#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012807.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012807
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o402
_journal_page_last  o404
_publ_section_title
;
(+)-3,11-Dioxoandrost-4-ene-17\b-carboxylic acid: catemeric
hydrogen bonding in a steroidal keto acid
;
loop_
_publ_author_name
  'Newman, Jacob M.'
  'Lalancette, Roger A.'
  'Thompson, Hugh W.'
_chemical_formula_moiety  'C20 H26 O4'
_chemical_formula_sum  'C20 H26 O4'
_chemical_formula_iupac  'C20 H26 O4'
_chemical_formula_weight  330.41
_chemical_melting_point  543
_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  6.699(2)
_cell_length_b  11.409(3)
_cell_length_c  11.764(3)
_cell_angle_alpha  90.00
_cell_angle_beta  94.98(2)
_cell_angle_gamma  90.00
_cell_volume  895.7(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.225
_diffrn_ambient_temperature  296(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
  O1 0.5654(5) 0.4336(3) 1.0660(3) 0.1145(12) Uani d . 1 . . O
  O2 -0.0837(4) 0.4693(2) 0.6111(2) 0.0634(7) Uani d . 1 . . O
  O3 -0.0381(5) 0.6385(3) 0.1058(2) 0.0923(9) Uani d . 1 . . O
  O4 -0.0811(6) 0.4650(3) 0.1819(3) 0.0926(9) Uani d . 1 . . O
  C1 0.2202(6) 0.4289(3) 0.8147(3) 0.0610(10) Uani d . 1 . . C
  C2 0.2677(7) 0.4239(4) 0.9436(3) 0.0769(12) Uani d . 1 . . C
  C3 0.4718(7) 0.4692(4) 0.9789(3) 0.0731(11) Uani d . 1 . . C
  C4 0.5462(6) 0.5626(3) 0.9109(3) 0.0637(9) Uani d . 1 . . C
  C5 0.4484(5) 0.6036(3) 0.8153(3) 0.0508(9) Uani d . 1 . . C
  C6 0.5225(5) 0.7108(3) 0.7567(3) 0.0592(9) Uani d . 1 . . C
  C7 0.5276(5) 0.6919(3) 0.6284(3) 0.0581(10) Uani d . 1 . . C
  C8 0.3268(4) 0.6520(3) 0.5721(3) 0.0438(7) Uani d . 1 . . C
  C9 0.2582(4) 0.5393(2) 0.6326(3) 0.0432(7) Uani d . 1 . . C
  C10 0.2503(5) 0.5523(3) 0.7644(3) 0.0460(8) Uani d . 1 . . C
  C11 0.0711(5) 0.4878(3) 0.5674(3) 0.0475(8) Uani d . 1 . . C
  C12 0.0858(5) 0.4657(3) 0.4422(3) 0.0541(9) Uani d . 1 . . C
  C13 0.1393(5) 0.5809(3) 0.3855(3) 0.0460(8) Uani d . 1 . . C
  C14 0.3369(4) 0.6266(3) 0.4454(3) 0.0478(8) Uani d . 1 . . C
  C15 0.3973(5) 0.7249(3) 0.3673(3) 0.0591(10) Uani d . 1 . . C
  C16 0.3272(6) 0.6814(4) 0.2462(3) 0.0748(11) Uani d . 1 . . C
  C17 0.1947(5) 0.5736(3) 0.2598(3) 0.0611(10) Uani d . 1 . . C
  C18 -0.0349(5) 0.6666(3) 0.3925(3) 0.0515(8) Uani d . 1 . . C
  C19 0.0792(5) 0.6361(4) 0.7939(3) 0.0639(10) Uani d . 1 . . C
  C20 0.0140(6) 0.5647(4) 0.1736(3) 0.0666(10) Uani d . 1 . . C
  H4 -0.212(8) 0.458(5) 0.133(4) 0.126(18) Uiso d . 1 . . H
  H1A 0.0823 0.4048 0.7962 0.073 Uiso calc R 1 . . H
  H1B 0.3056 0.3737 0.7791 0.073 Uiso calc R 1 . . H
  H2A 0.1696 0.4700 0.9801 0.092 Uiso calc R 1 . . H
  H2B 0.2576 0.3434 0.9692 0.092 Uiso calc R 1 . . H
  H4A 0.6692 0.5960 0.9351 0.076 Uiso calc R 1 . . H
  H6A 0.6562 0.7300 0.7898 0.071 Uiso calc R 1 . . H
  H6B 0.4356 0.7765 0.7697 0.071 Uiso calc R 1 . . H
  H7A 0.5657 0.7646 0.5934 0.070 Uiso calc R 1 . . H
  H7B 0.6284 0.6336 0.6154 0.070 Uiso calc R 1 . . H
  H8 0.2279 0.7140 0.5804 0.053 Uiso calc R 1 . . H
  H9 0.3642 0.4817 0.6236 0.052 Uiso calc R 1 . . H
  H12A -0.0411 0.4365 0.4074 0.065 Uiso calc R 1 . . H
  H12B 0.1880 0.4074 0.4321 0.065 Uiso calc R 1 . . H
  H14 0.4357 0.5639 0.4404 0.057 Uiso calc R 1 . . H
  H15A 0.5412 0.7370 0.3754 0.071 Uiso calc R 1 . . H
