# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Aldridge, S.' 'Calder, R. J.' 'Coles, Simon J.' 'Coombs, D.L.' 'Hursthouse, Michael B.' 'Jones, C.' 'Steed, Jon' _publ_contact_author_name 'Dr S Aldridge' _publ_contact_author_address ; Department of Chemistry Cardiff University of Wales PO Box 912 Park Place Cardiff CF10 3TB ; _publ_contact_author_email 'ALDRIDGES@CARDIFF.AC.UK' _publ_section_title ; Intramolecular base-stabilised adducts of main group halides ; data_sa3 _database_code_CSD 183227 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 B Br2 N2 Si' _chemical_formula_weight 349.95 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' 'B' 'B' 0.0013 0.0007 '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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8246(7) _cell_length_b 13.9297(17) _cell_length_c 14.2729(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.113(9) _cell_angle_gamma 90.00 _cell_volume 1354.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 6.043 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.0856 _exptl_absorpt_correction_T_max 0.1960 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 KappaCCD _diffrn_measurement_method '2o phi+omega frames 5s deg-1' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6753 _diffrn_reflns_av_R_equivalents 0.1559 _diffrn_reflns_av_sigmaI/netI 0.1351 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2643 _reflns_number_gt 2102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _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^)+(0.0192P)^2^+5.7537P] 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 0.0099(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2643 _refine_ls_number_parameters 141 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 Br1 Br 0.14982(10) 0.69915(5) 0.78675(4) 0.0150(2) Uani 1 1 d . . . Si1 Si -0.2701(3) 0.65438(12) 0.98388(12) 0.0089(4) Uani 1 1 d . . . N1 N 0.0839(7) 0.8561(4) 0.9247(4) 0.0084(11) Uani 1 1 d U . . C1 C 0.0077(9) 0.8080(4) 0.9979(4) 0.0082(12) Uani 1 1 d U . . B1 B -0.0285(10) 0.7823(5) 0.8574(5) 0.0108(15) Uani 1 1 d U . . Br2 Br -0.23482(9) 0.84358(4) 0.77175(4) 0.0132(2) Uani 1 1 d . . . N2 N -0.1016(7) 0.7402(4) 0.9495(4) 0.0088(11) Uani 1 1 d U . . C2 C 0.0509(9) 0.8370(5) 1.0899(5) 0.0115(13) Uani 1 1 d U . . H2 H -0.0004 0.8049 1.1420 0.014 Uiso 1 1 calc R . . C3 C 0.1736(8) 0.9155(4) 1.1005(4) 0.0084(13) Uani 1 1 d U . . H3 H 0.2091 0.9373 1.1621 0.010 Uiso 1 1 calc R . . C4 C 0.2480(9) 0.9645(4) 1.0245(4) 0.0114(13) Uani 1 1 d . . . H4 H 0.3286 1.0195 1.0350 0.014 Uiso 1 1 calc R . . C5 C 0.2038(9) 0.9325(5) 0.9340(4) 0.0102(13) Uani 1 1 d . . . C6 C 0.2769(10) 0.9763(5) 0.8468(4) 