# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H31 Br2 Cu N S2' _chemical_formula_weight 524.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 12.1800(7) _cell_length_b 6.6097(4) _cell_length_c 25.4001(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.9590(10) _cell_angle_gamma 90.00 _cell_volume 2007.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5759 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.50 _exptl_crystal_description Block _exptl_crystal_colour 'Dark Green' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Mesasured' _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 5.273 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1015 _exptl_absorpt_correction_T_max 0.5256 _exptl_absorpt_process_details ? _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 '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 13643 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4595 _reflns_number_gt 4059 _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^)+(0.0500P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4595 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.003 _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 0.31040(2) 0.41292(4) 0.608988(11) 0.01349(9) Uani 1 1 d . . . Br1 Br 0.43669(2) 0.75754(3) 0.622766(10) 0.01817(8) Uani 1 1 d . . . Br2 Br 0.11925(2) 0.50463(3) 0.590351(10) 0.01986(8) Uani 1 1 d . . . S1 S 0.31761(5) 0.38980(8) 0.70215(2) 0.01617(13) Uani 1 1 d . . . S2 S 0.32616(5) 0.39472(8) 0.51796(2) 0.01543(13) Uani 1 1 d . . . N1 N 0.45325(18) 0.2505(3) 0.62312(8) 0.0135(4) Uani 1 1 d . . . H1N H 0.437(2) 0.129(4) 0.6217(10) 0.013(7) Uiso 1 1 d . . . C1 C 0.5171(2) 0.2758(4) 0.67818(10) 0.0180(5) Uani 1 1 d . . . H1A H 0.5459 0.4160 0.6831 0.022 Uiso 1 1 calc R . . H1B H 0.5818 0.1824 0.6842 0.022 Uiso 1 1 calc R . . C2 C 0.4429(2) 0.2322(3) 0.71811(10) 0.0180(5) Uani 1 1 d . . . H2A H 0.4834 0.2622 0.7549 0.022 Uiso 1 1 calc R . . H2B H 0.4216 0.0874 0.7164 0.022 Uiso 1 1 calc R . . C3 C 0.5231(2) 0.2861(4) 0.58247(10) 0.0176(5) Uani 1 1 d . . . H3A H 0.5892 0.1961 0.5893 0.021 Uiso 1 1 calc R . . H3B H 0.5495 0.4280 0.5845 0.021 Uiso 1 1 calc R . . C4 C 0.4540(2) 0.2437(3) 0.52723(10) 0.0182(5) Uani 1 1 d . . . H4A H 0.4349 0.0981 0.5238 0.022 Uiso 1 1 calc R . . H4B H 0.4976 0.2788 0.4993 0.022 Uiso 1 1 calc R . . C5 C 0.2093(2) 0.2215(4) 0.71881(9) 0.0167(5) Uani 1 1 d . . . H5 H 0.1378 0.3001 0.7130 0.020 Uiso 1 1 calc R . . C6 C 0.2393(2) 0.1721(4) 0.77873(9) 0.0200(5) Uani 1 1 d . . . H6A H 0.3142 0.1083 0.7866 0.024 Uiso 1 1 calc R . . H6B H 0.2429 0.2992 0.7996 0.024 Uiso 1 1 calc R . . C7 C 0.1540(2) 0.0297(4) 0.79627(10) 0.0241(6) Uani 1 1 d . . . H7A H 0.0815 0.1005 0.7933 0.029 Uiso 1 1 calc R . . H7B H 0.1800 -0.0087 0.8343 0.029 Uiso 1 1 calc R . . C8 C 0.1382(2) -0.1612(4) 0.76144(10) 0.0233(5) Uani 1 1 d . . . H8A H 0.2092 -0.2378 0.7665 0.028 Uiso 1 1 calc R . . H8B H 0.0807 -0.2489 0.7726 0.028 Uiso 1 1 calc R . . C9 C 0.1019(2) -0.1043(4) 0.70263(10) 0.0216(5) Uani 1 1 d . . . H9A H 0.0291 -0.0335 0.6975 0.026 Uiso 1 1 calc R . . H9B H 0.0920 -0.2289 0.6806 0.026 Uiso 1 1 calc R . . C10 C 0.1884(2) 0.0328(4) 0.68366(10) 0.0197(5) Uani 1 1 d . . . H10A H 0.2594 -0.0421 0.6854 0.024 Uiso 1 1 calc R . . H10B H 0.1609 0.0730 0.6459 0.024 Uiso 1 1 calc R . . C11 C 0.2232(2) 0.2226(3) 0.47905(9) 0.0159(5) Uani 1 1 d . . . H11 H 0.1519 0.3001 0.4688 0.019 Uiso 1 1 calc R . . C12 C 0.1973(2) 0.0360(4) 0.51000(10) 0.0189(5) Uani 1 1 d . . . H12A H 0.1668 0.0786 0.5417 0.023 Uiso 1 1 calc R . . H12B H 0.2670 -0.0410 0.5227 0.023 Uiso 1 1 calc R . . C13 C 0.1123(2) -0.0990(4) 0.47400(10) 0.0215(5) Uani 1 1 d . . . H13A H 0.0983 -0.2214 0.4942 0.026 Uiso 1 1 calc R . . H13B H 0.0407 -0.0251 0.4638 0.026 Uiso 1 1 calc R . . C14 C 0.1536(2) -0.1616(4) 0.42365(10) 0.0221(5) Uani 1 1 d . . . H14A H 0.0959 -0.2448 0.4007 0.027 Uiso 1 1 calc R . . H14B H 0.2221 -0.2445 0.4335 0.027 Uiso 1 1 calc R . . C15 C 0.1788(3) 0.0256(4) 0.39272(10) 0.0273(6) Uani 1 1 d . . . H15A H 0.2094 -0.0175 0.3611 0.033 Uiso 1 1 calc R . . H15B H 0.1082 0.0997 0.3796 0.033 Uiso 1 1 calc R . . C16 C 0.2618(2) 0.1670(4) 0.42697(9) 0.0208(5) Uani 1 1 d . . . H16A H 0.2699 0.2918 0.4065 0.025 Uiso 1 1 calc R . . H16B H 0.3359 0.1005 0.4356 0.025 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 0.01528(16) 0.01213(15) 0.01299(15) -0.00031(10) 0.00254(12) 0.00108(11) Br1 0.02381(15) 0.00941(12) 0.02096(14) -0.00074(8) 