Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dan Li' _publ_contact_author_address ; Department of Chemistry Shantou University Shantou City Guangdong Province 515063 CHINA ; _publ_contact_author_email DLI@STU.EDU.CN _publ_section_title ; Syntheses of CuCN complexes by decomposing CuSCN: a feasibly way? ; loop_ _publ_author_name 'Dan Li' 'Tao Wu' 'Xuanjun Zhang' 'Xiao-Ping Zhou' # Attachment 'complex1.cif' data_0509a _database_code_depnum_ccdc_archive 'CCDC 293329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Cu2 N2 P2 S2' _chemical_formula_weight 641.63 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' P P 0.1023 0.0942 '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 10.0561(13) _cell_length_b 15.461(2) _cell_length_c 9.5055(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.044(2) _cell_angle_gamma 90.00 _cell_volume 1413.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1866 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.0 _exptl_crystal_description column _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 1.786 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7054 _exptl_absorpt_correction_T_max 0.8416 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7321 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2483 _reflns_number_gt 1957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.0700P] 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 2483 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.35308(6) 0.27987(4) 0.97652(5) 0.0794(2) Uani 1 1 d . . . N1 N 0.3804(4) 0.2565(2) 0.7921(4) 0.0832(11) Uani 1 1 d . . . P1 P 0.28669(8) 0.49463(6) 0.84452(8) 0.0432(2) Uani 1 1 d . . . S1 S 0.19712(10) 0.41105(7) 0.94307(10) 0.0640(3) Uani 1 1 d . . . C1 C 0.3775(4) 0.2438(2) 0.6744(3) 0.0575(9) Uani 1 1 d . . . C2 C 0.4753(3) 0.4927(2) 0.9172(3) 0.0466(8) Uani 1 1 d . . . H2A H 0.5094 0.4373 0.8948 0.056 Uiso 1 1 calc R . . H2B H 0.5140 0.5373 0.8691 0.056 Uiso 1 1 calc R . . C3 C 0.2352(3) 0.6040(2) 0.8701(3) 0.0490(8) Uani 1 1 d . . . C4 C 0.1334(4) 0.6202(3) 0.9366(4) 0.0694(11) Uani 1 1 d . . . H4 H 0.0915 0.5743 0.9707 0.083 Uiso 1 1 calc R . . C5 C 0.0928(5) 0.7040(3) 0.9534(6) 0.0923(15) Uani 1 1 d . . . H5 H 0.0223 0.7143 0.9964 0.111 Uiso 1 1 calc R . . C6 C 0.1559(5) 0.7717(3) 0.9070(6) 0.0956(16) Uani 1 1 d . . . H6 H 0.1299 0.8281 0.9199 0.115 Uiso 1 1 calc R . . C7 C 0.2566(6) 0.7564(3) 0.8420(6) 0.0964(15) Uani 1 1 d . . . H7 H 0.2998 0.8025 0.8103 0.116 Uiso 1 1 calc R . . C8 C 0.2955(4) 0.6732(3) 0.8224(5) 0.0765(12) Uani 1 1 d . . . H8 H 0.3638 0.6636 0.7761 0.092 Uiso 1 1 calc R . . C9 C 0.2506(3) 0.4756(2) 0.6486(3) 0.0459(8) Uani 1 1 d . . . C10 C 0.3263(4) 0.5161(3) 0.5679(4) 0.0661(10) Uani 1 1 d . . . H10 H 0.3974 0.5543 0.6132 0.079 Uiso 1 1 calc R . . C11 C 0.2950(5) 0.4991(3) 0.4176(4) 0.0787(13) Uani 1 1 d . . . H11 H 0.3447 0.5268 0.3620 0.094 Uiso 1 1 calc R . . C12 C 0.1917(5) 0.4420(3) 0.3515(4) 0.0768(12) Uani 1 1 d . . . H12 H 0.1721 0.4302 0.2515 0.092 Uiso 1 1 calc R . . C13 C 0.1183(5) 0.4027(3) 0.4311(4) 0.0835(14) Uani 1 1 d . . . H13 H 0.0475 0.3644 0.3855 0.100 Uiso 1 1 calc R . . C14 C 0.1471(4) 0.4189(3) 0.5799(4) 0.0673(11) Uani 1 1 d . . . H14 H 0.0961 0.3912 0.6339 0.081 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 Cu1 0.1139(5) 0.0954(5) 0.0375(3) -0.0125(2) 0.0354(3) -0.0374(3) N1 0.112(3) 0.077(2) 0.068(2) 0.0052(19) 0.037(2) 0.001(2) P1 0.0392(4) 0.0600(6) 0.0298(4) -0.0015(4) 0.0093(3) -0.0018(4) S1 0.0689(6) 0.0786(7) 0.0526(5) 0.0046(5) 0.0305(5) -0.0069(5) C1 0.092(3) 0.062(2) 0.0262(15) 0.0008(15) 0.0305(17) 0.011(2) C2 0.0431(17) 0.062(2) 0.0333(16) -0.0007(14) 0.0095(13) 0.0018(15) C3 0.0414(17) 0.064(2) 0.0370(16) -0.0102(15) 0.0046(14) -0.0012(16) C4 0.058(2) 0.076(3) 0.080(3) -0.019(2) 0.030(2) -0.006(2) C5 0.069(3) 0.090(4) 0.129(4) -0.036(3) 0.047(3) -0.003(3) C6 0.077(3) 0.081(4) 0.125(4) -0.028(3) 0.024(3) 0.011(3) C7 0.107(4) 0.066(3) 0.124(4) -0.007(3) 0.046(3) -0.003(3) C8 0.081(3) 0.069(3) 0.091(3) -0.009(2) 0.042(2) 0.000(2) C9 0.0446(18) 0.058(2) 0.0328(15) -0.0018(14) 0.0086(14) 0.0066(15) C10 0.071(2) 0.085(3) 0.0451(19) -0.0031(19) 0.0216(18) -0.010(2) C11 0.089(3) 0.110(4) 0.045(2) 0.010(2) 0.031(2) 0.006(3) C12 0.088(3) 0.098(3) 0.0334(18) -0.008(2) 0.002(2) 0.012(3) C13 0.087(3) 0.107(4) 0.044(2) -0.014(2) 0.000(2) -0.014(3) C14 0.063(2) 0.094(3) 0.0397(19) -0.0068(19) 0.0052(17) -0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.860(3) 4_566 ? Cu1 N1 1.887(4) . ? Cu1 S1 2.5263(13) . ? N1 C1 1.128(5) . ? P1 C3 1.805(4) . ? P1 C9 1.814(3) . ? P1 C2 1.818(3) . ? P1 S1 1.9630(13) . ? C1 Cu1 1.860(3) 4_565 ? C2 C2 1.522(5) 3_667 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.371(5) . ? C3 C4 1.375(5) . ? C4 C5 1.382(6) . ? C4 H4 0.9300 . ? C5 C6 1.362(7) . ? C5 H5 0.9300 . ? C6 C7 1.353(7) . ? C6 H6 0.9300 . ? C7 C8 1.373(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C14 1.371(5) . ? C9 C10 1.379(5) . ? C10 C11 1.395(5) . ? C10 H10 0.9300 . ? C11 C12 1.369(6) . ? C11 H11 0.9300 . ? C12 C13 1.347(6) . ? C12 H12 0.9300 . ? C13 C14 1.381(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N1 152.80(18) 4_566 . ? C1 Cu1 S1 100.29(13) 4_566 . ? N1 Cu1 S1 106.89(12) . . ? C1 N1 Cu1 170.6(4) . . ? C3 P1 C9 108.11(15) . . ? C3 P1 C2 105.80(15) . . ? C9 P1 C2 105.06(14) . . ? C3 P1 S1 111.26(12) . . ? C9 P1 S1 113.68(12) . . ? C2 P1 S1 112.42(11) . . ? P1 S1 Cu1 103.52(5) . . ? N1 C1 Cu1 174.0(4) . 4_565 ? C2 C2 P1 112.3(3) 3_667 . ? C2 C2 H2A 109.2 3_667 . ? P1 C2 H2A 109.2 . . ? C2 C2 H2B 109.2 3_667 . ? P1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C8 C3 C4 118.1(4) . . ? C8 C3 P1 121.0(3) . . ? C4 C3 P1 120.9(3) . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 119.7(5) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.5(5) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C3 C8 C7 121.0(4) . . ? C3 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C14 C9 C10 119.4(3) . . ? C14 C9 P1 119.2(3) . . ? C10 C9 P1 121.4(3) . . ? C9 C10 C11 119.3(4) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.6(4) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 120.4(4) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? 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 C1 Cu1 N1 C1 130(2) 4_566 . . . ? S1 Cu1 N1 C1 -47(2) . . . . ? C3 P1 S1 Cu1 -158.33(11) . . . . ? C9 P1 S1 Cu1 79.33(12) . . . . ? C2 P1 S1 Cu1 -39.87(12) . . . . ? C1 Cu1 S1 P1 130.96(13) 4_566 . . . ? N1 Cu1 S1 P1 -50.05(14) . . . . ? Cu1 N1 C1 Cu1 -20(6) . . . 4_565 ? C3 P1 C2 C2 66.1(4) . . . 3_667 ? C9 P1 C2 C2 -179.7(3) . . . 