -0.0724 0.079 Uiso 1 1 calc R . . H14B H -0.1440 0.4001 -0.1728 0.079 Uiso 1 1 calc R . . C15 C 0.1239(2) 0.25270(15) 0.4161(2) 0.0465(8) Uani 1 1 d . . . C16 C 0.1305(3) 0.16804(16) 0.4918(3) 0.0596(10) Uani 1 1 d . . . H16 H 0.1337 0.1393 0.5296 0.072 Uiso 1 1 calc R . . C17 C 0.1285(2) 0.16494(14) 0.4046(2) 0.0458(8) Uani 1 1 d . . . C18 C 0.1320(3) 0.11971(14) 0.3487(2) 0.0480(8) Uani 1 1 d . . . C19 C 0.1324(3) 0.06827(15) 0.3673(3) 0.0643(11) Uani 1 1 d . . . H19 H 0.1265 0.0542 0.4214 0.077 Uiso 1 1 calc R . . C20 C 0.1480(3) 0.08879(14) 0.2167(3) 0.0520(9) Uani 1 1 d . . . Cu1 Cu 0.10012(3) 0.333633(14) -0.03416(2) 0.03751(12) Uani 1 1 d . . . Cu2 Cu 0.14130(3) 0.207332(15) 0.23767(2) 0.03944(12) Uani 1 1 d . . . N1 N 0.11449(17) 0.25741(10) -0.01387(16) 0.0344(5) Uani 1 1 d . . . N2 N 0.11362(19) 0.33773(10) 0.09416(17) 0.0391(6) Uani 1 1 d . . . N3 N 0.0835(2) 0.41157(10) -0.05460(19) 0.0450(6) Uani 1 1 d . . . H3 H 0.1380 0.4225 -0.0722 0.054 Uiso 1 1 calc R . . N4 N 0.12557(19) 0.21318(11) 0.36119(18) 0.0434(6) Uani 1 1 d . . . N5 N 0.1386(2) 0.13174(11) 0.26235(18) 0.0451(6) Uani 1 1 d . . . N6 N 0.1209(2) 0.30297(12) 0.3931(2) 0.0551(8) Uani 1 1 d . . . H6A H 0.1199 0.3117 0.3391 0.066 Uiso 1 1 calc R . . H6B H 0.1200 0.3269 0.4323 0.066 Uiso 1 1 calc R . . N7 N 0.1575(3) 0.08933(12) 0.1334(2) 0.0718(10) Uani 1 1 d . . . H7A H 0.1578 0.1187 0.1060 0.086 Uiso 1 1 calc R . . H7B H 0.1633 0.0603 0.1067 0.086 Uiso 1 1 calc R . . O1 O 0.1318(2) 0.32799(9) -0.14825(17) 0.0576(7) Uani 1 1 d . . . O2 O 0.18515(17) 0.29404(9) -0.25869(15) 0.0476(6) Uani 1 1 d . . . O3 O 0.12874(16) 0.20140(8) 0.10827(14) 0.0417(5) Uani 1 1 d . . . O4 O 0.12485(16) 0.28131(8) 0.21252(14) 0.0414(5) Uani 1 1 d . . . O5 O -0.08024(19) 0.34374(10) -0.09094(17) 0.0593(7) Uani 1 1 d . . . H5A H -0.1096 0.3211 -0.1349 0.071 Uiso 1 1 d R . . O11 O 0.3343(4) -0.07480(17) 0.0753(4) 0.1409(18) Uani 1 1 d . . . O12 O 0.3427(4) -0.01107(18) 0.1841(3) 0.1335(16) Uani 1 1 d . . . O13 O 0.2408(3) -0.00133(14) 0.0501(3) 0.1127(13) Uani 1 1 d . . . O14 O 0.2114(4) -0.06591(19) 0.1447(3) 0.1372(17) Uani 1 1 d . . . S1 S 0.12619(7) 0.23238(5) 0.52385(6) 0.0587(3) Uani 1 1 d . . . S2 S 0.14544(9) 0.03196(4) 0.27673(8) 0.0674(3) Uani 1 1 d . . . Cl1 Cl 0.28356(9) -0.03926(4) 0.11493(7) 0.0661(3) 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 C1 0.0404(16) 0.054(2) 0.0337(16) 0.0087(14) 0.0097(13) 0.0120(14) C2 0.0332(15) 0.0448(17) 0.0295(15) -0.0011(13) 0.0051(12) 0.0062(13) C3 0.0347(15) 0.0413(17) 0.0320(15) -0.0010(13) 0.0060(12) 0.0067(12) C4 0.0509(19) 0.0443(18) 0.0397(18) -0.0036(14) 0.0113(15) -0.0004(15) C5 0.063(2) 0.0430(19) 0.052(2) -0.0075(16) 0.0116(18) -0.0006(16) C6 0.054(2) 0.057(2) 0.048(2) -0.0203(17) 0.0114(17) 0.0010(17) C7 0.0439(18) 0.060(2) 0.0337(17) -0.0055(15) 0.0103(14) 0.0058(15) C8 0.0307(14) 0.0369(16) 0.0329(15) 0.0015(13) 0.0060(12) 0.0062(12) C9 0.0340(15) 0.0396(17) 0.0334(16) -0.0006(13) 0.0076(12) 0.0069(12) C10 0.069(2) 0.0418(18) 0.0407(19) -0.0057(15) 0.0066(16) 0.0084(17) C11 0.068(2) 0.041(2) 0.061(2) -0.0074(17) 0.0031(19) -0.0018(17) C12 0.068(2) 0.0368(18) 0.053(2) -0.0048(16) 0.0094(18) 0.0046(16) C13 0.091(3) 0.044(2) 0.044(2) 0.0056(16) 0.0070(19) 0.022(2) C14 0.062(2) 0.054(2) 0.068(3) -0.015(2) -0.014(2) 0.0156(19) C15 0.0354(16) 0.070(2) 0.0347(17) -0.0017(16) 0.0090(13) 0.0080(15) C16 0.058(2) 0.078(3) 0.046(2) 0.0140(19) 0.0194(18) 0.0080(19) C17 0.0420(17) 0.059(2) 0.0386(18) 0.0086(16) 0.0137(14) 0.0068(15) C18 0.0464(18) 0.055(2) 0.0424(18) 0.0108(16) 0.0112(15) 0.0026(15) C19 0.079(3) 0.055(2) 0.061(3) 0.015(2) 0.022(2) 0.001(2) C20 0.059(2) 0.043(2) 0.053(2) 0.0077(16) 0.0114(17) 0.0070(16) Cu1 0.0436(2) 0.0350(2) 0.0358(2) 0.00311(15) 0.01298(16) 0.00589(15) Cu2 0.0483(2) 0.0403(2) 0.0315(2) 0.00344(16) 0.01281(16) 0.00841(16) N1 0.0375(13) 0.0354(13) 0.0316(12) 0.0006(10) 0.0105(10) 0.0058(10) N2 0.0461(15) 0.0358(14) 0.0340(14) -0.0021(11) 0.0064(11) 0.0056(11) N3 0.0503(15) 0.0376(15) 