data_k75h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 N O2 S' _chemical_formula_weight 305.42 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0826(17) _cell_length_b 8.2727(17) _cell_length_c 11.499(2) _cell_angle_alpha 93.787(2) _cell_angle_beta 96.492(2) _cell_angle_gamma 91.748(2) _cell_volume 761.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9279 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8400 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.13 _reflns_number_total 4304 _reflns_number_gt 3741 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0710P)^2^+0.3001P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4304 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.06376(4) 0.67731(4) 0.21520(4) 0.02673(12) Uani 1 1 d . . . O1 O -0.13232(13) 0.44045(14) 0.34885(10) 0.0273(2) Uani 1 1 d . . . O2 O -0.17799(12) 0.42037(13) 0.15100(9) 0.0258(2) Uani 1 1 d . . . N N -0.06272(16) 0.20459(15) 0.24707(12) 0.0259(3) Uani 1 1 d . . . C1 C -0.06634(16) 0.37950(16) 0.24764(12) 0.0208(3) Uani 1 1 d . . . C2 C 0.10558(16) 0.45982(16) 0.23691(12) 0.0207(3) Uani 1 1 d . . . C3 C 0.22551(18) 0.45427(17) 0.34980(14) 0.0252(3) Uani 1 1 d . . . H3A H 0.3334 0.5046 0.3355 0.030 Uiso 1 1 calc R . . H3B H 0.1814 0.5244 0.4113 0.030 Uiso 1 1 calc R . . C4 C 0.2618(2) 0.29057(19) 0.40064(14) 0.0295(3) Uani 1 1 d . . . H4A H 0.2973 0.2153 0.3385 0.035 Uiso 1 1 calc R . . H4B H 0.3554 0.3061 0.4642 0.035 Uiso 1 1 calc R . . C5 C 0.1133(2) 0.2138(2) 0.44901(15) 0.0336(3) Uani 1 1 d . . . H5A H 0.0600 0.2992 0.4946 0.040 Uiso 1 1 calc R . . H5B H 0.1547 0.1332 0.5042 0.040 Uiso 1 1 calc R . . C6 C -0.0196(2) 0.1300(2) 0.35793(15) 0.0323(3) Uani 1 1 d . . . H6A H 0.0172 0.0193 0.3388 0.039 Uiso 1 1 calc R . . H6B H -0.1231 0.1181 0.3957 0.039 Uiso 1 1 calc R . . C7 C -0.0031(2) 0.12938(18) 0.14038(15) 0.0303(3) Uani 1 1 d . . . H7A H -0.0855 0.1462 0.0721 0.036 Uiso 1 1 calc R . . H7B H 0.0031 0.0111 0.1478 0.036 Uiso 1 1 calc R . . C8 C 0.1675(2) 0.19622(19) 0.11658(14) 0.0304(3) Uani 1 1 d . . . H8A H 0.1903 0.1564 0.0371 0.036 Uiso 1 1 calc R . . H8B H 0.2552 0.1572 0.1741 0.036 Uiso 1 1 calc R . . C9 C 0.17196(19) 0.38248(19) 0.12593(14) 0.0268(3) Uani 1 1 d . . . H9A H 0.1052 0.4198 0.0559 0.032 Uiso 1 1 calc R . . H9B H 0.2884 0.4224 0.1247 0.032 Uiso 1 1 calc R . . C10 C -0.3077(2) 0.4509(3) 0.31905(19) 0.0543(6) Uani 1 1 d . . . H10A H -0.3433 0.5619 0.3385 0.065 Uiso 1 1 calc R . . H10B H -0.3692 0.3739 0.3624 0.065 Uiso 1 1 calc R . . C11 C -0.33989(19) 0.4087(2) 0.18971(17) 0.0360(4) Uani 1 1 d . . . H11A H -0.3895 0.2975 0.1730 0.043 Uiso 1 1 calc R . . H11B H -0.4156 0.4860 0.1511 0.043 Uiso 1 1 calc R . . C12 C 0.26801(18) 0.76611(17) 0.22006(14) 0.0252(3) Uani 1 1 d . . . C13 C 0.3485(2) 0.84241(19) 0.32372(15) 0.0327(3) Uani 1 1 d . . . H13 H 0.2968 0.8426 0.3939 0.039 Uiso 1 1 calc R . . C14 C 0.5047(2) 0.9184(2) 0.32441(19) 0.0423(4) Uani 1 1 d . . . H14 H 0.5594 0.9698 0.3953 0.051 Uiso 1 1 calc R . . C15 C 0.5807(2) 0.9194(2) 0.2228(2) 0.0462(5) Uani 1 1 d . . . H15 H 0.6874 0.9713 0.2238 0.055 Uiso 1 1 calc R . . C16 