# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yue-Wei Guo' _publ_contact_author_email ywguo@mail.shcnc.ac.cn loop_ _publ_author_name 'Jian-Rong Wang' 'Hai-Li Liu' 'Tibor Kurtan' 'Attila Mandi' 'Sandor Antus' 'J. Li' 'Hai-Yan Zhang' 'Yue-Wei Guo' # Attachment '- Crystal structure data for 8a.cif' data_cd29465 _database_code_depnum_ccdc_archive 'CCDC 767484' #TrackingRef '- Crystal structure data for 8a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H38 O8' _chemical_formula_weight 502.58 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 0.0000 '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 0.0000 '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 7.1487(8) _cell_length_b 13.2022(14) _cell_length_c 28.639(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2702.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1883 _cell_measurement_theta_min 5.266 _cell_measurement_theta_max 47.399 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.265 _exptl_crystal_size_min 0.137 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80505 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14115 _diffrn_reflns_av_R_equivalents 0.0774 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2887 _reflns_number_gt 1662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0426P)^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 SHELXL _refine_ls_extinction_coef 0.0007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2887 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 0.857 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 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 O1 O 0.7716(5) 1.3120(2) 0.19030(11) 0.1029(11) Uani 1 1 d . . . O2 O 0.3950(4) 0.66901(18) 0.15580(9) 0.0681(7) Uani 1 1 d . . . O3 O 0.3733(4) 1.07821(17) 0.07802(8) 0.0597(7) Uani 1 1 d . . . O4 O 0.0688(5) 1.0383(3) 0.08659(11) 0.0967(11) Uani 1 1 d . . . O5 O 0.5739(3) 0.90397(16) 0.07493(7) 0.0468(6) Uani 1 1 d . . . O6 O 0.3561(5) 0.8676(2) 0.02015(9) 0.0853(9) Uani 1 1 d . . . O7 O 0.9100(5) 0.4813(2) 0.08881(10) 0.0848(9) Uani 1 1 d . . . O8 O 0.9834(4) 0.51936(18) 0.16223(9) 0.0712(8) Uani 1 1 d . . . C1 C 0.8501(5) 1.0523(3) 0.19891(12) 0.0615(11) Uani 1 1 d . . . H1 H 0.9392 1.0062 0.2094 0.074 Uiso 1 1 calc R . . C2 C 0.8976(6) 1.1490(3) 0.19495(13) 0.0713(12) Uani 1 1 d . . . H2 H 1.0180 1.1696 0.2028 0.086 Uiso 1 1 calc R . . C3 C 0.7607(7) 1.2239(3) 0.17820(14) 0.0716(12) Uani 1 1 d . . . C4 C 0.6077(6) 1.1890(3) 0.14462(12) 0.0588(10) Uani 1 1 d . . . C5 C 0.6017(5) 1.0706(2) 0.14097(10) 0.0450(8) Uani 1 1 d . . . H5 H 0.6977 1.0523 0.1180 0.054 Uiso 1 1 calc R . . C6 C 0.4169(5) 1.0279(2) 0.12179(11) 0.0463(9) Uani 1 1 d . . . H6 H 0.3161 1.0394 0.1443 0.056 Uiso 1 1 calc R . . C7 C 0.4331(5) 0.9149(2) 0.11107(10) 0.0436(8) Uani 1 1 d . . . H7 H 0.3128 0.8901 0.0993 0.052 Uiso 1 1 calc R . . C8 C 0.4909(4) 0.8522(2) 0.15326(10) 0.0411(8) Uani 1 1 d . . . C9 C 0.6700(5) 0.8987(2) 0.17519(10) 0.0440(8) Uani 1 1 d . . . H9 H 0.7636 0.8949 0.1503 0.053 Uiso 1 1 calc R . . C10 C 0.6569(5) 1.0141(2) 0.18709(11) 0.0477(9) Uani 1 1 d . . . C11 C 0.7458(6) 0.8287(3) 0.21344(11) 0.0609(11) Uani 1 1 d . . . H11A H 0.6535 0.8242 0.2382 0.073 Uiso 1 1 calc R . . H11B H 0.8575 0.8591 0.2266 0.073 Uiso 1 1 calc R . . C12 C 0.7935(5) 0.7209(2) 0.19699(11) 0.0519(9) Uani 1 1 d . . . H12A H 0.9275 0.7107 0.1996 0.062 Uiso 1 1 calc R . . H12B H 0.7327 0.6726 0.2175 0.062 Uiso 1 1 calc R . . C13 C 0.7339(5) 0.6994(2) 0.14669(11) 0.0433(8) Uani 1 1 d . . . C14 C 0.5372(4) 0.7409(3) 0.13975(11) 0.0452(9) Uani 1 1 d . . . C15 C 0.4383(6) 0.6740(3) 0.10684(14) 0.0622(11) Uani 1 1 d . . . H15 H 0.3477 0.7018 0.0846 0.075 Uiso 1 1 calc R . . C16 C 0.5655(6) 0.5881(3) 0.09310(13) 0.0676(11) Uani 1 1 d . . . H16A H 0.6296 0.6022 0.0640 0.081 Uiso 1 1 calc R . . H16B H 0.4970 0.5250 0.0902 0.081 Uiso 1 1 calc R . . C17 C 0.7015(5) 0.5850(2) 0.13399(12) 0.0524(9) Uani 1 1 d . . . H17 H 0.6363 0.5534 0.1604 0.063 Uiso 1 1 calc R . . C18 C 0.8765(5) 0.7391(2) 0.11056(11) 0.0491(9) Uani 1 1 d . . . H18A H 0.8848 0.8115 0.1128 0.074 