data_a _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Jiaxi Xu' _publ_contact_author_address ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; _publ_contact_author_email Jxxu@pku.edu.cn _publ_contact_author_phone 86-10-62751497 _publ_contact_author_fax 86-10-62751708 loop_ _publ_author_name _publ_author_address 'Xu, Jiaxi' ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; 'Jiao, Lei' ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; 'Zhang, Qianfeng' ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; 'Liang, Yong' ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; 'Zhang, Shiwei' ;College of Chemistry and Molecular Engineering Peking University Beijing 100871 China ; _audit_creation_method SHELXL-97 _chemical_name_systematic '[1,5]benzothiazepine-derived beta-lactam derivative' _chemical_melting_point 449 _chemical_formula_moiety 'C32 H27 N O3 S2' _chemical_formula_sum 'C32 H27 N O3 S2' _chemical_formula_weight 537.67 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7629(16) _cell_length_b 8.5948(17) _cell_length_c 21.728(4) _cell_angle_alpha 81.54(3) _cell_angle_beta 85.90(3) _cell_angle_gamma 73.88(3) _cell_volume 1376.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8218 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8218 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4652 _reflns_number_gt 3294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0700P)^2^+0.0000P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4652 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 0.32725(8) 0.60955(7) 0.41172(2) 0.05697(19) Uani 1 1 d . . . S2 S 0.53987(7) 0.66464(8) 0.12916(2) 0.05220(18) Uani 1 1 d . . . O1 O 0.3672(2) 0.98488(19) 0.21526(7) 0.0630(4) Uani 1 1 d . . . O2 O 0.19085(18) 0.57824(18) 0.14579(7) 0.0506(4) Uani 1 1 d . . . O3 O 0.0535(2) 0.8104(2) 0.18506(8) 0.0669(5) Uani 1 1 d . . . N1 N 0.4670(2) 0.73232(19) 0.27719(7) 0.0403(4) Uani 1 1 d . . . C1 C 0.3942(3) 0.8385(3) 0.22724(10) 0.0452(5) Uani 1 1 d . . . C2 C 0.3731(2) 0.7007(2) 0.19266(9) 0.0392(5) Uani 1 1 d . . . C3 C 0.4404(2) 0.5829(2) 0.25535(8) 0.0376(4) Uani 1 1 d . . . C4 C 0.2918(3) 0.5243(2) 0.29293(8) 0.0405(5) Uani 1 1 d . . . H4A H 0.2639 0.4412 0.2727 0.049 Uiso 1 1 calc R . . H4B H 0.1847 0.6151 0.2932 0.049 Uiso 1 1 calc R . . C5 C 0.3420(3) 0.4541(2) 0.35991(9) 0.0429(5) Uani 1 1 d . . . H5 H 0.4648 0.3827 0.3599 0.051 Uiso 1 1 calc R . . C6 C 0.5038(3) 0.7023(2) 0.39035(9) 0.0462(5) Uani 1 1 d . . . C7 C 0.5485(3) 0.7588(2) 0.32974(9) 0.0426(5) Uani 1 1 d . . . C8 C 0.6758(3) 0.8473(3) 0.31935(11) 0.0530(6) Uani 1 1 d . . . H8 H 0.7067 0.8845 0.2788 0.064 Uiso 1 1 calc R . . C9 C 0.7563(3) 0.8803(3) 0.36867(11) 0.0622(6) Uani 1 1 d . . . H9 H 0.8406 0.9400 0.3612 0.075 Uiso 1 1 calc R . . C10 C 0.7126(3) 0.8257(3) 0.42826(12) 0.0648(7) Uani 1 1 d . . . H10 H 0.7656 0.8496 0.4615 0.078 Uiso 1 1 calc R . . C11 C 0.5899(3) 0.7352(3) 0.43917(10) 0.0583(6) Uani 1 1 d . . . H11 H 0.5638 0.6952 0.4799 0.070 Uiso 1 1 calc R . . C12 C 0.6070(2) 0.4430(2) 