Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Peter Skabara' 'Rory Berridge' 'Simon J. Coles' 'David J. Crouch' 'Mark Giles' ; M.B.Hursthouse ; 'Iain McCulloch' 'Howard J. Spencer' 'Shaun P. Wright' _publ_contact_author_name 'Dr Peter Skabara' _publ_contact_author_address ; Department of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UK ; _publ_contact_author_email PETER.SKABARA@MAN.AC.UK _publ_section_title ; Further evidence for spontaneous solid-state polymerisation reactions in 2,5-dibromothiophene derivatives ; data_03src0148 _database_code_CSD 213286 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H2 Br2 S3' _chemical_formula_weight 318.07 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' S S 0.1246 0.1234 '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 P2(1)/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 7.4164(2) _cell_length_b 11.0544(3) _cell_length_c 10.6791(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.3610(10) _cell_angle_gamma 90.00 _cell_volume 844.24(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5679 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 10.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0837 _exptl_absorpt_correction_T_max 0.6280 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8570 _diffrn_reflns_av_R_equivalents 0.1888 _diffrn_reflns_av_sigmaI/netI 0.1055 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1927 _reflns_number_gt 1757 _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^)+(0.0891P)^2^+1.3486P] 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 0.026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1927 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.253 _refine_ls_shift/su_mean 0.018 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 0.6155(8) 0.4167(5) 0.6574(5) 0.0270(12) Uani 1 1 d . . . H1A H 0.5394 0.3625 0.5900 0.032 Uiso 1 1 calc R . . H1B H 0.7177 0.4506 0.6244 0.032 Uiso 1 1 calc R . . C2 C 0.4004(7) 0.4541(5) 0.8083(4) 0.0193(9) Uani 1 1 d . . . C3 C 0.5182(6) 0.3555(5) 0.8642(4) 0.0204(10) Uani 1 1 d . . . C4 C 0.2521(7) 0.4679(5) 0.8606(4) 0.0192(9) Uani 1 1 d . . . C5 C 0.4556(7) 0.2964(5) 0.9569(5) 0.0224(10) Uani 1 1 d . . . S1 S 0.46955(18) 0.53934(14) 0.69100(12) 0.0239(3) Uani 1 1 d . . . S2 S 0.71376(18) 0.33122(13) 0.80562(13) 0.0254(4) Uani 1 1 d . . . S3 S 0.25358(17) 0.36076(13) 0.97879(11) 0.0220(3) Uani 1 1 d . . . Br1 Br 0.06418(7) 0.58434(5) 0.81547(5) 0.0247(3) Uani 1 1 d . . . Br2 Br 0.56645(8) 0.16509(6) 1.05586(6) 0.0306(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(3) 0.031(3) 0.026(2) 0.001(2) 0.015(2) -0.001(2) C2 0.022(2) 0.020(3) 0.016(2) 0.0004(19) 0.0069(18) -0.0029(19) C3 0.014(2) 0.027(3) 0.021(2) 0.000(2) 0.0068(18) -0.0006(19) C4 0.021(2) 0.018(2) 0.020(2) -0.0016(18) 0.0085(18) 0.0016(18) C5 0.021(2) 0.024(3) 0.023(2) -0.002(2) 0.0074(19) -0.0022(19) S1 0.0276(6) 0.0268(8) 0.0200(6) 0.0033(5) 0.0112(5) -0.0027(5) S2 0.0193(6) 0.0305(8) 0.0300(7) 0.0013(5) 0.0127(5) 