Uiso 1 1 calc R . . H18B H 0.8365 0.7206 0.0797 0.074 Uiso 1 1 calc R . . H18C H 0.9970 0.7098 0.1167 0.074 Uiso 1 1 calc R . . C19 C 0.5316(5) 1.0393(3) 0.22963(11) 0.0627(11) Uani 1 1 d . . . H19A H 0.5520 0.9901 0.2538 0.094 Uiso 1 1 calc R . . H19B H 0.4026 1.0380 0.2203 0.094 Uiso 1 1 calc R . . H19C H 0.5626 1.1055 0.2412 0.094 Uiso 1 1 calc R . . C20 C 0.8731(6) 0.5239(3) 0.12457(15) 0.0586(10) Uani 1 1 d . . . C21 C 0.1926(7) 1.0764(4) 0.06376(15) 0.0740(13) Uani 1 1 d . . . C22 C 0.1689(8) 1.1239(4) 0.01725(15) 0.1139(19) Uani 1 1 d . . . H22A H 0.0435 1.1129 0.0064 0.171 Uiso 1 1 calc R . . H22B H 0.2557 1.0942 -0.0044 0.171 Uiso 1 1 calc R . . H22C H 0.1923 1.1953 0.0196 0.171 Uiso 1 1 calc R . . C23 C 0.5165(7) 0.8833(3) 0.03065(13) 0.0603(11) Uani 1 1 d . . . C24 C 0.6780(7) 0.8830(3) -0.00209(12) 0.0956(16) Uani 1 1 d . . . H24A H 0.6998 0.8152 -0.0130 0.143 Uiso 1 1 calc R . . H24B H 0.7874 0.9074 0.0138 0.143 Uiso 1 1 calc R . . H24C H 0.6510 0.9262 -0.0282 0.143 Uiso 1 1 calc R . . C25 C 1.1452(6) 0.4553(3) 0.15905(15) 0.0864(13) Uani 1 1 d . . . H25A H 1.1142 0.3886 0.1699 0.130 Uiso 1 1 calc R . . H25B H 1.2438 0.4828 0.1780 0.130 Uiso 1 1 calc R . . H25C H 1.1860 0.4518 0.1271 0.130 Uiso 1 1 calc R . . C28 C 0.6729(6) 1.2342(3) 0.09738(13) 0.0818(14) Uani 1 1 d . . . H28A H 0.6909 1.3059 0.1007 0.123 Uiso 1 1 calc R . . H28B H 0.5796 1.2216 0.0740 0.123 Uiso 1 1 calc R . . H28C H 0.7886 1.2031 0.0882 0.123 Uiso 1 1 calc R . . C29 C 0.4233(6) 1.2388(3) 0.15913(14) 0.0823(13) Uani 1 1 d . . . H29A H 0.3804 1.2092 0.1878 0.123 Uiso 1 1 calc R . . H29B H 0.3314 1.2282 0.1352 0.123 Uiso 1 1 calc R . . H29C H 0.4426 1.3101 0.1635 0.123 Uiso 1 1 calc R . . C30 C 0.3196(5) 0.8515(3) 0.18661(12) 0.0602(10) Uani 1 1 d . . . H30A H 0.2848 0.9199 0.1940 0.090 Uiso 1 1 calc R . . H30B H 0.3515 0.8162 0.2148 0.090 Uiso 1 1 calc R . . H30C H 0.2166 0.8179 0.1717 0.090 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 O1 0.132(3) 0.062(2) 0.114(2) -0.0258(18) 0.005(2) -0.022(2) O2 0.0549(16) 0.0627(16) 0.087(2) -0.0009(14) 0.0122(16) -0.0163(14) O3 0.0723(19) 0.0577(15) 0.0490(14) 0.0041(12) -0.0058(14) 0.0134(14) O4 0.0580(19) 0.146(3) 0.086(2) 0.004(2) -0.0096(19) 0.024(2) O5 0.0496(14) 0.0559(14) 0.0351(12) -0.0067(11) 0.0053(12) 0.0080(12) O6 0.093(2) 0.111(2) 0.0518(17) -0.0133(15) -0.0178(18) -0.008(2) O7 0.097(2) 0.081(2) 0.0765(19) -0.0060(16) -0.0012(19) 0.0236(18) O8 0.0686(18) 0.0576(17) 0.087(2) -0.0008(14) -0.0200(17) 0.0122(14) C1 0.052(2) 0.067(3) 0.065(3) -0.026(2) -0.008(2) 0.002(2) C2 0.057(3) 0.082(3) 0.075(3) -0.030(2) 0.007(2) -0.020(3) C3 0.091(3) 0.057(3) 0.066(3) -0.012(2) 0.015(3) -0.010(3) C4 0.074(3) 0.048(2) 0.054(2) -0.0069(18) 0.014(2) -0.005(2) C5 0.049(2) 0.044(2) 0.0421(19) -0.0072(15) 0.0084(18) 0.0047(17) C6 0.048(2) 0.052(2) 0.0387(18) -0.0018(16) 0.0046(17) 0.0056(19) C7 0.040(2) 0.051(2) 0.0390(18) -0.0016(16) 0.0026(17) -0.0004(17) C8 0.0382(19) 0.048(2) 0.0369(17) -0.0006(16) 0.0012(16) -0.0053(17) C9 0.041(2) 0.054(2) 0.0367(17) -0.0040(16) -0.0038(16) 0.0034(17) C10 0.045(2) 0.054(2) 0.044(2) -0.0094(16) 0.0047(18) 0.0029(18) C11 0.071(3) 0.068(3) 0.044(2) -0.0090(19) -0.012(2) 0.005(2) C12 0.057(2) 0.054(2) 0.044(2) 0.0109(17) -0.0020(19) -0.0062(19) C13 0.045(2) 0.044(2) 0.041(2) 0.0021(16) -0.0006(18) -0.0012(16) C14 0.040(2) 0.051(2) 0.045(2) 0.0009(17) 0.0014(18) -0.0130(17) C15 0.055(2) 0.060(3) 0.072(3) -0.009(2) -0.019(2) -0.003(2) C16 0.075(3) 0.046(2) 0.081(3) -0.012(2) -0.024(3) -0.007(2) C17 0.056(2) 0.044(2) 0.058(2) 0.0045(17) -0.001(2) -0.0044(19) C18 0.050(2) 0.045(2) 0.053(2) 0.0002(16) 0.0056(19) 0.0024(18) C19 0.067(3) 0.080(3) 0.040(2) -0.0144(19) 0.004(2) 0.001(2) C20 0.071(3) 0.040(2) 0.065(3) 0.004(2) -0.007(3) 0.003(2) C21 0.073(3) 0.085(3) 0.064(3) -0.001(2) -0.017(3) 0.033(3) C22 0.136(5) 0.126(4) 0.079(3) 0.020(3) -0.039(3) 0.038(4) C23 0.080(3) 0.059(3) 0.041(2) -0.0054(18) -0.003(2) 0.009(2) C24 0.113(4) 0.128(4) 0.046(2) -0.005(2) 0.024(3) 0.023(3) C25 0.070(3) 0.073(3) 0.116(4) 0.012(3) -0.011(3) 0.017(3) C28 0.109(4) 0.060(3) 0.076(3) 