#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011009.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011009 loop_ _publ_author_name 'Chiaroni, Ang\`ele' 'Riche, Claude' 'Khuong-Huu, Qui' 'Nguyen-Ngoc, Hanh' 'Nguyen-Viet, Kinh' 'Khuong-Huu, Fran\,coise' _publ_section_title ; New limonoids from Harrisonia perforata (Blanco) Merr. ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 711 _journal_page_last 713 _journal_paper_doi 10.1107/S0108270100003565 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C27 H34 O10' _chemical_formula_weight 518.54 _chemical_name_common 'Haperforin D' _chemical_name_systematic ;methyl 6'-furanoyl-3-hydroxy-4,4,3',6',7a'-pentamethylperhydro-4H-furo[2,1-c]- pyran-2-spiro-1'-perhydroisobenzofuran-7'-spiro-2''-oxirane-3''-carboxylate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 99.44(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.148(5) _cell_length_b 11.225(7) _cell_length_c 11.356(8) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.0 _cell_measurement_theta_min 15.2 _cell_volume 1276.1(14) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'NONIUS (Riche, 1989) ' _computing_molecular_graphics 'R3M (Riche, 1983) and ORTEP (Johnson, 1965)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Nonius CAD4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents .0605 _diffrn_reflns_av_sigmaI/netI .0483 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3411 _diffrn_reflns_theta_max 66.89 _diffrn_reflns_theta_min 4.42 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .860 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 552 _exptl_crystal_size_max .350 _exptl_crystal_size_mid .350 _exptl_crystal_size_min .20 _refine_diff_density_max .374 _refine_diff_density_min -.398 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.087 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 334 _refine_ls_number_reflns 2385 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.183 _refine_ls_restrained_S_obs 1.089 _refine_ls_R_factor_all .0703 _refine_ls_R_factor_gt .0656 _refine_ls_shift/esd_mean .004 _refine_ls_shift/su_max -.023 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1223P)^2^+0.1273P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1692 _refine_ls_wR_factor_ref .1554 _reflns_number_gt 2368 _reflns_number_total 2389 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gs1076.cif _cod_data_source_block D _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1223P)^2^+0.1273P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1223P)^2^+0.1273P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2011009 _cod_database_fobs_code 2011009 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 C1 .0345(13) .0444(14) .0479(13) .0017(11) .0149(10) .0026(12) C2 .0396(14) .052(2) .0413(12) .0005(12) .0128(10) .0000(12) C3 .0373(13) .057(2) .0533(15) -.0058(12) .0185(11) -.0083(13) C4 .041(2) .076(2) .054(2) -.0005(15) .0198(13) -.012(2) C5 .035(2) .094(3) .081(2) .013(2) .0119(15) -.009(2) C6 .070(2) .086(3) .078(2) .038(2) .029(2) .018(2) C7 .057(2) .048(2) .067(2) .006(2) .0290(15) .000(2) C8 .0356(12) .0457(15) .0420(13) .0035(11) .0161(10) .0044(12) C9 .0433(14) .0437(15) .0539(15) .0038(12) .0254(12) .0089(13) C10 .0429(15) .045(2) .067(2) -.0009(13) .0278(13) .0007(14) C11 .055(2) .051(2) .063(2) .0017(15) .0357(14) .0058(15) C12 .069(2) .056(2) .0468(15) .006(2) .0306(14) .0086(14) C13 .049(2) .052(2) .0423(13) .0041(14) .0177(11) .0023(13) C14 .0423(14) .0441(14) .0385(12) .0009(11) .0160(10) .0062(11) C15 .0419(14) .057(2) .0481(14) .0055(13) .0114(11) .0031(14) C16 .049(2) .074(2) .054(2) .009(2) .0080(13) .005(2) C17 .049(2) .047(2) .0524(15) .0009(13) .0181(12) -.0024(13) C18 .064(2) .072(2) .050(2) .007(2) .0117(14) -.008(2) C19 .082(3) .050(2) .098(3) -.014(2) .045(2) -.004(2) C20 .0431(14) .046(2) .060(2) -.0001(13) .0148(12) -.0014(14) C21 .062(2) .053(2) .157(5) .003(2) .045(3) .031(3) C22 .050(2) .063(2) .070(2) .002(2) .0126(15) .014(2) C23 .049(2) .055(2) .097(3) .009(2) .024(2) .029(2) C28 .068(2) .102(4) .087(3) .001(3) .033(2) -.043(3) C29 .069(2) .115(4) .054(2) .015(3) .030(2) .011(2) C30 .0415(13) .0461(15) .0461(13) .0050(13) .0120(10) .0049(13) C31 .080(3) .137(6) .093(3) -.013(4) -.028(3) -.003(4) O1 .0500(11) .0454(12) .0527(11) .0071(9) .0203(9) .0047(9) O2 .0571(13) .0585(13) .0489(11) -.0117(11) .0254(9) -.0020(10) O4 .0390(11) .082(2) .0696(14) -.0042(12) .0225(10) -.0036(13) O7 .055(2) .163(5) .106(2) -.002(2) -.005(2) -.023(3) O10 .0418(11) .0639(14) .0635(13) -.0094(11) .0245(9) -.0145(11) O14 .0415(10) .0606(13) .0420(9) -.0036(9) .0140(8) .0074(10) O16 .081(2) .083(2) .075(2) .011(2) -.0023(15) .022(2) O16' .0589(14) .094(2) .0613(14) -.010(2) .0002(11) .007(2) O17 .0602(14) .0558(14) .086(2) .0083(12) .0417(13) .0019(13) O21 .090(2) .084(3) .175(4) .013(2) .069(3) .047(3) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 .3417(3) .3796(4) .8838(2) .0413(6) Uani d . 1 . C C2 .2893(3) .3384(4) .9969(2) .0435(6) Uani d . 1 . C H2 .3609 .3015 1.0535 .052 Uiso calc R 1 . H C3 .2482(3) .4577(4) 1.0446(3) .0478(7) Uani d . 1 . C H3 .3296 .4960 1.0861 .057 Uiso calc R 1 . H C4 .1472(3) .4560(5) 1.1306(3) .0557(8) Uani d . 1 . C C5 -.0262(3) .4443(6) .9550(4) .0698(11) Uani d . 1 . C C6 .0488(4) .5422(6) .9025(4) .0761(13) Uani d . 1 . C H6A .0236 .6183 .9326 .091 Uiso calc R 1 . H H6B .0218 .5426 .8165 .091 Uiso calc R 1 . H C7 .2003(4) .5298(4) .9308(3) .0552(8) Uani d . 1 . C H7 .2415 .6090 .9380 .066 Uiso calc R 1 . H C8 .3746(3) .2872(4) .7896(2) .0400(6) Uani d . 1 . C C9 .4618(3) .3705(4) .7256(3) .0450(7) Uani d . 