# 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 _publ_contact_author_name 'Carballo, Rosa' _publ_contact_author_email rcrial@uvigo.es _publ_section_title ; Metal coordination and in situ S\^aC bond cleavage of the bis(2-pyridylthio)methane ligand ; loop_ _publ_author_name A.Lago A.Amoedo R.Carballo E.Garcia E.Vazquez-Lopez # Attachment '- DT_ART_05_2010_000560_Mat_dep.cif' data_ligand _database_code_depnum_ccdc_archive 'CCDC 778412' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778412 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 I4 N2 S2' _chemical_formula_weight 742.94 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.4435(15) _cell_length_b 9.6542(16) _cell_length_c 11.7607(19) _cell_angle_alpha 95.607(3) _cell_angle_beta 100.683(3) _cell_angle_gamma 111.932(3) _cell_volume 960.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max .24 _exptl_crystal_size_mid .17 _exptl_crystal_size_min .06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 6.693 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.588231 _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 5582 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.02 _reflns_number_total 3998 _reflns_number_gt 2299 _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 'ORTEPIII, 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3998 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1122 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 -0.32448(10) -0.07463(11) 0.37785(10) 0.0791(3) Uani 1 1 d . . . I2 I 0.0000 0.0000 0.5000 0.0458(3) Uani 1 2 d S . . I3 I -0.54916(11) 0.28497(10) 0.01190(9) 0.0752(3) Uani 1 1 d . . . I4 I -0.5000 0.0000 0.0000 0.0651(4) Uani 1 2 d S . . I5 I -0.15746(13) 0.44663(10) 0.00424(8) 0.0827(4) Uani 1 1 d . . . S11 S -0.7105(3) -0.3704(3) 0.3613(3) 0.0501(7) Uani 1 1 d . . . N11 N -0.9924(9) -0.6169(9) 0.3008(7) 0.0357(18) Uani 1 1 d . . . C1 C -0.6475(13) -0.5071(12) 0.2969(10) 0.049(3) Uani 1 1 d . . . H1A H -0.5464 -0.4528 0.2801 0.059 Uiso 1 1 calc R . . H1B H -0.7217 -0.5607 0.2223 0.059 Uiso 1 1 calc R . . C12 C -0.9118(11) -0.4657(10) 0.3440(8) 0.038(2) Uani 1 1 d . . . C13 C -0.9922(13) -0.3816(13) 0.3809(10) 0.055(3) Uani 1 1 d . . . H13 H -0.9383 -0.2786 0.4124 0.066 Uiso 1 1 calc R . . C14 C -1.1502(15) -0.4504(15) 0.3710(11) 0.064(3) Uani 1 1 d . . . H14 H -1.2036 -0.3938 0.3957 0.076 Uiso 1 1 calc R . . C15 C -1.2315(14) -0.6031(16) 0.3247(12) 0.062(3) Uani 1 1 d . . . H15 H -1.3393 -0.6508 0.3174 0.075 Uiso 1 1 calc R . . C16 C -1.1472(12) -0.6828(13) 0.2895(10) 0.051(3) Uani 1 1 d . . . H16 H -1.2002 -0.7856 0.2570 0.061 Uiso 1 1 calc R . . S1 S -0.6289(3) -0.6469(3) 0.3850(3) 0.0505(7) Uani 1 1 d . . . N1 N -0.8925(10) -0.8302(9) 0.2293(7) 0.045(2) Uani 1 1 d . . . H111 H -0.9172 -0.7531 0.2359 0.053 Uiso 1 1 calc R . . C2 C -0.7556(12) -0.8200(12) 0.2870(9) 0.042(2) Uani 1 1 d . . . C3 C -0.7108(15) -0.9427(14) 0.2789(11) 0.059(3) Uani 1 1 d . . . H3 H -0.6135 -0.9338 0.3215 0.070 Uiso 1 1 calc R . . C4 C -0.8121(19) -1.0738(14) 0.2080(12) 0.073(4) Uani 1 1 d . . . H4 H -0.7831 -1.1556 0.1997 0.087 Uiso 1 1 calc R . . C5 C -0.960(2) -1.0890(15) 0.1467(13) 0.085(5) Uani 1 1 d . . . H5 H -1.0313 -1.1806 0.0994 0.102 Uiso 1 1 calc R . . C6 C -0.9957(15) -0.9637(13) 0.1586(11) 0.066(4) Uani 1 1 d . . . H6 H -1.0928 -0.9703 0.1173 0.079 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 0.0606(6) 0.0639(6) 0.1043(8) 0.0335(5) 0.0103(5) 0.0156(5) I2 0.0579(6) 0.0288(5) 0.0560(6) 0.0039(4) 0.0259(5) 0.0185(5) I3 0.0804(6) 0.0557(6) 0.0934(7) 0.0008(5) 0.0190(5) 0.0359(5) I4 0.0563(7) 0.0644(8) 0.0672(8) -0.0034(6) 0.0156(6) 0.0194(6) I5 0.1495(9) 0.0623(6) 0.0494(5) 0.0059(4) 0.0160(5) 0.0614(6) S11 0.0473(16) 0.0297(14) 0.072(2) 0.0006(13) 0.0125(14) 0.0166(13) N11 0.040(5) 0.031(4) 0.037(5) 0.007(3) 0.008(4) 0.016(4) C1 0.053(6) 0.047(6) 0.061(8) 0.022(5) 0.031(5) 0.024(5) C12 0.053(6) 0.026(5) 0.039(6) 0.000(4) 0.011(5) 0.023(5) C13 0.064(8) 0.042(6) 0.074(8) 0.000(6) 0.023(6) 0.035(6) C14 0.071(9) 0.075(9) 0.073(9) 0.012(7) 0.037(7) 0.051(8) C15 0.044(7) 0.074(9) 0.078(9) 0.026(7) 0.023(6) 0.027(7) C16 0.048(7) 0.041(6) 0.064(8) 0.007(5) 0.012(5) 0.020(6) S1 0.0510(16) 0.0433(16) 0.0608(19) 0.0073(13) 0.0067(13) 0.0267(14) N1 0.055(6) 0.033(5) 0.048(5) -0.005(4) 0.011(4) 0.024(4) C2 0.052(7) 0.042(6) 0.045(6) 0.015(5) 0.025(5) 0.023(5) C3 0.082(9) 0.058(8) 0.062(8) 0.022(6) 0.035(7) 0.045(7) C4 0.125(12) 0.042(7) 0.074(9) 0.009(7) 0.050(9) 0.047(8) C5 0.137(14) 0.039(7) 0.071(10) -0.007(6) 0.009(9) 0.040(9) C6 0.077(9) 0.039(7) 0.066(9) -0.012(6) 0.004(7) 0.017(7) _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 I2 2.9135(10) . ? I2 I1 2.9135(10) 2_556 ? I3 I4 2.9507(10) . ? I4 I3 2.9507(10) 2_455 ? I5 I5 2.785(2) 2_565 ? S11 C12 1.736(10) . ? S11 C1 1.797(10) . ? S11 S1 3.066(4) . ? N11 C16 1.333(12) . ? N11 C12 1.360(11) . ? C1 S1 1.819(11) . ? C12 C13 1.392(13) . ? C13 C14 1.364(16) . ? C14 C15 1.379(17) . ? C15 C16 1.385(16) . ? S1 C2 1.781(11) . ? N1 C2 1.308(12) . ? N1 C6 1.362(13) . ? C2 C3 1.399(14) . ? C3 C4 1.344(17) . ? C4 C5 1.392(19) . ? C5 C6 1.375(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 I2 I1 180.000(2) 2_556 . ? I3 I4 I3 180.0 . 