# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email francoise.colobert@unistra.fr _publ_contact_author_name 'Francoise Colobert' loop_ _publ_author_name 'Leermann, Timo' 'Broutin, Pierre-Emmanuel' 'Leroux, Frederic' 'Colobert, Francoise' # Attachment '- (aS)-4.cif' data_e2011a _database_code_depnum_ccdc_archive 'CCDC 871940' #TrackingRef '- (aS)-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H20 N4 O6 S' _chemical_formula_weight 636.62 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5048(3) _cell_length_b 18.9754(6) _cell_length_c 19.2401(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3470.1(2) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 15051 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5726 _reflns_number_gt 5091 _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^)+(0.1000P)^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 mixed _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 0.18(14) _refine_ls_number_reflns 5726 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2074 _refine_ls_wR_factor_gt 0.1969 _refine_ls_goodness_of_fit_ref 1.393 _refine_ls_restrained_S_all 1.393 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.003 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 0.16659(10) 0.68888(7) 0.21009(6) 0.0314(3) Uani 1 1 d . . . O1 O 0.2384(4) 0.7568(2) 0.1921(2) 0.0461(10) Uani 1 1 d . . . C1 C 0.2791(4) 0.6190(3) 0.1814(2) 0.0278(11) Uani 1 1 d . . . C5 C 0.4769(5) 0.5830(3) 0.1134(3) 0.0384(13) Uani 1 1 d . . . C4 C 0.4472(5) 0.5120(3) 0.1271(3) 0.0382(13) Uani 1 1 d . . . C6 C 0.3923(5) 0.6369(3) 0.1402(3) 0.0335(12) Uani 1 1 d . . . C2 C 0.2457(4) 0.5480(3) 0.1951(3) 0.0398(13) Uani 1 1 d . . . C3 C 0.3273(5) 0.4952(3) 0.1688(3) 0.0439(14) Uani 1 1 d . . . C7 C 0.5406(6) 0.4541(3) 0.0974(4) 0.0579(18) Uani 1 1 d . . . C8 C 0.1073(4) 0.7296(3) 0.3429(2) 0.0263(10) Uani 1 1 d . . . O10 O 0.3284(5) 0.7728(3) 0.4174(3) 0.0783(16) Uani 1 1 d . . . C11 C 0.2355(5) 0.7429(3) 0.4493(3) 0.0462(16) Uani 1 1 d . . . C9 C 0.1923(4) 0.6750(3) 0.3023(2) 0.0280(11) Uani 1 1 d . . . C12 C 0.2277(8) 0.7310(4) 0.5248(4) 0.070(2) Uani 1 1 d . . . O2 O 0.1219(3) 0.71540(19) 0.41637(18) 0.0347(9) Uani 1 1 d . . . C17 C -0.1179(4) 0.6610(3) 0.3370(2) 0.0278(11) Uani 1 1 d . . . C15 C -0.3331(4) 0.7124(2) 0.2934(3) 0.0271(11) Uani 1 1 d . . . C13 C -0.0491(4) 0.7255(2) 0.3267(2) 0.0225(10) Uani 1 1 d . . . C16 C -0.2598(4) 0.6558(3) 0.3213(2) 0.0268(11) Uani 1 1 d . . . C14 C -0.1205(4) 0.7842(2) 0.3011(2) 0.0239(10) Uani 1 1 d . . . O3 O -0.3165(3) 0.59092(18) 0.33431(19) 0.0350(9) Uani 1 1 d . . . O4 O -0.3276(3) 0.83538(18) 0.2584(2) 0.0409(9) Uani 1 1 d . . . C18 C -0.4746(5) 0.8297(3) 0.2390(4) 0.063(2) Uani 1 1 d . . . C19 C -0.0465(3) 0.8526(2) 0.2893(3) 0.0259(10) Uani 1 1 d . . . C24 C 0.0686(4) 0.9324(2) 0.2090(3) 0.0277(11) Uani 1 1 d . . . C25 C -0.0154(4) 0.8736(2) 0.2220(2) 0.0256(10) Uani 1 1 d . . . C23 C 0.1174(4) 0.9727(3) 0.2646(3) 0.0316(12) Uani 1 1 d . . . C22 C 0.0833(4) 0.9538(3) 0.3311(3) 0.0325(12) Uani 1 1 d . . . C20 C 0.0040(4) 0.8941(3) 0.3445(3) 0.0284(11) Uani 1 1 d . . . C21 C 0.0415(7) 0.9043(4) 0.4678(3) 0.0577(18) Uani 1 1 d . . . O5 O -0.0278(3) 0.8696(2) 0.40933(17) 0.0359(9) Uani 1 1 d . . . C27 C -0.0175(4) 0.9532(3) 0.0891(3) 0.0303(11) Uani 1 1 d . . . C26 C 0.1137(4) 0.9480(3) 0.1339(3) 0.0308(11) Uani 1 1 d . . . C28 C -0.2060(5) 1.0273(3) 0.0567(4) 0.0530(17) Uani 1 1 d . . . O6 O -0.0744(3) 1.0172(2) 0.0948(2) 0.0410(9) Uani 1 1 d . . . O7 O -0.0659(4) 0.9074(2) 0.0544(2) 0.0507(11) Uani 1 1 d . . . N1 N 0.2046(4) 0.8904(2) 0.1116(2) 0.0366(11) Uani 1 1 d . . . O9 O 0.3486(4) 0.83660(19) 0.0397(2) 0.0428(10) Uani 1 1 d . . . O8 O 0.2742(4) 0.9494(2) 0.0141(2) 0.0530(12) Uani 1 1 d . . . C29 C 0.2755(5) 0.8969(3) 0.0512(3) 0.0370(13) Uani 1 1 d . . . C33 C 0.5586(7) 0.8842(4) -0.0177(4) 0.067(2) Uani 1 1 d . . . C34 C 0.3500(7) 0.8376(5) -0.0890(4) 0.075(2) Uani 1 1 d . . . C31 C 0.4395(5) 0.8296(3) -0.0219(3) 0.0491(16) Uani 1 1 d . . . C32 C 0.4979(8) 0.7553(4) -0.0127(5) 0.079(3) Uani 1 1 d . . . C36 C -0.2632(4) 0.7760(3) 0.2843(3) 0.0262(11) Uani 1 1 d . . . C37 C -0.4604(4) 0.5797(3) 0.3200(3) 0.0463(15) Uani 1 1 d . . . 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 0.0254(4) 0.0396(9) 0.0291(6) 0.0019(6) -0.0032(4) 0.0055(4) O1 0.0531(19) 0.039(3) 0.046(2) 0.007(2) 0.0069(16) 0.0089(17) C1 0.0234(15) 0.030(3) 0.030(3) -0.004(2) -0.0077(16) 0.0009(16) C5 0.034(2) 0.045(4) 0.036(3) -0.006(3) 0.0038(19) -0.002(2) C4 0.036(2) 0.042(4) 0.036(3) -0.001(3) -0.0055(19) -0.002(2) C6 0.039(2) 0.034(3) 0.028(3) 0.000(2) 0.0026(18) -0.004(2) C2 0.0277(18) 0.043(4) 0.048(3) 0.001(3) 0.0017(18) -0.0095(19) C3 0.037(2) 0.037(4) 0.058(4) 0.000(3) -0.004(2) -0.001(2) C7 0.047(3) 0.047(4) 0.080(5) -0.023(4) 0.001(3) 0.014(3) C8 0.0221(16) 0.035(3) 0.021(2) 0.002(2) -0.0040(14) 0.0024(16) O10 0.060(2) 0.103(4) 0.072(3) -0.009(3) -0.023(2) -0.030(3) C11 0.039(2) 0.045(4) 0.055(4) -0.023(3) -0.019(2) 0.004(2) C9 0.0224(15) 0.034(3) 0.027(3) -0.003(2) -0.0028(14) 0.0050(15) C12 0.085(4) 0.085(6) 0.041(4) -0.016(4) -0.031(3) 0.022(4) O2 0.0313(13) 0.042(2) 0.031(2) -0.0054(16) -0.0093(13) 0.0004(13) C17 0.0216(15) 0.031(3) 0.031(3) -0.003(2) 0.0011(15) 0.0020(16) C15 0.0195(14) 0.022(3) 0.040(3) 0.004(2) -0.0039(17) 0.0017(14) C13 0.0197(15) 0.021(3) 0.027(2) -0.002(2) 0.0003(14) -0.0011(14) C16 0.0222(16) 0.028(3) 0.030(2) -0.003(2) 0.0020(15) -0.0023(15) C14 0.0235(15) 0.021(3) 0.027(3) -0.003(2) 0.0018(15) -0.0038(14) O3 0.0245(13) 0.025(2) 0.055(2) 0.0061(17) -0.0009(13) -0.0051(12) O4 0.0243(13) 0.030(2) 0.069(3) 0.0089(19) -0.0130(15) 0.0012(13) C18 0.026(2) 0.051(4) 0.112(6) 0.012(4) -0.028(3) 0.001(2) C19 0.0206(14) 0.024(3) 0.033(3) -0.002(2) -0.0010(16) 0.0014(14) C24 0.0239(15) 0.027(3) 0.032(3) -0.003(2) 0.0046(16) 0.0019(15) C25 0.0250(16) 0.017(3) 0.035(3) 0.000(2) -0.0013(16) 0.0039(15) C23 0.0293(18) 0.026(3) 0.039(3) -0.006(2) 0.0037(17) 0.0038(17) C22 0.0314(18) 0.021(3) 0.045(3) -0.004(2) -0.0012(19) -0.0002(17) C20 0.0253(16) 0.025(3) 0.035(3) 0.002(2) 0.0022(16) 0.0020(16) C21 0.074(4) 0.063(5) 0.037(3) -0.024(3) 0.003(3) -0.021(3) O5 0.0442(16) 0.038(2) 0.0254(19) -0.0078(17) 0.0025(13) -0.0105(15) C27 0.038(2) 0.022(3) 0.031(3) 0.003(2) 0.0046(18) -0.0005(19) C26 0.0264(17) 0.028(3) 0.038(3) -0.002(2) 0.0069(17) 0.0020(16) C28 0.041(2) 0.046(4) 0.072(4) -0.007(3) -0.021(3) 0.015(2) O6 0.0403(16) 0.032(3) 0.051(2) -0.0078(19) -0.0094(15) 0.0045(15) O7 0.065(2) 0.036(3) 0.052(3) -0.014(2) -0.0176(19) 0.0014(19) N1 0.0359(18) 0.033(3) 0.041(3) 0.000(2) 0.0137(16) 0.0048(16) O9 0.0461(17) 0.030(2) 0.053(2) -0.0014(19) 0.0243(16) 0.0034(15) O8 0.062(2) 0.038(3) 0.059(3) 0.015(2) 0.032(2) 0.0145(19) C29 0.0311(19) 0.031(4) 