# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhang, Junliang' _publ_contact_author_email jlzhang@chem.ecnu.edu.cn _publ_section_title ; Lewis Acid - Catalyzed Formal [3+2] Cycloadditions of N-Tosyl Aziridines with Electron-rich Alkenes via Selective Carbon-Carbon Bond Cleavage ; loop_ _publ_author_name J.Zhang L.Li X.Wu data_4a _database_code_depnum_ccdc_archive 'CCDC 795469' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N O7 S' _chemical_formula_weight 473.53 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 11.3198(5) _cell_length_b 13.9651(7) _cell_length_c 14.8228(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.0490(10) _cell_angle_gamma 90.00 _cell_volume 2273.13(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9352 _exptl_absorpt_correction_T_max 0.9597 _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 25746 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4008 _reflns_number_gt 3504 _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^)+(0.0583P)^2^+1.2572P] 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 4008 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1032 _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 S1 S 0.54131(4) 0.12432(3) 0.20623(3) 0.03132(15) Uani 1 1 d . . . O1 O 0.41795(13) 0.12687(10) 0.15229(9) 0.0422(4) Uani 1 1 d . . . O2 O 0.64040(14) 0.11720(10) 0.16219(10) 0.0440(4) Uani 1 1 d . . . O3 O 0.23782(12) 0.03282(11) 0.24905(10) 0.0446(4) Uani 1 1 d . . . O4 O 0.37089(12) 0.07813(10) 0.37871(9) 0.0395(3) Uani 1 1 d . . . O5 O 0.30213(12) -0.12599(10) 0.16640(10) 0.0431(4) Uani 1 1 d . . . O6 O 0.47895(11) -0.08318(10) 0.13540(8) 0.0356(3) Uani 1 1 d . . . O7 O 0.43719(11) -0.18163(8) 0.35698(8) 0.0304(3) Uani 1 1 d . . . N1 N 0.55026(12) 0.03338(10) 0.27764(9) 0.0247(3) Uani 1 1 d . . . C1 C 0.56745(16) 0.22881(12) 0.27493(12) 0.0294(4) Uani 1 1 d . . . C2 C 0.68617(17) 0.26217(13) 0.30623(14) 0.0356(4) Uani 1 1 d . . . H2A H 0.7519 0.2292 0.2907 0.043 Uiso 1 1 calc R . . C3 C 0.70693(17) 0.34344(14) 0.35995(15) 0.0387(5) Uani 1 1 d . . . H3A H 0.7880 0.3662 0.3815 0.046 Uiso 1 1 calc R . . C4 C 0.61252(18) 0.39311(13) 0.38358(15) 0.0383(5) Uani 1 1 d . . . C5 C 0.49402(18) 0.35992(14) 0.34956(15) 0.0396(5) Uani 1 1 d . . . H5A H 0.4280 0.3940 0.3635 0.048 Uiso 1 1 calc R . . C6 C 0.47112(16) 0.27785(13) 0.29565(13) 0.0345(4) Uani 1 1 d . . . H6A H 0.3901 0.2554 0.2731 0.041 Uiso 1 1 calc R . . C7 C 0.6394(2) 0.48051(17) 0.4441(2) 0.0606(7) Uani 1 1 d . . . H7A H 0.5632 0.5064 0.4543 0.091 Uiso 1 1 calc R . . H7B H 0.6789 0.5289 0.4135 0.091 Uiso 1 1 calc R . . H7C H 0.6937 0.4632 0.5041 0.091 Uiso 1 1 calc R . . C8 C 0.75249(15) 0.04142(12) 0.39166(12) 0.0254(4) Uani 1 1 d . . . C9 C 0.87271(17) 0.05429(14) 0.38897(14) 0.0378(5) Uani 1 1 d . . . H9A H 0.9014 0.0272 0.3395 0.045 Uiso 1 1 calc R . . C10 C 0.95167(19) 0.10611(17) 0.45757(17) 0.0507(6) Uani 1 1 d . . . H10A H 1.0341 0.1143 0.4550 0.061 Uiso 1 1 calc R . . C11 C 0.91108(19) 0.14585(16) 0.52948(15) 0.0445(5) Uani 1 1 d . . . H11A H 0.9652 0.1818 0.5763 0.053 Uiso 1 1 calc R . . C12 C 0.79224(18) 0.13339(14) 0.53345(14) 0.0374(4) Uani 1 1 d . . . H12A H 0.7643 0.1602 0.5834 0.045 Uiso 1 1 calc R . . C13 C 0.71299(17) 0.08186(13) 0.46486(12) 