# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Weidong Zhang' _publ_contact_author_email WDZHANGY@HOTMAIL.COM _publ_section_title ; Abiesatrines A-J: anti-inflammatory and anti-tumor triterpenoids from Abies georgei Orr ; loop_ _publ_author_name 'Weidong Zhang' 'Lin Feng' 'Su-Mei Li' 'Yong-Li Li' 'Yonghong Liu' ; Yun-Heng Shen ; 'Jian Tang' 'Jun-Mian Tian' 'Ning Wang' 'Liang Wu' 'Xian-Wen Yang' # Attachment '5-Abiesatrine_A.cif' data_f80314a _database_code_depnum_ccdc_archive 'CCDC 761403' #TrackingRef '5-Abiesatrine_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H50 O5' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 293(2) _chemical_formula_weight 502.71 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 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration ? 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 8.165(15) _cell_length_b 13.02(3) _cell_length_c 26.83(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2852(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 781 _cell_measurement_theta_min 2.164 _cell_measurement_theta_max 27.035 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9885 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 11872 _diffrn_reflns_av_R_equivalents 0.2995 _diffrn_reflns_av_sigmaI/netI 0.2853 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5047 _reflns_number_gt 2188 _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^)+(0.0633P)^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(3) _refine_ls_number_reflns 5047 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2828 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _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 1.0307(5) 0.7614(3) 0.05596(12) 0.0621(11) Uani 1 1 d . . . H1C H 1.1100 0.7783 0.0391 0.093 Uiso 1 1 calc R . . O2 O 0.4952(4) 0.3673(3) 0.10714(10) 0.0455(9) Uani 1 1 d . . . O3 O 0.5295(5) 0.3034(3) 0.02673(13) 0.0605(12) Uani 1 1 d . . . O4 O 0.5522(6) 0.3960(4) -0.04202(15) 0.1013(18) Uani 1 1 d . . . C1 C 1.0917(7) 0.6218(4) 0.1374(2) 0.0552(15) Uani 1 1 d . . . H1A H 1.1682 0.5768 0.1544 0.066 Uiso 1 1 calc R . . H1B H 1.0752 0.5947 0.1041 0.066 Uiso 1 1 calc R . . C2 C 1.1667(7) 0.7255(5) 0.1332(2) 0.0629(17) Uani 1 1 d . . . H2A H 1.2696 0.7207 0.1153 0.076 Uiso 1 1 calc R . . H2B H 1.1891 0.7523 0.1663 0.076 Uiso 1 1 calc R . . C3 C 1.0514(7) 0.7978(4) 0.10580(18) 0.0515(16) Uani 1 1 d . . . H3A H 1.1018 0.8660 0.1046 0.062 Uiso 1 1 calc R . . C4 C 0.8839(7) 0.8069(4) 0.13147(17) 0.0495(15) Uani 1 1 d . . . C5 C 0.8139(6) 0.6993(4) 0.14116(17) 0.0418(14) Uani 1 1 d . . . H5A H 0.7891 0.6718 0.1080 0.050 Uiso 1 1 calc R . . C6 C 0.6512(7) 0.6992(5) 0.1684(2) 0.0583(17) Uani 1 1 d . . . H6A H 0.6633 0.7378 0.1992 0.070 Uiso 1 1 calc R . . H6B H 0.5708 0.7345 0.1481 0.070 Uiso 1 1 calc R . . C7 C 0.5884(7) 0.5956(4) 0.18057(16) 0.0459(14) Uani 1 1 d . . . H7A H 0.4789 0.5906 0.1899 0.055 Uiso 1 1 calc R . . C8 C 0.6734(7) 0.5101(4) 0.17938(15) 0.0373(14) Uani 1 1 d . . . C9 C 0.8469(7) 0.5134(4) 0.16037(16) 0.0424(14) Uani 1 1 d . . . H9A H 0.9100 0.4668 0.1817 0.051 Uiso 1 1 calc R . . C10 C 0.9279(7) 0.6190(4) 0.16521(16) 0.0487(16) Uani 1 1 d . . . C11 C 0.8380(7) 0.4618(4) 0.10911(17) 0.0505(16) Uani 1 1 d . . . H11A H 0.7583 0.4970 0.0884 0.061 Uiso 1 1 calc R . . H11B H 0.9438 0.4660 0.0928 0.061 Uiso 1 1 calc R . . C12 C 0.7892(7) 0.3508(4) 0.11537(19) 0.0490(15) Uani 1 1 d . . . H12A H 0.8735 0.3161 0.1345 0.059 Uiso 1 1 calc R . . H12B H 0.7854 0.3190 0.0827 0.059 Uiso 1 1 calc R . . C13 C 0.6228(7) 0.3337(4) 0.14137(16) 0.0422(14) Uani 1 1 d . . . C14 C 0.5999(7) 0.4035(4) 0.18713(15) 0.0409(14) Uani 1 1 d . . . C15 C 0.6839(8) 0.3380(4) 0.22741(18) 0.0600(18) Uani 1 1 d . . . H15A H 0.8021 0.3405 0.2241 0.072 Uiso 1 1 calc R . . H15B H 0.6537 0.3609 0.2606 0.072 Uiso 1 1 calc R . . C16 C 0.6192(8) 0.2305(5) 0.21720(18) 0.0683(19) Uani 1 1 d . . . H16A H 0.5146 0.2203 0.2336 0.082 Uiso 1 1 calc R . . H16B H 0.6956 0.1792 0.2294 0.082 Uiso 1 1 calc R . . C17 C 0.5997(7) 0.2219(4) 0.15969(18) 0.0506(15) Uani 1 1 d . . . C18 C 0.7323(9) 0.1448(5) 0.1421(2) 0.083(2) Uani 1 1 d . . . H18A H 0.7263 0.1373 0.1065 0.125 Uiso 1 1 calc R . . H18B H 0.7139 0.0794 0.1576 0.125 Uiso 1 1 calc R . . H18C H 0.8387 0.1700 0.1512 0.125 Uiso 1 1 calc R . . C19 C 0.9565(8) 0.6358(5) 0.22130(17) 0.0666(19) Uani 1 1 d . . . H19A H 1.0292 0.5838 0.2337 0.100 Uiso 1 1 calc R . . H19B H 0.8538 0.6317 0.2386 0.100 Uiso 1 1 calc R . . H19C H 1.0042 0.7023 0.2266 0.100 Uiso 1 1 calc R . . C20 C 0.4325(8) 0.1813(4) 0.14505(19) 0.0588(17) Uani 1 1 d . . . H20A H 0.3515 0.2271 0.1603 0.071 Uiso 1 1 calc R . . C21 C 0.3883(10) 0.0731(5) 0.1611(2) 0.088(2) Uani 1 1 d . . . H21A H 0.3979 0.0675 0.1967 0.132 Uiso 1 1 calc R . . H21B H 0.4614 0.0250 0.1455 0.132 Uiso 1 1 calc R . . H21C H 0.2778 0.0582 0.1513 0.132 Uiso 1 1 calc R . . C22 C 0.4131(9) 0.1923(4) 0.0886(2) 0.074(2) Uani 1 1 d . . . H22A H 0.4961 0.1513 0.0721 0.088 Uiso 1 1 calc R . . H22B H 0.3068 0.1661 0.0788 0.088 Uiso 1 1 calc R . . C23 C 0.4283(7) 0.3012(5) 0.07183(18) 0.0534(16) Uani 1 1 d . . . C24 C 0.2728(7) 0.3563(5) 0.05472(19) 0.0565(17) Uani 1 1 d . . . H24A H 0.1944 0.3077 0.0412 0.068 Uiso 1 1 calc R . . H24B H 0.2223 0.3927 0.0823 0.068 Uiso 1 1 calc R . . C25 C 0.3285(8) 0.4305(5) 0.01502(18) 0.0587(17) Uani 1 1 d . . . H25A H 0.2466 0.4338 -0.0116 0.070 Uiso 1 1 calc R . . C26 C 0.3707(9) 0.5379(5) 0.0322(2) 0.0721(19) Uani 1 1 d . . . H26A H 0.4037 0.5785 0.0041 0.108 Uiso 1 1 calc R . . H26B H 0.4586 0.5348 0.0559 0.108 Uiso 1 1 calc R . . H26C H 0.2764 0.5686 0.0476 0.108 Uiso 1 1 calc R . . C27 C 0.4816(8) 