0.0003(5) S3 0.0224(6) 0.0264(7) 0.0202(6) 0.0022(5) 0.0110(5) -0.0013(5) Br1 0.0230(3) 0.0240(4) 0.0293(4) -0.00043(19) 0.0109(2) 0.00337(18) Br2 0.0265(3) 0.0294(4) 0.0347(4) 0.0127(2) 0.0062(3) 0.0004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S2 1.822(6) . ? C1 S1 1.829(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C4 1.368(6) . ? C2 C3 1.426(7) . ? C2 S1 1.749(5) . ? C3 C5 1.365(7) . ? C3 S2 1.746(5) . ? C4 S3 1.729(5) . ? C4 Br1 1.864(5) . ? C5 S3 1.729(5) . ? C5 Br2 1.855(6) . ? 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 S2 C1 S1 109.6(3) . . ? S2 C1 H1A 109.8 . . ? S1 C1 H1A 109.8 . . ? S2 C1 H1B 109.8 . . ? S1 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C4 C2 C3 112.6(4) . . ? C4 C2 S1 130.7(4) . . ? C3 C2 S1 116.7(3) . . ? C5 C3 C2 112.4(4) . . ? C5 C3 S2 131.3(4) . . ? C2 C3 S2 116.2(4) . . ? C2 C4 S3 111.8(4) . . ? C2 C4 Br1 126.7(4) . . ? S3 C4 Br1 121.4(3) . . ? C3 C5 S3 112.0(4) . . ? C3 C5 Br2 127.1(4) . . ? S3 C5 Br2 120.9(3) . . ? C2 S1 C1 92.4(2) . . ? C3 S2 C1 93.0(2) . . ? C5 S3 C4 91.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C2 C3 C5 0.4(6) . . . . ? S1 C2 C3 C5 178.4(4) . . . . ? C4 C2 C3 S2 -179.2(4) . . . . ? S1 C2 C3 S2 -1.2(5) . . . . ? C3 C2 C4 S3 0.0(5) . . . . ? S1 C2 C4 S3 -177.7(3) . . . . ? C3 C2 C4 Br1 -179.7(4) . . . . ? S1 C2 C4 Br1 2.6(7) . . . . ? C2 C3 C5 S3 -0.6(6) . . . . ? S2 C3 C5 S3 179.0(3) . . . . ? C2 C3 C5 Br2 -179.0(4) . . . . ? S2 C3 C5 Br2 0.5(8) . . . . ? C4 C2 S1 C1 -161.2(5) . . . . ? C3 C2 S1 C1 21.2(4) . . . . ? S2 C1 S1 C2 -32.9(3) . . . . ? C5 C3 S2 C1 160.9(5) . . . . ? C2 C3 S2 C1 -19.6(4) . . . . ? S1 C1 S2 C3 32.6(3) . . . . ? C3 C5 S3 C4 0.5(4) . . . . ? Br2 C5 S3 C4 179.1(3) . . . . ? C2 C4 S3 C5 -0.3(4) . . . . ? Br1 C4 S3 C5 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.583 _refine_diff_density_min -1.626 _refine_diff_density_rms 0.286 #===END data_03src0136 _database_code_CSD 213287 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Br2 S3' _chemical_formula_weight 332.09 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' S S 0.1246 0.1234 '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 P2(1)/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 13.1863(4) _cell_length_b 5.1102(2) _cell_length_c 14.3454(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.854(2) _cell_angle_gamma 90.00 _cell_volume 929.89(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8961 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 9.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3553 _exptl_absorpt_correction_T_max 0.7068 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9677 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2139 _reflns_number_gt 1951 _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^)+(0.0564P)^2^+1.3630P] 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 0.0059(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2139 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.3810(3) 