#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014724.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_2014724 loop_ _publ_author_name 'Andrade, L. C. R.' 'Paix\~ao, J. A.' 'de Almeida, M. J. M.' 'Fernandes Roleira, F. M.' 'Tavares da Silva, E. J.' _publ_section_title ; 17-Oxo-5\a-androstane-3\a,4\b-diyl diacetate and 17-oxo-5\b-androstane-3\a,4\b-diyl diacetate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o131 _journal_page_last o133 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C23 H34 O5' _chemical_formula_moiety 'C23 H34 O5' _chemical_formula_sum 'C23 H34 O5' _chemical_formula_weight 390.50 _chemical_name_systematic ; 17-Oxo-5\b-androstane-3\a,4\b-diyl diacetate ; _space_group_IT_number 170 _symmetry_cell_setting hexagonal _symmetry_space_group_name_Hall 'P 65' _symmetry_space_group_name_H-M 'P 65' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_formula_units_Z 6 _cell_length_a 22.885(3) _cell_length_b 22.885(4) _cell_length_c 7.9582(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18.46 _cell_measurement_theta_min 8.81 _cell_volume 3609.5(10) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w--2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 7826 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% 6.5 _diffrn_standards_interval_time 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.078 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1272 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.185 _refine_diff_density_min -0.160 _refine_ls_extinction_coef 0.0041(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 2953 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.870 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0463 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0825P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1184 _refine_ls_wR_factor_ref 0.1398 _reflns_number_gt 1369 _reflns_number_total 2953 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1786.cif _[local]_cod_data_source_block II _cod_original_cell_volume 3609.4(9) _cod_database_code 2014724 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z-1/6' '-y, x-y, z-1/3' '-x, -y, z-1/2' '-x+y, -x, z+1/3' 'y, -x+y, z+1/6' 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_type_symbol O3 0.08172(11) 0.25266(11) 0.2307(4) 0.0668(8) Uani d . 1 O O4 0.12401(11) 0.35112(11) -0.0174(4) 0.0627(7) Uani d . 1 O O17 -0.31483(14) 0.23121(19) 0.1126(5) 0.1158(12) Uani d . 