# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_gt225_0m _database_code_depnum_ccdc_archive 'CCDC 930418' #TrackingRef '18727_web_deposit_cif_file_0_guo,tao_1363850088.3o_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Br N O3 S' _chemical_formula_weight 464.41 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 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 10.6632(13) _cell_length_b 11.2585(14) _cell_length_c 19.059(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2288.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3134 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 24.98 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6568 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11804 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.51 _reflns_number_total 4255 _reflns_number_gt 3302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0000P)^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 SHELXL _refine_ls_extinction_coef 0.0037(5) _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 0.007(8) _chemical_absolute_configuration rm _refine_ls_number_reflns 4255 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 0.05862(5) 0.80531(3) 0.82947(2) 0.08905(18) Uani 1 1 d . . . S1 S 0.27634(7) 0.08408(6) 0.86425(4) 0.04303(18) Uani 1 1 d . . . O2 O 0.1189(2) 0.12548(15) 0.99278(10) 0.0515(5) Uani 1 1 d . . . C16 C 0.0418(3) 0.0797(2) 1.04110(13) 0.0411(6) Uani 1 1 d . . . C13 C 0.1135(3) 0.2539(2) 0.98037(14) 0.0415(6) Uani 1 1 d . . . H13 H 0.0334 0.2851 0.9975 0.050 Uiso 1 1 calc R . . C4 C 0.1049(3) 0.4009(2) 0.88117(13) 0.0416(7) Uani 1 1 d . . . O3 O -0.0268(2) 0.13976(18) 1.07660(11) 0.0602(6) Uani 1 1 d . . . O1 O 0.3729(2) 0.05296(18) 0.91730(10) 0.0566(5) Uani 1 1 d . . . N1 N 0.2415(2) 0.22757(17) 0.87138(11) 0.0409(5) Uani 1 1 d . . . H1 H 0.2959 0.2794 0.8582 0.049 Uiso 1 1 calc R . . C14 C 0.2179(3) 0.3102(3) 1.01954(14) 0.0494(7) Uani 1 1 d . . . H14 H 0.2992 0.2839 1.0112 0.059 Uiso 1 1 calc R . . C1 C 0.0746(3) 0.6402(3) 0.84788(16) 0.0560(8) Uani 1 1 d . . . C17 C 0.0513(3) -0.0505(2) 1.04605(12) 0.0421(7) Uani 1 1 d . . . C8 C 0.0122(3) 0.2004(3) 0.86489(16) 0.0525(7) Uani 1 1 d . . . H8A H 0.0164 0.2102 0.8149 0.079 Uiso 1 1 calc R . . H8B H -0.0663 0.2308 0.8818 0.079 Uiso 1 1 calc R . . H8C H 0.0188 0.1176 0.8763 0.079 Uiso 1 1 calc R . . C22 C -0.0488(3) -0.1102(3) 1.07647(15) 0.0548(8) Uani 1 1 d . . . H22 H -0.1179 -0.0678 1.0925 0.066 Uiso 1 1 calc R . . C20 C 0.0555(5) -0.2935(3) 1.06016(17) 0.0736(11) Uani 1 1 d . . . H20 H 0.0578 -0.3756 1.0652 0.088 Uiso 1 1 calc R . . C3 C 0.1770(3) 0.4549(2) 0.82952(17) 0.0569(8) Uani 1 1 d . . . H3 H 0.2364 0.4103 0.8054 0.068 Uiso 1 1 calc R . . C5 C 0.0147(3) 0.4702(3) 0.91367(16) 0.0559(8) Uani 1 1 d . . . H5 H -0.0371 0.4358 0.9473 0.067 Uiso 1 1 calc R . . C9 C 0.3596(3) 0.0890(3) 0.77927(14) 0.0505(8) Uani 1 1 d . . . C6 C -0.0006(3) 0.5890(3) 0.89764(16) 0.0609(9) Uani 1 1 d . . . H6 H -0.0614 0.6338 0.9205 0.073 Uiso 1 1 calc R . . C7 C 0.1206(3) 0.2687(2) 0.89950(13) 0.0381(6) Uani 1 1 d . . . C19 C 0.1559(4) -0.2350(3) 1.02940(18) 0.0741(11) Uani 1 1 d . . . H19 H 0.2251 -0.2782 1.0141 0.089 Uiso 1 1 calc R . . C11 C 0.2627(4) 0.1163(4) 0.72365(16) 0.0832(12) Uani 1 1 d . . . H11A H 0.2301 0.1949 0.7309 0.125 Uiso 1 1 calc R . . H11B H 0.1955 0.0597 0.7266 0.125 Uiso 1 1 calc R . . H11C H 0.3008 0.1117 0.6781 0.125 Uiso 1 1 calc R . . C2 C 0.1621(3) 0.5740(3) 0.81329(17) 0.0625(9) Uani 1 1 d . . . H2 H 0.2117 0.6088 0.7788 0.075 Uiso 1 1 calc R . . C18 C 0.1542(3) -0.1133(2) 1.02126(15) 0.0518(8) Uani 1 1 d . . . H18 H 0.2205 -0.0741 0.9996 0.062 Uiso 1 1 calc R . . C12 C 0.4131(4) -0.0362(3) 0.76919(18) 0.0808(12) Uani 1 1 d . . . H12A H 0.4476 -0.0431 0.7229 0.121 Uiso 1 1 calc R . . H12B H 0.3474 -0.0936 0.7751 0.121 Uiso 1 1 calc R . . H12C H 0.4777 -0.0501 0.8032 0.121 Uiso 1 1 calc R . . C21 C -0.0462(4) -0.2317(3) 1.08302(17) 0.0668(9) Uani 1 1 d . . . H21 H -0.1137 -0.2716 1.1030 0.080 Uiso 1 1 calc R . . C15 C 0.2008(4) 0.3943(3) 1.06469(19) 0.0758(11) Uani 1 1 d . . . H15A H 0.1203 0.4220 1.0738 0.091 Uiso 1 1 calc R . . H15B H 0.2691 0.4271 1.0881 0.091 Uiso 1 1 calc R . . C10 C 0.4651(4) 0.1785(3) 0.78031(18) 0.0762(10) Uani 1 1 d . . . H10A H 0.5127 0.1722 0.7377 0.114 Uiso 1 1 calc R . . H10B H 0.5187 0.1632 0.8198 0.114 Uiso 1 1 calc R . . H10C H 0.4308 0.2571 0.7841 0.114 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 0.1383(4) 0.03804(18) 0.0908(3) 0.00917(18) -0.0272(3) 0.0005(2) S1 0.0515(4) 0.0337(4) 0.0439(4) 0.0024(3) 0.0064(3) 0.0002(3) O2 0.0660(13) 0.0340(10) 0.0544(11) 0.0094(9) 0.0206(11) 0.0059(9) C16 0.0441(16) 0.0429(15) 0.0362(13) 0.0066(12) -0.0001(13) 0.0019(15) C13 0.0484(17) 0.0324(14) 0.0438(15) 0.0050(12) 0.0038(14) 0.0042(12) C4 0.0443(16) 0.0387(15) 0.0419(15) 0.0058(12) -0.0058(13) -0.0028(13) O3 0.0647(14) 0.0486(12) 0.0673(12) 0.0099(10) 0.0256(12) 0.0134(11) O1 0.0639(14) 0.0561(13) 0.0499(11) 0.0118(10) 0.0021(11) 0.0132(11) N1 0.0445(13) 0.0313(12) 0.0469(12) 0.0055(10) 