# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email JCHANT@POSTINO.UP.AC.ZA _publ_contact_author_name 'Dr Janine T Chantson' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Department of Chemistry University of Pretoria Pretoria 0002 SOUTH AFRICA ; _publ_section_title ; Synthesis and structure of 4,6-Disubstituted Dibenzothiophenes and their use in the preparation of binuclear Platinum(II) Complexes ; loop_ _publ_author_name 'Janine T. Chantson' 'Vimal Ichharam' 'Simon Lotz' data_up2_s _database_code_CSD 157702 _chemical_name_common 4,6-bis(trimethylsilyl)dibenzothiophene _audit_creation_date 2001-02-07T11:09:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H24 S Si2' _chemical_formula_sum 'C18 H24 S Si2' _chemical_formula_weight 328.61 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 15.169(2) _cell_length_b 8.4610(13) _cell_length_c 15.288(2) _cell_angle_alpha 90 _cell_angle_beta 94.228(3) _cell_angle_gamma 90 _cell_volume 1956.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 567(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Rhombohedral _exptl_crystal_colour Clear _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.44 _exptl_crystal_density_diffrn 1.115 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type Empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, G., 1997)' _exptl_absorpt_correction_T_min 0.8677 _exptl_absorpt_correction_T_max 0.8864 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 567(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13152 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.3 _diffrn_reflns_theta_full 28.3 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4839 _reflns_number_gt 3566 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART CCD 1K' _computing_cell_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_reduction 'SAINT (SMART Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, A.L.,2001)' _computing_publication_material 'WinGX (Farrugia, L., 1992)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0526P)^2^+0.4401P] 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_number_reflns 4839 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.234 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S1 S 0.09228(3) 0.19795(5) 0.37898(3) 0.05901(14) Uani 1 1 d . . . Si2 Si 0.12242(3) 0.25782(6) 0.60428(3) 0.05763(15) Uani 1 1 d . . . Si3 Si 0.00620(4) 0.29002(7) 0.16851(3) 0.06495(16) Uani 1 1 d . . . C9A C 0.19368(11) -0.0501(2) 0.40329(11) 0.0533(4) Uani 1 1 d . . . C4 C 0.08174(12) 0.1185(2) 0.20006(11) 0.0580(4) Uani 1 1 d . . . C5A C 0.15623(10) 0.07232(19) 0.44993(11) 0.0508(4) Uani 1 1 d . . . C4A C 0.11475(11) 0.08590(19) 0.28652(11) 0.0520(4) Uani 1 1 d . . . C6 C 0.16793(11) 0.0884(2) 0.54187(11) 0.0541(4) Uani 1 1 d . . . C9B C 0.17000(11) -0.0424(2) 0.30990(11) 0.0538(4) Uani 1 1 d . . . C8 C 0.25824(14) -0.1512(2) 0.53960(14) 0.0715(5) Uani 1 1 d . . . H8 H 0.2921(9) -0.224(2) 0.5702(8) 0.086 Uiso 1 1 calc R . . C7 C 0.22010(13) -0.0288(2) 0.58404(13) 0.0644(5) Uani 1 1 d . . . H7 H 0.2303(2) -0.0243(3) 0.6482(13) 0.077 Uiso 1 1 calc R . . C3 C 0.10913(14) 0.0125(2) 0.13756(13) 0.0684(5) Uani 1 1 d . . . H3 H 0.0894(5) 0.0280(4) 0.0790(14) 0.082 Uiso 1 1 calc