Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 _publ_section_title ;Stereoselective synthesis of functionalised thioesters using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes ; _publ_contact_author_name 'Prof. R.Jackson' _publ_contact_author_email R.F.W.JACKSON@SHEFFIELD.AC.UK loop_ _publ_author_name R.Jackson 'Harry Adams' 'Christopher G. Barber' 'Lorenzo Caggiano' 'Lyndsay Ann Evans' # Attachment 'Fig1.CIF' data_orj8m _database_code_depnum_ccdc_archive 'CCDC 653097' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O3 S' _chemical_formula_weight 251.29 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' 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 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 9.243(5) _cell_length_b 5.497(3) _cell_length_c 12.258(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.177(9) _cell_angle_gamma 90.00 _cell_volume 620.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1451 _cell_measurement_theta_min 5.296 _cell_measurement_theta_max 50.382 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9022 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 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 smart1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5727 _diffrn_reflns_av_R_equivalents 0.0954 _diffrn_reflns_av_sigmaI/netI 0.1122 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2147 _reflns_number_gt 1457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker smart' _computing_cell_refinement 'Bruker smart' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0700P)^2^+0.0489P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.14(19) _chemical_absolute_configuration UNK _refine_ls_number_reflns 2147 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1731 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 0.67124(16) 0.4569(3) 0.68438(12) 0.0356(4) Uani 1 1 d . . . N1 N 0.8291(5) 0.8094(9) 0.9554(4) 0.0313(12) Uani 1 1 d . . . H1N H 0.9075 0.6974 0.9638 0.07(2) Uiso 1 1 d R . . O1 O 0.8693(4) 1.2032(8) 1.0140(3) 0.0379(11) Uani 1 1 d . . . O2 O 0.6518(4) 1.0804(8) 0.9382(3) 0.0301(10) Uani 1 1 d . . . O4 O 0.8249(4) 0.8550(8) 0.7302(3) 0.0373(11) Uani 1 1 d . . . C1 C 0.7951(5) 1.0399(12) 0.9731(5) 0.0272(14) Uani 1 1 d . . . C2 C 0.7167(5) 0.6878(11) 0.8842(4) 0.0270(13) Uani 1 1 d . . . H2 H 0.7035 0.5156 0.9076 0.032 Uiso 1 1 calc R . . C3 C 0.5858(5) 0.8459(11) 0.9080(5) 0.0289(14) Uani 1 1 d . . . H3 H 0.5431 0.7776 0.9736 0.035 Uiso 1 1 calc R . . C4 C 0.7524(5) 0.7009(11) 0.7644(4) 0.0257(13) Uani 1 1 d . . . C5 C 0.7270(6) 0.5356(10) 0.5533(4) 0.0283(14) Uani 1 1 d . . . C6 C 0.8282(6) 0.3924(12) 0.5082(5) 0.0364(16) Uani 1 1 d . . . H6 H 0.8648 0.2500 0.5449 0.044 Uiso 1 1 calc R . . C7 C 0.8764(6) 0.4595(15) 0.4074(5) 0.0393(15) Uani 1 1 d . . . H7 H 0.9455 0.3599 0.3759 0.047 Uiso 1 1 calc R . . C8 C 0.8269(6) 0.6632(13) 0.3535(5) 0.0364(16) Uani 1 1 d . . . C9 C 0.7237(7) 0.8056(13) 0.3995(5) 0.0414(17) Uani 1 1 d . . . H9 H 0.6878 0.9485 0.3628 0.050 Uiso 1 1 calc R . . C10 C 0.6724(6) 0.7402(13) 0.4992(5) 