0.0317(4) Uani 1 1 d . . . H13A H 0.6307 0.0740 0.4678 0.038 Uiso 1 1 calc R . . C14 C 0.50120(18) -0.23841(13) 0.43553(14) 0.0374(4) Uani 1 1 d . . . H14A H 0.4566 -0.2992 0.4369 0.045 Uiso 1 1 calc R . . H14B H 0.5023 -0.2033 0.4937 0.045 Uiso 1 1 calc R . . C15 C 0.63117(18) -0.26083(13) 0.43170(14) 0.0380(4) Uani 1 1 d . . . H15A H 0.6298 -0.3036 0.3782 0.046 Uiso 1 1 calc R . . H15B H 0.6725 -0.2953 0.4891 0.046 Uiso 1 1 calc R . . C16 C 0.70362(16) -0.17071(13) 0.42215(13) 0.0315(4) Uani 1 1 d . . . H16A H 0.7176 -0.1320 0.4797 0.038 Uiso 1 1 calc R . . H16B H 0.7836 -0.1881 0.4109 0.038 Uiso 1 1 calc R . . C17 C 0.62856(15) -0.11412(12) 0.33989(12) 0.0264(4) Uani 1 1 d . . . H17A H 0.6182 -0.1555 0.2834 0.032 Uiso 1 1 calc R . . C18 C 0.50274(15) -0.09644(12) 0.35577(12) 0.0254(4) Uani 1 1 d . . . H18A H 0.5117 -0.0630 0.4167 0.031 Uiso 1 1 calc R . . C19 C 0.44339(14) -0.02676(12) 0.27660(11) 0.0237(4) Uani 1 1 d . . . C20 C 0.66980(15) -0.01525(12) 0.31492(11) 0.0260(4) Uani 1 1 d . . . H20A H 0.7112 -0.0230 0.2630 0.031 Uiso 1 1 calc R . . C21 C 0.34619(16) 0.03390(12) 0.30733(12) 0.0276(4) Uani 1 1 d . . . C22 C 0.1465(2) 0.0903(2) 0.27673(19) 0.0641(7) Uani 1 1 d . . . H22A H 0.0694 0.0855 0.2295 0.096 Uiso 1 1 calc R . . H22B H 0.1730 0.1573 0.2830 0.096 Uiso 1 1 calc R . . H22C H 0.1351 0.0672 0.3365 0.096 Uiso 1 1 calc R . . C23 C 0.39617(15) -0.08315(13) 0.18589(12) 0.0276(4) Uani 1 1 d . . . C24 C 0.4445(2) -0.1341(2) 0.04834(16) 0.0624(8) Uani 1 1 d . . . H24A H 0.5104 -0.1299 0.0162 0.094 Uiso 1 1 calc R . . H24B H 0.3703 -0.1056 0.0094 0.094 Uiso 1 1 calc R . . H24C H 0.4293 -0.2015 0.0603 0.094 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 0.0367(3) 0.0371(3) 0.0205(2) 0.00614(17) 0.00757(19) -0.00371(18) O1 0.0455(8) 0.0463(8) 0.0278(7) 0.0098(6) -0.0046(6) -0.0043(6) O2 0.0559(9) 0.0526(9) 0.0307(7) 0.0039(6) 0.0241(7) -0.0062(7) O3 0.0295(7) 0.0646(9) 0.0387(8) -0.0093(7) 0.0062(6) 0.0168(6) O4 0.0419(8) 0.0463(8) 0.0331(7) -0.0112(6) 0.0143(6) 0.0042(6) O5 0.0274(7) 0.0567(9) 0.0435(8) -0.0179(7) 0.0053(6) -0.0081(6) O6 0.0257(6) 0.0599(9) 0.0204(6) -0.0134(6) 0.0042(5) 0.0012(6) O7 0.0290(6) 0.0295(6) 0.0330(7) 0.0023(5) 0.0080(5) -0.0038(5) N1 0.0244(7) 0.0297(7) 0.0194(7) 0.0019(6) 0.0042(6) -0.0021(6) C1 0.0306(9) 0.0306(9) 0.0273(9) 0.0103(7) 0.0077(7) -0.0022(7) C2 0.0282(9) 0.0321(9) 0.0483(11) 0.0096(8) 0.0131(8) -0.0004(7) C3 0.0275(9) 0.0338(10) 0.0532(13) 0.0087(9) 0.0064(9) -0.0064(8) C4 0.0406(11) 0.0289(9) 0.0467(12) 0.0074(8) 0.0131(9) -0.0037(8) C5 0.0346(10) 0.0321(10) 0.0555(13) 0.0060(9) 0.0175(9) 0.0015(8) C6 0.0249(9) 0.0359(10) 0.0415(11) 0.0098(8) 0.0055(8) -0.0016(7) C7 0.0626(15) 0.0413(12) 0.0824(18) -0.0124(12) 0.0263(14) -0.0126(11) C8 0.0263(9) 0.0252(8) 0.0249(9) 0.0011(7) 0.0065(7) -0.0021(7) C9 0.0288(10) 0.0475(11) 0.0402(11) -0.0150(9) 0.0142(8) -0.0078(8) C10 0.0307(11) 0.0656(14) 0.0584(14) -0.0244(11) 0.0158(10) -0.0173(10) C11 0.0398(11) 0.0487(12) 0.0416(12) -0.0173(9) 0.0034(9) -0.0131(9) C12 0.0413(11) 0.0429(11) 0.0294(10) -0.0102(8) 0.0113(8) -0.0055(8) C13 0.0291(9) 0.0392(10) 0.0288(9) -0.0034(8) 0.0107(7) -0.0058(8) C14 0.0442(11) 0.0311(9) 0.0380(11) 0.0083(8) 0.0120(9) -0.0006(8) C15 0.0413(11) 0.0310(9) 