0.00344(11) -0.00197(9) Br2 0.01659(14) 0.02315(14) 0.01940(14) -0.00058(9) 0.00227(11) 0.00442(10) S1 0.0206(3) 0.0137(3) 0.0139(3) -0.0011(2) 0.0026(2) 0.0003(2) S2 0.0180(3) 0.0137(3) 0.0149(3) -0.0006(2) 0.0040(2) -0.0005(2) N1 0.0132(11) 0.0073(9) 0.0198(11) 0.0007(7) 0.0025(9) -0.0008(7) C1 0.0165(13) 0.0158(11) 0.0203(12) 0.0015(9) 0.0001(11) -0.0023(9) C2 0.0193(13) 0.0158(11) 0.0170(12) 0.0009(8) -0.0014(10) 0.0000(9) C3 0.0175(13) 0.0141(10) 0.0228(13) -0.0014(9) 0.0078(11) -0.0010(9) C4 0.0199(13) 0.0149(11) 0.0213(13) -0.0019(9) 0.0078(11) 0.0011(9) C5 0.0193(13) 0.0173(11) 0.0138(11) -0.0003(8) 0.0040(10) 0.0008(10) C6 0.0222(13) 0.0230(12) 0.0141(11) -0.0002(9) 0.0021(10) -0.0008(11) C7 0.0259(15) 0.0311(14) 0.0158(12) 0.0024(10) 0.0051(11) -0.0011(12) C8 0.0231(14) 0.0232(13) 0.0240(13) 0.0028(10) 0.0053(11) -0.0023(11) C9 0.0205(14) 0.0237(13) 0.0206(13) -0.0036(10) 0.0041(11) -0.0033(10) C10 0.0218(14) 0.0212(12) 0.0162(12) -0.0057(9) 0.0038(11) -0.0038(10) C11 0.0154(12) 0.0167(11) 0.0149(11) -0.0007(8) 0.0011(10) -0.0010(9) C12 0.0205(13) 0.0229(12) 0.0144(12) -0.0011(9) 0.0059(11) -0.0057(10) C13 0.0220(14) 0.0266(13) 0.0180(12) -0.0061(10) 0.0091(11) -0.0078(11) C14 0.0230(14) 0.0237(13) 0.0203(12) -0.0065(10) 0.0061(11) -0.0053(11) C15 0.0351(17) 0.0343(15) 0.0134(12) -0.0037(10) 0.0066(12) -0.0088(12) C16 0.0279(15) 0.0223(12) 0.0128(11) -0.0018(9) 0.0053(11) -0.0055(11) _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 N1 2.018(2) . ? Cu1 S1 2.3561(6) . ? Cu1 S2 2.3593(6) . ? Cu1 Br2 2.3650(4) . ? Cu1 Br1 2.7335(4) . ? S1 C2 1.828(3) . ? S1 C5 1.836(3) . ? S2 C4 1.827(3) . ? S2 C11 1.836(2) . ? N1 C1 1.475(3) . ? N1 C3 1.476(3) . ? C1 C2 1.509(4) . ? C3 C4 1.519(4) . ? C5 C10 1.526(3) . ? C5 C6 1.531(3) . ? C6 C7 1.529(4) . ? C7 C8 1.532(4) . ? C8 C9 1.522(3) . ? C9 C10 1.535(4) . ? C11 C12 1.527(3) . ? C11 C16 1.530(3) . ? C12 C13 1.531(3) . ? C13 C14 1.518(3) . ? C14 C15 1.527(4) . ? C15 C16 1.523(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 S1 85.45(6) . . ? N1 Cu1 S2 85.36(6) . . ? S1 Cu1 S2 170.58(2) . . ? N1 Cu1 Br2 162.70(6) . . ? S1 Cu1 Br2 93.726(19) . . ? S2 Cu1 Br2 94.434(19) . . ? N1 Cu1 Br1 88.59(6) . . ? S1 Cu1 Br1 90.736(17) . . ? S2 Cu1 Br1 91.107(17) . . ? Br2 Cu1 Br1 108.703(13) . . ? C2 S1 C5 102.10(12) . . ? C2 S1 Cu1 97.47(8) . . ? C5 S1 Cu1 112.31(8) . . ? C4 S2 C11 102.05(11) . . ? C4 S2 Cu1 97.34(8) . . ? C11 S2 Cu1 112.63(8) . . ? C1 N1 C3 112.0(2) . . ? C1 N1 Cu1 112.92(15) . . ? C3 N1 Cu1 112.50(15) . . ? N1 C1 C2 109.9(2) . . ? C1 C2 S1 108.85(16) . . ? N1 C3 C4 109.0(2) . . ? C3 C4 S2 109.10(16) . . ? C10 C5 C6 112.9(2) . . ? C10 C5 S1 114.02(17) . . ? C6 C5 S1 108.18(18) . . ? C7 C6 C5 111.9(2) . . ? C6 C7 C8 110.9(2) . . ? C9 C8 C7 110.2(2) . . ? C8 C9 C10 111.5(2) . . ? C5 C10 C9 110.3(2) . . ? C12 C11 C16 112.3(2) . . ? C12 C11 S2 114.20(17) . . ? C16 C11 S2 108.88(17) . . ? C11 C12 C13 110.2(2) . . ? C14 C13 C12 111.5(2) . . ? C13 C14 C15 110.1(2) . . ? C16 C15 C14 112.3(2) . . ? C15 C16 C11 111.2(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 H1N Br1 0.82(3) 2.46(3) 3.2644(19) 167(3) 1_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.226 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.126 _database_code_depnum_ccdc_archive 'CCDC 809868' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cl2 Cu N2 S2' _chemical_formula_weight 565.05 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6863(4) _cell_length_b 12.0925(6) _cell_length_c 13.6748(6) _cell_angle_alpha 69.5630(10) _cell_angle_beta 86.2650(10) _cell_angle_gamma 70.4570(10) _cell_volume 1266.26(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6985 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 582 _exptl_absorpt_coefficient_mu 1.256 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5503 _exptl_absorpt_correction_T_max 0.8054 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 16552 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5816 _reflns_number_gt 5197 _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^)+(0.0390P)^2^+0.5277P] 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 5816 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.0000 -0.5000 0.5000 0.02138(8) Uani 1 2 d S . . Cu2 Cu -0.5000 0.5000 0.0000 0.02409(8) Uani 1 2 d S . . Cl1 Cl 0.07912(5) -0.32161(4) 0.44784(3) 0.02960(10) Uani 1 1 d . . . Cl2 Cl -0.41352(6) 0.67246(4) -0.06114(4) 0.03349(11) Uani 1 1 d . . . S1 S -0.26703(5) -0.39832(4) 