Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'ProfD Yoshinori Fujimoto' _publ_contact_author_address ; Chemistry and Mterials Science Tokyo Institute of Technology O-okayama 2-12-1 Meguro-ku Tokyo 152-8551 ; _publ_contact_author_email FUJIMOTO@CMS.TITECH.AC.JP _publ_section_title ; Structure elucidation of cyasterone stereoisomers isolated from Cyathula officinalis ; loop_ _publ_author_name 'Yoshinori Fujimoto' 'Noriyuki Hara' 'Keiko Okuzumi' 'Hidehiro Uekusa' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 255170' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '28-epi-cyasterone 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H50 O11' _chemical_formula_weight 574.69 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.3374(17) _cell_length_b 7.6406(10) _cell_length_c 15.5158(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.311(4) _cell_angle_gamma 90.00 _cell_volume 1564.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6174 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCORE, RIGAKU(1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode UX-18' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU R-AXIS RAPID' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14750 _diffrn_reflns_av_R_equivalents 0.0896 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 68.24 _reflns_number_total 3076 _reflns_number_gt 1620 _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. Hydrogen atoms of crystalline waters of O91 to O94 could not be located and were not included to this model. The structure of terminal ring structure (C24 to C29, O7, and O8) was composed from the direct methods result and treated as a rigid group at the final refinement stage, because they showed large rotational motion around C23-C24 bond and thus caused poor convergence. ; _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^)+(0.2000P)^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 0.5(11) _refine_ls_number_reflns 3076 _refine_ls_number_parameters 356 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2112 _refine_ls_R_factor_gt 0.1447 _refine_ls_wR_factor_ref 0.4073 _refine_ls_wR_factor_gt 0.3689 _refine_ls_goodness_of_fit_ref 1.303 _refine_ls_restrained_S_all 1.303 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.1438(8) 1.0646(13) 0.0455(5) 0.110(3) Uani 1 1 d . . . H1 H 0.0892 1.1181 0.0363 0.156 Uiso 1 1 calc R . . O2 O 0.0365(8) 0.7546(13) -0.0125(5) 0.112(3) Uani 1 1 d . . . H2 H 0.0512 0.7820 -0.0599 0.167 Uiso 1 1 calc R . . O3 O -0.0357(7) 0.3410(11) 0.1842(4) 0.089(2) Uani 1 1 d . . . O4 O 0.3005(6) 0.5898(13) 0.4059(5) 0.092(2) Uani 1 1 d . . . H4 H 0.3033 0.6440 0.3607 0.138 Uiso 1 1 calc R . . O5 O 0.1328(5) 0.7139(14) 0.6753(4) 0.092(3) Uani 1 1 d . . . H5 H 0.1207 0.7631 0.7196 0.138 Uiso 1 1 calc R . . O6 O 0.2898(7) 0.7451(19) 0.8142(5) 0.115(3) Uani 1 1 d . . . H6 H 0.2889 0.6643 0.8475 0.173 Uiso 1 1 calc R . . C1 C 0.2498(9) 0.6829(14) 0.5693(7) 0.075(3) Uani 1 1 d . . . H1A H 0.3185 0.7135 0.5593 0.090 Uiso 1 1 calc R . . C2 C 0.1734(9) 0.7344(13) 0.4861(7) 0.075(3) Uani 1 1 d . . . C3 C 0.1998(10) 0.9023(13) 0.4418(7) 0.080(3) Uani 1 1 d . . . H3A H 0.1915 1.0016 0.4791 0.096 Uiso 1 1 calc R . . H3B H 0.2700 0.8984 0.4321 0.096 Uiso 1 1 calc R . . C4 C 0.1307(11) 0.9239(16) 0.3544(7) 0.086(4) Uani 1 1 d . . . H4A H 0.0621 0.9439 0.3661 0.104 Uiso 1 1 calc R . . H4B H 0.1517 1.0278 0.3259 0.104 Uiso 1 1 calc R . . C5 C 0.1288(9) 0.7710(15) 0.2912(6) 0.074(3) Uani 1 1 d . . . H5A H 0.1910 0.7786 0.2646 0.089 Uiso 1 1 calc R . . C6 C 0.0369(8) 0.7871(14) 0.2147(6) 0.068(3) Uani 1 1 d . . . C7 C 0.0508(11) 0.9359(16) 0.1543(7) 0.089(4) Uani 1 1 d . . . H7A H -0.0117 0.9498 0.1142 0.107 Uiso 1 1 calc R . . H7B H 0.0608 1.0422 0.1886 0.107 Uiso 1 1 calc R . . C8 C 0.1383(13) 0.9199(18) 0.1004(9) 0.105(4) Uani 1 1 d . . . H8 H 0.2015 0.9162 0.1413 0.126 Uiso 1 1 calc R . . C9 C 0.1296(13) 0.747(2) 0.0498(8) 0.112(5) Uani 1 1 d . . . H9 H 0.1881 0.7324 0.0189 0.135 Uiso 1 1 calc R . . C10 C 0.1229(11) 0.5934(18) 0.1102(7) 0.090(4) Uani 1 1 d . . . H10A H 0.1839 0.5874 0.1525 0.108 Uiso 1 1 calc R . . H10B H 0.1172 0.4854 0.0770 0.108 Uiso 1 1 calc R . . C11 C 0.0270(10) 0.6157(13) 0.1588(7) 0.077(3) Uani 1 1 d . . . H11 H -0.0334 0.6255 0.1149 0.092 Uiso 1 1 calc R . . C12 C 0.0164(10) 0.4614(13) 0.2116(8) 0.081(3) Uani 1 1 d . . . C13 C 0.0750(9) 0.4541(15) 0.3029(6) 0.074(3) Uani 1 1 d . . . H13 H 0.0723 0.3531 0.3359 0.089 Uiso 1 1 calc R . . C14 C 0.1301(9) 0.5892(16) 0.3368(7) 0.080(3) Uani 1 1 d . . . C15 C 0.1943(11) 0.5804(15) 0.4222(7) 0.080(3) Uani 1 1 d . . . C16 C 0.1926(10) 0.4225(15) 0.4768(7) 0.077(3) Uani 1 1 d . . . H16A