0.0389(16) Uani 1 1 d . . . H10 H 0.6005 0.8361 0.5295 0.047 Uiso 1 1 calc R . . C11 C 0.8852(7) 0.7400(15) 0.2461(5) 0.054(2) Uani 1 1 d . . . H11A H 0.9754 0.8321 0.2618 0.081 Uiso 1 1 calc R . . H11B H 0.8131 0.8422 0.2043 0.081 Uiso 1 1 calc R . . H11C H 0.9044 0.5951 0.2032 0.081 Uiso 1 1 calc R . . C12 C 0.4642(6) 0.8840(13) 0.8186(5) 0.0450(18) Uani 1 1 d . . . H12A H 0.3899 0.9897 0.8458 0.068 Uiso 1 1 calc R . . H12B H 0.4208 0.7267 0.7969 0.068 Uiso 1 1 calc R . . H12C H 0.5030 0.9605 0.7552 0.068 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 0.0381(8) 0.0385(9) 0.0303(8) -0.0030(8) 0.0038(6) -0.0077(7) N1 0.029(3) 0.037(3) 0.027(3) -0.001(2) -0.007(2) 0.008(2) O1 0.024(2) 0.044(3) 0.044(3) -0.006(2) -0.0041(18) -0.004(2) O2 0.0172(19) 0.038(2) 0.034(2) -0.002(2) -0.0009(16) 0.0030(17) O4 0.035(2) 0.045(3) 0.033(2) -0.003(2) 0.0074(18) -0.013(2) C1 0.016(3) 0.042(4) 0.024(3) 0.006(3) 0.003(2) 0.000(3) C2 0.029(3) 0.027(3) 0.025(3) -0.001(3) -0.002(2) -0.002(2) C3 0.023(3) 0.036(4) 0.028(3) 0.003(3) 0.006(2) -0.006(3) C4 0.021(3) 0.028(3) 0.027(3) -0.004(3) 0.000(2) -0.002(3) C5 0.027(3) 0.034(4) 0.023(3) -0.002(2) -0.006(2) -0.002(2) C6 0.032(3) 0.042(4) 0.034(4) -0.005(3) 0.000(3) -0.002(3) C7 0.028(3) 0.051(4) 0.039(3) -0.009(4) 0.002(3) 0.003(3) C8 0.028(3) 0.052(4) 0.027(3) -0.002(3) -0.006(3) -0.005(3) C9 0.042(4) 0.052(4) 0.028(4) 0.004(3) -0.011(3) -0.002(3) C10 0.030(3) 0.055(5) 0.030(4) -0.006(3) -0.001(3) 0.007(3) C11 0.041(4) 0.085(6) 0.035(4) 0.011(4) 0.000(3) -0.013(4) C12 0.022(3) 0.068(5) 0.044(4) -0.011(3) -0.004(3) 0.001(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 C5 1.784(6) . ? S1 C4 1.786(6) . ? N1 C1 1.328(8) . ? N1 C2 1.458(7) . ? N1 H1N 0.9500 . ? O1 C1 1.211(7) . ? O2 C1 1.373(6) . ? O2 C3 1.460(7) . ? O4 C4 1.180(6) . ? C2 C4 1.535(8) . ? C2 C3 1.540(8) . ? C2 H2 1.0000 . ? C3 C12 1.512(7) . ? C3 H3 1.0000 . ? C5 C6 1.376(8) . ? C5 C10 1.378(8) . ? C6 C7 1.400(8) . ? C6 H6 0.9500 . ? C7 C8 1.359(9) . ? C7 H7 0.9500 . ? C8 C9 1.392(9) . ? C8 C11 1.526(8) . ? C9 C10 1.397(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C5 S1 C4 99.9(3) . . ? C1 N1 C2 111.7(5) . . ? C1 N1 H1N 142.3 . . ? C2 N1 H1N 105.2 . . ? C1 O2 C3 107.8(4) . . ? O1 C1 N1 129.9(5) . . ? O1 C1 O2 120.2(5) . . ? N1 C1 O2 109.9(5) . . ? N1 C2 C4 110.4(4) . . ? N1 C2 C3 99.1(4) . . ? C4 C2 C3 113.3(4) . . ? N1 C2 H2 111.2 . . ? C4 C2 H2 111.2 . . ? C3 C2 H2 111.2 . . ? O2 C3 C12 109.1(5) . . ? O2 C3 C2 103.2(4) . . ? C12 C3 C2 119.1(5) . . ? O2 C3 H3 108.3 . . ? C12 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? O4 C4 C2 123.4(5) . . ? O4 C4 S1 124.6(4) . . ? C2 C4 S1 112.0(4) . . ? C6 C5 C10 120.4(6) . . ? C6 C5 S1 119.0(4) . . ? C10 C5 S1 120.5(5) . . ? C5 C6 C7 119.1(6) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.8(6) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 118.6(6) . . ? C7 C8 C11 121.2(6) . . ? C9 C8 C11 120.1(6) . . ? C8 C9 C10 120.6(6) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 119.5(6) . . ? C5 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.334 