3_667 ? S1 P1 C2 C2 -55.5(4) . . . 3_667 ? C9 P1 C3 C8 -60.8(3) . . . . ? C2 P1 C3 C8 51.4(3) . . . . ? S1 P1 C3 C8 173.7(3) . . . . ? C9 P1 C3 C4 118.6(3) . . . . ? C2 P1 C3 C4 -129.3(3) . . . . ? S1 P1 C3 C4 -6.9(3) . . . . ? C8 C3 C4 C5 0.6(6) . . . . ? P1 C3 C4 C5 -178.8(4) . . . . ? C3 C4 C5 C6 -1.5(7) . . . . ? C4 C5 C6 C7 1.2(9) . . . . ? C5 C6 C7 C8 0.0(9) . . . . ? C4 C3 C8 C7 0.7(6) . . . . ? P1 C3 C8 C7 -179.9(4) . . . . ? C6 C7 C8 C3 -1.0(8) . . . . ? C3 P1 C9 C14 -111.5(3) . . . . ? C2 P1 C9 C14 135.9(3) . . . . ? S1 P1 C9 C14 12.6(3) . . . . ? C3 P1 C9 C10 69.4(3) . . . . ? C2 P1 C9 C10 -43.2(3) . . . . ? S1 P1 C9 C10 -166.5(3) . . . . ? C14 C9 C10 C11 0.6(6) . . . . ? P1 C9 C10 C11 179.7(3) . . . . ? C9 C10 C11 C12 -0.9(6) . . . . ? C10 C11 C12 C13 0.9(7) . . . . ? C11 C12 C13 C14 -0.7(7) . . . . ? C10 C9 C14 C13 -0.4(6) . . . . ? P1 C9 C14 C13 -179.5(3) . . . . ? C12 C13 C14 C9 0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.670 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.060 # Attachment 'complex2.cif' data_1015am _database_code_depnum_ccdc_archive 'CCDC 293330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 Cu2 N8' _chemical_formula_weight 491.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4743(5) _cell_length_b 13.1830(8) _cell_length_c 17.4013(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1944.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4947 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.5 _exptl_crystal_description stick _exptl_crystal_colour black _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 2.213 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5762 _exptl_absorpt_correction_T_max 0.7470 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10161 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3411 _reflns_number_gt 3167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(13) _refine_ls_number_reflns 3411 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.79028(6) 0.62608(3) 0.78769(2) 0.05821(15) Uani 1 1 d . . . Cu2 Cu 1.05821(5) 1.02010(3) 0.97525(2) 0.04896(13) Uani 1 1 d . . . N1 N 1.0357(3) 0.67082(19) 0.83708(15) 0.0435(6) Uani 1 1 d . . . N2 N 0.7822(3) 0.78618(17) 0.82678(12) 0.0325(5) Uani 1 1 d . . . N3 N 0.5508(3) 0.71688(17) 0.73730(12) 0.0367(5) Uani 1 1 d . . . N4 N 0.6177(3) 0.91732(18) 0.87215(13) 0.0350(5) Uani 1 1 d . . . N5 N 0.8750(3) 0.89641(17) 0.92337(11) 0.0313(5) Uani 1 1 d . . . N6 N 0.8308(3) 1.06928(18) 1.00664(13) 0.0393(6) Uani 1 1 d . . . N7 N 1.1593(3) 0.9746(2) 1.06892(15) 0.0522(7) Uani 1 1 d . . . N8 N 0.8467(4) 0.5818(2) 0.68526(16) 0.0523(7) Uani 1 1 d . . . C1 C 1.1631(4) 0.6130(3) 0.8366(2) 0.0582(9) Uani 1 1 d . . . H1 H 1.1605 0.5537 0.8077 0.070 Uiso 1 1 calc R . . C2 C 1.2966(4) 0.6344(3) 0.8755(2) 0.0643(11) Uani 1 1 d . . . H2 H 1.3833 0.5913 0.8729 0.077 Uiso 1 1 calc R . . C3 C 1.3019(4) 0.7212(3) 0.9188(2) 0.0588(10) Uani 1 1 d . . . H3 H 1.3926 0.7379 0.9460 0.071 Uiso 1 1 calc R . . C4 C 1.1697(4) 0.7842(3) 0.92153(18) 0.0489(8) Uani 1 1 d . . . H4 H 1.1692 0.8429 0.9511 0.059 Uiso 1 1 calc R . . C5 C 1.0397(3) 0.7560(2) 0.87868(15) 0.0357(6) Uani 1 1 d . . . C6 C 0.8929(3) 0.8170(2) 0.87577(14) 0.0297(6) Uani 1 1 d . . . C7 C 0.7344(3) 0.94207(19) 0.91988(14) 0.0306(6) Uani 1 1 d . . . C8 C 0.7027(4) 1.0259(2) 0.97511(14) 0.0342(6) Uani 1 1 d . . . C9 C 0.8051(5) 1.1427(3) 1.05787(19) 0.0580(9) Uani 1 1 d . . . H9 H 0.8920 1.1745 1.0799 0.070 Uiso 1 1 calc R . . C10 C 0.6560(6) 1.1744(3) 1.0802(2) 0.0662(11) Uani 1 1 d . . . H10 H 0.6435 1.2254 1.1165 0.079 Uiso 1 1 calc R . . C11 C 0.5283(5) 1.1290(3) 1.0475(2) 0.0663(10) Uani 1 1 d . . . H11 H 0.4269 1.1484 1.0617 0.080 Uiso 1 1 calc R . . C12 C 0.5504(4) 1.0533(2) 0.99294(17) 0.0471(8) Uani 1 1 d . . . H12 H 0.4649 1.0222 0.9692 0.057 Uiso 1 1 calc R . . C13 C 0.6489(3) 0.8393(2) 0.82573(15) 0.0320(6) Uani 1 1 d . . . C14 C 0.5236(3) 0.8065(2) 0.77110(14) 0.0316(6) Uani 1 1 d . . . C15 C 0.3896(4) 0.8629(2) 0.75865(17) 0.0421(7) Uani 1 1 d . . . H15 H 0.3759 0.9254 0.7826 0.051 Uiso 1 1 calc R . . C16 C 0.2765(4) 0.8250(3) 0.71013(19) 0.0513(8) Uani 1 1 d . . . H16 H 0.1842 0.8612 0.7009 0.062 Uiso 1 1 calc R . . C17 C 0.3015(4) 0.7328(3) 0.67533(18) 0.0527(8) Uani 1 1 d . . . H17 H 0.2261 0.7052 0.6426 0.063 Uiso 1 1 calc R . . C18 C 0.4404(4) 0.6820(2) 0.68990(17) 0.0477(8) Uani 1 1 d . . . H18 H 0.4578 0.6203 0.6654 0.057 Uiso 1 1 calc R . . C19 C 1.2075(4) 0.9421(2) 1.12351(15) 0.0344(6) Uani 1 1 d . . . C20 C 0.8782(4) 0.5612(2) 0.62427(15) 0.0373(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0936(4) 0.0434(2) 0.0376(2) -0.00644(17) 0.0176(2) -0.0035(2) Cu2 0.0534(2) 0.0625(2) 0.03099(19) 0.00863(17) -0.00140(17) -0.0102(2) N1 0.0417(16) 0.0416(14) 0.0472(14) 0.0016(11) 0.0067(12) 0.0082(12) N2 0.0333(13) 0.0352(12) 0.0290(11) -0.0034(9) -0.0021(10) 0.0058(10) N3 0.0419(14) 0.0375(13) 0.0307(11) -0.0044(9) -0.0020(11) 0.0008(11) N4 0.0345(13) 0.0358(12) 0.0346(12) -0.0047(10) -0.0039(10) 0.0046(10) N5 0.0306(12) 0.0369(13) 0.0264(11) -0.0001(9) -0.0007(10) 0.0009(10) N6 0.0501(16) 0.0365(12) 0.0315(11) -0.0027(10) -0.0011(11) -0.0064(11) N7 0.0479(17) 0.0629(17) 0.0457(15) -0.0013(14) 0.0048(12) -0.0119(14) N8 0.0613(19) 0.0403(14) 0.0553(16) 0.0014(13) 0.0074(14) 0.0027(13) C1 0.052(2) 0.050(2) 0.072(2) 0.0075(18) 0.0156(19) 0.0184(16) C2 0.048(2) 0.073(3) 0.073(2) 0.035(2) 0.016(2) 0.024(2) C3 0.0335(18) 0.089(3) 0.0535(19) 0.032(2) -0.0048(17) 0.0001(19) C4 0.0411(19) 0.063(2) 0.0424(16) 0.0080(15) -0.0054(14) -0.0013(16) C5 0.0350(16) 0.0416(16) 0.0303(13) 0.0067(12) 0.0012(13) 0.0041(13) C6 0.0304(15) 0.0315(14) 0.0271(12) 0.0038(10) 0.0021(11) -0.0009(11) C7 0.0343(15) 0.0314(13) 0.0263(12) 0.0003(11) 0.0009(11) -0.0013(11) C8 0.0455(16) 0.0314(12) 0.0259(12) 0.0005(11) -0.0001(13) -0.0024(13) C9 0.081(3) 0.0473(19) 0.0455(18) -0.0159(15) 0.0003(18) -0.0140(19) C10 0.097(3) 0.0479(19) 0.054(2) -0.0231(17) 0.008(2) 0.005(2) C11 0.082(3) 0.054(2) 0.062(2) -0.0159(19) 0.019(2) 0.013(2) C12 0.052(2) 0.0456(17) 0.0435(16) -0.0087(13) 0.0069(15) 0.0054(15) C13 0.0357(16) 0.0294(14) 0.0310(13) -0.0010(11) -0.0013(12) 0.0012(12) C14 0.0340(17) 0.0342(14) 0.0266(14) 0.0022(10) -0.0005(11) 0.0009(12) C15 0.0463(18) 0.0397(16) 0.0404(16) -0.0004(13) -0.0112(13) 0.0070(14) C16 0.0475(19) 0.0546(18) 0.0518(18) 0.0089(16) -0.0175(16) 0.0073(15) C17 0.060(2) 0.0560(19) 0.0421(16) 0.0018(15) -0.0224(17) -0.0098(18) C18 0.059(2) 0.0453(17) 0.0394(16) -0.0099(13) -0.0110(16) -0.0044(16) C19 0.0382(15) 0.0386(15) 0.0265(13) 0.0003(11) -0.0052(13) -0.0047(13) C20 0.0477(17) 0.0372(15) 0.0269(13) -0.0080(11) 0.0042(13) 0.0079(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 C19 1.921(3) 4_467 ? Cu1 N8 1.936(3) . ? Cu1 N2 2.219(2) . ? Cu1 N1 2.326(3) . ? Cu2 C20 1.893(3) 3_756 ? Cu2 N7 1.937(3) . ? Cu2 N6 2.105(3) . ? Cu2 N5 2.426(2) . ? N1 C1 1.322(4) . ? N1 C5 1.337(4) . ? N2 C13 1.330(4) . ? N2 C6 1.331(3) . ? N3 C18 1.329(4) . ? N3 C14 1.340(3) . ? N4 C7 1.332(4) . ? N4 C13 1.334(3) . ? N5 C7 1.336(4) . ? N5 C6 1.344(3) . ? N6 C9 1.334(4) . ? N6 C8 1.344(4) . ? N7 C19 1.119(4) . ? N8 C20 1.127(4) . ? C1 C2 1.348(6) . ? C1 H1 0.9300 . ? C2 C3 1.370(6) . ? C2 H2 0.9300 . ? C3 C4 1.395(5) . ? C3 H3 0.9300 . ? C4 C5 1.381(4) . ? C4 H4 0.9300 . ? C5 C6 1.482(4) . ? C7 C8 1.489(4) . ? C8 C12 1.376(4) . ? C9 C10 1.386(6) . ? C9 H9 0.9300 . ? C10 C11 1.360(6) . ? C10 H10 0.9300 . ? C11 C12 1.390(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.489(4) . ? C14 C15 1.374(4) . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 C17 1.375(5) . ? C16 H16 0.9300 . ? C17 C18 1.379(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 Cu1 1.921(3) 4_567 ? C20 Cu2 1.893(3) 3_746 ? 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 C19 Cu1 N8 133.62(11) 4_467 . ? C19 Cu1 N2 100.81(10) 4_467 . ? N8 Cu1 N2 125.23(10) . . ? C19 Cu1 N1 98.51(11) 4_467 . ? N8 Cu1 N1 101.29(11) . . ? N2 Cu1 N1 70.91(9) . . ? C20 Cu2 N7 137.14(13) 3_756 . ? C20 Cu2 N6 114.19(11) 3_756 . ? N7 Cu2 N6 106.36(10) . . ? C20 Cu2 N5 91.94(10) 3_756 . ? N7 Cu2 N5 112.82(10) . . ? N6 Cu2 N5 73.61(8) . . ? C1 N1 C5 117.8(3) . . ? C1 N1 Cu1 125.6(2) . . ? C5 N1 Cu1 115.84(19) . . ? C13 N2 C6 116.5(2) . . ? C13 N2 Cu1 121.54(18) . . ? C6 N2 Cu1 117.71(17) . . ? C18 N3 C14 117.2(3) . . ? C7 N4 C13 114.8(2) . . ? C7 N5 C6 115.1(2) . . ? C7 N5 Cu2 106.55(16) . . ? C6 N5 Cu2 132.94(18) . . ? C9 N6 C8 116.7(3) . . ? C9 N6 Cu2 123.1(2) . . ? C8 N6 Cu2 120.18(18) . . ? C19 N7 Cu2 174.0(3) . . ? C20 N8 Cu1 176.3(3) . . ? N1 C1 C2 124.2(4) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 117.5(3) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 122.6(3) . . ? N1 C5 C6 114.6(2) . . ? C4 C5 C6 122.8(3) . . ? N2 C6 N5 123.6(2) . . ? N2 C6 C5 116.6(2) . . ? N5 C6 C5 119.7(2) . . ? N4 C7 N5 125.4(2) . . ? N4 C7 C8 116.8(2) . . ? N5 C7 C8 117.8(2) . . ? N6 C8 C12 123.7(3) . . ? N6 C8 C7 115.7(3) . . ? C12 C8 C7 120.6(3) . . ? N6 C9 C10 123.7(3) . . ? N6 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C11 C10 C9 118.4(3) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C8 C12 C11 118.0(3) . . ? C8 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? N2 C13 N4 124.5(3) . . ? N2 C13 C14 117.5(2) . . ? N4 C13 C14 118.0(2) . . ? N3 C14 C15 123.4(3) . . ? N3 C14 C13 114.4(2) . . ? C15 C14 C13 122.2(2) . . ? C16 C15 C14 118.5(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 119.0(3) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C18 118.7(3) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N3 C18 C17 123.1(3) . . ? N3 C18 H18 118.4 . . ? C17 C18 H18 118.4 . . ? N7 C19 Cu1 174.4(3) . 4_567 ? N8 C20 Cu2 175.9(3) . 3_746 ? 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 C19 Cu1 N1 C1 86.2(3) 4_467 . . . ? N8 Cu1 N1 C1 -51.6(3) . . . . ? N2 Cu1 N1 C1 -175.2(3) . . . . ? C19 Cu1 N1 C5 -83.7(2) 4_467 . . . ? N8 Cu1 N1 C5 138.5(2) . . . . ? N2 Cu1 N1 C5 14.86(19) . . . . ? C19 Cu1 N2 C13 -79.6(2) 4_467 . . . ? N8 Cu1 N2 C13 94.5(2) . . . . ? N1 Cu1 N2 C13 -175.0(2) . . . . ? C19 Cu1 N2 C6 76.5(2) 4_467 . . . ? N8 Cu1 N2 C6 -109.3(2) . . . . ? N1 Cu1 N2 C6 -18.81(18) . . . . ? C20 Cu2 N5 C7 -94.41(19) 3_756 . . . ? N7 Cu2 N5 C7 121.50(18) . . . . ? N6 Cu2 N5 C7 20.26(16) . . . . ? C20 Cu2 N5 C6 57.2(2) 3_756 . . . ? N7 Cu2 N5 C6 -86.9(2) . . . . ? N6 Cu2 N5 C6 171.9(2) . . . . ? C20 Cu2 N6 C9 -107.2(2) 3_756 . . . ? N7 Cu2 N6 C9 58.6(3) . . . . ? N5 Cu2 N6 C9 168.1(3) . . . . ? C20 Cu2 N6 C8 73.2(2) 3_756 . . . ? N7 Cu2 N6 C8 -121.0(2) . . . . ? N5 Cu2 N6 C8 -11.44(19) . . . . ? C20 Cu2 N7 C19 -138(3) 3_756 . . . ? N6 Cu2 N7 C19 61(3) . . . . ? N5 Cu2 N7 C19 -17(3) . . . . ? C19 Cu1 N8 C20 155(4) 4_467 . . . ? N2 Cu1 N8 C20 -17(4) . . . . ? N1 Cu1 N8 C20 -91(4) . . . . ? C5 N1 C1 C2 0.0(5) . . . . ? Cu1 N1 C1 C2 -169.7(3) . . . . ? N1 C1 C2 C3 0.4(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C1 N1 C5 C4 -1.1(4) . . . . ? Cu1 N1 C5 C4 169.6(2) . . . . ? C1 N1 C5 C6 179.6(3) . . . . ? Cu1 N1 C5 C6 -9.7(3) . . . . ? C3 C4 C5 N1 1.6(4) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? C13 N2 C6 N5 0.8(4) . . . . ? Cu1 N2 C6 N5 -156.6(2) . . . . ? C13 N2 C6 C5 178.2(2) . . . . ? Cu1 N2 C6 C5 20.9(3) . . . . ? C7 N5 C6 N2 1.7(4) . . . . ? Cu2 N5 C6 N2 -148.1(2) . . . . ? C7 N5 C6 C5 -175.6(2) . . . . ? Cu2 N5 C6 C5 34.6(3) . . . . ? N1 C5 C6 N2 -6.7(3) . . . . ? C4 C5 C6 N2 174.0(3) . . . . ? N1 C5 C6 N5 170.8(2) . . . . ? C4 C5 C6 N5 -8.5(4) . . . . ? C13 N4 C7 N5 0.8(4) . . . . ? C13 N4 C7 C8 -177.5(2) . . . . ? C6 N5 C7 N4 -2.6(4) . . . . ? Cu2 N5 C7 N4 154.8(2) . . . . ? C6 N5 C7 C8 175.7(2) . . . . ? Cu2 N5 C7 C8 -26.9(3) . . . . ? C9 N6 C8 C12 0.0(4) . . . . ? Cu2 N6 C8 C12 179.6(2) . . . . ? C9 N6 C8 C7 -178.2(3) . . . . ? Cu2 N6 C8 C7 1.4(3) . . . . ? N4 C7 C8 N6 -161.5(2) . . . . ? N5 C7 C8 N6 20.0(3) . . . . ? N4 C7 C8 C12 20.2(4) . . . . ? N5 C7 C8 C12 -158.3(3) . . . . ? C8 N6 C9 C10 0.9(5) . . . . ? Cu2 N6 C9 C10 -178.6(3) . . . . ? N6 C9 C10 C11 -0.7(6) . . . . ? C9 C10 C11 C12 -0.4(6) . . . . ? N6 C8 C12 C11 -1.1(5) . . . . ? C7 C8 C12 C11 177.1(3) . . . . ? C10 C11 C12 C8 1.2(5) . . . . ? C6 N2 C13 N4 -2.9(4) . . . . ? Cu1 N2 C13 N4 153.5(2) . . . . ? C6 N2 C13 C14 179.7(2) . . . . ? Cu1 N2 C13 C14 -23.8(3) . . . . ? C7 N4 C13 N2 2.1(4) . . . . ? C7 N4 C13 C14 179.5(2) . . . . ? C18 N3 C14 C15 -0.4(4) . . . . ? C18 N3 C14 C13 177.8(2) . . . . ? N2 C13 C14 N3 9.9(4) . . . . ? N4 C13 C14 N3 -167.7(2) . . . . ? N2 C13 C14 C15 -172.0(3) . . . . ? N4 C13 C14 C15 10.5(4) . . . . ? N3 C14 C15 C16 1.1(5) . . . . ? C13 C14 C15 C16 -177.0(3) . . . . ? C14 C15 C16 C17 -0.5(5) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? C14 N3 C18 C17 -0.8(5) . . . . ? C16 C17 C18 N3 1.3(5) . . . . ? Cu2 N7 C19 Cu1 54(5) . . . 4_567 ? Cu1 N8 C20 Cu2 145(3) . . . 3_746 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.447 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.052 # Attachment 'complex3.cif' data_1204cm _database_code_depnum_ccdc_archive 'CCDC 293331' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 Cu2 N8' _chemical_formula_weight 491.