0.2454(9) 0.3599(3) 0.0159(8) Uani 1 1 d . . . H1A H 0.3514 0.3819 0.3939 0.019 Uiso 1 1 calc R . . H1B H 0.3527 0.0743 0.3734 0.019 Uiso 1 1 calc R . . C2 C 0.5000(3) 0.2432(8) 0.3997(3) 0.0148(8) Uani 1 1 d . . . H2A H 0.5181 0.2567 0.4712 0.018 Uiso 1 1 calc R . . H2B H 0.5290 0.3995 0.3753 0.018 Uiso 1 1 calc R . . C3 C 0.4085(3) 0.0617(8) 0.1884(3) 0.0112(7) Uani 1 1 d . . . C4 C 0.5009(3) -0.0762(8) 0.2433(3) 0.0111(7) Uani 1 1 d . . . C5 C 0.3805(3) -0.0120(8) 0.0935(3) 0.0143(8) Uani 1 1 d . . . C6 C 0.5357(3) -0.2464(8) 0.1859(3) 0.0130(8) Uani 1 1 d . . . S1 S 0.33885(8) 0.3074(2) 0.23091(7) 0.0148(2) Uani 1 1 d . . . S2 S 0.56284(8) -0.0465(2) 0.36766(7) 0.0143(2) Uani 1 1 d . . . S3 S 0.46069(8) -0.2500(2) 0.06751(7) 0.0145(2) Uani 1 1 d . . . Br1 Br 0.27447(3) 0.13768(9) -0.00639(3) 0.01874(17) Uani 1 1 d . . . Br2 Br 0.65006(3) -0.47721(8) 0.22509(3) 0.01541(17) 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 0.017(2) 0.025(2) 0.0088(18) -0.0022(16) 0.0080(16) 0.0018(17) C2 0.019(2) 0.0152(19) 0.0116(18) -0.0033(15) 0.0064(16) -0.0013(16) C3 0.0108(18) 0.0141(17) 0.0113(18) 0.0000(15) 0.0074(15) 0.0004(15) C4 0.0116(19) 0.0122(17) 0.0083(17) 0.0028(14) 0.0006(14) -0.0010(15) C5 0.014(2) 0.020(2) 0.0093(19) 0.0009(14) 0.0037(16) 0.0014(15) C6 0.0145(19) 0.0152(18) 0.0100(18) 0.0027(14) 0.0044(15) -0.0014(15) S1 0.0162(5) 0.0178(5) 0.0120(5) 0.0002(4) 0.0067(4) 0.0045(4) S2 0.0186(5) 0.0162(5) 0.0070(5) 0.0003(4) 0.0014(4) 0.0018(4) S3 0.0173(5) 0.0198(5) 0.0084(5) -0.0024(4) 0.0067(4) 0.0007(4) Br1 0.0134(3) 0.0332(3) 0.0092(2) 0.00476(15) 0.00232(17) 0.00093(16) Br2 0.0159(3) 0.0165(2) 0.0162(3) 0.00279(14) 0.00837(18) 0.00378(14) _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 C2 1.516(6) . ? C1 S1 1.809(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 S2 1.816(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.362(6) . ? C3 C4 1.441(5) . ? C3 S1 1.760(4) . ? C4 C6 1.361(6) . ? C4 S2 1.754(4) . ? C5 S3 1.719(4) . ? C5 Br1 1.870(4) . ? C6 S3 1.716(4) . ? C6 Br2 1.876(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 C2 C1 S1 112.5(3) . . ? C2 C1 H1A 109.1 . . ? S1 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? S1 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C1 C2 S2 114.0(3) . . ? C1 C2 H2A 108.7 . . ? S2 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? S2 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C5 C3 C4 111.6(4) . . ? C5 C3 S1 121.2(3) . . ? C4 C3 S1 127.1(3) . . ? C6 C4 C3 110.9(3) . . ? C6 C4 S2 122.0(3) . . ? C3 C4 S2 127.1(3) . . ? C3 C5 S3 113.4(3) . . ? C3 C5 Br1 126.5(3) . . ? S3 C5 Br1 119.9(2) . . ? C4 C6 S3 114.0(3) . . ? C4 C6 Br2 126.7(3) . . ? S3 C6 Br2 119.3(2) . . ? C3 S1 C1 100.72(19) . . ? C4 S2 C2 102.12(19) . . ? C6 S3 C5 90.01(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.243 _refine_diff_density_min -1.467 _refine_diff_density_rms 0.208 #===END data_03src0125 _database_code_CSD 213288 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 Br2 S3' _chemical_formula_weight 346.12 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' S S 0.1246 0.1234 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7028(2) _cell_length_b 9.1688(3) _cell_length_c 15.0660(5) _cell_angle_alpha 75.4570(10) _cell_angle_beta 89.666(2) _cell_angle_gamma 64.081(2) _cell_volume 1039.