1 O O20 0.18538(16) 0.29103(17) 0.3172(7) 0.1378(18) Uani d . 1 O O22 0.05760(16) 0.26578(17) -0.1883(4) 0.0990(10) Uani d . 1 O C1 0.0375(2) 0.3760(2) 0.4114(6) 0.0788(12) Uani d . 1 C H1A 0.0828 0.4100 0.4443 0.095 Uiso calc R 1 H H1B 0.0072 0.3725 0.5010 0.095 Uiso calc R 1 H C2 0.0351(2) 0.3081(2) 0.3946(5) 0.0717(11) Uani d . 1 C H2A 0.0471 0.2958 0.5003 0.086 Uiso calc R 1 H H2B -0.0100 0.2730 0.3634 0.086 Uiso calc R 1 H C3 0.08484(17) 0.31670(16) 0.2603(5) 0.0573(10) Uani d . 1 C H3 0.1305 0.3504 0.2961 0.069 Uiso calc R 1 H C4 0.06884(16) 0.33755(16) 0.0952(5) 0.0504(9) Uani d . 1 C H4 0.0264 0.3010 0.0502 0.061 Uiso calc R 1 H C5 0.06531(16) 0.40238(15) 0.1082(5) 0.0542(9) Uani d . 1 C H5 0.1108 0.4387 0.1364 0.065 Uiso calc R 1 H C6 0.04707(17) 0.42064(18) -0.0605(5) 0.0662(11) Uani d . 1 C H6A 0.0563 0.4669 -0.0563 0.079 Uiso calc R 1 H H6B 0.0753 0.4179 -0.1475 0.079 Uiso calc R 1 H C7 -0.02616(17) 0.37473(18) -0.1059(5) 0.0580(9) Uani d . 1 C H7A -0.0338 0.3296 -0.1255 0.070 Uiso calc R 1 H H7B -0.0359 0.3904 -0.2097 0.070 Uiso calc R 1 H C8 -0.07444(15) 0.37179(15) 0.0302(4) 0.0471(8) Uani d . 1 C H8 -0.0691 0.4168 0.0416 0.057 Uiso calc R 1 H C9 -0.05700(15) 0.35191(15) 0.2007(4) 0.0486(8) Uani d . 1 C H9 -0.0615 0.3075 0.1834 0.058 Uiso calc R 1 H C10 0.01821(18) 0.39998(16) 0.2502(5) 0.0577(10) Uani d . 1 C C11 -0.10806(19) 0.3422(2) 0.3384(5) 0.0671(11) Uani d . 1 C H11A -0.0984 0.3239 0.4376 0.081 Uiso calc R 1 H H11B -0.1023 0.3858 0.3680 0.081 Uiso calc R 1 H C12 -0.18131(18) 0.2955(2) 0.2876(6) 0.0703(11) Uani d . 1 C H12A -0.1894 0.2499 0.2742 0.084 Uiso calc R 1 H H12B -0.2109 0.2950 0.3755 0.084 Uiso calc R 1 H C13 -0.19691(17) 0.31856(18) 0.1262(5) 0.0594(9) Uani d . 1 C C14 -0.14760(16) 0.32248(16) -0.0104(4) 0.0505(8) Uani d . 1 C H14 -0.1515 0.2778 -0.0129 0.061 Uiso calc R 1 H C15 -0.17840(19) 0.3285(2) -0.1740(5) 0.0661(11) Uani d . 1 C H15A -0.1620 0.3143 -0.2691 0.079 Uiso calc R 1 H H15B -0.1689 0.3743 -0.1924 0.079 Uiso calc R 1 H C16 -0.2551(2) 0.2795(2) -0.1439(7) 0.0861(14) Uani d . 1 C H16A -0.2816 0.2985 -0.1877 0.103 Uiso calc R 1 H H16B -0.2697 0.2364 -0.1983 0.103 Uiso calc R 1 H C17 -0.2630(2) 0.2710(2) 0.0429(6) 0.0732(12) Uani d . 1 C C18 -0.1973(2) 0.3857(2) 0.1485(7) 0.0837(13) Uani d . 1 C H18A -0.1537 0.4203 0.1859 0.126 Uiso calc R 1 H H18B -0.2307 0.3796 0.2303 0.126 Uiso calc R 1 H H18C -0.2078 0.3987 0.0430 0.126 Uiso calc R 1 H C19 0.0318(2) 0.47211(18) 0.2829(8) 0.0966(17) Uani d . 