0.0395(11) 0.0040(8) 0.0052(9) 0.0043(8) C16 0.0294(9) 0.0315(9) 0.0310(10) -0.0021(7) 0.0027(7) 0.0038(7) C17 0.0256(9) 0.0293(9) 0.0239(9) -0.0056(7) 0.0056(7) -0.0008(7) C18 0.0275(9) 0.0269(8) 0.0227(9) 0.0002(7) 0.0075(7) -0.0005(7) C19 0.0229(8) 0.0290(8) 0.0197(8) -0.0009(6) 0.0062(6) -0.0014(6) C20 0.0235(8) 0.0323(9) 0.0228(8) -0.0022(7) 0.0067(7) 0.0003(7) C21 0.0295(9) 0.0315(9) 0.0238(9) 0.0021(7) 0.0103(7) 0.0014(7) C22 0.0395(12) 0.0881(19) 0.0652(16) -0.0150(14) 0.0136(11) 0.0285(13) C23 0.0211(8) 0.0359(9) 0.0246(9) -0.0039(7) 0.0031(7) 0.0038(7) C24 0.0384(12) 0.114(2) 0.0308(12) -0.0380(13) 0.0006(9) 0.0101(13) _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 O1 1.4313(14) . ? S1 O2 1.4317(14) . ? S1 N1 1.6406(14) . ? S1 C1 1.7628(19) . ? O3 C21 1.318(2) . ? O3 C22 1.445(2) . ? O4 C21 1.198(2) . ? O5 C23 1.194(2) . ? O6 C23 1.334(2) . ? O6 C24 1.442(2) . ? O7 C18 1.405(2) . ? O7 C14 1.449(2) . ? N1 C19 1.470(2) . ? N1 C20 1.495(2) . ? C1 C6 1.384(3) . ? C1 C2 1.391(3) . ? C2 C3 1.374(3) . ? C2 H2A 0.9500 . ? C3 C4 1.388(3) . ? C3 H3A 0.9500 . ? C4 C5 1.393(3) . ? C4 C7 1.502(3) . ? C5 C6 1.385(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.383(2) . ? C8 C13 1.390(2) . ? C8 C20 1.510(2) . ? C9 C10 1.384(3) . ? C9 H9A 0.9500 . ? C10 C11 1.376(3) . ? C10 H10A 0.9500 . ? C11 C12 1.372(3) . ? C11 H11A 0.9500 . ? C12 C13 1.383(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.519(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.527(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.526(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(2) . ? C17 C20 1.531(2) . ? C17 H17A 1.0000 . ? C18 C19 1.547(2) . ? C18 H18A 1.0000 . ? C19 C23 1.538(2) . ? C19 C21 1.542(2) . ? C20 H20A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 O1 S1 O2 120.87(9) . . ? O1 S1 N1 106.19(8) . . ? O2 S1 N1 107.93(8) . . ? O1 S1 C1 107.84(9) . . ? O2 S1 C1 106.30(9) . . ? N1 S1 C1 107.02(8) . . ? C21 O3 C22 115.07(16) . . ? C23 O6 C24 115.33(15) . . ? C18 O7 C14 108.13(13) . . ? C19 N1 C20 114.40(13) . . ? C19 N1 S1 120.92(11) . . ? C20 N1 S1 119.92(11) . . ? C6 C1 C2 120.64(18) . . ? C6 C1 S1 120.47(14) . . ? C2 C1 S1 118.87(14) . . ? C3 C2 C1 119.04(18) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.68(18) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 118.36(19) . . ? C3 C4 C7 120.00(19) . . ? C5 C4 C7 121.65(19) . . ? C6 C5 C4 120.87(18) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C1 C6 C5 119.36(17) . . ? C1 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 118.36(16) . . ? C9 C8 C20 118.75(15) . . ? C13 C8 C20 122.89(15) . . ? C8 C9 C10 120.75(18) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C11 C10 C9 120.18(19) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C12 C11 C10 119.83(18) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.15(18) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C8 120.73(17) . . ? C12 C13 H13A 119.6 . . ? C8 C13 H13A 119.6 . . ? O7 C14 C15 112.51(15) . . ? O7 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? O7 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 112.37(15) . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 107.06(14) . . ? C17 C16 H16A 110.3 . . ? C15 C16 H16A 110.3 . . ? C17 C16 H16B 110.3 . . ? C15 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? C18 C17 C16 108.75(14) . . ? C18 C17 C20 104.07(13) . . ? C16 C17 C20 121.10(14) . . ? C18 C17 H17A 107.4 . . ? C16 C17 H17A 107.4 . . ? C20 C17 H17A 107.4 . . ? O7 C18 C17 112.48(14) . . ? O7 C18 C19 114.15(13) . . ? C17 C18 C19 103.63(13) . . ? O7 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? N1 C19 C23 114.35(13) . . ? N1 C19 C21 109.11(13) . . ? C23 C19 C21 114.71(13) . . ? N1 C19 C18 98.44(12) . . ? C23 C19 C18 109.63(13) . . ? C21 C19 C18 109.33(13) . . ? N1 C20 C8 112.35(13) . . ? N1 C20 C17 101.38(13) . . ? C8 C20 C17 117.40(14) . . ? N1 C20 H20A 108.4 . . ? C8 C20 H20A 108.4 . . ? C17 C20 H20A 108.4 . . ? O4 C21 O3 124.42(16) . . ? O4 C21 C19 120.91(16) . . ? O3 C21 C19 114.67(14) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 O6 124.81(16) . . ? O5 C23 C19 124.64(15) . . ? O6 C23 C19 110.39(13) . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 O1 S1 N1 C19 0.34(15) . . . . ? O2 S1 N1 C19 -130.62(13) . . . . ? C1 S1 N1 C19 115.33(13) . . . . ? O1 S1 N1 C20 154.56(12) . . . . ? O2 S1 N1 C20 23.60(14) . . . . ? C1 S1 N1 C20 -90.46(13) . . . . ? O1 S1 C1 C6 22.48(17) . . . . ? O2 S1 C1 C6 153.45(14) . . . . ? N1 S1 C1 C6 -91.40(15) . . . . ? O1 S1 C1 C2 -156.17(14) . . . . ? O2 S1 C1 C2 -25.19(16) . . . . ? N1 S1 C1 C2 89.96(15) . . . . ? C6 C1 C2 C3 1.5(3) . . . . ? S1 C1 C2 C3 -179.85(14) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C2 C3 C4 C7 178.7(2) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C7 C4 C5 C6 -178.4(2) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? S1 C1 C6 C5 -179.82(14) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C13 C8 C9 C10 0.0(3) . . . . ? C20 C8 C9 C10 179.70(19) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C8 0.5(3) . . . . ? C9 C8 C13 C12 -0.2(3) . . . . ? C20 C8 C13 C12 -179.86(17) . . . . ? C18 O7 C14 C15 -58.05(19) . . . . ? O7 C14 C15 C16 54.5(2) . . . . ? C14 C15 C16 C17 -51.9(2) . . . . ? C15 C16 C17 C18 54.98(18) . . . . ? C15 C16 C17 C20 175.29(15) . . . . ? C14 O7 C18 C17 63.76(17) . . . . ? C14 O7 C18 C19 -178.53(14) . . . . ? C16 C17 C18 O7 -64.38(17) . . . . ? C20 C17 C18 O7 165.26(13) . . . . ? C16 C17 C18 C19 171.85(13) . . . . ? C20 C17 C18 C19 41.49(16) . . . . ? C20 N1 C19 C23 -90.80(16) . . . . ? S1 N1 C19 C23 64.75(17) . . . . ? C20 N1 C19 C21 139.23(14) . . . . ? S1 N1 C19 C21 -65.23(16) . . . . ? C20 N1 C19 C18 25.30(16) . . . . ? S1 N1 C19 C18 -179.16(11) . . . . ? O7 C18 C19 N1 -162.31(13) . . . . ? C17 C18 C19 N1 -39.63(15) . . . . ? O7 C18 C19 C23 -42.61(18) . . . . ? C17 C18 C19 C23 80.06(15) . . . . ? O7 C18 C19 C21 83.94(17) . . . . ? C17 C18 C19 C21 -153.39(13) . . . . ? C19 N1 C20 C8 -127.14(14) . . . . ? S1 N1 C20 C8 77.05(16) . . . . ? C19 N1 C20 C17 -0.96(17) . . . . ? S1 N1 C20 C17 -156.77(11) . . . . ? C9 C8 C20 N1 -133.31(17) . . . . ? C13 C8 C20 N1 46.3(2) . . . . ? C9 C8 C20 C17 109.72(19) . . . . ? C13 C8 C20 C17 -70.7(2) . . . . ? C18 C17 C20 N1 -24.81(15) . . . . ? C16 C17 C20 N1 -147.38(15) . . . . ? C18 C17 C20 C8 97.97(16) . . . . ? C16 C17 C20 C8 -24.6(2) . . . . ? C22 O3 C21 O4 0.1(3) . . . . ? C22 O3 C21 C19 -179.32(18) . . . . ? N1 C19 C21 O4 -53.1(2) . . . . ? C23 