  H15B 0.3313 0.7978 0.3841 0.071 Uiso calc R 1 . . H
  H16A 0.2518 0.7423 0.2039 0.090 Uiso calc R 1 . . H
  H16B 0.4417 0.6608 0.2052 0.090 Uiso calc R 1 . . H
  H17 0.2772 0.5035 0.2524 0.073 Uiso calc R 1 . . H
  H18A -0.0695 0.6711 0.4699 0.077 Uiso calc R 1 . . H
  H18B -0.1486 0.6396 0.3443 0.077 Uiso calc R 1 . . H
  H18C 0.0041 0.7428 0.3677 0.077 Uiso calc R 1 . . H
  H19A 0.0786 0.6420 0.8753 0.096 Uiso calc R 1 . . H
  H19B -0.0472 0.6056 0.7622 0.096 Uiso calc R 1 . . H
  H19C 0.1005 0.7122 0.7625 0.096 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 0.133(3) 0.132(3) 0.0690(19) -0.045(2) -0.0405(19) 0.036(2)
  O2 0.0581(15) 0.0667(16) 0.0651(15) -0.0216(14) 0.0031(12) 0.0022(13)
  O3 0.115(2) 0.089(2) 0.0677(17) -0.002(2) -0.0210(16) 0.0205(18)
  O4 0.121(3) 0.081(2) 0.0706(19) -0.017(2) -0.0248(18) 0.0159(16)
  C1 0.074(2) 0.062(2) 0.047(2) -0.015(2) 0.0030(18) 0.0010(18)
  C2 0.100(3) 0.080(3) 0.051(2) -0.026(2) 0.009(2) 0.002(2)
  C3 0.090(3) 0.088(3) 0.040(2) -0.018(3) -0.003(2) 0.000(2)
  C4 0.067(2) 0.073(2) 0.049(2) -0.017(2) -0.0035(18) -0.004(2)
  C5 0.0543(19) 0.054(2) 0.045(2) -0.0014(17) 0.0099(16) -0.0106(15)
  C6 0.054(2) 0.058(2) 0.064(2) -0.0145(19) -0.0030(18) -0.0010(18)
  C7 0.053(2) 0.061(2) 0.059(2) -0.0069(18) 0.0024(18) 0.0082(17)
  C8 0.0394(16) 0.0426(18) 0.0497(17) 0.0028(15) 0.0051(14) 0.0022(14)
  C9 0.0451(17) 0.0393(16) 0.0451(17) 0.0054(16) 0.0033(14) -0.0025(14)
  C10 0.0508(19) 0.0456(18) 0.0419(17) -0.0086(17) 0.0057(15) -0.0036(15)
  C11 0.054(2) 0.0344(17) 0.053(2) -0.0070(17) -0.0001(16) 0.0047(15)
  C12 0.064(2) 0.0429(18) 0.054(2) -0.0012(18) -0.0051(17) -0.0015(17)
  C13 0.0488(18) 0.0445(19) 0.0445(18) 0.0088(16) 0.0037(15) 0.0070(15)
  C14 0.0391(17) 0.0505(18) 0.054(2) 0.0119(15) 0.0060(15) 0.0064(17)
  C15 0.046(2) 0.071(2) 0.062(2) 0.0029(19) 0.0102(18) 0.0155(18)
  C16 0.075(3) 0.088(3) 0.063(2) 0.007(2) 0.016(2) 0.019(2)
  C17 0.068(2) 0.067(2) 0.049(2) 0.018(2) 0.0062(17) 0.0003(18)
  C18 0.0437(18) 0.0492(18) 0.061(2) 0.0043(16) 0.0016(16) 0.0034(16)
  C19 0.053(2) 0.074(2) 0.066(2) 0.002(2) 0.0134(18) -0.012(2)
  C20 0.090(3) 0.067(2) 0.043(2) 0.012(3) 0.005(2) 0.003(2)
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(5) ?
  O2 C11 . 1.215(4) ?
  O3 C20 . 1.192(4) Y
  O4 C20 . 1.311(5) Y
  C1 C2 . 1.524(5) ?
  C1 C10 . 1.547(5) ?
  C2 C3 . 1.487(6) ?
  C3 C4 . 1.447(5) ?
  C4 C5 . 1.336(5) ?
  C5 C6 . 1.509(5) ?
  C5 C10 . 1.525(4) ?
  C6 C7 . 1.528(5) ?
  C7 C8 . 1.517(4) ?
  C8 C14 . 1.526(4) ?
  C8 C9 . 1.557(4) ?
  C9 C11 . 1.528(4) ?
  C9 C10 . 1.563(4) ?
  C10 C19 . 1.555(5) ?
  C11 C12 . 1.507(4) ?
  C12 C13 . 1.530(4) ?
  C13 C18 . 1.530(4) ?
  C13 C14 . 1.536(5) ?
  C13 C17 . 1.558(4) ?
  C14 C15 . 1.527(4) ?
  C15 C16 . 1.542(5) ?
  C16 C17 . 1.533(5) ?
  C17 C20 . 1.514(5) ?
  O4 H4 . 1.01(6) ?
  C1 H1A . 0.9700 ?
  C1 H1B . 0.9700 ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C4 H4A . 0.9300 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8 . 0.9800 ?
  C9 H9 . 0.9800 ?
  C12 H12A . 0.9700 ?
  C12 H12B . 0.9700 ?
  C14 H14 . 0.9800 ?
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 H17 . 0.9800 ?
  C18 H18A . 0.9600 ?
  C18 H18B . 0.9600 ?
  C18 H18C . 0.9600 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?