1 C H19A 0.0180 0.4876 0.1868 0.145 Uiso calc R 1 H H19B 0.0791 0.5016 0.3025 0.145 Uiso calc R 1 H H19C 0.0067 0.4721 0.3797 0.145 Uiso calc R 1 H C20 0.13576(19) 0.2479(2) 0.2602(7) 0.0809(14) Uani d . 1 C C21 0.1253(2) 0.1802(2) 0.2039(9) 0.111(2) Uani d . 1 C H21A 0.0842 0.1448 0.2512 0.167 Uiso calc R 1 H H21B 0.1625 0.1753 0.2413 0.167 Uiso calc R 1 H H21C 0.1227 0.1775 0.0835 0.167 Uiso calc R 1 H C22 0.1128(2) 0.3105(2) -0.1460(6) 0.0728(11) Uani d . 1 C C23 0.1771(3) 0.3281(3) -0.2352(8) 0.126(2) Uani d . 1 C H23A 0.2064 0.3762 -0.2342 0.189 Uiso calc R 1 H H23B 0.1673 0.3125 -0.3493 0.189 Uiso calc R 1 H H23C 0.1989 0.3070 -0.1794 0.189 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 O3 0.0515(13) 0.0587(13) 0.096(2) 0.0322(11) -0.0187(13) -0.0035(14) O4 0.0515(13) 0.0682(15) 0.0676(17) 0.0294(12) 0.0071(13) -0.0090(15) O17 0.0577(16) 0.127(3) 0.128(3) 0.0207(18) 0.025(2) 0.014(3) O20 0.074(2) 0.098(2) 0.245(5) 0.0457(19) -0.073(3) -0.032(3) O22 0.090(2) 0.112(2) 0.071(2) 0.0321(19) -0.0024(19) -0.029(2) C1 0.076(2) 0.111(3) 0.061(3) 0.056(2) -0.010(2) -0.031(3) C2 0.074(2) 0.098(3) 0.051(3) 0.049(2) -0.007(2) 0.008(2) C3 0.0490(19) 0.0510(19) 0.068(3) 0.0221(15) -0.009(2) -0.0051(19) C4 0.0466(17) 0.0491(17) 0.059(2) 0.0263(15) -0.0023(17) -0.0062(18) C5 0.0487(17) 0.0406(17) 0.071(3) 0.0205(15) -0.0036(19) -0.0078(18) C6 0.063(2) 0.059(2) 0.081(3) 0.0346(18) 0.018(2) 0.023(2) C7 0.064(2) 0.073(2) 0.050(2) 0.0430(19) 0.0133(19) 0.0141(19) C8 0.062(2) 0.0435(17) 0.046(2) 0.0337(16) 0.0073(17) 0.0064(16) C9 0.0545(19) 0.0466(17) 0.050(2) 0.0292(15) 0.0043(17) -0.0010(17) C10 0.064(2) 0.0545(19) 0.058(2) 0.0324(17) -0.009(2) -0.0180(19) C11 0.082(3) 0.083(3) 0.050(3) 0.052(2) 0.011(2) 0.001(2) C12 0.065(2) 0.081(3) 0.064(3) 0.035(2) 0.019(2) 0.012(2) C13 0.057(2) 0.068(2) 0.063(3) 0.0381(18) 0.009(2) 0.007(2) C14 0.0545(18) 0.0503(18) 0.052(2) 0.0304(15) 0.0071(17) 0.0080(17) C15 0.070(2) 0.083(3) 0.059(3) 0.048(2) -0.002(2) 0.003(2) C16 0.068(3) 0.092(3) 0.097(4) 0.039(2) -0.013(3) -0.005(3) C17 0.060(2) 0.086(3) 0.078(3) 0.040(2) 0.010(2) 0.008(2) C18 0.094(3) 0.093(3) 0.092(3) 0.068(3) 0.006(3) -0.003(3) C19 0.089(3) 0.059(2) 0.143(5) 0.038(2) -0.002(3) -0.038(3) C20 0.049(2) 0.066(2) 0.124(4) 0.027(2) -0.013(3) 0.009(3) C21 0.093(3) 0.082(3) 0.181(6) 0.060(3) -0.021(4) -0.001(4) C22 0.077(3) 0.089(3) 0.058(3) 0.046(2) 0.010(2) 0.000(3) C23 0.103(4) 0.183(5) 0.093(4) 0.073(4) 0.034(4) -0.022(4) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C20 