#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/56/2005613.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_2005613 loop_ _publ_author_name 'Ramos Silva, M.' 'Paix\~ao, J. A.' 'de Almeida, M.-J. M.' 'Tavares da Silva, E. J.' 'S\'a e Melo, M. L.' 'Campos Neves, A. S.' _publ_contact_author ; J.A.Paix\~ao Fac. Ci\^encias e Tecnologia Departamento de F\'isica Universidade de Coimbra P-3000 Coimbra Portugal ; _publ_section_title ; 3\b,4\a-Dihydroxy-5\b-androstan-17-one ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2892 _journal_page_last 2894 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C19 H30 O3' _chemical_formula_sum 'C19 H30 O3' _chemical_formula_weight 306.43 _chemical_melting_point 494(2) _chemical_name_systematic 3\b,4\a-dihydroxy-5\b-androstan-17-one _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3280(10) _cell_length_b 13.208(2) _cell_length_c 20.069(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.85 _cell_measurement_theta_min 7.84 _cell_volume 1677.4(6) _computing_cell_refinement 'CAD-4 software (Enraf Nonius, 1989)' _computing_data_collection 'CAD-4 software (Enraf Nonius, 1989)' _computing_data_reduction 'Enraf-Nonius SDP-Plus (Frenz, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'MULTAN11/82 (Main et al., 1982)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method 'profile data from \w scans' _diffrn_radiation_monochromator 'equatorial mounted graphite' _diffrn_radiation_source 'fine focus Enraf Nonius Mo tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 6517 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 1.85 _diffrn_standards_decay_% 4.7 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_crystal_colour 'colourless; transparent' _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'good crystal quality; needle' _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.164 _refine_diff_density_min -0.143 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.004 _refine_ls_goodness_of_fit_obs 1.065 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2898 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_restrained_S_obs 1.065 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_obs 0.0424 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0364P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1204 _refine_ls_wR_factor_obs 0.0883 _reflns_number_observed 1510 _reflns_number_total 2901 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file fg1119.cif _[local]_cod_data_source_block androstan _[local]_cod_cif_authors_sg_Hall P_2ac_2ab _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '221(2)_C' was changed to '494(2)' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2005613 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol O3 1 0.4054(4) 0.6098(2) 0.47989(11) 0.0608(7) Uani d . O H3 1 0.4331(38) 0.5506(2) 0.4713(15) 0.073 Uiso calc R H O4 1 0.0482(4) 0.7286(2) 0.59497(11) 0.0587(7) Uani d . O H4 1 -0.0099(25) 0.7771(16) 0.5772(11) 0.070 Uiso calc R H O17 1 -0.0519(4) 0.5953(2) 0.95499(11) 0.0678(8) Uani d . O C1 1 0.4169(6) 0.5221(2) 0.61565(15) 0.0483(9) Uani d . C H11 1 0.5413(6) 0.5143(2) 0.58790(15) 0.058 Uiso calc R H H12 1 0.4080(6) 0.4632(2) 0.64432(15) 0.058 Uiso calc R H C2 1 0.2250(7) 0.5244(2) 0.57144(15) 0.0516(10) Uani d . C H21 1 0.0988(7) 0.5279(2) 0.59879(15) 0.062 Uiso calc R H H22 1 0.2188(7) 0.4624(2) 0.54561(15) 0.062 Uiso calc R H C3 1 0.2303(6) 0.6138(2) 0.52490(14) 0.0469(9) Uani d . C H31 1 0.0991(6) 0.6149(2) 0.49899(14) 0.056 Uiso calc R H C4 1 0.2469(6) 0.7108(2) 0.56376(15) 0.0425(8) Uani d . C H41 1 0.2718(6) 0.7659(2) 0.53200(15) 0.051 Uiso calc R H C5 1 0.4284(5) 0.7113(2) 0.61422(14) 0.0398(8) Uani d . C H51 1 0.5577(5) 0.7114(2) 0.58735(14) 0.048 Uiso calc R H C6 1 0.4353(7) 0.8099(2) 0.6541(2) 0.0598(11) Uani d . C H61 1 0.5782(7) 0.8203(2) 0.6702(2) 0.072 Uiso calc R H H62 1 0.4013(7) 0.8658(2) 0.6246(2) 0.072 Uiso calc R H C7 1 0.2844(7) 0.8120(2) 0.7131(2) 0.0577(11) Uani d . C H71 1 0.3103(7) 0.8726(2) 0.7391(2) 0.069 Uiso calc R H H72 1 0.1403(7) 0.8150(2) 0.6968(2) 0.069 Uiso calc R H C8 1 0.3086(5) 0.7198(2) 0.75779(14) 0.0411(8) Uani d . C H81 1 0.4518(5) 0.7202(2) 0.77644(14) 0.049 Uiso calc R H C9 1 0.2808(5) 0.6224(2) 0.71682(13) 0.0326(7) Uani d . C H91 1 0.1420(5) 0.6275(2) 0.69545(13) 0.039 Uiso calc R H C10 1 0.4458(5) 0.6160(2) 0.65929(13) 0.0369(7) Uani d . C C11 1 0.2746(6) 0.5259(2) 0.76022(14) 0.0453(9) Uani d . C H111 1 0.2270(6) 0.4698(2) 0.73287(14) 0.054 Uiso calc R H H112 1 0.4172(6) 0.5107(2) 0.77489(14) 0.054 Uiso calc R H C12 1 0.1323(5) 0.5332(2) 0.82120(14) 0.0439(9) Uani d . C H121 1 -0.0144(5) 0.5343(2) 0.80718(14) 0.053 Uiso calc R H H122 1 0.1531(5) 0.4741(2) 0.84913(14) 0.053 Uiso calc R H C13 1 0.1806(5) 0.6273(2) 0.86063(14) 0.0390(8) Uani d . C C14 1 0.1528(5) 0.7198(2) 0.81476(14) 0.0424(8) Uani d . C H141 1 0.0124(5) 0.7132(2) 0.79463(14) 0.051 Uiso calc R H C15 1 0.1398(7) 0.8092(2) 0.8628(2) 0.0705(13) Uani d . C H151 1 0.0713(7) 0.8669(2) 0.8421(2) 0.085 Uiso calc R H H152 1 0.2791(7) 