# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_9 _database_code_CSD 183077 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Boyd, D.' 'Allenmark, Stig' 'Alves-Areias, Andre' 'Andersson, Malin A.' 'Dalton, Howard' 'Holt, Robert' 'Kennedy, Martina' 'Luckarift, Heather' 'Malone, J.' 'Sharma, Narain D.' 'Shepherd, Steven' _publ_contact_author_name 'Prof D Boyd' _publ_contact_author_address ; Department of Chemistry Queens University Belfast BT9 5AG NORTHERN IRELAND ; _publ_requested_journal 'Chemical Communications' _publ_contact_author_email dr.boyd@qub.ac.uk _publ_section_title ; Enzyme-catalysed oxygenation and deoxygenation routes to chiral thiosulfinates ; _audit_creation_method 'SHELXL-97' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 O S2' _chemical_formula_weight 184.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7121(10) _cell_length_b 4.7053(9) _cell_length_c 11.6358(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.587(11) _cell_angle_gamma 90.00 _cell_volume 412.09(12) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 5.9 _cell_measurement_theta_max 27.7 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .50 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 5.323 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1453 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 69.87 _reflns_number_total 1167 _reflns_number_gt 1067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0615P)^2^+0.1483P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(3) _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 -0.06(5) _refine_ls_number_reflns 1167 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _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 S1 S 0.63279(16) 0.3630(3) 0.32481(11) 0.0441(5) Uani 1 1 d . . . S2 S 0.5752(2) 0.2866(4) 0.14110(12) 0.0592(6) Uani 1 1 d . . . O1 O 0.6397(5) 0.0887(10) 0.3874(3) 0.0578(12) Uani 1 1 d . . . C1 C 0.4196(7) 0.5195(13) 0.3312(4) 0.0432(14) Uani 1 1 d . . . H1A H 0.4217 0.5793 0.4112 0.052 Uiso 1 1 calc R . . H1B H 0.3996 0.6864 0.2811 0.052 Uiso 1 1 calc R . . C2 C 0.2720(6) 0.3148(12) 0.2924(4) 0.0355(13) Uani 1 1 d . . . C3 C 0.1791(7) 0.1970(15) 0.3716(5) 0.0504(16) Uani 1 1 d . . . H3 H 0.2069 0.2515 0.4503 0.060 Uiso 1 1 calc R . . C4 C 0.0485(7) 0.0032(16) 0.3339(6) 0.0605(18) Uani 1 1 d . . . H4 H -0.0131 -0.0724 0.3872 0.073 Uiso 1 1 calc R . . C5 C 0.0059(7) -0.0830(16) 0.2182(6) 0.0637(19) Uani 1 1 d . . . H5 H -0.0846 -0.2144 0.1935 0.076 Uiso 1 1 calc R . . C6 C 0.0983(8) 0.0267(16) 0.1385(5) 0.0581(18) Uani 1 1 d . . . H6 H 0.0709 -0.0324 0.0604 0.070 Uiso 1 1 calc R . . C7 C 0.2312(6) 0.2240(12) 0.1756(4) 0.0381(13) Uani 1 1 d . . . C8 C 0.3363(7) 0.3516(15) 0.0925(4) 0.0548(15) Uani 1 1 d . . . H8A H 0.3153 0.5549 0.0869 0.066 Uiso 1 1 calc R . . H8B H 0.2949 0.2710 0.0146 0.066 