1 . C H9 .4027 .4321 .6849 .054 Uiso calc R 1 . H C10 .5506(3) .4301(4) .8297(3) .0496(7) Uani d . 1 . C H10 .6263 .3776 .8582 .060 Uiso calc R 1 . H C11 .5254(4) .3063(4) .6305(3) .0531(8) Uani d . 1 . C H11A .5739 .3629 .5893 .064 Uiso calc R 1 . H H11B .5880 .2468 .6678 .064 Uiso calc R 1 . H C12 .4170(4) .2472(4) .5423(3) .0550(8) Uani d . 1 . C H12A .4587 .2042 .4842 .066 Uiso calc R 1 . H H12B .3612 .3087 .4999 .066 Uiso calc R 1 . H C13 .3263(3) .1594(4) .5987(3) .0468(7) Uani d . 1 . C C14 .2683(3) .2296(4) .6958(2) .0406(6) Uani d . 1 . C C15 .1306(3) .2815(4) .6744(3) .0486(7) Uani d . 1 . C H15 .1221 .3519 .7235 .058 Uiso calc R 1 . H C16 .0269(4) .2765(5) .5647(3) .0589(9) Uani d . 1 . C C17 .4072(3) .0464(4) .6414(3) .0482(7) Uani d . 1 . C C18 .2206(4) .1108(5) .4972(3) .0618(9) Uani d . 1 . C H18A .1637 .1747 .4635 .093 Uiso calc R 1 . H H18B .1679 .0512 .5283 .093 Uiso calc R 1 . H H18C .2642 .0763 .4365 .093 Uiso calc R 1 . H C19 .6028(5) .5517(5) .8063(5) .0731(11) Uani d . 1 . C H19A .6574 .5809 .8775 .110 Uiso calc R 1 . H H19B .5291 .6050 .7831 .110 Uiso calc R 1 . H H19C .6552 .5467 .7433 .110 Uiso calc R 1 . H C20 .3526(3) -.0513(4) .7058(3) .0492(7) Uani d . 1 . C C21 .2329(5) -.0688(5) .7469(6) .088(2) Uani d . 1 . C H21 .1626 -.0147 .7398 .105 Uiso calc R 1 . H C22 .4252(4) -.1539(5) .7385(4) .0608(9) Uani d . 1 . C H22 .5097 -.1706 .7211 .073 Uiso calc R 1 . H C23 .3551(4) -.2249(5) .7990(4) .0655(10) Uani d . 1 . C H23 .3848 -.2964 .8354 .079 Uiso calc R 1 . H C28 .1360(5) .5813(6) 1.1824(5) .0831(15) Uani d . 1 . C H28A .1145 .6374 1.1184 .125 Uiso calc R 1 . H H28B .2195 .6028 1.2303 .125 Uiso calc R 1 . H H28C .0669 .5818 1.2309 .125 Uiso calc R 1 . H C29 .1811(4) .3630(7) 1.2279(3) .0768(13) Uani d . 1 . C H29A .1154 .3649 1.2798 .115 Uiso calc R 1 . H H29B .2676 .3797 1.2732 .115 Uiso calc R 1 . H H29C .1818 .2854 1.1923 .115 Uiso calc R 1 . H C30 .4587(3) .1895(4) .8634(3) .0440(6) Uani d . 1 . C H30A .5252 .2262 .9221 .066 Uiso calc R 1 . H H30B .5016 .1410 .8112 .066 Uiso calc R 1 . H H30C .4013 .1407 .9026 .066 Uiso calc R 1 . H C31 -.1611(6) .1723(9) .4668(5) .108(2) Uani d . 1 . C H31A -.2122 .1023 .4773 .162 Uiso calc R 1 . H H31B -.1251 .1657 .3939 .162 Uiso calc R 1 . H H31C -.2177 .2412 .4630 .162 Uiso calc R 1 . H O1 .2442(2) .4654(3) .8336(2) .0480(5) Uani d . 1 . O O2 .1793(2) .2612(4) .9714(2) .0530(6) Uani d . 1 . O HO2 .1650 .2465 .8997 .051 Uiso calc R 1 . H O4 .0151(2) .4182(4) 1.0686(2) .0618(7) Uani d . 1 . O O7 -.1231(4) .3961(7) .9026(4) .110(2) Uani d . 1 . O O10 .4660(2) .4386(4) .9212(2) .0546(6) Uani d . 1 . O O14 .1587(2) .1745(3) .7438(2) .0473(5) Uani d . 1 . O O16 .0167(4) .3540(4) .4901(3) .0815(9) Uani d . 1 . O O16' -.0534(3) .1840(5) .5658(2) .0725(8) Uani d . 1 . O O17 .5166(3) .0316(4) .6119(3) .0641(7) Uani d . 1 . O O21 .2348(4) -.1762(5) .7988(5) .111(2) Uani d . 