0.8292(2) 0.8781(2) 0.085 Uiso calc R H C16 1 0.0068(8) 0.7672(2) 0.9201(2) 0.0782(14) Uani d . C H161 1 0.0568(8) 0.7931(2) 0.9624(2) 0.094 Uiso calc R H H162 1 -0.1403(8) 0.7860(2) 0.9146(2) 0.094 Uiso calc R H C17 1 0.0321(6) 0.6534(3) 0.9171(2) 0.0505(9) Uani d . C C18 1 0.3991(6) 0.6206(3) 0.8931(2) 0.0664(12) Uani d . C H181 1 0.4027(13) 0.5640(11) 0.9231(9) 0.100 Uiso calc R H H182 1 0.4271(16) 0.6818(8) 0.9174(9) 0.100 Uiso calc R H H183 1 0.5047(7) 0.6118(17) 0.8593(2) 0.100 Uiso calc R H C19 1 0.6725(5) 0.6107(3) 0.6877(2) 0.0669(11) Uani d . C H191 1 0.6947(14) 0.6661(11) 0.7178(10) 0.100 Uiso calc R H H192 1 0.7726(5) 0.6147(19) 0.6519(2) 0.100 Uiso calc R H H193 1 0.6910(13) 0.5479(9) 0.7111(11) 0.100 Uiso calc R 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 O17 0.090(2) 0.058(2) 0.0554(14) 0.006(2) 0.025(2) 0.0115(13) O3 0.094(2) 0.0437(13) 0.0449(12) -0.009(2) 0.0203(14) 0.0012(13) O4 0.053(2) 0.068(2) 0.0554(13) 0.0142(15) 0.0061(14) 0.0229(12) C1 0.064(2) 0.040(2) 0.042(2) 0.014(2) 0.013(2) 0.0074(15) C2 0.072(3) 0.042(2) 0.040(2) -0.018(2) 0.006(2) -0.001(2) C3 0.056(2) 0.048(2) 0.037(2) -0.007(2) 0.000(2) 0.006(2) C4 0.047(2) 0.040(2) 0.040(2) 0.005(2) 0.006(2) 0.011(2) C5 0.044(2) 0.034(2) 0.042(2) -0.008(2) 0.005(2) 0.0010(14) C6 0.090(3) 0.043(2) 0.047(2) -0.026(2) 0.009(2) 0.001(2) C7 0.098(3) 0.027(2) 0.048(2) -0.013(2) 0.012(2) -0.005(2) C8 0.052(2) 0.036(2) 0.035(2) -0.009(2) 0.000(2) 0.0001(15) C9 0.033(2) 0.031(2) 0.0334(15) -0.001(2) -0.0040(14) 0.0016(14) C10 0.033(2) 0.044(2) 0.034(2) 0.001(2) -0.001(2) 0.0023(15) C11 0.066(3) 0.032(2) 0.037(2) 0.008(2) 0.006(2) 0.0046(14) C12 0.060(2) 0.033(2) 0.039(2) 0.003(2) 0.005(2) 0.0034(15) C13 0.046(2) 0.041(2) 0.030(2) 0.003(2) -0.0035(15) 0.0011(15) C14 0.057(2) 0.033(2) 0.037(2) -0.001(2) 0.001(2) -0.005(2) C15 0.125(4) 0.036(2) 0.051(2) 0.000(2) 0.018(2) -0.009(2) C16 0.128(4) 0.051(2) 0.056(2) 0.012(3) 0.031(3) -0.001(2) C17 0.064(2) 0.050(2) 0.038(2) 0.005(2) 0.004(2) 0.002(2) C18 0.061(3) 0.096(3) 0.042(2) 0.006(3) -0.012(2) 0.005(2) C19 0.039(2) 0.103(3) 0.059(2) 0.009(2) 0.002(2) 0.014(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -2 4 2 1 6 -2 -1 7 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 H3 109.5(2) no C4 O4 H4 109.5(2) no C2 C1 C10 114.7(3) yes C2 C1 H11 108.6(2) no C10 C1 H11 108.6(2) no C2 C1 H12 108.6(2) no C10 C1 H12 108.6(2) no H11 C1 H12 107.6 no C1 C2 C3 111.3(3) yes C1 C2 H21 109.4(2) no C3 C2 H21 109.4(2) no C1 C2 H22 109.4(2) no C3 C2 H22 109.4(2) no H21 C2 H22 