# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1876 data_global #===================================================================== # 1. SUBMITION DETAILS _publ_contact_author ; Baltazar de Castro CEQUP/Dep. Qumica Faculdade de Ci^ncias da Universidade do Porto R. Campo Alegre, 687, 4150 Porto Portugal ; _publ_contact_author_phone '++ - 351-22-608 28 92 ' _publ_contact_author_fax '++ - 351-22-608 29 59 ' _publ_contact_author_email 'bcastro@fc.up.pt' _publ_requested_journal 'Dalton Transactions' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #======================================================================= # 2. Processing Sumary #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Nickel Complex with an Asymmetric N2OS coordination sphere C16H18N2NiOS2' ; loop_ _publ_author_name _publ_author_address 'Baltazar de Castro' ; CEQUP/Dep. Qumica Faculdade de Ci^ncias da Universidade do Porto R. Campo Alegre, 687, 4150 Porto Portugal 'Gomes, Lgia R.' ; CEQUP/Dep. Qumica Faculdade de Ci^ncias da Universidade do Porto R. Campo Alegre, 687, 4150 Porto Portugal 'Pereira, Eulalia' ; CEQUP/Dep. Qumica Faculdade de Ci^ncias da Universidade do Porto R. Campo Alegre, 687, 4150 Porto Portugal ; #======================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ref a ref b ref c ; _publ_section_figure_captions ; Fig.1 : Structure of ****** with atom labeling scheme. The hydrogen atoms are omitted for clarity. ; _publ_section_acknowledgements ; ; #================================================================ data_l3 _audit_creation_method SHELXL _chemical_name_systematic ; 2-{[1,2-ethanediyilbis(nitrilomethyllidyne)]-2'dichlorophenolate) benzenethiolate}nickel(II) ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H14 Cl2 N2 Ni O S' _chemical_formula_weight 423.95 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' .2850 1.1130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz '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 7.511(2) _cell_length_b 11.616(4) _cell_length_c 19.228(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1677.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 378 _cell_measurement_theta_min 9.5 _cell_measurement_theta_max 56.3 _exptl_crystal_description 'Transparent needles ' _exptl_crystal_colour 'Dark orange ' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method ? _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.576 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Stoe-IPDS _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12282 _diffrn_reflns_av_R_equivalents 0.1252 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 5.04 _diffrn_reflns_theta_max 28.07 _reflns_number_total 4011 _reflns_number_observed 2699 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe Expose' _computing_cell_refinement 'Stoe Expose' _computing_data_reduction 'Stoe - Integrate' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics 'Ortep' _computing_publication_material 'SHELXL-93' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 305 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.1064P)^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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 3706 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_obs 0.0656 _refine_ls_wR_factor_all 0.2009 _refine_ls_wR_factor_obs 0.1562 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_goodness_of_fit_obs 