data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 N O4 S' _chemical_formula_weight 423.51 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.9080(3) _cell_length_b 6.08900(10) _cell_length_c 22.6160(4) _cell_angle_alpha 90.00 _cell_angle_beta 123.9211(6) _cell_angle_gamma 90.00 _cell_volume 2274.92(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6241 _cell_measurement_theta_min 1.08 _cell_measurement_theta_max 30.76 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method 'Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5623 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.76 _reflns_number_total 5623 _reflns_number_gt 3930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Bruker-Nonius, 1998)' _computing_cell_refinement 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; Altamore, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. and Camalli, M. J. Appl. Cryst. (1994) 27, 435-436 Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box 811, 2600 Av, Delft, The Netherlands. Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. Univ. of G\"ottingen, Germany. ; _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^)+(0.0415P)^2^+2.4962P] 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 5623 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1421 _refine_ls_R_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1714 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.792 _diffrn_reflns_theta_full 30.76 _diffrn_measured_fraction_theta_full 0.792 _refine_diff_density_max 0.302 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.049 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 0.79756(5) -0.19603(17) 0.10260(4) 0.0607(3) Uani 1 1 d . . . O1 O 0.76084(12) 0.0691(3) 0.33757(9) 0.0469(5) Uani 1 1 d . . . O2 O 0.82957(15) -0.1573(5) 0.31097(12) 0.0715(8) Uani 1 1 d . . . O3 O 0.78861(19) -0.4303(5) 0.09554(17) 0.0974(11) Uani 1 1 d . . . O4 O 0.74642(14) -0.0599(6) 0.04116(11) 0.0829(9) Uani 1 1 d . . . N1 N 0.73360(13) 0.0767(4) 0.22806(11) 0.0404(6) Uani 1 1 d . . . C1 C 0.67223(17) 0.2500(5) 0.20866(14) 0.0447(7) Uani 1 1 d . . . H1 H 0.6888 0.3435 0.2488 0.054 Uiso 1 1 d R . . C2 C 0.58889(17) 0.1583(6) 0.18190(16) 0.0501(8) Uani 1 1 d . . . C3 C 0.5775(2) -0.0251(7) 0.2100(2) 0.0635(9) Uani 1 1 d . . . H3 H 0.6233 -0.1031 0.2480 0.076 Uiso 1 1 d R . . C4 C 0.5000(3) -0.0983(9) 0.1854(3) 0.0939(15) Uani 1 1 d . . . H4 H 0.4947 -0.2304 0.2056 0.113 Uiso 1 1 d R . . C5 C 0.4342(3) 0.0173(11) 0.1324(3) 0.1112(19) Uani 1 1 d . . . H5 H 0.3795 -0.0239 0.1144 0.133 Uiso 1 1 d R . . C6 C 0.4448(3) 0.2024(10) 0.1041(3) 