0.60322(3) 0.02765(10) Uani 1 1 d . . . S2 S -0.21240(5) 0.35295(4) -0.08394(3) 0.02767(11) Uani 1 1 d . . . N1 N -0.17492(17) -0.41136(13) 0.38311(11) 0.0235(3) Uani 1 1 d . . . N2 N -0.32587(17) 0.42124(13) 0.11695(11) 0.0227(3) Uani 1 1 d . . . C1 C -0.1298(2) -0.38098(17) 0.28403(13) 0.0293(4) Uani 1 1 d . . . H1 H -0.0188 -0.4004 0.2723 0.035 Uiso 1 1 calc R . . C2 C -0.2409(2) -0.32229(19) 0.19903(15) 0.0387(5) Uani 1 1 d . . . H2 H -0.2054 -0.3031 0.1314 0.046 Uiso 1 1 calc R . . C3 C -0.4059(3) -0.2924(2) 0.21612(16) 0.0414(5) Uani 1 1 d . . . H3 H -0.4837 -0.2541 0.1603 0.050 Uiso 1 1 calc R . . C4 C -0.4529(2) -0.32054(18) 0.31761(15) 0.0336(4) Uani 1 1 d . . . H4 H -0.5635 -0.2990 0.3308 0.040 Uiso 1 1 calc R . . C5 C -0.3354(2) -0.38098(16) 0.40010(14) 0.0247(3) Uani 1 1 d . . . C6 C -0.3870(2) -0.41616(17) 0.51070(14) 0.0274(4) Uani 1 1 d . . . H6A H -0.3824 -0.5028 0.5343 0.033 Uiso 1 1 calc R . . H6B H -0.5002 -0.3653 0.5110 0.033 Uiso 1 1 calc R . . C7 C -0.3152(2) -0.22968(17) 0.55204(16) 0.0343(4) Uani 1 1 d . . . H7A H -0.2401 -0.2080 0.5855 0.041 Uiso 1 1 calc R . . H7B H -0.2982 -0.2036 0.4777 0.041 Uiso 1 1 calc R . . C8 C -0.4867(2) -0.15923(16) 0.56838(14) 0.0289(4) Uani 1 1 d . . . C9 C -0.6082(2) -0.10727(18) 0.48839(16) 0.0365(4) Uani 1 1 d . . . H9 H -0.5833 -0.1192 0.4248 0.044 Uiso 1 1 calc R . . C10 C -0.7654(3) -0.0382(2) 0.5020(2) 0.0504(6) Uani 1 1 d . . . H10 H -0.8458 -0.0044 0.4481 0.060 Uiso 1 1 calc R . . C11 C -0.8027(3) -0.0195(2) 0.5954(2) 0.0583(7) Uani 1 1 d . . . H11 H -0.9077 0.0289 0.6038 0.070 Uiso 1 1 calc R . . C12 C -0.6858(3) -0.0719(2) 0.6762(2) 0.0546(6) Uani 1 1 d . . . H12 H -0.7122 -0.0603 0.7398 0.065 Uiso 1 1 calc R . . C13 C -0.5275(3) -0.14244(19) 0.66310(16) 0.0412(5) Uani 1 1 d . . . H13 H -0.4487 -0.1785 0.7182 0.049 Uiso 1 1 calc R . . C14 C -0.3760(2) 0.40848(17) 0.21375(13) 0.0273(4) Uani 1 1 d . . . H14 H -0.4878 0.4327 0.2231 0.033 Uiso 1 1 calc R . . C15 C -0.2686(2) 0.36078(18) 0.30034(14) 0.0320(4) Uani 1 1 d . . . H15 H -0.3076 0.3540 0.3664 0.038 Uiso 1 1 calc R . . C16 C -0.1033(2) 0.32354(19) 0.28704(15) 0.0362(4) Uani 1 1 d . . . H16 H -0.0284 0.2915 0.3439 0.043 Uiso 1 1 calc R . . C17 C -0.0503(2) 0.33465(18) 0.18752(16) 0.0331(4) Uani 1 1 d . . . H17 H 0.0610 0.3088 0.1771 0.040 Uiso 1 1 calc R . . C18 C -0.1634(2) 0.38431(16) 0.10361(14) 0.0250(3) Uani 1 1 d . . . C19 C -0.1062(2) 0.40070(19) -0.00521(15) 0.0311(4) Uani 1 1 d . . . H19A H 0.0095 0.3530 -0.0002 0.037 Uiso 1 1 calc R . . H19B H -0.1185 0.4882 -0.0409 0.037 Uiso 1 1 calc R . . C20 C -0.1610(2) 0.18819(17) -0.00370(14) 0.0310(4) Uani 1 1 d . . . H20A H -0.0460 0.1545 0.0193 0.037 Uiso 1 1 calc R . . H20B H -0.2243 0.1804 0.0579 0.037 Uiso 1 1 calc R . . C21 C -0.1948(2) 0.11332(16) -0.06260(14) 0.0269(4) Uani 1 1 d . . . C22 C -0.2761(2) 0.02858(18) -0.01589(16) 0.0352(4) Uani 1 1 d . . . H22 H -0.3110 0.0195 0.0514 0.042 Uiso 1 1 calc R . . C23 C -0.3060(2) -0.04230(19) -0.06778(19) 0.0436(5) Uani 1 1 d . . . H23 H -0.3598 -0.0992 -0.0352 0.052 Uiso 1 1 calc R . . C24 C -0.2561(3) -0.0288(2) -0.16802(19) 0.0457(5) Uani 1 1 d . . . H24 H -0.2771 -0.0758 -0.2035 0.055 Uiso 1 1 calc R . . C25 C -0.1751(3) 0.0547(2) -0.21497(17) 0.0425(5) Uani 1 1 d . . . H25 H -0.1410 0.0639 -0.2824 0.051 Uiso 1 1 calc R . . C26 C -0.1437(2) 0.12524(18) -0.16281(15) 0.0336(4) Uani 1 1 d . . . H26 H -0.0880 0.1809 -0.1952 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 Cu1 0.01830(14) 0.02347(15) 0.01907(14) -0.00429(11) -0.00060(10) -0.00584(11) Cu2 0.02582(16) 0.02936(16) 0.02030(15) -0.00724(12) 0.00002(11) -0.01442(12) Cl1 0.0296(2) 0.0263(2) 0.0314(2) -0.00730(17) 0.00166(17) -0.01035(17) Cl2 0.0381(2) 0.0330(2) 0.0330(2) -0.00762(19) -0.00078(19) -0.0199(2) S1 0.0236(2) 0.0293(2) 0.0264(2) -0.00852(17) 0.00106(16) -0.00555(17) S2 0.0299(2) 0.0302(2) 0.0249(2) -0.01245(17) 0.00262(17) -0.00975(18) N1 0.0206(7) 0.0238(7) 0.0226(7) -0.0056(6) -0.0005(5) -0.0053(5) N2 0.0243(7) 0.0262(7) 0.0213(7) -0.0103(6) 0.0022(5) -0.0110(6) C1 0.0263(9) 0.0313(9) 0.0241(8) -0.0062(7) 0.0021(7) -0.0058(7) C2 0.0383(11) 0.0428(11) 0.0227(9) -0.0036(8) -0.0019(8) -0.0060(9) C3 0.0355(11) 0.0438(12) 0.0316(10) -0.0047(9) -0.0124(8) -0.0028(9) C4 0.0223(9) 0.0333(10) 0.0379(10) -0.0090(8) -0.0056(7) -0.0024(7) C5 0.0217(8) 0.0225(8) 0.0291(9) -0.0088(7) -0.0006(7) -0.0060(6) C6 0.0189(8) 0.0304(9) 0.0324(9) -0.0101(7) 0.0037(7) -0.0086(7) C7 0.0295(9) 0.0298(9) 