data_igs10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 N O3 S' _chemical_formula_weight 359.47 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.6482(7) _cell_length_b 10.2749(5) _cell_length_c 13.7082(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.1450(10) _cell_angle_gamma 90.00 _cell_volume 1871.98(16) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9933 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 30.55 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9431 _exptl_absorpt_correction_T_max 0.9538 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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_reflns_number 29321 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 30.57 _reflns_number_total 5757 _reflns_number_gt 4416 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0651P)^2^+0.8883P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5757 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.66521(3) 0.34675(4) 0.07320(3) 0.03125(11) Uani 1 1 d . . . N N 0.73852(10) 0.42898(12) 0.01771(10) 0.0314(3) Uani 1 1 d . . . O1 O 0.89913(10) 1.01072(12) 0.07454(9) 0.0417(3) Uani 1 1 d . . . O2 O 0.72966(10) 0.27714(12) 0.15389(8) 0.0386(3) Uani 1 1 d . . . O3 O 0.59244(10) 0.43666(12) 0.09519(10) 0.0422(3) Uani 1 1 d . . . C1 C 0.83404(13) 0.37119(16) 0.00785(13) 0.0356(3) Uani 1 1 d . . . H1A H 0.8511 0.2979 0.0556 0.043 Uiso 1 1 calc R . . H1B H 0.8880 0.4371 0.0257 0.043 Uiso 1 1 calc R . . C2 C 0.82986(14) 0.32161(17) -0.09821(14) 0.0398(4) Uani 1 1 d . . . H2B H 0.7770 0.2526 -0.1145 0.048 Uiso 1 1 calc R . . C3 C 0.79927(15) 0.43504(18) -0.17114(13) 0.0420(4) Uani 1 1 d . . . H3B H 0.8507 0.5046 -0.1559 0.050 Uiso 1 1 calc R . . H3C H 0.7950 0.4048 -0.2406 0.050 Uiso 1 1 calc R . . C4 C 0.69795(15) 0.48856(17) -0.16202(13) 0.0411(4) Uani 1 1 d . . . H4A H 0.6461 0.4204 -0.1827 0.049 Uiso 1 1 calc R . . H4B H 0.6799 0.5630 -0.2084 0.049 Uiso 1 1 calc R . . C5 C 0.69715(12) 0.53342(15) -0.05535(12) 0.0332(3) Uani 1 1 d . . . H5A H 0.6253 0.5470 -0.0524 0.040 Uiso 1 1 calc R . . C6 C 0.75353(12) 0.66025(14) -0.02174(11) 0.0302(3) Uani 1 1 d . . . C7 C 0.76461(12) 0.70057(15) 0.07712(11) 0.0313(3) Uani 1 1 d . . . H7A H 0.7389 0.6470 0.1220 0.038 Uiso 1 1 calc R . . C8 C 0.81213(12) 0.81671(15) 0.11237(11) 0.0323(3) Uani 1 1 d . . . H8A H 0.8184 0.8418 0.1802 0.039 Uiso 1 1 calc R . . C9 C 0.85012(12) 0.89546(15) 0.04784(12) 0.0319(3) Uani 1 1 d . . . C10 C 0.83903(14) 0.85835(16) -0.05186(12) 0.0375(4) Uani 1 1 d . . . H10A H 0.8640 0.9127 -0.0968 0.045 Uiso 1 1 calc R . . C11 C 0.79170(14) 0.74220(16) -0.08549(12) 0.0366(3) Uani 1 1 d . . . H11A H 0.7850 0.7177 -0.1535 0.044 Uiso 1 1 calc R . . C12 C 0.93035(16) 0.2623(2) -0.10343(18) 0.0538(5) Uani 1 1 d . . . H12A H 0.9282 0.2344 -0.1722 0.081 Uiso 1 1 calc R . . H12B H 0.9441 0.1870 -0.0585 0.081 Uiso 1 1 calc R . . H12C H 0.9837 0.3272 -0.0829 0.081 Uiso 1 1 calc R . . C13 C 0.91855(16) 1.04646(18) 0.17778(14) 0.0452(4) Uani 1 1 d . . . H13A H 0.9591 1.1261 0.1884 0.068 Uiso 1 1 calc R . . H13B H 0.9553 0.9761 0.2187 0.068 Uiso 1 1 calc R . . H13C H 0.8547 1.0617 0.1971 0.068 Uiso 1 1 calc R . . C14 C 0.59904(11) 0.23059(14) -0.01144(11) 0.0293(3) Uani 1 1 d . . . C15 C 0.63849(12) 0.10633(15) -0.01437(12) 0.0339(3) Uani 1 1 d . . . H15A H 0.7001 0.0832 0.0301 0.041 Uiso 1 1 calc R . . C16 C 0.58720(13) 0.01663(16) -0.08254(13) 0.0377(4) Uani 1 1 d . . . H16A H 0.6139 -0.0685 -0.0842 0.045 Uiso 1 1 calc R . . C17 C 0.49722(13) 0.04912(16) -0.14863(12) 0.0352(3) Uani 1 1 d . . . C18 C 0.45929(13) 0.17431(17) -0.14465(13) 0.0380(4) Uani 1 1 d . . . H18A H 0.3980 0.1977 -0.1896 0.046 Uiso 1 1 calc R . . C19 C 0.50885(12) 0.26526(16) -0.07675(13) 0.0358(3) Uani 1 1 d . . . H19A H 0.4818 0.3502 -0.0746 0.043 Uiso 1 1 calc R . . C20 C 0.43999(17) -0.0483(2) -0.22201(15) 0.0518(5) Uani 1 1 d . . . H20A H 0.4704 -0.1346 -0.2073 0.078 Uiso 1 1 calc R . . H20B H 0.4426 -0.0226 -0.2902 0.078 Uiso 1 1 calc R . . H20C H 0.3698 -0.0510 -0.2162 0.078 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 0.0381(2) 0.02568(18) 0.02959(18) -0.00328(13) 0.00692(14) 0.00164(14) N 0.0339(6) 0.0247(6) 0.0337(6) 0.0031(5) 0.0038(5) 0.0024(5) O1 0.0540(7) 0.0308(6) 0.0391(6) -0.0026(5) 0.0083(5) -0.0072(5) O2 0.0485(7) 0.0358(6) 0.0291(5) 0.0021(4) 0.0035(5) -0.0008(5) O3 0.0492(7) 0.0330(6) 0.0476(7) -0.0096(5) 0.0179(6) 0.0045(5) C1 0.0345(8) 0.0340(8) 0.0375(8) 0.0042(6) 0.0067(6) 0.0064(6) C2 0.0416(9) 0.0330(8) 0.0460(9) -0.0033(7) 0.0125(7) 0.0000(7) C3 0.0559(11) 0.0385(9) 0.0306(8) -0.0046(7) 0.0079(7) 0.0001(8) C4 0.0505(10) 0.0361(8) 0.0300(7) -0.0013(6) -0.0046(7) 0.0011(7) C5 0.0355(8) 0.0275(7) 0.0326(7) 0.0023(6) -0.0004(6) 0.0035(6) C6 0.0344(7) 0.0254(6) 0.0286(7) 0.0024(5) 0.0027(6) 0.0058(5) C7 0.0347(7) 0.0295(7) 0.0301(7) 0.0031(6) 0.0083(6) 0.0028(6) C8 0.0375(8) 0.0314(7) 0.0280(7) -0.0002(5) 0.0075(6) 0.0035(6) C9 0.0357(8) 0.0254(7) 0.0334(7) 0.0010(5) 0.0055(6) 0.0027(6) C10 0.0506(10) 0.0313(8) 0.0314(7) 0.0047(6) 