# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Tarlok Lobana' _publ_contact_author_email tarlokslobana@yahoo.co.in loop_ _publ_author_name T.S.Lobana S.Khanna R.J.Butcher data_1 _database_code_depnum_ccdc_archive 'CCDC 710209' #TrackingRef '- cif files IC-C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Cu2 I2 N8 S2' _chemical_formula_weight 891.56 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' I I -0.4742 1.8119 '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 11.1959(14) _cell_length_b 22.689(3) _cell_length_c 11.9788(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.885(2) _cell_angle_gamma 90.00 _cell_volume 2940.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4324 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 31.65 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.014 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 3.721 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.490 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11154 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3637 _reflns_number_gt 3140 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'Apex2 v2.1-4' _computing_data_reduction 'Apex2 v2.1-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0358P)^2^+27.4186P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3637 _refine_ls_number_parameters 187 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C1 C 0.2712(4) 0.25952(19) 0.2712(4) 0.0206(9) Uani 1 1 d . . . H1 H 0.2993 0.2212 0.2585 0.025 Uiso 1 1 calc R . . C2 C 0.1946(4) 0.2661(2) 0.3451(4) 0.0244(9) Uani 1 1 d . . . H2 H 0.1714 0.2328 0.3828 0.029 Uiso 1 1 calc R . . C3 C 0.1528(4) 0.3210(2) 0.3631(4) 0.0256(10) Uani 1 1 d . . . H3 H 0.0991 0.3262 0.4121 0.031 Uiso 1 1 calc R . . C4 C 0.1903(4) 0.3695(2) 0.3082(4) 0.0212(9) Uani 1 1 d . . . H4 H 0.1632 0.4081 0.3200 0.025 Uiso 1 1 calc R . . C5 C 0.2675(4) 0.36006(17) 0.2366(3) 0.0149(7) Uani 1 1 d . . . C6 C 0.3105(4) 0.40769(17) 0.1718(3) 0.0132(7) Uani 1 1 d . . . C7 C 0.2633(3) 0.46912(17) 0.1734(3) 0.0123(7) Uani 1 1 d . . . C8 C 0.2904(4) 0.50275(18) 0.2735(4) 0.0171(8) Uani 1 1 d . . . H8 H 0.3437 0.4876 0.3424 0.021 Uiso 1 1 calc R . . C9 C 0.2392(4) 0.55897(19) 0.2729(4) 0.0198(8) Uani 1 1 d . . . H9 H 0.2584 0.5823 0.3411 0.024 Uiso 1 1 calc R . . C10 C 0.1605(4) 0.58047(19) 0.1729(4) 0.0193(8) Uani 1 1 d . . . H10 H 0.1248 0.6185 0.1728 0.023 Uiso 1 1 calc R . . C11 C 0.1330(4) 0.54707(19) 0.0723(4) 0.0186(8) Uani 1 1 d . . . H11 H 0.0793 0.5623 0.0037 0.022 Uiso 1 1 calc R . . C12 C 0.1843(4) 0.49131(17) 0.0723(3) 0.0143(7) Uani 1 1 d . . . H12 H 0.1657 0.4683 0.0037 0.017 Uiso 1 1 calc R . . C13 C 0.4953(3) 0.40271(17) -0.0180(3) 0.0142(7) Uani 1 1 d . . . Cu1 Cu 0.39130(4) 0.30376(2) 0.08871(4) 0.01294(11) Uani 1 1 d . . . I1 I 0.40205(2) 0.191996(12) 0.06053(2) 0.01924(9) Uani 1 1 d . . . N1 N 0.3066(3) 0.30511(14) 0.2176(3) 0.0151(6) Uani 1 1 d . . . N2 N 0.3822(3) 0.39053(14) 0.1093(3) 0.0121(6) Uani 1 1 d . . . N3 N 0.4352(3) 0.43036(14) 0.0507(3) 0.0123(6) Uani 1 1 d . . . N4 N 0.5578(3) 0.43688(16) -0.0753(3) 0.0176(7) Uani 1 1 d D . . H4B H 0.600(4) 0.418(2) -0.117(4) 0.021 Uiso 1 1 d D . . H4A H 0.561(5) 0.4761(9) -0.067(4) 0.021 Uiso 1 1 d D . . S1 S 0.49536(10) 0.32730(4) -0.04060(9) 0.0189(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 C1 0.028(2) 0.017(2) 0.018(2) 0.0030(16) 0.0081(17) -0.0063(17) C2 0.029(2) 0.022(2) 0.026(2) 0.0054(18) 0.0116(18) -0.0110(19) C3 0.031(2) 0.026(2) 0.026(2) 0.0026(19) 0.0202(19) -0.0083(19) C4 0.025(2) 0.020(2) 0.025(2) -0.0008(17) 0.0160(17) -0.0041(17) C5 0.0180(18) 0.0131(19) 0.0150(18) -0.0003(14) 0.0069(15) -0.0044(15) C6 0.0149(17) 0.0120(18) 0.0134(17) 0.0001(14) 0.0052(14) -0.0022(14) C7 0.0111(16) 0.0109(18) 0.0174(18) 0.0008(14) 0.0083(14) -0.0012(14) C8 0.0210(19) 0.014(2) 0.0163(19) -0.0007(15) 0.0044(15) 0.0009(15) C9 0.024(2) 0.016(2) 0.020(2) -0.0044(16) 0.0070(16) 0.0021(16) C10 0.0184(19) 0.0136(19) 0.027(2) -0.0023(16) 0.0077(16) 0.0015(15) C11 0.0138(18) 0.021(2) 0.020(2) 0.0039(16) 0.0030(15) 0.0009(15) C12 0.0156(17) 0.0140(19) 0.0147(18) -0.0022(14) 0.0061(14) -0.0024(14) C13 0.0138(17) 0.0116(18) 0.0188(19) 0.0038(14) 0.0073(14) -0.0002(14) Cu1 0.0164(2) 0.0080(2) 0.0168(2) 0.00139(17) 0.00854(18) -0.00068(17) I1 0.02006(14) 0.01472(15) 0.02281(15) 0.00045(10) 0.00528(10) 0.00114(10) N1 0.0188(16) 0.0118(16) 0.0157(16) 0.0006(12) 0.0061(13) -0.0022(13) N2 0.0153(15) 0.0109(15) 0.0118(15) 0.0022(12) 0.0063(12) -0.0032(12) N3 0.0166(15) 0.0070(15) 0.0146(15) 0.0007(12) 0.0067(12) -0.0016(12) N4 0.0196(16) 0.0124(17) 0.0271(18) 0.0001(14) 0.0175(14) 0.0010(13) S1 0.0242(5) 0.0094(4) 0.0295(5) -0.0002(4) 0.0186(4) 0.0004(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 C1 N1 1.330(5) . ? C1 C2 1.391(6) . ? C1 H1 0.9500 . ? C2 C3 1.365(7) . ? C2 H2 0.9500 . ? C3 C4 1.401(6) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 H4 0.9500 . ? C5 N1 1.360(5) . ? C5 C6 1.481(5) . ? C6 N2 1.291(5) . ? C6 C7 1.492(5) . ? C7 C8 1.387(5) . ? C7 C12 1.397(5) . ? C8 C9 1.398(6) . ? C8 H8 0.9500 . ? C9 C10 1.381(6) . ? C9 H9 0.9500 . ? C10 C11 1.389(6) . ? C10 H10 0.9500 . ? C11 C12 1.389(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N3 1.344(5) . ? C13 N4 1.346(5) . ? C13 S1 1.733(4) . ? Cu1 N2 1.990(3) . ? Cu1 N1 2.009(3) . ? Cu1 S1 2.2292(11) . ? Cu1 I1 2.5650(6) . ? N2 N3 1.369(4) . ? N4 H4B 0.882(19) . ? N4 H4A 0.895(19) . ? 