# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [dichloridobis(pyrimidin2-2(1H)-thione-kN:kS)nickel(II)] ; _chemical_formula_moiety 'C8 H8 Cl2 N4 Ni S2' _chemical_formula_structural 'C8 H8 Cl2 N4 Ni S2' _chemical_formula_sum 'C8 H8 Cl2 N4 Ni S2' _chemical_formula_weight 353.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 12.2435(7) _cell_length_b 8.1093(4) _cell_length_c 14.0786(7) _cell_angle_alpha 90.00 _cell_angle_beta 115.450(3) _cell_angle_gamma 90.00 _cell_volume 1262.17(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4754 _cell_measurement_theta_min 6.77 _cell_measurement_theta_max 69.70 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 9.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.1345 _exptl_absorpt_correction_T_max 0.3037 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 4754 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 6.77 _diffrn_reflns_theta_max 69.70 _reflns_number_total 1162 _reflns_number_gt 1063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+1.0414P] 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 1162 _refine_ls_number_parameters 81 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Ni1 Ni 0.5000 0.18119(6) 0.2500 0.0156(2) Uani 1 2 d S . . S1 S 0.65621(5) 0.40027(6) 0.36450(4) 0.0178(2) Uani 1 1 d . . . C1 C 0.5874(2) 0.3304(3) 0.43743(17) 0.0150(5) Uani 1 1 d . . . C2 C 0.5549(2) 0.3166(3) 0.59154(18) 0.0203(5) Uani 1 1 d . . . H2 H 0.5798 0.3451 0.6633 0.024 Uiso 1 1 calc R . . C3 C 0.4560(2) 0.2193(3) 0.54170(19) 0.0228(5) Uani 1 1 d . . . H3 H 0.4073 0.1850 0.5754 0.027 Uiso 1 1 calc R . . C4 C 0.4294(2) 0.1724(3) 0.43880(19) 0.0197(5) Uani 1 1 d . . . H4 H 0.3626 0.1012 0.4028 0.024 Uiso 1 1 calc R . . Cl1 Cl 0.65471(5) -0.02560(6) 0.29657(4) 0.0183(2) Uani 1 1 d . . . N1 N 0.49442(17) 0.2238(2) 0.38946(15) 0.0166(4) Uani 1 1 d . . . N2 N 0.61749(18) 0.3726(2) 0.53958(16) 0.0182(4) Uani 1 1 d . . . H2A H 0.684(3) 0.433(4) 0.578(3) 0.022 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 Ni1 0.0144(3) 0.0188(3) 0.0115(3) 0.000 0.0037(2) 0.000 S1 0.0151(3) 0.0196(3) 0.0179(3) -0.0010(2) 0.0063(2) -0.0022(2) C1 0.0132(11) 0.0157(10) 0.0129(11) -0.0010(8) 0.0026(8) 0.0037(8) C2 0.0252(13) 0.0202(11) 0.0135(12) 0.0020(9) 0.0064(10) 0.0067(9) C3 0.0292(14) 0.0219(11) 0.0210(13) 0.0023(10) 0.0143(10) 0.0012(10) C4 0.0207(12) 0.0184(11) 0.0192(12) 0.0015(9) 0.0077(9) -0.0001(9) Cl1 0.0166(3) 0.0204(3) 0.0138(3) 0.00052(19) 0.0026(2) 0.00045(19) N1 0.0149(10) 0.0178(9) 0.0148(9) -0.0005(7) 0.0042(8) -0.0001(7) N2 0.0173(11) 0.0187(9) 0.0134(10) -0.0012(8) 0.0015(8) 0.0028(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.023(2) . ? Ni1 N1 2.023(2) 2_655 ? Ni1 Cl1 2.4005(6) 2_655 ? Ni1 Cl1 2.4005(6) . ? Ni1 S1 2.6005(6) . ? Ni1 S1 2.6005(6) 2_655 ? S1 C1 1.682(2) . ? C1 N1 1.356(3) . ? C1 N2 1.366(3) . ? C2 N2 1.345(3) . ? C2 C3 1.360(4) . ? C2 H2 0.9500 . ? C3 C4 1.394(4) . ? C3 H3 0.9500 . ? C4 N1 1.328(3) . ? C4 H4 0.9500 . ? N2 H2A 0.90(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 160.35(11) . 2_655 ? N1 Ni1 Cl1 91.86(6) . 2_655 ? N1 Ni1 Cl1 101.88(6) 2_655 2_655 ? N1 Ni1 Cl1 101.88(5) . . ? N1 Ni1 Cl1 91.86(6) 2_655 . ? Cl1 Ni1 Cl1 91.37(3) 2_655 . ? N1 Ni1 S1 66.70(6) . . ? N1 Ni1 S1 99.35(6) 2_655 . ? Cl1 Ni1 S1 158.488(18) 2_655 . ? Cl1 Ni1 S1 91.382(17) . . ? N1 Ni1 S1 99.35(6) . 2_655 ? N1 Ni1 S1 66.70(6) 2_655 2_655 ? Cl1 Ni1 S1 91.382(17) 2_655 2_655 ? Cl1 Ni1 S1 158.488(18) . 2_655 ? S1 Ni1 S1 93.82(3) . 2_655 ? C1 S1 Ni1 73.76(8) . . ? N1 C1 N2 118.2(2) . . ? N1 C1 S1 116.37(17) . . ? N2 C1 S1 125.40(18) . . ? N2 C2 C3 120.3(2) . . ? N2 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 116.9(2) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? N1 C4 C3 122.2(2) . . ? N1 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 N1 C1 120.2(2) . . ? C4 N1 Ni1 137.02(16) . . ? C1 N1 Ni1 102.77(15) . . ? C2 N2 C1 121.9(2) . . ? C2 N2 H2A 116(2) . . ? C1 N2 H2A 122(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 Ni1 S1 C1 3.46(10) . . . . ? N1 Ni1 S1 C1 168.99(10) 2_655 . . . ? Cl1 Ni1 S1 C1 -1.62(10) 2_655 . . . ? Cl1 Ni1 S1 C1 -98.89(8) . . . . ? S1 Ni1 S1 C1 101.99(8) 2_655 . . . ? Ni1 S1 C1 N1 -5.29(15) . . . . ? Ni1 S1 C1 N2 174.8(2) . . . . ? N2 C2 C3 C4 4.5(3) . . . . ? C2 C3 C4 N1 -2.2(4) . . . . ? C3 C4 N1 C1 -2.6(3) . . . . ? C3 C4 N1 Ni1 175.06(18) . . . . ? N2 C1 N1 C4 5.0(3) . . . . ? S1 C1 N1 C4 -174.97(17) . . . . ? N2 C1 N1 Ni1 -173.38(16) . . . . ? S1 C1 N1 Ni1 6.70(18) . . . . ? N1 Ni1 N1 C4 130.8(2) 2_655 . . . ? Cl1 Ni1 N1 C4 -4.0(2) 2_655 . . . ? Cl1 Ni1 N1 C4 -95.8(2) . . . . ? S1 Ni1 N1 C4 177.9(2) . . . . ? S1 Ni1 N1 C4 87.7(2) 2_655 . . . ? N1 Ni1 N1 C1 -51.35(13) 2_655 . . . ? Cl1 Ni1 N1 C1 173.92(13) 2_655 . . . ? Cl1 Ni1 N1 C1 82.12(13) . . . . ? S1 Ni1 N1 C1 -4.22(12) . . . . ? S1 Ni1 N1 C1 -94.37(13) 2_655 . . . ? C3 C2 N2 C1 -2.2(3) . . . . ? N1 C1 N2 C2 -2.7(3) . . . . ? S1 C1 N2 C2 177.25(17) . . . . ? 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 N2 H2A Cl1 0.90(3) 2.14(3) 3.018(2) 163(3) 7_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 69.70 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.677 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 937856' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [dibromidobis(pyrimidin2-2(1H)-thione-kN:kS)nickel(II)] ; _chemical_formula_moiety 'C8 H8 Br2 N4 Ni S2' _chemical_formula_structural 'C8 H8 Br2 N4 Ni S2' _chemical_formula_sum 'C8 H8 Br2 N4 Ni S2' _chemical_formula_weight 442.83 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 12.3010(7) _cell_length_b 8.1427(5) _cell_length_c 14.4506(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.723(2) _cell_angle_gamma 90.00 _cell_volume 1314.75(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6462 _cell_measurement_theta_min 6.73 _cell_measurement_theta_max 70.85 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 12.