# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Alves-Areias, Andre' 'Boyd, D.' 'Dalton, Howard' 'Haughey, Simon A.' 'Holt, Robert' 'King, Alistair' 'Malone, J.' 'McMurray, Brian T.' 'Sharma, Narain D.' _publ_requested_journal 'J. Chem. Soc. Perkin Trans. 1' _publ_contact_author_name 'Prof D Boyd' _publ_contact_author_address ; Department of Chemistry Queens University Belfast BT9 5AG NORTHERN IRELAND ; _publ_contact_author_email dr.boyd@qub.ac.uk _publ_section_title ; Dioxygenase-catalysed mono-, di- and tri-oxygenation of dialkyl sulfides and thioacetals: chemoenzymatic synthesis of enantiopure cis-diol sulfoxides. ; #===END data_20 _database_code_CSD 171330 _audit_creation_method 'SHELXL-97' _chemical_name_systematic ;(1S,2S)-2-phenyl-1,3-dithiane-1-oxide ; _chemical_name_common ? _chemical_melting_point 155-157 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 O S2' _chemical_formula_weight 212.32 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 P2(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 5.6341(17) _cell_length_b 10.142(4) _cell_length_c 18.013(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1029.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.474 _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 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3 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 2775 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2362 _reflns_number_gt 2117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _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^)+(0.0427P)^2^+0.1052P] 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 refined _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 0.00(8) _refine_ls_number_reflns 2362 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.94261(8) 0.64334(5) 0.07942(3) 0.04081(13) Uani 1 1 d . . . O1 O 0.9280(3) 0.63018(16) -0.00327(8) 0.0585(4) Uani 1 1 d . . . C2 C 0.6544(4) 0.58919(17) 0.11468(10) 0.0359(4) Uani 1 1 d . . . H2 H 0.532(4) 0.641(2) 0.0883(11) 0.045(6) Uiso 1 1 d . . . S3 S 0.62750(12) 0.62603(5) 0.21263(3) 0.05496(17) Uani 1 1 d . . . C4 C 0.6585(5) 0.8034(2) 0.21217(14) 0.0568(6) Uani 1 1 d . . . H4A H 0.539(5) 0.846(2) 0.1811(13) 0.062(7) Uiso 1 1 d . . . H4B H 0.640(4) 0.828(2) 0.2635(14) 0.058(7) Uiso 1 1 d . . . C5 C 0.8907(5) 0.8483(2) 0.18039(12) 0.0525(5) Uani 1 1 d . . . H5A H 0.899(5) 0.936(3) 0.1864(14) 0.065(8) Uiso 1 1 d . . . H5B H 1.016(5) 0.810(2) 0.2057(13) 0.055(7) Uiso 1 1 d . . . C6 C 0.9151(4) 0.8173(2) 0.09816(11) 0.0451(5) Uani 1 1 d . . . H6A H 0.770(4) 0.851(3) 0.0694(13) 0.053(6) Uiso 1 1 d . . . H6B H 1.071(5) 0.853(2) 0.0761(13) 0.055(6) Uiso 1 1 d . . . C1' C 0.6312(3) 0.44175(17) 0.10596(9) 0.0351(4) Uani 1 1 d . . . C2' C 0.4364(4) 0.38691(19) 0.07063(11) 0.0422(4) Uani 