0.008(2) 0.013(3) -0.006(3) C29 0.094(3) 0.061(3) 0.091(3) -0.024(2) 0.016(3) 0.011(3) C30 0.051(2) 0.073(3) 0.056(2) -0.0026(19) 0.0142(19) -0.006(2) _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 O1 C3 1.217(4) . ? O2 C15 1.437(4) . ? O2 C14 1.464(4) . ? O3 C21 1.355(5) . ? O3 C6 1.453(4) . ? O4 C21 1.210(5) . ? O5 C23 1.361(4) . ? O5 C7 1.451(4) . ? O6 C23 1.203(5) . ? O7 C20 1.198(4) . ? O8 C20 1.337(4) . ? O8 C25 1.436(5) . ? C1 C2 1.327(5) . ? C1 C10 1.509(5) . ? C1 H1 0.9300 . ? C2 C3 1.471(6) . ? C2 H2 0.9300 . ? C3 C4 1.528(6) . ? C4 C29 1.530(5) . ? C4 C28 1.551(5) . ? C4 C5 1.567(4) . ? C5 C6 1.538(5) . ? C5 C10 1.567(4) . ? C5 H5 0.9800 . ? C6 C7 1.527(4) . ? C6 H6 0.9800 . ? C7 C8 1.522(4) . ? C7 H7 0.9800 . ? C8 C9 1.552(4) . ? C8 C30 1.553(4) . ? C8 C14 1.556(4) . ? C9 C11 1.532(4) . ? C9 C10 1.564(4) . ? C9 H9 0.9800 . ? C10 C19 1.548(4) . ? C11 C12 1.537(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.529(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.522(4) . ? C13 C18 1.544(4) . ? C13 C17 1.571(4) . ? C14 C15 1.472(5) . ? C15 C16 1.506(5) . ? C15 H15 0.9800 . ? C16 C17 1.522(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.493(5) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C22 1.482(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.488(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 C15 O2 C14 61.0(2) . . ? C21 O3 C6 117.2(3) . . ? C23 O5 C7 118.4(3) . . ? C20 O8 C25 116.8(3) . . ? C2 C1 C10 122.5(4) . . ? C2 C1 H1 118.8 . . ? C10 C1 H1 118.8 . . ? C1 C2 C3 120.3(4) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.9 . . ? O1 C3 C2 120.5(4) . . ? O1 C3 C4 120.9(4) . . ? C2 C3 C4 118.6(3) . . ? C3 C4 C29 108.4(3) . . ? C3 C4 C28 102.6(3) . . ? C29 C4 C28 109.3(3) . . ? C3 C4 C5 111.2(3) . . ? C29 C4 C5 115.0(3) . . ? C28 C4 C5 109.5(3) . . ? C6 C5 C10 110.0(3) . . ? C6 C5 C4 114.4(3) . . ? C10 C5 C4 114.3(3) . . ? C6 C5 H5 105.8 . . ? C10 C5 H5 105.8 . . ? C4 C5 H5 105.8 . . ? O3 C6 C7 106.8(2) . . ? O3 C6 C5 109.0(3) . . ? C7 C6 C5 111.4(3) . . ? O3 C6 H6 109.9 . . ? C7 C6 H6 109.9 . . ? C5 C6 H6 109.9 . . ? O5 C7 C8 108.9(2) . . ? O5 C7 C6 107.1(2) . . ? C8 C7 C6 113.1(3) . . ? O5 C7 H7 109.2 . . ? C8 C7 H7 109.2 . . ? C6 C7 H7 109.2 . . ? C7 C8 C9 109.3(3) . . ? C7 C8 C30 106.1(3) . . ? C9 C8 C30 113.8(2) . . ? C7 C8 C14 112.0(2) . . ? C9 C8 C14 107.4(3) . . ? C30 C8 C14 108.4(3) . . ? C11 C9 C8 110.0(3) . . ? C11 C9 C10 116.9(3) . . ? C8 C9 C10 115.1(3) . . ? C11 C9 H9 104.4 . . ? C8 C9 H9 104.4 . . ? C10 C9 H9 104.4 . . ? C1 C10 C19 106.3(3) . . ? C1 C10 C9 108.6(3) . . ? C19 C10 C9 114.6(3) . . ? C1 C10 C5 105.1(3) . . ? C19 C10 C5 114.5(3) . . ? C9 C10 C5 107.2(2) . . ? C9 C11 C12 114.7(3) . . ? C9 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C9 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 113.5(3) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 108.3(3) . . ? C14 C13 C18 113.6(3) . . ? C12 C13 C18 112.6(3) . . ? C14 C13 C17 100.3(3) . . ? C12 C13 C17 116.0(3) . . ? C18 C13 C17 105.6(3) . . ? O2 C14 C15 58.6(2) . . ? O2 C14 C13 111.6(3) . . ? C15 C14 C13 108.2(3) . . ? O2 C14 C8 112.7(3) . . ? C15 C14 C8 128.6(3) . . ? C13 C14 C8 120.3(3) . . ? O2 C15 C14 60.4(2) . . ? O2 C15 C16 110.5(3) . . ? C14 C15 C16 109.2(3) . . ? O2 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 101.8(3) . . ? C15 C16 H16A 111.4 . . ? C17 C16 H16A 111.4 . . ? C15 C16 H16B 111.4 . . ? C17 C16 H16B 111.4 . . ? H16A C16 H16B 109.3 . . ? C20 C17 C16 113.6(3) . . ? C20 C17 C13 116.1(3) . . ? C16 C17 C13 104.3(3) . . ? C20 C17 H17 107.5 . . ? C16 C17 H17 107.5 . . ? C13 C17 H17 107.