0.0149(14) Uani 1 1 d . . . H6A H 0.3740 0.9336 0.8206 0.022 Uiso 1 1 calc R . . H6B H 0.3378 1.0385 0.8620 0.022 Uiso 1 1 calc R . . H6C H 0.1667 0.9855 0.8008 0.022 Uiso 1 1 calc R . . C7 C -0.4957(11) 0.7153(5) 1.0203(5) 0.0243(17) Uani 1 1 d . . . H7A H -0.4616 0.7604 1.0713 0.036 Uiso 1 1 calc R . . H7B H -0.5879 0.6673 1.0421 0.036 Uiso 1 1 calc R . . H7C H -0.5568 0.7503 0.9668 0.036 Uiso 1 1 calc R . . C8 C -0.1537(11) 0.5862(5) 1.0839(5) 0.0182(15) Uani 1 1 d . . . H8A H -0.0249 0.5628 1.0670 0.027 Uiso 1 1 calc R . . H8B H -0.2371 0.5316 1.0987 0.027 Uiso 1 1 calc R . . H8C H -0.1377 0.6283 1.1388 0.027 Uiso 1 1 calc R . . C9 C -0.3229(11) 0.5800(5) 0.8773(5) 0.0178(15) Uani 1 1 d . . . H9A H -0.3926 0.6189 0.8289 0.027 Uiso 1 1 calc R . . H9B H -0.4046 0.5251 0.8931 0.027 Uiso 1 1 calc R . . H9C H -0.1993 0.5568 0.8536 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0250(4) 0.0149(4) 0.0050(4) -0.0049(3) 0.0008(3) 0.0057(3) Si1 0.0163(9) 0.0082(8) 0.0017(8) 0.0004(7) -0.0038(7) 0.0006(7) N1 0.0112(17) 0.0087(17) 0.0049(17) -0.0025(15) -0.0028(14) -0.0001(15) C1 0.0100(19) 0.0086(19) 0.0059(19) -0.0010(16) -0.0001(15) 0.0017(16) B1 0.013(2) 0.011(2) 0.009(2) -0.0004(17) 0.0003(17) -0.0001(17) Br2 0.0204(4) 0.0129(4) 0.0054(4) -0.0008(2) -0.0077(3) 0.0028(3) N2 0.0121(17) 0.0079(17) 0.0061(17) -0.0015(15) -0.0021(14) -0.0009(15) C2 0.0129(19) 0.013(2) 0.009(2) 0.0005(16) 0.0005(16) 0.0014(16) C3 0.0107(19) 0.0096(19) 0.0046(19) -0.0007(16) -0.0021(15) 0.0022(16) C4 0.016(3) 0.011(3) 0.007(3) -0.005(3) -0.007(2) -0.001(3) C5 0.010(3) 0.011(3) 0.009(3) -0.005(3) -0.003(2) 0.005(3) C6 0.018(3) 0.019(3) 0.007(3) 0.002(3) 0.000(3) -0.005(3) C7 0.033(4) 0.023(4) 0.016(4) -0.001(3) 0.001(3) 0.006(3) C8 0.025(4) 0.019(3) 0.009(3) 0.009(3) -0.007(3) -0.005(3) C9 0.029(4) 0.014(3) 0.009(3) -0.002(3) -0.004(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 B1 1.993(7) . ? Si1 N2 1.747(5) . ? Si1 C8 1.857(7) . ? Si1 C7 1.857(8) . ? Si1 C9 1.860(7) . ? N1 C5 1.345(8) . ? N1 C1 1.367(8) . ? N1 B1 1.577(9) . ? C1 N2 1.368(8) . ? C1 C2 1.390(9) . ? B1 N2 1.547(9) . ? B1 Br2 2.004(7) . ? C2 C3 1.381(9) . ? C3 C4 1.400(9) . ? C4 C5 1.384(8) . ? C5 C6 1.496(9) . ? 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 N2 Si1 C8 107.8(3) . . ? N2 Si1 C7 109.5(3) . . ? C8 Si1 C7 110.2(3) . . ? N2 Si1 C9 104.6(3) . . ? C8 Si1 C9 113.6(3) . . ? C7 Si1 C9 110.9(3) . . ? C5 N1 C1 124.5(5) . . ? C5 N1 B1 148.1(5) . . ? C1 N1 B1 87.4(5) . . ? N1 C1 N2 99.9(5) . . ? N1 C1 C2 120.7(6) . . ? N2 C1 C2 139.4(6) . . ? N2 B1 N1 84.1(5) . . ? N2 B1 Br1 116.3(4) . . ? N1 B1 Br1 113.3(4) . . ? N2 B1 Br2 115.6(4) . . ? N1 B1 Br2 113.4(4) . . ? Br1 B1 Br2 111.5(3) . . ? C1 N2 B1 88.6(5) . . ? C1 N2 Si1 132.8(5) . . ? B1 N2 Si1 138.2(4) . . ? C3 C2 C1 115.4(6) . . ? C2 C3 C4 123.0(6) . . ? C5 C4 C3 119.7(6) . . ? N1 C5 C4 116.6(6) . . ? N1 C5 C6 118.0(5) . . ? C4 C5 C6 125.4(6) . . ? 