1 1 d . . . H2' H 0.319(5) 0.445(2) 0.0473(13) 0.052(7) Uiso 1 1 d . . . C3' C 0.4113(4) 0.2507(2) 0.06699(12) 0.0488(5) Uani 1 1 d . . . H3' H 0.280(5) 0.215(2) 0.0423(14) 0.057(7) Uiso 1 1 d . . . C4' C 0.5805(5) 0.1693(2) 0.09784(12) 0.0504(5) Uani 1 1 d . . . H4' H 0.561(5) 0.081(2) 0.0933(12) 0.052(6) Uiso 1 1 d . . . C5' C 0.7768(4) 0.2239(2) 0.13202(13) 0.0511(5) Uani 1 1 d . . . H5' H 0.893(5) 0.164(2) 0.1555(13) 0.057(7) Uiso 1 1 d . . . C6' C 0.8018(4) 0.3588(2) 0.13608(11) 0.0437(4) Uani 1 1 d . . . H6' H 0.934(5) 0.3933(19) 0.1578(11) 0.044(6) 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 0.0386(2) 0.0418(2) 0.0421(2) -0.0042(2) 0.00389(19) 0.0020(2) O1 0.0664(10) 0.0679(9) 0.0413(7) -0.0127(7) 0.0167(7) -0.0126(10) C2 0.0380(9) 0.0364(9) 0.0334(8) -0.0025(7) 0.0025(8) 0.0032(8) S3 0.0852(4) 0.0436(3) 0.0361(2) -0.0059(2) 0.0164(2) -0.0046(3) C4 0.0795(16) 0.0407(11) 0.0501(12) -0.0106(10) 0.0111(13) 0.0027(11) C5 0.0754(16) 0.0364(10) 0.0456(11) -0.0064(9) -0.0085(10) -0.0039(11) C6 0.0536(13) 0.0386(9) 0.0432(10) 0.0026(8) -0.0007(9) -0.0030(9) C1' 0.0391(9) 0.0363(9) 0.0298(8) -0.0018(7) 0.0044(7) 0.0022(8) C2' 0.0389(9) 0.0458(10) 0.0420(9) -0.0042(8) -0.0009(8) 0.0050(9) C3' 0.0502(12) 0.0505(11) 0.0457(10) -0.0096(9) 0.0018(10) -0.0084(10) C4' 0.0666(14) 0.0360(9) 0.0487(11) -0.0028(8) 0.0082(10) -0.0040(10) C5' 0.0603(13) 0.0396(11) 0.0534(12) 0.0080(9) -0.0014(11) 0.0057(10) C6' 0.0463(10) 0.0437(10) 0.0411(9) 0.0020(8) -0.0071(8) -0.0027(10) _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 1.4978(15) . ? S1 C6 1.803(2) . ? S1 C2 1.828(2) . ? C2 C1' 1.509(2) . ? C2 S3 1.8099(19) . ? S3 C4 1.807(2) . ? C4 C5 1.499(4) . ? C5 C6 1.520(3) . ? C1' C2' 1.386(3) . ? C1' C6' 1.388(3) . ? C2' C3' 1.390(3) . ? C3' C4' 1.378(3) . ? C4' C5' 1.382(3) . ? C5' C6' 1.377(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 O1 S1 C6 105.59(9) . . ? O1 S1 C2 105.66(9) . . ? C6 S1 C2 98.78(10) . . ? C1' C2 S3 107.38(12) . . ? C1' C2 S1 109.77(13) . . ? S3 C2 S1 110.54(10) . . ? C4 S3 C2 101.13(10) . . ? C5 C4 S3 112.87(17) . . ? C4 C5 C6 112.9(2) . . ? C5 C6 S1 113.12(15) . . ? C2' C1' C6' 119.02(18) . . ? C2' C1' C2 120.93(17) . . ? C6' C1' C2 120.01(18) . . ? C1' C2' C3' 120.1(2) . . ? C4' C3' C2' 120.4(2) . . ? C3' C4' C5' 119.6(2) . . ? C6' C5' C4' 120.2(2) . . ? C5' C6' C1' 120.7(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 O1 S1 C2 C1' 71.48(15) . . . . ? C6 S1 C2 C1' -179.51(14) . . . . ? O1 S1 C2 S3 -170.25(10) . . . . ? C6 S1 C2 S3 -61.24(12) . . . . ? C1' C2 S3 C4 -179.90(16) . . . . ? S1 C2 S3 C4 60.38(14) . . . . ? C2 S3 C4 C5 -59.6(2) . . . . ? S3 C4 C5 C6 66.1(3) . . . . ? C4 C5 C6 S1 -69.0(2) . . . . ? O1 S1 C6 C5 171.78(17) . . . . ? C2 S1 C6 C5 62.71(19) . . . . ? S3 C2 C1' C2' 112.32(17) . . . . ? S1 C2 