H 0.2316 0.3294 0.4551 0.092 Uiso 1 1 calc R . . H16B H 0.1236 0.3821 0.4761 0.092 Uiso 1 1 calc R . . C17 C 0.2398(11) 0.4738(16) 0.5703(7) 0.088(4) Uani 1 1 d . . . H17A H 0.3058 0.4198 0.5856 0.106 Uiso 1 1 calc R . . H17B H 0.1964 0.4372 0.6121 0.106 Uiso 1 1 calc R . . C18 C 0.0642(7) 0.7294(16) 0.4972(7) 0.070(3) Uani 1 1 d . . . H18A H 0.0500 0.6221 0.5252 0.105 Uiso 1 1 calc R . . H18B H 0.0231 0.7363 0.4411 0.105 Uiso 1 1 calc R . . H18C H 0.0491 0.8267 0.5323 0.105 Uiso 1 1 calc R . . C19 C -0.0602(8) 0.8131(16) 0.2493(8) 0.083(3) Uani 1 1 d . . . H19A H -0.1147 0.8215 0.2017 0.125 Uiso 1 1 calc R . . H19B H -0.0568 0.9190 0.2829 0.125 Uiso 1 1 calc R . . H19C H -0.0720 0.7157 0.2856 0.125 Uiso 1 1 calc R . . C20 C 0.2313(12) 0.761(2) 0.6588(7) 0.101(4) Uani 1 1 d . . . C21 C 0.2483(11) 0.9594(19) 0.6570(8) 0.098(4) Uani 1 1 d . . . H21A H 0.2003 1.0109 0.6120 0.146 Uiso 1 1 calc R . . H21B H 0.3158 0.9828 0.6456 0.146 Uiso 1 1 calc R . . H21C H 0.2393 1.0086 0.7123 0.146 Uiso 1 1 calc R . . C22 C 0.3111(10) 0.6776(19) 0.7316(7) 0.094(4) Uani 1 1 d . . . H22 H 0.2980 0.5514 0.7314 0.112 Uiso 1 1 calc R . . C23 C 0.4271(7) 0.7025(13) 0.7280(7) 0.107(4) Uani 1 1 d G . . H23A H 0.4422 0.6562 0.6731 0.129 Uiso 1 1 calc R . . H23B H 0.4419 0.8268 0.7289 0.129 Uiso 1 1 calc R . . C24 C 0.4960(6) 0.6160(12) 0.8009(5) 0.124(5) Uani 1 1 d G . . H24 H 0.4765 0.6502 0.8571 0.149 Uiso 1 1 calc R . . C25 C 0.6076(6) 0.6548(14) 0.8003(7) 0.161(9) Uani 1 1 d G . . H25 H 0.6436 0.6406 0.8596 0.193 Uiso 1 1 calc R . . C26 C 0.5783(7) 0.3805(14) 0.7433(8) 0.169(9) Uani 1 1 d G . . C27 C 0.4949(7) 0.4169(13) 0.7926(8) 0.178(9) Uani 1 1 d G . . H27 H 0.4308 0.3794 0.7587 0.214 Uiso 1 1 calc R . . C28 C 0.6346(8) 0.8257(16) 0.7667(12) 0.35(3) Uani 1 1 d G . . H28A H 0.7068 0.8336 0.7698 0.532 Uiso 1 1 calc R . . H28B H 0.6110 0.9172 0.8011 0.532 Uiso 1 1 calc R . . H28C H 0.6035 0.8379 0.7072 0.532 Uiso 1 1 calc R . . C29 C 0.5113(12) 0.321(2) 0.8777(11) 0.35(3) Uani 1 1 d G . . H29A H 0.4563 0.3453 0.9096 0.523 Uiso 1 1 calc R . . H29B H 0.5739 0.3581 0.9111 0.523 Uiso 1 1 calc R . . H29C H 0.5141 0.1972 0.8670 0.523 Uiso 1 1 calc R . . O7 O 0.6401(6) 0.5157(15) 0.7452(8) 0.190(7) Uani 1 1 d G . . O8 O 0.5945(10) 0.2477(18) 0.7066(11) 0.323(15) Uani 1 1 d G . . O91 O 0.2752(10) 1.081(2) -0.0801(8) 0.164(5) Uani 1 1 d . . . O92 O 0.2861(15) 0.477(3) 0.9316(11) 0.238(10) Uani 1 1 d . . . O93 O 0.508(5) 0.660(9) 0.482(2) 0.28(3) Uani 0.50 1 d P . . O94 O 0.473(2) 0.458(9) 0.500(3) 0.26(3) Uani 0.50 1 d P . . 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 0.164(8) 0.089(6) 0.071(5) 0.025(5) -0.004(5) -0.032(6) O2 0.200(9) 0.071(5) 0.065(5) 0.002(5) 0.021(5) -0.027(6) O3 0.152(7) 0.065(5) 0.051(4) 0.002(4) 0.022(4) -0.008(5) O4 0.106(6) 0.098(6) 0.076(5) -0.003(5) 0.024(4) -0.006(5) O5 0.084(5) 0.127(7) 0.066(4) 0.001(5) 0.012(4) 0.008(5) O6 0.118(6) 0.151(9) 0.070(5) 0.002(6) -0.009(4) 0.012(7) C1 0.094(7) 0.055(6) 0.077(7) -0.007(5) 0.013(6) 0.002(6) C2 0.130(9) 0.033(5) 0.058(6) -0.006(5) 0.000(6) 0.009(6) C3 0.140(10) 0.043(5) 0.061(6) -0.014(5) 0.025(6) -0.011(6) C4 0.141(10) 0.065(8) 0.053(6) 0.003(6) 0.012(6) -0.009(7) C5 0.111(8) 0.063(7) 0.051(5) -0.001(5) 0.019(5) -0.009(6) C6 0.096(7) 0.063(7) 0.041(5) -0.008(5) 0.001(5) 0.000(6) C7 0.153(11) 0.060(7) 0.052(6) 0.005(6) 0.005(7) -0.019(7) C8 0.152(12) 0.074(9) 0.086(8) 0.016(8) 0.008(9) 0.007(8) C9 0.191(14) 0.085(10) 0.055(6) -0.005(7) -0.002(8) -0.005(10) C10 0.149(11) 0.068(7) 0.057(6) -0.005(6) 0.024(6) 0.001(8) C11 0.127(9) 0.042(6) 0.066(6) 0.007(5) 0.033(6) 0.011(6) C12 0.135(10) 0.031(5) 0.079(7) -0.024(5) 0.026(7) -0.023(6) C13 0.120(8) 0.051(6) 0.053(5) 0.002(5) 0.016(6) -0.031(6) C14 0.115(9) 0.055(6) 0.073(7) -0.003(6) 0.023(6) 0.004(7) C15 0.137(10) 0.045(6) 0.058(6) -0.013(5) 0.014(6) 0.010(6) C16 0.104(8) 0.053(6) 0.073(7) 0.010(5) 0.014(6) 0.000(6) C17 0.145(10) 0.062(7) 0.053(6) 0.002(5) -0.005(6) 0.003(7) C18 0.070(6) 0.068(7) 0.071(6) -0.007(6) 0.009(5) 0.012(6) C19 0.084(7) 0.063(7) 0.100(8) 0.002(7) 0.007(6) 0.009(6) C20 0.154(12) 0.091(10) 0.055(7) 0.004(7) 0.009(7) -0.004(9) C21 0.144(11) 0.078(9) 0.073(8) -0.005(7) 0.023(7) 0.012(8) C22 0.139(10) 0.093(10) 0.046(6) 0.009(6) 0.001(6) 0.008(8) C23 0.117(10) 0.116(12) 0.084(8) -0.020(8) -0.001(7) -0.015(9) C24 0.161(14) 0.086(10) 0.120(12) 0.009(10) 0.003(10) 0.048(10) C25 0.094(11) 0.102(14) 0.27(3) -0.006(16) -0.016(13) -0.021(10) C26 0.24(3) 0.078(13) 0.19(2) 0.006(14) 0.046(19) 0.014(15) C27 0.163(17) 0.121(17) 0.25(3) 0.025(19) 0.018(17) 0.050(14) C28 0.136(19) 0.19(3) 0.69(8) 0.09(4) -0.12(3) -0.05(2) C29 0.39(5) 0.36(6) 0.28(4) 0.10(4) -0.01(4) 