0.0102(12) -0.0033(10) C14 0.0513(17) 0.0497(17) 0.0473(15) 0.0001(16) -0.0049(15) 0.0045(16) C1 0.075(2) 0.0383(15) 0.0546(18) 0.0064(14) -0.0191(18) -0.0027(16) C17 0.0552(19) 0.0402(15) 0.0308(13) 0.0027(11) -0.0012(14) -0.0010(14) C8 0.0478(16) 0.0514(17) 0.0584(17) -0.0026(15) -0.0029(15) -0.0097(14) C22 0.060(2) 0.0540(18) 0.0508(16) 0.0107(14) 0.0037(17) -0.0033(16) C20 0.124(3) 0.0350(17) 0.062(2) 0.0042(15) 0.001(2) -0.011(2) C3 0.0591(19) 0.0493(18) 0.0623(18) 0.0140(17) 0.0076(18) 0.0033(15) C5 0.067(2) 0.0467(17) 0.0538(18) 0.0086(15) 0.0030(16) 0.0093(15) C9 0.062(2) 0.0426(16) 0.0465(16) 0.0005(14) 0.0082(15) 0.0064(15) C6 0.075(2) 0.0506(19) 0.0571(19) 0.0001(16) -0.0063(18) 0.0166(17) C7 0.0405(15) 0.0332(14) 0.0407(14) 0.0000(12) 0.0032(13) -0.0003(12) C19 0.109(3) 0.0455(19) 0.068(2) -0.0024(17) 0.011(2) 0.018(2) C11 0.099(3) 0.108(3) 0.0430(17) -0.003(2) -0.004(2) 0.017(2) C2 0.065(2) 0.054(2) 0.069(2) 0.0205(17) 0.0034(18) -0.0075(17) C18 0.065(2) 0.0412(16) 0.0495(16) 0.0015(14) 0.0073(17) 0.0071(15) C12 0.106(3) 0.061(2) 0.076(2) -0.0066(18) 0.034(2) 0.017(2) C21 0.089(3) 0.053(2) 0.0585(19) 0.0101(16) -0.002(2) -0.021(2) C15 0.077(3) 0.067(2) 0.083(2) -0.015(2) -0.022(2) 0.014(2) C10 0.083(2) 0.078(2) 0.068(2) 0.0051(19) 0.032(2) -0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.900(3) . ? S1 O1 1.485(2) . ? S1 N1 1.663(2) . ? S1 C9 1.848(3) . ? O2 C16 1.338(3) . ? O2 C13 1.466(3) . ? C16 O3 1.204(3) . ? C16 C17 1.473(4) . ? C13 C14 1.482(4) . ? C13 C7 1.552(4) . ? C13 H13 0.9800 . ? C4 C5 1.385(4) . ? C4 C3 1.389(4) . ? C4 C7 1.537(4) . ? N1 C7 1.471(3) . ? N1 H1 0.8600 . ? C14 C15 1.292(4) . ? C14 H14 0.9300 . ? C1 C2 1.364(4) . ? C1 C6 1.369(4) . ? C17 C18 1.387(4) . ? C17 C22 1.388(4) . ? C8 C7 1.537(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C22 C21 1.374(4) . ? C22 H22 0.9300 . ? C20 C21 1.360(5) . ? C20 C19 1.387(5) . ? C20 H20 0.9300 . ? C3 C2 1.385(4) . ? C3 H3 0.9300 . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C9 C10 1.510(4) . ? C9 C11 1.512(5) . ? C9 C12 1.532(4) . ? C6 H6 0.9300 . ? C19 C18 1.379(4) . ? C19 H19 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C2 H2 0.9300 . ? C18 H18 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C21 H21 0.9300 . ? C15 H15A 0.9300 . ? C15 H15B 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 109.18(12) . . ? O1 S1 C9 105.68(13) . . ? N1 S1 C9 98.63(12) . . ? C16 O2 C13 117.8(2) . . ? O3 C16 O2 122.9(2) . . ? O3 C16 C17 124.4(3) . . ? O2 C16 C17 112.7(2) . . ? O2 C13 C14 108.1(2) . . ? O2 C13 C7 105.3(2) . . ? C14 C13 C7 114.7(2) . . ? O2 C13 H13 109.5 . . ? C14 C13 H13 109.5 . . ? C7 C13 H13 109.5 . . ? C5 C4 C3 117.0(3) . . ? C5 C4 C7 121.3(2) . . ? C3 C4 C7 121.6(3) . . ? C7 N1 S1 122.12(16) . . ? C7 N1 H1 118.9 . . ? S1 N1 H1 118.9 . . ? C15 C14 C13 122.9(3) . . ? C15 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C2 C1 C6 120.4(3) . . ? C2 C1 Br1 120.4(2) . . ? C6 C1 Br1 119.2(3) . . ? C18 C17 C22 120.2(3) . . ? C18 C17 C16 122.7(3) . . ? C22 C17 C16 117.1(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C21 C22 C17 120.3(4) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? C21 C20 C19 120.5(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C6 C5 C4 121.9(3) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C10 C9 C11 112.5(3) . . ? C10 C9 C12 109.8(3) . . ? C11 C9 C12 110.7(3) . . ? C10 C9 S1 111.5(2) . . ? C11 C9 S1 107.0(2) . . ? C12 C9 S1 105.2(2) . . ? C1 C6 C5 119.5(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N1 C7 C8 110.2(2) . . ? N1 C7 C4 108.5(2) . . ? C8 C7 C4 107.8(2) . . ? N1 C7 C13 111.7(2) . . ? C8 C7 C13 109.6(2) . . ? C4 C7 C13 108.9(2) . . ? C18 C19 C20 120.6(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C19 C18 C17 118.6(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C20 C21 C22 119.8(4) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 C13 O2 C16 O3 -3.5(4) . . . . ? C13 O2 C16 C17 177.0(2) . . . . ? C16 O2 C13 C14 99.2(3) . . . . ? C16 O2 C13 C7 -137.8(2) . . . . ? O1 S1 N1 C7 -108.9(2) . . . . ? C9 S1 N1 C7 141.1(2) . . . . ? O2 C13 C14 C15 -124.5(3) . . . . ? C7 C13 C14 C15 118.4(3) . . . . ? O3 C16 C17 C18 -159.9(3) . . . . ? O2 C16 C17 C18 19.6(4) . . . . ? O3 C16 C17 C22 20.6(4) . . . . ? O2 C16 C17 C22 -159.8(2) . . . . ? C18 C17 C22 C21 0.8(4) . . . . ? C16 C17 C22 C21 -179.8(3) . . . . ? C5 C4 C3 C2 2.3(4) . . . . ? C7 C4 C3 C2 179.9(3) . . . . ? C3 C4 C5 C6 -2.3(4) . . . . ? C7 C4 C5 C6 -179.9(3) . . . . ? O1 S1 C9 C10 -58.6(3) . . . . ? N1 S1 C9 C10 54.2(2) . . . . ? O1 S1 C9 C11 178.1(2) . . . . ? N1 S1 C9 C11 -69.1(2) . . . . ? O1 S1 C9 C12 60.3(3) . . . . ? N1 S1 C9 C12 173.1(2) . . . . ? C2 C1 C6 C5 1.4(5) . . . . ? Br1 C1 C6 C5 -176.9(2) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? S1 N1 C7 C8 -47.6(3) . . . . ? S1 N1 C7 C4 -165.31(17) . . . . ? S1 N1 C7 C13 74.6(3) . . . . ? C5 C4 C7 N1 -165.4(2) . . . . ? C3 C4 C7 N1 17.1(3) . . . . ? C5 C4 C7 C8 75.3(3) . . . . ? C3 C4 C7 C8 -102.2(3) . . . . ? C5 C4 C7 C13 -43.6(3) . . . . ? C3 C4 C7 C13 139.0(3) . . . . ? O2 