C1' C2' -127.47(17) . . . . ? S3 C2 C1' C6' -65.1(2) . . . . ? S1 C2 C1' C6' 55.1(2) . . . . ? C6' C1' C2' C3' 1.3(3) . . . . ? C2 C1' C2' C3' -176.21(18) . . . . ? C1' C2' C3' C4' -0.5(3) . . . . ? C2' C3' C4' C5' -0.5(3) . . . . ? C3' C4' C5' C6' 0.8(3) . . . . ? C4' C5' C6' C1' -0.1(3) . . . . ? C2' C1' C6' C5' -1.0(3) . . . . ? C2 C1' C6' C5' 176.55(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.159 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 #===END data_22 _database_code_CSD 171331 _audit_creation_method 'SHELXL-97' _chemical_name_systematic ; cis-(1S,2R)-3-(1'S,2'S-1'-oxo-1',3'-dithian-2'-yl)cyclohexa-3,5-diene-1,2-diol ; _chemical_name_common ? _chemical_melting_point 112 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 O3 S2' _chemical_formula_weight 246.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.2634(7) _cell_length_b 10.0356(14) _cell_length_c 10.9997(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.184(2) _cell_angle_gamma 90.00 _cell_volume 576.46(14) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 28.0 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8778 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\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 6184 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2396 _reflns_number_gt 2238 _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^)+(0.0649P)^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 refined _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 -0.06(9) _refine_ls_number_reflns 2396 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8539(5) 1.2089(3) 0.7221(3) 0.0251(6) Uani 1 1 d . . . H1 H 0.718(6) 1.226(3) 0.666(3) 0.023(7) Uiso 1 1 d . . . O1 O 0.8873(4) 1.3258(2) 0.7955(2) 0.0311(5) Uani 1 1 d . . . HO1 H 0.983(9) 1.314(5) 0.860(4) 0.053(11) Uiso 1 1 d . . . C2 C 0.7845(5) 1.0879(3) 0.7958(2) 0.0230(5) Uani 1 1 d . . . H2 H 0.618(6) 1.105(3) 0.823(3) 0.024(8) Uiso 1 1 d . . . O2 O 0.9777(4) 1.0759(2) 0.89997(18) 0.0313(5) Uani 1 1 d . . . HO2 H 0.938(7) 1.014(4) 0.939(3) 0.043(11) Uiso 1 1 d . . . C3 C 0.7737(5) 0.9614(2) 0.7167(2) 0.0195(5) Uani 1 1 d . . . C4 C 0.9333(5) 0.9505(3) 0.6303(2) 0.0238(5) Uani 1 1 d . . . H4 H 0.941(6) 0.874(3) 0.582(3) 0.025(7) Uiso 1 1 d . . . C5 C 1.1088(5) 1.0586(3) 0.6068(3) 0.0285(6) Uani 1 1 d . . . H5 H 1.251(6) 1.042(3) 0.558(3) 0.029(8) Uiso 1 1 d . . . C6 C 1.0807(6) 1.1802(3) 0.6528(3) 0.0283(6) Uani 1 1 d . . . H6 H 1.190(6) 1.253(4) 0.638(3) 0.027(7) Uiso 1 1 d . . . S1' S 0.75739(10) 0.75269(5) 0.87799(5) 0.02002(16) Uani 1 1 d . . . O1' O 0.7830(4) 0.84883(17) 0.98633(16) 0.0284(4) Uani 1 1 d . . . C2' C 0.5952(5) 0.8504(2) 0.7476(2) 0.0193(5) Uani 1 1 d . . . H2' H 0.448(6) 0.892(3) 0.781(3) 0.020(7) Uiso 1 1 d . . . S3' S 0.51783(12) 0.73684(6) 0.61916(5) 