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O7 C20 O8 122.6(4) . . ? O7 C20 C17 126.1(4) . . ? O8 C20 C17 111.3(3) . . ? O4 C21 O3 122.8(4) . . ? O4 C21 C22 125.3(5) . . ? O3 C21 C22 111.9(5) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O6 C23 O5 123.7(4) . . ? O6 C23 C24 125.6(4) . . ? O5 C23 C24 110.7(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 H25A 109.5 . . ? O8 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O8 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C8 C30 H30A 109.5 . . ? C8 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C8 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 C10 C1 C2 C3 -0.4(6) . . . . ? C1 C2 C3 O1 152.0(4) . . . . ? C1 C2 C3 C4 -29.2(5) . . . . ? O1 C3 C4 C29 -43.0(5) . . . . ? C2 C3 C4 C29 138.3(4) . . . . ? O1 C3 C4 C28 72.6(5) . . . . ? C2 C3 C4 C28 -106.2(4) . . . . ? O1 C3 C4 C5 -170.4(4) . . . . ? C2 C3 C4 C5 10.8(5) . . . . ? C3 C4 C5 C6 160.7(3) . . . . ? C29 C4 C5 C6 36.9(4) . . . . ? C28 C4 C5 C6 -86.7(4) . . . . ? C3 C4 C5 C10 32.5(4) . . . . ? C29 C4 C5 C10 -91.3(4) . . . . ? C28 C4 C5 C10 145.2(3) . . . . ? C21 O3 C6 C7 80.7(4) . . . . ? C21 O3 C6 C5 -158.9(3) . . . . ? C10 C5 C6 O3 -177.5(2) . . . . ? C4 C5 C6 O3 52.3(3) . . . . ? C10 C5 C6 C7 -59.8(3) . . . . ? C4 C5 C6 C7 169.9(2) . . . . ? C23 O5 C7 C8 132.2(3) . . . . ? C23 O5 C7 C6 -105.2(3) . . . . ? O3 C6 C7 O5 56.5(3) . . . . ? C5 C6 C7 O5 -62.5(3) . . . . ? O3 C6 C7 C8 176.4(3) . . . . ? C5 C6 C7 C8 57.5(4) . . . . ? O5 C7 C8 C9 66.9(3) . . . . ? C6 C7 C8 C9 -52.0(3) . . . . ? O5 C7 C8 C30 -170.0(2) . . . . ? C6 C7 C8 C30 71.1(4) . . . . ? O5 C7 C8 C14 -52.0(3) . . . . ? C6 C7 C8 C14 -170.8(3) . . . . ? C7 C8 C9 C11 -172.2(3) . . . . ? C30 C8 C9 C11 69.4(3) . . . . ? C14 C8 C9 C11 -50.5(3) . . . . ? C7 C8 C9 C10 53.1(3) . . . . ? C30 C8 C9 C10 -65.3(4) . . . . ? C14 C8 C9 C10 174.8(2) . . . . ? C2 C1 C10 C19 -79.9(4) . . . . ? C2 C1 C10 C9 156.4(3) . . . . ? C2 C1 C10 C5 41.9(4) . . . . ? C11 C9 C10 C1 59.6(4) . . . . ? C8 C9 C10 C1 -169.0(3) . . . . ? C11 C9 C10 C19 -59.1(4) . . . . ? C8 C9 C10 C19 72.4(3) . . . . ? C11 C9 C10 C5 172.7(3) . . . . ? C8 C9 C10 C5 -55.9(3) . . . . ? C6 C5 C10 C1 172.8(3) . . . . ? C4 C5 C10 C1 -56.9(3) . . . . ? C6 C5 C10 C19 -70.9(3) . . . . ? C4 C5 C10 C19 59.4(4) . . . . ? C6 C5 C10 C9 57.3(3) . . . . ? C4 C5 C10 C9 -172.4(3) . . . . ? C8 C9 C11 C12 58.2(4) . . . . ? C10 C9 C11 C12 -168.1(3) . . . . ? C9 C11 C12 C13 -7.1(5) . . . . ? C11 C12 C13 C14 -44.3(4) . . . . ? C11 C12 C13 C18 82.2(4) . . . . ? C11 C12 C13 C17 -156.1(3) . . . . ? C15 O2 C14 C13 -98.7(3) . . . . ? C15 O2 C14 C8 122.4(3) . . . . ? C12 C13 C14 O2 -83.7(3) . . . . ? C18 C13 C14 O2 150.4(3) . . . . ? C17 C13 C14 O2 38.2(3) . . . . ? C12 C13 C14 C15 -146.3(3) . . . . ? C18 C13 C14 C15 87.8(3) . . . . ? C17 C13 C14 C15 -24.4(3) . . . . ? C12 C13 C14 C8 51.7(4) . . . . ? C18 C13 C14 C8 -74.2(4) . . . . ? C17 C13 C14 C8 173.6(3) . . . . ? C7 C8 C14 O2 -108.3(3) . . . . ? C9 C8 C14 O2 131.7(3) . . . . ? C30 C8 C14 O2 8.4(4) . . . . ? C7 C8 C14 C15 -41.1(5) . . . . ? C9 C8 C14 C15 -161.1(3) . . . . ? C30 C8 C14 C15 75.6(4) . . . . ? C7 C8 C14 C13 116.8(3) . . . . ? C9 C8 C14 C13 -3.1(4) . . . . ? C30 C8 C14 C13 -126.5(3) . . . . ? C14 O2 C15 C16 101.0(3) . . . . ? C13 C14 C15 O2 104.6(3) . . . . ? C8 C14 C15 O2 -95.3(4) . . . . ? O2 C14 C15 C16 -103.2(3) . . . . ? C13 C14 C15 C16 1.4(4) . . . . ? C8 C14 C15 C16 161.5(3) . . . . ? O2 C15 C16 C17 -41.6(4) . . . . ? C14 C15 C16 C17 23.1(4) . . . . ? C15 C16 C17 C20 -165.5(3) . . . . ? C15 C16 C17 C13 -38.1(3) . . . . ? C14 C13 C17 C20 164.5(3) . . . . ? C12 C13 C17 C20 -79.2(4) . . . . ? C18 C13 C17 C20 46.2(4) . . . . ? C14 C13 C17 C16 38.7(3) . . . . ? C12 C13 C17 C16 155.0(3) . . . . ? C18 C13 C17 C16 -79.6(3) . . . . ? C25 O8 C20 O7 -3.6(5) . . . . ? C25 O8 C20 C17 174.6(3) . . . . ? C16 C17 C20 O7 1.3(5) . . . . ? C13 C17 C20 O7 -119.6(4) . . . . ? C16 C17 C20 O8 -176.9(3) . . . . ? C13 C17 C20 O8 62.2(4) . . . . ? C6 O3 C21 O4 2.7(6) . . . . ? C6 O3 C21 C22 -176.0(3) . . . . ? C7 O5 C23 O6 -4.6(5) . . . . ? C7 O5 C23 C24 175.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.131 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.031 data_cd29661 _database_code_depnum_ccdc_archive 'CCDC 767486' #TrackingRef '- Crystal structure data for 11a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H50 O4' _chemical_formula_weight 486.71 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 0.0000 '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 0.0000 '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 10.2080(8) _cell_length_b 15.3825(12) _cell_length_c 17.7371(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2785.