0.0486(16) 0.0040(12) 0.0148(13) 0.0027(12) N4 0.0442(15) 0.0531(17) 0.0348(14) 0.0006(12) 0.0129(12) 0.0064(12) N5 0.0523(16) 0.0427(15) 0.0411(15) 0.0038(12) 0.0127(13) 0.0064(12) N6 0.0627(19) 0.0546(19) 0.0481(18) -0.0109(15) 0.0133(15) 0.0090(15) N7 0.123(3) 0.0411(18) 0.056(2) 0.0005(15) 0.031(2) 0.0160(18) O1 0.0889(19) 0.0454(14) 0.0508(15) 0.0114(11) 0.0411(14) 0.0194(13) O2 0.0496(13) 0.0630(15) 0.0345(12) 0.0098(10) 0.0181(10) 0.0148(11) O3 0.0583(14) 0.0342(12) 0.0319(11) 0.0019(9) 0.0095(10) 0.0104(10) O4 0.0547(13) 0.0400(12) 0.0301(11) -0.0002(9) 0.0112(10) 0.0099(10) O5 0.0644(16) 0.0513(15) 0.0527(16) -0.0112(12) -0.0055(12) -0.0008(12) O11 0.181(4) 0.092(3) 0.182(5) 0.000(3) 0.107(4) 0.043(3) O12 0.164(4) 0.136(4) 0.087(3) -0.020(3) 0.003(3) -0.055(3) O13 0.173(4) 0.077(2) 0.081(3) 0.008(2) 0.014(3) 0.019(2) O14 0.154(4) 0.152(4) 0.132(4) -0.018(3) 0.087(3) -0.066(3) S1 0.0536(5) 0.0895(7) 0.0354(4) -0.0017(5) 0.0155(4) 0.0119(5) S2 0.0865(8) 0.0427(5) 0.0728(7) 0.0103(5) 0.0180(6) 0.0023(5) Cl1 0.0939(7) 0.0544(6) 0.0575(6) 0.0012(5) 0.0330(5) -0.0055(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.250(4) . ? C1 O1 1.266(4) . ? C1 C2 1.492(4) . ? C2 C7 1.404(4) . ? C2 C3 1.408(4) . ? C3 C4 1.400(4) . ? C3 N1 1.424(4) . ? C4 C5 1.378(5) . ? C4 H4 0.9300 . ? C5 C6 1.385(5) . ? C5 H5 0.9300 . ? C6 C7 1.358(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O3 1.264(3) . ? C8 N1 1.309(4) . ? C8 C9 1.518(4) . ? C9 O4 1.280(4) . ? C9 N2 1.281(4) . ? C10 N2 1.460(4) . ? C10 C11 1.515(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.496(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N3 1.484(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N3 1.467(4) . ? C13 C14 1.487(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O5 1.431(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N4 1.319(4) . ? C15 N6 1.326(5) . ? C15 S1 1.734(3) . ? C16 C17 1.342(5) . ? C16 S1 1.717(4) . ? C16 H16 0.9300 . ? C17 N4 1.395(4) . ? C17 C18 1.446(5) . ? C18 C19 1.341(5) . ? C18 N5 1.392(4) . ? C19 S2 1.720(4) . ? C19 H19 0.9300 . ? C20 N7 1.322(5) . ? C20 N5 1.324(4) . ? C20 S2 1.724(4) . ? Cu1 O1 1.918(2) . ? Cu1 N2 1.947(3) . ? Cu1 N1 1.969(2) . ? Cu1 N3 2.015(3) . ? Cu1 O5 2.477(3) . ? Cu2 O4 1.926(2) . ? Cu2 N5 1.964(3) . ? Cu2 O3 1.968(2) . ? Cu2 N4 1.974(3) . ? Cu2 O2 2.368(2) 7 ? N3 H3 0.9100 . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N7 H7A 0.8600 . ? N7 H7B 0.8600 . ? O2 Cu2 2.368(2) 7 ? O5 H5A 0.9120 . ? O11 Cl1 1.378(4) . ? O12 Cl1 1.386(4) . ? O13 Cl1 1.417(4) . ? O14 Cl1 1.379(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 121.1(3) . . ? O2 C1 C2 117.6(3) . . ? O1 C1 C2 121.3(3) . . ? C7 C2 C3 117.8(3) . . ? C7 C2 C1 116.0(3) . . ? C3 C2 C1 126.2(3) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 N1 121.1(3) . . ? C2 C3 N1 119.9(3) . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 122.7(3) . . ? C6 C7 H7 118.7 . . ? C2 C7 H7 118.7 . . ? O3 C8 N1 130.2(3) . . ? O3 C8 C9 114.9(3) . . ? N1 C8 C9 114.9(3) . . ? O4 C9 N2 127.9(3) . . ? O4 C9 C8 115.6(3) . . ? N2 C9 C8 116.5(3) . . ? N2 C10 C11 110.8(3) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 112.0(3) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C11 113.8(3) . . ? N3 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? N3 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? N3 C13 C14 112.8(3) . . ? N3 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N3 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O5 C14 C13 110.7(3) . . ? O5 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? O5 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N4 C15 N6 124.7(3) . . ? N4 C15 S1 112.9(3) . . ? N6 C15 S1 122.4(3) . . ? C17 C16 S1 110.6(3) . . ? C17 C16 H16 124.7 . . ? S1 C16 H16 124.7 . . ? C16 C17 N4 114.9(3) . . ? C16 C17 C18 130.4(3) . . ? N4 C17 C18 114.7(3) . . ? C19 C18 N5 114.9(3) . . ? C19 C18 C17 130.6(3) . . ? N5 C18 C17 114.5(3) . . ? C18 C19 S2 110.4(3) . . ? C18 C19 H19 124.8 . . ? S2 C19 H19 124.8 . . ? N7 C20 N5 123.6(3) . . ? N7 C20 S2 123.4(3) . . ? N5 C20 S2 113.0(3) . . ? O1 Cu1 N2 161.59(12) . . ? O1 Cu1 N1 92.02(10) . . ? N2 Cu1 N1 84.79(10) . . ? O1 Cu1 N3 88.46(11) . . ? N2 Cu1 N3 94.95(11) . . ? N1 Cu1 N3 179.19(10) . . ? O1 Cu1 O5 96.75(11) . . ? N2 Cu1 O5 101.64(10) . . ? N1 Cu1 O5 102.47(9) . . ? N3 Cu1 O5 76.82(10) . . ? O4 Cu2 N5 172.17(10) . . ? O4 Cu2 O3 83.84(9) . . ? N5 Cu2 O3 96.90(10) . . ? O4 Cu2 N4 94.91(10) . . ? N5 Cu2 N4 82.85(11) . . ? O3 Cu2 N4 168.82(10) . . ? O4 Cu2 O2 96.42(9) . 