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 C5 N1 C1 N2 179.2(5) . . . . ? B1 N1 C1 N2 -1.3(5) . . . . ? C5 N1 C1 C2 0.3(9) . . . . ? B1 N1 C1 C2 179.8(6) . . . . ? C5 N1 B1 N2 -179.7(9) . . . . ? C1 N1 B1 N2 1.1(4) . . . . ? C5 N1 B1 Br1 64.1(11) . . . . ? C1 N1 B1 Br1 -115.0(5) . . . . ? C5 N1 B1 Br2 -64.3(11) . . . . ? C1 N1 B1 Br2 116.5(5) . . . . ? N1 C1 N2 B1 1.3(5) . . . . ? C2 C1 N2 B1 179.9(8) . . . . ? N1 C1 N2 Si1 -172.5(5) . . . . ? C2 C1 N2 Si1 6.1(12) . . . . ? N1 B1 N2 C1 -1.1(4) . . . . ? Br1 B1 N2 C1 112.1(5) . . . . ? Br2 B1 N2 C1 -114.2(5) . . . . ? N1 B1 N2 Si1 172.0(5) . . . . ? Br1 B1 N2 Si1 -74.8(7) . . . . ? Br2 B1 N2 Si1 58.9(8) . . . . ? C8 Si1 N2 C1 -50.8(6) . . . . ? C7 Si1 N2 C1 69.1(6) . . . . ? C9 Si1 N2 C1 -172.0(6) . . . . ? C8 Si1 N2 B1 138.6(6) . . . . ? C7 Si1 N2 B1 -101.5(7) . . . . ? C9 Si1 N2 B1 17.4(7) . . . . ? N1 C1 C2 C3 -0.1(9) . . . . ? N2 C1 C2 C3 -178.5(7) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? C2 C3 C4 C5 -2.0(9) . . . . ? C1 N1 C5 C4 -1.3(9) . . . . ? B1 N1 C5 C4 179.7(8) . . . . ? C1 N1 C5 C6 179.2(6) . . . . ? B1 N1 C5 C6 0.2(13) . . . . ? C3 C4 C5 N1 2.1(8) . . . . ? C3 C4 C5 C6 -178.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.645 _refine_diff_density_min -1.401 _refine_diff_density_rms 0.219 data_cj135 _database_code_CSD 183228 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 B F N O2' _chemical_formula_weight 146.96 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z' 'x, -y, z+1/2' '-x, -y, z+1/2' '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' _cell_length_a 9.800(2) _cell_length_b 12.045(2) _cell_length_c 5.9433(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 701.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type sortav _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'kappa CCD' _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 1698 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 628 _reflns_number_gt 439 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1652P)^2^+0.0323P] 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 0.017(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(5) _refine_ls_number_reflns 628 _refine_ls_number_parameters 59 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1072 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.2531 _refine_ls_wR_factor_gt 0.2346 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 O1 O 0.0000 0.6764(5) 0.5236(9) 0.0791(19) Uani 