0.049(3) 0.006(3) 0.017(2) 0.0019(18) C33 0.057(3) 0.055(5) 0.089(5) -0.005(4) 0.037(3) -0.005(3) C34 0.062(4) 0.104(7) 0.058(5) -0.017(4) 0.022(3) 0.007(4) C31 0.043(2) 0.048(4) 0.056(4) -0.008(3) 0.022(2) 0.007(2) C32 0.105(6) 0.023(4) 0.109(6) 0.006(4) 0.065(5) 0.025(4) C36 0.0237(16) 0.020(3) 0.035(3) 0.003(2) -0.0036(16) 0.0039(15) C37 0.0244(17) 0.040(4) 0.074(4) 0.012(3) -0.012(2) -0.0111(19) _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 1.499(4) . ? S1 C1 1.791(5) . ? S1 C9 1.810(5) . ? C1 C6 1.379(6) . ? C1 C2 1.408(7) . ? C5 C6 1.400(7) . ? C5 C4 1.401(8) . ? C4 C3 1.430(7) . ? C4 C7 1.525(7) . ? C2 C3 1.364(7) . ? C8 O2 1.446(6) . ? C8 C13 1.522(5) . ? C8 C9 1.529(6) . ? O10 C11 1.217(8) . ? C11 O2 1.356(5) . ? C11 C12 1.472(9) . ? C17 C16 1.385(5) . ? C17 C13 1.402(6) . ? C15 C16 1.387(6) . ? C15 C36 1.389(6) . ? C13 C14 1.394(6) . ? C16 O3 1.368(6) . ? C14 C36 1.403(5) . ? C14 C19 1.494(6) . ? O3 C37 1.411(5) . ? O4 C36 1.376(5) . ? O4 C18 1.450(5) . ? C19 C25 1.387(7) . ? C19 C20 1.406(7) . ? C24 C23 1.394(7) . ? C24 C25 1.395(6) . ? C24 C26 1.535(7) . ? C23 C22 1.369(7) . ? C22 C20 1.385(6) . ? C20 O5 1.364(6) . ? C21 O5 1.460(7) . ? C27 O7 1.189(6) . ? C27 O6 1.334(6) . ? C27 C26 1.519(6) . ? C26 N1 1.458(6) . ? C28 O6 1.463(6) . ? N1 C29 1.349(6) . ? O9 C29 1.357(6) . ? O9 C31 1.472(6) . ? O8 C29 1.224(6) . ? C33 C31 1.536(8) . ? C34 C31 1.553(10) . ? C31 C32 1.525(9) . ? 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 C1 107.1(2) . . ? O1 S1 C9 106.8(2) . . ? C1 S1 C9 96.5(2) . . ? C6 C1 C2 121.3(5) . . ? C6 C1 S1 117.4(4) . . ? C2 C1 S1 121.0(3) . . ? C6 C5 C4 121.1(4) . . ? C5 C4 C3 118.8(5) . . ? C5 C4 C7 120.3(5) . . ? C3 C4 C7 120.9(5) . . ? C1 C6 C5 118.7(5) . . ? C3 C2 C1 120.3(4) . . ? C2 C3 C4 119.8(5) . . ? O2 C8 C13 106.5(3) . . ? O2 C8 C9 108.8(4) . . ? C13 C8 C9 112.1(4) . . ? O10 C11 O2 121.4(6) . . ? O10 C11 C12 127.3(5) . . ? O2 C11 C12 111.3(6) . . ? C8 C9 S1 109.3(3) . . ? C11 O2 C8 117.5(4) . . ? C16 C17 C13 119.0(4) . . ? C16 C15 C36 118.8(3) . . ? C14 C13 C17 121.4(3) . . ? C14 C13 C8 120.4(4) . . ? C17 C13 C8 118.2(4) . . ? O3 C16 C17 114.0(4) . . ? O3 C16 C15 124.7(3) . . ? C17 C16 C15 121.3(4) . . ? C13 C14 C36 117.6(4) . . ? C13 C14 C19 121.2(3) . . ? C36 C14 C19 121.1(4) . . ? C16 O3 C37 118.9(4) . . ? C36 O4 C18 117.5(4) . . ? C25 C19 C20 118.2(4) . . ? C25 C19 C14 119.4(4) . . ? C20 C19 C14 122.2(4) . . ? C23 C24 C25 119.4(5) . . ? C23 C24 C26 121.6(4) . . ? C25 C24 C26 118.9(4) . . ? C19 C25 C24 121.3(4) . . ? C22 C23 C24 119.7(5) . . ? C23 C22 C20 121.2(5) . . ? O5 C20 C22 124.7(4) . . ? O5 C20 C19 115.1(4) . . ? C22 C20 C19 120.2(4) . . ? C20 O5 C21 116.8(4) . . ? O7 C27 O6 123.7(4) . . ? O7 C27 C26 126.1(5) . . ? O6 C27 C26 110.2(4) . . ? N1 C26 C27 111.6(4) . . ? N1 C26 C24 107.4(4) . . ? C27 C26 C24 108.5(3) . . ? C27 O6 C28 115.2(4) . . ? C29 N1 C26 118.7(4) . . ? C29 O9 C31 120.5(4) . . ? O8 C29 N1 124.9(5) . . ? O8 C29 O9 126.6(5) . . ? N1 C29 O9 108.6(5) . . ? O9 C31 C32 101.7(5) . . ? O9 C31 C33 109.2(5) . . ? C32 C31 C33 110.4(5) . . ? O9 C31 C34 109.8(4) . . ? C32 C31 C34 112.7(6) . . ? C33 C31 C34 112.4(6) . . ? O4 C36 C15 123.0(3) . . ? O4 C36 C14 115.0(4) . . ? C15 C36 C14 121.9(4) . . ? _diffrn_measured_fraction_theta_max 0.773 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.773 _refine_diff_density_max 0.503 