data_2014724 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o131 _journal_page_last o133 _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 ; 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.' _chemical_formula_moiety 'C23 H34 O5' _chemical_formula_sum 'C23 H34 O5' _chemical_formula_iupac 'C23 H34 O5' _chemical_formula_weight 390.50 _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 65' _symmetry_space_group_name_Hall 'P 65' 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' _cell_length_a 22.885(3) _cell_length_b 22.885(4) _cell_length_c 7.9582(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3609.4(9) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.078 _diffrn_ambient_temperature 293(2) 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 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_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_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 ?