data_k08254 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O4 S' _chemical_formula_sum 'C21 H23 N O4 S' _chemical_formula_weight 385.46 _chemical_absolute_configuration 'ad' 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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.7600(3) _cell_length_b 8.8993(3) _cell_length_c 27.2380(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1881.02(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 11329 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.199 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11329 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4147 _reflns_number_gt 2979 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0495P)^2^+0.4721P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(10) _refine_ls_number_reflns 4147 _refine_ls_number_parameters 248 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.060 _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 0.45496(9) 0.64044(8) 0.40403(3) 0.03293(19) Uani 1 1 d . A -1 O1 O 0.4276(3) 0.5958(2) 0.45397(7) 0.0442(5) Uani 1 1 d . A -1 O2 O 0.6271(2) 0.6372(2) 0.38574(8) 0.0436(5) Uani 1 1 d . A -1 O3 O 0.1653(3) 0.3229(2) 0.36247(9) 0.0492(6) Uani 1 1 d . A -1 O4 O 0.7134(3) 0.0503(3) 0.37026(9) 0.0507(7) Uani 0.897(4) 1 d P A -1 N1 N 0.3218(3) 0.5366(3) 0.36728(8) 0.0301(5) Uani 1 1 d . A -1 C1 C 0.3540(4) 0.8171(3) 0.39168(11) 0.0377(7) Uani 1 1 d . A -1 H1A H 0.3021 0.8582 0.4221 0.045 Uiso 1 1 calc R A -1 H1B H 0.4399 0.8901 0.3793 0.045 Uiso 1 1 calc R A -1 C2 C 0.2156(3) 0.7901(3) 0.35336(10) 0.0310(6) Uani 1 1 d . A -1 C3 C 0.2602(4) 0.8233(3) 0.29867(11) 0.0365(7) Uani 1 1 d . A -1 C4 C 0.0887(4) 0.7553(4) 0.28045(11) 0.0407(8) Uani 1 1 d . A -1 H4A H 0.0721 0.7605 0.2441 0.049 Uiso 1 1 calc R A -1 C5 C 0.0957(4) 0.5944(4) 0.30119(11) 0.0448(8) Uani 1 1 d . A -1 H5A H 0.1744 0.5299 0.2818 0.054 Uiso 1 1 calc R A -1 H5B H -0.0201 0.5479 0.3021 0.054 Uiso 1 1 calc R A -1 C6 C 0.1662(3) 0.6224(3) 0.35347(10) 0.0322(6) Uani 1 1 d . A -1 H6A H 0.0731 0.6043 0.3781 0.039 Uiso 1 1 calc R A -1 C7 C -0.0472(4) 0.8434(4) 0.31043(11) 0.0428(7) Uani 1 1 d . A -1 H7A H -0.0784 0.9386 0.2938 0.051 Uiso 1 1 calc R A -1 H7B H -0.1527 0.7828 0.3154 0.051 Uiso 1 1 calc R A -1 C8 C 0.0445(4) 0.8740(3) 0.35979(10) 0.0384(7) Uani 1 1 d . A -1 H8A H 0.0635 0.9829 0.3649 0.046 Uiso 1 1 calc R A -1 H8B H -0.0223 0.8332 0.3877 0.046 Uiso 1 1 calc R A -1 C9 C 0.4221(4) 0.7456(4) 0.27906(12) 0.0494(9) Uani 1 1 d . A -1 H9A H 0.4398 0.7739 0.2447 0.074 Uiso 1 1 calc R A -1 H9B H 0.4080 0.6364 0.2814 0.074 Uiso 1 1 calc R A -1 H9C H 0.5221 0.7768 0.2985 0.074 Uiso 1 1 calc R A -1 C10 C 0.2815(5) 0.9918(4) 0.28767(12) 0.0506(9) Uani 1 1 d . A -1 H10A H 0.1802 1.0465 0.2996 0.076 Uiso 1 1 calc R A -1 