1.057 _refine_ls_restrained_S_all 1.107 _refine_ls_restrained_S_obs 1.057 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni1 Ni -0.09725(10) -0.27354(7) -0.50246(5) 0.0317(2) Uani 1 d . . S1 S -0.0664(2) -0.2591(2) -0.39082(9) 0.0371(4) Uani 1 d . . N1 N -0.0349(7) -0.2716(5) -0.5987(3) 0.0350(13) Uani 1 d . . N2 N -0.1318(7) -0.4330(5) -0.5035(3) 0.0350(12) Uani 1 d . . O1 O -0.1292(6) -0.1157(4) -0.4981(2) 0.0384(10) Uani 1 d . . C1 C -0.0035(10) -0.3906(7) -0.3545(4) 0.037(2) Uani 1 d . . C2 C 0.0589(10) -0.3900(7) -0.2857(4) 0.042(2) Uani 1 d . . H2 H 0.0676(10) -0.3195(7) -0.2620(4) 0.050 Uiso 1 calc R . C3 C 0.1076(11) -0.4887(8) -0.2522(4) 0.050(2) Uani 1 d . . H3 H 0.1439(11) -0.4856(8) -0.2055(4) 0.060 Uiso 1 calc R . C4 C 0.1036(11) -0.5947(7) -0.2871(4) 0.047(2) Uani 1 d . . H4 H 0.1454(11) -0.6624(7) -0.2658(4) 0.056 Uiso 1 calc R . C5 C 0.0359(10) -0.5958(7) -0.3540(4) 0.042(2) Uani 1 d . . H5 H 0.0241(10) -0.6670(7) -0.3767(4) 0.051 Uiso 1 calc R . C6 C -0.0155(9) -0.4967(6) -0.3891(4) 0.036(2) Uani 1 d . . C7 C -0.0950(10) -0.5117(7) -0.4576(4) 0.040(2) Uani 1 d . . H7 H -0.1231(10) -0.5877(7) -0.4701(4) 0.047 Uiso 1 calc R . C8 C -0.2349(9) -0.4727(7) -0.5643(3) 0.036(2) Uani 1 d . . H8A H -0.3422(9) -0.4252(7) -0.5686(3) 0.043 Uiso 1 calc R . H8B H -0.2731(9) -0.5522(7) -0.5562(3) 0.043 Uiso 1 calc R . C9 C -0.1322(10) -0.4676(7) -0.6326(4) 0.040(2) Uani 1 d . . H9A H -0.2138(10) -0.4459(7) -0.6702(4) 0.048 Uiso 1 calc R . H9B H -0.0850(10) -0.5443(7) -0.6433(4) 0.048 Uiso 1 calc R . C10 C 0.0215(10) -0.3816(6) -0.6301(4) 0.036(2) Uani 1 d . . H10A H 0.1196(10) -0.4143(6) -0.6029(4) 0.043 Uiso 1 calc R . H10B H 0.0651(10) -0.3676(6) -0.6774(4) 0.043 Uiso 1 calc R . C11 C 0.0028(9) -0.1808(6) -0.6338(4) 0.0338(15) Uani 1 d . . H11 H 0.0473(9) -0.1920(6) -0.6790(4) 0.041 Uiso 1 calc R . C12 C -0.0166(9) -0.0638(6) -0.6107(4) 0.0324(14) Uani 1 d . . C13 C 0.0389(9) 0.0226(6) -0.6561(4) 0.0351(15) Uani 1 d . . H13 H 0.0827(9) 0.0030(6) -0.7004(4) 0.042 Uiso 1 calc R . C14 C 0.0296(9) 0.1373(6) -0.6363(4) 0.037(2) Uani 1 d . . C15 C -0.0412(9) 0.1648(6) -0.5715(4) 0.037(2) Uani 1 d . . H15 H -0.0489(9) 0.2423(6) -0.5578(4) 0.044 Uiso 1 calc R . C16 C -0.0990(10) 0.0811(6) -0.5279(4) 0.0345(14) Uani 1 d . . C17 C -0.0852(9) -0.0374(6) -0.5440(4) 0.0341(14) Uani 1 d . . Cl1 Cl -0.1850(3) 0.1198(2) -0.44698(10) 0.0445(5) Uani 1 d . . Cl2 Cl 0.1053(3) 0.2444(2) -0.69179(10) 0.0478(4) Uani 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 0.0331(4) 0.0284(4) 0.0335(4) -0.0024(4) 0.0014(4) 0.0002(3) S1 0.0428(8) 0.0336(9) 0.0348(9) -0.0028(7) -0.0020(6) 0.0034(8) N1 0.032(3) 0.023(3) 0.049(3) -0.005(3) -0.001(2) -0.002(2) N2 0.032(3) 0.041(3) 0.032(3) -0.002(3) -0.001(3) 0.002(2) O1 0.040(2) 0.042(3) 0.033(2) 0.000(3) 0.006(2) 0.000(2) C1 0.035(3) 0.041(4) 0.035(4) -0.006(3) -0.003(3) -0.005(3) C2 0.044(4) 0.043(4) 0.038(4) -0.007(3) -0.006(3) 0.004(3) C3 0.054(5) 0.057(5) 0.038(4) 0.005(4) -0.007(4) 0.004(4) C4 0.046(4) 0.043(4) 0.051(5) 0.014(3) -0.004(4) 0.000(4) C5 0.046(4) 0.040(4) 0.041(4) -0.002(3) 0.005(3) -0.003(3) C6 0.028(3) 0.039(4) 0.040(4) -0.002(3) 0.001(3) -0.002(3) C7 0.031(3) 0.043(4) 0.045(4) -0.011(3) -0.001(3) -0.002(3) C8 0.031(3) 0.040(4) 0.035(4) -0.004(3) -0.004(3) -0.001(3) C9 0.044(4) 0.035(4) 0.041(4) -0.006(3) 0.010(3) -0.007(3) C10 0.039(4) 0.029(4) 0.040(4) -0.006(3) 0.005(3) 0.003(3) C11 