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.6163(8) _cell_length_b 15.7573(14) _cell_length_c 14.2116(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.956(2) _cell_angle_gamma 90.00 _cell_volume 1919.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1107 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 21.7 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 2.242 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5828 _exptl_absorpt_correction_T_max 0.6384 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4983 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1700 _reflns_number_gt 1356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+32.4587P] 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 1700 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.2289 _refine_ls_wR_factor_gt 0.2152 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.71125(16) 0.36553(10) 0.88330(11) 0.1006(8) Uani 1 1 d . . . N1 N 0.7661(7) 0.4930(4) 0.9387(4) 0.0478(15) Uani 1 1 d . . . N2 N 0.9170(7) 0.4062(4) 0.8111(4) 0.0411(14) Uani 1 1 d . . . N3 N 1.0000 0.5368(5) 0.7500 0.048(2) Uani 1 2 d S . . N4 N 1.1214(10) 0.2335(5) 0.7186(7) 0.075(2) Uani 0.50 1 d P A 1 N5 N 0.5476(9) 0.3719(5) 0.7812(6) 0.061(2) Uani 0.50 1 d P . 3 N6 N 0.7406(10) 0.2784(5) 0.9760(6) 0.063(2) Uani 0.50 1 d P . 5 C1 C 0.7104(9) 0.5325(6) 1.0118(6) 0.058(2) Uani 1 1 d . . . H1 H 0.6389 0.5035 1.0446 0.069 Uiso 1 1 calc R . . C2 C 0.7523(11) 0.6131(6) 1.0412(7) 0.064(2) Uani 1 1 d . . . H2 H 0.7092 0.6381 1.0918 0.077 Uiso 1 1 calc R . . C3 C 0.8581(11) 0.6552(6) 0.9946(7) 0.065(2) Uani 1 1 d . . . H3 H 0.8923 0.7087 1.0150 0.078 Uiso 1 1 calc R . . C4 C 0.9155(9) 0.6183(5) 0.9164(6) 0.054(2) Uani 1 1 d . . . H4 H 0.9839 0.6475 0.8816 0.065 Uiso 1 1 calc R . . C5 C 0.8674(8) 0.5365(5) 0.8922(5) 0.0444(17) Uani 1 1 d . . . C6 C 0.9316(8) 0.4914(4) 0.8134(5) 0.0415(16) Uani 1 1 d . . . C7 C 1.0000 0.3676(6) 0.7500 0.041(2) Uani 1 2 d S . . C8 C 1.0000 0.2725(6) 0.7500 0.045(2) Uani 1 2 d S . . C9 C 1.1214(10) 0.2335(5) 0.7186(7) 0.075(2) Uani 0.50 1 d P A 2 H9 H 1.2036 0.2636 0.6971 0.090 Uiso 0.50 1 calc PR A 2 C10 C 1.1188(15) 0.1465(7) 0.7199(9) 0.095(4) Uani 1 1 d . . . H10 H 1.2022 0.1170 0.6991 0.115 Uiso 1 1 calc R A 1 C11 C 1.0000 0.1026(9) 0.7500 0.097(6) Uani 1 2 d S . . H11 H 1.0000 0.0436 0.7500 0.116 Uiso 1 2 calc SR . . C12 C 0.5476(9) 0.3719(5) 0.7812(6) 0.061(2) Uani 0.50 1 d P . 4 C13 C 0.7406(10) 0.2784(5) 0.9760(6) 0.063(2) Uani 0.50 1 d P . 6 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 0.0774(10) 0.1053(12) 0.1110(12) 0.0629(9) -0.0286(8) -0.0366(8) N1 0.044(4) 0.046(4) 0.052(4) 0.004(3) 0.001(3) -0.002(3) N2 0.041(3) 0.034(3) 0.048(3) 0.001(3) -0.001(3) -0.003(3) N3 0.047(5) 0.034(5) 0.062(6) 0.000 0.005(4) 0.000 N4 0.069(6) 0.057(5) 0.102(7) 0.007(5) 0.019(5) 0.008(4) N5 0.050(5) 0.054(5) 0.078(6) 0.014(4) -0.004(3) -0.006(3) N6 0.065(5) 0.056(5) 0.065(5) 0.018(4) -0.007(4) -0.020(4) C1 0.047(5) 0.079(6) 0.048(5) 0.002(4) 0.007(4) 0.002(4) C2 0.060(5) 0.072(6) 0.059(5) -0.020(5) 0.003(4) 0.011(5) C3 0.057(5) 0.058(5) 0.081(6) -0.022(5) 0.007(5) 0.005(4) C4 0.047(4) 0.045(5) 0.072(6) -0.006(4) 0.013(4) 0.000(3) C5 0.040(4) 0.039(4) 0.054(4) 0.000(3) 0.003(3) 0.004(3) C6 0.035(4) 0.039(4) 0.050(4) 0.000(3) -0.001(3) -0.002(3) C7 0.040(5) 0.035(5) 0.046(6) 0.000 -0.005(5) 0.000 C8 0.053(6) 0.034(5) 0.046(6) 0.000 -0.004(5) 0.000 C9 0.069(6) 0.057(5) 0.102(7) 0.007(5) 0.019(5) 0.008(4) C10 0.105(9) 0.074(8) 0.108(9) -0.007(7) 0.012(7) 0.045(7) C11 0.143(17) 0.030(7) 0.108(13) 0.000 -0.029(12) 0.000 C12 0.050(5) 0.054(5) 0.078(6) 0.014(4) -0.004(3) -0.006(3) C13 0.065(5) 0.056(5) 0.065(5) 0.018(4) -0.007(4) -0.020(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N6 1.902(7) . ? Cu1 N5 1.919(8) . ? Cu1 N1 2.191(7) . ? Cu1 N2 2.232(6) . ? N1 C5 1.337(10) . ? N1 C1 1.342(10) . ? N2 C7 1.329(7) . ? N2 C6 1.347(9) . ? N3 C6 1.335(8) . ? N3 C6 1.335(8) 2_756 ? N4 C8 1.329(9) . ? N4 C10 1.371(14) . ? N5 N5 1.143(15) 2_656 ? N6 N6 1.125(14) 7_657 ? C1 C2 1.374(12) . ? C1 H1 0.9300 . ? C2 C3 1.354(13) . ? C2 H2 0.9300 . ? C3 C4 1.390(12) . ? C3 H3 0.9300 . ? C4 C5 1.386(10) . ? C4 H4 0.9300 . ? C5 C6 1.482(10) . ? C7 N2 1.329(7) 2_756 ? C7 C8 1.499(13) . ? C8 C9 1.329(10) 2_756 ? C8 N4 1.329(10) 2_756 ? C10 C11 1.343(15) . ? C10 H10 0.9300 . ? C11 C10 1.343(15) 2_756 ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu1 N5 126.6(3) . . ? N6 Cu1 N1 113.9(3) . . ? N5 Cu1 N1 109.8(3) . . ? N6 Cu1 N2 118.1(3) . . ? N5 Cu1 N2 101.2(3) . . ? N1 Cu1 N2 75.5(2) . . ? C5 N1 C1 116.6(7) . . ? C5 N1 Cu1 114.8(5) . . ? C1 N1 Cu1 128.5(6) . . ? C7 N2 C6 114.6(7) . . ? C7 N2 Cu1 132.5(5) . . ? C6 N2 Cu1 110.6(5) . . ? C6 N3 C6 115.1(9) . 2_756 ? C8 N4 C10 116.3(9) . . ? N5 N5 Cu1 176.6(6) 2_656 . ? N6 N6 Cu1 173.4(12) 7_657 . ? N1 C1 C2 124.1(8) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 118.2(8) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.0(8) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 117.7(8) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 123.2(7) . . ? N1 C5 C6 116.2(6) . . ? C4 C5 C6 120.6(7) . . ? N3 C6 N2 124.4(7) . . ? N3 C6 C5 118.6(6) . . ? N2 C6 C5 117.1(6) . . ? N2 C7 N2 125.5(9) . 2_756 ? N2 C7 C8 117.2(4) . . ? N2 C7 C8 117.2(4) 2_756 . ? C9 C8 N4 0.0(8) 2_756 2_756 ? C9 C8 N4 125.0(11) 2_756 . ? N4 C8 N4 125.0(11) 2_756 . ? C9 C8 C7 117.5(5) 2_756 . ? N4 C8 C7 117.5(5) 2_756 . ? N4 C8 C7 117.5(5) . . ? C11 C10 N4 122.3(11) . . ? C11 C10 H10 118.9 . . ? N4 C10 H10 118.9 . . ? C10 C11 C10 117.9(14) . 2_756 ? C10 C11 H11 121.1 . . ? C10 C11 H11 121.1 2_756 . ? 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 N6 Cu1 N1 C5 126.7(6) . . . . ? N5 Cu1 N1 C5 -84.8(6) . . . . ? N2 Cu1 N1 C5 12.0(5) . . . . ? N6 Cu1 N1 C1 -54.0(7) . . . . ? N5 Cu1 N1 C1 94.4(7) . . . . ? N2 Cu1 N1 C1 -168.7(7) . . . . ? N6 Cu1 N2 C7 68.6(6) . . . . ? N5 Cu1 N2 C7 -74.0(6) . . . . ? N1 Cu1 N2 C7 178.2(6) . . . . ? N6 Cu1 N2 C6 -130.1(5) . . . . ? N5 Cu1 N2 C6 87.3(5) . . . . ? N1 Cu1 N2 C6 -20.4(5) . . . . ? N6 Cu1 N5 N5 -57(17) . . . 2_656 ? N1 Cu1 N5 N5 160(17) . . . 2_656 ? N2 Cu1 N5 N5 81(17) . . . 2_656 ? N5 Cu1 N6 N6 61(9) . . . 7_657 ? N1 Cu1 N6 N6 -156(9) . . . 7_657 ? N2 Cu1 N6 N6 -71(9) . . . 7_657 ? C5 N1 C1 C2 -0.7(12) . . . . ? Cu1 N1 C1 C2 -180.0(6) . . . . ? N1 C1 C2 C3 -0.9(14) . . . . ? C1 C2 C3 C4 3.1(14) . . . . ? C2 C3 C4 C5 -3.5(13) . . . . ? C1 N1 C5 C4 0.2(11) . . . . ? Cu1 N1 C5 C4 179.6(6) . . . . ? C1 N1 C5 C6 178.3(6) . . . . ? Cu1 N1 C5 C6 -2.3(8) . . . . ? C3 C4 C5 N1 1.9(12) . . . . ? C3 C4 C5 C6 -176.2(7) . . . . ? C6 N3 C6 N2 -6.0(5) 2_756 . . . ? C6 N3 C6 C5 173.7(7) 2_756 . . . ? C7 N2 C6 N3 11.3(9) . . . . ? Cu1 N2 C6 N3 -153.7(5) . . . . ? C7 N2 C6 C5 -168.5(5) . . . . ? Cu1 N2 C6 C5 26.5(7) . . . . ? N1 C5 C6 N3 163.1(6) . . . . ? C4 C5 C6 N3 -18.8(10) . . . . ? N1 C5 C6 N2 -17.2(10) . . . . ? C4 C5 C6 N2 161.0(7) . . . . ? C6 N2 C7 N2 -5.2(4) . . . 