#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013148.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_2013148
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o167
_journal_page_last  o170
_publ_section_title
;
The epimeric 9-oxobicyclo[3.3.1]nonane-3-carboxylic acids: hydrogen-bonding
patterns of the endo acid and the lactol of the exo acid
;
loop_
_publ_author_name
  'Papadakis, Markos M.'
  'Pavon, Jorge A.'
  'Lalancette, Roger A.'
  'Thompson, Hugh W.'
_chemical_formula_moiety  'C10 H14 O3'
_chemical_formula_sum  'C10 H14 O3'
_chemical_formula_weight  182.21
_chemical_melting_point  404
_symmetry_cell_setting  'triclinic'
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  6.6170(10)
_cell_length_b  7.3160(10)
_cell_length_c  10.421(2)
_cell_angle_alpha  71.470(10)
_cell_angle_beta  73.44(2)
_cell_angle_gamma  77.290(10)
_cell_volume  453.81(13)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.333
_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 0.8706(2) 0.8265(2) 0.46312(14) 0.0561(4) Uani d . 1 . . O
  O2 0.8195(2) 0.10089(19) 0.90893(15) 0.0554(4) Uani d . 1 . . O
  O3 1.0978(2) 0.2324(2) 0.90087(18) 0.0607(4) Uani d . 1 . . O
  C1 0.6182(3) 0.6068(3) 0.59638(19) 0.0400(5) Uani d . 1 . . C
  C2 0.6791(3) 0.4122(3) 0.7012(2) 0.0431(5) Uani d . 1 . . C
  C3 0.8636(3) 0.4217(3) 0.75880(19) 0.0394(5) Uani d . 1 . . C
  C4 0.8174(3) 0.5993(3) 0.81780(19) 0.0415(5) Uani d . 1 . . C
  C5 0.7591(3) 0.7915(3) 0.70982(19) 0.0391(5) Uani d . 1 . . C
  C6 0.5307(3) 0.8922(3) 0.7583(2) 0.0457(5) Uani d . 1 . . C
  C7 0.3613(3) 0.7696(3) 0.7749(2) 0.0470(5) Uani d . 1 . . C
  C8 0.3889(3) 0.7034(3) 0.6455(2) 0.0455(5) Uani d . 1 . . C
  C9 0.7651(3) 0.7493(3) 0.57578(19) 0.0386(4) Uani d . 1 . . C
  C10 0.9228(3) 0.2367(3) 0.8624(2) 0.0423(5) Uani d . 1 . . C
  H3 1.125(4) 0.115(4) 0.967(3) 0.080 Uiso d . 1 . . H
  H1 0.6318 0.5824 0.5069 0.048 Uiso calc R 1 . . H
  H2A 0.5564 0.3817 0.7775 0.052 Uiso calc R 1 . . H
  H2B 0.7192 0.3086 0.6555 0.052 Uiso calc R 1 . . H
  H3A 0.9878 0.4411 0.6801 0.047 Uiso calc R 1 . . H
  H4A 0.9421 0.6081 0.8457 0.050 Uiso calc R 1 . . H
  H4B 0.7008 0.5811 0.8998 0.050 Uiso calc R 1 . . H
  H5 0.8614 0.8804 0.6918 0.047 Uiso calc R 1 . . H
  H6A 0.5175 0.9171 0.8465 0.055 Uiso calc R 1 . . H
  H6B 0.5064 1.0166 0.6909 0.055 Uiso calc R 1 . . H
  H7A 0.3689 0.6561 0.8539 0.056 Uiso calc R 1 . . H
  H7B 0.2215 0.8452 0.7940 0.056 Uiso calc R 1 . . H
  H8A 0.3530 0.8150 0.5712 0.055 Uiso calc R 1 . . H
  H8B 0.2910 0.6115 0.6655 0.055 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 0.0579(9) 0.0587(9) 0.0442(8) -0.0183(7) 0.0080(7) -0.0145(7)
  O2 0.0549(9) 0.0459(8) 0.0662(10) -0.0143(7) -0.0196(8) -0.0065(7)
  O3 0.0521(10) 0.0502(9) 0.0822(11) -0.0088(7) -0.0307(8) -0.0071(8)
  C1 0.0418(11) 0.0447(10) 0.0387(10) -0.0071(8) -0.0074(8) -0.0196(8)
  C2 0.0428(11) 0.0381(10) 0.0538(11) -0.0075(9) -0.0108(9) -0.0191(9)
  C3 0.0359(11) 0.0382(10) 0.0449(11) -0.0056(8) -0.0044(8) -0.0165(9)
  C4 0.0405(11) 0.0449(11) 0.0440(11) -0.0071(9) -0.0081(9) -0.0198(9)
  C5 0.0402(11) 0.0374(10) 0.0435(10) -0.0114(8) -0.0049(8) -0.0166(8)
  C6 0.0502(12) 0.0418(11) 0.0477(11) -0.0028(9) -0.0072(9) -0.0220(9)
  C7 0.0374(11) 0.0503(12) 0.0532(12) -0.0019(9) -0.0035(9) -0.0232(10)
  C8 0.0414(11) 0.0457(11) 0.0526(12) -0.0077(9) -0.0112(9) -0.0163(9)
  C9 0.0358(10) 0.0360(10) 0.0406(11) -0.0031(8) -0.0028(9) -0.0126(8)
  C10 0.0362(11) 0.0427(11) 0.0497(11) -0.0016(9) -0.0066(9) -0.0206(9)
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 C9 . 1.212(2) ?
  O2 C10 . 1.222(2) y
  O3 C10 . 1.320(2) y
  C1 C9 . 1.504(2) ?
  C1 C8 . 1.542(3) ?
  C1 C2 . 1.547(3) ?
  C2 C3 . 1.528(3) ?
  C3 C10 . 1.493(3) ?
  C3 C4 . 1.545(2) ?
  C4 C5 . 1.548(3) ?
  C5 C9 . 1.511(2) ?
  C5 C6 . 1.547(3) ?
  C6 C7 . 1.524(3) ?
  C7 C8 . 1.523(3) ?
  O3 H3 . 0.93(3) ?
  C1 H1 . 0.9800 ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 H3A . 0.9800 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 H5 . 0.9800 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
_cod_database_code 2013148