C 0.5007(2) 0.8446(3) 0.1195(2) 0.0448(4) Uani 1 1 d . . . H16 H 0.5525 0.8458 0.0494 0.054 Uiso 1 1 calc R . . C17 C 0.3452(2) 0.7679(2) 0.11787(16) 0.0332(3) Uani 1 1 d . . . H17 H 0.2912 0.7164 0.0467 0.040 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 0.01954(18) 0.01961(18) 0.0415(2) 0.00853(14) 0.00214(14) 0.00014(12) O1 0.0205(5) 0.0321(6) 0.0296(5) -0.0013(4) 0.0071(4) -0.0007(4) O2 0.0177(5) 0.0284(5) 0.0306(5) 0.0050(4) -0.0016(4) -0.0011(4) N 0.0234(6) 0.0200(5) 0.0345(7) 0.0050(5) 0.0035(5) -0.0022(4) C1 0.0171(6) 0.0207(6) 0.0245(6) 0.0025(5) 0.0019(5) -0.0006(4) C2 0.0176(6) 0.0181(6) 0.0267(6) 0.0052(5) 0.0021(5) 0.0004(4) C3 0.0204(6) 0.0228(6) 0.0314(7) 0.0049(5) -0.0024(5) -0.0009(5) C4 0.0298(7) 0.0262(7) 0.0317(8) 0.0073(6) -0.0026(6) 0.0020(6) C5 0.0375(9) 0.0324(8) 0.0318(8) 0.0120(6) 0.0024(6) -0.0011(6) C6 0.0335(8) 0.0275(7) 0.0370(8) 0.0106(6) 0.0055(6) -0.0035(6) C7 0.0323(8) 0.0219(7) 0.0351(8) -0.0026(6) 0.0000(6) 0.0000(5) C8 0.0315(8) 0.0288(7) 0.0317(8) -0.0014(6) 0.0089(6) 0.0047(6) C9 0.0239(7) 0.0282(7) 0.0301(7) 0.0050(6) 0.0090(5) 0.0015(5) C10 0.0206(8) 0.0913(17) 0.0505(12) -0.0109(11) 0.0099(8) 0.0066(9) C11 0.0172(7) 0.0411(9) 0.0489(10) 0.0031(7) 0.0007(6) 0.0002(6) C12 0.0218(6) 0.0187(6) 0.0349(8) 0.0077(5) 0.0004(5) -0.0018(5) C13 0.0353(8) 0.0250(7) 0.0364(8) 0.0024(6) -0.0005(6) -0.0016(6) C14 0.0352(9) 0.0307(8) 0.0564(11) 0.0028(8) -0.0132(8) -0.0067(7) C15 0.0255(8) 0.0388(10) 0.0737(14) 0.0123(9) 0.0015(8) -0.0088(7) C16 0.0339(9) 0.0459(10) 0.0577(12) 0.0146(9) 0.0151(8) -0.0054(7) C17 0.0310(8) 0.0317(8) 0.0376(8) 0.0104(6) 0.0036(6) -0.0036(6) _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 C12 1.7799(15) . ? S C2 1.8684(14) . ? O1 C1 1.4044(17) . ? O1 C10 1.427(2) . ? O2 C1 1.4161(16) . ? O2 C11 1.4316(19) . ? N C1 1.4478(18) . ? N C6 1.464(2) . ? N C7 1.475(2) . ? C1 C2 1.5430(18) . ? C2 C3 1.534(2) . ? C2 C9 1.547(2) . ? C3 C4 1.534(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.518(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.530(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.537(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.497(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.392(2) . ? C12 C13 1.394(2) . ? C13 C14 1.392(2) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? 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 C12 S C2 102.52(6) . . ? C1 O1 C10 107.26(12) . . ? C1 O2 C11 105.11(11) . . ? C1 N C6 119.02(13) . . ? C1 N C7 112.91(12) . . ? C6 N C7 118.04(12) . . ? O1 C1 O2 106.34(11) . . ? O1 C1 N 109.23(11) . . ? O2 C1 N 108.53(11) . . ? O1 C1 C2 111.59(11) . . ? O2 C1 C2 107.99(10) . . ? N C1 C2 112.90(11) . . ? C3 C2 C1 112.11(11) . . ? C3 C2 C9 114.27(12) . . ? C1 C2 C9 108.38(11) . . ? C3 C2 S 107.59(9) . . ? C1 C2 S 105.02(9) . . ? C9 C2 S 109.02(9) . . ? C4 C3 C2 119.45(12) . . ? C4 C3 H3A 107.5 . . ? C2 C3 H3A 107.5 . . ? C4 C3 H3B 107.5 . . ? C2 C3 H3B 107.5 . . ? H3A C3 H3B 107.0 . . ? C5 C4 C3 113.39(13) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 115.75(14) . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5B 108.3 . . ? C6 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N C6 C5 118.92(13) . . ? N C6 H6A 107.6 . . ? C5 C6 H6A 107.6 . . ? N C6 H6B 107.6 . . ? C5 C6 H6B 107.6 . . ? H6A C6 H6B 107.0 . . ? N C7 C8 113.89(12) . . ? N C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 110.28(12) . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C2 114.75(12) . . ? C8 C9 H9A 108.6 . . ? C2 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C2 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O1 C10 C11 105.94(14) . . ? O1 C10 H10A 110.5 . . ? C11 C10 H10A 110.5 . . ? O1 C10 H10B 110.5 . . ? C11 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? O2 C11 C10 103.73(13) . . ? O2 C11 H11A 111.0 . . ? C10 C11 H11A 111.0 . . ? O2 C11 H11B 111.0 . . ? C10 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? C17 C12 C13 119.24(14) . . ? C17 C12 S 119.83(12) . . ? C13 C12 S 120.83(13) . . ? C14 C13 C12 120.01(17) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.45(18) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.74(17) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.29(18) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.26(17) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? 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 C10 O1 C1 O2 25.17(17) . . . . ? C10 O1 C1 N -91.77(17) . . . . ? C10 O1 C1 C2 142.69(15) . . . . ? C11 O2 C1 O1 -35.05(14) . . . . ? C11 O2 C1 N 82.34(14) . . . . ? C11 O2 C1 C2 -154.95(12) . . . . ? C6 N C1 O1 -38.12(16) . . . . ? C7 N C1 O1 177.00(11) . . . . ? C6 N C1 O2 -153.66(12) . . . . ? C7 N C1 O2 61.46(15) . . . . ? C6 N C1 C2 86.66(15) . . . . ? C7 N C1 C2 -58.22(15) . . . . ? O1 C1 C2 C3 51.14(15) . . . . ? O2 C1 C2 C3 167.66(11) . . . . ? N C1 C2 C3 -72.35(15) . . . . ? O1 C1 C2 C9 178.19(11) . . . . ? O2 C1 C2 C9 -65.28(13) . . . . ? N C1 C2 C9 54.71(14) . . . . ? O1 C1 C2 S -65.40(12) . . . . ? O2 C1 C2 S 51.13(12) . . . . ? N C1 C2 S 171.12(10) . . . . ? C12 S C2 C3 54.17(11) . . . . ? C12 S C2 C1 173.76(9) . . . . ? C12 S C2 C9 -70.26(11) . . . . ? C1 C2 C3 C4 55.71(17) . . . . ? C9 C2 C3 C4 -68.10(17) . . . . ? S C2 C3 C4 170.69(11) . . . . ? C2 C3 C4 C5 -68.62(19) . . . . ? C3 C4 C5 C6 78.33(18) . . . . ? C1 N C6 C5 -36.9(2) . . . . ? C7 N C6 C5 106.16(17) . . . . ? C4 C5 C6 N -39.0(2) . . . . ? C1 N C7 C8 54.97(17) . . . . ? C6 N C7 C8 -90.28(16) . . . . ? N C7 C8 C9 -48.61(18) . . . . ? C7 C8 C9 C2 48.08(18) . . . . ? C3 C2 C9 C8 75.26(16) . . . . ? C1 C2 C9 C8 -50.53(16) . . . . ? S C2 C9 C8 -164.33(11) . . . . ? C1 O1 C10 C11 -5.9(2) . . . . ? C1 O2 C11 C10 30.24(18) . . . . ? O1 C10 C11 O2 -15.1(2) . . . . ? C2 S C12 C17 87.59(13) . . . . ? C2 S C12 C13 -96.11(13) . . . . ? C17 C12 C13 C14 -0.4(2) . . . . ? S C12 C13 C14 -176.72(12) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C17 -0.4(3) . . . . ? C15 C16 C17 C12 0.2(3) . . . . ? C13 C12 C17 C16 0.1(2) . . . . ? S C12 C17 C16 176.50(14) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 30.13 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.583 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.068