0.19(5) O7 0.181(13) 0.145(13) 0.243(17) -0.061(13) 0.029(11) -0.015(10) O8 0.225(16) 0.21(2) 0.58(4) -0.16(3) 0.21(2) -0.064(16) O91 0.177(11) 0.179(13) 0.132(9) 0.005(11) 0.005(8) -0.052(10) O92 0.264(18) 0.30(3) 0.151(12) 0.065(15) 0.031(12) 0.131(18) O93 0.34(5) 0.39(9) 0.12(3) -0.05(4) 0.04(3) -0.08(6) O94 0.11(2) 0.48(8) 0.18(3) 0.15(4) 0.026(19) -0.01(3) _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 C8 1.404(16) . ? O1 H1 0.8200 . ? O2 C9 1.461(17) . ? O2 H2 0.8200 . ? O3 C12 1.194(12) . ? O4 C15 1.476(14) . ? O4 H4 0.8200 . ? O5 C20 1.421(16) . ? O5 H5 0.8200 . ? O6 C22 1.446(14) . ? O6 H6 0.8200 . ? C1 C20 1.565(16) . ? C1 C2 1.574(15) . ? C1 C17 1.603(16) . ? C1 H1A 0.9800 . ? C2 C18 1.491(14) . ? C2 C3 1.521(15) . ? C2 C15 1.590(14) . ? C3 C4 1.535(17) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.523(16) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C14 1.558(17) . ? C5 C6 1.583(14) . ? C5 H5A 0.9800 . ? C6 C7 1.502(15) . ? C6 C19 1.487(15) . ? C6 C11 1.565(15) . ? C7 C8 1.53(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.53(2) . ? C8 H8 0.9800 . ? C9 C10 1.51(2) . ? C9 H9 0.9800 . ? C10 C11 1.586(17) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.455(15) . ? C11 H11 0.9800 . ? C12 C13 1.517(16) . ? C13 C14 1.330(16) . ? C13 H13 0.9300 . ? C14 C15 1.471(16) . ? C15 C16 1.476(16) . ? C16 C17 1.546(16) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? 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 1.573(17) . ? C20 C21 1.53(2) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.568(16) . ? C22 H22 0.9800 . ? C23 C24 1.503(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.520(5) . ? C24 C27 1.527(5) . ? C24 H24 0.9800 . ? C25 O7 1.468(5) . ? C25 C28 1.469(5) . ? C25 H25 0.9800 . ? C26 O8 1.198(4) . ? C26 O7 1.319(5) . ? C26 C27 1.465(5) . ? C27 C29 1.500(5) . ? C27 H27 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? O93 O94 1.64(8) . ? 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 C8 O1 H1 112.0 . . ? C9 O2 H2 109.5 . . ? C15 O4 H4 109.5 . . ? C20 O5 H5 109.5 . . ? C22 O6 H6 109.5 . . ? C20 C1 C2 117.7(10) . . ? C20 C1 C17 110.4(11) . . ? C2 C1 C17 102.3(9) . . ? C20 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? C17 C1 H1A 108.7 . . ? C18 C2 C3 111.6(9) . . ? C18 C2 C15 108.4(9) . . ? C3 C2 C15 105.6(8) . . ? C18 C2 C1 115.2(9) . . ? C3 C2 C1 114.6(10) . . ? C15 C2 C1 100.1(8) . . ? C4 C3 C2 110.0(9) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 116.0(10) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C14 113.2(8) . . ? C4 C5 C6 111.2(10) . . ? C14 C5 C6 111.5(9) . . ? C4 C5 H5A 106.9 . . ? C14 C5 H5A 106.9 . . ? C6 C5 H5A 106.9 . . ? C7 C6 C19 108.5(9) . . ? C7 C6 C11 107.2(7) . . ? C19 C6 C11 107.7(9) . . ? C7 C6 C5 112.0(9) . . ? C19 C6 C5 111.1(8) . . ? C11 C6 C5 110.2(9) . . ? C8 C7 C6 116.8(11) . . ? C8 C7 H7A 108.1 . . ? C6 C7 H7A 108.1 . . ? C8 C7 H7B 108.1 . . ? C6 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? O1 C8 C7 112.2(12) . . ? O1 C8 C9 112.1(10) . . ? C7 C8 C9 109.9(13) . . ? O1 C8 H8 107.5 . . ? C7 C8 H8 107.5 . . ? C9 C8 H8 107.5 . . ? O2 C9 C10 108.8(13) . . ? O2 C9 C8 107.3(13) . . ? C10 C9 C8 111.0(9) . . ? O2 C9 H9 109.9 . . ? C10 C9 H9 109.9 . . ? C8 C9 H9 109.9 . . ? C9 C10 C11 109.6(12) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C6 111.9(8) . . ? C12 C11 C10 109.4(10) . . ? C6 C11 C10 110.1(10) . . ? C12 C11 H11 108.4 . . ? C6 C11 H11 108.4 . . ? C10 C11 H11 108.4 . . ? O3 C12 C11 121.5(11) . . ? O3 C12 C13 120.0(10) . . ? C11 C12 C13 118.5(10) . . ? C14 C13 C12 121.4(10) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 122.5(11) . . ? C13 C14 C5 122.9(10) . . ? C15 C14 C5 114.6(10) . . ? O4 C15 C16 103.4(10) . . ? O4 C15 C14 107.0(9) . . ? C16 C15 C14 120.0(11) . . ? O4 C15 C2 109.2(10) . . ? C16 C15 C2 103.2(8) . . ? C14 C15 C2 113.4(10) . . ? C15 C16 C17 107.1(9) . . ? C15 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? C15 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? C16 C17 C1 105.4(9) . . ? C16 C17 H17A 110.7 . . ? C1 C17 H17A 110.7 . . ? C16 C17 H17B 110.7 . . ? C1 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 C22 108.3(10) . . ? O5 C20 C21 113.5(13) . . ? C22 C20 C21 109.2(12) . . ? O5 C20 C1 109.3(10) . . ? C22 C20 C1 107.7(11) . . ? C21 C20 C1 108.7(11) . . ? 