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.079 # Attachment 'Fig2.CIF' data_orj21m _database_code_depnum_ccdc_archive 'CCDC 653098' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 O4 S' _chemical_formula_weight 252.28 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 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 7.5636(11) _cell_length_b 10.4554(16) _cell_length_c 15.375(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1215.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5648 _cell_measurement_theta_min 4.711 _cell_measurement_theta_max 53.983 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8943 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details 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 SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13372 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2758 _reflns_number_gt 2416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 '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^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _chemical_absolute_configuration unk _refine_ls_number_reflns 2758 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.26312(6) 0.91807(4) 0.09964(3) 0.03377(13) Uani 1 1 d . . . O1 O 0.07973(19) 1.24294(13) 0.19531(10) 0.0471(4) Uani 1 1 d . . . O2 O 0.34424(16) 1.14863(11) 0.17869(8) 0.0323(3) Uani 1 1 d . . . O3 O 0.18890(16) 1.11372(11) 0.29863(8) 0.0355(3) Uani 1 1 d . . . O4 O 0.53329(17) 0.83941(11) 0.19601(9) 0.0378(3) Uani 1 1 d . . . C1 C 0.1934(2) 1.17534(16) 0.22246(13) 0.0339(4) Uani 1 1 d . . . C2 C 0.4432(2) 1.05348(15) 0.22510(12) 0.0294(4) Uani 1 1 d . . . H2 H 0.5692 1.0814 0.2304 0.035 Uiso 1 1 calc R . . C3 C 0.3568(2) 1.05122(15) 0.31555(12) 0.0299(4) Uani 1 1 d . . . H3 H 0.4279 1.1054 0.3561 0.036 Uiso 1 1 calc R . . C4 C 0.4347(2) 0.92496(16) 0.17740(12) 0.0291(4) Uani 1 1 d . . . C5 C 0.2694(2) 0.75384(16) 0.07031(11) 0.0293(4) Uani 1 1 d . . . C6 C 0.2041(2) 0.66030(17) 0.12628(12) 0.0301(4) Uani 1 1 d . . . H6 H 0.1644 0.6830 0.1828 0.036 Uiso 1 1 calc R . . C7 C 0.1972(2) 0.53362(16) 0.09914(13) 0.0334(4) Uani 1 1 d . . . H7 H 0.1542 0.4700 0.1378 0.040 Uiso 1 1 calc R . . C8 C 0.2523(3) 0.49857(17) 0.01625(13) 0.0359(4) Uani 1 1 d . . . C9 C 0.3161(2) 0.59367(19) -0.03814(12) 0.0363(4) Uani 1 1 d . . . H9 H 0.3540 0.5714 -0.0951 0.044 Uiso 1 1 calc R . . C10 C 0.3262(2) 0.72048(18) -0.01200(13) 0.0348(4) Uani 1 1 d . . . H10 H 0.3718 0.7837 -0.0503 0.042 Uiso 1 1 calc R . . C11 C 0.2388(3) 0.36132(18) -0.01388(14) 0.0493(5) Uani 1 1 d . . . H11A H 0.1193 0.3451 -0.0359 0.074 Uiso 1 1 calc R . . H11B H 0.2632 0.3039 0.0351 0.074 Uiso 1 1 calc R . . H11C H 0.3250 0.3460 -0.0603 0.074 Uiso 1 1 calc R . . C12 C 0.3229(3) 0.92216(17) 0.35780(12) 0.0370(4) Uani 1 1 d . . . H12A H 0.2643 0.9348 0.4140 0.056 Uiso 1 1 calc R . . H12B H 0.4356 0.8778 0.3667 0.056 Uiso 1 1 calc R . . H12C H 0.2469 0.8706 0.3199 0.056 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 0.0312(2) 0.0290(2) 0.0411(3) 0.00245(19) -0.0062(2) 0.00225(18) O1 