C13 C7 N1 -64.6(3) . . . . ? C14 C13 C7 N1 54.1(3) . . . . ? O2 C13 C7 C8 57.8(3) . . . . ? C14 C13 C7 C8 176.6(2) . . . . ? O2 C13 C7 C4 175.5(2) . . . . ? C14 C13 C7 C4 -65.7(3) . . . . ? C21 C20 C19 C18 -0.2(5) . . . . ? C6 C1 C2 C3 -1.4(5) . . . . ? Br1 C1 C2 C3 176.9(2) . . . . ? C4 C3 C2 C1 -0.6(5) . . . . ? C20 C19 C18 C17 1.6(5) . . . . ? C22 C17 C18 C19 -1.8(4) . . . . ? C16 C17 C18 C19 178.8(3) . . . . ? C19 C20 C21 C22 -0.9(5) . . . . ? C17 C22 C21 C20 0.6(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.218 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.036 data_gt8_0m _database_code_depnum_ccdc_archive 'CCDC 930419' #TrackingRef '18728_web_deposit_cif_file_1_guo,tao_1363850088.3a_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H27 N O3 S' _chemical_formula_weight 301.44 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 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 6.2080(9) _cell_length_b 14.513(2) _cell_length_c 19.432(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1750.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1244 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 18.02 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6757 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9086 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3250 _reflns_number_gt 2222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0303P)^2^+0.2986P] 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 _chemical_absolute_configuration rm _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(12) _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 -0.04(11) _refine_ls_number_reflns 3250 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.42421(14) 0.00561(5) 0.89751(4) 0.0437(2) Uani 1 1 d . . . O1 O 0.3222(4) 0.04784(13) 0.96063(10) 0.0521(6) Uani 1 1 d . . . C7 C 0.5926(5) 0.14035(19) 0.81888(13) 0.0374(7) Uani 1 1 d . . . N1 N 0.6315(4) 0.06740(15) 0.87145(11) 0.0406(6) Uani 1 1 d . . . H1 H 0.7584 0.0578 0.8877 0.049 Uiso 1 1 calc R . . C6 C 0.5123(5) 0.09487(19) 0.75237(15) 0.0410(8) Uani 1 1 d . . . C12 C 0.5657(7) -0.0965(2) 0.93124(15) 0.0514(8) Uani 1 1 d . . . C1 C 0.6315(6) 0.0246(2) 0.72289(15) 0.0582(10) Uani 1 1 d . . . H1A H 0.7547 0.0034 0.7451 0.070 Uiso 1 1 calc R . . C5 C 0.3303(6) 0.1246(2) 0.71844(16) 0.0529(9) Uani 1 1 d . . . H5 H 0.2488 0.1723 0.7370 0.064 Uiso 1 1 calc R . . C8 C 0.4383(6) 0.2135(2) 0.84689(14) 0.0502(8) Uani 1 1 d . . . H8A H 0.2998 0.1862 0.8551 0.075 Uiso 1 1 calc R . . H8B H 0.4242 0.2624 0.8140 0.075 Uiso 1 1 calc R . . H8C H 0.4942 0.2377 0.8892 0.075 Uiso 1 1 calc R . . C13 C 0.3836(7) -0.1597(2) 0.95596(19) 0.0773(12) Uani 1 1 d . . . H13A H 0.4437 -0.2161 0.9733 0.116 Uiso 1 1 calc R . . H13B H 0.2889 -0.1731 0.9182 0.116 Uiso 1 1 calc R . . H13C H 0.3042 -0.1295 0.9919 0.116 Uiso 1 1 calc R . . C9 C 0.8163(5) 0.1837(2) 0.80602(16) 0.0489(8) Uani 1 1 d . . . H9A H 0.8673 0.2110 0.8486 0.059 Uiso 1 1 calc R . . H9B H 0.9163 0.1353 0.7933 0.059 Uiso 1 1 calc R . . C10 C 0.8176(6) 0.2561(2) 0.75091(17) 0.0583(10) Uani 1 1 d . . . H10 H 0.7785 0.2385 0.7066 0.070 Uiso 1 1 calc R . . C2 C 0.5706(9) -0.0146(3) 0.66096(17) 0.0768(12) Uani 1 1 d . . . H2 H 0.6541 -0.0610 0.6415 0.092 Uiso 1 1 calc R . . C14 C 0.7103(6) -0.0707(2) 0.99070(18) 0.0705(11) Uani 1 1 d . . . H14A H 0.7651 -0.1257 1.0119 0.106 Uiso 1 1 calc R . . H14B H 0.6294 -0.0360 1.0239 0.106 Uiso 1 1 calc R . . H14C H 0.8282 -0.0342 0.9741 0.106 Uiso 1 1 calc R . . C15 C 0.6887(8) -0.1403(2) 0.8724(2) 0.0881(14) Uani 1 1 d . . . H15A H 0.8087 -0.1019 0.8603 0.132 Uiso 1 1 calc R . . H15B H 0.5952 -0.1469 0.8334 0.132 Uiso 1 1 calc R . . H15C H 0.7402 -0.1998 0.8863 0.132 Uiso 1 1 calc R . . C4 C 0.2671(7) 0.0841(3) 0.65686(18) 0.0775(13) Uani 1 1 d . . . H4 H 0.1425 0.1041 0.6349 0.093 Uiso 1 1 calc R . . C3 C 0.3871(9) 0.0150(3) 0.62831(19) 0.0836(14) Uani 1 1 d . . . H3 H 0.3447 -0.0118 0.5870 0.100 Uiso 1 1 calc R . . O2 O 0.9457(5) 0.1498(2) 0.97844(14) 0.0621(7) Uani 1 1 d . . . O3 O 0.5537(6) 0.16824(18) 0.05021(14) 0.0644(7) Uani 1 1 d . . . C11 C 0.8694(7) 0.3410(3) 0.7608(2) 0.0788(13) Uani 1 1 d . . . H11A H 0.9093 0.3610 0.8044 0.095 Uiso 1 1 calc R . . H11B H 0.8668 0.3824 0.7242 0.095 Uiso 1 1 calc R . . H3A H 0.470(8) 0.128(3) 0.021(2) 0.109(17) Uiso 1 1 d . . . H3B H 0.685(7) 0.162(2) 0.0375(18) 0.070(14) Uiso 1 1 d . . . H2A H 1.036(6) 0.116(2) 0.9680(16) 0.049(12) Uiso 1 1 d . . . H2B H 0.982(6) 0.203(2) 0.9761(19) 0.082(16) 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 0.0427(4) 0.0462(4) 0.0422(4) 0.0002(4) 0.0016(4) -0.0048(5) O1 0.0507(14) 0.0530(12) 0.0525(13) -0.0011(11) 0.0142(12) 0.0030(12) C7 0.0360(18) 0.0396(15) 0.0364(15) 0.0023(12) 0.0000(15) 0.0037(16) N1 0.0311(15) 0.0476(14) 0.0432(14) 0.0103(11) 0.0021(12) 0.0031(12) C6 0.044(2) 0.0420(16) 0.0371(16) 0.0027(14) 0.0041(15) -0.0043(15) C12 0.066(2) 0.0384(16) 0.0494(18) -0.0002(14) 0.005(2) -0.0021(19) C1 0.074(3) 0.055(2) 0.0456(18) -0.0021(15) 0.0089(18) 0.0087(19) C5 0.048(2) 0.066(2) 0.0451(19) 