Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Dolling, Ben' 'Gillon, Amy L.' 'Orpen, A.' 'Starbuck, Jonathan' 'Wang, Xi-Meng' _publ_contact_author_name 'Prof A Orpen' _publ_contact_author_address ; Prof A Orpen School of Chemistry The University Cantock's Close BRISTOL BS8 1TS U.K. ; _publ_contact_author_email 'guy.orpen@bristol.ac.uk' data_1clbipy _database_code_CSD 154205 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H5 Cl N' _chemical_formula_weight 114.55 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.687(4) _cell_length_b 12.0981(19) _cell_length_c 7.0707(17) _cell_angle_alpha 90.00 _cell_angle_beta 112.565(18) _cell_angle_gamma 90.00 _cell_volume 1002.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 71 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'none' _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.605 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.802930 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 3127 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1151 _reflns_number_gt 1001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1151 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.34820(3) -0.13805(3) 0.22812(5) 0.01909(14) Uani 1 1 d . . . N1 N 0.5000 0.07450(14) 0.2500 0.0190(4) Uani 1 2 d S . . H1 H 0.5000 -0.001(3) 0.2500 0.042(8) Uiso 1 2 d S . . N2 N 0.5000 0.64967(13) 0.2500 0.0197(4) Uani 1 2 d S . . H2 H 0.5000 0.726(2) 0.2500 0.029(6) Uiso 1 2 d S . . C1 C 0.58678(13) 0.12780(11) 0.2278(2) 0.0208(3) Uani 1 1 d . . . H1A H 0.6467 0.0871 0.2110 0.025 Uiso 1 1 calc R . . C2 C 0.58957(12) 0.24157(11) 0.2291(2) 0.0190(3) Uani 1 1 d . . . H2A H 0.6518 0.2797 0.2158 0.023 Uiso 1 1 calc R . . C3 C 0.5000 0.30018(15) 0.2500 0.0147(4) Uani 1 2 d S . . C4 C 0.5000 0.42310(15) 0.2500 0.0153(4) Uani 1 2 d S . . C5 C 0.39764(12) 0.48234(11) 0.1875(2) 0.0191(3) Uani 1 1 d . . . H5 H 0.3268 0.4442 0.1445 0.023 Uiso 1 1 calc R . . C6 C 0.39982(13) 0.59649(12) 0.1885(2) 0.0204(3) Uani 1 1 d . . . H6 H 0.3305 0.6371 0.1457 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0154(2) 0.01355(19) 0.0281(2) -0.00155(12) 0.00808(15) -0.00103(12) N1 0.0255(9) 0.0119(8) 0.0201(8) 0.000 0.0094(7) 0.000 N2 0.0278(10) 0.0118(8) 0.0186(8) 0.000 0.0078(7) 0.000 C1 0.0236(8) 0.0160(7) 0.0254(7) 0.0010(5) 0.0121(6) 0.0036(5) C2 0.0194(7) 0.0162(7) 0.0233(7) 0.0020(5) 0.0104(6) 0.0014(5) C3 0.0168(9) 0.0120(9) 0.0145(8) 0.000 0.0052(7) 0.000 C4 0.0192(9) 0.0127(9) 0.0157(8) 0.000 0.0085(7) 0.000 C5 0.0169(7) 0.0168(7) 0.0230(7) -0.0003(5) 0.0069(5) 0.0001(5) C6 0.0216(7) 0.0162(7) 0.0224(7) 0.0010(5) 0.0073(6) 0.0039(5) _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 N1 C1 1.3363(17) 2_655 ? N1 C1 1.3363(17) . ? N2 C6 1.3396(17) . ? N2 C6 1.3396(17) 2_655 ? C1 C2 1.3768(18) . ? C2 C3 1.3947(16) . ? C3 C2 1.3947(16) 2_655 ? C3 C4 1.487(3) . ? C4 C5 1.3982(17) 2_655 ? C4 C5 1.3982(17) . ? C5 C6 1.3812(19) . ? 