R . . C9 C 0.24540(13) -0.1633(2) 0.44988(14) 0.0667(5) Uani 1 1 d . . . H9 H 0.2713(6) -0.247(2) 0.4200(8) 0.08 Uiso 1 1 calc R . . C1 C 0.19460(13) -0.1438(2) 0.24370(14) 0.0673(5) Uani 1 1 d . . . H1 H 0.2309(9) -0.229(2) 0.2573(4) 0.081 Uiso 1 1 calc R . . C2 C 0.16450(15) -0.1151(3) 0.15849(15) 0.0742(6) Uani 1 1 d . . . H2 H 0.1820(5) -0.1844(17) 0.1123(12) 0.089 Uiso 1 1 calc R . . C10 C 0.06495(16) 0.4792(2) 0.19202(16) 0.0811(6) Uani 1 1 d . . . H10A H 0.0830(3) 0.4849(3) 0.2526(9) 0.122 Uiso 1 1 calc R . . H10B H 0.0266(5) 0.5647(12) 0.1766(3) 0.122 Uiso 1 1 calc R . . H10C H 0.1152(7) 0.4847(3) 0.1589(5) 0.122 Uiso 1 1 calc R . . C13 C 0.00284(15) 0.2877(3) 0.57315(16) 0.0886(8) Uani 1 1 d . . . H13A H -0.0266(5) 0.2025(14) 0.5861(3) 0.133 Uiso 1 1 calc R . . H13B H -0.0049(2) 0.3060(5) 0.5166(10) 0.133 Uiso 1 1 calc R . . H13C H -0.0165(4) 0.3687(14) 0.6021(5) 0.133 Uiso 1 1 calc R . . C14 C 0.18590(16) 0.4371(3) 0.57782(17) 0.0885(7) Uani 1 1 d . . . H14A H 0.2448(9) 0.4212(4) 0.5935(3) 0.133 Uiso 1 1 calc R . . H14B H 0.1660(3) 0.5220(13) 0.6082(5) 0.133 Uiso 1 1 calc R . . H14C H 0.17831(19) 0.4568(4) 0.5187(9) 0.133 Uiso 1 1 calc R . . C15 C 0.13688(19) 0.2157(3) 0.72414(15) 0.0935(8) Uani 1 1 d . . . H15A H 0.1057(6) 0.1288(16) 0.7363(3) 0.14 Uiso 1 1 calc R . . H15B H 0.1173(4) 0.2987(15) 0.7542(6) 0.14 Uiso 1 1 calc R . . H15C H 0.1946(10) 0.1993(4) 0.7399(3) 0.14 Uiso 1 1 calc R . . C11 C -0.09375(16) 0.2785(3) 0.2318(2) 0.0981(9) Uani 1 1 d . . . H11A H -0.0776(3) 0.2828(3) 0.2891(11) 0.147 Uiso 1 1 calc R . . H11B H -0.1219(5) 0.1878(16) 0.2197(3) 0.147 Uiso 1 1 calc R . . H11C H -0.1296(7) 0.3592(15) 0.2172(3) 0.147 Uiso 1 1 calc R . . C12 C -0.0289(2) 0.2788(4) 0.04961(17) 0.1196(12) Uani 1 1 d . . . H12A H -0.0583(7) 0.185(2) 0.0379(3) 0.179 Uiso 1 1 calc R . . H12B H 0.0203(11) 0.2837(4) 0.0175(7) 0.179 Uiso 1 1 calc R . . H12C H -0.0661(8) 0.3624(19) 0.0343(4) 0.179 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 S1 0.0692(3) 0.0530(2) 0.0539(2) -0.00227(18) -0.00182(19) 0.0134(2) Si2 0.0564(3) 0.0595(3) 0.0564(3) -0.0022(2) 0.0004(2) -0.0025(2) Si3 0.0744(4) 0.0605(3) 0.0577(3) 0.0002(2) -0.0098(2) 0.0008(2) C9A 0.0484(9) 0.0469(8) 0.0644(10) 0.0016(7) 0.0025(7) -0.0021(7) C4 0.0640(11) 0.0517(9) 0.0576(10) -0.0039(8) -0.0004(8) -0.0084(8) C5A 0.0466(9) 0.0455(8) 0.0596(9) 0.0036(7) -0.0001(7) -0.0018(7) C4A 0.0537(9) 0.0464(8) 0.0560(9) -0.0037(7) 0.0042(7) -0.0049(7) C6 0.0520(9) 0.0529(9) 0.0568(9) 0.0042(7) 0.0000(7) -0.0056(7) C9B 0.0506(9) 0.0471(8) 0.0642(10) -0.0031(7) 0.0065(7) -0.0039(7) C8 0.0739(13) 0.0607(11) 0.0782(13) 0.0125(10) -0.0071(10) 0.0105(10) C7 0.0665(11) 0.0632(11) 0.0619(11) 0.0090(9) -0.0052(8) -0.0017(9) C3 0.0824(14) 0.0654(12) 0.0566(10) -0.0111(9) 0.0005(9) -0.0085(10) C9 0.0646(11) 0.0546(10) 0.0806(13) 0.0011(9) 0.0039(9) 0.0101(9) C1 0.0669(12) 0.0564(11) 0.0788(13) -0.0112(9) 0.0069(10) 0.0048(9) C2 0.0841(14) 0.0653(12) 0.0739(13) -0.0214(10) 0.0110(10) 0.0005(11) C10 0.0894(16) 0.0576(12) 0.0960(15) 0.0004(11) 0.0042(12) 0.0020(11) C13 0.0615(13) 0.116(2) 0.0878(16) -0.0162(14) 0.0042(11) 0.0080(12) C14 0.0933(17) 0.0669(13) 0.1059(18) -0.0103(12) 0.0123(13) -0.0155(12) C15 0.115(2) 0.1044(19) 