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 4.593 _cell_measurement_theta_max 45.376 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.429 _exptl_crystal_size_mid 0.336 _exptl_crystal_size_min 0.231 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.31383 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14775 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2936 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0924P)^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 10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2936 _refine_ls_number_parameters 329 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 O1 O -0.0272(3) 0.43168(19) 1.01676(14) 0.0726(8) Uani 1 1 d . . . O2 O -0.1865(3) 0.48723(19) 0.27584(13) 0.0663(8) Uani 1 1 d . . . O3 O -0.1325(3) 0.3549(2) 0.15124(15) 0.0712(8) Uani 1 1 d D . . O4 O 0.1293(2) 0.34180(15) 0.28712(12) 0.0479(6) Uani 1 1 d . . . C1 C 0.0223(4) 0.5168(2) 0.83633(19) 0.0493(8) Uani 1 1 d . . . H1A H 0.0531 0.5709 0.8145 0.059 Uiso 1 1 calc R . . H1B H -0.0726 0.5167 0.8336 0.059 Uiso 1 1 calc R . . C2 C 0.0638(4) 0.5132(2) 0.9191(2) 0.0592(10) Uani 1 1 d . . . H2A H 0.1583 0.5193 0.9224 0.071 Uiso 1 1 calc R . . H2B H 0.0246 0.5616 0.9460 0.071 Uiso 1 1 calc R . . C3 C 0.0238(4) 0.4307(2) 0.9552(2) 0.0518(9) Uani 1 1 d . . . C4 C 0.0549(3) 0.3458(2) 0.91434(17) 0.0424(7) Uani 1 1 d . . . C5 C 0.0300(3) 0.35560(18) 0.82767(16) 0.0371(7) Uani 1 1 d . . . H5 H -0.0656 0.3556 0.8223 0.045 Uiso 1 1 calc R . . C6 C 0.0760(3) 0.2761(2) 0.78367(17) 0.0443(8) Uani 1 1 d . . . H6A H 0.1664 0.2640 0.7967 0.053 Uiso 1 1 calc R . . H6B H 0.0239 0.2262 0.7987 0.053 Uiso 1 1 calc R . . C7 C 0.0658(3) 0.28704(19) 0.70016(17) 0.0395(7) Uani 1 1 d . . . H7 H 0.0791 0.2382 0.6702 0.047 Uiso 1 1 calc R . . C8 C 0.0391(3) 0.36120(19) 0.66575(17) 0.0364(7) Uani 1 1 d . . . C9 C 0.0088(3) 0.44240(18) 0.71111(17) 0.0391(7) Uani 1 1 d . . . H9 H -0.0859 0.4418 0.7203 0.047 Uiso 1 1 calc R . . C10 C 0.0754(3) 0.44081(19) 0.78987(17) 0.0391(7) Uani 1 1 d . . . C11 C 0.0376(5) 0.5260(2) 0.6662(2) 0.0629(11) Uani 1 1 d . . . H11A H 0.0035 0.5751 0.6944 0.075 Uiso 1 1 calc R . . H11B H 0.1318 0.5331 0.6628 0.075 Uiso 1 1 calc R . . C12 C -0.0197(4) 0.5294(2) 0.58595(19) 0.0516(9) Uani 1 1 d . . . H12A H -0.0983 0.5648 0.5867 0.062 Uiso 1 1 calc R . . H12B H 0.0431 0.5579 0.5531 0.062 Uiso 1 1 calc R . . C13 C -0.0535(3) 0.4404(2) 0.55248(17) 0.0394(7) Uani 1 1 d . . . C14 C 0.0454(3) 0.3706(2) 0.58046(17) 0.0408(7) Uani 1 1 d . . . C15 C 0.0090(4) 0.2916(2) 0.53306(17) 0.0530(9) Uani 1 1 d . . . H15A H -0.0634 0.2601 0.5556 0.064 Uiso 1 1 calc R . . H15B H 0.0830 0.2525 0.5278 0.064 Uiso 1 1 calc R . . C16 C -0.0308(4) 0.3304(2) 0.45569(19) 0.0565(9) Uani 1 1 d . . . H16A H 0.0339 0.3158 0.4177 0.068 Uiso 1 1 calc R . . H16B H -0.1149 0.3074 0.4399 0.068 Uiso 1 1 calc R . . C17 C -0.0390(3) 0.4296(2) 0.46577(17) 0.0442(8) Uani 1 1 d . . . H17 H 0.0470 0.4531 0.4522 0.053 Uiso 1 1 calc R . . C18 C -0.1944(3) 0.4158(2) 0.57514(18) 0.0465(8) Uani 1 1 d . . . H18A H -0.2151 0.3593 0.5554 0.070 Uiso 1 1 calc R . . H18B H -0.2544 0.4578 0.5550 0.070 Uiso 1 1 calc R . . H18C H -0.2014 0.4149 0.6291 0.070 Uiso 1 1 calc R . . C19 C 0.2243(3) 0.4475(2) 0.7810(2) 0.0544(9) Uani 1 1 d . . . H19A H 0.2546 0.4019 0.7484 0.082 Uiso 1 1 calc R . . H19B H 0.2652 0.4420 0.8294 0.082 Uiso 1 1 calc R . . H19C H 0.2463 0.5029 0.7594 0.082 Uiso 1 1 calc R . . C20 C -0.1390(3) 0.4724(2) 0.41316(17) 0.0466(8) Uani 1 1 d . . . H20 H -0.2225 0.4414 0.4176 0.056 Uiso 1 1 calc R . . C21 C -0.1621(4) 0.5685(3) 0.4288(2) 0.0628(10) Uani 1 1 d . . . H21A H -0.0797 0.5985 0.4295 0.094 Uiso 1 1 calc R . . H21B H -0.2045 0.5751 0.4768 0.094 Uiso 1 1 calc R . . H21C H -0.2167 0.5926 0.3900 0.094 Uiso 1 1 calc R . . C22 C -0.0919(3) 0.4658(2) 0.33286(18) 0.0473(8) Uani 1 1 d . . . H22 H -0.0047 0.4904 0.3242 0.057 Uiso 1 1 calc R . . C23 C -0.1314(3) 0.4018(2) 