1 2 d S . . O2 O 0.1150(5) 0.8467(4) 0.5016(10) 0.111(2) Uani 0.50 1 d P . . F1 F 0.1150(5) 0.8467(4) 0.5016(10) 0.111(2) Uani 0.50 1 d P . . N1 N 0.0000 0.7918(5) 0.8434(11) 0.064(2) Uani 1 2 d S . . B1 B 0.0000 0.7896(9) 0.5714(12) 0.058(3) Uani 1 2 d S . . C1 C 0.0000 0.6122(6) 0.707(2) 0.096(3) Uani 1 2 d S . . H1A H 0.0800 0.5647 0.7039 0.115 Uiso 0.50 1 calc PR . . H1B H -0.0800 0.5647 0.7039 0.115 Uiso 0.50 1 calc PR . . C2 C 0.0000 0.6762(10) 0.9152(18) 0.112(4) Uani 1 2 d SU . . H2A H -0.0805 0.6597 1.0041 0.134 Uiso 0.50 1 calc PR . . H2B H 0.0805 0.6597 1.0041 0.134 Uiso 0.50 1 calc PR . . C3 C 0.1282(11) 0.8498(9) 0.9242(12) 0.109(3) Uani 1 1 d . . . C4 C 0.1790(10) 0.8977(7) 0.736(2) 0.065(3) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.121(4) 0.070(4) 0.046(3) -0.018(3) 0.000 0.000 O2 0.105(3) 0.103(3) 0.125(5) 0.025(3) 0.053(3) -0.007(3) F1 0.105(3) 0.103(3) 0.125(5) 0.025(3) 0.053(3) -0.007(3) N1 0.122(6) 0.045(3) 0.027(2) 0.004(3) 0.000 0.000 B1 0.068(5) 0.085(7) 0.020(4) 0.006(4) 0.000 0.000 C1 0.172(8) 0.056(4) 0.059(5) -0.012(6) 0.000 0.000 C2 0.178(9) 0.094(6) 0.063(6) 0.030(5) 0.000 0.000 C3 0.147(7) 0.130(7) 0.050(4) -0.028(4) -0.033(4) -0.018(6) C4 0.084(6) 0.068(5) 0.043(5) 0.015(5) 0.010(5) -0.018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.336(14) . ? O1 B1 1.393(12) . ? O2 B1 1.384(8) . ? O2 C4 1.649(14) . ? N1 C2 1.456(14) . ? N1 C3 1.516(9) . ? N1 C3 1.516(9) 2 ? N1 B1 1.616(7) . ? B1 F1 1.384(8) 2 ? B1 O2 1.384(8) 2 ? C1 C2 1.459(16) . ? C3 C4 1.351(15) . ? 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 O1 B1 113.6(6) . . ? B1 O2 C4 104.0(6) . . ? C2 N1 C3 110.4(6) . . ? C2 N1 C3 110.4(6) . 2 ? C3 N1 C3 112.0(8) . 2 ? C2 N1 B1 106.1(9) . . ? C3 N1 B1 108.9(5) . . ? C3 N1 B1 108.9(5) 2 . ? O2 B1 F1 109.0(8) . 2 ? O2 B1 O2 109.0(8) . 2 ? F1 B1 O2 0.0(3) 2 2 ? O2 B1 O1 115.2(5) . . ? F1 B1 O1 115.2(5) 2 . ? O2 B1 O1 115.2(5) 2 . ? O2 B1 N1 107.0(6) . . ? F1 B1 N1 107.0(6) 2 . ? O2 B1 N1 107.0(6) 2 . ? O1 B1 N1 102.7(8) . . ? O1 C1 C2 112.7(5) . . ? N1 C2 C1 104.9(9) . . ? C4 C3 N1 103.9(7) . . ? C3 C4 O2 113.6(6) . . ? 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 C4 O2 B1 F1 109.1(7) . . . 2 ? C4 O2 B1 O2 109.1(7) . . . 2 ? C4 O2 B1 O1 -119.7(6) . . . . ? C4 O2 B1 N1 -6.3(8) . . . . ? C1 O1 B1 O2 115.9(5) . . . . ? C1 O1 B1 F1 -115.9(5) . . . 2 ? C1 O1 B1 O2 -115.9(5) . . . 2 ? C1 O1 B1 N1 0.000(3) . . . . ? C2 N1 B1 O2 -121.6(5) . . . . ? C3 N1 B1 O2 -2.8(9) . . . . ? C3 N1 B1 O2 119.6(5) 2 . . . ? C2 N1 B1 F1 121.6(5) . . . 2 ? C3 N1 B1 F1 -119.6(5) . . . 2 ? C3 N1 B1 F1 2.8(9) 2 . . 2 ? C2 N1 B1 O2 121.6(5) . . . 2 ? C3 N1 B1 O2 -119.6(5) . . . 2 ? C3 N1 B1 O2 2.8(9) 2 . . 