0.0035(17) -0.0013(18) -0.0025(19) C8 0.055(2) 0.0501(17) 0.0458(18) -0.0023(14) 0.0027(19) 0.0124(19) C13 0.092(3) 0.053(2) 0.087(3) 0.0121(19) 0.007(3) -0.022(2) C9 0.0411(19) 0.055(2) 0.0507(19) 0.0081(16) 0.0023(17) -0.0062(18) C10 0.052(2) 0.068(2) 0.055(2) 0.0103(19) 0.0041(19) -0.009(2) C2 0.124(4) 0.061(2) 0.046(2) -0.0067(18) 0.017(3) -0.007(3) C14 0.083(3) 0.055(2) 0.074(3) 0.0146(19) -0.010(2) 0.011(2) C15 0.116(4) 0.056(2) 0.092(3) -0.008(2) 0.021(3) 0.024(2) C4 0.075(3) 0.108(3) 0.049(2) 0.010(2) -0.015(2) -0.023(3) C3 0.120(4) 0.088(3) 0.044(2) -0.011(2) -0.001(3) -0.030(3) O2 0.0540(18) 0.0555(17) 0.0768(18) -0.0018(15) 0.0015(16) 0.0058(18) O3 0.0597(19) 0.0631(16) 0.0702(17) -0.0126(13) 0.0079(17) 0.0024(16) C11 0.078(3) 0.072(3) 0.086(3) 0.016(2) 0.011(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.510(2) . ? S1 N1 1.648(2) . ? S1 C12 1.843(3) . ? C7 N1 1.491(3) . ? C7 C8 1.529(4) . ? C7 C6 1.534(4) . ? C7 C9 1.545(4) . ? N1 H1 0.8600 . ? C6 C5 1.377(4) . ? C6 C1 1.384(4) . ? C12 C14 1.510(5) . ? C12 C15 1.514(5) . ? C12 C13 1.533(5) . ? C1 C2 1.384(5) . ? C1 H1A 0.9300 . ? C5 C4 1.390(4) . ? C5 H5 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C9 C10 1.500(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.288(4) . ? C10 H10 0.9300 . ? C2 C3 1.373(6) . ? C2 H2 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C4 C3 1.367(5) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? O2 H2A 0.78(3) . ? O2 H2B 0.80(3) . ? O3 H3A 0.97(5) . ? O3 H3B 0.85(4) . ? C11 H11A 0.9300 . ? C11 H11B 0.9300 . ? 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 N1 110.86(12) . . ? O1 S1 C12 103.73(13) . . ? N1 S1 C12 100.06(15) . . ? N1 C7 C8 110.5(2) . . ? N1 C7 C6 108.9(2) . . ? C8 C7 C6 113.2(3) . . ? N1 C7 C9 104.8(2) . . ? C8 C7 C9 109.7(2) . . ? C6 C7 C9 109.3(2) . . ? C7 N1 S1 118.1(2) . . ? C7 N1 H1 121.0 . . ? S1 N1 H1 121.0 . . ? C5 C6 C1 118.1(3) . . ? C5 C6 C7 122.3(3) . . ? C1 C6 C7 119.4(3) . . ? C14 C12 C15 112.4(4) . . ? C14 C12 C13 110.3(3) . . ? C15 C12 C13 110.9(3) . . ? C14 C12 S1 110.9(2) . . ? C15 C12 S1 108.0(2) . . ? C13 C12 S1 103.9(3) . . ? C6 C1 C2 121.1(4) . . ? C6 C1 H1A 119.4 . . ? C2 C1 H1A 119.4 . . ? C6 C5 C4 120.7(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C9 C7 114.0(3) . . ? C10 C9 H9A 108.8 . . ? C7 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C7 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 124.4(4) . . ? C11 C10 H10 117.8 . . ? C9 C10 H10 117.8 . . ? C3 C2 C1 120.0(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? H2A O2 H2B 113(4) . . ? H3A O3 H3B 106(3) . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? 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 C8 C7 N1 S1 62.2(3) . . . . ? C6 C7 N1 S1 -62.8(3) . . . . ? C9 C7 N1 S1 -179.70(19) . . . . ? O1 S1 N1 C7 -92.3(2) . . . . ? C12 S1 N1 C7 158.72(19) . . . . ? N1 C7 C6 C5 129.6(3) . . . . ? C8 C7 C6 C5 6.2(4) . . . . ? C9 C7 C6 C5 -116.4(3) . . . . ? N1 C7 C6 C1 -53.9(4) . . . . ? C8 C7 C6 C1 -177.3(3) . . . . ? C9 C7 C6 C1 60.0(3) . . . . ? O1 S1 C12 C14 -52.1(3) . . . . ? N1 S1 C12 C14 62.4(3) . . . . ? O1 S1 C12 C15 -175.7(3) . . . . ? N1 S1 C12 C15 -61.2(3) . . . . ? O1 S1 C12 C13 66.4(2) . . . . ? N1 S1 C12 C13 -179.1(2) . . . . ? C5 C6 C1 C2 0.2(5) . . . . ? C7 C6 C1 C2 -176.4(3) . . . . ? C1 C6 C5 C4 0.9(5) . . . . ? C7 C6 C5 C4 177.4(3) . . . . ? N1 C7 C9 C10 176.5(2) . . . . ? C8 C7 C9 C10 -64.9(3) . . . . ? C6 C7 C9 C10 59.9(3) . . . . ? C7 C9 C10 C11 118.6(4) . . . . ? C6 C1 C2 C3 -1.1(5) . . . . ? C6 C5 C4 C3 -1.1(5) . . . . ? C5 C4 C3 C2 0.2(6) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.187 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.038 data_gt262_0m _database_code_depnum_ccdc_archive 'CCDC 930420' #TrackingRef '18729_web_deposit_cif_file_2_guo,tao_1363850088.3p_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H29 N O3 S' _chemical_formula_weight 351.49 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 9.2088(19) _cell_length_b 10.632(2) _cell_length_c 10.884(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.969(2) _cell_angle_gamma 90.00 _cell_volume 1007.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2357 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.37 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6837 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5155 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.51 _reflns_number_total 3380 _reflns_number_gt 3036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0401P)^2^+0.2920P] 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 0.031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _chemical_absolute_configuration rm _refine_ls_number_reflns 3380 _refine_ls_number_parameters 224 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.099 _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 -0.02705(7) 0.16656(7) 0.79175(6) 0.0488(2) Uani 1 1 d . . . O2 O 0.1072(2) 0.34962(19) 0.64944(18) 0.0523(5) Uani 1 1 d . . . N1 N -0.1563(2) 0.1955(2) 0.6481(2) 0.0433(6) Uani 1 1 d . . . H1 H -0.2206 0.1373 0.6115 0.052 Uiso 1 1 calc R . . C11 C -0.1654(3) 0.3167(3) 0.5806(2) 0.0411(6) Uani 1 1 d . . . C7 C 0.2249(3) 0.4204(3) 0.6421(3) 0.0438(6) Uani 1 1 d . . . O1 O 0.0910(2) 0.0786(2) 0.7761(2) 0.0699(7) Uani 1 1 d . . . C6 C 0.3514(3) 0.4267(3) 0.7685(3) 0.0456(6) Uani 1 1 d . . . O3 O 0.2252(2) 0.4738(2) 0.5458(2) 0.0596(6) Uani 1 1 d . . . C13 C -0.3146(3) 0.3105(3) 0.4604(3) 0.0485(7) Uani 1 1 d . . . H13 H -0.2998 0.2429 0.4044 0.058 Uiso 1 1 calc R . . C8 C -0.0270(3) 0.3375(3) 0.5325(2) 0.0440(6) Uani 1 1 d . . . H8 H -0.0414 0.4158 0.4825 0.053 Uiso 1 1 calc R . . C16 C -0.1459(3) 0.0718(3) 0.8656(3) 0.0545(8) Uani 1 1 d . . . C1 C 0.3608(3) 0.3473(3) 0.8705(3) 0.0576(8) Uani 1 1 d . . . H1A H 0.2869 0.2852 0.8616 0.069 Uiso 1 1 calc R . . C9 C 0.0007(3) 0.2319(3) 0.4523(3) 0.0535(7) Uani 1 1 d . . . H9 H 0.0436 0.1580 0.4944 0.064 Uiso 1 1 calc R . . C5 C 0.4645(3) 0.5173(3) 0.7823(3) 0.0590(8) Uani 1 1 d . . . H5 H 0.4601 0.5700 0.7129 0.071 Uiso 1 1 calc R . . C4 C 0.5823(4) 0.5295(4) 0.8971(4) 0.0662(9) Uani 1 1 d . . . H4 H 0.6574 0.5904 0.9053 0.079 Uiso 1 1 calc R . . C3 C 0.5901(4) 0.4519(4) 1.0007(3) 0.0664(9) Uani 1 1 d . . . H3 H 0.6688 0.4619 1.0793 0.080 Uiso 1 1 calc R . . C12 C -0.1744(4) 0.4240(3) 0.6723(3) 0.0580(8) Uani 1 1 d . . . H12A H -0.2635 0.4129 0.6986 0.087 Uiso 1 1 calc R . . H12B H -0.1814 0.5031 0.6281 0.087 Uiso 1 1 calc R . . H12C H -0.0840 0.4233 0.7476 0.087 Uiso 1 1 calc R . . C15 C -0.4571(3) 0.2770(4) 0.4955(4) 0.0730(10) Uani 1 1 d . . . H15A H -0.4806 0.3444 0.5446 0.110 Uiso 1 1 calc R . . H15B H -0.4383 0.2014 0.5465 0.110 Uiso 1 1 calc R . . H15C H -0.5421 0.2640 0.4174 0.110 Uiso 1 1 calc R . . C2 C 0.4812(4) 0.3598(4) 0.9874(4) 0.0701(10) Uani 1 1 d . . . H2 H 0.4878 0.3058 1.0562 0.084 Uiso 1 1 calc R . . C14 C -0.3444(4) 0.4314(4) 0.3789(3) 0.0719(10) Uani 1 1 d . . . H14A H -0.4338 0.4205 0.3038 0.108 Uiso 1 1 calc R . . H14B H -0.2572 0.4493 0.3518 0.108 Uiso 1 1 calc R . . H14C H -0.3608 0.5001 0.4302 0.108 Uiso 1 1 calc R . . C17 C -0.0338(5) 0.0292(5) 0.9965(4) 0.0958(15) Uani 1 1 d . . . H17A H 0.0126 0.1016 1.0467 0.144 Uiso 1 1 calc R . . H17B H 0.0446 -0.0226 0.9822 0.144 Uiso 1 1 calc R . . H17C H -0.0883 -0.0181 1.0427 0.144 Uiso 1 1 calc R . . C19 C -0.2658(5) 0.1569(5) 0.8844(4) 0.0945(13) Uani 1 1 d . . . H19A H -0.3468 0.1676 0.8032 0.142 Uiso 1 1 calc R . . H19B H -0.2210 0.2373 0.9151 0.142 Uiso 1 1 calc R . . H19C H -0.3068 0.1208 0.9470 0.142 Uiso 1 1 calc R . . C10 C -0.0321(4) 0.2377(4) 0.3259(3) 0.0745(10) Uani 1 1 d . . . H10A H -0.0751 0.3105 0.2814 0.089 Uiso 1 1 calc R . . H10B H -0.0125 0.1691 0.2807 0.089 Uiso 1 1 calc R . . C18 C -0.2143(4) -0.0396(4) 0.7827(4) 0.0763(10) Uani 1 1 d . . . H18A H -0.2724 -0.0885 0.8245 0.114 Uiso 1 1 calc R . . H18B H -0.1337 -0.0904 0.7709 0.114 Uiso 1 1 calc R . . H18C H -0.2806 -0.0113 0.6997 0.114 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 0.0388(3) 0.0631(5) 0.0378(3) 0.0049(3) 0.0034(2) -0.0041(3) O2 0.0387(10) 0.0669(14) 0.0426(11) 0.0096(9) 0.0012(8) -0.0086(9) N1 0.0360(11) 0.0497(15) 0.0379(12) -0.0016(9) 0.0033(9) -0.0049(9) C11 0.0391(14) 0.0435(15) 0.0360(14) -0.0030(11) 0.0060(10) 0.0013(11) C7 0.0368(14) 0.0439(15) 0.0490(16) 0.0045(13) 0.0117(11) 0.0058(12) O1 0.0412(11) 0.0897(17) 0.0777(16) 0.0272(13) 0.0177(11) 0.0162(11) C6 0.0341(13) 0.0496(17) 0.0507(16) -0.0011(13) 0.0107(11) 0.0029(12) O3 0.0524(12) 0.0689(14) 0.0534(12) 0.0183(11) 0.0113(10) -0.0050(10) C13 0.0398(15) 0.0635(19) 0.0367(15) -0.0022(13) 0.0050(11) 0.0045(13) C8 0.0391(14) 0.0479(16) 0.0366(14) 0.0049(12) 0.0007(11) 0.0005(12) C16 0.0497(16) 0.071(2) 0.0419(16) 0.0074(14) 0.0136(12) -0.0023(15) C1 0.0434(16) 0.072(2) 0.0512(18) 0.0046(16) 0.0072(13) -0.0083(15) C9 0.0529(17) 0.0520(18) 0.0568(19) 0.0056(15) 0.0194(14) 0.0040(14) C5 0.0452(16) 0.060(2) 0.067(2) 0.0069(16) 0.0105(15) -0.0020(14) C4 0.0435(17) 0.066(2) 0.080(2) -0.0099(19) 0.0078(16) -0.0077(14) C3 0.0449(17) 0.093(3) 0.0509(19) -0.0157(18) 0.0016(14) 0.0019(17) C12 0.0650(19) 0.0520(18) 0.0531(18) -0.0084(14) 0.0138(15) 0.0029(15) C15 0.0439(19) 0.099(3) 0.070(2) 0.0059(19) 0.0101(16) -0.0012(17) C2 0.0523(19) 0.098(3) 0.0508(19) 0.0075(18) 0.0037(15) -0.0040(18) C14 0.056(2) 0.090(3) 0.059(2) 0.0220(19) 0.0023(16) 0.0092(18) C17 0.080(3) 0.137(4) 0.058(2) 0.038(3) 0.0072(19) -0.014(3) C19 0.101(3) 0.100(3) 0.109(3) 0.016(3) 0.071(3) 0.011(3) C10 0.093(3) 0.076(2) 0.060(2) -0.0037(19) 0.032(2) 0.007(2) C18 0.075(2) 0.079(2) 0.079(3) 0.001(2) 0.031(2) -0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.485(2) . ? S1 N1 1.657(2) . ? S1 C16 1.852(3) . ? O2 C7 1.343(3) . ? O2 C8 1.463(3) . ? N1 C11 1.472(3) . ? N1 H1 0.8600 . ? C11 C12 1.535(4) . ? C11 C8 1.544(4) . ? C11 C13 1.561(3) . ? C7 O3 1.193(3) . ? C7 C6 1.487(4) . ? C6 C1 1.375(4) . ? C6 C5 1.391(4) . ? C13 C14 1.535(5) . ? C13 C15 1.523(4) . ? C13 H13 0.9800 . ? C8 C9 1.494(4) . ? C8 H8 0.9800 . ? C16 C19 1.493(5) . ? C16 C18 1.498(5) . ? C16 C17 1.531(4) . ? C1 C2 1.396(4) . ? C1 H1A 0.9300 . ? C9 C10 1.311(4) . ? C9 H9 0.9300 . ? C5 C4 1.369(4) . ? C5 H5 0.9300 . ? C4 C3 1.381(5) . ? C4 H4 0.9300 . ? C3 C2 1.376(5) . ? C3 H3 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C2 H2 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C10 H10A 0.9300 . ? C10 H10B 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 109.69(13) . . ? O1 S1 C16 105.36(14) . . ? N1 S1 C16 99.56(12) . . ? C7 O2 C8 117.9(2) . . ? C11 N1 S1 122.74(17) . . ? C11 N1 H1 118.6 . . ? S1 N1 H1 118.6 . . ? N1 C11 C12 109.4(2) . . ? N1 C11 C8 112.0(2) . . ? C12 C11 C8 109.8(2) . . ? N1 C11 C13 105.9(2) . . ? C12 C11 C13 111.0(2) . . ? C8 C11 C13 108.7(2) . . ? O3 C7 O2 123.5(3) . . ? O3 C7 C6 124.5(3) . . ? O2 C7 C6 112.0(2) . . ? C1 C6 C5 119.3(3) . . ? C1 C6 C7 123.0(3) . . ? C5 C6 C7 117.7(3) . . ? C14 C13 C15 109.5(3) . . ? C14 C13 C11 113.1(3) . . ? C15 C13 C11 113.3(3) . . ? C14 C13 H13 106.8 . . ? C15 C13 H13 106.8 . . ? C11 C13 H13 106.8 . . ? O2 C8 C9 108.6(2) . . ? O2 C8 C11 105.9(2) . . ? C9 C8 C11 114.1(2) . . ? O2 C8 H8 109.4 . . ? C9 C8 H8 109.4 . . ? C11 C8 H8 109.4 . . ? C19 C16 C18 112.1(3) . . ? C19 C16 C17 110.9(3) . . ? C18 C16 C17 110.5(3) . . ? C19 C16 S1 107.3(2) . . ? C18 C16 S1 111.2(2) . . ? C17 C16 S1 104.5(2) . . ? C6 C1 C2 120.0(3) . . ? C6 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C10 C9 C8 123.6(3) . . ? C10 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 N1 C11 -107.4(2) . . . . ? C16 S1 N1 C11 142.4(2) . . . . ? S1 N1 C11 C12 -52.7(3) . . . . ? S1 N1 C11 C8 69.4(3) . . . . ? S1 N1 C11 C13 -172.33(18) . . . . ? C8 O2 C7 O3 0.3(4) . . . . ? C8 O2 C7 C6 178.7(2) . . . . ? O3 C7 C6 C1 -167.9(3) . . . . ? O2 C7 C6 C1 13.7(4) . . . . ? O3 C7 C6 C5 11.8(4) . . . . ? O2 C7 C6 C5 -166.5(3) . . . . ? N1 C11 C13 C14 179.0(2) . . . . ? C12 C11 C13 C14 60.4(3) . . . . ? C8 C11 C13 C14 -60.5(3) . . . . ? N1 C11 C13 C15 53.7(3) . . . . ? C12 C11 C13 C15 -65.0(3) . . . . ? C8 C11 C13 C15 174.1(3) . . . . ? C7 O2 C8 C9 86.1(3) . . . . ? C7 O2 C8 C11 -151.0(2) . . . . ? N1 C11 C8 O2 -66.5(3) . . . . ? C12 C11 C8 O2 55.3(3) . . . . ? C13 C11 C8 O2 176.8(2) . . . . ? N1 C11 C8 C9 52.8(3) . . . . ? C12 C11 C8 C9 174.6(2) . . . . ? C13 C11 C8 C9 -63.8(3) . . . . ? O1 S1 C16 C19 179.5(2) . . . . ? N1 S1 C16 C19 -66.9(3) . . . . ? O1 S1 C16 C18 -57.6(3) . . . . ? N1 S1 C16 C18 56.0(3) . . . . ? O1 S1 C16 C17 61.7(3) . . . . ? N1 S1 C16 C17 175.3(3) . . . . ? C5 C6 C1 C2 1.4(5) . . . . ? C7 C6 C1 C2 -178.8(3) . . . . ? O2 C8 C9 C10 -136.7(3) . . . . ? C11 C8 C9 C10 105.5(4) . . . . ? C1 C6 C5 C4 -1.5(5) . . . . ? C7 C6 C5 C4 178.7(3) . . . . ? C6 C5 C4 C3 0.0(5) . . . . ? C5 C4 C3 C2 1.7(6) . . . . ? C4 C3 C2 C1 -1.8(6) . . . . ? C6 C1 C2 C3 0.3(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 H1 O3 0.86 2.43 3.089(3) 133.8 2_546 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.216 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.039 data_ybh028_0m _database_code_depnum_ccdc_archive 'CCDC 932618' #TrackingRef '19231_web_deposit_cif_file_0_TaoGuo_1365121252.1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl N O S' _chemical_formula_weight 257.77 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' Cl Cl 0.1484 0.1585 '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 9.6100(14) _cell_length_b 11.5839(17) _cell_length_c 12.0682(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1343.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2540 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 22.81 _exptl_crystal_description ? _exptl_crystal_colour yellow-green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6786 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6984 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.51 _reflns_number_total 2503 _reflns_number_gt 2193 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0382P)^2^+0.0736P] 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 SHELXL _refine_ls_extinction_coef 0.025(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 -0.02(6) _refine_ls_number_reflns 2503 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.003 _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 0.02047(6) 0.84923(5) 1.16739(4) 0.04565(16) Uani 1 1 d . . . Cl1 Cl -0.14931(8) 0.86225(7) 0.48885(5) 0.0743(2) Uani 1 1 d . . . N1 N -0.00390(18) 0.87087(14) 1.02863(13) 0.0462(4) Uani 1 1 d . . . C7 C 0.0399(2) 0.79593(18) 0.95850(17) 0.0423(5) Uani 1 1 d . . . C4 C -0.0009(2) 0.81543(16) 0.84104(17) 0.0421(4) Uani 1 1 d . . . O1 O -0.11724(16) 0.87742(15) 1.21558(12) 0.0595(4) Uani 1 1 d . . . C2 C -0.1498(2) 0.91166(19) 0.70763(18) 0.0470(5) Uani 1 1 d . . . H2 H -0.2186 0.9655 0.6916 0.056 Uiso 1 1 calc R . . C3 C -0.1031(2) 0.89699(18) 0.81440(17) 0.0443(5) Uani 1 1 d . . . H3 H -0.1404 0.9425 0.8705 0.053 Uiso 1 1 calc R . . C1 C -0.0923(2) 0.8446(2) 0.62459(17) 0.0502(5) Uani 1 1 d . . . C6 C 0.0109(2) 0.7657(2) 0.64680(19) 0.0558(6) Uani 1 1 d . . . H6 H 0.0502 0.7229 0.5896 0.067 Uiso 1 1 calc R . . C5 C 0.0558(2) 0.75051(19) 0.7543(2) 0.0512(6) Uani 1 1 d . . . H5 