0.27806(18) 0.0494(8) Uani 1 1 d . . . H23 H -0.1891 0.3555 0.2964 0.059 Uiso 1 1 calc R . . C24 C -0.0467(3) 0.3794(2) 0.21113(18) 0.0488(8) Uani 1 1 d . . . H24 H 0.0004 0.4320 0.1957 0.059 Uiso 1 1 calc R . . C25 C 0.0536(4) 0.3080(2) 0.22559(18) 0.0489(8) Uani 1 1 d . . . C26 C 0.1399(4) 0.2977(3) 0.1563(2) 0.0715(11) Uani 1 1 d . . . H26A H 0.2059 0.2547 0.1660 0.107 Uiso 1 1 calc R . . H26B H 0.1811 0.3522 0.1448 0.107 Uiso 1 1 calc R . . H26C H 0.0872 0.2797 0.1142 0.107 Uiso 1 1 calc R . . C27 C -0.0110(5) 0.2228(3) 0.2465(3) 0.0731(12) Uani 1 1 d . . . H27A H -0.0584 0.2297 0.2929 0.110 Uiso 1 1 calc R . . H27B H 0.0548 0.1788 0.2527 0.110 Uiso 1 1 calc R . . H27C H -0.0705 0.2058 0.2073 0.110 Uiso 1 1 calc R . . C28 C -0.0338(4) 0.2744(2) 0.94499(19) 0.0549(9) Uani 1 1 d . . . H28A H -0.1231 0.2869 0.9319 0.082 Uiso 1 1 calc R . . H28B H -0.0255 0.2718 0.9989 0.082 Uiso 1 1 calc R . . H28C H -0.0087 0.2196 0.9236 0.082 Uiso 1 1 calc R . . C29 C 0.1973(4) 0.3238(3) 0.9368(2) 0.0644(11) Uani 1 1 d . . . H29A H 0.2033 0.3189 0.9907 0.097 Uiso 1 1 calc R . . H29B H 0.2547 0.3692 0.9197 0.097 Uiso 1 1 calc R . . H29C H 0.2226 0.2697 0.9140 0.097 Uiso 1 1 calc R . . C30 C 0.1890(4) 0.3942(3) 0.5610(2) 0.0639(11) Uani 1 1 d . . . H30A H 0.2469 0.3526 0.5839 0.096 Uiso 1 1 calc R . . H30B H 0.2086 0.4512 0.5799 0.096 Uiso 1 1 calc R . . H30C H 0.2006 0.3932 0.5073 0.096 Uiso 1 1 calc R . . C31 C 0.2339(4) 0.2903(3) 0.3127(3) 0.0729(12) Uani 1 1 d . . . H31A H 0.3001 0.2872 0.2743 0.109 Uiso 1 1 calc R . . H31B H 0.2027 0.2328 0.3238 0.109 Uiso 1 1 calc R . . H31C H 0.2704 0.3156 0.3575 0.109 Uiso 1 1 calc R . . H3 H -0.106(5) 0.374(3) 0.1114(18) 0.099(19) Uiso 1 1 d 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 O1 0.097(2) 0.079(2) 0.0420(14) -0.0062(13) 0.0058(14) 0.0094(17) O2 0.0593(15) 0.093(2) 0.0467(14) 0.0198(13) 0.0007(12) 0.0291(14) O3 0.0589(17) 0.113(2) 0.0419(15) 0.0024(16) -0.0136(13) -0.0146(16) O4 0.0460(12) 0.0520(14) 0.0458(12) -0.0040(10) -0.0073(10) 0.0035(10) C1 0.061(2) 0.0376(18) 0.0496(19) -0.0031(15) -0.0044(17) -0.0024(16) C2 0.079(3) 0.049(2) 0.049(2) -0.0124(17) -0.009(2) -0.0024(19) C3 0.053(2) 0.063(2) 0.0396(18) -0.0057(17) -0.0131(15) 0.0036(18) C4 0.0432(18) 0.0460(19) 0.0381(16) 0.0021(15) -0.0051(13) 0.0044(14) C5 0.0332(15) 0.0367(16) 0.0414(16) 0.0015(13) -0.0040(13) -0.0009(13) C6 0.0572(19) 0.0347(17) 0.0411(17) 0.0042(13) -0.0046(15) 0.0042(14) C7 0.0522(18) 0.0280(16) 0.0385(16) 0.0014(13) 0.0039(14) 0.0063(13) C8 0.0359(15) 0.0338(16) 0.0396(16) 0.0041(13) 0.0029(13) -0.0009(13) C9 0.0429(16) 0.0301(15) 0.0444(17) 0.0059(13) -0.0021(13) 0.0000(12) C10 0.0391(15) 0.0352(16) 0.0429(17) 0.0027(14) -0.0047(13) -0.0020(12) C11 0.108(3) 0.0298(18) 0.051(2) 0.0083(15) -0.010(2) -0.009(2) C12 0.072(2) 0.0347(18) 0.0482(19) 0.0112(15) 0.0012(17) 0.0016(16) C13 0.0442(16) 0.0365(17) 0.0376(16) 0.0096(13) 0.0052(13) 0.0056(13) C14 0.0411(17) 0.0388(17) 0.0425(17) 0.0062(14) 0.0068(14) 0.0066(13) C15 0.077(3) 0.045(2) 0.0372(17) 0.0042(15) 0.0061(17) 0.0158(17) C16 0.082(3) 0.050(2) 0.0377(17) 0.0087(15) 0.0061(18) 0.0109(19) C17 0.0472(17) 0.0472(19) 0.0382(16) 0.0108(14) 0.0077(14) 0.0074(15) C18 0.0477(18) 0.051(2) 0.0413(17) 0.0083(15) 0.0061(15) 0.0044(15) C19 0.0451(18) 0.061(2) 0.057(2) 0.0065(18) -0.0009(16) -0.0080(16) C20 0.0470(19) 0.054(2) 0.0387(17) 0.0117(15) 0.0044(15) 0.0105(15) C21 0.077(3) 0.063(3) 0.048(2) 0.0097(18) 0.0034(18) 0.025(2) C22 0.0460(18) 0.055(2) 0.0408(17) 0.0165(15) -0.0004(15) 0.0078(15) C23 0.0413(17) 0.065(2) 0.0425(18) 0.0118(16) -0.0017(15) -0.0025(16) C24 0.0470(18) 0.063(2) 0.0360(16) 0.0016(15) -0.0039(15) -0.0049(15) C25 0.056(2) 0.053(2) 0.0380(17) -0.0069(15) -0.0023(15) -0.0089(15) C26 0.082(3) 0.078(3) 0.055(2) -0.017(2) 0.008(2) 0.008(2) C27 0.079(3) 0.058(2) 0.082(3) 0.002(2) -0.010(2) -0.017(2) C28 0.072(2) 0.054(2) 0.0387(18) 0.0104(16) 0.0009(17) -0.0012(19) C29 0.060(2) 0.083(3) 0.050(2) 0.0029(19) -0.0115(18) 0.020(2) C30 0.047(2) 0.087(3) 0.058(2) 0.025(2) 0.0117(18) 0.0071(19) C31 0.060(2) 0.079(3) 0.080(3) 0.000(2) -0.016(2) 