# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ana Lago' _publ_contact_author_email ABLAGO@UVIGO.ES _publ_section_title ; Molecular metallocycles, acyclic metallodimers and 2D coordination polymers containing the twisted ligand bis(pyrimidin-2-ylthio)methane ; loop_ _publ_author_name 'Ana Lago' 'Almundena Amoedo' 'Rosa Carballo' 'Emilia Garcia-Martinez' 'Ezequiel M. Vazquez-Lopez' # Attachment 'B915942H.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 742451' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Cl2 Co N4 S2' _chemical_formula_weight 366.14 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pcca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 15.0349(12) _cell_length_b 12.3787(9) _cell_length_c 15.7636(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2933.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812145 _exptl_absorpt_correction_T_max 1.000000 _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 15131 _diffrn_reflns_av_R_equivalents 0.0756 _diffrn_reflns_av_sigmaI/netI 0.1392 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.04 _reflns_number_total 3482 _reflns_number_gt 1465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker ORTEPIII and PLATON' _computing_publication_material 'Bruker SHELX97' _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 w=1/[\s^2^(Fo^2^)+(0.0141P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3482 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1686 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0629 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 0.788 _refine_ls_restrained_S_all 0.788 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.14482(3) 0.24883(4) 0.03998(3) 0.04311(14) Uani 1 d . . . S11 S -0.18576(7) 0.22804(7) 0.26095(6) 0.0511(3) Uani 1 d . . . S1 S -0.05592(7) 0.19541(8) 0.11585(6) 0.0517(3) Uani 1 d . . . Cl1 Cl 0.27731(7) 0.32821(7) 0.04509(7) 0.0589(3) Uani 1 d . . . Cl2 Cl 0.10054(7) 0.20437(8) -0.09026(6) 0.0617(3) Uani 1 d . . . C1 C -0.1700(2) 0.1998(3) 0.1509(2) 0.0506(11) Uani 1 d . . . H1A H -0.2010 0.2545 0.1182 0.061 Uiso 1 calc R . . H1B H -0.1975 0.1308 0.1382 0.061 Uiso 1 calc R . . N1 N 0.0542(2) 0.3563(2) 0.08980(17) 0.0420(8) Uani 1 d . . . C2 C -0.0285(3) 0.3330(3) 0.1170(2) 0.0408(10) Uani 1 d . . . N3 N -0.0888(2) 0.4037(3) 0.14409(19) 0.0532(9) Uani 1 d . . . C4 C -0.0634(3) 0.5064(3) 0.1443(2) 0.0647(13) Uani 1 d . . . H4 H -0.1036 0.5586 0.1623 0.078 Uiso 1 calc R . . C5 C 0.0200(3) 0.5388(3) 0.1189(3) 0.0666(14) Uani 1 d . . . H5 H 0.0366 0.6112 0.1202 0.080 Uiso 1 calc R . . C6 C 0.0773(3) 0.4614(3) 0.0920(2) 0.0542(11) Uani 1 d . . . H6 H 0.1340 0.4815 0.0746 0.065 Uiso 1 calc R . . N11 N -0.14538(19) 0.1079(2) 0.39169(19) 0.0404(8) Uani 1 d . . . C12 C -0.1533(2) 0.1051(3) 0.3063(3) 0.0399(9) Uani 1 d . . . N13 N -0.1385(2) 0.0204(3) 0.25754(19) 0.0534(9) Uani 1 d . . . C14 C -0.1163(3) -0.0704(3) 0.2977(3) 0.0616(13) Uani 1 d . . . H14 H -0.1042 -0.1314 0.2653 0.074 Uiso 1 calc R . . C15 C -0.1105(3) -0.0786(3) 0.3842(3) 0.0574(12) Uani 1 d . . . H15 H -0.0975 -0.1437 0.4109 0.069 Uiso 1 calc R . . C16 C -0.1249(2) 0.0147(3) 0.4294(2) 0.0497(11) Uani 1 d . . . H16 H -0.1201 0.0129 0.4882 0.060 Uiso 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 Co1 0.0426(3) 0.0441(3) 0.0427(3) -0.0031(3) 0.0065(3) -0.0048(3) S11 0.0551(8) 0.0559(7) 0.0422(6) 0.0042(5) 0.0008(5) 0.0073(5) S1 0.0401(7) 0.0544(7) 0.0605(7) -0.0021(5) 0.0074(6) -0.0042(5) Cl1 0.0486(7) 0.0584(6) 0.0697(7) -0.0099(6) 0.0121(6) -0.0151(5) Cl2 0.0583(8) 0.0801(8) 0.0468(7) -0.0090(5) -0.0005(6) -0.0066(6) C1 0.035(3) 0.076(3) 0.042(2) 0.005(2) -0.0022(19) -0.005(2) N1 0.049(2) 0.037(2) 0.0394(19) 0.0030(15) 0.0020(18) -0.0045(16) C2 0.041(3) 0.047(3) 0.034(2) 0.0041(19) -0.002(2) -0.001(2) N3 0.048(3) 0.053(2) 0.059(2) 0.0018(19) 0.0077(18) 0.011(2) C4 0.071(4) 0.056(3) 0.067(3) 0.000(3) 0.013(3) 0.025(3) C5 0.074(4) 0.045(3) 0.081(4) -0.004(2) 0.009(3) 0.005(3) C6 0.057(3) 0.047(3) 0.058(3) 0.004(2) 0.011(2) -0.004(2) N11 0.036(2) 0.0410(19) 0.044(2) 0.0074(16) 0.0047(18) -0.0003(15) C12 0.026(2) 0.044(2) 0.050(3) -0.002(2) -0.001(2) -0.0027(18) N13 0.051(3) 0.050(2) 0.059(2) -0.016(2) 0.0022(19) 0.0029(18) C14 0.051(3) 0.048(3) 0.086(4) -0.022(3) 0.005(3) 0.001(2) C15 0.054(3) 0.039(3) 0.080(4) 0.002(3) -0.002(3) 0.002(2) C16 0.049(3) 0.044(3) 0.056(3) 0.011(2) 0.003(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N11 2.050(3) 3 ? Co1 N1 2.060(3) . ? Co1 Cl1 2.2227(11) . ? Co1 Cl2 2.2274(11) . ? Co1 S11 3.2082(11) 3 ? Co1 S1 3.3131(12) . ? S11 C12 1.751(3) . ? S11 C1 1.785(3) . ? S1 C2 1.752(4) . ? S1 C1 1.803(3) . ? N1 C2 1.347(4) . ? N1 C6 1.347(4) . ? C2 N3 1.330(4) . ? N3 C4 1.327(4) . ? C4 C5 1.376(5) . ? C5 C6 1.356(5) . ? N11 C16 1.334(4) . ? N11 C12 1.351(4) . ? N11 Co1 2.050(3) 3 ? C12 N13 1.320(4) . ? N13 C14 1.332(4) . ? C14 C15 1.371(5) . ? C15 C16 1.375(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 N11 Co1 N1 110.61(11) 3 . ? N11 Co1 Cl1 110.70(9) 3 . ? N1 Co1 Cl1 107.05(9) . . ? N11 Co1 Cl2 105.99(9) 3 . ? N1 Co1 Cl2 108.27(8) . . ? Cl1 Co1 Cl2 114.24(4) . . ? N11 Co1 S11 54.34(9) 3 3 ? N1 Co1 S11 78.80(8) . 3 ? Cl1 Co1 S11 80.10(4) . 3 ? Cl2 Co1 S11 159.91(4) . 3 ? N11 Co1 S1 69.16(8) 3 . ? N1 Co1 S1 52.33(9) . . ? Cl1 Co1 S1 153.07(4) . . ? Cl2 Co1 S1 90.64(4) . . ? S11 Co1 S1 78.79(3) 3 . ? C12 S11 C1 100.96(18) . . ? C2 S1 C1 101.01(17) . . ? C2 S1 Co1 66.14(14) . . ? C1 S1 Co1 166.23(12) . . ? S11 C1 S1 115.47(19) . . ? C2 N1 C6 115.9(3) . . ? C2 N1 Co1 126.4(2) . . ? C6 N1 Co1 117.6(3) . . ? N3 C2 N1 126.1(3) . . ? N3 C2 S1 118.9(3) . . ? N1 C2 S1 115.0(3) . . ? C4 N3 C2 115.8(4) . . ? N3 C4 C5 122.7(4) . . ? C6 C5 C4 117.6(4) . . ? N1 C6 C5 121.8(4) . . ? C16 N11 C12 116.2(3) . . ? C16 N11 Co1 120.0(3) . 3 ? C12 N11 Co1 123.1(2) . 3 ? N13 C12 N11 125.9(3) . . ? N13 C12 S11 120.0(3) . . ? N11 C12 S11 114.1(3) . . ? C12 N13 C14 115.9(3) . . ? N13 C14 C15 123.4(4) . . ? C14 C15 C16 116.4(4) . . ? N11 C16 C15 122.1(4) . . ? 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 N11 Co1 S1 C2 142.32(16) 3 . . . ? N1 Co1 S1 C2 2.00(17) . . . . ? Cl1 Co1 S1 C2 47.41(15) . . . . ? Cl2 Co1 S1 C2 -110.80(13) . . . . ? S11 Co1 S1 C2 86.41(13) 3 . . . ? N11 Co1 S1 C1 164.3(5) 3 . . . ? N1 Co1 S1 C1 24.0(5) . . . . ? Cl1 Co1 S1 C1 69.4(5) . . . . ? Cl2 Co1 S1 C1 -88.8(5) . . . . ? S11 Co1 S1 C1 108.4(5) 3 . . . ? C12 S11 C1 S1 -73.8(2) . . . . ? C2 S1 C1 S11 -73.5(2) . . . . ? Co1 S1 C1 S11 -94.0(5) . . . . ? N11 Co1 N1 C2 -42.6(3) 3 . . . ? Cl1 Co1 N1 C2 -163.2(3) . . . . ? Cl2 Co1 N1 C2 73.2(3) . . . . ? S11 Co1 N1 C2 -87.4(3) 3 . . . ? S1 Co1 N1 C2 -2.9(2) . . . . ? N11 Co1 N1 C6 140.9(3) 3 . . . ? Cl1 Co1 N1 C6 20.3(3) . . . . ? Cl2 Co1 N1 C6 -103.3(3) . . . . ? S11 Co1 N1 C6 96.1(3) 3 . . . ? S1 Co1 N1 C6 -179.4(3) . . . . ? C6 N1 C2 N3 1.2(5) . . . . ? Co1 N1 C2 N3 -175.4(3) . . . . ? C6 N1 C2 S1 -178.6(2) . . . . ? Co1 N1 C2 S1 4.9(4) . . . . ? C1 S1 C2 N3 2.8(3) . . . . ? Co1 S1 C2 N3 177.6(3) . . . . ? C1 S1 C2 N1 -177.4(3) . . . . ? Co1 S1 C2 N1 -2.7(2) . . . . ? N1 C2 N3 C4 -0.5(6) . . . . ? S1 C2 N3 C4 179.3(3) . . . . ? C2 N3 C4 C5 -0.5(6) . . . . ? N3 C4 C5 C6 0.8(7) . . . . ? C2 N1 C6 C5 -0.9(5) . . . . ? Co1 N1 C6 C5 176.0(3) . . . . ? C4 C5 C6 N1 0.0(6) . . . . ? C16 N11 C12 N13 -3.5(5) . . . . ? Co1 N11 C12 N13 167.1(3) 3 . . . ? C16 N11 C12 S11 177.0(3) . . . . ? Co1 N11 C12 S11 -12.4(4) 3 . . . ? C1 S11 C12 N13 -9.3(3) . . . . ? C1 S11 C12 N11 170.3(3) . . . . ? N11 C12 N13 C14 2.2(5) . . . . ? S11 C12 N13 C14 -178.3(3) . . . . ? C12 N13 C14 C15 1.3(6) . . . . ? N13 C14 C15 C16 -3.0(6) . . . . ? C12 N11 C16 C15 1.5(5) . . . . ? Co1 N11 C16 C15 -169.4(3) 3 . . . ? C14 C15 C16 N11 1.5(6) . . . . ? 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 C1 H1A Cl1 0.97 2.75 3.564(3) 141.8 6 C1 H1B N13 0.97 2.49 2.826(5) 100.1 . C6 H6 Cl1 0.93 2.75 3.479(4) 136.4 2_565 _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.509 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.057 #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 742452' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 I2 N4 S2 Zn' _chemical_formula_weight 555.48 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3042(10) _cell_length_b 16.8885(15) _cell_length_c 17.0363(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.906(2) _cell_angle_gamma 90.00 _cell_volume 3111.