2 ? C2 N1 B1 O1 0.000(3) . . . . ? C3 N1 B1 O1 118.8(5) . . . . ? C3 N1 B1 O1 -118.8(5) 2 . . . ? B1 O1 C1 C2 0.000(6) . . . . ? C3 N1 C2 C1 -117.8(6) . . . . ? C3 N1 C2 C1 117.8(6) 2 . . . ? B1 N1 C2 C1 0.000(5) . . . . ? O1 C1 C2 N1 0.000(6) . . . . ? C2 N1 C3 C4 128.5(10) . . . . ? C3 N1 C3 C4 -108.1(9) 2 . . . ? B1 N1 C3 C4 12.4(9) . . . . ? N1 C3 C4 O2 -16.9(9) . . . . ? B1 O2 C4 C3 15.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.262 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.058 data_s92 _database_code_CSD 183229 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 Cl3 N2 Si Sn' _chemical_formula_weight 404.36 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' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2498(18) _cell_length_b 9.7081(19) _cell_length_c 17.738(4) _cell_angle_alpha 93.62(3) _cell_angle_beta 90.61(3) _cell_angle_gamma 104.26(3) _cell_volume 1540.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18630 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _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 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 2.235 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.6634 _exptl_absorpt_correction_T_max 0.8074 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23521 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 27.46 _reflns_number_total 6924 _reflns_number_gt 5961 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _computing_publication_material ? _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^)+(0.0440P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6924 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.002 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 C1 C 0.0035(3) 0.2624(2) 0.26032(14) 0.0220(5) Uani 1 1 d . . . C2 C -0.1285(3) 0.2912(3) 0.28861(16) 0.0285(6) Uani 1 1 d . . . H2 H -0.1519 0.2828 0.3404 0.034 Uiso 1 1 calc R . . C3 C -0.2222(3) 0.3317(3) 0.23862(18) 0.0339(7) Uani 1 1 d . . . H3 H -0.3115 0.3523 0.2566 0.041 Uiso 1 1 calc R . . C4 C -0.1904(3) 0.3435(3) 0.16267(18) 0.0346(7) Uani 1 1 d . . . H4 H -0.2568 0.3721 0.1293 0.042 Uiso 1 1 calc R . . C5 C -0.0614(3) 0.3132(3) 0.13620(16) 0.0290(6) Uani 1 1 d . . . C6 C -0.0159(3) 0.3179(3) 0.05529(16) 0.0426(7) Uani 1 1 d . . . H6A H 0.0866 0.3759 0.0526 0.064 Uiso 1 1 calc R . . H6B H -0.0831 0.3598 0.0263 0.064 Uiso 1 1 calc R . . H6C H -0.0215 0.2210 0.0341 0.064 Uiso 1 1 calc R . . C7 C 0.0405(3) 0.2912(3) 0.45393(17) 0.0401(7) Uani 1 1 d . . . H7A H 0.0370 0.3838 0.4361 0.060 Uiso 1 1 calc R . . H7B H 0.0815 0.3042 0.5058 0.060 Uiso 1 1 calc R . . H7C H -0.0605 0.2287 0.4527 0.060 Uiso 1 1 calc R . . C8 C 0.1392(4) 0.0213(3) 