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 N1 C1 C2 122.2(4) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 119.4(4) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.1(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 118.7(4) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.7(4) . . ? N1 C5 C6 114.8(3) . . ? C4 C5 C6 123.5(4) . . ? N2 C6 C5 114.7(3) . . ? N2 C6 C7 124.3(3) . . ? C5 C6 C7 120.7(3) . . ? C8 C7 C12 120.0(4) . . ? C8 C7 C6 121.7(4) . . ? C12 C7 C6 118.2(3) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 119.7(4) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.6(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C7 119.8(4) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? N3 C13 N4 116.9(3) . . ? N3 C13 S1 125.2(3) . . ? N4 C13 S1 117.9(3) . . ? N2 Cu1 N1 80.82(13) . . ? N2 Cu1 S1 84.35(9) . . ? N1 Cu1 S1 164.68(10) . . ? N2 Cu1 I1 179.54(10) . . ? N1 Cu1 I1 99.42(10) . . ? S1 Cu1 I1 95.44(3) . . ? C1 N1 C5 118.9(4) . . ? C1 N1 Cu1 128.1(3) . . ? C5 N1 Cu1 112.2(3) . . ? C6 N2 N3 121.0(3) . . ? C6 N2 Cu1 115.4(3) . . ? N3 N2 Cu1 123.2(2) . . ? C13 N3 N2 110.9(3) . . ? C13 N4 H4B 116(3) . . ? C13 N4 H4A 122(3) . . ? H4B N4 H4A 121(5) . . ? C13 S1 Cu1 96.12(13) . . ? 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 C1 C2 C3 0.6(7) . . . . ? C1 C2 C3 C4 -1.2(7) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? C3 C4 C5 N1 0.6(7) . . . . ? C3 C4 C5 C6 178.4(4) . . . . ? N1 C5 C6 N2 -2.1(5) . . . . ? C4 C5 C6 N2 -180.0(4) . . . . ? N1 C5 C6 C7 172.9(3) . . . . ? C4 C5 C6 C7 -5.0(6) . . . . ? N2 C6 C7 C8 -119.0(4) . . . . ? C5 C6 C7 C8 66.5(5) . . . . ? N2 C6 C7 C12 64.7(5) . . . . ? C5 C6 C7 C12 -109.9(4) . . . . ? C12 C7 C8 C9 -0.4(6) . . . . ? C6 C7 C8 C9 -176.7(4) . . . . ? C7 C8 C9 C10 0.8(6) . . . . ? C8 C9 C10 C11 -0.9(6) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C10 C11 C12 C7 0.0(6) . . . . ? C8 C7 C12 C11 0.0(6) . . . . ? C6 C7 C12 C11 176.4(3) . . . . ? C2 C1 N1 C5 0.7(6) . . . . ? C2 C1 N1 Cu1 -168.6(3) . . . . ? C4 C5 N1 C1 -1.3(6) . . . . ? C6 C5 N1 C1 -179.2(4) . . . . ? C4 C5 N1 Cu1 169.6(3) . . . . ? C6 C5 N1 Cu1 -8.4(4) . . . . ? N2 Cu1 N1 C1 -179.0(4) . . . . ? S1 Cu1 N1 C1 -164.4(3) . . . . ? I1 Cu1 N1 C1 1.4(4) . . . . ? N2 Cu1 N1 C5 11.2(3) . . . . ? S1 Cu1 N1 C5 25.8(6) . . . . ? I1 Cu1 N1 C5 -168.4(3) . . . . ? C5 C6 N2 N3 -175.7(3) . . . . ? C7 C6 N2 N3 9.5(6) . . . . ? C5 C6 N2 Cu1 11.9(4) . . . . ? C7 C6 N2 Cu1 -162.9(3) . . . . ? N1 Cu1 N2 C6 -13.0(3) . . . . ? S1 Cu1 N2 C6 170.9(3) . . . . ? N1 Cu1 N2 N3 174.8(3) . . . . ? S1 Cu1 N2 N3 -1.3(3) . . . . ? N4 C13 N3 N2 -176.2(3) . . . . ? S1 C13 N3 N2 5.4(5) . . . . ? C6 N2 N3 C13 -173.6(4) . . . . ? Cu1 N2 N3 C13 -1.8(4) . . . . ? N3 C13 S1 Cu1 -5.8(4) . . . . ? N4 C13 S1 Cu1 175.8(3) . . . . ? N2 Cu1 S1 C13 3.02(17) . . . . ? N1 Cu1 S1 C13 -11.4(4) . . . . ? I1 Cu1 S1 C13 -177.39(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A N3 0.895(19) 2.13(2) 3.026(5) 178(5) 5_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.086 _refine_diff_density_min -1.148 _refine_diff_density_rms 0.148 data_2 _database_code_depnum_ccdc_archive 'CCDC 710210' #TrackingRef '- cif files IC-C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H54 Cu2 I2 N8 P2 S2' _chemical_formula_sum 'C62 H54 Cu2 I2 N8 P2 S2' _chemical_formula_weight 1418.07 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7052(6) _cell_length_b 12.3415(4) _cell_length_c 13.1671(5) _cell_angle_alpha 62.760(4) _cell_angle_beta 64.620(4) _cell_angle_gamma 67.984(4) _cell_volume 1489.66(11) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9047 _cell_measurement_theta_min 4.6572 _cell_measurement_theta_max 32.5439 _exptl_crystal_description prism _exptl_crystal_colour 'pale olive-brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.920 _exptl_absorpt_correction_T_min 0.71929 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 22101 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 32.62 _reflns_number_total 9728 _reflns_number_gt 6047 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0422P)^2^] 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 9728 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 Cu Cu 0.85319(3) 0.07631(3) 0.52317(3) 0.02804(8) Uani 1 1 d . . . I I 0.756078(19) 0.223728(17) 0.349885(17) 0.03605(6) Uani 1 1 d . . . S S 1.05506(6) 0.13288(6) 0.46827(6) 0.02649(13) Uani 1 1 d . . . P P 0.71128(6) 0.06366(6) 0.70749(6) 0.02483(14) Uani 1 1 d . . . N1 N 1.0813(2) 0.0847(2) 0.6782(2) 0.0376(6) Uani 1 1 d . . . H1A H 1.0672 0.1064 0.7383 0.045 Uiso 1 1 calc R . . H1B H 1.1298 0.0109 0.6758 0.045 Uiso 1 1 calc R . . N2 N 0.9563(2) 0.2743(2) 0.5962(2) 0.0300(5) Uani 1 1 d . . . H2A H 0.9200 0.3256 0.5397 0.036 Uiso 1 1 calc R . . N3 N 0.9372(2) 0.3097(2) 0.6887(2) 0.0292(5) Uani 1 1 d . . . N4 N 0.8397(2) 0.4996(2) 0.4904(2) 0.0325(5) Uani 1 1 d . . . C1 C 1.0300(3) 0.1622(2) 0.5921(2) 0.0266(5) Uani 1 1 d . . . C2 C 0.8743(3) 0.4224(2) 0.6837(2) 0.0271(5) Uani 1 1 d . . . C3 C 0.8155(3) 0.5221(2) 0.5899(2) 0.0300(6) Uani 1 1 d . . . C4 C 0.7361(3) 0.6340(3) 0.6046(3) 0.0419(7) Uani 1 1 d . . . H4A H 0.7200 0.6492 0.6746 0.050 Uiso 1 1 calc R . . C5 C 0.6808(3) 0.7231(3) 0.5163(3) 0.0543(9) Uani 1 1 d . . . H5A H 0.6268 0.8000 0.5253 0.065 Uiso 1 1 calc R . . C6 C 0.7042(3) 0.6997(3) 0.4162(3) 0.0475(8) Uani 1 1 d . . . H6A H 0.6665 0.7591 0.3550 0.057 Uiso 1 1 calc R . . C7 C 0.7846(3) 0.5868(3) 0.4068(3) 0.0401(7) Uani 1 1 d . . . H7A H 0.8016 0.5703 0.3373 0.048 Uiso 1 1 calc R . . C8 C 0.8626(3) 0.4518(2) 0.7868(2) 0.0286(6) Uani 1 1 d . . . C9 C 0.9179(3) 0.5442(3) 0.7664(3) 0.0382(7) Uani 1 1 d . . . H9A H 0.9589 0.5924 0.6864 0.046 Uiso 1 1 calc R . . C10 C 0.9141(3) 0.5670(3) 0.8615(3) 0.0413(7) Uani 1 1 d . . . H10A H 0.9545 0.6291 0.8464 0.050 Uiso 1 1 calc R . . C11 C 0.8524(3) 0.5006(3) 0.9773(3) 0.0426(7) Uani 1 1 d . . . H11A H 0.8491 0.5169 1.0425 0.051 Uiso 1 1 calc R . . C12 C 0.7952(3) 0.4098(3) 0.9985(3) 0.0482(8) Uani 1 1 d . . . H12A H 0.7513 0.3643 1.0787 0.058 Uiso 1 1 calc R . . C13 C 0.8007(3) 0.3837(3) 0.9038(3) 0.0396(7) Uani 1 1 d . . . H13A H 0.7623 0.3199 0.9193 0.048 Uiso 1 1 calc R . . C1A C 0.6154(2) -0.0471(2) 0.7515(2) 0.0284(5) Uani 1 1 d . . . C2A C 0.6119(3) -0.1578(3) 0.8493(3) 0.0395(7) Uani 1 1 d . . . H2AA H 0.6602 -0.1797 0.9010 0.047 Uiso 1 1 calc R . . C3A C 0.5388(3) -0.2367(3) 0.8723(3) 0.0520(8) Uani 1 1 d . . . H3AA H 0.5383 -0.3132 0.9390 0.062 Uiso 1 1 calc R . . C4A C 0.4663(3) -0.2054(4) 0.7991(3) 