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9904 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 8.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2611 _exptl_absorpt_correction_T_max 0.7313 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 8771 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4709 _reflns_number_gt 4088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _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^)+(0.1073P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0088(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4709 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.033 _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 1.1912(5) 0.0522(5) 0.5415(3) 0.0158(8) Uani 1 1 d . . . C2 C 1.0004(5) 0.2324(5) 0.3992(3) 0.0154(8) Uani 1 1 d . . . C3 C 0.9228(5) 0.2678(5) 0.4752(3) 0.0156(8) Uani 1 1 d . . . C4 C 1.0360(5) 0.1616(5) 0.5592(3) 0.0141(8) Uani 1 1 d . . . C5 C 0.7303(6) 0.5635(5) 0.5249(3) 0.0189(9) Uani 1 1 d . . . H5A H 0.8304 0.5811 0.5037 0.023 Uiso 1 1 calc R . . H5B H 0.6267 0.6737 0.5035 0.023 Uiso 1 1 calc R . . C6 C 0.7531(5) 0.5105(5) 0.6295(3) 0.0182(9) Uani 1 1 d . . . H6A H 0.6652 0.4727 0.6506 0.022 Uiso 1 1 calc R . . H6B H 0.7294 0.6111 0.6509 0.022 Uiso 1 1 calc R . . C7 C 0.9302(5) 0.3702(5) 0.6767(3) 0.0172(9) Uani 1 1 d . . . H7A H 0.9391 0.3688 0.7424 0.021 Uiso 1 1 calc R . . H7B H 1.0194 0.3995 0.6481 0.021 Uiso 1 1 calc R . . C8 C 0.4454(5) 0.2883(5) 1.0835(3) 0.0160(8) Uani 1 1 d . . . C9 C 0.7181(6) 0.2547(6) 1.0246(3) 0.0190(9) Uani 1 1 d . . . C10 C 0.4380(5) 0.2995(5) 0.9916(3) 0.0144(8) Uani 1 1 d . . . C11 C 0.5992(5) 0.2813(5) 0.9563(3) 0.0157(8) Uani 1 1 d . . . C12 C 0.6028(6) 0.1416(6) 0.8107(4) 0.0252(10) Uani 1 1 d . . . H12A H 0.6628 0.1185 0.7561 0.030 Uiso 1 1 calc R . . H12B H 0.6599 0.0382 0.8628 0.030 Uiso 1 1 calc R . . C13 C 0.4171(6) 0.1749(6) 0.7902(3) 0.0230(10) Uani 1 1 d . . . H13A H 0.4174 0.0903 0.7602 0.028 Uiso 1 1 calc R . . H13B H 0.3546 0.2874 0.7453 0.028 Uiso 1 1 calc R . . C14 C 0.3175(6) 0.1694(6) 0.8741(3) 0.0205(9) Uani 1 1 d . . . H14A H 0.3900 0.0649 0.9229 0.025 Uiso 1 1 calc R . . H14B H 0.2135 0.1604 0.8560 0.025 Uiso 1 1 calc R . . S1 S 1.20660(13) 0.07003(13) 0.42531(8) 0.0168(2) Uani 1 1 d . . . S2 S 0.70836(13) 0.41830(13) 0.46861(8) 0.0170(2) Uani 1 1 d . . . S3 S 0.97933(14) 0.15798(13) 0.67176(8) 0.0166(2) Uani 1 1 d . . . S4 S 0.64193(14) 0.25566(14) 1.13030(8) 0.0192(2) Uani 1 1 d . . . S5 S 0.24995(13) 0.34548(14) 0.92439(8) 0.0174(2) Uani 1 1 d . . . S6 S 0.63166(15) 0.31027(15) 0.83945(8) 0.0224(3) Uani 1 1 d . . . Br1 Br 1.38182(5) -0.10946(5) 0.62578(3) 0.02182(16) Uani 