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 . . ? O6 C22 C20 107.0(11) . . ? O6 C22 C23 108.0(9) . . ? C20 C22 C23 119.6(10) . . ? O6 C22 H22 107.2 . . ? C20 C22 H22 107.2 . . ? C23 C22 H22 107.2 . . ? C24 C23 C22 114.7(7) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 C25 113.7 . . ? C23 C24 C27 112.1 . . ? C25 C24 C27 101.0 . . ? C23 C24 H24 109.9 . . ? C25 C24 H24 109.9 . . ? C27 C24 H24 109.9 . . ? O7 C25 C28 109.2 . . ? O7 C25 C24 103.6 . . ? C28 C25 C24 117.8 . . ? O7 C25 H25 108.6 . . ? C28 C25 H25 108.6 . . ? C24 C25 H25 108.6 . . ? O8 C26 O7 121.3 . . ? O8 C26 C27 127.7 . . ? O7 C26 C27 111.0 . . ? C26 C27 C29 110.0 . . ? C26 C27 C24 103.6 . . ? C29 C27 C24 114.5 . . ? C26 C27 H27 109.5 . . ? C29 C27 H27 109.5 . . ? C24 C27 H27 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 O7 C25 110.2 . . ? 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 C20 C1 C2 C18 -44.3(14) . . . . ? C17 C1 C2 C18 76.9(12) . . . . ? C20 C1 C2 C3 87.2(13) . . . . ? C17 C1 C2 C3 -151.6(10) . . . . ? C20 C1 C2 C15 -160.3(11) . . . . ? C17 C1 C2 C15 -39.1(12) . . . . ? C18 C2 C3 C4 -55.7(11) . . . . ? C15 C2 C3 C4 61.9(12) . . . . ? C1 C2 C3 C4 171.1(10) . . . . ? C2 C3 C4 C5 -54.7(13) . . . . ? C3 C4 C5 C14 39.8(14) . . . . ? C3 C4 C5 C6 166.2(10) . . . . ? C4 C5 C6 C7 69.2(11) . . . . ? C14 C5 C6 C7 -163.5(9) . . . . ? C4 C5 C6 C19 -52.3(12) . . . . ? C14 C5 C6 C19 75.0(11) . . . . ? C4 C5 C6 C11 -171.5(9) . . . . ? C14 C5 C6 C11 -44.2(11) . . . . ? C19 C6 C7 C8 -170.8(11) . . . . ? C11 C6 C7 C8 -54.8(13) . . . . ? C5 C6 C7 C8 66.2(13) . . . . ? C6 C7 C8 O1 179.3(10) . . . . ? C6 C7 C8 C9 53.9(14) . . . . ? O1 C8 C9 O2 -60.7(16) . . . . ? C7 C8 C9 O2 64.7(13) . . . . ? O1 C8 C9 C10 -179.5(14) . . . . ? C7 C8 C9 C10 -54.1(16) . . . . ? O2 C9 C10 C11 -58.6(13) . . . . ? C8 C9 C10 C11 59.2(16) . . . . ? C7 C6 C11 C12 178.2(11) . . . . ? C19 C6 C11 C12 -65.3(13) . . . . ? C5 C6 C11 C12 56.0(13) . . . . ? C7 C6 C11 C10 56.3(12) . . . . ? C19 C6 C11 C10 172.8(9) . . . . ? C5 C6 C11 C10 -65.9(11) . . . . ? C9 C10 C11 C12 175.6(11) . . . . ? C9 C10 C11 C6 -61.0(13) . . . . ? C6 C11 C12 O3 144.6(11) . . . . ? C10 C11 C12 O3 -93.0(15) . . . . ? C6 C11 C12 C13 -36.4(15) . . . . ? C10 C11 C12 C13 85.9(12) . . . . ? O3 C12 C13 C14 -176.9(12) . . . . ? C11 C12 C13 C14 4.2(18) . . . . ? C12 C13 C14 C15 -174.7(11) . . . . ? C12 C13 C14 C5 7.6(19) . . . . ? C4 C5 C14 C13 140.1(12) . . . . ? C6 C5 C14 C13 13.9(15) . . . . ? C4 C5 C14 C15 -37.7(14) . . . . ? C6 C5 C14 C15 -164.0(9) . . . . ? C13 C14 C15 O4 112.0(12) . . . . ? C5 C14 C15 O4 -70.1(12) . . . . ? C13 C14 C15 C16 -5.1(17) . . . . ? C5 C14 C15 C16 172.7(10) . . . . ? C13 C14 C15 C2 -127.5(12) . . . . ? C5 C14 C15 C2 50.3(14) . . . . ? C18 C2 C15 O4 176.5(8) . . . . ? C3 C2 C15 O4 56.8(11) . . . . ? C1 C2 C15 O4 -62.5(10) . . . . ? C18 C2 C15 C16 -74.0(11) . . . . ? C3 C2 C15 C16 166.3(11) . . . . ? C1 C2 C15 C16 47.0(11) . . . . ? C18 C2 C15 C14 57.2(12) . . . . ? C3 C2 C15 C14 -62.4(13) . . . . ? C1 C2 C15 C14 178.3(10) . . . . ? O4 C15 C16 C17 78.2(11) . . . . ? C14 C15 C16 C17 -162.8(11) . . . . ? C2 C15 C16 C17 -35.6(13) . . . . ? C15 C16 C17 C1 10.3(14) . . . . ? C20 C1 C17 C16 145.3(11) . . . . ? C2 C1 C17 C16 19.2(14) . . . . ? C2 C1 C20 O5 57.6(14) . . . . ? C17 C1 C20 O5 -59.2(14) . . . . ? C2 C1 C20 C22 175.0(10) . . . . ? C17 C1 C20 C22 58.2(14) . . . . ? C2 C1 C20 C21 -66.8(15) . . . . ? C17 C1 C20 C21 176.4(12) . . . . ? O5 C20 C22 O6 -59.2(14) . . . . ? C21 C20 C22 O6 64.8(14) . . . . ? C1 C20 C22 O6 -177.3(11) . . . . ? O5 C20 C22 C23 177.7(10) . . . . ? C21 C20 C22 C23 -58.2(15) . . . . ? C1 C20 C22 C23 59.6(15) . . . . ? O6 C22 C23 C24 57.6(12) . . . . ? C20 C22 C23 C24 -179.8(10) . . . . ? C22 C23 C24 C25 -175.1(8) . . . . ? C22 C23 C24 C27 71.1(8) . . . . ? C23 C24 C25 O7 -89.1 . . . . ? C27 C24 C25 O7 31.2 . . . . ? C23 C24 C25 C28 31.6 . . . . ? C27 C24 C25 C28 151.9 . . . . ? O8 C26 C27 C29 72.9 . . . . ? O7 C26 C27 C29 -105.2 . . . . ? O8 C26 C27 C24 -164.2 . . . . ? O7 C26 C27 C24 17.7 . . . . ? C23 C24 C27 C26 91.9 . . . . ? C25 C24 C27 C26 -29.5 . . . . ? C23 C24 C27 C29 -148.3 . . . . ? C25 C24 C27 C29 90.3 . . . . ? O8 C26 O7 C25 -175.2 . . . . ? C27 C26 O7 C25 3.0 . . . . ? C28 C25 O7 C26 -148.8 . . . . ? C24 C25 O7 C26 -22.5 . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.613 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.088 data_cyasterone1 _database_code_depnum_ccdc_archive 'CCDC 255171' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'cyasterone 1' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H56 O11' _chemical_formula_weight 616.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.6542(11) _cell_length_b 7.7755(4) _cell_length_c 15.7636(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.215(3) _cell_angle_gamma 90.00 _cell_volume 1647.