0.0605(12) -0.0040(12) 0.0042(12) 0.0199(15) C11 0.0685(14) 0.104(2) 0.120(2) 0.0224(16) 0.0000(13) 0.0114(13) C12 0.171(3) 0.107(2) 0.0731(16) -0.0068(14) -0.0408(18) 0.026(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 C4A 1.7561(17) . ? S1 C5A 1.7586(16) . ? Si2 C14 1.857(2) . ? Si2 C13 1.858(2) . ? Si2 C15 1.864(2) . ? Si2 C6 1.8812(19) . ? Si3 C10 1.854(2) . ? Si3 C12 1.859(3) . ? Si3 C11 1.861(3) . ? Si3 C4 1.890(2) . ? C9A C9 1.399(2) . ? C9A C5A 1.401(2) . ? C9A C9B 1.448(2) . ? C4 C3 1.396(3) . ? C4 C4A 1.406(2) . ? C5A C6 1.410(2) . ? C4A C9B 1.401(2) . ? C6 C7 1.396(2) . ? C9B C1 1.398(2) . ? C8 C9 1.375(3) . ? C8 C7 1.388(3) . ? C3 C2 1.390(3) . ? C1 C2 1.370(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 C4A S1 C5A 92.24(8) . . ? C14 Si2 C13 110.19(12) . . ? C14 Si2 C15 110.17(12) . . ? C13 Si2 C15 108.64(12) . . ? C14 Si2 C6 107.24(10) . . ? C13 Si2 C6 111.19(9) . . ? C15 Si2 C6 109.39(10) . . ? C10 Si3 C12 109.42(14) . . ? C10 Si3 C11 110.05(12) . . ? C12 Si3 C11 108.71(15) . . ? C10 Si3 C4 109.87(9) . . ? C12 Si3 C4 109.56(11) . . ? C11 Si3 C4 109.20(10) . . ? C9 C9A C5A 118.69(17) . . ? C9 C9A C9B 128.47(17) . . ? C5A C9A C9B 112.82(15) . . ? C3 C4 C4A 114.48(17) . . ? C3 C4 Si3 121.62(14) . . ? C4A C4 Si3 123.90(13) . . ? C9A C5A C6 123.53(15) . . ? C9A C5A S1 111.03(12) . . ? C6 C5A S1 125.43(13) . . ? C9B C4A C4 123.81(16) . . ? C9B C4A S1 111.15(13) . . ? C4 C4A S1 125.04(14) . . ? C7 C6 C5A 114.66(16) . . ? C7 C6 Si2 121.57(14) . . ? C5A C6 Si2 123.71(13) . . ? C1 C9B C4A 118.50(17) . . ? C1 C9B C9A 128.75(17) . . ? C4A C9B C9A 112.76(15) . . ? C9 C8 C7 120.69(19) . . ? C8 C7 C6 123.11(18) . . ? C2 C3 C4 123.13(19) . . ? C8 C9 C9A 119.32(19) . . ? C2 C1 C9B 119.4(2) . . ? C1 C2 C3 120.64(19) . . ? data_up3_s _database_code_CSD 168281 _chemical_name_common '4,6-dibromo dibenzothiophene' _audit_creation_date 2001-07-31T14:27:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4,6-dibromo dibenzothiophene ; _chemical_formula_sum 'C12 H6 Br2 S' _chemical_formula_moiety 'C12 H6 Br2 S' _chemical_formula_weight 342.05 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_space_group_name_H-M P21/c _cell_length_a 10.4977(17) _cell_length_b 8.5629(14) _cell_length_c 12.947(2) _cell_angle_alpha 90 _cell_angle_beta 106.813(3) _cell_angle_gamma 90 _cell_volume 1114.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 28.32 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_colour clear _exptl_crystal_description 'plate like' _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.423 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.1998 _exptl_absorpt_correction_T_max 0.7079 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_number 7581 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2766 _reflns_number_gt 1860 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0932P)^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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0063(10) _refine_ls_number_reflns 2766 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.02 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.128 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C7 C 0.5749(4) -0.2110(4) 0.5639(3) 0.0420(10) Uani 1 1 d . . . C6 C 0.4312(5) -0.2093(4) 0.5352(3) 0.0414(10) Uani 1 1 d . . . C5 C 0.3372(5) -0.2876(5) 0.4515(4) 0.0511(12) Uani 1 1 d . . . H5 H 0.3654 -0.3527 0.4049 0.061 Uiso 1 1 calc R . . C8 C 0.6595(5) -0.2922(5) 0.5165(4) 0.0478(11) Uani 1 1 d . . . H8 H 0.6241 -0.3559 0.4569 0.057 Uiso 1 1 calc R . . C9 C 0.7943(6) -0.2772(6) 0.5583(4) 0.0577(13) Uani 1 1 d . . . H9 H 0.8498 -0.3324 0.5269 0.069 Uiso 1 1 calc R . . Br1 Br 0.83985(6) 0.02992(6) 0.81486(4) 0.0606(2) Uani 1 1 d . . . Br2 Br 0.19268(5) 0.03891(6) 0.68534(4) 0.0563(2) Uani 1 1 d . . . S S 0.51292(12) -0.02192(13) 0.70399(9) 0.0439(3) Uani 1 1 d . . . C11 C 0.7681(4) -0.1005(5) 0.6939(4) 0.0442(10) Uani 1 1 d . . . C1 C 0.3841(4) -0.1117(4) 0.6045(3) 0.0405(9) Uani 1 1 d . . . C12 C 0.6317(4) -0.1137(4) 0.6534(3) 0.0411(9) Uani 1 1 d . . . C2 C 0.2495(4) -0.0934(5) 0.5900(3) 0.0436(10) Uani 1 1 d . . . C3 C 0.1580(5) -0.1708(5) 0.5078(4) 0.0513(11) Uani 1 1 d . . . H3 H 0.0673 -0.1587 0.4982 0.062 Uiso 1 1 calc R . . C4 C 0.2037(6) -0.2679(6) 0.4388(4) 0.0585(13) Uani 1 1 d . . . H4 H 0.1422 -0.32 0.3832 0.07 Uiso 1 1 calc R . . C10 C 0.8509(5) -0.1814(6) 0.6469(4) 0.0539(12) Uani 1 1 d . . . H10 H 0.9428 -0.1722 0.6739 0.065 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 C7 0.058(3) 0.033(2) 0.034(2) 0.0010(16) 0.013(2) -0.0002(18) C6 0.057(3) 0.031(2) 0.031(2) 0.0003(15) 0.0037(19) -0.0014(18) C5 0.070(3) 0.040(2) 0.038(2) -0.0054(19) 0.007(2) -0.005(2) C8 0.064(3) 0.042(2) 0.040(2) -0.0030(18) 0.018(2) 0.000(2) C9 0.071(3) 0.054(3) 0.055(3) -0.003(2) 0.031(3) 0.003(3) Br1 0.0631(4) 0.0633(4) 0.0499(3) -0.0092(2) 0.0077(2) -0.0173(2) Br2 0.0556(4) 0.0618(4) 0.0521(3) -0.0006(2) 0.0163(2) 0.0079(2) S 0.0503(7) 0.0438(6) 0.0355(6) -0.0068(4) 0.0092(5) -0.0017(5) C11 0.051(3) 0.039(2) 0.042(2) 0.0027(18) 0.013(2) -0.0049(19) C1 0.053(2) 0.034(2) 0.031(2) 0.0043(16) 0.0074(18) 0.0004(18) C12 0.054(3) 0.035(2) 0.035(2) 0.0021(16) 0.0124(19) -0.0016(18) C2 0.051(3) 0.037(2) 0.041(2) 0.0085(18) 0.011(2) 0.003(2) C3 0.052(3) 0.050(3) 0.044(3) 0.005(2) 0.002(2) -0.004(2) C4 0.066(3) 0.052(3) 0.043(3) -0.004(2) -0.006(2) -0.009(3) C10 0.052(3) 0.056(3) 0.058(3) 0.009(2) 0.023(2) -0.001(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C7 C8 1.402(6) . ? C7 C12 1.411(6) . ? C7 C6 1.446(6) . ? C6 C5 1.407(6) . ? C6 C1 1.416(6) . ? C5 C4 1.374(7) . ? C8 C9 1.367(7) . ? C9 C10 1.396(7) . ? Br1 C11 1.893(4) . ? Br2 C2 1.894(4) . ? S C12 1.753(4) . ? S C1 1.753(4) . ? C11 C12 1.380(6) . ? C11 C10 1.382(6) . ? C1 C2 1.379(6) . ? C2 C3 1.379(6) . ? C3 C4 1.402(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 C8 C7 C12 118.9(4) . . ? C8 C7 C6 129.7(4) . . ? C12 C7 C6 111.5(4) . . ? C5 C6 C1 118.3(4) . . ? C5 C6 C7 129.8(4) . . ? C1 C6 C7 111.9(4) . . ? C4 C5 C6 119.9(4) . . ? C9 C8 C7 119.6(4) . . ? C8 C9 C10 121.8(5) . . ? C12 S C1 90.6(2) . . ? C12 C11 C10 120.5(4) . . ? C12 C11 Br1 118.9(3) . . ? C10 C11 Br1 120.6(4) . . ? C2 C1 C6 120.9(4) . . ? C2 C1 S 126.3(3) . . ? C6 C1 S 112.8(3) . . ? C11 C12 C7 120.3(4) . . ? C11 C12 S 126.4(3) . . ? C7 C12 S 113.2(3) . . ? C1 C2 C3 120.5(4) . . ? C1 C2 Br2 118.9(3) . . ? C3 C2 Br2 120.7(4) . . ? C2 C3 C4 119.1(5) . . ? C5 C4 C3 121.4(4) . . ? C11 C10 C9 118.9(5) . . ?