2_756 ? Cu1 N2 C7 N2 155.6(6) . . . 2_756 ? C6 N2 C7 C8 174.8(4) . . . . ? Cu1 N2 C7 C8 -24.4(6) . . . . ? C10 N4 C8 C9 -0.3(8) . . . 2_756 ? C10 N4 C8 N4 -0.3(8) . . . 2_756 ? C10 N4 C8 C7 179.7(8) . . . . ? N2 C7 C8 C9 24.9(6) . . . 2_756 ? N2 C7 C8 C9 -155.1(6) 2_756 . . 2_756 ? N2 C7 C8 N4 24.9(6) . . . 2_756 ? N2 C7 C8 N4 -155.1(6) 2_756 . . 2_756 ? N2 C7 C8 N4 -155.1(6) . . . . ? N2 C7 C8 N4 24.9(6) 2_756 . . . ? C8 N4 C10 C11 0.7(16) . . . . ? N4 C10 C11 C10 -0.3(9) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.892 _refine_diff_density_min -1.661 _refine_diff_density_rms 0.115 # Attachment 'complex4.cif' data_0427am _database_code_depnum_ccdc_archive 'CCDC 293332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 Cu2 N8 S' _chemical_formula_weight 523.52 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9991(16) _cell_length_b 18.333(4) _cell_length_c 8.3381(18) _cell_angle_alpha 90.00 _cell_angle_beta 112.652(4) _cell_angle_gamma 90.00 _cell_volume 987.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1943 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 24.1 _exptl_crystal_description hexagonal _exptl_crystal_colour black _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 2.286 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6214 _exptl_absorpt_correction_T_max 0.6973 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5066 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2678 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1403P)^2^+0.1479P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 2678 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1879 _refine_ls_wR_factor_gt 0.1835 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 0.67311(18) 0.79075(7) 0.35853(19) 0.0555(4) Uani 1 1 d . . . Cu2 Cu 0.0881(2) 0.51103(7) 0.29049(15) 0.0527(4) Uani 1 1 d . . . N1 N 0.6400(11) 0.7128(5) 0.5659(10) 0.0411(18) Uani 1 1 d . . . N2 N 0.2985(10) 0.5985(4) 0.2186(9) 0.0301(15) Uani 1 1 d . . . N3 N 0.0195(11) 0.4980(4) 0.0340(9) 0.0336(16) Uani 1 1 d . . . N4 N 0.2376(10) 0.6646(4) -0.0425(9) 0.0310(15) Uani 1 1 d . . . N5 N 0.5192(11) 0.8312(4) 0.0625(11) 0.0392(17) Uani 1 1 d . . . N6 N 0.4425(9) 0.7163(4) 0.2222(8) 0.0287(15) Uani 1 1 d . . . N7 N 0.9085(18) 0.5919(6) 0.3173(13) 0.064(3) Uani 1 1 d . . . N8 N 0.2658(14) 0.3822(6) 0.5230(12) 0.053(2) Uani 1 1 d . . . S1 S 0.9698(4) 0.74480(18) 0.3234(4) 0.0558(7) Uani 1 1 d . . . C1 C 0.7282(15) 0.7184(7) 0.7352(13) 0.049(2) Uani 1 1 d . . . H1 H 0.8171 0.7572 0.7842 0.058 Uiso 1 1 calc R . . C2 C 0.6907(16) 0.6666(8) 0.8444(12) 0.059(4) Uani 1 1 d . . . H2 H 0.7522 0.6719 0.9645 0.071 Uiso 1 1 calc R . . C3 C 0.5668(15) 0.6101(8) 0.7751(13) 0.050(3) Uani 1 1 d . . . H3 H 0.5441 0.5751 0.8465 0.060 Uiso 1 1 calc R . . C4 C 0.4731(14) 0.6037(6) 0.5986(13) 0.043(2) Uani 1 1 d . . . H4 H 0.3862 0.5646 0.5483 0.052 Uiso 1 1 calc R . . C5 C 0.5106(11) 0.6573(5) 0.4956(10) 0.0304(17) Uani 1 1 d . . . C6 C 0.4140(11) 0.6568(5) 0.3024(10) 0.0278(16) Uani 1 1 d . . . C7 C 0.2140(12) 0.6068(5) 0.0462(10) 0.0298(17) Uani 1 1 d . . . C8 C 0.0817(13) 0.5466(5) -0.0580(11) 0.0321(17) Uani 1 1 d . . . C9 C -0.0998(16) 0.4420(6) -0.0565(14) 0.046(2) Uani 1 1 d . . . H9 H -0.1429 0.4072 0.0035 0.056 Uiso 1 1 calc R . . C10 C -0.1603(17) 0.4343(7) -0.2341(16) 0.057(3) Uani 1 1 d . . . H10 H -0.2419 0.3951 -0.2923 0.068 Uiso 1 1 calc R . . C11 C -0.0976(14) 0.4857(7) -0.3225(12) 0.048(3) Uani 1 1 d . . . H11 H -0.1389 0.4824 -0.4425 0.057 Uiso 1 1 calc R . . C12 C 0.0230(14) 0.5403(6) -0.2355(11) 0.038(2) Uani 1 1 d . . . H12 H 0.0683 0.5747 -0.2950 0.046 Uiso 1 1 calc R . . C13 C 0.3530(10) 0.7179(5) 0.0536(10) 0.0259(16) Uani 1 1 d . . . C14 C 0.3848(11) 0.7829(5) -0.0385(11) 0.0293(17) Uani 1 1 d . . . C15 C 0.2840(14) 0.7919(7) -0.2176(11) 0.043(2) Uani 1 1 d . . . H15 H 0.1913 0.7571 -0.2852 0.052 Uiso 1 1 calc R . . C16 C 0.3257(18) 0.8534(7) -0.2905(15) 0.058(3) Uani 1 1 d . . . H16 H 0.2584 0.8613 -0.4094 0.069 Uiso 1 1 calc R . . C17 C 0.4650(17) 0.9034(7) -0.1907(15) 0.058(3) Uani 1 1 d . . . H17 H 0.4977 0.9446 -0.2404 0.070 Uiso 1 1 calc R . . C18 C 0.5562(16) 0.8914(6) -0.0140(15) 0.051(3) Uani 1 1 d . . . H18 H 0.6472 0.9262 0.0554 0.061 Uiso 1 1 calc R . . C19 C 0.9331(13) 0.6574(6) 0.3240(11) 0.039(2) Uani 1 1 d . . . C20 C 0.2055(15) 0.4337(5) 0.4424(11) 0.036(2) 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 0.0538(7) 0.0320(7) 0.0731(9) -0.0242(7) 0.0161(6) -0.0067(6) Cu2 0.0831(9) 0.0315(7) 0.0451(6) 0.0139(6) 0.0266(6) 0.0125(6) N1 0.046(4) 0.031(5) 0.043(4) -0.005(4) 0.014(3) -0.003(3) N2 0.034(3) 0.022(4) 0.035(4) 0.000(3) 0.014(3) 0.001(3) N3 0.047(4) 0.014(4) 0.044(4) -0.004(3) 0.023(3) -0.005(3) N4 0.040(3) 0.024(4) 0.030(3) 0.000(3) 0.014(3) -0.004(3) N5 0.046(4) 0.020(4) 0.052(4) 0.004(4) 0.019(4) -0.005(3) N6 0.032(3) 0.021(4) 0.030(3) -0.003(3) 0.009(2) -0.001(3) N7 0.105(7) 0.043(7) 0.049(5) 0.011(4) 0.035(5) 0.044(6) N8 0.060(5) 0.041(6) 0.055(5) 0.007(5) 0.018(4) -0.005(4) S1 0.0500(12) 0.0504(18) 0.0678(16) -0.0110(14) 0.0234(11) 0.0024(12) C1 0.054(5) 0.038(6) 0.048(5) -0.019(5) 0.013(4) -0.007(5) C2 0.058(6) 0.090(11) 0.023(4) -0.005(5) 0.009(4) 0.032(6) C3 0.055(5) 0.054(7) 0.043(5) 0.011(5) 0.022(4) 0.013(5) C4 0.049(5) 0.035(6) 0.045(5) 0.007(4) 0.019(4) 0.003(4) C5 0.032(3) 0.031(5) 0.024(4) 0.002(3) 0.006(3) 0.000(3) C6 0.033(4) 0.020(4) 0.029(4) 0.003(3) 0.010(3) 0.005(3) C7 0.042(4) 0.025(5) 0.024(4) 0.002(3) 0.015(3) 0.001(4) C8 0.044(4) 0.016(4) 0.038(4) -0.006(4) 0.017(3) -0.006(3) C9 0.063(5) 0.024(5) 0.060(6) -0.015(5) 0.033(5) -0.021(4) C10 0.065(6) 0.041(7) 0.066(7) -0.034(6) 0.027(5) -0.022(5) C11 0.049(5) 0.059(7) 0.034(4) -0.019(5) 0.014(4) -0.012(5) C12 0.052(5) 0.033(5) 0.032(4) -0.003(4) 0.019(3) -0.006(4) C13 0.021(3) 0.024(4) 0.035(4) -0.001(3) 0.013(3) 0.003(3) C14 0.031(3) 0.020(4) 0.038(4) 0.000(4) 0.015(3) -0.003(3) C15 0.060(5) 0.040(6) 0.027(4) 0.011(4) 0.014(4) -0.002(5) C16 0.076(7) 0.046(7) 0.044(6) 0.028(5) 0.014(5) -0.007(6) C17 0.071(6) 0.040(7) 0.067(7) 0.028(6) 0.031(6) -0.011(5) C18 0.055(5) 0.025(6) 0.066(6) 0.011(5) 0.017(5) -0.018(4) C19 0.040(4) 0.054(7) 0.027(4) 0.000(4) 0.016(3) 0.007(4) C20 0.063(5) 0.016(5) 0.037(5) 0.012(4) 0.026(4) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N8 1.909(10) 2_656 ? Cu1 N6 2.085(7) . ? Cu1 N1 2.322(9) . ? Cu1 S1 