H 0.1246 0.6963 0.7694 0.061 Uiso 1 1 calc R . . C8 C 0.1227(3) 0.6896(2) 0.9841(2) 0.0688(7) Uani 1 1 d . . . H8A H 0.2147 0.6974 0.9542 0.103 Uiso 1 1 calc R . . H8B H 0.0781 0.6236 0.9517 0.103 Uiso 1 1 calc R . . H8C H 0.1283 0.6796 1.0630 0.103 Uiso 1 1 calc R . . C12 C 0.1611(4) 0.9723(4) 1.3162(2) 0.1038(12) Uani 1 1 d . . . H12A H 0.2267 1.0317 1.3348 0.156 Uiso 1 1 calc R . . H12B H 0.1977 0.8985 1.3378 0.156 Uiso 1 1 calc R . . H12C H 0.0751 0.9861 1.3544 0.156 Uiso 1 1 calc R . . C9 C 0.1353(2) 0.9731(2) 1.19169(18) 0.0526(6) Uani 1 1 d . . . C10 C 0.2691(3) 0.9509(3) 1.1302(3) 0.0823(9) Uani 1 1 d . . . H10A H 0.2519 0.9534 1.0519 0.123 Uiso 1 1 calc R . . H10B H 0.3045 0.8763 1.1501 0.123 Uiso 1 1 calc R . . H10C H 0.3361 1.0091 1.1495 0.123 Uiso 1 1 calc R . . C11 C 0.0654(3) 1.0845(2) 1.1555(3) 0.0952(11) Uani 1 1 d . . . H11A H 0.1234 1.1489 1.1747 0.143 Uiso 1 1 calc R . . H11B H -0.0228 1.0918 1.1922 0.143 Uiso 1 1 calc R . . H11C H 0.0513 1.0832 1.0768 0.143 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 0.0465(3) 0.0460(3) 0.0444(3) 0.0047(2) -0.0026(2) -0.0004(2) Cl1 0.0934(5) 0.0793(5) 0.0503(3) -0.0027(3) -0.0163(3) -0.0017(4) N1 0.0517(10) 0.0437(9) 0.0431(9) -0.0010(8) -0.0041(8) 0.0054(9) C7 0.0368(11) 0.0410(11) 0.0492(12) 0.0029(9) 0.0015(9) 0.0003(9) C4 0.0364(11) 0.0430(10) 0.0469(11) -0.0010(9) 0.0019(9) -0.0012(8) O1 0.0438(9) 0.0791(12) 0.0556(9) 0.0020(8) 0.0052(7) -0.0022(8) C2 0.0419(12) 0.0461(12) 0.0531(13) 0.0041(10) 0.0001(10) 0.0006(9) C3 0.0428(11) 0.0436(12) 0.0466(11) 0.0004(9) 0.0055(10) 0.0030(9) C1 0.0529(13) 0.0521(13) 0.0457(12) -0.0005(11) -0.0031(9) -0.0076(12) C6 0.0545(14) 0.0631(14) 0.0498(13) -0.0130(11) 0.0068(11) 0.0036(12) C5 0.0446(13) 0.0520(13) 0.0570(13) -0.0062(11) 0.0001(10) 0.0091(10) C8 0.0755(18) 0.0694(16) 0.0615(15) 0.0011(13) -0.0048(14) 0.0342(13) C12 0.108(3) 0.149(3) 0.0551(15) -0.0130(18) -0.0098(16) -0.053(2) C9 0.0485(14) 0.0577(14) 0.0517(13) -0.0046(11) 0.0002(10) -0.0085(11) C10 0.0498(16) 0.099(2) 0.098(2) -0.0120(18) 0.0120(14) -0.0190(15) C11 0.095(2) 0.0476(16) 0.143(3) -0.0153(18) -0.010(2) -0.0032(14) _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 1.4820(16) . ? S1 N1 1.7093(17) . ? S1 C9 1.834(2) . ? Cl1 C1 1.739(2) . ? N1 C7 1.283(2) . ? C7 C4 1.488(3) . ? C7 C8 1.499(3) . ? C4 C5 1.399(3) . ? C4 C3 1.400(3) . ? C2 C3 1.375(3) . ? C2 C1 1.383(3) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C1 C6 1.374(3) . ? C6 C5 1.379(3) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C12 C9 1.523(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C9 C11 1.519(4) . ? C9 C10 1.506(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 103.29(9) . . ? O1 S1 C9 107.59(11) . . ? N1 S1 C9 97.14(9) . . ? C7 N1 S1 120.13(14) . . ? N1 C7 C4 116.06(17) . . ? N1 C7 C8 126.4(2) . . ? C4 C7 C8 117.47(18) . . ? C5 C4 C3 117.63(19) . . ? C5 C4 C7 121.91(18) . . ? C3 C4 C7 120.39(18) . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C6 C1 C2 121.34(19) . . ? C6 C1 Cl1 119.28(17) . . ? C2 C1 Cl1 119.37(18) . . ? C1 C6 C5 119.6(2) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C9 C10 112.4(2) . . ? C11 C9 C12 111.2(3) . . ? C10 C9 C12 110.3(2) . . ? C11 C9 S1 110.62(17) . . ? C10 C9 S1 107.54(17) . . ? C12 C9 S1 104.51(18) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N1 C7 -134.05(17) . . . . ? C9 S1 N1 C7 115.92(18) . . . . ? S1 N1 C7 C4 172.97(14) . . . . ? S1 N1 C7 C8 -4.6(3) . . . . ? N1 C7 C4 C5 170.61(19) . . . . ? C8 C7 C4 C5 -11.6(3) . . . . ? N1 C7 C4 C3 -12.3(3) . . . . ? C8 C7 C4 C3 165.5(2) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C5 C4 C3 C2 1.7(3) . . . . ? C7 C4 C3 C2 -175.6(2) . . . . ? C3 C2 C1 C6 -0.9(3) . . . . ? C3 C2 C1 Cl1 -179.70(18) . . . . ? C2 C1 C6 C5 1.8(3) . . . . ? Cl1 C1 C6 C5 -179.42(19) . . . . ? C1 C6 C5 C4 -0.9(4) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C7 C4 C5 C6 176.4(2) . . . . ? O1 S1 C9 C11 -49.8(2) . . . . ? N1 S1 C9 C11 56.6(2) . . . . ? O1 S1 C9 C10 -172.87(17) . . . . ? N1 S1 C9 C10 -66.45(18) . . . . ? O1 S1 C9 C12 69.9(2) . . . . ? N1 S1 C9 C12 176.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.154 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.033 data_gt066_0m _database_code_depnum_ccdc_archive 'CCDC 932619' #TrackingRef '19232_web_deposit_cif_file_1_TaoGuo_1365121252.1s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cl N O S' _chemical_formula_weight 243.74 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' Cl Cl 0.1484 0.1585 '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 5.615(16) _cell_length_b 10.35(3) _cell_length_c 11.29(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.90(3) _cell_angle_gamma 90.00 _cell_volume 640(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1287 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.87 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6466 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2996 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1884 _reflns_number_gt 