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 C1 N1 C1 122.30(18) 2_655 . ? C6 N2 C6 122.59(17) . 2_655 ? N1 C1 C2 120.12(14) . . ? C1 C2 C3 119.28(14) . . ? C2 C3 C2 118.88(17) 2_655 . ? C2 C3 C4 120.56(9) 2_655 . ? C2 C3 C4 120.56(9) . . ? C5 C4 C5 118.32(17) 2_655 . ? C5 C4 C3 120.84(9) 2_655 . ? C5 C4 C3 120.84(9) . . ? C6 C5 C4 119.77(14) . . ? N2 C6 C5 119.77(14) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.356 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.054 data_3govan _database_code_CSD 154206 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl6 N2 Pt' _chemical_formula_weight 565.99 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Pt' 'Pt' -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ibam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 7.4757(17) _cell_length_b 12.837(2) _cell_length_c 15.362(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1474.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 98 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 10.590 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.446068 _exptl_absorpt_correction_T_max 0.694163 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 4298 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.48 _reflns_number_total 884 _reflns_number_gt 782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0276P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00125(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 884 _refine_ls_number_parameters 51 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0474 _refine_ls_wR_factor_gt 0.0463 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 Pt1 Pt 0.0000 0.0000 0.0000 0.01278(11) Uani 1 4 d S . . Cl1 Cl -0.14855(15) 0.15920(7) 0.0000 0.0188(2) Uani 1 2 d S . . Cl2 Cl -0.27225(15) -0.08672(9) 0.0000 0.0244(3) Uani 1 2 d S . . Cl3 Cl 0.0000 0.0000 0.15093(8) 0.0234(3) Uani 1 2 d S . . N1 N -0.5000 0.2702(3) 0.2500 0.0233(9) Uani 1 2 d S . . H1A H -0.5000 0.3372 0.2500 0.028 Uiso 1 2 calc SR . . C1 C -0.4447(5) 0.2207(3) 0.1784(2) 0.0229(7) Uani 1 1 d . . . H1B H -0.4069 0.2585 0.1301 0.028 Uiso 1 1 calc R . . C2 C -0.4440(5) 0.1128(3) 0.17643(19) 0.0200(6) Uani 1 1 d . . . H2A H -0.4066 0.0775 0.1268 0.024 Uiso 1 1 calc R . . C3 C -0.5000 0.0574(4) 0.2500 0.0173(9) Uani 1 2 d S . . 