2.362(3) . ? Cu1 N5 2.399(8) . ? Cu2 C20 1.867(9) . ? Cu2 N7 2.011(9) 1_455 ? Cu2 N3 2.017(7) . ? Cu2 N2 2.404(7) . ? N1 C1 1.309(13) . ? N1 C5 1.338(12) . ? N2 C7 1.336(10) . ? N2 C6 1.359(11) . ? N3 C8 1.353(11) . ? N3 C9 1.354(12) . ? N4 C13 1.323(11) . ? N4 C7 1.338(11) . ? N5 C14 1.328(12) . ? N5 C18 1.349(12) . ? N6 C13 1.300(10) . ? N6 C6 1.334(11) . ? N7 C19 1.211(16) . ? N7 Cu2 2.011(9) 1_655 ? N8 C20 1.142(12) . ? N8 Cu1 1.909(10) 2_646 ? S1 C19 1.624(12) . ? C1 C2 1.408(18) . ? C1 H1 0.9300 . ? C2 C3 1.332(19) . ? C2 H2 0.9300 . ? C3 C4 1.366(15) . ? C3 H3 0.9300 . ? C4 C5 1.394(14) . ? C4 H4 0.9300 . ? C5 C6 1.488(11) . ? C7 C8 1.486(11) . ? C8 C12 1.379(12) . ? C9 C10 1.382(16) . ? C9 H9 0.9300 . ? C10 C11 1.368(17) . ? C10 H10 0.9300 . ? C11 C12 1.331(14) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.482(12) . ? C14 C15 1.394(12) . ? C15 C16 1.365(16) . ? C15 H15 0.9300 . ? C16 C17 1.364(18) . ? C16 H16 0.9300 . ? C17 C18 1.380(17) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Cu1 N6 146.0(3) 2_656 . ? N8 Cu1 N1 102.8(4) 2_656 . ? N6 Cu1 N1 74.0(3) . . ? N8 Cu1 S1 110.2(3) 2_656 . ? N6 Cu1 S1 103.4(2) . . ? N1 Cu1 S1 102.6(2) . . ? N8 Cu1 N5 100.6(4) 2_656 . ? N6 Cu1 N5 72.2(3) . . ? N1 Cu1 N5 145.3(3) . . ? S1 Cu1 N5 92.9(2) . . ? C20 Cu2 N7 127.9(4) . 1_455 ? C20 Cu2 N3 119.5(4) . . ? N7 Cu2 N3 107.6(3) 1_455 . ? C20 Cu2 N2 121.6(3) . . ? N7 Cu2 N2 90.3(4) 1_455 . ? N3 Cu2 N2 74.5(3) . . ? C1 N1 C5 119.3(9) . . ? C1 N1 Cu1 127.9(7) . . ? C5 N1 Cu1 112.8(6) . . ? C7 N2 C6 113.2(7) . . ? C7 N2 Cu2 106.5(5) . . ? C6 N2 Cu2 134.1(5) . . ? C8 N3 C9 116.5(7) . . ? C8 N3 Cu2 121.7(6) . . ? C9 N3 Cu2 121.6(6) . . ? C13 N4 C7 115.2(7) . . ? C14 N5 C18 117.6(8) . . ? C14 N5 Cu1 112.0(6) . . ? C18 N5 Cu1 130.3(7) . . ? C13 N6 C6 117.2(7) . . ? C13 N6 Cu1 121.6(6) . . ? C6 N6 Cu1 119.7(5) . . ? C19 N7 Cu2 130.7(9) . 1_655 ? C20 N8 Cu1 171.7(9) . 2_646 ? C19 S1 Cu1 101.8(3) . . ? N1 C1 C2 121.1(10) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 119.7(9) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.8(11) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 118.5(10) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 121.5(8) . . ? N1 C5 C6 115.3(7) . . ? C4 C5 C6 123.2(8) . . ? N6 C6 N2 124.0(7) . . ? N6 C6 C5 116.4(7) . . ? N2 C6 C5 119.6(7) . . ? N2 C7 N4 125.9(8) . . ? N2 C7 C8 117.6(7) . . ? N4 C7 C8 116.5(7) . . ? N3 C8 C12 121.7(8) . . ? N3 C8 C7 114.9(7) . . ? C12 C8 C7 123.4(8) . . ? N3 C9 C10 122.9(9) . . ? N3 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 118.5(9) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 119.5(9) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C8 120.8(9) . . ? C11 C12 H12 119.6 . . ? C8 C12 H12 119.6 . . ? N6 C13 N4 124.5(8) . . ? N6 C13 C14 118.1(7) . . ? N4 C13 C14 117.3(7) . . ? N5 C14 C15 122.9(8) . . ? N5 C14 C13 114.8(7) . . ? C15 C14 C13 122.3(8) . . ? C16 C15 C14 117.9(10) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C17 C16 C15 120.6(10) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 118.2(9) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? N5 C18 C17 122.8(10) . . ? N5 C18 H18 118.6 . . ? C17 C18 H18 118.6 . . ? N7 C19 S1 176.7(8) . . ? N8 C20 Cu2 173.5(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 N8 Cu1 N1 C1 -27.7(9) 2_656 . . . ? N6 Cu1 N1 C1 -172.7(9) . . . . ? S1 Cu1 N1 C1 86.7(8) . . . . ? N5 Cu1 N1 C1 -158.9(7) . . . . ? N8 Cu1 N1 C5 151.1(6) 2_656 . . . ? N6 Cu1 N1 C5 6.1(6) . . . . ? S1 Cu1 N1 C5 -94.4(6) . . . . ? N5 Cu1 N1 C5 19.9(9) . . . . ? C20 Cu2 N2 C7 133.6(6) . . . . ? N7 Cu2 N2 C7 -90.0(6) 1_455 . . . ? N3 Cu2 N2 C7 18.2(5) . . . . ? C20 Cu2 N2 C6 -77.1(8) . . . . ? N7 Cu2 N2 C6 59.3(8) 1_455 . . . ? N3 Cu2 N2 C6 167.5(8) . . . . ? C20 Cu2 N3 C8 -129.6(7) . . . . ? N7 Cu2 N3 C8 73.5(8) 1_455 . . . ? N2 Cu2 N3 C8 -11.7(6) . . . . ? C20 Cu2 N3 C9 53.7(8) . . . . ? N7 Cu2 N3 C9 -103.1(8) 1_455 . . . ? N2 Cu2 N3 C9 171.6(8) . . . . ? N8 Cu1 N5 C14 -152.2(6) 2_656 . . . ? N6 Cu1 N5 C14 -6.6(5) . . . . ? N1 Cu1 N5 C14 -20.5(9) . . . . ? S1 Cu1 N5 C14 96.6(6) . . . . ? N8 Cu1 N5 C18 31.6(10) 2_656 . . . ? N6 Cu1 N5 C18 177.3(9) . . . . ? N1 Cu1 N5 C18 163.4(8) . . . . ? S1 Cu1 N5 C18 -79.6(9) . . . . ? N8 Cu1 N6 C13 92.9(8) 2_656 . . . ? N1 Cu1 N6 C13 -177.8(6) . . . . ? S1 Cu1 N6 C13 -78.3(6) . . . . ? N5 Cu1 N6 C13 10.4(6) . . . . ? N8 Cu1 N6 C6 -101.2(8) 2_656 . . . ? N1 Cu1 N6 C6 -11.9(6) . . . . ? S1 Cu1 N6 C6 87.6(6) . . . . ? N5 Cu1 N6 C6 176.3(6) . . . . ? N8 Cu1 S1 C19 150.4(4) 2_656 . . . ? N6 Cu1 S1 C19 -34.8(4) . . . . ? N1 Cu1 S1 C19 41.5(4) . . . . ? N5 Cu1 S1 C19 -107.2(4) . . . . ? C5 N1 C1 C2 0.6(14) . . . . ? Cu1 N1 C1 C2 179.4(7) . . . . ? N1 C1 C2 C3 1.4(16) . . . . ? C1 C2 C3 C4 -1.6(16) . . . . ? C2 C3 C4 C5 0.0(15) . . . . ? C1 N1 C5 C4 -2.3(13) . . . . ? Cu1 N1 C5 C4 178.8(7) . . . . ? C1 N1 C5 C6 178.5(8) . . . . ? Cu1 N1 C5 C6 -0.5(9) . . . . ? C3 C4 C5 N1 2.0(14) . . . . ? C3 C4 C5 C6 -178.8(8) . . . . ? C13 N6 C6 N2 0.1(11) . . . . ? Cu1 N6 C6 N2 -166.4(5) . . . . ? C13 N6 C6 C5 -177.6(6) . . . . ? Cu1 N6 C6 C5 15.9(9) . . . . ? C7 N2 C6 N6 -0.4(10) . . . . ? Cu2 N2 C6 N6 -148.1(6) . . . . ? C7 N2 C6 C5 177.3(7) . . . . ? Cu2 N2 C6 C5 29.5(10) . . . . ? N1 C5 C6 N6 -9.4(10) . . . . ? C4 C5 C6 N6 171.4(8) . . . . ? N1 C5 C6 N2 172.8(7) . . . . ? C4 C5 C6 N2 -6.4(12) . . . . ? C6 N2 C7 N4 0.9(11) . . . . ? Cu2 N2 C7 N4 157.4(7) . . . . ? C6 N2 C7 C8 -179.1(7) . . . . ? Cu2 N2 C7 C8 -22.6(8) . . . . ? C13 N4 C7 N2 -1.2(11) . . . . ? C13 N4 C7 C8 178.8(7) . . . . ? C9 N3 C8 C12 1.3(13) . . . . ? Cu2 N3 C8 C12 -175.5(7) . . . . ? C9 N3 C8 C7 -179.4(8) . . . . ? Cu2 N3 C8 C7 3.7(10) . . . . ? N2 C7 C8 N3 15.5(11) . . . . ? N4 C7 C8 N3 -164.5(7) . . . . ? N2 C7 C8 C12 -165.2(8) . . . . ? N4 C7 C8 C12 14.8(12) . . . . ? C8 N3 C9 C10 -1.1(14) . . . . ? Cu2 N3 C9 C10 175.7(8) . . . . ? N3 C9 C10 C11 -0.3(17) . . . . ? C9 C10 C11 C12 1.5(17) . . . . ? C10 C11 C12 C8 -1.4(16) . . . . ? N3 C8 C12 C11 -0.1(14) . . . . ? C7 C8 C12 C11 -179.3(9) . . . . ? C6 N6 C13 N4 -0.4(10) . . . . ? Cu1 N6 C13 N4 165.8(6) . . . . ? C6 N6 C13 C14 -179.2(7) . . . . ? Cu1 N6 C13 C14 -12.9(9) . . . . ? C7 N4 C13 N6 0.9(11) . . . . ? C7 N4 C13 C14 179.7(6) . . . . ? C18 N5 C14 C15 0.5(13) . . . . ? Cu1 N5 C14 C15 -176.2(7) . . . . ? C18 N5 C14 C13 179.4(8) . . . . ? Cu1 N5 C14 C13 2.7(8) . . . . ? N6 C13 C14 N5 5.7(10) . . . . ? N4 C13 C14 N5 -173.2(7) . . . . ? N6 C13 C14 C15 -175.4(8) . . . . ? N4 C13 C14 C15 5.7(11) . . . . ? N5 C14 C15 C16 -0.4(14) . . . . ? C13 C14 C15 C16 -179.2(9) . . . . ? C14 C15 C16 C17 1.4(18) . . . . ? C15 C16 C17 C18 -2.3(19) . . . . ? C14 N5 C18 C17 -1.6(16) . . . . ? Cu1 N5 C18 C17 174.4(8) . . . . ? C16 C17 C18 N5 2.5(19) . . . . ? Cu2 N7 C19 S1 46(17) 1_655 . . . ? Cu1 S1 C19 N7 135(16) . . . . ? Cu1 N8 C20 Cu2 -36(12) 2_646 . . . ? N7 Cu2 C20 N8 116(7) 1_455 . . . ? N3 Cu2 C20 N8 -36(7) . . . . ? N2 Cu2 C20 N8 -125(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.080 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.168 # Attachment 'complex5.cif' data_1219am _database_code_depnum_ccdc_archive 'CCDC 293333' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 Cu2 N8 S2' _chemical_formula_weight 555.