#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/48/2004843.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_2004843 loop_ _publ_author_name 'Casta\~neda-Acosta, J.' 'Fischer, N. H.' 'Fronczek, F. R.' _publ_section_title ; The Guaianolide 11\bH,13-Dihydromicheliolide ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1263 _journal_page_last 1266 _journal_paper_doi 10.1107/S0108270195015435 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C15 H22 O3' _chemical_formula_sum 'C15 H22 O3' _chemical_formula_weight 250.34 _chemical_name_systematic ; azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,7,8,9,9a,9b-octahydro-9-hydroxy- 3,6,9-trimethyl-[3S-(3\a,3a\a,9\a,9a\a,9b\b)] ; _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 101.29(1) _cell_angle_beta 97.70(1) _cell_angle_gamma 118.42(1) _cell_formula_units_Z 2 _cell_length_a 8.5033(8) _cell_length_b 8.8856(6) _cell_length_c 10.773(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 299 _cell_measurement_theta_max 13 _cell_measurement_theta_min 9 _cell_volume 677.24(14) _computing_cell_refinement CAD-4 _computing_data_collection 'CAD-4 (Enraf-Nonius, 1977)' _computing_data_reduction 'PROCESS MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIF in MolEN' _computing_structure_refinement 'LSFM MolEN' _computing_structure_solution 'RANTAN (Yao, 1981), DIRDIF (Beurskens, 1984)' _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3099 _diffrn_reflns_theta_max 27.5 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.228 _exptl_crystal_description needle_fragment _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.21 _refine_diff_density_min -0.06 _refine_ls_abs_structure_details ; assumed to correspond to accepted absolute configuration of sesquiterpene lactones from higher plants (Fischer, Olivier & Fischer, 1979). ; _refine_ls_extinction_coef '0.13(2) x 10^-5^' _refine_ls_extinction_method 'isotropic (Zachariasen, 1963)' _refine_ls_goodness_of_fit_obs 2.72 _refine_ls_hydrogen_treatment 'H atoms: see text' _refine_ls_number_parameters 331 _refine_ls_number_reflns 2776 _refine_ls_R_factor_obs 0.040 _refine_ls_shift/esd_max 0.014 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.048 _reflns_number_observed 2776 _reflns_number_total 3099 _reflns_observed_criterion >2.0\s(I) _cod_data_source_file bk1193.cif _cod_data_source_block 1 _cod_depositor_comments ; Updating space group information. Antanas Vaitkus, 2018-06-14 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 677.2(3) _cod_database_code 2004843 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,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 O1A 0.0742(8) 0.0242(5) 0.0340(7) 0.0214(5) 0.0106(6) 0.0062(5) O2A 0.1100(10) 0.0459(7) 0.0364(8) 0.0347(7) 0.0198(8) 0.0104(6) O3A 0.0831(7) 0.0424(5) 0.0480(8) 0.0427(4) 