1 . O loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .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 O10 C1 O1 109.0(3) O10 C1 C2 107.5(2) O1 C1 C2 102.9(2) O10 C1 C8 103.5(2) O1 C1 C8 112.6(2) C2 C1 C8 120.9(3) O2 C2 C3 111.1(2) O2 C2 C1 112.7(2) C3 C2 C1 100.6(3) C2 C3 C4 117.8(3) C2 C3 C7 103.3(2) C4 C3 C7 113.1(3) O4 C4 C29 103.3(3) O4 C4 C3 110.6(3) C29 C4 C3 112.2(3) O4 C4 C28 109.2(3) C29 C4 C28 111.9(4) C3 C4 C28 109.5(3) O7 C5 O4 119.4(5) O7 C5 C6 124.0(5) O4 C5 C6 116.4(4) C5 C6 C7 113.9(3) O1 C7 C6 108.1(3) O1 C7 C3 106.5(3) C6 C7 C3 113.3(3) C14 C8 C9 108.7(2) C14 C8 C30 109.9(3) C9 C8 C30 112.1(2) C14 C8 C1 123.4(2) C9 C8 C1 97.1(2) C30 C8 C1 105.1(2) C10 C9 C11 119.5(3) C10 C9 C8 102.3(2) C11 C9 C8 112.8(3) O10 C10 C19 109.4(3) O10 C10 C9 103.9(2) C19 C10 C9 116.3(3) C12 C11 C9 109.3(3) C11 C12 C13 114.9(3) C18 C13 C17 102.3(3) C18 C13 C14 114.4(3) C17 C13 C14 116.0(2) C18 C13 C12 107.7(3) C17 C13 C12 109.2(3) C14 C13 C12 106.9(3) O14 C14 C15 58.4(2) O14 C14 C8 114.4(2) C15 C14 C8 118.8(3) O14 C14 C13 117.0(3) C15 C14 C13 122.4(3) C8 C14 C13 113.8(2) O14 C15 C16 118.3(3) O14 C15 C14 59.4(2) C16 C15 C14 129.2(3) O16 C16 O16' 126.2(4) O16 C16 C15 121.7(4) O16' C16 C15 111.9(3) O17 C17 C20 117.8(3) O17 C17 C13 119.0(3) C20 C17 C13 122.9(3) C22 C20 C21 104.4(3) C22 C20 C17 121.7(3) C21 C20 C17 133.9(4) O21 C21 C20 108.9(4) C23 C22 C20 109.3(3) C22 C23 O21 108.6(4) C1 O1 C7 108.2(2) C5 O4 C4 121.4(3) C1 O10 C10 110.7(2) C15 O14 C14 62.3(2) C16 O16' C31 117.0(4) C23 O21 C21 108.5(4) 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 C1 O10 . 1.426(4) ? C1 O1 . 1.430(4) ? C1 C2 . 1.540(4) ? C1 C8 . 1.565(4) ? C2 O2 . 1.405(4) ? C2 C3 . 1.528(5) ? C3 C4 . 1.528(4) ? C3 C7 . 1.535(5) ? C4 O4 . 1.471(4) ? C4 C29 . 1.518(6) ? C4 C28 . 1.535(7) ? C5 O7 . 1.193(6) ? C5 O4 . 1.322(5) ? C5 C6 . 1.514(8) ? C6 C7 . 1.524(6) ? C7 O1 . 1.449(4) ? C8 C14 . 1.530(4) ? C8 C9 . 1.548(4) ? C8 C30 . 1.549(4) ? C9 C10 . 1.519(5) ? C9 C11 . 1.526(4) ? C10 O10 . 1.456(3) ? C10 C19 . 1.502(5) ? C11 C12 . 1.514(6) ? C12 C13 . 1.556(5) ? C13 C18 . 1.540(5) ? C13 C17 . 1.546(5) ? C13 C14 . 1.548(4) ? C14 O14 . 1.455(3) ? C14 C15 . 1.496(4) ? C15 O14 . 1.439(4) ? C15 C16 . 1.494(5) ? C16 O16 . 1.207(5) ? C16 O16' . 1.322(6) ? C17 O17 . 1.223(4) ? C17 C20 . 1.475(5) ? C20 C22 . 1.385(6) ? C20 C21 . 1.385(6) ? C21 O21 . 1.341(7) ? C22 C23 . 1.332(6) ? C23 O21 . 1.337(6) ? C31 O16' . 1.440(5) ? 