0.3783(5) -0.0039(2) 0.0620(18) Uani 1 1 d . . . C28 C 0.7680(8) 0.8661(4) 0.09702(19) 0.0628(17) Uani 1 1 d . . . H28A H 0.6616 0.8701 0.1121 0.094 Uiso 1 1 calc R . . H28B H 0.7600 0.8311 0.0656 0.094 Uiso 1 1 calc R . . H28C H 0.8098 0.9341 0.0918 0.094 Uiso 1 1 calc R . . C29 C 0.9084(8) 0.8735(4) 0.17790(18) 0.0670(18) Uani 1 1 d . . . H29A H 0.8060 0.8809 0.1951 0.100 Uiso 1 1 calc R . . H29B H 0.9480 0.9399 0.1682 0.100 Uiso 1 1 calc R . . H29C H 0.9867 0.8413 0.1996 0.100 Uiso 1 1 calc R . . C30 C 0.4201(7) 0.4138(4) 0.20248(17) 0.0576(17) Uani 1 1 d . . . H30A H 0.3738 0.3467 0.2072 0.086 Uiso 1 1 calc R . . H30B H 0.3608 0.4493 0.1768 0.086 Uiso 1 1 calc R . . H30C H 0.4129 0.4518 0.2331 0.086 Uiso 1 1 calc R . . O5 O 0.8056(7) 0.6739(5) 0.9926(2) 0.1122(19) Uani 1 1 d . . . H5 H 0.8708 0.7049 1.0104 0.168 Uiso 1 1 calc R . . C31 C 0.8726(10) 0.5820(7) 0.9783(2) 0.096(2) Uani 1 1 d . . . H31A H 0.9209 0.5892 0.9458 0.144 Uiso 1 1 calc R . . H31B H 0.7886 0.5305 0.9771 0.144 Uiso 1 1 calc R . . H31C H 0.9553 0.5620 1.0018 0.144 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 0.056(3) 0.073(3) 0.058(2) -0.006(2) 0.0026(19) -0.011(2) O2 0.051(2) 0.039(2) 0.0459(17) -0.0043(18) -0.0136(17) 0.003(2) O3 0.059(3) 0.069(3) 0.054(2) -0.016(2) -0.007(2) 0.020(2) O4 0.111(4) 0.125(4) 0.068(3) 0.002(3) 0.033(3) 0.028(4) C1 0.037(4) 0.045(4) 0.084(3) 0.009(3) -0.005(3) 0.003(3) C2 0.037(4) 0.068(5) 0.083(4) -0.001(4) -0.006(3) 0.000(4) C3 0.050(4) 0.045(4) 0.060(3) -0.003(3) 0.001(3) -0.010(3) C4 0.050(4) 0.043(4) 0.055(3) -0.001(3) 0.003(3) -0.005(3) C5 0.042(4) 0.033(3) 0.050(3) -0.005(3) -0.001(3) 0.009(3) C6 0.051(4) 0.050(4) 0.074(3) -0.003(3) 0.010(3) 0.005(4) C7 0.049(4) 0.037(4) 0.051(3) -0.007(3) 0.011(3) 0.002(3) C8 0.044(4) 0.035(4) 0.032(2) -0.004(2) 0.000(2) 0.004(3) C9 0.036(4) 0.042(4) 0.049(3) 0.000(3) -0.001(3) 0.009(3) C10 0.048(4) 0.047(4) 0.051(3) 0.005(3) -0.012(3) 0.002(3) C11 0.039(4) 0.056(4) 0.056(3) -0.008(3) 0.007(3) 0.006(3) C12 0.048(4) 0.038(4) 0.061(3) -0.001(3) 0.001(3) 0.010(3) C13 0.046(4) 0.031(3) 0.050(3) 0.001(3) 0.000(3) 0.011(3) C14 0.042(4) 0.043(4) 0.037(2) -0.006(2) -0.002(3) 0.009(3) C15 0.074(5) 0.057(4) 0.049(3) 0.005(3) -0.011(3) 0.003(4) C16 0.082(5) 0.058(5) 0.065(3) 0.021(3) -0.006(3) 0.004(4) C17 0.051(4) 0.032(4) 0.069(3) -0.001(3) -0.004(3) 0.006(3) C18 0.093(6) 0.039(4) 0.117(5) 0.003(4) 0.009(4) 0.020(4) C19 0.068(5) 0.068(5) 0.064(3) 0.007(3) -0.029(3) -0.020(4) C20 0.073(5) 0.032(4) 0.071(4) -0.004(3) -0.004(3) -0.010(4) C21 0.099(6) 0.050(5) 0.115(5) 0.011(4) -0.001(4) -0.012(5) C22 0.095(6) 0.039(4) 0.087(4) -0.006(3) -0.016(4) -0.020(4) C23 0.056(4) 0.053(4) 0.051(3) -0.008(3) -0.009(3) -0.013(4) C24 0.044(4) 0.067(4) 0.058(3) -0.008(3) -0.009(3) -0.002(3) C25 0.052(4) 0.076(5) 0.049(3) -0.001(3) -0.007(3) 0.012(4) C26 