data_2203336 loop_ _publ_author_name 'Asilo\'e J. Mora' 'Gerzon E. Delgado' 'Gavin B. M. Vaughan' 'Patrick Martin' 'Tom\'as Visbal' 'Alfredo Usubillaga' _publ_section_title ; Peracetyled glucosil ester of kaurenic acid ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o334 _journal_page_last o336 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C34 H48 O11' _chemical_formula_moiety 'C34 H48 O11' _chemical_formula_sum 'C34 H48 O11' _chemical_formula_weight 632.72 _chemical_name_common ? _chemical_name_systematic ; (4\a)-Kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-\a-D-glucopyranoside ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 106.578(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 15.3738(8) _cell_length_b 7.2254(2) _cell_length_c 15.9661(9) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 19.273 _cell_measurement_theta_min 2.437 _cell_volume 1699.82(14) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997) ; _computing_publication_material ; SHELXL97 and PLATON (Speck, 2000) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 0.70 _diffrn_measured_fraction_theta_full 0.764 _diffrn_measured_fraction_theta_max 0.764 _diffrn_measurement_device 'Bruker fixed kappa goniometer' _diffrn_measurement_method '\f scan 0.1\% interval' _diffrn_radiation_monochromator 'double crystal Si' _diffrn_radiation_source 'Beamline ID-11 ESRF' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.53378 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8193 _diffrn_reflns_theta_full 18.08 _diffrn_reflns_theta_max 18.08 _diffrn_reflns_theta_min 10.25 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.057 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 680 _exptl_crystal_size_max .15 _exptl_crystal_size_mid .03 _exptl_crystal_size_min .03 _refine_diff_density_max 0.202 _refine_diff_density_min -0.179 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 406 _refine_ls_number_reflns 2336 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0462 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.2167P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1239 _refine_ls_wR_factor_ref 0.1252 _reflns_number_gt 2240 _reflns_number_total 2336 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.15717(15) 0.4151(4) 0.34328(18) 0.0517(7) Uani d . 1 . . O O2 0.11242(14) 0.1960(4) 0.24137(13) 0.0441(6) Uani d . 1 . . O O3 -0.00812(17) 0.4872(4) 0.14644(14) 0.0479(6) Uani d . 1 . . O O4 0.0774(3) 0.4190(8) 0.0582(4) 0.1058(18) Uani d . 