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 _geom_hbond_publ_flag O2 HO2 O14 1_555 .82 1.94 2.738(3) 164.9 yes 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_publ_flag O10 C1 C2 O2 -169.6(3) ? O1 C1 C2 O2 75.4(3) ? C8 C1 C2 O2 -51.3(3) ? O10 C1 C2 C3 72.0(3) ? O1 C1 C2 C3 -43.0(3) yes C8 C1 C2 C3 -169.6(2) ? O2 C2 C3 C4 39.4(4) ? C1 C2 C3 C4 158.9(3) ? O2 C2 C3 C7 -86.0(3) ? C1 C2 C3 C7 33.4(3) yes C2 C3 C4 O4 -68.3(4) ? C2 C3 C4 C29 46.5(4) ? C7 C3 C4 C29 167.0(4) ? C2 C3 C4 C28 171.4(3) ? C7 C3 C4 C28 -68.1(4) ? O7 C5 C6 C7 -137.4(5) ? C5 C6 C7 O1 93.2(4) ? C2 C3 C7 O1 -13.2(3) yes C3 C7 O1 C1 -14.6(3) yes C7 O1 C1 C2 36.3(3) yes C4 C3 C7 C6 -23.0(5) yes C3 C7 C6 C5 -24.5(5) yes C7 C6 C5 O4 47.5(5) yes C6 C5 O4 C4 -17.0(6) yes C5 O4 C4 C3 -32.7(5) yes O4 C4 C3 C7 52.3(4) yes O10 C1 C8 C9 -42.2(3) yes C1 C8 C9 C10 45.1(3) yes C8 C9 C10 O10 -32.9(3) yes C9 C10 O10 C1 5.5(3) yes C10 O10 C1 C8 23.9(3) yes C13 C14 C15 C16 .7(5) yes C14 C15 C16 O16 -92.8(5) yes C4 C3 C7 O1 -141.7(3) ? C2 C3 C7 C6 105.5(3) ? O10 C1 C8 C14 -160.1(3) ? O1 C1 C8 C14 -42.5(3) ? C2 C1 C8 C14 79.6(3) ? O1 C1 C8 C9 75.5(3) ? C2 C1 C8 C9 -162.4(2) ? O10 C1 C8 C30 73.0(3) ? O1 C1 C8 C30 -169.3(2) ? C2 C1 C8 C30 -47.3(3) ? C14 C8 C9 C10 174.0(2) ? C30 C8 C9 C10 -64.3(3) ? C14 C8 C9 C11 -56.3(3) ? C30 C8 C9 C11 65.4(3) ? C1 C8 C9 C11 174.8(3) ? C11 C9 C10 O10 -158.3(3) ? C11 C9 C10 C19 81.4(4) ? C8 C9 C10 C19 -153.3(3) ? C10 C9 C11 C12 175.8(3) ? C8 C9 C11 C12 55.6(4) ? C9 C11 C12 C13 -56.1(4) ? C11 C12 C13 C18 178.5(3) ? C11 C12 C13 C17 -71.1(4) ? C11 C12 C13 C14 55.1(4) ? C9 C8 C14 O14 -164.6(2) ? C30 C8 C14 O14 72.5(3) ? C1 C8 C14 O14 -52.3(4) ? C9 C8 C14 C15 -98.6(3) ? C30 C8 C14 C15 138.4(3) ? C1 C8 C14 C15 13.7(4) ? C9 C8 C14 C13 57.2(3) ? C30 C8 C14 C13 -65.8(3) ? C1 C8 C14 C13 169.5(2) ? C18 C13 C14 O14 48.3(4) ? C17 C13 C14 O14 -70.5(3) ? C12 C13 C14 O14 167.4(2) ? C18 C13 C14 C15 -19.8(4) ? C17 C13 C14 C15 -138.6(3) ? C12 C13 C14 C15 99.3(3) ? C18 C13 C14 C8 -174.6(3) ? C17 C13 C14 C8 66.6(3) ? C12 C13 C14 C8 -55.5(3) ? O14 C14 C15 O14 .0000(10) ? C8 C14 C15 O14 -102.5(3) ? C13 C14 C15 O14 103.9(3) ? O14 C14 C15 C16 -103.2(4) ? C8 C14 C15 C16 154.3(3) ? O14 C15 C16 O16 -165.0(4) ? O14 C15 C16 O16' 19.3(4) ? C14 C15 C16 O16' 91.4(4) ? C18 C13 C17 O17 103.3(3) ? C14 C13 C17 O17 -131.5(3) ? C12 C13 C17 O17 -10.6(4) ? C18 C13 C17 C20 -70.0(4) ? C14 C13 C17 C20 55.3(4) ? C12 C13 C17 C20 176.1(3) ? O17 C17 C20 C22 3.9(5) ? C13 C17 C20 C22 177.2(3) ? O17 C17 C20 C21 -176.3(5) ? C13 C17 C20 C21 -3.0(7) ? C22 C20 C21 O21 -1.0(7) ? C17 C20 C21 O21 179.1(5) ? C21 C20 C22 C23 -2.2(6) ? C17 C20 C22 C23 177.6(4) ? C20 C22 C23 O21 4.7(6) ? O10 C1 O1 C7 -77.6(3) ? C8 C1 O1 C7 168.1(2) ? C6 C7 O1 C1 -136.6(3) ? O7 C5 O4 C4 167.7(5) ? C29 C4 O4 C5 -153.0(4) ? C28 C4 O4 C5 87.8(4) ? O1 C1 O10 C10 -96.2(3) ? C2 C1 O10 C10 152.9(3) ? C19 C10 O10 C1 130.4(3) ? C16 C15 O14 C14 121.1(3) ? C14 C15 O14 C14 .0000(10) ? C15 C14 O14 C15 .0000(10) ? C8 C14 O14 C15 110.0(3) ? C13 C14 O14 C15 -113.2(3) ? O16 C16 O16' C31 2.0(7) ? C15 C16 O16' C31 177.6(5) ? C22 C23 O21 C21 -5.4(7) ? C20 C21 O21 C23 3.9(8) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21182500 2 PubChem 139057742