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.1726 _exptl_absorpt_correction_T_max 0.3847 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 6462 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 6.73 _diffrn_reflns_theta_max 70.85 _reflns_number_total 1228 _reflns_number_gt 1168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+5.1530P] 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 1228 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.61382(4) 0.20640(5) 0.70041(3) 0.0239(2) Uani 1 1 d . . . Ni1 Ni 0.5000 0.42637(11) 0.7500 0.0162(3) Uani 1 2 d S . . S1 S 0.54080(8) 0.64337(11) 0.63743(7) 0.0198(3) Uani 1 1 d . . . C1 C 0.4011(3) 0.5737(4) 0.5683(3) 0.0171(7) Uani 1 1 d . . . C2 C 0.2170(4) 0.5613(5) 0.4212(3) 0.0225(8) Uani 1 1 d . . . H2 H 0.1709 0.5908 0.3521 0.027 Uiso 1 1 calc R . . C3 C 0.1683(4) 0.4643(5) 0.4706(3) 0.0252(8) Uani 1 1 d . . . H3 H 0.0870 0.4300 0.4390 0.030 Uiso 1 1 calc R . . C4 C 0.2433(4) 0.4171(5) 0.5703(3) 0.0211(8) Uani 1 1 d . . . H4 H 0.2125 0.3475 0.6063 0.025 Uiso 1 1 calc R . . N1 N 0.3563(3) 0.4667(4) 0.6159(2) 0.0175(6) Uani 1 1 d . . . N2 N 0.3303(3) 0.6157(4) 0.4698(2) 0.0203(7) Uani 1 1 d . . . H2A H 0.356(6) 0.664(8) 0.436(5) 0.039(16) 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 0.0256(3) 0.0252(3) 0.0217(3) -0.00047(13) 0.0107(2) 0.00000(14) Ni1 0.0143(5) 0.0177(5) 0.0161(5) 0.000 0.0059(4) 0.000 S1 0.0171(5) 0.0203(5) 0.0232(5) 0.0019(3) 0.0097(4) -0.0013(3) C1 0.0191(18) 0.0162(18) 0.0176(17) -0.0015(13) 0.0093(15) 0.0023(13) C2 0.025(2) 0.0195(19) 0.0178(17) -0.0041(14) 0.0043(16) 0.0048(14) C3 0.0210(19) 0.023(2) 0.026(2) -0.0045(15) 0.0038(16) -0.0010(15) C4 0.0201(19) 0.0189(19) 0.0240(18) -0.0028(14) 0.0088(16) 0.0001(14) N1 0.0172(15) 0.0161(15) 0.0197(15) -0.0007(11) 0.0084(12) 0.0000(12) N2 0.0235(16) 0.0202(17) 0.0188(15) 0.0000(13) 0.0105(14) 0.0039(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.5536(7) . ? Ni1 N1 2.031(3) 2_656 ? Ni1 N1 2.031(3) . ? Ni1 Br1 2.5536(7) 2_656 ? Ni1 S1 2.5891(10) 2_656 ? Ni1 S1 2.5891(11) . ? S1 C1 1.684(4) . ? C1 N1 1.360(5) . ? C1 N2 1.366(5) . ? C2 N2 1.347(6) . ? C2 C3 1.361(6) . ? C2 H2 0.9500 . ? C3 C4 1.401(6) . ? C3 H3 0.9500 . ? C4 N1 1.327(5) . ? C4 H4 0.9500 . ? N2 H2A 0.79(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 Ni1 N1 161.36(18) 2_656 . ? N1 Ni1 Br1 101.91(9) 2_656 2_656 ? N1 Ni1 Br1 91.19(9) . 2_656 ? N1 Ni1 Br1 91.19(9) 2_656 . ? N1 Ni1 Br1 101.91(9) . . ? Br1 Ni1 Br1 90.92(3) 2_656 . ? N1 Ni1 S1 67.04(9) 2_656 2_656 ? N1 Ni1 S1 99.74(9) . 2_656 ? Br1 Ni1 S1 91.68(2) 2_656 2_656 ? Br1 Ni1 S1 158.14(2) . 2_656 ? N1 Ni1 S1 99.74(9) 2_656 . ? N1 Ni1 S1 67.04(9) . . ? Br1 Ni1 S1 158.14(2) 2_656 . ? Br1 Ni1 S1 91.68(2) . . ? S1 Ni1 S1 93.92(5) 2_656 . ? C1 S1 Ni1 74.03(13) . . ? N1 C1 N2 118.1(3) . . ? N1 C1 S1 116.4(3) . . ? N2 C1 S1 125.5(3) . . ? N2 C2 C3 120.3(4) . . ? N2 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 116.9(4) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? N1 C4 C3 122.0(4) . . ? N1 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 N1 C1 120.3(3) . . ? C4 N1 Ni1 137.5(3) . . ? C1 N1 Ni1 102.2(2) . . ? C2 N2 C1 122.1(4) . . ? C2 N2 H2A 116(5) . . ? C1 N2 H2A 122(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 Ni1 S1 C1 -169.60(16) 2_656 . . . ? N1 Ni1 S1 C1 -3.33(15) . . . . ? Br1 Ni1 S1 C1 2.22(16) 2_656 . . . ? Br1 Ni1 S1 C1 98.90(13) . . . . ? S1 Ni1 S1 C1 -102.24(13) 2_656 . . . ? Ni1 S1 C1 N1 5.1(2) . . . . ? Ni1 S1 C1 N2 -175.0(3) . . . . ? N2 C2 C3 C4 -3.8(6) . . . . ? C2 C3 C4 N1 1.3(6) . . . . ? C3 C4 N1 C1 3.6(6) . . . . ? C3 C4 N1 Ni1 -175.7(3) . . . . ? N2 C1 N1 C4 -5.9(5) . . . . ? S1 C1 N1 C4 174.0(3) . . . . ? N2 C1 N1 Ni1 173.7(3) . . . . ? S1 C1 N1 Ni1 -6.4(3) . . . . ? N1 Ni1 N1 C4 -129.5(4) 2_656 . . . ? Br1 Ni1 N1 C4 5.6(4) 2_656 . . . ? Br1 Ni1 N1 C4 96.8(4) . . . . ? S1 Ni1 N1 C4 -86.3(4) 2_656 . . . ? S1 Ni1 N1 C4 -176.5(4) . . . . ? N1 Ni1 N1 C1 51.1(2) 2_656 . . . ? Br1 Ni1 N1 C1 -173.9(2) 2_656 . . . ? Br1 Ni1 N1 C1 -82.7(2) . . . . ? S1 Ni1 N1 C1 94.2(2) 2_656 . . . ? S1 Ni1 N1 C1 4.05(19) . . . . ? C3 C2 N2 C1 1.5(6) . . . . ? N1 C1 N2 C2 3.4(5) . . . . ? S1 C1 N2 C2 -176.5(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 N2 H2A Br1 0.79(7) 2.40(7) 3.168(4) 166(6) 5_666 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 70.85 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.943 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.180 _database_code_depnum_ccdc_archive 'CCDC 937857' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [triaquachlorido(2,2'-sulfanediyldipyrimidine-kN,kN')nickel(II)] chloride ; _chemical_formula_moiety 'C8 H12 Cl N4 Ni O3 S, Cl' _chemical_formula_structural 'C8 H12 Cl N4 Ni O3 S, Cl' _chemical_formula_sum 'C8 H12 Cl2 N4 Ni O3 S' _chemical_formula_weight 373.89 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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/n _symmetry_space_group_name_Hall '-C 2ybc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x, -y+1/2, z-1/2' _cell_length_a 25.525(2) _cell_length_b 8.6097(8) _cell_length_c 13.0673(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.747(6) _cell_angle_gamma 90.00 _cell_volume 2749.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7268 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 66.99 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 7.