data_2006300
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  903
_journal_page_last  906
_publ_section_title
;
(+)-3-Oxoandrost-4-ene-17\b-carboxylic Acid:
Catemeric Hydrogen Bonding in a Steroidal Keto Acid
;
loop_
_publ_author_name
 'Brunskill, Andrew P. J.'
 'Lalancette*, Roger A.'
 'Thompson, Hugh W.'
_chemical_name_common
;
(+)-4-Androsten-3-one-17\b-carboxylic Acid
;
_chemical_formula_moiety  'C20 H28 O3'
_chemical_formula_sum  'C20 H28 O3'
_chemical_formula_structural  'C20 H28 O3'
_chemical_formula_analytical  'C20 H28 O3'
_chemical_formula_weight  316.44
_chemical_melting_point  527K
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
_cell_length_a  6.9880(10)
_cell_length_b  11.2540(10)
_cell_length_c  11.480(2)
_cell_angle_alpha  90.00
_cell_angle_beta  102.060(10)
_cell_angle_gamma  90.00
_cell_volume  882.9(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.190
_exptl_crystal_density_meas  1.1910(10)
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs   .053
_refine_ls_wR_factor_obs   .113
loop_
_atom_site_label
_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_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
 O1  -.0578(3) 1.3491(2)  .6122(2)  .0655(6) Uani d . 1 . O
 O2  .6414(4)  .3838(2)  .8409(2)  .0879(8) Uani d . 1 . O
 O3  .6183(4)  .4524(2)  .6579(2)  .0785(7) Uani d . 1 . O
 H3  .728(6)  .415(4)  .661(3)  .089(13) Uiso d . 1 . H
 C1  .2305(4) 1.0874(2)  .5843(2)  .0465(6) Uani d . 1 . C
 C2  .1948(4) 1.2208(2)  .5811(3)  .0541(7) Uani d . 1 . C
 C3  .0280(4) 1.2548(2)  .6370(2)  .0499(7) Uani d . 1 . C
 C4  -.0195(4) 1.1746(2)  .7262(2)  .0498(7) Uani d . 1 . C
 C5  .0814(3) 1.0751(2)  .7637(2)  .0412(6) Uani d . 1 . C
 C6  .0379(4) 1.0058(3)  .8660(2)  .0510(7) Uani d . 1 . C
 C7  .0338(4)  .8727(2)  .8465(2)  .0479(6) Uani d . 1 . C
 C8  .2228(3)  .8313(2)  .8132(2)  .0363(5) Uani d . 1 . C
 C9  .2500(3)  .8949(2)  .6988(2)  .0348(5) Uani d . 1 . C
 C10  .2516(3) 1.0335(2)  .7091(2)  .0355(5) Uani d . 1 . C
 C11  .4274(4)  .8469(2)  .6531(2)  .0490(7) Uani d . 1 . C
 C12  .4323(4)  .7116(2)  .6440(2)  .0491(7) Uani d . 1 . C
 C13  .4156(4)  .6532(2)  .7614(2)  .0394(6) Uani d . 1 . C
 C14  .2258(3)  .6975(2)  .7932(2)  .0382(6) Uani d . 1 . C
 C15  .1965(4)  .6147(2)  .8942(3)  .0507(7) Uani d . 1 . C
 C16  .2777(5)  .4934(3)  .8632(3)  .0581(7) Uani d . 1 . C
 C17  .3779(4)  .5167(2)  .7580(2)  .0465(6) Uani d . 1 . C
 C18  .5964(4)  .6801(2)  .8592(2)  .0488(6) Uani d . 1 . C
 C19  .4419(4) 1.0781(3)  .7921(3)  .0573(7) Uani d . 1 . C
 C20  .5590(4)  .4436(2)  .7597(3)  .0535(7) Uani d . 1 . C
 H1A  .3486 1.0711  .5553  .052(5) Uiso calc R 1 . H
 H1B  .1225 1.0488  .5309  .052(5) Uiso calc R 1 . H
 H2A  .3124 1.2608  .6226  .061(6) Uiso calc R 1 . H
 H2B  .1678 1.2476  .4989  .061(6) Uiso calc R 1 . H
 H4A  -.1262 1.1933  .7595  .057(8) Uiso calc R 1 . H
 H6A  -.0881 1.0308  .8803  .061(6) Uiso calc R 1 . H
 H6B  .1360 1.0242  .9368  .061(6) Uiso calc R 1 . H
 H7A  -.0765  .8520  .7833  .049(5) Uiso calc R 1 . H
 H7B  .0176  .8327  .9186  .049(5) Uiso calc R 1 . H
 H8B  .3327  .8522  .8780  .038(6) Uiso calc R 1 . H