0.0983(16) Uani 1 1 d . . . H6 H 0.3990 0.2818 0.0666 0.118 Uiso 1 1 d R . . C7 C 0.5216(2) 0.2769(7) 0.12769(19) 0.0696(11) Uani 1 1 d . . . C8 C 0.5332(3) 0.4678(8) 0.09511(19) 0.0817(13) Uani 1 1 d . . . H8 H 0.4893 0.5667 0.0656 0.098 Uiso 1 1 d R . . C9 C 0.6027(3) 0.5139(7) 0.10489(19) 0.0771(11) Uani 1 1 d . . . H9 H 0.6069 0.6388 0.0812 0.092 Uiso 1 1 d R . . C10 C 0.6749(2) 0.3725(6) 0.15115(16) 0.0574(9) Uani 1 1 d . . . H10 H 0.7229 0.4611 0.1740 0.069 Uiso 1 1 d R . . C11 C 0.6868(2) 0.1871(6) 0.11229(16) 0.0568(9) Uani 1 1 d . . . H11A H 0.6349 0.1232 0.0786 0.068 Uiso 1 1 d R . . H11B H 0.7098 0.2431 0.0876 0.068 Uiso 1 1 d R . . C12 C 0.74190(16) 0.0306(5) 0.17153(14) 0.0424(7) Uani 1 1 d . . . C13 C 0.79049(18) -0.1239(6) 0.17307(15) 0.0498(8) Uani 1 1 d . . . H13 H 0.8236 -0.1966 0.2182 0.060 Uiso 1 1 d R . . C14 C 0.89902(18) -0.1395(6) 0.13304(15) 0.0471(8) Uani 1 1 d . . . C15 C 0.9573(2) -0.2975(6) 0.1708(2) 0.0702(10) Uani 1 1 d . . . H15 H 0.9422 -0.4337 0.1816 0.084 Uiso 1 1 d R . . C16 C 1.0361(3) -0.2551(8) 0.1914(2) 0.0872(13) Uani 1 1 d . . . H16 H 1.0774 -0.3636 0.2177 0.105 Uiso 1 1 d R . . C17 C 1.0552(2) -0.0640(8) 0.1744(2) 0.0761(12) Uani 1 1 d . . . H17 H 1.1097 -0.0350 0.1887 0.091 Uiso 1 1 d R . . C18 C 0.9977(2) 0.0910(7) 0.1382(2) 0.0758(11) Uani 1 1 d . . . H18 H 1.0099 0.2288 0.1255 0.091 Uiso 1 1 d R . . C19 C 0.9187(2) 0.0561(6) 0.11717(19) 0.0611(9) Uani 1 1 d . . . H19 H 0.8784 0.1681 0.0920 0.073 Uiso 1 1 d R . . C20 C 0.77982(17) -0.0181(5) 0.29484(14) 0.0442(7) Uani 1 1 d . . . C21 C 0.7960(2) -0.0187(6) 0.41053(15) 0.0554(9) Uani 1 1 d . . . C22 C 0.8844(3) 0.0344(10) 0.4557(2) 0.1087(18) Uani 1 1 d . . . H22A H 0.9137 -0.0676 0.4459 0.130 Uiso 1 1 d R . . H22B H 0.9035 0.0251 0.5051 0.130 Uiso 1 1 d R . . H22C H 0.8924 0.1808 0.4450 0.130 Uiso 1 1 d R . . C23 C 0.7772(3) -0.2596(7) 0.4066(2) 0.0915(15) Uani 1 1 d . . . H23A H 0.7236 -0.2857 0.3655 0.110 Uiso 1 1 d R . . H23B H 0.7801 -0.3042 0.4487 0.110 Uiso 1 1 d R . . H23C H 0.8155 -0.3426 0.4026 0.110 Uiso 1 1 d R . . C24 C 0.7489(3) 0.1092(7) 0.4334(2) 0.0807(12) Uani 1 1 d . . . H24A H 0.7626 0.2618 0.4369 0.097 Uiso 1 1 d R . . H24B H 0.7625 0.0574 0.4790 0.097 Uiso 1 1 d R . . H24C H 0.6919 0.0907 0.3989 0.097 Uiso 1 1 d 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 0.0584(5) 0.0865(8) 0.0517(5) -0.0286(4) 0.0397(4) -0.0279(5) O1 0.0530(11) 0.0584(15) 0.0358(10) 0.0055(9) 0.0287(9) 0.0075(10) O2 0.0732(15) 0.099(2) 0.0553(13) 0.0224(13) 0.0442(12) 0.0401(15) O3 0.132(3) 0.092(2) 0.125(2) -0.0674(19) 0.107(2) -0.0685(19) O4 0.0526(13) 0.156(3) 