data_ww672m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O3 S' _chemical_formula_weight 327.39 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 7.6885(2) _cell_length_b 13.6801(3) _cell_length_c 8.0672(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.7250(10) _cell_angle_gamma 90.00 _cell_volume 812.61(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 9527 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 33.13 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 15740 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 33.22 _reflns_number_total 6053 _reflns_number_gt 4894 _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^)+(0.0559P)^2^+0.0579P] 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 noref _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 0.09(6) _refine_ls_number_reflns 6053 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 S S 0.50349(5) 0.52153(4) 0.49807(4) 0.04180(9) Uani 1 1 d . . . O1 O 0.38140(18) 0.58775(10) 0.38370(14) 0.0539(3) Uani 1 1 d . . . O2 O 0.64552(18) 0.47685(13) 0.44317(15) 0.0626(4) Uani 1 1 d . . . O3 O 0.1529(2) 0.70935(13) 0.7961(3) 0.0817(5) Uani 1 1 d . . . N N 0.60256(17) 0.58370(10) 0.67695(15) 0.0406(3) Uani 1 1 d . . . C1 C 0.72837(17) 0.52867(12) 0.81118(16) 0.0385(3) Uani 1 1 d . . . C2 C 0.8916(2) 0.49656(14) 0.7917(2) 0.0510(4) Uani 1 1 d . . . H2 H 0.9262 0.5145 0.6932 0.061 Uiso 1 1 calc R . . C3 C 1.0042(2) 0.43795(16) 0.9175(2) 0.0550(4) Uani 1 1 d . . . H3 H 1.1148 0.4157 0.9036 0.066 Uiso 1 1 calc R . . C4 C 0.9550(3) 0.41188(14) 1.0634(2) 0.0524(4) Uani 1 1 d . . . H4 H 1.0308 0.3709 1.1471 0.063 Uiso 1 1 calc R . . C5 C 0.7947(2) 0.44615(11) 1.08594(19) 0.0448(3) Uani 1 1 d . . . H5 H 0.7630 0.4292 1.1864 0.054 Uiso 1 1 calc R . . C6 C 0.67920(19) 0.50562(9) 0.96166(16) 0.0366(3) Uani 1 1 d . . . C7 C 0.5110(2) 0.54354(10) 0.98130(17) 0.0401(3) Uani 1 1 d . . . H7 H 0.4656 0.5189 1.0693 0.048 Uiso 1 1 calc R . . C8 C 0.4186(2) 0.61370(11) 0.8753(2) 0.0420(3) Uani 1 1 d . . . C9 C 0.4932(2) 0.65619(11) 0.7375(2) 0.0455(3) Uani 1 1 d . . . H9 H 0.3903 0.6766 0.6382 0.055 Uiso 1 1 calc R . . C10 C 0.2488(3) 0.65192(14) 0.8956(3) 0.0587(4) Uani 1 1 d . . . H10 H 0.2118 0.6308 0.9911 0.070 Uiso 1 1 calc R . . C11 C 0.6113(3) 0.74606(13) 0.8070(3) 0.0643(5) Uani 1 1 d . . . H11A H 0.7079 0.7279 0.9092 0.096 Uiso 1 1 calc R . . H11B H 0.5371 0.7966 0.8369 0.096 Uiso 1 1 calc R . . H11C H 0.6635 0.7704 0.7190 0.096 Uiso 1 1 calc R . . C12 C 0.37554(18) 0.42698(10) 0.55326(15) 0.0336(2) Uani 1 1 d . . . C13 C 0.18848(19) 0.43420(10) 0.50384(18) 0.0379(3) Uani 1 1 d . . . H13 H 0.1305 0.4904 0.4467 0.045 Uiso 1 1 calc R . . C14 C 0.0873(2) 0.35729(12) 0.5398(2) 0.0462(3) Uani 1 1 d . . . H14 H -0.0402 0.3609 0.5034 0.055 Uiso 1 1 calc R . . C15 C 0.1716(2) 0.27508(13) 0.62863(19) 0.0476(3) Uani 1 1 d . . . C16 C 0.3594(2) 0.27068(12) 0.67931(18) 0.0473(3) Uani 1 1 d . . . H16 H 0.4178 0.2159 0.7413 0.057 Uiso 1 1 calc R . . C17 C 0.4623(2) 0.34491(12) 0.6407(2) 0.0430(3) Uani 1 1 d . . . H17 H 0.5896 0.3401 0.6731 0.052 Uiso 1 1 calc R . . C18 C 0.0600(3) 0.19202(17) 0.6667(3) 0.0783(7) Uani 1 1 d . . . H18A H 0.0877 0.1834 0.7909 0.118 Uiso 1 1 calc R . . H18B H 0.0885 0.1324 0.6149 0.118 Uiso 1 1 calc R . . H18C H -0.0681 0.2068 0.6187 0.118 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 S 0.04418(16) 0.0590(2) 0.02213(12) 0.00218(12) 0.00941(10) -0.00765(15) O1 0.0616(7) 0.0633(7) 0.0289(5) 0.0140(5) 0.0004(5) -0.0126(5) O2 0.0539(7) 0.1060(11) 0.0344(5) -0.0072(6) 0.0233(5) -0.0047(7) O3 0.0701(9) 0.0688(9) 0.0976(12) -0.0027(9) 0.0104(9) 0.0222(8) N 0.0431(6) 0.0472(6) 0.0278(5) 