# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jiao, Ning' 'Xiang, Shi-Kai' 'Zhang, Bo' 'Zhang, Li-He' 'Cui, Yuxin' _publ_contact_author_name 'Dr Jiao Ning' _publ_contact_author_email jiaoning@bjmu.edu.cn _publ_section_title ; The Versitale Roles Performance of Ammonium Salt Catalysts in Enantioselective Reduction and Alkylation of a,b-Unsaturated Aldehydes: Iminium Catalysis, Enamine Catalysis and Acid Catalysis ; # Attachment '- 6.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 806745' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 O4 S' _chemical_formula_weight 484.58 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 6.2731(2) _cell_length_b 16.1518(6) _cell_length_c 24.6855(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2501.18(15) _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 0.52 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9196 _exptl_absorpt_correction_T_max 0.9790 _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 27819 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4329 _reflns_number_gt 3703 _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^)+(0.0148P)^2^+0.8903P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 4329 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 0.51566(12) 0.46443(5) 0.80759(3) 0.05665(19) Uani 1 1 d . . . O1 O 0.7386(3) 0.44944(14) 0.81103(9) 0.0816(7) Uani 1 1 d . . . O2 O 0.4389(4) 0.53554(12) 0.77959(7) 0.0746(6) Uani 1 1 d . . . O3 O 0.4383(3) 0.46887(11) 0.86780(6) 0.0482(4) Uani 1 1 d . . . O4 O -0.1724(3) 0.40321(11) 1.01704(7) 0.0516(5) Uani 1 1 d . . . C1 C -0.0162(4) 0.43337(15) 1.05122(10) 0.0456(6) Uani 1 1 d . . . C2 C -0.0738(5) 0.44479(17) 1.10459(11) 0.0589(8) Uani 1 1 d . . . H2A H -0.2127 0.4342 1.1157 0.071 Uiso 1 1 calc R . . C3 C 0.0755(6) 0.4719(2) 1.14117(12) 0.0708(9) Uani 1 1 d . . . H3A H 0.0378 0.4804 1.1772 0.085 Uiso 1 1 calc R . . C4 C 0.2799(6) 0.48653(19) 1.12446(12) 0.0695(9) Uani 1 1 d . . . H4A H 0.3816 0.5042 1.1493 0.083 Uiso 1 1 calc R . . C5 C 0.3363(5) 0.47516(17) 1.07089(10) 0.0563(7) Uani 1 1 d . . . H5A H 0.4760 0.4852 1.0601 0.068 Uiso 1 1 calc R . . C6 C 0.1879(4) 0.44906(14) 1.03285(10) 0.0428(6) Uani 1 1 d . . . C7 C 0.2400(4) 0.43600(13) 0.97359(9) 0.0389(6) Uani 1 1 d . . . H7A H 0.3893 0.4187 0.9708 0.047 Uiso 1 1 calc R . . C8 C 0.1015(4) 0.36663(14) 0.95259(9) 0.0399(6) Uani 1 1 d . . . C9 C -0.1006(4) 0.35568(14) 0.97375(10) 0.0429(6) Uani 1 1 d . . . C10 C -0.2399(5) 0.29637(16) 0.95463(11) 0.0533(7) Uani 1 1 d . . . H10A H -0.3750 0.2906 0.9697 0.064 Uiso 1 1 calc R . . C11 C -0.1752(5) 0.24593(17) 0.91288(12) 0.0605(8) Uani 1 1 d . . . H11A H -0.2687 0.2069 0.8987 0.073 Uiso 1 1 calc R . . C12 C 0.0277(5) 0.25310(16) 0.89201(11) 0.0588(8) Uani 