0.013(2) _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 O1 C3 1.209(4) . ? O2 C23 1.430(4) . ? O2 C22 1.436(4) . ? O3 C24 1.427(4) . ? O3 H3 0.81(2) . ? O4 C31 1.405(4) . ? O4 C25 1.435(4) . ? C1 C2 1.528(5) . ? C1 C10 1.529(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.480(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.527(5) . ? C4 C28 1.523(5) . ? C4 C29 1.545(5) . ? C4 C5 1.565(4) . ? C5 C6 1.525(4) . ? C5 C10 1.544(4) . ? C5 H5 0.9800 . ? C6 C7 1.494(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.322(4) . ? C7 H7 0.9300 . ? C8 C9 1.518(4) . ? C8 C14 1.521(4) . ? C9 C11 1.541(4) . ? C9 C10 1.554(4) . ? C9 H9 0.9800 . ? C10 C19 1.532(4) . ? C11 C12 1.540(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.531(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.541(5) . ? C13 C17 1.554(4) . ? C13 C14 1.555(4) . ? C14 C15 1.525(5) . ? C14 C30 1.548(5) . ? C15 C16 1.551(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.539(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.531(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.506(4) . ? C20 C21 1.523(5) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.441(5) . ? C22 H22 0.9800 . ? C23 C24 1.508(5) . ? C23 H23 0.9800 . ? C24 C25 1.524(5) . ? C24 H24 0.9800 . ? C25 C27 1.514(5) . ? C25 C26 1.521(5) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 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 C23 O2 C22 60.4(2) . . ? C24 O3 H3 110(4) . . ? C31 O4 C25 116.8(3) . . ? C2 C1 C10 113.1(3) . . ? C2 C1 H1A 109.0 . . ? C10 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? C10 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 111.7(3) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? O1 C3 C2 120.0(3) . . ? O1 C3 C4 121.9(3) . . ? C2 C3 C4 118.1(3) . . ? C28 C4 C3 108.9(3) . . ? C28 C4 C29 108.0(3) . . ? C3 C4 C29 105.1(3) . . ? C28 C4 C5 108.9(3) . . ? C3 C4 C5 110.5(2) . . ? C29 C4 C5 115.3(3) . . ? C6 C5 C10 111.5(2) . . ? C6 C5 C4 112.0(2) . . ? C10 C5 C4 117.4(2) . . ? C6 C5 H5 104.9 . . ? C10 C5 H5 104.9 . . ? C4 C5 H5 104.9 . . ? C7 C6 C5 113.3(2) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 124.7(3) . . ? C8 C7 H7 117.6 . . ? C6 C7 H7 117.6 . . ? C7 C8 C9 120.5(3) . . ? C7 C8 C14 122.2(3) . . ? C9 C8 C14 117.2(2) . . ? C8 C9 C11 112.0(3) . . ? C8 C9 C10 112.0(2) . . ? C11 C9 C10 113.2(3) . . ? C8 C9 H9 106.3 . . ? C11 C9 H9 106.3 . . ? C10 C9 H9 106.3 . . ? C1 C10 C19 110.8(3) . . ? C1 C10 C5 108.0(3) . . ? C19 C10 C5 113.6(3) . . ? C1 C10 C9 108.5(2) . . ? C19 C10 C9 109.9(3) . . ? C5 C10 C9 105.8(2) . . ? C12 C11 C9 115.7(3) . . ? C12 C11 H11A 108.4 . . ? C9 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C9 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? C13 C12 C11 114.5(2) . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C18 109.2(3) . . ? C12 C13 C17 117.3(3) . . ? C18 C13 C17 108.7(3) . . ? C12 C13 C14 110.3(3) . . ? C18 C13 C14 110.7(2) . . ? C17 C13 C14 100.4(2) . . ? C8 C14 C15 117.5(3) . . ? C8 C14 C30 106.5(3) . . ? C15 C14 C30 107.1(3) . . ? C8 C14 C13 110.8(2) . . ? C15 C14 C13 102.5(3) . . ? C30 C14 C13 112.5(3) . . ? C14 C15 C16 104.2(3) . . ? C14 C15 H15A 110.9 . . ? C16 C15 H15A 110.9 . . ? C14 C15 H15B 110.9 . . ? C16 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? C17 C16 C15 107.0(3) . . ? 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 . . ? C20 C17 C16 113.1(3) . . ? C20 C17 C13 119.6(3) . . ? C16 C17 C13 103.1(2) . . ? C20 C17 H17 106.8 . . ? C16 C17 H17 106.8 . . ? C13 C17 H17 106.8 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C20 C21 106.7(3) . . ? C22 C20 C17 109.6(3) . . ? C21 C20 C17 114.2(3) . . ? C22 C20 H20 108.8 . . ? C21 C20 H20 108.8 . . ? C17 C20 H20 108.