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10590 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 68.195 _exptl_crystal_description block _exptl_crystal_colour transparent _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7509 _exptl_absorpt_correction_T_max 0.9279 _exptl_absorpt_process_details 'ABSCORE, Rigaku' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'RIGAKU UX-18 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU R-AXIS RAPID' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18438 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 68.22 _reflns_number_total 5428 _reflns_number_gt 5250 _reflns_threshold_expression >2\s(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^)+(0.0854P)^2^+1.7591P] 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 SHELXL _refine_ls_extinction_coef 0.0201(14) _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 0.1(3) _refine_ls_number_reflns 5428 _refine_ls_number_parameters 389 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.86878(18) 0.6597(3) 0.94375(15) 0.0351(6) Uani 1 1 d . . . H1 H 0.9244 0.7088 0.9540 0.053 Uiso 1 1 calc R . . O2 O 0.96158(18) 0.3498(3) 1.01132(14) 0.0340(6) Uani 1 1 d . . . H2 H 0.9426 0.3783 1.0572 0.051 Uiso 1 1 calc R . . O3 O 1.04890(19) -0.0674(3) 0.82070(14) 0.0311(5) Uani 1 1 d . . . O4 O 0.71697(17) 0.1910(4) 0.59866(15) 0.0369(6) Uani 1 1 d . . . H4 H 0.7191 0.2411 0.6462 0.055 Uiso 1 1 calc R . . O5 O 0.86066(17) 0.2887(3) 0.32320(15) 0.0337(6) Uani 1 1 d . . . H5 H 0.8651 0.3298 0.2747 0.051 Uiso 1 1 calc R . . O6 O 0.6969(2) 0.3375(4) 0.19661(14) 0.0400(6) Uani 1 1 d . . . H6 H 0.6920 0.2567 0.1607 0.060 Uiso 1 1 calc R . . O7 O 0.3349(2) 0.1126(5) 0.2706(2) 0.0629(9) Uani 1 1 d . . . O8 O 0.3572(3) -0.1676(6) 0.2656(3) 0.0748(11) Uani 1 1 d . . . O9 O 0.7224(3) -0.2180(4) 1.0207(2) 0.0621(10) Uani 1 1 d . . . H9 H 0.7664 -0.2467 0.9923 0.093 Uiso 1 1 calc R . . O10 O 0.5327(3) 0.1493(11) 0.4885(3) 0.126(2) Uani 1 1 d . . . H10 H 0.5871 0.1463 0.5230 0.189 Uiso 1 1 calc R . . O11 O 0.6868(3) 0.1103(5) 1.0607(2) 0.0648(10) Uani 1 1 d . . . H11 H 0.6900 0.0030 1.0665 0.097 Uiso 1 1 calc R . . C1 C 0.7628(2) 0.2640(4) 0.4363(2) 0.0259(7) Uani 1 1 d . . . H1A H 0.6957 0.2952 0.4487 0.031 Uiso 1 1 calc R . . C2 C 0.8385(2) 0.3144(4) 0.51747(19) 0.0270(7) Uani 1 1 d . . . C3 C 0.8231(3) 0.4889(5) 0.5588(2) 0.0352(8) Uani 1 1 d . . . H3A H 0.8356 0.5822 0.5193 0.042 Uiso 1 1 calc R . . H3B H 0.7532 0.4982 0.5672 0.042 Uiso 1 1 calc R . . C4 C 0.8924(3) 0.5116(5) 0.6456(2) 0.0351(8) Uani 1 1 d . . . H4A H 0.8727 0.6174 0.6732 0.042 Uiso 1 1 calc R . . H4B H 0.9610 0.5289 0.6349 0.042 Uiso 1 1 calc R . . C5 C 0.8931(2) 0.3602(5) 0.70945(19) 0.0271(7) Uani 1 1 d . . . H5A H 0.8302 0.3712 0.7333 0.033 Uiso 1 1 calc R . . C6 C 0.9788(2) 0.3726(4) 0.78789(19) 0.0265(7) Uani 1 1 d . . . C7 C 0.9653(3) 0.5285(4) 0.8455(2) 0.0279(7) Uani 1 1 d . . . H7A H 1.0257 0.5411 0.8902 0.033 Uiso 1 1 calc R . . H7B H 0.9586 0.6340 0.8098 0.033 Uiso 1 1 calc R . . C8 C 0.8744(3) 0.5126(5) 0.8896(2) 0.0281(7) Uani 1 1 d . . . H8 H 0.8133 0.5103 0.8440 0.034 Uiso 1 1 calc R . . C9 C 0.8778(3) 0.3469(5) 0.9421(2) 0.0309(7) Uani 1 1 d . . . H9A H 0.8152 0.3364 0.9664 0.037 Uiso 1 1 calc R . . C10 C 0.8877(3) 0.1917(5) 0.8854(2) 0.0299(7) Uani 1 1 d . . . H10A H 0.8279 0.1827 0.8397 0.036 Uiso 1 1 calc R . . H10B H 0.8924 0.0855 0.9205 0.036 Uiso 1 1 calc R . . C11 C 0.9820(3) 0.2093(4) 0.8434(2) 0.0267(7) Uani 1 1 d . . . H11A H 1.0411 0.2181 0.8908 0.032 Uiso 1 1 calc R . . C12 C 0.9950(2) 0.0519(4) 0.7910(2) 0.0260(7) Uani 1 1 d . . . C13 C 0.9375(2) 0.0466(4) 0.7031(2) 0.0265(7) Uani 1 1 d . . . H13 H 0.9351 -0.0574 0.6712 0.032 Uiso 1 1 calc R . . C14 C 0.8882(2) 0.1851(4) 0.66644(19) 0.0240(7) Uani 1 1 d . . . C15 C 0.8172(2) 0.1723(5) 0.5809(2) 0.0254(7) Uani 1 1 d . . . C16 C 0.8133(3) 0.0072(5) 0.5288(2) 0.0305(8) Uani 1 1 d . . . H16A H 0.7712 -0.0801 0.5506 0.037 Uiso 1 1 calc R . . H16B H 0.8808 -0.0408 0.5308 0.037 Uiso 1 1 calc R . . C17 C 0.7670(3) 0.0641(5) 0.4360(2) 0.0302(8) Uani 1 1 d . . . H17A H 0.6993 0.0157 0.4192 0.036 Uiso 1 1 calc R . . H17B H 0.8084 0.0234 0.3944 0.036 Uiso 1 1 calc R . . C18 C 0.9465(3) 0.2981(5) 0.5026(2) 0.0325(8) Uani 1 1 d . . . H18A H 0.9617 0.3934 0.4663 0.049 Uiso 1 1 calc R . . H18B H 0.9547 0.1886 0.4738 0.049 Uiso 1 1 calc R . . H18C H 0.9920 0.3019 0.5581 0.049 Uiso 1 1 calc R . . C19 C 1.0816(3) 0.3927(5) 0.7607(2) 0.0311(8) Uani 1 1 d . . . H19A H 1.0901 0.3024 0.7193 0.047 Uiso 1 1 calc R . . H19B H 1.1341 0.3829 0.8116 0.047 Uiso 1 1 calc R . . H19C H 1.0856 0.5057 0.7340 0.047 Uiso 1 1 calc R . . C20 C 0.7692(2) 0.3443(5) 0.34745(19) 0.0283(7) Uani 1 1 d . . . C21 C 0.7665(3) 0.5411(5) 0.3480(2) 0.0331(8) Uani 1 1 d . . . H21A H 0.8296 0.5852 0.3800 0.050 Uiso 1 1 calc R . . H21B H 