O3 C3 118.8(3) C22 O4 C4 119.2(3) C2 C1 C10 114.6(3) 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 C3 C2 C1 106.8(3) C3 C2 H2A 110.4 C1 C2 H2A 110.4 C3 C2 H2B 110.4 C1 C2 H2B 110.4 H2A C2 H2B 108.6 O3 C3 C2 109.4(3) O3 C3 C4 106.4(3) C2 C3 C4 112.0(3) O3 C3 H3 109.7 C2 C3 H3 109.7 C4 C3 H3 109.7 O4 C4 C3 106.5(3) O4 C4 C5 107.3(3) C3 C4 C5 112.8(3) O4 C4 H4 110.1 C3 C4 H4 110.1 C5 C4 H4 110.1 C6 C5 C4 111.1(3) C6 C5 C10 111.9(3) C4 C5 C10 112.9(3) C6 C5 H5 106.8 C4 C5 H5 106.8 C10 C5 H5 106.8 C7 C6 C5 112.4(3) C7 C6 H6A 109.1 C5 C6 H6A 109.1 C7 C6 H6B 109.1 C5 C6 H6B 109.1 H6A C6 H6B 107.9 C6 C7 C8 112.8(3) C6 C7 H7A 109.0 C8 C7 H7A 109.0 C6 C7 H7B 109.0 C8 C7 H7B 109.0 H7A C7 H7B 107.8 C14 C8 C7 112.9(3) C14 C8 C9 108.7(3) C7 C8 C9 110.4(2) C14 C8 H8 108.3 C7 C8 H8 108.3 C9 C8 H8 108.3 C11 C9 C8 112.3(2) C11 C9 C10 114.5(3) C8 C9 C10 111.7(3) C11 C9 H9 105.9 C8 C9 H9 105.9 C10 C9 H9 105.9 C5 C10 C19 108.8(3) C5 C10 C1 107.6(3) C19 C10 C1 107.5(3) C5 C10 C9 110.2(3) C19 C10 C9 111.0(3) C1 C10 C9 111.7(3) C12 C11 C9 113.8(3) C12 C11 H11A 108.8 C9 C11 H11A 108.8 C12 C11 H11B 108.8 C9 C11 H11B 108.8 H11A C11 H11B 107.7 C13 C12 C11 110.7(3) C13 C12 H12A 109.5 C11 C12 H12A 109.5 C13 C12 H12B 109.5 C11 C12 H12B 109.5 H12A C12 H12B 108.1 C12 C13 C17 116.9(3) C12 C13 C14 109.2(3) C17 C13 C14 100.0(3) C12 C13 C18 111.8(4) C17 C13 C18 105.4(3) C14 C13 C18 113.0(3) C8 C14 C15 120.4(3) C8 C14 C13 113.5(3) C15 C14 C13 104.5(3) C8 C14 H14 105.8 C15 C14 H14 105.8 C13 C14 H14 105.8 C14 C15 C16 102.1(3) C14 C15 H15A 111.3 C16 C15 H15A 111.3 C14 C15 H15B 111.3 C16 C15 H15B 111.3 H15A C15 H15B 109.2 C17 C16 C15 105.3(4) C17 C16 H16A 110.7 C15 C16 H16A 110.7 C17 C16 H16B 110.7 C15 C16 H16B 110.7 H16A C16 H16B 108.8 O17 C17 C16 124.1(4) O17 C17 C13 126.5(4) C16 C17 C13 109.3(4) C13 C18 H18A 109.5 C13 C18 H18B 109.5 H18A C18 H18B 109.5 C13 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 O20 C20 O3 124.0(4) O20 C20 C21 124.9(4) O3 C20 C21 111.0(4) 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 O22 C22 O4 124.3(4) O22 C22 C23 124.5(4) O4 C22 C23 111.1(4) C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O3 C20 1.315(4) yes O3 C3 1.451(4) ? O4 C22 1.319(5) yes O4 C4 1.449(4) ? O17 C17 1.210(5) ? O20 C20 1.161(5) yes O22 C22 1.211(5) ? C1 C2 1.532(5) ? C1 C10 1.544(6) ? C1 H1A 0.9700 ? C1 H1B 0.9700 ? C2 C3 1.502(5) yes C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.505(5) ? C3 H3 0.9800 ? C4 C5 1.529(4) ? C4 H4 0.9800 ? C5 C6 