0.0225(6) 0.0132(6) C1A 0.0416(8) 0.0319(7) 0.0357(9) 0.0191(5) 0.0099(7) 0.0112(6) C2A 0.0720(10) 0.0376(8) 0.0430(10) 0.0310(6) 0.0230(9) 0.0169(7) C3A 0.0780(10) 0.0360(7) 0.0480(10) 0.0338(6) 0.0234(9) 0.0188(7) C4A 0.0600(10) 0.0253(6) 0.0420(10) 0.0228(6) 0.0168(8) 0.0112(7) C5A 0.0426(8) 0.0244(6) 0.0359(9) 0.0173(5) 0.0124(7) 0.0093(6) C6A 0.0462(8) 0.0232(6) 0.0326(9) 0.0158(5) 0.0112(7) 0.0071(6) C7A 0.0457(8) 0.0209(6) 0.0380(9) 0.0155(5) 0.0086(7) 0.0085(6) C8A 0.0740(10) 0.0256(7) 0.0460(10) 0.0272(6) 0.0174(9) 0.0090(7) C9A 0.0780(10) 0.0254(8) 0.0420(10) 0.0160(8) 0.0100(10) 0.0004(9) C10A 0.0434(8) 0.0338(8) 0.0350(10) 0.0174(6) 0.0058(8) 0.0063(7) C11A 0.0574(9) 0.0275(7) 0.0420(10) 0.0217(6) 0.0129(8) 0.0118(7) C12A 0.0630(10) 0.0318(7) 0.0390(10) 0.0231(6) 0.0112(9) 0.0126(7) C13A 0.091(2) 0.0350(8) 0.0540(10) 0.0256(8) 0.0270(10) 0.0236(8) C14A 0.0530(10) 0.0456(9) 0.0400(10) 0.0237(7) 0.0116(9) 0.0048(9) C15A 0.0630(10) 0.0267(8) 0.0640(10) 0.0153(7) 0.0170(10) 0.0105(9) O1B 0.0764(8) 0.0273(6) 0.0439(7) 0.0206(5) 0.0272(6) 0.0096(5) O2B 0.142(2) 0.0455(9) 0.0573(9) 0.0306(9) 0.0531(9) 0.0161(8) O3B 0.0581(8) 0.0240(6) 0.0560(10) 0.0107(5) 0.0054(8) 0.0026(6) C1B 0.0441(8) 0.0360(8) 0.0380(10) 0.0180(6) 0.0141(7) 0.0114(7) C2B 0.0910(10) 0.0500(10) 0.0460(10) 0.0337(9) 0.0270(10) 0.0230(8) C3B 0.0790(10) 0.0305(8) 0.0630(10) 0.0226(8) 0.0330(10) 0.0206(8) C4B 0.0511(9) 0.0256(7) 0.0440(10) 0.0166(6) 0.0148(8) 0.0109(7) C5B 0.0396(8) 0.0221(6) 0.0379(9) 0.0124(5) 0.0086(7) 0.0073(6) C6B 0.0436(8) 0.0263(7) 0.0368(9) 0.0162(5) 0.0106(7) 0.0074(7) C7B 0.0382(8) 0.0219(7) 0.0410(10) 0.0119(5) 0.0082(7) 0.0071(7) C8B 0.0500(10) 0.0221(7) 0.0460(10) 0.0103(6) 0.0080(9) 0.0044(8) C9B 0.0690(10) 0.0285(8) 0.0510(10) 0.0222(7) 0.0190(10) 0.0020(9) C10B 0.0421(9) 0.0357(9) 0.0390(10) 0.0143(6) 0.0120(8) 0.0045(8) C11B 0.0510(10) 0.0281(8) 0.0460(10) 0.0136(6) 0.0167(8) 0.0113(7) C12B 0.0740(10) 0.0338(9) 0.0500(10) 0.0209(8) 0.0300(10) 0.0156(8) C13B 0.101(2) 0.0400(10) 0.0630(10) 0.0280(10) 0.0320(10) 0.0267(9) C14B 0.0620(10) 0.0580(10) 0.0410(10) 0.0236(9) 0.0150(10) 0.0050(10) C15B 0.0700(10) 0.0400(8) 0.075(2) 0.0326(7) 0.0280(10) 0.0224(9) 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 O1A 0 0 0 0.0467(5) Uani ? O2A -0.0228(3) -0.0571(2) 0.1897(2) 0.0669(7) Uani ? O3A -0.0534(2) 0.2618(2) -0.1212(2) 0.0527(5) Uani ? C1A -0.0774(3) -0.0988(2) -0.3707(2) 0.0362(6) Uani ? C2A -0.0151(3) 0.0525(3) -0.4327(2) 0.0483(7) Uani ? C3A -0.0274(4) 0.1977(3) -0.3402(2) 0.0503(7) Uani ? C4A 0.0209(3) 0.1812(2) -0.2044(2) 0.0417(6) Uani ? C5A -0.0845(3) -0.0262(2) -0.2315(2) 0.0340(5) Uani ? C6A -0.0123(3) -0.0924(2) -0.1327(2) 0.0351(6) Uani ? C7A -0.1314(3) -0.2894(2) -0.1422(2) 0.0359(6) Uani ? C8A -0.1095(3) -0.4125(3) -0.2490(2) 0.0483(7) Uani ? C9A -0.1974(4) -0.4276(3) -0.3868(3) 0.0553(8) Uani ? C10A -0.1213(3) -0.2644(3) -0.4352(2) 0.0396(6) Uani ? C11A -0.0736(3) -0.2906(2) -0.0035(2) 0.0422(6) Uani ? C12A -0.0305(3) -0.1085(3) 0.0763(2) 0.0452(7) Uani ? C13A -0.2097(4) -0.4446(3) 0.0382(3) 0.0605(9) Uani ? C14A -0.1045(3) -0.3047(3) -0.5735(2) 0.0483(7) Uani ? C15A 0.2281(4) 0.2694(3) -0.1507(3) 0.0553(8) Uani ? O1B 0.4020(2) 0.6677(2) 0.1061(2) 0.0508(5) Uani ? O2B 0.4767(3) 0.7420(3) -0.0721(2) 0.0864(9) Uani ? O3B 0.0829(2) 0.3534(2) 0.1612(2) 0.0534(6) Uani ? C1B 0.3384(3) 0.7353(3) 0.4525(2) 0.0399(6) Uani ? C2B 0.2845(4) 0.5835(3) 0.5131(3) 0.0611(9) Uani ? C3B 0.1521(4) 0.4166(3) 0.3989(3) 0.0575(8) Uani ? C4B 0.2282(3) 0.4567(3) 0.2817(2) 0.0414(6) Uani ? C5B 0.2876(3) 0.6567(2) 0.3034(2) 0.0352(6) Uani ? C6B 0.4410(3) 0.7632(2) 0.2438(2) 0.0367(6) Uani ? C7B 0.4691(3) 0.9435(2) 0.2378(2) 0.0360(6) Uani ? C8B 0.5605(3) 1.0892(3) 0.3682(2) 0.0444(7) Uani ? C9B 0.4385(4) 1.0557(3) 0.4624(3) 0.0524(8) Uani ? C10B 0.4050(3) 0.9061(3) 0.5216(2) 0.0426(7) Uani ? C11B 0.5693(3) 0.9756(3) 0.1310(2) 0.0445(7) Uani ? C12B 0.4810(4) 0.7872(3) 0.0405(2) 0.0539(8) Uani ? C13B 0.5613(5) 1.1050(3) 0.0614(3) 0.069(1) Uani ? C14B 0.4356(4) 0.9589(4) 0.6690(3) 0.0586(9) Uani ? C15B 0.3829(4) 0.4192(3) 0.2768(3) 0.0581(8) Uani ? H3OA 0.006(4) 0.288(4) -0.040(3) 0.08(1) Uiso ? H3OB 0.056(4) 0.244(4) 0.153(3) 0.09(1) Uiso ? H141A -0.1345 -0.2357 -0.6181 0.0628 Uiso calc H141B 0.5488 1.0700 0.7080 0.0762 Uiso calc H21A -0.0947 0.0136 -0.5177 0.0627 Uiso calc H22A 0.1085 0.0952 -0.4389 0.0627 Uiso calc H31A -0.1492 0.1779 -0.3612 0.0654 Uiso calc H32A 0.0585 0.3128 -0.3450 0.0654 Uiso calc H5A -0.2074 -0.0688 -0.2236 0.0442 Uiso calc H6A 0.1017 -0.0706 -0.1508 0.0456 Uiso calc H7A -0.2611 -0.3366 -0.1696 0.0467 Uiso calc H81A -0.1659 -0.5287 -0.2379 0.0627 Uiso calc H82A 0.0191 -0.3671 -0.2398 0.0627 Uiso calc H91A -0.3241 -0.4673 -0.3920 0.0719 Uiso calc H92A -0.1888 -0.5166 -0.4456 0.0719 Uiso calc H11A 0.0274 -0.3099 0.0080 0.0549 Uiso calc H131A -0.1589 -0.4314 0.1265 0.0786 Uiso calc H132A -0.3223 -0.4446 0.0315 0.0786 Uiso calc H133A -0.2335 -0.5545 -0.0171 0.0786 Uiso calc H142A -0.1873 -0.4286 -0.6181 0.0628 Uiso calc H143A 0.0190 -0.2753 -0.5718 0.0628 Uiso calc H151A 0.2740 0.2136 -0.2076 0.0718 Uiso calc H152A 0.2866 0.3930 -0.1448 0.0718 Uiso calc H153A 0.2539 0.2569 -0.0660 0.0718 Uiso calc H21B 0.2248 0.5960 0.5796 0.0794 Uiso calc H22B 0.3902 0.5796 0.5494 0.0794 Uiso calc H31B 0.0300 0.3965 0.3850 0.0747 Uiso calc H32B 0.1511 0.3146 0.4145 0.0747 Uiso calc H5B 0.1888 0.6638 0.2579 0.0458 Uiso calc H6B 0.5471 0.7796 0.3008 0.0478 Uiso calc H7B 0.3576 0.9448 0.2177 0.0469 Uiso calc H81B 0.5895 1.2000 0.3528 0.0578 Uiso calc H82B 0.6714 1.0959 0.4077 0.0578 Uiso calc H91B 0.3210 1.0301 0.4162 0.0681 Uiso