#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008471.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_2008471 loop_ _publ_author_name 'Addlagatta Anthony' 'Mariusz Jask\'olski' 'Ashwini Nangia' _publ_section_title ; Androst-4-ene-3,6,17-trione ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 787 _journal_page_last 789 _journal_paper_doi 10.1107/S0108270199000517 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C19 H24 O3' _chemical_formula_sum 'C19 H24 O3' _chemical_formula_weight 300.38 _chemical_melting_point 495 _chemical_name_common androst-4-ene-3,6,17-trione _chemical_name_systematic ; Androst-4-ene-3,6,17-trione ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.2842(6) _cell_length_b 13.4500(10) _cell_length_c 16.503(2) _cell_measurement_reflns_used 52 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 84 _cell_measurement_theta_min 16 _cell_volume 1616.8(3) _computing_cell_refinement 'KM-4 Software' _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1989)' _computing_data_reduction 'KM-4 Software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)' _computing_publication_material SHELX97 _computing_structure_refinement SHELX97 _computing_structure_solution 'SHELX97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.934 _diffrn_measured_fraction_theta_max 0.934 _diffrn_measurement_device_type 'Kuma KM-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.015 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1603 _diffrn_reflns_theta_full 68.10 _diffrn_reflns_theta_max 68.10 _diffrn_reflns_theta_min 4.24 _diffrn_standards_decay_% 'less than 2.1' _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.652 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.169 _refine_diff_density_min -0.166 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.1(5) _refine_ls_extinction_coef 0.0053(7) _refine_ls_extinction_method 'SHELX97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment fixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 1603 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.035 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2880P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.101 _reflns_number_gt 1436 _reflns_number_total 1603 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ka1312.cif _[local]_cod_data_source_block AT _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '495 K' was changed to '495' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '495 K' was changed to '495' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2880P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2880P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008471 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_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 C1 -.4059(3) -.2769(2) -.69328(16) .0578(6) Uani d . 1 . . C H11 -.4757 -.3318 -.7157 .060 Uiso calc R 1 . . H H12 -.4601 -.2598 -.6414 .049 Uiso calc R 1 . . H C2 -.4237(4) -.18809(19) -.74971(16) .0650(7) Uani d . 1 . . C H21 -.3953 -.2090 -.8046 .076 Uiso calc R 1 . . H H22 -.5498 -.1649 -.7490 .084 Uiso calc R 1 . . H C3 -.2990(5) -.10347(19) -.72666(16) .0661(7) Uani d . 1 . . C O3 -.3292(4) -.01776(14) -.74626(15) .1024(9) Uani d . 1 . . O C4 -.1338(4) -.12864(18) -.68187(15) .0565(6) Uani d . 1 . . C H41 -.0550 -.0773 -.6671 .082 Uiso calc R 1 . . H C5 -.0887(3) -.22118(17) -.66066(13) .0470(5) Uani d . 