1 1 d . . . H12A H 0.0727 0.2178 0.8645 0.071 Uiso 1 1 calc R . . C13 C 0.1635(5) 0.31260(15) 0.91192(10) 0.0502(7) Uani 1 1 d . . . H13A H 0.3004 0.3167 0.8977 0.060 Uiso 1 1 calc R . . C14 C 0.0990(5) 0.70822(17) 0.94653(12) 0.0614(8) Uani 1 1 d . . . H14A H 0.0061 0.6820 0.9704 0.074 Uiso 1 1 calc R . . C15 C 0.0421(6) 0.7834(2) 0.92412(15) 0.0804(10) Uani 1 1 d . . . H15A H -0.0895 0.8068 0.9323 0.096 Uiso 1 1 calc R . . C16 C 0.1791(8) 0.8236(2) 0.88997(16) 0.0908(12) Uani 1 1 d . . . H16A H 0.1423 0.8748 0.8755 0.109 Uiso 1 1 calc R . . C17 C 0.3689(8) 0.7884(2) 0.87729(15) 0.0938(12) Uani 1 1 d . . . H17A H 0.4622 0.8155 0.8540 0.113 Uiso 1 1 calc R . . C18 C 0.4244(6) 0.71243(18) 0.89876(13) 0.0709(9) Uani 1 1 d . . . H18A H 0.5539 0.6886 0.8891 0.085 Uiso 1 1 calc R . . C19 C 0.2918(4) 0.67135(15) 0.93413(10) 0.0468(6) Uani 1 1 d . . . C20 C 0.3514(4) 0.58964(15) 0.96067(10) 0.0439(6) Uani 1 1 d . . . H20A H 0.3158 0.5961 0.9991 0.053 Uiso 1 1 calc R . . C21 C 0.2109(4) 0.51720(13) 0.94006(9) 0.0387(6) Uani 1 1 d . . . H21A H 0.0634 0.5347 0.9464 0.046 Uiso 1 1 calc R . . C22 C 0.2276(4) 0.50321(15) 0.87960(10) 0.0431(6) Uani 1 1 d . . . H22A H 0.1175 0.4651 0.8678 0.052 Uiso 1 1 calc R . . H22B H 0.2085 0.5552 0.8605 0.052 Uiso 1 1 calc R . . C23 C 0.3895(5) 0.37658(17) 0.78155(10) 0.0505(7) Uani 1 1 d . . . C24 C 0.4882(5) 0.30047(18) 0.78407(12) 0.0612(7) Uani 1 1 d . . . H24A H 0.6240 0.2956 0.7988 0.073 Uiso 1 1 calc R . . C25 C 0.3836(6) 0.23157(19) 0.76451(13) 0.0719(9) Uani 1 1 d . . . H25A H 0.4506 0.1802 0.7660 0.086 Uiso 1 1 calc R . . C26 C 0.1818(6) 0.2373(2) 0.74281(13) 0.0685(9) Uani 1 1 d . . . C27 C 0.0871(5) 0.3140(2) 0.74099(12) 0.0691(9) Uani 1 1 d . . . H27A H -0.0492 0.3187 0.7265 0.083 Uiso 1 1 calc R . . C28 C 0.1878(5) 0.38380(19) 0.75988(11) 0.0592(8) Uani 1 1 d . . . H28A H 0.1209 0.4351 0.7581 0.071 Uiso 1 1 calc R . . C29 C 0.0666(7) 0.1618(2) 0.72191(18) 0.1132(15) Uani 1 1 d . . . H29A H -0.0721 0.1776 0.7091 0.170 Uiso 1 1 calc R . . H29B H 0.0519 0.1221 0.7506 0.170 Uiso 1 1 calc R . . H29C H 0.1466 0.1378 0.6927 0.170 Uiso 1 1 calc R . . C30 C 0.5914(4) 0.57331(17) 0.95904(12) 0.0584(8) Uani 1 1 d . . . H30A H 0.6661 0.6208 0.9726 0.088 Uiso 1 1 calc R . . H30B H 0.6346 0.5628 0.9224 0.088 Uiso 1 1 calc R . . H30C H 0.6242 0.5260 0.9811 0.088 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 0.0638(5) 0.0607(4) 0.0454(4) -0.0021(4) 0.0149(4) -0.0092(4) O1 0.0527(13) 0.1025(17) 0.0895(16) -0.0236(14) 0.0244(12) -0.0145(12) O2 0.1186(19) 0.0579(11) 0.0473(11) 0.0107(10) 0.0151(12) -0.0109(13) O3 0.0484(10) 0.0558(10) 0.0403(9) 0.0013(9) 0.0025(8) 0.0028(9) O4 0.0441(10) 0.0604(11) 0.0502(11) 0.0018(9) 0.0023(9) 0.0026(9) C1 0.0527(16) 0.0442(14) 