data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Richard S. Grainger' 'Simon Bedford' 'Jonathan Steed' 'Patrizia Tisselli' _publ_contact_author_name 'Dr Richard S Grainger' _publ_contact_author_address ; Chemistry King's College London London WC2R 2LS UNITED KINGDOM ; _publ_contact_author_email RICHARD.GRAINGER@KCL.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Stereoselective synthesis of 2,5-disubstituted-1,4-oxathiane-S-oxides ; data_C:\structs\Grainger\stb8b1\STB8B1.CIF _database_code_depnum_ccdc_archive 'CCDC 252383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common stb8b1 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 O2 S' _chemical_formula_weight 210.28 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 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 10.5744(4) _cell_length_b 9.1217(3) _cell_length_c 11.7111(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.825(2) _cell_angle_gamma 90.00 _cell_volume 1016.80(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9186 _exptl_absorpt_correction_T_max 0.9446 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack Z. Otwinowski and W. Minor, in Methods in Enzymology, ed. C. W. Carter and R. M. Sweet, Academic Press: London, 1997, vol. 276, pp 307. ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 0.71 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3828 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2303 _reflns_number_gt 2052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.0000P)^2^+0.6956P] 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 0.023(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2303 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _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 0.31918(4) 0.31273(5) 0.23089(4) 0.01734(17) Uani 1 1 d . . . O1 O 0.34774(13) 0.16170(14) 0.19479(12) 0.0219(3) Uani 1 1 d . . . O2 O 0.00484(12) 0.32296(13) 0.02187(11) 0.0179(3) Uani 1 1 d . . . C1 C 0.15727(17) 0.29968(19) 0.24764(16) 0.0167(4) Uani 1 1 d . . . H1A H 0.1733 0.2402 0.3234 0.020 Uiso 1 1 calc R . . H1B H 0.1275 0.3989 0.2602 0.020 Uiso 1 1 calc R . . C2 C 0.04147(17) 0.22984(19) 0.13077(15) 0.0156(3) Uani 1 1 d . . . H2 H 0.0766 0.1343 0.1139 0.019 Uiso 1 1 calc R . . C3 C 0.11707(18) 0.3395(2) -0.01457(17) 0.0194(4) Uani 1 1 d . . . H3A H 0.0823 0.3945 -0.0954 0.023 Uiso 1 1 calc R . . H3B H 0.1471 0.2413 -0.0293 0.023 Uiso 1 1 calc R . . C4 C 0.24301(17) 0.41935(19) 0.08497(17) 0.0187(4) Uani 1 1 d . . . H4 H 0.2106 0.5156 0.1035 0.022 Uiso 1 1 calc R . . C5 C 0.35702(19) 0.4479(2) 0.04080(19) 0.0273(4) Uani 1 1 d . . . H5A H 0.3884 0.3544 0.0206 0.041 Uiso 1 1 calc R . . H5B H 0.4368 0.4974 0.1084 0.041 Uiso 1 1 calc R . . H5C H 0.3191 0.5101 -0.0350 0.041 Uiso 1 1 calc R . . C6 C -0.09311(17) 0.20236(18) 0.14286(16) 0.0162(3) Uani 1 1 d . . . C7 C -0.18468(18) 0.09587(19) 0.06574(16) 0.0186(4) Uani 1 1 d . . . H7 H -0.1593 0.0399 0.0105 0.022 Uiso 1 1 calc R . . C8 C -0.31301(19) 0.0705(2) 0.06853(18) 0.0230(4) Uani 1 1 d . . . H8 H -0.3747 -0.0023 0.0152 0.028 Uiso 1 1 calc R . . C9 C -0.35110(19) 0.1512(2) 0.14908(18) 0.0222(4) Uani 1 1 d . . . H9 H -0.4388 0.1341 0.1510 0.027 Uiso 1 1 calc R . . C10 C -0.2603(2) 0.2567(2) 0.22650(18) 