0.0111(7) -0.0005(7) C11 0.0518(10) 0.0307(7) 0.0262(7) 0.0021(6) 0.0065(6) 0.0039(7) C12 0.0517(11) 0.0455(10) 0.0709(14) 0.0027(10) 0.0281(10) 0.0065(9) C13 0.0521(11) 0.0374(9) 0.0410(9) -0.0059(7) -0.0001(8) -0.0007(8) C14 0.0311(7) 0.0260(6) 0.0308(7) -0.0024(5) 0.0069(6) 0.0019(5) C15 0.0328(7) 0.0284(7) 0.0385(8) -0.0028(6) 0.0039(6) 0.0054(6) C16 0.0410(9) 0.0287(7) 0.0450(9) -0.0076(6) 0.0129(7) 0.0015(6) C17 0.0386(8) 0.0378(8) 0.0313(7) -0.0055(6) 0.0121(6) -0.0083(6) C18 0.0326(8) 0.0419(9) 0.0369(8) 0.0014(7) 0.0028(6) -0.0001(6) C19 0.0343(8) 0.0305(7) 0.0412(8) 0.0007(6) 0.0055(6) 0.0057(6) C20 0.0577(12) 0.0547(11) 0.0431(10) -0.0169(9) 0.0117(9) -0.0175(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O2 1.4375(12) . ? S O3 1.4375(12) . ? S N 1.6248(14) . ? S C14 1.7635(15) . ? N C1 1.466(2) . ? N C5 1.4888(19) . ? O1 C9 1.3684(19) . ? O1 C13 1.427(2) . ? C1 C2 1.529(2) . ? C2 C12 1.517(3) . ? C2 C3 1.530(3) . ? C3 C4 1.519(3) . ? C4 C5 1.536(2) . ? C5 C6 1.530(2) . ? C6 C7 1.392(2) . ? C6 C11 1.397(2) . ? C7 C8 1.391(2) . ? C8 C9 1.384(2) . ? C9 C10 1.394(2) . ? C10 C11 1.385(2) . ? C14 C15 1.390(2) . ? C14 C19 1.394(2) . ? C15 C16 1.384(2) . ? C16 C17 1.391(2) . ? C17 C18 1.392(2) . ? C17 C20 1.505(2) . ? C18 C19 1.382(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S O3 119.30(8) . . ? O2 S N 106.54(7) . . ? O3 S N 107.00(7) . . ? O2 S C14 107.56(7) . . ? O3 S C14 107.34(7) . . ? N S C14 108.76(7) . . ? C1 N C5 116.04(13) . . ? C1 N S 119.19(10) . . ? C5 N S 120.67(11) . . ? C9 O1 C13 117.20(14) . . ? N C1 C2 112.38(13) . . ? C12 C2 C1 109.88(16) . . ? C12 C2 C3 112.98(16) . . ? C1 C2 C3 108.24(14) . . ? C4 C3 C2 109.88(15) . . ? C3 C4 C5 113.00(14) . . ? N C5 C6 108.87(12) . . ? N C5 C4 109.91(13) . . ? C6 C5 C4 115.49(14) . . ? C7 C6 C11 117.14(14) . . ? C7 C6 C5 118.85(14) . . ? C11 C6 C5 123.95(14) . . ? C8 C7 C6 122.16(15) . . ? C9 C8 C7 119.50(14) . . ? O1 C9 C8 124.50(14) . . ? O1 C9 C10 115.89(14) . . ? C8 C9 C10 119.61(15) . . ? C11 C10 C9 120.04(15) . . ? C10 C11 C6 121.55(15) . . ? C15 C14 C19 120.51(14) . . ? C15 C14 S 119.80(12) . . ? C19 C14 S 119.66(12) . . ? C16 C15 C14 119.44(15) . . ? C15 C16 C17 121.07(15) . . ? C16 C17 C18 118.51(15) . . ? C16 C17 C20 121.53(16) . . ? C18 C17 C20 119.95(17) . . ? C19 C18 C17 121.44(15) . . ? C18 C19 C14 119.02(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.57 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.599 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.055