0.24775(8) 0.0377(4) Uani 1 1 d . . . C13 C 0.7722(3) 0.4349(3) 0.26993(10) 0.0490(5) Uani 1 1 d . . . H13 H 0.7860 0.5201 0.2893 0.059 Uiso 1 1 calc R . . C14 C 0.9175(3) 0.3008(3) 0.26349(11) 0.0590(6) Uani 1 1 d . . . H14 H 1.0272 0.2954 0.2795 0.071 Uiso 1 1 calc R . . C15 C 0.9005(3) 0.1760(3) 0.23372(11) 0.0586(6) Uani 1 1 d . . . H15 H 0.9994 0.0878 0.2286 0.070 Uiso 1 1 calc R . . C16 C 0.7374(3) 0.1814(3) 0.21139(10) 0.0538(6) Uani 1 1 d . . . H16 H 0.7254 0.0966 0.1914 0.065 Uiso 1 1 calc R . . C17 C 0.5910(3) 0.3134(2) 0.21870(9) 0.0470(5) Uani 1 1 d . . . H17 H 0.4804 0.3158 0.2041 0.056 Uiso 1 1 calc R . . C18 C 0.2158(3) 0.3539(2) 0.38865(9) 0.0424(5) Uani 1 1 d . . . C19 C 0.0434(3) 0.4274(3) 0.41022(10) 0.0519(5) Uani 1 1 d . . . H19 H 0.0054 0.5403 0.4095 0.062 Uiso 1 1 calc R . . C20 C -0.0717(3) 0.3337(3) 0.43275(11) 0.0610(6) Uani 1 1 d . . . H20 H -0.1866 0.3839 0.4471 0.073 Uiso 1 1 calc R . . C21 C -0.0183(4) 0.1686(3) 0.43414(11) 0.0629(7) Uani 1 1 d . . . H21 H -0.0963 0.1060 0.4493 0.075 Uiso 1 1 calc R . . C22 C 0.1515(4) 0.0949(3) 0.41304(12) 0.0690(7) Uani 1 1 d . . . H22 H 0.1879 -0.0180 0.4137 0.083 Uiso 1 1 calc R . . C23 C 0.2686(3) 0.1864(3) 0.39097(11) 0.0579(6) Uani 1 1 d . . . H23 H 0.3840 0.1347 0.3776 0.069 Uiso 1 1 calc R . . C24 C 0.1863(3) 0.7061(3) 0.17394(9) 0.0421(5) Uani 1 1 d . . . C25 C 0.0211(3) 0.5687(3) 0.12400(12) 0.0656(7) Uani 1 1 d . . . H25A H -0.0309 0.6651 0.0951 0.079 Uiso 1 1 calc R . . H25B H -0.0631 0.5618 0.1588 0.079 Uiso 1 1 calc R . . C26 C 0.0598(4) 0.4190(4) 0.09236(15) 0.1003(11) Uani 1 1 d . . . H26A H -0.0495 0.4093 0.0773 0.150 Uiso 1 1 calc R . . H26B H 0.1106 0.3244 0.1214 0.150 Uiso 1 1 calc R . . H26C H 0.1433 0.4271 0.0580 0.150 Uiso 1 1 calc R . . C27 C 0.4220(3) 0.7850(3) 0.06408(9) 0.0478(5) Uani 1 1 d . . . C28 C 0.4560(4) 0.7158(3) 0.00947(11) 0.0731(7) Uani 1 1 d . . . H28 H 0.5346 0.6122 0.0090 0.088 Uiso 1 1 calc R . . C29 C 0.3739(5) 0.7996(4) -0.04423(12) 0.0946(10) Uani 1 1 d . . . H29 H 0.3979 0.7533 -0.0811 0.114 Uiso 1 1 calc R . . C30 C 0.2564(4) 0.9520(4) -0.04333(12) 0.0824(9) Uani 1 1 d . . . H30 H 0.1983 1.0076 -0.0794 0.099 Uiso 1 1 calc R . . C31 C 0.2247(4) 1.0215(3) 0.01013(12) 0.0753(8) Uani 1 1 d . . . H31 H 0.1457 1.1250 0.0104 0.090 Uiso 1 1 calc R . . C32 C 0.3095(3) 0.9393(3) 0.06443(11) 0.0636(6) Uani 1 1 d . . . H32 H 0.2901 0.9885 0.1006 0.076 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 S1 0.0774(4) 0.0615(4) 0.0415(3) -0.0165(3) 0.0074(3) -0.0318(3) S2 0.0402(3) 0.0688(4) 0.0415(3) 0.0005(3) -0.0009(2) -0.0088(3) O1 0.0816(11) 0.0386(9) 0.0686(10) 0.0014(7) -0.0225(9) -0.0153(8) O2 0.0417(8) 0.0562(9) 0.0573(9) -0.0158(7) -0.0059(7) -0.0138(7) O3 0.0429(8) 0.0643(11) 0.0899(12) -0.0284(9) -0.0091(8) 0.0025(8) N1 0.0488(10) 0.0344(9) 0.0386(9) -0.0049(7) -0.0074(8) -0.0114(8) C1 0.0451(12) 0.0443(13) 0.0472(12) -0.0063(10) -0.0065(10) -0.0124(10) C2 0.0397(10) 0.0397(11) 0.0372(10) -0.0029(9) -0.0048(9) -0.0091(9) C3 0.0427(11) 0.0372(11) 