2_455 ? C12 S11 C1 105.5(5) . . ? C12 S11 S1 96.4(3) . . ? C1 S11 S1 32.2(3) . . ? C16 N11 C12 120.7(9) . . ? S11 C1 S1 116.0(6) . . ? N11 C12 C13 119.0(9) . . ? N11 C12 S11 123.8(7) . . ? C13 C12 S11 117.2(8) . . ? C14 C13 C12 120.0(10) . . ? C13 C14 C15 120.5(10) . . ? C14 C15 C16 117.7(11) . . ? N11 C16 C15 122.0(10) . . ? C2 S1 C1 101.4(5) . . ? C2 S1 S11 117.0(4) . . ? C1 S1 S11 31.8(3) . . ? C2 N1 C6 119.5(9) . . ? N1 C2 C3 122.1(10) . . ? N1 C2 S1 118.0(7) . . ? C3 C2 S1 119.8(9) . . ? C4 C3 C2 118.3(12) . . ? C3 C4 C5 121.1(12) . . ? C6 C5 C4 117.5(12) . . ? N1 C6 C5 121.5(12) . . ? 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 H111 N1 C2 -84.6 . . . . ? H111 N1 C2 S1 3.6 . . . . ? N1 C2 S1 C1 -44.2(9) . . . . ? C2 S1 C1 S11 123.6(7) . . . . ? S1 C1 S11 C12 -77.2(7) . . . . ? C1 S11 C12 N11 6.1(10) . . . . ? S11 C12 N11 H111 -7.0 . . . . ? C12 N11 H111 N1 117.8 . . . . ? 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 C1 H1B N1 0.97 2.52 3.025(14) 112.7 . _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 1.524 _refine_diff_density_min -1.620 _refine_diff_density_rms 0.221 data_1 _database_code_depnum_ccdc_archive 'CCDC 778413' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778413 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Cl2 Co N2 O S2' _chemical_formula_weight 382.18 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.0433(3) _cell_length_b 10.9345(4) _cell_length_c 14.3021(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.6077(12) _cell_angle_gamma 90.00 _cell_volume 1526.55(8) _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 .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6465 _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 5583 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 28.32 _reflns_number_total 1894 _reflns_number_gt 1549 _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 'ORTEPIII, 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.9793P] 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 1894 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Co1 Co 0.0000 0.15760(4) 0.2500 0.03155(13) Uani 1 2 d S . . Cl1 Cl 0.13600(6) 0.27694(6) 0.18210(5) 0.04846(17) Uani 1 1 d . . . S1 S -0.06462(6) -0.09359(5) 0.33712(4) 0.04074(16) Uani 1 1 d . . . N1 N 0.12909(17) 0.07514(16) 0.36443(13) 0.0342(4) Uani 1 1 d . . . C1 C 0.0000 -0.1818(3) 0.2500 0.0395(7) Uani 1 2 d S . . H1A H -0.0730 -0.2343 0.2155 0.047 Uiso 0.50 1 calc PR . . H1B H 0.0730 -0.2343 0.2845 0.047 Uiso 0.50 1 calc PR . . C2 C 0.0926(2) -0.0295(2) 0.40097(16) 0.0350(5) Uani 1 1 d . . . C3 C 0.1705(3) -0.0830(2) 0.48302(18) 0.0480(6) Uani 1 1 d . . . H3 H 0.1421 -0.1551 0.5068 0.058 Uiso 1 1 calc R . . C4 C 0.2906(3) -0.0277(3) 0.5290(2) 0.0583(7) Uani 1 1 d . . . H4 H 0.3443 -0.0614 0.5851 0.070 Uiso 1 1 calc R . . C5 C 0.3310(3) 0.0778(3) 0.4917(2) 0.0557(7) Uani 1 1 d . . . H5 H 0.4130 0.1157 0.5214 0.067 Uiso 1 1 calc R . . C6 C 0.2482(2) 0.1267(2) 0.40978(19) 0.0459(6) Uani 1 1 d . . . H6 H 0.2757 0.1984 0.3848 0.055 Uiso 1 1 calc R . . O1 O 0.0000 0.5282(3) 0.2500 0.1084(14) Uani 1 2 d S . . H1 H 0.0838 0.4810 0.2650 0.130 Uiso 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 Co1 0.0297(2) 0.0316(2) 0.0325(2) 0.000 0.00574(16) 0.000 Cl1 0.0481(3) 0.0515(4) 0.0475(4) 0.0046(3) 0.0147(3) -0.0133(3) S1 0.0371(3) 0.0412(3) 0.0480(3) 0.0019(3) 0.0181(2) -0.0060(2) N1 0.0328(8) 0.0332(9) 0.0351(10) 0.0003(8) 0.0052(7) -0.0013(7) C1 0.0419(16) 0.0256(15) 0.051(2) 0.000 0.0104(15) 0.000 C2 0.0373(10) 0.0349(11) 0.0350(11) 0.0013(9) 0.0128(9) 0.0035(9) C3 0.0607(15) 0.0475(15) 0.0373(13) 0.0089(11) 0.0143(11) 0.0118(12) C4 0.0627(17) 0.0683(19) 0.0375(13) 0.0002(13) -0.0013(12) 0.0207(15) C5 0.0429(13) 0.0657(19) 0.0506(15) -0.0122(14) -0.0045(11) 0.0019(13) C6 0.0402(12) 0.0455(13) 0.0482(14) -0.0016(11) 0.0027(11) -0.0051(10) O1 0.145(4) 0.055(2) 0.099(3) 0.000 -0.024(3) 0.000 _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 N1 2.0430(18) 2 ? Co1 N1 2.0430(18) . ? Co1 Cl1 2.2662(6) . ? Co1 Cl1 2.2662(6) 2 ? Co1 S1 3.1461(7) . ? S1 C2 1.771(2) . ? S1 C1 1.8123(17) . ? N1 C6 1.343(3) . ? N1 C2 1.344(3) . ? N1 N1 3.667(4) 2 ? C1 S1 1.8123(17) 2 ? C2 C3 1.378(3) . ? C3 C4 1.371(4) . ? C4 C5 1.372(4) . ? C5 C6 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 127.62(10) 2 . ? N1 Co1 Cl1 104.11(5) 2 . ? N1 Co1 Cl1 105.34(5) . . ? N1 Co1 Cl1 105.34(5) 2 2 ? N1 Co1 Cl1 104.11(5) . 2 ? Cl1 Co1 Cl1 109.69(4) . 2 ? N1 Co1 S1 77.34(5) 2 . ? N1 Co1 S1 56.54(5) . . ? Cl1 Co1 S1 150.89(2) . . ? Cl1 Co1 S1 97.57(2) 2 . ? C2 S1 C1 98.34(8) . . ? C2 S1 Co1 67.49(7) . . ? C1 S1 Co1 92.97(8) . . ? C6 N1 C2 117.6(2) . . ? C6 N1 Co1 121.78(16) . . ? C2 N1 Co1 120.48(14) . . ? C6 N1 N1 142.51(16) . 2 ? C2 N1 N1 98.43(13) . 2 ? Co1 N1 N1 26.19(5) . 2 ? S1 C1 S1 115.69(17) . 2 ? N1 C2 C3 122.7(2) . . ? N1 C2 S1 115.33(16) . . ? C3 C2 S1 122.01(19) . . ? C4 C3 C2 118.8(3) . . ? C3 C4 C5 119.4(2) . . ? C4 C5 C6 118.9(2) . . ? N1 C6 C5 122.6(2) . . ? 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 Co1 N1 C2 -35.78(15) 2 . . . ? Co1 N1 C2 S1 5.0(2) . . . . ? N1 C2 S1 C1 86.74(18) . . . . ? C2 S1 C1 S1 -67.67(7) . . . 2 ? S1 C1 S1 C2 -67.67(7) . . 2 2 ? C1 S1 C2 N1 86.74(18) . 2 2 2 ? S1 C2 N1 Co1 5.0(2) 2 2 2 . ? C2 N1 Co1 N1 -35.78(15) 2 2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 Cl1 0.97 2.64 3.314(3) 127 . C4 H4 O1 0.93 2.53 3.359(3) 148.4 7_556 C1 H1A Cl1 0.97 2.85 3.5834(7) 133.0 3_445 C6 H6 S1 0.93 2.95 3.859(3) 164.7 3 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.309 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.061 data_2 _database_code_depnum_ccdc_archive 'CCDC 778414' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778414 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Br2 Co N2 S2' _chemical_formula_weight 453.08 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' Co Co 0.3494 0.9721 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.7216(12) _cell_length_b 14.0186(13) _cell_length_c 16.9669(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3025.9(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 blue _exptl_crystal_size_max .36 _exptl_crystal_size_mid .22 _exptl_crystal_size_min .17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.989 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 6.675 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7531 _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 19014 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3640 _reflns_number_gt 1883 _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 'ORTEPIII, 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0177P)^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 3640 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0444 _refine_ls_goodness_of_fit_ref 0.768 _refine_ls_restrained_S_all 0.768 _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 Co1 Co 0.47330(4) 0.79723(3) 0.67003(3) 0.03600(13) Uani 1 1 d . . . Br1 Br 0.64442(3) 0.75658(3) 0.61969(2) 0.04816(11) Uani 1 1 d . . . Br2 Br 0.36551(3) 0.65736(3) 0.65913(3) 0.06071(13) Uani 1 1 d . . . C1 C 0.3729(3) 1.0353(2) 0.7465(2) 0.0481(10) Uani 1 1 d . . . H1A H 0.3953 1.0685 0.7937 0.058 Uiso 1 1 calc R . . H1B H 0.3177 1.0731 0.7224 0.058 Uiso 1 1 calc R . . S1 S 0.31757(7) 0.92151(7) 0.77538(6) 0.0463(3) Uani 1 1 d . . . N1 N 0.4980(2) 0.82850(18) 0.78624(16) 0.0356(7) Uani 1 1 d . . . C2 C 0.4276(3) 0.8782(2) 0.8286(2) 0.0381(9) Uani 1 1 d . . . C3 C 0.4409(3) 0.8963(3) 0.9071(2) 0.0534(11) Uani 1 1 d . . . H3 H 0.3901 0.9303 0.9348 0.064 Uiso 1 1 calc R . . C4 C 0.5288(4) 0.8645(3) 0.9447(2) 0.0636(12) Uani 1 1 d . . . H4 H 0.5387 0.8763 0.9982 0.076 Uiso 1 1 calc R . . C5 C 0.6026(3) 0.8148(3) 0.9023(2) 0.0537(11) Uani 1 1 d . . . H5 H 0.6636 0.7928 0.9264 0.064 Uiso 1 1 calc R . . C6 C 0.5850(3) 0.7980(2) 0.8234(2) 0.0432(9) Uani 1 1 d . . . H6 H 0.6351 0.7643 0.7949 0.052 Uiso 1 1 calc R . . S11 S 0.48296(8) 1.03035(6) 0.67893(5) 0.0446(2) Uani 1 1 d . . . N11 N 0.4141(2) 0.88922(19) 0.58755(16) 0.0347(7) Uani 1 1 d . . . C12 C 0.4174(2) 0.9850(2) 0.59477(19) 0.0348(9) Uani 1 1 d . . . C13 C 0.3771(3) 1.0449(2) 0.5379(2) 0.0431(10) Uani 1 1 d . . . H13 H 0.3787 1.1106 0.5451 0.052 Uiso 1 1 calc R . . C14 C 0.3344(3) 1.0068(3) 0.4706(2) 0.0508(11) Uani 1 1 d . . . H14 H 0.3077 1.0465 0.4315 0.061 Uiso 1 1 calc R . . C15 C 0.3314(3) 0.9100(3) 0.4615(2) 0.0496(10) Uani 1 1 d . . . H15 H 0.3035 0.8827 0.4161 0.060 Uiso 1 1 calc R . . C16 C 0.3707(3) 0.8539(3) 0.5212(2) 0.0438(9) Uani 1 1 d . . . H16 H 0.3671 0.7880 0.5155 0.053 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 Co1 0.0386(3) 0.0363(3) 0.0331(3) 0.0006(2) -0.0030(2) -0.0002(2) Br1 0.0461(2) 0.0513(2) 0.0470(2) -0.00304(19) 0.0046(2) 0.0066(2) Br2 0.0591(3) 0.0499(2) 0.0731(3) 0.0083(2) -0.0058(3) -0.0177(2) C1 0.058(3) 0.047(2) 0.039(2) -0.0027(18) -0.001(2) 0.0141(19) S1 0.0382(5) 0.0605(7) 0.0402(6) 0.0028(5) 0.0023(5) 0.0018(5) N1 0.0388(19) 0.0375(18) 0.0305(18) 0.0045(14) -0.0027(14) -0.0004(14) C2 0.043(2) 0.039(2) 0.032(2) 0.0029(18) 0.0010(19) -0.0009(17) C3 0.058(3) 0.067(3) 0.035(3) -0.004(2) 0.002(2) 0.009(2) C4 0.082(3) 0.073(3) 0.036(3) 0.000(2) -0.015(3) 0.001(3) C5 0.056(3) 0.054(3) 0.051(3) 0.005(2) -0.014(2) 0.006(2) C6 0.048(2) 0.042(2) 0.040(3) 0.0058(19) 0.000(2) 0.0048(19) S11 0.0518(6) 0.0431(6) 0.0389(6) -0.0004(5) -0.0030(5) -0.0079(5) N11 0.0373(18) 0.0352(18) 0.0315(19) -0.0005(13) 0.0008(14) -0.0048(14) C12 0.033(2) 0.038(2) 0.034(2) 0.0022(17) 0.0000(17) -0.0018(17) C13 0.043(2) 0.038(2) 0.048(3) 0.0078(19) -0.001(2) 0.0003(18) C14 0.043(3) 0.062(3) 0.047(3) 0.022(2) -0.008(2) -0.007(2) C15 0.050(3) 0.062(3) 0.036(2) 0.007(2) -0.0113(19) -0.019(2) C16 0.045(2) 0.043(2) 0.043(3) 0.0010(19) 0.002(2) -0.0138(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.044(3) . ? Co1 N11 2.047(3) . ? Co1 Br2 2.3998(6) . ? Co1 Br1 2.4069(6) . ? Co1 S1 3.1868(11) . ? Co1 S11 3.2739(10) . ? C1 S1 1.811(3) . ? C1 S11 1.811(3) . ? S1 C2 1.773(3) . ? N1 C2 1.343(4) . ? N1 C6 1.343(4) . ? N1 N11 3.637(4) . ? C2 C3 1.367(5) . ? C3 C4 1.363(5) . ? C4 C5 1.374(5) . ? C5 C6 1.376(5) . ? S11 C12 1.771(3) . ? N11 C16 1.348(4) . ? N11 C12 1.349(4) . ? C12 C13 1.378(4) . ? C13 C14 1.374(5) . ? C14 C15 1.366(5) . ? C15 C16 1.377(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N11 125.52(11) . . ? N1 Co1 Br2 109.72(7) . . ? N11 Co1 Br2 104.58(8) . . ? N1 Co1 Br1 104.70(8) . . ? N11 Co1 Br1 103.86(8) . . ? Br2 Co1 Br1 107.22(2) . . ? N1 Co1 S1 55.76(8) . . ? N11 Co1 S1 79.05(8) . . ? Br2 Co1 S1 97.74(3) . . ? Br1 Co1 S1 152.96(3) . . ? N1 Co1 S11 74.67(7) . . ? N11 Co1 S11 54.30(8) . . ? Br2 Co1 S11 147.20(3) . . ? Br1 Co1 S11 102.63(2) . . ? S1 Co1 S11 56.75(3) . . ? S1 C1 S11 116.01(17) . . ? C2 S1 C1 97.64(16) . . ? C2 S1 Co1 66.89(12) . . ? C1 S1 Co1 95.04(11) . . ? C2 N1 C6 117.6(3) . . ? C2 N1 Co1 121.6(2) . . ? C6 N1 Co1 120.8(2) . . ? C2 N1 N11 100.3(2) . . ? C6 N1 N11 138.7(2) . . ? Co1 N1 N11 27.26(6) . . ? N1 C2 C3 122.3(3) . . ? N1 C2 S1 115.6(3) . . ? C3 C2 S1 122.0(3) . . ? C4 C3 C2 119.8(4) . . ? C3 C4 C5 118.8(4) . . ? C4 C5 C6 119.0(4) . . ? N1 C6 C5 122.5(3) . . ? C12 S11 C1 99.21(16) . . ? C12 S11 Co1 65.59(11) . . ? C1 S11 Co1 92.18(10) . . ? C16 N11 C12 117.1(3) . . ? C16 N11 Co1 119.3(2) . . ? C12 N11 Co1 123.6(2) . . ? C16 N11 N1 143.9(2) . . ? C12 N11 N1 98.0(2) . . ? Co1 N11 N1 27.22(6) . . ? N11 C12 C13 122.1(3) . . ? N11 C12 S11 116.5(2) . . ? C13 C12 S11 121.4(3) . . ? C14 C13 C12 119.5(3) . . ? C15 C14 C13 119.4(3) . . ? C14 C15 C16 118.3(3) . . ? N11 C16 C15 123.