0.02541(17) Uani 1 1 d . . . C4' C 0.2945(6) 0.6248(3) 0.6820(3) 0.0287(6) Uani 1 1 d . . . H4'A H 0.160(6) 0.675(3) 0.693(3) 0.025(8) Uiso 1 1 d . . . H4'B H 0.249(6) 0.563(4) 0.613(3) 0.032(9) Uiso 1 1 d . . . C5' C 0.4090(6) 0.5514(3) 0.7980(3) 0.0298(6) Uani 1 1 d . . . H5'A H 0.274(6) 0.495(3) 0.823(3) 0.027(8) Uiso 1 1 d . . . H5'B H 0.562(7) 0.492(4) 0.785(3) 0.044(10) Uiso 1 1 d . . . C6' C 0.4935(5) 0.6457(3) 0.9040(3) 0.0254(6) Uani 1 1 d . . . H6'A H 0.357(6) 0.708(3) 0.923(3) 0.023(7) Uiso 1 1 d . . . H6'B H 0.552(7) 0.599(4) 0.963(3) 0.044(10) 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 C1 0.0244(13) 0.0236(13) 0.0247(12) 0.0038(9) -0.0071(10) -0.0015(10) O1 0.0352(12) 0.0227(9) 0.0321(11) 0.0008(8) -0.0089(9) -0.0010(8) C2 0.0221(13) 0.0241(12) 0.0216(13) -0.0024(10) -0.0016(10) -0.0024(10) O2 0.0395(12) 0.0278(10) 0.0233(10) 0.0051(8) -0.0095(8) -0.0098(8) C3 0.0199(11) 0.0209(11) 0.0167(11) 0.0049(9) -0.0013(9) -0.0005(9) C4 0.0244(13) 0.0251(13) 0.0216(13) 0.0031(10) 0.0027(10) 0.0017(10) C5 0.0220(14) 0.0360(15) 0.0274(14) 0.0085(11) 0.0026(11) 0.0000(11) C6 0.0238(13) 0.0300(13) 0.0296(14) 0.0104(11) -0.0022(11) -0.0065(11) S1' 0.0192(3) 0.0216(3) 0.0186(3) 0.0027(2) -0.00029(19) -0.0004(2) O1' 0.0412(12) 0.0247(10) 0.0177(9) 0.0010(7) -0.0031(8) 0.0004(8) C2' 0.0228(13) 0.0194(11) 0.0150(12) 0.0001(8) -0.0002(9) 0.0014(10) S3' 0.0280(3) 0.0285(3) 0.0196(3) -0.0035(3) 0.0024(2) -0.0062(3) C4' 0.0264(15) 0.0274(13) 0.0312(15) 0.0013(11) -0.0004(11) -0.0076(12) C5' 0.0269(15) 0.0253(13) 0.0357(17) 0.0049(12) -0.0017(12) -0.0082(12) C6' 0.0228(13) 0.0278(13) 0.0256(14) 0.0077(11) 0.0032(10) -0.0032(11) _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 O1 1.422(3) . ? C1 C6 1.522(4) . ? C1 C2 1.530(4) . ? C2 O2 1.438(3) . ? C2 C3 1.536(4) . ? C3 C4 1.349(4) . ? C3 C2' 1.523(3) . ? C4 C5 1.469(4) . ? C5 C6 1.336(4) . ? S1' O1' 1.5262(19) . ? S1' C6' 1.807(3) . ? S1' C2' 1.855(2) . ? C2' S3' 1.821(2) . ? S3' C4' 1.824(3) . ? C4' C5' 1.530(4) . ? C5' C6' 1.525(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 O1 C1 C6 113.1(2) . . ? O1 C1 C2 112.0(2) . . ? C6 C1 C2 111.7(2) . . ? O2 C2 C1 107.3(2) . . ? O2 C2 C3 110.8(2) . . ? C1 C2 C3 110.5(2) . . ? C4 C3 C2' 123.6(2) . . ? C4 C3 C2 119.0(2) . . ? C2' C3 C2 117.3(2) . . ? C3 C4 C5 121.6(3) . . ? C6 C5 C4 120.4(3) . . ? C5 C6 C1 119.6(3) . . ? O1' S1' C6' 104.28(13) . . ? O1' S1' C2' 104.88(10) . . ? C6' S1' C2' 98.54(12) . . ? C3 C2' S3' 111.67(17) . . ? C3 C2' S1' 108.81(16) . . ? S3' C2' S1' 107.79(12) . . ? C2' S3' C4' 100.62(13) . . ? C5' C4' S3' 114.1(2) . . ? C6' C5' C4' 112.7(2) . . ? C5' C6' S1' 113.8(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 O1 C1 C2 O2 -54.1(3) . . . . ? C6 C1 C2 O2 73.8(3) . . . . ? O1 C1 C2 C3 -175.0(2) . . . . ? C6 C1 C2 C3 -47.0(3) . . . . ? O2 C2 C3 C4 -85.9(3) . . . . ? C1 C2 C3 C4 32.8(3) . . . . ? O2 C2 C3 C2' 89.5(3) . . . . ? C1 C2 C3 C2' -151.8(2) . . . . ? C2' C3 C4 C5 -177.7(2) . . . . ? C2 C3 C4 C5 -2.6(3) . . . . ? C3 C4 C5 C6 -13.3(4) . . . . ? C4 C5 C6 C1 -4.4(4) . . . . ? O1 C1 C6 C5 162.5(2) . . . . ? C2 C1 C6 C5 35.1(3) . . . . ? C4 C3 C2' S3' -24.7(3) . . . . ? C2 C3 C2' S3' 160.04(17) . . . . ? C4 C3 C2' S1' 94.1(2) . . . . ? C2 C3 C2' S1' -81.1(2) . . . . ? O1' S1' C2' C3 66.30(19) . . . . ? C6' S1' C2' C3 173.64(18) . . . . ? O1' S1' C2' S3' -172.44(12) . . . . ? C6' S1' C2' S3' -65.11(15) . . . . ? C3 C2' S3' C4' -177.17(18) . . . . ? S1' C2' S3' C4' 63.37(16) . . . . ? C2' S3' C4' C5' -60.1(2) . . . . ? S3' C4' C5' C6' 62.4(3) . . . . ? C4' C5' C6' S1' -65.9(3) . . . . ? O1' S1' C6' C5' 172.60(19) . . . . ? C2' S1' C6' C5' 64.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.341 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.062 #===END data_24 _database_code_CSD 171332 _audit_creation_method 'SHELXL-97' _chemical_name_systematic ;(1S,2S)-2-phenyl-1,3-dithiolane-1-oxide ; _chemical_name_common ? _chemical_melting_point 85-89 _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 O S2' _chemical_formula_weight 198.29 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 orthorhombic _symmetry_space_group_name_H-M P2(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 6.2383(5) _cell_length_b 8.6358(7) _cell_length_c 17.1061(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 921.55(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.0 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.524 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8179 _exptl_absorpt_correction_T_max 0.9025 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\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 10088 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.18 _reflns_number_total 2009 _reflns_number_gt 1967 _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^)+(0.0471P)^2^+0.1101P] 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 refined _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 -0.07(7) _refine_ls_number_reflns 2009 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 0.92454(6) 0.62524(4) 0.18005(2) 0.02433(11) Uani 1 1 d . . . O1 O 0.9234(2) 0.61314(14) 0.26759(7) 0.0356(3) Uani 1 1 d . . . C2 C 1.0797(3) 0.45994(18) 0.14187(8) 0.0229(3) Uani 1 1 d . . . H2 H 1.024(4) 0.369(2) 0.1648(12) 0.032(5) Uiso 1 1 d . . . S3 S 1.34881(7) 0.48247(5) 0.17990(3) 0.02980(12) Uani 1 1 d . . . C4 C 1.3450(3) 0.6935(2) 0.18960(14) 0.0403(5) Uani 1 1 d . . . H4A H 1.348(5) 0.709(4) 0.2521(18) 0.069(9) Uiso 1 1 d . . . H4B H 1.466(5) 0.733(3) 0.1621(14) 0.044(7) Uiso 1 1 d . . . C5 C 1.1387(3) 0.75734(18) 0.15578(10) 0.0254(3) Uani 