7 ? N5 Cu2 O2 91.39(10) . 7 ? O3 Cu2 O2 89.00(8) . 7 ? N4 Cu2 O2 102.17(9) . 7 ? C8 N1 C3 123.2(3) . . ? C8 N1 Cu1 111.4(2) . . ? C3 N1 Cu1 125.3(2) . . ? C9 N2 C10 118.3(3) . . ? C9 N2 Cu1 112.3(2) . . ? C10 N2 Cu1 129.4(2) . . ? C13 N3 C12 111.3(3) . . ? C13 N3 Cu1 108.4(2) . . ? C12 N3 Cu1 118.4(2) . . ? C13 N3 H3 106.0 . . ? C12 N3 H3 106.0 . . ? Cu1 N3 H3 106.0 . . ? C15 N4 C17 111.5(3) . . ? C15 N4 Cu2 134.4(2) . . ? C17 N4 Cu2 113.5(2) . . ? C20 N5 C18 111.4(3) . . ? C20 N5 Cu2 134.2(2) . . ? C18 N5 Cu2 114.2(2) . . ? C15 N6 H6A 120.0 . . ? C15 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C20 N7 H7A 120.0 . . ? C20 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? C1 O1 Cu1 131.3(2) . . ? C1 O2 Cu2 116.7(2) . 7 ? C8 O3 Cu2 112.62(18) . . ? C9 O4 Cu2 112.91(19) . . ? C14 O5 Cu1 104.7(2) . . ? C14 O5 H5A 112.8 . . ? Cu1 O5 H5A 116.1 . . ? C16 S1 C15 90.15(18) . . ? C19 S2 C20 90.28(19) . . ? O11 Cl1 O14 108.4(3) . . ? O11 Cl1 O12 114.0(4) . . ? O14 Cl1 O12 110.4(3) . . ? O11 Cl1 O13 108.1(3) . . ? O14 Cl1 O13 110.5(3) . . ? O12 Cl1 O13 105.4(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 O2 C1 C2 C7 -11.9(4) . . . . ? O1 C1 C2 C7 166.1(3) . . . . ? O2 C1 C2 C3 168.7(3) . . . . ? O1 C1 C2 C3 -13.2(5) . . . . ? C7 C2 C3 C4 -4.2(4) . . . . ? C1 C2 C3 C4 175.2(3) . . . . ? C7 C2 C3 N1 176.6(3) . . . . ? C1 C2 C3 N1 -4.1(5) . . . . ? C2 C3 C4 C5 3.6(5) . . . . ? N1 C3 C4 C5 -177.1(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C7 -2.7(6) . . . . ? C5 C6 C7 C2 2.1(5) . . . . ? C3 C2 C7 C6 1.4(5) . . . . ? C1 C2 C7 C6 -178.0(3) . . . . ? O3 C8 C9 O4 -1.6(4) . . . . ? N1 C8 C9 O4 179.4(2) . . . . ? O3 C8 C9 N2 178.7(3) . . . . ? N1 C8 C9 N2 -0.3(4) . . . . ? N2 C10 C11 C12 62.6(4) . . . . ? C10 C11 C12 N3 -77.6(4) . . . . ? N3 C13 C14 O5 -51.3(4) . . . . ? S1 C16 C17 N4 1.3(4) . . . . ? S1 C16 C17 C18 179.0(3) . . . . ? C16 C17 C18 C19 4.4(7) . . . . ? N4 C17 C18 C19 -177.8(4) . . . . ? C16 C17 C18 N5 -173.6(4) . . . . ? N4 C17 C18 N5 4.2(4) . . . . ? N5 C18 C19 S2 2.0(4) . . . . ? C17 C18 C19 S2 -176.1(3) . . . . ? O3 C8 N1 C3 1.3(5) . . . . ? C9 C8 N1 C3 -179.9(2) . . . . ? O3 C8 N1 Cu1 178.8(3) . . . . ? C9 C8 N1 Cu1 -2.5(3) . . . . ? C4 C3 N1 C8 18.5(4) . . . . ? C2 C3 N1 C8 -162.3(3) . . . . ? C4 C3 N1 Cu1 -158.6(2) . . . . ? C2 C3 N1 Cu1 20.6(4) . . . . ? O1 Cu1 N1 C8 165.0(2) . . . . ? N2 Cu1 N1 C8 3.2(2) . . . . ? N3 Cu1 N1 C8 -69(8) . . . . ? O5 Cu1 N1 C8 -97.6(2) . . . . ? O1 Cu1 N1 C3 -17.6(2) . . . . ? N2 Cu1 N1 C3 -179.4(2) . . . . ? N3 Cu1 N1 C3 109(8) . . . . ? O5 Cu1 N1 C3 79.8(2) . . . . ? O4 C9 N2 C10 3.8(5) . . . . ? C8 C9 N2 C10 -176.6(3) . . . . ? O4 C9 N2 Cu1 -176.7(2) . . . . ? C8 C9 N2 Cu1 2.9(3) . . . . ? C11 C10 N2 C9 158.1(3) . . . . ? C11 C10 N2 Cu1 -21.3(4) . . . . ? O1 Cu1 N2 C9 -84.1(4) . . . . ? N1 Cu1 N2 C9 -3.4(2) . . . . ? N3 Cu1 N2 C9 175.8(2) . . . . ? O5 Cu1 N2 C9 98.3(2) . . . . ? O1 Cu1 N2 C10 95.4(4) . . . . ? N1 Cu1 N2 C10 176.1(3) . . . . ? N3 Cu1 N2 C10 -4.7(3) . . . . ? O5 Cu1 N2 C10 -82.2(3) . . . . ? C14 C13 N3 C12 -73.2(4) . . . . ? C14 C13 N3 Cu1 58.7(3) . . . . ? C11 C12 N3 C13 169.9(3) . . . . ? C11 C12 N3 Cu1 43.4(4) . . . . ? O1 Cu1 N3 C13 64.6(2) . . . . ? N2 Cu1 N3 C13 -133.5(2) . . . . ? N1 Cu1 N3 C13 -62(8) . . . . ? O5 Cu1 N3 C13 -32.7(2) . . . . ? O1 Cu1 N3 C12 -167.5(3) . . . . ? N2 Cu1 N3 C12 -5.6(3) . . . . ? N1 Cu1 N3 C12 66(8) . . . . ? O5 Cu1 N3 C12 95.2(2) . . . . ? N6 C15 N4 C17 -179.9(3) . . . . ? S1 C15 N4 C17 0.1(4) . . . . ? N6 C15 N4 Cu2 9.2(5) . . . . ? S1 C15 N4 Cu2 -170.74(18) . . . . ? C16 C17 N4 C15 -0.9(4) . . . . ? C18 C17 N4 C15 -179.1(3) . . . . ? C16 C17 N4 Cu2 172.0(3) . . . . ? C18 C17 N4 Cu2 -6.2(4) . . . . ? O4 Cu2 N4 C15 -12.0(3) . . . . ? N5 Cu2 N4 C15 175.5(3) . . . . ? O3 Cu2 N4 C15 -95.1(6) . . . . ? O2 Cu2 N4 C15 85.6(3) 7 . . . ? O4 Cu2 N4 C17 177.2(2) . . . . ? N5 Cu2 N4 C17 4.8(2) . . . . ? O3 Cu2 N4 C17 94.2(5) . . . . ? O2 Cu2 N4 C17 -85.1(2) 7 . . . ? N7 C20 N5 C18 -178.8(4) . . . . ? S2 C20 N5 C18 1.8(4) . . . . ? N7 C20 N5 Cu2 -3.8(6) . . . . ? S2 C20 N5 Cu2 176.74(19) . . . . ? C19 C18 N5 C20 -2.4(4) . . . . ? C17 C18 N5 C20 175.9(3) . . . . ? C19 C18 N5 Cu2 -178.5(3) . . . . ? C17 C18 N5 Cu2 -0.1(4) . . . . ? O4 Cu2 N5 C20 108.8(8) . . . . ? O3 Cu2 N5 C20 13.9(3) . . . . ? N4 Cu2 N5 C20 -177.4(4) . . . . ? O2 Cu2 N5 C20 -75.3(3) 7 . . . ? O4 Cu2 N5 C18 -76.3(8) . . . . ? O3 Cu2 N5 C18 -171.3(2) . . . . ? N4 Cu2 N5 C18 -2.5(2) . . . . ? O2 Cu2 N5 C18 99.6(2) 7 . . . ? O2 C1 O1 Cu1 -169.3(2) . . . . ? C2 C1 O1 Cu1 12.8(5) . . . . ? N2 Cu1 O1 C1 80.3(5) . . . . ? N1 Cu1 O1 C1 0.8(3) . . . . ? N3 Cu1 O1 C1 -178.6(3) . . . . ? O5 Cu1 O1 C1 -102.0(3) . . . . ? O1 C1 O2 Cu2 94.2(3) . . . 7 ? C2 C1 O2 Cu2 -87.8(3) . . . 7 ? N1 C8 O3 Cu2 177.3(3) . . . . ? C9 C8 O3 Cu2 -1.5(3) . . . . ? O4 Cu2 O3 C8 2.8(2) . . . . ? N5 Cu2 O3 C8 175.0(2) . . . . ? N4 Cu2 O3 C8 87.0(6) . . . . ? O2 Cu2 O3 C8 -93.7(2) 7 . . . ? N2 C9 O4 Cu2 -176.4(3) . . . . ? C8 C9 O4 Cu2 4.0(3) . . . . ? N5 Cu2 O4 C9 -99.6(8) . . . . ? O3 Cu2 O4 C9 -3.8(2) . . . . ? N4 Cu2 O4 C9 -172.6(2) . . . . ? O2 Cu2 O4 C9 84.5(2) 7 . . . ? C13 C14 O5 Cu1 19.3(4) . . . . ? O1 Cu1 O5 C14 -79.2(2) . . . . ? N2 Cu1 O5 C14 100.1(2) . . . . ? N1 Cu1 O5 C14 -172.8(2) . . . . ? N3 Cu1 O5 C14 7.6(2) . . . . ? C17 C16 S1 C15 -1.0(3) . . . . ? N4 C15 S1 C16 0.5(3) . . . . ? N6 C15 S1 C16 -179.5(3) . . . . ? C18 C19 S2 C20 -0.8(3) . . . . ? N7 C20 S2 C19 180.0(4) . . . . ? N5 C20 S2 C19 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.773 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.079 data_a _database_code_depnum_ccdc_archive 'CCDC 805256' #TrackingRef 'a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cl Cu2 N5 O10 S2' _chemical_formula_weight 747.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.8016(15) _cell_length_b 11.8840(14) _cell_length_c 12.652(3) _cell_angle_alpha 103.236(3) _cell_angle_beta 101.213(3) _cell_angle_gamma 117.145(2) _cell_volume 1442.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 1.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7407 _exptl_absorpt_correction_T_max 0.9487 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 7415 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0998 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.51 _reflns_number_total 5287 _reflns_number_gt 2890 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0647P)^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 5287 _refine_ls_number_parameters 403 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1525 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 1.014 _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 0.22054(9) -0.18839(8) 0.10307(7) 0.0462(3) Uani 1 1 d . . . Cu2 Cu 0.19582(8) 0.24136(8) 0.25302(7) 0.0383(3) Uani 1 1 d . . . S1 S 0.5995(2) 0.68843(19) 0.38852(18) 0.0576(6) Uani 1 1 d . . . S2 S 0.1034(2) 0.4031(2) 0.56107(19) 0.0680(6) Uani 1 1 d . . . O1 O 0.0942(5) 0.3028(5) 0.1666(4) 0.0474(12) Uani 1 1 d . . . O2 O 0.0106(4) 0.3489(4) 0.0233(4) 0.0476(12) Uani 1 1 d . . . O3 O 0.2105(5) -0.0534(4) 0.0448(4) 0.0454(12) Uani 1 1 d . . . O4 O 0.2148(4) 0.1103(4) 0.3150(3) 0.0406(11) Uani 1 1 d . . . O5 O 0.2820(5) -0.2531(5) -0.0197(4) 0.0573(14) Uani 1 1 d . . . H5A H 0.2499 -0.2638 -0.0915 0.086 Uiso 1 1 d R . . N1 N 0.2031(5) 0.1405(5) 0.1126(4) 0.0341(12) Uani 1 1 d . . . N2 N 0.2111(5) -0.0882(5) 0.2410(4) 0.0408(14) Uani 1 1 d . . . N3 N 0.2268(7) -0.3316(6) 