0.0421(8) 0.0382(7) 0.0612(10) 0.0094(7) -0.0011(7) 0.0107(6) O2 0.0336(7) 0.0258(6) 0.0375(7) 0.0073(5) 0.0031(6) 0.0012(5) O3 0.0303(6) 0.0355(6) 0.0406(7) 0.0053(5) 0.0042(6) 0.0031(5) O4 0.0328(7) 0.0341(6) 0.0467(8) -0.0031(6) -0.0051(6) 0.0089(6) C1 0.0308(9) 0.0258(8) 0.0452(11) 0.0011(8) 0.0017(9) -0.0001(7) C2 0.0246(8) 0.0258(8) 0.0378(10) 0.0036(7) -0.0023(8) -0.0015(6) C3 0.0284(9) 0.0274(8) 0.0338(10) 0.0010(7) -0.0011(8) -0.0005(7) C4 0.0233(8) 0.0282(8) 0.0358(10) 0.0032(8) 0.0049(7) -0.0003(7) C5 0.0219(8) 0.0322(8) 0.0339(9) -0.0012(7) -0.0049(8) 0.0002(7) C6 0.0253(8) 0.0357(8) 0.0292(9) -0.0007(7) 0.0009(7) -0.0008(7) C7 0.0290(9) 0.0342(8) 0.0370(10) 0.0045(8) -0.0044(9) -0.0043(7) C8 0.0265(8) 0.0392(9) 0.0419(11) -0.0070(8) -0.0071(9) 0.0014(8) C9 0.0291(9) 0.0496(10) 0.0303(9) -0.0062(8) 0.0015(8) 0.0025(9) C10 0.0262(9) 0.0431(10) 0.0352(10) 0.0058(8) 0.0021(8) -0.0007(8) C11 0.0521(13) 0.0433(10) 0.0526(13) -0.0156(9) -0.0068(12) -0.0018(10) C12 0.0430(10) 0.0304(9) 0.0378(10) 0.0060(8) 0.0015(9) -0.0013(9) _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 C4 1.7658(18) . ? S1 C5 1.7759(18) . ? O1 C1 1.189(2) . ? O2 C1 1.354(2) . ? O2 C2 1.4351(19) . ? O3 C1 1.337(2) . ? O3 C3 1.451(2) . ? O4 C4 1.199(2) . ? C2 C4 1.532(2) . ? C2 C3 1.537(3) . ? C2 H2 1.0000 . ? C3 C12 1.519(2) . ? C3 H3 1.0000 . ? C5 C10 1.381(3) . ? C5 C6 1.393(2) . ? C6 C7 1.390(2) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.386(3) . ? C8 C11 1.511(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C5 101.06(8) . . ? C1 O2 C2 109.60(13) . . ? C1 O3 C3 110.58(14) . . ? O1 C1 O3 125.14(18) . . ? O1 C1 O2 123.90(18) . . ? O3 C1 O2 110.95(15) . . ? O2 C2 C4 110.36(14) . . ? O2 C2 C3 103.80(13) . . ? C4 C2 C3 113.68(13) . . ? O2 C2 H2 109.6 . . ? C4 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? O3 C3 C12 109.21(14) . . ? O3 C3 C2 101.72(13) . . ? C12 C3 C2 118.18(14) . . ? O3 C3 H3 109.1 . . ? C12 C3 H3 109.1 . . ? C2 C3 H3 109.1 . . ? O4 C4 C2 120.90(16) . . ? O4 C4 S1 126.02(14) . . ? C2 C4 S1 113.01(12) . . ? C10 C5 C6 119.93(16) . . ? C10 C5 S1 119.02(14) . . ? C6 C5 S1 120.83(13) . . ? C7 C6 C5 119.80(17) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 121.02(17) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 117.93(16) . . ? C9 C8 C11 121.33(18) . . ? C7 C8 C11 120.73(18) . . ? C8 C9 C10 122.01(17) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C5 C10 C9 119.30(17) . . ? C5 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.224 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.043 # Attachment 'Fig3.CIF' data_orj57m _database_code_depnum_ccdc_archive 'CCDC 653099' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Br N O3 S' _chemical_formula_weight 388.32 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.587(3) _cell_length_b 5.2659(18) _cell_length_c 19.647(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.641(6) _cell_angle_gamma 90.00 _cell_volume 884.