#------------------------------------------------------------------------------ #$Date: 2016-02-14 04:40:26 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003302.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_2003302 loop_ _publ_author_name 'Hooft, R. W. W.' 'Kroon, J.' _publ_contact_author ; Rob W. W. Hooft EMBL Meyerhofstr. 1 D-69117 Heidelberg B.R.D ; _publ_section_title 3'-Methoxyspiro[bicyclo[3.1.0]hexane-6,16'-estra-1',3',5'(10')-trien]-17'-one _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 721 _journal_page_last 723 _journal_paper_doi 10.1107/S0108270194008899 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C24 H30 O2' _chemical_formula_structural 'C24 H30 O2' _chemical_formula_sum 'C24 H30 O2' _chemical_formula_weight 350.50 _chemical_name_systematic ;3'-methoxy spiro [bicyclo[3.1.0] hexane-6,16'-estra [1,3,5(10)] triene]-17'-one ; _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 'PLATON option' _cell_angle_alpha 90 _cell_angle_beta 93.473(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.6532(6) _cell_length_b 7.1539(4) _cell_length_c 20.3786(13) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.20 _cell_measurement_theta_min 12.47 _cell_volume 968.17(12) _computing_cell_refinement 'SET4 (Boer & Duisenberg, 1984)' _computing_data_collection 'ARGUS (Schreurs & Duisenberg, unpublished)' _computing_data_reduction 'HELENA (Spek, 1993)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material ' PLATON93 (Spek, 1990). User interface software: S (Spek, 1994)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf Nonius CAD-4F' _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_radiation_monochromator 'Ni filter' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 4773 _diffrn_reflns_reduction_process ; Data were averaged ; _diffrn_reflns_theta_max 74.99 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.54 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_T_min 0.662 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'ABSORB by Spek, A.L.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.202 _exptl_crystal_description plate-like _exptl_crystal_F_000 380 _exptl_crystal_size_max 1.25 _exptl_crystal_size_mid 0.85 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.16 _refine_diff_density_min -0.11 _refine_ls_abs_structure_details ; The absolute structure was selected to comply with the known chirality ; _refine_ls_goodness_of_fit_obs 0.18 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 326 _refine_ls_number_reflns 2128 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.030 _refine_ls_shift/esd_max 0.02 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ' Calculated weights (McCandlish, Stout & Andrews,1975) with p = 0.02' _refine_ls_wR_factor_obs 0.034 _reflns_number_observed 2128 _reflns_number_total 2160 _reflns_observed_criterion >2.5sigma(I) _cod_data_source_file ab1170.cif _cod_data_source_block org34146 