calc H92B 0.4940 1.1633 0.5328 0.0681 Uiso calc H11B 0.6997 1.0360 0.1664 0.0579 Uiso calc H131B 0.6288 1.1139 -0.0030 0.0893 Uiso calc H132B 0.4358 1.0628 0.0203 0.0893 Uiso calc H133B 0.6141 1.2197 0.1233 0.0893 Uiso calc H142B 0.4411 0.8693 0.7017 0.0762 Uiso calc H143B 0.3361 0.9707 0.6897 0.0762 Uiso calc H151B 0.4779 0.4877 0.3566 0.0756 Uiso calc H152B 0.3362 0.2952 0.2653 0.0756 Uiso calc H153B 0.4320 0.4508 0.2055 0.0756 Uiso calc loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C6A O1A C12A 110.30(10) yes C4A O3A H3OA 108(2) yes C2A C1A C5A 107.8(2) yes C2A C1A C10A 122.6(2) yes C5A C1A C10A 129.5(2) yes C1A C2A C3A 104.5(2) yes C2A C3A C4A 104.8(2) yes O3A C4A C3A 107.6(2) yes O3A C4A C5A 111.5(2) yes O3A C4A C15A 111.1(2) yes C3A C4A C5A 101.8(2) yes C3A C4A C15A 111.4(2) yes C5A C4A C15A 113.0(2) yes C1A C5A C4A 104.4(2) yes C1A C5A C6A 112.8(2) yes C4A C5A C6A 115.50(10) yes O1A C6A C5A 109.9(2) yes O1A C6A C7A 103.1(2) yes C5A C6A C7A 116.8(2) yes C6A C7A C8A 112.9(2) yes C6A C7A C11A 102.40(10) yes C8A C7A C11A 115.8(2) yes C7A C8A C9A 113.2(3) yes C8A C9A C10A 119.7(2) yes C1A C10A C9A 127.0(2) yes C1A C10A C14A 119.9(2) yes C9A C10A C14A 112.9(2) yes C7A C11A C12A 101.8(2) yes C7A C11A C13A 116.9(2) yes C12A C11A C13A 113.7(2) yes O1A C12A O2A 120.9(2) yes O1A C12A C11A 109.8(2) yes O2A C12A C11A 129.4(2) yes C6B O1B C12B 109.4(2) yes C4B O3B H3OB 103(2) yes C2B C1B C5B 108.5(2) yes C2B C1B C10B 123.6(2) yes C5B C1B C10B 127.7(2) yes C1B C2B C3B 103.9(2) yes C2B C3B C4B 104.5(2) yes O3B C4B C3B 110.6(2) yes O3B C4B C5B 107.5(2) yes O3B C4B C15B 110.0(2) yes C3B C4B C5B 102.7(2) yes C3B C4B C15B 111.1(3) yes C5B C4B C15B 114.6(2) yes C1B C5B C4B 104.3(2) yes C1B C5B C6B 112.50(10) yes C4B C5B C6B 116.3(2) yes O1B C6B C5B 110.90(10) yes O1B C6B C7B 102.9(2) yes C5B C6B C7B 116.1(2) yes C6B C7B C8B 114.9(2) yes C6B C7B C11B 101.5(2) yes C8B C7B C11B 117.1(2) yes C7B C8B C9B 113.0(2) yes C8B C9B C10B 117.8(3) yes C1B C10B C9B 124.8(2) yes C1B C10B C14B 120.8(2) yes C9B C10B C14B 114.2(2) yes C7B C11B C12B 101.5(2) yes C7B C11B C13B 117.3(3) yes C12B C11B C13B 113.1(2) yes O1B C12B O2B 122.2(2) yes O1B C12B C11B 109.8(2) yes O2B C12B C11B 128.0(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1A C6A 1.465(2) yes O1A C12A 1.343(3) yes O2A C12A 1.198(3) yes O3A C4A 1.430(3) yes O3A H3OA 0.88(3) yes C1A C2A 1.517(3) yes C1A C5A 1.533(3) yes C1A C10A 1.340(3) yes C2A C3A 1.524(4) yes C3A C4A 1.520(4) yes C4A C5A 1.559(3) yes C4A C15A 1.512(4) yes C5A C6A 1.507(4) yes C6A C7A 1.521(3) yes C7A C8A 1.522(4) yes C7A C11A 1.513(3) yes C8A C9A 1.520(4) yes C9A C10A 1.513(4) yes C10A C14A 1.505(4) yes C11A C12A 1.516(3) yes C11A C13A 1.512(3) yes O1B C6B 1.462(3) yes O1B C12B 1.350(3) yes O2B C12B 1.191(3) yes O3B C4B 1.442(3) yes O3B H3OB 0.87(4) yes