C19 C21 O4 177.15(16) . . . . ? C18 C19 C21 O4 53.6(2) . . . . ? N1 C19 C21 O3 126.40(16) . . . . ? C23 C19 C21 O3 -3.4(2) . . . . ? C18 C19 C21 O3 -126.97(16) . . . . ? C24 O6 C23 O5 4.5(3) . . . . ? C24 O6 C23 C19 -179.97(18) . . . . ? N1 C19 C23 O5 -169.87(17) . . . . ? C21 C19 C23 O5 -42.7(2) . . . . ? C18 C19 C23 O5 80.7(2) . . . . ? N1 C19 C23 O6 14.6(2) . . . . ? C21 C19 C23 O6 141.78(14) . . . . ? C18 C19 C23 O6 -94.78(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.296 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.046 # Attachment '5a.cif' data_5a _database_code_depnum_ccdc_archive 'CCDC 795470' #TrackingRef '5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O7 S' _chemical_formula_weight 461.52 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 10.2984(3) _cell_length_b 12.7982(3) _cell_length_c 17.1922(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.1090(10) _cell_angle_gamma 90.00 _cell_volume 2262.61(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9023 _exptl_absorpt_correction_T_max 0.9494 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 25747 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3989 _reflns_number_gt 3430 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_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^)+(0.0480P)^2^+0.9764P] 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 3989 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.46714(4) 0.63372(4) 0.24528(3) 0.04535(15) Uani 1 1 d . . . O1 O 0.40167(16) 0.69312(13) 0.30134(9) 0.0688(4) Uani 1 1 d . . . O2 O 0.56841(13) 0.56292(11) 0.27000(8) 0.0555(4) Uani 1 1 d . . . O3 O 0.81461(13) 0.59929(12) 0.09980(9) 0.0617(4) Uani 1 1 d . . . O4 O 0.60629(11) 0.55332(9) 0.09944(7) 0.0443(3) Uani 1 1 d . . . O5 O 0.72179(15) 0.77070(12) 0.29888(8) 0.0647(4) Uani 1 1 d . . . O6 O 0.85832(13) 0.65658(11) 0.24924(8) 0.0564(4) Uani 1 1 d . . . O7 O 0.65124(14) 0.78192(10) 0.04469(7) 0.0546(4) Uani 1 1 d . . . N1 N 0.53120(14) 0.71522(10) 0.18370(8) 0.0403(3) Uani 1 1 d . . . C1 C 0.0390(2) 0.38566(19) 0.07658(13) 0.0673(6) Uani 1 1 d . . . H1A H -0.0373 0.4285 0.0694 0.101 Uiso 1 1 calc R . . H1B H 0.0195 0.3257 0.1074 0.101 Uiso 1 1 calc R . . H1C H 0.0663 0.3633 0.0267 0.101 Uiso 1 1 calc R . . C2 C 0.14630(19) 0.44778(16) 0.11769(11) 0.0513(5) Uani 1 1 d . . . C3 C 0.26767(19) 0.40401(16) 0.13469(12) 0.0533(5) Uani 1 1 d . . . H3A H 0.2825 0.3350 0.1208 0.064 Uiso 1 1 calc R . . C4 C 0.36675(18) 0.46033(14) 0.17161(11) 0.0479(4) Uani 1 1 d . . . H4A H 0.4476 0.4297 0.1823 0.057 Uiso 1 1 calc R . . C5 C 0.34511(17) 0.56262(14) 0.19265(10) 0.0432(4) Uani 1 1 d . . . C6 C 0.22404(19) 0.60712(16) 0.17748(13) 0.0566(5) Uani 1 1 d . . . H6A H 0.2087 0.6756 0.1925 0.068 Uiso 1 1 calc R . . C7 C 0.12633(19) 0.54988(17) 0.14016(14) 0.0595(5) Uani 1 1 d . . . H7A H 0.0453 0.5805 0.1299 0.071 Uiso 1 1 calc R . . C8 C 0.36485(17) 0.83832(13) 0.12326(10) 0.0421(4) Uani 1 1 d . . . C9 C 0.27250(19) 0.91160(15) 0.14084(12) 0.0508(5) Uani 1 1 d . . . H9A H 0.2832 0.9499 0.1867 0.061 Uiso 1 1 calc R . . C10 C 0.1645(2) 0.92888(17) 0.09135(15) 0.0649(6) Uani 1 1 d . . . H10A H 0.1032 0.9785 0.1041 0.078 Uiso 1 1 calc R . . C11 C 0.1477(2) 0.87311(18) 0.02355(14) 0.0640(6) Uani 1 