0.0353(11) -0.0137(14) 0.0218(10) -0.0033(16) N1 0.0394(12) 0.0510(17) 0.0345(11) 0.0002(10) 0.0229(10) -0.0027(11) C1 0.0450(15) 0.048(2) 0.0375(14) -0.0031(13) 0.0208(12) -0.0005(13) C2 0.0401(15) 0.062(2) 0.0470(16) -0.0105(15) 0.0234(13) -0.0007(14) C3 0.0501(18) 0.069(3) 0.079(2) -0.010(2) 0.0406(18) -0.0104(17) C4 0.069(3) 0.092(4) 0.136(4) -0.021(3) 0.066(3) -0.022(2) C5 0.046(2) 0.139(5) 0.142(5) -0.042(4) 0.049(3) -0.020(3) C6 0.051(2) 0.121(5) 0.096(3) -0.018(3) 0.024(2) 0.008(3) C7 0.0471(19) 0.090(3) 0.060(2) -0.015(2) 0.0228(16) 0.0062(19) C8 0.078(3) 0.091(3) 0.051(2) 0.013(2) 0.0207(19) 0.031(2) C9 0.092(3) 0.073(3) 0.055(2) 0.0146(19) 0.034(2) 0.012(2) C10 0.064(2) 0.059(2) 0.0443(16) 0.0063(15) 0.0266(15) -0.0064(17) C11 0.0608(19) 0.070(3) 0.0412(16) 0.0028(15) 0.0294(15) -0.0068(17) C12 0.0406(14) 0.055(2) 0.0364(13) -0.0088(13) 0.0243(12) -0.0156(13) C13 0.0458(16) 0.069(2) 0.0410(15) -0.0116(14) 0.0285(13) -0.0145(15) C14 0.0494(16) 0.059(2) 0.0434(15) -0.0071(14) 0.0326(13) -0.0048(15) C15 0.086(3) 0.051(3) 0.093(3) 0.013(2) 0.062(2) 0.009(2) C16 0.066(2) 0.093(4) 0.107(3) 0.018(3) 0.051(2) 0.030(2) C17 0.053(2) 0.092(3) 0.090(3) -0.005(2) 0.044(2) -0.005(2) C18 0.068(2) 0.074(3) 0.094(3) 0.010(2) 0.049(2) -0.012(2) C19 0.0529(19) 0.058(3) 0.070(2) 0.0143(18) 0.0326(17) 0.0007(16) C20 0.0412(15) 0.057(2) 0.0409(14) 0.0019(13) 0.0267(12) 0.0011(14) C21 0.074(2) 0.058(2) 0.0397(15) 0.0074(14) 0.0349(16) 0.0083(17) C22 0.073(3) 0.173(6) 0.049(2) -0.001(3) 0.015(2) 0.007(3) C23 0.158(5) 0.066(3) 0.086(3) 0.016(2) 0.090(3) 0.017(3) C24 0.125(3) 0.081(3) 0.062(2) 0.012(2) 0.068(2) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.435(3) . ? S1 O4 1.440(3) . ? S1 C13 1.733(3) . ? S1 C14 1.766(3) . ? O1 C20 1.329(3) . ? O1 C21 1.487(3) . ? O2 C20 1.196(4) . ? N1 C20 1.382(3) . ? N1 C12 1.406(3) . ? N1 C1 1.483(4) . ? C1 C2 1.520(4) . ? C1 C10 1.526(4) . ? C1 H1 0.9601 . ? C2 C3 1.365(5) . ? C2 C7 1.410(5) . ? C3 C4 1.390(5) . ? C3 H3 0.9599 . ? C4 C5 1.376(7) . ? C4 H4 0.9598 . ? C5 C6 1.370(8) . ? C5 H5 0.9602 . ? C6 C7 1.384(6) . ? C6 H6 0.9600 . ? C7 C8 1.462(6) . ? C8 C9 1.304(6) . ? C8 H8 0.9601 . ? C9 C10 1.491(5) . ? C9 H9 0.9600 . ? C10 C11 1.528(5) . ? C10 H10 0.9599 . ? C11 C12 1.506(4) . ? C11 H11A 0.9599 . ? C11 H11B 0.9601 . ? C12 C13 1.335(4) . ? C13 H13 0.9601 . ? C14 C19 1.363(5) . ? C14 C15 1.377(5) . ? C15 C16 1.387(5) . ? C15 H15 0.9599 . ? C16 C17 1.346(6) . ? C16 H16 0.9599 . ? C17 C18 1.351(6) . ? C17 H17 0.9600 . ? C18 C19 1.383(5) . ? C18 H18 0.9601 . ? C19 H19 0.9601 . ? C21 C22 1.496(5) . ? C21 C23 1.505(5) . ? C21 C24 