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 Co1 N1 C2 42.5(3) . . . . ? Co1 N1 C2 S1 -4.4(3) . . . . ? N1 C2 S1 C1 -89.7(3) . . . . ? C2 S1 C1 S11 66.2(2) . . . . ? S1 C1 S11 C12 66.7(2) . . . . ? C1 S11 C12 N11 -90.0(3) . . . . ? S11 C12 N11 Co1 3.0(3) . . . . ? C12 N11 Co1 N1 22.3(3) . . . . ? 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 C15 H15 Br1 0.93 2.88 3.606(4) 136.2 4_466 C1 H1B Br2 0.97 2.83 3.785(3) 170.3 8_665 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.410 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.076 data_3 _database_code_depnum_ccdc_archive 'CCDC 778415' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778415 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Co I2 N2 O0.50 S2' _chemical_formula_weight 556.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' I I -0.4742 1.8119 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.9682(9) _cell_length_b 7.8880(8) _cell_length_c 24.778(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.605(3) _cell_angle_gamma 90.00 _cell_volume 1747.2(3) _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 green _exptl_crystal_size_max .16 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 4.744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6456 _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 11345 _diffrn_reflns_av_R_equivalents 0.0854 _diffrn_reflns_av_sigmaI/netI 0.1534 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.08 _reflns_number_total 4199 _reflns_number_gt 1712 _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 'ORTEPIII, 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^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 4199 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1469 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.03966(9) 0.91934(10) 0.40375(3) 0.0600(3) Uani 1 1 d . . . I2 I -0.36218(10) 0.61315(8) 0.37819(3) 0.0663(3) Uani 1 1 d . . . Co1 Co -0.23663(15) 0.90541(16) 0.36418(4) 0.0391(4) Uani 1 1 d . . . S11 S -0.5399(3) 1.0410(3) 0.32483(9) 0.0439(7) Uani 1 1 d . . . S1 S -0.2714(3) 1.2532(3) 0.29353(10) 0.0493(7) Uani 1 1 d . . . N11 N -0.3495(9) 1.0624(9) 0.4115(3) 0.038(2) Uani 1 1 d . . . N1 N -0.2040(9) 0.9252(10) 0.2842(3) 0.040(2) Uani 1 1 d . . . C1 C -0.4708(11) 1.2229(11) 0.2888(4) 0.048(3) Uani 1 1 d . . . H1A H -0.5051 1.2119 0.2508 0.058 Uiso 1 1 calc R . . H1B H -0.5163 1.3244 0.3022 0.058 Uiso 1 1 calc R . . C2 C -0.2128(12) 1.0745(13) 0.2567(4) 0.049(3) Uani 1 1 d . . . C3 C -0.1824(13) 1.0890(14) 0.2023(4) 0.064(3) Uani 1 1 d . . . H3 H -0.1941 1.1924 0.1844 0.077 Uiso 1 1 calc R . . C4 C -0.1358(14) 0.9513(19) 0.1762(5) 0.079(4) Uani 1 1 d . . . H4 H -0.1150 0.9588 0.1401 0.094 Uiso 1 1 calc R . . C5 C -0.1191(12) 0.7968(16) 0.2039(5) 0.066(3) Uani 1 1 d . . . H5 H -0.0840 0.7011 0.1870 0.079 Uiso 1 1 calc R . . C6 C -0.1564(11) 0.7902(13) 0.2571(4) 0.048(3) Uani 1 1 d . . . H6 H -0.1479 0.6867 0.2752 0.058 Uiso 1 1 calc R . . C12 C -0.4890(12) 1.1094(11) 0.3923(3) 0.039(2) Uani 1 1 d . . . C13 C -0.5819(12) 1.2010(13) 0.4222(4) 0.049(3) Uani 1 1 d . . . H13 H -0.6769 1.2316 0.4077 0.059 Uiso 1 1 calc R . . C14 C -0.5338(13) 1.2464(13) 0.4729(4) 0.058(3) Uani 1 1 d . . . H14 H -0.5966 1.3054 0.4943 0.069 Uiso 1 1 calc R . . C15 C -0.3885(13) 1.2041(13) 0.4931(4) 0.053(3) Uani 1 1 d . . . H15 H -0.3518 1.2387 0.5275 0.064 Uiso 1 1 calc R . . C16 C -0.3020(12) 1.1115(12) 0.4615(4) 0.051(3) Uani 1 1 d . . . H16 H -0.2061 1.0812 0.4753 0.061 Uiso 1 1 calc R . . O O 0.0615(19) 0.4531(16) 0.4784(5) 0.082(6) Uani 0.50 1 d P . . 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 0.0487(5) 0.0852(6) 0.0444(4) 0.0039(4) -0.0059(3) 0.0051(5) I2 0.1017(8) 0.0428(4) 0.0555(5) -0.0028(4) 0.0137(4) -0.0133(5) Co1 0.0465(10) 0.0396(8) 0.0310(7) -0.0037(6) 0.0014(6) 0.0008(7) S11 0.0421(18) 0.0495(16) 0.0391(15) -0.0063(12) -0.0020(13) -0.0054(14) S1 0.054(2) 0.0459(16) 0.0476(16) -0.0004(13) 0.0033(14) -0.0087(15) N11 0.045(6) 0.040(5) 0.028(4) 0.005(4) -0.003(4) -0.001(4) N1 0.039(6) 0.049(5) 0.032(4) -0.009(4) 0.004(4) 0.012(4) C1 0.052(8) 0.040(6) 0.051(6) 0.002(5) 0.001(5) 0.007(6) C2 0.043(7) 0.059(7) 0.045(6) -0.004(6) -0.001(5) -0.003(6) C3 0.081(10) 0.076(9) 0.035(6) 0.008(6) 0.003(6) -0.015(8) C4 0.067(10) 0.125(12) 0.045(8) -0.039(8) 0.014(7) -0.011(9) C5 0.053(9) 0.094(10) 0.052(8) -0.024(7) 0.013(7) 0.008(8) C6 0.038(7) 0.051(7) 0.054(7) -0.014(5) -0.003(6) 0.011(6) C12 0.049(7) 0.040(6) 0.027(5) 0.010(4) 0.004(5) -0.003(5) C13 0.049(8) 0.065(7) 0.033(6) -0.002(5) 0.005(5) 0.008(6) C14 0.072(10) 0.065(8) 0.039(7) -0.010(6) 0.019(6) 0.000(7) C15 0.070(9) 0.056(7) 0.034(6) -0.003(5) 0.003(6) -0.002(7) C16 0.052(8) 0.065(7) 0.034(6) -0.014(6) -0.007(5) 0.005(6) O 0.108(16) 0.052(10) 0.077(12) 0.050(8) -0.056(10) -0.018(10) _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 Co1 2.5929(15) . ? I2 Co1 2.6011(15) . ? Co1 N11 2.031(7) . ? Co1 N1 2.033(7) . ? Co1 S11 3.011(3) . ? Co1 S1 3.256(3) . ? S11 C12 1.780(9) . ? S11 C1 1.825(9) . ? S1 C2 1.782(10) . ? S1 C1 1.799(10) . ? N11 C16 1.335(10) . ? N11 C12 1.354(11) . ? N11 N1 3.673(10) . ? N1 C6 1.346(11) . ? N1 C2 1.359(11) . ? C2 C3 1.401(13) . ? C3 C4 1.347(14) . ? C4 C5 1.400(15) . ? C5 C6 1.388(13) . ? C12 C13 1.365(12) . ? C13 C14 1.343(12) . ? C14 C15 1.398(14) . ? C15 C16 1.358(13) . ? O O 1.76(3) 3_566 ? 