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_Hall 'P 2y1' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2003302 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O3 0.0536(7) 0.0040(7) 0.0194(5) 0.0595(8) 0.0003(7) 0.0515(6) O17 0.0480(7) -0.0156(7) 0.0221(7) 0.0597(9) -0.0080(8) 0.0923(10) C1 0.0524(10) -0.0092(9) 0.0113(7) 0.0567(11) -0.0163(9) 0.0513(9) C2 0.0587(10) -0.0002(10) 0.0102(7) 0.0599(11) -0.0133(8) 0.0443(8) C3 0.0427(8) 0.0073(7) 0.0062(6) 0.0532(10) 0.0049(7) 0.0350(7) C4 0.0440(8) 0.0020(7) 0.0061(6) 0.0420(8) 0.0035(7) 0.0428(7) C5 0.0410(7) 0.0036(7) 0.0047(6) 0.0392(7) 0.0028(6) 0.0373(6) C6 0.0508(9) -0.0053(7) 0.0179(7) 0.0392(9) -0.0054(7) 0.0548(9) C7 0.0489(9) 0.0008(7) 0.0170(7) 0.0342(8) -0.0006(7) 0.0546(9) C8 0.0383(7) -0.0007(6) 0.0047(6) 0.0339(7) 0.0002(6) 0.0382(7) C9 0.0390(8) -0.0001(7) 0.0021(6) 0.0413(8) -0.0030(6) 0.0389(7) C10 0.0410(8) 0.0004(7) 0.0010(6) 0.0436(9) -0.0020(6) 0.0361(7) C11 0.0542(10) -0.0090(9) 0.0152(8) 0.0433(9) -0.0130(8) 0.0591(10) C12 0.0471(9) -0.0096(8) 0.0082(7) 0.0445(10) -0.0071(8) 0.0583(9) C13 0.0350(7) -0.0023(7) 0.0046(6) 0.0381(8) 0.0030(6) 0.0464(7) C14 0.0393(8) 0.0000(7) 0.0067(6) 0.0376(8) 0.0010(7) 0.0401(7) C15 0.0501(10) -0.0070(8) 0.0178(7) 0.0460(9) -0.0068(8) 0.0493(8) C16 0.0417(8) -0.0037(8) 0.0100(6) 0.0506(9) 0.0005(8) 0.0434(7) C17 0.0385(8) -0.0032(7) 0.0052(6) 0.0459(9) 0.0049(8) 0.0516(8) C18 0.0446(9) 0.0024(9) 0.0036(8) 0.0512(11) 0.0176(9) 0.0616(10) C19 0.0771(14) 0.0088(12) 0.0355(12) 0.0666(14) -0.0032(11) 0.0669(12) C20 0.0533(10) -0.0132(10) 0.0092(7) 0.0703(13) 0.0050(9) 0.0415(8) C21 0.0736(14) -0.0232(14) 0.0032(9) 0.101(2) -0.0063(11) 0.0456(9) C22 0.0811(15) -0.0212(14) 0.0272(11) 0.0799(16) -0.0240(12) 0.0600(11) C23 0.0751(15) 0.0071(12) 0.0202(11) 0.0701(14) -0.0163(12) 0.0662(12) C24 0.0450(9) -0.0023(9) 0.0107(7) 0.0652(11) -0.0077(9) 0.0457(8) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O3 1 1.3279(2) 0.38260 0.03044(6) 0.0542(4) Uani O17 1 0.0740(2) 0.0902(3) 0.32949(8) 0.0659(5) Uani C1 1 0.8731(3) 0.1739(4) 0.09316(9) 0.0531(6) Uani C2 1 1.0412(3) 0.1914(4) 0.05617(8) 0.0540(6) Uani C3 1 1.1596(3) 0.3482(3) 0.06438(7) 0.0435(5) Uani C4 1 1.1116(3) 0.4835(3) 0.10969(8) 0.0428(4) Uani C5 1 0.9438(3) 0.4651(3) 0.14706(7) 0.0391(4) Uani C6 1 0.9069(3) 0.6141(3) 0.19784(9) 0.0477(5) Uani C7 1 0.6986(3) 0.6023(3) 0.22493(9) 0.0453(5) Uani C8 1 0.6452(2) 0.4002(3) 0.24049(7) 0.0367(4) Uani C9 1 0.6295(3) 0.2874(3) 0.17588(8) 0.0397(4) Uani C10 1 0.8200(2) 0.3071(3) 0.13878(7) 0.0403(5) Uani C11 1 0.5679(3) 0.0833(3) 0.18689(10) 0.0517(6) Uani C12 1 0.3762(3) 0.0643(4) 0.22528(9) 0.0498(5) Uani C13 1 0.4000(2) 0.1750(3) 0.28894(8) 0.0397(4) Uani C14 1 0.4471(2) 0.3796(3) 0.27334(7) 0.0388(4) Uani C15 1 0.4104(3) 0.4873(4) 0.33683(9) 0.0479(5) Uani C16 1 0.2348(3) 0.3800(4) 0.36391(7) 0.0449(5) Uani C17 1 0.2137(2) 0.1992(3) 0.32745(8) 0.0452(5) Uani C18 1 0.5568(3) 0.0840(4) 