0.41274(18) 0.0444(8) Uani 1 1 d . . . H8A H 0.0336 -0.0295 0.4076 0.067 Uiso 1 1 calc R . . H8B H 0.1751 0.0172 0.4645 0.067 Uiso 1 1 calc R . . H8C H 0.1972 -0.0235 0.3773 0.067 Uiso 1 1 calc R . . C9 C 0.3585(3) 0.3120(4) 0.40759(19) 0.0466(8) Uani 1 1 d . . . H9A H 0.4251 0.2558 0.3867 0.070 Uiso 1 1 calc R . . H9B H 0.3796 0.3330 0.4619 0.070 Uiso 1 1 calc R . . H9C H 0.3748 0.4015 0.3825 0.070 Uiso 1 1 calc R . . C10 C -0.6235(3) -0.2808(2) 0.23682(14) 0.0228(5) Uani 1 1 d . . . C11 C -0.7693(3) -0.3217(3) 0.20651(17) 0.0312(6) Uani 1 1 d . . . H11 H -0.7879 -0.3250 0.1536 0.037 Uiso 1 1 calc R . . C12 C -0.8838(3) -0.3567(3) 0.25508(18) 0.0341(7) Uani 1 1 d . . . H12 H -0.9833 -0.3845 0.2353 0.041 Uiso 1 1 calc R . . C13 C -0.8591(3) -0.3528(3) 0.33282(17) 0.0339(7) Uani 1 1 d . . . H13 H -0.9404 -0.3780 0.3657 0.041 Uiso 1 1 calc R . . C14 C -0.7148(3) -0.3120(3) 0.36124(16) 0.0306(6) Uani 1 1 d . . . C15 C -0.6719(4) -0.2989(3) 0.44378(16) 0.0415(7) Uani 1 1 d . . . H15A H -0.5938 -0.3491 0.4518 0.062 Uiso 1 1 calc R . . H15B H -0.7594 -0.3409 0.4729 0.062 Uiso 1 1 calc R . . H15C H -0.6345 -0.1980 0.4605 0.062 Uiso 1 1 calc R . . C16 C -0.3029(3) -0.3231(3) 0.08276(18) 0.0404(7) Uani 1 1 d . . . H16A H -0.2145 -0.2922 0.1164 0.061 Uiso 1 1 calc R . . H16B H -0.2733 -0.3102 0.0303 0.061 Uiso 1 1 calc R . . H16C H -0.3496 -0.4239 0.0886 0.061 Uiso 1 1 calc R . . C17 C -0.3524(4) -0.0234(3) 0.09754(18) 0.0433(8) Uani 1 1 d . . . H17A H -0.4260 0.0318 0.1089 0.065 Uiso 1 1 calc R . . H17B H -0.3192 -0.0097 0.0456 0.065 Uiso 1 1 calc R . . H17C H -0.2666 0.0091 0.1327 0.065 Uiso 1 1 calc R . . C18 C -0.6028(4) -0.2759(3) 0.04223(16) 0.0409(7) Uani 1 1 d . . . H18A H -0.6517 -0.3755 0.0499 0.061 Uiso 1 1 calc R . . H18B H -0.5704 -0.2679 -0.0101 0.061 Uiso 1 1 calc R . . H18C H -0.6731 -0.2167 0.0523 0.061 Uiso 1 1 calc R . . N1 N 0.1149(2) 0.2182(2) 0.29565(12) 0.0233(4) Uani 1 1 d . . . N2 N 0.0295(2) 0.2721(2) 0.18542(12) 0.0243(4) Uani 1 1 d . . . N3 N -0.4883(2) -0.2394(2) 0.20267(12) 0.0247(5) Uani 1 1 d . . . N4 N -0.6020(2) -0.2777(2) 0.31259(12) 0.0244(5) Uani 1 1 d . . . Cl1 Cl 0.14769(9) 0.01469(8) 0.09993(4) 0.0446(2) Uani 1 1 d . . . Cl2 Cl 0.40315(8) 0.07721(8) 0.25131(5) 0.04184(18) Uani 1 1 d . . . Cl3 Cl 0.39713(7) 0.38054(7) 0.15316(5) 0.03904(18) Uani 1 1 d . . . Cl4 Cl -0.30297(8) -0.38795(8) 0.36123(4) 0.03809(17) Uani 1 1 d . . . Cl5 Cl -0.12398(7) -0.11446(9) 0.24907(5) 0.04330(19) Uani 1 1 d . . . Cl6 Cl -0.34435(8) -0.01164(8) 0.39134(4) 0.03954(18) Uani 1 1 d . . . Sn1 Sn 0.229335(18) 0.185994(17) 0.198833(9) 0.02289(8) Uani 1 1 d . . . Sn2 Sn -0.358360(17) -0.199702(18) 0.301483(9) 0.02414(8) Uani 1 1 d . . . Si1 Si 