0.7117 0.5802 0.3757 0.050 Uiso 1 1 calc R . . H21C H 0.7566 0.5839 0.2886 0.050 Uiso 1 1 calc R . . C22 C 0.6821(3) 0.2717(5) 0.2789(2) 0.0329(8) Uani 1 1 d . . . H22 H 0.6872 0.1435 0.2782 0.040 Uiso 1 1 calc R . . C23 C 0.5788(3) 0.3214(6) 0.2942(2) 0.0415(9) Uani 1 1 d . . . H23A H 0.5673 0.4439 0.2785 0.050 Uiso 1 1 calc R . . H23B H 0.5776 0.3106 0.3566 0.050 Uiso 1 1 calc R . . C24 C 0.4928(3) 0.2165(6) 0.2449(3) 0.0461(10) Uani 1 1 d . . . H24 H 0.4888 0.2332 0.1815 0.055 Uiso 1 1 calc R . . C25 C 0.3927(3) 0.2728(7) 0.2721(3) 0.0550(12) Uani 1 1 d . . . H25 H 0.4076 0.3159 0.3328 0.066 Uiso 1 1 calc R . . C26 C 0.3941(4) -0.0213(7) 0.2680(3) 0.0592(13) Uani 1 1 d . . . C27 C 0.4972(3) 0.0230(7) 0.2666(3) 0.0516(11) Uani 1 1 d . . . H27 H 0.5359 0.0086 0.3262 0.062 Uiso 1 1 calc R . . C28 C 0.3339(4) 0.4040(7) 0.2184(4) 0.0654(14) Uani 1 1 d . . . H28A H 0.3144 0.3601 0.1595 0.098 Uiso 1 1 calc R . . H28B H 0.3740 0.5083 0.2175 0.098 Uiso 1 1 calc R . . H28C H 0.2742 0.4310 0.2423 0.098 Uiso 1 1 calc R . . C29 C 0.5422(5) -0.0909(9) 0.2076(5) 0.086(2) Uani 1 1 d . . . H29A H 0.5379 -0.2110 0.2255 0.128 Uiso 1 1 calc R . . H29B H 0.6122 -0.0596 0.2102 0.128 Uiso 1 1 calc R . . H29C H 0.5061 -0.0770 0.1485 0.128 Uiso 1 1 calc R . . C30 C 0.7016(4) -0.3591(7) 1.0722(3) 0.0560(11) Uani 1 1 d . . . H30A H 0.7639 -0.4159 1.0976 0.084 Uiso 1 1 calc R . . H30B H 0.6583 -0.4413 1.0361 0.084 Uiso 1 1 calc R . . H30C H 0.6680 -0.3173 1.1182 0.084 Uiso 1 1 calc R . . C31 C 0.4607(4) 0.1758(9) 0.5312(4) 0.0722(16) Uani 1 1 d . . . H31A H 0.4887 0.1966 0.5920 0.108 Uiso 1 1 calc R . . H31B H 0.4174 0.0744 0.5264 0.108 Uiso 1 1 calc R . . H31C H 0.4219 0.2761 0.5074 0.108 Uiso 1 1 calc R . . C32 C 0.6054(4) 0.1532(8) 0.9958(3) 0.0719(15) Uani 1 1 d . . . H32A H 0.5670 0.2460 1.0164 0.108 Uiso 1 1 calc R . . H32B H 0.5627 0.0521 0.9819 0.108 Uiso 1 1 calc R . . H32C H 0.6298 0.1913 0.9441 0.108 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 0.0400(13) 0.0314(15) 0.0342(12) -0.0121(11) 0.0069(10) 0.0028(11) O2 0.0450(13) 0.0347(15) 0.0217(11) -0.0018(10) 0.0041(9) 0.0057(12) O3 0.0447(14) 0.0255(13) 0.0235(11) 0.0029(9) 0.0071(10) 0.0041(11) O4 0.0281(12) 0.0554(18) 0.0290(12) 0.0012(11) 0.0102(9) 0.0017(11) O5 0.0364(12) 0.0395(15) 0.0271(11) 0.0027(10) 0.0104(10) -0.0008(11) O6 0.0560(15) 0.0388(16) 0.0234(11) 0.0041(11) 0.0023(10) -0.0084(13) O7 0.0519(18) 0.055(2) 0.083(2) 0.0072(17) 0.0138(17) -0.0012(16) O8 0.062(2) 0.070(3) 0.097(3) 0.018(2) 0.0258(19) -0.003(2) O9 0.084(2) 0.052(2) 0.0590(19) 0.0132(16) 0.0345(17) 0.0288(18) O10 0.053(2) 0.249(8) 0.075(3) -0.032(4) 0.012(2) -0.028(4) O11 0.094(3) 0.054(2) 0.0442(17) -0.0061(14) 0.0064(17) 0.0133(19) C1 0.0277(16) 0.0268(19) 0.0223(15) -0.0013(12) 0.0022(13) -0.0014(13) C2 0.0332(17) 0.025(2) 0.0220(14) 0.0004(13) 0.0016(12) 0.0024(14) C3 0.053(2) 0.027(2) 0.0238(17) -0.0014(14) 0.0043(15) 0.0029(16) C4 0.059(2) 0.0173(19) 0.0273(17) 0.0015(13) 0.0037(16) 0.0009(16) C5 0.0324(16) 0.0239(19) 0.0243(15) -0.0009(13) 0.0029(12) 0.0036(14) C6 0.0326(17) 0.0215(18) 0.0243(15) -0.0021(13) 0.0022(12) -0.0004(13) C7 0.0398(18) 0.0178(18) 0.0258(16) -0.0038(13) 0.0053(13) -0.0020(14) C8 0.0325(17) 0.0280(19) 0.0229(16) -0.0076(13) 0.0024(13) 0.0025(14) C9 0.0375(18) 0.030(2) 0.0253(15) -0.0020(14) 0.0066(13) 0.0013(16) C10 0.0391(18) 0.0234(19) 0.0287(17) -0.0034(13) 0.0098(14) -0.0036(14) C11 0.0352(17) 0.0217(18) 0.0240(16) -0.0020(13) 0.0072(13) 0.0005(14) C12 0.0340(17) 0.0218(18) 0.0232(15) 0.0002(12) 0.0080(13) -0.0048(13) C13 0.0359(17) 0.0208(18) 0.0231(15) -0.0020(12) 0.0060(13) 0.0005(13) C14 0.0255(15) 0.0243(19) 0.0228(15) -0.0019(12) 0.0061(12) -0.0038(13) C15 0.0247(15) 0.030(2) 0.0227(15) -0.0008(13) 0.0060(12) 0.0014(13) C16 0.0364(18) 0.031(2) 0.0240(16) -0.0024(14) 0.0043(13) 0.0012(15) C17 0.0374(18) 0.027(2) 0.0254(16) -0.0005(13) 0.0044(14) -0.0032(14) C18 0.0381(18) 0.034(2) 0.0267(16) 0.0010(14) 0.0080(14) -0.0054(15) C19 0.0356(18) 0.027(2) 0.0316(17) -0.0005(13) 0.0075(14) -0.0014(14) C20 0.0321(16) 0.031(2) 0.0217(15) 0.0001(13) 0.0038(12) -0.0015(15) C21 0.0424(19) 0.028(2) 0.0274(17) 0.0023(14) 0.0029(14) -0.0017(15) C22 0.0401(19) 0.032(2) 0.0257(16) 0.0007(14) 0.0026(14) -0.0066(15) C23 0.0356(18) 0.052(3) 0.0340(18) 0.0008(17) -0.0006(14) -0.0035(18) C24 0.041(2) 0.045(3) 0.049(2) -0.0011(19) -0.0003(18) -0.0074(18) C25 0.040(2) 0.065(3) 0.056(3) -0.001(2) -0.001(2) -0.010(2) C26 0.071(3) 0.058(3) 0.052(3) 0.018(2) 0.017(2) -0.018(3) C27 0.047(2) 0.054(3) 0.052(2) -0.003(2) 0.0025(19) 0.002(2) C28 0.069(3) 0.054(3) 0.072(3) -0.004(2) 0.007(3) 0.002(2) C29 0.082(4) 0.067(4) 0.120(5) -0.029(4) 