0.0398(14) 0.0060(11) -0.0008(14) 0.0059(12) C2 0.0654(19) 0.0654(18) 0.0460(17) 0.0067(14) 0.0122(15) 0.0071(15) C3 0.099(3) 0.075(2) 0.0380(16) -0.0020(15) 0.0057(17) 0.001(2) C4 0.091(3) 0.075(2) 0.0429(18) -0.0019(15) -0.0102(17) -0.0110(19) C5 0.0625(18) 0.0614(18) 0.0451(17) 0.0020(13) -0.0044(14) -0.0078(15) C6 0.0511(15) 0.0389(13) 0.0383(14) 0.0046(11) -0.0021(12) 0.0005(12) C7 0.0384(13) 0.0411(13) 0.0372(14) 0.0036(11) -0.0002(11) 0.0010(10) C8 0.0484(15) 0.0384(13) 0.0330(13) 0.0066(10) -0.0028(12) -0.0007(11) C9 0.0479(15) 0.0416(13) 0.0393(14) 0.0079(11) -0.0019(12) 0.0025(11) C10 0.0515(17) 0.0497(15) 0.0588(18) 0.0123(14) -0.0062(14) -0.0088(14) C11 0.075(2) 0.0478(16) 0.0592(19) 0.0061(15) -0.0159(18) -0.0187(16) C12 0.084(2) 0.0419(14) 0.0506(16) -0.0029(12) -0.0023(17) -0.0037(16) C13 0.0587(18) 0.0467(15) 0.0452(15) 0.0049(13) 0.0053(14) -0.0003(13) C14 0.064(2) 0.0508(17) 0.070(2) -0.0087(15) 0.0080(16) 0.0007(15) C15 0.085(3) 0.059(2) 0.096(3) -0.0190(19) -0.007(2) 0.0236(19) C16 0.138(4) 0.0477(19) 0.086(3) 0.0061(18) -0.012(3) 0.017(2) C17 0.122(3) 0.064(2) 0.095(3) 0.030(2) 0.016(3) 0.002(2) C18 0.074(2) 0.0621(19) 0.077(2) 0.0165(17) 0.0156(18) 0.0070(17) C19 0.0558(17) 0.0405(14) 0.0441(15) -0.0039(12) -0.0003(13) -0.0038(13) C20 0.0440(15) 0.0443(14) 0.0433(15) 0.0003(11) 0.0000(12) -0.0034(12) C21 0.0358(13) 0.0410(14) 0.0393(14) 0.0026(11) 0.0018(11) 0.0021(11) C22 0.0431(15) 0.0429(13) 0.0433(16) 0.0048(11) -0.0035(12) 0.0001(11) C23 0.0560(17) 0.0585(17) 0.0371(14) -0.0017(13) 0.0075(14) 0.0004(14) C24 0.0549(18) 0.0656(18) 0.0631(18) -0.0031(15) 0.0007(16) 0.0070(16) C25 0.078(2) 0.0561(19) 0.082(2) -0.0112(16) 0.007(2) 0.0133(17) C26 0.070(2) 0.066(2) 0.070(2) -0.0180(16) 0.0080(18) -0.0057(18) C27 0.061(2) 0.081(2) 0.065(2) -0.0125(17) -0.0063(16) 0.0048(17) C28 0.070(2) 0.0586(17) 0.0488(17) -0.0038(14) 0.0030(15) 0.0074(16) C29 0.109(3) 0.086(3) 0.144(4) -0.041(3) 0.001(3) -0.018(3) C30 0.0496(16) 0.0554(16) 0.070(2) 0.0072(14) -0.0125(14) -0.0068(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 O1 1.422(2) . ? S1 O2 1.424(2) . ? S1 O3 1.5653(17) . ? S1 C23 1.747(3) . ? O3 C22 1.463(3) . ? O4 C1 1.382(3) . ? O4 C9 1.391(3) . ? C1 C2 1.378(4) . ? C1 C6 1.382(4) . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.368(5) . ? C3 H3A 0.9300 . ? C4 C5 1.381(4) . ? C4 H4A 0.9300 . ? C5 C6 1.388(4) . ? C5 H5A 0.9300 . ? C6 C7 1.514(3) . ? C7 C8 1.510(3) . ? C7 C21 1.562(3) . ? C7 H7A 0.9800 . ? C8 C9 1.382(3) . ? C8 C13 1.386(3) . ? C9 C10 1.380(3) . ? C10 C11 1.375(4) . ? C10 H10A 0.9300 . ? C11 C12 1.378(4) . ? C11 H11A 0.9300 . ? C12 C13 1.375(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.382(4) . ? C14 C19 1.382(4) . ? C14 H14A 0.9300 . ? C15 