1 d . . . H11A H 0.0752 0.8849 -0.0099 0.077 Uiso 1 1 calc R . . C12 C 0.2386(2) 0.79972(19) 0.00527(13) 0.0613(5) Uani 1 1 d . . . H12A H 0.2273 0.7616 -0.0407 0.074 Uiso 1 1 calc R . . C13 C 0.34626(19) 0.78222(17) 0.05456(12) 0.0558(5) Uani 1 1 d . . . H13A H 0.4071 0.7323 0.0417 0.067 Uiso 1 1 calc R . . C14 C 0.67026(16) 0.70749(13) 0.16940(10) 0.0399(4) Uani 1 1 d . . . C15 C 0.69537(18) 0.81011(15) 0.12240(11) 0.0486(4) Uani 1 1 d . . . C16 C 0.6032(2) 0.88683(15) 0.15738(13) 0.0572(5) Uani 1 1 d . . . H16A H 0.5788 0.9411 0.1200 0.069 Uiso 1 1 calc R . . H16B H 0.6444 0.9194 0.2033 0.069 Uiso 1 1 calc R . . C17 C 0.48283(19) 0.82514(13) 0.17915(11) 0.0459(4) Uani 1 1 d . . . H17A H 0.4594 0.8470 0.2312 0.055 Uiso 1 1 calc R . . C18 C 0.70662(16) 0.61407(14) 0.11947(10) 0.0410(4) Uani 1 1 d . . . C19 C 0.6388(2) 0.45983(15) 0.05718(12) 0.0567(5) Uani 1 1 d . . . H19A H 0.5612 0.4201 0.0451 0.085 Uiso 1 1 calc R . . H19B H 0.6989 0.4184 0.0887 0.085 Uiso 1 1 calc R . . H19C H 0.6777 0.4790 0.0098 0.085 Uiso 1 1 calc R . . C20 C 0.75186(18) 0.71423(14) 0.24747(11) 0.0460(4) Uani 1 1 d . . . C21 C 0.9436(2) 0.6680(2) 0.31794(14) 0.0730(7) Uani 1 1 d . . . H21A H 1.0183 0.6240 0.3137 0.110 Uiso 1 1 calc R . . H21B H 0.8982 0.6482 0.3630 0.110 Uiso 1 1 calc R . . H21C H 0.9710 0.7395 0.3229 0.110 Uiso 1 1 calc R . . C22 C 0.8368(2) 0.84524(18) 0.12589(14) 0.0660(6) Uani 1 1 d . . . H22A H 0.8446 0.9080 0.0959 0.099 Uiso 1 1 calc R . . H22B H 0.8896 0.7914 0.1049 0.099 Uiso 1 1 calc R . . H22C H 0.8654 0.8584 0.1791 0.099 Uiso 1 1 calc R . . C23 C 0.6622(3) 0.8591(2) -0.01326(15) 0.0925(9) Uani 1 1 d . . . H23A H 0.6303 0.8318 -0.0627 0.139 Uiso 1 1 calc R . . H23B H 0.7518 0.8787 -0.0162 0.139 Uiso 1 1 calc R . . H23C H 0.6120 0.9192 -0.0004 0.139 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 0.0477(3) 0.0459(3) 0.0428(3) -0.00239(19) 0.00532(19) -0.0027(2) O1 0.0779(10) 0.0714(10) 0.0596(9) -0.0193(7) 0.0248(8) -0.0081(8) O2 0.0551(8) 0.0549(8) 0.0554(8) 0.0123(6) -0.0067(6) -0.0033(6) O3 0.0386(8) 0.0784(10) 0.0685(9) -0.0197(8) 0.0051(6) 0.0002(7) O4 0.0412(7) 0.0415(6) 0.0500(7) -0.0107(5) 0.0014(5) -0.0031(5) O5 0.0741(10) 0.0675(9) 0.0510(8) -0.0185(7) -0.0116(7) 0.0045(8) O6 0.0492(8) 0.0648(9) 0.0531(8) -0.0048(7) -0.0158(6) 0.0037(7) O7 0.0604(8) 0.0548(8) 0.0472(7) 0.0088(6) -0.0090(6) -0.0155(6) N1 0.0385(8) 0.0349(7) 0.0472(8) -0.0038(6) 0.0004(6) 0.0006(6) C1 0.0610(13) 0.0773(15) 0.0622(13) 0.0131(11) -0.0097(10) -0.0217(11) C2 0.0467(11) 0.0610(12) 0.0462(10) 0.0119(9) 0.0036(8) -0.0132(9) C3 0.0532(12) 0.0456(10) 0.0617(12) -0.0015(9) 0.0071(9) -0.0064(9) C4 0.0412(10) 0.0444(10) 0.0585(11) 0.0021(8) 0.0069(8) 0.0002(8) C5 0.0385(9) 0.0430(10) 0.0488(10) 0.0020(8) 0.0092(7) -0.0036(7) C6 0.0440(11) 0.0469(11) 0.0797(14) -0.0005(10) 0.0096(10) 0.0038(9) C7 0.0375(10) 0.0611(13) 0.0797(14) 0.0125(11) 0.0021(9) 0.0002(9) C8 0.0458(10) 0.0377(9) 0.0435(9) -0.0006(7) 0.0074(7) 0.0022(7) C9 0.0537(11) 0.0429(10) 0.0570(11) -0.0034(8) 0.0136(9) 0.0041(9) C10 0.0491(12) 0.0553(12) 0.0910(17) 0.0034(12) 0.0092(11) 0.0140(10) C11 0.0455(12) 0.0688(14) 0.0766(15) 0.0150(12) -0.0058(10) 0.0014(10) C12 0.0497(12) 0.0789(15) 0.0548(12) -0.0082(11) -0.0031(9) -0.0026(11) C13 