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 0.0393(6) 0.0499(10) 0.0450(7) -0.0013(7) 0.0130(5) -0.0047(8) S2 0.0597(8) 0.0836(15) 0.0409(7) 0.0019(8) 0.0253(6) 0.0067(8) O1 0.060(3) 0.062(3) 0.051(2) 0.017(2) 0.0131(18) 0.006(2) C1 0.052(3) 0.040(4) 0.041(3) -0.004(3) 0.017(2) 0.000(3) C2 0.036(2) 0.035(4) 0.037(2) -0.003(3) 0.0114(18) 0.004(3) C3 0.038(3) 0.065(5) 0.050(3) 0.004(3) 0.016(2) 0.004(3) C4 0.041(3) 0.073(5) 0.072(4) 0.012(4) 0.022(3) -0.003(3) C5 0.041(3) 0.060(5) 0.083(4) 0.000(4) -0.002(3) -0.007(3) C6 0.051(3) 0.064(5) 0.049(3) -0.010(3) -0.010(3) 0.009(3) C7 0.041(3) 0.036(3) 0.035(2) 0.000(2) 0.004(2) 0.009(3) C8 0.073(4) 0.062(4) 0.031(2) 0.008(3) 0.016(2) 0.009(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 S1 O1 1.477(4) . ? S1 C1 1.817(5) . ? S1 S2 2.117(2) . ? S2 C8 1.831(5) . ? C1 C2 1.484(7) . ? C2 C7 1.393(6) . ? C2 C3 1.400(7) . ? C3 C4 1.359(9) . ? C4 C5 1.375(9) . ? C5 C6 1.386(9) . ? C6 C7 1.380(8) . ? C7 C8 1.516(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 O1 S1 C1 105.6(3) . . ? O1 S1 S2 109.06(19) . . ? C1 S1 S2 96.75(17) . . ? C8 S2 S1 105.02(16) . . ? C2 C1 S1 111.4(4) . . ? C7 C2 C3 118.8(5) . . ? C7 C2 C1 119.4(4) . . ? C3 C2 C1 121.7(4) . . ? C4 C3 C2 120.2(5) . . ? C3 C4 C5 121.1(6) . . ? C4 C5 C6 119.8(6) . . ? C7 C6 C5 119.7(6) . . ? C6 C7 C2 120.4(5) . . ? C6 C7 C8 122.1(5) . . ? C2 C7 C8 117.5(5) . . ? C7 C8 S2 112.3(4) . . ? _diffrn_measured_fraction_theta_max 0.783 _diffrn_reflns_theta_full 69.87 _diffrn_measured_fraction_theta_full 0.783 _refine_diff_density_max 0.352 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.066 data_12 _database_code_CSD 185045 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 O2 S' _chemical_formula_weight 170.22 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 orthorhombic _symmetry_space_group_name_H-M 'P 2(1) 2(1) 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.7031(6) _cell_length_b 7.2523(9) _cell_length_c 22.561(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 769.53(17) _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 needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.8689 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8932 _diffrn_reflns_av_R_equivalents 0.0992 _diffrn_reflns_av_sigmaI/netI 0.1194 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.67 _reflns_number_total 1810 _reflns_number_gt 1081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0621P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.26(17) _refine_ls_number_reflns 1810 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.846 _refine_ls_shift/su_max 0.367 _refine_ls_shift/su_mean 0.019 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 0.6572(8) 0.3619(6) 0.95192(17) 0.0304(9) Uani 1 1 d . . . H1 H 0.5954 0.4002 0.9901 0.036 Uiso 1 1 calc R . . S2 S 0.5697(2) 0.15443(14) 0.92094(5) 0.0351(3) Uani 1 1 d . . . C3 C 0.7555(9) 0.2041(5) 0.85816(17) 0.0281(9) Uani 1 1 d . . . H3 H 0.7701 0.1233 0.8252 0.034 Uiso 1 1 calc R . . C3A C 0.8807(8) 0.3732(5) 0.86078(15) 0.0243(8) Uani 1 1 d . . . C4 C 1.0455(8) 0.4613(5) 0.81110(15) 0.0235(8) Uani 1 1 d . . . H4 H 1.1772 0.3681 0.7934 0.028 Uiso 1 1 calc R . . O4 O 0.8559(6) 0.5294(4) 0.76558(11) 0.0268(6) Uani 1 1 d . . . H4A H 0.7862 0.4400 0.7469 0.040 Uiso 1 1 calc R . . C5 C 1.2190(7) 0.6219(5) 0.83546(15) 0.0225(8) Uani 1 1 d . . . H5 H 1.3684 0.5699 0.8622 0.027 Uiso 1 1 calc R . . O5 O 1.3590(5) 0.7229(4) 0.78978(12) 0.0315(7) Uani 1 1 d . . . H5A H 1.4922 0.6592 0.7758 0.047 Uiso 1 1 calc R . . C6 C 1.0360(9) 0.7510(5) 0.87188(16) 0.0286(9) Uani 1 1 d . . . H6A H 0.8664 0.7881 0.8487 0.034 Uiso 1 1 calc R . . H6B H 1.1449 0.8636 0.8819 0.034 Uiso 1 1 calc R . . C7 C 0.9435(9) 0.6528(5) 0.92877(16) 0.0314(8) Uani 1 1 d . . . H7A H 1.1089 0.6406 0.9556 0.038 Uiso 1 1 calc R . . H7B H 0.7976 0.7279 0.9492 0.038 Uiso 1 1 calc R . . C7A C 0.8253(7) 0.4665(5) 0.91593(17) 0.0256(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 C1 0.031(2) 0.037(2) 0.0233(19) 0.0010(19) -0.0031(16) 0.004(2) S2 0.0379(6) 0.0349(6) 0.0326(5) 0.0076(5) 0.0001(5) -0.0070(5) C3 0.035(2) 0.022(2) 0.027(2) 0.0039(16) -0.0002(18) -0.0009(18) C3A 0.027(2) 0.024(2) 0.0221(18) 0.0007(16) -0.0008(16) 0.0013(17) C4 0.026(2) 0.0203(19) 0.0244(19) 0.0022(15) -0.0025(17) 0.0031(18) O4 0.0296(15) 0.0282(15) 0.0226(14) -0.0017(12) -0.0029(11) 0.0021(13) C5 0.0172(18) 0.028(2) 0.0227(19) 0.0056(17) -0.0014(15) 0.0026(17) O5 0.0274(16) 0.0302(15) 0.0370(16) 0.0120(13) 0.0056(12) 0.0011(12) C6 0.032(2) 0.024(2) 0.030(2) -0.0054(17) -0.0042(18) 0.0003(19) C7 0.037(2) 0.032(2) 0.0260(18) -0.0061(18) 0.0010(19) 0.003(2) C7A 0.024(2) 0.0254(19) 0.027(2) 0.0032(18) -0.0040(17) 0.0051(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7A 1.364(5) . ? C1 S2 1.709(4) . ? S2 C3 1.703(4) . ? C3 C3A 1.362(5) . ? C3A C7A 1.440(5) . ? C3A C4 1.505(5) . ? C4 O4 1.447(4) . ? C4 C5 1.524(5) . ? C5 O5 1.426(4) . ? C5 C6 1.514(5) . ? C6 C7 1.531(5) . ? C7 C7A 1.489(5) . ? 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 C7A C1 S2 112.7(3) . . ? C3 S2 C1 91.74(19) . . ? C3A C3 S2 112.1(3) . . ? C3 C3A C7A 112.5(3) . . ? C3 C3A C4 124.9(3) . . ? C7A C3A C4 122.5(3) . . ? O4 C4 C3A 110.9(3) . . ? O4 C4 C5 109.0(3) . . ? C3A C4 C5 109.4(3) . . ? O5 C5 C6 109.7(3) . . ? O5 C5 C4 112.3(3) . . ? C6 C5 C4 111.3(3) . . ? C5 C6 C7 109.2(3) . . ? C7A C7 C6 111.4(3) . . ? C1 C7A C3A 111.0(3) . . ? C1 C7A C7 127.2(4) . . ? C3A C7A C7 121.8(3) . . ? 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 C7A C1 S2 C3 -0.5(3) . . . . ? C1 S2 C3 C3A 0.1(3) . . . . ? S2 C3 C3A C7A 0.3(4) . . . . ? S2 C3 C3A C4 -176.4(3) . . . . ? C3 C3A C4 O4 75.3(4) . . . . ? C7A C3A C4 O4 -101.0(4) . . . . ? C3 C3A C4 C5 -164.5(3) . . . . ? C7A C3A C4 C5 19.2(5) . . . . ? O4 C4 C5 O5 -53.0(4) . . . . ? C3A C4 C5 O5 -174.3(3) . . . . ? O4 C4 C5 C6 70.5(4) . . . . ? C3A C4 C5 C6 -50.8(4) . . . . ? O5 C5 C6 C7 -166.8(3) . . . . ? C4 C5 C6 C7 68.3(4) . . . . ? C5 C6 C7 C7A -49.2(4) . . . . ? S2 C1 C7A C3A 0.7(4) . . . . ? S2 C1 C7A C7 -179.3(3) . . . . ? C3 C3A C7A C1 -0.6(5) . . . . ? C4 C3A C7A C1 176.1(3) . . . . ? C3 C3A C7A C7 179.4(3) . . . . ? C4 C3A C7A C7 -3.8(5) . . . . ? C6 C7 C7A C1 -161.2(4) . . . . ? C6 C7 C7A C3A 18.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.67 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.302 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.072 #===END data_23 _database_code_CSD 185046 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 O S2' _chemical_formula_weight 214.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 2(1) 2(1) 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.3436(7) _cell_length_b 10.2450(6) _cell_length_c 9.2608(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1171.12(12) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 11.6 _cell_measurement_theta_max 27.6 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 3.809 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method 'omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1703 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.61 _diffrn_reflns_theta_max 63.16 _reflns_number_total 1428 _reflns_number_gt 1355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0801P)^2^+0.1337P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0210(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 -0.05(4) _refine_ls_number_reflns 1428 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.31025(8) 0.53353(11) 0.06961(11) 0.0554(4) Uani 1 1 d . . . S2 S 0.39267(8) 0.72535(11) 0.02863(11) 0.0536(4) Uani 1 1 d . . . O1 O 0.2987(3) 0.5148(4) 0.2127(3) 0.0867(11) Uani 1 1 d . . . C1 C 0.4189(3) 0.4185(4) 0.0179(4) 0.0483(10) Uani 1 1 d . . . C2 C 0.4313(3) 0.3923(5) -0.1140(4) 0.0588(13) Uani 1 1 d . . . H2 H 0.3900 0.4339 -0.1843 0.071 Uiso 1 1 calc R . . C3 C 0.5105(4) 0.2972(5) -0.1523(5) 0.0709(13) Uani 1 1 d . . . H3 H 0.5179 0.2789 -0.2501 0.085 Uiso 1 1 calc R . . C4 C 0.5750(4) 0.2319(6) -0.0624(6) 0.0744(14) Uani 1 1 d . . . H4 H 0.6260 0.1720 -0.0952 0.089 Uiso 1 1 calc R . . C5 C 0.5626(4) 0.2562(5) 0.0688(6) 0.0748(15) Uani 1 1 d . . . H5 H 0.6040 0.2134 0.1381 0.090 Uiso 1 1 calc R . . C6 C 0.4833(4) 0.3514(5) 0.1106(4) 0.0610(12) Uani 1 1 d . . . H6 H 0.4754 0.3684 0.2087 0.073 Uiso 1 1 calc R . . C7 C 0.2793(4) 0.8545(4) 0.0096(4) 0.0558(11) Uani 1 1 d . . . C8 C 0.2063(5) 0.8511(7) 0.1281(6) 0.099(2) Uani 1 1 d . . . H8A H 0.1538 0.9196 0.1179 0.149 Uiso 1 1 calc R . . H8B H 0.2458 0.8630 0.2164 0.149 Uiso 1 1 calc R . . H8C H 0.1700 0.7682 0.1301 0.149 Uiso 1 1 calc R . . C9 