# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 868567' #TrackingRef 'compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 O6 S' _chemical_formula_sum 'C12 H14 O6 S' _chemical_formula_weight 286.29 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.170(2) _cell_length_b 7.029(2) _cell_length_c 22.066(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.99(2) _cell_angle_gamma 90.00 _cell_volume 1254.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1212 _cell_measurement_theta_min 2.8932 _cell_measurement_theta_max 24.9988 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.42876 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6494 _diffrn_reflns_av_R_equivalents 0.0914 _diffrn_reflns_av_sigmaI/netI 0.0943 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2213 _reflns_number_gt 1382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1099P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2213 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2191 _refine_ls_wR_factor_gt 0.1921 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 S1 S 0.15662(15) 0.23876(17) 0.69701(5) 0.0293(4) Uani 1 1 d . . . O1 O 0.0104(4) 0.2704(4) 0.72549(15) 0.0362(9) Uani 1 1 d . . . O2 O 0.3139(4) 0.2371(4) 0.73625(15) 0.0346(9) Uani 1 1 d . . . O3 O 0.2050(4) -0.2723(4) 0.43362(15) 0.0316(9) Uani 1 1 d . . . O4 O 0.3839(4) -0.0643(4) 0.40165(13) 0.0307(8) Uani 1 1 d . . . O5 O 0.4426(4) 0.3634(4) 0.41350(14) 0.0317(8) Uani 1 1 d . . . O6 O 0.1853(4) 0.2668(4) 0.37519(14) 0.0258(8) Uani 1 1 d . . . C1 C 0.1676(6) 0.3992(6) 0.6351(2) 0.0306(11) Uani 1 1 d . . . H1A H 0.0639 0.4664 0.6244 0.037 Uiso 1 1 calc R . . H1B H 0.2556 0.4912 0.6453 0.037 Uiso 1 1 calc R . . C2 C 0.1391(6) 0.0292(6) 0.6521(2) 0.0326(12) Uani 1 1 d . . . H2A H 0.2114 -0.0696 0.6713 0.039 Uiso 1 1 calc R . . H2B H 0.0263 -0.0176 0.6466 0.039 Uiso 1 1 calc R . . C3 C 0.1890(5) 0.0855(6) 0.5924(2) 0.0260(11) Uani 1 1 d . . . C4 C 0.2029(5) 0.2710(6) 0.5836(2) 0.0238(11) Uani 1 1 d . . . C5 C 0.2513(6) 0.3547(6) 0.52613(19) 0.0281(11) Uani 1 1 d . . . H5A H 0.3536 0.4252 0.5362 0.034 Uiso 1 1 calc R . . H5B H 0.1667 0.4438 0.5090 0.034 Uiso 1 1 calc R . . C6 C 0.2743(5) 0.2072(6) 0.4788(2) 0.0255(11) Uani 1 1 d . . . C7 C 0.2589(5) 0.0198(6) 0.48810(19) 0.0251(11) Uani 1 1 d . . . C8 C 0.2154(6) -0.0644(6) 0.54623(19) 0.0273(11) Uani 1 1 d . . . H8A H 0.3035 -0.1487 0.5636 0.033 Uiso 1 1 calc R . . H8B H 0.1154 -0.1395 0.5370 0.033 Uiso 1 1 calc R . . C9 C 0.2766(6) -0.1226(6) 0.4397(2) 0.0266(11) Uani 1 1 d . . . C10 C 0.3134(6) 0.2863(6) 0.4196(2) 0.0249(11) Uani 1 1 d . . . C11 C 0.3887(6) -0.1778(7) 0.3471(2) 0.0339(12) Uani 1 1 d . . . H11A H 0.4685 -0.1252 0.3237 0.051 Uiso 1 1 calc R . . H11B H 0.2817 -0.1773 0.3228 0.051 Uiso 1 1 calc R . . H11C H 0.4192 -0.3061 0.3586 0.051 Uiso 1 1 calc R . . C12 C 0.2114(6) 0.3254(7) 0.3145(2) 0.0353(12) Uani 1 1 d . . . H12A H 0.1116 0.3069 0.2866 0.053 Uiso 1 1 calc R . . H12B H 0.2986 0.2508 0.3015 0.053 Uiso 1 1 calc R . . H12C H 0.2415 0.4575 0.3151 0.053 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 0.0250(7) 0.0380(8) 0.0258(7) -0.0021(5) 0.0069(5) -0.0011(5) O1 0.028(2) 0.049(2) 0.033(2) -0.0003(16) 0.0117(16) 0.0036(15) O2 0.0274(19) 0.043(2) 0.032(2) -0.0040(15) -0.0008(15) 0.0048(15) O3 0.038(2) 0.0218(18) 0.036(2) -0.0025(14) 0.0087(16) -0.0070(15) O4 0.0300(18) 0.0301(18) 0.0338(19) -0.0071(14) 0.0112(15) -0.0022(14) O5 0.029(2) 0.0310(19) 0.036(2) -0.0040(15) 0.0098(15) -0.0030(15) O6 0.0211(18) 0.0329(19) 0.0248(18) -0.0007(13) 0.0078(14) -0.0004(13) C1 0.027(3) 0.031(3) 0.034(3) -0.004(2) 0.003(2) -0.002(2) C2 0.034(3) 0.032(3) 0.032(3) -0.002(2) 0.006(2) 0.000(2) C3 0.020(2) 0.024(3) 0.034(3) -0.002(2) 0.006(2) 0.0000(19) C4 0.018(2) 0.029(3) 0.024(3) -0.0046(19) 0.003(2) -0.0023(18) C5 0.031(3) 0.020(2) 0.033(3) -0.001(2) 0.005(2) -0.004(2) C6 0.020(2) 0.027(3) 0.030(3) -0.0035(19) 0.004(2) -0.0025(19) C7 0.020(2) 0.025(3) 0.029(3) -0.007(2) 0.0012(19) -0.0025(19) C8 0.027(3) 0.026(3) 0.028(3) -0.002(2) 0.000(2) -0.001(2) C9 0.028(3) 0.025(3) 0.026(3) 0.003(2) 0.004(2) 0.007(2) C10 0.025(3) 0.022(2) 0.028(3) -0.0038(19) 0.004(2) 0.0058(19) C11 0.031(3) 0.038(3) 0.033(3) -0.014(2) 0.006(2) -0.002(2) C12 0.032(3) 0.049(3) 0.026(3) 0.005(2) 0.006(2) -0.004(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 S1 O1 1.442(3) . ? S1 O2 1.446(4) . ? S1 C2 1.770(5) . ? S1 C1 1.783(5) . ? O3 C9 1.203(5) . ? O4 C9 1.359(5) . ? O4 C11 1.450(5) . ? O5 C10 1.211(5) . ? O6 C10 1.338(5) . ? O6 C12 1.444(5) . ? C1 C4 1.508(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.485(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.325(6) . ? C3 C8 1.503(6) . ? C4 C5 1.501(6) . ? C5 C6 1.501(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.341(6) . ? C6 C10 1.495(6) . ? C7 C9 1.485(6) . ? C7 C8 1.500(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 117.5(2) . . ? O1 S1 C2 111.4(2) . . ? O2 S1 C2 108.9(2) . . ? O1 S1 C1 111.7(2) . . ? O2 S1 C1 109.2(2) . . ? C2 S1 C1 96.1(2) . . ? C9 O4 C11 116.2(4) . . ? C10 O6 C12 116.6(4) . . ? C4 C1 S1 103.6(3) . . ? C4 C1 H1A 111.0 . . ? S1 C1 H1A 111.0 . . ? C4 C1 H1B 111.0 . . ? S1 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? C3 C2 S1 105.3(3) . . ? C3 C2 H2A 110.7 . . ? S1 C2 H2A 110.7 . . ? C3 C2 H2B 110.7 . . ? S1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 115.6(4) . . ? C4 C3 C8 124.5(4) . . ? C2 C3 C8 119.8(4) . . ? C3 C4 C5 123.2(4) . . ? C3 C4 C1 116.6(4) . . ? C5 C4 C1 120.2(4) . . ? C4 C5 C6 112.9(4) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C10 122.3(4) . . ? C7 C6 C5 123.3(4) . . ? C10 C6 C5 114.4(4) . . ? C6 C7 C9 122.1(4) . . ? C6 C7 C8 123.8(4) . . ? C9 C7 C8 114.0(4) . . ? C7 C8 C3 112.2(4) . . ? C7 C8 H8A 109.2 . . ? C3 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C3 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O3 C9 O4 122.7(4) . . ? O3 C9 C7 125.1(4) . . ? O4 C9 C7 112.1(4) . . ? O5 C10 O6 124.7(4) . . ? O5 C10 C6 124.0(4) . . ? O6 C10 C6 111.2(4) . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 H12A 109.5 . . ? O6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.822 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.145 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 868568' #TrackingRef 'compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Br2 O2 S' _chemical_formula_sum 'C6 H8 Br2 O2 S' _chemical_formula_weight 304.00 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' O O 0.0106 0.0060 '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 9.330(5) _cell_length_b 9.624(5) _cell_length_c 12.480(5) _cell_angle_alpha 70.661(5) _cell_angle_beta 73.733(5) _cell_angle_gamma 63.117(5) _cell_volume 931.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2890 _cell_measurement_theta_min 3.2409 _cell_measurement_theta_max 24.9961 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 8.874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.50302 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4223 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5407 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3278 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; DIAMOND (Brandenburg, 2006) MERCURY (Bruno et al. 2002) ; _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0188P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3278 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 1.15913(7) -0.28951(7) 0.20679(5) 0.02200(16) Uani 1 1 d . . . Br2 Br 0.80929(7) -0.15032(7) -0.18885(5) 0.02283(16) Uani 1 1 d . . . Br3 Br 0.85627(6) 0.23265(6) 0.50454(5) 0.01965(15) Uani 1 1 d . . . Br4 Br 0.18754(6) 0.31728(7) 0.46684(5) 0.02261(16) Uani 1 1 d . . . S1 S 0.68679(17) -0.41274(17) 0.20626(11) 0.0186(3) Uani 1 1 d . . . S2 S 0.67442(16) 0.08177(16) 0.22775(11) 0.0158(3) Uani 1 1 d . . . C1 C 0.8697(6) -0.4258(7) 0.2335(4) 0.0193(13) Uani 1 1 d . . . H1A H 0.8484 -0.3761 0.2955 0.023 Uiso 1 1 calc R . . H1B H 0.9456 -0.5366 0.2531 0.023 Uiso 1 1 calc R . . C2 C 0.6548(6) -0.2329(6) 0.0951(4) 0.0174(12) Uani 1 1 d . . . H2A H 0.6109 -0.2349 0.0340 0.021 Uiso 1 1 calc R . . H2B H 0.5813 -0.1394 0.1250 0.021 Uiso 1 1 calc R . . C3 C 0.8241(6) -0.2329(6) 0.0527(4) 