0.33795(10) 0.0525(6) Uani C19 1 1.3937(4) 0.2395(5) -0.01082(12) 0.0689(8) Uani C20 1 0.1855(3) 0.3681(4) 0.43600(8) 0.0548(6) Uani C21 1 0.2735(4) 0.5146(5) 0.48256(10) 0.0734(9) Uani C22 1 0.2168(4) 0.7029(5) 0.45177(11) 0.0727(8) Uani C23 1 0.0350(4) 0.6674(5) 0.40359(12) 0.0698(8) Uani C24 1 0.0411(3) 0.4619(4) 0.38802(8) 0.0516(5) Uani H1 1 0.795(3) 0.061(4) 0.0882(11) 0.0639(12) Uiso H2 1 1.067(3) 0.093(4) 0.0272(10) 0.0639(12) Uiso H4 1 1.202(3) 0.598(4) 0.1149(11) 0.0639(12) Uiso H8 1 0.761(3) 0.347(4) 0.2709(11) 0.0639(12) Uiso H9 1 0.522(4) 0.344(4) 0.1462(11) 0.0639(12) Uiso H14 1 0.342(4) 0.415(4) 0.2404(12) 0.0639(12) Uiso H20 1 0.157(3) 0.238(4) 0.4522(11) 0.0639(12) Uiso H24 1 -0.084(4) 0.397(4) 0.3737(12) 0.0639(12) Uiso H61 1 1.012(3) 0.598(4) 0.2356(11) 0.0639(12) Uiso H62 1 0.937(3) 0.737(4) 0.1765(11) 0.0639(12) Uiso H71 1 0.707(3) 0.684(4) 0.2668(11) 0.0639(12) Uiso H72 1 0.595(4) 0.648(4) 0.1894(12) 0.0639(12) Uiso H111 1 0.538(4) 0.022(4) 0.1439(11) 0.0639(12) Uiso H112 1 0.679(4) 0.012(4) 0.2109(11) 0.0639(12) Uiso H121 1 0.259(3) 0.113(4) 0.1988(11) 0.0639(12) Uiso H122 1 0.351(4) -0.071(4) 0.2334(12) 0.0639(12) Uiso H151 1 0.535(4) 0.476(4) 0.3686(11) 0.0639(12) Uiso H152 1 0.370(3) 0.615(4) 0.3281(11) 0.0639(12) Uiso H181 1 0.566(3) 0.157(4) 0.3799(12) 0.0639(12) Uiso H182 1 0.690(3) 0.079(4) 0.3191(10) 0.0639(12) Uiso H183 1 0.514(4) -0.047(4) 0.3487(11) 0.0639(12) Uiso H191 1 1.414(4) 0.130(4) 0.0121(12) 0.0639(12) Uiso H192 1 1.507(4) 0.284(4) -0.0314(11) 0.0639(12) Uiso H193 1 1.292(4) 0.207(4) -0.0457(11) 0.0639(12) Uiso H211 1 0.221(3) 0.488(4) 0.5283(11) 0.0639(12) Uiso H212 1 0.425(3) 0.491(4) 0.4898(11) 0.0639(12) Uiso H221 1 0.335(4) 0.753(4) 0.4283(11) 0.0639(12) Uiso H222 1 0.186(4) 0.808(4) 0.4842(11) 0.0639(12) Uiso H231 1 0.048(4) 0.744(4) 0.3648(12) 0.0639(12) Uiso H232 1 -0.088(3) 0.693(4) 0.4265(11) 0.0639(12) Uiso loop_ _atom_type_symbol _atom_type_scat_source O 'International Tables (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4' H 'International Tables (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4' C 'International Tables (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 2 1 2 -5 -4 1 2 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 C3 O3 C19 117.51(16) yes C2 C1 C10 123.0(2) yes C1 C2 C3 118.7(2) yes O3 C3 C2 124.29(16) yes O3 C3 C4 115.94(17) yes C2 C3 C4 119.77(18) yes C3 C4 C5 121.41(19) yes C4 C5 C6 118.31(18) yes C4 C5 C10 119.59(17) yes C6 C5 C10 122.04(16) yes C5 C6 C7 113.36(17) yes C6 C7 C8 110.83(16) yes C7 C8 C9 108.83(14) yes C7 C8 C14 113.70(16) yes C9 C8 C14 108.02(14) yes C8 C9 C10 111.13(15) yes C8 C9 C11 112.17(15) yes C10 C9 C11 113.47(17) yes C1 C10 C5 117.46(15) yes C1 C10 C9 121.43(18) yes C5 C10 C9 121.05(16) yes C9 C11 C12 113.20(18) yes C11 C12 C13 109.91(17) yes C12 C13 C14 109.41(15) yes C12 C13 C17 117.06(14) yes C12 C13 C18 111.34(18) yes C14 C13 C17 100.48(15) yes C14 C13 C18 113.44(15) yes