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.6872 _exptl_absorpt_correction_T_max 0.8229 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\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 7268 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 66.99 _reflns_number_total 2354 _reflns_number_gt 2174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+50.3673P] 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 2354 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 1.294 _refine_ls_restrained_S_all 1.294 _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 Ni1 Ni 0.42026(4) 0.30724(13) 0.30025(9) 0.0209(3) Uani 1 1 d . . . N1 N 0.3489(2) 0.2346(7) 0.3314(4) 0.0255(13) Uani 1 1 d . . . N2 N 0.2702(3) 0.2851(9) 0.3902(5) 0.0435(19) Uani 1 1 d . . . N3 N 0.3780(2) 0.4949(7) 0.2146(4) 0.0230(12) Uani 1 1 d . . . N4 N 0.3230(2) 0.7201(7) 0.2041(5) 0.0291(14) Uani 1 1 d . . . C1 C 0.3394(3) 0.0803(10) 0.3355(6) 0.0314(17) Uani 1 1 d . . . H1 H 0.3625 0.0106 0.3156 0.038 Uiso 1 1 calc R . . C2 C 0.2961(3) 0.0235(11) 0.3687(6) 0.042(2) Uani 1 1 d . . . H2 H 0.2895 -0.0825 0.3710 0.050 Uiso 1 1 calc R . . C3 C 0.2632(4) 0.1316(13) 0.3981(7) 0.052(3) Uani 1 1 d . . . H3 H 0.2351 0.0967 0.4244 0.062 Uiso 1 1 calc R . . C4 C 0.3126(3) 0.3269(9) 0.3563(6) 0.0302(17) Uani 1 1 d . . . C5 C 0.3933(3) 0.5459(9) 0.1316(5) 0.0294(16) Uani 1 1 d . . . H5 H 0.4162 0.4841 0.1048 0.035 Uiso 1 1 calc R . . C6 C 0.3764(3) 0.6879(9) 0.0836(6) 0.0365(19) Uani 1 1 d . . . H6 H 0.3880 0.7243 0.0266 0.044 Uiso 1 1 calc R . . C7 C 0.3416(3) 0.7716(9) 0.1249(6) 0.0324(17) Uani 1 1 d . . . H7 H 0.3304 0.8692 0.0964 0.039 Uiso 1 1 calc R . . C8 C 0.3421(3) 0.5817(8) 0.2447(5) 0.0234(15) Uani 1 1 d . . . S1 S 0.31528(7) 0.5329(2) 0.35080(15) 0.0323(5) Uani 1 1 d . . . Cl1 Cl 0.40507(7) 0.1440(2) 0.14555(13) 0.0266(4) Uani 1 1 d . . . Cl2 Cl 0.44961(6) 0.78330(19) 0.38789(13) 0.0248(4) Uani 1 1 d . . . O1W O 0.4644(2) 0.1378(6) 0.3968(4) 0.0443(15) Uani 1 1 d . . . H11 H 0.4607 0.0390 0.3981 0.066 Uiso 1 1 d R . . H12 H 0.4879 0.1597 0.4560 0.066 Uiso 1 1 d R . . O2W O 0.4922(2) 0.3878(7) 0.2769(5) 0.0400(14) Uani 1 1 d . . . H21 H 0.5071 0.3455 0.2322 0.060 Uiso 1 1 d R . . H22 H 0.5165 0.4581 0.3083 0.060 Uiso 1 1 d R . . O3W O 0.44279(19) 0.4341(6) 0.4396(3) 0.0255(11) Uani 1 1 d . . . H31 H 0.4427 0.5336 0.4316 0.038 Uiso 1 1 d R . . H32 H 0.4326 0.4198 0.4961 0.038 Uiso 1 1 d 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 Ni1 0.0175(6) 0.0269(6) 0.0175(6) 0.0006(5) 0.0039(5) -0.0001(5) N1 0.024(3) 0.039(4) 0.012(3) -0.005(2) 0.004(2) -0.005(3) N2 0.040(4) 0.061(5) 0.039(4) -0.020(4) 0.027(3) -0.022(4) N3 0.021(3) 0.033(3) 0.014(3) -0.002(2) 0.004(2) -0.002(2) N4 0.023(3) 0.038(4) 0.023(3) 0.000(3) 0.001(2) 0.002(3) C1 0.031(4) 0.042(5) 0.022(4) -0.007(3) 0.010(3) -0.004(3) C2 0.038(4) 0.056(6) 0.032(4) -0.013(4) 0.013(4) -0.019(4) C3 0.045(5) 0.079(7) 0.043(5) -0.031(5) 0.030(4) -0.033(5) C4 0.027(4) 0.046(5) 0.020(4) -0.011(3) 0.010(3) -0.011(3) C5 0.036(4) 0.036(4) 0.019(4) -0.001(3) 0.012(3) 0.000(3) C6 0.052(5) 0.035(4) 0.029(4) 0.005(3) 0.024(4) 0.004(4) C7 0.035(4) 0.034(4) 0.025(4) 0.006(3) 0.004(3) 0.006(3) C8 0.014(3) 0.033(4) 0.021(4) -0.005(3) 0.001(3) -0.001(3) S1 0.0288(9) 0.0451(11) 0.0277(10) -0.0103(8) 0.0154(8) -0.0047(8) Cl1 0.0278(8) 0.0332(9) 0.0200(8) -0.0037(7) 0.0088(7) 0.0005(7) Cl2 0.0249(8) 0.0265(9) 0.0215(8) 0.0024(7) 0.0044(7) -0.0013(7) O1W 0.050(3) 0.024(3) 0.037(3) 0.000(2) -0.024(3) 0.003(3) O2W 0.025(3) 0.045(4) 0.055(4) -0.018(3) 0.020(3) -0.008(2) O3W 0.033(3) 0.026(3) 0.016(2) -0.002(2) 0.005(2) -0.005(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 Ni1 O1W 2.042(5) . ? Ni1 O3W 2.058(5) . ? Ni1 O2W 2.067(5) . ? Ni1 N1 2.074(6) . ? Ni1 N3 2.081(6) . ? Ni1 Cl1 2.400(2) . ? N1 C4 1.330(9) . ? N1 C1 1.355(10) . ? N2 C4 1.331(9) . ? N2 C3 1.341(13) . ? N3 C8 1.326(9) . ? N3 C5 1.330(9) . ? N4 C7 1.333(9) . ? N4 C8 1.337(9) . ? C1 C2 1.387(10) . ? C2 C3 1.380(13) . ? C4 S1 1.778(8) . ? C5 C6 1.385(11) . ? C6 C7 1.370(11) . ? C8 S1 1.765(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 O1W Ni1 O3W 82.4(2) . . ? O1W Ni1 O2W 88.6(2) . . ? O3W Ni1 O2W 85.3(2) . . ? O1W Ni1 N1 91.3(2) . . ? O3W Ni1 N1 91.4(2) . . ? O2W Ni1 N1 176.7(2) . . ? O1W Ni1 N3 174.3(2) . . ? O3W Ni1 N3 91.9(2) . . ? O2W Ni1 N3 90.3(2) . . ? N1 Ni1 N3 89.5(2) . . ? O1W Ni1 Cl1 91.65(17) . . ? O3W Ni1 Cl1 172.78(15) . . ? O2W Ni1 Cl1 90.40(16) . . ? N1 Ni1 Cl1 92.92(16) . . ? N3 Ni1 Cl1 93.95(16) . . ? C4 N1 C1 115.5(6) . . ? C4 N1 Ni1 125.5(5) . . ? C1 N1 Ni1 118.7(5) . . ? C4 N2 C3 115.5(7) . . ? C8 N3 C5 116.5(6) . . ? C8 N3 Ni1 125.0(5) . . ? C5 N3 Ni1 117.8(5) . . ? C7 N4 C8 115.7(6) . . ? N1 C1 C2 121.8(8) . . ? C3 C2 C1 116.9(8) . . ? N2 C3 C2 122.6(8) . . ? N1 C4 N2 127.6(8) . . ? N1 C4 S1 123.2(5) . . ? N2 C4 S1 109.1(6) . . ? N3 C5 C6 122.3(7) . . ? C7 C6 C5 116.0(7) . . ? N4 C7 C6 123.2(7) . . ? N3 C8 N4 126.0(6) . . ? N3 C8 S1 123.8(5) . . ? N4 C8 S1 110.1(5) . . ? C8 S1 C4 107.3(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 O1W H11 Cl2 0.86 2.22 3.073(6) 175.7 1_545 O1W H12 Cl2 0.85 2.25 3.104(5) 179.6 5_666 O2W H21 Cl2 0.86 2.23 3.081(5) 168.8 4_545 O2W H22 Cl1 0.88 2.50 3.351(5) 164.2 4 O3W H31 Cl2 0.86 2.24 3.098(5) 169.7 . O3W H32 Cl1 0.86 2.32 3.181(5) 174.5 8_556 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 66.99 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.560 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.120 _database_code_depnum_ccdc_archive 'CCDC 937858' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [chlorido-tris(mu-chlorido)(2,2'-sulfanediyldipyrimidine-kN,kN') (2,2'-trisulfane-1,3diyldipyrimidine-kN,kS,kN')dinickel(II)]] ; _chemical_formula_moiety 'C16 H12 Cl4 N8 Ni2 S4' _chemical_formula_structural 'C16 H12 Cl4 N8 Ni2 S4' _chemical_formula_sum 'C16 H12 Cl4 N8 Ni2 S4' _chemical_formula_weight 703.80 _chemical_compound_source 'synthesis as described' 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' Ni Ni 0.3393 1.1124 '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 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 8.9227(3) _cell_length_b 25.2712(8) _cell_length_c 10.9981(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.274(2) _cell_angle_gamma 90.00 _cell_volume 2423.25(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9962 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 30.37 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.5893 _exptl_absorpt_correction_T_max 0.6491 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46856 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 29.13 _reflns_number_total 6519 _reflns_number_gt 5549 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0252P)^2^+3.8881P] 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 6519 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Ni1 Ni 