0.0348(10) -0.0070(8) -0.0058(9) -0.0116(9) C4 0.0417(11) 0.0428(12) 0.0380(10) -0.0082(9) -0.0021(9) -0.0115(9) C5 0.0464(11) 0.0403(12) 0.0424(11) -0.0089(9) -0.0020(9) -0.0106(10) C6 0.0574(13) 0.0388(12) 0.0437(12) -0.0087(9) -0.0082(10) -0.0116(10) C7 0.0497(12) 0.0349(11) 0.0448(12) -0.0100(9) -0.0091(10) -0.0097(10) C8 0.0610(14) 0.0498(14) 0.0544(13) -0.0061(11) -0.0075(11) -0.0242(12) C9 0.0707(15) 0.0614(16) 0.0665(16) -0.0124(13) -0.0125(13) -0.0330(14) C10 0.0796(17) 0.0602(16) 0.0638(16) -0.0140(12) -0.0249(13) -0.0253(14) C11 0.0782(16) 0.0578(15) 0.0429(12) -0.0117(11) -0.0114(11) -0.0202(13) C12 0.0416(10) 0.0389(11) 0.0319(9) -0.0022(8) -0.0032(8) -0.0105(9) C13 0.0462(12) 0.0481(13) 0.0540(13) -0.0127(10) -0.0082(10) -0.0104(10) C14 0.0444(12) 0.0586(15) 0.0703(15) -0.0103(12) -0.0113(11) -0.0045(11) C15 0.0564(14) 0.0480(14) 0.0588(14) -0.0065(11) -0.0004(12) 0.0059(11) C16 0.0700(15) 0.0426(13) 0.0465(12) -0.0109(10) -0.0044(11) -0.0084(11) C17 0.0523(12) 0.0434(12) 0.0443(11) -0.0093(9) -0.0076(10) -0.0082(10) C18 0.0506(12) 0.0386(12) 0.0374(10) -0.0053(9) -0.0037(9) -0.0106(10) C19 0.0548(13) 0.0429(13) 0.0563(13) -0.0083(10) 0.0082(11) -0.0117(11) C20 0.0606(14) 0.0683(17) 0.0565(14) -0.0089(12) 0.0079(12) -0.0234(13) C21 0.0775(17) 0.0625(17) 0.0564(14) 0.0012(12) -0.0049(13) -0.0358(15) C22 0.0875(19) 0.0390(14) 0.0832(18) -0.0050(12) -0.0106(16) -0.0209(14) C23 0.0582(14) 0.0450(14) 0.0689(15) -0.0120(11) -0.0010(12) -0.0094(12) C24 0.0429(11) 0.0443(12) 0.0372(11) -0.0061(9) -0.0049(9) -0.0075(10) C25 0.0521(13) 0.0864(19) 0.0672(15) -0.0179(14) -0.0166(12) -0.0262(13) C26 0.092(2) 0.126(3) 0.106(2) -0.052(2) -0.0050(19) -0.049(2) C27 0.0542(12) 0.0528(14) 0.0385(11) 0.0027(10) -0.0044(10) -0.0216(11) C28 0.101(2) 0.0617(17) 0.0500(14) -0.0065(12) -0.0111(14) -0.0094(15) C29 0.148(3) 0.086(2) 0.0439(15) -0.0088(14) -0.0211(17) -0.017(2) C30 0.112(2) 0.080(2) 0.0511(15) 0.0122(14) -0.0280(15) -0.0228(19) C31 0.0874(19) 0.0652(18) 0.0618(16) 0.0046(14) -0.0179(14) -0.0046(15) C32 0.0761(16) 0.0623(17) 0.0467(13) -0.0049(11) -0.0093(12) -0.0088(14) _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 C6 1.771(2) . ? S1 C5 1.845(2) . ? S2 C27 1.771(2) . ? S2 C2 1.823(2) . ? O1 C1 1.208(2) . ? O2 C24 1.325(2) . ? O2 C25 1.459(3) . ? O3 C24 1.200(2) . ? N1 C1 1.356(3) . ? N1 C7 1.419(2) . ? N1 C3 1.503(2) . ? C1 C2 1.543(3) . ? C2 C24 1.521(3) . ? C2 C3 1.599(3) . ? C3 C4 1.523(3) . ? C3 C12 1.520(3) . ? C4 C5 1.525(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C18 1.521(3) . ? C5 H5 0.9800 . ? C6 C7 1.389(3) . ? C6 C11 1.395(3) . ? C7 C8 1.393(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.363(3) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.382(3) . ? C12 C17 1.396(3) . ? C13 C14 1.387(3) . ? C13 H13 0.9300 . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 C16 1.375(3) . ? C15 H15 0.9300 . ? C16 C17 1.384(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.377(3) . ? C18 C19 1.393(3) . ? C19 C20 1.381(3) . ? C19 H19 0.9300 . ? C20 C21 1.359(3) . ? C20 H20 0.9300 . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C25 C26 1.495(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.381(3) . ? C27 C32 1.372(3) . ? C28 C29 1.375(4) . ? C28 H28 0.9300 . ? C29 C30 1.375(4) . ? C29 H29 0.9300 . ? C30 C31 1.360(4) . ? C30 H30 0.9300 . ? C31 C32 1.390(3) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 C6 S1 C5 108.24(9) . . ? C27 S2 C2 102.72(10) . . ? C24 O2 C25 116.92(18) . . ? C1 N1 C7 130.18(17) . . ? C1 N1 C3 96.05(15) . . ? C7 N1 C3 133.69(16) . . ? O1 C1 N1 131.7(2) . . ? O1 C1 C2 135.4(2) . . ? N1 C1 C2 92.80(16) . . ? C24 C2 C1 118.27(17) . . ? C24 C2 C3 115.07(16) . . ? C1 C2 C3 85.23(14) . . ? C24 C2 S2 112.81(13) . . ? C1 C2 S2 110.86(13) . . ? C3 C2 S2 111.77(13) . . ? N1 C3 C4 111.72(15) . . ? N1 C3 C12 117.00(15) . . ? C4 C3 C12 111.80(16) . . ? N1 C3 C2 85.39(13) . . ? C4 C3 C2 113.42(15) . . ? C12 C3 C2 115.16(15) . . ? C3 C4 C5 112.91(15) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C18 C5 C4 109.98(16) . . ? C18 C5 S1 106.04(13) . . ? C4 C5 S1 114.28(14) . . ? C18 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? S1 C5 H5 108.8 . . ? C7 C6 C11 118.55(19) . . ? C7 C6 S1 124.88(16) . . ? C11 C6 S1 116.20(16) . . ? C8 C7 C6 119.52(19) . . ? C8 C7 N1 117.95(17) . . ? C6 C7 N1 122.52(17) . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 121.3(2) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? C13 C12 C17 118.33(19) . . ? C13 C12 C3 123.34(18) . . ? C17 C12 C3 118.29(17) . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.9(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C23 C18 C19 118.42(19) . . ? C23 C18 C5 119.77(18) . . ? C19 C18 C5 121.73(18) . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.6(2) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 120.5(2) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? O3 C24 O2 125.35(19) . . ? O3 C24 C2 123.88(19) . . ? O2 C24 C2 110.74(17) . . ? O2 C25 C26 107.4(2) . . ? O2 C25 H25A 110.2 . . ? C26 C25 H25A 110.2 . . ? O2 C25 H25B 110.2 . . ? C26 C25 H25B 110.2 . . ? H25A C25 H25B 108.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C32 119.9(2) . . ? C28 C27 S2 115.23(18) . . ? C32 C27 S2 124.78(17) . . ? C29 C28 C27 120.2(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C30 C29 C28 119.8(3) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 120.1(3) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.6(3) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C27 C32 C31 119.3(2) . . ? C27 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? 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 C7 N1 C1 O1 -5.7(4) . . . . ? C3 N1 C1 O1 177.3(2) . . . . ? C7 N1 C1 C2 171.14(18) . . . . ? C3 N1 C1 C2 -5.87(15) . . . . ? O1 C1 C2 C24 -61.9(3) . . . . ? N1 C1 C2 C24 121.47(18) . . . . ? O1 C1 C2 C3 -177.9(3) . . . . ? N1 C1 C2 C3 5.50(14) . . . . ? O1 C1 C2 S2 70.6(3) . . . . ? N1 C1 C2 S2 -106.00(14) . . . . ? C27 S2 C2 C24 40.07(16) . . . . ? C27 S2 C2 C1 -95.17(15) . . . . ? C27 S2 C2 C3 171.60(13) . . . . ? C1 