Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;Development of new thiazole-based iridium catalysts and their applications in the asymmetric hydrogenation of trisubstituted olefins ; _publ_contact_author_name 'Prof. Pher Andersson' _publ_contact_author_email PHERA@KEMI.UU.SE loop_ _publ_author_name P.G.Andersson M.Ali P.Cheruku A.Paptchikhine # Attachment 'tome2_n.cif' data_tome2 _database_code_depnum_ccdc_archive 'CCDC 664206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 N2 O3 S2' _chemical_formula_sum 'C28 H30 N2 O3 S2' _chemical_formula_weight 506.66 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 14.5931(6) _cell_length_b 21.5413(8) _cell_length_c 8.0149(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2519.52(17) _cell_formula_units_Z 4 _cell_measurement_temperature 0(2) _cell_measurement_reflns_used 9014 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .45 _exptl_crystal_size_mid .43 _exptl_crystal_size_min .40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9014 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5403 _reflns_number_gt 4047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0347P)^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 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 0.07(7) _refine_ls_number_reflns 5403 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.45187(5) 0.10390(3) 1.07549(8) 0.02813(17) Uani 1 1 d . . . S2 S 0.69034(5) 0.05038(3) 0.53496(10) 0.0387(2) Uani 1 1 d . . . O1 O 0.53756(12) 0.07374(8) 1.0448(2) 0.0358(5) Uani 1 1 d . . . O2 O 0.45568(15) 0.16571(8) 1.1391(2) 0.0423(5) Uani 1 1 d . . . O3 O 0.38098(12) 0.09820(8) 0.6193(2) 0.0297(4) Uani 1 1 d . . . N1 N 0.38710(14) 0.10224(9) 0.8996(2) 0.0228(5) Uani 1 1 d . . . N2 N 0.66899(15) 0.14990(9) 0.7055(3) 0.0259(5) Uani 1 1 d . . . C1 C 0.41955(18) 0.11821(11) 0.7422(3) 0.0249(6) Uani 1 1 d . . . C2 C 0.50082(17) 0.16204(11) 0.7316(3) 0.0265(6) Uani 1 1 d . . . H2 H 0.5143 0.1789 0.8452 0.032 Uiso 1 1 calc R . . C3 C 0.58298(18) 0.12701(11) 0.6692(3) 0.0270(6) Uani 1 1 d . . . C4 C 0.73310(18) 0.11414(11) 0.6408(3) 0.0275(6) Uani 1 1 d . . . C5 C 0.5824(2) 0.07392(12) 0.5789(4) 0.0363(7) Uani 1 1 d . . . H5 H 0.5285 0.0527 0.5446 0.044 Uiso 1 1 calc R . . C6 C 0.83110(18) 0.12545(11) 0.6544(3) 0.0269(6) Uani 1 1 d . . . C7 C 0.89387(19) 0.08329(12) 0.5903(4) 0.0361(7) Uani 1 1 d . . . H7 H 0.8725 0.0462 0.5392 0.043 Uiso 1 1 calc R . . C8 C 0.9864(2) 0.09434(12) 0.5998(4) 0.0403(8) Uani 1 1 d . . . H8 H 1.0285 0.0649 0.5559 0.048 Uiso 1 1 calc R . . C9 C 1.0182(2) 0.14803(12) 0.6727(4) 0.0364(7) Uani 1 1 d . . . H9 H 1.0821 0.1561 0.6770 0.044 Uiso 1 1 calc R . . C10 C 0.9576(2) 0.18969(12) 0.7388(3) 0.0342(7) Uani 1 1 d . . . H10 H 0.9798 0.2263 0.7913 0.041 Uiso 1 1 calc R . . C11 C 0.86425(19) 0.17901(11) 0.7298(3) 0.0308(7) Uani 1 1 d . . . H11 H 0.8227 0.2084 0.7753 0.037 Uiso 1 1 calc R . . C12 C 0.47508(18) 0.21654(11) 