0.10779(3) 0.162075(12) 0.23602(3) 0.01126(7) Uani 1 1 d . . . Ni2 Ni 0.15512(3) 0.123361(13) -0.01561(3) 0.01153(7) Uani 1 1 d . . . S1 S 0.16881(8) 0.06777(3) 0.48421(6) 0.01902(14) Uani 1 1 d . . . S2 S 0.15399(7) 0.00000(2) -0.14808(6) 0.01632(13) Uani 1 1 d . . . S3 S -0.00357(7) 0.05137(2) -0.10506(6) 0.01311(12) Uani 1 1 d . . . S4 S -0.11408(7) 0.08384(3) -0.26923(6) 0.01769(13) Uani 1 1 d . . . C1 C -0.1968(3) 0.13677(10) 0.2818(2) 0.0176(5) Uani 1 1 d . . . H1 H -0.2240 0.1660 0.2271 0.021 Uiso 1 1 calc R . . C2 C -0.3119(3) 0.10783(11) 0.3154(3) 0.0218(6) Uani 1 1 d . . . H2 H -0.4171 0.1163 0.2859 0.026 Uiso 1 1 calc R . . C3 C -0.2657(3) 0.06581(11) 0.3945(3) 0.0219(6) Uani 1 1 d . . . H3 H -0.3419 0.0435 0.4159 0.026 Uiso 1 1 calc R . . C4 C -0.0165(3) 0.08635(10) 0.4055(2) 0.0157(5) Uani 1 1 d . . . C5 C 0.3804(3) 0.19819(10) 0.4126(2) 0.0164(5) Uani 1 1 d . . . H5 H 0.3666 0.2273 0.3568 0.020 Uiso 1 1 calc R . . C6 C 0.5065(3) 0.19713(11) 0.5079(3) 0.0200(5) Uani 1 1 d . . . H6 H 0.5807 0.2247 0.5194 0.024 Uiso 1 1 calc R . . C7 C 0.5209(3) 0.15411(12) 0.5867(3) 0.0236(6) Uani 1 1 d . . . H7 H 0.6096 0.1515 0.6518 0.028 Uiso 1 1 calc R . . C8 C 0.2954(3) 0.12100(10) 0.4798(2) 0.0160(5) Uani 1 1 d . . . C9 C 0.4747(3) 0.10814(11) -0.0518(3) 0.0190(5) Uani 1 1 d . . . H9 H 0.4897 0.1419 -0.0132 0.023 Uiso 1 1 calc R . . C10 C 0.5951(3) 0.08420(11) -0.0891(3) 0.0212(6) Uani 1 1 d . . . H10 H 0.6923 0.1010 -0.0781 0.025 Uiso 1 1 calc R . . C11 C 0.5705(3) 0.03517(11) -0.1426(3) 0.0200(5) Uani 1 1 d . . . H11 H 0.6529 0.0177 -0.1681 0.024 Uiso 1 1 calc R . . C12 C 0.3246(3) 0.03789(10) -0.1227(2) 0.0144(5) Uani 1 1 d . . . C13 C 0.1899(3) 0.19857(10) -0.2200(3) 0.0180(5) Uani 1 1 d . . . H13 H 0.2743 0.2114 -0.1593 0.022 Uiso 1 1 calc R . . C14 C 0.1554(3) 0.22219(10) -0.3353(3) 0.0198(5) Uani 1 1 d . . . H14 H 0.2182 0.2494 -0.3570 0.024 Uiso 1 1 calc R . . C15 C 0.0270(3) 0.20502(11) -0.4177(2) 0.0191(5) Uani 1 1 d . . . H15 H -0.0045 0.2230 -0.4948 0.023 Uiso 1 1 calc R . . C16 C -0.0070(3) 0.14153(10) -0.2820(2) 0.0138(5) Uani 1 1 d . . . Cl1 Cl 0.04047(7) 0.24689(2) 0.28540(6) 0.01553(12) Uani 1 1 d . . . Cl2 Cl -0.06942(6) 0.16157(2) 0.03350(5) 0.01382(11) Uani 1 1 d . . . Cl3 Cl 0.29367(6) 0.19211(2) 0.10175(5) 0.01378(12) Uani 1 1 d . . . Cl4 Cl 0.18931(7) 0.07489(2) 0.17531(6) 0.01414(12) Uani 1 1 d . . . N1 N -0.0474(2) 0.12561(8) 0.32280(19) 0.0137(4) Uani 1 1 d . . . N2 N -0.1192(3) 0.05518(9) 0.4418(2) 0.0197(5) Uani 1 1 d . . . N3 N 0.2745(2) 0.15914(8) 0.39520(19) 0.0137(4) Uani 1 1 d . . . N4 N 0.4161(3) 0.11610(9) 0.5755(2) 0.0232(5) Uani 1 1 d . . . N5 N 0.3359(2) 0.08512(8) -0.06852(19) 0.0135(4) Uani 1 1 d . . . N6 N 0.4346(2) 0.01127(9) -0.1601(2) 0.0188(5) Uani 1 1 d . . . N7 N 0.1067(2) 0.15769(8) -0.19119(19) 0.0137(4) Uani 1 1 d . . . N8 N -0.0553(3) 0.16370(9) -0.3926(2) 0.0173(4) 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 Ni1 0.01289(14) 0.01113(15) 0.01028(15) -0.00046(11) 0.00361(11) 0.00010(11) Ni2 0.01054(14) 0.01417(16) 0.01051(15) -0.00240(12) 0.00361(11) -0.00191(11) S1 0.0250(3) 0.0138(3) 0.0181(3) 0.0039(2) 0.0042(3) 0.0009(2) S2 0.0144(3) 0.0135(3) 0.0226(3) -0.0041(2) 0.0074(2) -0.0021(2) S3 0.0123(3) 0.0148(3) 0.0131(3) -0.0009(2) 0.0046(2) -0.0022(2) S4 0.0152(3) 0.0221(3) 0.0146(3) 0.0013(2) 0.0007(2) -0.0051(2) C1 0.0207(12) 0.0162(12) 0.0172(13) -0.0024(10) 0.0069(10) 0.0004(10) C2 0.0203(13) 0.0247(14) 0.0235(14) -0.0064(11) 0.0117(11) -0.0026(11) C3 0.0276(14) 0.0202(13) 0.0218(14) -0.0056(11) 0.0142(11) -0.0075(11) C4 0.0232(12) 0.0127(12) 0.0125(12) -0.0036(9) 0.0069(10) -0.0006(10) C5 0.0192(12) 0.0148(12) 0.0163(12) -0.0028(10) 0.0061(10) 0.0009(9) C6 0.0186(12) 0.0208(13) 0.0197(13) -0.0071(11) 0.0021(10) 0.0001(10) C7 0.0222(13) 0.0247(15) 0.0202(14) -0.0039(11) -0.0037(11) 0.0047(11) C8 0.0218(12) 0.0112(11) 0.0147(12) -0.0031(9) 0.0033(10) 0.0035(9) C9 0.0151(12) 0.0213(13) 0.0216(14) -0.0057(11) 0.0064(10) -0.0032(10) C10 0.0134(12) 0.0259(14) 0.0257(15) -0.0060(12) 0.0071(10) -0.0032(10) C11 0.0151(12) 0.0213(13) 0.0257(14) -0.0014(11) 0.0091(10) 0.0012(10) C12 0.0136(11) 0.0173(12) 0.0132(12) 0.0009(9) 0.0045(9) -0.0021(9) C13 0.0176(12) 0.0184(13) 0.0186(13) -0.0028(10) 0.0053(10) -0.0037(10) C14 0.0270(14) 0.0143(12) 0.0205(14) 0.0000(10) 0.0104(11) -0.0021(10) C15 0.0275(14) 0.0171(13) 0.0135(12) 0.0000(10) 0.0063(10) 0.0058(10) C16 0.0140(11) 0.0148(12) 0.0141(12) -0.0012(9) 0.0063(9) -0.0004(9) Cl1 0.0206(3) 0.0123(3) 0.0148(3) 0.0008(2) 0.0062(2) 0.0032(2) Cl2 0.0114(2) 0.0173(3) 0.0131(3) -0.0016(2) 0.0034(2) -0.0004(2) Cl3 0.0136(3) 0.0138(3) 0.0143(3) -0.0026(2) 0.0039(2) -0.0026(2) Cl4 0.0178(3) 0.0120(3) 0.0135(3) -0.0011(2) 0.0053(2) 0.0012(2) N1 0.0177(10) 0.0119(10) 0.0129(10) -0.0009(8) 0.0061(8) -0.0002(8) N2 0.0297(12) 0.0150(11) 0.0173(11) -0.0026(9) 0.0117(9) -0.0058(9) N3 0.0182(10) 0.0113(10) 0.0116(10) -0.0022(8) 0.0030(8) 0.0021(8) N4 0.0280(12) 0.0196(12) 0.0192(12) 0.0003(9) -0.0014(10) 0.0052(10) N5 0.0121(9) 0.0173(10) 0.0119(10) -0.0027(8) 0.0041(8) -0.0015(8) N6 0.0169(10) 0.0170(11) 0.0248(12) -0.0024(9) 0.0092(9) 0.0017(8) N7 0.0131(9) 0.0163(10) 0.0124(10) -0.0003(8) 0.0043(8) -0.0005(8) N8 0.0215(11) 0.0173(11) 0.0133(10) -0.0016(9) 0.0044(8) 0.0021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 2.044(2) . ? Ni1 N1 2.059(2) . ? Ni1 Cl1 2.3214(7) . ? Ni1 Cl2 2.4421(7) . ? Ni1 Cl4 2.4568(7) . ? Ni1 Cl3 2.5591(7) . ? Ni2 N5 2.067(2) . ? Ni2 N7 2.077(2) . ? Ni2 Cl3 2.3525(6) . ? Ni2 S3 2.3854(7) . ? Ni2 Cl2 2.3871(6) . ? Ni2 Cl4 2.3937(7) . ? S1 C4 1.759(3) . ? S1 C8 1.764(3) . ? S2 C12 1.769(2) . ? S2 S3 2.0417(9) . ? S3 S4 2.0368(9) . ? S4 C16 1.765(3) . ? C1 N1 1.343(3) . ? C1 C2 1.374(4) . ? C1 H1 0.9500 . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 N2 1.328(4) . ? C3 H3 0.9500 . ? C4 N2 1.332(3) . ? C4 N1 1.335(3) . ? C5 N3 1.351(3) . ? C5 C6 1.366(4) . ? C5 H5 0.9500 . ? C6 C7 1.379(4) . ? C6 H6 0.9500 . ? C7 N4 1.328(4) . ? C7 H7 0.9500 . ? C8 N3 1.325(3) . ? C8 N4 1.342(3) . ? C9 N5 1.346(3) . ? C9 C10 1.369(4) . ? C9 H9 0.9500 . ? C10 C11 1.370(4) . ? C10 H10 0.9500 . ? C11 N6 1.332(3) . ? C11 H11 0.9500 . ? C12 N6 1.325(3) . ? C12 N5 1.328(3) . ? C13 N7 1.348(3) . ? C13 C14 1.376(4) . ? C13 H13 0.9500 . ? C14 C15 1.372(4) . ? C14 H14 0.9500 . ? C15 N8 1.338(3) . ? C15 H15 0.9500 . ? C16 N8 1.325(3) . ? C16 N7 1.328(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ni1 N1 91.47(8) . . ? N3 Ni1 Cl1 90.60(6) . . ? N1 Ni1 Cl1 94.12(6) . . ? N3 Ni1 Cl2 173.42(6) . . ? N1 Ni1 Cl2 92.95(6) . . ? Cl1 Ni1 Cl2 93.93(2) . . ? N3 Ni1 Cl4 89.81(6) . . ? N1 Ni1 Cl4 89.53(6) . . ? Cl1 Ni1 Cl4 176.32(2) . . ? Cl2 Ni1 Cl4 85.36(2) . . ? N3 Ni1 Cl3 93.56(6) . . ? N1 Ni1 Cl3 169.25(6) . . ? Cl1 Ni1 Cl3 95.33(2) . . ? Cl2 Ni1 Cl3 81.29(2) . . ? Cl4 Ni1 Cl3 80.99(2) . . ? N5 Ni2 N7 87.35(8) . . ? N5 Ni2 Cl3 98.58(6) . . ? N7 Ni2 Cl3 100.53(6) . . ? N5 Ni2 S3 87.57(6) . . ? N7 Ni2 S3 86.98(6) . . ? Cl3 Ni2 S3 170.45(3) . . ? N5 Ni2 Cl2 174.53(6) . . ? N7 Ni2 Cl2 91.31(6) . . ? Cl3 Ni2 Cl2 86.88(2) . . ? S3 Ni2 Cl2 87.06(2) . . ? N5 Ni2 Cl4 92.64(6) . . ? N7 Ni2 Cl4 172.69(6) . . ? Cl3 Ni2 Cl4 86.70(2) . . ? S3 Ni2 Cl4 85.71(2) . . ? Cl2 Ni2 Cl4 88.00(2) . . ? C4 S1 C8 108.87(12) . . ? C12 S2 S3 103.35(9) . . ? S4 S3 S2 106.15(4) . . ? S4 S3 Ni2 101.03(3) . . ? S2 S3 Ni2 101.70(3) . . ? C16 S4 S3 103.60(9) . . ? N1 C1 C2 122.9(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 116.1(3) . . ? C1 C2 H2 122.0 . . ? C3 C2 H2 122.0 . . ? N2 C3 C2 122.7(3) . . ? N2 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? N2 C4 N1 126.0(2) . . ? N2 C4 S1 109.2(2) . . ? N1 C4 S1 124.7(2) . . ? N3 C5 C6 122.1(2) . . ? N3 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C7 116.7(3) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? N4 C7 C6 122.8(3) . . ? N4 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? N3 C8 N4 125.9(2) . . ? N3 C8 S1 125.4(2) . . ? N4 C8 S1 108.7(2) . . ? N5 C9 C10 121.8(2) . . ? N5 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C10 C11 117.7(2) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? N6 C11 C10 122.0(2) . . ? N6 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? N6 C12 N5 127.2(2) . . ? N6 C12 S2 110.19(19) . . ? N5 C12 S2 122.53(18) . . ? N7 C13 C14 121.5(2) . . ? N7 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 117.6(2) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? N8 C15 C14 121.9(3) . . ? N8 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? N8 C16 N7 127.4(2) . . ? N8 C16 S4 110.28(18) . . ? N7 C16 S4 122.28(19) . . ? Ni2 Cl2 Ni1 78.27(2) . . ? Ni2 Cl3 Ni1 76.592(19) . . ? Ni2 Cl4 Ni1 77.86(2) . . ? C4 N1 C1 115.6(2) . . ? C4 N1 Ni1 125.93(17) . . ? C1 N1 Ni1 117.87(17) . . ? C3 N2 C4 116.4(2) . . ? C8 N3 C5 116.2(2) . . ? C8 N3 Ni1 126.58(18) . . ? C5 N3 Ni1 117.04(17) . . ? C7 N4 C8 116.0(2) . . ? C12 N5 C9 115.4(2) . . ? C12 N5 Ni2 123.85(16) . . ? C9 N5 Ni2 120.70(17) . . ? C12 N6 C11 115.9(2) . . ? C16 N7 C13 115.4(2) . . ? C16 N7 Ni2 123.06(17) . . ? C13 N7 Ni2 121.50(17) . . ? C16 N8 C15 115.7(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 C12 S2 S3 S4 95.88(9) . . . . ? C12 S2 S3 Ni2 -9.39(9) . . . . ? N5 Ni2 S3 S4 -102.16(7) . . . . ? N7 Ni2 S3 S4 -14.68(6) . . . . ? Cl2 Ni2 S3 S4 76.79(3) . . . . ? Cl4 Ni2 S3 S4 165.01(3) . . . . ? N5 Ni2 S3 S2 7.10(7) . . . . ? N7 Ni2 S3 S2 94.57(6) . . . . ? Cl2 Ni2 S3 S2 -173.96(3) . . . . ? Cl4 Ni2 S3 S2 -85.74(3) . . . . ? S2 S3 S4 C16 -91.85(9) . . . . ? Ni2 S3 S4 C16 13.91(9) . . . . ? N1 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 N2 3.7(4) . . . . ? C8 S1 C4 N2 -159.67(18) . . . . ? C8 S1 C4 N1 20.3(3) . . . . ? N3 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 N4 -2.5(4) . . . . ? C4 S1 C8 N3 -24.2(3) . . . . ? C4 S1 C8 N4 156.27(18) . . . . ? N5 C9 C10 C11 -1.0(4) . . . . ? C9 C10 C11 N6 0.8(4) . . . . ? S3 S2 C12 N6 -173.23(17) . . . . ? S3 S2 C12 N5 9.4(2) . . . . ? N7 C13 C14 C15 4.2(4) . . . . ? C13 C14 C15 N8 -5.9(4) . . . . ? S3 S4 C16 N8 172.60(16) . . . . ? S3 S4 C16 N7 -6.1(2) . . . . ? N7 Ni2 Cl2 Ni1 -146.56(6) . . . . ? Cl3 Ni2 Cl2 Ni1 -46.08(2) . . . . ? S3 Ni2 Cl2 Ni1 126.54(2) . . . . ? Cl4 Ni2 Cl2 Ni1 40.73(2) . . . . ? N1 Ni1 Cl2 Ni2 -128.88(6) . . . . ? Cl1 Ni1 Cl2 Ni2 136.78(2) . . . . ? Cl4 Ni1 Cl2 Ni2 -39.60(2) . . . . ? Cl3 Ni1 Cl2 Ni2 41.981(19) . . . . ? N5 Ni2 Cl3 Ni1 -136.58(6) . . . . ? N7 Ni2 Cl3 Ni1 134.53(6) . . . . ? Cl2 Ni2 Cl3 Ni1 43.78(2) . . . . ? Cl4 Ni2 Cl3 Ni1 -44.397(19) . . . . ? N3 Ni1 Cl3 Ni2 132.79(6) . . . . ? N1 Ni1 Cl3 Ni2 15.1(3) . . . . ? Cl1 Ni1 Cl3 Ni2 -136.27(2) . . . . ? Cl2 Ni1 Cl3 Ni2 -43.09(2) . . . . ? Cl4 Ni1 Cl3 Ni2 43.55(2) . . . . ? N5 Ni2 Cl4 Ni1 144.93(6) . . . . ? Cl3 Ni2 Cl4 Ni1 46.48(2) . . . . ? S3 Ni2 Cl4 Ni1 -127.70(2) . . . . ? Cl2 Ni2 Cl4 Ni1 -40.51(2) . . . . ? N3 Ni1 Cl4 Ni2 -135.99(6) . . . . ? N1 Ni1 Cl4 Ni2 132.54(6) . . . . ? Cl2 Ni1 Cl4 Ni2 39.538(19) . . . . ? Cl3 Ni1 Cl4 Ni2 -42.360(19) . . . . ? N2 C4 N1 C1 6.0(4) . . . . ? S1 C4 N1 C1 -173.99(19) . . . . ? N2 C4 N1 Ni1 -164.7(2) . . . . ? S1 C4 N1 Ni1 15.4(3) . . . . ? C2 C1 N1 C4 -4.2(4) . . . . ? C2 C1 N1 Ni1 167.2(2) . . . . ? N3 Ni1 N1 C4 -38.5(2) . . . . ? Cl1 Ni1 N1 C4 -129.2(2) . . . . ? Cl2 Ni1 N1 C4 136.6(2) . . . . ? Cl4 Ni1 N1 C4 51.3(2) . . . . ? Cl3 Ni1 N1 C4 79.3(4) . . . . ? N3 Ni1 N1 C1 151.02(19) . . . . ? Cl1 Ni1 N1 C1 60.31(18) . . . . ? Cl2 Ni1 N1 C1 -33.85(18) . . . . ? Cl4 Ni1 N1 C1 -119.18(18) . . . . ? Cl3 Ni1 N1 C1 -91.1(4) . . . . ? C2 C3 N2 C4 -2.3(4) . . . . ? N1 C4 N2 C3 -2.8(4) . . . . ? S1 C4 N2 C3 177.15(19) . . . . ? N4 C8 N3 C5 -4.6(4) . . . . ? S1 C8 N3 C5 176.03(19) . . . . ? N4 C8 N3 Ni1 170.9(2) . . . . ? S1 C8 N3 Ni1 -8.5(3) . . . . ? C6 C5 N3 C8 3.6(4) . . . . ? C6 C5 N3 Ni1 -172.4(2) . . . . ? N1 Ni1 N3 C8 34.9(2) . . . . ? Cl1 Ni1 N3 C8 129.0(2) . . . . ? Cl4 Ni1 N3 C8 -54.6(2) . . . . ? Cl3 Ni1 N3 C8 -135.6(2) . . . . ? N1 Ni1 N3 C5 -149.64(18) . . . . ? Cl1 Ni1 N3 C5 -55.50(17) . . . . ? Cl4 Ni1 N3 C5 120.84(17) . . . . ? Cl3 Ni1 N3 C5 39.87(17) . . . . ? C6 C7 N4 C8 1.8(4) . . . . ? N3 C8 N4 C7 2.0(4) . . . . ? S1 C8 N4 C7 -178.6(2) . . . . ? N6 C12 N5 C9 0.8(4) . . . . ? S2 C12 N5 C9 177.7(2) . . . . ? N6 C12 N5 Ni2 179.3(2) . . . . ? S2 C12 N5 Ni2 -3.8(3) . . . . ? C10 C9 N5 C12 0.3(4) . . . . ? C10 C9 N5 Ni2 -178.3(2) . . . . ? N7 Ni2 N5 C12 -90.2(2) . . . . ? Cl3 Ni2 N5 C12 169.53(19) . . . . ? S3 Ni2 N5 C12 -3.1(2) . . . . ? Cl4 Ni2 N5 C12 82.5(2) . . . . ? N7 Ni2 N5 C9 88.2(2) . . . . ? Cl3 Ni2 N5 C9 -12.1(2) . . . . ? S3 Ni2 N5 C9 175.3(2) . . . . ? N5 C12 N6 C11 -1.1(4) . . . . ? S2 C12 N6 C11 -178.2(2) . . . . ? C10 C11 N6 C12 0.2(4) . . . . ? N8 C16 N7 C13 -6.3(4) . . . . ? S4 C16 N7 C13 172.22(19) . . . . ? N8 C16 N7 Ni2 173.4(2) . . . . ? S4 C16 N7 Ni2 -8.1(3) . . . . ? C14 C13 N7 C16 1.4(4) . . . . ? C14 C13 N7 Ni2 -178.3(2) . . . . ? N5 Ni2 N7 C16 102.9(2) . . . . ? Cl3 Ni2 N7 C16 -158.87(18) . . . . ? S3 Ni2 N7 C16 15.19(19) . . . . ? Cl2 Ni2 N7 C16 -71.80(19) . . . . ? N5 Ni2 N7 C13 -77.4(2) . . . . ? Cl3 Ni2 N7 C13 20.8(2) . . . . ? S3 Ni2 N7 C13 -165.15(19) . . . . ? Cl2 Ni2 N7 C13 107.86(19) . . . . ? N7 C16 N8 C15 4.7(4) . . . . ? S4 C16 N8 C15 -173.91(18) . . . . ? C14 C15 N8 C16 1.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.011 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 937859' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [acetonitriledibromido(2,2'-trisulfane-1,3-diyldipyrimidine-kN,kN')nickel(II)] ; _chemical_formula_moiety 'C10 H9 Br2 N5 Ni S3' _chemical_formula_structural 'C10 H9 Br2 N5 Ni S3' _chemical_formula_sum 'C10 H9 Br2 N5 Ni S3' _chemical_formula_weight 513.93 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.0843(3) _cell_length_b 13.1454(6) _cell_length_c 17.2097(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.955(3) _cell_angle_gamma 90.00 _cell_volume 1600.54(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16063 _cell_measurement_theta_min 4.23 _cell_measurement_theta_max 71.01 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 11.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.2374 _exptl_absorpt_correction_T_max 0.3395 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\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 16063 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 71.01 _reflns_number_total 3037 _reflns_number_gt 2843 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+1.7948P] 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 3037 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.13321(4) 0.25631(2) 0.031903(17) 0.01878(12) Uani 1 1 d . . . Br2 Br 0.17010(4) 0.42479(3) 0.205606(19) 0.02365(12) Uani 1 1 d . . . Ni1 Ni 0.35210(7) 0.27635(4) 0.15283(3) 0.01624(14) Uani 1 1 d . . . S1 S 0.19741(10) 0.02777(6) 0.16710(5) 0.02355(19) Uani 1 1 d . . . S2 S 0.12855(10) 0.16797(6) 0.21003(4) 0.01899(18) Uani 1 1 d . . . S3 S 0.22853(11) 0.16311(7) 0.32399(4) 0.02538(19) Uani 1 1 d . . . C1 C 0.4208(4) 0.0477(3) 0.12804(17) 0.0182(6) Uani 1 1 d . . . C2 C 0.6644(5) -0.0365(3) 0.07645(19) 0.0238(7) Uani 1 1 d . . . H2 H 0.7235 -0.0977 0.0613 0.029 Uiso 1 1 calc R . . C3 C 0.7542(5) 0.0552(3) 0.06577(19) 0.0236(7) Uani 1 1 d . . . H3 H 0.8739 0.0581 0.0434 0.028 Uiso 1 1 calc R . . C4 C 0.6642(4) 0.1426(3) 0.08864(17) 0.0198(6) Uani 1 1 d . . . H4 H 0.7242 0.2064 0.0820 0.024 Uiso 1 1 calc R . . C5 C 0.4599(4) 0.2129(3) 0.32026(19) 0.0220(6) Uani 1 1 d . . . C6 C 0.7339(5) 0.2326(3) 0.3913(2) 0.0283(7) Uani 1 1 d . . . H6 H 0.8092 0.2229 0.4380 0.034 Uiso 1 1 calc R . . C7 C 0.8095(4) 0.2844(3) 0.3307(2) 0.0232(7) Uani 1 1 d . . . H7 H 0.9349 0.3102 0.3347 0.028 Uiso 1 1 calc R . . C8 C 0.6954(4) 0.2973(2) 0.26384(19) 0.0202(6) Uani 1 1 d . . . H8 H 0.7445 0.3322 0.2210 0.024 Uiso 1 1 calc R . . C9 C 0.6356(4) 0.4176(2) 0.06689(18) 0.0204(6) Uani 1 1 d . . . C10 C 0.7672(5) 0.4792(3) 0.0247(2) 0.0263(7) Uani 1 1 d . . . H10A H 0.8967 0.4653 0.0446 0.039 Uiso 1 1 calc R . . H10B H 0.7385 0.5514 0.0318 0.039 Uiso 1 1 calc R . . H10C H 0.7549 0.4623 -0.0308 0.039 Uiso 1 1 calc R . . N1 N 0.4945(3) 0.1404(2) 0.11997(14) 0.0170(5) Uani 1 1 d . . . N2 N 0.4956(4) -0.0408(2) 0.10782(16) 0.0225(6) Uani 1 1 d . . . N3 N 0.5170(4) 0.2621(2) 0.25758(15) 0.0192(5) Uani 1 1 d . . . N4 N 0.5584(4) 0.1955(2) 0.38656(16) 0.0253(6) Uani 1 1 d . . . N5 N 0.5363(4) 0.3678(2) 0.09947(15) 0.0203(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01848(18) 0.0230(2) 0.01458(18) 0.00161(12) -0.00232(12) -0.00028(10) Br2 0.02524(19) 0.0247(2) 0.02113(19) -0.00145(13) 0.00271(14) 0.00478(12) Ni1 0.0152(3) 0.0202(3) 0.0133(3) 0.0015(2) 0.0007(2) -0.00016(19) S1 0.0187(3) 0.0215(4) 0.0309(4) 0.0020(3) 0.0049(3) -0.0013(3) S2 0.0156(3) 0.0242(4) 0.0172(4) 0.0030(3) 0.0014(3) 0.0010(3) S3 0.0205(4) 0.0401(5) 0.0157(4) 0.0083(3) 0.0014(3) -0.0001(3) C1 0.0179(13) 0.0231(15) 0.0133(13) 0.0005(12) -0.0012(11) 0.0018(11) C2 0.0246(15) 0.0283(18) 0.0185(14) -0.0033(14) 0.0005(12) 0.0063(12) C3 0.0210(15) 0.0309(17) 0.0189(15) -0.0031(14) 0.0009(12) 0.0032(13) C4 0.0160(14) 0.0255(16) 0.0179(14) 0.0029(13) 0.0014(11) -0.0016(11) C5 0.0202(14) 0.0267(16) 0.0191(15) -0.0019(14) 0.0013(12) 0.0031(12) C6 0.0299(18) 0.0295(19) 0.0245(16) -0.0003(15) -0.0074(14) 0.0062(14) C7 0.0194(14) 0.0260(17) 0.0238(16) -0.0059(14) -0.0029(13) 0.0029(12) C8 0.0168(14) 0.0222(16) 0.0213(15) -0.0034(13) -0.0011(12) 0.0005(11) C9 0.0191(14) 0.0244(16) 0.0175(15) -0.0006(13) -0.0003(12) 0.0001(12) C10 0.0273(16) 0.0269(17) 0.0252(16) 0.0043(14) 0.0057(13) -0.0050(13) N1 0.0164(11) 0.0214(13) 0.0129(11) -0.0001(10) -0.0017(9) 0.0011(9) N2 0.0220(13) 0.0238(14) 0.0215(13) -0.0007(12) -0.0002(10) 0.0020(10) N3 0.0216(13) 0.0214(13) 0.0145(12) -0.0010(11) -0.0002(10) 0.0023(10) N4 0.0256(13) 0.0336(16) 0.0165(13) 0.0018(12) -0.0018(11) 0.0031(11) N5 0.0203(12) 0.0232(14) 0.0175(12) 0.0003(11) 0.0011(10) 0.0005(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 Br1 Ni1 2.5441(6) . ? Br2 Ni1 2.5329(6) . ? Ni1 N5 2.028(3) . ? Ni1 N3 2.105(3) . ? Ni1 N1 2.142(3) . ? Ni1 S2 2.3807(9) . ? S1 C1 1.771(3) . ? S1 S2 2.0537(11) . ? S2 S3 2.0515(11) . ? S3 C5 1.769(3) . ? C1 N2 1.332(4) . ? C1 N1 1.336(4) . ? C2 N2 