N1 C3 C4 -107.72(17) . . . . ? C7 N1 C3 C4 75.5(3) . . . . ? C1 N1 C3 C12 121.62(17) . . . . ? C7 N1 C3 C12 -55.2(3) . . . . ? C1 N1 C3 C2 5.67(14) . . . . ? C7 N1 C3 C2 -171.16(19) . . . . ? C24 C2 C3 N1 -124.03(17) . . . . ? C1 C2 C3 N1 -4.97(12) . . . . ? S2 C2 C3 N1 105.60(13) . . . . ? C24 C2 C3 C4 -12.3(2) . . . . ? C1 C2 C3 C4 106.72(17) . . . . ? S2 C2 C3 C4 -142.71(14) . . . . ? C24 C2 C3 C12 118.24(18) . . . . ? C1 C2 C3 C12 -122.70(16) . . . . ? S2 C2 C3 C12 -12.13(19) . . . . ? N1 C3 C4 C5 -69.1(2) . . . . ? C12 C3 C4 C5 64.2(2) . . . . ? C2 C3 C4 C5 -163.61(16) . . . . ? C3 C4 C5 C18 -163.28(16) . . . . ? C3 C4 C5 S1 77.60(19) . . . . ? C6 S1 C5 C18 167.96(13) . . . . ? C6 S1 C5 C4 -70.73(16) . . . . ? C5 S1 C6 C7 47.1(2) . . . . ? C5 S1 C6 C11 -139.95(17) . . . . ? C11 C6 C7 C8 -0.5(3) . . . . ? S1 C6 C7 C8 172.22(16) . . . . ? C11 C6 C7 N1 -179.49(18) . . . . ? S1 C6 C7 N1 -6.7(3) . . . . ? C1 N1 C7 C8 -47.3(3) . . . . ? C3 N1 C7 C8 128.5(2) . . . . ? C1 N1 C7 C6 131.6(2) . . . . ? C3 N1 C7 C6 -52.5(3) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? N1 C7 C8 C9 178.4(2) . . . . ? C7 C8 C9 C10 0.3(4) . . . . ? C8 C9 C10 C11 1.0(4) . . . . ? C9 C10 C11 C6 -2.2(4) . . . . ? C7 C6 C11 C10 1.9(3) . . . . ? S1 C6 C11 C10 -171.46(19) . . . . ? N1 C3 C12 C13 11.8(3) . . . . ? C4 C3 C12 C13 -118.8(2) . . . . ? C2 C3 C12 C13 109.8(2) . . . . ? N1 C3 C12 C17 -170.41(16) . . . . ? C4 C3 C12 C17 59.0(2) . . . . ? C2 C3 C12 C17 -72.4(2) . . . . ? C17 C12 C13 C14 -0.2(3) . . . . ? C3 C12 C13 C14 177.58(19) . . . . ? C12 C13 C14 C15 1.6(3) . . . . ? C13 C14 C15 C16 -1.7(4) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C12 0.9(3) . . . . ? C13 C12 C17 C16 -1.0(3) . . . . ? C3 C12 C17 C16 -178.95(17) . . . . ? C4 C5 C18 C23 98.5(2) . . . . ? S1 C5 C18 C23 -137.51(18) . . . . ? C4 C5 C18 C19 -78.4(2) . . . . ? S1 C5 C18 C19 45.7(2) . . . . ? C23 C18 C19 C20 -0.6(3) . . . . ? C5 C18 C19 C20 176.2(2) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 0.5(4) . . . . ? C21 C22 C23 C18 -1.2(4) . . . . ? C19 C18 C23 C22 1.3(3) . . . . ? C5 C18 C23 C22 -175.7(2) . . . . ? C25 O2 C24 O3 3.1(3) . . . . ? C25 O2 C24 C2 -178.82(18) . . . . ? C1 C2 C24 O3 -0.9(3) . . . . ? C3 C2 C24 O3 97.6(2) . . . . ? S2 C2 C24 O3 -132.5(2) . . . . ? C1 C2 C24 O2 -178.92(16) . . . . ? C3 C2 C24 O2 -80.4(2) . . . . ? S2 C2 C24 O2 49.4(2) . . . . ? C24 O2 C25 C26 178.2(2) . . . . ? C2 S2 C27 C28 -141.12(19) . . . . ? C2 S2 C27 C32 41.6(2) . . . . ? C32 C27 C28 C29 -1.6(4) . . . . ? S2 C27 C28 C29 -179.0(2) . . . . ? C27 C28 C29 C30 -0.7(5) . . . . ? C28 C29 C30 C31 1.7(5) . . . . ? C29 C30 C31 C32 -0.5(5) . . . . ? C28 C27 C32 C31 2.8(4) . . . . ? S2 C27 C32 C31 179.91(19) . . . . ? C30 C31 C32 C27 -1.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.182 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 _chemical_compound_source synthetic _exptl_crystal_recrystallization_method 'from ethyl acetate - petroleum ether' _chemical_name_common '[1,5]benzothiazepine-derived beta-lactam derivative'