0.0248(4) Uani 1 1 d . . . H10 H -0.2858 0.3122 0.2819 0.030 Uiso 1 1 calc R . . C11 C -0.13159(19) 0.2825(2) 0.22390(18) 0.0229(4) Uani 1 1 d . . . H11 H -0.0699 0.3551 0.2777 0.028 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 0.0135(2) 0.0180(2) 0.0185(2) 0.00008(16) 0.00505(17) -0.00042(16) O1 0.0197(6) 0.0185(6) 0.0280(7) 0.0026(5) 0.0110(5) 0.0057(5) O2 0.0143(6) 0.0229(6) 0.0167(6) 0.0029(5) 0.0070(5) -0.0003(5) C1 0.0158(8) 0.0178(8) 0.0171(8) -0.0008(7) 0.0078(7) 0.0005(7) C2 0.0153(8) 0.0150(8) 0.0181(8) 0.0002(6) 0.0087(7) 0.0003(6) C3 0.0170(8) 0.0248(9) 0.0186(8) 0.0013(7) 0.0098(7) -0.0016(7) C4 0.0164(8) 0.0169(8) 0.0228(9) 0.0035(7) 0.0084(7) 0.0001(7) C5 0.0191(9) 0.0334(11) 0.0304(10) 0.0066(9) 0.0118(8) -0.0040(8) C6 0.0162(8) 0.0162(8) 0.0177(8) 0.0023(7) 0.0086(7) 0.0016(7) C7 0.0201(8) 0.0173(8) 0.0200(8) -0.0017(7) 0.0103(7) -0.0001(7) C8 0.0199(9) 0.0231(9) 0.0251(9) -0.0008(8) 0.0089(8) -0.0051(7) C9 0.0179(8) 0.0254(9) 0.0261(9) 0.0057(8) 0.0122(7) 0.0010(7) C10 0.0260(9) 0.0279(10) 0.0282(10) -0.0029(8) 0.0190(8) -0.0004(8) C11 0.0217(9) 0.0242(9) 0.0261(9) -0.0074(8) 0.0134(8) -0.0047(7) _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 1.5097(13) . ? S1 C1 1.8102(17) . ? S1 C4 1.8209(18) . ? O2 C3 1.4333(19) . ? O2 C2 1.438(2) . ? C1 C2 1.523(2) . ? C2 C6 1.511(2) . ? C3 C4 1.520(2) . ? C4 C5 1.527(2) . ? C6 C7 1.391(2) . ? C6 C11 1.392(2) . ? C7 C8 1.391(2) . ? C8 C9 1.388(3) . ? C9 C10 1.383(3) . ? C10 C11 1.394(2) . ? 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 106.52(8) . . ? O1 S1 C4 106.58(8) . . ? C1 S1 C4 94.83(8) . . ? C3 O2 C2 112.83(12) . . ? C2 C1 S1 111.00(11) . . ? O2 C2 C6 106.27(13) . . ? O2 C2 C1 110.52(13) . . ? C6 C2 C1 113.99(13) . . ? O2 C3 C4 112.60(14) . . ? C3 C4 C5 112.28(15) . . ? C3 C4 S1 110.19(12) . . ? C5 C4 S1 108.49(12) . . ? C7 C6 C11 118.82(15) . . ? C7 C6 C2 118.20(15) . . ? C11 C6 C2 122.93(15) . . ? C6 C7 C8 120.75(16) . . ? C9 C8 C7 120.17(17) . . ? C10 C9 C8 119.40(16) . . ? C9 C10 C11 120.58(17) . . ? C6 C11 C10 120.28(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.400 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.067 data_C:\structs\Grainger\stb8b2\STB8B2.CIF _database_code_depnum_ccdc_archive 'CCDC 252384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common stb8b2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 O2 S' _chemical_formula_weight 210.28 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5387(5) _cell_length_b 6.0000(5) _cell_length_c 11.4544(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.308(5) _cell_angle_gamma 90.00 _cell_volume 517.97(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8487 _exptl_absorpt_correction_T_max 0.9723 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack Z. Otwinowski and W. Minor, in Methods in Enzymology, ed. C. W. Carter and R. M. Sweet, Academic Press: London, 1997, vol. 276, pp 307. Twinning of best sample ameliorated by data collection at DX=55 with 0.5o frames but still overall precision is poor. ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 0.71 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 1518 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1115 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1518 _reflns_number_gt 1457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.1335P)^2^+1.7507P] 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 0.09(6) _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 0.2(3) _refine_ls_number_reflns 1518 _refine_ls_number_parameters 129 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.1100 _refine_ls_wR_factor_ref 0.2753 _refine_ls_wR_factor_gt 0.2717 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.178 _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 0.7105(2) 0.6422(4) 0.03777(16) 0.0291(7) Uani 1 1 d . . . O2 O 0.7429(7) 0.9284(11) 0.2661(5) 0.0316(15) Uani 1 1 d . . . C1 C 0.5621(10) 0.656(2) 0.1612(7) 0.0309(18) Uani 1 1 d . . . H1A H 0.4390 0.6232 0.1346 0.037 Uiso 1 1 calc R . . H1B H 0.5977 0.5440 0.2206 0.037 Uiso 1 1 calc R . . O1 O 0.7268(8) 0.3977(11) 0.0074(5) 0.0325(15) Uani 1 1 d . . . C4 C 0.9123(10) 0.7248(16) 0.1183(7) 0.029(2) Uani 1 1 d . . . H4 H 1.0042 0.7559 0.0588 0.035 Uiso 1 1 calc R . . C11 C 0.3395(10) 1.1163(17) 0.3100(7) 0.0312(19) Uani 1 1 d . . . H11 H 0.3596 1.2269 0.2524 0.037 Uiso 1 1 calc R . . C6 C 0.4350(11) 0.9217(16) 0.3068(7) 0.0278(19) Uani 1 1 d . . . C8 C 0.2812(11) 0.8008(17) 0.4805(8) 0.036(2) Uani 1 1 d . . . H8 H 0.2611 0.6915 0.5388 0.043 Uiso 1 1 calc R . . C9 C 0.1842(11) 0.9994(18) 0.4815(8) 0.035(2) Uani 1 1 d . . . H9 H 0.0995 1.0264 0.5400 0.042 Uiso 1 1 calc R . . C5 C 0.9844(11) 0.5434(18) 0.1950(8) 0.034(2) Uani 1 1 d . . . H5A H 0.8960 0.5030 0.2528 0.051 Uiso 1 1 calc R . . H5B H 1.0928 0.5953 0.2352 0.051 Uiso 1 1 calc R . . H5C H 1.0116 0.4127 0.1473 0.051 Uiso 1 1 calc R . . C3 C 0.8744(11) 0.9471(15) 0.1797(8) 0.031(2) Uani 1 1 d . . . H3A H 0.9856 1.0030 0.2168 0.037 Uiso 1 1 calc R . . H3B H 0.8348 1.0578 0.1205 0.037 Uiso 1 1 calc R . . C2 C 0.5712(10) 0.8874(18) 0.2138(8) 0.036(2) Uani 1 1 d . . . H2 H 0.5495 0.9991 0.1503 0.043 Uiso 1 1 calc R . . C7 C 0.4064(12) 0.7605(16) 0.3960(7) 0.031(2) Uani 1 1 d . . . H7 H 0.4728 0.6259 0.3975 0.037 Uiso 1 1 calc R . . C10 C 0.2142(10) 1.157(2) 0.3948(7) 0.0350(19) Uani 1 1 d . . . H10 H 0.1490 1.2925 0.3936 0.042 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 0.0372(11) 0.0293(13) 0.0209(10) -0.0029(10) 0.0009(6) 0.0021(10) O2 0.035(3) 0.033(4) 0.028(3) -0.009(3) 0.005(2) -0.003(3) C1 0.031(4) 0.030(5) 0.032(4) -0.005(5) 0.003(3) -0.004(4) O1 0.048(3) 0.026(4) 0.024(3) -0.013(3) -0.002(2) 0.002(2) C4 0.028(4) 0.038(5) 0.021(4) -0.010(4) 0.000(3) -0.006(3) C11 0.037(4) 0.027(5) 0.030(4) 0.005(4) 0.002(3) -0.001(4) C6 0.038(4) 0.030(5) 0.016(4) -0.006(4) 0.002(3) 0.000(4) C8 0.044(5) 0.036(6) 0.028(5) 0.004(4) 0.001(3) -0.007(4) C9 0.035(4) 0.045(7) 0.026(5) 0.001(4) 0.004(3) -0.002(4) C5 0.041(5) 0.032(5) 0.029(5) -0.002(4) -0.002(3) 0.003(4) C3 0.038(4) 0.020(4) 0.036(5) -0.008(4) 0.004(4) -0.007(3) C2 0.028(4) 0.042(6) 0.038(5) 0.001(5) 0.006(3) 0.004(4) C7 0.040(5) 0.027(5) 0.025(4) 0.003(4) -0.001(3) 0.002(4) C10 0.041(4) 0.030(5) 0.035(4) -0.009(5) 0.006(3) 0.004(5) _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 1.514(7) . ? S1 C1 1.825(8) . ? S1 C4 1.829(8) . ? O2 C3 1.421(10) . ? O2 C2 1.435(10) . ? C1 C2 1.514(15) . ? C4 C5 1.493(13) . ? C4 C3 1.538(12) . ? C11 C6 1.373(13) . ? C11 C10 1.392(11) . ? C6 C7 1.427(13) . ? C6 C2 1.510(11) . ? C8 C7 1.389(13) . ? C8 C9 1.398(14) . ? C9 C10 1.393(14) . ? 