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.086 # Attachment '- (aS)-5.cif' data_fctl100920 _database_code_depnum_ccdc_archive 'CCDC 871941' #TrackingRef '- (aS)-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H41 N O9 S' _chemical_formula_sum 'C33 H41 N O9 S' _chemical_formula_weight 627.73 _chemical_absolute_configuration rmad 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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.6718(5) _cell_length_b 11.6816(6) _cell_length_c 14.2167(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.9350(10) _cell_angle_gamma 90.00 _cell_volume 1644.01(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.01 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9558 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details sadabs _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17874 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.04 _reflns_number_total 6187 _reflns_number_gt 5867 _reflns_threshold_expression I>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, 1997)' _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^)+(0.0358P)^2^+0.3232P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 6187 _refine_ls_number_parameters 410 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.91622(14) 1.10812(13) 0.82225(10) 0.0215(3) Uani 1 1 d . . . C2 C 0.83951(17) 1.20070(14) 0.82934(12) 0.0287(3) Uani 1 1 d . . . H2 H 0.8758 1.2553 0.8821 0.034 Uiso 1 1 calc R . . C3 C 0.70966(18) 1.21304(16) 0.75887(12) 0.0351(4) Uani 1 1 d . . . H3 H 0.6559 1.2755 0.7645 0.042 Uiso 1 1 calc R . . C4 C 0.65644(17) 1.13532(18) 0.67965(12) 0.0363(4) Uani 1 1 d . . . C5 C 0.73597(17) 1.04451(17) 0.67357(13) 0.0374(4) Uani 1 1 d . . . H5 H 0.7013 0.9913 0.6194 0.045 Uiso 1 1 calc R . . C6 C 0.86569(16) 1.02943(15) 0.74505(12) 0.0303(3) Uani 1 1 d . . . H6 H 0.9188 0.9658 0.7408 0.036 Uiso 1 1 calc R . . C7 C 0.5166(2) 1.1506(3) 0.59985(16) 0.0619(7) Uani 1 1 d . . . H7A H 0.5186 1.1346 0.5328 0.093 Uiso 1 1 calc R . . H7B H 0.4864 1.2295 0.6017 0.093 Uiso 1 1 calc R . . H7C H 0.4540 1.0977 0.6133 0.093 Uiso 1 1 calc R . . C8 C 1.05493(14) 1.00053(14) 1.00288(10) 0.0231(3) Uani 1 1 d . . . H8A H 1.0305 0.9234 0.9726 0.028 Uiso 1 1 calc R . . H8B H 1.1401 0.9929 1.0627 0.028 Uiso 1 1 calc R . . C9 C 0.94541(13) 1.04028(13) 1.03897(10) 0.0190(3) Uani 1 1 d . . . H9 H 0.8572 1.0399 0.9800 0.023 Uiso 1 1 calc R . . C10 C 0.86026(15) 1.20833(15) 1.08664(12) 0.0283(3) Uani 1 1 d . . . H10A H 0.7870 1.2154 1.0201 0.043 Uiso 1 1 calc R . . H10B H 0.8852 1.2845 1.1167 0.043 Uiso 1 1 calc R . . H10C H 0.8301 1.1609 1.1310 0.043 Uiso 1 1 calc R . . C11 C 0.93401(14) 0.96144(12) 1.12061(10) 0.0183(3) Uani 1 1 d . . . C12 C 1.03994(14) 0.96086(13) 1.21616(10) 0.0209(3) Uani 1 1 d . . . H12 H 1.1170 1.0080 1.2288 0.025 Uiso 1 1 calc R . . C13 C 1.03042(15) 0.89088(14) 1.29129(10) 0.0224(3) Uani 1 1 d . . . C14 C 0.91486(15) 0.82569(14) 1.27485(10) 0.0234(3) Uani 1 1 d . . . H14 H 0.9078 0.7798 1.3278 0.028 Uiso 1 1 calc R . . C15 C 0.81037(14) 0.82806(13) 1.18090(10) 0.0201(3) Uani 1 1 d . . . C16 C 0.82012(13) 0.89377(12) 1.10073(10) 0.0170(3) Uani 1 1 d . . . C17 C 1.25305(16) 0.93735(17) 1.40733(12) 0.0339(4) Uani 1 1 d . . . H17A H 1.2921 0.9147 1.3577 0.051 Uiso 1 1 calc R . . H17B H 1.3157 0.9174 1.4757 0.051 Uiso 1 1 calc R . . H17C H 1.2371 1.0201 1.4031 0.051 Uiso 1 1 calc R . . C18 C 