1 . . O O5 -0.18295(15) 0.3512(4) 0.05705(13) 0.0440(6) Uani d . 1 . . O O6 -0.2517(4) 0.5713(10) 0.1126(2) 0.127(3) Uani d . 1 . . O O7 -0.25293(15) 0.0944(4) 0.16372(15) 0.0480(6) Uani d . 1 . . O O8 -0.3051(2) -0.0004(8) 0.0244(2) 0.0836(12) Uani d . 1 . . O O9 -0.05559(18) -0.1936(4) 0.35920(15) 0.0506(6) Uani d . 1 . . O O10 -0.07349(17) -0.4984(4) 0.34740(16) 0.0509(6) Uani d . 1 . . O O11 -0.00857(14) 0.0371(4) 0.24671(14) 0.0428(6) Uani d . 1 . . O C1 0.2917(2) -0.1345(5) 0.4280(2) 0.0472(8) Uani d . 1 . . C H1A 0.2659 -0.2257 0.4605 0.057 Uiso calc R 1 . . H H1B 0.3542 -0.1746 0.4315 0.057 Uiso calc R 1 . . H C2 0.2348(2) -0.1359(5) 0.3317(2) 0.0495(8) Uani d . 1 . . C H2A 0.2388 -0.2594 0.3063 0.059 Uiso calc R 1 . . H H2B 0.1704 -0.1125 0.3281 0.059 Uiso calc R 1 . . H C3 0.2675(2) 0.0103(6) 0.2796(2) 0.0457(8) Uani d . 1 . . C H3A 0.2271 0.0101 0.2190 0.055 Uiso calc R 1 . . H H3B 0.3292 -0.0232 0.2773 0.055 Uiso calc R 1 . . H C4 0.27010(18) 0.2062(5) 0.31713(19) 0.0388(7) Uani d . 1 . . C C5 0.32695(16) 0.2014(5) 0.41536(18) 0.0354(7) Uani d . 1 . . C H5A 0.3881 0.1572 0.4138 0.042 Uiso calc R 1 . . H C6 0.34584(19) 0.3883(5) 0.4613(2) 0.0398(7) Uani d . 1 . . C H6A 0.3621 0.4799 0.4221 0.048 Uiso calc R 1 . . H H6B 0.2907 0.4327 0.4752 0.048 Uiso calc R 1 . . H C7 0.4232(2) 0.3700(6) 0.5449(2) 0.0450(8) Uani d . 1 . . C H7A 0.4789 0.3326 0.5298 0.054 Uiso calc R 1 . . H H7B 0.4348 0.4923 0.5738 0.054 Uiso calc R 1 . . H C8 0.40454(18) 0.2304(5) 0.60854(19) 0.0413(8) Uani d . 1 . . C C9 0.37266(18) 0.0446(5) 0.5623(2) 0.0407(7) Uani d . 1 . . C H9A 0.4270 -0.0032 0.5465 0.049 Uiso calc R 1 . . H C10 0.29612(18) 0.0547(5) 0.47248(19) 0.0373(7) Uani d . 1 . . C C11 0.3563(2) -0.0994(6) 0.6279(2) 0.0525(9) Uani d . 1 . . C H11A 0.3162 -0.1978 0.5946 0.063 Uiso calc R 1 . . H H11B 0.4151 -0.1575 0.6584 0.063 Uiso calc R 1 . . H C12 0.3135(3) -0.0230(7) 0.6971(3) 0.0594(11) Uani d . 1 . . C H12A 0.2476 -0.0047 0.6703 0.071 Uiso calc R 1 . . H H12B 0.3215 -0.1142 0.7450 0.071 Uiso calc R 1 . . H C13 0.3565(2) 0.1602(7) 0.7346(2) 0.0565(10) Uani d . 1 . . C H13A 0.3330 0.2048 0.7833 0.068 Uiso calc R 1 . . H C14 0.3399(2) 0.3006(6) 0.6603(2) 0.0460(8) Uani d . 1 . . C H14A 0.3559 0.4275 0.6828 0.055 Uiso calc R 1 . . H H14B 0.2758 0.2986 0.6239 0.055 Uiso calc R 1 . . H C15 0.4914(2) 0.2005(7) 0.6857(2) 0.0549(9) Uani d . 1 . . C H15A 0.5298 0.1027 0.6712 0.066 Uiso calc R 1 . . H H15B 0.5271 0.3163 0.6989 0.066 Uiso calc R 1 . . H C16 0.4589(3) 0.1429(8) 0.7628(3) 0.0596(10) Uani d . 