C1B C2B 1.515(4) yes C1B C5B 1.530(3) yes C1B C10B 1.343(3) yes C2B C3B 1.518(3) yes C3B C4B 1.522(4) yes C4B C5B 1.555(3) yes C4B C15B 1.508(5) yes C5B C6B 1.515(3) yes C6B C7B 1.519(3) yes C7B C8B 1.513(3) yes C7B C11B 1.514(4) yes C8B C9B 1.516(4) yes C9B C10B 1.509(4) yes C10B C14B 1.514(4) yes C11B C12B 1.511(3) yes C11B C13B 1.513(5) 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 C12A O1A C6A C5A 148.3(2) C12A O1A C6A C7A 23.2(2) C6A O1A C12A O2A 178.4(3) C6A O1A C12A C11A -2.0(3) H3OA O3A C4A C3A -160(2) C5A C1A C2A C3A -11.8(3) C10A C1A C2A C3A 166.3(3) C2A C1A C5A C4A -13.4(3) C2A C1A C5A C6A -139.6(2) C10A C1A C5A C4A 168.7(3) C10A C1A C5A C6A 42.5(4) C2A C1A C10A C9A -175.4(3) C2A C1A C10A C14A 1.7(4) C5A C1A C10A C9A 2.3(5) C5A C1A C10A C14A 179.4(3) C1A C2A C3A C4A 33.4(3) C2A C3A C4A O3A -158.5(2) C2A C3A C4A C5A -41.3(3) C2A C3A C4A C15A 79.4(3) O3A C4A C5A C1A 147.6(2) O3A C4A C5A C6A -87.8(3) C3A C4A C5A C1A 33.2(3) C3A C4A C5A C6A 157.7(2) C15A C4A C5A C1A -86.4(2) C15A C4A C5A C6A 38.1(3) C1A C5A C6A O1A 172.6(2) C1A C5A C6A C7A -70.6(3) C4A C5A C6A O1A 52.5(3) C4A C5A C6A C7A 169.4(2) O1A C6A C7A C8A -159.6(2) O1A C6A C7A C11A -34.3(2) C5A C6A C7A C8A 79.8(3) C5A C6A C7A C11A -154.9(2) C6A C7A C8A C9A -71.5(3) C11A C7A C8A C9A 170.9(2) C6A C7A C11A C12A 32.6(3) C6A C7A C11A C13A 157.1(2) C8A C7A C11A C12A 155.9(2) C8A C7A C11A C13A -79.6(3) C7A C8A C9A C10A 64.9(4) C8A C9A C10A C1A -46.2(5) C8A C9A C10A C14A 136.6(3) C7A C11A C12A O1A -20.0(3) C7A C11A C12A O2A 159.5(3) C13A C11A C12A O1A -146.6(2) C13A C11A C12A O2A 32.9(4) C12B O1B C6B C5B 151.0(2) C12B O1B C6B C7B 26.3(3) C6B O1B C12B O2B 176.2(3) C6B O1B C12B C11B -3.8(3) H3OB O3B C4B C5B 179(2) C5B C1B C2B C3B -16.7(3) C10B C1B C2B C3B 158.3(3) C2B C1B C5B C4B -7.9(3) C2B C1B C5B C6B -134.7(2) C10B C1B C5B C4B 177.3(3) C10B C1B C5B C6B 50.5(4) C2B C1B C10B C9B -172.4(3) C2B C1B C10B C14B 1.6(5) C5B C1B C10B C9B 1.7(5) C5B C1B C10B C14B 175.7(3) C1B C2B C3B C4B 35.6(3) C2B C3B C4B O3B -154.8(2) C2B C3B C4B C5B -40.4(3) C2B C3B C4B C15B 82.6(3) O3B C4B C5B C1B 146.0(2) O3B C4B C5B C6B -89.5(3) C3B C4B C5B C1B 29.3(3) C3B C4B C5B C6B 153.8(2) C15B C4B C5B C1B -91.4(3) C15B C4B C5B C6B 33.1(3) C1B C5B C6B O1B 169.9(2) C1B C5B C6B C7B -73.2(3) C4B C5B C6B O1B 49.7(3) C4B C5B C6B C7B 166.7(2) O1B C6B C7B C8B -164.7(2) O1B C6B C7B C11B -37.4(2) C5B C6B C7B C8B 73.9(3) C5B C6B C7B C11B -158.7(2) C6B C7B C8B C9B -68.5(3) C11B C7B C8B C9B 172.5(2) C6B C7B C11B C12B 34.4(3) C6B C7B C11B C13B 158.2(2) C8B C7B C11B C12B 160.3(2) C8B C7B C11B C13B -75.9(3) C7B C8B C9B C10B 71.0(3) C8B C9B C10B C1B -54.6(4) C8B C9B C10B C14B 131.0(3) C7B C11B C12B O1B -20.2(3) C7B C11B C12B O2B 159.9(4) C13B C11B C12B O1B -146.7(3) C13B C11B C12B O2B 33.3(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054892