0.079(5) 0.070(5) 0.067(3) 0.007(3) -0.002(3) 0.005(4) C27 0.053(5) 0.079(5) 0.053(3) -0.012(4) -0.002(3) 0.013(4) C28 0.063(5) 0.046(4) 0.079(4) 0.013(3) -0.006(3) 0.009(4) C29 0.081(5) 0.043(4) 0.077(3) -0.016(3) -0.001(3) -0.012(4) C30 0.064(5) 0.043(4) 0.066(3) -0.010(3) 0.019(3) -0.005(4) O5 0.088(4) 0.116(5) 0.132(4) -0.047(3) -0.051(3) 0.034(4) C31 0.085(6) 0.115(7) 0.089(4) -0.013(5) -0.004(4) 0.005(6) _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 1.429(6) . ? O1 H1C 0.8200 . ? O2 C23 1.392(6) . ? O2 C13 1.456(6) . ? O3 C27 1.336(7) . ? O3 C23 1.465(7) . ? O4 C27 1.195(7) . ? C1 C2 1.486(8) . ? C1 C10 1.532(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.521(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.536(8) . ? C3 H3A 0.9800 . ? C4 C28 1.531(7) . ? C4 C29 1.531(7) . ? C4 C5 1.536(8) . ? C5 C6 1.516(8) . ? C5 C10 1.541(7) . ? C5 H5A 0.9800 . ? C6 C7 1.479(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.313(7) . ? C7 H7A 0.9300 . ? C8 C9 1.506(8) . ? C8 C14 1.527(8) . ? C9 C11 1.532(7) . ? C9 C10 1.532(8) . ? C9 H9A 0.9800 . ? C10 C19 1.538(7) . ? C11 C12 1.508(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.544(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.539(7) . ? C13 C17 1.548(8) . ? C14 C30 1.531(8) . ? C14 C15 1.538(7) . ? C15 C16 1.521(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.555(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.516(8) . ? C17 C18 1.551(8) . ? 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 C21 1.517(8) . ? C20 C22 1.529(8) . ? C20 H20A 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.492(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.529(8) . ? C24 C25 1.508(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C27 1.511(8) . ? C25 C26 1.513(9) . ? C25 H25A 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 . ? O5 C31 1.372(9) . ? O5 H5 0.8200 . ? 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 C3 O1 H1C 109.5 . . ? C23 O2 C13 121.6(4) . . ? C27 O3 C23 111.0(4) . . ? C2 C1 C10 114.7(5) . . ? C2 C1 H1A 108.6 . . ? C10 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? C10 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C1 C2 C3 110.1(5) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C2 108.7(5) . . ? O1 C3 C4 109.9(4) . . ? C2 C3 C4 112.5(5) . . ? O1 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C28 C4 C29 106.7(5) . . ? C28 C4 C3 108.6(4) . . ? C29 C4 C3 107.0(5) . . ? C28 C4 C5 109.3(5) . . ? C29 C4 C5 115.3(4) . . ? C3 C4 C5 109.7(5) . . ? C6 C5 C4 114.1(5) . . ? C6 C5 C10 109.1(4) . . ? C4 C5 C10 117.7(5) . . ? C6 C5 H5A 104.9 . . ? C4 C5 H5A 104.9 . . ? C10 C5 H5A 104.9 . . ? C7 C6 C5 114.2(5) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 125.8(6) . . ? C8 C7 H7A 117.1 . . ? C6 C7 H7A 117.1 . . ? C7 C8 C9 118.8(5) . . ? C7 