0.0450(11) -0.0129(8) 0.0019(8) -0.0120(8) C8 0.0297(9) 0.0228(8) 0.0360(10) -0.0115(7) 0.0024(7) -0.0098(7) C9 0.0361(10) 0.0308(10) 0.0418(11) -0.0130(8) -0.0037(8) -0.0086(8) C10 0.0331(11) 0.0368(11) 0.0760(17) -0.0181(11) -0.0064(11) -0.0051(9) C11 0.0395(13) 0.0386(12) 0.097(2) -0.0289(13) 0.0206(13) -0.0111(10) C12 0.0726(17) 0.0453(13) 0.0583(15) -0.0301(12) 0.0344(13) -0.0281(12) C13 0.0549(13) 0.0358(11) 0.0366(11) -0.0138(9) 0.0047(9) -0.0189(10) C14 0.0274(9) 0.0331(9) 0.0251(8) -0.0115(7) 0.0042(7) -0.0135(7) C15 0.0372(10) 0.0384(10) 0.0231(8) -0.0113(8) 0.0019(7) -0.0154(8) C16 0.0343(10) 0.0419(11) 0.0315(10) -0.0109(8) -0.0084(8) -0.0115(8) C17 0.0231(9) 0.0361(10) 0.0409(11) -0.0166(9) -0.0015(8) -0.0069(7) C18 0.0251(8) 0.0266(8) 0.0293(9) -0.0149(7) 0.0037(7) -0.0110(7) C19 0.0286(9) 0.0417(10) 0.0337(10) -0.0208(8) 0.0092(7) -0.0183(8) C20 0.0330(10) 0.0297(9) 0.0282(9) -0.0110(7) -0.0026(7) -0.0060(7) C21 0.0218(8) 0.0254(8) 0.0304(9) -0.0106(7) -0.0042(7) -0.0020(7) C22 0.0303(10) 0.0350(10) 0.0358(10) -0.0089(8) 0.0004(8) -0.0084(8) C23 0.0336(11) 0.0308(10) 0.0646(15) -0.0122(10) -0.0075(10) -0.0112(8) C24 0.0395(11) 0.0389(11) 0.0647(15) -0.0304(11) -0.0140(10) -0.0043(9) C25 0.0413(11) 0.0482(12) 0.0420(11) -0.0280(10) -0.0005(9) -0.0063(9) C26 0.0322(10) 0.0358(10) 0.0360(10) -0.0174(8) 0.0044(8) -0.0105(8) _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 N1 2.0107(14) 2_546 ? Cu1 N1 2.0107(14) . ? Cu1 Cl1 2.3426(4) . ? Cu1 Cl1 2.3427(4) 2_546 ? Cu1 S1 2.7860(4) . ? Cu1 S1 2.7860(4) 2_546 ? Cu2 N2 2.0100(14) 2_465 ? Cu2 N2 2.0100(14) . ? Cu2 Cl2 2.3154(4) . ? Cu2 Cl2 2.3154(4) 2_465 ? S1 C6 1.8017(18) . ? S1 C7 1.8150(19) . ? S2 C19 1.8064(18) . ? S2 C20 1.8206(18) . ? N1 C1 1.343(2) . ? N1 C5 1.345(2) . ? N2 C14 1.339(2) . ? N2 C18 1.351(2) . ? C1 C2 1.378(3) . ? C2 C3 1.382(3) . ? C3 C4 1.378(3) . ? C4 C5 1.387(2) . ? C5 C6 1.503(2) . ? C7 C8 1.495(2) . ? C8 C13 1.386(3) . ? C8 C9 1.390(3) . ? C9 C10 1.382(3) . ? C10 C11 1.373(4) . ? C11 C12 1.372(4) . ? C12 C13 1.394(3) . ? C14 C15 1.383(2) . ? C15 C16 1.375(3) . ? C16 C17 1.383(3) . ? C17 C18 1.383(2) . ? C18 C19 1.505(2) . ? C20 C21 1.508(2) . ? C21 C26 1.386(3) . ? C21 C22 1.388(3) . ? C22 C23 1.379(3) . ? C23 C24 1.381(3) . ? C24 C25 1.376(3) . ? C25 C26 1.384(3) . ? 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 Cu1 N1 180.0 2_546 . ? N1 Cu1 Cl1 91.05(4) 2_546 . ? N1 Cu1 Cl1 88.95(4) . . ? N1 Cu1 Cl1 88.95(4) 2_546 2_546 ? N1 Cu1 Cl1 91.05(4) . 2_546 ? Cl1 Cu1 Cl1 180.0 . 2_546 ? N1 Cu1 S1 101.05(4) 2_546 . ? N1 Cu1 S1 78.95(4) . . ? Cl1 Cu1 S1 93.615(14) . . ? Cl1 Cu1 S1 86.386(14) 2_546 . ? N1 Cu1 S1 78.95(4) 2_546 2_546 ? N1 Cu1 S1 101.05(4) . 2_546 ? Cl1 Cu1 S1 86.385(15) . 2_546 ? Cl1 Cu1 S1 93.615(14) 2_546 2_546 ? S1 Cu1 S1 180.0 . 2_546 ? N2 Cu2 N2 179.999(1) 2_465 . ? N2 Cu2 Cl2 90.83(4) 2_465 . ? N2 Cu2 Cl2 89.17(4) . . ? N2 Cu2 Cl2 89.17(4) 2_465 2_465 ? N2 Cu2 Cl2 90.83(4) . 2_465 ? Cl2 Cu2 Cl2 180.0 . 2_465 ? C6 S1 C7 99.96(9) . . ? C6 S1 Cu1 84.87(6) . . ? C7 S1 Cu1 107.34(6) . . ? C19 S2 C20 99.03(9) . . ? C1 N1 C5 118.61(14) . . ? C1 N1 Cu1 118.74(11) . . ? C5 N1 Cu1 122.64(11) . . ? C14 N2 C18 118.54(15) . . ? C14 N2 Cu2 117.07(11) . . ? C18 N2 Cu2 124.36(11) . . ? N1 C1 C2 122.80(17) . . ? C1 C2 C3 118.78(18) . . ? C4 C3 C2 118.63(17) . . ? C3 C4 C5 119.99(17) . . ? N1 C5 C4 121.16(16) . . ? N1 C5 C6 118.96(15) . . ? C4 C5 C6 119.87(16) . . ? C5 C6 S1 115.50(12) . . ? C8 C7 S1 113.47(13) . . ? C13 C8 C9 118.50(18) . . ? C13 C8 C7 120.70(18) . . ? C9 C8 C7 120.79(17) . . ? C10 C9 C8 120.9(2) . . ? C11 C10 C9 119.9(2) . . ? C12 C11 C10 120.3(2) . . ? C11 C12 C13 120.0(2) . . ? C8 C13 C12 120.4(2) . . ? N2 C14 C15 122.80(16) . . ? C16 C15 C14 118.83(17) . . ? C15 C16 C17 118.78(17) . . ? C18 C17 C16 119.84(17) . . ? N2 C18 C17 121.20(16) . . ? N2 C18 C19 118.82(15) . . ? C17 C18 C19 119.97(16) . . ? C18 C19 S2 115.09(12) . . ? C21 C20 S2 111.78(12) . . ? C26 C21 C22 118.54(17) . . ? C26 C21 C20 121.43(17) . . ? C22 C21 C20 120.02(17) . . ? C23 C22 C21 120.94(19) . . ? C22 C23 C24 120.1(2) . . ? C25 C24 C23 119.42(19) . . ? C24 C25 C26 120.6(2) . . ? C25 C26 C21 120.35(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.537 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 809869' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Cu2 I2 N2 S' _chemical_formula_weight 583.