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 129.3(3) . . ? N11 Co1 I1 105.1(2) . . ? N1 Co1 I1 99.1(2) . . ? N11 Co1 I2 102.8(2) . . ? N1 Co1 I2 107.2(2) . . ? I1 Co1 I2 113.44(5) . . ? N11 Co1 S11 59.4(2) . . ? N1 Co1 S11 81.6(2) . . ? I1 Co1 S11 156.68(7) . . ? I2 Co1 S11 88.20(6) . . ? N11 Co1 S1 76.48(19) . . ? N1 Co1 S1 55.0(2) . . ? I1 Co1 S1 102.41(7) . . ? I2 Co1 S1 142.64(7) . . ? S11 Co1 S1 58.78(7) . . ? C12 S11 C1 98.6(4) . . ? C12 S11 Co1 69.3(4) . . ? C1 S11 Co1 96.0(3) . . ? C2 S1 C1 101.2(5) . . ? C2 S1 Co1 65.8(3) . . ? C1 S1 Co1 88.6(3) . . ? C16 N11 C12 117.7(8) . . ? C16 N11 Co1 125.2(7) . . ? C12 N11 Co1 116.9(6) . . ? C16 N11 N1 140.7(7) . . ? C12 N11 N1 99.2(5) . . ? Co1 N11 N1 25.35(16) . . ? C6 N1 C2 116.4(8) . . ? C6 N1 Co1 120.0(7) . . ? C2 N1 Co1 123.2(6) . . ? C6 N1 N11 144.0(7) . . ? C2 N1 N11 99.5(6) . . ? Co1 N1 N11 25.32(16) . . ? S1 C1 S11 116.6(5) . . ? N1 C2 C3 123.0(10) . . ? N1 C2 S1 115.9(8) . . ? C3 C2 S1 121.1(9) . . ? C4 C3 C2 119.2(11) . . ? C3 C4 C5 119.4(11) . . ? C6 C5 C4 118.3(11) . . ? N1 C6 C5 123.6(10) . . ? N11 C12 C13 122.7(8) . . ? N11 C12 S11 114.1(7) . . ? C13 C12 S11 123.2(8) . . ? C14 C13 C12 119.0(10) . . ? C13 C14 C15 119.4(10) . . ? C16 C15 C14 118.8(9) . . ? N11 C16 C15 122.4(10) . . ? 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 N1 C2 22.6(9) . . . . ? Co1 N1 C2 S1 -5.3(11) . . . . ? N1 C2 S1 C1 -80.2(8) . . . . ? C2 S1 C1 S11 67.8(6) . . . . ? S1 C1 S11 C12 66.8(6) . . . . ? C1 S11 C12 N11 -89.1(7) . . . . ? S11 C12 N11 Co1 -6.3(9) . . . . ? C12 N11 Co1 N1 49.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.217 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.154 data_4 _database_code_depnum_ccdc_archive 'CCDC 778416' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778416 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Br2 N2 Ni O S2' _chemical_formula_weight 470.88 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' Ni Ni 0.3393 1.1124 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.1669(14) _cell_length_b 10.7108(15) _cell_length_c 14.823(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.067(2) _cell_angle_gamma 90.00 _cell_volume 1565.7(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 block _exptl_crystal_colour brown _exptl_crystal_size_max .32 _exptl_crystal_size_mid .17 _exptl_crystal_size_min .17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.998 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 6.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6449 _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 4719 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 28.04 _reflns_number_total 1828 _reflns_number_gt 1382 _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 'ORTEPIII, 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^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 1828 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 Br1 Br 0.13601(3) 0.27361(3) 0.18236(2) 0.04163(11) Uani 1 1 d . . . Ni1 Ni 0.0000 0.12976(5) 0.2500 0.02842(14) Uani 1 2 d S . . S1 S 0.05993(8) -0.08004(7) 0.16563(6) 0.03786(19) Uani 1 1 d . . . N1 N -0.1383(2) 0.0817(2) 0.13246(16) 0.0315(5) Uani 1 1 d . . . C1 C 0.0000 -0.1716(4) 0.2500 0.0358(10) Uani 1 2 d S . . H1A H 0.0731 -0.2251 0.2827 0.043 Uiso 0.50 1 calc PR . . H1B H -0.0731 -0.2251 0.2173 0.043 Uiso 0.50 1 calc PR . . C2 C -0.0975(3) -0.0232(3) 0.09844(19) 0.0325(7) Uani 1 1 d . . . C3 C -0.1696(3) -0.0793(3) 0.0178(2) 0.0464(8) Uani 1 1 d . . . H3 H -0.1384 -0.1519 -0.0044 0.056 Uiso 1 1 calc R . . C4 C -0.2895(4) -0.0242(4) -0.0289(2) 0.0565(10) Uani 1 1 d . . . H4 H -0.3402 -0.0591 -0.0839 0.068 Uiso 1 1 calc R . . C5 C -0.3336(3) 0.0823(3) 0.0061(2) 0.0517(9) Uani 1 1 d . . . H5 H -0.4148 0.1198 -0.0243 0.062 Uiso 1 1 calc R . . C6 C -0.2553(3) 0.1327(3) 0.0871(2) 0.0429(8) Uani 1 1 d . . . H6 H -0.2851 0.2049 0.1109 0.051 Uiso 1 1 calc R . . O1 O 0.0000 0.5386(3) 0.2500 0.0962(15) Uani 1 2 d S . . H11 H 0.0871 0.5007 0.2569 0.115 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04048(19) 0.04462(19) 0.0407(2) 0.00467(15) 0.01161(14) -0.00841(14) Ni1 0.0261(3) 0.0299(3) 0.0281(3) 0.000 0.0045(2) 0.000 S1 0.0334(4) 0.0417(4) 0.0408(5) -0.0011(4) 0.0134(3) 0.0038(3) N1 0.0297(13) 0.0350(13) 0.0288(13) -0.0002(11) 0.0049(10) -0.0002(10) C1 0.038(2) 0.028(2) 0.040(3) 0.000 0.0075(19) 0.000 C2 0.0346(16) 0.0355(15) 0.0287(16) -0.0017(13) 0.0103(13) -0.0035(13) C3 0.055(2) 0.0487(19) 0.0355(18) -0.0099(16) 0.0110(16) -0.0072(16) C4 0.061(2) 0.069(2) 0.0318(19) -0.0009(18) -0.0031(17) -0.020(2) C5 0.0394(19) 0.065(2) 0.044(2) 0.0133(19) -0.0023(16) -0.0020(17) C6 0.0394(18) 0.0439(17) 0.042(2) 0.0041(16) 0.0030(15) 0.0041(15) O1 0.117(4) 0.055(2) 0.102(4) 0.000 -0.002(3) 0.000 _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 Ni1 2.4424(5) . ? Ni1 N1 2.021(2) . ? Ni1 N1 2.021(2) 2 ? Ni1 Br1 2.4424(5) 2 ? Ni1 S1 2.7119(9) . ? Ni1 S1 2.7119(9) 2 ? S1 C2 1.775(3) . ? S1 C1 1.808(2) . ? N1 C6 1.333(4) . ? N1 C2 1.338(3) . ? C1 S1 1.808(2) 2 ? C2 C3 1.379(4) . ? C3 C4 1.379(5) . ? C4 C5 1.373(5) . ? C5 C6 1.380(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 150.51(13) . 2 ? N1 Ni1 Br1 98.71(7) . . ? N1 Ni1 Br1 99.77(7) 2 . ? N1 Ni1 Br1 99.77(7) . 2 ? N1 Ni1 Br1 98.71(7) 2 2 ? Br1 Ni1 Br1 101.77(3) . 2 ? N1 Ni1 S1 65.09(7) . . ? N1 Ni1 S1 89.96(7) 2 . ? Br1 Ni1 S1 96.91(2) . . ? Br1 Ni1 S1 157.68(2) 2 . ? N1 Ni1 S1 89.96(7) . 2 ? N1 Ni1 S1 65.09(7) 2 2 ? Br1 Ni1 S1 157.68(2) . 2 ? Br1 Ni1 S1 96.91(2) 2 2 ? S1 Ni1 S1 68.10(4) . 2 ? C2 S1 C1 99.48(10) . . ? C2 S1 Ni1 72.62(9) . . ? C1 S1 Ni1 88.82(11) . . ? C6 N1 C2 118.3(2) . . ? C6 N1 Ni1 132.8(2) . . ? C2 N1 Ni1 108.91(18) . . ? S1 C1 S1 114.3(2) . 2 ? N1 C2 C3 123.0(3) . . ? N1 C2 S1 113.4(2) . . ? C3 C2 S1 123.6(2) . . ? C2 C3 C4 117.9(3) . . ? C5 C4 C3 119.7(3) . . ? C4 C5 C6 118.8(3) . . ? N1 C6 C5 122.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 N1 C2 -51.4(3) 2_656 . . . ? Ni1 N1 C2 S1 -0.8(2) . . . . ? N1 C2 S1 C1 86.3(2) . . . . ? C2 S1 C1 S1 -139.72(10) . . . 2_656 ? S1 C1 S1 C2 -9.9(2) . . 2_656 2_656 ? C1 S1 C2 N1 33.0(3) . 2_656 2_656 2_656 ? S1 C2 N1 Ni1 -12.47(19) 2_656 2_656 2_656 . ? C2 N1 Ni1 N1 -15.2(2) 2_656 2_656 . . ? 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 O1 H11 Br1 0.96 2.77 3.413(3) 126 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.419 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.086 data_5 _database_code_depnum_ccdc_archive 'CCDC 778417' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778417 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 Br4 Cu2 N4 S4' _chemical_formula_weight 915.38 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 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.097(6) _cell_length_b 8.801(5) _cell_length_c 15.687(7) _cell_angle_alpha 90.00 _cell_angle_beta 120.36(3) _cell_angle_gamma 90.00 _cell_volume 1441.1(13) _cell_formula_units_Z 2 _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 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 7.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2542 _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 7583 _diffrn_reflns_av_R_equivalents 0.1438 _diffrn_reflns_av_sigmaI/netI 0.3343 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.10 _reflns_number_total 3235 _reflns_number_gt 1202 _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^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3235 _refine_ls_number_parameters 133 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.2102 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 0.773 _refine_ls_restrained_S_all 0.772 _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 Br1 Br 0.75996(10) -0.68121(12) -0.01717(8) 0.0321(3) Uani 1 1 d . . . Br2 Br 0.85030(12) -1.20030(13) -0.03265(9) 0.0460(4) Uani 1 1 d . . . Cu1 Cu 0.77590(11) -0.95267(13) -0.02394(9) 0.0190(3) Uani 1 1 d . . . S1 S 0.6541(3) -1.1455(3) 0.0881(2) 0.0347(8) Uani 1 1 d . . . S11 S 0.5105(3) -0.9934(3) 0.1691(2) 0.0347(8) Uani 1 1 d . . . N1 N 0.8478(7) -0.9693(8) 0.1225(5) 0.0215(10) Uani 1 1 d U . . C2 C 0.7923(8) -1.0416(10) 0.1678(7) 0.0215(10) Uani 1 1 d U . . C3 C 0.8482(9) -1.0389(10) 0.2692(7) 0.0215(10) Uani 1 1 d U . . H3 H 0.8087 -1.0887 0.2990 0.026 Uiso 1 1 calc R . . C4 C 0.9597(8) -0.9649(10) 0.3256(7) 0.0215(10) Uani 1 1 d U . . H4 H 0.9964 -0.9618 0.3939 0.026 Uiso 1 1 calc R . . C5 C 1.0187(9) -0.8934(10) 0.2804(7) 0.0215(10) Uani 1 1 d U . . H5 H 1.0970 -0.8444 0.3175 0.026 Uiso 1 1 calc R . . C6 C 0.9582(9) -0.8973(10) 0.1793(7) 0.0215(10) Uani 1 1 d . . . H6 H 0.9963 -0.8469 0.1486 0.026 Uiso 1 1 calc R . . N11 N 0.3018(8) -1.0707(8) 0.1699(6) 0.022(2) Uani 1 1 d . . . C12 C 0.4269(9) -1.0532(10) 0.2293(7) 0.019(2) Uani 1 1 d . . . C13 C 0.4817(10) -1.0750(11) 0.3298(8) 0.032(3) Uani 1 1 d . . . H13 H 0.5691 -1.0597 0.3714 0.038 Uiso 1 1 calc R . . C14 C 0.4079(11) -1.1187(11) 0.3681(8) 0.031(3) Uani 1 1 d . . . H14 H 0.4446 -1.1394 0.4352 0.038 Uiso 1 1 calc R . . C15 C 0.2782(12) -1.1316(11) 0.3057(9) 0.038(3) Uani 1 1 d . . . H15 H 0.2251 -1.1538 0.3309 0.045 Uiso 1 1 calc R . . C16 C 0.2271(10) -1.1120(11) 0.2063(8) 0.033(3) Uani 1 1 d . . . H16 H 0.1399 -1.1273 0.1637 0.039 Uiso 1 1 calc R . . C1 C 0.5789(9) -1.1751(11) 0.1585(7) 0.032(3) Uani 1 1 d . . . H1A H 0.6409 -1.2123 0.2237 0.039 Uiso 1 1 calc R . . H1B H 0.5116 -1.2504 0.1265 0.039 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 Br1 0.0381(7) 0.0215(6) 0.0347(7) 0.0003(6) 0.0171(6) 0.0061(6) Br2 0.0758(9) 0.0309(7) 0.0414(8) 0.0074(7) 0.0371(7) 0.0275(8) Cu1 0.0175(7) 0.0198(8) 0.0235(7) 0.0022(6) 0.0131(6) 0.0022(6) S1 0.0240(16) 0.051(2) 0.0298(17) -0.0084(15) 0.0142(14) -0.0179(15) S11 0.0272(17) 0.0257(17) 0.059(2) 0.0099(16) 0.0275(17) -0.0028(14) N1 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) C2 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) C3 