0.16100(8) 0.20922(8) 0.39166(4) 0.02720(16) Uani 1 1 d . . . Si2 Si -0.43809(8) -0.21478(7) 0.10756(4) 0.02591(16) 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 C1 0.0201(11) 0.0169(12) 0.0270(13) -0.0012(10) -0.0005(10) 0.0017(9) C2 0.0228(12) 0.0276(14) 0.0341(15) -0.0032(11) 0.0051(11) 0.0054(10) C3 0.0199(12) 0.0297(15) 0.0515(19) -0.0078(13) -0.0016(13) 0.0077(11) C4 0.0264(13) 0.0241(14) 0.0528(19) 0.0013(13) -0.0128(13) 0.0063(11) C5 0.0250(12) 0.0260(14) 0.0345(15) 0.0042(11) -0.0058(12) 0.0031(10) C6 0.0407(16) 0.053(2) 0.0334(16) 0.0146(14) -0.0057(14) 0.0083(14) C7 0.0428(16) 0.0457(18) 0.0299(15) -0.0028(13) 0.0043(13) 0.0082(14) C8 0.057(2) 0.0398(17) 0.0365(17) 0.0124(14) -0.0012(15) 0.0101(15) C9 0.0338(15) 0.059(2) 0.0432(18) -0.0056(15) -0.0054(14) 0.0066(14) C10 0.0229(12) 0.0165(12) 0.0278(13) -0.0005(10) -0.0009(10) 0.0033(9) C11 0.0275(14) 0.0304(15) 0.0339(15) -0.0025(12) -0.0050(12) 0.0052(11) C12 0.0197(12) 0.0288(15) 0.0519(19) -0.0029(13) -0.0038(13) 0.0044(11) C13 0.0247(13) 0.0322(15) 0.0438(17) -0.0009(13) 0.0108(13) 0.0059(11) C14 0.0320(14) 0.0270(14) 0.0340(15) 0.0007(11) 0.0090(12) 0.0096(11) C15 0.0413(15) 0.052(2) 0.0315(16) 0.0020(14) 0.0096(14) 0.0124(14) C16 0.0429(16) 0.0403(17) 0.0400(17) -0.0006(14) 0.0105(14) 0.0149(14) C17 0.060(2) 0.0280(15) 0.0393(17) 0.0069(13) 0.0158(16) 0.0045(14) C18 0.0510(18) 0.0470(18) 0.0262(15) 0.0006(13) -0.0038(14) 0.0155(15) N1 0.0219(10) 0.0262(11) 0.0234(11) 0.0023(8) 0.0026(9) 0.0087(8) N2 0.0228(10) 0.0238(11) 0.0269(11) 0.0037(9) 0.0011(9) 0.0067(9) N3 0.0220(10) 0.0241(11) 0.0250(11) -0.0011(9) -0.0014(9) 0.0007(8) N4 0.0220(10) 0.0249(11) 0.0270(11) 0.0014(9) 0.0020(9) 0.0072(9) Cl1 0.0513(4) 0.0406(4) 0.0395(4) -0.0141(3) 0.0042(4) 0.0105(3) Cl2 0.0409(4) 0.0436(4) 0.0507(4) 0.0083(3) 0.0025(3) 0.0275(3) Cl3 0.0279(3) 0.0328(4) 0.0571(5) 0.0147(3) 0.0118(3) 0.0056(3) Cl4 0.0379(4) 0.0372(4) 0.0431(4) 0.0055(3) -0.0033(3) 0.0161(3) Cl5 0.0233(3) 0.0503(4) 0.0492(5) 0.0009(4) 0.0031(3) -0.0037(3) Cl6 0.0443(4) 0.0332(4) 0.0376(4) -0.0126(3) -0.0084(3) 0.0070(3) Sn1 0.02254(11) 0.02243(11) 0.02519(12) 0.00226(7) 0.00433(8) 0.00808(7) Sn2 0.02095(11) 0.02538(11) 0.02432(12) -0.00169(8) -0.00238(8) 0.00334(7) Si1 0.0282(4) 0.0294(4) 0.0227(4) 0.0017(3) -0.0005(3) 0.0048(3) Si2 0.0322(4) 0.0218(4) 0.0235(4) 0.0009(3) 0.0022(3) 0.0062(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.358(3) . ? C1 N1 1.371(3) . ? C1 C2 1.408(3) . ? C1 Sn1 2.611(2) . ? C2 C3 1.374(4) . ? C3 C4 1.388(4) . ? C4 C5 1.378(4) . ? C5 N2 1.350(3) . ? C5 C6 1.500(4) . ? C7 Si1 1.856(3) . ? C8 Si1 1.848(3) . ? C9 Si1 1.863(3) . ? C10 N4 1.354(3) . ? C10 N3 1.376(3) . ? C10 C11 1.400(4) . ? C10 Sn2 2.612(3) . ? C11 C12 1.363(4) . ? C12 C13 1.392(4) . ? C13 C14 1.375(4) . ? C14 N4 1.353(3) . ? C14 C15 1.502(4) . ? C16 Si2 1.861(3) . ? C17 Si2 1.853(3) . ? C18 Si2 1.856(3) . ? N1 Si1 1.764(2) . ? N1 Sn1 2.074(2) . ? N2 Sn1 2.224(2) . ? N3 Si2 1.770(2) . ? N3 Sn2 2.075(2) . ? N4 Sn2 2.209(2) . ? Cl1 Sn1 2.3235(11) . ? Cl2 Sn1 2.3441(9) . ? Cl3 Sn1 2.3256(11) . ? Cl4 Sn2 2.3279(9) . ? Cl5 Sn2 2.3464(10) . ? Cl6 Sn2 2.3244(10) . ? 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 N2 C1 N1 110.4(2) . . ? N2 C1 C2 118.8(2) . . ? N1 C1 C2 130.7(2) . . ? N2 C1 Sn1 58.44(12) . . ? N1 C1 Sn1 52.13(12) . . ? C2 C1 Sn1 173.70(18) . . ? C3 C2 C1 117.6(3) . . ? C2 C3 C4 122.0(3) . . ? C5 C4 C3 119.3(3) . . ? N2 C5 C4 118.5(3) . . ? N2 C5 C6 116.9(2) . . ? C4 C5 C6 124.6(3) . . ? N4 C10 N3 109.8(2) . . ? N4 C10 C11 119.0(2) . . ? N3 C10 C11 131.2(2) . . ? N4 C10 Sn2 57.70(13) . . ? N3 C10 Sn2 52.14(12) . . ? C11 C10 Sn2 176.35(19) . . ? C12 C11 C10 118.1(3) . . ? C11 C12 C13 121.9(3) . . ? C14 C13 C12 118.9(3) . . ? N4 C14 C13 118.8(3) . . ? N4 C14 C15 116.6(2) . . ? C13 C14 C15 124.6(3) . . ? C1 N1 Si1 132.69(17) . . ? C1 N1 Sn1 96.42(15) . . ? Si1 N1 Sn1 130.56(11) . . ? C5 N2 C1 123.8(2) . . ? C5 N2 Sn1 145.79(18) . . ? C1 N2 Sn1 90.22(15) . . ? C10 N3 Si2 132.88(18) . . ? C10 N3 Sn2 96.30(16) . . ? Si2 N3 Sn2 130.69(11) . . ? C14 N4 C10 123.3(2) . . ? C14 N4 Sn2 145.54(19) . . ? C10 N4 Sn2 91.09(15) . . ? N1 Sn1 N2 62.73(8) . . ? N1 Sn1 Cl1 127.00(6) . . ? N2 Sn1 Cl1 91.64(6) . . ? N1 Sn1 Cl3 118.44(7) . . ? N2 Sn1 Cl3 95.51(6) . . ? Cl1 Sn1 Cl3 108.99(4) . . ? N1 Sn1 Cl2 98.93(6) . . ? N2 Sn1 Cl2 161.00(6) . . ? Cl1 Sn1 Cl2 96.43(4) . . ? Cl3 Sn1 Cl2 98.05(3) . . ? N1 Sn1 C1 31.45(8) . . ? N2 Sn1 C1 31.34(8) . . ? Cl1 Sn1 C1 110.47(6) . . ? Cl3 Sn1 C1 110.88(6) . . ? Cl2 Sn1 C1 130.00(6) . . ? N3 Sn2 N4 62.76(8) . . ? N3 Sn2 Cl6 126.03(6) . . ? N4 Sn2 Cl6 92.58(6) . . ? N3 Sn2 Cl4 119.98(6) . . ? N4 Sn2 Cl4 94.28(6) . . ? Cl6 Sn2 Cl4 108.33(3) . . ? N3 Sn2 Cl5 98.82(6) . . ? N4 Sn2 Cl5 161.45(6) . . ? Cl6 Sn2 Cl5 97.40(4) . . ? Cl4 Sn2 Cl5 97.33(4) . . ? N3 Sn2 C10 31.56(8) . . ? N4 Sn2 C10 31.20(8) . . ? Cl6 Sn2 C10 111.25(6) . . ? Cl4 Sn2 C10 110.03(6) . . ? Cl5 Sn2 C10 130.32(6) . . ? N1 Si1 C8 109.66(13) . . ? N1 Si1 C7 110.85(13) . . ? C8 Si1 C7 109.75(15) . . ? N1 Si1 C9 107.12(14) . . ? C8 Si1 C9 110.61(16) . . ? C7 Si1 C9 108.82(14) . . ? N3 Si2 C17 109.02(12) . . ? N3 Si2 C18 111.36(12) . . ? C17 Si2 C18 109.63(16) . . ? N3 Si2 C16 108.36(13) . . ? C17 Si2 C16 110.46(15) . . ? C18 Si2 C16 108.00(14) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.736 _refine_diff_density_min -1.075 _refine_diff_density_rms 0.116