0.67751(18) 0.70504(16) 1.23943(13) 0.0337(4) Uani 1 1 d . . . H18A H 0.7466 0.6450 1.2618 0.050 Uiso 1 1 calc R . . H18B H 0.5876 0.6700 1.2158 0.050 Uiso 1 1 calc R . . H18C H 0.6878 0.7566 1.2962 0.050 Uiso 1 1 calc R . . C19 C 0.70993(13) 0.88695(12) 0.99797(10) 0.0177(3) Uani 1 1 d . . . C20 C 0.58835(14) 0.94555(13) 0.97818(11) 0.0219(3) Uani 1 1 d . . . C21 C 0.48418(14) 0.93683(14) 0.88379(11) 0.0254(3) Uani 1 1 d . . . H21 H 0.4001 0.9736 0.8714 0.031 Uiso 1 1 calc R . . C22 C 0.50425(14) 0.87380(14) 0.80778(11) 0.0234(3) Uani 1 1 d . . . H22 H 0.4336 0.8693 0.7429 0.028 Uiso 1 1 calc R . . C23 C 0.62537(13) 0.81708(13) 0.82440(10) 0.0190(3) Uani 1 1 d . . . C24 C 0.72635(13) 0.82324(12) 0.92086(10) 0.0177(3) Uani 1 1 d . . . H24 H 0.8085 0.7828 0.9342 0.021 Uiso 1 1 calc R . . C25 C 0.47876(18) 1.0950(2) 1.03259(14) 0.0466(5) Uani 1 1 d . . . H25A H 0.4794 1.1414 0.9754 0.070 Uiso 1 1 calc R . . H25B H 0.4949 1.1443 1.0917 0.070 Uiso 1 1 calc R . . H25C H 0.3908 1.0573 1.0145 0.070 Uiso 1 1 calc R . . C26 C 0.64184(13) 0.74743(13) 0.73918(10) 0.0209(3) Uani 1 1 d . . . H26 H 0.5855 0.7843 0.6735 0.025 Uiso 1 1 calc R . . C27 C 0.58800(14) 0.62658(14) 0.73951(11) 0.0253(3) Uani 1 1 d . . . C28 C 0.3912(2) 0.5117(2) 0.6877(2) 0.0575(6) Uani 1 1 d . . . H28A H 0.4332 0.4541 0.6587 0.086 Uiso 1 1 calc R . . H28B H 0.2945 0.5165 0.6466 0.086 Uiso 1 1 calc R . . H28C H 0.4038 0.4898 0.7572 0.086 Uiso 1 1 calc R . . C29 C 0.80665(14) 0.75644(13) 0.65892(10) 0.0217(3) Uani 1 1 d . . . C30 C 0.99808(15) 0.76790(17) 0.60288(12) 0.0306(3) Uani 1 1 d . . . C31 C 0.9534(3) 0.87996(19) 0.54759(17) 0.0509(6) Uani 1 1 d . . . H31A H 0.8557 0.8779 0.5090 0.076 Uiso 1 1 calc R . . H31B H 1.0006 0.8920 0.5010 0.076 Uiso 1 1 calc R . . H31C H 0.9748 0.9428 0.5968 0.076 Uiso 1 1 calc R . . C32 C 1.14795(19) 0.7699(3) 0.66459(16) 0.0688(8) Uani 1 1 d . . . H32A H 1.1687 0.8330 0.7134 0.103 Uiso 1 1 calc R . . H32B H 1.1973 0.7806 0.6194 0.103 Uiso 1 1 calc R . . H32C H 1.1750 0.6972 0.7011 0.103 Uiso 1 1 calc R . . C33 C 0.9599(2) 0.66623(18) 0.53226(14) 0.0414(4) Uani 1 1 d . . . H33A H 0.9815 0.5954 0.5721 0.062 Uiso 1 1 calc R . . H33B H 1.0107 0.6687 0.4873 0.062 Uiso 1 1 calc R . . H33C H 0.8629 0.6686 0.4915 0.062 Uiso 1 1 calc R . . N1 N 0.77975(11) 0.74352(12) 0.74419(9) 0.0217(3) Uani 1 1 d . . . O1 O 1.15693(11) 1.01543(12) 0.86184(8) 0.0324(3) Uani 1 1 d . . . O2 O 0.97551(10) 1.15579(9) 1.07503(7) 0.0217(2) Uani 1 1 d . . . O3 O 1.12840(11) 0.87885(11) 1.38614(8) 0.0303(3) Uani 1 1 d . . . O4 O 0.69283(10) 0.76829(11) 1.15875(8) 0.0280(2) Uani 1 1 d . . . O5 O 0.58233(10) 1.01042(11) 1.05613(8) 0.0294(2) Uani 1 1 d . . . O6 O 0.65459(12) 0.54527(11) 0.78045(10) 0.0374(3) Uani 1 1 d . . . O7 O 0.45409(11) 0.62277(12) 0.68861(10) 0.0411(3) Uani 1 1 d . . . O8 O 0.72162(11) 0.77061(13) 0.57481(8) 0.0341(3) Uani 1 1 d . . . O9 O 0.94078(10) 0.75336(11) 0.68253(7) 0.0263(2) Uani 1 1 d . . . S1 S 1.08647(3) 1.09252(3) 0.91072(3) 0.02316(8) Uani 1 1 d . . . H1N H 0.8444(17) 0.7201(15) 0.7988(13) 0.022(4) Uiso 1 1 d . . . 