0.0523(9) Uani 1 1 d . . . H4AA H 0.4164 -0.2602 0.8154 0.063 Uiso 1 1 calc R . . C5A C 0.4669(3) -0.0943(3) 0.7024(3) 0.0485(8) Uani 1 1 d . . . H5AA H 0.4154 -0.0714 0.6532 0.058 Uiso 1 1 calc R . . C6A C 0.5421(3) -0.0165(3) 0.6773(3) 0.0387(7) Uani 1 1 d . . . H6AA H 0.5443 0.0586 0.6091 0.046 Uiso 1 1 calc R . . C1B C 0.7764(2) 0.0038(2) 0.8316(2) 0.0264(5) Uani 1 1 d . . . C2B C 0.7325(3) 0.0586(3) 0.9172(3) 0.0390(7) Uani 1 1 d . . . H2BA H 0.6637 0.1310 0.9140 0.047 Uiso 1 1 calc R . . C3B C 0.7895(3) 0.0074(3) 1.0076(3) 0.0516(9) Uani 1 1 d . . . H3BA H 0.7593 0.0452 1.0658 0.062 Uiso 1 1 calc R . . C4B C 0.8896(3) -0.0981(3) 1.0135(3) 0.0513(9) Uani 1 1 d . . . H4BA H 0.9276 -0.1327 1.0759 0.062 Uiso 1 1 calc R . . C5B C 0.9341(3) -0.1526(3) 0.9285(3) 0.0441(7) Uani 1 1 d . . . H5BA H 1.0023 -0.2254 0.9324 0.053 Uiso 1 1 calc R . . C6B C 0.8787(3) -0.1006(3) 0.8376(3) 0.0380(7) Uani 1 1 d . . . H6BA H 0.9113 -0.1371 0.7779 0.046 Uiso 1 1 calc R . . C1C C 0.5861(2) 0.2010(2) 0.7269(2) 0.0258(5) Uani 1 1 d . . . C2C C 0.6066(3) 0.3189(3) 0.6455(3) 0.0356(6) Uani 1 1 d . . . H2CA H 0.6843 0.3265 0.5796 0.043 Uiso 1 1 calc R . . C3C C 0.5138(3) 0.4258(3) 0.6603(3) 0.0430(7) Uani 1 1 d . . . H3CA H 0.5292 0.5060 0.6053 0.052 Uiso 1 1 calc R . . C4C C 0.3997(3) 0.4156(3) 0.7544(3) 0.0430(7) Uani 1 1 d . . . H4CA H 0.3370 0.4888 0.7647 0.052 Uiso 1 1 calc R . . C5C C 0.3765(3) 0.2993(3) 0.8336(3) 0.0393(7) Uani 1 1 d . . . H5CA H 0.2970 0.2924 0.8973 0.047 Uiso 1 1 calc R . . C6C C 0.4691(3) 0.1928(3) 0.8203(2) 0.0332(6) Uani 1 1 d . . . H6CA H 0.4527 0.1130 0.8755 0.040 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 Cu 0.03074(18) 0.02976(17) 0.02365(16) -0.01267(13) -0.00709(14) -0.00431(14) I 0.04369(12) 0.03177(10) 0.03412(10) -0.01209(7) -0.02029(9) 0.00025(8) S 0.0312(3) 0.0252(3) 0.0265(3) -0.0137(2) -0.0081(3) -0.0051(3) P 0.0255(3) 0.0254(3) 0.0239(3) -0.0127(3) -0.0053(3) -0.0037(3) N1 0.0574(16) 0.0260(12) 0.0399(13) -0.0178(10) -0.0279(13) 0.0025(11) N2 0.0364(13) 0.0279(11) 0.0333(12) -0.0176(9) -0.0151(10) -0.0013(10) N3 0.0369(13) 0.0273(11) 0.0292(11) -0.0160(9) -0.0093(10) -0.0066(10) N4 0.0354(13) 0.0337(12) 0.0321(12) -0.0157(10) -0.0135(10) -0.0026(10) C1 0.0297(14) 0.0243(12) 0.0290(13) -0.0127(10) -0.0073(11) -0.0075(11) C2 0.0319(14) 0.0244(12) 0.0274(13) -0.0129(10) -0.0082(11) -0.0054(11) C3 0.0328(15) 0.0282(13) 0.0299(13) -0.0139(11) -0.0091(12) -0.0040(11) C4 0.0482(19) 0.0388(17) 0.0405(17) -0.0239(14) -0.0179(15) 0.0059(14) C5 0.059(2) 0.0407(18) 0.062(2) -0.0266(16) -0.0331(19) 0.0177(16) C6 0.050(2) 0.0434(18) 0.0475(19) -0.0140(15) -0.0262(17) 0.0018(15) C7 0.0407(17) 0.0439(17) 0.0368(16) -0.0174(13) -0.0181(14) 0.0005(14) C8 0.0368(15) 0.0233(12) 0.0271(13) -0.0135(10) -0.0110(12) -0.0010(11) C9 0.0566(19) 0.0313(15) 0.0282(14) -0.0129(11) -0.0091(14) -0.0131(14) C10 0.057(2) 0.0343(16) 0.0422(17) -0.0207(13) -0.0183(15) -0.0078(14) C11 0.0489(19) 0.0500(18) 0.0361(16) -0.0256(14) -0.0207(15) 0.0035(15) C12 0.047(2) 0.070(2) 0.0222(14) -0.0131(14) -0.0057(14) -0.0176(17) C13 0.0463(18) 0.0423(17) 0.0329(15) -0.0110(13) -0.0110(14) -0.0172(14) C1A 0.0253(14) 0.0310(14) 0.0302(13) -0.0177(11) -0.0025(11) -0.0062(11) C2A 0.0442(18) 0.0359(16) 0.0388(16) -0.0104(13) -0.0120(14) -0.0141(14) C3A 0.060(2) 0.0457(19) 0.0478(19) -0.0107(15) -0.0076(17) -0.0271(17) C4A 0.0396(19) 0.063(2) 0.066(2) -0.0369(19) -0.0015(17) -0.0233(17) C5A 0.0422(19) 0.060(2) 0.060(2) -0.0338(18) -0.0165(17) -0.0125(16) C6A 0.0388(17) 0.0419(17) 0.0425(17) -0.0179(13) -0.0153(14) -0.0096(13) C1B 0.0257(13) 0.0298(13) 0.0252(12) -0.0117(10) -0.0051(11) -0.0086(11) C2B 0.0383(17) 0.0445(17) 0.0406(16) -0.0274(14) -0.0119(14) -0.0005(13) C3B 0.060(2) 0.066(2) 0.0454(19) -0.0349(17) -0.0229(17) -0.0033(18) C4B 0.055(2) 0.064(2) 0.0453(19) -0.0182(17) -0.0270(17) -0.0121(18) C5B 0.0403(18) 0.0450(18) 0.0437(18) -0.0148(14) -0.0193(15) -0.0001(14) C6B 0.0396(17) 0.0392(16) 0.0374(16) -0.0199(13) -0.0140(14) -0.0006(13) C1C 0.0266(13) 0.0249(12) 0.0281(13) -0.0133(10) -0.0090(11) -0.0025(10) C2C 0.0363(16) 0.0327(15) 0.0330(15) -0.0149(12) -0.0015(13) -0.0097(12) C3C 0.0502(19) 0.0295(15) 0.0410(17) -0.0119(13) -0.0111(15) -0.0049(14) C4C 0.0448(19) 0.0331(16) 0.0426(17) -0.0196(13) -0.0128(15) 0.0071(13) C5C 0.0331(16) 0.0374(16) 0.0322(15) -0.0144(12) -0.0021(13) 0.0009(13) C6C 0.0341(16) 0.0287(14) 0.0275(14) -0.0101(11) -0.0037(12) -0.0041(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu P 2.2506(7) . ? Cu S 2.3644(7) 2_756 ? Cu S 2.4298(7) . ? Cu I 2.5847(4) . ? S C1 1.711(3) . ? S Cu 2.3644(7) 2_756 ? P C1C 1.816(3) . ? P C1A 1.826(3) . ? P C1B 1.827(3) . ? N1 C1 1.311(3) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C1 1.340(3) . ? N2 N3 1.380(3) . ? N2 H2A 0.8800 . ? N3 C2 1.293(3) . ? N4 C7 1.338(4) . ? N4 C3 1.352(3) . ? C2 C3 1.489(4) . ? C2 C8 1.499(3) . ? C3 C4 1.392(4) . ? C4 C5 1.386(4) . ? C4 H4A 0.9500 . ? C5 C6 1.370(5) . ? C5 H5A 0.9500 . ? C6 C7 1.385(4) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C9 1.384(4) . ? C8 C13 1.385(4) . ? C9 C10 1.384(4) . ? C9 H9A 0.9500 . ? C10 C11 1.369(4) . ? C10 H10A 0.9500 . ? C11 C12 1.378(5) . ? C11 H11A 0.9500 . ? C12 C13 1.395(4) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C1A C2A 1.383(4) . ? C1A C6A 1.404(4) . ? C2A C3A 1.380(4) . ? C2A H2AA 0.9500 . ? C3A C4A 1.382(5) . ? C3A H3AA 0.9500 . ? C4A C5A 1.380(5) . ? C4A H4AA 0.9500 . ? C5A C6A 1.378(4) . ? C5A H5AA 0.9500 . ? C6A H6AA 0.9500 . ? C1B C2B 1.390(4) . ? C1B C6B 1.390(4) . ? C2B C3B 1.392(4) . ? C2B H2BA 0.9500 . ? C3B C4B 1.384(5) . ? C3B H3BA 0.9500 . ? C4B C5B 1.381(5) . ? C4B H4BA 0.9500 . ? C5B C6B 1.384(4) . ? C5B H5BA 0.9500 . ? C6B H6BA 0.9500 . ? C1C C2C 1.391(4) . ? C1C C6C 1.395(4) . ? C2C C3C 1.391(4) . ? C2C H2CA 0.9500 . ? C3C C4C 1.378(4) . ? C3C H3CA 0.9500 . ? C4C C5C 1.378(4) . ? C4C H4CA 0.9500 . ? C5C C6C 1.383(4) . ? C5C H5CA 0.9500 . ? C6C H6CA 0.9500 . ? 