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 3.814(3) _cell_length_b 16.187(11) _cell_length_c 17.468(12) _cell_angle_alpha 113.292(10) _cell_angle_beta 92.875(12) _cell_angle_gamma 95.627(11) _cell_volume 981.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1645 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 22.3 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.881 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 2.409 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5318 _exptl_absorpt_correction_T_max 0.7139 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7077 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3448 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+0.0436P] 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 3448 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1717 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 0.5009(2) 0.52917(5) 0.18092(5) 0.0422(3) Uani 1 1 d . . . Cu2 Cu 0.8404(2) 0.16385(5) 0.06574(5) 0.0413(3) Uani 1 1 d . . . N1 N 0.5646(13) 0.6702(3) 0.1681(3) 0.0292(11) Uani 1 1 d . . . N2 N 0.4270(12) 0.6295(3) 0.2968(3) 0.0249(11) Uani 1 1 d . . . N3 N 0.4481(13) 0.4577(3) 0.2749(3) 0.0284(11) Uani 1 1 d . . . N4 N 0.2393(13) 0.6658(3) 0.4317(3) 0.0308(12) Uani 1 1 d . . . N5 N 0.1724(16) 0.7986(4) 0.5862(3) 0.0433(14) Uani 1 1 d . . . N6 N 0.3010(14) 0.7780(3) 0.3758(3) 0.0297(12) Uani 1 1 d . . . N7 N 0.8963(14) 0.2891(3) 0.0822(3) 0.0335(12) Uani 1 1 d . . . N8 N 0.2290(14) -0.0589(4) 0.0438(3) 0.0354(12) Uani 1 1 d . . . S1 S 0.9517(4) 0.47179(9) 0.10180(9) 0.0253(4) Uani 1 1 d . . . S2 S 0.3399(4) 0.13020(10) 0.13736(9) 0.0306(4) Uani 1 1 d . . . C1 C 0.6396(17) 0.6885(4) 0.1027(4) 0.0363(15) Uani 1 1 d . . . H1 H 0.6973 0.6416 0.0552 0.044 Uiso 1 1 calc R . . C2 C 0.6370(16) 0.7730(4) 0.1010(4) 0.0339(14) Uani 1 1 d . . . H2 H 0.6944 0.7827 0.0539 0.041 Uiso 1 1 calc R . . C3 C 0.5476(18) 0.8423(4) 0.1705(4) 0.0399(16) Uani 1 1 d . . . H3 H 0.5379 0.8997 0.1710 0.048 Uiso 1 1 calc R . . C4 C 0.4721(16) 0.8246(4) 0.2399(4) 0.0299(14) Uani 1 1 d . . . H4 H 0.4163 0.8705 0.2883 0.036 Uiso 1 1 calc R . . C5 C 0.4806(14) 0.7392(4) 0.2362(3) 0.0204(12) Uani 1 1 d . . . C6 C 0.3979(15) 0.7148(4) 0.3072(3) 0.0248(12) Uani 1 1 d . . . C7 C 0.2316(16) 0.7505(4) 0.4374(3) 0.0284(13) Uani 1 1 d . . . C8 C 0.1435(16) 0.8188(4) 0.5174(4) 0.0316(14) Uani 1 1 d . . . C9 C 0.046(2) 0.8985(4) 0.5208(4) 0.050(2) Uani 1 1 d . . . H9 H 0.0295 0.9108 0.4731 0.060 Uiso 1 1 calc R . . C10 C -0.025(3) 0.9595(5) 0.5959(5) 0.067(3) Uani 1 1 d . . . H10 H -0.0939 1.0143 0.5992 0.081 Uiso 1 1 calc R . . C11 C 0.000(2) 0.9433(5) 0.6660(4) 0.0495(19) Uani 1 1 d . . . H11 H -0.0505 0.9861 0.7170 0.059 Uiso 1 1 calc R . . C12 C 0.0995(19) 0.8630(5) 0.6599(4) 0.0467(18) Uani 1 1 d . . . H12 H 0.1191 0.8514 0.7079 0.056 Uiso 1 1 calc R . . C13 C 0.3345(15) 0.6077(4) 0.3602(3) 0.0250(12) Uani 1 1 d . . . C14 C 0.3462(15) 0.5124(4) 0.3487(3) 0.0253(12) Uani 1 1 d . . . C15 C 0.2541(17) 0.4827(4) 0.4100(4) 0.0307(14) Uani 1 1 d . . . H15 H 0.1831 0.5223 0.4601 0.037 Uiso 1 1 calc R . . C16 C 0.2702(19) 0.3937(4) 0.3951(4) 0.0393(16) Uani 1 1 d . . . H16 H 0.2127 0.3722 0.4356 0.047 Uiso 1 1 calc R . . C17 C 0.3707(18) 0.3362(4) 0.3205(4) 0.0368(15) Uani 1 1 d . . . H17 H 0.3797 0.2753 0.3091 0.044 Uiso 1 1 calc R . . C18 C 0.4578(17) 0.3712(4) 0.2632(4) 0.0312(14) Uani 1 1 d . . . H18 H 0.5284 0.3321 0.2128 0.037 Uiso 1 1 calc R . . C19 C 0.9181(14) 0.3646(4) 0.0909(3) 0.0240(12) Uani 1 1 d . . . C20 C 0.2745(15) 0.0182(4) 0.0827(3) 0.0255(13) 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 0.0379(5) 0.0350(5) 0.0344(5) -0.0071(4) 0.0066(4) 0.0064(4) Cu2 0.0590(6) 0.0181(4) 0.0420(5) 0.0074(4) 0.0048(4) 0.0042(4) N1 0.037(3) 0.026(3) 0.025(3) 0.009(2) 0.006(2) 0.005(2) N2 0.034(3) 0.021(3) 0.021(2) 0.008(2) 0.005(2) 0.007(2) N3 0.041(3) 0.025(3) 0.023(3) 0.012(2) 0.004(2) 0.005(2) N4 0.041(3) 0.029(3) 0.021(3) 0.007(2) 0.009(2) 0.008(2) N5 0.060(4) 0.038(3) 0.027(3) 0.008(3) 0.006(3) 0.005(3) N6 0.048(3) 0.022(3) 0.019(2) 0.006(2) 0.009(2) 0.010(2) N7 0.041(3) 0.025(3) 0.032(3) 0.008(2) 0.007(2) 0.004(2) N8 0.044(3) 0.029(3) 0.035(3) 0.014(3) 0.002(2) 0.008(2) S1 0.0261(8) 0.0199(7) 0.0311(8) 0.0106(6) 0.0055(6) 0.0050(6) S2 0.0323(8) 0.0225(8) 0.0281(8) 0.0005(6) 0.0031(6) 0.0049(6) C1 0.038(4) 0.040(4) 0.026(3) 0.008(3) 0.009(3) 0.007(3) C2 0.041(4) 0.040(4) 0.027(3) 0.020(3) 0.007(3) 0.001(3) C3 0.051(4) 0.036(4) 0.044(4) 0.027(3) 0.003(3) 0.011(3) C4 0.042(4) 0.021(3) 0.027(3) 0.007(3) 0.009(3) 0.012(3) C5 0.025(3) 0.020(3) 0.015(3) 0.005(2) 0.003(2) 0.005(2) C6 0.027(3) 0.021(3) 0.024(3) 0.006(3) 0.001(2) 0.005(2) C7 0.038(3) 0.023(3) 0.022(3) 0.005(3) 0.006(3) 0.005(3) C8 0.040(4) 0.028(3) 0.021(3) 0.004(3) 0.008(3) 0.006(3) C9 0.103(6) 0.027(4) 0.020(3) 0.005(3) 0.014(4) 0.027(4) C10 0.113(8) 0.033(4) 0.057(5) 0.012(4) 0.023(5) 0.037(5) C11 0.063(5) 0.040(4) 0.026(4) -0.009(3) 0.013(3) 0.011(4) C12 0.058(5) 0.050(5) 0.025(3) 0.007(3) 0.012(3) 0.003(4) C13 0.031(3) 0.023(3) 0.018(3) 0.004(2) 0.003(2) 0.005(2) C14 0.031(3) 0.019(3) 0.025(3) 0.007(2) 0.006(2) 0.006(2) C15 0.046(4) 0.023(3) 0.020(3) 0.004(2) 0.010(3) 0.007(3) C16 0.060(5) 0.028(3) 0.033(4) 0.016(3) 0.011(3) 0.002(3) C17 0.055(4) 0.022(3) 0.032(3) 0.010(3) 0.004(3) 0.003(3) C18 0.046(4) 0.020(3) 0.026(3) 0.005(3) 0.011(3) 0.008(3) C19 0.025(3) 0.024(3) 0.022(3) 0.007(2) 0.006(2) 0.005(2) C20 0.029(3) 0.031(4) 0.020(3) 0.013(3) 0.003(2) 0.007(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 Cu1 N2 2.089(5) . ? Cu1 S1 2.2949(19) . ? Cu1 S1 2.339(2) 1_455 ? Cu1 N3 2.358(5) . ? Cu1 N1 2.371(5) . ? Cu2 N7 1.921(5) . ? Cu2 N8 1.977(5) 2_655 ? Cu2 S2 2.449(2) 1_655 ? Cu2 S2 2.466(2) . ? N1 C1 1.326(8) . ? N1 C5 1.351(7) . ? N2 C6 1.335(7) . ? N2 C13 1.341(7) . ? N3 C18 1.339(7) . ? N3 C14 1.346(7) . ? N4 C13 1.327(7) . ? N4 C7 1.339(7) . ? N5 C12 1.361(9) . ? N5 C8 1.367(8) . ? N6 C6 1.331(7) . ? N6 C7 1.343(7) . ? N7 C19 1.164(7) . ? N8 C20 1.150(7) . ? N8 Cu2 1.977(5) 2_655 ? S1 C19 1.660(6) . ? S1 Cu1 2.339(2) 1_655 ? S2 C20 1.668(6) . ? S2 Cu2 2.449(2) 1_455 ? C1 C2 1.381(9) . ? C1 H1 0.9300 . ? C2 C3 1.375(9) . ? C2 H2 0.9300 . ? C3 C4 1.388(8) . ? C3 H3 0.9300 . ? C4 C5 1.362(8) . ? C4 H4 0.9300 . ? C5 C6 1.481(8) . ? C7 C8 1.478(8) . ? C8 C9 1.357(9) . ? C9 C10 1.355(10) . ? C9 H9 0.9300 . ? C10 C11 1.351(10) . ? C10 H10 0.9300 . ? C11 C12 1.357(10) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.479(8) . ? C14 C15 1.384(8) . ? C15 C16 1.368(8) . ? C15 H15 0.9300 . ? C16 C17 1.368(9) . ? C16 H16 0.9300 . ? C17 C18 1.370(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 S1 139.66(14) . . ? N2 Cu1 S1 108.92(14) . 