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) C4 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) C5 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) C6 0.016(2) 0.023(3) 0.023(2) 0.004(2) 0.009(2) 0.001(2) N11 0.030(6) 0.019(5) 0.022(5) 0.004(4) 0.017(5) 0.003(4) C12 0.011(6) 0.020(6) 0.026(6) -0.004(5) 0.010(5) -0.002(5) C13 0.031(7) 0.016(6) 0.042(8) -0.008(6) 0.014(7) -0.004(6) C14 0.043(8) 0.039(8) 0.024(6) 0.002(6) 0.026(7) -0.001(6) C15 0.043(8) 0.038(8) 0.054(9) 0.002(7) 0.040(7) 0.001(6) C16 0.026(7) 0.040(7) 0.034(7) 0.012(6) 0.017(6) 0.002(6) C1 0.036(7) 0.025(6) 0.043(7) 0.003(6) 0.025(6) -0.003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cu1 2.404(2) . ? Br2 Cu1 2.3881(19) . ? Cu1 N11 1.999(8) 3_635 ? Cu1 N1 2.009(7) . ? S1 C2 1.755(10) . ? S1 C1 1.769(9) . ? S11 C12 1.777(9) . ? S11 C1 1.846(9) . ? N1 C6 1.333(10) . ? N1 C2 1.357(10) . ? C2 C3 1.378(12) . ? C3 C4 1.349(11) . ? C4 C5 1.386(11) . ? C5 C6 1.370(12) . ? N11 C12 1.325(11) . ? N11 C16 1.339(11) . ? N11 Cu1 1.999(8) 3_635 ? C12 C13 1.381(12) . ? C13 C14 1.359(13) . ? C14 C15 1.371(14) . ? C15 C16 1.367(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 N11 Cu1 N1 177.3(3) 3_635 . ? N11 Cu1 Br2 90.0(2) 3_635 . ? N1 Cu1 Br2 92.4(2) . . ? N11 Cu1 Br1 86.9(2) 3_635 . ? N1 Cu1 Br1 91.1(2) . . ? Br2 Cu1 Br1 161.92(6) . . ? C2 S1 C1 103.7(5) . . ? C12 S11 C1 101.1(4) . . ? C6 N1 C2 117.9(8) . . ? C6 N1 Cu1 115.9(6) . . ? C2 N1 Cu1 126.1(6) . . ? N1 C2 C3 120.7(9) . . ? N1 C2 S1 114.6(7) . . ? C3 C2 S1 124.5(7) . . ? C4 C3 C2 120.7(9) . . ? C3 C4 C5 119.1(10) . . ? C6 C5 C4 118.0(9) . . ? N1 C6 C5 123.6(9) . . ? C12 N11 C16 120.6(9) . . ? C12 N11 Cu1 120.1(7) . 3_635 ? C16 N11 Cu1 119.2(7) . 3_635 ? N11 C12 C13 120.3(9) . . ? N11 C12 S11 114.5(7) . . ? C13 C12 S11 125.1(8) . . ? C14 C13 C12 120.0(10) . . ? C13 C14 C15 118.6(11) . . ? C16 C15 C14 119.9(10) . . ? N11 C16 C15 120.4(10) . . ? S1 C1 S11 108.9(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 C15 H15 Br1 0.93 2.84 3.600(11) 139.1 2_645 C13 H13 Br1 0.93 2.97 3.743(10) 141.9 4_546 C4 H4 Br2 0.93 3.07 3.703(10) 127.2 2_755 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 28.10 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.967 _refine_diff_density_min -1.613 _refine_diff_density_rms 0.199 data_6 _database_code_depnum_ccdc_archive 'CCDC 778418' #TrackingRef '- DT_ART_05_2010_000560_Mat_dep.cif' ############### # CCDC 778418 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Br2 Cu N3 S2' _chemical_formula_weight 498.74 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 8.8365(17) _cell_length_b 12.617(3) _cell_length_c 15.658(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.709(4) _cell_angle_gamma 90.00 _cell_volume 1720.6(6) _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 'dark green' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.925 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 6.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.578853 _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 9780 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.1312 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3888 _reflns_number_gt 1917 _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 '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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0196P)^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 3888 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 0.760 _refine_ls_restrained_S_all 0.760 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.29796(7) 0.84989(5) 0.21331(4) 0.03162(17) Uani 1 1 d . . . Br1 Br 0.13611(6) 0.89261(5) 0.07846(4) 0.04398(18) Uani 1 1 d . . . Br2 Br 0.45600(6) 0.90740(5) 0.34558(4) 0.04566(18) Uani 1 1 d . . . C1 C 0.6241(6) 1.1243(4) 0.1152(3) 0.0381(14) Uani 1 1 d . . . H1A H 0.5838 1.1947 0.1007 0.046 Uiso 1 1 calc R . . H1B H 0.6820 1.1021 0.0709 0.046 Uiso 1 1 calc R . . S1 S 0.46911(16) 1.03356(11) 0.11926(9) 0.0393(4) Uani 1 1 d . . . N1 N 0.4849(4) 0.8294(3) 0.1575(2) 0.0318(11) Uani 1 1 d . . . C2 C 0.5591(5) 0.9078(4) 0.1236(3) 0.0280(12) Uani 1 1 d . . . C3 C 0.6941(6) 0.8871(4) 0.0917(3) 0.0363(14) Uani 1 1 d . . . H3 H 0.7465 0.9417 0.0695 0.044 Uiso 1 1 calc R . . C4 C 0.7491(6) 0.7847(5) 0.0935(3) 0.0457(16) Uani 1 1 d . . . H4 H 0.8386 0.7697 0.0719 0.055 Uiso 1 1 calc R . . C5 C 0.6714(6) 0.7055(4) 0.1272(3) 0.0430(15) Uani 1 1 d . . . H5 H 0.7071 0.6360 0.1286 0.052 Uiso 1 1 calc R . . C6 C 0.5417(6) 0.7298(4) 0.1583(3) 0.0388(14) Uani 1 1 d . . . H6 H 0.4895 0.6756 0.1812 0.047 Uiso 1 1 calc R . . S11 S 0.74847(16) 1.12638(11) 0.22007(9) 0.0368(4) Uani 1 1 d . . . N11 N 0.8832(4) 1.3147(3) 0.2296(2) 0.0305(11) Uani 1 1 d . . . C12 C 0.8945(6) 1.2150(4) 0.2005(3) 0.0287(12) Uani 1 1 d . . . C13 C 1.0130(6) 1.1836(5) 0.1580(3) 0.0436(15) Uani 1 1 d . . . H13 H 1.0156 1.1153 0.1360 0.052 Uiso 1 1 calc R . . C14 C 1.1257(6) 1.2552(5) 0.1492(3) 0.0458(16) Uani 1 1 d . . . H14 H 1.2073 1.2351 0.1222 0.055 Uiso 1 1 calc R . . C15 C 1.1188(6) 1.3569(5) 0.1802(3) 0.0417(15) Uani 1 1 d . . . H15 H 1.1950 1.4060 0.1746 0.050 Uiso 1 1 calc R . . C16 C 0.9957(6) 1.3841(4) 0.2198(3) 0.0416(15) Uani 1 1 d . . . H16 H 0.9900 1.4528 0.2405 0.050 Uiso 1 1 calc R . . N111 N -0.0003(6) 0.5959(4) 0.0961(4) 