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 106.1(5) . . ? O1 S1 C4 107.9(4) . . ? C1 S1 C4 96.6(4) . . ? C3 O2 C2 111.1(6) . . ? C2 C1 S1 109.1(6) . . ? C5 C4 C3 115.6(7) . . ? C5 C4 S1 112.7(6) . . ? C3 C4 S1 107.7(6) . . ? C6 C11 C10 122.1(9) . . ? C11 C6 C7 118.0(8) . . ? C11 C6 C2 120.0(8) . . ? C7 C6 C2 121.9(8) . . ? C7 C8 C9 121.2(8) . . ? C10 C9 C8 118.6(8) . . ? O2 C3 C4 112.9(7) . . ? O2 C2 C6 107.7(7) . . ? O2 C2 C1 110.8(7) . . ? C6 C2 C1 112.4(8) . . ? C8 C7 C6 119.8(8) . . ? C11 C10 C9 120.2(10) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.721 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.139 data_C:\structs\Grainger\pt1812\PT1812.CIF _database_code_depnum_ccdc_archive 'CCDC 252385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common pt1812 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 N O2 S' _chemical_formula_weight 241.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 20.9699(9) _cell_length_b 20.9699(9) _cell_length_c 11.2756(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4958.3(4) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9075 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack Z. Otwinowski and W. Minor, in Methods in Enzymology, ed. C. W. Carter and R. M. Sweet, Academic Press: London, 1997, vol. 276, pp 307. ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3252 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.40 _reflns_number_total 2136 _reflns_number_gt 1417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.0336P)^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_coef 0.0014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2136 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.78490(3) 0.38087(3) 0.13402(5) 0.0212(2) Uani 1 1 d . . . O1 O 0.89776(7) 0.29873(7) 0.21811(13) 0.0245(5) Uani 1 1 d . . . N1 N 0.77242(10) 0.44883(9) 0.0922(2) 0.0253(6) Uani 1 1 d . . . O2 O 0.73413(7) 0.33326(7) 0.13369(13) 0.0249(4) Uani 1 1 d . . . C2 C 0.84778(11) 0.31142(11) 0.3014(2) 0.0215(6) Uani 1 1 d . . . H2 H 0.8134 0.2789 0.2910 0.026 Uiso 1 1 calc R . . C3 C 0.82025(10) 0.37721(10) 0.2764(2) 0.0214(6) Uani 1 1 d . . . H3A H 0.8546 0.4094 0.2818 0.026 Uiso 1 1 calc R . . H3B H 0.7878 0.3875 0.3373 0.026 Uiso 1 1 calc R . . C5 C 0.84851(10) 0.35161(11) 0.0437(2) 0.0212(6) Uani 1 1 d . . . H5 H 0.8832 0.3843 0.0412 0.025 Uiso 1 1 calc R . . C6 C 0.87468(12) 0.29063(11) 0.10036(19) 0.0270(6) Uani 1 1 d . . . H6A H 0.8405 0.2581 0.1011 0.032 Uiso 1 1 calc R . . H6B H 0.9098 0.2742 0.0503 0.032 Uiso 1 1 calc R . . C7 C 0.82453(11) 0.33991(11) -0.08202(19) 0.0275(6) Uani 1 1 d . . . H7A H 0.8589 0.3216 -0.1300 0.041 Uiso 1 1 calc R . . H7B H 0.8108 0.3804 -0.1171 0.041 Uiso 1 1 calc R . . H7C H 0.7885 0.3102 -0.0798 0.041 Uiso 1 1 calc R . . C8 C 0.87508(11) 0.30583(10) 0.4284(2) 0.0203(6) Uani 1 1 d . . . C9 C 0.92341(11) 0.35728(11) 0.4512(2) 0.0234(6) Uani 1 1 d . . . H9 H 0.9627 0.3551 0.4095 0.028 Uiso 1 1 calc R . . C10 C 0.91500(11) 0.40530(12) 0.5251(2) 0.0280(7) Uani 1 1 d . . . H10 H 0.9485 0.4355 0.5335 0.034 Uiso 1 1 calc R . . C11 C 0.85551(12) 