1 . . C C17 0.5094(3) 0.0892(10) 0.8405(3) 0.0784(15) Uani d . 1 . . C H17A 0.5736 0.0838 0.8525 0.094 Uiso calc R 1 . . H H17B 0.4816 0.0560 0.8844 0.094 Uiso calc R 1 . . H C18 0.17505(19) 0.2847(5) 0.30522(19) 0.0369(7) Uani d . 1 . . C C19 0.3139(2) 0.3340(6) 0.2638(2) 0.0491(8) Uani d . 1 . . C H19A 0.2771 0.3343 0.2026 0.074 Uiso calc R 1 . . H H19B 0.3751 0.2894 0.2676 0.074 Uiso calc R 1 . . H H19C 0.3176 0.4600 0.2873 0.074 Uiso calc R 1 . . H C20 0.20100(19) 0.0949(5) 0.4832(2) 0.0424(7) Uani d . 1 . . C H20A 0.1563 0.0994 0.4255 0.064 Uiso calc R 1 . . H H20B 0.2019 0.2141 0.5127 0.064 Uiso calc R 1 . . H H20C 0.1845 -0.0034 0.5181 0.064 Uiso calc R 1 . . H C21 0.02061(19) 0.2181(5) 0.23823(18) 0.0385(7) Uani d . 1 . . C H21A 0.0142 0.2982 0.2872 0.046 Uiso calc R 1 . . H C22 -0.0330(2) 0.2975(5) 0.14946(19) 0.0401(7) Uani d . 1 . . C H22A -0.0200 0.2262 0.1007 0.048 Uiso calc R 1 . . H C23 -0.1337(2) 0.2897(5) 0.14314(17) 0.0393(7) Uani d . 1 . . C H23A -0.1465 0.3748 0.1876 0.047 Uiso calc R 1 . . H C24 -0.1613(2) 0.0933(5) 0.15930(18) 0.0401(7) Uani d . 1 . . C H24A -0.1550 0.0086 0.1118 0.048 Uiso calc R 1 . . H C25 -0.10006(19) 0.0282(5) 0.24883(18) 0.0390(7) Uani d . 1 . . C H25A -0.1086 0.1121 0.2957 0.047 Uiso calc R 1 . . H C26 0.0503(3) 0.5329(8) 0.1005(2) 0.0584(11) Uani d . 1 . . C C27 0.0771(4) 0.7266(9) 0.1124(3) 0.0729(13) Uani d . 1 . . C H27A 0.1194 0.7546 0.0784 0.109 Uiso calc R 1 . . H H27B 0.1067 0.7504 0.1744 0.109 Uiso calc R 1 . . H H27C 0.0231 0.8051 0.0924 0.109 Uiso calc R 1 . . H C28 -0.2405(3) 0.4936(8) 0.0504(2) 0.0666(13) Uani d . 1 . . C C29 -0.2843(5) 0.5410(12) -0.0429(3) 0.101(2) Uani d . 1 . . C H29A -0.3249 0.6471 -0.0462 0.151 Uiso calc R 1 . . H H29B -0.3193 0.4347 -0.0726 0.151 Uiso calc R 1 . . H H29C -0.2375 0.5726 -0.0712 0.151 Uiso calc R 1 . . H C30 -0.3190(2) 0.0444(7) 0.0906(3) 0.0568(10) Uani d . 1 . . C C31 -0.4111(3) 0.0675(10) 0.1055(3) 0.0777(15) Uani d . 1 . . C H31A -0.4584 0.0321 0.0524 0.116 Uiso calc R 1 . . H H31B -0.4195 0.1970 0.1196 0.116 Uiso calc R 1 . . H H31C -0.4150 -0.0118 0.1541 0.116 Uiso calc R 1 . . H C32 -0.1155(2) -0.1676(6) 0.2710(2) 0.0460(8) Uani d . 1 . . C H32A -0.1797 -0.1874 0.2694 0.055 Uiso calc R 1 . . H H32B -0.0997 -0.2543 0.2296 0.055 Uiso calc R 1 . . H C33 -0.0371(2) -0.3666(5) 0.3866(2) 0.0415(7) Uani d . 1 . . C C34 0.0355(3) -0.3722(7) 0.4725(2) 0.0580(9) Uani d . 