0.034(3) 0.034(4) 0.034(4) -0.003(3) -0.003(3) 0.002(3) C12 0.035(3) 0.033(4) 0.029(4) -0.004(3) 0.002(3) 0.006(3) C13 0.040(4) 0.032(4) 0.033(4) -0.005(3) -0.004(3) 0.003(3) C14 0.042(4) 0.033(4) 0.035(4) -0.004(3) -0.005(3) 0.002(3) C15 0.038(3) 0.031(4) 0.042(4) -0.002(3) -0.004(3) 0.004(3) C16 0.037(3) 0.031(3) 0.036(3) -0.002(3) 0.002(3) 0.001(3) C17 0.031(3) 0.031(3) 0.040(4) -0.001(3) 0.004(3) -0.008(3) Cl1 0.0532(10) 0.0334(9) 0.0468(10) -0.0056(8) 0.0102(9) 0.0028(8) Cl2 0.0639(10) 0.0372(10) 0.0424(9) 0.0053(8) 0.0006(8) -0.0047(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 Ni1 O1 1.851(5) . ? Ni1 N2 1.871(6) . ? Ni1 N1 1.909(6) . ? Ni1 S1 2.166(2) . ? S1 C1 1.744(8) . ? N1 C11 1.284(9) . ? N1 C10 1.476(9) . ? N2 C7 1.301(9) . ? N2 C8 1.476(8) . ? O1 C17 1.310(8) . ? C1 C2 1.403(10) . ? C1 C6 1.404(10) . ? C2 C3 1.365(11) . ? C2 H2 0.94 . ? C3 C4 1.402(11) . ? C3 H3 0.94 . ? C4 C5 1.383(11) . ? C4 H4 0.94 . ? C5 C6 1.389(11) . ? C5 H5 0.94 . ? C6 C7 1.455(10) . ? C7 H7 0.94 . ? C8 C9 1.525(9) . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C9 C10 1.527(10) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C11 C12 1.437(9) . ? C11 H11 0.94 . ? C12 C13 1.394(10) . ? C12 C17 1.415(9) . ? C13 C14 1.388(10) . ? C13 H13 0.94 . ? C14 C15 1.393(10) . ? C14 Cl2 1.735(8) . ? C15 C16 1.354(10) . ? C15 H15 0.94 . ? C16 C17 1.415(9) . ? C16 Cl1 1.743(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 O1 Ni1 N2 164.4(2) . . ? O1 Ni1 N1 93.7(2) . . ? N2 Ni1 N1 92.0(3) . . ? O1 Ni1 S1 83.8(2) . . ? N2 Ni1 S1 95.9(2) . . ? N1 Ni1 S1 159.0(2) . . ? C1 S1 Ni1 111.0(3) . . ? C11 N1 C10 115.6(6) . . ? C11 N1 Ni1 125.0(5) . . ? C10 N1 Ni1 117.2(5) . . ? C7 N2 C8 115.5(6) . . ? C7 N2 Ni1 131.2(5) . . ? C8 N2 Ni1 113.0(5) . . ? C17 O1 Ni1 128.6(4) . . ? C2 C1 C6 118.2(8) . . ? C2 C1 S1 117.6(6) . . ? C6 C1 S1 124.2(6) . . ? C3 C2 C1 122.0(8) . . ? C3 C2 H2 119.0(5) . . ? C1 C2 H2 119.0(5) . . ? C2 C3 C4 120.4(7) . . ? C2 C3 H3 119.8(5) . . ? C4 C3 H3 119.8(4) . . ? C5 C4 C3 117.4(7) . . ? C5 C4 H4 121.3(5) . . ? C3 C4 H4 121.3(5) . . ? C4 C5 C6 123.2(7) . . ? C4 C5 H5 118.4(5) . . ? C6 C5 H5 118.4(5) . . ? C5 C6 C1 118.6(7) . . ? C5 C6 C7 117.1(7) . . ? C1 C6 C7 124.0(7) . . ? N2 C7 C6 128.1(7) . . ? N2 C7 H7 115.9(4) . . ? C6 C7 H7 115.9(4) . . ? N2 C8 C9 113.9(5) . . ? N2 C8 H8A 108.8(4) . . ? C9 C8 H8A 108.8(4) . . ? N2 C8 H8B 108.8(4) . . ? C9 C8 H8B 108.8(4) . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 112.4(6) . . ? C8 C9 H9A 109.1(4) . . ? C10 C9 H9A 109.1(4) . . ? C8 C9 H9B 109.1(4) . . ? C10 C9 H9B 109.1(4) . . ? H9A C9 H9B 107.9 . . ? N1 C10 C9 111.2(6) . . ? N1 C10 H10A 109.4(4) . . ? C9 C10 H10A 109.4(4) . . ? N1 C10 H10B 109.4(4) . . ? C9 C10 H10B 109.4(4) . . ? H10A C10 H10B 108.0 . . ? N1 C11 C12 126.3(7) . . ? N1 C11 H11 116.9(4) . . ? C12 C11 H11 116.9(4) . . ? C13 C12 C17 121.3(6) . . ? C13 C12 C11 117.2(6) . . ? C17 C12 C11 121.5(7) . . ? C14 C13 C12 120.3(7) . . ? C14 C13 H13 119.8(4) . . ? C12 C13 H13 119.8(4) . . ? C13 C14 C15 119.0(7) . . ? C13 C14 Cl2 120.2(6) . . ? C15 C14 Cl2 120.7(6) . . ? C16 C15 C14 120.8(7) . . ? C16 C15 H15 119.6(4) . . ? C14 C15 H15 119.6(4) . . ? C15 C16 C17 122.6(7) . . ? C15 C16 Cl1 119.1(5) . . ? C17 C16 Cl1 118.2(5) . . ? O1 C17 C12 123.5(6) . . ? O1 C17 C16 120.6(6) . . ? C12 C17 C16 115.9(6) . . ? _refine_diff_density_max .893 _refine_diff_density_min -.750 _refine_diff_density_rms .159