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7667(4) _cell_length_b 8.2376(4) _cell_length_c 12.2411(6) _cell_angle_alpha 92.5260(10) _cell_angle_beta 93.7820(10) _cell_angle_gamma 109.7160(10) _cell_volume 733.82(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6921 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 2.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 7.229 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1601 _exptl_absorpt_correction_T_max 0.8123 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 9485 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3358 _reflns_number_gt 3218 _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^)+(0.0207P)^2^+0.7417P] 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 3358 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.003 _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 0.57506(5) 0.59877(5) 0.92348(3) 0.03151(9) Uani 1 1 d . . . Cu2 Cu -0.39048(4) 0.55693(5) 0.58811(3) 0.02560(9) Uani 1 1 d . . . I1 I 0.37672(3) 0.69379(3) 1.057767(15) 0.03022(6) Uani 1 1 d . . . I2 I -0.40199(2) 0.77302(2) 0.437411(14) 0.02713(6) Uani 1 1 d . . . S1 S 0.46690(8) 0.63912(8) 0.73502(5) 0.01957(12) Uani 1 1 d . . . N1 N 0.7985(3) 0.7912(3) 0.87786(19) 0.0233(4) Uani 1 1 d . . . N2 N -0.1253(3) 0.5839(3) 0.62959(19) 0.0234(4) Uani 1 1 d . . . C1 C 0.9714(4) 0.8108(4) 0.9167(2) 0.0277(6) Uani 1 1 d . . . H1 H 0.9894 0.7344 0.9674 0.033 Uiso 1 1 calc R . . C2 C 1.1229(4) 0.9386(4) 0.8851(3) 0.0307(6) Uani 1 1 d . . . H2 H 1.2414 0.9500 0.9150 0.037 Uiso 1 1 calc R . . C3 C 1.0986(4) 1.0493(4) 0.8092(3) 0.0339(7) Uani 1 1 d . . . H3 H 1.1998 1.1377 0.7867 0.041 Uiso 1 1 calc R . . C4 C 0.9213(4) 1.0275(4) 0.7664(3) 0.0312(6) Uani 1 1 d . . . H4 H 0.9013 1.0992 0.7130 0.037 Uiso 1 1 calc R . . C5 C 0.7751(4) 0.8998(3) 0.8032(2) 0.0231(5) Uani 1 1 d . . . C6 C 0.5797(4) 0.8716(4) 0.7603(2) 0.0256(5) Uani 1 1 d . . . H6A H 0.5773 0.9295 0.6923 0.031 Uiso 1 1 calc R . . H6B H 0.5177 0.9179 0.8145 0.031 Uiso 1 1 calc R . . C7 C 0.0139(4) 0.7075(4) 0.5914(2) 0.0282(6) Uani 1 1 d . . . H7 H -0.0136 0.7823 0.5427 0.034 Uiso 1 1 calc R . . C8 C 0.1970(4) 0.7308(4) 0.6201(2) 0.0279(6) Uani 1 1 d . . . H8 H 0.2909 0.8177 0.5904 0.033 Uiso 1 1 calc R . . C9 C 0.2386(3) 0.6237(3) 0.6934(2) 0.0200(5) Uani 1 1 d . . . C10 C 0.0962(4) 0.4964(4) 0.7341(2) 0.0295(6) Uani 1 1 d . . . H10 H 0.1200 0.4221 0.7844 0.035 Uiso 1 1 calc R . . C11 C -0.0827(4) 0.4804(4) 0.6991(3) 0.0305(6) Uani 1 1 d . . . H11 H -0.1790 0.3919 0.7259 0.037 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 0.02770(19) 0.02916(19) 0.0387(2) 0.01188(15) 0.01027(15) 0.00849(15) Cu2 0.01829(16) 0.02751(18) 0.03083(18) 0.00275(13) -0.00056(13) 0.00801(14) I1 0.03243(11) 0.02907(11) 0.03378(11) 0.00748(8) 0.00833(8) 0.01487(8) I2 0.02979(11) 0.02082(10) 0.02975(10) 0.00703(7) 0.00309(7) 0.00656(8) S1 0.0165(3) 0.0194(3) 0.0228(3) 0.0020(2) -0.0001(2) 0.0064(2) N1 0.0198(10) 0.0220(11) 0.0268(11) 0.0026(9) 0.0015(9) 0.0055(9) N2 0.0178(10) 0.0271(12) 0.0268(11) 0.0028(9) 0.0013(8) 0.0095(9) C1 0.0221(13) 0.0293(14) 0.0317(14) 0.0018(11) -0.0008(11) 0.0093(12) C2 0.0182(13) 0.0330(16) 0.0388(16) -0.0015(12) 0.0016(11) 0.0066(12) C3 0.0238(14) 0.0291(15) 0.0418(17) 0.0042(13) 0.0065(12) -0.0009(12) C4 0.0306(15) 0.0264(15) 0.0352(15) 0.0080(12) 0.0036(12) 0.0072(12) C5 0.0226(13) 0.0194(12) 0.0256(13) -0.0027(10) 0.0000(10) 0.0060(10) C6 0.0217(13) 0.0181(12) 0.0353(14) 0.0010(10) -0.0029(11) 0.0059(10) C7 0.0222(13) 0.0296(15) 0.0348(15) 0.0110(12) 0.0020(11) 0.0106(12) C8 0.0182(12) 0.0264(14) 0.0385(15) 0.0123(12) 0.0020(11) 0.0055(11) C9 0.0159(11) 0.0212(12) 0.0233(12) -0.0017(9) 0.0003(9) 0.0075(10) C10 0.0226(13) 0.0291(15) 0.0367(15) 0.0128(12) 0.0011(11) 0.0079(12) C11 0.0187(13) 0.0305(15) 0.0409(16) 0.0124(12) 0.0041(11) 0.0050(11) _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 N1 2.046(2) . ? Cu1 S1 2.4775(7) . ? Cu1 I1 2.5782(4) 2_667 ? Cu1 I1 2.5927(4) . ? Cu1 Cu1 2.6066(7) 2_667 ? Cu2 N2 2.023(2) . ? Cu2 S1 2.3625(7) 1_455 ? Cu2 Cu2 2.5861(7) 2_466 ? Cu2 I2 2.6372(4) . ? Cu2 I2 2.6431(4) 2_466 ? I1 Cu1 2.5782(4) 2_667 ? I2 Cu2 2.6431(4) 2_466 ? S1 C9 1.773(3) . ? S1 C6 1.819(3) . ? S1 Cu2 2.3624(7) 1_655 ? N1 C1 1.348(3) . ? N1 C5 1.352(4) . ? N2 C11 1.334(4) . ? N2 C7 1.338(4) . ? C1 C2 1.380(4) . ? C2 C3 1.378(5) . ? C3 C4 1.390(4) . ? C4 C5 1.379(4) . ? C5 C6 1.510(4) . ? C7 C8 1.388(4) . ? C8 C9 1.382(4) . ? C9 C10 1.381(4) . ? C10 C11 1.387(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 S1 78.46(7) . . ? N1 Cu1 I1 114.36(7) . 