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 C1 0.0245(6) 0.0228(7) 0.0183(6) 0.0024(5) 0.0090(5) -0.0028(6) C2 0.0407(9) 0.0235(8) 0.0230(7) 0.0003(6) 0.0130(6) 0.0026(7) C3 0.0419(9) 0.0359(10) 0.0298(8) 0.0062(7) 0.0160(7) 0.0130(8) C4 0.0307(8) 0.0478(11) 0.0276(7) 0.0043(7) 0.0076(6) 0.0074(8) C5 0.0360(9) 0.0398(10) 0.0281(8) -0.0083(7) 0.0025(7) 0.0011(8) C6 0.0328(8) 0.0268(9) 0.0292(8) -0.0045(6) 0.0091(6) 0.0034(7) C7 0.0392(11) 0.092(2) 0.0393(10) -0.0056(11) -0.0022(8) 0.0231(12) C8 0.0242(7) 0.0251(7) 0.0197(6) 0.0037(6) 0.0078(5) 0.0001(6) C9 0.0186(6) 0.0217(7) 0.0158(6) 0.0014(5) 0.0054(5) -0.0024(5) C10 0.0280(8) 0.0268(8) 0.0313(8) 0.0003(6) 0.0124(6) 0.0028(6) C11 0.0197(6) 0.0189(7) 0.0172(6) 0.0005(5) 0.0077(5) 0.0012(5) C12 0.0185(6) 0.0241(7) 0.0186(6) 0.0002(5) 0.0051(5) -0.0028(5) C13 0.0242(7) 0.0278(8) 0.0146(6) -0.0006(5) 0.0066(5) 0.0016(6) C14 0.0285(7) 0.0256(7) 0.0186(6) 0.0035(6) 0.0117(5) -0.0002(6) C15 0.0216(6) 0.0202(7) 0.0210(6) -0.0013(5) 0.0110(5) -0.0004(5) C16 0.0166(6) 0.0190(7) 0.0161(6) -0.0009(5) 0.0070(5) 0.0014(5) C17 0.0270(8) 0.0440(10) 0.0223(7) 0.0019(7) -0.0004(6) -0.0045(7) C18 0.0366(9) 0.0371(10) 0.0329(8) 0.0016(7) 0.0194(7) -0.0116(7) C19 0.0155(6) 0.0196(7) 0.0176(6) 0.0015(5) 0.0056(5) -0.0002(5) C20 0.0199(7) 0.0231(7) 0.0238(7) -0.0012(6) 0.0094(5) 0.0016(6) C21 0.0165(6) 0.0315(8) 0.0274(7) -0.0011(6) 0.0072(6) 0.0047(6) C22 0.0173(6) 0.0290(8) 0.0205(6) -0.0005(6) 0.0031(5) 0.0007(6) C23 0.0169(6) 0.0210(7) 0.0193(6) 0.0004(5) 0.0069(5) -0.0026(5) C24 0.0145(6) 0.0189(7) 0.0200(6) 0.0019(5) 0.0067(5) 0.0011(5) C25 0.0409(9) 0.0548(12) 0.0385(9) -0.0125(9) 0.0083(7) 0.0269(10) C26 0.0161(6) 0.0274(8) 0.0174(6) -0.0011(6) 0.0040(5) -0.0004(6) C27 0.0210(7) 0.0301(8) 0.0256(7) -0.0097(6) 0.0097(5) -0.0039(6) C28 0.0392(10) 0.0478(13) 0.0797(16) -0.0218(12) 0.0156(10) -0.0221(10) C29 0.0234(6) 0.0212(7) 0.0209(6) -0.0031(6) 0.0086(5) -0.0016(6) C30 0.0316(8) 0.0422(10) 0.0263(7) -0.0013(7) 0.0203(6) -0.0034(7) C31 0.0836(16) 0.0339(11) 0.0584(12) 0.0030(9) 0.0533(12) -0.0032(10) C32 0.0326(10) 0.140(3) 0.0433(11) -0.0059(14) 0.0254(9) -0.0076(14) C33 0.0651(13) 0.0343(10) 0.0382(9) -0.0024(8) 0.0346(9) 0.0032(9) N1 0.0163(5) 0.0326(7) 0.0157(5) 0.0001(5) 0.0055(4) -0.0001(5) O1 0.0280(5) 0.0440(7) 0.0304(6) 0.0004(5) 0.0169(4) 0.0028(5) O2 0.0217(5) 0.0206(5) 0.0223(5) 0.0002(4) 0.0075(4) -0.0023(4) O3 0.0273(5) 0.0425(7) 0.0165(5) 0.0054(5) 0.0029(4) -0.0044(5) O4 0.0262(5) 0.0326(6) 0.0260(5) 0.0031(5) 0.0106(4) -0.0087(5) O5 0.0260(5) 0.0361(7) 0.0253(5) -0.0055(5) 0.0088(4) 0.0104(5) O6 0.0318(6) 0.0290(6) 0.0527(7) -0.0001(6) 0.0175(5) 0.0001(5) O7 0.0213(5) 0.0405(8) 0.0537(7) -0.0110(6) 0.0050(5) -0.0096(5) O8 0.0288(5) 0.0531(8) 0.0185(5) 0.0019(5) 0.0068(4) 0.0024(6) O9 0.0219(5) 0.0403(7) 0.0200(5) 0.0009(5) 0.0115(4) -0.0006(5) S1 0.02238(15) 0.02724(18) 0.02134(15) -0.00031(14) 0.00987(12) -0.00511(15) _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 C1 C6 1.378(2) . ? C1 C2 1.383(2) . ? C1 S1 1.7914(14) . ? C2 C3 1.381(2) . ? C2 H2 0.9500 . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 C7 1.511(2) . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.514(2) . ? C8 S1 1.8205(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O2 1.4366(18) . ? C9 C11 1.5217(19) . ? C9 H9 1.0000 . ? C10 O2 1.4381(18) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.3875(19) . ? C11 C12 1.4058(18) . ? C12 C13 1.378(2) . ? C12 H12 0.9500 . ? C13 O3 1.3703(16) . ? C13 C14 1.393(2) . ? C14 C15 1.3840(19) . ? C14 H14 0.9500 . ? C15 O4 1.3657(17) . ? C15 C16 1.4099(19) . ? C16 C19 1.4967(18) . ? C17 O3 1.424(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O4 