#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012569.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_2012569
_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-acetic acid'
_chemical_formula_moiety  'C8 H12 O3'
_chemical_formula_sum  'C8 H12 O3'
_chemical_formula_weight  156.18
_chemical_melting_point  351
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  6.625(2)
_cell_length_b  5.6690(10)
_cell_length_c  21.841(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.33(2)
_cell_angle_gamma  90.00
_cell_volume  820.3(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  241(2)
_exptl_crystal_density_diffrn  1.265
_diffrn_ambient_temperature  241(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  .4354(3) 1.2427(4)  .24060(8)  .0728(6) Uani d . 1 . . O
  O2  .9507(3)  .7174(3)  .04788(8)  .0726(7) Uani d . 1 . . O
  O3  .8410(3)  .3523(3)  .05366(9)  .0759(7) Uani d . 1 . . O
  C1  .6287(3)  .8371(4)  .13399(9)  .0438(6) Uani d . 1 . . C
  C2  .5437(4)  .8791(5)  .19864(10)  .0521(7) Uani d . 1 . . C
  C3  .4123(3) 1.0940(5)  .20135(10)  .0507(7) Uani d . 1 . . C
  C4  .2548(4) 1.1152(5)  .15228(11)  .0588(7) Uani d . 1 . . C
  C5  .3413(4) 1.0669(5)  .08862(10)  .0561(7) Uani d . 1 . . C
  C6  .4571(4)  .8376(5)  .08710(10)  .0538(7) Uani d . 1 . . C
  C7  .7492(4)  .6092(5)  .13351(10)  .0508(6) Uani d . 1 . . C
  C8  .8545(3)  .5613(5)  .07400(10)  .0445(6) Uani d . 1 . . C
  H3  .9167  .3366  .0238  .114 Uiso calc R 1 . . H
  H1  .7213  .9687  .1241  .053 Uiso calc R 1 . . H
  H2A  .4650  .7410  .2111  .063 Uiso calc R 1 . . H
  H2B  .6560  .8972  .2277  .063 Uiso calc R 1 . . H
  H4A  .1974 1.2745  .1531  .071 Uiso calc R 1 . . H
  H4B  .1457 1.0031  .1604  .071 Uiso calc R 1 . . H
  H5A  .2308 1.0605  .0587  .067 Uiso calc R 1 . . H
  H5B  .4312 1.1966  .0771  .067 Uiso calc R 1 . . H
  H6A  .5125  .8138  .0461  .065 Uiso calc R 1 . . H
  H6B  .3650  .7066  .0957  .065 Uiso calc R 1 . . H
  H7A  .8503  .6153  .1664  .061 Uiso calc R 1 . . H
  H7B  .6579  .4776  .1423  .061 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  .0752(13)  .0841(15)  .0592(11)  .0082(11)  .0059(10)  -.0206(11)
  O2  .0850(14)  .0670(13)  .0661(12)  -.0178(11)  .0378(11)  -.0142(10)
  O3  .0927(15)  .0632(13)  .0723(13)  -.0152(11)  .0451(11)  -.0174(10)
  C1  .0439(12)  .0553(14)  .0323(11)  -.0045(11)  .0063(9)  -.0024(10)
  C2  .0553(14)  .0696(17)  .0315(12)  .0056(13)  .0058(10)  -.0041(11)
  C3  .0472(13)  .0688(17)  .0364(12)  -.0027(13)  .0134(10)  -.0047(12)
  C4  .0501(14)  .0725(19)  .0537(15)  .0078(14)  .0057(12)  .0009(13)
  C5  .0512(14)  .0739(18)  .0433(13)  -.0007(14)  -.0011(11)  .0030(13)
  C6  .0541(14)  .0704(18)  .0371(12)  -.0019(13)  .0017(11)  -.0058(12)
  C7  .0518(14)  .0629(16)  .0379(12)  -.0015(13)  .0066(11)  -.0006(11)
  C8  .0389(12)  .0550(15)  .0397(12)  -.0037(12)  .0057(10)  -.0019(12)
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 . 1.211(3) ?
  O2 C8 . 1.232(3) y
  O3 C8 . 1.269(3) y
  C1 C7 . 1.519(3) ?
  C1 C6 . 1.526(3) ?
  C1 C2 . 1.542(3) ?
  C2 C3 . 1.499(4) ?
  C3 C4 . 1.496(3) ?
  C4 C5 . 1.532(3) ?
  C5 C6 . 1.510(4) ?
  C7 C8 . 1.504(3) ?
  O3 H3 .  .8300 ?
  C1 H1 .  .9900 ?
  C2 H2A .  .9800 ?
  C2 H2B .  .9800 ?
  C4 H4A .  .9800 ?
  C4 H4B .  .9800 ?
  C5 H5A .  .9800 ?
  C5 H5B .  .9800 ?
  C6 H6A .  .9800 ?
  C6 H6B .  .9800 ?
  C7 H7A .  .9800 ?
  C7 H7B .  .9800 ?