C16 1.367(5) . ? C15 H15A 0.9300 . ? C16 C17 1.356(6) . ? C16 H16A 0.9300 . ? C17 C18 1.381(4) . ? C17 H17A 0.9300 . ? C18 C19 1.376(4) . ? C18 H18A 0.9300 . ? C19 C20 1.520(3) . ? C20 C30 1.529(4) . ? C20 C21 1.551(3) . ? C20 H20A 0.9800 . ? C21 C22 1.513(3) . ? C21 H21A 0.9800 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.378(4) . ? C23 C28 1.379(4) . ? C24 C25 1.379(4) . ? C24 H24A 0.9300 . ? C25 C26 1.378(5) . ? C25 H25A 0.9300 . ? C26 C27 1.373(4) . ? C26 C29 1.509(4) . ? C27 C28 1.374(4) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 119.93(15) . . ? O1 S1 O3 104.85(12) . . ? O2 S1 O3 108.61(11) . . ? O1 S1 C23 109.21(14) . . ? O2 S1 C23 108.86(13) . . ? O3 S1 C23 104.24(11) . . ? C22 O3 S1 119.12(15) . . ? C1 O4 C9 115.74(19) . . ? C2 C1 C6 122.1(3) . . ? C2 C1 O4 116.4(3) . . ? C6 C1 O4 121.4(2) . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 117.1(2) . . ? C1 C6 C7 119.4(2) . . ? C5 C6 C7 123.5(2) . . ? C8 C7 C6 108.13(19) . . ? C8 C7 C21 111.95(19) . . ? C6 C7 C21 111.72(18) . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? C21 C7 H7A 108.3 . . ? C9 C8 C13 116.8(2) . . ? C9 C8 C7 119.5(2) . . ? C13 C8 C7 123.7(2) . . ? C10 C9 C8 122.7(2) . . ? C10 C9 O4 116.2(2) . . ? C8 C9 O4 121.1(2) . . ? C11 C10 C9 118.7(3) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 119.8(3) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C8 121.7(3) . . ? C12 C13 H13A 119.2 . . ? C8 C13 H13A 119.2 . . ? C15 C14 C19 121.1(3) . . ? C15 C14 H14A 119.5 . . ? C19 C14 H14A 119.5 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C16 C17 C18 120.3(4) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C19 C18 C17 121.3(3) . . ? C19 C18 H18A 119.3 . . ? C17 C18 H18A 119.3 . . ? C18 C19 C14 117.5(3) . . ? C18 C19 C20 122.9(3) . . ? C14 C19 C20 119.6(2) . . ? C19 C20 C30 112.4(2) . . ? C19 C20 C21 111.9(2) . . ? C30 C20 C21 114.9(2) . . ? C19 C20 H20A 105.6 . . ? C30 C20 H20A 105.6 . . ? C21 C20 H20A 105.6 . . ? C22 C21 C20 113.4(2) . . ? C22 C21 C7 112.92(19) . . ? C20 C21 C7 113.15(19) . . ? C22 C21 H21A 105.5 . . ? C20 C21 H21A 105.5 . . ? C7 C21 H21A 105.5 . . ? O3 C22 C21 108.39(19) . . ? O3 C22 H22A 110.0 . . ? C21 C22 H22A 110.0 . . ? O3 C22 H22B 110.0 . . ? C21 C22 H22B 110.0 . . ? H22A C22 H22B 108.4 . . ? C24 C23 C28 120.3(3) . . ? C24 C23 S1 120.3(2) . . ? C28 C23 S1 119.3(2) . . ? C23 C24 C25 119.4(3) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C26 C25 C24 121.2(3) . . ? C26 C25 H25A 119.4 . . ? C24 C25 H25A 119.4 . . ? C27 C26 C25 118.1(3) . . ? C27 C26 C29 120.7(3) . . ? C25 C26 C29 121.2(3) . . ? C26 C27 C28 122.0(3) . . ? C26 C27 H27A 119.0 . . ? C28 C27 H27A 119.0 . . ? C27 C28 C23 118.9(3) . . ? C27 C28 H28A 120.5 . . ? C23 C28 H28A 120.