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 P Cu S 105.27(3) . 2_756 ? P Cu S 117.93(3) . . ? S Cu S 96.80(2) 2_756 . ? P Cu I 114.08(2) . . ? S Cu I 115.776(19) 2_756 . ? S Cu I 106.10(2) . . ? C1 S Cu 116.54(9) . 2_756 ? C1 S Cu 100.66(9) . . ? Cu S Cu 83.20(2) 2_756 . ? C1C P C1A 101.93(12) . . ? C1C P C1B 104.35(12) . . ? C1A P C1B 103.79(12) . . ? C1C P Cu 118.93(9) . . ? C1A P Cu 107.85(8) . . ? C1B P Cu 117.89(9) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 120.3(2) . . ? C1 N2 H2A 119.9 . . ? N3 N2 H2A 119.9 . . ? C2 N3 N2 118.1(2) . . ? C7 N4 C3 118.6(2) . . ? N1 C1 N2 119.7(2) . . ? N1 C1 S 124.3(2) . . ? N2 C1 S 115.99(19) . . ? N3 C2 C3 128.1(2) . . ? N3 C2 C8 113.5(2) . . ? C3 C2 C8 118.4(2) . . ? N4 C3 C4 120.8(2) . . ? N4 C3 C2 117.8(2) . . ? C4 C3 C2 121.3(2) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 117.9(3) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? N4 C7 C6 123.5(3) . . ? N4 C7 H7A 118.3 . . ? C6 C7 H7A 118.3 . . ? C9 C8 C13 119.2(2) . . ? C9 C8 C2 120.3(2) . . ? C13 C8 C2 120.4(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 119.4(3) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C11 C12 C13 120.9(3) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C8 C13 C12 119.3(3) . . ? C8 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C2A C1A C6A 118.6(3) . . ? C2A C1A P 125.2(2) . . ? C6A C1A P 116.2(2) . . ? C3A C2A C1A 120.4(3) . . ? C3A C2A H2AA 119.8 . . ? C1A C2A H2AA 119.8 . . ? C2A C3A C4A 120.6(3) . . ? C2A C3A H3AA 119.7 . . ? C4A C3A H3AA 119.7 . . ? C5A C4A C3A 119.8(3) . . ? C5A C4A H4AA 120.1 . . ? C3A C4A H4AA 120.1 . . ? C6A C5A C4A 120.0(3) . . ? C6A C5A H5AA 120.0 . . ? C4A C5A H5AA 120.0 . . ? C5A C6A C1A 120.7(3) . . ? C5A C6A H6AA 119.7 . . ? C1A C6A H6AA 119.7 . . ? C2B C1B C6B 118.7(3) . . ? C2B C1B P 124.0(2) . . ? C6B C1B P 117.3(2) . . ? C1B C2B C3B 119.9(3) . . ? C1B C2B H2BA 120.1 . . ? C3B C2B H2BA 120.1 . . ? C4B C3B C2B 120.7(3) . . ? C4B C3B H3BA 119.6 . . ? C2B C3B H3BA 119.6 . . ? C5B C4B C3B 119.7(3) . . ? C5B C4B H4BA 120.2 . . ? C3B C4B H4BA 120.2 . . ? C4B C5B C6B 119.6(3) . . ? C4B C5B H5BA 120.2 . . ? C6B C5B H5BA 120.2 . . ? C5B C6B C1B 121.4(3) . . ? C5B C6B H6BA 119.3 . . ? C1B C6B H6BA 119.3 . . ? C2C C1C C6C 118.5(2) . . ? C2C C1C P 119.2(2) . . ? C6C C1C P 122.3(2) . . ? C3C C2C C1C 120.3(3) . . ? C3C C2C H2CA 119.8 . . ? C1C C2C H2CA 119.8 . . ? C4C C3C C2C 120.2(3) . . ? C4C C3C H3CA 119.9 . . ? C2C C3C H3CA 119.9 . . ? C5C C4C C3C 120.1(3) . . ? C5C C4C H4CA 120.0 . . ? C3C C4C H4CA 120.0 . . ? C4C C5C C6C 120.0(3) . . ? C4C C5C H5CA 120.0 . . ? C6C C5C H5CA 120.0 . . ? C5C C6C C1C 120.9(3) . . ? C5C C6C H6CA 119.5 . . ? C1C C6C H6CA 119.5 . . ? 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 P Cu S C1 -4.50(9) . . . . ? S Cu S C1 -115.81(9) 2_756 . . . ? I Cu S C1 124.83(9) . . . . ? P Cu S Cu 111.32(3) . . . 2_756 ? S Cu S Cu 0.0 2_756 . . 2_756 ? I Cu S Cu -119.36(2) . . . 2_756 ? S Cu P C1C -161.66(9) 2_756 . . . ? S Cu P C1C 91.86(10) . . . . ? I Cu P C1C -33.64(10) . . . . ? S Cu P C1A -46.44(10) 2_756 . . . ? S Cu P C1A -152.92(9) . . . . ? I Cu P C1A 81.57(9) . . . . ? S Cu P C1B 70.55(10) 2_756 . . . ? S Cu P C1B -35.93(10) . . . . ? I Cu P C1B -161.44(9) . . . . ? C1 N2 N3 C2 174.4(2) . . . . ? N3 N2 C1 N1 1.8(4) . . . . ? N3 N2 C1 S -175.98(18) . . . . ? Cu S C1 N1 14.6(3) 2_756 . . . ? Cu S C1 N1 102.2(2) . . . . ? Cu S C1 N2 -167.77(16) 2_756 . . . ? Cu S C1 N2 -80.1(2) . . . . ? N2 N3 C2 C3 1.3(4) . . . . ? N2 N3 C2 C8 -178.3(2) . . . . ? C7 N4 C3 C4 -0.7(4) . . . . ? C7 N4 C3 C2 178.1(2) . . . . ? N3 C2 C3 N4 -7.3(4) . . . . ? C8 C2 C3 N4 172.3(2) . . . . ? N3 C2 C3 C4 171.5(3) . . . . ? C8 C2 C3 C4 -8.9(4) . . . . ? N4 C3 C4 C5 0.3(5) . . . . ? C2 C3 C4 C5 -178.4(3) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C4 C5 C6 C7 -0.7(5) . . . . ? C3 N4 C7 C6 0.3(5) . . . . ? C5 C6 C7 N4 0.4(5) . . . . ? N3 C2 C8 C9 117.4(3) . . . . ? C3 C2 C8 C9 -62.3(4) . . . . ? N3 C2 C8 C13 -60.2(4) . . . . ? C3 C2 C8 C13 120.2(3) . . . . ? C13 C8 C9 C10 1.3(4) . . . . ? C2 C8 C9 C10 -176.2(3) . . . . ? C8 C9 C10 C11 -1.7(5) . . . . ? C9 C10 C11 C12 0.6(5) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C9 C8 C13 C12 0.1(4) . . . . ? C2 C8 C13 C12 177.7(3) . . . . ? C11 C12 C13 C8 -1.2(5) . . . . ? C1C P C1A C2A -115.9(2) . . . . ? C1B P C1A C2A -7.7(3) . . . . ? Cu P C1A C2A 118.1(2) . . . . ? C1C P C1A C6A 65.3(2) . . . . ? C1B P C1A C6A 173.6(2) . . . . ? Cu P C1A C6A -60.6(2) . . . . ? C6A C1A C2A C3A 0.7(4) . . . . ? P C1A C2A C3A -178.1(2) . . . . ? C1A C2A C3A C4A -1.0(5) . . . . ? C2A C3A C4A C5A -0.1(5) . . . . ? C3A C4A C5A C6A 1.7(5) . . . . ? C4A C5A C6A C1A -2.1(5) . . . . ? C2A C1A C6A C5A 0.9(4) . . . . ? P C1A C6A C5A 179.7(2) . . . . ? C1C P C1B C2B 0.1(3) . . . . ? C1A P C1B C2B -106.3(2) . . . . ? Cu P C1B C2B 134.5(2) . . . . ? C1C P C1B C6B -177.8(2) . . . . ? C1A P C1B C6B 75.8(2) . . . . ? Cu P C1B C6B -43.4(2) . . . . ? C6B C1B C2B C3B -1.1(4) . . . . ? P C1B C2B C3B -179.0(2) . . . . ? C1B C2B C3B C4B -0.1(5) . . . . ? C2B C3B C4B C5B 0.4(6) . . . . ? C3B C4B C5B C6B 0.5(5) . . . . ? C4B C5B C6B C1B -1.8(5) . . . . ? C2B C1B C6B C5B 2.1(4) . . . . ? P C1B C6B C5B -179.9(2) . . . . ? C1A P C1C C2C -142.7(2) . . . . ? C1B P C1C C2C 109.5(2) . . . . ? Cu P C1C C2C -24.4(2) . . . . ? C1A P C1C C6C 36.8(2) . . . . ? C1B P C1C C6C -71.0(2) . . . . ? Cu P C1C C6C 155.14(19) . . . . ? C6C C1C C2C C3C 2.3(4) . . . . ? P C1C C2C C3C -178.2(2) . . . . ? C1C C2C C3C C4C -1.2(5) . . . . ? C2C C3C C4C C5C -0.7(5) . . . . ? C3C C4C C5C C6C 1.5(5) . . . . ? C4C C5C C6C C1C -0.4(4) . . . . ? C2C C1C C6C C5C -1.4(4) . . . . ? P C1C C6C C5C 179.