1.4242(19) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.3892(19) . ? C19 C20 1.3994(19) . ? C20 O5 1.3637(18) . ? C20 C21 1.390(2) . ? C21 C22 1.389(2) . ? C21 H21 0.9500 . ? C22 C23 1.392(2) . ? C22 H22 0.9500 . ? C23 C24 1.3939(18) . ? C23 C26 1.5230(19) . ? C24 H24 0.9500 . ? C25 O5 1.426(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N1 1.4474(17) . ? C26 C27 1.525(2) . ? C26 H26 1.0000 . ? C27 O6 1.199(2) . ? C27 O7 1.3399(17) . ? C28 O7 1.459(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O8 1.2125(17) . ? C29 O9 1.3431(16) . ? C29 N1 1.3545(18) . ? C30 O9 1.4840(17) . ? C30 C33 1.509(3) . ? C30 C31 1.510(3) . ? C30 C32 1.510(2) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N1 H1N 0.868(18) . ? O1 S1 1.4998(12) . ? 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 C1 C2 120.92(14) . . ? C6 C1 S1 118.94(12) . . ? C2 C1 S1 120.08(11) . . ? C3 C2 C1 119.32(15) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.96(16) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.49(15) . . ? C5 C4 C7 120.12(18) . . ? C3 C4 C7 121.37(18) . . ? C4 C5 C6 121.29(16) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 119.00(15) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? 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 S1 115.88(11) . . ? C9 C8 H8A 108.3 . . ? S1 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? S1 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? O2 C9 C8 108.11(11) . . ? O2 C9 C11 111.55(11) . . ? C8 C9 C11 111.38(12) . . ? O2 C9 H9 108.6 . . ? C8 C9 H9 108.6 . . ? C11 C9 H9 108.6 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 121.40(13) . . ? C16 C11 C9 120.20(12) . . ? C12 C11 C9 118.39(12) . . ? C13 C12 C11 119.09(13) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? O3 C13 C12 124.98(14) . . ? O3 C13 C14 114.29(13) . . ? C12 C13 C14 120.73(13) . . ? C15 C14 C13 119.65(13) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O4 C15 C14 123.50(13) . . ? O4 C15 C16 115.52(12) . . ? C14 C15 C16 120.99(13) . . ? C11 C16 C15 117.98(12) . . ? C11 C16 C19 122.56(12) . . ? C15 C16 C19 119.46(12) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 118.96(12) . . ? C24 C19 C16 120.94(12) . . ? C20 C19 C16 120.10(12) . . ? O5 C20 C21 124.17(13) . . ? O5 C20 C19 115.47(12) . . ? C21 C20 C19 120.35(13) . . ? C22 C21 C20 119.32(13) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 121.58(13) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C22 C23 C24 118.04(13) . . ? C22 C23 C26 119.68(12) . . ? C24 C23 C26 122.25(12) . . ? C19 C24 C23 121.66(12) . . ? C19 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1 C26 C23 113.27(11) . . ? N1 C26 C27 110.37(12) . . ? C23 C26 C27 109.67(11) . . ? N1 C26 H26 107.8 . . ? C23 C26 H26 107.8 . . ? C27 C26 H26 107.8 . . ? O6 C27 O7 123.73(15) . . ? O6 C27 C26 125.40(13) . . ? O7 C27 C26 110.87(13) . . ? O7 C28 H28A 109.5 . . ? O7 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O7 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O8 C29 O9 125.81(13) . . ? O8 C29 N1 124.56(13) . . ? O9 C29 N1 109.62(11) . . ? O9 C30 C33 109.38(14) . . ? O9 C30 C31 110.87(14) . . ? C33 C30 C31 112.44(15) . . ? O9 C30 C32 101.97(12) . . ? C33 C30 C32 111.24(19) . . ? C31 C30 C32 110.5(2) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 N1 C26 120.26(11) . . ? C29 N1 H1N 118.2(11) . . ? C26 N1 H1N 120.5(11) . . ? C9 O2 C10 110.79(11) . . ? C13 O3 C17 117.91(12) . . ? C15 O4 C18 116.83(12) . . ? C20 O5 C25 117.51(12) . . ? C27 O7 C28 115.37(15) . . ? C29 O9 C30 120.71(11) . . ? O1 S1 C1 106.76(7) . . ? O1 S1 C8 103.79(7) . . ? C1 S1 C8 98.84(6) . . ? 