0.1530(5) 0.0578(18) Uani 1 1 d . . . H3 H 0.1423 -0.4070 0.1157 0.069 Uiso 1 1 calc R . . N4 N 0.3908(5) 0.4527(5) 0.3255(4) 0.0387(13) Uani 1 1 d . . . N5 N 0.1812(5) 0.3326(5) 0.3986(4) 0.0381(13) Uani 1 1 d . . . C1 C 0.0758(7) 0.3001(6) 0.0631(6) 0.0392(16) Uani 1 1 d . . . C2 C 0.1354(6) 0.2453(6) -0.0127(5) 0.0355(15) Uani 1 1 d . . . C3 C 0.1984(6) 0.1724(6) 0.0107(5) 0.0346(15) Uani 1 1 d . . . C4 C 0.2611(7) 0.1380(7) -0.0638(6) 0.0470(18) Uani 1 1 d . . . H4 H 0.3075 0.0954 -0.0455 0.056 Uiso 1 1 calc R . . C5 C 0.2548(7) 0.1664(7) -0.1637(6) 0.0485(18) Uani 1 1 d . . . H5 H 0.2972 0.1437 -0.2120 0.058 Uiso 1 1 calc R . . C6 C 0.1856(7) 0.2287(7) -0.1920(6) 0.0518(19) Uani 1 1 d . . . H6 H 0.1777 0.2442 -0.2611 0.062 Uiso 1 1 calc R . . C7 C 0.1284(7) 0.2676(6) -0.1181(6) 0.0429(17) Uani 1 1 d . . . H7 H 0.0831 0.3104 -0.1381 0.051 Uiso 1 1 calc R . . C8 C 0.2093(6) 0.0356(6) 0.1199(5) 0.0324(15) Uani 1 1 d . . . C9 C 0.2138(6) 0.0209(7) 0.2373(5) 0.0363(16) Uani 1 1 d . . . C10 C 0.2123(8) -0.1176(7) 0.3475(6) 0.0505(19) Uani 1 1 d . . . H10A H 0.1461 -0.1050 0.3750 0.061 Uiso 1 1 calc R . . H10B H 0.3010 -0.0536 0.4065 0.061 Uiso 1 1 calc R . . C11 C 0.1809(11) -0.2578(10) 0.3308(8) 0.088(3) Uani 1 1 d . . . H11A H 0.1939 -0.2654 0.4063 0.106 Uiso 1 1 calc R . . H11B H 0.0851 -0.3189 0.2858 0.106 Uiso 1 1 calc R . . C12 C 0.2534(10) -0.3089(9) 0.2763(8) 0.081(3) Uani 1 1 d . . . H12A H 0.2317 -0.3941 0.2862 0.097 Uiso 1 1 calc R . . H12B H 0.3499 -0.2454 0.3173 0.097 Uiso 1 1 calc R . . C13 C 0.3142(9) -0.3623(8) 0.1060(8) 0.073(3) Uani 1 1 d . . . H13A H 0.2989 -0.4490 0.1083 0.088 Uiso 1 1 calc R . . H13B H 0.4080 -0.2933 0.1525 0.088 Uiso 1 1 calc R . . C14 C 0.2891(10) -0.3681(9) -0.0163(8) 0.081(3) Uani 1 1 d . . . H14A H 0.3622 -0.3669 -0.0413 0.098 Uiso 1 1 calc R . . H14B H 0.2046 -0.4508 -0.0673 0.098 Uiso 1 1 calc R . . C15 C 0.4960(7) 0.5197(7) 0.2971(6) 0.0476(18) Uani 1 1 d . . . C16 C 0.4969(7) 0.6663(7) 0.4664(6) 0.0481(19) Uani 1 1 d . . . H16 H 0.5111 0.7335 0.5314 0.058 Uiso 1 1 calc R . . C17 C 0.3880(7) 0.5340(7) 0.4204(6) 0.0410(17) Uani 1 1 d . . . C18 C 0.2728(7) 0.4699(7) 0.4585(6) 0.0425(17) Uani 1 1 d . . . C19 C 0.2429(8) 0.5221(7) 0.5463(6) 0.057(2) Uani 1 1 d . . . H19 H 0.2929 0.6133 0.5938 0.068 Uiso 1 1 calc R . . C20 C 0.0876(7) 0.2826(7) 0.4457(6) 0.0491(19) Uani 1 1 d . . . C21 C 0.5277(8) 0.4600(8) 0.1994(7) 0.065(2) Uani 1 1 d . . . H21A H 0.5020 0.3686 0.1918 0.098 Uiso 1 1 calc R . . H21B H 0.6233 0.5130 0.2138 0.098 Uiso 1 1 calc R . . H21C H 0.4785 0.4598 0.1293 0.098 Uiso 1 1 calc R . . C22 C -0.0206(8) 0.1349(8) 0.4030(7) 0.073(3) Uani 1 1 d . . . H22A H -0.0566 0.0997 0.3200 0.109 Uiso 1 1 calc R . . H22B H -0.0921 0.1248 0.4329 0.109 Uiso 1 1 calc R . . H22C H 0.0176 0.0857 0.4287 0.109 Uiso 1 1 calc R . . O6 O 0.1113(6) -0.3407(6) -0.2294(5) 0.092(2) Uani 1 1 d . . . H6A H 0.1389 -0.2963 -0.2759 0.139 Uiso 1 1 d R . . H6B H 0.0381 -0.3363 -0.2180 0.139 Uiso 1 1 d R . . Cl1 Cl 0.5893(3) 0.0847(3) 0.2969(2) 0.0895(8) Uani 1 1 d D . . O7A O 0.7243(7) 0.1535(11) 0.3178(12) 0.168(10) Uani 0.691(14) 1 d PD A 1 O8A O 0.5167(10) -0.0415(7) 0.2120(8) 0.120(5) Uani 0.691(14) 1 d PD A 1 O9A O 0.5326(9) 0.1620(8) 0.2575(9) 0.105(5) Uani 0.691(14) 1 d PD A 1 O10A O 0.5589(11) 0.0797(13) 0.3997(7) 0.154(7) Uani 0.691(14) 1 d PD A 1 O7B O 0.7289(11) 0.1899(17) 0.351(2) 0.077(10) Uani 0.309(14) 1 d PD A 2 O8B O 0.511(2) 0.123(2) 0.341(2) 0.157(14) Uiso 0.309(14) 1 d PD A 2 O9B O 0.581(2) -0.0283(17) 0.325(2) 0.131(12) Uiso 0.309(14) 1 d PD A 2 O10B O 0.555(3) 0.049(3) 0.1786(9) 0.22(2) Uiso 0.309(14) 1 d PD A 2 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 0.0686(6) 0.0417(6) 0.0456(5) 0.0187(4) 0.0206(5) 0.0403(5) Cu2 0.0479(5) 0.0348(5) 0.0339(5) 0.0082(4) 0.0115(4) 0.0260(4) S1 0.0476(12) 0.0397(12) 0.0630(13) 0.0114(10) 0.0077(10) 0.0135(10) S2 0.0828(16) 0.0632(15) 0.0625(14) 0.0137(12) 0.0413(12) 0.0398(13) O1 0.058(3) 0.055(3) 0.038(3) 0.012(2) 0.009(2) 