C 0.2149(5) 0.8189(6) -0.1146(5) 0.0869(17) Uani 1 1 d . . . H9A H 0.1879 0.7317 -0.1025 0.130 Uiso 1 1 calc R . . H9B H 0.2589 0.8230 -0.1999 0.130 Uiso 1 1 calc R . . H9C H 0.1552 0.8783 -0.1239 0.130 Uiso 1 1 calc R . . C10 C 0.3352(5) 0.9989(5) -0.0028(8) 0.0934(18) Uani 1 1 d . . . H10A H 0.2799 1.0637 -0.0155 0.140 Uiso 1 1 calc R . . H10B H 0.3835 1.0007 -0.0840 0.140 Uiso 1 1 calc R . . H10C H 0.3751 1.0171 0.0839 0.140 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 0.0479(6) 0.0588(8) 0.0596(7) 0.0005(5) 0.0140(5) -0.0052(5) S2 0.0439(6) 0.0606(7) 0.0562(6) 0.0065(5) 0.0045(4) -0.0052(5) O1 0.111(3) 0.091(3) 0.0578(19) 0.0105(17) 0.0430(19) 0.008(2) C1 0.042(2) 0.059(3) 0.044(2) 0.000(2) 0.0008(18) -0.0068(19) C2 0.050(2) 0.083(4) 0.043(2) -0.005(2) -0.0023(19) 0.002(2) C3 0.064(3) 0.090(4) 0.060(2) -0.017(3) 0.003(2) 0.000(3) C4 0.048(3) 0.079(4) 0.096(4) -0.008(3) 0.007(3) 0.005(3) C5 0.065(3) 0.081(4) 0.078(3) 0.016(3) -0.015(3) 0.005(3) C6 0.066(3) 0.072(3) 0.045(2) 0.009(2) -0.006(2) -0.007(3) C7 0.057(3) 0.060(3) 0.051(2) -0.002(2) 0.0066(19) 0.003(2) C8 0.110(4) 0.116(5) 0.071(3) 0.010(3) 0.041(4) 0.041(4) C9 0.085(3) 0.107(5) 0.068(3) -0.005(3) -0.020(3) 0.021(3) C10 0.091(4) 0.069(4) 0.120(5) 0.008(4) -0.001(3) -0.003(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 S1 O1 1.346(3) . ? S1 C1 1.849(4) . ? S1 S2 2.2453(15) . ? S2 C7 1.934(5) . ? C1 C2 1.260(6) . ? C1 C6 1.356(6) . ? C2 C3 1.425(7) . ? C3 C4 1.332(7) . ? C4 C5 1.250(7) . ? C5 C6 1.435(7) . ? C7 C8 1.420(6) . ? C7 C9 1.445(6) . ? C7 C10 1.637(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 O1 S1 C1 103.9(2) . . ? O1 S1 S2 109.83(18) . . ? C1 S1 S2 100.70(13) . . ? C7 S2 S1 106.65(14) . . ? C2 C1 C6 115.8(4) . . ? C2 C1 S1 118.3(3) . . ? C6 C1 S1 125.7(3) . . ? C1 C2 C3 118.0(4) . . ? C4 C3 C2 126.7(5) . . ? C5 C4 C3 115.7(5) . . ? C4 C5 C6 118.8(5) . . ? C1 C6 C5 125.0(4) . . ? C8 C7 C9 105.1(4) . . ? C8 C7 C10 110.1(5) . . ? C9 C7 C10 113.9(4) . . ? C8 C7 S2 111.8(4) . . ? C9 C7 S2 107.3(3) . . ? C10 C7 S2 108.6(3) . . ? 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 O1 S1 S2 C7 -90.9(2) . . . . ? C1 S1 S2 C7 159.97(18) . . . . ? O1 S1 C1 C2 164.3(4) . . . . ? S2 S1 C1 C2 -82.0(4) . . . . ? O1 S1 C1 C6 -11.0(4) . . . . ? S2 S1 C1 C6 102.8(4) . . . . ? C6 C1 C2 C3 -0.3(7) . . . . ? S1 C1 C2 C3 -176.0(3) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C2 C3 C4 C5 1.2(8) . . . . ? C3 C4 C5 C6 -1.0(7) . . . . ? C2 C1 C6 C5 0.4(7) . . . . ? S1 C1 C6 C5 175.8(3) . . . . ? C4 C5 C6 C1 0.2(8) . . . . ? S1 S2 C7 C8 52.1(4) . . . . ? S1 S2 C7 C9 -62.6(4) . . . . ? S1 S2 C7 C10 173.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.770 _diffrn_reflns_theta_full 63.16 _diffrn_measured_fraction_theta_full 0.770 _refine_diff_density_max 0.256 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.045 #===END