#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013978.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_2013978
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o242
_journal_page_last  o244
_publ_section_title
;
(+-)-7-Oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-1-acetic acid: catemeric
hydrogen bonding and diastereomeric disorder in a bicyclic unsaturated \e-keto
acid
;
loop_
_publ_author_name
  'Davison, Mark'
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_formula_moiety  'C12 H16 O3'
_chemical_formula_sum  'C12 H16 O3'
_chemical_formula_iupac  'C12 H16 O3'
_chemical_formula_weight  208.25
_chemical_melting_point  368
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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  10.354(2)
_cell_length_b  8.269(2)
_cell_length_c  13.512(3)
_cell_angle_alpha  90.00
_cell_angle_beta  108.27(2)
_cell_angle_gamma  90.00
_cell_volume  1098.5(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.259
_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 0.0518(2) 0.6571(3) 0.18194(15) 0.0798(8) Uani d . 1 A . O
  O2 0.5207(4) 0.2789(4) 0.6612(4) 0.1271(13) Uani d . 1 A . O
  O3 0.4088(3) 0.0841(4) 0.5669(2) 0.1077(10) Uani d . 1 A . O
  H3 0.4639 0.0303 0.6116 0.162 Uiso calc R 1 . . H
  C1 0.2924(7) 0.4849(9) 0.5399(4) 0.0503(17) Uani d P 0.656(11) A 1 C
  H1A 0.3802 0.5379 0.5725 0.060 Uiso calc PR 0.656(11) A 1 H
  C1' 0.2446(14) 0.4157(14) 0.5152(8) 0.042(3) Uani d P 0.344(11) A 2 C
  H1'A 0.1930 0.3228 0.4780 0.051 Uiso calc PR 0.344(11) A 2 H
  C2 0.2188(4) 0.4589(5) 0.6234(2) 0.0816(12) Uani d . 1 . . C
  H2A 0.1257 0.4238 0.5911 0.098 Uiso calc R 1 A 1 H
  H2B 0.2660 0.3789 0.6745 0.098 Uiso calc R 1 A 1 H
  C3 0.2232(4) 0.6210(5) 0.6726(3) 0.0888(12) Uani d . 1 A . C
  H3A 0.3171 0.6533 0.7048 0.107 Uiso calc R 1 . . H
  H3B 0.1800 0.6152 0.7266 0.107 Uiso calc R 1 . . H
  C4 0.1518(4) 0.7444(5) 0.5930(2) 0.0855(11) Uani d . 1 . . C
  H4B 0.1631 0.8498 0.6262 0.103 Uiso calc R 1 A . H
  H4C 0.0554 0.7199 0.5694 0.103 Uiso calc R 1 . . H
  C4a 0.2017(3) 0.7540(4) 0.4980(2) 0.0688(10) Uani d . 1 A . C
  H4A 0.2950 0.7957 0.5219 0.083 Uiso calc R 1 . . H
  C5 0.1179(4) 0.8711(4) 0.4183(2) 0.0770(11) Uani d . 1 . . C
  H5A 0.1413 0.9805 0.4435 0.092 Uiso calc R 1 A . H
  H5B 0.0225 0.8543 0.4105 0.092 Uiso calc R 1 . . H
  C6 0.1385(4) 0.8541(4) 0.3131(2) 0.0714(10) Uani d . 1 A . C
  H6A 0.0790 0.9286 0.2641 0.086 Uiso calc R 1 . . H
  H6B 0.2317 0.8809 0.3187 0.086 Uiso calc R 1 . . H
  C7 0.1083(3) 0.6861(4) 0.2746(2) 0.0577(8) Uani d . 1 . . C
  C8 0.1547(3) 0.5592(4) 0.3513(2) 0.0604(8) Uani d . 1 A . C