1 . . C H34A 0.0472 -0.5010 0.4917 0.087 Uiso calc R 1 . . H H34B 0.0155 -0.3023 0.5162 0.087 Uiso calc R 1 . . H H34C 0.0913 -0.3169 0.4656 0.087 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0391(11) 0.0441(15) 0.0674(14) 0.0033(10) 0.0078(9) -0.0113(12) O2 0.0344(10) 0.0580(16) 0.0405(10) -0.0010(10) 0.0116(8) -0.0094(10) O3 0.0511(12) 0.0528(16) 0.0426(11) -0.0035(10) 0.0179(9) 0.0057(10) O4 0.112(3) 0.119(4) 0.119(3) -0.055(3) 0.086(3) -0.042(3) O5 0.0469(11) 0.0556(16) 0.0292(9) 0.0080(10) 0.0104(8) 0.0044(9) O6 0.168(4) 0.173(6) 0.0466(15) 0.121(5) 0.042(2) 0.027(2) O7 0.0357(10) 0.0640(17) 0.0409(10) -0.0063(10) 0.0052(8) 0.0047(10) O8 0.0662(17) 0.116(3) 0.0536(17) -0.0047(19) -0.0072(13) -0.0135(18) O9 0.0675(15) 0.0424(15) 0.0347(11) -0.0016(11) 0.0029(9) 0.0018(10) O10 0.0547(13) 0.0492(16) 0.0517(12) -0.0019(11) 0.0198(10) -0.0001(11) O11 0.0372(10) 0.0433(14) 0.0457(10) 0.0026(9) 0.0082(8) 0.0024(9) C1 0.0415(15) 0.039(2) 0.0588(18) 0.0030(13) 0.0108(13) -0.0002(15) C2 0.0503(16) 0.0354(19) 0.0601(18) -0.0028(14) 0.0113(14) -0.0072(15) C3 0.0412(14) 0.049(2) 0.0495(16) 0.0017(14) 0.0174(12) -0.0094(15) C4 0.0336(13) 0.0436(19) 0.0425(15) -0.0031(13) 0.0162(11) -0.0038(13) C5 0.0261(11) 0.0400(18) 0.0433(14) 0.0000(12) 0.0152(10) -0.0024(12) C6 0.0379(13) 0.0412(18) 0.0432(14) -0.0054(12) 0.0163(12) -0.0002(13) C7 0.0355(13) 0.055(2) 0.0459(15) -0.0100(13) 0.0131(11) -0.0053(15) C8 0.0303(13) 0.053(2) 0.0424(15) 0.0038(13) 0.0139(11) -0.0012(14) C9 0.0306(12) 0.047(2) 0.0467(15) 0.0086(12) 0.0150(12) 0.0047(13) C10 0.0286(12) 0.0383(18) 0.0459(14) 0.0012(11) 0.0120(11) 0.0025(13) C11 0.0478(16) 0.050(2) 0.0583(18) 0.0073(15) 0.0129(14) 0.0125(16) C12 0.0509(17) 0.076(3) 0.0551(18) 0.0052(18) 0.0210(14) 0.023(2) C13 0.0468(17) 0.082(3) 0.0442(15) 0.0100(18) 0.0183(13) 0.0073(18) C14 0.0381(14) 0.060(2) 0.0435(15) 0.0070(15) 0.0175(12) -0.0020(14) C15 0.0358(14) 0.077(3) 0.0508(17) 0.0046(17) 0.0111(12) -0.0004(18) C16 0.0510(18) 0.078(3) 0.0486(17) 0.0103(18) 0.0128(14) 0.0032(18) C17 0.067(2) 0.108(4) 0.054(2) 0.018(3) 0.0065(17) 0.005(2) C18 0.0360(14) 0.0359(19) 0.0392(14) -0.0025(12) 0.0113(11) 0.0020(12) C19 0.0485(16) 0.056(2) 0.0484(15) -0.0080(15) 0.0224(12) -0.0018(15) C20 0.0323(13) 0.048(2) 0.0508(15) -0.0002(12) 0.0174(11) 0.0055(14) C21 0.0351(13) 0.0449(19) 0.0355(13) 0.0003(13) 0.0099(10) -0.0007(12) C22 0.0427(14) 0.0437(19) 0.0353(13) 0.0006(13) 0.0134(11) 0.0008(12) C23 0.0400(14) 0.051(2) 0.0263(12) 0.0009(13) 0.0078(10) 0.0013(12) C24 0.0361(14) 0.050(2) 0.0320(13) -0.0015(13) 0.0058(10) -0.0003(12) C25 0.0355(13) 0.048(2) 0.0322(12) -0.0030(13) 0.0069(10) -0.0002(12) C26 