0.041(3) O2 0.052(3) 0.044(3) 0.055(3) 0.021(3) 0.012(2) 0.033(3) O3 0.073(3) 0.040(3) 0.041(3) 0.018(2) 0.023(3) 0.039(3) O4 0.056(3) 0.041(3) 0.032(3) 0.012(2) 0.015(2) 0.031(3) O5 0.074(4) 0.050(3) 0.064(3) 0.018(3) 0.032(3) 0.043(3) N1 0.040(3) 0.032(3) 0.035(3) 0.011(3) 0.015(3) 0.022(3) N2 0.055(4) 0.044(4) 0.036(3) 0.019(3) 0.014(3) 0.034(3) N3 0.080(5) 0.048(4) 0.067(5) 0.028(3) 0.021(4) 0.049(4) N4 0.043(3) 0.033(3) 0.034(3) 0.009(3) 0.009(3) 0.019(3) N5 0.040(3) 0.033(3) 0.038(3) 0.006(3) 0.011(3) 0.021(3) C1 0.046(4) 0.032(4) 0.042(4) 0.011(3) 0.010(3) 0.025(4) C2 0.033(4) 0.026(4) 0.036(4) 0.010(3) 0.004(3) 0.011(3) C3 0.048(4) 0.024(4) 0.025(3) 0.008(3) 0.008(3) 0.015(3) C4 0.065(5) 0.038(4) 0.043(4) 0.020(4) 0.023(4) 0.027(4) C5 0.063(5) 0.044(5) 0.048(4) 0.021(4) 0.034(4) 0.028(4) C6 0.060(5) 0.040(4) 0.047(5) 0.021(4) 0.014(4) 0.018(4) C7 0.047(4) 0.034(4) 0.044(4) 0.013(3) 0.007(3) 0.023(4) C8 0.032(4) 0.029(4) 0.032(4) 0.006(3) 0.007(3) 0.017(3) C9 0.041(4) 0.036(4) 0.031(4) 0.009(3) 0.005(3) 0.023(4) C10 0.073(5) 0.056(5) 0.042(4) 0.026(4) 0.022(4) 0.043(5) C11 0.151(10) 0.098(8) 0.082(7) 0.065(6) 0.058(7) 0.093(8) C12 0.111(8) 0.060(6) 0.081(7) 0.035(5) 0.014(6) 0.055(6) C13 0.084(7) 0.054(6) 0.098(7) 0.025(5) 0.025(6) 0.051(5) C14 0.114(8) 0.066(6) 0.099(8) 0.026(6) 0.053(6) 0.069(6) C15 0.042(4) 0.042(5) 0.051(5) 0.013(4) 0.008(4) 0.021(4) C16 0.056(5) 0.032(4) 0.046(4) 0.008(4) 0.005(4) 0.022(4) C17 0.055(5) 0.034(4) 0.034(4) 0.008(3) 0.007(3) 0.029(4) C18 0.055(5) 0.037(4) 0.037(4) 0.011(3) 0.011(4) 0.029(4) C19 0.073(6) 0.041(5) 0.058(5) 0.011(4) 0.024(4) 0.033(4) C20 0.050(5) 0.047(5) 0.049(5) 0.011(4) 0.016(4) 0.028(4) C21 0.052(5) 0.059(5) 0.060(5) 0.007(4) 0.022(4) 0.017(4) C22 0.063(6) 0.053(6) 0.086(7) 0.013(5) 0.034(5) 0.021(5) O6 0.111(5) 0.115(5) 0.081(4) 0.038(4) 0.048(4) 0.076(5) Cl1 0.0722(18) 0.0650(17) 0.105(2) 0.0070(16) 0.0307(16) 0.0275(15) O7A 0.088(12) 0.124(13) 0.34(3) 0.108(15) 0.125(14) 0.061(10) O8A 0.154(10) 0.037(6) 0.116(9) -0.013(6) 0.008(8) 0.044(6) O9A 0.087(7) 0.069(7) 0.131(10) 0.021(6) 0.001(6) 0.041(6) O10A 0.147(12) 0.225(16) 0.078(8) 0.048(9) 0.047(8) 0.088(11) O7B 0.047(17) 0.057(15) 0.087(16) -0.017(12) -0.021(12) 0.035(13) _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 1.929(5) . ? Cu1 O3 1.953(4) . ? Cu1 N3 1.973(5) . ? Cu1 O5 1.982(5) . ? Cu1 O2 2.407(4) 2 ? Cu2 N1 1.944(5) . ? Cu2 O1 1.954(4) . ? Cu2 O4 1.974(4) . ? Cu2 N5 1.995(5) . ? Cu2 N4 2.301(5) . ? S1 C16 1.673(7) . ? S1 C15 1.733(7) . ? S2 C19 1.692(8) . ? S2 C20 1.706(7) . ? O1 C1 1.276(7) . ? O2 C1 1.253(7) . ? O2 Cu1 2.407(4) 2 ? O3 C8 1.257(7) . ? O4 C9 1.265(7) . ? O5 C14 1.416(8) . ? O5 H5A 0.8690 . ? N1 C8 1.304(7) . ? N1 C3 1.423(7) . ? N2 C9 1.295(7) . ? N2 C10 1.467(8) . ? N3 C13 1.426(9) . ? N3 C12 1.465(10) . ? N3 H3 0.9100 . ? N4 C15 1.306(8) . ? N4 C17 1.375(8) . ? N5 C20 1.321(8) . ? N5 C18 1.382(8) . ? C1 C2 1.494(9) . ? C2 C7 1.412(8) . ? C2 C3 1.418(8) . ? C3 C4 1.405(9) . ? C4 C5 1.378(9) . ? C4 H4 0.9300 . ? C5 C6 1.379(9) . ? C5 H5 0.9300 . ? C6 C7 1.369(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.528(8) . ? C10 C11 1.484(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.445(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.497(11) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C21 1.480(10) . ? C16 C17 1.382(9) . ? C16 H16 0.9300 . ? C17 C18 1.462(10) . ? C18 C19 1.335(9) . ? C19 H19 0.9300 . ? C20 C22 1.503(10) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O6 H6A 0.8893 . ? O6 H6B 0.9251 . ? Cl1 O7A 1.351(7) . ? Cl1 O8B 1.356(10) . ? Cl1 O8A 1.367(6) . ? Cl1 O10B 1.380(10) . ? Cl1 O10A 1.422(7) . ? Cl1 O7B 1.427(9) . ? Cl1 O9B 1.433(10) . ? Cl1 O9A 1.476(6) . ? 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 O3 84.4(2) . . ? N2 Cu1 N3 98.5(2) . . ? O3 Cu1 N3 176.8(2) . . ? N2 Cu1 O5 164.7(2) . . ? O3 Cu1 O5 93.54(19) . . ? N3 Cu1 O5 84.0(2) . . ? N2 Cu1 O2 106.03(19) . 2 ? O3 Cu1 O2 87.87(17) . 2 ? N3 Cu1 O2 90.1(2) . 