C17 C13 C18 104.76(14) yes C8 C14 C13 112.14(15) yes C8 C14 C15 120.51(15) yes C13 C14 C15 105.00(15) yes C14 C15 C16 102.47(18) yes C15 C16 C17 107.82(16) yes C15 C16 C20 126.07(18) yes C15 C16 C24 127.1(2) yes C17 C16 C20 114.3(2) yes C17 C16 C24 115.94(18) yes C20 C16 C24 58.40(13) yes O17 C17 C13 126.51(19) yes O17 C17 C16 125.96(16) yes C13 C17 C16 107.52(15) yes C16 C20 C21 118.0(2) yes C16 C20 C24 60.70(13) yes C21 C20 C24 108.1(2) yes C20 C21 C22 106.16(19) yes C21 C22 C23 106.5(3) yes C22 C23 C24 105.5(2) yes C16 C24 C20 60.90(13) yes C16 C24 C23 118.5(2) yes C20 C24 C23 109.05(19) yes C2 C1 H1 117.7(13) no C10 C1 H1 119.2(13) no C1 C2 H2 117.1(14) no C3 C2 H2 124.2(14) no C3 C4 H4 118.2(13) no C5 C4 H4 120.4(13) no C5 C6 H61 107.8(15) no C5 C6 H62 105.9(14) no C7 C6 H61 108.6(12) no C7 C6 H62 114.4(12) no H61 C6 H62 106(2) no C6 C7 H71 105.2(12) no C6 C7 H72 108.3(15) no C8 C7 H71 111.5(15) no C8 C7 H72 107.1(16) no H71 C7 H72 114(2) no C7 C8 H8 107.4(15) no C9 C8 H8 109.2(14) no C14 C8 H8 109.6(12) no C8 C9 H9 108.4(15) no C10 C9 H9 104.5(14) no C11 C9 H9 106.7(16) no C9 C11 H111 109.5(16) no C9 C11 H112 111.1(16) no C12 C11 H111 106.4(15) no C12 C11 H112 108.4(14) no H111 C11 H112 108(2) no C11 C12 H121 110.0(13) no C11 C12 H122 108.8(15) no C13 C12 H121 108.8(15) no C13 C12 H122 111.9(14) no H121 C12 H122 107(2) no C8 C14 H14 106.1(15) no C13 C14 H14 104.1(17) no C15 C14 H14 107.8(16) no C14 C15 H151 109.2(14) no C14 C15 H152 112.1(13) no C16 C15 H151 109.8(15) no C16 C15 H152 109.3(12) no H151 C15 H152 113(2) no C13 C18 H181 109.7(14) no C13 C18 H182 110.5(13) no C13 C18 H183 110.1(14) no H181 C18 H182 110.0(18) no H181 C18 H183 108(2) no H182 C18 H183 109(2) no O3 C19 H191 110.9(16) no O3 C19 H192 107.8(17) no O3 C19 H193 112.3(16) no H191 C19 H192 115(2) no H191 C19 H193 104(2) no H192 C19 H193 107(2) no C16 C20 H20 114.9(13) no C21 C20 H20 120.6(13) no C24 C20 H20 120.3(12) no C20 C21 H211 107.5(15) no C20 C21 H212 108.5(15) no C22 C21 H211 116.5(15) no C22 C21 H212 115.0(16) no H211 C21 H212 102.9(17) no C21 C22 H221 109.2(16) no C21 C22 H222 115.8(14) no C23 C22 H221 111.2(13) no C23 C22 H222 110.6(15) no H221 C22 H222 104(2) no C22 C23 H231 108.8(16) no C22 C23 H232 108.2(13) no C24 C23 H231 112.0(16) no C24 C23 H232 108.4(17) no H231 C23 H232 114(2) no C16 C24 H24 116.1(16) no C20 C24 H24 118.9(16) no C23 C24 H24 119.4(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O3 C3 1.374(2) yes O3 C19 1.411(3) yes O17 C17 1.216(2) yes C1 C2 1.392(3) yes C1 C10 1.392(3) yes C2 C3 1.375(3) yes C3 C4 1.388(3) yes C4 C5 1.395(3) yes C5 C6 1.516(3) yes C5 C10 1.403(3) yes C6 C7 1.525(3) yes C7 C8 1.527(3) yes C8 C9 1.542(2) yes C8 C14 1.5211(19) yes C9 C10 1.521(2) yes C9 C11 1.537(3) yes C11 C12 1.542(3) yes C12 C13 1.520(3) yes C13 C14 1.534(3) yes C13 C17 1.517(2) yes C13 C18 1.544(3) yes C14 C15 1.538(3) yes C15 C16 1.529(3) yes C16 C17 1.494(3) yes C16 C20 1.527(2) yes