108.0 no O3 C3 C4 107.8(3) yes O3 C3 C2 112.3(3) yes C4 C3 C2 110.4(2) yes O3 C3 H31 108.8(2) no C4 C3 H31 108.8(2) no C2 C3 H31 108.8(2) no O4 C4 C3 107.9(3) yes O4 C4 C5 111.8(2) yes C3 C4 C5 113.5(3) yes O4 C4 H41 107.8(2) no C3 C4 H41 107.8(2) no C5 C4 H41 107.8(2) no C6 C5 C4 111.8(3) yes C6 C5 C10 112.5(2) yes C4 C5 C10 115.8(3) yes C6 C5 H51 105.2(2) no C4 C5 H51 105.2(2) no C10 C5 H51 105.2(2) no C7 C6 C5 113.8(3) yes C7 C6 H61 108.8(2) no C5 C6 H61 108.8(2) no C7 C6 H62 108.8(2) no C5 C6 H62 108.8(2) no H61 C6 H62 107.7 no C8 C7 C6 112.4(3) yes C8 C7 H71 109.1(2) no C6 C7 H71 109.1(2) no C8 C7 H72 109.1(2) no C6 C7 H72 109.1(2) no H71 C7 H72 107.8 no C14 C8 C7 112.4(3) yes C14 C8 C9 109.3(2) yes C7 C8 C9 110.1(2) yes C14 C8 H81 108.3(2) no C7 C8 H81 108.3(2) no C9 C8 H81 108.3(2) no C8 C9 C11 113.1(2) yes C8 C9 C10 111.4(2) yes C11 C9 C10 113.0(2) yes C8 C9 H91 106.3(2) no C11 C9 H91 106.3(2) no C10 C9 H91 106.3(2) no C1 C10 C19 106.6(3) yes C1 C10 C5 108.3(2) yes C19 C10 C5 108.6(3) yes C1 C10 C9 112.8(3) yes C19 C10 C9 110.5(2) yes C5 C10 C9 109.9(3) yes C12 C11 C9 114.6(3) yes C12 C11 H111 108.6(2) no C9 C11 H111 108.6(2) no C12 C11 H112 108.6(2) no C9 C11 H112 108.6(2) no H111 C11 H112 107.6 no C13 C12 C11 110.7(3) yes C13 C12 H121 109.5(2) no C11 C12 H121 109.5(2) no C13 C12 H122 109.5(2) no C11 C12 H122 109.5(2) no H121 C12 H122 108.1 no C12 C13 C17 117.1(3) yes C12 C13 C18 111.0(3) yes C17 C13 C18 104.8(2) yes C12 C13 C14 108.5(2) yes C17 C13 C14 101.4(2) yes C18 C13 C14 113.8(3) yes C8 C14 C15 120.9(3) yes C8 C14 C13 112.2(3) yes C15 C14 C13 104.0(2) yes C8 C14 H141 106.3(2) no C15 C14 H141 106.3(2) no C13 C14 H141 106.3(2) no C14 C15 C16 102.9(3) yes C14 C15 H151 111.2(2) no C16 C15 H151 111.2(2) no C14 C15 H152 111.2(2) no C16 C15 H152 111.2(2) no H151 C15 H152 109.1 no C17 C16 C15 105.9(3) yes C17 C16 H161 110.6(2) no C15 C16 H161 110.6(2) no C17 C16 H162 110.6(2) no C15 C16 H162 110.6(2) no H161 C16 H162 108.7 no O17 C17 C13 127.1(3) yes O17 C17 C16 124.2(3) yes C13 C17 C16 108.7(3) yes C13 C18 H181 109.5(2) no C13 C18 H182 109.5(2) no H181 C18 H182 109.5 no C13 C18 H183 109.5(2) no H181 C18 H183 109.5 no H182 C18 H183 109.5 no C10 C19 H191 109.5(2) no C10 C19 H192 109.5(2) no H191 C19 H192 109.5 no C10 C19 H193 109.5(2) no H191 C19 H193 109.5 no H192 C19 H193 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O3 C3 1.430(4) yes O3 H3 0.82 no O4 C4 1.424(4) yes O4 H4 0.82 no O17 C17 1.204(4) yes C1 C2 1.504(5) yes C1 C10 1.529(4) yes C1 H11 0.97 no C1 H12 0.97 