1 1 d . . . H5A H 1.103(3) 0.861(2) 0.1751(11) 0.028(5) Uiso 1 1 d . . . H5B H 1.138(3) 0.760(2) 0.1008(12) 0.024(4) Uiso 1 1 d . . . C1' C 1.0499(3) 0.45455(16) 0.05365(8) 0.0215(3) Uani 1 1 d . . . C2' C 1.2123(3) 0.4922(2) 0.00119(9) 0.0268(3) Uani 1 1 d . . . H2' H 1.349(3) 0.524(2) 0.0204(11) 0.022(5) Uiso 1 1 d . . . C3' C 1.1745(3) 0.4835(2) -0.07909(10) 0.0311(4) Uani 1 1 d . . . H3' H 1.296(4) 0.504(3) -0.1183(14) 0.043(6) Uiso 1 1 d . . . C4' C 0.9739(3) 0.44031(19) -0.10714(9) 0.0290(4) Uani 1 1 d . . . H4' H 0.948(4) 0.432(3) -0.1606(13) 0.036(6) Uiso 1 1 d . . . C5' C 0.8110(3) 0.4045(2) -0.05487(10) 0.0280(3) Uani 1 1 d . . . H5' H 0.677(4) 0.375(3) -0.0723(12) 0.035(5) Uiso 1 1 d . . . C6' C 0.8492(3) 0.41034(19) 0.02526(9) 0.0251(3) Uani 1 1 d . . . H6' H 0.739(3) 0.387(3) 0.0597(12) 0.031(5) 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 0.02446(18) 0.02365(19) 0.02487(19) -0.00149(14) 0.00480(16) -0.00071(14) O1 0.0527(8) 0.0289(6) 0.0252(6) -0.0034(4) 0.0133(5) -0.0035(6) C2 0.0274(7) 0.0194(7) 0.0219(7) 0.0002(5) 0.0009(6) 0.0007(6) S3 0.0329(2) 0.0261(2) 0.0304(2) -0.00311(16) -0.01032(18) 0.00879(16) C4 0.0286(8) 0.0243(8) 0.0680(14) -0.0008(8) -0.0103(10) -0.0020(7) C5 0.0275(8) 0.0194(7) 0.0293(7) 0.0034(5) 0.0013(6) -0.0005(7) C1' 0.0257(7) 0.0172(7) 0.0217(7) 0.0001(5) -0.0009(6) 0.0015(6) C2' 0.0241(7) 0.0282(8) 0.0282(8) 0.0015(6) 0.0004(6) -0.0008(7) C3' 0.0334(8) 0.0346(8) 0.0252(8) 0.0037(7) 0.0070(7) 0.0027(8) C4' 0.0402(9) 0.0257(8) 0.0210(7) 0.0000(5) -0.0035(7) 0.0037(7) C5' 0.0296(8) 0.0244(7) 0.0301(8) -0.0013(6) -0.0059(7) -0.0011(7) C6' 0.0258(7) 0.0226(7) 0.0269(8) 0.0010(6) 0.0016(6) -0.0021(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 1.5011(12) . ? S1 C5 1.8054(17) . ? S1 C2 1.8444(16) . ? C2 C1' 1.5213(19) . ? C2 S3 1.8107(18) . ? S3 C4 1.8301(19) . ? C4 C5 1.515(3) . ? C1' C2' 1.391(2) . ? C1' C6' 1.396(2) . ? C2' C3' 1.395(2) . ? C3' C4' 1.391(3) . ? C4' C5' 1.388(2) . ? C5' C6' 1.392(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 C5 106.07(8) . . ? O1 S1 C2 107.56(7) . . ? C5 S1 C2 91.09(8) . . ? C1' C2 S3 118.24(12) . . ? C1' C2 S1 108.11(10) . . ? S3 C2 S1 106.04(8) . . ? C2 S3 C4 97.33(8) . . ? C5 C4 S3 109.80(13) . . ? C4 C5 S1 108.12(12) . . ? C2' C1' C6' 119.49(14) . . ? C2' C1' C2 122.93(14) . . ? C6' C1' C2 117.58(14) . . ? C1' C2' C3' 119.94(16) . . ? C4' C3' C2' 120.40(15) . . ? C5' C4' C3' 119.73(14) . . ? C4' C5' C6' 120.05(15) . . ? C5' C6' C1' 120.38(15) . . ? 