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B I 0.88 2.81 3.674(2) 167.5 2_756 N2 H2A N4 0.88 1.91 2.603(3) 134.3 . _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.917 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.100 data_3 _database_code_depnum_ccdc_archive 'CCDC 710211' #TrackingRef '- cif files IC-C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Br2 Cu2 N8 S2' _chemical_formula_weight 797.54 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 10.9775(12) _cell_length_b 22.299(2) _cell_length_c 11.9300(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.245(2) _cell_angle_gamma 90.00 _cell_volume 2803.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5765 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 31.76 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 4.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.540 _exptl_absorpt_correction_T_max 0.634 _exptl_absorpt_process_details 'Apex2 v2.1-4 (Bruker, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14150 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3499 _reflns_number_gt 3053 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'Apex2 v2.1-4' _computing_data_reduction 'Apex2 v2.1-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0296P)^2^+3.2879P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3499 _refine_ls_number_parameters 187 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _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 Br1 Br 0.397404(19) 0.195173(8) 0.059989(18) 0.01662(6) Uani 1 1 d . . . C1 C 0.2728(2) 0.25572(9) 0.26910(18) 0.0180(4) Uani 1 1 d . . . H1 H 0.3019 0.2170 0.2558 0.022 Uiso 1 1 calc R . . C2 C 0.1977(2) 0.26143(10) 0.34393(19) 0.0208(4) Uani 1 1 d . . . H2 H 0.1770 0.2272 0.3824 0.025 Uiso 1 1 calc R . . C3 C 0.1531(2) 0.31727(10) 0.3622(2) 0.0220(4) Uani 1 1 d . . . H3 H 0.1000 0.3221 0.4123 0.026 Uiso 1 1 calc R . . C4 C 0.1874(2) 0.36674(9) 0.30565(18) 0.0179(4) Uani 1 1 d . . . H4 H 0.1578 0.4057 0.3166 0.022 Uiso 1 1 calc R . . C5 C 0.26487(18) 0.35821(9) 0.23369(17) 0.0133(4) Uani 1 1 d . . . C6 C 0.30621(18) 0.40688(8) 0.16894(16) 0.0121(4) Uani 1 1 d . . . C7 C 0.25784(18) 0.46898(8) 0.16978(17) 0.0117(4) Uani 1 1 d . . . C8 C 0.28056(19) 0.50274(9) 0.27180(17) 0.0153(4) Uani 1 1 d . . . H8 H 0.3322 0.4870 0.3433 0.018 Uiso 1 1 calc R . . C9 C 0.2276(2) 0.55959(9) 0.26891(19) 0.0185(4) Uani 1 1 d . . . H9 H 0.2442 0.5828 0.3384 0.022 Uiso 1 1 calc R . . C10 C 0.15063(19) 0.58264(9) 0.16512(19) 0.0183(4) Uani 1 1 d . . . H10 H 0.1136 0.6213 0.1636 0.022 Uiso 1 1 calc R . . C11 C 0.12800(19) 0.54904(9) 0.06365(18) 0.0177(4) Uani 1 1 d . . . H11 H 0.0753 0.5648 -0.0074 0.021 Uiso 1 1 calc R . . C12 C 0.18158(18) 0.49261(9) 0.06502(17) 0.0141(4) Uani 1 1 d . . . H12 H 0.1665 0.4701 -0.0051 0.017 Uiso 1 1 calc R . . C13 C 0.49148(18) 0.40212(9) -0.02137(17) 0.0137(4) Uani 1 1 d . . . Cu1 Cu 0.38658(2) 0.301294(10) 0.08399(2) 0.01252(7) Uani 1 1 d . . . N1 N 0.30600(16) 0.30263(7) 0.21486(15) 0.0135(3) Uani 1 1 d . . . N2 N 0.37883(15) 0.38932(7) 0.10588(14) 0.0115(3) Uani 1 1 d . . . N3 N 0.43215(15) 0.42980(7) 0.04759(14) 0.0126(3) Uani 1 1 d . . . N4 N 0.55455(17) 0.43648(8) -0.07776(16) 0.0168(4) Uani 1 1 d D . . H4A H 0.596(2) 0.4187(10) -0.1188(19) 0.020 Uiso 1 1 d D . . H4B H 0.561(2) 0.4754(7) -0.067(2) 0.020 Uiso 1 1 d D . . S1 S 0.48838(5) 0.32535(2) -0.04697(5) 0.01737(11) 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 Br1 0.01815(11) 0.01041(10) 0.02061(11) 0.00012(7) 0.00428(8) 0.00155(7) C1 0.0232(11) 0.0126(9) 0.0177(10) 0.0023(8) 0.0048(8) -0.0036(8) C2 0.0250(11) 0.0178(10) 0.0215(11) 0.0046(8) 0.0098(9) -0.0066(8) C3 0.0253(11) 0.0236(11) 0.0217(10) 0.0007(9) 0.0145(9) -0.0050(9) C4 0.0210(10) 0.0158(9) 0.0201(10) -0.0013(8) 0.0109(8) -0.0010(8) C5 0.0154(9) 0.0118(9) 0.0132(9) 0.0006(7) 0.0046(7) -0.0023(7) C6 0.0126(9) 0.0114(9) 0.0121(9) -0.0003(7) 0.0032(7) -0.0012(7) C7 0.0114(9) 0.0097(8) 0.0158(9) 0.0010(7) 0.0068(7) -0.0014(7) C8 0.0178(10) 0.0139(9) 0.0133(9) -0.0015(7) 0.0029(8) 0.0006(8) C9 0.0222(11) 0.0136(9) 0.0199(10) -0.0048(8) 0.0064(9) 0.0009(8) C10 0.0174(10) 0.0115(9) 0.0260(11) 0.0010(8) 0.0062(8) 0.0025(8) C11 0.0137(9) 0.0184(10) 0.0195(10) 0.0054(8) 0.0024(8) -0.0006(8) C12 0.0135(9) 0.0162(9) 0.0132(9) -0.0001(7) 0.0049(7) -0.0028(7) C13 0.0122(9) 0.0126(9) 0.0159(9) -0.0003(7) 0.0033(7) -0.0002(7) Cu1 0.01575(12) 0.00799(12) 0.01575(13) 0.00007(9) 0.00759(10) -0.00033(9) N1 0.0157(8) 0.0105(8) 0.0145(8) 0.0007(6) 0.0048(7) -0.0012(6) N2 0.0123(8) 0.0096(7) 0.0126(8) 0.0000(6) 0.0034(6) -0.0015(6) N3 0.0148(8) 0.0098(7) 0.0150(8) 0.0007(6) 0.0073(7) -0.0023(6) N4 0.0201(9) 0.0118(8) 0.0238(9) -0.0003(7) 0.0148(7) -0.0008(7) S1 0.0218(3) 0.0107(2) 0.0251(3) -0.00244(19) 0.0156(2) -0.00084(19) _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 Br1 Cu1 2.3906(4) . ? C1 N1 1.333(2) . ? C1 C2 1.380(3) . ? C1 H1 0.9500 . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 N1 1.359(2) . ? C5 C6 1.475(3) . ? C6 N2 1.300(2) . ? C6 C7 1.484(3) . ? C7 C8 1.393(3) . ? C7 C12 1.398(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.388(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N4 1.334(2) . ? C13 N3 1.335(2) . ? C13 S1 1.737(2) . ? Cu1 N2 1.9851(16) . ? Cu1 N1 1.9984(17) . ? Cu1 S1 2.2258(6) . ? N2 N3 1.367(2) . ? N4 H4A 0.853(16) . ? N4 H4B 0.878(16) . ? 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 N1 C1 C2 122.4(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.29(19) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.7(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.17(19) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 121.30(18) . . ? N1 C5 C6 114.79(17) . . ? C4 C5 C6 123.89(18) . . ? N2 C6 C5 114.17(17) . . ? N2 C6 C7 124.30(17) . . ? C5 C6 C7 121.32(17) . . ? C8 C7 C12 119.56(17) . . ? C8 C7 C6 122.22(17) . . ? C12 C7 C6 118.13(17) . . ? C9 C8 C7 119.97(19) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.37(19) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.65(19) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.56(19) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.88(18) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? N4 C13 N3 117.17(17) . . ? N4 C13 S1 117.69(15) . . ? N3 C13 S1 125.10(15) . . ? N2 Cu1 N1 80.67(6) . . ? N2 Cu1 S1 84.40(5) . . ? N1 Cu1 S1 164.51(5) . . ? N2 Cu1 Br1 179.32(5) . . ? N1 Cu1 Br1 98.97(5) . . ? S1 Cu1 Br1 95.912(16) . . ? C1 N1 C5 119.13(18) . . ? C1 N1 Cu1 127.46(14) . . ? C5 N1 Cu1 112.51(12) . . ? C6 N2 N3 120.96(16) . . ? C6 N2 Cu1 115.46(13) . . ? N3 N2 Cu1 123.08(12) . . ? C13 N3 N2 111.12(15) . . ? C13 N4 H4A 117.2(16) . . ? C13 N4 H4B 121.7(16) . . ? H4A N4 H4B 121(2) . . ? C13 S1 Cu1 95.91(7) . . ? 