1 1 d . . . Br2 Br 0.90879(6) 0.33951(6) 0.27495(3) 0.01948(16) Uani 1 1 d . . . Br3 Br 0.27042(6) 0.30766(6) 1.15911(3) 0.02045(16) Uani 1 1 d . . . Br4 Br 0.93959(6) 0.23631(6) 1.01402(4) 0.02640(17) 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 0.016(2) 0.0132(19) 0.019(2) -0.0053(17) 0.0013(16) -0.0073(16) C2 0.0163(19) 0.0164(19) 0.017(2) -0.0081(17) 0.0021(16) -0.0087(16) C3 0.0126(19) 0.0133(19) 0.019(2) -0.0042(17) 0.0008(16) -0.0046(16) C4 0.018(2) 0.0138(19) 0.012(2) -0.0047(16) 0.0024(16) -0.0075(16) C5 0.016(2) 0.017(2) 0.021(2) -0.0068(18) 0.0013(17) -0.0035(17) C6 0.015(2) 0.015(2) 0.022(2) -0.0083(18) 0.0040(17) -0.0022(16) C7 0.0126(19) 0.019(2) 0.022(2) -0.0116(18) 0.0027(17) -0.0064(17) C8 0.017(2) 0.017(2) 0.017(2) -0.0061(17) 0.0030(16) -0.0099(17) C9 0.019(2) 0.020(2) 0.022(2) -0.0081(18) 0.0072(18) -0.0114(18) C10 0.014(2) 0.0158(19) 0.014(2) -0.0022(16) 0.0017(16) -0.0087(16) C11 0.018(2) 0.018(2) 0.016(2) -0.0068(17) 0.0072(16) -0.0104(17) C12 0.027(2) 0.028(2) 0.027(3) -0.017(2) 0.010(2) -0.013(2) C13 0.023(2) 0.022(2) 0.024(3) -0.010(2) 0.0017(19) -0.0085(19) C14 0.018(2) 0.019(2) 0.027(3) -0.0080(19) -0.0018(18) -0.0100(18) S1 0.0147(5) 0.0182(5) 0.0186(6) -0.0088(4) 0.0054(4) -0.0064(4) S2 0.0111(5) 0.0188(5) 0.0189(6) -0.0078(4) 0.0002(4) -0.0035(4) S3 0.0190(5) 0.0157(5) 0.0136(5) -0.0041(4) 0.0041(4) -0.0065(4) S4 0.0208(5) 0.0230(5) 0.0165(5) -0.0059(4) -0.0004(4) -0.0119(4) S5 0.0146(5) 0.0200(5) 0.0166(5) -0.0056(4) 0.0001(4) -0.0065(4) S6 0.0285(6) 0.0285(6) 0.0182(6) -0.0097(5) 0.0090(5) -0.0183(5) Br1 0.0150(3) 0.0201(3) 0.0222(3) -0.00625(19) -0.00071(18) -0.00045(18) Br2 0.0214(3) 0.0259(3) 0.0135(3) -0.00670(19) 0.00176(17) -0.0121(2) Br3 0.0221(3) 0.0251(3) 0.0172(3) -0.00853(19) 0.00739(18) -0.0119(2) Br4 0.0167(3) 0.0328(3) 0.0347(3) -0.0126(2) 0.0040(2) -0.0139(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.359(6) . ? C1 S1 1.727(5) . ? C1 Br1 1.868(4) . ? C2 C3 1.363(6) . ? C2 S1 1.723(4) . ? C2 Br2 1.875(4) . ? C3 C4 1.442(6) . ? C3 S2 1.755(4) . ? C4 S3 1.759(4) . ? C5 C6 1.514(6) . ? C5 S2 1.822(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.535(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S3 1.822(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.361(6) . ? C8 S4 1.725(4) . ? C8 Br3 1.869(4) . ? C9 C11 1.362(6) . ? C9 S4 1.722(5) . ? C9 Br4 1.869(4) . ? C10 C11 1.454(6) . ? C10 S5 1.756(4) . ? C11 S6 1.753(4) . ? C12 C13 1.526(6) . ? C12 S6 1.822(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.532(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 S5 1.818(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C4 C1 S1 113.5(3) . . ? C4 C1 Br1 128.3(4) . . ? S1 C1 Br1 118.2(2) . . ? C3 C2 S1 113.5(3) . . ? C3 C2 Br2 127.5(3) . . ? S1 C2 Br2 118.9(2) . . ? C2 C3 C4 111.5(4) . . ? C2 C3 S2 122.9(3) . . ? C4 C3 S2 125.5(3) . . ? C1 C4 C3 111.5(4) . . ? C1 C4 S3 122.9(3) . . ? C3 C4 S3 125.4(3) . . ? C6 C5 S2 116.4(3) . . ? C6 C5 H5A 108.2 . . ? S2 