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 C2 C1' 170.27(11) . . . . ? C5 S1 C2 C1' -82.49(12) . . . . ? O1 S1 C2 S3 -62.01(9) . . . . ? C5 S1 C2 S3 45.23(9) . . . . ? C1' C2 S3 C4 93.84(13) . . . . ? S1 C2 S3 C4 -27.59(11) . . . . ? C2 S3 C4 C5 -5.51(17) . . . . ? S3 C4 C5 S1 38.05(18) . . . . ? O1 S1 C5 C4 57.66(15) . . . . ? C2 S1 C5 C4 -50.97(14) . . . . ? S3 C2 C1' C2' -11.3(2) . . . . ? S1 C2 C1' C2' 109.09(16) . . . . ? S3 C2 C1' C6' 169.04(12) . . . . ? S1 C2 C1' C6' -70.60(15) . . . . ? C6' C1' C2' C3' -0.9(3) . . . . ? C2 C1' C2' C3' 179.47(15) . . . . ? C1' C2' C3' C4' 1.3(3) . . . . ? C2' C3' C4' C5' -0.5(3) . . . . ? C3' C4' C5' C6' -0.6(3) . . . . ? C4' C5' C6' C1' 1.0(2) . . . . ? C2' C1' C6' C5' -0.3(2) . . . . ? C2 C1' C6' C5' 179.42(14) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.383 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.086 #===END data_27 _database_code_CSD 171333 _audit_creation_method 'SHELXL-97' _chemical_name_systematic ; cis-(1S,2R)-3-(R-methylsulfinylmethyl)cyclohexa-3,5-diene-1,2-diol ; _chemical_name_common ? _chemical_melting_point 123 _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 O3 S' _chemical_formula_weight 188.24 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 P2(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 5.3260(10) _cell_length_b 8.8440(10) _cell_length_c 18.602(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 876.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.333 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _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_% 0 _diffrn_reflns_number 938 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 938 _reflns_number_gt 843 _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^)+(0.0556P)^2^+0.1884P] 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 refined _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.002(2) _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 -0.26(19) _refine_ls_number_reflns 938 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 -0.1305(6) -0.4907(4) 0.87437(19) 0.0218(8) Uani 1 1 d . . . H1 H -0.243(9) -0.407(5) 0.896(2) 0.039(12) Uiso 1 1 d . . . O1 O -0.2635(5) -0.5885(3) 0.82697(16) 0.0285(7) Uani 1 1 d . . . HO1 H -0.393(10) -0.556(6) 0.823(3) 0.039(16) Uiso 1 1 d . . . C2 C 0.0706(7) -0.4018(4) 0.83474(19) 0.0176(8) Uani 1 1 d . . . H2 H -0.008(6) -0.333(4) 0.8019(17) 0.012(9) Uiso 1 1 d . . . O2 O 0.2382(5) -0.4979(3) 0.79505(13) 0.0214(6) Uani 1 1 d . . . HO2 H 0.181(8) -0.509(5) 0.759(2) 0.030(13) Uiso 1 1 d . . . C3 C 0.2320(6) -0.3147(4) 0.88729(19) 0.0170(7) Uani 1 1 d . . . C4 C 0.2736(7) -0.3728(4) 0.9523(2) 0.0205(8) Uani 1 1 d . . . H4 H 0.365(8) -0.323(4) 0.984(2) 0.031(12) Uiso 1 1 d . . . C5 C 0.1612(7) -0.5160(4) 0.9750(2) 0.0251(8) Uani 1 1 d . . . H5 H 0.214(8) -0.559(5) 1.018(2) 0.034(12) Uiso 1 1 d . . . C6 C -0.0241(8) -0.5755(4) 0.9376(2) 0.0260(10) Uani 1 1 d . . . H6 H -0.076(8) -0.660(5) 0.9507(19) 0.025(11) Uiso 1 1 d . . . C1' C 0.3522(8) -0.1721(4) 0.8608(2) 0.0188(8) Uani 1 1 d . . . H1'A H 0.376(7) -0.174(4) 0.8158(18) 