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 C1 C2 C3 1.2(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 N1 1.5(3) . . . . ? C3 C4 C5 C6 179.46(19) . . . . ? N1 C5 C6 N2 -1.8(2) . . . . ? C4 C5 C6 N2 -179.88(19) . . . . ? N1 C5 C6 C7 173.18(17) . . . . ? C4 C5 C6 C7 -4.9(3) . . . . ? N2 C6 C7 C8 -122.8(2) . . . . ? C5 C6 C7 C8 62.7(3) . . . . ? N2 C6 C7 C12 60.5(3) . . . . ? C5 C6 C7 C12 -113.9(2) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? C6 C7 C8 C9 -176.68(18) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C7 0.8(3) . . . . ? C8 C7 C12 C11 -0.8(3) . . . . ? C6 C7 C12 C11 175.97(18) . . . . ? C2 C1 N1 C5 0.1(3) . . . . ? C2 C1 N1 Cu1 -168.17(16) . . . . ? C4 C5 N1 C1 -1.4(3) . . . . ? C6 C5 N1 C1 -179.62(17) . . . . ? C4 C5 N1 Cu1 168.51(16) . . . . ? C6 C5 N1 Cu1 -9.7(2) . . . . ? N2 Cu1 N1 C1 -178.52(19) . . . . ? S1 Cu1 N1 C1 -162.86(15) . . . . ? Br1 Cu1 N1 C1 0.89(18) . . . . ? N2 Cu1 N1 C5 12.54(13) . . . . ? S1 Cu1 N1 C5 28.2(3) . . . . ? Br1 Cu1 N1 C5 -168.04(13) . . . . ? C5 C6 N2 N3 -175.23(16) . . . . ? C7 C6 N2 N3 10.0(3) . . . . ? C5 C6 N2 Cu1 12.7(2) . . . . ? C7 C6 N2 Cu1 -162.11(14) . . . . ? N1 Cu1 N2 C6 -14.16(14) . . . . ? S1 Cu1 N2 C6 170.00(14) . . . . ? N1 Cu1 N2 N3 173.91(15) . . . . ? S1 Cu1 N2 N3 -1.93(13) . . . . ? N4 C13 N3 N2 -175.89(17) . . . . ? S1 C13 N3 N2 6.4(2) . . . . ? C6 N2 N3 C13 -173.28(17) . . . . ? Cu1 N2 N3 C13 -1.8(2) . . . . ? N4 C13 S1 Cu1 175.30(15) . . . . ? N3 C13 S1 Cu1 -7.00(18) . . . . ? N2 Cu1 S1 C13 3.78(8) . . . . ? N1 Cu1 S1 C13 -11.8(2) . . . . ? Br1 Cu1 S1 C13 -175.62(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B N3 0.878(16) 2.125(16) 3.002(2) 177(2) 5_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.467 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.081 data_4 _database_code_depnum_ccdc_archive 'CCDC 710212' #TrackingRef '- cif files IC-C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H54 Br2 Cu2 N8 P2 S2' _chemical_formula_sum 'C62 H54 Br2 Cu2 N8 P2 S2' _chemical_formula_weight 1324.09 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' Br Br -0.2901 2.4595 '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 11.8176(18) _cell_length_b 12.2666(17) _cell_length_c 12.9683(19) _cell_angle_alpha 61.805(15) _cell_angle_beta 65.714(14) _cell_angle_gamma 67.653(14) _cell_volume 1469.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3597 _cell_measurement_theta_min 4.6510 _cell_measurement_theta_max 32.5505 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow-brown' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 2.256 _exptl_absorpt_correction_T_min 0.84735 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 24020 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.1520 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 32.65 _reflns_number_total 9721 _reflns_number_gt 4085 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0256P)^2^] 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 9721 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1302 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0546 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _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 Cu Cu 0.15025(3) 0.42241(3) -0.01919(3) 0.04073(9) Uani 1 1 d . . . Br Br 0.23235(3) 0.28991(2) 0.15527(3) 0.05532(9) Uani 1 1 d . . . S S -0.04992(6) 0.36536(5) 0.03150(5) 0.03668(14) Uani 1 1 d . . . P P 0.29004(6) 0.43418(5) -0.20283(5) 0.03385(14) Uani 1 1 d . . . N1 N -0.0761(2) 0.42166(17) -0.18440(18) 0.0503(6) Uani 1 1 d . . . H1A H -0.0622 0.4027 -0.2451 0.060 Uiso 1 1 calc R . . H1B H -0.1226 0.4947 -0.1825 0.060 Uiso 1 1 calc R . . N2 N 0.04554(18) 0.22626(16) -0.09879(17) 0.0409(5) Uani 1 1 d . . . H2A H 0.0798 0.1727 -0.0410 0.049 Uiso 1 1 calc R . . N3 N 0.06569(19) 0.19423(16) -0.19404(17) 0.0386(5) Uani 1 1 d . . . N4 N 0.15718(19) -0.00593(17) 0.01379(18) 0.0413(5) Uani 1 1 d . . . C1 C -0.0264(2) 0.33910(19) -0.0944(2) 0.0353(5) Uani 1 1 d . . . C2 C 0.1266(2) 0.0797(2) -0.1870(2) 0.0372(6) Uani 1 1 d . . . C3 C 0.1825(2) -0.0243(2) -0.0886(2) 0.0382(6) Uani 1 1 d . . . C4 C 0.2091(3) -0.0983(2) 0.1017(2) 0.0534(7) Uani 1 1 d . . . H4A H 0.1924 -0.0841 0.1715 0.064 Uiso 1 1 calc R . . C5 C 0.2848(3) -0.2112(3) 0.0948(3) 0.0647(8) Uani 1 1 d . . . H5A H 0.3183 -0.2734 0.1586 0.078 Uiso 1 1 calc R . . C6 C 0.3104(3) -0.2311(3) -0.0088(3) 0.0683(9) Uani 1 1 d . . . H6A H 0.3619 -0.3076 -0.0163 0.082 Uiso 1 1 calc R . . C7 C 0.2599(3) -0.1379(2) -0.1014(3) 0.0569(7) Uani 1 1 d . . . H7A H 0.2773 -0.1507 -0.1722 0.068 Uiso 1 1 calc R . . C8 C 0.1397(2) 0.05254(19) -0.2930(2) 0.0378(6) Uani 1 1 d . . . C9 C 0.0838(3) -0.0375(2) -0.2753(2) 0.0525(7) Uani 1 1 d . . . H9A H 0.0405 -0.0835 -0.1967 0.063 Uiso 1 1 calc R . . C10 C 0.0911(3) -0.0602(2) -0.3721(3) 0.0621(8) Uani 1 1 d . . . H10A H 0.0523 -0.1207 -0.3588 0.075 Uiso 1 1 calc R . . C11 C 0.1550(3) 0.0053(3) -0.4874(3) 0.0635(8) Uani 1 1 d . . . H11A H 0.1593 -0.0095 -0.5530 0.076 Uiso 1 1 calc R . . C12 C 0.2126(3) 0.0927(3) -0.5059(3) 0.0691(9) Uani 1 1 d . . . H12A H 0.2587 0.1356 -0.5843 0.083 Uiso 1 1 calc R . . C13 C 0.2034(3) 0.1186(3) -0.4096(2) 0.0555(7) Uani 1 1 d . . . H13A H 0.2404 0.1809 -0.4239 0.067 Uiso 1 1 calc R . . C1A C 0.4115(2) 0.29232(19) -0.2185(2) 0.0353(5) Uani 1 1 d . . . C2A C 0.3879(2) 0.1745(2) -0.1348(2) 0.0493(7) Uani 1 1 d . . . H2AA H 0.3127 0.1694 -0.0713 0.059 Uiso 1 1 calc R . . C3A C 0.4757(3) 0.0648(2) -0.1454(3) 