0.0465(11) 0.0635(13) 0.0571(12) -0.0162(10) 0.0002(9) 0.0104(9) C14 0.0370(9) 0.0399(9) 0.0421(9) -0.0019(7) -0.0034(7) -0.0044(7) C15 0.0495(11) 0.0431(10) 0.0519(10) 0.0030(8) -0.0084(8) -0.0126(8) C16 0.0642(13) 0.0370(10) 0.0682(13) -0.0040(9) -0.0168(10) -0.0078(9) C17 0.0575(11) 0.0354(9) 0.0445(10) -0.0081(7) -0.0014(8) 0.0057(8) C18 0.0361(10) 0.0460(10) 0.0402(9) -0.0010(7) -0.0030(7) -0.0008(7) C19 0.0652(13) 0.0465(11) 0.0583(12) -0.0161(9) 0.0041(10) 0.0003(9) C20 0.0474(10) 0.0440(10) 0.0457(10) -0.0018(8) -0.0060(8) -0.0056(8) C21 0.0678(14) 0.0797(16) 0.0678(14) -0.0012(12) -0.0309(12) -0.0013(12) C22 0.0573(13) 0.0643(13) 0.0751(15) 0.0093(11) -0.0093(11) -0.0254(11) C23 0.127(2) 0.0828(18) 0.0656(15) 0.0264(13) -0.0177(15) -0.0292(17) _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 O1 1.4255(15) . ? S1 O2 1.4288(14) . ? S1 N1 1.6491(15) . ? S1 C5 1.7615(18) . ? O3 C18 1.195(2) . ? O4 C18 1.324(2) . ? O4 C19 1.448(2) . ? O5 C20 1.195(2) . ? O6 C20 1.320(2) . ? O6 C21 1.440(2) . ? O7 C23 1.411(3) . ? O7 C15 1.434(2) . ? N1 C14 1.469(2) . ? N1 C17 1.493(2) . ? C1 C2 1.506(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.381(3) . ? C2 C3 1.386(3) . ? C3 C4 1.376(3) . ? C3 H3A 0.9300 . ? C4 C5 1.379(3) . ? C4 H4A 0.9300 . ? C5 C6 1.383(3) . ? C6 C7 1.375(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.381(2) . ? C8 C13 1.387(3) . ? C8 C17 1.517(3) . ? C9 C10 1.381(3) . ? C9 H9A 0.9300 . ? C10 C11 1.370(3) . ? C10 H10A 0.9300 . ? C11 C12 1.374(3) . ? C11 H11A 0.9300 . ? C12 C13 1.377(3) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C18 1.530(2) . ? C14 C20 1.547(2) . ? C14 C15 1.571(2) . ? C15 C16 1.513(3) . ? C15 C22 1.522(3) . ? C16 C17 1.533(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 O1 S1 O2 120.10(10) . . ? O1 S1 N1 108.49(8) . . ? O2 S1 N1 106.33(8) . . ? O1 S1 C5 105.81(9) . . ? O2 S1 C5 108.31(8) . . ? N1 S1 C5 107.22(8) . . ? C18 O4 C19 114.68(14) . . ? C20 O6 C21 115.51(17) . . ? C23 O7 C15 116.63(16) . . ? C14 N1 C17 112.34(14) . . ? C14 N1 S1 119.49(11) . . ? C17 N1 S1 119.06(12) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 118.01(18) . . ? C7 C2 C1 120.93(19) . . ? C3 C2 C1 121.1(2) . . ? C4 C3 C2 121.54(19) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 119.45(18) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 119.89(18) . . ? C4 C5 S1 120.26(14) . . ? C6 C5 S1 119.67(15) . . ? C7 C6 C5 119.88(19) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C6 C7 C2 121.21(19) . . ? C6 C7 H7A 119.4 . . ? C2 C7 H7A 119.4 . . ? C9 C8 C13 118.24(18) . . ? C9 C8 C17 118.32(16) . . ? C13 C8 C17 123.42(16) . . ? C10 C9 C8 121.00(19) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C12 C13 C8 120.62(19) . . ? C12 C13 H13A 119.7 . . ? C8 C13 H13A 119.7 . . ? N1 C14 C18 114.64(13) . . ? N1 C14 C20 109.85(14) . . ? C18 C14 C20 113.10(14) . . ? N1 C14 C15 102.65(14) . . ? C18 C14 C15 108.22(14) . . ? C20 C14 C15 107.63(13) . . ? O7 C15 C16 111.08(16) . . ? O7 C15 C22 111.43(17) . . ? C16 C15 C22 114.35(17) . . ? O7 C15 C14 102.48(13) . . ? C16 C15 C14 102.35(15) . . ? C22 C15 C14 114.24(16) . . ? C15 C16 C17 107.22(14) . . ? C15 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? C15 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? N1 C17 C8 113.04(14) . . ? N1 C17 C16 103.07(15) . . ? C8 C17 C16 114.75(16) . . ? N1 C17 H17A 108.6 . . ? C8 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? O3 C18 O4 123.97(17) . . ? O3 C18 C14 122.84(16) . . ? O4 C18 C14 113.18(14) . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 O6 124.66(17) . . ? O5 C20 C14 121.67(17) . . ? O6 C20 C14 113.59(16) . . ? O6 C21 H21A 109.5 . . ? O6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C22 H22A 109.5 . . ? C15 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C15 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O7 C23 H23A 109.5 . . ? O7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 O1 S1 N1 C14 126.75(13) . . . . ? O2 S1 N1 C14 -3.71(14) . . . . ? C5 S1 N1 C14 -119.40(13) . . . . ? O1 S1 N1 C17 -17.71(15) . . . . ? O2 S1 N1 C17 -148.17(13) . . . . ? C5 S1 N1 C17 96.14(14) . . . . ? C7 C2 C3 C4 -1.1(3) . . . . ? C1 C2 C3 C4 179.42(19) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C3 C4 C5 S1 176.07(15) . . . . ? O1 S1 C5 C4 -139.84(16) . . . . ? O2 S1 C5 C4 -9.85(18) . . . . ? N1 S1 C5 C4 104.51(16) . . . . ? O1 S1 C5 C6 35.36(18) . . . . ? O2 S1 C5 C6 165.35(15) . . . . ? N1 S1 C5 C6 -80.28(17) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? S1 C5 C6 C7 -176.45(16) . . . . ? C5 C6 C7 C2 0.4(3) . . . . ? C3 C2 C7 C6 0.7(3) . . . . ? C1 C2 C7 C6 -179.8(2) . . . . ? C13 C8 C9 C10 -0.1(3) . . . . ? C17 C8 C9 C10 178.48(18) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 0.2(3) . . . . ? C17 C8 C13 C12 -178.32(19) . . . . ? C17 N1 C14 C18 -139.52(15) . . . . ? S1 N1 C14 C18 73.80(17) . . . . ? C17 N1 C14 C20 91.84(17) . . . . ? S1 N1 C14 C20 -54.84(17) . . . . ? C17 N1 C14 C15 -22.42(17) . . . . ? S1 N1 C14 C15 -169.11(11) . . . . ? C23 O7 C15 C16 71.9(2) . . . . ? C23 O7 C15 C22 -56.8(3) . . . . ? C23 O7 C15 C14 -179.4(2) . . . . ? N1 C14 C15 O7 -81.73(16) . . . . ? C18 C14 C15 O7 39.84(17) . . . . ? C20 C14 C15 O7 162.39(15) . . . . ? N1 C14 C15 C16 33.45(16) . . . . ? C18 C14 C15 C16 155.03(14) . . . . ? C20 C14 C15 C16 -82.43(17) . . . . ? N1 C14 C15 C22 157.61(17) . . . . ? C18 C14 C15 C22 -80.82(19) . . . . ? C20 C14 C15 C22 41.7(2) . . . . ? O7 C15 C16 C17 75.17(19) . . . . ? C22 C15 C16 C17 -157.66(17) . . . . ? C14 C15 C16 C17 -33.58(18) . . . . ? C14 N1 C17 C8 126.57(16) . . . . ? S1 N1 C17 C8 -86.59(17) . . . . ? C14 N1 C17 C16 2.11(19) . . . . ? S1 N1 C17 C16 148.95(13) . . . . ? C9 C8 C17 N1 146.39(16) . . . . ? C13 C8 C17 N1 -35.1(3) . . . . ? C9 C8 C17 C16 -95.8(2) . . . . ? C13 C8 C17 C16 82.7(2) . . . . ? C15 C16 C17 N1 20.35(19) . . . . ? C15 C16 C17 C8 -102.98(18) . . . . ? C19 O4 C18 O3 5.7(3) . . . . ? C19 O4 C18 C14 -175.52(15) . . . . ? N1 C14 C18 O3 176.69(17) . . . . ? C20 C14 C18 O3 -56.3(2) . . . . ? C15 C14 C18 O3 62.8(2) . . . . ? N1 C14 C18 O4 -2.1(2) . . . . ? C20 C14 C18 O4 124.90(16) . . . . ? C15 C14 C18 O4 -115.96(16) . . . . ? C21 O6 C20 O5 -2.4(3) . . . . ? C21 O6 C20 C14 174.37(17) . . . . ? N1 C14 C20 O5 -37.3(2) . . . . ? C18 C14 C20 O5 -166.81(17) . . . . ? C15 C14 C20 O5 73.7(2) . . . . ? N1 C14 C20 O6 145.85(15) . . . . ? C18 C14 C20 O6 16.4(2) . . . . ? C15 C14 C20 O6 -103.12(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.035