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 C23 59.6(2) . . ? O2 C22 C20 115.9(3) . . ? C23 C22 C20 126.5(3) . . ? O2 C22 H22 114.3 . . ? C23 C22 H22 114.3 . . ? C20 C22 H22 114.3 . . ? O2 C23 C22 60.0(2) . . ? O2 C23 C24 114.4(3) . . ? C22 C23 C24 121.8(3) . . ? O2 C23 H23 116.1 . . ? C22 C23 H23 116.1 . . ? C24 C23 H23 116.1 . . ? O3 C24 C23 107.1(3) . . ? O3 C24 C25 110.3(3) . . ? C23 C24 C25 114.7(3) . . ? O3 C24 H24 108.2 . . ? C23 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? O4 C25 C27 111.2(3) . . ? O4 C25 C26 110.0(3) . . ? C27 C25 C26 111.1(3) . . ? O4 C25 C24 103.2(3) . . ? C27 C25 C24 111.9(3) . . ? C26 C25 C24 109.2(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C14 C30 H30A 109.5 . . ? C14 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C14 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O4 C31 H31A 109.5 . . ? O4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 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 C10 C1 C2 C3 -56.7(4) . . . . ? C1 C2 C3 O1 -134.3(4) . . . . ? C1 C2 C3 C4 48.6(4) . . . . ? O1 C3 C4 C28 22.9(5) . . . . ? C2 C3 C4 C28 -160.1(3) . . . . ? O1 C3 C4 C29 -92.6(4) . . . . ? C2 C3 C4 C29 84.4(4) . . . . ? O1 C3 C4 C5 142.4(3) . . . . ? C2 C3 C4 C5 -40.5(4) . . . . ? C28 C4 C5 C6 -67.6(3) . . . . ? C3 C4 C5 C6 172.9(3) . . . . ? C29 C4 C5 C6 53.9(4) . . . . ? C28 C4 C5 C10 161.5(3) . . . . ? C3 C4 C5 C10 41.9(4) . . . . ? C29 C4 C5 C10 -77.0(4) . . . . ? C10 C5 C6 C7 -40.5(4) . . . . ? C4 C5 C6 C7 -174.3(3) . . . . ? C5 C6 C7 C8 9.8(5) . . . . ? C6 C7 C8 C9 -3.4(5) . . . . ? C6 C7 C8 C14 172.8(3) . . . . ? C7 C8 C9 C11 155.9(3) . . . . ? C14 C8 C9 C11 -20.4(4) . . . . ? C7 C8 C9 C10 27.5(4) . . . . ? C14 C8 C9 C10 -148.9(3) . . . . ? C2 C1 C10 C19 -68.7(4) . . . . ? C2 C1 C10 C5 56.3(4) . . . . ? C2 C1 C10 C9 170.6(3) . . . . ? C6 C5 C10 C1 178.6(3) . . . . ? C4 C5 C10 C1 -50.3(3) . . . . ? C6 C5 C10 C19 -58.1(4) . . . . ? C4 C5 C10 C19 73.1(4) . . . . ? C6 C5 C10 C9 62.5(3) . . . . ? C4 C5 C10 C9 -166.3(3) . . . . ? C8 C9 C10 C1 -170.8(2) . . . . ? C11 C9 C10 C1 61.4(4) . . . . ? C8 C9 C10 C19 67.8(3) . . . . ? C11 C9 C10 C19 -60.0(4) . . . . ? C8 C9 C10 C5 -55.2(3) . . . . ? C11 C9 C10 C5 177.1(3) . . . . ? C8 C9 C11 C12 49.1(4) . . . . ? C10 C9 C11 C12 176.9(3) . . . . ? C9 C11 C12 C13 -20.5(5) . . . . ? C11 C12 C13 C18 87.9(4) . . . . ? C11 C12 C13 C17 -147.9(3) . . . . ? C11 C12 C13 C14 -34.0(4) . . . . ? C7 C8 C14 C15 33.0(5) . . . . ? C9 C8 C14 C15 -150.7(3) . . . . ? C7 C8 C14 C30 -87.0(4) . . . . ? C9 C8 C14 C30 89.2(3) . . . . ? C7 C8 C14 C13 150.3(3) . . . . ? C9 C8 C14 C13 -33.4(4) . . . . ? C12 C13 C14 C8 61.8(3) . . . . ? C18 C13 C14 C8 -59.2(4) . . . . ? C17 C13 C14 C8 -173.8(3) . . . . ? C12 C13 C14 C15 -172.0(3) . . . . ? C18 C13 C14 C15 67.0(3) . . . . ? C17 C13 C14 C15 -47.6(3) . . . . ? C12 C13 C14 C30 -57.3(4) . . . . ? C18 C13 C14 C30 -178.2(3) . . . . ? C17 C13 C14 C30 67.1(3) . . . . ? C8 C14 C15 C16 157.2(3) . . . . ? C30 C14 C15 C16 -83.1(3) . . . . ? C13 C14 C15 C16 35.4(3) . . . . ? C14 C15 C16 C17 -9.7(4) . . . . ? C15 C16 C17 C20 -150.4(3) . . . . ? C15 C16 C17 C13 -19.8(4) . . . . ? C12 C13 C17 C20 -73.1(4) . . . . ? C18 C13 C17 C20 51.3(4) . . . . ? C14 C13 C17 C20 167.4(3) . . . . ? C12 C13 C17 C16 160.3(3) . . . . ? C18 C13 C17 C16 -75.2(3) . . . . ? C14 C13 C17 C16 40.9(3) . . . . ? C16 C17 C20 C22 -68.0(4) . . . . ? C13 C17 C20 C22 170.3(3) . . . . ? C16 C17 C20 C21 172.4(3) . . . . ? C13 C17 C20 C21 50.7(4) . . . . ? C23 O2 C22 C20 -118.8(3) . . . . ? C21 C20 C22 O2 -68.0(4) . . . . ? C17 C20 C22 O2 167.9(3) . . . . ? C21 C20 C22 C23 -138.0(3) . . . . ? C17 C20 C22 C23 97.9(4) . . . . ? C22 O2 C23 C24 -113.9(3) . . . . ? C20 C22 C23 O2 101.3(4) . . . . ? O2 C22 C23 C24 101.8(3) . . . . ? C20 C22 C23 C24 -156.9(3) . . . . ? O2 C23 C24 O3 -80.7(4) . . . . ? C22 C23 C24 O3 -149.4(3) . . . . ? O2 C23 C24 C25 156.5(3) . . . . ? C22 C23 C24 C25 87.9(4) . . . . ? C31 O4 C25 C27 61.3(4) . . . . ? C31 O4 C25 C26 -62.2(4) . . . . ? C31 O4 C25 C24 -178.6(3) . . . . ? O3 C24 C25 O4 -179.1(3) . . . . ? C23 C24 C25 O4 -58.0(4) . . . . ? O3 C24 C25 C27 -59.4(4) . . . . ? C23 C24 C25 C27 61.6(4) . . . . ? O3 C24 C25 C26 64.0(4) . . . . ? C23 C24 C25 C26 -175.0(3) . . . . ? 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 O3 H3 O1 0.81(2) 2.06(2) 2.871(4) 174(5) 1_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.275 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.051