2_667 ? S1 Cu1 I1 113.52(2) . 2_667 ? N1 Cu1 I1 116.00(7) . . ? S1 Cu1 I1 107.50(2) . . ? I1 Cu1 I1 119.461(14) 2_667 . ? N1 Cu1 Cu1 147.57(7) . 2_667 ? S1 Cu1 Cu1 133.93(3) . 2_667 ? I1 Cu1 Cu1 60.006(15) 2_667 2_667 ? I1 Cu1 Cu1 59.455(15) . 2_667 ? N2 Cu2 S1 112.71(7) . 1_455 ? N2 Cu2 Cu2 134.03(7) . 2_466 ? S1 Cu2 Cu2 113.22(2) 1_455 2_466 ? N2 Cu2 I2 108.85(7) . . ? S1 Cu2 I2 104.29(2) 1_455 . ? Cu2 Cu2 I2 60.789(14) 2_466 . ? N2 Cu2 I2 110.96(7) . 2_466 ? S1 Cu2 I2 98.02(2) 1_455 2_466 ? Cu2 Cu2 I2 60.561(14) 2_466 2_466 ? I2 Cu2 I2 121.350(13) . 2_466 ? Cu1 I1 Cu1 60.540(14) 2_667 . ? Cu2 I2 Cu2 58.651(13) . 2_466 ? C9 S1 C6 101.83(12) . . ? C9 S1 Cu2 111.26(9) . 1_655 ? C6 S1 Cu2 105.60(10) . 1_655 ? C9 S1 Cu1 124.40(9) . . ? C6 S1 Cu1 89.64(10) . . ? Cu2 S1 Cu1 117.51(3) 1_655 . ? C1 N1 C5 118.0(2) . . ? C1 N1 Cu1 122.3(2) . . ? C5 N1 Cu1 119.68(18) . . ? C11 N2 C7 117.3(2) . . ? C11 N2 Cu2 120.65(19) . . ? C7 N2 Cu2 122.03(19) . . ? N1 C1 C2 122.6(3) . . ? C3 C2 C1 119.2(3) . . ? C2 C3 C4 118.6(3) . . ? C5 C4 C3 119.4(3) . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C6 116.3(2) . . ? C4 C5 C6 121.6(3) . . ? C5 C6 S1 106.48(19) . . ? N2 C7 C8 123.2(3) . . ? C9 C8 C7 118.8(3) . . ? C10 C9 C8 118.7(2) . . ? C10 C9 S1 118.4(2) . . ? C8 C9 S1 122.9(2) . . ? C9 C10 C11 118.7(3) . . ? N2 C11 C10 123.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.658 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.134 _database_code_depnum_ccdc_archive 'CCDC 809870' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_P1 #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 Cu2 I2 N9' _chemical_formula_weight 894.49 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' 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 10.1742(4) _cell_length_b 11.7158(5) _cell_length_c 13.8012(5) _cell_angle_alpha 95.6190(10) _cell_angle_beta 90.2230(10) _cell_angle_gamma 94.1080(10) _cell_volume 1632.88(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7876 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.44 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 3.228 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3064 _exptl_absorpt_correction_T_max 0.7384 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 21424 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7492 _reflns_number_gt 6585 _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^)+(0.0395P)^2^+0.9102P] 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 7492 _refine_ls_number_parameters 383 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.029 _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 Cu1 Cu 0.12246(4) 0.53378(4) 0.53922(3) 0.03016(10) Uani 1 1 d . . . Cu2 Cu 0.62517(4) 0.53831(4) -0.03150(3) 0.02908(10) Uani 1 1 d . . . I1 I -0.02105(2) 0.675867(18) 0.452402(15) 0.02940(7) Uani 1 1 d . . . I2 I 0.47489(2) 0.672162(18) 0.076921(15) 0.02868(7) Uani 1 1 d . . . N1 N 0.2901(2) 0.5223(2) 0.45590(18) 0.0246(5) Uani 1 1 d . . . N2 N 0.7053(2) 0.4083(3) 0.27495(19) 0.0284(6) Uani 1 1 d . . . N3 N 0.8084(3) 0.3816(2) 0.32830(19) 0.0282(6) Uani 1 1 d . . . N4 N 0.8409(3) 0.2791(2) 0.29350(19) 0.0290(6) Uani 1 1 d . . . N5 N 0.7916(2) 0.5275(2) 0.05388(18) 0.0248(6) Uani 1 1 d . . . N6 N 1.2077(2) 0.4082(2) 0.21139(18) 0.0222(5) Uani 1 1 d . . . N7 N 1.3044(3) 0.3763(2) 0.14949(18) 0.0242(5) Uani 1 1 d . . . N8 N 1.3261(3) 0.2689(2) 0.16189(19) 0.0271(6) Uani 1 1 d . . . C1 C 0.3463(3) 0.6173(3) 0.4211(2) 0.0277(7) Uani 1 1 d . . . H1 H 0.3068 0.6863 0.4341 0.033 Uiso 1 1 calc R . . C2 C 0.4594(3) 0.6169(3) 0.3671(2) 0.0291(7) Uani 1 1 d . . . H2 H 0.4942 0.6844 0.3437 0.035 Uiso 1 1 calc R . . C3 C 0.5218(3) 0.5157(3) 0.3476(2) 0.0260(7) Uani 1 1 d . . . C4 C 0.4650(3) 0.4172(3) 0.3834(2) 0.0257(6) Uani 1 1 d . . . H4 H 0.5034 0.3475 0.3719 0.031 Uiso 1 1 calc R . . C5 C 0.3503(3) 0.4245(3) 0.4364(2) 0.0261(7) Uani 1 1 d . . . H5 H 0.3128 0.3580 0.4599 0.031 Uiso 1 1 calc R . . C6 C 0.6490(3) 0.5185(3) 0.2920(2) 0.0317(8) Uani 1 1 d . . . H6A H 0.6335 0.5472 0.2297 0.038 Uiso 1 1 calc R . . H6B H 0.7128 0.5724 0.3278 0.038 Uiso 1 1 calc R . . C7 C 0.6704(3) 0.3217(3) 0.2067(2) 0.0334(8) Uani 1 1 d . . . H7 H 0.6024 0.3183 0.1611 0.040 Uiso 1 1 calc R . . C8 C 0.7566(3) 0.2396(3) 0.2189(2) 0.0296(7) Uani 1 1 d . . . C9 C 0.7708(4) 0.1286(3) 0.1605(3) 0.0368(8) Uani 1 1 d . . . C10 C 0.6683(5) 0.0763(4) 0.1027(4) 0.0696(15) Uani 1 1 d . . . H10 H 0.5887 0.1105 0.1007 0.083 