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 970 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 2.454 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4557 _exptl_absorpt_correction_T_max 0.9526 _exptl_absorpt_process_details 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 SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6409 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3063 _reflns_number_gt 2555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.037(12) _chemical_absolute_configuration unk _refine_ls_number_reflns 3063 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.76957(6) 0.68338(11) 0.83917(3) 0.03916(18) Uani 1 1 d . . . S1 S 0.98738(15) 0.6052(2) 0.72344(7) 0.0339(4) Uani 1 1 d . . . N1 N 0.4268(5) 0.5377(7) 0.7868(2) 0.0217(9) Uani 1 1 d . . . H1A H 0.4363 0.6511 0.8198 0.026 Uiso 1 1 d R . . O1 O 0.7837(4) 0.2797(7) 0.6644(2) 0.0435(10) Uani 1 1 d . . . O2 O 0.4078(4) 0.1155(6) 0.80900(19) 0.0286(9) Uani 1 1 d . . . O3 O 0.3046(4) 0.4147(6) 0.87559(17) 0.0243(8) Uani 1 1 d . . . C1 C 0.8149(6) 0.4193(9) 0.7119(3) 0.0265(11) Uani 1 1 d . . . C2 C 0.7018(6) 0.4423(9) 0.7668(3) 0.0257(12) Uani 1 1 d . . . H2A H 0.6965 0.2717 0.7887 0.031 Uiso 1 1 calc R . . C3 C 0.5358(6) 0.5069(8) 0.7354(3) 0.0210(11) Uani 1 1 d . . . H3A H 0.4982 0.3603 0.7059 0.025 Uiso 1 1 calc R . . C4 C 0.3809(6) 0.3364(9) 0.8232(3) 0.0234(12) Uani 1 1 d . . . C5 C 0.2334(5) 0.2288(9) 0.9191(2) 0.0246(11) Uani 1 1 d . . . C6 C 0.1597(7) 0.4034(10) 0.9690(3) 0.0344(13) Uani 1 1 d . . . H6A H 0.2421 0.4993 0.9958 0.052 Uiso 1 1 calc R . . H6B H 0.1018 0.3014 0.9997 0.052 Uiso 1 1 calc R . . H6C H 0.0879 0.5218 0.9434 0.052 Uiso 1 1 calc R . . C7 C 0.1095(6) 0.0776(10) 0.8765(3) 0.0328(13) Uani 1 1 d . . . H7A H 0.1597 -0.0341 0.8453 0.049 Uiso 1 1 calc R . . H7B H 0.0382 0.1941 0.8500 0.049 Uiso 1 1 calc R . . H7C H 0.0504 -0.0251 0.9067 0.049 Uiso 1 1 calc R . . C8 C 0.3577(6) 0.0633(9) 0.9566(3) 0.0314(13) Uani 1 1 d . . . H8A H 0.4350 0.1707 0.9829 0.047 Uiso 1 1 calc R . . H8B H 0.4096 -0.0373 0.9235 0.047 Uiso 1 1 calc R . . H8C H 0.3090 -0.0508 0.9877 0.047 Uiso 1 1 calc R . . C9 C 1.0789(6) 0.5221(9) 0.6490(3) 0.0258(12) Uani 1 1 d . . . C10 C 1.1760(6) 0.3106(9) 0.6499(3) 0.0265(12) Uani 1 1 d . . . H10A H 1.1875 0.2016 0.6886 0.032 Uiso 1 1 calc R . . C11 C 1.2561(6) 0.2612(9) 0.5932(3) 0.0290(12) Uani 1 1 d . . . H11A H 1.3216 0.1157 0.5934 0.035 Uiso 1 1 calc R . . C12 C 1.2432(6) 0.4176(9) 0.5364(2) 0.0229(11) Uani 1 1 d . . . C13 C 1.1425(5) 0.6300(9) 0.5365(3) 0.0288(12) Uani 1 1 d . . . H13A H 1.1299 0.7388 0.4978 0.035 Uiso 1 1 calc R . . C14 C 1.0628(5) 0.6799(11) 0.5924(2) 0.0279(10) Uani 1 1 d . . . H14A H 0.9962 0.8240 0.5922 0.033 Uiso 1 1 calc R . . C15 C 0.5277(6) 0.7413(9) 0.6904(3) 0.0307(13) Uani 1 1 d . . . H15A H 0.4191 0.7704 0.6718 0.046 Uiso 1 1 calc R . . H15B H 0.5931 0.7162 0.6528 0.046 Uiso 1 1 calc R . . H15C H 0.5656 0.8887 0.7177 0.046 Uiso 1 1 calc R . . C16 C 1.3304(6) 0.3598(11) 0.4750(3) 0.0342(13) Uani 1 1 d . . . H16A H 1.3961 0.2093 0.4844 0.051 Uiso 1 1 calc R . . H16B H 1.3965 0.5050 0.4657 0.051 Uiso 1 1 calc R . . H16C H 1.2552 