0.0151(12) Uani 1 1 d . . . C4 C 0.9345(6) -0.3356(6) 0.1214(4) 0.0167(12) Uani 1 1 d . . . C5 C 1.1099(6) -0.3641(7) 0.0978(4) 0.0198(13) Uani 1 1 d . . . H5A H 1.1364 -0.3074 0.0199 0.024 Uiso 1 1 calc R . . H5B H 1.1758 -0.4777 0.1047 0.024 Uiso 1 1 calc R . . C6 C 0.8497(7) -0.1157(7) -0.0546(4) 0.0216(13) Uani 1 1 d . . . H6A H 0.9606 -0.1243 -0.0680 0.026 Uiso 1 1 calc R . . H6B H 0.7774 -0.0081 -0.0459 0.026 Uiso 1 1 calc R . . C7 C 0.5074(6) 0.2589(6) 0.2577(4) 0.0158(12) Uani 1 1 d . . . H7A H 0.5171 0.3539 0.2027 0.019 Uiso 1 1 calc R . . H7B H 0.4049 0.2567 0.2565 0.019 Uiso 1 1 calc R . . C8 C 0.7912(6) 0.0710(6) 0.3224(4) 0.0142(12) Uani 1 1 d . . . H8A H 0.8549 -0.0396 0.3572 0.017 Uiso 1 1 calc R . . H8B H 0.8637 0.1256 0.2826 0.017 Uiso 1 1 calc R . . C9 C 0.5201(6) 0.2545(6) 0.3769(4) 0.0132(12) Uani 1 1 d . . . C10 C 0.6648(6) 0.1546(6) 0.4111(4) 0.0148(12) Uani 1 1 d . . . C11 C 0.7097(6) 0.1256(6) 0.5242(4) 0.0159(12) Uani 1 1 d . . . H11A H 0.7637 0.0113 0.5553 0.019 Uiso 1 1 calc R . . H11B H 0.6124 0.1675 0.5778 0.019 Uiso 1 1 calc R . . C12 C 0.3810(6) 0.3629(6) 0.4417(4) 0.0165(12) Uani 1 1 d . . . H12A H 0.3582 0.4733 0.3993 0.020 Uiso 1 1 calc R . . H12B H 0.4079 0.3491 0.5152 0.020 Uiso 1 1 calc R . . O1 O 0.7247(5) -0.5423(4) 0.1554(3) 0.0248(9) Uani 1 1 d . . . O2 O 0.5596(4) -0.3908(4) 0.3035(3) 0.0228(9) Uani 1 1 d . . . O3 O 0.6241(4) -0.0507(4) 0.2723(3) 0.0207(9) Uani 1 1 d . . . O4 O 0.7497(4) 0.1082(4) 0.1091(3) 0.0244(9) 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 Br1 0.0271(3) 0.0256(3) 0.0187(3) -0.0015(2) -0.0083(3) -0.0149(3) Br2 0.0286(3) 0.0334(4) 0.0122(3) -0.0037(2) -0.0039(3) -0.0179(3) Br3 0.0170(3) 0.0231(3) 0.0236(3) -0.0092(2) -0.0057(3) -0.0080(2) Br4 0.0125(3) 0.0255(3) 0.0269(3) -0.0044(3) 0.0007(3) -0.0085(2) S1 0.0230(8) 0.0243(8) 0.0137(7) -0.0066(6) 0.0033(6) -0.0160(7) S2 0.0183(8) 0.0196(7) 0.0127(7) -0.0065(6) -0.0004(6) -0.0094(6) C1 0.025(3) 0.027(3) 0.012(3) -0.003(2) -0.005(3) -0.016(3) C2 0.020(3) 0.020(3) 0.013(3) -0.006(2) -0.001(3) -0.009(2) C3 0.019(3) 0.025(3) 0.012(3) -0.010(2) 0.001(3) -0.016(3) C4 0.017(3) 0.024(3) 0.012(3) -0.011(2) 0.005(3) -0.010(3) C5 0.025(3) 0.025(3) 0.016(3) -0.009(2) 0.000(3) -0.014(3) C6 0.030(3) 0.030(3) 0.012(3) -0.003(2) -0.007(3) -0.017(3) C7 0.014(3) 0.026(3) 0.013(3) -0.007(2) -0.001(2) -0.011(2) C8 0.013(3) 0.019(3) 0.015(3) -0.006(2) 0.000(2) -0.010(2) C9 0.015(3) 0.017(3) 0.013(3) -0.006(2) 0.003(2) -0.013(2) C10 0.016(3) 0.021(3) 0.012(3) -0.004(2) 0.002(2) -0.013(2) C11 0.015(3) 0.022(3) 0.015(3) -0.007(2) 0.000(2) -0.011(2) C12 0.014(3) 0.020(3) 0.020(3) -0.008(2) 0.001(3) -0.010(2) O1 0.038(3) 0.022(2) 0.024(2) -0.0087(18) -0.001(2) -0.0199(19) O2 0.023(2) 0.034(2) 