0.6135(3) 0.0320(7) Uani 1 1 d . . . H12A H 0.5278 0.2453 0.6047 0.038 Uiso 1 1 calc R . . H12B H 0.4624 0.1999 0.5007 0.038 Uiso 1 1 calc R . . C13 C 0.39238(19) 0.25186(11) 0.6744(3) 0.0276(6) Uani 1 1 d . . . C14 C 0.3055(2) 0.23992(12) 0.6126(4) 0.0349(7) Uani 1 1 d . . . H14 H 0.2980 0.2095 0.5279 0.042 Uiso 1 1 calc R . . C15 C 0.2290(2) 0.27156(13) 0.6719(4) 0.0412(8) Uani 1 1 d . . . H15 H 0.1698 0.2621 0.6299 0.049 Uiso 1 1 calc R . . C16 C 0.2397(2) 0.31655(14) 0.7915(4) 0.0460(8) Uani 1 1 d . . . H16 H 0.1879 0.3384 0.8326 0.055 Uiso 1 1 calc R . . C17 C 0.3260(2) 0.32980(13) 0.8518(4) 0.0460(9) Uani 1 1 d . . . H17 H 0.3336 0.3615 0.9329 0.055 Uiso 1 1 calc R . . C18 C 0.4010(2) 0.29760(12) 0.7957(4) 0.0385(8) Uani 1 1 d . . . H18 H 0.4598 0.3067 0.8406 0.046 Uiso 1 1 calc R . . C19 C 0.31019(17) 0.05795(11) 0.9111(3) 0.0252(6) Uani 1 1 d . . . H19 H 0.3279 0.0171 0.8611 0.030 Uiso 1 1 calc R . . C20 C 0.28818(17) 0.05009(11) 1.0982(3) 0.0251(6) Uani 1 1 d . . . C21 C 0.37742(18) 0.05565(11) 1.1950(3) 0.0267(6) Uani 1 1 d . . . H21A H 0.4052 0.0142 1.2113 0.032 Uiso 1 1 calc R . . H21B H 0.3661 0.0744 1.3059 0.032 Uiso 1 1 calc R . . C22 C 0.20963(19) 0.09750(12) 1.1308(3) 0.0310(7) Uani 1 1 d . . . C23 C 0.15175(19) 0.07319(13) 0.9829(3) 0.0352(7) Uani 1 1 d . . . H23 H 0.0916 0.0947 0.9678 0.042 Uiso 1 1 calc R . . C24 C 0.21854(17) 0.08066(13) 0.8360(3) 0.0319(7) Uani 1 1 d . . . H24A H 0.2227 0.1245 0.7999 0.038 Uiso 1 1 calc R . . H24B H 0.1999 0.0547 0.7399 0.038 Uiso 1 1 calc R . . C25 C 0.14442(18) 0.00327(13) 1.0216(4) 0.0369(7) Uani 1 1 d . . . H25A H 0.1364 -0.0211 0.9179 0.044 Uiso 1 1 calc R . . H25B H 0.0923 -0.0052 1.0972 0.044 Uiso 1 1 calc R . . C26 C 0.23678(17) -0.01249(11) 1.1069(3) 0.0304(7) Uani 1 1 d . . . H26A H 0.2276 -0.0259 1.2239 0.036 Uiso 1 1 calc R . . H26B H 0.2701 -0.0454 1.0454 0.036 Uiso 1 1 calc R . . C27 C 0.2350(2) 0.16705(12) 1.1173(4) 0.0411(8) Uani 1 1 d . . . H27A H 0.1790 0.1921 1.1188 0.062 Uiso 1 1 calc R . . H27B H 0.2682 0.1743 1.0128 0.062 Uiso 1 1 calc R . . H27C H 0.2740 0.1787 1.2118 0.062 Uiso 1 1 calc R . . C28 C 0.1652(2) 0.08943(13) 1.3029(4) 0.0433(8) Uani 1 1 d . . . H28A H 0.1144 0.1189 1.3147 0.065 Uiso 1 1 calc R . . H28B H 0.2109 0.0973 1.3900 0.065 Uiso 1 1 calc R . . H28C H 0.1420 0.0470 1.3139 0.065 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 0.0354(4) 0.0286(3) 0.0203(3) 0.0043(3) -0.0051(3) -0.0080(3) S2 0.0398(5) 0.0331(4) 0.0432(5) -0.0124(4) 0.0152(4) -0.0025(3) O1 0.0276(11) 0.0395(10) 0.0402(12) 0.0137(10) -0.0041(10) -0.0054(9) O2 0.0701(15) 0.0294(10) 0.0274(10) -0.0017(9) -0.0041(11) -0.0176(10) O3 0.0372(11) 0.0339(10) 0.0181(10) -0.0001(9) 0.0016(9) -0.0031(9) N1 0.0264(12) 0.0252(10) 0.0169(11) 0.0009(10) -0.0003(9) -0.0011(10) N2 0.0306(14) 0.0241(10) 0.0231(12) 0.0019(10) 0.0036(11) 0.0030(10) C1 0.0267(16) 0.0258(14) 0.0222(14) -0.0018(12) 0.0032(12) 0.0070(11) C2 0.0313(16) 