1 . . C C6 .0889(3) -.23415(17) -.61567(16) .0540(6) Uani d . 1 . . C O6 .2111(3) -.17302(14) -.62107(15) .0821(6) Uani d . 1 . . O C7 .1083(4) -.32178(17) -.56080(17) .0599(7) Uani d . 1 . . C H71 .0703 -.3022 -.5068 .084 Uiso calc R 1 . . H H72 .2371 -.3397 -.5580 .056 Uiso calc R 1 . . H C8 -.0016(3) -.41398(15) -.58566(14) .0421(5) Uani d . 1 . . C H81 .0548 -.4437 -.6338 .032 Uiso calc R 1 . . H C9 -.2003(3) -.38372(16) -.60556(13) .0434(5) Uani d . 1 . . C H91 -.2452 -.3460 -.5587 .065 Uiso calc R 1 . . H C10 -.2070(3) -.31163(16) -.67901(13) .0452(5) Uani d . 1 . . C C11 -.3301(3) -.47317(18) -.61532(17) .0582(6) Uani d . 1 . . C H111 -.4555 -.4490 -.6175 .076 Uiso calc R 1 . . H H112 -.3040 -.5054 -.6666 .095 Uiso calc R 1 . . H C12 -.3155(3) -.55029(19) -.54766(17) .0588(7) Uani d . 1 . . C H121 -.3604 -.5222 -.4973 .081 Uiso calc R 1 . . H H122 -.3902 -.6078 -.5608 .062 Uiso calc R 1 . . H C13 -.1163(3) -.58170(16) -.53773(14) .0458(5) Uani d . 1 . . C C14 -.0015(3) -.48960(16) -.51749(13) .0445(5) Uani d . 1 . . C H141 -.0607 -.4576 -.4710 .048 Uiso calc R 1 . . H C15 .1803(4) -.53243(19) -.48662(18) .0611(7) Uani d . 1 . . C H151 .2475 -.4838 -.4549 .070 Uiso calc R 1 . . H H152 .2568 -.5549 -.5311 .061 Uiso calc R 1 . . H C16 .1171(5) -.6201(2) -.43387(17) .0713(8) Uani d . 1 . . C H161 .2015 -.6755 -.4387 .109 Uiso calc R 1 . . H H162 .1097 -.6005 -.3774 .098 Uiso calc R 1 . . H C17 -.0711(4) -.64792(19) -.46615(15) .0566(6) Uani d . 1 . . C O17 -.1665(4) -.71428(15) -.43982(12) .0810(6) Uani d . 1 . . O C18 -.0474(4) -.63870(18) -.61228(15) .0580(6) Uani d . 1 . . C H181 .0760 -.6610 -.6029 .101 Uiso calc R 1 . . H H182 -.0496 -.5957 -.6587 .096 Uiso calc R 1 . . H H183 -.1253 -.6950 -.6219 .093 Uiso calc R 1 . . H C19 -.1294(4) -.36021(18) -.75663(14) .0595(7) Uani d . 1 . . C H191 -.0024 -.3766 -.7485 .094 Uiso calc R 1 . . H H192 -.1403 -.3146 -.8011 .070 Uiso calc R 1 . . H H193 -.1972 -.4196 -.7685 .085 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 C1 .0548(14) .0620(15) .0566(14) .0088(13) -.0081(12) .0053(13) C2 .0730(16) .0667(15) .0552(14) .0179(14) -.0122(13) .0067(13) C3 .093(2) .0544(14) .0511(14) .0201(15) .0013(14) .0021(12) O3 .142(2) .0569(11) .1086(18) .0222(14) -.0377(17) .0131(12) C4 .0722(16) .0449(12) .0525(14) .0046(13) .0027(12) .0025(12) C5 .0559(13) .0440(11) .0412(12) .0025(11) .0068(10) -.0016(10) C6 .0512(12) .0429(11) .0677(15) -.0037(11) .0022(12) -.0038(12) O6 .0645(11) .0601(10) .1218(17) -.0177(10) -.0025(12) .0157(12) C7 .0543(13) .0502(13) .0751(17) -.0072(11) -.0169(13) .0038(13) C8 .0404(10) .0399(10) .0460(11) -.0004(10) -.0015(9) -.0007(9) C9 .0415(11) .0445(11) .0442(11) .0023(10) -.0001(9) .0001(10) C10 .0511(12) .0442(11) .0401(11) .0031(10) -.0019(9) -.0014(10) C11 .0426(11) .0599(14) .0723(16) -.0073(11) -.0114(12) .0152(13) C12 .0503(13) .0573(13) .0688(17) -.0082(11) .0040(12) .0133(13) C13 .0505(12) .0438(11) .0431(12) -.0005(10) .0017(10) .0031(10) C14 .0458(11) .0441(11) .0435(11) .0031(10) -.0019(9) -.0016(10) C15 .0552(14) .0573(13) .0708(16) .0035(12) -.0191(12) .0045(13) C16 .092(2) .0598(15) .0622(16) .0106(16) -.0192(15) .0083(14) C17 .0765(16) .0491(13) .0441(12) .0059(13) .0072(12) .0020(11) O17 .1068(16) .0722(12) .0640(11) -.0166(12) .0086(11) .0245(10) C18 .0766(17) .0492(12) .0481(13) -.0053(13) .0041(12) -.0052(11) C19 .0816(18) .0532(13) .0438(13) .0055(14) .0011(12) -.0014(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 '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 C2 C1 C10 114.4(2) C2 C1 H11 108.7 C10 C1 H11 108.7 C2 C1 H12 108.7 C10 C1 H12 108.7 H11 C1 H12 107.6 C3 C2 C1 112.8(2) C3 C2 H21 109.0 C1 C2 H21 109.0 C3 C2 H22 109.0 C1 C2 H22 109.0 H21 C2 H22 107.8 O3 C3 C4 120.4(3) O3 C3 C2 122.7(3) C4 C3 C2 116.9(2) C5 C4 C3 123.7(3) C5 C4 H41 118.1 C3 C4 H41 118.1 C4 C5 C6 116.8(2) C4 C5 C10 123.7(2) C6 C5 C10 119.56(19) O6 C6 C7 120.6(2) O6 C6 C5 121.1(2) C7 C6 C5 118.2(2) C6 C7 C8 115.3(2) C6 C7 H71 108.5 C8 C7 H71 108.5 C6 C7 H72 108.5 C8 C7 H72 108.5 H71 C7 H72 107.5 C14 C8 C7 110.13(18) C14 C8 C9 109.63(17) C7 C8 C9 109.54(18) C14 C8 H81 109.2 C7 C8 H81 109.2 C9 C8 H81 109.2 C11 C9 C8 113.17(18) C11 C9 C10 112.78(18) C8 C9 C10 111.17(17) C11 C9 H91 106.4 C8 C9 H91 106.4 C10 C9 H91 106.4 C5 C10 C1 108.67(19) C5 C10 C19 107.22(19) C1 C10 C19 110.2(2) C5 C10 C9 109.04(17) C1 C10 C9 109.77(18) C19 C10 C9 111.82(17) C12 C11 C9 114.3(2) C12 C11 H111 108.7 C9 C11 H111 108.7 C12 C11 H112 108.7 C9 C11 H112 108.7 H111 C11 H112 107.6 C13 C12 C11 109.54(19) C13 C12 H121 109.8 C11 C12 H121 109.8 C13 C12 H122 109.8 C11 C12 H122 109.8 H121 C12 H122 108.2 C17 C13 C12 117.1(2) C17 C13 C14 100.74(18) C12 C13 C14 108.66(19) C17 C13 C18 105.08(18) C12 C13 C18 111.4(2) C14 C13 C18 113.59(19) C8 C14 C15 119.96(19) C8 C14 C13 112.36(17) C15 C14 C13 103.92(17) C8 C14 H141 106.6 C15 C14 H141 106.6 C13 C14 H141 106.6 C14 C15 C16 102.6(2) C14 C15 H151 111.2 C16 C15 H151 111.2 C14 C15 H152 111.2 C16 C15 H152 111.2 H151 C15 H152 109.2 C17 C16 C15 105.1(2) C17 C16 H161 110.7 C15 C16 H161 110.7 C17 C16 H162 110.7 C15 C16 H162 110.7 H161 C16 H162 108.8 O17 C17 C13 126.0(3) O17 C17 C16 125.0(2) C13 C17 C16 109.0(2) C13 C18 H181 109.5 C13 C18 H182 109.5 H181 C18 H182 109.5 C13 C18 H183 109.5 H181 C18 H183 109.5 H182 C18 H183 109.5 C10 C19 H191 109.5 C10 C19 H192 109.5 H191 C19 H192 109.5 C10 C19 H193 109.5 H191 C19 H193 109.5 H192 C19 H193 109.5 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 C1 C2 . 1.520(3) ? C1 C10 . 1.540(3) ? C1 H11 . .9700 ? C1 H12 . .9700 ? C2 C3 . 1.505(4) ? C2 H21 . .9700 ? C2 H22 . .9700 ? C3 O3 . 1.217(3) ? C3 C4 . 1.452(4) ? C4 C5 . 1.334(3) ? C4 H41 . .9300 ? C5 C6 . 1.502(3) ? C5 C10 . 1.521(3) ? C6 O6 . 1.215(3) ? C6 C7 . 1.493(3) ? C7 C8 . 1.532(3) ? C7 H71 . .9700 ? C7 H72 . .9700 ? C8 C14 . 1.517(3) ? C8 C9 . 1.539(3) ? C8 H81 . .9800 ? C9 C11 . 1.539(3) ? C9 C10 . 1.553(3) ? C9 H91 . .9800 ? C10 C19 . 1.545(3) ? C11 C12 . 1.528(3) ? C11 H111 . .9700 ? C11 H112 . .9700 ? C12 C13 . 1.520(3) ? C12 H121 . .9700 ? C12 H122 . .9700 ? C13 C17 . 1.516(3) ? C13 C14 . 1.532(3) ? C13 C18 . 1.534(3) ? C14 C15 . 1.531(3) ? C14 H141 . .9800 ? C15 C16 . 1.536(4) ? C15 H151 . .9700 ? C15 H152 . .9700 ? C16 C17 . 1.518(4) ? C16 H161 . .9700 ? C16 H162 . .9700 ? C17 O17 . 1.212(3) ? C18 H181 . .9600 ? C18 H182 . .9600 ? C18 H183 . .9600 ? C19 H191 . .9600 ? C19 H192 . .9600 ? C19 H193 . .9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C1 H12 O6 1_455 0.97 2.68 3.340(3) 125 C2 H21 O17 2_444 0.97 2.50 3.464(3) 172 C2 H22 O6 1_455 0.97 2.74 3.409(4) 127 C16 H161 O17 4_534 0.97 2.67 3.434(4) 136 C16 H162 O3 4_544 0.97 2.63 3.525(4) 154 C18 H181 O17 4_534 0.96 2.61 3.514(4) 156 C19 H192 O17 2_444 0.96 2.71 3.515(4) 141