1.515(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9599 . ? C23 H23A 0.9599 . ? C23 H23B 0.9602 . ? C23 H23C 0.9602 . ? C24 H24A 0.9600 . ? C24 H24B 0.9599 . ? C24 H24C 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 O3 S1 O4 119.17(19) . . ? O3 S1 C13 106.59(16) . . ? O4 S1 C13 111.40(17) . . ? O3 S1 C14 106.31(18) . . ? O4 S1 C14 107.63(15) . . ? C13 S1 C14 104.73(13) . . ? C20 O1 C21 121.0(2) . . ? C20 N1 C12 124.4(2) . . ? C20 N1 C1 123.8(2) . . ? C12 N1 C1 111.6(2) . . ? N1 C1 C2 113.1(3) . . ? N1 C1 C10 100.7(2) . . ? C2 C1 C10 112.9(2) . . ? N1 C1 H1 110.5 . . ? C2 C1 H1 108.5 . . ? C10 C1 H1 111.0 . . ? C3 C2 C7 120.0(3) . . ? C3 C2 C1 122.9(3) . . ? C7 C2 C1 117.0(3) . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 122.6 . . ? C3 C4 H4 118.1 . . ? C6 C5 C4 120.5(4) . . ? C6 C5 H5 116.8 . . ? C4 C5 H5 122.6 . . ? C5 C6 C7 121.0(5) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 118.4 . . ? C6 C7 C2 118.4(4) . . ? C6 C7 C8 121.2(4) . . ? C2 C7 C8 120.3(3) . . ? C9 C8 C7 122.5(4) . . ? C9 C8 H8 116.9 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.8 . . ? C9 C10 C1 113.7(3) . . ? C9 C10 C11 114.9(3) . . ? C1 C10 C11 102.7(3) . . ? C9 C10 H10 109.5 . . ? C1 C10 H10 108.3 . . ? C11 C10 H10 107.2 . . ? C12 C11 C10 103.1(2) . . ? C12 C11 H11A 112.1 . . ? C10 C11 H11A 108.2 . . ? C12 C11 H11B 113.2 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 109.5 . . ? C13 C12 N1 124.6(3) . . ? C13 C12 C11 128.8(3) . . ? N1 C12 C11 106.6(3) . . ? C12 C13 S1 125.7(3) . . ? C12 C13 H13 114.2 . . ? S1 C13 H13 120.1 . . ? C19 C14 C15 120.5(3) . . ? C19 C14 S1 120.1(3) . . ? C15 C14 S1 119.4(3) . . ? C14 C15 C16 118.8(4) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 122.1 . . ? C17 C16 C15 120.8(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.9(4) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 119.5 . . ? C17 C18 C19 121.2(4) . . ? C17 C18 H18 121.4 . . ? C19 C18 H18 117.4 . . ? C14 C19 C18 118.9(3) . . ? C14 C19 H19 120.7 . . ? C18 C19 H19 120.5 . . ? O2 C20 O1 125.8(3) . . ? O2 C20 N1 124.3(3) . . ? O1 C20 N1 110.0(3) . . ? O1 C21 C22 109.0(3) . . ? O1 C21 C23 109.8(3) . . ? C22 C21 C23 114.2(4) . . ? O1 C21 C24 101.4(3) . . ? C22 C21 C24 111.9(3) . . ? C23 C21 C24 109.8(3) . . ? C21 C22 H22A 109.8 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.1 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 108.9 . . ? C21 C23 H23B 110.0 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 108.8 . . ? C21 C24 H24B 109.8 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.7 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ?