#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009019.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_2009019
loop_
_publ_author_name
'Thompson, H. W.'
'Lalancette, R. A.'
'Brunskill, A. P. J.'
_publ_section_title
;
 (+)-3-Oxoandrosta-1,4-diene-17\b-carboxylic acid: catemeric hydrogen
 bonding in a steroidal keto acid
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1680
_journal_page_last               1682
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C20 H26 O3'
_chemical_formula_sum            'C20 H26 O3'
_chemical_formula_weight         314.41
_chemical_melting_point          554
_chemical_name_systematic
;
(+)-3-Oxoandrosta-1,4-diene-17\b-carboxylic Acid
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5970(10)
_cell_length_b                   11.4680(10)
_cell_length_c                   11.1030(10)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.40
_cell_measurement_theta_min      3.57
_cell_volume                     839.53(17)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.072
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        'No decay. Variation < 2'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Sheldrick; 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular plate'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details 'Flack, (1983).'
_refine_ls_abs_structure_Flack   -1.1(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.090
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0301P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                2007
_reflns_number_total             2951
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fg1554.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21
_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_cell_volume        839.5(2)
_cod_database_code               2009019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_type_symbol
O1 0.4354(4) 0.1191(2) 0.4815(2) 0.0673(8) Uani d . 1 O
O2 1.0614(4) 0.3346(2) 1.4355(2) 0.0632(7) Uani d . 1 O
O3 1.0814(4) 0.1541(2) 1.3646(2) 0.0644(7) Uani d . 1 O
C1 0.8455(5) 0.1613(3) 0.6896(2) 0.0433(8) Uani d . 1 C
C2 0.7309(5) 0.1119(3) 0.6032(2) 0.0444(9) Uani d . 1 C
C3 0.5427(5) 0.1658(3) 0.5615(3) 0.0446(8) Uani d . 1 C
C4 0.4899(5) 0.2757(3) 0.6159(2) 0.0422(8) Uani d . 1 C
C5 0.6023(4) 0.3253(3) 0.7044(2) 0.0367(8) Uani d . 1 C
C6 0.5382(5) 0.4356(3) 0.7655(3) 0.0467(9) Uani d . 1 C
C7 0.5232(5) 0.4157(3) 0.9007(3) 0.0452(8) Uani d . 1 C
C8 0.7143(4) 0.3623(3) 0.9577(2) 0.0340(7) Uani d . 1 C
C9 0.7730(5) 0.2494(3) 0.8913(2) 0.0344(7) Uani d . 1 C
C10 0.7977(4) 0.2721(3) 0.7524(2) 0.0358(7) Uani d . 1 C
C11 0.9525(5) 0.1863(3) 0.9510(2) 0.0418(8) Uani d . 1 C
C12 0.9280(5) 0.1664(3) 1.0866(2) 0.0414(8) Uani d . 1 C
C13 0.8854(4) 0.2806(2) 1.1504(2) 0.0330(7) Uani d . 1 C
C14 0.6933(4) 0.3350(3) 1.0911(2) 0.0355(7) Uani d . 1 C
C15 0.6365(5) 0.4329(3) 1.1782(2) 0.0433(8) Uani d . 1 C
C16 0.6869(5) 0.3806(3) 1.3036(3) 0.0566(10) Uani d . 1 C
C17 0.8173(5) 0.2710(3) 1.2831(3) 0.0422(8) Uani d . 1 C
C18 1.0719(4) 0.3603(3) 1.1463(3) 0.0401(8) Uani d . 1 C
C19 0.9754(5) 0.3564(3) 0.7305(3) 0.0482(8) Uani d . 1 C
C20 0.9957(5) 0.2589(3) 1.3703(3) 0.0469(9) Uani d . 1 C
H3 1.1805 0.1515 1.4111 0.074(13) Uiso calc R 1 H
H1A 0.9654 0.1236 0.7126 0.039(5) Uiso calc R 1 H
H2A 0.7718 0.0420 0.5692 0.039(5) Uiso calc R 1 H
H4A 0.3727 0.3136 0.5881 0.039(5) Uiso calc R 1 H
H6A 0.4077 0.4606 0.7320 0.052(3) Uiso calc R 1 H
H6B 0.6361 0.4968 0.7511 0.052(3) Uiso calc R 1 H
H7A 0.4968 0.4896 0.9396 0.052(3) Uiso calc R 1 H
H7B 0.4093 0.3645 0.9148 0.052(3) Uiso calc R 1 H
H8A 0.8252 0.4184 0.9501 0.025(3) Uiso calc R 1 H
H9A 0.6568 0.1967 0.8974 0.025(3) Uiso calc R 1 H
H11A 1.0745 0.2315 0.9393 0.052(3) Uiso calc R 1 H
H11B 0.9693 0.1115 0.9118 0.052(3) Uiso calc R 1 H
H12A 0.8172 0.1125 1.0986 0.052(3) Uiso calc R 1 H
H12B 1.0510 0.1318 1.1210 0.052(3) Uiso calc R 1 H
H14A 0.5864 0.2760 1.0957 0.025(3) Uiso calc R 1 H
H15A 0.4936 0.4522 1.1693 0.052(3) Uiso calc R 1 H
H15B 0.7161 0.5025 1.1646 0.052(3) Uiso calc R 1 H
H16A 0.5633 0.3598 1.3434 0.052(3) Uiso calc R 1 H
H16B 0.7613 0.4365 1.3535 0.052(3) Uiso calc R 1 H
H17A 0.7310 0.2019 1.2901 0.025(3) Uiso calc R 1 H
H18A 1.0528 0.4266 1.1975 0.058(4) Uiso calc R 1 H
H18B 1.0894 0.3862 1.0651 0.058(4) Uiso calc R 1 H
H18C 1.1901 0.3179 1.1738 0.058(4) Uiso calc R 1 H
H19A 0.9588 0.4259 0.7773 0.058(4) Uiso calc R 1 H
H19B 0.9767 0.3763 0.6465 0.058(4) Uiso calc R 1 H
H19C 1.1011 0.3193 0.7539 0.058(4) 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
O1 0.0772(19) 0.0664(18) 0.0565(15) 0.0066(15) -0.0248(14) -0.0186(14)
O2 0.0812(18) 0.0633(16) 0.0441(13) -0.0005(15) -0.0152(12) -0.0165(14)
O3 0.0822(19) 0.0565(17) 0.0524(15) 0.0076(15) -0.0288(14) -0.0026(13)
C1 0.044(2) 0.050(2) 0.0352(17) 0.0125(18) -0.0012(15) -0.0025(16)
C2 0.060(2) 0.041(2) 0.0331(17) 0.0070(18) 0.0009(16) -0.0083(15)
C3 0.053(2) 0.050(2) 0.0301(16) -0.0009(18) -0.0023(16) 0.0002(16)
C4 0.044(2) 0.047(2) 0.0345(17) 0.0088(18) -0.0051(14) -0.0015(17)
C5 0.0426(19) 0.0371(19) 0.0303(16) 0.0020(16) 0.0018(15) 0.0043(15)
C6 0.052(2) 0.046(2) 0.0413(19) 0.0132(19) -0.0084(15) 0.0012(17)
C7 0.0432(19) 0.049(2) 0.0428(19) 0.0126(17) -0.0002(15) -0.0032(17)
C8 0.0367(17) 0.0322(18) 0.0330(15) -0.0014(15) -0.0010(13) 0.0013(14)
C9 0.0361(17) 0.0337(18) 0.0332(16) -0.0006(16) -0.0040(13) 0.0015(14)
C10 0.0356(17) 0.0397(19) 0.0318(16) 0.0032(16) -0.0027(13) -0.0055(15)
C11 0.054(2) 0.036(2) 0.0355(17) 0.0129(17) -0.0031(16) -0.0063(15)
C12 0.053(2) 0.0338(18) 0.0370(17) 0.0035(17) -0.0093(15) 0.0016(15)
C13 0.0384(18) 0.0314(18) 0.0290(16) -0.0010(16) -0.0010(14) -0.0005(14)
C14 0.0324(17) 0.0400(18) 0.0340(16) -0.0052(15) 0.0008(13) -0.0020(15)
C15 0.0410(19) 0.052(2) 0.0372(18) 0.0048(18) 0.0056(14) -0.0037(17)
C16 0.060(2) 0.075(3) 0.0351(19) 0.006(2) 0.0085(16) -0.0063(17)
C17 0.048(2) 0.045(2) 0.0329(17) -0.0079(18) 0.0027(14) 0.0028(17)
C18 0.0357(18) 0.045(2) 0.0399(17) -0.0029(17) 0.0023(14) -0.0018(16)
C19 0.047(2) 0.058(2) 0.0402(18) -0.0032(19) 0.0043(14) -0.0015(18)
C20 0.063(2) 0.049(2) 0.0290(18) -0.004(2) 0.0032(16) 0.0054(17)
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'
H H 0.0000 0.0000 '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'
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
C2 C1 C10 125.3(3) ?
C1 C2 C3 120.7(3) ?
O1 C3 C4 122.4(3) ?
O1 C3 C2 120.5(3) ?
C4 C3 C2 117.0(3) ?
C5 C4 C3 122.8(3) ?
C4 C5 C6 122.1(3) ?
C4 C5 C10 122.3(3) ?
C6 C5 C10 115.6(3) ?
C5 C6 C7 110.2(3) ?
C8 C7 C6 113.0(3) ?
C7 C8 C14 112.7(2) ?
C7 C8 C9 110.9(2) ?
C14 C8 C9 108.9(2) ?
C11 C9 C8 113.2(2) ?
C11 C9 C10 113.6(2) ?
C8 C9 C10 111.4(2) ?
C1 C10 C5 111.9(2) ?
C1 C10 C19 106.6(3) ?
C5 C10 C19 109.6(3) ?
C1 C10 C9 110.4(2) ?
C5 C10 C9 107.3(2) ?
C19 C10 C9 111.1(2) ?
C9 C11 C12 113.1(3) ?
