#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012606.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_2012606
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o159
_journal_page_last  o161
_publ_section_title
;
2-cis-3-trans-3-Ethyl-2,6,6-trimethyl-4-oxocyclohexanecarboxylic
acid: an intermediate in the synthesis of a highly potent estrogen
;
loop_
_publ_author_name
  'Xie, Songwen'
  'Hou, Yuqing'
  'Meyers, Cal Y.'
  'Robinson, Paul D.'
_chemical_formula_moiety  'C12 H20 O3'
_chemical_formula_sum  'C12 H20 O3'
_chemical_formula_weight  212.28
_chemical_melting_point  394.8-396.2
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  13.716(3)
_cell_length_b  14.103(3)
_cell_length_c  6.214(4)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1202.0(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.173
_diffrn_ambient_temperature  296
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  .00322(19)  .46507(17)  .8007(3)  .0866(8) Uani d . 1 . . O
  O2  .11705(15)  .37785(12)  .6441(3)  .0640(5) Uani d . 1 . . O
  O3  -.11480(14)  .74515(12)  .5400(3)  .0668(6) Uani d . 1 . . O
  C1  .06744(18)  .51509(15)  .4579(4)  .0396(6) Uani d . 1 . . C
  C2  -.02975(17)  .52046(15)  .3359(4)  .0396(6) Uani d . 1 . . C
  C3  -.10728(17)  .58157(16)  .4493(4)  .0406(6) Uani d . 1 . . C
  C4  -.06654(17)  .67269(17)  .5414(4)  .0421(6) Uani d . 1 . . C
  C5  .03150(17)  .66974(18)  .6450(5)  .0499(6) Uani d . 1 . . C
  C6  .10828(17)  .61406(17)  .5165(4)  .0439(6) Uani d . 1 . . C
  C7  .05804(19)  .45200(17)  .6528(4)  .0477(6) Uani d . 1 . . C
  C8  -.0684(2)  .42062(17)  .2848(5)  .0583(8) Uani d . 1 . . C
  C9  -.19889(18)  .59936(19)  .3139(5)  .0572(7) Uani d . 1 . . C
  C10  -.1801(2)  .6456(2)  .0973(5)  .0725(9) Uani d . 1 . . C
  C11  .20128(19)  .6041(2)  .6514(5)  .0632(8) Uani d . 1 . . C
  C12  .13336(19)  .66809(18)  .3110(5)  .0565(7) Uani d . 1 . . C
  H1  .1148  .4851  .3613  .047 Uiso calc R 1 . . H
  H2  .1075  .3438  .7489  .096 Uiso calc R 1 . . H
  H2A  -.0160  .5510  .1976  .048 Uiso calc R 1 . . H
  H3  -.1290  .5443  .5735  .049 Uiso calc R 1 . . H
  H5A  .0251  .6413  .7864  .060 Uiso calc R 1 . . H
  H5B  .0545  .7342  .6646  .060 Uiso calc R 1 . . H
  H8A  -.0890  .3904  .4155  .087 Uiso calc R 1 . . H
  H8B  -.0177  .3838  .2189  .087 Uiso calc R 1 . . H
  H8C  -.1227  .4254  .1880  .087 Uiso calc R 1 . . H
  H9A  -.2315  .5392  .2902  .069 Uiso calc R 1 . . H
  H9B  -.2429  .6394  .3955  .069 Uiso calc R 1 . . H
  H10A  -.1438  .7031  .1177  .109 Uiso calc R 1 . . H
  H10B  -.2412  .6600  .0292  .109 Uiso calc R 1 . . H
  H10C  -.1435  .6030  .0078  .109 Uiso calc R 1 . . H
  H11A  .2489  .5686  .5719  .095 Uiso calc R 1 . . H
  H11B  .1864  .5716  .7830  .095 Uiso calc R 1 . . H
  H11C  .2267  .6659  .6836  .095 Uiso calc R 1 . . H
  H12A  .1668  .7257  .3474  .085 Uiso calc R 1 . . H
  H12B  .0745  .6830  .2346  .085 Uiso calc R 1 . . H
  H12C  .1746  .6296  .2218  .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
  O1  .1171(18)  .0871(15)  .0557(12)  .0325(14)  .0391(15)  .0269(13)
  O2  .0734(12)  .0458(10)  .0728(12)  .0116(10)  .0072(12)  .0237(10)
  O3  .0666(12)  .0465(10)  .0873(14)  .0195(10)  -.0200(12)  -.0267(11)
  C1  .0448(13)  .0340(12)  .0400(12)  .0035(10)  .0100(12)  .0020(11)
  C2  .0499(14)  .0321(12)  .0368(12)  -.0037(10)  .0073(12)  -.0021(11)
  C3  .0445(13)  .0389(12)  .0384(12)  -.0044(11)  .0052(12)  -.0028(11)
  C4  .0453(13)  .0421(13)  .0391(12)  .0042(12)  .0015(12)  -.0084(11)
  C5  .0550(15)  .0428(13)  .0519(14)  .0016(12)  -.0103(14)  -.0108(13)
  C6  .0401(13)  .0410(13)  .0506(15)  .0008(11)  -.0019(12)  .0027(12)
  C7  .0565(15)  .0378(13)  .0488(15)  .0035(12)  .0028(15)  .0059(13)
  C8  .0736(18)  .0403(14)  .0611(16)  -.0112(14)  .0075(16)  -.0137(14)
  C9  .0419(14)  .0549(16)  .075(2)  -.0084(12)  -.0026(15)  -.0121(16)
  C10  .0670(19)  .085(2)  .066(2)  .0071(16)  -.0192(16)  -.0026(18)
  C11  .0499(15)  .0621(17)  .078(2)  -.0011(13)  -.0132(16)  .0091(17)
  C12  .0535(15)  .0485(14)  .0674(18)  -.0076(13)  .0043(15)  .0150(15)
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 C7 . 1.201(3) no
  O2 C7 . 1.323(3) no
  O3 C4 . 1.218(3) no
  C1 C7 . 1.509(4) no
  C1 C2 . 1.535(3) no
  C1 C6 . 1.547(3) no
  C2 C8 . 1.538(3) yes
  C2 C3 . 1.539(3) no
  C3 C4 . 1.514(3) no
  C3 C9 . 1.533(4) yes
  C4 C5 . 1.491(3) no
  C5 C6 . 1.537(3) no
  C6 C12 . 1.526(4) yes
  C6 C11 . 1.533(4) yes
  C9 C10 . 1.518(4) no
  O2 H2 .  .8200 no
  C1 H1 .  .9800 no
  C2 H2A .  .9800 no
  C3 H3 .  .9800 no
  C5 H5A .  .9700 no
  C5 H5B .  .9700 no
  C8 H8A .  .9600 no
  C8 H8B .  .9600 no
  C8 H8C .  .9600 no
  C9 H9A .  .9700 no
  C9 H9B .  .9700 no
  C10 H10A .  .9600 no
  C10 H10B .  .9600 no
  C10 H10C .  .9600 no
  C11 H11A .  .9600 no
  C11 H11B .  .9600 no
  C11 H11C .  .9600 no
  C12 H12A .  .9600 no
  C12 H12B .  .9600 no
  C12 H12C .  .9600 no