H10B H 0.2930 1.0066 0.2522 0.076 Uiso 1 1 calc R A -1 H10C H 0.3849 1.0297 0.3042 0.076 Uiso 1 1 calc R A -1 C11 C 0.3018(4) 0.3818(3) 0.37338(10) 0.0354(7) Uani 1 1 d . A -1 C12 C 0.4518(4) 0.2922(3) 0.39081(10) 0.0330(6) Uani 1 1 d D A -1 C13 C 0.6055(4) 0.3076(3) 0.36856(11) 0.0385(7) Uani 1 1 d D A -1 H13A H 0.6199 0.3838 0.3445 0.046 Uiso 1 1 calc R A -1 C14 C 0.7500(4) 0.2106(4) 0.38048(12) 0.0475(8) Uani 1 1 d . A -1 H14A H 0.8686 0.2486 0.3732 0.057 Uiso 1 1 calc R A -1 C15 C 0.7299(4) 0.1051(4) 0.42115(12) 0.0459(8) Uani 1 1 d . A -1 H15A H 0.8366 0.0762 0.4394 0.055 Uiso 1 1 calc R A -1 C16 C 0.5677(4) 0.1014(3) 0.44844(11) 0.0350(7) Uani 1 1 d . A -1 C17 C 0.5516(5) 0.0096(3) 0.48996(11) 0.0465(8) Uani 1 1 d . A -1 H17A H 0.6479 -0.0461 0.5015 0.056 Uiso 1 1 calc R A -1 C18 C 0.3955(5) 0.0003(4) 0.51412(12) 0.0515(9) Uani 1 1 d . A -1 H18A H 0.3841 -0.0631 0.5420 0.062 Uiso 1 1 calc R A -1 C19 C 0.2560(5) 0.0828(4) 0.49793(11) 0.0484(9) Uani 1 1 d . A -1 H19A H 0.1488 0.0759 0.5146 0.058 Uiso 1 1 calc R A -1 C20 C 0.2719(4) 0.1752(3) 0.45753(11) 0.0391(7) Uani 1 1 d . A -1 H20A H 0.1752 0.2318 0.4468 0.047 Uiso 1 1 calc R A -1 C21 C 0.4269(4) 0.1871(3) 0.43212(10) 0.0310(6) Uani 1 1 d . A -1 O4A O 0.5004(19) 0.1827(17) 0.3498(6) 0.0507(7) Uani 0.103(4) 1 d PD A -2 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 0.0287(4) 0.0322(4) 0.0378(4) 0.0009(3) -0.0064(3) -0.0015(3) O1 0.0498(14) 0.0474(12) 0.0354(11) 0.0042(9) -0.0087(10) 0.0012(10) O2 0.0220(10) 0.0414(12) 0.0673(14) 0.0023(11) 0.0009(9) -0.0047(9) O3 0.0342(12) 0.0362(12) 0.0773(16) 0.0061(11) -0.0116(11) -0.0083(10) O4 0.0448(16) 0.0420(14) 0.0652(17) -0.0098(12) 0.0053(13) 0.0082(12) N1 0.0271(12) 0.0266(12) 0.0366(13) 0.0020(10) -0.0056(10) -0.0011(10) C1 0.0397(17) 0.0282(14) 0.0454(18) -0.0041(12) -0.0051(14) -0.0025(13) C2 0.0265(14) 0.0303(14) 0.0361(16) 0.0004(12) -0.0017(12) 0.0025(12) C3 0.0306(16) 0.0417(17) 0.0373(16) 0.0059(13) 0.0021(13) 0.0012(14) C4 0.045(2) 0.0474(18) 0.0297(16) 0.0011(13) -0.0073(14) 0.0016(15) C5 0.0464(19) 0.0441(18) 0.0438(18) -0.0055(14) -0.0113(15) -0.0005(15) C6 0.0239(13) 0.0345(15) 0.0382(16) 0.0024(13) -0.0037(12) 0.0021(13) C7 0.0307(15) 0.0532(18) 0.0446(17) 0.0121(15) -0.0041(14) 0.0080(17) C8 0.0333(14) 0.0419(16) 0.0400(16) 0.0017(14) 0.0045(14) 0.0089(16) C9 0.041(2) 0.063(2) 0.0441(19) 0.0114(16) 0.0107(15) 0.0089(17) C10 0.046(2) 0.051(2) 0.055(2) 0.0165(16) 0.0028(16) -0.0025(17) C11 0.0296(16) 0.0336(16) 0.0429(17) 0.0032(13) 0.0024(13) -0.0022(13) C12 0.0268(14) 0.0255(13) 0.0466(17) -0.0014(12) 0.0018(14) -0.0027(13) C13 0.0362(17) 0.0390(17) 0.0402(17) -0.0009(14) 0.0022(14) -0.0052(13) C14 0.0333(17) 0.0404(18) 0.069(2) -0.0087(16) 0.0114(16) 0.0014(15) C15 0.0330(17) 0.0471(19) 0.058(2) 