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'palid yellow' _exptl_crystal_size_max .89 _exptl_crystal_size_mid .85 _exptl_crystal_size_min .54 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 5.803 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8123 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 17674 _diffrn_reflns_av_R_equivalents 0.0930 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.06 _reflns_number_total 7082 _reflns_number_gt 4632 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELX97' _computing_publication_material 'Bruker SHELX97' _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^)+(0.0918P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7082 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.51998(6) -0.02459(5) -0.35483(5) 0.0637(2) Uani 1 1 d . . . I2 I -0.33657(7) -0.17812(5) -0.48797(5) 0.0750(3) Uani 1 1 d . . . I3 I 0.36988(5) 0.10715(4) 0.06879(3) 0.04651(18) Uani 1 1 d . . . I4 I 0.49668(6) 0.16100(5) -0.14098(4) 0.0656(2) Uani 1 1 d . . . Zn1 Zn -0.32167(9) -0.06941(6) -0.38203(6) 0.0428(3) Uani 1 1 d . . . Zn2 Zn 0.32390(8) 0.10876(6) -0.08743(6) 0.0372(2) Uani 1 1 d . . . S1 S -0.1993(2) 0.03420(14) -0.21397(14) 0.0474(5) Uani 1 1 d . . . S11 S 0.03361(19) 0.08136(15) -0.08091(13) 0.0460(5) Uani 1 1 d . . . N1 N -0.2003(6) -0.1106(4) -0.2705(4) 0.0397(16) Uani 1 1 d . . . N3 N -0.0843(6) -0.0907(4) -0.1311(4) 0.0433(17) Uani 1 1 d . . . C1 C -0.1309(7) 0.0691(5) -0.1108(5) 0.0389(18) Uani 1 1 d . . . H1A H -0.1682 0.1196 -0.1047 0.047 Uiso 1 1 calc R . . H1B H -0.1515 0.0321 -0.0732 0.047 Uiso 1 1 calc R . . C2 C -0.1575(7) -0.0659(5) -0.2035(5) 0.0369(18) Uani 1 1 d . . . C4 C -0.0585(9) -0.1682(6) -0.1257(6) 0.051(2) Uani 1 1 d . . . H4 H -0.0114 -0.1885 -0.0756 0.061 Uiso 1 1 calc R . . C5 C -0.0990(9) -0.2194(6) -0.1915(6) 0.051(2) Uani 1 1 d . . . H5 H -0.0795 -0.2730 -0.1867 0.062 Uiso 1 1 calc R . . C6 C -0.1688(8) -0.1876(5) -0.2637(6) 0.047(2) Uani 1 1 d . . . H6 H -0.1954 -0.2201 -0.3096 0.057 Uiso 1 1 calc R . . N11 N 0.1652(6) 0.1769(4) -0.1420(4) 0.0394(16) Uani 1 1 d . . . N13 N -0.0519(6) 0.1949(4) -0.1896(5) 0.0445(17) Uani 1 1 d . . . C12 C 0.0481(7) 0.1590(5) -0.1442(5) 0.0340(17) Uani 1 1 d . . . C14 C -0.0331(8) 0.2551(6) -0.2350(7) 0.057(3) Uani 1 1 d . . . H14 H -0.1022 0.2810 -0.2682 0.069 Uiso 1 1 calc R . . C15 C 0.0792(9) 0.2812(6) -0.2363(7) 0.060(3) Uani 1 1 d . . . H15 H 0.0884 0.3244 -0.2679 0.072 Uiso 1 1 calc R . . C16 C 0.1805(9) 0.2395(6) -0.1877(6) 0.053(2) Uani 1 1 d . . . H16 H 0.2599 0.2550 -0.1865 0.064 Uiso 1 1 calc R . . S21 S -0.0275(2) -0.05184(15) -0.38321(16) 0.0506(6) Uani 1 1 d . . . S31 S 0.1910(2) 0.04268(15) -0.27835(13) 0.0510(6) Uani 1 1 d . . . N21 N -0.2338(6) 0.0299(4) -0.4130(4) 0.0401(16) Uani 1 1 d . . . N23 N -0.0585(8) 0.0996(5) -0.4273(5) 0.059(2) Uani 1 1 d . . . C21 C 0.1258(8) -0.0150(6) -0.3695(5) 0.050(2) Uani 1 1 d . . . H21A H 0.1252 0.0173 -0.4167 0.060 Uiso 1 1 calc R . . H21B H 0.1800 -0.0597 -0.3689 0.060 Uiso 1 1 calc R . . C22 C -0.1134(8) 0.0357(5) -0.4106(5) 0.041(2) Uani 1 1 d . . . C24 C -0.1300(12) 0.1639(7) -0.4522(8) 0.072(3) Uani 1 1 d . . . H24 H -0.0943 0.2100 -0.4649 0.086 Uiso 1 1 calc R . . C25 C -0.2566(12) 0.1634(7) -0.4597(8) 0.072(3) Uani 1 1 d . . . H25 H -0.3060 0.2075 -0.4783 0.087 Uiso 1 1 calc R . . C26 C -0.3041(10) 0.0953(6) -0.4385(6) 0.056(3) Uani 1 1 d . . . H26 H -0.3876 0.0936 -0.4415 0.067 Uiso 1 1 calc R . . N31 N 0.2748(6) -0.0078(4) -0.1258(4) 0.0361(15) Uani 1 1 d . . . N33 N 0.1876(7) -0.1051(5) -0.2271(5) 0.0505(19) Uani 1 1 d . . . C32 C 0.2204(7) -0.0315(5) -0.2034(5) 0.0392(19) Uani 1 1 d . . . C34 C 0.2120(9) -0.1587(6) -0.1675(6) 0.052(2) Uani 1 1 d . . . H34 H 0.1884 -0.2108 -0.1813 0.062 Uiso 1 1 calc R . . C35 C 0.2712(8) -0.1413(6) -0.0853(6) 0.052(2) Uani 1 1 d . . . H35 H 0.2885 -0.1800 -0.0447 0.062 Uiso 1 1 calc R . . C36 C 0.3014(8) -0.0646(6) -0.0688(6) 0.046(2) Uani 1 1 d . . . H36 H 0.3430 -0.0506 -0.0151 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0397(3) 0.0808(5) 0.0684(5) 0.0000(4) 0.0121(3) 0.0088(3) I2 0.0743(5) 0.0567(5) 0.0697(5) -0.0302(4) -0.0172(4) 0.0148(3) I3 0.0470(3) 0.0597(4) 0.0310(3) -0.0049(3) 0.0085(2) -0.0062(3) I4 0.0422(3) 0.0950(6) 0.0601(4) 0.0243(4) 0.0160(3) -0.0094(3) Zn1 0.0359(5) 0.0407(6) 0.0434(6) -0.0058(4) -0.0016(4) 0.0039(4) Zn2 0.0359(5) 0.0420(6) 0.0309(5) 0.0032(4) 0.0055(4) -0.0037(4) S1 0.0550(13) 0.0423(13) 0.0343(11) 0.0004(9) -0.0037(10) 0.0036(10) S11 0.0364(10) 0.0611(15) 0.0370(11) 0.0175(10) 0.0052(9) -0.0026(10) N1 0.040(4) 0.034(4) 0.043(4) 0.003(3) 0.009(3) 0.004(3) N3 0.043(4) 0.050(5) 0.035(4) 0.014(3) 0.007(3) 0.006(3) C1 0.036(4) 0.046(5) 0.034(4) 0.003(4) 0.010(3) 0.003(3) C2 0.026(4) 0.046(5) 0.035(4) -0.003(4) 0.005(3) 0.002(3) C4 0.053(5) 0.062(7) 0.037(5) 0.017(5) 0.013(4) 0.014(5) C5 0.056(5) 0.046(6) 0.057(6) 0.016(5) 0.024(5) 0.015(4) C6 0.044(5) 0.045(5) 0.053(5) 0.002(4) 0.014(4) 0.007(4) N11 0.041(4) 0.045(4) 0.035(4) 0.003(3) 0.015(3) -0.002(3) N13 0.040(4) 0.050(5) 0.044(4) 0.016(3) 0.014(3) 0.009(3) C12 0.037(4) 0.037(5) 0.029(4) 0.002(3) 0.012(3) 0.000(3) C14 0.045(5) 0.064(7) 0.070(7) 0.030(5) 0.027(5) 0.011(5) C15 0.049(5) 0.060(7) 0.074(7) 0.035(6) 0.021(5) 0.008(5) C16 0.047(5) 0.049(6) 0.064(6) 0.011(5) 0.018(5) -0.007(4) S21 0.0414(11) 0.0568(15) 0.0516(13) -0.0014(11) 0.0105(10) 0.0066(10) S31 0.0575(14) 0.0605(16) 0.0310(11) -0.0006(10) 0.0067(10) 0.0007(11) N21 0.038(3) 0.047(4) 0.029(3) -0.006(3) 0.001(3) 0.006(3) N23 0.066(5) 0.063(6) 0.053(5) -0.008(4) 0.024(4) -0.005(4) C21 0.046(5) 0.079(7) 0.028(4) -0.006(4) 0.015(4) 0.005(5) C22 0.042(4) 0.052(6) 0.028(4) -0.007(4) 0.008(3) 0.006(4) C24 0.086(9) 0.049(7) 0.082(8) 0.006(6) 0.027(7) 0.000(6) C25 0.083(8) 0.048(7) 0.078(8) 0.012(6) 0.011(7) 0.007(6) C26 0.065(6) 0.050(6) 0.048(5) -0.004(5) 0.007(5) 0.006(5) N31 0.032(3) 0.045(4) 0.029(3) 0.002(3) 0.005(3) -0.005(3) N33 0.044(4) 0.064(6) 0.043(4) -0.013(4) 0.013(3) 0.004(4) C32 0.033(4) 0.044(5) 0.040(5) 0.001(4) 0.010(3) 0.004(3) C34 0.052(5) 0.042(6) 0.066(7) -0.015(5) 0.026(5) -0.002(4) C35 0.050(5) 0.048(6) 0.061(6) 0.010(5) 0.022(5) 0.004(4) C36 0.041(4) 0.053(6) 0.039(5) 0.002(4) 0.005(4) 0.000(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 I1 Zn1 2.5332(12) . ? I2 Zn1 2.5455(12) . ? I3 Zn2 2.5592(11) . ? I4 Zn2 2.5419(11) . ? Zn1 N21 2.093(7) . ? Zn1 N1 2.112(7) . ? Zn2 N31 2.097(7) . ? Zn2 N11 2.106(7) . ? S1 C2 1.750(9) . ? S1 C1 1.801(8) . ? S11 C12 1.735(8) . ? S11 C1 1.791(8) . ? N1 C2 1.336(10) . ? N1 C6 1.344(11) . ? N3 C4 1.337(12) . ? N3 C2 1.338(10) . ? C4 C5 1.385(14) . ? C5 C6 1.364(13) . ? N11 C12 1.348(10) . ? N11 C16 1.353(11) . ? N13 C12 1.317(10) . ? N13 C14 1.332(11) . ? C14 C15 1.350(13) . ? C15 C16 1.393(13) . ? S21 C22 1.757(9) . ? S21 C21 1.792(9) . ? S31 C32 1.751(9) . ? S31 C21 1.798(9) . ? N21 C22 1.353(11) . ? N21 C26 1.357(12) . ? N23 C22 1.316(12) . ? N23 C24 1.348(14) . ? C24 C25 1.399(16) . ? C25 C26 1.362(15) . ? N31 C36 1.335(11) . ? N31 C32 1.347(10) . ? N33 C32 1.326(11) . ? N33 C34 1.327(13) . ? C34 C35 1.397(14) . ? C35 C36 1.349(13) . ? 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 N21 Zn1 N1 105.0(3) . . ? N21 Zn1 I1 108.48(19) . . ? N1 Zn1 I1 108.1(2) . . ? N21 Zn1 I2 109.71(19) . . ? N1 Zn1 I2 106.98(19) . . ? I1 Zn1 I2 117.75(4) . . ? N31 Zn2 N11 105.1(3) . . ? N31 Zn2 I4 112.04(18) . . ? N11 Zn2 I4 107.25(18) . . ? N31 Zn2 I3 105.61(18) . . ? N11 Zn2 I3 110.77(19) . . ? I4 Zn2 I3 115.59(4) . . ? C2 S1 C1 101.0(4) . . ? C12 S11 C1 100.9(4) . . ? C2 N1 C6 116.9(8) . . ? C2 N1 Zn1 124.1(5) . . ? C6 N1 Zn1 118.8(6) . . ? C4 N3 C2 115.7(8) . . ? S11 C1 S1 115.5(4) . . ? N1 C2 N3 125.7(8) . . ? N1 C2 S1 116.0(6) . . ? N3 C2 S1 118.2(6) . . ? N3 C4 C5 122.8(8) . . ? C6 C5 C4 116.9(9) . . ? N1 C6 C5 121.8(9) . . ? C12 N11 C16 116.6(7) . . ? C12 N11 Zn2 126.4(5) . . ? C16 N11 Zn2 116.5(6) . . ? C12 N13 C14 116.0(7) . . ? N13 C12 N11 125.5(7) . . ? N13 C12 S11 119.5(6) . . ? N11 C12 S11 115.0(6) . . ? N13 C14 C15 124.6(9) . . ? C14 C15 C16 116.1(9) . . ? N11 C16 C15 121.1(8) . . ? C22 S21 C21 100.4(5) . . ? C32 S31 C21 100.7(5) . . ? C22 N21 C26 116.2(8) . . ? C22 N21 Zn1 126.7(6) . . ? C26 N21 Zn1 117.1(6) . . ? C22 N23 C24 116.8(9) . . ? S21 C21 S31 116.0(5) . . ? N23 C22 N21 125.9(8) . . ? N23 C22 S21 119.2(7) . . ? N21 C22 S21 114.8(7) . . ? N23 C24 C25 121.8(11) . . ? C26 C25 C24 117.0(10) . . ? N21 C26 C25 122.2(10) . . ? C36 N31 C32 116.2(7) . . ? C36 N31 Zn2 117.7(6) . . ? C32 N31 Zn2 126.1(6) . . ? C32 N33 C34 115.4(8) . . ? N33 C32 N31 125.8(8) . . ? N33 C32 S31 118.1(7) . . ? N31 C32 S31 116.0(6) . . ? N33 C34 C35 123.8(9) . . ? C36 C35 C34 115.3(9) . . ? N31 C36 C35 123.4(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Zn1 N1 C2 54.5(7) . . . . ? I1 Zn1 N1 C2 -61.2(7) . . . . ? I2 Zn1 N1 C2 171.1(6) . . . . ? N21 Zn1 N1 C6 -129.5(6) . . . . ? I1 Zn1 N1 C6 114.8(6) . . . . ? I2 Zn1 N1 C6 -12.9(7) . . . . ? C12 S11 C1 S1 66.8(6) . . . . ? C2 S1 C1 S11 75.2(5) . . . . ? C6 N1 C2 N3 1.3(12) . . . . ? Zn1 N1 C2 N3 177.4(6) . . . . ? C6 N1 C2 S1 179.8(6) . . . . ? Zn1 N1 C2 S1 -4.1(9) . . . . ? C4 N3 C2 N1 -3.6(12) . . . . ? C4 N3 C2 S1 177.9(6) . . . . ? C1 S1 C2 N1 177.0(6) . . . . ? C1 S1 C2 N3 -4.4(7) . . . . ? C2 N3 C4 C5 3.2(13) . . . . ? N3 C4 C5 C6 -0.6(14) . . . . ? C2 N1 C6 C5 1.6(13) . . . . ? Zn1 N1 C6 C5 -174.7(7) . . . . ? C4 C5 C6 N1 -1.9(14) . . . . ? N31 Zn2 N11 C12 45.8(7) . . . . ? I4 Zn2 N11 C12 165.2(6) . . . . ? I3 Zn2 N11 C12 -67.8(7) . . . . ? N31 Zn2 N11 C16 -125.8(7) . . . . ? I4 Zn2 N11 C16 -6.4(7) . . . . ? I3 Zn2 N11 C16 120.6(6) . . . . ? C14 N13 C12 N11 -2.0(13) . . . . ? C14 N13 C12 S11 178.5(7) . . . . ? C16 N11 C12 N13 3.4(13) . . . . ? Zn2 N11 C12 N13 -168.1(7) . . . . ? C16 N11 C12 S11 -177.0(7) . . . . ? Zn2 N11 C12 S11 11.5(9) . . . . ? C1 S11 C12 N13 6.5(8) . . . . ? C1 S11 C12 N11 -173.2(6) . . . . ? C12 N13 C14 C15 -0.8(16) . . . . ? N13 C14 C15 C16 1.7(18) . . . . ? C12 N11 C16 C15 -2.2(14) . . . . ? Zn2 N11 C16 C15 170.2(9) . . . . ? C14 C15 C16 N11 -0.1(17) . . . . ? N1 Zn1 N21 C22 45.6(7) . . . . ? I1 Zn1 N21 C22 161.0(6) . . . . ? I2 Zn1 N21 C22 -69.1(7) . . . . ? N1 Zn1 N21 C26 -134.7(6) . . . . ? I1 Zn1 N21 C26 -19.2(6) . . . . ? I2 Zn1 N21 C26 110.6(6) . . . . ? C22 S21 C21 S31 73.6(6) . . . . ? C32 S31 C21 S21 72.7(6) . . . . ? C24 N23 C22 N21 -3.0(14) . . . . ? C24 N23 C22 S21 176.5(8) . . . . ? C26 N21 C22 N23 3.1(13) . . . . ? Zn1 N21 C22 N23 -177.2(7) . . . . ? C26 N21 C22 S21 -176.4(6) . . . . ? Zn1 N21 C22 S21 3.3(9) . . . . ? C21 S21 C22 N23 10.3(8) . . . . ? C21 S21 C22 N21 -170.1(6) . . . . ? C22 N23 C24 C25 0.4(17) . . . . ? N23 C24 C25 C26 1.7(19) . . . . ? C22 N21 C26 C25 -0.6(14) . . . . ? Zn1 N21 C26 C25 179.6(8) . . . . ? C24 C25 C26 N21 -1.6(17) . . . . ? N11 Zn2 N31 C36 -132.3(6) . . . . ? I4 Zn2 N31 C36 111.5(6) . . . . ? I3 Zn2 N31 C36 -15.1(6) . . . . ? N11 Zn2 N31 C32 49.0(7) . . . . ? I4 Zn2 N31 C32 -67.2(7) . . . . ? I3 Zn2 N31 C32 166.2(6) . . . . ? C34 N33 C32 N31 -0.1(12) . . . . ? C34 N33 C32 S31 -179.8(6) . . . . ? C36 N31 C32 N33 2.6(12) . . . . ? Zn2 N31 C32 N33 -178.7(6) . . . . ? C36 N31 C32 S31 -177.7(6) . . . . ? Zn2 N31 C32 S31 1.0(9) . . . . ? C21 S31 C32 N33 -2.3(8) . . . . ? C21 S31 C32 N31 177.9(6) . . . . ? C32 N33 C34 C35 -1.8(13) . . . . ? N33 C34 C35 C36 1.0(14) . . . . ? C32 N31 C36 C35 -3.3(12) . . . . ? Zn2 N31 C36 C35 177.8(7) . . . . ? C34 C35 C36 N31 1.7(13) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 2.239 _refine_diff_density_min -1.869 _refine_diff_density_rms 0.219 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 742453' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Cd I2 N4 S2' _chemical_formula_weight 602.51 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4674(8) _cell_length_b 17.3623(12) _cell_length_c 17.0098(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.2470(10) _cell_angle_gamma 90.00 _cell_volume 3234.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .34 _exptl_crystal_size_mid .31 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 5.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.546283 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 19090 _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.03 _reflns_number_total 7418 _reflns_number_gt 4232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELX97' _computing_publication_material 'Bruker SHELX97' _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^)+(0.0337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7418 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 Cd1 Cd 0.33463(4) 0.10901(3) -0.07882(3) 0.04921(15) Uani 1 1 d . . . Cd2 Cd -0.33168(5) -0.06199(3) -0.39904(4) 0.05700(17) Uani 1 1 d . . . I1 I 0.38062(4) 0.08925(3) 0.08569(3) 0.05550(15) Uani 1 1 d . . . I2 I 0.50337(5) 0.17544(4) -0.13732(4) 0.0858(2) Uani 1 1 d . . . I3 I -0.53280(5) -0.00961(4) -0.36592(4) 0.07390(19) Uani 1 1 d . . . I4 I -0.33890(6) -0.18769(4) -0.49221(4) 0.0977(3) Uani 1 1 d . . . S1 S 0.03219(16) 0.08596(11) -0.08331(11) 0.0534(5) Uani 1 1 d . . . S11 S -0.19574(17) 0.03781(11) -0.21720(11) 0.0560(5) Uani 1 1 d . . . S21 S -0.80983(18) 0.04592(12) -0.27651(11) 0.0587(5) Uani 1 1 d . . . S31 S -1.02912(16) -0.03536(11) -0.39230(11) 0.0543(5) Uani 1 1 d . . . C32 C -1.1071(6) 0.0520(4) -0.4136(4) 0.0463(17) Uani 1 1 d . . . C36 C -0.2911(7) 0.1135(5) -0.4380(4) 0.058(2) Uani 1 1 d . . . H36 H -0.3745 0.1125 -0.4443 0.069 Uiso 1 1 calc R . . N3 N -0.0540(5) 0.2015(4) -0.1876(3) 0.0550(16) Uani 1 1 d . . . N23 N -0.8147(5) -0.1020(4) -0.2360(3) 0.0552(16) Uani 1 1 d . . . C26 C 0.2959(6) -0.0704(5) -0.0756(4) 0.055(2) Uani 1 1 d . . . H26 H 0.3348 -0.0596 -0.0205 0.066 Uiso 1 1 calc R . . C16 C -0.1644(6) -0.1769(4) -0.2632(4) 0.055(2) Uani 1 1 d . . . H16 H -0.1913 -0.2089 -0.3088 0.066 Uiso 1 1 calc R . . C22 C -0.7821(5) -0.0320(4) -0.2078(4) 0.0440(17) Uani 1 1 d . . . N33 N -1.0481(6) 0.1155(4) -0.4202(4) 0.0644(18) Uani 1 1 d . . . C14 C -0.0532(6) -0.1575(5) -0.1265(4) 0.057(2) Uani 1 1 d . . . H14 H -0.0039 -0.1763 -0.0764 0.068 Uiso 1 1 calc R . . C1 C -0.1308(6) 0.0735(4) -0.1147(4) 0.0496(18) Uani 1 1 d . . . H1A H -0.1515 0.0382 -0.0767 0.060 Uiso 1 1 calc R . . H1B H -0.1683 0.1227 -0.1102 0.060 Uiso 1 1 calc R . . C12 C -0.1525(6) -0.0587(4) -0.2047(4) 0.0461(17) Uani 1 1 d . . . C24 C -0.7935(7) -0.1576(5) -0.1794(5) 0.061(2) Uani 1 1 d . . . H24 H -0.8205 -0.2072 -0.1960 0.074 Uiso 1 1 calc R . . C25 C 0.2666(6) -0.1448(4) -0.0974(5) 0.0563(19) Uani 1 1 d . . . H25 H 0.2859 -0.1848 -0.0592 0.068 Uiso 1 1 calc R . . C15 C -0.0931(7) -0.2080(5) -0.1902(5) 0.063(2) Uani 1 1 d . . . H15 H -0.0735 -0.2601 -0.1848 0.076 Uiso 1 1 calc R . . C21 C -0.8741(6) -0.0020(4) -0.3736(4) 0.057(2) Uani 1 1 d . . . H21A H -0.8229 -0.0459 -0.3763 0.068 Uiso 1 1 calc R . . H21B H -0.8716 0.0331 -0.4175 0.068 Uiso 1 1 calc R . . C5 C 0.0785(8) 0.2914(5) -0.2223(5) 0.072(2) Uani 1 1 d . . . H5 H 0.0885 0.3361 -0.2498 0.087 Uiso 1 1 calc R . . C35 C -0.2392(8) 0.1813(5) -0.4472(5) 0.076(3) Uani 1 1 d . . . H35 H -0.2848 0.2264 -0.4592 0.091 Uiso 1 1 calc R . . C4 C -0.0337(7) 0.2637(5) -0.2266(5) 0.068(2) Uani 1 1 d . . . H4 H -0.1012 0.2903 -0.2592 0.082 Uiso 1 1 calc R . . C6 C 0.1775(7) 0.2499(4) -0.1749(5) 0.062(2) Uani 1 1 d . . . H6 H 0.2561 0.2669 -0.1704 0.074 Uiso 1 1 calc R . . C34 C -1.1143(9) 0.1809(5) -0.4378(5) 0.081(3) Uani 1 1 d . . . H34 H -1.0758 0.2267 -0.4439 0.097 Uiso 1 1 calc R . . N31 N -0.2274(5) 0.0472(3) -0.4203(3) 0.0467(14) Uani 1 1 d . . . N1 N 0.1622(5) 0.1858(3) -0.1354(3) 0.0457(14) Uani 1 1 d . . . N13 N -0.0811(5) -0.0823(4) -0.1320(3) 0.0531(15) Uani 1 1 d . . . N21 N 0.2719(4) -0.0122(3) -0.1288(3) 0.0418(13) Uani 1 1 d . . . N11 N -0.1961(4) -0.1037(3) -0.2709(3) 0.0471(14) Uani 1 1 d . . . C2 C 0.0461(6) 0.1655(4) -0.1415(4) 0.0450(17) 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 Cd1 0.0439(3) 0.0545(3) 0.0430(3) 0.0065(2) 0.0032(2) -0.0084(2) Cd2 0.0414(3) 0.0489(3) 0.0715(4) -0.0121(3) 0.0025(3) 0.0039(2) I1 0.0537(3) 0.0680(3) 0.0411(3) -0.0011(2) 0.0084(2) -0.0083(2) I2 0.0522(3) 0.1138(5) 0.0876(4) 0.0429(4) 0.0150(3) -0.0149(3) I3 0.0460(3) 0.0878(4) 0.0854(4) 0.0000(3) 0.0157(3) 0.0109(3) I4 0.1041(5) 0.0684(4) 0.0872(5) -0.0340(3) -0.0232(4) 0.0265(4) S1 0.0451(10) 0.0609(12) 0.0496(11) 0.0131(9) 0.0071(8) -0.0047(9) S11 0.0594(12) 0.0508(12) 0.0476(11) -0.0025(9) -0.0001(9) 0.0006(9) S21 0.0628(12) 0.0659(14) 0.0397(10) -0.0003(9) 0.0034(9) 0.0001(10) S31 0.0433(11) 0.0621(13) 0.0542(11) -0.0037(9) 0.0091(9) 0.0079(9) C32 0.052(5) 0.053(5) 0.029(4) -0.007(3) 0.006(3) 0.003(4) C36 0.049(4) 0.062(5) 0.055(5) -0.005(4) 0.005(4) 0.007(4) N3 0.044(4) 0.069(4) 0.051(4) 0.011(3) 0.012(3) 0.013(3) N23 0.056(4) 0.057(4) 0.052(4) -0.012(3) 0.015(3) -0.005(3) C26 0.041(4) 0.067(6) 0.049(4) -0.001(4) 0.002(3) -0.004(4) C16 0.051(4) 0.053(5) 0.060(5) -0.006(4) 0.015(4) 0.015(4) C22 0.030(4) 0.060(5) 0.043(4) -0.003(3) 0.012(3) 0.002(3) N33 0.061(4) 0.065(5) 0.070(5) 0.004(4) 0.025(3) -0.006(4) C14 0.049(4) 0.068(6) 0.051(5) 0.008(4) 0.012(4) 0.010(4) C1 0.047(4) 0.053(5) 0.047(4) -0.005(3) 0.010(3) -0.004(3) C12 0.044(4) 0.045(4) 0.051(4) -0.004(3) 0.016(3) -0.001(3) C24 0.054(5) 0.056(5) 0.083(6) -0.014(5) 0.032(4) -0.009(4) C25 0.053(5) 0.052(5) 0.064(5) 0.007(4) 0.019(4) 0.001(4) C15 0.065(5) 0.058(5) 0.066(5) 0.008(4) 0.020(4) 0.019(4) C21 