1.338(4) . ? C2 C3 1.380(5) . ? C2 H2 0.9500 . ? C3 C4 1.381(5) . ? C3 H3 0.9500 . ? C4 N1 1.343(4) . ? C4 H4 0.9500 . ? C5 N4 1.326(4) . ? C5 N3 1.338(4) . ? C6 N4 1.334(5) . ? C6 C7 1.376(5) . ? C6 H6 0.9500 . ? C7 C8 1.383(5) . ? C7 H7 0.9500 . ? C8 N3 1.345(4) . ? C8 H8 0.9500 . ? C9 N5 1.131(4) . ? C9 C10 1.457(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 N5 Ni1 N3 95.68(11) . . ? N5 Ni1 N1 92.98(10) . . ? N3 Ni1 N1 84.46(10) . . ? N5 Ni1 S2 177.46(8) . . ? N3 Ni1 S2 86.80(8) . . ? N1 Ni1 S2 86.69(7) . . ? N5 Ni1 Br2 93.28(8) . . ? N3 Ni1 Br2 91.84(7) . . ? N1 Ni1 Br2 173.02(7) . . ? S2 Ni1 Br2 87.19(2) . . ? N5 Ni1 Br1 94.03(7) . . ? N3 Ni1 Br1 168.26(8) . . ? N1 Ni1 Br1 88.46(7) . . ? S2 Ni1 Br1 83.45(2) . . ? Br2 Ni1 Br1 94.186(19) . . ? C1 S1 S2 103.75(11) . . ? S3 S2 S1 103.85(5) . . ? S3 S2 Ni1 102.10(4) . . ? S1 S2 Ni1 102.29(4) . . ? C5 S3 S2 103.21(11) . . ? N2 C1 N1 127.4(3) . . ? N2 C1 S1 110.2(2) . . ? N1 C1 S1 122.4(2) . . ? N2 C2 C3 121.2(3) . . ? N2 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C2 C3 C4 117.8(3) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? N1 C4 C3 122.1(3) . . ? N1 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? N4 C5 N3 127.5(3) . . ? N4 C5 S3 110.6(2) . . ? N3 C5 S3 121.8(2) . . ? N4 C6 C7 122.2(3) . . ? N4 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C6 C7 C8 117.2(3) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? N3 C8 C7 122.1(3) . . ? N3 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? N5 C9 C10 178.3(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 N1 C4 115.1(3) . . ? C1 N1 Ni1 122.8(2) . . ? C4 N1 Ni1 122.1(2) . . ? C1 N2 C2 116.3(3) . . ? C5 N3 C8 115.1(3) . . ? C5 N3 Ni1 123.8(2) . . ? C8 N3 Ni1 121.0(2) . . ? C5 N4 C6 115.9(3) . . ? C9 N5 Ni1 177.2(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 C1 S1 S2 S3 -92.39(11) . . . . ? C1 S1 S2 Ni1 13.56(11) . . . . ? N3 Ni1 S2 S3 10.92(8) . . . . ? N1 Ni1 S2 S3 95.55(7) . . . . ? Br2 Ni1 S2 S3 -81.08(4) . . . . ? Br1 Ni1 S2 S3 -175.62(4) . . . . ? N3 Ni1 S2 S1 -96.37(8) . . . . ? N1 Ni1 S2 S1 -11.74(7) . . . . ? Br2 Ni1 S2 S1 171.63(4) . . . . ? Br1 Ni1 S2 S1 77.09(4) . . . . ? S1 S2 S3 C5 91.62(12) . . . . ? Ni1 S2 S3 C5 -14.47(12) . . . . ? S2 S1 C1 N2 171.2(2) . . . . ? S2 S1 C1 N1 -10.1(3) . . . . ? N2 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 N1 -0.3(5) . . . . ? S2 S3 C5 N4 -167.0(2) . . . . ? S2 S3 C5 N3 14.0(3) . . . . ? N4 C6 C7 C8 0.3(5) . . . . ? C6 C7 C8 N3 0.6(5) . . . . ? N2 C1 N1 C4 -0.8(4) . . . . ? S1 C1 N1 C4 -179.3(2) . . . . ? N2 C1 N1 Ni1 178.3(2) . . . . ? S1 C1 N1 Ni1 -0.2(3) . . . . ? C3 C4 N1 C1 0.7(4) . . . . ? C3 C4 N1 Ni1 -178.5(2) . . . . ? N5 Ni1 N1 C1 -168.8(2) . . . . ? N3 Ni1 N1 C1 95.8(2) . . . . ? S2 Ni1 N1 C1 8.7(2) . . . . ? Br1 Ni1 N1 C1 -74.8(2) . . . . ? N5 Ni1 N1 C4 10.3(2) . . . . ? N3 Ni1 N1 C4 -85.1(2) . . . . ? S2 Ni1 N1 C4 -172.2(2) . . . . ? Br1 Ni1 N1 C4 104.2(2) . . . . ? N1 C1 N2 C2 0.6(5) . . . . ? S1 C1 N2 C2 179.2(2) . . . . ? C3 C2 N2 C1 -0.2(5) . . . . ? N4 C5 N3 C8 -0.1(5) . . . . ? S3 C5 N3 C8 178.8(2) . . . . ? N4 C5 N3 Ni1 175.9(3) . . . . ? S3 C5 N3 Ni1 -5.3(4) . . . . ? C7 C8 N3 C5 -0.7(5) . . . . ? C7 C8 N3 Ni1 -176.8(2) . . . . ? N5 Ni1 N3 C5 175.5(3) . . . . ? N1 Ni1 N3 C5 -92.1(3) . . . . ? S2 Ni1 N3 C5 -5.1(2) . . . . ? Br2 Ni1 N3 C5 82.0(2) . . . . ? Br1 Ni1 N3 C5 -38.9(5) . . . . ? N5 Ni1 N3 C8 -8.8(3) . . . . ? N1 Ni1 N3 C8 83.6(2) . . . . ? S2 Ni1 N3 C8 170.6(2) . . . . ? Br2 Ni1 N3 C8 -102.3(2) . . . . ? Br1 Ni1 N3 C8 136.8(3) . . . . ? N3 C5 N4 C6 0.9(5) . . . . ? S3 C5 N4 C6 -178.1(3) . . . . ? C7 C6 N4 C5 -1.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 71.01 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.807 _refine_diff_density_min -0.930 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 937860' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound-6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [dichlorido-bis(mu-chlorido)bis(2,2'-sulfanediyldipyrimidine-kN,kN')dinickel(II)]] ; _chemical_formula_moiety 'C20 H18 Cl4 N10 Ni2 S2' _chemical_formula_structural 'C20 H18 Cl4 N10 Ni2 S2' _chemical_formula_sum 'C20 H18 Cl4 N10 Ni2 S2' _chemical_formula_weight 721.78 _chemical_compound_source 'synthesis as described' 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' Ni Ni 0.3393 1.1124 '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 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1780(4) _cell_length_b 8.6442(4) _cell_length_c 10.4860(5) _cell_angle_alpha 71.129(2) _cell_angle_beta 69.852(2) _cell_angle_gamma 83.106(3) _cell_volume 658.48(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 29.76 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 2.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_special_details ; ? ; _exptl_absorpt_correction_T_min 0.6872 _exptl_absorpt_correction_T_max 0.8229 _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33471 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3140 _reflns_number_gt 2796 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.3805P] 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 3140 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.16072(3) 0.94918(3) 0.85212(2) 0.01024(8) Uani 1 1 d . . . S1 S 0.16182(7) 1.31896(6) 0.57269(5) 0.01648(12) Uani 1 1 d . . . C1 C 0.2446(3) 0.8570(2) 0.5869(2) 0.0159(4) Uani 1 1 d . . . H1 H 0.2675 0.7552 0.6485 0.019 Uiso 1 1 calc R . . C2 C 0.2515(3) 0.8652(3) 0.4524(2) 0.0187(4) Uani 1 1 d . . . H2 H 0.2820 0.7726 0.4187 0.022 Uiso 1 1 calc R . . C3 C 0.2121(3) 1.0146(3) 0.36785(19) 0.0193(4) Uani 1 1 d . . . H3 H 0.2075 1.0224 0.2767 0.023 Uiso 1 1 calc R . . C4 C 0.1862(2) 1.1288(2) 0.53988(19) 0.0142(4) Uani 1 1 d . . . C5 C 0.3997(3) 1.1725(2) 0.86179(19) 0.0156(4) Uani 1 1 d . . . H5 H 0.4173 1.0764 0.9320 0.019 Uiso 1 1 calc R . . C6 C 0.4821(3) 1.3136(2) 0.8380(2) 0.0176(4) Uani 1 1 d . . . H6 H 0.5594 1.3163 0.8871 0.021 Uiso 1 1 calc R . . C7 C 0.4465(3) 1.4512(2) 0.7388(2) 0.0206(4) Uani 1 1 d . . . H7 H 0.4953 1.5524 0.7241 0.025 Uiso 