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 Pt1 0.01939(15) 0.00848(14) 0.01047(15) 0.000 0.000 0.00010(8) Cl1 0.0278(6) 0.0110(5) 0.0175(5) 0.000 0.000 0.0039(4) Cl2 0.0227(6) 0.0186(5) 0.0318(6) 0.000 0.000 -0.0049(4) Cl3 0.0428(7) 0.0158(5) 0.0116(5) 0.000 0.000 0.0053(4) N1 0.024(2) 0.0126(19) 0.033(2) 0.000 -0.0043(15) 0.000 C1 0.0247(16) 0.0170(16) 0.0271(19) 0.0051(13) -0.0025(14) -0.0028(13) C2 0.0205(15) 0.0183(16) 0.0212(17) -0.0001(13) -0.0016(12) 0.0004(13) C3 0.016(2) 0.016(2) 0.020(2) 0.000 -0.0051(15) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pt1 Cl3 2.3185(13) 9 ? Pt1 Cl3 2.3185(13) . ? Pt1 Cl2 2.3198(11) 9 ? Pt1 Cl2 2.3198(11) . ? Pt1 Cl1 2.3258(11) 9 ? Pt1 Cl1 2.3258(11) . ? N1 C1 1.336(4) 7_345 ? N1 C1 1.336(4) . ? C1 C2 1.385(4) . ? C2 C3 1.399(4) . ? C3 C2 1.399(4) 7_345 ? C3 C3 1.474(9) 2_455 ? 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 Cl3 Pt1 Cl3 180.0 9 . ? Cl3 Pt1 Cl2 90.0 9 9 ? Cl3 Pt1 Cl2 90.0 . 9 ? Cl3 Pt1 Cl2 90.0 9 . ? Cl3 Pt1 Cl2 90.0 . . ? Cl2 Pt1 Cl2 180.00(5) 9 . ? Cl3 Pt1 Cl1 90.0 9 9 ? Cl3 Pt1 Cl1 90.0 . 9 ? Cl2 Pt1 Cl1 90.16(4) 9 9 ? Cl2 Pt1 Cl1 89.84(4) . 9 ? Cl3 Pt1 Cl1 90.0 9 . ? Cl3 Pt1 Cl1 90.0 . . ? Cl2 Pt1 Cl1 89.84(4) 9 . ? Cl2 Pt1 Cl1 90.16(4) . . ? Cl1 Pt1 Cl1 180.0 9 . ? C1 N1 C1 123.2(4) 7_345 . ? N1 C1 C2 119.6(3) . . ? C1 C2 C3 119.3(3) . . ? C2 C3 C2 118.9(4) 7_345 . ? C2 C3 C3 120.5(2) 7_345 2_455 ? C2 C3 C3 120.5(2) . 2_455 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.139 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.124 data_2sauchie _database_code_CSD 154207 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl6 N2 Os' _chemical_formula_weight 561.10 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Os' 'Os' -1.2165 7.6030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ibam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 7.3602(10) _cell_length_b 12.8184(18) _cell_length_c 15.606(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1472.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 65 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 9.734 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.342003 _exptl_absorpt_correction_T_max 0.491499 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'w\ rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 4502 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.53 _reflns_number_total 883 _reflns_number_gt 659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0279P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 883 _refine_ls_number_parameters 50 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0539 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Os1 Os 0.5000 0.5000 0.5000 0.01510(11) Uani 1 4 d S . . Cl1 Cl 0.5000 0.5000 0.34952(9) 0.0262(3) Uani 1 2 d S . . Cl2 Cl 0.6501(2) 0.33975(14) 0.5000 0.0209(4) Uani 1 2 d S . . Cl3 Cl 0.2211(2) 0.41521(15) 0.5000 0.0270(4) Uani 1 2 d S . . N1 N 0.0000 0.2291(4) 0.2500 0.0259(12) Uani 1 2 d S . . H1 H 0.0000 0.1620 0.2500 0.031 Uiso 1 2 calc SR . . C1 C -0.0520(7) 0.2793(4) 0.3214(3) 0.0255(13) Uani 1 1 d . . . H1A H -0.0865 0.2418 0.3698 0.031 Uiso 1 1 calc R . . C2 C -0.0538(6) 0.3868(4) 0.3224(3) 0.0200(11) Uani 1 1 d . . . H2 H -0.0907 0.4224 0.3713 0.024 Uiso 1 1 calc R . . C3 C 0.0000 0.4418(5) 0.2500 0.0180(12) Uani 1 2 d S . . 