0.045(4) 0.089(6) 0.035(4) -0.005(4) 0.008(3) 0.009(4) C5 0.076(6) 0.053(5) 0.099(7) 0.034(5) 0.042(5) 0.011(4) C35 0.080(7) 0.062(6) 0.082(6) 0.010(5) 0.017(5) 0.007(5) C4 0.046(5) 0.079(6) 0.081(6) 0.029(5) 0.020(4) 0.024(4) C6 0.059(5) 0.056(5) 0.073(6) 0.008(4) 0.023(4) -0.001(4) C34 0.101(8) 0.056(6) 0.094(7) 0.002(5) 0.039(6) -0.013(5) N31 0.039(3) 0.056(4) 0.041(3) -0.004(3) 0.004(3) 0.007(3) N1 0.045(3) 0.047(4) 0.043(3) 0.004(3) 0.009(3) -0.005(3) N13 0.047(4) 0.058(4) 0.051(4) 0.010(3) 0.010(3) 0.005(3) N21 0.033(3) 0.049(4) 0.041(3) 0.004(3) 0.008(2) -0.001(3) N11 0.035(3) 0.050(4) 0.053(4) -0.009(3) 0.008(3) 0.003(3) C2 0.049(4) 0.055(5) 0.033(4) -0.002(3) 0.015(3) -0.005(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 Cd1 N21 2.304(5) . ? Cd1 N1 2.342(5) . ? Cd1 I2 2.6846(7) . ? Cd1 I1 2.7112(7) . ? Cd2 N31 2.326(6) . ? Cd2 N11 2.385(5) . ? Cd2 I4 2.6839(8) . ? Cd2 I3 2.6897(8) . ? S1 C2 1.734(7) . ? S1 C1 1.798(6) . ? S11 C12 1.742(7) . ? S11 C1 1.791(6) . ? S21 C22 1.754(7) . ? S21 C21 1.801(6) . ? S31 C32 1.744(7) . ? S31 C21 1.806(7) . ? C32 N33 1.316(9) . ? C32 N31 1.354(8) 1_455 ? C36 C35 1.348(10) . ? C36 N31 1.349(8) . ? N3 C4 1.325(9) . ? N3 C2 1.337(8) . ? N23 C22 1.318(8) . ? N23 C24 1.335(9) . ? C26 N21 1.331(8) . ? C26 C25 1.359(9) . ? C16 N11 1.318(8) . ? C16 C15 1.378(9) . ? C22 N21 1.347(7) 1_455 ? N33 C34 1.349(10) . ? C14 N13 1.341(9) . ? C14 C15 1.364(10) . ? C12 N13 1.330(8) . ? C12 N11 1.339(8) . ? C24 C25 1.379(10) 1_455 ? C25 C24 1.379(10) 1_655 ? C5 C4 1.355(10) . ? C5 C6 1.383(10) . ? C35 C34 1.393(11) 1_655 ? C6 N1 1.338(8) . ? C34 C35 1.393(11) 1_455 ? N31 C32 1.354(8) 1_655 ? N1 C2 1.351(8) . ? N21 C22 1.347(7) 1_655 ? 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 N21 Cd1 N1 103.60(18) . . ? N21 Cd1 I2 115.85(13) . . ? N1 Cd1 I2 102.50(14) . . ? N21 Cd1 I1 102.09(13) . . ? N1 Cd1 I1 112.24(13) . . ? I2 Cd1 I1 119.73(2) . . ? N31 Cd2 N11 99.43(18) . . ? N31 Cd2 I4 119.89(14) . . ? N11 Cd2 I4 100.98(14) . . ? N31 Cd2 I3 105.60(14) . . ? N11 Cd2 I3 106.16(13) . . ? I4 Cd2 I3 121.36(3) . . ? C2 S1 C1 100.9(3) . . ? C12 S11 C1 101.1(3) . . ? C22 S21 C21 101.4(3) . . ? C32 S31 C21 100.1(4) . . ? N33 C32 N31 125.6(7) . 1_455 ? N33 C32 S31 120.1(6) . . ? N31 C32 S31 114.2(5) 1_455 . ? C35 C36 N31 122.8(7) . . ? C4 N3 C2 115.3(6) . . ? C22 N23 C24 115.7(6) . . ? N21 C26 C25 123.5(7) . . ? N11 C16 C15 122.7(7) . . ? N23 C22 N21 126.5(6) . 1_455 ? N23 C22 S21 119.5(5) . . ? N21 C22 S21 114.0(5) 1_455 . ? C32 N33 C34 117.0(7) . . ? N13 C14 C15 123.6(7) . . ? S11 C1 S1 115.3(4) . . ? N13 C12 N11 125.1(6) . . ? N13 C12 S11 119.0(5) . . ? N11 C12 S11 116.0(5) . . ? N23 C24 C25 122.9(7) . 1_455 ? C26 C25 C24 116.0(7) . 1_655 ? C14 C15 C16 115.7(7) . . ? S21 C21 S31 115.0(4) . . ? C4 C5 C6 116.6(7) . . ? C36 C35 C34 117.2(8) . 1_655 ? N3 C4 C5 124.6(7) . . ? N1 C6 C5 121.3(7) . . ? N33 C34 C35 121.4(8) . 1_455 ? C36 N31 C32 115.9(6) . 1_655 ? C36 N31 Cd2 117.5(5) . . ? C32 N31 Cd2 126.6(5) 1_655 . ? C6 N1 C2 116.8(6) . . ? C6 N1 Cd1 117.4(5) . . ? C2 N1 Cd1 125.2(4) . . ? C12 N13 C14 115.7(6) . . ? C26 N21 C22 115.2(6) . 1_655 ? C26 N21 Cd1 117.6(4) . . ? C22 N21 Cd1 127.1(4) 1_655 . ? C16 N11 C12 117.2(6) . . ? C16 N11 Cd2 118.0(4) . . ? C12 N11 Cd2 124.8(5) . . ? N3 C2 N1 125.3(6) . . ? N3 C2 S1 119.9(5) . . ? N1 C2 S1 114.8(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 S31 C32 N33 6.7(6) . . . . ? C21 S31 C32 N31 -171.9(5) . . . 1_455 ? C24 N23 C22 N21 1.5(10) . . . 1_455 ? C24 N23 C22 S21 -178.2(5) . . . . ? C21 S21 C22 N23 -2.9(6) . . . . ? C21 S21 C22 N21 177.4(5) . . . 1_455 ? N31 C32 N33 C34 -2.4(11) 1_455 . . . ? S31 C32 N33 C34 179.2(6) . . . . ? C12 S11 C1 S1 74.5(5) . . . . ? C2 S1 C1 S11 71.7(5) . . . . ? C1 S11 C12 N13 -4.3(6) . . . . ? C1 S11 C12 N11 175.1(5) . . . . ? C22 N23 C24 C25 -4.7(11) . . . 1_455 ? N21 C26 C25 C24 -1.5(11) . . . 1_655 ? N13 C14 C15 C16 0.9(12) . . . . ? N11 C16 C15 C14 -2.3(12) . . . . ? C22 S21 C21 S31 74.4(5) . . . . ? C32 S31 C21 S21 74.4(5) . . . . ? N31 C36 C35 C34 0.3(12) . . . 1_655 ? C2 N3 C4 C5 0.1(12) . . . . ? C6 C5 C4 N3 1.5(14) . . . . ? C4 C5 C6 N1 -0.1(12) . . . . ? C32 N33 C34 C35 1.1(12) . . . 1_455 ? C35 C36 N31 C32 -1.3(10) . . . 1_655 ? C35 C36 N31 Cd2 176.3(6) . . . . ? N11 Cd2 N31 C36 -129.1(5) . . . . ? I4 Cd2 N31 C36 122.4(4) . . . . ? I3 Cd2 N31 C36 -19.2(5) . . . . ? N11 Cd2 N31 C32 48.3(5) . . . 1_655 ? I4 Cd2 N31 C32 -60.3(5) . . . 1_655 ? I3 Cd2 N31 C32 158.1(5) . . . 1_655 ? C5 C6 N1 C2 -2.6(11) . . . . ? C5 C6 N1 Cd1 168.6(6) . . . . ? N21 Cd1 N1 C6 -128.7(5) . . . . ? I2 Cd1 N1 C6 -7.8(5) . . . . ? I1 Cd1 N1 C6 121.9(5) . . . . ? N21 Cd1 N1 C2 41.6(5) . . . . ? I2 Cd1 N1 C2 162.5(5) . . . . ? I1 Cd1 N1 C2 -67.7(5) . . . . ? N11 C12 N13 C14 -0.4(11) . . . . ? S11 C12 N13 C14 178.9(5) . . . . ? C15 C14 N13 C12 0.4(11) . . . . ? C25 C26 N21 C22 -1.4(10) . . . 1_655 ? C25 C26 N21 Cd1 -178.3(6) . . . . ? N1 Cd1 N21 C26 -132.5(5) . . . . ? I2 Cd1 N21 C26 116.1(5) . . . . ? I1 Cd1 N21 C26 -15.8(5) . . . . ? N1 Cd1 N21 C22 50.9(5) . . . 1_655 ? I2 Cd1 N21 C22 -60.5(5) . . . 1_655 ? I1 Cd1 N21 C22 167.7(5) . . . 1_655 ? C15 C16 N11 C12 2.2(11) . . . . ? C15 C16 N11 Cd2 -175.6(6) . . . . ? N13 C12 N11 C16 -0.9(11) . . . . ? S11 C12 N11 C16 179.8(5) . . . . ? N13 C12 N11 Cd2 176.9(5) . . . . ? S11 C12 N11 Cd2 -2.5(8) . . . . ? N31 Cd2 N11 C16 -132.2(5) . . . . ? I4 Cd2 N11 C16 -9.1(5) . . . . ? I3 Cd2 N11 C16 118.4(5) . . . . ? N31 Cd2 N11 C12 50.0(6) . . . . ? I4 Cd2 N11 C12 173.2(5) . . . . ? I3 Cd2 N11 C12 -59.4(6) . . . . ? C4 N3 C2 N1 -3.2(11) . . . . ? C4 N3 C2 S1 176.9(6) . . . . ? C6 N1 C2 N3 4.5(10) . . . . ? Cd1 N1 C2 N3 -165.9(5) . . . . ? C6 N1 C2 S1 -175.7(5) . . . . ? Cd1 N1 C2 S1 14.0(7) . . . . ? C1 S1 C2 N3 4.6(6) . . . . ? C1 S1 C2 N1 -175.2(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 C25 H25 I4 0.93 3.04 3.795(7) 139.8 4_656 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.360 _refine_diff_density_min -1.264 _refine_diff_density_rms 0.130 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 742454' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Cu2 N12 O12 S4' _chemical_formula_weight 847.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 25.859(5) _cell_length_b 8.1003(14) _cell_length_c 14.496(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.560(3) _cell_angle_gamma 90.00 _cell_volume 3002.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 1.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.703066 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9735 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.1310 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3605 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0268P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3605 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1127 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 0.807 _refine_ls_restrained_S_all 0.807 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C9 C 0.28633(16) 0.3294(5) 0.1587(3) 0.0452(11) Uani 1 1 d . . . H9 H 0.2708 0.3640 0.0999 0.054 Uiso 1 1 calc R . . O1 O 0.38893(10) 0.2272(3) -0.07152(16) 0.0434(7) Uani 1 1 d . . . Cu1 Cu 0.368340(18) 0.23846(6) 0.05445(3) 0.03781(16) Uani 1 1 d . . . S1 S 0.49330(4) 0.15730(12) 0.07411(6) 0.0359(3) Uani 1 1 d . . . S2 S 0.58018(4) 0.14449(13) 0.22958(6) 0.0395(3) Uani 1 1 d . . . N1 N 0.42757(12) 0.3986(4) 0.09367(19) 0.0315(7) Uani 1 1 d . . . N2 N 0.51785(12) 0.4701(4) 0.1182(2) 0.0375(8) Uani 1 1 d . . . C1 C 0.56334(13) 0.1561(5) 0.1037(2) 0.0339(9) Uani 1 1 d . . . H1A H 0.5779 0.2558 0.0808 0.041 Uiso 1 1 calc R . . H1B H 0.5778 0.0619 0.0750 0.041 Uiso 1 1 calc R . . C5 C 0.47898(16) 0.3630(4) 0.0982(2) 0.0325(9) Uani 1 1 d . . . C2 C 0.50436(18) 0.6240(5) 0.1367(2) 0.0437(11) Uani 1 1 d . . . H2 H 0.5307 0.7018 0.1522 0.052 Uiso 1 1 calc R . . C4 C 0.41531(17) 0.5545(5) 0.1116(2) 0.0398(10) Uani 1 1 d . . . H4 H 0.3804 0.5838 0.1090 0.048 Uiso 1 1 calc R . . C3 C 0.45352(19) 0.6724(5) 0.1340(3) 0.0462(11) Uani 1 1 d . . . H3 H 0.4450 0.7807 0.1467 0.055 Uiso 1 1 calc R . . O4 O 0.30666(12) 0.0734(4) 0.01036(19) 0.0629(9) Uani 1 1 d . . . O5 O 0.37616(11) -0.0399(3) 0.07791(19) 0.0538(8) Uani 1 1 d . . . N12 N 0.32953(15) -0.0572(5) 0.0427(2) 0.0444(9) Uani 1 1 d . . . O6 O 0.30781(13) -0.1898(4) 0.0396(2) 0.0768(11) Uani 1 1 d . . . N11 N 0.35792(15) 0.3383(5) -0.1167(2) 0.0504(9) Uani 1 1 d . . . O3 O 0.36042(13) 0.3642(4) -0.1981(2) 0.0744(10) Uani 1 1 d . . . O2 O 0.32858(12) 0.4117(4) -0.0701(2) 0.0646(9) Uani 1 1 d . . . N4 N 0.66886(12) 0.2255(4) 0.1699(2) 0.0400(8) Uani 1 1 d . . . N3 N 0.33553(11) 0.2691(4) 0.16905(19) 0.0334(7) Uani 1 1 d . . . C6 C 0.64433(14) 0.2208(4) 0.2439(2) 0.0312(9) Uani 1 1 d . . . C7 C 0.71738(16) 0.2873(5) 0.1824(3) 0.0485(12) Uani 1 1 d . . . H7 H 0.7354 0.2941 0.1315 0.058 Uiso 1 1 calc R . . C8 C 0.74155(16) 0.3414(5) 0.2684(3) 0.0500(11) Uani 1 1 d . . . H8 H 0.7753 0.3841 0.2764 0.060 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 C9 0.034(3) 0.058(3) 0.040(2) 0.000(2) -0.008(2) 0.006(2) O1 0.0440(17) 0.0528(18) 0.0329(14) 0.0016(13) 0.0041(13) 0.0077(15) Cu1 0.0344(3) 0.0486(3) 0.0293(2) -0.0013(2) 0.0008(2) -0.0004(3) S1 0.0294(6) 0.0403(6) 0.0362(5) -0.0091(5) -0.0014(5) 0.0020(5) S2 0.0315(6) 0.0610(7) 0.0252(5) -0.0013(5) 0.0021(4) -0.0106(5) N1 0.033(2) 0.034(2) 0.0264(16) 0.0021(14) 0.0007(15) 0.0038(16) N2 0.037(2) 0.039(2) 0.0354(18) -0.0043(15) 0.0032(16) -0.0035(17) C1 0.033(2) 0.045(2) 0.0229(18) -0.0085(17) 0.0008(17) 0.0063(19) C5 0.035(2) 0.038(2) 0.0232(19) 0.0053(17) -0.0013(18) 0.000(2) C2 0.058(3) 0.039(3) 0.034(2) 0.0007(19) 0.006(2) -0.005(2) C4 0.043(3) 0.039(3) 0.037(2) 0.0080(19) 0.005(2) 0.009(2) C3 0.064(3) 0.031(2) 0.043(2) -0.0003(19) 0.008(2) 0.005(2) O4 0.050(2) 0.084(2) 0.0511(19) -0.0039(17) -0.0048(16) 0.0249(18) O5 0.0399(19) 0.062(2) 0.056(2) -0.0042(15) -0.0037(16) -0.0003(16) N12 0.044(3) 0.058(3) 0.033(2) -0.0102(18) 0.0126(19) -0.003(2) O6 0.085(3) 0.076(3) 0.077(2) -0.0220(19) 0.036(2) -0.042(2) N11 0.049(3) 0.063(3) 0.039(2) -0.004(2) 0.004(2) -0.004(2) O3 0.078(2) 0.112(3) 0.0319(17) 0.0159(18) 0.0029(17) 0.002(2) O2 0.062(2) 0.072(2) 0.059(2) 0.0021(17) 0.0071(18) 0.0252(18) N4 0.033(2) 0.057(2) 0.0316(17) -0.0010(16) 0.0075(16) 0.0022(17) N3 0.0245(18) 0.043(2) 0.0302(16) -0.0031(15) -0.0038(14) 0.0014(16) C6 0.026(2) 0.035(2) 0.031(2) 0.0020(17) 0.0022(17) 0.0009(18) C7 0.035(3) 0.067(3) 0.046(3) 0.009(2) 0.015(2) 0.003(2) C8 0.025(2) 0.062(3) 0.062(3) 0.008(2) 0.003(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 N3 1.350(4) . ? C9 C8 1.369(5) 2_655 ? O1 N11 1.313(4) . ? O1 Cu1 1.979(2) . ? Cu1 N3 1.990(3) . ? Cu1 N1 2.023(3) . ? Cu1 O4 2.106(3) . ? Cu1 O5 2.285(3) . ? Cu1 O2 2.394(3) . ? S1 C5 1.753(4) . ? S1 C1 1.798(4) . ? S2 C6 1.753(4) . ? S2 C1 1.814(3) . ? N1 C4 1.337(4) . ? N1 C5 1.352(4) . ? N2 C5 1.326(4) . ? N2 C2 1.333(4) . ? C2 C3 1.367(5) . ? C4 C3 1.378(5) . ? O4 N12 1.267(4) . ? O5 N12 1.245(4) . ? N12 O6 1.210(4) . ? N11 O3 1.210(4) . ? N11 O2 1.240(4) . ? N4 C6 1.326(4) . ? N4 C7 1.338(5) . ? N3 C6 1.349(4) 2_655 ? C6 N3 1.349(4) 2_655 ? C7 C8 1.380(5) . ? C8 C9 1.369(5) 2_655 ? 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 N3 C9 C8 122.4(4) . 2_655 ? N11 O1 Cu1 101.5(2) . . ? O1 Cu1 N3 169.34(11) . . ? O1 Cu1 N1 89.56(11) . . ? N3 Cu1 N1 94.85(12) . . ? O1 Cu1 O4 89.22(11) . . ? N3 Cu1 O4 86.26(11) . . ? N1 Cu1 O4 178.67(11) . . ? O1 Cu1 O5 93.55(10) . . ? N3 Cu1 O5 92.18(11) . . ? N1 Cu1 O5 122.99(11) . . ? O4 Cu1 O5 57.65(11) . . ? O1 Cu1 O2 58.36(10) . . ? N3 Cu1 O2 111.59(11) . . ? N1 Cu1 O2 93.34(11) . . ? O4 Cu1 O2 85.56(12) . . ? O5 Cu1 O2 135.17(10) . . ? C5 S1 C1 101.11(18) . . ? C6 S2 C1 100.50(17) . . ? C4 N1 C5 116.9(3) . . ? C4 N1 Cu1 117.9(3) . . ? C5 N1 Cu1 125.1(2) . . ? C5 N2 C2 116.3(4) . . ? S1 C1 S2 108.84(19) . . ? N2 C5 N1 125.4(3) . . ? N2 C5 S1 119.3(3) . . ? N1 C5 S1 115.3(3) . . ? N2 C2 C3 122.8(4) . . ? N1 C4 C3 121.2(4) . . ? C2 C3 C4 117.5(4) . . ? N12 O4 Cu1 97.3(2) . . ? N12 O5 Cu1 89.5(2) . . ? O6 N12 O5 122.1(4) . . ? O6 N12 O4 122.6(4) . . ? O5 N12 O4 115.3(4) . . ? O3 N11 O2 125.0(4) . . ? O3 N11 O1 119.2(4) . . ? O2 N11 O1 115.8(3) . . ? N11 O2 Cu1 84.3(2) . . ? C6 N4 C7 116.9(3) . . ? C6 N3 C9 115.8(3) 2_655 . ? C6 N3 Cu1 126.3(2) 2_655 . ? C9 N3 Cu1 117.6(2) . . ? N4 C6 N3 125.7(3) . 2_655 ? N4 C6 S2 118.2(3) . . ? N3 C6 S2 116.1(3) 2_655 . ? N4 C7 C8 122.1(4) . . ? C9 C8 C7 117.1(4) 2_655 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.561 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.097 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 742455' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H24 Br4 Cu2 N12 S6' _chemical_formula_weight 1155.66 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9410(8) _cell_length_b 12.1361(15) _cell_length_c 12.3184(15) _cell_angle_alpha 75.178(2) _cell_angle_beta 76.019(2) _cell_angle_gamma 76.433(2) _cell_volume 956.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 5.656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2363 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5781 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.1034 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.01 _reflns_number_total 4014 _reflns_number_gt 2393 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0375P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4014 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.17630(10) 0.35336(6) 0.31594(5) 0.03195(18) Uani 1 1 d . . . Br1 Br -0.13119(9) 0.29526(5) 0.42838(5) 0.04555(18) Uani 1 1 d . . . Br2 Br 0.33656(10) 0.51723(5) 0.22346(5) 0.04847(19) Uani 1 1 d . . . S1 S 0.4944(2) 0.23046(15) 0.13492(13) 0.0478(4) Uani 1 1 d . . . C1 C 0.6381(8) 0.1581(5) 0.0211(4) 0.0383(14) Uani 1 1 d . . . H1A H 0.5645 0.1808 -0.0412 0.046 Uiso 1 1 calc R . . H1B H 0.7654 0.1853 -0.0074 0.046 Uiso 1 1 calc R . . N1 N 0.1184(6) 0.3367(3) 0.1702(3) 0.0275(10) Uani 1 1 d . . . C2 C 0.2627(8) 0.2892(5) 0.0906(5) 0.0348(13) Uani 1 1 d . . . N3 N 0.2391(7) 0.2847(4) -0.0120(4) 0.0400(12) Uani 1 1 d . . . C4 C 0.0550(9) 0.3300(5) -0.0368(5) 0.0382(14) Uani 1 1 d . . . H4 H 0.0330 0.3273 -0.1075 0.046 Uiso 1 1 calc R . . C5 C -0.1018(8) 0.3800(5) 0.0370(5) 0.0363(14) Uani 1 1 d . . . H5 H -0.2275 0.4120 0.0173 0.044 Uiso 1 1 calc R . . C6 C -0.0647(8) 0.3807(5) 0.1413(5) 0.0367(14) Uani 1 1 d . . . H6 H -0.1692 0.4125 0.1940 0.044 Uiso 1 1 calc R . . S11 S 0.6905(2) 0.00338(14) 0.05997(14) 0.0468(4) Uani 1 1 d . . . N11 N 0.9398(7) -0.1297(4) 0.1868(4) 0.0397(12) Uani 1 1 d . . . C12 C 0.8588(8) -0.0194(5) 0.1533(4) 0.0335(13) Uani 1 1 d . . . N13 N 0.8897(7) 0.0722(4) 0.1829(4) 0.0434(13) Uani 1 1 d . . . C14 C 1.0198(10) 0.0480(6) 0.2544(5) 0.0541(18) Uani 1 1 d . . . H14 H 1.0487 0.1086 0.2775 0.065 Uiso 1 1 calc R . . C15 C 1.1117(9) -0.0639(6) 0.2944(5) 0.0505(17) Uani 1 1 d . . . H15 H 1.2016 -0.0803 0.3440 0.061 Uiso 1 1 calc R . . C16 C 1.0644(9) -0.1503(5) 0.2577(5) 0.0463(16) Uani 1 1 d . . . H16 H 1.1231 -0.2267 0.2842 0.056 Uiso 1 1 calc R . . S21 S 0.3756(3) 0.10606(14) 0.43452(14) 0.0570(5) Uani 1 1 d . . . C21 C 0.4034(17) -0.0225(9) 0.5504(9) 0.042(3) Uani 0.50 1 d P . . H21A H 0.3468 0.0037 0.6216 0.050 Uiso 0.50 1 calc PR . . H21B H 0.3170 -0.0721 0.5445 0.050 Uiso 0.50 1 calc PR . . N21 N 0.2906(7) 0.3224(4) 0.4575(4) 0.0360(11) Uani 1 1 d . . . C22 C 0.3653(8) 0.2140(5) 0.5082(5) 0.0349(13) Uani 1 1 d . . . N23 N 0.4292(7) 0.1844(4) 0.6066(4) 0.0390(12) Uani 1 1 d . . . C24 C 0.4139(9) 0.2711(6) 0.6585(5) 0.0460(16) Uani 1 1 d . . . H24 H 0.4546 0.2534 0.7286 0.055 Uiso 1 1 calc R . . C25 C 0.3416(9) 0.3845(5) 0.6140(5) 0.0450(16) Uani 1 1 d . . . H25 H 0.3341 0.4433 0.6515 0.054 Uiso 1 1 calc R . . C26 C 0.2807(9) 0.4073(5) 0.5116(5) 0.0446(15) Uani 1 1 d . . . H26 H 0.2313 0.4835 0.4785 0.054 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 0.0325(4) 0.0328(4) 0.0305(4) -0.0038(3) -0.0102(3) -0.0047(3) Br1 0.0373(4) 0.0519(4) 0.0409(4) -0.0032(3) -0.0007(3) -0.0097(3) Br2 0.0597(5) 0.0440(4) 0.0471(4) 0.0029(3) -0.0222(3) -0.0214(3) S1 0.0325(9) 0.0733(12) 0.0388(9) -0.0226(8) -0.0108(7) 0.0043(8) C1 0.031(3) 0.044(4) 0.036(3) -0.009(3) -0.004(3) 0.000(3) N1 0.029(3) 0.028(2) 0.025(2) -0.0028(19) -0.007(2) -0.0065(19) C2 0.035(3) 0.033(3) 0.036(3) -0.003(3) -0.011(3) -0.005(3) N3 0.041(3) 0.047(3) 0.035(3) -0.009(2) -0.016(2) -0.006(2) C4 0.048(4) 0.045(4) 0.030(3) -0.007(3) -0.016(3) -0.017(3) C5 0.030(3) 0.040(3) 0.043(4) -0.002(3) -0.018(3) -0.010(3) C6 0.026(3) 0.039(3) 0.039(3) -0.002(3) -0.002(3) -0.005(3) S11 0.0430(10) 0.0486(10) 0.0557(10) -0.0136(8) -0.0198(8) -0.0084(7) N11 0.038(3) 0.036(3) 0.045(3) -0.006(2) -0.010(2) -0.008(2) C12 0.021(3) 0.048(4) 0.032(3) -0.014(3) -0.002(2) -0.004(3) N13 0.039(3) 0.043(3) 0.051(3) -0.014(3) -0.020(3) 0.001(2) C14 0.066(5) 0.051(4) 0.060(4) -0.014(3) -0.031(4) -0.015(3) C15 0.048(4) 0.054(4) 0.052(4) -0.009(3) -0.025(3) -0.002(3) C16 0.046(4) 0.032(4) 0.053(4) -0.003(3) -0.009(3) 0.001(3) S21 0.0930(15) 0.0359(9) 0.0458(10) -0.0067(8) -0.0276(10) -0.0065(9) C21 0.050(8) 0.028(6) 0.045(7) -0.008(6) 0.004(6) -0.013(6) N21 0.041(3) 0.037(3) 0.033(3) -0.004(2) -0.015(2) -0.009(2) C22 0.034(3) 0.034(3) 0.033(3) -0.001(3) -0.010(3) -0.004(3) N23 0.035(3) 0.039(3) 0.036(3) 0.002(2) -0.010(2) -0.002(2) C24 0.043(4) 0.059(4) 0.039(4) -0.010(3) -0.017(3) -0.006(3) C25 0.051(4) 0.047(4) 0.044(4) -0.017(3) -0.014(3) -0.009(3) C26 0.053(4) 0.034(3) 0.049(4) -0.010(3) -0.018(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.999(4) . ? Cu N21 2.002(4) . ? Cu Br1 2.3977(10) . ? Cu Br2 2.3993(10) . ? Cu S21 3.1370(17) . ? Cu S1 3.1385(16) . ? S1 C2 1.755(5) . ? S1 C1 1.810(5) . ? C1 S11 1.786(5) . ? N1 C6 1.353(6) . ? N1 C2 1.357(6) . ? C2 N3 1.329(6) . ? N3 C4 1.342(7) . ? C4 C5 1.369(7) . ? C5 C6 1.373(7) . ? S11 C12 1.761(5) . ? N11 C16 1.314(7) . ? N11 C12 1.325(6) . ? C12 N13 1.330(6) . ? N13 C14 1.343(7) . ? C14 C15 1.378(8) . ? C15 C16 1.373(8) . ? S21 C21 1.651(11) 2_656 ? S21 C22 1.754(5) . ? S21 C21 1.833(11) . ? C21 S21 1.651(11) 2_656 ? N21 C26 1.343(6) . ? N21 C22 1.344(6) . ? C22 N23 1.326(6) . ? N23 C24 1.337(7) . ? C24 C25 1.368(8) . ? C25 C26 1.368(7) . ? 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 Cu N21 162.07(17) . . ? N1 Cu Br1 93.30(13) . . ? N21 Cu Br1 90.44(14) . . ? N1 Cu Br2 93.22(12) . . ? N21 Cu Br2 93.97(14) . . ? Br1 Cu Br2 144.17(4) . . ? N1 Cu S21 106.62(12) . . ? N21 Cu S21 56.39(13) . . ? Br1 Cu S21 83.56(5) . . ? Br2 Cu S21 127.69(5) . . ? N1 Cu S1 55.97(12) . . ? N21 Cu S1 108.54(13) . . ? Br1 Cu S1 127.73(4) . . ? Br2 Cu S1 84.18(4) . . ? S21 Cu S1 69.65(5) . . ? C2 S1 C1 102.5(3) . . ? C2 S1 Cu 67.72(18) . . ? C1 S1 Cu 169.53(19) . . ? S11 C1 S1 115.4(3) . . ? C6 N1 C2 115.9(4) . . ? C6 N1 Cu 121.4(4) . . ? C2 N1 Cu 122.5(3) . . ? N3 C2 N1 125.6(5) . . ? N3 C2 S1 120.9(4) . . ? N1 C2 S1 113.5(4) . . ? C2 N3 C4 116.3(5) . . ? N3 C4 C5 123.2(5) . . ? C4 C5 C6 116.8(5) . . ? N1 C6 C5 122.3(5) . . ? C12 S11 C1 101.1(3) . . ? C16 N11 C12 115.8(5) . . ? N11 C12 N13 127.6(5) . . ? N11 C12 S11 113.9(4) . . ? N13 C12 S11 118.5(4) . . ? C12 N13 C14 115.1(5) . . ? N13 C14 C15 121.8(5) . . ? C16 C15 C14 116.9(5) . . ? N11 C16 C15 122.9(5) . . ? C21 S21 C22 102.4(4) 2_656 . ? C21 S21 C21 57.4(6) 2_656 . ? C22 S21 C21 99.7(4) . . ? C21 S21 Cu 142.5(4) 2_656 . ? C22 S21 Cu 66.90(18) . . ? C21 S21 Cu 156.1(3) . . ? S21 C21 S21 122.6(6) 2_656 . ? C26 N21 C22 116.9(5) . . ? C26 N21 Cu 121.7(4) . . ? C22 N21 Cu 121.2(4) . . ? N23 C22 N21 125.4(5) . . ? N23 C22 S21 119.3(4) . . ? N21 C22 S21 115.3(4) . . ? C22 N23 C24 115.9(5) . . ? N23 C24 C25 123.4(5) . . ? C24 C25 C26 116.7(5) . . ? N21 C26 C25 121.7(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 N1 Cu S1 C2 2.8(2) . . . . ? N21 Cu S1 C2 172.7(2) . . . . ? Br1 Cu S1 C2 67.1(2) . . . . ? Br2 Cu S1 C2 -95.0(2) . . . . ? S21 Cu S1 C2 131.1(2) . . . . ? N1 Cu S1 C1 -18.3(11) . . . . ? N21 Cu S1 C1 151.5(11) . . . . ? Br1 Cu S1 C1 45.9(11) . . . . ? Br2 Cu S1 C1 -116.2(11) . . . . ? S21 Cu S1 C1 109.9(11) . . . . ? C2 S1 C1 S11 -111.4(3) . . . . ? Cu S1 C1 S11 -91.4(11) . . . . ? N21 Cu N1 C6 148.4(6) . . . . ? Br1 Cu N1 C6 46.7(4) . . . . ? Br2 Cu N1 C6 -98.1(4) . . . . ? S21 Cu N1 C6 130.9(4) . . . . ? S1 Cu N1 C6 -178.8(5) . . . . ? N21 Cu N1 C2 -36.8(8) . . . . ? Br1 Cu N1 C2 -138.5(4) . . . . ? Br2 Cu N1 C2 76.7(4) . . . . ? S21 Cu N1 C2 -54.3(4) . . . . ? S1 Cu N1 C2 -4.0(3) . . . . ? C6 N1 C2 N3 1.3(8) . . . . ? Cu N1 C2 N3 -173.8(4) . . . . ? C6 N1 C2 S1 -178.4(4) . . . . ? Cu N1 C2 S1 6.5(6) . . . . ? C1 S1 C2 N3 -7.3(5) . . . . ? Cu S1 C2 N3 176.5(5) . . . . ? C1 S1 C2 N1 172.4(4) . . . . ? Cu S1 C2 N1 -3.8(3) . . . . ? N1 C2 N3 C4 -0.9(8) . . . . ? S1 C2 N3 C4 178.7(4) . . . . ? C2 N3 C4 C5 0.8(8) . . . . ? N3 C4 C5 C6 -1.1(8) . . . . ? C2 N1 C6 C5 -1.5(8) . . . . ? Cu N1 C6 C5 173.6(4) . . . . ? C4 C5 C6 N1 1.4(8) . . . . ? S1 C1 S11 C12 -68.2(4) . . . . ? C16 N11 C12 N13 0.2(9) . . . . ? C16 N11 C12 S11 -179.2(4) . . . . ? C1 S11 C12 N11 -173.4(4) . . . . ? C1 S11 C12 N13 7.1(5) . . . . ? N11 C12 N13 C14 0.6(9) . . . . ? S11 C12 N13 C14 179.9(5) . . . . ? C12 N13 C14 C15 -0.7(9) . . . . ? N13 C14 C15 C16 0.1(10) . . . . ? C12 N11 C16 C15 -0.9(9) . . . . ? C14 C15 C16 N11 0.8(10) . . . . ? N1 Cu S21 C21 95.9(7) . . . 2_656 ? N21 Cu S21 C21 -77.7(7) . . . 2_656 ? Br1 Cu S21 C21 -172.5(7) . . . 2_656 ? Br2 Cu S21 C21 -11.8(7) . . . 2_656 ? S1 Cu S21 C21 53.1(6) . . . 2_656 ? N1 Cu S21 C22 176.0(2) . . . . ? N21 Cu S21 C22 2.4(3) . . . . ? Br1 Cu S21 C22 -92.5(2) . . . . ? Br2 Cu S21 C22 68.3(2) . . . . ? S1 Cu S21 C22 133.2(2) . . . . ? N1 Cu S21 C21 -124.7(9) . . . . ? N21 Cu S21 C21 61.7(9) . . . . ? Br1 Cu S21 C21 -33.1(9) . . . . ? Br2 Cu S21 C21 127.6(9) . . . . ? S1 Cu S21 C21 -167.5(9) . . . . ? C21 S21 C21 S21 0.0 2_656 . . 2_656 ? C22 S21 C21 S21 -98.6(7) . . . 2_656 ? Cu S21 C21 S21 -152.0(4) . . . 2_656 ? N1 Cu N21 C26 162.2(5) . . . . ? Br1 Cu N21 C26 -95.7(5) . . . . ? Br2 Cu N21 C26 48.7(5) . . . . ? S21 Cu N21 C26 -177.6(5) . . . . ? S1 Cu N21 C26 133.9(4) . . . . ? N1 Cu N21 C22 -23.5(9) . . . . ? Br1 Cu N21 C22 78.6(4) . . . . ? Br2 Cu N21 C22 -137.0(4) . . . . ? S21 Cu N21 C22 -3.3(4) . . . . ? S1 Cu N21 C22 -51.8(5) . . . . ? C26 N21 C22 N23 0.2(9) . . . . ? Cu N21 C22 N23 -174.4(4) . . . . ? C26 N21 C22 S21 -179.9(4) . . . . ? Cu N21 C22 S21 5.5(6) . . . . ? C21 S21 C22 N23 -41.2(6) 2_656 . . . ? C21 S21 C22 N23 17.4(6) . . . . ? Cu S21 C22 N23 176.7(5) . . . . ? C21 S21 C22 N21 138.9(5) 2_656 . . . ? C21 S21 C22 N21 -162.6(6) . . . . ? Cu S21 C22 N21 -3.3(4) . . . . ? N21 C22 N23 C24 0.9(9) . . . . ? S21 C22 N23 C24 -179.0(5) . . . . ? C22 N23 C24 C25 -1.3(9) . . . . ? N23 C24 C25 C26 0.8(10) . . . . ? C22 N21 C26 C25 -0.8(9) . . . . ? Cu N21 C26 C25 173.8(4) . . . . ? C24 C25 C26 N21 0.3(9) . . . . ? 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 C1 H1A N3 0.97 2.31 2.902(7) 118.9 . C6 H6 Br1 0.93 2.92 3.370(6) 111.2 . C21 H21A N23 0.97 2.35 2.823(12) 109.6 . _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.743 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.113 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 742456' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cu N4 O4 S2' _chemical_formula_weight 417.94 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0986(12) _cell_length_b 7.6458(11) _cell_length_c 27.468(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.606(3) _cell_angle_gamma 90.00 _cell_volume 1700.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max .16 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 1.555 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.798226 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9195 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.2539 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.12 _reflns_number_total 3873 _reflns_number_gt 1486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0067P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3873 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1866 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 0.739 _refine_ls_restrained_S_all 0.739 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.07525(8) -0.08880(9) 0.03402(2) 0.03133(19) Uani 1 1 d . . . S1 S 0.30371(19) -0.01206(19) 0.14265(5) 0.0441(4) Uani 1 1 d . . . S2 S 0.3348(2) -0.0790(2) 0.25189(5) 0.0577(5) Uani 1 1 d . . . O1 O -0.0238(4) 0.0764(5) 0.07888(12) 0.0451(10) Uani 1 1 d . . . O2 O 0.1489(4) -0.2328(5) -0.02046(13) 0.0453(11) Uani 1 1 d . . . O5 O 0.2578(4) 0.0681(5) 0.02090(12) 0.0432(10) Uani 1 1 d . . . O6 O -0.1305(4) -0.2215(5) 0.03746(13) 0.0450(11) Uani 1 1 d . . . N1 N 0.2021(5) -0.2650(6) 0.08714(14) 0.0327(12) Uani 1 1 d . . . N2 N 0.3726(6) -0.3502(6) 0.15412(16) 0.0460(14) Uani 1 1 d . . . N3 N 0.1947(7) 0.1220(8) 0.31377(18) 0.0654(17) Uani 1 1 d . . . N4 N 0.2382(6) 0.2487(7) 0.23656(17) 0.0478(14) Uani 1 1 d . . . C1 C 0.4320(6) -0.0220(7) 0.19594(17) 0.0450(16) Uani 1 1 d . . . H1A H 0.4842 0.0913 0.2002 0.054 Uiso 1 1 calc R . . H1B H 0.5191 -0.1062 0.1901 0.054 Uiso 1 1 calc R . . C2 C 0.3598(7) -0.5133(8) 0.1396(2) 0.0525(18) Uani 1 1 d . . . H2 H 0.4160 -0.5987 0.1573 0.063 Uiso 1 1 calc R . . C3 C 0.2680(7) -0.5648(8) 0.09981(19) 0.0502(17) Uani 1 1 d . . . H3 H 0.2587 -0.6817 0.0908 0.060 Uiso 1 1 calc R . . C4 C 0.1916(7) -0.4353(8) 0.07429(17) 0.0427(15) Uani 1 1 d . . . H4 H 0.1295 -0.4650 0.0468 0.051 Uiso 1 1 calc R . . C5 C 0.2922(6) -0.2346(7) 0.12600(19) 0.0312(14) Uani 1 1 d . . . C6 C 0.2455(6) 0.1204(8) 0.2686(2) 0.0451(16) Uani 1 1 d . . . C7 C 0.1692(7) 0.3934(9) 0.2529(2) 0.0633(19) Uani 1 1 d . . . H7 H 0.1588 0.4870 0.2315 0.076 Uiso 1 1 calc R . . C8 C 0.1120(7) 0.4153(10) 0.2991(3) 0.068(2) Uani 1 1 d . . . H8 H 0.0658 0.5196 0.3099 0.082 Uiso 1 1 calc R . . C9 C 0.1283(8) 0.2710(12) 0.3283(3) 0.076(2) Uani 1 1 d . . . H9 H 0.0905 0.2781 0.3601 0.091 Uiso 1 1 calc R . . C30 C -0.2008(7) 0.3052(8) 0.10208(19) 0.078(2) Uani 1 1 d . . . H30A H -0.1661 0.2668 0.1339 0.117 Uiso 1 1 calc R . . H30B H -0.3182 0.2916 0.0988 0.117 Uiso 1 1 calc R . . H30C H -0.1721 0.4261 0.0979 0.117 Uiso 1 1 calc R . . C31 C -0.1162(7) 0.1975(8) 0.0641(2) 0.0378(15) Uani 1 1 d . . . C34 C 0.2534(7) 0.1820(7) -0.0120(2) 0.0380(15) Uani 1 1 d . . . C35 C 0.4132(7) 0.2756(7) -0.0227(2) 0.069(2) Uani 1 1 d . . . H35A H 0.4980 0.2345 -0.0008 0.103 Uiso 1 1 calc R . . H35B H 0.3984 0.3991 -0.0183 0.103 Uiso 1 1 calc R . . H35C H 0.4448 0.2525 -0.0556 0.103 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 0.0352(4) 0.0286(4) 0.0302(4) 0.0012(4) -0.0026(3) 0.0010(4) S1 0.0605(11) 0.0297(9) 0.0417(10) -0.0024(7) -0.0168(8) 0.0034(8) S2 0.0814(13) 0.0476(11) 0.0438(10) 0.0087(10) -0.0117(9) 0.0023(11) O1 0.054(3) 0.050(3) 0.031(2) -0.003(2) -0.0047(19) 0.014(2) O2 0.070(3) 0.036(3) 0.030(2) -0.006(2) -0.003(2) 0.017(2) O5 0.037(2) 0.044(3) 0.049(3) 0.008(2) -0.0015(19) -0.004(2) O6 0.041(3) 0.047(3) 0.046(3) 0.014(2) -0.008(2) -0.008(2) N1 0.044(3) 0.026(3) 0.028(3) -0.006(2) -0.005(2) 0.002(2) N2 0.072(4) 0.030(3) 0.035(3) -0.004(3) -0.011(3) 0.013(3) N3 0.084(4) 0.074(5) 0.038(4) -0.004(3) 0.012(3) -0.011(4) N4 0.059(4) 0.040(4) 0.044(3) -0.003(3) -0.002(3) 0.006(3) C1 0.044(4) 0.040(4) 0.051(4) -0.005(3) -0.009(3) 0.005(3) C2 0.073(5) 0.034(4) 0.051(5) 0.014(3) -0.006(4) 0.012(4) C3 0.093(5) 0.021(4) 0.036(4) 0.002(3) -0.014(3) 0.005(4) C4 0.057(4) 0.046(4) 0.025(3) -0.001(3) -0.003(3) -0.005(4) C5 0.035(4) 0.028(4) 0.031(3) 0.004(3) 0.002(3) 0.008(3) C6 0.041(4) 0.057(5) 0.037(4) -0.004(4) -0.009(3) -0.002(3) C7 0.068(5) 0.055(5) 0.066(5) -0.009(4) -0.002(4) 0.008(4) C8 0.049(4) 0.076(6) 0.079(6) -0.032(5) 0.014(4) 0.006(4) C9 0.067(6) 0.104(7) 0.056(5) -0.011(5) 0.026(4) -0.022(5) C30 0.112(6) 0.081(6) 0.042(4) -0.008(4) 0.013(4) 0.054(5) C31 0.034(4) 0.038(4) 0.042(4) 0.002(3) 0.009(3) -0.007(3) C34 0.041(4) 0.027(4) 0.045(4) -0.009(3) 0.003(3) -0.007(3) C35 0.058(5) 0.068(5) 0.080(5) 0.009(4) 0.008(4) -0.031(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.940(4) . ? Cu1 O1 1.944(4) . ? Cu1 O6 1.954(4) . ? Cu1 O2 1.956(3) . ? Cu1 N1 2.228(4) . ? Cu1 Cu1 2.6028(13) 3 ? S1 C5 1.764(5) . ? S1 C1 1.788(5) . ? S2 C6 1.750(6) . ? S2 C1 1.788(5) . ? O1 C31 1.255(6) . ? O2 C31 1.254(6) 3 ? O5 C34 1.256(6) . ? O6 C34 1.247(6) 3 ? N1 C5 1.307(6) . ? N1 C4 1.352(6) . ? N2 C2 1.313(6) . ? N2 C5 1.338(6) . ? N3 C6 1.312(6) . ? N3 C9 1.323(8) . ? N4 C6 1.319(6) . ? N4 C7 1.321(7) . ? C2 C3 1.374(7) . ? C3 C4 1.359(7) . ? C7 C8 1.365(7) . ? C8 C9 1.370(9) . ? C30 C31 1.500(7) . ? C31 O2 1.254(6) 3 ? C34 O6 1.247(6) 3 ? C34 C35 1.510(7) . ? 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 O5 Cu1 O1 92.09(16) . . ? O5 Cu1 O6 169.01(15) . . ? O1 Cu1 O6 87.07(15) . . ? O5 Cu1 O2 88.09(15) . . ? O1 Cu1 O2 169.10(14) . . ? O6 Cu1 O2 90.68(16) . . ? O5 Cu1 N1 98.54(16) . . ? O1 Cu1 N1 99.68(15) . . ? O6 Cu1 N1 92.40(16) . . ? O2 Cu1 N1 91.06(15) . . ? O5 Cu1 Cu1 84.04(11) . 3 ? O1 Cu1 Cu1 85.58(11) . 3 ? O6 Cu1 Cu1 84.97(11) . 3 ? O2 Cu1 Cu1 83.61(11) . 3 ? N1 Cu1 Cu1 174.02(12) . 3 ? C5 S1 C1 101.5(2) . . ? C6 S2 C1 101.5(3) . . ? C31 O1 Cu1 121.5(4) . . ? C31 O2 Cu1 123.1(4) 3 . ? C34 O5 Cu1 123.1(4) . . ? C34 O6 Cu1 121.5(4) 3 . ? C5 N1 C4 114.6(4) . . ? C5 N1 Cu1 132.6(4) . . ? C4 N1 Cu1 112.6(3) . . ? C2 N2 C5 114.6(5) . . ? C6 N3 C9 115.2(6) . . ? C6 N4 C7 114.3(5) . . ? S1 C1 S2 117.2(3) . . ? N2 C2 C3 123.6(6) . . ? C4 C3 C2 116.2(6) . . ? N1 C4 C3 122.7(5) . . ? N1 C5 N2 128.2(5) . . ? N1 C5 S1 114.2(4) . . ? N2 C5 S1 117.6(4) . . ? N3 C6 N4 127.7(6) . . ? N3 C6 S2 113.0(5) . . ? N4 C6 S2 119.3(5) . . ? N4 C7 C8 124.6(7) . . ? C7 C8 C9 114.4(7) . . ? N3 C9 C8 123.7(7) . . ? O2 C31 O1 126.0(5) 3 . ? O2 C31 C30 116.9(5) 3 . ? O1 C31 C30 117.0(5) . . ? O6 C34 O5 126.0(6) 3 . ? O6 C34 C35 117.2(6) 3 . ? O5 C34 C35 116.7(6) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.411 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.086 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 742457' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Br Cu N4 S2' _chemical_formula_weight 379.76 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 7.4615(8) _cell_length_b 19.921(2) _cell_length_c 8.8263(9) _cell_angle_alpha 90.00 _cell_angle_beta 111.281(2) _cell_angle_gamma 90.00 _cell_volume 1222.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max .37 _exptl_crystal_size_mid .21 _exptl_crystal_size_min .19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 5.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635693 _exptl_absorpt_correction_T_max 1.000000 _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 7275 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.02 _reflns_number_total 2800 _reflns_number_gt 1854 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELX97' _computing_publication_material 'Bruker SHELX97' _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 w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2800 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.13333(6) 0.531829(19) 0.34906(5) 0.04304(13) Uani 1 d . . . Cu Cu 0.05341(7) 0.56823(3) 0.58332(7) 0.04764(16) Uani 1 d . . . S1 S 0.06942(14) 0.63195(5) 0.91543(13) 0.0443(3) Uani 1 d . . . S11 S 0.12945(15) 0.77104(5) 1.06886(16) 0.0530(3) Uani 1 d . . . N3 N 0.4507(5) 0.61249(15) 1.0581(4) 0.0411(8) Uani 1 d . . . N1 N 0.2960(4) 0.57654(14) 0.7836(4) 0.0348(7) Uani 1 d . . . N11 N -0.1487(4) 0.85781(14) 1.0171(4) 0.0373(7) Uani 1 d . . . N13 N -0.2386(6) 0.74366(16) 1.0041(6) 0.0727(14) Uani 1 d . . . C1 C 0.1288(6) 0.68182(19) 1.0968(5) 0.0471(10) Uani 1 d . . . H1A H 0.0378 0.6714 1.1487 0.056 Uiso 1 calc R . . H1B H 0.2553 0.6685 1.1709 0.056 Uiso 1 calc R . . C2 C 0.2965(5) 0.60505(17) 0.9233(5) 0.0350(9) Uani 1 d . . . C4 C 0.6167(6) 0.5888(2) 1.0537(6) 0.0463(11) Uani 1 d . . . H4 H 0.7273 0.5936 1.1459 0.056 Uiso 1 calc R . . C5 C 0.6317(6) 0.55800(19) 0.9207(6) 0.0447(10) Uani 1 d . . . H5 H 0.7479 0.5411 0.9208 0.054 Uiso 1 calc R . . C6 C 0.4640(5) 0.55347(18) 0.7859(5) 0.0394(9) Uani 1 d . . . H6 H 0.4690 0.5333 0.6925 0.047 Uiso 1 calc R . . C12 C -0.1118(5) 0.79138(18) 1.0246(5) 0.0385(9) Uani 1 d . . . C14 C -0.4182(7) 0.7638(2) 0.9768(9) 0.095(2) Uani 1 d . . . H14 H -0.5121 0.7310 0.9610 0.114 Uiso 1 calc R . . C15 C -0.4722(6) 0.8286(2) 0.9707(6) 0.0589(13) Uani 1 d . . . H15 H -0.5976 0.8412 0.9554 0.071 Uiso 1 calc R . . C16 C -0.3310(6) 0.8745(2) 0.9883(5) 0.0432(10) Uani 1 d . . . H16 H -0.3633 0.9198 0.9798 0.052 Uiso 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 Br1 0.0504(3) 0.0363(2) 0.0473(2) 0.0000(2) 0.0237(2) -0.00234(18) Cu 0.0412(3) 0.0457(3) 0.0545(3) -0.0013(3) 0.0155(2) 0.0079(2) S1 0.0360(6) 0.0474(6) 0.0509(6) -0.0061(5) 0.0175(5) 0.0060(4) S11 0.0402(6) 0.0419(6) 0.0831(9) -0.0095(6) 0.0297(6) -0.0006(5) N3 0.0361(19) 0.0357(17) 0.047(2) -0.0001(15) 0.0098(16) 0.0035(14) N1 0.0368(19) 0.0257(15) 0.045(2) 0.0010(14) 0.0185(15) 0.0001(13) N11 0.0369(19) 0.0315(16) 0.0417(19) 0.0023(15) 0.0123(15) -0.0017(13) N13 0.046(2) 0.0311(18) 0.132(4) 0.007(2) 0.022(2) -0.0038(16) C1 0.058(3) 0.044(2) 0.043(2) 0.000(2) 0.022(2) 0.014(2) C2 0.035(2) 0.0237(18) 0.048(3) 0.0050(17) 0.0168(19) 0.0011(15) C4 0.028(2) 0.044(2) 0.059(3) 0.006(2) 0.007(2) -0.0026(17) C5 0.038(2) 0.033(2) 0.071(3) 0.002(2) 0.028(2) 0.0033(17) C6 0.038(2) 0.0337(19) 0.054(3) 0.0018(19) 0.026(2) 0.0022(16) C12 0.042(2) 0.030(2) 0.045(2) 0.0000(18) 0.0178(19) -0.0018(16) C14 0.038(3) 0.044(3) 0.188(7) 0.020(4) 0.025(4) -0.007(2) C15 0.032(2) 0.054(3) 0.086(4) 0.009(3) 0.016(2) 0.002(2) C16 0.038(2) 0.039(2) 0.048(3) 0.003(2) 0.0091(19) 0.0036(17) _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 Cu 2.4600(7) . ? Br1 Cu 2.6218(7) 3_566 ? Cu N1 2.027(3) . ? Cu N11 2.037(3) 4_575 ? Cu Br1 2.6219(7) 3_566 ? Cu Cu 3.0555(11) 3_566 ? Cu S1 3.1566(12) . ? Cu S11 3.2625(12) 4_575 ? S1 C2 1.754(4) . ? S1 C1 1.798(4) . ? S11 C12 1.745(4) . ? S11 C1 1.795(4) . ? N3 C2 1.330(5) . ? N3 C4 1.340(5) . ? N1 C6 1.328(4) . ? N1 C2 1.356(5) . ? N11 C16 1.332(5) . ? N11 C12 1.349(4) . ? N11 Cu 2.037(3) 4_576 ? N13 C12 1.307(5) . ? N13 C14 1.334(6) . ? C4 C5 1.364(6) . ? C5 C6 1.382(5) . ? C14 C15 1.349(6) . ? C15 C16 1.361(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu Br1 Cu 73.84(2) . 3_566 ? N1 Cu N11 121.68(12) . 