0.0554(18) 0.087(3) 0.0376(15) -0.023(2) 0.0206(14) -0.0106(18) C27 0.085(3) 0.080(3) 0.056(2) -0.032(3) 0.0235(18) 0.003(2) C28 0.071(2) 0.093(3) 0.0394(17) 0.035(2) 0.0226(15) 0.017(2) C29 0.123(4) 0.135(6) 0.0428(19) 0.076(4) 0.020(2) 0.025(3) C30 0.0434(16) 0.065(3) 0.050(2) -0.0050(17) -0.0055(14) 0.0090(17) C31 0.0421(18) 0.101(4) 0.079(2) -0.008(2) -0.0008(17) 0.020(3) C32 0.0444(15) 0.053(2) 0.0363(14) -0.0050(14) 0.0050(11) 0.0008(14) C33 0.0440(15) 0.044(2) 0.0404(14) -0.0038(14) 0.0182(12) 0.0015(14) C34 0.066(2) 0.057(3) 0.0451(16) 0.0044(17) 0.0067(14) 0.0118(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 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 0.0056 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C18 O2 C21 . . 117.8(2) ? C26 O3 C22 . . 118.6(3) ? C28 O5 C23 . . 117.9(3) ? C30 O7 C24 . . 117.4(3) ? C33 O9 C32 . . 117.2(3) ? C21 O11 C25 . . 113.0(2) ? C10 C1 C2 . . 114.0(3) ? C10 C1 H1A . . 108.8 ? C2 C1 H1A . . 108.8 ? C10 C1 H1B . . 108.8 ? C2 C1 H1B . . 108.8 ? H1A C1 H1B . . 107.6 ? C3 C2 C1 . . 111.1(3) ? C3 C2 H2A . . 109.4 ? C1 C2 H2A . . 109.4 ? C3 C2 H2B . . 109.4 ? C1 C2 H2B . . 109.4 ? H2A C2 H2B . . 108.0 ? C2 C3 C4 . . 113.8(3) ? C2 C3 H3A . . 108.8 ? C4 C3 H3A . . 108.8 ? C2 C3 H3B . . 108.8 ? C4 C3 H3B . . 108.8 ? H3A C3 H3B . . 107.7 ? C18 C4 C3 . . 112.2(3) ? C18 C4 C19 . . 105.2(3) ? C3 C4 C19 . . 107.8(2) ? C18 C4 C5 . . 112.0(2) ? C3 C4 C5 . . 108.4(3) ? C19 C4 C5 . . 111.2(2) ? C6 C5 C10 . . 111.7(2) ? C6 C5 C4 . . 116.0(3) ? C10 C5 C4 . . 115.2(2) ? C6 C5 H5A . . 104.1 ? C10 C5 H5A . . 104.1 ? C4 C5 H5A . . 104.1 ? C7 C6 C5 . . 109.8(3) ? C7 C6 H6A . . 109.7 ? C5 C6 H6A . . 109.7 ? C7 C6 H6B . . 109.7 ? C5 C6 H6B . . 109.7 ? H6A C6 H6B . . 108.2 ? C8 C7 C6 . . 113.3(2) ? 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 ? C7 C8 C9 . . 110.7(3) ? C7 C8 C14 . . 114.4(3) ? C9 C8 C14 . . 112.1(3) ? C7 C8 C15 . . 109.9(3) ? C9 C8 C15 . . 110.0(3) ? C14 C8 C15 . . 99.2(2) ? C8 C9 C11 . . 110.6(3) ? C8 C9 C10 . . 116.6(3) ? C11 C9 C10 . . 115.0(3) ? C8 C9 H9A . . 104.3 ? C11 C9 H9A . . 104.3 ? C10 C9 H9A . . 104.3 ? C1 C10 C20 . . 107.5(3) ? C1 C10 C5 . . 108.4(2) ? C20 C10 C5 . . 113.1(3) ? C1 C10 C9 . . 107.7(3) ? C20 C10 C9 . . 113.1(2) ? C5 C10 C9 . . 106.9(2) ? C12 C11 C9 . . 115.5(4) ? C12 C11 H11A . . 108.4 ? C9 C11 H11A . . 108.4 ? C12 C11 H11B . . 108.4 ? C9 C11 H11B . . 108.4 ? H11A C11 H11B . . 107.5 ? C13 C12 C11 . . 111.5(3) ? C13 C12 H12A . . 109.3 ? C11 C12 H12A . . 109.3 ? C13 C12 H12B . . 