0.0616(8) Uani 1 1 d . . . H3AA H 0.4591 -0.0139 -0.0889 0.074 Uiso 1 1 calc R . . C4A C 0.5872(3) 0.0706(2) -0.2384(3) 0.0599(8) Uani 1 1 d . . . H4AA H 0.6457 -0.0036 -0.2459 0.072 Uiso 1 1 calc R . . C5A C 0.6113(3) 0.1875(2) -0.3206(3) 0.0585(8) Uani 1 1 d . . . H5AA H 0.6871 0.1923 -0.3835 0.070 Uiso 1 1 calc R . . C6A C 0.5246(2) 0.2972(2) -0.3108(2) 0.0471(6) Uani 1 1 d . . . H6AA H 0.5423 0.3756 -0.3670 0.057 Uiso 1 1 calc R . . C1B C 0.3878(2) 0.5422(2) -0.2459(2) 0.0368(5) Uani 1 1 d . . . C2B C 0.4574(2) 0.5097(2) -0.1669(2) 0.0493(7) Uani 1 1 d . . . H2BA H 0.4528 0.4356 -0.0974 0.059 Uiso 1 1 calc R . . C3B C 0.5323(3) 0.5849(3) -0.1898(3) 0.0621(8) Uani 1 1 d . . . H3BA H 0.5808 0.5604 -0.1381 0.074 Uiso 1 1 calc R . . C4B C 0.5353(3) 0.6968(3) -0.2898(3) 0.0702(9) Uani 1 1 d . . . H4BA H 0.5841 0.7494 -0.3043 0.084 Uiso 1 1 calc R . . C5B C 0.4669(3) 0.7316(3) -0.3684(3) 0.0688(9) Uani 1 1 d . . . H5BA H 0.4697 0.8074 -0.4361 0.083 Uiso 1 1 calc R . . C6B C 0.3932(3) 0.6533(2) -0.3466(2) 0.0540(7) Uani 1 1 d . . . H6BA H 0.3475 0.6764 -0.4003 0.065 Uiso 1 1 calc R . . C1C C 0.2261(2) 0.4990(2) -0.3322(2) 0.0356(5) Uani 1 1 d . . . C2C C 0.1254(2) 0.6051(2) -0.3407(2) 0.0505(7) Uani 1 1 d . . . H2CA H 0.0934 0.6398 -0.2813 0.061 Uiso 1 1 calc R . . C3C C 0.0715(3) 0.6603(2) -0.4353(3) 0.0629(8) Uani 1 1 d . . . H3CA H 0.0055 0.7330 -0.4407 0.075 Uiso 1 1 calc R . . C4C C 0.1154(3) 0.6078(3) -0.5213(3) 0.0676(9) Uani 1 1 d . . . H4CA H 0.0791 0.6447 -0.5851 0.081 Uiso 1 1 calc R . . C5C C 0.2122(3) 0.5016(3) -0.5132(3) 0.0728(9) Uani 1 1 d . . . H5CA H 0.2410 0.4655 -0.5711 0.087 Uiso 1 1 calc R . . C6C C 0.2682(3) 0.4467(2) -0.4189(2) 0.0557(7) Uani 1 1 d . . . H6CA H 0.3344 0.3743 -0.4143 0.067 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 Cu 0.04215(19) 0.04418(16) 0.03320(18) -0.01898(13) -0.00714(14) -0.00540(13) Br 0.0682(2) 0.04709(15) 0.05119(18) -0.01966(13) -0.03231(16) 0.00456(13) S 0.0433(4) 0.0330(3) 0.0371(3) -0.0182(3) -0.0093(3) -0.0079(3) P 0.0337(4) 0.0350(3) 0.0328(3) -0.0175(3) -0.0063(3) -0.0050(3) N1 0.0705(16) 0.0372(11) 0.0511(14) -0.0246(10) -0.0285(13) 0.0023(10) N2 0.0528(13) 0.0327(10) 0.0451(12) -0.0228(9) -0.0203(11) 0.0001(9) N3 0.0486(13) 0.0349(10) 0.0388(12) -0.0213(9) -0.0110(10) -0.0080(9) N4 0.0445(13) 0.0413(11) 0.0401(12) -0.0198(9) -0.0147(10) -0.0031(9) C1 0.0371(14) 0.0288(11) 0.0436(15) -0.0167(11) -0.0113(12) -0.0073(10) C2 0.0418(15) 0.0348(12) 0.0397(14) -0.0211(11) -0.0082(12) -0.0080(11) C3 0.0388(14) 0.0363(12) 0.0417(15) -0.0207(11) -0.0089(12) -0.0057(11) C4 0.0608(19) 0.0571(17) 0.0473(17) -0.0253(14) -0.0257(15) 0.0001(14) C5 0.070(2) 0.0564(17) 0.062(2) -0.0201(15) -0.0364(17) 0.0075(15) C6 0.079(2) 0.0506(17) 0.075(2) -0.0338(16) -0.0396(19) 0.0190(15) C7 0.066(2) 0.0504(16) 0.0567(18) -0.0338(14) -0.0240(16) 0.0087(14) C8 0.0434(15) 0.0300(12) 0.0365(14) -0.0152(11) -0.0082(12) -0.0049(11) C9 0.079(2) 0.0402(14) 0.0403(16) -0.0190(12) -0.0134(15) -0.0143(13) C10 0.086(2) 0.0489(16) 0.068(2) -0.0350(16) -0.0286(19) -0.0067(15) C11 0.070(2) 0.073(2) 0.055(2) -0.0425(17) -0.0255(17) 0.0080(17) C12 0.067(2) 0.095(2) 0.0320(17) -0.0212(16) -0.0005(15) -0.0240(19) C13 0.0620(19) 0.0614(17) 0.0426(17) -0.0151(14) -0.0080(15) -0.0272(15) C1A 0.0365(14) 0.0344(12) 0.0334(13) -0.0161(10) -0.0091(11) -0.0033(10) C2A 0.0452(16) 0.0421(14) 0.0536(17) -0.0191(13) -0.0058(14) -0.0106(12) C3A 0.073(2) 0.0343(14) 0.065(2) -0.0139(13) -0.0176(18) -0.0078(14) C4A 0.063(2) 0.0443(16) 0.066(2) -0.0297(15) -0.0216(18) 0.0096(14) C5A 0.0449(17) 0.0581(18) 0.0523(18) -0.0289(15) -0.0020(14) 0.0058(14) C6A 0.0465(16) 0.0381(13) 0.0403(15) -0.0145(11) -0.0050(13) -0.0017(12) C1B 0.0340(14) 0.0353(12) 0.0405(14) -0.0222(11) -0.0057(12) -0.0025(10) C2B 0.0481(17) 0.0499(15) 0.0526(17) -0.0228(13) -0.0134(14) -0.0105(13) C3B 0.0542(19) 0.071(2) 0.078(2) -0.0413(18) -0.0188(17) -0.0148(16) C4B 0.059(2) 0.082(2) 0.092(3) -0.049(2) -0.006(2) -0.0352(18) C5B 0.072(2) 0.0594(18) 0.070(2) -0.0157(16) -0.0097(19) -0.0327(16) C6B 0.0572(18) 0.0543(16) 0.0516(18) -0.0152(14) -0.0150(15) -0.0207(14) C1C 0.0339(14) 0.0361(12) 0.0354(14) -0.0166(10) -0.0042(11) -0.0087(10) C2C 0.0529(18) 0.0520(15) 0.0512(17) -0.0296(13) -0.0181(15) 0.0004(13) C3C 0.067(2) 0.0560(17) 0.067(2) -0.0228(15) -0.0384(18) 0.0056(14) C4C 0.081(2) 0.074(2) 0.058(2) -0.0229(16) -0.0390(19) -0.0098(18) C5C 0.088(2) 0.086(2) 0.063(2) -0.0492(18) -0.0362(19) 0.0051(19) C6C 0.0562(18) 0.0574(16) 0.0577(18) -0.0371(14) -0.0186(15) 0.0055(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 Cu P 2.2454(8) . ? Cu S 2.3716(7) 2_565 ? Cu Br 2.4152(6) . ? Cu S 2.4622(8) . ? S C1 1.703(2) . ? S Cu 2.3716(7) 2_565 ? P C1A 1.823(2) . ? P C1B 1.827(2) . ? P C1C 1.828(2) . ? N1 C1 1.315(3) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C1 1.335(3) . ? N2 N3 1.372(2) . ? N2 H2A 0.8600 . ? N3 C2 1.289(3) . ? N4 C4 1.336(3) . ? N4 C3 1.345(3) . ? C2 C3 1.486(3) . ? C2 C8 1.498(3) . ? C3 C7 1.390(3) . ? C4 C5 1.355(3) . ? C4 H4A 0.9300 . ? C5 C6 1.369(4) . ? C5 H5A 0.9300 . ? C6 C7 1.370(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C13 1.372(3) . ? C8 C9 1.378(3) . ? C9 C10 1.373(3) . ? C9 H9A 0.9300 . ? C10 C11 1.360(4) . ? C10 H10A 0.9300 . ? C11 C12 1.359(4) . ? C11 H11A 0.9300 . ? C12 C13 1.381(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C1A C6A 1.378(3) . ? C1A C2A 1.385(3) . ? C2A C3A 1.379(3) . ? C2A H2AA 0.9300 . ? C3A C4A 1.370(4) . ? C3A H3AA 0.9300 . ? C4A C5A 1.376(4) . ? C4A H4AA 0.9300 . ? C5A C6A 1.372(3) . ? C5A H5AA 0.9300 . ? C6A H6AA 0.9300 . ? C1B C6B 1.373(3) . ? C1B C2B 1.393(3) . ? C2B C3B 1.366(3) . ? C2B H2BA 0.9300 . ? C3B C4B 1.372(4) . ? C3B H3BA 0.9300 . ? C4B C5B 1.370(4) . ? C4B H4BA 0.9300 . ? C5B C6B 1.392(4) . ? C5B H5BA 0.9300 . ? C6B H6BA 0.9300 . ? C1C C6C 1.380(3) . ? C1C C2C 1.384(3) . ? C2C C3C 1.378(3) . ? C2C H2CA 0.9300 . ? C3C C4C 1.370(4) . ? C3C H3CA 0.9300 . ? C4C C5C 1.361(4) . ? C4C H4CA 0.9300 . ? C5C C6C 1.392(3) . ? C5C H5CA 0.9300 . ? C6C H6CA 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 P Cu S 106.58(3) . 