C16 C24 1.524(3) yes C20 C21 1.508(4) yes C20 C24 1.488(3) yes C21 C22 1.524(5) yes C22 C23 1.532(4) yes C23 C24 1.505(5) yes C1 H1 0.96(3) no C2 H2 0.94(3) no C4 H4 1.02(3) no C6 H61 1.01(2) no C6 H62 1.01(3) no C7 H71 1.03(2) no C7 H72 1.02(3) no C8 H8 1.03(2) no C9 H9 0.99(3) no C11 H111 0.99(2) no C11 H112 1.00(3) no C12 H121 0.98(2) no C12 H122 1.00(3) no C14 H14 0.97(3) no C15 H151 1.02(3) no C15 H152 0.97(3) no C18 H181 1.00(3) no C18 H182 0.99(2) no C18 H183 1.01(3) no C19 H191 0.92(3) no C19 H192 0.94(3) no C19 H193 0.98(2) no C20 H20 1.01(3) no C21 H211 1.03(2) no C21 H212 1.02(2) no C22 H221 1.01(3) no C22 H222 1.03(3) no C23 H231 0.97(3) no C23 H232 0.98(2) no C24 H24 0.98(3) no 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 C19 O3 C3 C2 -6.3(3) no C19 O3 C3 C4 173.39(18) no C10 C1 C2 C3 -0.7(3) no C2 C1 C10 C5 0.0(11) no C2 C1 C10 C9 177.02(19) no C1 C2 C3 O3 -179.36(18) no C1 C2 C3 C4 1.0(3) no O3 C3 C4 C5 179.75(15) no C2 C3 C4 C5 -0.6(3) no C3 C4 C5 C6 177.11(17) no C3 C4 C5 C10 -0.2(3) no C4 C5 C6 C7 167.68(17) no C10 C5 C6 C7 -15.1(3) no C4 C5 C10 C1 0.5(3) no C4 C5 C10 C9 -176.59(16) no C6 C5 C10 C1 -176.73(17) no C6 C5 C10 C9 6.2(3) no C5 C6 C7 C8 44.1(2) no C6 C7 C8 C9 -64.64(18) no C6 C7 C8 C14 174.92(13) no C7 C8 C9 C10 54.02(19) no C7 C8 C9 C11 -177.78(15) no C14 C8 C9 C10 177.90(16) no C14 C8 C9 C11 -53.9(2) no C7 C8 C14 C13 -179.30(13) no C7 C8 C14 C15 -55.0(2) no C9 C8 C14 C13 59.81(17) no C9 C8 C14 C15 -175.86(18) no C8 C9 C10 C1 157.19(17) no C8 C9 C10 C5 -25.9(2) no C11 C9 C10 C1 29.7(2) no C11 C9 C10 C5 -153.38(16) no C8 C9 C11 C12 52.3(2) no C10 C9 C11 C12 179.28(15) no C9 C11 C12 C13 -53.1(2) no C11 C12 C13 C14 56.6(2) no C11 C12 C13 C17 169.98(18) no C11 C12 C13 C18 -69.6(2) no C12 C13 C14 C8 -62.59(16) no C12 C13 C14 C15 164.84(14) no C17 C13 C14 C8 173.64(12) no C17 C13 C14 C15 41.08(15) no C18 C13 C14 C8 62.38(18) no C18 C13 C14 C15 -70.18(17) no C12 C13 C17 O17 30.6(3) no C12 C13 C17 C16 -150.67(18) no C14 C13 C17 O17 148.91(19) no C14 C13 C17 C16 -32.38(16) no C18 C13 C17 O17 -93.2(2) no C18 C13 C17 C16 85.5(2) no C8 C14 C15 C16 -161.86(17) no C13 C14 C15 C16 -34.22(18) no C14 C15 C16 C17 13.7(2) no C14 C15 C16 C20 153.9(2) no C14 C15 C16 C24 -131.30(18) no C15 C16 C17 O17 -169.30(19) no C15 C16 C17 C13 12.0(2) no C20 C16 C17 O17 45.3(3) no C20 C16 C17 C13 -133.44(17) no C24 C16 C17 O17 -19.9(3) no C24 C16 C17 C13 161.39(15) no C15 C16 C20 C21 19.3(4) no C15 C16 C20 C24 115.3(3) no C17 C16 C20 C21 157.3(2) no C17 C16 C20 C24 -106.6(2) no C24 C16 C20 C21 -96.0(3) no C15 C16 C24 C20 -113.7(2) no C15 C16 C24 C23 -16.6(3) no C17 C16 C24 C20 103.7(2) no C17 C16 C24 C23 -159.22(18) no C20 C16 C24 C23 97.0(2) no C16 C20 C21 C22 52.7(3) no C24 C20 C21 C22 -13.1(2) no C16 C20 C24 C23 -112.7(2) no C21 C20 C24 C16 112.5(2) no C21 C20 C24 C23 -0.2(2) no C20 C21 C22 C23 21.2(2) no C21 C22 C23 C24 -21.2(2) no C22 C23 C24 C16 -53.2(2) no C22 C23 C24 C20 13.4(2) no