1533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0398P)^2^+0.0826P] 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 0.039(4) _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 -0.02(12) _refine_ls_number_reflns 1884 _refine_ls_number_parameters 140 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.125 _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 1.38135(13) 0.99703(9) 0.72736(7) 0.0672(3) Uani 1 1 d U . . Cl1 Cl 0.04275(16) 0.99093(14) 0.20760(8) 0.0934(4) Uani 1 1 d U . . C8 C 1.2805(4) 0.9932(5) 0.8731(3) 0.0621(8) Uani 1 1 d U . . C1 C 0.3240(6) 0.9756(4) 0.3101(3) 0.0663(10) Uani 1 1 d U . . N1 N 1.0998(5) 1.0251(3) 0.6371(3) 0.0653(8) Uani 1 1 d U . . C4 C 0.7727(7) 0.9518(3) 0.4738(3) 0.0606(9) Uani 1 1 d U . . C3 C 0.6496(7) 1.0695(4) 0.4597(3) 0.0679(10) Uani 1 1 d U . . H3 H 0.7174 1.1403 0.5059 0.081 Uiso 1 1 calc R . . C7 C 1.0093(7) 0.9379(4) 0.5605(3) 0.0635(9) Uani 1 1 d U . . H7 H 1.0971 0.8619 0.5594 0.076 Uiso 1 1 calc R . . C9 C 1.1202(7) 0.8767(4) 0.8757(4) 0.0826(12) Uani 1 1 d U . . H9A H 1.0967 0.8644 0.9566 0.124 Uiso 1 1 calc R . . H9B H 1.1972 0.8015 0.8512 0.124 Uiso 1 1 calc R . . H9C H 0.9648 0.8899 0.8210 0.124 Uiso 1 1 calc R . . C2 C 0.4239(7) 1.0828(4) 0.3763(4) 0.0741(10) Uani 1 1 d U . . H2 H 0.3435 1.1619 0.3658 0.089 Uiso 1 1 calc R . . C5 C 0.6668(7) 0.8474(4) 0.4046(3) 0.0735(10) Uani 1 1 d U . . H5 H 0.7478 0.7684 0.4128 0.088 Uiso 1 1 calc R . . C11 C 1.1518(8) 1.1207(5) 0.8863(4) 0.0877(13) Uani 1 1 d U . . H11A H 1.0005 1.1248 0.8267 0.131 Uiso 1 1 calc R . . H11B H 1.2545 1.1915 0.8745 0.131 Uiso 1 1 calc R . . H11C H 1.1195 1.1259 0.9662 0.131 Uiso 1 1 calc R . . C6 C 0.4435(7) 0.8583(4) 0.3237(3) 0.0766(11) Uani 1 1 d U . . H6 H 0.3743 0.7871 0.2787 0.092 Uiso 1 1 calc R . . O1 O 1.4698(5) 0.8661(3) 0.7085(2) 0.0864(8) Uani 1 1 d U . . C10 C 1.5200(6) 0.9829(6) 0.9698(3) 0.0940(13) Uani 1 1 d U . . H10A H 1.4849 0.9842 1.0492 0.141 Uiso 1 1 calc R . . H10B H 1.6238 1.0545 0.9617 0.141 Uiso 1 1 calc R . . H10C H 1.6009 0.9036 0.9589 0.141 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 0.0593(4) 0.0711(6) 0.0731(6) -0.0003(6) 0.0186(4) -0.0047(5) Cl1 0.0848(6) 0.1181(9) 0.0710(6) 0.0054(8) 0.0036(4) -0.0050(7) C8 0.0520(14) 0.073(2) 0.0613(18) 0.003(2) 0.0128(12) 0.004(2) C1 0.0766(19) 0.072(3) 0.0504(18) 0.006(2) 0.0137(14) -0.008(2) N1 0.0732(16) 0.063(2) 0.0591(17) -0.0025(15) 0.0130(13) -0.0046(14) C4 0.073(2) 0.055(2) 0.057(2) -0.0025(16) 0.0209(17) -0.0057(16) C3 0.080(2) 0.057(3) 0.065(2) -0.0061(19) 0.0151(19) -0.0063(18) C7 0.076(2) 0.057(2) 0.062(2) 0.0013(19) 0.0238(18) 0.0039(16) C9 0.069(2) 0.086(3) 0.095(3) 0.011(3) 0.024(2) -0.004(2) C2 0.089(3) 0.061(2) 0.073(3) 0.007(2) 0.017(2) 0.0045(19) C5 0.094(3) 0.054(2) 0.069(2) -0.008(2) 0.011(2) 0.0014(19) C11 0.096(3) 0.083(3) 0.085(3) -0.013(3) 0.025(2) 0.012(3) C6 0.093(3) 0.067(3) 0.066(2) -0.010(2) 0.009(2) -0.011(2) O1 0.0726(15) 0.0896(19) 0.100(2) -0.0095(16) 0.0248(13) 0.0190(14) C10 0.0617(18) 0.141(4) 0.075(2) 0.003(3) 0.0066(16) 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 O1 1.475(5) . ? S1 N1 1.704(5) . ? S1 C8 1.857(5) . ? Cl1 C1 1.745(5) . ? C8 C9 1.509(7) . ? C8 C11 1.527(7) . ? C8 C10 1.535(5) . ? C1 C6 1.379(7) . ? C1 C2 1.384(6) . ? N1 C7 1.274(5) . ? C4 C5 1.388(6) . ? C4 C3 1.392(6) . ? C4 C7 1.471(6) . ? C3 C2 1.406(6) . ? C3 H3 0.9300 . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C2 H2 0.9300 . ? C5 C6 1.381(6) . ? C5 H5 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C6 H6 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 111.59(17) . . ? O1 S1 C8 106.7(2) . . ? N1 S1 C8 96.2(2) . . ? C9 C8 C11 113.0(3) . . ? C9 C8 C10 111.2(4) . . ? C11 C8 C10 110.4(4) . . ? C9 C8 S1 109.6(3) . . ? C11 C8 S1 108.2(3) . . ? C10 C8 S1 103.8(3) . . ? C6 C1 C2 121.1(4) . . ? C6 C1 Cl1 120.0(3) . . ? C2 C1 Cl1 118.9(3) . . ? C7 N1 S1 117.5(3) . . ? C5 C4 C3 118.5(4) . . ? C5 C4 C7 120.6(4) . . ? C3 C4 C7 120.9(3) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? N1 C7 C4 123.2(3) . . ? N1 C7 H7 118.4 . . ? C4 C7 H7 118.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C2 C3 118.6(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? 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 . . ? C1 C6 C5 119.5(4) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 C8 C9 -47.8(3) . . . . ? N1 S1 C8 C9 67.0(3) . . . . ? O1 S1 C8 C11 -171.4(3) . . . . ? N1 S1 C8 C11 -56.7(3) . . . . ? O1 S1 C8 C10 71.2(3) . . . . ? N1 S1 C8 C10 -174.1(3) . . . . ? O1 S1 N1 C7 -5.0(3) . . . . ? C8 S1 N1 C7 -115.7(3) . . . . ? C5 C4 C3 C2 -0.6(5) . . . . ? C7 C4 C3 C2 179.7(3) . . . . ? S1 N1 C7 C4 -177.5(2) . . . . ? C5 C4 C7 N1 -170.7(3) . . . . ? C3 C4 C7 N1 9.0(5) . . . . ? C6 C1 C2 C3 -0.9(5) . . . . ? Cl1 C1 C2 C3 179.4(3) . . . . ? C4 C3 C2 C1 1.3(5) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C7 C4 C5 C6 179.3(3) . . . . ? C2 C1 C6 C5 0.0(6) . . . . ? Cl1 C1 C6 C5 179.6(3) . . . . ? C4 C5 C6 C1 0.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.158 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.053