0.004(8) Uiso 1 1 d . . . H1'B H 0.515(10) -0.149(5) 0.881(2) 0.042(13) Uiso 1 1 d . . . S2' S 0.15662(15) -0.01116(9) 0.88294(5) 0.0193(3) Uani 1 1 d . . . O2' O -0.0890(4) -0.0330(3) 0.84374(13) 0.0241(6) Uani 1 1 d . . . C3' C 0.3261(8) 0.1309(4) 0.8358(2) 0.0225(9) Uani 1 1 d . . . H3'A H 0.486(10) 0.138(5) 0.861(2) 0.041(14) Uiso 1 1 d . . . H3'B H 0.351(8) 0.105(5) 0.785(2) 0.036(12) Uiso 1 1 d . . . H3'C H 0.246(9) 0.227(5) 0.842(2) 0.038(12) 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 C1 0.0134(16) 0.0158(16) 0.036(2) -0.0073(17) 0.0007(15) -0.0020(17) O1 0.0132(14) 0.0244(15) 0.0478(18) -0.0096(13) -0.0021(14) -0.0040(13) C2 0.0129(16) 0.0169(17) 0.0231(19) 0.0013(15) 0.0001(16) 0.0012(15) O2 0.0163(11) 0.0264(14) 0.0216(13) -0.0040(13) -0.0009(11) 0.0014(12) C3 0.0118(15) 0.0129(15) 0.0263(17) -0.0015(15) 0.0025(17) 0.0026(14) C4 0.0169(18) 0.0172(18) 0.0273(19) -0.0043(15) -0.0009(17) 0.0002(16) C5 0.0288(19) 0.0223(18) 0.0242(18) 0.0069(16) 0.0033(17) 0.003(2) C6 0.031(2) 0.0171(19) 0.030(2) 0.0012(17) 0.0115(19) -0.0047(19) C1' 0.0155(18) 0.0173(16) 0.024(2) 0.0009(15) 0.0011(16) 0.0016(18) S2' 0.0149(4) 0.0163(4) 0.0267(5) 0.0008(4) 0.0000(4) -0.0012(4) O2' 0.0153(12) 0.0279(14) 0.0291(13) 0.0040(12) -0.0027(11) 0.0002(12) C3' 0.021(2) 0.0152(18) 0.032(2) -0.0003(16) 0.000(2) -0.0021(18) _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 O1 1.424(4) . ? C1 C6 1.505(5) . ? C1 C2 1.520(5) . ? C2 O2 1.437(4) . ? C2 C3 1.512(5) . ? C3 C4 1.332(5) . ? C3 C1' 1.498(5) . ? C4 C5 1.463(5) . ? C5 C6 1.317(6) . ? C1' S2' 1.811(4) . ? S2' O2' 1.510(2) . ? S2' C3' 1.779(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 O1 C1 C6 111.6(3) . . ? O1 C1 C2 111.4(3) . . ? C6 C1 C2 111.8(3) . . ? O2 C2 C3 106.3(3) . . ? O2 C2 C1 112.4(3) . . ? C3 C2 C1 110.5(3) . . ? C4 C3 C1' 123.5(3) . . ? C4 C3 C2 119.0(3) . . ? C1' C3 C2 117.3(3) . . ? C3 C4 C5 121.8(3) . . ? C6 C5 C4 120.0(4) . . ? C5 C6 C1 119.7(3) . . ? C3 C1' S2' 110.0(3) . . ? O2' S2' C3' 106.98(17) . . ? O2' S2' C1' 106.74(17) . . ? C3' S2' C1' 98.71(18) . . ? 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 C1 C2 O2 -53.9(4) . . . . ? C6 C1 C2 O2 71.7(4) . . . . ? O1 C1 C2 C3 -172.4(3) . . . . ? C6 C1 C2 C3 -46.8(4) . . . . ? O2 C2 C3 C4 -89.9(4) . . . . ? C1 C2 C3 C4 32.3(4) . . . . ? O2 C2 C3 C1' 85.7(4) . . . . ? C1 C2 C3 C1' -152.2(3) . . . . ? C1' C3 C4 C5 -177.2(3) . . . . ? C2 C3 C4 C5 -1.9(5) . . . . ? C3 C4 C5 C6 -14.0(5) . . . . ? C4 C5 C6 C1 -4.0(5) . . . . ? O1 C1 C6 C5 160.3(3) . . . . ? C2 C1 C6 C5 34.8(5) . . . . ? C4 C3 C1' S2' -90.3(4) . . . . ? C2 C3 C1' S2' 94.3(3) . . . . ? C3 C1' S2' O2' -62.3(3) . . . . ? C3 C1' S2' C3' -173.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.605 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.056 #===END