0.3277 0.4351 0.051 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 Br1 0.0314(3) 0.0553(3) 0.0306(3) -0.0169(3) 0.0022(2) -0.0045(3) S1 0.0275(7) 0.0441(9) 0.0312(8) -0.0128(6) 0.0078(6) -0.0129(6) N1 0.025(2) 0.0193(19) 0.021(2) -0.0027(16) 0.0037(18) -0.0057(17) O1 0.038(2) 0.047(2) 0.047(3) -0.0214(19) 0.0163(19) -0.0138(17) O2 0.033(2) 0.0183(19) 0.036(2) 0.0011(15) 0.0142(17) 0.0020(15) O3 0.031(2) 0.0173(15) 0.0272(19) 0.0003(14) 0.0140(16) -0.0002(14) C1 0.021(3) 0.027(3) 0.031(3) -0.002(2) 0.000(2) 0.000(2) C2 0.024(3) 0.027(3) 0.027(3) -0.006(2) 0.005(2) -0.006(2) C3 0.026(3) 0.015(2) 0.023(3) -0.0018(19) 0.006(2) -0.0028(19) C4 0.020(3) 0.022(3) 0.027(3) 0.002(2) -0.002(2) -0.003(2) C5 0.028(3) 0.021(3) 0.027(3) 0.003(2) 0.013(2) -0.005(2) C6 0.041(4) 0.030(3) 0.036(3) 0.001(3) 0.024(3) -0.002(2) C7 0.029(3) 0.032(3) 0.038(3) 0.008(2) 0.004(3) -0.004(2) C8 0.037(3) 0.027(3) 0.029(3) 0.002(2) -0.005(3) -0.001(2) C9 0.026(3) 0.028(3) 0.024(3) -0.005(2) 0.002(2) -0.009(2) C10 0.027(3) 0.027(3) 0.024(3) 0.005(2) 0.000(2) -0.006(2) C11 0.027(3) 0.028(3) 0.032(3) 0.000(2) 0.001(2) 0.001(2) C12 0.017(3) 0.027(2) 0.024(3) 0.001(2) -0.001(2) -0.003(2) C13 0.023(3) 0.035(3) 0.028(3) 0.007(2) 0.000(2) -0.007(2) C14 0.023(2) 0.026(2) 0.034(3) -0.007(3) 0.001(2) -0.005(3) C15 0.035(3) 0.032(3) 0.026(3) 0.007(2) 0.012(2) 0.003(2) C16 0.034(3) 0.035(3) 0.035(3) 0.002(2) 0.006(3) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.952(5) . ? S1 C1 1.771(5) . ? S1 C9 1.781(5) . ? N1 C4 1.359(6) . ? N1 C3 1.451(6) . ? N1 H1A 0.8799 . ? O1 C1 1.197(6) . ? O2 C4 1.224(6) . ? O3 C4 1.338(6) . ? O3 C5 1.472(5) . ? C1 C2 1.526(7) . ? C2 C3 1.534(7) . ? C2 H2A 1.0000 . ? C3 C15 1.516(6) . ? C3 H3A 1.0000 . ? C5 C8 1.512(7) . ? C5 C7 1.514(7) . ? C5 C6 1.526(7) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.385(7) . ? C9 C10 1.391(7) . ? C10 C11 1.390(7) . ? C10 H10A 0.9500 . ? C11 C12 1.381(7) . ? C11 H11A 0.9500 . ? C12 C13 1.414(7) . ? C12 C16 1.513(7) . ? C13 C14 1.375(6) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C1 S1 C9 100.9(2) . . ? C4 N1 C3 121.3(4) . . ? C4 N1 H1A 98.7 . . ? C3 N1 H1A 124.8 . . ? C4 O3 C5 120.3(4) . . ? O1 C1 C2 119.4(5) . . ? O1 C1 S1 124.0(4) . . ? C2 C1 S1 116.6(4) . . ? C1 C2 C3 111.4(4) . . ? C1 C2 Br1 113.7(3) . . ? C3 C2 Br1 110.3(3) . . ? C1 C2 H2A 107.0 . . ? C3 C2 H2A 107.0 . . ? Br1 C2 H2A 107.0 . . ? N1 C3 C15 108.6(4) . . ? N1 C3 C2 112.5(4) . . ? C15 C3 C2 113.7(4) . . ? N1 C3 H3A 107.2 . . ? C15 C3 H3A 107.2 . . ? C2 C3 H3A 107.2 . . ? O2 C4 O3 125.9(5) . . ? O2 C4 N1 123.4(5) . . ? O3 C4 N1 110.7(4) . . ? O3 C5 C8 110.7(4) . . ? O3 C5 C7 109.8(4) . . ? C8 C5 C7 113.0(4) . . ? O3 C5 C6 101.2(4) . . ? C8 C5 C6 110.6(4) . . ? C7 C5 C6 111.0(4) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 120.1(5) . . ? C14 C9 S1 119.7(4) . . ? C10 C9 S1 120.0(4) . . ? C11 C10 C9 119.0(5) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? C12 C11 C10 121.9(4) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C11 C12 C13 118.2(4) . . ? C11 C12 C16 121.1(4) . . ? C13 C12 C16 120.7(4) . . ? C14 C13 C12 120.3(5) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C9 120.6(5) . . ? C13 C14 H14A 119.7 . . ? C9 C14 H14A 119.7 . . ? C3 C15 H15A 109.5 . . ? C3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 H1A O2 0.88 2.46 3.080(5) 127.5 1_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.521 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.079 # Attachment 'Fig4.CIF' data_orj56m _database_code_depnum_ccdc_archive 'CCDC 653100' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O3 S' _chemical_formula_weight 251.29 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' 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 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 5.249(3) _cell_length_b 5.794(3) _cell_length_c 20.357(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.212(10) _cell_angle_gamma 90.00 _cell_volume 617.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1541 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 24.99 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8973 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details 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 smart1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6821 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.66 _reflns_number_total 2777 _reflns_number_gt 2263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker smart' _computing_cell_refinement 'Bruker smart' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0515P)^2^+0.5125P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(13) _chemical_absolute_configuration unk _refine_ls_number_reflns 2777 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.88103(17) 0.94450(15) 0.28891(5) 0.0264(2) Uani 1 1 d . . . N1 N 0.6784(7) 1.1608(5) 0.06584(16) 0.0273(8) Uani 1 1 d . . . H1A H 0.6225 1.1143 0.0262 0.033 Uiso 1 1 calc R . . O1 O 0.5291(6) 1.5353(5) 0.06025(14) 0.0336(7) Uani 1 1 d . . . O2 O 0.7495(5) 1.3968(4) 0.14970(12) 0.0238(6) Uani 1 1 d . . . O3 O 0.4637(5) 1.1114(5) 0.22411(13) 0.0273(6) Uani 1 1 d . . . C1 C 0.6402(8) 1.3749(6) 0.08827(19) 0.0235(8) Uani 1 1 d . . . C2 C 0.8517(7) 1.1797(6) 0.17306(18) 0.0201(8) Uani 1 1 d . . . H2 H 1.0353 1.1949 0.1894 0.024 Uiso 1 1 calc R . . C3 C 0.8199(7) 1.0136(6) 0.11278(18) 0.0238(8) Uani 1 1 d . . . H3 H 0.7120 0.8787 0.1237 0.029 Uiso 1 1 calc R . . C4 C 0.6910(7) 1.0896(6) 0.22723(18) 0.0212(8) Uani 1 1 d . . . C5 C 0.6394(7) 0.8080(7) 0.3319(2) 0.0244(8) Uani 1 1 d . . . C6 C 0.5293(8) 0.6053(7) 0.3054(2) 0.0284(9) Uani 1 1 d . . . H6 H 0.5773 0.5465 0.2645 0.034 Uiso 1 1 calc R . . C7 C 0.3482(8) 0.4915(6) 0.34007(19) 0.0274(9) Uani 1 1 d . . . H7 H 0.2698 0.3555 0.3220 0.033 Uiso 1 1 calc R . . C8 C 0.2802(7) 0.5713(7) 0.39984(19) 0.0260(9) Uani 1 1 d . . . C9 C 0.3914(8) 0.7738(7) 0.4254(2) 0.0305(10) Uani 1 1 d . . . H9 H 0.3449 0.8324 0.4665 0.037 Uiso 1 1 calc R . . C10 C 0.5709(8) 0.8899(7) 0.3906(2) 0.0295(9) Uani 1 1 d . . . H10 H 0.6462 1.0280 0.4081 0.035 Uiso 1 1 calc R . . C11 C 0.0854(7) 0.4400(8) 0.43636(19) 0.0309(9) Uani 1 1 d . . . H11A H -0.0870 0.4832 0.4189 0.046 Uiso 1 1 calc R . . H11B H 0.1069 0.4778 0.4834 0.046 Uiso 1 1 calc R . . H11C H 0.1100 0.2738 0.4304 0.046 Uiso 1 1 calc R . . C12 C 1.0686(8) 0.9295(12) 0.0895(3) 0.0612(17) Uani 1 1 d . . . H12A H 1.0348 0.8150 0.0545 0.092 Uiso 1 1 calc R . . H12B H 1.1707 0.8588 0.1264 0.092 Uiso 1 1 calc R . . H12C H 1.1625 1.0600 0.0724 0.092 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 0.0216(4) 0.0299(5) 0.0275(5) 0.0090(4) -0.0004(4) -0.0029(4) N1 0.042(2) 0.0207(17) 0.0179(17) -0.0020(13) -0.0068(15) 0.0038(15) O1 0.0514(19) 0.0240(15) 0.0237(15) 0.0029(12) -0.0085(14) 0.0049(14) O2 0.0384(15) 0.0138(14) 0.0183(13) 0.0006(10) -0.0039(11) 0.0027(11) O3 0.0201(14) 0.0349(16) 0.0271(15) -0.0002(12) 0.0024(12) 0.0040(12) C1 0.029(2) 0.0218(19) 0.019(2) -0.0008(14) -0.0035(16) -0.0017(15) C2 0.0229(19) 0.0179(18) 0.020(2) 0.0016(15) 0.0015(16) -0.0012(15) C3 0.0250(19) 0.022(2) 0.024(2) -0.0028(15) 0.0001(16) 0.0006(15) C4 0.027(2) 0.0201(18) 0.0167(19) -0.0035(14) 0.0020(15) -0.0024(15) C5 0.0226(19) 0.0213(19) 0.029(2) 0.0061(16) -0.0007(16) 0.0007(15) C6 0.038(2) 0.024(2) 0.025(2) 0.0049(16) 0.0111(18) -0.0021(18) C7 0.037(2) 0.019(2) 0.027(2) 0.0023(15) 0.0046(17) -0.0056(16) C8 0.0230(19) 0.026(2) 0.028(2) 0.0065(17) 0.0000(16) 0.0012(16) C9 0.035(2) 0.031(2) 0.026(2) -0.0008(17) 0.0047(19) -0.0021(19) C10 0.032(2) 0.028(2) 0.028(2) -0.0012(16) 0.0007(17) -0.0062(17) C11 0.0314(19) 0.033(2) 0.029(2) 0.004(2) 0.0075(16) -0.005(2) C12 0.034(2) 0.094(4) 0.054(3) -0.044(4) -0.003(2) 0.024(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 C4 1.759(4) . ? S1 C5 1.779(4) . ? N1 C1 1.342(5) . ? N1 C3 1.445(5) . ? N1 H1A 0.8800 . ? O1 C1 1.217(5) . ? O2 C1 1.343(5) . ? O2 C2 1.435(4) . ? O3 C4 1.197(4) . ? C2 C4 1.529(5) . ? C2 C3 1.559(5) . ? C2 H2 1.0000 . ? C3 C12 1.502(5) . ? C3 H3 1.0000 . ? C5 C10 1.358(5) . ? C5 C6 1.400(6) . ? C6 C7 1.392(5) . ? C6 H6 0.9500 . ? C7 C8 1.373(5) . ? C7 H7 0.9500 . ? C8 C9 1.394(6) . ? C8 C11 1.513(5) . ? C9 C10 1.393(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C5 100.14(18) . . ? C1 N1 C3 113.8(3) . . ? C1 N1 H1A 123.1 . . ? C3 N1 H1A 123.1 . . ? C1 O2 C2 110.5(3) . . ? O1 C1 N1 128.7(4) . . ? O1 C1 O2 121.5(3) . . ? N1 C1 O2 109.9(3) . . ? O2 C2 C4 109.0(3) . . ? O2 C2 C3 105.3(3) . . ? C4 C2 C3 108.9(3) . . ? O2 C2 H2 111.1 . . ? C4 C2 H2 111.1 . . ? C3 C2 H2 111.1 . . ? N1 C3 C12 113.5(4) . . ? N1 C3 C2 100.2(3) . . ? C12 C3 C2 113.8(3) . . ? N1 C3 H3 109.7 . . ? C12 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? O3 C4 C2 121.8(3) . . ? O3 C4 S1 126.8(3) . . ? C2 C4 S1 111.3(3) . . ? C10 C5 C6 120.3(4) . . ? C10 C5 S1 121.5(3) . . ? C6 C5 S1 118.2(3) . . ? C7 C6 C5 118.6(4) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 119.1(4) . . ? C7 C8 C11 119.7(4) . . ? C9 C8 C11 121.3(4) . . ? C10 C9 C8 119.7(4) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C5 C10 C9 120.8(4) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.462 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.072