0.0007(15) -0.0075(15) 0.0076(15) C16 0.0346(17) 0.0306(14) 0.0398(16) -0.0049(12) -0.0073(13) -0.0012(13) C17 0.053(2) 0.0409(17) 0.0460(18) 0.0021(14) -0.0191(17) -0.0048(18) C18 0.071(3) 0.0442(19) 0.0390(18) 0.0022(15) -0.0036(18) -0.0147(18) C19 0.056(2) 0.0416(17) 0.048(2) -0.0014(14) 0.0165(18) -0.0055(17) C20 0.0396(17) 0.0308(15) 0.0471(18) -0.0033(13) 0.0070(15) -0.0014(14) C21 0.0323(17) 0.0258(13) 0.0350(15) -0.0048(11) 0.0002(13) -0.0025(12) O4A 0.0448(16) 0.0420(14) 0.0652(17) -0.0098(12) 0.0053(13) 0.0082(12) _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 O2 1.426(2) . ? S1 O1 1.433(2) . ? S1 N1 1.710(2) . ? S1 C1 1.789(3) . ? O3 C11 1.219(3) . ? O4 C15 1.475(4) . ? O4 C14 1.480(4) . ? N1 C11 1.397(4) . ? N1 C6 1.477(3) . ? C1 C2 1.517(4) . ? C2 C8 1.533(4) . ? C2 C6 1.541(4) . ? C2 C3 1.557(4) . ? C3 C9 1.530(4) . ? C3 C10 1.538(4) . ? C3 C4 1.544(4) . ? C4 C5 1.540(4) . ? C4 C7 1.547(4) . ? C5 C6 1.546(4) . ? C7 C8 1.545(4) . ? C11 C12 1.488(4) . ? C12 C13 1.345(4) . ? C12 C21 1.476(4) . ? C13 C14 1.452(4) . ? C14 C15 1.460(5) . ? C15 C16 1.462(4) . ? C16 C17 1.400(4) . ? C16 C21 1.404(4) . ? C17 C18 1.381(5) . ? C18 C19 1.380(5) . ? C19 C20 1.379(4) . ? C20 C21 1.392(4) . ? 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 S1 O1 117.69(13) . . ? O2 S1 N1 110.54(12) . . ? O1 S1 N1 108.45(12) . . ? O2 S1 C1 111.24(14) . . ? O1 S1 C1 110.94(14) . . ? N1 S1 C1 95.75(13) . . ? C15 O4 C14 59.2(2) . . ? C11 N1 C6 116.7(2) . . ? C11 N1 S1 122.04(19) . . ? C6 N1 S1 111.34(17) . . ? C2 C1 S1 107.48(19) . . ? C1 C2 C8 117.2(2) . . ? C1 C2 C6 109.1(2) . . ? C8 C2 C6 104.8(2) . . ? C1 C2 C3 118.1(2) . . ? C8 C2 C3 102.1(2) . . ? C6 C2 C3 103.9(2) . . ? C9 C3 C10 106.5(3) . . ? C9 C3 C4 114.7(3) . . ? C10 C3 C4 114.3(3) . . ? C9 C3 C2 115.5(2) . . ? C10 C3 C2 113.3(2) . . ? C4 C3 C2 92.4(2) . . ? C5 C4 C3 102.5(2) . . ? C5 C4 C7 107.6(3) . . ? C3 C4 C7 102.7(2) . . ? C4 C5 C6 101.6(2) . . ? N1 C6 C2 107.3(2) . . ? N1 C6 C5 116.2(2) . . ? C2 C6 C5 104.0(2) . . ? C8 C7 C4 103.6(2) . . ? C2 C8 C7 102.3(2) . . ? O3 C11 N1 119.4(3) . . ? O3 C11 C12 121.8(3) . . ? N1 C11 C12 118.7(2) . . ? C13 C12 C21 121.6(3) . . ? C13 C12 C11 119.7(3) . . ? C21 C12 C11 118.7(2) . . ? C12 C13 C14 121.6(3) . . ? C13 C14 C15 118.0(3) . . ? C13 C14 O4 112.5(3) . . ? C15 C14 O4 60.2(2) . . ? C14 C15 C16 119.5(3) . . ? C14 C15 O4 60.6(2) . . ? C16 C15 O4 113.3(3) . . ? C17 C16 C21 120.2(3) . . ? C17 C16 C15 120.0(3) . . ? C21 C16 C15 119.7(3) . . ? C18 C17 C16 119.9(3) . . ? C19 C18 C17 120.3(3) . . ? C20 C19 C18 120.1(3) . . ? C19 C20 C21 121.3(3) . . ? C20 C21 C16 118.2(3) . . ? C20 C21 C12 122.7(3) . . ? C16 C21 C12 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.251 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.055