4_575 ? N1 Cu Br1 110.19(9) . . ? N11 Cu Br1 110.63(9) 4_575 . ? N1 Cu Br1 104.11(8) . 3_566 ? N11 Cu Br1 102.47(9) 4_575 3_566 ? Br1 Cu Br1 106.15(2) . 3_566 ? N1 Cu Cu 119.14(8) . 3_566 ? N11 Cu Cu 117.96(9) 4_575 3_566 ? Br1 Cu Cu 55.504(19) . 3_566 ? Br1 Cu Cu 50.651(18) 3_566 3_566 ? N1 Cu S1 55.68(9) . . ? N11 Cu S1 75.52(9) 4_575 . ? Br1 Cu S1 163.75(3) . . ? Br1 Cu S1 86.47(3) 3_566 . ? Cu Cu S1 136.06(3) 3_566 . ? N1 Cu S11 80.85(8) . 4_575 ? N11 Cu S11 53.12(9) 4_575 4_575 ? Br1 Cu S11 99.08(3) . 4_575 ? Br1 Cu S11 150.39(3) 3_566 4_575 ? Cu Cu S11 150.81(4) 3_566 4_575 ? S1 Cu S11 72.13(3) . 4_575 ? C2 S1 C1 102.20(19) . . ? C2 S1 Cu 67.93(14) . . ? C1 S1 Cu 164.43(15) . . ? C12 S11 C1 101.93(19) . . ? C2 N3 C4 116.3(4) . . ? C6 N1 C2 116.1(3) . . ? C6 N1 Cu 121.6(3) . . ? C2 N1 Cu 122.3(2) . . ? C16 N11 C12 115.5(3) . . ? C16 N11 Cu 118.2(2) . 4_576 ? C12 N11 Cu 125.4(3) . 4_576 ? C12 N13 C14 115.9(4) . . ? S11 C1 S1 115.9(2) . . ? N3 C2 N1 125.2(3) . . ? N3 C2 S1 120.7(3) . . ? N1 C2 S1 114.1(3) . . ? N3 C4 C5 123.3(4) . . ? C4 C5 C6 116.0(4) . . ? N1 C6 C5 123.0(4) . . ? N13 C12 N11 125.6(4) . . ? N13 C12 S11 119.9(3) . . ? N11 C12 S11 114.5(3) . . ? C15 C14 N13 124.1(4) . . ? C16 C15 C14 115.6(4) . . ? N11 C16 C15 123.3(4) . . ? 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 Cu Br1 Cu N1 112.14(9) 3_566 . . . ? Cu Br1 Cu N11 -110.44(10) 3_566 . . 4_575 ? Cu Br1 Cu Br1 0.000(1) 3_566 . . 3_566 ? Cu Br1 Cu S1 139.88(11) 3_566 . . . ? Cu Br1 Cu S11 -164.34(3) 3_566 . . 4_575 ? N1 Cu S1 C2 0.58(15) . . . . ? N11 Cu S1 C2 -145.84(16) 4_575 . . . ? Br1 Cu S1 C2 -31.36(17) . . . . ? Br1 Cu S1 C2 110.31(12) 3_566 . . . ? Cu Cu S1 C2 98.70(13) 3_566 . . . ? S11 Cu S1 C2 -90.45(12) 4_575 . . . ? N1 Cu S1 C1 53.3(5) . . . . ? N11 Cu S1 C1 -93.1(5) 4_575 . . . ? Br1 Cu S1 C1 21.4(5) . . . . ? Br1 Cu S1 C1 163.0(5) 3_566 . . . ? Cu Cu S1 C1 151.4(5) 3_566 . . . ? S11 Cu S1 C1 -37.7(5) 4_575 . . . ? N11 Cu N1 C6 -142.6(3) 4_575 . . . ? Br1 Cu N1 C6 -10.7(3) . . . . ? Br1 Cu N1 C6 102.7(3) 3_566 . . . ? Cu Cu N1 C6 50.2(3) 3_566 . . . ? S1 Cu N1 C6 178.4(3) . . . . ? S11 Cu N1 C6 -107.1(3) 4_575 . . . ? N11 Cu N1 C2 38.2(3) 4_575 . . . ? Br1 Cu N1 C2 170.1(2) . . . . ? Br1 Cu N1 C2 -76.4(3) 3_566 . . . ? Cu Cu N1 C2 -129.0(2) 3_566 . . . ? S1 Cu N1 C2 -0.8(2) . . . . ? S11 Cu N1 C2 73.7(2) 4_575 . . . ? C12 S11 C1 S1 85.9(3) . . . . ? C2 S1 C1 S11 100.8(2) . . . . ? Cu S1 C1 S11 51.8(6) . . . . ? C4 N3 C2 N1 -0.9(5) . . . . ? C4 N3 C2 S1 178.3(3) . . . . ? C6 N1 C2 N3 1.3(5) . . . . ? Cu N1 C2 N3 -179.4(3) . . . . ? C6 N1 C2 S1 -177.9(3) . . . . ? Cu N1 C2 S1 1.3(3) . . . . ? C1 S1 C2 N3 12.6(3) . . . . ? Cu S1 C2 N3 179.9(3) . . . . ? C1 S1 C2 N1 -168.2(3) . . . . ? Cu S1 C2 N1 -0.8(2) . . . . ? C2 N3 C4 C5 -0.5(5) . . . . ? N3 C4 C5 C6 1.3(6) . . . . ? C2 N1 C6 C5 -0.4(5) . . . . ? Cu N1 C6 C5 -179.6(3) . . . . ? C4 C5 C6 N1 -0.8(6) . . . . ? C14 N13 C12 N11 -1.4(8) . . . . ? C14 N13 C12 S11 177.6(5) . . . . ? C16 N11 C12 N13 0.9(6) . . . . ? Cu N11 C12 N13 169.9(4) 4_576 . . . ? C16 N11 C12 S11 -178.1(3) . . . . ? Cu N11 C12 S11 -9.1(5) 4_576 . . . ? C1 S11 C12 N13 -6.8(4) . . . . ? C1 S11 C12 N11 172.3(3) . . . . ? C12 N13 C14 C15 -0.4(10) . . . . ? N13 C14 C15 C16 2.5(10) . . . . ? C12 N11 C16 C15 1.4(6) . . . . ? Cu N11 C16 C15 -168.4(4) 4_576 . . . ? C14 C15 C16 N11 -2.9(8) . . . . ? 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 C14 H14 N3 0.93 2.56 3.326(6) 139.8 1_455 C16 H16 Br1 0.93 2.89 3.538(4) 128.3 2_556 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.803 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.094 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 742458' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Cu I N4 S2' _chemical_formula_weight 426.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 7.5969(6) _cell_length_b 20.2299(15) _cell_length_c 9.0204(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.2450(10) _cell_angle_gamma 90.00 _cell_volume 1283.12(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .25 _exptl_crystal_size_mid .22 _exptl_crystal_size_min .12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 4.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.706557 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 7881 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3003 _reflns_number_gt 2289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0217P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3003 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 I I 0.36515(3) 0.465398(11) 0.66244(3) 0.03748(8) Uani 1 1 d . . . Cu Cu 0.45382(6) 0.43253(2) 0.41725(6) 0.04303(13) Uani 1 1 d . . . S1 S 0.43455(13) 0.36294(5) 0.09412(12) 0.0421(2) Uani 1 1 d . . . S2 S 0.37334(14) 0.27467(5) 0.44516(15) 0.0499(3) Uani 1 1 d . . . N1 N 0.2124(4) 0.42076(13) 0.2167(4) 0.0333(7) Uani 1 1 d . . . N2 N 0.6526(4) 0.35796(13) 0.4881(3) 0.0332(7) Uani 1 1 d . . . N3 N 0.0600(4) 0.38433(15) -0.0531(4) 0.0408(7) Uani 1 1 d . . . N4 N 0.7358(5) 0.24410(16) 0.5199(5) 0.0692(12) Uani 1 1 d . . . C1 C 0.0427(5) 0.44368(17) 0.2090(5) 0.0408(9) Uani 1 1 d . . . H1 H 0.0364 0.4640 0.2993 0.049 Uiso 1 1 calc R . . C2 C -0.1200(5) 0.43877(19) 0.0765(5) 0.0424(9) Uani 1 1 d . . . H2 H -0.2350 0.4555 0.0742 0.051 Uiso 1 1 calc R . . C3 C -0.1055(5) 0.40796(19) -0.0533(5) 0.0462(10) Uani 1 1 d . . . H3 H -0.2145 0.4031 -0.1454 0.055 Uiso 1 1 calc R . . C4 C 0.2113(5) 0.39204(16) 0.0818(4) 0.0333(8) Uani 1 1 d . . . C5 C 0.3702(6) 0.31314(17) -0.0839(5) 0.0438(9) Uani 1 1 d . . . H5A H 0.2433 0.3258 -0.1557 0.053 Uiso 1 1 calc R . . H5B H 0.4563 0.3236 -0.1371 0.053 Uiso 1 1 calc R . . C6 C 0.6130(5) 0.29290(17) 0.4887(4) 0.0371(8) Uani 1 1 d . . . C7 C 0.8348(5) 0.37258(18) 0.5175(4) 0.0381(8) Uani 1 1 d . . . H7 H 0.8698 0.4167 0.5191 0.046 Uiso 1 1 calc R . . C8 C 0.9703(5) 0.3251(2) 0.5453(6) 0.0569(12) Uani 1 1 d . . . H8 H 1.0957 0.3359 0.5629 0.068 Uiso 1 1 calc R . . C9 C 0.9153(6) 0.2619(2) 0.5462(8) 0.085(2) Uani 1 1 d . . . H9 H 1.0065 0.2288 0.5660 0.102 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 I 0.04010(14) 0.03274(13) 0.04344(15) 0.00146(11) 0.02017(11) -0.00237(10) Cu 0.0332(3) 0.0441(3) 0.0508(3) 0.0016(2) 0.0147(2) 0.0049(2) S1 0.0314(5) 0.0476(5) 0.0478(6) -0.0060(5) 0.0154(5) 0.0070(4) S2 0.0358(5) 0.0397(5) 0.0795(8) 0.0080(5) 0.0279(6) -0.0017(4) N1 0.0317(16) 0.0286(15) 0.0425(18) -0.0001(13) 0.0173(14) 0.0012(12) N2 0.0284(16) 0.0291(15) 0.0424(18) 0.0008(13) 0.0139(14) 0.0008(12) N3 0.0332(17) 0.0409(18) 0.045(2) -0.0035(15) 0.0114(15) 0.0036(13) N4 0.038(2) 0.0341(19) 0.122(4) -0.007(2) 0.015(2) 0.0033(15) C1 0.040(2) 0.0353(19) 0.053(3) -0.0004(18) 0.024(2) 0.0032(16) C2 0.029(2) 0.043(2) 0.057(3) 0.004(2) 0.0179(19) 0.0043(16) C3 0.031(2) 0.047(2) 0.053(3) -0.0029(19) 0.0070(19) 0.0029(17) C4 0.0304(19) 0.0275(18) 0.043(2) 0.0033(16) 0.0152(17) 0.0021(14) C5 0.046(2) 0.039(2) 0.049(2) 0.0027(18) 0.022(2) 0.0143(17) C6 0.033(2) 0.035(2) 0.044(2) -0.0011(17) 0.0149(18) -0.0003(15) C7 0.0309(19) 0.035(2) 0.046(2) -0.0022(17) 0.0118(17) -0.0024(15) C8 0.028(2) 0.054(3) 0.083(4) -0.019(2) 0.014(2) 0.0020(19) C9 0.032(2) 0.045(3) 0.160(6) -0.020(3) 0.016(3) 0.011(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I Cu 2.6298(6) . ? I Cu 2.7240(5) 3_666 ? Cu N1 2.045(3) . ? Cu N2 2.057(3) . ? Cu I 2.7241(5) 3_666 ? S1 C4 1.759(3) . ? S1 C5 1.800(4) . ? S2 C6 1.750(3) . ? S2 C5 1.795(4) 4_566 ? N1 C4 1.346(4) . ? N1 C1 1.347(4) . ? N2 C7 1.340(4) . ? N2 C6 1.350(4) . ? N3 C4 1.330(4) . ? N3 C3 1.344(5) . ? N4 C6 1.314(4) . ? N4 C9 1.342(5) . ? C1 C2 1.359(5) . ? C2 C3 1.367(6) . ? C5 S2 1.795(4) 4_565 ? C7 C8 1.360(5) . ? C8 C9 1.347(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu I Cu 69.763(19) . 3_666 ? N1 Cu N2 119.76(11) . . ? N1 Cu I 110.11(8) . . ? N2 Cu I 108.41(8) . . ? N1 Cu I 103.20(8) . 3_666 ? N2 Cu I 104.67(8) . 3_666 ? I Cu I 110.236(19) . 3_666 ? C4 S1 C5 101.62(17) . . ? C6 S2 C5 101.34(18) . 4_566 ? C4 N1 C1 115.1(3) . . ? C4 N1 Cu 123.1(2) . . ? C1 N1 Cu 121.8(3) . . ? C7 N2 C6 115.4(3) . . ? C7 N2 Cu 118.8(2) . . ? C6 N2 Cu 125.3(2) . . ? C4 N3 C3 116.4(3) . . ? C6 N4 C9 115.4(3) . . ? N1 C1 C2 123.7(4) . . ? C1 C2 C3 116.4(3) . . ? N3 C3 C2 122.6(4) . . ? N3 C4 N1 125.8(3) . . ? N3 C4 S1 119.8(3) . . ? N1 C4 S1 114.3(3) . . ? S2 C5 S1 116.1(2) 4_565 . ? N4 C6 N2 126.3(3) . . ? N4 C6 S2 118.9(3) . . ? N2 C6 S2 114.8(2) . . ? N2 C7 C8 122.3(3) . . ? C9 C8 C7 117.2(4) . . ? N4 C9 C8 123.4(4) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.561 _refine_diff_density_min -0.771 _refine_diff_density_rms 0.137