109.3 ? C11 C12 H12B . . 109.3 ? H12A C12 H12B . . 108.0 ? C16 C13 C12 . . 110.1(4) ? C16 C13 C14 . . 102.4(3) ? C12 C13 C14 . . 108.3(3) ? C16 C13 H13A . . 111.9 ? C12 C13 H13A . . 111.9 ? C14 C13 H13A . . 111.9 ? C13 C14 C8 . . 101.9(3) ? C13 C14 H14A . . 111.4 ? C8 C14 H14A . . 111.4 ? C13 C14 H14B . . 111.4 ? C8 C14 H14B . . 111.4 ? H14A C14 H14B . . 109.3 ? C16 C15 C8 . . 106.0(3) ? C16 C15 H15A . . 110.5 ? C8 C15 H15A . . 110.5 ? C16 C15 H15B . . 110.5 ? C8 C15 H15B . . 110.5 ? H15A C15 H15B . . 108.7 ? C17 C16 C15 . . 127.1(4) ? C17 C16 C13 . . 125.9(4) ? C15 C16 C13 . . 107.0(3) ? C16 C17 H17A . . 120.0 ? C16 C17 H17B . . 120.0 ? H17A C17 H17B . . 120.0 ? O1 C18 O2 . . 122.8(3) ? O1 C18 C4 . . 125.5(3) ? O2 C18 C4 . . 111.6(3) ? C4 C19 H19A . . 109.5 ? C4 C19 H19B . . 109.5 ? H19A C19 H19B . . 109.5 ? C4 C19 H19C . . 109.5 ? H19A C19 H19C . . 109.5 ? H19B C19 H19C . . 109.5 ? C10 C20 H20A . . 109.5 ? C10 C20 H20B . . 109.5 ? H20A C20 H20B . . 109.5 ? C10 C20 H20C . . 109.5 ? H20A C20 H20C . . 109.5 ? H20B C20 H20C . . 109.5 ? O11 C21 O2 . . 103.7(3) ? O11 C21 C22 . . 109.6(3) ? O2 C21 C22 . . 110.1(2) ? O11 C21 H21A . . 111.1 ? O2 C21 H21A . . 111.1 ? C22 C21 H21A . . 111.1 ? O3 C22 C23 . . 108.1(3) ? O3 C22 C21 . . 108.2(3) ? C23 C22 C21 . . 108.4(2) ? O3 C22 H22A . . 110.7 ? C23 C22 H22A . . 110.7 ? C21 C22 H22A . . 110.7 ? O5 C23 C24 . . 110.7(3) ? O5 C23 C22 . . 107.4(2) ? C24 C23 C22 . . 110.5(3) ? O5 C23 H23A . . 109.4 ? C24 C23 H23A . . 109.4 ? C22 C23 H23A . . 109.4 ? O7 C24 C23 . . 109.2(3) ? O7 C24 C25 . . 107.7(2) ? C23 C24 C25 . . 108.4(2) ? O7 C24 H24A . . 110.5 ? C23 C24 H24A . . 110.5 ? C25 C24 H24A . . 110.5 ? O11 C25 C32 . . 105.9(3) ? O11 C25 C24 . . 108.1(2) ? C32 C25 C24 . . 114.3(3) ? O11 C25 H25A . . 109.5 ? C32 C25 H25A . . 109.5 ? C24 C25 H25A . . 109.5 ? O4 C26 O3 . . 121.6(5) ? O4 C26 C27 . . 126.7(4) ? O3 C26 C27 . . 111.7(4) ? C26 C27 H27A . . 109.5 ? C26 C27 H27B . . 109.5 ? H27A C27 H27B . . 109.5 ? C26 C27 H27C . . 109.5 ? H27A C27 H27C . . 109.5 ? H27B C27 H27C . . 109.5 ? O6 C28 O5 . . 122.9(3) ? O6 C28 C29 . . 126.3(4) ? O5 C28 C29 . . 110.8(4) ? C28 C29 H29A . . 109.5 ? C28 C29 H29B . . 109.5 ? H29A C29 H29B . . 109.5 ? C28 C29 H29C . . 109.5 ? H29A C29 H29C . . 109.5 ? H29B C29 H29C . . 109.5 ? O8 C30 O7 . . 124.0(4) ? O8 C30 C31 . . 126.0(3) ? O7 C30 C31 . . 109.8(4) ? C30 C31 H31A . . 109.5 ? C30 C31 H31B . . 109.5 ? H31A C31 H31B . . 109.5 ? C30 C31 H31C . . 109.5 ? H31A C31 H31C . . 109.5 ? H31B C31 H31C . . 109.5 ? O9 C32 C25 . . 