Uiso 1 1 calc R . . C11 C 0.6839(8) -0.0259(5) 0.0483(5) 0.093(2) Uani 1 1 d . . . H11 H 0.6144 -0.0596 0.0090 0.112 Uiso 1 1 calc R . . C12 C 0.7971(7) -0.0791(4) 0.0499(4) 0.0812(19) Uani 1 1 d . . . H12 H 0.8054 -0.1487 0.0127 0.097 Uiso 1 1 calc R . . C13 C 0.8981(7) -0.0292(5) 0.1068(5) 0.0869(19) Uani 1 1 d . . . H13 H 0.9769 -0.0648 0.1086 0.104 Uiso 1 1 calc R . . C14 C 0.8850(5) 0.0742(4) 0.1622(4) 0.0701(15) Uani 1 1 d . . . H14 H 0.9551 0.1072 0.2012 0.084 Uiso 1 1 calc R . . C15 C 0.8542(3) 0.4301(3) 0.0529(2) 0.0259(7) Uani 1 1 d . . . H15 H 0.8175 0.3644 0.0166 0.031 Uiso 1 1 calc R . . C16 C 0.9706(3) 0.4232(3) 0.1035(2) 0.0228(6) Uani 1 1 d . . . H16 H 1.0105 0.3540 0.1009 0.027 Uiso 1 1 calc R . . C17 C 1.0270(3) 0.5193(3) 0.1579(2) 0.0218(6) Uani 1 1 d . . . C18 C 0.9616(3) 0.6198(3) 0.1603(2) 0.0265(7) Uani 1 1 d . . . H18 H 0.9958 0.6862 0.1970 0.032 Uiso 1 1 calc R . . C19 C 0.8464(3) 0.6203(3) 0.1082(2) 0.0271(7) Uani 1 1 d . . . H19 H 0.8041 0.6883 0.1107 0.032 Uiso 1 1 calc R . . C20 C 1.1551(3) 0.5205(3) 0.2134(2) 0.0257(7) Uani 1 1 d . . . H20A H 1.2197 0.5730 0.1861 0.031 Uiso 1 1 calc R . . H20B H 1.1415 0.5495 0.2806 0.031 Uiso 1 1 calc R . . C21 C 1.1671(3) 0.3213(3) 0.2629(2) 0.0259(7) Uani 1 1 d . . . H21 H 1.1013 0.3210 0.3095 0.031 Uiso 1 1 calc R . . C22 C 1.2430(3) 0.2328(3) 0.2322(2) 0.0257(7) Uani 1 1 d . . . C23 C 1.2403(4) 0.1159(3) 0.2620(3) 0.0335(8) Uani 1 1 d . . . C24 C 1.1570(5) 0.0836(4) 0.3355(3) 0.0529(11) Uani 1 1 d . . . H24 H 1.1067 0.1376 0.3688 0.064 Uiso 1 1 calc R . . C25 C 1.1488(6) -0.0286(4) 0.3594(4) 0.0718(15) Uani 1 1 d . . . H25 H 1.0919 -0.0497 0.4082 0.086 Uiso 1 1 calc R . . C26 C 1.2219(6) -0.1075(4) 0.3129(4) 0.0709(15) Uani 1 1 d . . . H26 H 1.2144 -0.1831 0.3286 0.085 Uiso 1 1 calc R . . C27 C 1.3049(7) -0.0772(5) 0.2442(5) 0.105(3) Uani 1 1 d . . . H27 H 1.3568 -0.1315 0.2131 0.127 Uiso 1 1 calc R . . C28 C 1.3153(6) 0.0355(4) 0.2182(4) 0.083(2) Uani 1 1 d . . . H28 H 1.3743 0.0553 0.1703 0.100 Uiso 1 1 calc R . . N1S N 0.5354(10) 0.1377(9) 0.4400(8) 0.181(4) Uani 1 1 d DU . . C1S C 0.6072(13) 0.0756(11) 0.4117(9) 0.194(4) Uani 1 1 d D . . C2S C 0.6763(13) -0.0274(9) 0.3836(8) 0.194(4) Uani 1 1 d D . . H2S1 H 0.6555 -0.0836 0.4285 0.291 Uiso 1 1 calc R . . H2S2 H 0.7696 -0.0079 0.3849 0.291 Uiso 1 1 calc R . . H2S3 H 0.6492 -0.0584 0.3191 0.291 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 0.0247(2) 0.0364(2) 0.0295(2) 0.00252(17) 0.00464(16) 0.00411(17) Cu2 0.0239(2) 0.0344(2) 0.0301(2) 0.00602(17) -0.00124(16) 0.00600(17) I1 0.02615(12) 0.03085(12) 0.03236(12) 0.00735(9) 0.00445(9) 0.00412(9) I2 0.02458(12) 0.02865(12) 0.03271(12) 0.00063(9) 0.00224(8) 0.00436(8) N1 0.0201(13) 0.0328(15) 0.0213(13) 0.0038(11) -0.0002(10) 0.0026(11) N2 0.0175(13) 0.0460(17) 0.0227(13) 0.0052(12) 0.0038(10) 0.0059(12) N3 0.0224(14) 0.0371(16) 0.0252(13) 0.0020(12) -0.0004(11) 0.0059(12) N4 0.0249(14) 0.0355(16) 0.0263(14) 0.0024(12) -0.0016(11) 0.0009(12) N5 0.0207(13) 0.0325(15) 0.0225(13) 0.0073(11) 0.0018(10) 0.0053(11) N6 0.0169(12) 0.0285(14) 0.0213(12) 0.0021(10) -0.0017(10) 0.0038(10) N7 0.0228(13) 0.0276(14) 0.0231(13) 0.0039(11) 0.0021(10) 0.0057(11) N8 0.0271(14) 0.0289(14) 0.0261(14) 0.0035(11) 0.0024(11) 0.0056(11) C1 0.0222(16) 0.0328(17) 0.0288(16) 0.0042(13) 0.0002(13) 0.0049(13) C2 0.0228(16) 0.0348(18) 0.0318(17) 0.0126(14) 0.0009(13) 0.0025(13) C3 0.0178(15) 0.0424(19) 0.0182(14) 0.0041(13) -0.0002(11) 0.0035(13) C4 0.0204(15) 0.0339(17) 0.0227(15) 0.0012(13) -0.0005(12) 0.0047(13) C5 0.0226(16) 0.0335(17) 0.0217(15) 0.0020(13) -0.0020(12) -0.0001(13) C6 0.0212(16) 0.045(2) 0.0315(17) 0.0118(15) 0.0093(13) 0.0083(14) C7 0.0196(16) 0.057(2) 0.0229(16) 0.0055(15) -0.0004(13) -0.0030(15) C8 0.0221(16) 0.0402(19) 0.0254(16) 0.0040(14) 0.0007(13) -0.0065(14) C9 0.042(2) 0.0353(19) 0.0314(18) 0.0042(15) -0.0034(15) -0.0104(16) C10 0.069(3) 0.061(3) 0.074(3) -0.005(3) -0.028(3) -0.008(3) C11 0.135(6) 0.052(3) 0.087(4) -0.009(3) -0.054(4) -0.016(4) C12 0.150(6) 0.034(3) 0.055(3) -0.008(2) -0.019(4) -0.002(3) C13 0.102(5) 0.058(3) 0.097(4) -0.025(3) -0.014(4) 0.027(3) C14 0.063(3) 0.057(3) 0.084(4) -0.027(3) -0.019(3) 0.010(2) C15 0.0221(16) 0.0310(17) 0.0248(15) 0.0044(13) 0.0043(12) 0.0009(13) C16 0.0198(15) 0.0254(16) 0.0247(15) 0.0070(12) 0.0008(12) 0.0048(12) C17 0.0200(15) 0.0284(16) 0.0177(14) 0.0052(12) 0.0028(11) 0.0026(12) C18 0.0246(16) 0.0284(16) 0.0268(16) 0.0031(13) 0.0010(13) 0.0027(13) C19 