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 Os1 0.02242(18) 0.01188(17) 0.01100(16) 0.000 0.000 0.0002(2) Cl1 0.0480(9) 0.0186(7) 0.0121(6) 0.000 0.000 0.0051(12) Cl2 0.0298(9) 0.0145(8) 0.0186(8) 0.000 0.000 0.0049(7) Cl3 0.0247(9) 0.0216(9) 0.0346(10) 0.000 0.000 -0.0051(8) N1 0.027(3) 0.015(3) 0.035(3) 0.000 -0.005(4) 0.000 C1 0.026(3) 0.023(3) 0.027(3) 0.012(2) -0.003(2) -0.004(2) C2 0.021(2) 0.021(3) 0.017(2) 0.001(2) -0.0023(18) 0.0013(19) C3 0.015(3) 0.017(3) 0.022(3) 0.000 -0.002(4) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Os1 Cl3 2.3225(17) 9_666 ? Os1 Cl3 2.3225(17) . ? Os1 Cl2 2.3325(17) . ? Os1 Cl2 2.3325(17) 9_666 ? Os1 Cl1 2.3484(14) . ? Os1 Cl1 2.3484(14) 9_666 ? N1 C1 1.343(6) . ? N1 C1 1.343(6) 7_445 ? C1 C2 1.379(7) . ? C2 C3 1.389(6) . ? C3 C2 1.389(6) 7_445 ? C3 C3 1.492(12) 2_565 ? 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 Cl3 Os1 Cl3 180.0 9_666 . ? Cl3 Os1 Cl2 89.63(6) 9_666 . ? Cl3 Os1 Cl2 90.37(6) . . ? Cl3 Os1 Cl2 90.37(6) 9_666 9_666 ? Cl3 Os1 Cl2 89.63(6) . 9_666 ? Cl2 Os1 Cl2 180.00(7) . 9_666 ? Cl3 Os1 Cl1 90.0 9_666 . ? Cl3 Os1 Cl1 90.0 . . ? Cl2 Os1 Cl1 90.0 . . ? Cl2 Os1 Cl1 90.0 9_666 . ? Cl3 Os1 Cl1 90.0 9_666 9_666 ? Cl3 Os1 Cl1 90.0 . 9_666 ? Cl2 Os1 Cl1 90.0 . 9_666 ? Cl2 Os1 Cl1 90.0 9_666 9_666 ? Cl1 Os1 Cl1 180.0 . 9_666 ? C1 N1 C1 122.8(6) . 7_445 ? N1 C1 C2 119.4(5) . . ? C1 C2 C3 119.7(5) . . ? C2 C3 C2 119.0(6) 7_445 . ? C2 C3 C3 120.5(3) 7_445 2_565 ? C2 C3 C3 120.5(3) . 2_565 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.517 _refine_diff_density_min -0.929 _refine_diff_density_rms 0.171 data_4nitshil _database_code_CSD 154208 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl5 Fe N2' _chemical_formula_weight 391.30 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ama2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.651(2) _cell_length_b 11.6816(15) _cell_length_c 7.2764(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1415.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.990 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.869677 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 4523 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1671 _reflns_number_gt 1408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0222P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(2) _refine_ls_number_reflns 1671 _refine_ls_number_parameters 90 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Fe1 Fe 0.5000 0.0000 0.02531(7) 0.01824(14) Uani 1 2 d S . . Cl1 Cl 0.64607(4) 0.01485(5) 0.02346(11) 0.02403(16) Uani 1 1 d . . . Cl2 Cl 0.49262(4) 0.16582(7) -0.12892(12) 0.0334(2) Uani 1 1 d . . . Cl3 Cl 0.5000 0.0000 0.33373(15) 0.0288(3) Uani 1 2 d S . . N1 N 0.7500 -0.0880(3) -0.3117(5) 0.0264(8) Uani 1 2 d S . . H1 H 0.7500 -0.0528 -0.2079 0.032 Uiso 1 2 calc SR . . N2 N 0.7500 -0.3722(3) -1.1516(5) 0.0216(8) Uani 1 2 d S . . H2 H 0.7500 -0.4079 -1.2550 0.026 Uiso 1 2 calc SR . . C1 C 0.6799(2) -0.1145(3) -0.3893(5) 0.0376(9) Uani 1 1 d . . . H1A H 0.6319 -0.0943 -0.3322 0.045 Uiso 1 1 calc R . . C2 C 0.6789(2) -0.1718(3) -0.5548(5) 0.0320(9) Uani 1 1 d . . . H2A H 0.6302 -0.1908 -0.6094 0.038 Uiso 1 1 calc R . . C3 C 0.7500 -0.2011(3) -0.6396(6) 0.0174(8) Uani 1 2 d S . . C4 C 0.7500 -0.2622(3) -0.8198(6) 0.0154(8) Uani 1 2 d S . . C5 C 0.67833(19) -0.2903(3) -0.9065(5) 0.0283(8) Uani 1 1 d . . . H5 H 0.6296 -0.2720 -0.8516 0.034 Uiso 1 1 calc R . . C6 C 0.6795(2) -0.3460(3) -1.0755(4) 0.0302(8) Uani 1 1 d . . . H6 H 0.6318 -0.3646 -1.1347 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0140(3) 0.0238(3) 0.0169(3) 0.000 0.000 -0.0012(2) Cl1 0.0143(3) 0.0359(3) 0.0219(3) -0.0095(5) 0.0002(4) -0.0016(3) Cl2 0.0215(4) 0.0346(4) 0.0442(5) 0.0167(3) -0.0021(5) -0.0047(3) Cl3 0.0200(6) 0.0480(6) 0.0184(4) 0.000 0.000 -0.0048(5) N1 0.041(2) 0.0230(17) 0.0153(17) -0.0061(16) 0.000 0.000 N2 0.029(2) 0.0190(16) 0.0169(18) -0.0063(14) 0.000 0.000 C1 0.035(2) 0.0414(19) 0.036(2) -0.0179(17) 0.0187(17) -0.0131(17) C2 0.0233(18) 0.0424(19) 0.0305(19) -0.0179(17) 0.0051(14) -0.0111(17) C3 0.020(2) 0.0133(17) 0.019(2) -0.0016(16) 0.000 0.000 C4 0.016(2) 0.0144(17) 0.0156(19) 0.0004(17) 0.000 0.000 C5 0.0190(19) 0.0427(19) 0.0231(16) -0.0107(15) 0.0013(14) -0.0010(15) C6 0.0221(18) 0.043(2) 0.0251(18) -0.0114(16) -0.0037(14) -0.0069(16) _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 Fe1 Cl2 2.2421(8) . ? Fe1 Cl2 2.2421(8) 2_655 ? Fe1 Cl3 2.2442(12) . ? Fe1 Cl1 2.4384(8) 2_655 ? Fe1 Cl1 2.4385(8) . ? N1 C1 1.334(4) . ? N1 C1 1.334(4) 4_655 ? N2 C6 1.333(4) . ? N2 C6 1.333(4) 4_655 ? C1 C2 1.378(4) . ? C2 C3 1.379(4) . ? C3 C2 1.379(4) 4_655 ? C3 C4 1.493(5) . ? C4 C5 1.389(4) . ? C4 C5 1.389(4) 4_655 ? C5 C6 1.391(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Fe1 Cl2 119.93(5) . 2_655 ? Cl2 Fe1 Cl3 120.04(3) . . ? Cl2 Fe1 Cl3 120.03(3) 2_655 . ? Cl2 Fe1 Cl1 90.23(3) . 2_655 ? Cl2 Fe1 Cl1 89.46(3) 2_655 2_655 ? Cl3 Fe1 Cl1 90.32(2) . 2_655 ? Cl2 Fe1 Cl1 89.45(3) . . ? Cl2 Fe1 Cl1 90.23(3) 2_655 . ? Cl3 Fe1 Cl1 90.32(2) . . ? Cl1 Fe1 Cl1 179.37(4) 2_655 . ? C1 N1 C1 122.3(4) . 4_655 ? C6 N2 C6 123.3(4) . 4_655 ? N1 C1 C2 119.5(3) . . ? C1 C2 C3 120.1(3) . . ? C2 C3 C2 118.4(4) 4_655 . ? C2 C3 C4 120.8(2) 4_655 . ? C2 C3 C4 120.8(2) . . ? C5 C4 C5 118.4(4) . 4_655 ? C5 C4 C3 120.80(19) . . ? C5 C4 C3 120.79(19) 4_655 . ? C4 C5 C6 120.0(3) . . ? N2 C6 C5 119.2(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.068