104.6(3) ? O9 C32 H32A . . 110.8 ? C25 C32 H32A . . 110.8 ? O9 C32 H32B . . 110.8 ? C25 C32 H32B . . 110.8 ? H32A C32 H32B . . 108.9 ? O10 C33 O9 . . 123.8(3) ? O10 C33 C34 . . 125.1(3) ? O9 C33 C34 . . 111.1(3) ? C33 C34 H34A . . 109.5 ? C33 C34 H34B . . 109.5 ? H34A C34 H34B . . 109.5 ? C33 C34 H34C . . 109.5 ? H34A C34 H34C . . 109.5 ? H34B C34 H34C . . 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C18 . 1.195(4) yes O2 C18 . 1.348(4) yes O2 C21 . 1.407(4) yes O3 C26 . 1.353(5) ? O3 C22 . 1.427(5) yes O4 C26 . 1.211(7) ? O5 C28 . 1.341(6) ? O5 C23 . 1.437(4) ? O6 C28 . 1.194(6) ? O7 C30 . 1.360(5) ? O7 C24 . 1.431(4) ? O8 C30 . 1.180(6) ? O9 C33 . 1.328(5) ? O9 C32 . 1.459(4) ? O10 C33 . 1.189(5) ? O11 C21 . 1.402(5) yes O11 C25 . 1.418(4) ? C1 C10 . 1.533(5) ? C1 C2 . 1.536(5) ? C1 H1A . 0.9900 ? C1 H1B . 0.9900 ? C2 C3 . 1.517(6) ? C2 H2A . 0.9900 ? C2 H2B . 0.9900 ? C3 C4 . 1.533(5) ? C3 H3A . 0.9900 ? C3 H3B . 0.9900 ? C4 C18 . 1.528(4) yes C4 C19 . 1.536(5) yes C4 C5 . 1.563(4) ? C5 C6 . 1.524(5) ? C5 C10 . 1.558(4) ? C5 H5A . 1.0000 ? C6 C7 . 1.520(4) ? C6 H6A . 0.9900 ? C6 H6B . 0.9900 ? C7 C8 . 1.516(5) ? C7 H7A . 0.9900 ? C7 H7B . 0.9900 ? C8 C9 . 1.543(5) ? C8 C14 . 1.548(4) ? C8 C15 . 1.552(4) ? C9 C11 . 1.547(5) ? C9 C10 . 1.576(4) ? C9 H9A . 1.0000 ? C10 C20 . 1.547(4) ? C11 C12 . 1.541(6) ? C11 H11A . 0.9900 ? C11 H11B . 0.9900 ? C12 C13 . 1.523(8) ? C12 H12A . 0.9900 ? C12 H12B . 0.9900 ? C13 C16 . 1.513(5) ? C13 C14 . 1.527(6) ? C13 H13A . 1.0000 ? C14 H14A . 0.9900 ? C14 H14B . 0.9900 ? C15 C16 . 1.513(5) ? C15 H15A . 0.9900 ? C15 H15B . 0.9900 ? C16 C17 . 1.321(7) ? C17 H17A . 0.9500 ? C17 H17B . 0.9500 ? C19 H19A . 0.9800 ? C19 H19B . 0.9800 ? C19 H19C . 0.9800 ? C20 H20A . 0.9800 ? C20 H20B . 0.9800 ? C20 H20C . 0.9800 ? C21 C22 . 1.533(4) yes C21 H21A . 1.0000 ? C22 C23 . 1.524(4) ? C22 H22A . 1.0000 ? C23 C24 . 1.523(5) ? C23 H23A . 1.0000 ? C24 C25 . 1.544(4) ? C24 H24A . 1.0000 ? C25 C32 . 1.494(6) ? C25 H25A . 1.0000 ? C26 C27 . 1.456(8) ? C27 H27A . 0.9800 ? C27 H27B . 0.9800 ? C27 H27C . 0.9800 ? C28 C29 . 1.489(5) ? C29 H29A . 0.9800 ? C29 H29B . 0.9800 ? C29 H29C . 0.9800 ? C30 C31 . 1.510(7) ? C31 H31A . 0.9800 ? C31 H31B . 0.9800 ? C31 H31C . 0.9800 ? C32 H32A . 0.9900 ? C32 H32B . 0.9900 ? C33 C34 . 1.501(5) ? C34 H34A . 0.9800 ? C34 H34B . 0.9800 ? C34 H34C . 0.9800 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C13 H13A O6 2_546 1.00 2.54 3.348(5) 138 C21 H21A O10 1_565 1.00 2.38 3.281(4) 150 C27 H27C O4 2 0.98 2.59 3.361(8) 135