0.053(4) -0.035(3) C30 0.060(3) 0.056(3) 0.058(3) 0.000(2) 0.025(2) 0.006(2) C31 0.049(3) 0.102(5) 0.067(3) 0.001(3) 0.014(2) -0.002(3) C32 0.087(4) 0.062(4) 0.060(3) -0.011(3) -0.005(3) 0.015(3) _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 C8 1.438(4) . ? O1 H1 0.8400 . ? O2 C9 1.434(4) . ? O2 H2 0.8400 . ? O3 C12 1.224(4) . ? O4 C15 1.452(4) . ? O4 H4 0.8400 . ? O5 C20 1.436(4) . ? O5 H5 0.8400 . ? O6 C22 1.441(4) . ? O6 H6 0.8400 . ? O7 C26 1.323(7) . ? O7 C25 1.472(6) . ? O8 C26 1.242(6) . ? O9 C30 1.423(6) . ? O9 H9 0.8400 . ? O10 C31 1.301(6) . ? O10 H10 0.8400 . ? O11 C32 1.411(6) . ? O11 H11 0.8400 . ? C1 C2 1.546(4) . ? C1 C20 1.550(4) . ? C1 C17 1.555(5) . ? C1 H1A 1.0000 . ? C2 C3 1.535(5) . ? C2 C18 1.539(5) . ? C2 C15 1.553(4) . ? C3 C4 1.530(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.547(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C14 1.518(5) . ? C5 C6 1.548(4) . ? C5 H5A 1.0000 . ? C6 C11 1.538(5) . ? C6 C7 1.545(5) . ? C6 C19 1.546(5) . ? C7 C8 1.531(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.528(5) . ? C8 H8 1.0000 . ? C9 C10 1.523(5) . ? C9 H9A 1.0000 . ? C10 C11 1.555(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.505(5) . ? C11 H11A 1.0000 . ? C12 C13 1.467(4) . ? C13 C14 1.345(5) . ? C13 H13 0.9500 . ? C14 C15 1.517(4) . ? C15 C16 1.520(5) . ? C16 C17 1.552(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.530(6) . ? C20 C22 1.563(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.522(5) . ? C22 H22 1.0000 . ? C23 C24 1.524(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C27 1.541(7) . ? C24 C25 1.566(6) . ? C24 H24 1.0000 . ? C25 C28 1.471(7) . ? C25 H25 1.0000 . ? C26 C27 1.453(7) . ? C27 C29 1.493(8) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 C8 O1 H1 109.5 . . ? C9 O2 H2 109.5 . . ? C15 O4 H4 109.5 . . ? C20 O5 H5 109.5 . . ? C22 O6 H6 109.5 . . ? C26 O7 C25 109.7(3) . . ? C30 O9 H9 109.5 . . ? C31 O10 H10 109.5 . . ? C32 O11 H11 109.5 . . ? C2 C1 C20 120.6(3) . . ? C2 C1 C17 103.7(3) . . ? C20 C1 C17 113.0(3) . . ? C2 C1 H1A 106.2 . . ? C20 C1 H1A 106.2 . . ? C17 C1 H1A 106.2 . . ? C3 C2 C18 110.2(3) . . ? C3 C2 C1 117.0(3) . . ? C18 C2 C1 111.8(3) . . ? C3 C2 C15 107.5(3) . . ? C18 C2 C15 109.5(3) . . ? C1 C2 C15 100.3(3) . . ? C4 C3 C2 111.9(3) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 115.2(3) . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C14 C5 C4 113.4(2) . . ? C14 C5 C6 112.3(3) . . ? C4 C5 C6 112.9(3) . . ? C14 C5 H5A 105.8 . . ? C4 C5 H5A 105.8 . . ? C6 C5 H5A 105.8 . . ? C11 C6 C7 107.9(2) . . ? C11 C6 C19 107.8(3) . . ? C7 C6 C19 107.0(3) . . ? C11 C6 C5 110.1(3) . . ? C7 C6 C5 111.5(3) . . ? C19 C6 C5 112.3(3) . . ? C8 C7 C6 113.2(3) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O1 C8 C9 110.4(3) . . ? O1 C8 C7 109.8(3) . . ? C9 C8 C7 111.4(3) . . ? O1 C8 H8 108.4 . . ? C9 C8 H8 108.4 . . ? C7 C8 H8 108.4 . . ? O2 C9 C10 108.5(3) . . ? O2 C9 C8 110.0(3) . . ? C10 C9 C8 110.3(3) . . ? O2 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C9 C10 C11 110.3(3) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C6 110.7(2) . . ? C12 C11 C10 110.4(3) . . ? C6 C11 C10 111.9(3) . . ? C12 C11 H11A 107.9 . . ? C6 C11 H11A 107.9 . . ? C10 C11 H11A 107.9 . . ? O3 C12 C13 121.7(3) . . ? O3 C12 C11 121.9(3) . . ? C13 C12 C11 116.4(3) . . ? C14 C13 C12 121.8(3) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 121.4(3) . . ? C13 C14 C5 123.2(3) . . ? C15 C14 C5 115.2(3) . . ? O4 C15 C14 107.4(2) . . ? O4 C15 C16 104.2(3) . . ? C14 C15 C16 119.4(3) . . ? O4 C15 C2 110.1(3) . . ? C14 C15 C2 111.3(3) . . ? C16 C15 C2 104.2(2) . . ? C15 C16 C17 103.8(3) . . ? C15 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? C15 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C16 C17 C1 106.9(3) . . ? C16 C17 H17A 110.3 . . ? C1 C17 H17A 110.3 . . ? C16 C17 H17B 110.3 . . ? C1 C17 H17B 110.3 . . ? H17A C17 H17B 108.6 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 C21 109.0(3) . . ? O5 C20 C1 108.1(3) . . ? C21 C20 C1 113.1(3) . . ? O5 C20 C22 107.3(3) . . ? C21 C20 C22 110.4(3) . . ? C1 C20 C22 108.8(3) . . ? 