 H9A  .1345  .8749  .6375  .029(6) Uiso calc R 1 . H
 H11A  .4257  .8805  .5750  .049(5) Uiso calc R 1 . H
 H11B  .5464  .8735  .7062  .049(5) Uiso calc R 1 . H
 H12A  .3250  .6851  .5815  .059(6) Uiso calc R 1 . H
 H12B  .5538  .6873  .6229  .059(6) Uiso calc R 1 . H
 H14A  .1202  .6800  .7246  .033(6) Uiso calc R 1 . H
 H15A  .0590  .6084  .8967  .059(6) Uiso calc R 1 . H
 H15B  .2681  .6433  .9706  .059(6) Uiso calc R 1 . H
 H16A  .3711  .4625  .9310  .065(6) Uiso calc R 1 . H
 H16B  .1724  .4363  .8410  .065(6) Uiso calc R 1 . H
 H17A  .2836  .4984  .6842  .049(7) Uiso calc R 1 . H
 H18A  .5826  .6425  .9320  .059(5) Uiso calc R 1 . H
 H18B  .6085  .7644  .8711  .059(5) Uiso calc R 1 . H
 H18C  .7112  .6502  .8356  .059(5) Uiso calc R 1 . H
 H19A  .5527 1.0537  .7607  .083(6) Uiso calc R 1 . H
 H19B  .4392 1.1633  .7967  .083(6) Uiso calc R 1 . H
 H19C  .4517 1.0451  .8702  .083(6) 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  .0758(14)  .0488(11)  .0727(13)  .0273(10)  .0171(11)  .0072(10)
 O2  .105(2)  .078(2)  .083(2)  .0415(14)  .0256(14)  .0326(14)
 O3  .095(2)  .077(2)  .0701(14)  .0431(14)  .0314(13)  .0179(12)
 C1  .057(2)  .0376(12)  .050(2)  .0084(12)  .0236(12)  .0039(11)
 C2  .065(2)  .0367(13)  .064(2)  .0073(13)  .0217(15)  .0076(12)
 C3  .052(2)  .0416(14)  .054(2)  .0075(12)  .0058(12)  -.0067(12)
 C4  .0473(15)  .0497(15)  .056(2)  .0108(13)  .0187(13)  -.0065(13)
 C5  .0401(13)  .0444(13)  .0400(13)  .0023(11)  .0102(10)  -.0100(11)
 C6  .052(2)  .060(2)  .0475(15)  .0133(13)  .0236(12)  .0009(13)
 C7  .0469(14)  .052(2)  .051(2)  .0054(12)  .0249(13)  .0088(12)
 C8  .0333(12)  .0441(13)  .0332(12)  -.0002(10)  .0104(10)  .0038(9)
 C9  .0353(12)  .0357(11)  .0341(12)  .0024(9)  .0087(10)  -.0008(9)
 C10  .0357(12)  .0331(12)  .0384(12)  .0021(9)  .0092(10)  -.0006(9)
 C11  .058(2)  .0435(14)  .055(2)  .0130(12)  .0334(14)  .0155(12)
 C12  .066(2)  .0378(13)  .051(2)  .0141(12)  .0288(14)  .0049(11)
 C13  .0440(14)  .0328(12)  .0444(14)  .0037(10)  .0158(12)  .0055(10)
 C14  .0345(12)  .0443(14)  .0355(12)  -.0012(10)  .0065(10)  .0032(10)
 C15  .046(2)  .055(2)  .055(2)  -.0011(12)  .0177(13)  .0144(13)
 C16  .066(2)  .0459(15)  .065(2)  -.0087(13)  .0175(15)  .0100(13)
 C17  .055(2)  .0354(13)  .0468(14)  -.0004(12)  .0052(12)  .0036(11)
 C18  .0383(14)  .0442(14)  .062(2)  .0029(11)  .0066(12)  .0053(12)
 C19  .049(2)  .053(2)  .067(2)  -.0073(14)  .0057(14)  -.0073(14)
 C20  .069(2)  .0332(12)  .059(2)  .0058(13)  .0130(15)  .0052(13)
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
 O1 C3 . 1.223(3) Y
 O2 C20 . 1.195(3) Y
 O3 C20 . 1.322(4) Y
 O3 H3 .  .87(4) Y
 C1 C2 . 1.522(4) ?
 C1 C10 . 1.534(3) ?
 C2 C3 . 1.493(4) ?
 C3 C4 . 1.454(4) ?
 C4 C5 . 1.345(4) ?
 C5 C6 . 1.493(4) ?
 C5 C10 . 1.529(3) ?
 C6 C7 . 1.514(4) ?
 C7 C8 . 1.522(3) ?
 C8 C14 . 1.523(3) ?
 C8 C9 . 1.542(3) ?
 C9 C11 . 1.542(3) ?
 C9 C10 . 1.565(3) ?
 C10 C19 . 1.548(4) ?
 C11 C12 . 1.527(4) ?
 C12 C13 . 1.525(3) ?
 C13 C14 . 1.530(3) ?
 C13 C18 . 1.535(4) ?
 C13 C17 . 1.558(3) ?
 C14 C15 . 1.534(3) ?
 C15 C16 . 1.547(4) ?
 C16 C17 . 1.541(4) ?
 C17 C20 . 1.506(4) ?