0.014(2) -0.0072(18) 0.0033(18) -0.0163(19) O3 0.027(2) 0.023(2) 0.017(2) -0.0052(17) -0.0020(18) -0.0152(18) O4 0.032(2) 0.033(2) 0.011(2) -0.0115(17) 0.0064(18) -0.016(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 Br1 C5 1.968(5) . ? Br2 C6 1.974(5) . ? Br3 C11 1.977(5) . ? Br4 C12 1.964(5) . ? S1 O2 1.436(4) . ? S1 O1 1.443(4) . ? S1 C1 1.773(5) . ? S1 C2 1.784(5) . ? S2 O4 1.442(4) . ? S2 O3 1.442(3) . ? S2 C8 1.769(5) . ? S2 C7 1.780(5) . ? C1 C4 1.508(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.518(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.337(7) . ? C3 C6 1.479(7) . ? C4 C5 1.489(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.509(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.505(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.345(7) . ? C9 C12 1.474(7) . ? C10 C11 1.486(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 O2 S1 O1 117.7(2) . . ? O2 S1 C1 112.4(2) . . ? O1 S1 C1 108.7(3) . . ? O2 S1 C2 112.1(2) . . ? O1 S1 C2 108.4(2) . . ? C1 S1 C2 95.2(2) . . ? O4 S2 O3 117.5(2) . . ? O4 S2 C8 112.7(2) . . ? O3 S2 C8 109.0(2) . . ? O4 S2 C7 111.4(2) . . ? O3 S2 C7 108.9(2) . . ? C8 S2 C7 94.9(2) . . ? C4 C1 S1 103.6(4) . . ? C4 C1 H1A 111.0 . . ? S1 C1 H1A 111.0 . . ? C4 C1 H1B 111.0 . . ? S1 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? C3 C2 S1 103.4(4) . . ? C3 C2 H2A 111.1 . . ? S1 C2 H2A 111.1 . . ? C3 C2 H2B 111.1 . . ? S1 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? C4 C3 C6 126.2(5) . . ? C4 C3 C2 115.3(4) . . ? C6 C3 C2 118.4(5) . . ? C3 C4 C5 126.1(5) . . ? C3 C4 C1 115.1(4) . . ? C5 C4 C1 118.8(5) . . ? C4 C5 Br1 110.4(3) . . ? C4 C5 H5A 109.6 . . ? Br1 C5 H5A 109.6 . . ? C4 C5 H5B 109.6 . . ? Br1 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C3 C6 Br2 112.1(3) . . ? C3 C6 H6A 109.2 . . ? Br2 C6 H6A 109.2 . . ? C3 C6 H6B 109.2 . . ? Br2 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C9 C7 S2 103.3(3) . . ? C9 C7 H7A 111.1 . . ? S2 C7 H7A 111.1 . . ? C9 C7 H7B 111.1 . . ? S2 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C10 C8 S2 103.4(3) . . ? C10 C8 H8A 111.1 . . ? S2 C8 H8A 111.1 . . ? C10 C8 H8B 111.1 . . ? S2 C8 H8B 111.1 . . ? H8A C8 H8B 109.1 . . ? C10 C9 C12 126.1(5) . . ? C10 C9 C7 114.9(4) . . ? C12 C9 C7 118.9(4) . . ? C9 C10 C11 126.2(5) . . ? C9 C10 C8 114.8(5) . . ? C11 C10 C8 119.0(5) . . ? C10 C11 Br3 109.4(3) . . ? C10 C11 H11A 109.8 . . ? Br3 C11 H11A 109.8 . . ? C10 C11 H11B 109.8 . . ? Br3 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C9 C12 Br4 110.4(3) . . ? C9 C12 H12A 109.6 . . ? Br4 C12 H12A 109.6 . . ? C9 C12 H12B 109.6 . . ? Br4 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.904 _refine_diff_density_min -0.950 _refine_diff_density_rms 0.174