  H8A 0.1482 0.4524 0.3286 0.072 Uiso calc R 1 . . H
  C8a 0.2068(3) 0.5891(4) 0.4539(2) 0.0609(9) Uani d . 1 . . C
  C9 0.3161(7) 0.3199(8) 0.4995(4) 0.059(2) Uani d P 0.656(11) A 1 C
  H9A 0.3432 0.3321 0.4374 0.070 Uiso calc PR 0.656(11) A 1 H
  H9B 0.2329 0.2570 0.4816 0.070 Uiso calc PR 0.656(11) A 1 H
  C9' 0.3987(11) 0.4037(14) 0.5386(7) 0.054(4) Uani d P 0.344(11) A 2 C
  H9'A 0.4457 0.4861 0.5879 0.065 Uiso calc PR 0.344(11) A 2 H
  H9'B 0.4238 0.4139 0.4755 0.065 Uiso calc PR 0.344(11) A 2 H
  C10 0.4309(6) 0.2311(7) 0.5864(4) 0.0935(14) Uani d . 1 . . C
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 0.1065(19) 0.0716(16) 0.0478(12) 0.0016(14) 0.0048(12) 0.0019(11)
  O2 0.111(3) 0.0520(17) 0.211(4) 0.0012(18) 0.039(3) -0.001(2)
  O3 0.109(2) 0.099(2) 0.0893(19) 0.0200(19) -0.0060(15) 0.0171(18)
  C1 0.054(4) 0.049(4) 0.045(3) -0.002(3) 0.012(3) -0.005(3)
  C1' 0.050(7) 0.033(7) 0.039(5) -0.012(5) 0.008(5) 0.004(5)
  C2 0.087(3) 0.107(3) 0.0580(19) 0.031(2) 0.0336(18) 0.023(2)
  C3 0.089(3) 0.127(4) 0.0495(18) -0.009(3) 0.0203(18) -0.003(2)
  C4 0.105(3) 0.092(3) 0.0573(19) -0.002(2) 0.0218(19) -0.021(2)
  C4a 0.063(2) 0.079(2) 0.0531(17) -0.0074(18) 0.0027(15) -0.0035(17)
  C5 0.091(3) 0.060(2) 0.068(2) -0.0024(19) 0.0065(18) -0.0094(17)
  C6 0.084(2) 0.056(2) 0.0636(19) -0.0083(18) 0.0076(17) 0.0122(16)
  C7 0.0619(18) 0.058(2) 0.0516(17) 0.0014(16) 0.0154(14) 0.0040(16)
  C8 0.076(2) 0.0525(18) 0.0567(17) 0.0127(17) 0.0274(15) 0.0077(16)
  C8a 0.0568(19) 0.077(2) 0.0540(17) 0.0165(16) 0.0244(15) 0.0125(17)
  C9 0.065(4) 0.052(4) 0.053(3) 0.007(3) 0.011(3) -0.002(3)
  C9' 0.047(7) 0.065(7) 0.049(5) -0.002(6) 0.012(4) 0.017(5)
  C10 0.102(3) 0.087(4) 0.109(4) 0.034(3) 0.059(3) 0.035(3)
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 . 1.228(3) ?
  O2 C10 . 1.205(5) y
  O3 C10 . 1.250(6) y
  O3 H3 . 0.8200 ?
  C1 C8a . 1.495(6) ?
  C1 C9 . 1.518(11) ?
  C1 C2 . 1.562(7) ?
  C1 H1A . 0.9800 ?
  C1' C9' . 1.53(2) ?
  C1' C2 . 1.607(12) ?
  C1' C8a . 1.640(10) ?
  C1' H1'A . 0.9800 ?
  C2 C3 . 1.491(5) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C4 . 1.499(5) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 C4a . 1.529(4) ?
  C4 H4B . 0.9700 ?
  C4 H4C . 0.9700 ?
  C4a C8a . 1.496(5) ?
  C4a C5 . 1.504(4) ?
  C4a H4A . 0.9800 ?
  C5 C6 . 1.508(4) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 C7 . 1.483(4) ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 C8 . 1.447(4) ?
  C8 C8a . 1.343(4) ?
  C8 H8A . 0.9300 ?
  C9 C10 . 1.567(7) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C9' C10 . 1.559(10) ?
  C9' H9'A . 0.9700 ?
  C9' H9'B . 0.9700 ?