no C2 C3 1.507(4) yes C2 H21 0.97 no C2 H22 0.97 no C3 C4 1.504(4) yes C3 H31 0.98 no C4 C5 1.531(4) yes C4 H41 0.98 no C5 C6 1.530(4) yes C5 C10 1.553(4) yes C5 H51 0.98 no C6 C7 1.522(4) yes C6 H61 0.97 no C6 H62 0.97 no C7 C8 1.520(4) yes C7 H71 0.97 no C7 H72 0.97 no C8 C14 1.510(4) yes C8 C9 1.536(4) yes C8 H81 0.98 no C9 C11 1.544(4) yes C9 C10 1.559(4) yes C9 H91 0.98 no C10 C19 1.545(4) yes C11 C12 1.523(4) yes C11 H111 0.97 no C11 H112 0.97 no C12 C13 1.506(4) yes C12 H121 0.97 no C12 H122 0.97 no C13 C17 1.512(4) yes C13 C18 1.531(4) yes C13 C14 1.539(4) yes C14 C15 1.527(4) yes C14 H141 0.98 no C15 C16 1.528(5) yes C15 H151 0.97 no C15 H152 0.97 no C16 C17 1.513(4) yes C16 H161 0.97 no C16 H162 0.97 no C18 H181 0.96 no C18 H182 0.96 no C18 H183 0.96 no C19 H191 0.96 no C19 H192 0.96 no C19 H193 0.96 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 C10 C1 C2 C3 59.0(4) no C1 C2 C3 O3 63.0(3) no C1 C2 C3 C4 -57.3(4) no O3 C3 C4 O4 164.6(2) no C2 C3 C4 O4 -72.4(4) no O3 C3 C4 C5 -71.0(3) no C2 C3 C4 C5 52.0(4) no O4 C4 C5 C6 -56.0(3) no C3 C4 C5 C6 -178.3(3) no O4 C4 C5 C10 74.6(3) no C3 C4 C5 C10 -47.6(4) no C4 C5 C6 C7 82.9(3) no C10 C5 C6 C7 -49.4(4) no C5 C6 C7 C8 51.6(4) no C6 C7 C8 C14 -177.7(3) no C6 C7 C8 C9 -55.6(4) no C14 C8 C9 C11 -48.7(4) no C7 C8 C9 C11 -172.6(3) no C14 C8 C9 C10 -177.2(2) no C7 C8 C9 C10 58.9(4) no C2 C1 C10 C19 -167.1(3) no C2 C1 C10 C5 -50.5(4) no C2 C1 C10 C9 71.4(3) no C6 C5 C10 C1 174.9(3) no C4 C5 C10 C1 44.6(4) no C6 C5 C10 C19 -69.8(4) no C4 C5 C10 C19 160.0(3) no C6 C5 C10 C9 51.2(4) no C4 C5 C10 C9 -79.1(3) no C8 C9 C10 C1 -177.6(3) no C11 C9 C10 C1 53.8(3) no C8 C9 C10 C19 63.2(3) no C11 C9 C10 C19 -65.4(4) no C8 C9 C10 C5 -56.6(3) no C11 C9 C10 C5 174.9(2) no C8 C9 C11 C12 46.3(4) no C10 C9 C11 C12 173.9(3) no C9 C11 C12 C13 -50.7(4) no C11 C12 C13 C17 171.4(3) no C11 C12 C13 C18 -68.3(3) no C11 C12 C13 C14 57.5(3) no C7 C8 C14 C15 -55.6(4) no C9 C8 C14 C15 -178.1(3) no C7 C8 C14 C13 -178.9(3) no C9 C8 C14 C13 58.6(3) no C12 C13 C14 C8 -64.0(3) no C17 C13 C14 C8 172.2(3) no C18 C13 C14 C8 60.2(3) no C12 C13 C14 C15 163.7(3) no C17 C13 C14 C15 39.8(3) no C18 C13 C14 C15 -72.1(3) no C8 C14 C15 C16 -166.7(3) no C13 C14 C15 C16 -39.6(4) no C14 C15 C16 C17 23.5(4) no C12 C13 C17 O17 38.1(5) no C18 C13 C17 O17 -85.4(4) no C14 C13 C17 O17 155.9(4) no C12 C13 C17 C16 -143.1(3) no C18 C13 C17 C16 93.4(3) no C14 C13 C17 C16 -25.2(4) no C15 C16 C17 O17 -179.8(4) no C15 C16 C17 C13 1.3(4) no _journal_paper_doi 10.1107/S0108270196008839