1.526(5) ? C5 C10 1.544(5) ? C5 H5 0.9800 ? C6 C7 1.511(5) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.525(5) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C14 1.514(4) ? C8 C9 1.546(5) ? C8 H8 0.9800 ? C9 C11 1.534(5) ? C9 C10 1.560(5) ? C9 H9 0.9800 ? C10 C19 1.541(5) ? C11 C12 1.524(5) ? C11 H11A 0.9700 ? C11 H11B 0.9700 ? C12 C13 1.498(6) ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 C17 1.505(5) ? C13 C14 1.537(5) ? C13 C18 1.551(5) ? C14 C15 1.519(5) ? C14 H14 0.9800 ? C15 C16 1.558(6) ? C15 H15A 0.9700 ? C15 H15B 0.9700 ? C16 C17 1.499(7) ? C16 H16A 0.9700 ? C16 H16B 0.9700 ? 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 1.513(6) ? C21 H21A 0.9600 ? C21 H21B 0.9600 ? C21 H21C 0.9600 ? C22 C23 1.496(6) ? C23 H23A 0.9600 ? C23 H23B 0.9600 ? C23 H23C 0.9600 ? 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 C10 C1 C2 C3 60.8(4) C20 O3 C3 C2 -117.8(4) C20 O3 C3 C4 121.1(4) C1 C2 C3 O3 -176.3(3) C1 C2 C3 C4 -58.6(4) C22 O4 C4 C3 111.6(4) C22 O4 C4 C5 -127.4(3) O3 C3 C4 O4 -66.5(3) C2 C3 C4 O4 174.0(3) O3 C3 C4 C5 176.0(2) C2 C3 C4 C5 56.6(4) O4 C4 C5 C6 64.6(3) C3 C4 C5 C6 -178.4(3) O4 C4 C5 C10 -168.7(3) C3 C4 C5 C10 -51.8(4) C4 C5 C6 C7 73.2(4) C10 C5 C6 C7 -54.1(4) C5 C6 C7 C8 54.6(4) C6 C7 C8 C14 -176.4(3) C6 C7 C8 C9 -54.6(4) C14 C8 C9 C11 -50.6(3) C7 C8 C9 C11 -174.9(3) C14 C8 C9 C10 179.2(3) C7 C8 C9 C10 54.9(3) C6 C5 C10 C19 -68.1(4) C4 C5 C10 C19 165.7(3) C6 C5 C10 C1 175.8(3) C4 C5 C10 C1 49.6(4) C6 C5 C10 C9 53.8(3) C4 C5 C10 C9 -72.4(4) C2 C1 C10 C5 -56.2(4) C2 C1 C10 C19 -173.2(4) C2 C1 C10 C9 64.9(4) C11 C9 C10 C5 176.1(3) C8 C9 C10 C5 -54.8(3) C11 C9 C10 C19 -63.3(4) C8 C9 C10 C19 65.8(4) C11 C9 C10 C1 56.6(4) C8 C9 C10 C1 -174.3(3) C8 C9 C11 C12 50.8(4) C10 C9 C11 C12 179.6(3) C9 C11 C12 C13 -53.7(4) C11 C12 C13 C17 169.0(3) C11 C12 C13 C14 56.5(4) C11 C12 C13 C18 -69.4(4) C7 C8 C14 C15 -55.5(4) C9 C8 C14 C15 -178.3(3) C7 C8 C14 C13 179.6(3) C9 C8 C14 C13 56.8(3) C12 C13 C14 C8 -60.9(4) C17 C13 C14 C8 175.9(3) C18 C13 C14 C8 64.3(4) C12 C13 C14 C15 166.1(3) C17 C13 C14 C15 42.8(3) C18 C13 C14 C15 -68.8(4) C8 C14 C15 C16 -168.2(3) C13 C14 C15 C16 -39.2(4) C14 C15 C16 C17 19.9(4) C15 C16 C17 O17 -172.6(4) C15 C16 C17 C13 6.8(5) C12 C13 C17 O17 31.6(6) C14 C13 C17 O17 149.3(4) C18 C13 C17 O17 -93.3(5) C12 C13 C17 C16 -147.8(4) C14 C13 C17 C16 -30.1(4) C18 C13 C17 C16 87.3(4) C3 O3 C20 O20 4.2(8) C3 O3 C20 C21 -173.6(4) C4 O4 C22 O22 7.9(6) C4 O4 C22 C23 -173.5(4) C19 C10 C13 C18 0.7(4)