1_455 ? S1 Cu1 S1 110.78(8) . 1_455 ? N2 Cu1 N3 73.27(18) . . ? S1 Cu1 N3 106.63(13) . . ? S1 Cu1 N3 99.38(13) 1_455 . ? N2 Cu1 N1 72.39(17) . . ? S1 Cu1 N1 95.85(13) . . ? S1 Cu1 N1 96.94(13) 1_455 . ? N3 Cu1 N1 145.18(16) . . ? N7 Cu2 N8 125.7(2) . 2_655 ? N7 Cu2 S2 111.04(16) . 1_655 ? N8 Cu2 S2 102.42(16) 2_655 1_655 ? N7 Cu2 S2 110.87(16) . . ? N8 Cu2 S2 102.23(17) 2_655 . ? S2 Cu2 S2 101.82(8) 1_655 . ? C1 N1 C5 117.0(5) . . ? C1 N1 Cu1 129.6(4) . . ? C5 N1 Cu1 113.1(3) . . ? C6 N2 C13 115.6(5) . . ? C6 N2 Cu1 122.2(4) . . ? C13 N2 Cu1 120.8(4) . . ? C18 N3 C14 116.2(5) . . ? C18 N3 Cu1 130.9(4) . . ? C14 N3 Cu1 112.3(4) . . ? C13 N4 C7 115.6(5) . . ? C12 N5 C8 116.7(6) . . ? C6 N6 C7 115.0(5) . . ? C19 N7 Cu2 177.6(5) . . ? C20 N8 Cu2 150.5(5) . 2_655 ? C19 S1 Cu1 104.0(2) . . ? C19 S1 Cu1 100.8(2) . 1_655 ? Cu1 S1 Cu1 110.78(8) . 1_655 ? C20 S2 Cu2 96.2(2) . 1_455 ? C20 S2 Cu2 97.5(2) . . ? Cu2 S2 Cu2 101.82(8) 1_455 . ? N1 C1 C2 123.8(6) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C3 C2 C1 118.6(6) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 118.4(6) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.3(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 123.0(5) . . ? N1 C5 C6 114.6(5) . . ? C4 C5 C6 122.4(5) . . ? N6 C6 N2 124.7(5) . . ? N6 C6 C5 118.6(5) . . ? N2 C6 C5 116.7(5) . . ? N4 C7 N6 124.6(5) . . ? N4 C7 C8 117.5(5) . . ? N6 C7 C8 117.8(5) . . ? C9 C8 N5 122.7(5) . . ? C9 C8 C7 120.0(6) . . ? N5 C8 C7 117.3(5) . . ? C10 C9 C8 117.8(6) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? C11 C10 C9 122.1(7) . . ? C11 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? C10 C11 C12 118.1(6) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C11 C12 N5 122.6(7) . . ? C11 C12 H12 118.7 . . ? N5 C12 H12 118.7 . . ? N4 C13 N2 124.3(5) . . ? N4 C13 C14 118.8(5) . . ? N2 C13 C14 116.9(5) . . ? N3 C14 C15 123.1(5) . . ? N3 C14 C13 115.4(5) . . ? C15 C14 C13 121.5(5) . . ? C16 C15 C14 118.3(5) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C17 C16 C15 120.0(6) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 118.0(6) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? N3 C18 C17 124.4(5) . . ? N3 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? N7 C19 S1 179.0(5) . . ? N8 C20 S2 178.8(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C1 178.8(6) . . . . ? S1 Cu1 N1 C1 38.3(5) . . . . ? S1 Cu1 N1 C1 -73.5(5) 1_455 . . . ? N3 Cu1 N1 C1 168.9(5) . . . . ? N2 Cu1 N1 C5 -7.5(4) . . . . ? S1 Cu1 N1 C5 -148.0(4) . . . . ? S1 Cu1 N1 C5 100.2(4) 1_455 . . . ? N3 Cu1 N1 C5 -17.3(6) . . . . ? S1 Cu1 N2 C6 87.4(5) . . . . ? S1 Cu1 N2 C6 -82.0(4) 1_455 . . . ? N3 Cu1 N2 C6 -176.5(5) . . . . ? N1 Cu1 N2 C6 9.4(4) . . . . ? S1 Cu1 N2 C13 -106.5(4) . . . . ? S1 Cu1 N2 C13 84.1(4) 1_455 . . . ? N3 Cu1 N2 C13 -10.3(4) . . . . ? N1 Cu1 N2 C13 175.6(5) . . . . ? N2 Cu1 N3 C18 179.7(6) . . . . ? S1 Cu1 N3 C18 -42.5(6) . . . . ? S1 Cu1 N3 C18 72.7(5) 1_455 . . . ? N1 Cu1 N3 C18 -170.5(5) . . . . ? N2 Cu1 N3 C14 9.4(4) . . . . ? S1 Cu1 N3 C14 147.2(4) . . . . ? S1 Cu1 N3 C14 -97.7(4) 1_455 . . . ? N1 Cu1 N3 C14 19.2(6) . . . . ? N8 Cu2 N7 C19 65(12) 2_655 . . . ? S2 Cu2 N7 C19 -171(12) 1_655 . . . ? S2 Cu2 N7 C19 -58(12) . . . . ? N2 Cu1 S1 C19 118.3(3) . . . . ? S1 Cu1 S1 C19 -72.5(2) 1_455 . . . ? N3 Cu1 S1 C19 34.7(2) . . . . ? N1 Cu1 S1 C19 -172.2(2) . . . . ? N2 Cu1 S1 Cu1 10.7(2) . . . 1_655 ? S1 Cu1 S1 Cu1 180.0 1_455 . . 1_655 ? N3 Cu1 S1 Cu1 -72.83(15) . . . 1_655 ? N1 Cu1 S1 Cu1 80.28(14) . . . 1_655 ? N7 Cu2 S2 C20 159.8(2) . . . . ? N8 Cu2 S2 C20 23.7(2) 2_655 . . . ? S2 Cu2 S2 C20 -82.0(2) 1_655 . . . ? N7 Cu2 S2 Cu2 61.82(18) . . . 1_455 ? N8 Cu2 S2 Cu2 -74.32(16) 2_655 . . 1_455 ? S2 Cu2 S2 Cu2 180.0 1_655 . . 1_455 ? C5 N1 C1 C2 0.2(9) . . . . ? Cu1 N1 C1 C2 173.7(5) . . . . ? N1 C1 C2 C3 -0.8(10) . . . . ? C1 C2 C3 C4 1.5(10) . . . . ? C2 C3 C4 C5 -1.6(10) . . . . ? C1 N1 C5 C4 -0.3(9) . . . . ? Cu1 N1 C5 C4 -174.8(5) . . . . ? C1 N1 C5 C6 179.8(5) . . . . ? Cu1 N1 C5 C6 5.2(6) . . . . ? C3 C4 C5 N1 1.0(9) . . . . ? C3 C4 C5 C6 -179.0(6) . . . . ? C7 N6 C6 N2 0.2(9) . . . . ? C7 N6 C6 C5 -179.8(5) . . . . ? C13 N2 C6 N6 3.1(9) . . . . ? Cu1 N2 C6 N6 169.9(5) . . . . ? C13 N2 C6 C5 -176.9(5) . . . . ? Cu1 N2 C6 C5 -10.0(7) . . . . ? N1 C5 C6 N6 -177.8(5) . . . . ? C4 C5 C6 N6 2.2(9) . . . . ? N1 C5 C6 N2 2.1(7) . . . . ? C4 C5 C6 N2 -177.8(5) . . . . ? C13 N4 C7 N6 2.2(9) . . . . ? C13 N4 C7 C8 -177.2(5) . . . . ? C6 N6 C7 N4 -3.0(9) . . . . ? C6 N6 C7 C8 176.4(5) . . . . ? C12 N5 C8 C9 -0.2(10) . . . . ? C12 N5 C8 C7 178.3(6) . . . . ? N4 C7 C8 C9 -163.7(7) . . . . ? N6 C7 C8 C9 16.8(10) . . . . ? N4 C7 C8 N5 17.7(9) . . . . ? N6 C7 C8 N5 -161.8(6) . . . . ? N5 C8 C9 C10 -0.3(12) . . . . ? C7 C8 C9 C10 -178.8(8) . . . . ? C8 C9 C10 C11 0.4(14) . . . . ? C9 C10 C11 C12 -0.1(14) . . . . ? C10 C11 C12 N5 -0.5(12) . . . . ? C8 N5 C12 C11 0.6(11) . . . . ? C7 N4 C13 N2 1.5(9) . . . . ? C7 N4 C13 C14 -179.4(5) . . . . ? C6 N2 C13 N4 -4.0(8) . . . . ? Cu1 N2 C13 N4 -171.0(5) . . . . ? C6 N2 C13 C14 176.9(5) . . . . ? Cu1 N2 C13 C14 9.9(7) . . . . ? C18 N3 C14 C15 -0.2(9) . . . . ? Cu1 N3 C14 C15 171.6(5) . . . . ? C18 N3 C14 C13 -179.5(5) . . . . ? Cu1 N3 C14 C13 -7.7(6) . . . . ? N4 C13 C14 N3 -179.5(5) . . . . ? N2 C13 C14 N3 -0.3(8) . . . . ? N4 C13 C14 C15 1.2(9) . . . . ? N2 C13 C14 C15 -179.6(6) . . . . ? N3 C14 C15 C16 0.5(10) . . . . ? C13 C14 C15 C16 179.8(6) . . . . ? C14 C15 C16 C17 -0.9(10) . . . . ? C15 C16 C17 C18 0.9(11) . . . . ? C14 N3 C18 C17 0.3(9) . . . . ? Cu1 N3 C18 C17 -169.8(5) . . . . ? C16 C17 C18 N3 -0.6(10) . . . . ? Cu2 N7 C19 S1 -91(36) . . . . ? Cu1 S1 C19 N7 148(35) . . . . ? Cu1 S1 C19 N7 -97(35) 1_655 . . . ? Cu2 N8 C20 S2 2(26) 2_655 . . . ? Cu2 S2 C20 N8 50(26) 1_455 . . . ? Cu2 S2 C20 N8 -53(26) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.946 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.167