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 C6 C1 C2 C3 1.1(2) . . . . ? S1 C1 C2 C3 178.28(12) . . . . ? C1 C2 C3 C4 -1.6(3) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C2 C3 C4 C7 -177.56(19) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C7 C4 C5 C6 179.00(19) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? S1 C1 C6 C5 -176.93(14) . . . . ? C4 C5 C6 C1 -1.2(3) . . . . ? S1 C8 C9 O2 -53.38(13) . . . . ? S1 C8 C9 C11 -176.27(10) . . . . ? O2 C9 C11 C16 127.12(13) . . . . ? C8 C9 C11 C16 -111.98(14) . . . . ? O2 C9 C11 C12 -51.72(17) . . . . ? C8 C9 C11 C12 69.18(17) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? C9 C11 C12 C13 179.26(13) . . . . ? C11 C12 C13 O3 177.32(14) . . . . ? C11 C12 C13 C14 -3.1(2) . . . . ? O3 C13 C14 C15 -178.12(13) . . . . ? C12 C13 C14 C15 2.3(2) . . . . ? C13 C14 C15 O4 -178.95(14) . . . . ? C13 C14 C15 C16 1.3(2) . . . . ? C12 C11 C16 C15 3.0(2) . . . . ? C9 C11 C16 C15 -175.80(13) . . . . ? C12 C11 C16 C19 -175.98(13) . . . . ? C9 C11 C16 C19 5.2(2) . . . . ? O4 C15 C16 C11 176.34(13) . . . . ? C14 C15 C16 C11 -3.9(2) . . . . ? O4 C15 C16 C19 -4.63(19) . . . . ? C14 C15 C16 C19 175.15(13) . . . . ? C11 C16 C19 C24 76.41(19) . . . . ? C15 C16 C19 C24 -102.57(16) . . . . ? C11 C16 C19 C20 -103.34(16) . . . . ? C15 C16 C19 C20 77.68(18) . . . . ? C24 C19 C20 O5 -177.05(13) . . . . ? C16 C19 C20 O5 2.7(2) . . . . ? C24 C19 C20 C21 2.1(2) . . . . ? C16 C19 C20 C21 -178.12(14) . . . . ? O5 C20 C21 C22 176.07(15) . . . . ? C19 C20 C21 C22 -3.0(2) . . . . ? C20 C21 C22 C23 1.3(2) . . . . ? C21 C22 C23 C24 1.3(2) . . . . ? C21 C22 C23 C26 179.02(15) . . . . ? C20 C19 C24 C23 0.5(2) . . . . ? C16 C19 C24 C23 -179.23(13) . . . . ? C22 C23 C24 C19 -2.2(2) . . . . ? C26 C23 C24 C19 -179.89(13) . . . . ? C22 C23 C26 N1 149.90(14) . . . . ? C24 C23 C26 N1 -32.43(19) . . . . ? C22 C23 C26 C27 -86.31(16) . . . . ? C24 C23 C26 C27 91.36(15) . . . . ? N1 C26 C27 O6 30.6(2) . . . . ? C23 C26 C27 O6 -94.92(17) . . . . ? N1 C26 C27 O7 -150.36(12) . . . . ? C23 C26 C27 O7 84.17(14) . . . . ? O8 C29 N1 C26 -0.7(2) . . . . ? O9 C29 N1 C26 178.07(13) . . . . ? C23 C26 N1 C29 -136.89(14) . . . . ? C27 C26 N1 C29 99.71(16) . . . . ? C8 C9 O2 C10 165.65(11) . . . . ? C11 C9 O2 C10 -71.56(13) . . . . ? C12 C13 O3 C17 -4.0(2) . . . . ? C14 C13 O3 C17 176.40(15) . . . . ? C14 C15 O4 C18 2.9(2) . . . . ? C16 C15 O4 C18 -177.35(14) . . . . ? C21 C20 O5 C25 -15.9(2) . . . . ? C19 C20 O5 C25 163.21(16) . . . . ? O6 C27 O7 C28 1.5(2) . . . . ? C26 C27 O7 C28 -177.63(15) . . . . ? O8 C29 O9 C30 0.0(3) . . . . ? N1 C29 O9 C30 -178.78(14) . . . . ? C33 C30 O9 C29 -67.4(2) . . . . ? C31 C30 O9 C29 57.2(2) . . . . ? C32 C30 O9 C29 174.78(19) . . . . ? C6 C1 S1 O1 18.54(14) . . . . ? C2 C1 S1 O1 -158.68(12) . . . . ? C6 C1 S1 C8 -88.85(13) . . . . ? C2 C1 S1 C8 93.93(13) . . . . ? C9 C8 S1 O1 -159.99(10) . . . . ? C9 C8 S1 C1 -50.19(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.868(18) 2.213(18) 3.0760(15) 172.4(15) 2_747 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.183 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.033