1 1 calc R . . C8 C 0.2795(3) 1.3034(2) 0.68957(19) 0.0144(4) Uani 1 1 d . . . C9 C -0.0724(3) 0.6549(2) 0.88563(18) 0.0143(4) Uani 1 1 d . . . C10 C -0.1822(3) 0.5415(2) 0.8755(2) 0.0188(4) Uani 1 1 d . . . H10A H -0.2761 0.6024 0.8418 0.028 Uiso 1 1 calc R . . H10B H -0.2325 0.4626 0.9696 0.028 Uiso 1 1 calc R . . H10C H -0.1120 0.4833 0.8084 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.42058(6) 0.79620(6) 0.83881(4) 0.01462(11) Uani 1 1 d . . . Cl2 Cl -0.10887(6) 1.10033(5) 0.89465(4) 0.01247(11) Uani 1 1 d . . . N1 N 0.2065(2) 0.98857(19) 0.63491(15) 0.0130(3) Uani 1 1 d . . . N2 N 0.1806(2) 1.1475(2) 0.41047(16) 0.0168(3) Uani 1 1 d . . . N3 N 0.2950(2) 1.1657(2) 0.78915(16) 0.0135(3) Uani 1 1 d . . . N4 N 0.3465(2) 1.4475(2) 0.66306(18) 0.0189(4) Uani 1 1 d . . . N5 N 0.0125(2) 0.7451(2) 0.89155(16) 0.0143(3) 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 Ni1 0.01025(14) 0.01072(14) 0.00925(12) -0.00339(9) -0.00107(9) -0.00360(9) S1 0.0208(3) 0.0138(2) 0.0141(2) -0.00195(17) -0.00636(18) -0.00227(19) C1 0.0127(9) 0.0179(10) 0.0164(8) -0.0065(7) -0.0013(7) -0.0038(7) C2 0.0146(10) 0.0249(11) 0.0177(9) -0.0124(8) 0.0009(7) -0.0056(8) C3 0.0158(10) 0.0304(11) 0.0122(8) -0.0082(8) -0.0011(7) -0.0079(8) C4 0.0095(9) 0.0187(10) 0.0131(8) -0.0052(7) -0.0006(6) -0.0042(7) C5 0.0146(10) 0.0175(10) 0.0145(8) -0.0055(7) -0.0026(7) -0.0035(8) C6 0.0146(10) 0.0216(10) 0.0193(9) -0.0112(8) -0.0031(7) -0.0040(8) C7 0.0231(11) 0.0161(10) 0.0231(10) -0.0095(8) -0.0029(8) -0.0062(8) C8 0.0129(9) 0.0163(9) 0.0133(8) -0.0062(7) -0.0009(7) -0.0029(7) C9 0.0147(10) 0.0139(9) 0.0117(8) -0.0021(7) -0.0024(7) -0.0016(7) C10 0.0190(11) 0.0157(10) 0.0226(9) -0.0039(8) -0.0072(8) -0.0073(8) Cl1 0.0119(2) 0.0153(2) 0.0157(2) -0.00550(17) -0.00216(16) -0.00123(17) Cl2 0.0122(2) 0.0145(2) 0.01054(19) -0.00451(16) -0.00221(15) -0.00187(17) N1 0.0123(8) 0.0151(8) 0.0116(7) -0.0049(6) -0.0021(6) -0.0035(6) N2 0.0135(8) 0.0233(9) 0.0114(7) -0.0033(6) -0.0011(6) -0.0061(7) N3 0.0121(8) 0.0150(8) 0.0117(7) -0.0047(6) -0.0002(6) -0.0035(6) N4 0.0224(10) 0.0127(8) 0.0211(8) -0.0047(6) -0.0056(7) -0.0041(7) N5 0.0138(8) 0.0140(8) 0.0145(7) -0.0044(6) -0.0028(6) -0.0031(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 Ni1 N3 2.0829(16) . ? Ni1 N1 2.0941(15) . ? Ni1 N5 2.1090(16) . ? Ni1 Cl1 2.3504(5) . ? Ni1 Cl2 2.4031(5) . ? Ni1 Cl2 2.4386(5) 2_577 ? S1 C4 1.761(2) . ? S1 C8 1.766(2) . ? C1 N1 1.349(2) . ? C1 C2 1.372(3) . ? C1 H1 0.9500 . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 N2 1.330(3) . ? C3 H3 0.9500 . ? C4 N2 1.330(2) . ? C4 N1 1.332(2) . ? C5 N3 1.344(2) . ? C5 C6 1.374(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 N4 1.331(3) . ? C7 H7 0.9500 . ? C8 N4 1.328(2) . ? C8 N3 1.332(2) . ? C9 N5 1.134(2) . ? C9 C10 1.456(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? Cl2 Ni1 2.4385(5) 2_577 ? 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 Ni1 N1 86.28(6) . . ? N3 Ni1 N5 172.06(6) . . ? N1 Ni1 N5 87.09(6) . . ? N3 Ni1 Cl1 90.99(5) . . ? N1 Ni1 Cl1 90.41(5) . . ? N5 Ni1 Cl1 93.42(5) . . ? N3 Ni1 Cl2 89.22(5) . . ? N1 Ni1 Cl2 96.32(5) . . ? N5 Ni1 Cl2 87.18(5) . . ? Cl1 Ni1 Cl2 173.260(17) . . ? N3 Ni1 Cl2 94.20(4) . 2_577 ? N1 Ni1 Cl2 179.25(5) . 2_577 ? N5 Ni1 Cl2 92.48(4) . 2_577 ? Cl1 Ni1 Cl2 89.001(17) . 2_577 ? Cl2 Ni1 Cl2 84.265(17) . 2_577 ? C4 S1 C8 106.19(9) . . ? N1 C1 C2 122.26(19) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 116.96(18) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? N2 C3 C2 121.93(17) . . ? N2 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? N2 C4 N1 126.56(18) . . ? N2 C4 S1 110.51(15) . . ? N1 C4 S1 122.93(14) . . ? N3 C5 C6 122.31(19) . . ? N3 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C7 116.49(19) . . ? C5 C6 H6 121.8 . . ? C7 C6 H6 121.8 . . ? N4 C7 C6 122.50(18) . . ? N4 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? N4 C8 N3 126.40(18) . . ? N4 C8 S1 109.91(14) . . ? N3 C8 S1 123.69(14) . . ? N5 C9 C10 178.8(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Ni1 Cl2 Ni1 95.735(17) . 2_577 ? C4 N1 C1 115.36(16) . . ? C4 N1 Ni1 126.70(13) . . ? C1 N1 Ni1 117.62(13) . . ? C3 N2 C4 116.44(18) . . ? C8 N3 C5 115.84(16) . . ? C8 N3 Ni1 126.59(13) . . ? C5 N3 Ni1 117.41(13) . . ? C8 N4 C7 116.22(18) . . ? C9 N5 Ni1 165.09(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.9(3) . . . . ? C1 C2 C3 N2 4.5(3) . . . . ? C8 S1 C4 N2 -149.80(14) . . . . ? C8 S1 C4 N1 30.46(18) . . . . ? N3 C5 C6 C7 2.5(3) . . . . ? C5 C6 C7 N4 -4.0(3) . . . . ? C4 S1 C8 N4 147.13(14) . . . . ? C4 S1 C8 N3 -33.33(18) . . . . ? N3 Ni1 Cl2 Ni1 -94.30(4) . . . 2_577 ? N1 Ni1 Cl2 Ni1 179.53(4) . . . 2_577 ? N5 Ni1 Cl2 Ni1 92.78(4) . . . 2_577 ? Cl2 Ni1 Cl2 Ni1 0.0 2_577 . . 2_577 ? N2 C4 N1 C1 8.1(3) . . . . ? S1 C4 N1 C1 -172.23(14) . . . . ? N2 C4 N1 Ni1 -165.28(15) . . . . ? S1 C4 N1 Ni1 14.4(2) . . . . ? C2 C1 N1 C4 -3.8(3) . . . . ? C2 C1 N1 Ni1 170.17(15) . . . . ? N3 Ni1 N1 C4 -45.42(16) . . . . ? N5 Ni1 N1 C4 130.21(16) . . . . ? Cl1 Ni1 N1 C4 -136.39(16) . . . . ? N3 Ni1 N1 C1 141.37(15) . . . . ? N5 Ni1 N1 C1 -43.00(14) . . . . ? Cl1 Ni1 N1 C1 50.40(14) . . . . ? C2 C3 N2 C4 -1.0(3) . . . . ? N1 C4 N2 C3 -5.7(3) . . . . ? S1 C4 N2 C3 174.53(14) . . . . ? N4 C8 N3 C5 -5.3(3) . . . . ? S1 C8 N3 C5 175.28(14) . . . . ? N4 C8 N3 Ni1 170.06(15) . . . . ? S1 C8 N3 Ni1 -9.4(2) . . . . ? C6 C5 N3 C8 1.8(3) . . . . ? C6 C5 N3 Ni1 -174.02(14) . . . . ? N1 Ni1 N3 C8 42.43(15) . . . . ? Cl1 Ni1 N3 C8 132.78(15) . . . . ? Cl2 Ni1 N3 C8 -53.96(15) . . . . ? Cl2 Ni1 N3 C8 -138.15(15) 2_577 . . . ? N1 Ni1 N3 C5 -142.31(14) . . . . ? Cl1 Ni1 N3 C5 -51.97(13) . . . . ? Cl2 Ni1 N3 C5 121.30(13) . . . . ? Cl2 Ni1 N3 C5 37.11(13) 2_577 . . . ? N3 C8 N4 C7 3.9(3) . . . . ? S1 C8 N4 C7 -176.57(15) . . . . ? C6 C7 N4 C8 1.0(3) . . . . ? N1 Ni1 N5 C9 -27.6(6) . . . . ? Cl1 Ni1 N5 C9 -117.9(6) . . . . ? Cl2 Ni1 N5 C9 68.8(6) . . . . ? Cl2 Ni1 N5 C9 153.0(6) 2_577 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.853 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 937861'