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C20 C30 H30A 109.5 . . ? C20 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C20 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 O3 C22 165.32(18) . . . . ? O2 S1 O3 C22 36.0(2) . . . . ? C23 S1 O3 C22 -79.9(2) . . . . ? C9 O4 C1 C2 -150.2(2) . . . . ? C9 O4 C1 C6 28.2(3) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? O4 C1 C2 C3 177.8(2) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C2 C1 C6 C5 1.6(4) . . . . ? O4 C1 C6 C5 -176.7(2) . . . . ? C2 C1 C6 C7 -179.4(2) . . . . ? O4 C1 C6 C7 2.3(3) . . . . ? C4 C5 C6 C1 -1.4(4) . . . . ? C4 C5 C6 C7 179.7(2) . . . . ? C1 C6 C7 C8 -31.0(3) . . . . ? C5 C6 C7 C8 148.0(2) . . . . ? C1 C6 C7 C21 92.7(3) . . . . ? C5 C6 C7 C21 -88.4(3) . . . . ? C6 C7 C8 C9 32.3(3) . . . . ? C21 C7 C8 C9 -91.2(3) . . . . ? C6 C7 C8 C13 -148.7(2) . . . . ? C21 C7 C8 C13 87.8(3) . . . . ? C13 C8 C9 C10 -2.4(4) . . . . ? C7 C8 C9 C10 176.6(2) . . . . ? C13 C8 C9 O4 175.8(2) . . . . ? C7 C8 C9 O4 -5.2(3) . . . . ? C1 O4 C9 C10 151.6(2) . . . . ? C1 O4 C9 C8 -26.7(3) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? O4 C9 C10 C11 -178.2(2) . . . . ? C9 C10 C11 C12 2.1(4) . . . . ? C10 C11 C12 C13 -2.0(4) . . . . ? C11 C12 C13 C8 -0.4(4) . . . . ? C9 C8 C13 C12 2.6(4) . . . . ? C7 C8 C13 C12 -176.4(2) . . . . ? C19 C14 C15 C16 -1.4(5) . . . . ? C14 C15 C16 C17 1.5(6) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C19 -1.3(6) . . . . ? C17 C18 C19 C14 1.2(5) . . . . ? C17 C18 C19 C20 -177.1(3) . . . . ? C15 C14 C19 C18 0.1(4) . . . . ? C15 C14 C19 C20 178.5(3) . . . . ? C18 C19 C20 C30 18.7(4) . . . . ? C14 C19 C20 C30 -159.6(3) . . . . ? C18 C19 C20 C21 -112.4(3) . . . . ? C14 C19 C20 C21 69.4(3) . . . . ? C19 C20 C21 C22 59.9(3) . . . . ? C30 C20 C21 C22 -69.8(3) . . . . ? C19 C20 C21 C7 -169.8(2) . . . . ? C30 C20 C21 C7 60.4(3) . . . . ? C8 C7 C21 C22 -49.5(3) . . . . ? C6 C7 C21 C22 -170.9(2) . . . . ? C8 C7 C21 C20 -179.9(2) . . . . ? C6 C7 C21 C20 58.6(3) . . . . ? S1 O3 C22 C21 -168.18(15) . . . . ? C20 C21 C22 O3 70.7(2) . . . . ? C7 C21 C22 O3 -59.7(3) . . . . ? O1 S1 C23 C24 20.7(3) . . . . ? O2 S1 C23 C24 153.3(2) . . . . ? O3 S1 C23 C24 -90.9(2) . . . . ? O1 S1 C23 C28 -161.1(2) . . . . ? O2 S1 C23 C28 -28.5(3) . . . . ? O3 S1 C23 C28 87.3(2) . . . . ? C28 C23 C24 C25 0.2(4) . . . . ? S1 C23 C24 C25 178.4(2) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? C24 C25 C26 C27 0.2(5) . . . . ? C24 C25 C26 C29 -179.4(3) . . . . ? C25 C26 C27 C28 0.2(5) . . . . ? C29 C26 C27 C28 179.8(3) . . . . ? C26 C27 C28 C23 -0.3(5) . . . . ? C24 C23 C28 C27 0.1(4) . . . . ? S1 C23 C28 C27 -178.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.209 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.031