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? S2 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? C5 C6 C7 116.4(4) . . ? C5 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C5 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? C6 C7 S3 116.2(3) . . ? C6 C7 H7A 108.2 . . ? S3 C7 H7A 108.2 . . ? C6 C7 H7B 108.2 . . ? S3 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C10 C8 S4 113.2(3) . . ? C10 C8 Br3 127.7(3) . . ? S4 C8 Br3 119.2(2) . . ? C11 C9 S4 113.5(3) . . ? C11 C9 Br4 128.0(4) . . ? S4 C9 Br4 118.3(3) . . ? C8 C10 C11 111.7(4) . . ? C8 C10 S5 123.1(3) . . ? C11 C10 S5 125.0(3) . . ? C9 C11 C10 111.1(4) . . ? C9 C11 S6 123.7(3) . . ? C10 C11 S6 124.8(3) . . ? C13 C12 S6 116.0(3) . . ? C13 C12 H12A 108.3 . . ? S6 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? S6 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 115.5(4) . . ? C12 C13 H13A 108.4 . . ? C14 C13 H13A 108.4 . . ? C12 C13 H13B 108.4 . . ? C14 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? C13 C14 S5 117.4(3) . . ? C13 C14 H14A 107.9 . . ? S5 C14 H14A 107.9 . . ? C13 C14 H14B 107.9 . . ? S5 C14 H14B 107.9 . . ? H14A C14 H14B 107.2 . . ? C2 S1 C1 89.9(2) . . ? C3 S2 C5 102.2(2) . . ? C4 S3 C7 102.3(2) . . ? C9 S4 C8 90.5(2) . . ? C10 S5 C14 103.1(2) . . ? C11 S6 C12 103.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C2 C3 C4 1.4(5) . . . . ? Br2 C2 C3 C4 -178.3(3) . . . . ? S1 C2 C3 S2 -175.9(2) . . . . ? Br2 C2 C3 S2 4.5(6) . . . . ? S1 C1 C4 C3 -0.9(5) . . . . ? Br1 C1 C4 C3 179.5(3) . . . . ? S1 C1 C4 S3 174.3(2) . . . . ? Br1 C1 C4 S3 -5.3(6) . . . . ? C2 C3 C4 C1 -0.3(5) . . . . ? S2 C3 C4 C1 176.9(3) . . . . ? C2 C3 C4 S3 -175.4(3) . . . . ? S2 C3 C4 S3 1.8(6) . . . . ? S2 C5 C6 C7 74.3(4) . . . . ? C5 C6 C7 S3 -73.1(5) . . . . ? S4 C8 C10 C11 -0.1(5) . . . . ? Br3 C8 C10 C11 178.8(3) . . . . ? S4 C8 C10 S5 -175.9(2) . . . . ? Br3 C8 C10 S5 3.0(6) . . . . ? S4 C9 C11 C10 -1.4(5) . . . . ? Br4 C9 C11 C10 -176.0(3) . . . . ? S4 C9 C11 S6 172.7(2) . . . . ? Br4 C9 C11 S6 -1.9(6) . . . . ? C8 C10 C11 C9 1.0(5) . . . . ? S5 C10 C11 C9 176.7(3) . . . . ? C8 C10 C11 S6 -173.0(3) . . . . ? S5 C10 C11 S6 2.7(6) . . . . ? S6 C12 C13 C14 -72.8(5) . . . . ? C12 C13 C14 S5 73.5(5) . . . . ? C3 C2 S1 C1 -1.5(3) . . . . ? Br2 C2 S1 C1 178.1(3) . . . . ? C4 C1 S1 C2 1.4(3) . . . . ? Br1 C1 S1 C2 -178.9(3) . . . . ? C2 C3 S2 C5 -121.8(4) . . . . ? C4 C3 S2 C5 61.4(4) . . . . ? C6 C5 S2 C3 -80.3(4) . . . . ? C1 C4 S3 C7 121.9(4) . . . . ? C3 C4 S3 C7 -63.6(4) . . . . ? C6 C7 S3 C4 78.9(4) . . . . ? C11 C9 S4 C8 1.2(4) . . . . ? Br4 C9 S4 C8 176.3(3) . . . . ? C10 C8 S4 C9 -0.6(4) . . . . ? Br3 C8 S4 C9 -179.6(3) . . . . ? C8 C10 S5 C14 -124.6(4) . . . . ? C11 C10 S5 C14 60.1(4) . . . . ? C13 C14 S5 C10 -79.8(4) . . . . ? C9 C11 S6 C12 122.2(4) . . . . ? C10 C11 S6 C12 -64.6(4) . . . . ? C13 C12 S6 C11 80.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.810 _refine_diff_density_min -1.188 _refine_diff_density_rms 0.262 #===END