2 ? O5 Cu1 O2 88.96(18) . 2 ? N1 Cu2 O1 91.78(19) . . ? N1 Cu2 O4 85.17(19) . . ? O1 Cu2 O4 154.36(19) . . ? N1 Cu2 N5 176.0(2) . . ? O1 Cu2 N5 90.12(19) . . ? O4 Cu2 N5 91.60(19) . . ? N1 Cu2 N4 105.9(2) . . ? O1 Cu2 N4 91.81(19) . . ? O4 Cu2 N4 113.53(18) . . ? N5 Cu2 N4 77.5(2) . . ? C16 S1 C15 90.8(4) . . ? C19 S2 C20 89.8(4) . . ? C1 O1 Cu2 129.4(4) . . ? C1 O2 Cu1 116.3(4) . 2 ? C8 O3 Cu1 111.9(4) . . ? C9 O4 Cu2 110.3(4) . . ? C14 O5 Cu1 112.4(5) . . ? C14 O5 H5A 108.6 . . ? Cu1 O5 H5A 123.6 . . ? C8 N1 C3 122.4(5) . . ? C8 N1 Cu2 112.4(4) . . ? C3 N1 Cu2 125.1(4) . . ? C9 N2 C10 119.4(5) . . ? C9 N2 Cu1 113.3(4) . . ? C10 N2 Cu1 127.1(4) . . ? C13 N3 C12 115.1(7) . . ? C13 N3 Cu1 107.3(5) . . ? C12 N3 Cu1 116.6(5) . . ? C13 N3 H3 105.6 . . ? C12 N3 H3 105.6 . . ? Cu1 N3 H3 105.6 . . ? C15 N4 C17 111.9(6) . . ? C15 N4 Cu2 138.4(5) . . ? C17 N4 Cu2 109.4(4) . . ? C20 N5 C18 111.8(6) . . ? C20 N5 Cu2 129.1(5) . . ? C18 N5 Cu2 118.9(5) . . ? O2 C1 O1 120.3(6) . . ? O2 C1 C2 117.8(6) . . ? O1 C1 C2 121.8(5) . . ? C7 C2 C3 116.5(6) . . ? C7 C2 C1 117.2(6) . . ? C3 C2 C1 126.3(6) . . ? C4 C3 C2 119.9(6) . . ? C4 C3 N1 120.6(5) . . ? C2 C3 N1 119.5(6) . . ? C5 C4 C3 120.8(6) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.0(7) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 119.8(6) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C2 122.7(6) . . ? C6 C7 H7 118.6 . . ? C2 C7 H7 118.6 . . ? O3 C8 N1 129.3(6) . . ? O3 C8 C9 117.0(5) . . ? N1 C8 C9 113.6(5) . . ? O4 C9 N2 128.7(6) . . ? O4 C9 C8 118.2(5) . . ? N2 C9 C8 113.1(5) . . ? N2 C10 C11 112.6(6) . . ? N2 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 120.4(8) . . ? C12 C11 H11A 107.2 . . ? C10 C11 H11A 107.2 . . ? C12 C11 H11B 107.2 . . ? C10 C11 H11B 107.2 . . ? H11A C11 H11B 106.9 . . ? C11 C12 N3 116.6(7) . . ? C11 C12 H12A 108.2 . . ? N3 C12 H12A 108.2 . . ? C11 C12 H12B 108.2 . . ? N3 C12 H12B 108.2 . . ? H12A C12 H12B 107.3 . . ? N3 C13 C14 110.9(7) . . ? N3 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O5 C14 C13 107.4(6) . . ? O5 C14 H14A 110.2 . . ? C13 C14 H14A 110.2 . . ? O5 C14 H14B 110.2 . . ? C13 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N4 C15 C21 124.7(6) . . ? N4 C15 S1 112.8(5) . . ? C21 C15 S1 122.5(6) . . ? C17 C16 S1 110.3(5) . . ? C17 C16 H16 124.8 . . ? S1 C16 H16 124.8 . . ? N4 C17 C16 114.1(7) . . ? N4 C17 C18 116.5(6) . . ? C16 C17 C18 129.4(6) . . ? C19 C18 N5 113.1(7) . . ? C19 C18 C17 130.1(7) . . ? N5 C18 C17 116.8(6) . . ? C18 C19 S2 112.2(6) . . ? C18 C19 H19 123.9 . . ? S2 C19 H19 123.9 . . ? N5 C20 C22 123.6(6) . . ? N5 C20 S2 113.0(5) . . ? C22 C20 S2 123.4(6) . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? H6A O6 H6B 108.2 . . ? O7A Cl1 O8B 130.7(12) . . ? O7A Cl1 O8A 115.6(6) . . ? O8B Cl1 O8A 113.6(11) . . ? O7A Cl1 O10B 94.2(13) . . ? O8B Cl1 O10B 113.7(7) . . ? O8A Cl1 O10B 50.8(10) . . ? O7A Cl1 O10A 112.2(6) . . ? O8B Cl1 O10A 50.9(11) . . ? O8A Cl1 O10A 111.0(5) . . ? O10B Cl1 O10A 153.5(12) . . ? O7A Cl1 O7B 20.5(12) . . ? O8B Cl1 O7B 110.5(7) . . ? O8A Cl1 O7B 136.0(11) . . ? O10B Cl1 O7B 108.8(7) . . ? O10A Cl1 O7B 97.5(12) . . ? O7A Cl1 O9B 97.1(11) . . ? O8B Cl1 O9B 110.0(7) . . ? O8A Cl1 O9B 60.9(9) . . ? O10B Cl1 O9B 108.5(7) . . ? O10A Cl1 O9B 66.4(10) . . ? O7B Cl1 O9B 104.9(6) . . ? O7A Cl1 O9A 108.6(5) . . ? O8B Cl1 O9A 52.8(11) . . ? O8A Cl1 O9A 105.4(4) . . ? O10B Cl1 O9A 69.7(11) . . ? O10A Cl1 O9A 103.1(5) . . ? O7B Cl1 O9A 99.7(9) . . ? O9B Cl1 O9A 154.2(9) . . ? 