0.0035(5) 0.0043(4) -0.0103(5) C1 0.0387(6) 0.0473(7) 0.0270(5) 0.0018(6) 0.0055(4) -0.0103(6) C2 0.0412(7) 0.0764(12) 0.0354(7) 0.0030(7) 0.0109(6) -0.0082(7) C3 0.0409(7) 0.0765(12) 0.0449(9) -0.0043(8) 0.0081(6) 0.0017(7) C4 0.0568(9) 0.0575(10) 0.0372(7) 0.0009(7) 0.0045(7) 0.0083(7) C5 0.0593(9) 0.0451(8) 0.0285(6) 0.0024(5) 0.0104(6) 0.0017(6) C6 0.0467(6) 0.0369(6) 0.0258(5) -0.0019(4) 0.0097(5) -0.0058(5) C7 0.0510(8) 0.0409(7) 0.0298(6) -0.0044(5) 0.0138(6) -0.0041(5) C8 0.0489(7) 0.0377(6) 0.0372(7) -0.0075(5) 0.0090(6) -0.0029(5) C9 0.0543(8) 0.0384(7) 0.0355(7) 0.0025(5) 0.0000(6) -0.0048(6) C10 0.0610(10) 0.0505(9) 0.0627(11) -0.0135(8) 0.0149(9) 0.0050(8) C11 0.0863(13) 0.0402(8) 0.0547(10) 0.0063(7) 0.0016(9) -0.0200(8) C12 0.0395(6) 0.0370(6) 0.0235(5) -0.0042(4) 0.0076(4) 0.0013(5) C13 0.0403(6) 0.0368(6) 0.0337(6) -0.0001(5) 0.0060(5) 0.0038(5) C14 0.0410(7) 0.0477(8) 0.0448(8) 0.0019(6) 0.0044(6) -0.0034(6) C15 0.0630(9) 0.0374(6) 0.0371(6) -0.0013(6) 0.0060(6) -0.0092(7) C16 0.0645(9) 0.0340(6) 0.0370(6) 0.0002(6) 0.0046(6) 0.0080(7) C17 0.0433(7) 0.0468(7) 0.0364(7) -0.0026(5) 0.0073(5) 0.0110(6) C18 0.0892(15) 0.0626(12) 0.0705(14) 0.0144(10) 0.0027(12) -0.0321(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O2 1.4285(14) . ? S O1 1.4334(13) . ? S N 1.6593(13) . ? S C12 1.7582(14) . ? O3 C10 1.210(3) . ? N C1 1.4394(18) . ? N C9 1.472(2) . ? C1 C2 1.381(2) . ? C1 C6 1.4072(17) . ? C2 C3 1.384(2) . ? C2 H2 0.9400 . ? C3 C4 1.382(3) . ? C3 H3 0.9400 . ? C4 C5 1.379(2) . ? C4 H4 0.9400 . ? C5 C6 1.3941(19) . ? C5 H5 0.9400 . ? C6 C7 1.444(2) . ? C7 C8 1.344(2) . ? C7 H7 0.9400 . ? C8 C10 1.459(2) . ? C8 C9 1.507(2) . ? C9 C11 1.536(2) . ? C9 H9 0.9900 . ? C10 H10 0.9400 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 C13 1.3810(19) . ? C12 C17 1.390(2) . ? C13 C14 1.388(2) . ? C13 H13 0.9400 . ? C14 C15 1.390(2) . ? C14 H14 0.9400 . ? C15 C16 1.384(2) . ? C15 C18 1.508(2) . ? C16 C17 1.377(2) . ? C16 H16 0.9400 . ? C17 H17 0.9400 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S O1 119.23(8) . . ? O2 S N 106.76(8) . . ? O1 S N 106.71(8) . . ? O2 S C12 107.28(9) . . ? O1 S C12 108.51(7) . . ? N S C12 107.89(6) . . ? C1 N C9 115.29(11) . . ? C1 N S 115.28(10) . . ? C9 N S 118.09(10) . . ? C2 C1 C6 120.36(13) . . ? C2 C1 N 121.12(12) . . ? C6 C1 N 118.49(12) . . ? C1 C2 C3 119.86(14) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 120.48(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 119.89(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.81(14) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.52(13) . . ? C5 C6 C7 122.43(12) . . ? C1 C6 C7 119.05(12) . . ? C8 C7 C6 120.87(13) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C10 120.75(15) . . ? C7 C8 C9 120.05(14) . . ? C10 C8 C9 119.18(15) . . ? N C9 C8 111.12(12) . . ? N C9 C11 109.05(15) . . ? C8 C9 C11 110.48(14) . . ? N C9 H9 108.7 . . ? C8 C9 H9 108.7 . . ? C11 C9 H9 108.7 . . ? O3 C10 C8 123.5(2) . . ? O3 C10 H10 118.2 . . ? C8 C10 H10 118.2 . . ? 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 . . ? C13 C12 C17 120.79(14) . . ? C13 C12 S 119.10(11) . . ? C17 C12 S 120.07(11) . . ? C12 C13 C14 119.03(13) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C13 C14 C15 121.00(14) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 118.65(15) . . ? C16 C15 C18 120.89(17) . . ? C14 C15 C18 120.45(17) . . ? C17 C16 C15 121.29(15) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C12 119.18(14) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.22 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.310 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.044