#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012568.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_2012568
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o154
_journal_page_last  o156
_publ_section_title
;
(+-)-3-Oxocyclohexanecarboxylic and -acetic acids: contrasting
hydrogen-bonding patterns in two homologous keto acids
;
loop_
_publ_author_name
  'Barcon, Alan'
  'Brunskill, Andrew P. J.'
  'Lalancette, Roger A.'
  'Thompson, Hugh W.'
_chemical_name_common  'cyclohexanone-3-carboxylic acid'
_chemical_formula_moiety  'C7 H10 O3'
_chemical_formula_sum  'C7 H10 O3'
_chemical_formula_weight  142.15
_chemical_melting_point  344
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  6.3346(17)
_cell_length_b  10.758(3)
_cell_length_c  11.012(3)
_cell_angle_alpha  90.00
_cell_angle_beta  94.202(17)
_cell_angle_gamma  90.00
_cell_volume  748.4(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.262
_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  .9648(3)  .82762(18)  .85285(17)  .0772(6) Uani d . 1 . . O
  O2  .4742(3)  .7526(2)  .46565(16)  .0916(7) Uani d . 1 . . O
  O3  .2145(3)  .66753(18)  .56032(15)  .0756(6) Uani d . 1 . . O
  C1  .5417(3)  .6873(2)  .67418(19)  .0462(6) Uani d . 1 . . C
  C2  .7397(4)  .7681(2)  .6814(2)  .0547(6) Uani d . 1 . . C
  C3  .8843(4)  .7422(2)  .7935(2)  .0567(6) Uani d . 1 . . C
  C4  .9277(4)  .6081(2)  .8232(3)  .0679(8) Uani d . 1 . . C
  C5  .7290(4)  .5273(2)  .8102(2)  .0676(8) Uani d . 1 . . C
  C6  .6022(4)  .5499(2)  .6887(2)  .0631(7) Uani d . 1 . . C
  C7  .4111(4)  .7079(2)  .5551(2)  .0505(6) Uani d . 1 . . C
  H3  .1480  .6799  .4947  .080 Uiso calc R 1 . . H
  H1  .4559  .7105  .7411  .048(6) Uiso calc R 1 . . H
  H2A  .8164  .7537  .6096  .073(8) Uiso calc R 1 . . H
  H2B  .6981  .8549  .6814  .062(7) Uiso calc R 1 . . H
  H4A  .9901  .6020  .9061  .077(8) Uiso calc R 1 . . H
  H4B 1.0300  .5764  .7695  .104(11) Uiso calc R 1 . . H
  H5A  .6408  .5455  .8764  .076(8) Uiso calc R 1 . . H
  H5B  .7694  .4404  .8161  .084(9) Uiso calc R 1 . . H
  H6A  .4748  .4995  .6846  .092(9) Uiso calc R 1 . . H
  H6B  .6858  .5250  .6224  .072(8) 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  .0714(12)  .0784(13)  .0764(13)  -.0169(10)  -.0302(10)  .0056(10)
  O2  .0828(14)  .1439(19)  .0462(10)  -.0330(13)  -.0081(9)  .0250(12)
  O3  .0498(10)  .1197(16)  .0556(11)  -.0071(11)  -.0077(8)  .0055(10)
  C1  .0436(12)  .0540(14)  .0409(12)  .0010(11)  .0021(9)  -.0025(10)
  C2  .0527(14)  .0538(15)  .0558(14)  .0017(12)  -.0078(12)  .0067(12)
  C3  .0438(13)  .0668(17)  .0580(14)  -.0018(13)  -.0061(11)  .0084(14)
  C4  .0613(16)  .0720(18)  .0673(17)  .0117(14)  -.0154(14)  .0112(14)
  C5  .0793(19)  .0558(17)  .0668(17)  .0066(14)  .0000(14)  .0125(13)
  C6  .0689(18)  .0589(17)  .0608(15)  -.0036(14)  -.0003(13)  -.0021(13)
  C7  .0502(14)  .0598(15)  .0410(12)  -.0002(12)  -.0007(10)  -.0043(11)
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 . 1.218(3) ?
  O2 C7 . 1.191(3) y
  O3 C7 . 1.324(3) y
  C1 C7 . 1.515(3) ?
  C1 C2 . 1.523(3) ?
  C1 C6 . 1.533(3) ?
  C2 C3 . 1.508(3) ?
  C3 C4 . 1.500(3) ?
  C4 C5 . 1.528(4) ?
  C5 C6 . 1.529(3) ?
  O3 H3 .  .8200 ?
  C1 H1 .  .9800 ?
  C2 H2A .  .9700 ?
  C2 H2B .  .9700 ?
  C4 H4A .  .9700 ?
  C4 H4B .  .9700 ?
  C5 H5A .  .9700 ?
  C5 H5B .  .9700 ?
  C6 H6A .  .9700 ?
  C6 H6B .  .9700 ?