C13 C12 C11 110.8(2) ?
C12 C13 C18 109.8(3) ?
C12 C13 C14 108.2(2) ?
C18 C13 C14 113.3(2) ?
C12 C13 C17 116.3(2) ?
C18 C13 C17 109.1(2) ?
C14 C13 C17 100.0(2) ?
C8 C14 C15 119.6(3) ?
C8 C14 C13 113.5(2) ?
C15 C14 C13 104.0(2) ?
C14 C15 C16 103.5(2) ?
C15 C16 C17 106.8(3) ?
C20 C17 C16 114.1(3) ?
C20 C17 C13 111.8(3) ?
C16 C17 C13 105.1(3) ?
O2 C20 O3 122.4(3) ?
O2 C20 C17 125.4(3) y
O3 C20 C17 112.1(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.239(3) y
O2 C20 1.202(4) y
O3 C20 1.331(4) y
C1 C2 1.328(4) ?
C1 C10 1.489(4) ?
C2 C3 1.449(4) ?
C3 C4 1.445(4) ?
C4 C5 1.339(4) ?
C5 C6 1.502(4) ?
C5 C10 1.507(4) ?
C6 C7 1.525(4) ?
C7 C8 1.520(4) ?
C8 C14 1.525(4) ?
C8 C9 1.545(4) ?
C9 C11 1.521(4) ?
C9 C10 1.577(4) ?
C10 C19 1.545(4) ?
C11 C12 1.536(4) ?
C12 C13 1.520(4) ?
C13 C18 1.534(4) ?
C13 C14 1.540(4) ?
C13 C17 1.559(4) ?
C14 C15 1.536(4) ?
C15 C16 1.543(4) ?
C16 C17 1.544(4) ?
C17 C20 1.505(4) ?
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 0.6(5) ?
C1 C2 C3 O1 -179.5(3) ?
C1 C2 C3 C4 1.4(4) ?
O1 C3 C4 C5 178.3(3) ?
C2 C3 C4 C5 -2.7(4) ?
C3 C4 C5 C6 -175.9(3) ?
C3 C4 C5 C10 1.9(5) ?
C4 C5 C6 C7 122.1(3) ?
C10 C5 C6 C7 -55.8(4) ?
C5 C6 C7 C8 52.3(4) ?
C6 C7 C8 C14 -176.2(3) ?
C6 C7 C8 C9 -53.8(4) ?
C7 C8 C9 C11 -174.9(3) ?
C14 C8 C9 C11 -50.4(3) ?
C7 C8 C9 C10 55.6(3) ?
C14 C8 C9 C10 -179.8(2) ?
C2 C1 C10 C5 -1.4(4) ?
C2 C1 C10 C19 -121.1(3) ?
C2 C1 C10 C9 118.0(3) ?
C4 C5 C10 C1 0.1(4) ?
C6 C5 C10 C1 178.1(3) ?
C4 C5 C10 C19 118.2(3) ?
C6 C5 C10 C19 -63.9(3) ?
C4 C5 C10 C9 -121.0(3) ?
C6 C5 C10 C9 56.9(3) ?
C11 C9 C10 C1 53.1(3) ?
C8 C9 C10 C1 -177.6(2) ?
C11 C9 C10 C5 175.2(3) ?
C8 C9 C10 C5 -55.5(3) ?
C11 C9 C10 C19 -65.0(3) ?
C8 C9 C10 C19 64.3(3) ?
C8 C9 C11 C12 50.8(4) ?
C10 C9 C11 C12 179.1(3) ?
C9 C11 C12 C13 -54.4(4) ?
C11 C12 C13 C18 -66.7(3) ?
C11 C12 C13 C14 57.4(3) ?
C11 C12 C13 C17 168.9(3) ?
C7 C8 C14 C15 -56.8(4) ?
C9 C8 C14 C15 179.7(3) ?
C7 C8 C14 C13 179.9(3) ?
C9 C8 C14 C13 56.4(3) ?
C12 C13 C14 C8 -60.9(3) ?
C18 C13 C14 C8 61.1(3) ?
C17 C13 C14 C8 177.0(3) ?
C12 C13 C14 C15 167.7(2) ?
C18 C13 C14 C15 -70.4(3) ?
C17 C13 C14 C15 45.5(3) ?
C8 C14 C15 C16 -165.2(3) ?
C13 C14 C15 C16 -37.4(3) ?
C14 C15 C16 C17 13.9(4) ?
C15 C16 C17 C20 137.0(3) ?
C15 C16 C17 C13 14.2(3) ?
C12 C13 C17 C20 83.3(3) ?
C18 C13 C17 C20 -41.4(4) ?
C14 C13 C17 C20 -160.5(3) ?
C12 C13 C17 C16 -152.4(3) ?
C18 C13 C17 C16 82.8(3) ?
C14 C13 C17 C16 -36.3(3) ?
C16 C17 C20 O2 -14.2(5) y
C13 C17 C20 O2 104.9(4) ?
C16 C17 C20 O3 168.3(3) ?
C13 C17 C20 O3 -72.6(3) ?