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 . . ? O6 C22 C23 109.5(3) . . ? O6 C22 C20 106.5(3) . . ? C23 C22 C20 114.3(3) . . ? O6 C22 H22 108.8 . . ? C23 C22 H22 108.8 . . ? C20 C22 H22 108.8 . . ? C22 C23 C24 115.8(3) . . ? C22 C23 H23A 108.3 . . ? C24 C23 H23A 108.3 . . ? C22 C23 H23B 108.3 . . ? C24 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 C27 114.4(4) . . ? C23 C24 C25 109.9(4) . . ? C27 C24 C25 102.3(4) . . ? C23 C24 H24 110.0 . . ? C27 C24 H24 110.0 . . ? C25 C24 H24 110.0 . . ? C28 C25 O7 109.9(4) . . ? C28 C25 C24 116.7(4) . . ? O7 C25 C24 104.5(4) . . ? C28 C25 H25 108.5 . . ? O7 C25 H25 108.5 . . ? C24 C25 H25 108.5 . . ? O8 C26 O7 118.4(5) . . ? O8 C26 C27 127.3(5) . . ? O7 C26 C27 114.3(4) . . ? C26 C27 C29 112.1(4) . . ? C26 C27 C24 103.6(4) . . ? C29 C27 C24 116.4(5) . . ? C26 C27 H27 108.1 . . ? C29 C27 H27 108.1 . . ? C24 C27 H27 108.1 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O9 C30 H30A 109.5 . . ? O9 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O9 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O10 C31 H31A 109.5 . . ? O10 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O10 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O11 C32 H32A 109.5 . . ? O11 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O11 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C20 C1 C2 C3 77.2(4) . . . . ? C17 C1 C2 C3 -155.0(3) . . . . ? C20 C1 C2 C18 -51.1(4) . . . . ? C17 C1 C2 C18 76.7(3) . . . . ? C20 C1 C2 C15 -167.0(3) . . . . ? C17 C1 C2 C15 -39.3(3) . . . . ? C18 C2 C3 C4 -59.7(4) . . . . ? C1 C2 C3 C4 171.2(3) . . . . ? C15 C2 C3 C4 59.5(4) . . . . ? C2 C3 C4 C5 -50.0(4) . . . . ? C3 C4 C5 C14 39.2(4) . . . . ? C3 C4 C5 C6 168.4(3) . . . . ? C14 C5 C6 C11 -44.2(3) . . . . ? C4 C5 C6 C11 -174.0(3) . . . . ? C14 C5 C6 C7 -163.9(3) . . . . ? C4 C5 C6 C7 66.3(4) . . . . ? C14 C5 C6 C19 76.0(4) . . . . ? C4 C5 C6 C19 -53.8(4) . . . . ? C11 C6 C7 C8 -54.9(4) . . . . ? C19 C6 C7 C8 -170.7(3) . . . . ? C5 C6 C7 C8 66.2(4) . . . . ? C6 C7 C8 O1 178.3(3) . . . . ? C6 C7 C8 C9 55.7(4) . . . . ? O1 C8 C9 O2 -58.2(3) . . . . ? C7 C8 C9 O2 64.1(3) . . . . ? O1 C8 C9 C10 -177.9(3) . . . . ? C7 C8 C9 C10 -55.6(3) . . . . ? O2 C9 C10 C11 -63.5(4) . . . . ? C8 C9 C10 C11 57.1(3) . . . . ? C7 C6 C11 C12 180.0(3) . . . . ? C19 C6 C11 C12 -64.8(3) . . . . ? C5 C6 C11 C12 58.1(3) . . . . ? C7 C6 C11 C10 56.3(3) . . . . ? C19 C6 C11 C10 171.5(3) . . . . ? C5 C6 C11 C10 -65.6(3) . . . . ? C9 C10 C11 C12 177.0(3) . . . . ? C9 C10 C11 C6 -59.2(3) . . . . ? C6 C11 C12 O3 140.2(3) . . . . ? C10 C11 C12 O3 -95.2(4) . . . . ? C6 C11 C12 C13 -41.4(4) . . . . ? C10 C11 C12 C13 83.1(3) . . . . ? O3 C12 C13 C14 -171.5(3) . . . . ? C11 C12 C13 C14 10.1(5) . . . . ? C12 C13 C14 C15 -171.1(3) . . . . ? C12 C13 C14 C5 4.3(5) . . . . ? C4 C5 C14 C13 143.3(3) . . . . ? C6 C5 C14 C13 13.8(4) . . . . ? C4 C5 C14 C15 -41.0(4) . . . . ? C6 C5 C14 C15 -170.5(3) . . . . ? C13 C14 C15 O4 108.6(3) . . . . ? C5 C14 C15 O4 -67.2(4) . . . . ? C13 C14 C15 C16 -9.5(5) . . . . ? C5 C14 C15 C16 174.7(3) . . . . ? C13 C14 C15 C2 -130.9(3) . . . . ? C5 C14 C15 C2 53.3(3) . . . . ? C3 C2 C15 O4 57.8(3) . . . . ? C18 C2 C15 O4 177.4(3) . . . . ? C1 C2 C15 O4 -64.9(3) . . . . ? C3 C2 C15 C14 -61.1(3) . . . . ? C18 C2 C15 C14 58.5(3) . . . . ? C1 C2 C15 C14 176.2(3) . . . . ? C3 C2 C15 C16 168.9(3) . . . . ? C18 C2 C15 C16 -71.4(3) . . . . ? C1 C2 C15 C16 46.2(3) . . . . ? O4 C15 C16 C17 81.1(3) . . . . ? C14 C15 C16 C17 -159.2(3) . . . . ? C2 C15 C16 C17 -34.3(3) . . . . ? C15 C16 C17 C1 9.2(4) . . . . ? C2 C1 C17 C16 19.3(4) . . . . ? C20 C1 C17 C16 151.6(3) . . . . ? C2 C1 C20 O5 64.9(4) . . . . ? C17 C1 C20 O5 -58.5(4) . . . . ? C2 C1 C20 C21 -55.8(4) . . . . ? C17 C1 C20 C21 -179.2(3) . . . . ? C2 C1 C20 C22 -178.9(3) . . . . ? C17 C1 C20 C22 57.7(4) . . . . ? O5 C20 C22 O6 -58.1(4) . . . . ? C21 C20 C22 O6 60.6(4) . . . . ? C1 C20 C22 O6 -174.8(3) . . . . ? O5 C20 C22 C23 -179.1(3) . . . . ? C21 C20 C22 C23 -60.4(4) . . . . ? C1 C20 C22 C23 64.2(4) . . . . ? O6 C22 C23 C24 76.6(4) . . . . ? C20 C22 C23 C24 -164.1(3) . . . . ? C22 C23 C24 C27 61.4(5) . . . . ? C22 C23 C24 C25 175.9(3) . . . . ? C26 O7 C25 C28 141.0(5) . . . . ? C26 O7 C25 C24 14.9(5) . . . . ? C23 C24 C25 C28 94.2(5) . . . . ? C27 C24 C25 C28 -143.8(4) . . . . ? C23 C24 C25 O7 -144.2(4) . . . . ? C27 C24 C25 O7 -22.2(4) . . . . ? C25 O7 C26 O8 -179.4(5) . . . . ? C25 O7 C26 C27 -0.5(6) . . . . ? O8 C26 C27 C29 38.1(8) . . . . ? O7 C26 C27 C29 -140.6(5) . . . . ? O8 C26 C27 C24 164.4(5) . . . . ? O7 C26 C27 C24 -14.3(5) . . . . ? C23 C24 C27 C26 140.4(4) . . . . ? C25 C24 C27 C26 21.6(5) . . . . ? C23 C24 C27 C29 -96.1(5) . . . . ? C25 C24 C27 C29 145.1(5) . . . . ? 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 O1 H1 O2 0.84 1.90 2.733(4) 169.3 2_757 O2 H2 O3 0.84 1.95 2.753(3) 158.7 2_757 O4 H4 O8 0.84 2.01 2.754(4) 147.2 2_656 O5 H5 O3 0.84 2.22 2.986(3) 152.5 2_756 O6 H6 O11 0.84 1.94 2.762(4) 167.2 1_554 O9 H9 O1 0.84 1.86 2.688(4) 170.0 1_545 O10 H10 O4 0.84 1.98 2.811(5) 168.0 . O11 H11 O9 0.84 1.94 2.694(5) 148.0 . _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.585 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.065