0.0262(13) 0.0221(14) 0.0021(13) 0.0062(13) -0.0006(11) C3 0.0341(17) 0.0237(13) 0.0232(15) 0.0029(12) 0.0062(13) -0.0022(11) C4 0.0341(16) 0.0252(13) 0.0231(14) 0.0040(12) 0.0072(13) -0.0002(12) C5 0.0373(17) 0.0367(15) 0.0349(16) -0.0111(15) 0.0113(14) -0.0066(13) C6 0.0345(17) 0.0246(13) 0.0215(14) 0.0073(12) 0.0061(13) 0.0020(12) C7 0.0362(18) 0.0310(13) 0.0409(18) 0.0001(14) 0.0157(15) -0.0031(13) C8 0.0440(19) 0.0333(15) 0.0436(19) 0.0067(16) 0.0176(15) 0.0088(14) C9 0.0289(17) 0.0398(16) 0.0404(18) 0.0157(16) 0.0015(14) 0.0022(13) C10 0.0381(18) 0.0292(14) 0.0355(17) 0.0088(13) -0.0056(15) 0.0007(13) C11 0.0353(18) 0.0262(13) 0.0310(17) 0.0037(13) 0.0010(14) 0.0108(12) C12 0.0394(18) 0.0281(13) 0.0284(15) 0.0066(13) 0.0030(14) -0.0011(12) C13 0.0356(18) 0.0240(13) 0.0231(15) 0.0085(12) 0.0017(13) 0.0015(12) C14 0.0433(19) 0.0293(13) 0.0322(17) 0.0060(13) -0.0049(16) -0.0016(13) C15 0.0316(18) 0.0384(16) 0.054(2) 0.0247(17) -0.0084(16) -0.0002(14) C16 0.052(2) 0.0434(17) 0.042(2) 0.0134(17) 0.0052(17) 0.0237(15) C17 0.057(2) 0.0388(16) 0.0425(19) -0.0073(16) -0.0120(18) 0.0240(16) C18 0.043(2) 0.0315(14) 0.0408(19) 0.0016(15) -0.0133(16) 0.0094(13) C19 0.0294(15) 0.0294(12) 0.0168(12) 0.0016(12) 0.0002(12) -0.0039(12) C20 0.0279(16) 0.0272(13) 0.0201(13) 0.0032(12) -0.0014(12) -0.0013(11) C21 0.0391(17) 0.0243(12) 0.0167(13) 0.0029(12) -0.0016(12) -0.0025(11) C22 0.0345(17) 0.0356(14) 0.0228(14) 0.0068(13) 0.0051(13) -0.0006(13) C23 0.0307(17) 0.0486(16) 0.0263(15) 0.0059(14) 0.0026(13) 0.0039(13) C24 0.0328(17) 0.0429(15) 0.0201(14) 0.0029(13) -0.0017(13) -0.0016(13) C25 0.0332(17) 0.0507(17) 0.0267(15) 0.0045(15) -0.0015(14) -0.0140(14) C26 0.0347(17) 0.0335(13) 0.0229(15) 0.0021(13) 0.0010(13) -0.0066(12) C27 0.051(2) 0.0374(15) 0.0350(17) 0.0045(15) 0.0115(16) 0.0085(14) C28 0.054(2) 0.0467(17) 0.0295(16) 0.0054(15) 0.0082(15) 0.0057(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 S1 O2 1.4268(18) . ? S1 O1 1.4305(19) . ? S1 N1 1.698(2) . ? S1 C21 1.783(2) . ? S2 C5 1.692(3) . ? S2 C4 1.731(3) . ? O3 C1 1.214(3) . ? N1 C1 1.391(3) . ? N1 C19 1.476(3) . ? N2 C4 1.318(3) . ? N2 C3 1.380(3) . ? C1 C2 1.518(4) . ? C2 C3 1.503(3) . ? C2 C12 1.554(3) . ? C2 H2 1.0000 . ? C3 C5 1.353(4) . ? C4 C6 1.455(4) . ? C5 H5 0.9500 . ? C6 C7 1.388(3) . ? C6 C11 1.389(3) . ? C7 C8 1.374(4) . ? C7 H7 0.9500 . ? C8 C9 1.376(4) . ? C8 H8 0.9500 . ? C9 C10 1.366(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.508(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.385(4) . ? C13 C18 1.390(4) . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 C16 1.372(4) . ? C15 H15 0.9500 . ? C16 C17 1.379(4) . ? C16 H16 0.9500 . ? C17 C18 1.372(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.543(4) . ? C19 C24 1.546(3) . ? C19 H19 1.0000 . ? C20 C21 1.521(3) . ? C20 C26 1.544(3) . ? C20 C22 1.557(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C28 1.534(4) . ? C22 C23 1.547(4) . ? C22 C27 1.547(3) . ? C23 C24 1.537(4) . ? C23 C25 1.541(4) . ? C23 H23 1.0000 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.549(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 O2 S1 O1 116.83(12) . . ? O2 S1 N1 109.77(11) . . ? O1 S1 N1 109.52(11) . . ? O2 S1 C21 112.06(12) . . ? O1 S1 C21 111.13(11) . . ? N1 S1 C21 95.43(11) . . ? C5 S2 C4 89.76(13) . . ? C1 N1 C19 118.4(2) . . ? C1 N1 S1 123.95(18) . . ? C19 N1 S1 112.68(16) . . ? C4 N2 C3 110.7(2) . . ? O3 C1 N1 119.4(2) . . ? O3 C1 C2 122.5(2) . . ? N1 C1 C2 118.1(2) . . ? C3 C2 C1 109.2(2) . . ? C3 C2 C12 111.7(2) . . ? C1 C2 C12 108.4(2) . . ? C3 C2 H2 109.2 . . ? C1 C2 H2 109.2 . . ? C12 C2 H2 109.2 . . ? C5 C3 N2 114.9(2) . . ? C5 C3 C2 126.7(3) . . ? N2 C3 C2 118.4(2) . . ? N2 C4 C6 124.8(2) . . ? N2 C4 S2 113.6(2) . . ? C6 C4 S2 121.60(19) . . ? C3 C5 S2 111.0(2) . . ? C3 C5 H5 124.5 . . ? S2 C5 H5 124.5 . . ? C7 C6 C11 118.3(3) . . ? C7 C6 C4 120.8(2) . . ? C11 C6 C4 120.9(2) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.2(2) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C13 C12 C2 112.2(2) . . ? C13 C12 H12A 109.2 . . ? C2 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C2 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C18 117.7(3) . . ? C14 C13 C12 121.5(2) . . ? C18 C13 C12 120.8(3) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 121.0(3) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? N1 C19 C20 106.8(2) . . ? N1 C19 C24 115.4(2) . . ? C20 C19 C24 103.5(2) . . ? N1 C19 H19 110.3 . . ? C20 C19 H19 110.3 . . ? C24 C19 H19 110.3 . . ? C21 C20 C19 108.0(2) . . ? C21 C20 C26 117.5(2) . . ? C19 C20 C26 103.9(2) . . ? C21 C20 C22 119.5(2) . . ? C19 C20 C22 104.2(2) . . ? C26 C20 C22 102.0(2) . . ? C20 C21 S1 107.07(17) . . ? C20 C21 H21A 110.3 . . ? S1 C21 H21A 110.3 . . ? C20 C21 H21B 110.3 . . ? S1 C21 H21B 110.3 . . ? H21A C21 H21B 108.6 . . ? C28 C22 C23 114.8(2) . . ? C28 C22 C27 105.9(2) . . ? C23 C22 C27 113.9(2) . . ? C28 C22 C20 112.8(2) . . ? C23 C22 C20 92.9(2) . . ? C27 C22 C20 116.5(2) . . ? C24 C23 C25 107.5(2) . . ? C24 C23 C22 101.9(2) . . ? C25 C23 C22 102.4(2) . . ? C24 C23 H23 114.6 . . ? C25 C23 H23 114.6 . . ? C22 C23 H23 114.6 . . ? C23 C24 C19 102.5(2) . . ? C23 C24 H24A 111.3 . . ? C19 C24 H24A 111.3 . . ? C23 C24 H24B 111.3 . . ? C19 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? C23 C25 C26 104.0(2) . . ? C23 C25 H25A 110.9 . . ? C26 C25 H25A 110.9 . . ? C23 C25 H25B 110.9 . . ? C26 C25 H25B 110.9 . . ? H25A C25 H25B 109.0 . . ? C20 C26 C25 102.2(2) . . ? C20 C26 H26A 111.3 . . ? C25 C26 H26A 111.3 . . ? C20 C26 H26B 111.3 . . ? C25 C26 H26B 111.3 . . ? H26A C26 H26B 109.2 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 C28 H28A 109.5 . . ? C22 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C22 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.288 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.050