2_565 ? P Cu Br 116.47(3) . . ? S Cu Br 113.79(2) 2_565 . ? P Cu S 117.44(3) . . ? S Cu S 94.44(3) 2_565 . ? Br Cu S 106.19(2) . . ? C1 S Cu 114.79(8) . 2_565 ? C1 S Cu 101.17(8) . . ? Cu S Cu 85.56(2) 2_565 . ? C1A P C1B 101.61(10) . . ? C1A P C1C 104.19(10) . . ? C1B P C1C 103.82(10) . . ? C1A P Cu 119.08(8) . . ? C1B P Cu 108.26(8) . . ? C1C P Cu 117.74(8) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 121.10(18) . . ? C1 N2 H2A 119.4 . . ? N3 N2 H2A 119.4 . . ? C2 N3 N2 117.67(18) . . ? C4 N4 C3 118.64(19) . . ? N1 C1 N2 119.2(2) . . ? N1 C1 S 124.02(16) . . ? N2 C1 S 116.80(16) . . ? N3 C2 C3 128.2(2) . . ? N3 C2 C8 113.72(19) . . ? C3 C2 C8 118.12(18) . . ? N4 C3 C7 120.3(2) . . ? N4 C3 C2 118.36(19) . . ? C7 C3 C2 121.3(2) . . ? N4 C4 C5 123.8(2) . . ? N4 C4 H4A 118.1 . . ? C5 C4 H4A 118.1 . . ? C4 C5 C6 117.9(2) . . ? C4 C5 H5A 121.0 . . ? C6 C5 H5A 121.0 . . ? C5 C6 C7 119.9(2) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C6 C7 C3 119.4(2) . . ? C6 C7 H7A 120.3 . . ? C3 C7 H7A 120.3 . . ? C13 C8 C9 118.4(2) . . ? C13 C8 C2 121.3(2) . . ? C9 C8 C2 120.2(2) . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C8 C13 C12 120.1(3) . . ? C8 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C6A C1A C2A 118.7(2) . . ? C6A C1A P 122.91(17) . . ? C2A C1A P 118.39(18) . . ? C3A C2A C1A 120.2(3) . . ? C3A C2A H2AA 119.9 . . ? C1A C2A H2AA 119.9 . . ? C4A C3A C2A 120.7(3) . . ? C4A C3A H3AA 119.7 . . ? C2A C3A H3AA 119.7 . . ? C3A C4A C5A 119.1(2) . . ? C3A C4A H4AA 120.5 . . ? C5A C4A H4AA 120.5 . . ? C6A C5A C4A 120.7(3) . . ? C6A C5A H5AA 119.7 . . ? C4A C5A H5AA 119.7 . . ? C5A C6A C1A 120.6(2) . . ? C5A C6A H6AA 119.7 . . ? C1A C6A H6AA 119.7 . . ? C6B C1B C2B 118.8(2) . . ? C6B C1B P 124.67(19) . . ? C2B C1B P 116.47(18) . . ? C3B C2B C1B 121.1(3) . . ? C3B C2B H2BA 119.4 . . ? C1B C2B H2BA 119.4 . . ? C2B C3B C4B 119.5(3) . . ? C2B C3B H3BA 120.3 . . ? C4B C3B H3BA 120.3 . . ? C5B C4B C3B 120.6(3) . . ? C5B C4B H4BA 119.7 . . ? C3B C4B H4BA 119.7 . . ? C4B C5B C6B 119.8(3) . . ? C4B C5B H5BA 120.1 . . ? C6B C5B H5BA 120.1 . . ? C1B C6B C5B 120.1(3) . . ? C1B C6B H6BA 120.0 . . ? C5B C6B H6BA 120.0 . . ? C6C C1C C2C 118.0(2) . . ? C6C C1C P 124.47(18) . . ? C2C C1C P 117.50(17) . . ? C3C C2C C1C 121.4(2) . . ? C3C C2C H2CA 119.3 . . ? C1C C2C H2CA 119.3 . . ? C4C C3C C2C 119.8(2) . . ? C4C C3C H3CA 120.1 . . ? C2C C3C H3CA 120.1 . . ? C5C C4C C3C 119.9(3) . . ? C5C C4C H4CA 120.0 . . ? C3C C4C H4CA 120.0 . . ? C4C C5C C6C 120.4(2) . . ? C4C C5C H5CA 119.8 . . ? C6C C5C H5CA 119.8 . . ? C1C C6C C5C 120.4(2) . . ? C1C C6C H6CA 119.8 . . ? C5C C6C H6CA 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 P Cu S C1 3.14(8) . . . . ? S Cu S C1 114.41(8) 2_565 . . . ? Br Cu S C1 -129.23(7) . . . . ? P Cu S Cu -111.28(3) . . . 2_565 ? S Cu S Cu 0.0 2_565 . . 2_565 ? Br Cu S Cu 116.35(2) . . . 2_565 ? S Cu P C1A 165.65(8) 2_565 . . . ? Br Cu P C1A 37.43(9) . . . . ? S Cu P C1A -90.13(9) . . . . ? S Cu P C1B 50.43(8) 2_565 . . . ? Br Cu P C1B -77.78(8) . . . . ? S Cu P C1B 154.66(8) . . . . ? S Cu P C1C -66.80(8) 2_565 . . . ? Br Cu P C1C 164.98(8) . . . . ? S Cu P C1C 37.42(8) . . . . ? C1 N2 N3 C2 -173.9(2) . . . . ? N3 N2 C1 N1 -1.5(3) . . . . ? N3 N2 C1 S 177.31(16) . . . . ? Cu S C1 N1 -10.4(2) 2_565 . . . ? Cu S C1 N1 -100.7(2) . . . . ? Cu S C1 N2 170.79(15) 2_565 . . . ? Cu S C1 N2 80.55(18) . . . . ? N2 N3 C2 C3 -1.8(4) . . . . ? N2 N3 C2 C8 177.90(19) . . . . ? C4 N4 C3 C7 0.8(4) . . . . ? C4 N4 C3 C2 -178.8(2) . . . . ? N3 C2 C3 N4 8.1(4) . . . . ? C8 C2 C3 N4 -171.6(2) . . . . ? N3 C2 C3 C7 -171.5(3) . . . . ? C8 C2 C3 C7 8.8(4) . . . . ? C3 N4 C4 C5 -1.2(4) . . . . ? N4 C4 C5 C6 0.8(5) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C5 C6 C7 C3 -0.4(5) . . . . ? N4 C3 C7 C6 0.0(4) . . . . ? C2 C3 C7 C6 179.5(3) . . . . ? N3 C2 C8 C13 61.2(3) . . . . ? C3 C2 C8 C13 -119.0(3) . . . . ? N3 C2 C8 C9 -116.7(2) . . . . ? C3 C2 C8 C9 63.1(3) . . . . ? C13 C8 C9 C10 -0.3(4) . . . . ? C2 C8 C9 C10 177.7(2) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 -2.1(5) . . . . ? C9 C8 C13 C12 -1.2(4) . . . . ? C2 C8 C13 C12 -179.1(2) . . . . ? C11 C12 C13 C8 2.5(4) . . . . ? C1B P C1A C6A -38.2(2) . . . . ? C1C P C1A C6A 69.4(2) . . . . ? Cu P C1A C6A -156.93(17) . . . . ? C1B P C1A C2A 142.68(18) . . . . ? C1C P C1A C2A -109.66(19) . . . . ? Cu P C1A C2A 24.0(2) . . . . ? C6A C1A C2A C3A -0.9(4) . . . . ? P C1A C2A C3A 178.20(19) . . . . ? C1A C2A C3A C4A 0.1(4) . . . . ? C2A C3A C4A C5A 0.8(4) . . . . ? C3A C4A C5A C6A -0.7(4) . . . . ? C4A C5A C6A C1A -0.1(4) . . . . ? C2A C1A C6A C5A 1.0(4) . . . . ? P C1A C6A C5A -178.12(19) . . . . ? C1A P C1B C6B 115.3(2) . . . . ? C1C P C1B C6B 7.3(2) . . . . ? Cu P C1B C6B -118.5(2) . . . . ? C1A P C1B C2B -67.21(19) . . . . ? C1C P C1B C2B -175.16(17) . . . . ? Cu P C1B C2B 58.97(18) . . . . ? C6B C1B C2B C3B -1.5(4) . . . . ? P C1B C2B C3B -179.1(2) . . . . ? C1B C2B C3B C4B 2.5(4) . . . . ? C2B C3B C4B C5B -1.9(5) . . . . ? C3B C4B C5B C6B 0.3(5) . . . . ? C2B C1B C6B C5B -0.1(4) . . . . ? P C1B C6B C5B 177.3(2) . . . . ? C4B C5B C6B C1B 0.7(4) . . . . ? C1A P C1C C6C -1.0(2) . . . . ? C1B P C1C C6C 105.0(2) . . . . ? Cu P C1C C6C -135.4(2) . . . . ? C1A P C1C C2C 176.41(19) . . . . ? C1B P C1C C2C -77.6(2) . . . . ? Cu P C1C C2C 42.0(2) . . . . ? C6C C1C C2C C3C -2.5(4) . . . . ? P C1C C2C C3C 179.9(2) . . . . ? C1C C2C C3C C4C 1.9(4) . . . . ? C2C C3C C4C C5C -0.1(5) . . . . ? C3C C4C C5C C6C -0.9(5) . . . . ? C2C C1C C6C C5C 1.5(4) . . . . ? P C1C C6C C5C 178.9(2) . . . . ? C4C C5C C6C C1C 0.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B Br 0.86 2.59 3.4338(19) 168.6 2_565 N2 H2A N4 0.86 1.92 2.604(3) 135.6 . _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.399 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.066