0.0698(17) Uani 1 1 d . . . C111 C 0.0991(8) 0.5990(5) 0.0594(4) 0.0498(16) Uani 1 1 d . . . C112 C 0.2277(7) 0.6007(5) 0.0121(4) 0.072(2) Uani 1 1 d . . . H11A H 0.3078 0.5553 0.0405 0.108 Uiso 1 1 calc R . . H11B H 0.2659 0.6718 0.0107 0.108 Uiso 1 1 calc R . . H11C H 0.1940 0.5762 -0.0460 0.108 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 0.0233(4) 0.0365(4) 0.0372(4) 0.0007(3) 0.0112(3) -0.0010(3) Br1 0.0297(4) 0.0614(4) 0.0410(4) 0.0065(3) 0.0065(3) -0.0060(3) Br2 0.0367(4) 0.0581(4) 0.0433(4) -0.0089(3) 0.0098(3) -0.0083(3) C1 0.034(3) 0.038(4) 0.042(3) 0.008(3) 0.005(3) -0.011(3) S1 0.0286(9) 0.0373(9) 0.0538(9) 0.0037(7) 0.0125(7) -0.0022(7) N1 0.027(3) 0.038(3) 0.033(3) -0.002(2) 0.011(2) -0.002(2) C2 0.022(3) 0.033(3) 0.028(3) -0.001(2) 0.001(2) -0.002(2) C3 0.030(3) 0.040(4) 0.040(3) 0.002(3) 0.007(3) -0.008(3) C4 0.033(4) 0.056(4) 0.051(4) -0.009(3) 0.017(3) 0.001(3) C5 0.037(4) 0.035(4) 0.061(4) 0.000(3) 0.019(3) 0.001(3) C6 0.034(4) 0.039(4) 0.047(4) -0.001(3) 0.017(3) -0.003(3) S11 0.0347(9) 0.0379(9) 0.0393(8) 0.0019(6) 0.0107(7) -0.0055(6) N11 0.019(3) 0.034(3) 0.039(3) 0.000(2) 0.008(2) 0.000(2) C12 0.022(3) 0.030(3) 0.032(3) 0.005(2) -0.001(3) 0.001(2) C13 0.035(4) 0.050(4) 0.050(4) -0.008(3) 0.019(3) 0.005(3) C14 0.030(4) 0.059(5) 0.052(4) -0.004(3) 0.017(3) 0.009(3) C15 0.027(3) 0.054(4) 0.049(4) 0.001(3) 0.020(3) -0.004(3) C16 0.035(4) 0.043(4) 0.047(4) -0.006(3) 0.010(3) -0.009(3) N111 0.070(4) 0.065(4) 0.082(4) 0.006(3) 0.034(4) 0.009(3) C111 0.057(5) 0.042(4) 0.048(4) -0.001(3) 0.002(4) 0.002(3) C112 0.048(5) 0.107(6) 0.061(5) -0.011(4) 0.013(4) -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 Cu N11 2.011(4) 2_645 ? Cu N1 2.011(4) . ? Cu Br1 2.4031(9) . ? Cu Br2 2.4064(9) . ? Cu S11 3.0582(16) 2_645 ? Cu S1 3.2522(15) . ? C1 S1 1.794(5) . ? C1 S11 1.816(5) . ? S1 C2 1.771(5) . ? N1 C2 1.344(6) . ? N1 C6 1.353(6) . ? C2 C3 1.394(6) . ? C3 C4 1.379(6) . ? C4 C5 1.368(7) . ? C5 C6 1.354(6) . ? S11 C12 1.773(5) . ? N11 C12 1.346(6) . ? N11 C16 1.352(6) . ? N11 Cu 2.011(4) 2_655 ? C12 C13 1.389(6) . ? C13 C14 1.369(7) . ? C14 C15 1.376(7) . ? C15 C16 1.383(6) . ? N111 C111 1.128(7) . ? C111 C112 1.457(8) . ? 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 Cu N1 159.83(17) 2_645 . ? N11 Cu Br1 92.29(12) 2_645 . ? N1 Cu Br1 93.33(12) . . ? N11 Cu Br2 94.23(11) 2_645 . ? N1 Cu Br2 90.71(11) . . ? Br1 Cu Br2 149.49(3) . . ? N11 Cu S11 58.79(12) 2_645 2_645 ? N1 Cu S11 101.37(13) . 2_645 ? Br1 Cu S11 114.35(4) . 2_645 ? Br2 Cu S11 94.37(4) . 2_645 ? N11 Cu S1 145.57(12) 2_645 . ? N1 Cu S1 54.27(13) . . ? Br1 Cu S1 72.28(3) . . ? Br2 Cu S1 85.88(4) . . ? S11 Cu S1 155.62(4) 2_645 . ? S1 C1 S11 109.1(2) . . ? C2 S1 C1 103.4(2) . . ? C2 S1 Cu 65.43(16) . . ? C1 S1 Cu 152.45(17) . . ? C2 N1 C6 118.8(4) . . ? C2 N1 Cu 124.6(3) . . ? C6 N1 Cu 116.5(3) . . ? N1 C2 C3 120.5(5) . . ? N1 C2 S1 115.4(4) . . ? C3 C2 S1 124.1(4) . . ? C4 C3 C2 119.2(5) . . ? C5 C4 C3 119.6(5) . . ? C6 C5 C4 118.9(5) . . ? N1 C6 C5 122.9(5) . . ? C12 S11 C1 101.5(2) . . ? C12 N11 C16 118.0(4) . . ? C12 N11 Cu 117.8(3) . 2_655 ? C16 N11 Cu 124.2(4) . 2_655 ? N11 C12 C13 122.2(5) . . ? N11 C12 S11 115.7(4) . . ? C13 C12 S11 122.2(4) . . ? C14 C13 C12 118.7(5) . . ? C13 C14 C15 120.2(5) . . ? C14 C15 C16 118.3(5) . . ? N11 C16 C15 122.6(5) . . ? N111 C111 C112 178.9(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S11 C1 S1 C2 -71.2(3) . . . . ? S11 C1 S1 Cu -9.0(6) . . . . ? N11 Cu S1 C2 -177.5(3) 2_645 . . . ? N1 Cu S1 C2 -2.9(2) . . . . ? Br1 Cu S1 C2 -110.60(17) . . . . ? Br2 Cu S1 C2 91.00(17) . . . . ? S11 Cu S1 C2 -0.5(2) 2_645 . . . ? N11 Cu S1 C1 111.4(4) 2_645 . . . ? N1 Cu S1 C1 -73.9(4) . . . . ? Br1 Cu S1 C1 178.3(4) . . . . ? Br2 Cu S1 C1 19.9(4) . . . . ? S11 Cu S1 C1 -71.6(4) 2_645 . . . ? N11 Cu N1 C2 175.4(4) 2_645 . . . ? Br1 Cu N1 C2 69.5(4) . . . . ? Br2 Cu N1 C2 -80.3(4) . . . . ? S11 Cu N1 C2 -174.9(3) 2_645 . . . ? S1 Cu N1 C2 4.2(3) . . . . ? N11 Cu N1 C6 -7.5(7) 2_645 . . . ? Br1 Cu N1 C6 -113.4(3) . . . . ? Br2 Cu N1 C6 96.8(3) . . . . ? S11 Cu N1 C6 2.2(4) 2_645 . . . ? S1 Cu N1 C6 -178.8(4) . . . . ? C6 N1 C2 C3 -1.6(7) . . . . ? Cu N1 C2 C3 175.5(3) . . . . ? C6 N1 C2 S1 176.1(3) . . . . ? Cu N1 C2 S1 -6.9(5) . . . . ? C1 S1 C2 N1 157.1(4) . . . . ? Cu S1 C2 N1 3.8(3) . . . . ? C1 S1 C2 C3 -25.3(5) . . . . ? Cu S1 C2 C3 -178.6(5) . . . . ? N1 C2 C3 C4 1.5(7) . . . . ? S1 C2 C3 C4 -175.9(4) . . . . ? C2 C3 C4 C5 -0.6(8) . . . . ? C3 C4 C5 C6 -0.2(8) . . . . ? C2 N1 C6 C5 0.7(7) . . . . ? Cu N1 C6 C5 -176.5(4) . . . . ? C4 C5 C6 N1 0.1(8) . . . . ? S1 C1 S11 C12 177.8(3) . . . . ? C16 N11 C12 C13 -2.9(7) . . . . ? Cu N11 C12 C13 178.2(4) 2_655 . . . ? C16 N11 C12 S11 177.0(4) . . . . ? Cu N11 C12 S11 -1.9(5) 2_655 . . . ? C1 S11 C12 N11 100.8(4) . . . . ? C1 S11 C12 C13 -79.3(5) . . . . ? N11 C12 C13 C14 3.1(8) . . . . ? S11 C12 C13 C14 -176.7(4) . . . . ? C12 C13 C14 C15 -1.6(8) . . . . ? C13 C14 C15 C16 -0.1(8) . . . . ? C12 N11 C16 C15 1.1(7) . . . . ? Cu N11 C16 C15 179.9(4) 2_655 . . . ? C14 C15 C16 N11 0.4(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 C1 H1A Br2 0.97 2.85 3.713(5) 148.5 2_655 C4 H4 N111 0.93 2.61 3.248(8) 126.6 1_655 C6 H6 S11 0.93 2.88 3.681(5) 145.2 2_645 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.514 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.102