0.41493(12) 0.5965(2) 0.0369(7) Uani 1 1 d . . . H11A H 0.8672 0.4216 0.6806 0.044 Uiso 1 1 calc R . . H11B H 0.8334 0.4538 0.5683 0.044 Uiso 1 1 calc R . . C12 C 0.81130(12) 0.35965(12) 0.5875(2) 0.0322(7) Uani 1 1 d . . . H12 H 0.7751 0.3589 0.6381 0.039 Uiso 1 1 calc R . . C13 C 0.81942(11) 0.31172(12) 0.5137(2) 0.0264(6) Uani 1 1 d . . . H13 H 0.7884 0.2787 0.5138 0.032 Uiso 1 1 calc R . . C14 C 0.90603(11) 0.24002(11) 0.4426(2) 0.0296(7) Uani 1 1 d . . . H14A H 0.9411 0.2357 0.3857 0.044 Uiso 1 1 calc R . . H14B H 0.8742 0.2068 0.4277 0.044 Uiso 1 1 calc R . . H14C H 0.9226 0.2356 0.5234 0.044 Uiso 1 1 calc R . . H1 H 0.7516(11) 0.4641(11) 0.139(2) 0.024(9) Uiso 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 S1 0.0185(4) 0.0208(4) 0.0243(4) 0.0002(3) 0.0006(3) -0.0004(3) O1 0.0222(10) 0.0317(11) 0.0198(10) -0.0031(8) 0.0013(8) 0.0060(7) N1 0.0285(14) 0.0181(13) 0.0293(14) 0.0027(11) 0.0042(12) 0.0059(10) O2 0.0191(10) 0.0244(10) 0.0311(10) 0.0022(8) -0.0018(8) -0.0053(7) C2 0.0178(14) 0.0211(14) 0.0256(15) -0.0025(12) 0.0025(12) 0.0003(11) C3 0.0181(14) 0.0231(15) 0.0229(15) -0.0011(11) 0.0006(11) 0.0002(11) C5 0.0188(14) 0.0203(14) 0.0246(15) -0.0019(12) 0.0027(12) -0.0002(11) C6 0.0281(15) 0.0280(16) 0.0247(16) -0.0036(13) 0.0011(13) 0.0047(12) C7 0.0276(15) 0.0289(16) 0.0260(15) 0.0001(12) 0.0028(13) -0.0001(12) C8 0.0202(14) 0.0194(14) 0.0213(14) -0.0003(11) -0.0010(12) -0.0008(11) C9 0.0206(14) 0.0242(16) 0.0254(15) 0.0016(13) 0.0002(12) -0.0041(11) C10 0.0314(17) 0.0252(16) 0.0275(16) 0.0015(13) -0.0078(13) -0.0049(12) C11 0.0451(18) 0.0333(17) 0.0323(17) -0.0069(13) -0.0006(15) 0.0032(14) C12 0.0320(17) 0.0400(18) 0.0245(16) 0.0014(14) 0.0081(13) 0.0051(14) C13 0.0235(15) 0.0285(16) 0.0274(15) 0.0092(14) -0.0008(13) -0.0022(12) C14 0.0325(16) 0.0266(16) 0.0297(16) 0.0005(13) -0.0062(13) 0.0000(12) _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 O2 1.4594(15) . ? S1 N1 1.524(2) . ? S1 C3 1.770(2) . ? S1 C5 1.787(2) . ? O1 C6 1.423(2) . ? O1 C2 1.432(2) . ? C2 C3 1.522(3) . ? C2 C8 1.546(3) . ? C5 C7 1.524(3) . ? C5 C6 1.531(3) . ? C8 C9 1.502(3) . ? C8 C13 1.517(3) . ? C8 C14 1.533(3) . ? C9 C10 1.319(3) . ? C10 C11 1.498(3) . ? C11 C12 1.488(3) . ? C12 C13 1.316(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 O2 S1 N1 120.91(10) . . ? O2 S1 C3 106.15(10) . . ? N1 S1 C3 113.17(11) . . ? O2 S1 C5 107.95(10) . . ? N1 S1 C5 105.83(12) . . ? C3 S1 C5 100.92(11) . . ? C6 O1 C2 112.65(16) . . ? O1 C2 C3 108.94(18) . . ? O1 C2 C8 108.80(17) . . ? C3 C2 C8 112.37(18) . . ? C2 C3 S1 111.48(15) . . ? C7 C5 C6 111.83(18) . . ? C7 C5 S1 109.82(15) . . ? C6 C5 S1 108.47(15) . . ? O1 C6 C5 114.29(18) . . ? C9 C8 C13 110.61(19) . . ? C9 C8 C14 110.06(19) . . ? C13 C8 C14 109.43(19) . . ? C9 C8 C2 110.71(18) . . ? C13 C8 C2 107.20(18) . . ? C14 C8 C2 108.75(17) . . ? C10 C9 C8 124.5(2) . . ? C9 C10 C11 123.6(2) . . ? C12 C11 C10 112.2(2) . . ? C13 C12 C11 123.9(2) . . ? C12 C13 C8 124.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N1 0.76(2) 2.55(2) 3.2697(15) 157(2) 4_565 _diffrn_measured_fraction_theta_max 0.755 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.755 _refine_diff_density_max 0.256 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.053