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 Cu2 O1 C1 -14.7(6) . . . . ? O4 Cu2 O1 C1 -97.2(7) . . . . ? N5 Cu2 O1 C1 168.9(6) . . . . ? N4 Cu2 O1 C1 91.4(6) . . . . ? N2 Cu1 O3 C8 3.1(4) . . . . ? N3 Cu1 O3 C8 160(4) . . . . ? O5 Cu1 O3 C8 -161.7(4) . . . . ? O2 Cu1 O3 C8 109.5(4) 2 . . . ? N1 Cu2 O4 C9 -4.2(4) . . . . ? O1 Cu2 O4 C9 79.8(6) . . . . ? N5 Cu2 O4 C9 173.5(4) . . . . ? N4 Cu2 O4 C9 -109.5(4) . . . . ? N2 Cu1 O5 C14 104.6(9) . . . . ? O3 Cu1 O5 C14 -173.7(5) . . . . ? N3 Cu1 O5 C14 4.3(5) . . . . ? O2 Cu1 O5 C14 -85.9(5) 2 . . . ? O1 Cu2 N1 C8 -151.3(4) . . . . ? O4 Cu2 N1 C8 3.2(4) . . . . ? N5 Cu2 N1 C8 -33(3) . . . . ? N4 Cu2 N1 C8 116.3(4) . . . . ? O1 Cu2 N1 C3 27.0(5) . . . . ? O4 Cu2 N1 C3 -178.5(5) . . . . ? N5 Cu2 N1 C3 145(3) . . . . ? N4 Cu2 N1 C3 -65.3(5) . . . . ? O3 Cu1 N2 C9 -5.2(5) . . . . ? N3 Cu1 N2 C9 176.1(5) . . . . ? O5 Cu1 N2 C9 77.7(9) . . . . ? O2 Cu1 N2 C9 -91.3(5) 2 . . . ? O3 Cu1 N2 C10 -180.0(6) . . . . ? N3 Cu1 N2 C10 1.3(6) . . . . ? O5 Cu1 N2 C10 -97.1(9) . . . . ? O2 Cu1 N2 C10 93.9(5) 2 . . . ? N2 Cu1 N3 C13 -144.0(5) . . . . ? O3 Cu1 N3 C13 59(5) . . . . ? O5 Cu1 N3 C13 20.9(5) . . . . ? O2 Cu1 N3 C13 109.8(5) 2 . . . ? N2 Cu1 N3 C12 -13.2(6) . . . . ? O3 Cu1 N3 C12 -170(4) . . . . ? O5 Cu1 N3 C12 151.7(6) . . . . ? O2 Cu1 N3 C12 -119.4(6) 2 . . . ? N1 Cu2 N4 C15 2.6(7) . . . . ? O1 Cu2 N4 C15 -89.8(7) . . . . ? O4 Cu2 N4 C15 94.2(7) . . . . ? N5 Cu2 N4 C15 -179.5(7) . . . . ? N1 Cu2 N4 C17 175.3(4) . . . . ? O1 Cu2 N4 C17 82.9(4) . . . . ? O4 Cu2 N4 C17 -93.1(4) . . . . ? N5 Cu2 N4 C17 -6.8(4) . . . . ? N1 Cu2 N5 C20 -27(3) . . . . ? O1 Cu2 N5 C20 91.7(6) . . . . ? O4 Cu2 N5 C20 -62.7(6) . . . . ? N4 Cu2 N5 C20 -176.5(6) . . . . ? N1 Cu2 N5 C18 159(3) . . . . ? O1 Cu2 N5 C18 -83.0(4) . . . . ? O4 Cu2 N5 C18 122.6(4) . . . . ? N4 Cu2 N5 C18 8.8(4) . . . . ? Cu1 O2 C1 O1 -101.8(6) 2 . . . ? Cu1 O2 C1 C2 80.8(6) 2 . . . ? Cu2 O1 C1 O2 -177.5(4) . . . . ? Cu2 O1 C1 C2 -0.3(9) . . . . ? O2 C1 C2 C7 7.7(9) . . . . ? O1 C1 C2 C7 -169.6(6) . . . . ? O2 C1 C2 C3 -172.2(6) . . . . ? O1 C1 C2 C3 10.5(10) . . . . ? C7 C2 C3 C4 6.0(9) . . . . ? C1 C2 C3 C4 -174.1(6) . . . . ? C7 C2 C3 N1 -177.0(5) . . . . ? C1 C2 C3 N1 2.9(9) . . . . ? C8 N1 C3 C4 -30.0(9) . . . . ? Cu2 N1 C3 C4 151.8(5) . . . . ? C8 N1 C3 C2 153.0(6) . . . . ? Cu2 N1 C3 C2 -25.2(8) . . . . ? C2 C3 C4 C5 -4.2(10) . . . . ? N1 C3 C4 C5 178.8(6) . . . . ? C3 C4 C5 C6 -0.4(10) . . . . ? C4 C5 C6 C7 2.9(11) . . . . ? C5 C6 C7 C2 -0.8(11) . . . . ? C3 C2 C7 C6 -3.6(10) . . . . ? C1 C2 C7 C6 176.5(6) . . . . ? Cu1 O3 C8 N1 -179.8(5) . . . . ? Cu1 O3 C8 C9 -0.8(7) . . . . ? C3 N1 C8 O3 -1.1(10) . . . . ? Cu2 N1 C8 O3 177.3(5) . . . . ? C3 N1 C8 C9 179.9(5) . . . . ? Cu2 N1 C8 C9 -1.8(6) . . . . ? Cu2 O4 C9 N2 -172.9(6) . . . . ? Cu2 O4 C9 C8 4.4(7) . . . . ? C10 N2 C9 O4 -1.6(10) . . . . ? Cu1 N2 C9 O4 -176.8(5) . . . . ? C10 N2 C9 C8 -178.9(5) . . . . ? Cu1 N2 C9 C8 5.8(7) . . . . ? O3 C8 C9 O4 179.0(6) . . . . ? N1 C8 C9 O4 -1.9(8) . . . . ? O3 C8 C9 N2 -3.4(8) . . . . ? N1 C8 C9 N2 175.8(5) . . . . ? C9 N2 C10 C11 168.4(7) . . . . ? Cu1 N2 C10 C11 -17.1(9) . . . . ? N2 C10 C11 C12 50.9(11) . . . . ? C10 C11 C12 N3 -68.6(12) . . . . ? C13 N3 C12 C11 171.0(8) . . . . ? Cu1 N3 C12 C11 43.9(10) . . . . ? C12 N3 C13 C14 -173.6(7) . . . . ? Cu1 N3 C13 C14 -42.0(8) . . . . ? Cu1 O5 C14 C13 -27.2(8) . . . . ? N3 C13 C14 O5 46.1(9) . . . . ? C17 N4 C15 C21 179.5(6) . . . . ? Cu2 N4 C15 C21 -7.9(11) . . . . ? C17 N4 C15 S1 0.7(7) . . . . ? Cu2 N4 C15 S1 173.3(3) . . . . ? C16 S1 C15 N4 0.0(5) . . . . ? C16 S1 C15 C21 -178.8(6) . . . . ? C15 S1 C16 C17 -0.8(5) . . . . ? C15 N4 C17 C16 -1.4(8) . . . . ? Cu2 N4 C17 C16 -176.1(4) . . . . ? C15 N4 C17 C18 178.9(5) . . . . ? Cu2 N4 C17 C18 4.1(6) . . . . ? S1 C16 C17 N4 1.4(7) . . . . ? S1 C16 C17 C18 -178.9(5) . . . . ? C20 N5 C18 C19 -3.0(8) . . . . ? Cu2 N5 C18 C19 172.5(5) . . . . ? C20 N5 C18 C17 174.8(6) . . . . ? Cu2 N5 C18 C17 -9.6(7) . . . . ? N4 C17 C18 C19 -179.9(6) . . . . ? C16 C17 C18 C19 0.4(12) . . . . ? N4 C17 C18 N5 2.7(8) . . . . ? C16 C17 C18 N5 -177.0(6) . . . . ? N5 C18 C19 S2 1.8(8) . . . . ? C17 C18 C19 S2 -175.7(5) . . . . ? C20 S2 C19 C18 -0.1(6) . . . . ? C18 N5 C20 C22 -176.5(6) . . . . ? Cu2 N5 C20 C22 8.5(10) . . . . ? C18 N5 C20 S2 2.9(7) . . . . ? Cu2 N5 C20 S2 -172.1(3) . . . . ? C19 S2 C20 N5 -1.6(5) . . . . ? C19 S2 C20 C22 177.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.532 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.093