C8 C14 124.1(5) . . ? C9 C8 C14 116.2(5) . . ? C8 C9 C11 104.3(4) . . ? C8 C9 C10 113.7(5) . . ? C11 C9 C10 119.3(4) . . ? C8 C9 H9A 106.2 . . ? C11 C9 H9A 106.2 . . ? C10 C9 H9A 106.2 . . ? C1 C10 C9 110.9(5) . . ? C1 C10 C19 109.9(5) . . ? C9 C10 C19 106.0(4) . . ? C1 C10 C5 107.9(4) . . ? C9 C10 C5 108.2(5) . . ? C19 C10 C5 113.9(5) . . ? C12 C11 C9 109.4(4) . . ? C12 C11 H11A 109.8 . . ? C9 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? C9 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 114.9(4) . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? O2 C13 C14 103.8(4) . . ? O2 C13 C12 107.5(4) . . ? C14 C13 C12 112.4(4) . . ? O2 C13 C17 113.3(4) . . ? C14 C13 C17 106.7(4) . . ? C12 C13 C17 112.8(5) . . ? C8 C14 C30 109.5(5) . . ? C8 C14 C15 115.2(5) . . ? C30 C14 C15 106.7(4) . . ? C8 C14 C13 112.4(4) . . ? C30 C14 C13 112.5(4) . . ? C15 C14 C13 100.3(4) . . ? C16 C15 C14 103.3(5) . . ? C16 C15 H15A 111.1 . . ? C14 C15 H15A 111.1 . . ? C16 C15 H15B 111.1 . . ? C14 C15 H15B 111.1 . . ? H15A C15 H15B 109.1 . . ? C15 C16 C17 106.3(4) . . ? C15 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? C15 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C20 C17 C13 110.9(5) . . ? C20 C17 C18 108.9(5) . . ? C13 C17 C18 115.3(5) . . ? C20 C17 C16 112.0(5) . . ? C13 C17 C16 103.6(4) . . ? C18 C17 C16 106.1(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 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 . . ? C17 C20 C21 117.7(5) . . ? C17 C20 C22 108.5(5) . . ? C21 C20 C22 110.2(5) . . ? C17 C20 H20A 106.6 . . ? C21 C20 H20A 106.6 . . ? C22 C20 H20A 106.6 . . ? 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 . . ? C23 C22 C20 112.3(5) . . ? C23 C22 H22A 109.1 . . ? C20 C22 H22A 109.1 . . ? C23 C22 H22B 109.1 . . ? C20 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? O2 C23 O3 109.2(5) . . ? O2 C23 C22 114.5(4) . . ? O3 C23 C22 108.3(5) . . ? O2 C23 C24 103.9(5) . . ? O3 C23 C24 102.2(4) . . ? C22 C23 C24 117.9(5) . . ? C25 C24 C23 105.2(5) . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C24 C25 C27 101.5(5) . . ? C24 C25 C26 116.5(5) . . ? C27 C25 C26 109.3(6) . . ? C24 C25 H25A 109.7 . . ? C27 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? 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 . . ? O4 C27 O3 121.7(6) . . ? O4 C27 C25 126.9(6) . . ? O3 C27 C25 111.3(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 . . ? C31 O5 H5 109.5 . . ? O5 C31 H31A 109.5 . . ? O5 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O5 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? 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 O5 H5 O1 0.82 1.93 2.750(7) 172.7 1_556 O1 H1C O5 0.82 1.91 2.729(7) 172.7 4_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.166 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.042