0.0246(16) 0.0301(17) 0.0281(16) 0.0049(13) 0.0015(13) 0.0097(13) C20 0.0227(16) 0.0257(16) 0.0287(16) 0.0003(13) -0.0005(13) 0.0048(12) C21 0.0194(15) 0.0349(18) 0.0237(15) 0.0044(13) -0.0004(12) 0.0016(13) C22 0.0226(16) 0.0319(17) 0.0226(15) 0.0044(13) -0.0027(12) 0.0002(13) C23 0.038(2) 0.0302(18) 0.0329(18) 0.0042(14) 0.0010(15) 0.0047(15) C24 0.065(3) 0.040(2) 0.057(3) 0.017(2) 0.022(2) 0.007(2) C25 0.092(4) 0.050(3) 0.079(4) 0.036(3) 0.023(3) 0.004(3) C26 0.094(4) 0.041(3) 0.083(4) 0.028(3) 0.011(3) 0.012(3) C27 0.157(7) 0.048(3) 0.122(5) 0.027(3) 0.071(5) 0.053(4) C28 0.118(5) 0.050(3) 0.090(4) 0.025(3) 0.066(4) 0.037(3) N1S 0.190(5) 0.172(5) 0.179(5) 0.018(4) -0.025(4) 0.001(4) C1S 0.238(12) 0.201(12) 0.147(7) 0.039(8) 0.019(7) 0.014(9) C2S 0.238(12) 0.201(12) 0.147(7) 0.039(8) 0.019(7) 0.014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.066(3) . ? Cu1 N3 2.087(3) 2_666 ? Cu1 I1 2.6085(5) 2_566 ? Cu1 I1 2.6578(5) . ? Cu1 Cu1 2.7452(8) 2_566 ? Cu2 N5 2.078(3) . ? Cu2 N7 2.096(3) 2_765 ? Cu2 I2 2.6158(5) 2_665 ? Cu2 I2 2.6340(5) . ? Cu2 Cu2 2.8093(8) 2_665 ? I1 Cu1 2.6085(5) 2_566 ? I2 Cu2 2.6158(5) 2_665 ? N1 C5 1.341(4) . ? N1 C1 1.347(4) . ? N2 C7 1.341(4) . ? N2 N3 1.351(4) . ? N2 C6 1.449(4) . ? N3 N4 1.315(4) . ? N3 Cu1 2.087(3) 2_666 ? N4 C8 1.361(4) . ? N5 C19 1.344(4) . ? N5 C15 1.344(4) . ? N6 C21 1.340(4) . ? N6 N7 1.354(3) . ? N6 C20 1.453(4) . ? N7 N8 1.320(4) . ? N7 Cu2 2.096(3) 2_765 ? N8 C22 1.368(4) . ? C1 C2 1.373(4) . ? C2 C3 1.388(5) . ? C3 C4 1.389(5) . ? C3 C6 1.507(4) . ? C4 C5 1.383(4) . ? C7 C8 1.369(5) . ? C8 C9 1.478(5) . ? C9 C14 1.366(6) . ? C9 C10 1.380(6) . ? C10 C11 1.369(8) . ? C11 C12 1.349(9) . ? C12 C13 1.354(8) . ? C13 C14 1.383(7) . ? C15 C16 1.384(4) . ? C16 C17 1.378(4) . ? C17 C18 1.391(4) . ? C17 C20 1.508(4) . ? C18 C19 1.374(4) . ? C21 C22 1.372(4) . ? C22 C23 1.467(5) . ? C23 C28 1.352(6) . ? C23 C24 1.388(5) . ? C24 C25 1.383(6) . ? C25 C26 1.345(7) . ? C26 C27 1.329(7) . ? C27 C28 1.398(7) . ? N1S C1S 1.113(5) . ? C1S C2S 1.460(5) . ? 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 Cu1 N3 103.74(10) . 2_666 ? N1 Cu1 I1 106.73(8) . 2_566 ? N3 Cu1 I1 115.18(8) 2_666 2_566 ? N1 Cu1 I1 104.58(7) . . ? N3 Cu1 I1 108.02(8) 2_666 . ? I1 Cu1 I1 117.171(16) 2_566 . ? N1 Cu1 Cu1 121.15(7) . 2_566 ? N3 Cu1 Cu1 134.73(8) 2_666 2_566 ? I1 Cu1 Cu1 59.464(16) 2_566 2_566 ? I1 Cu1 Cu1 57.707(16) . 2_566 ? N5 Cu2 N7 104.31(10) . 2_765 ? N5 Cu2 I2 106.84(8) . 2_665 ? N7 Cu2 I2 114.96(7) 2_765 2_665 ? N5 Cu2 I2 104.76(7) . . ? N7 Cu2 I2 109.51(7) 2_765 . ? I2 Cu2 I2 115.297(16) 2_665 . ? N5 Cu2 Cu2 120.57(7) . 2_665 ? N7 Cu2 Cu2 134.92(7) 2_765 2_665 ? I2 Cu2 Cu2 57.961(15) 2_665 2_665 ? I2 Cu2 Cu2 57.336(15) . 2_665 ? Cu1 I1 Cu1 62.829(16) 2_566 . ? Cu2 I2 Cu2 64.703(16) 2_665 . ? C5 N1 C1 117.0(3) . . ? C5 N1 Cu1 123.4(2) . . ? C1 N1 Cu1 119.5(2) . . ? C7 N2 N3 110.4(3) . . ? C7 N2 C6 128.0(3) . . ? N3 N2 C6 121.6(3) . . ? N4 N3 N2 107.6(2) . . ? N4 N3 Cu1 124.1(2) . 2_666 ? N2 N3 Cu1 126.8(2) . 2_666 ? N3 N4 C8 108.3(3) . . ? C19 N5 C15 116.9(3) . . ? C19 N5 Cu2 121.0(2) . . ? C15 N5 Cu2 122.0(2) . . ? C21 N6 N7 110.5(2) . . ? C21 N6 C20 127.5(3) . . ? N7 N6 C20 121.9(2) . . ? N8 N7 N6 107.5(2) . . ? N8 N7 Cu2 124.0(2) . 2_765 ? N6 N7 Cu2 126.87(19) . 2_765 ? N7 N8 C22 108.3(3) . . ? N1 C1 C2 122.9(3) . . ? C1 C2 C3 119.9(3) . . ? C2 C3 C4 117.7(3) . . ? C2 C3 C6 119.0(3) . . ? C4 C3 C6 123.3(3) . . ? C5 C4 C3 118.8(3) . . ? N1 C5 C4 123.6(3) . . ? N2 C6 C3 114.5(3) . . ? N2 C7 C8 105.0(3) . . ? N4 C8 C7 108.6(3) . . ? N4 C8 C9 121.9(3) . . ? C7 C8 C9 129.3(3) . . ? C14 C9 C10 117.9(4) . . ? C14 C9 C8 121.3(3) . . ? C10 C9 C8 120.8(4) . . ? C11 C10 C9 119.9(5) . . ? C12 C11 C10 122.0(5) . . ? C11 C12 C13 118.8(5) . . ? C12 C13 C14 120.4(6) . . ? C9 C14 C13 121.1(5) . . ? N5 C15 C16 123.0(3) . . ? C17 C16 C15 119.7(3) . . ? C16 C17 C18 117.5(3) . . ? C16 C17 C20 123.4(3) . . ? C18 C17 C20 119.1(3) . . ? C19 C18 C17 119.6(3) . . ? N5 C19 C18 123.3(3) . . ? N6 C20 C17 113.6(3) . . ? N6 C21 C22 105.4(3) . . ? N8 C22 C21 108.3(3) . . ? N8 C22 C23 122.1(3) . . ? C21 C22 C23 129.6(3) . . ? C28 C23 C24 117.8(4) . . ? C28 C23 C22 122.0(4) . . ? C24 C23 C22 120.2(3) . . ? C25 C24 C23 120.1(4) . . ? C26 C25 C24 120.8(5) . . ? C27 C26 C25 119.7(5) . . ? C26 C27 C28 120.8(5) . . ? C23 C28 C27 120.7(5) . . ? N1S C1S C2S 165.2(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.855 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 918965'