#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012754.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_2012754
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o321
_journal_page_last  o322
_publ_section_title
;
(+-)-12-Oxotricyclo[6.2.2.0^1,6^]dodecane-10-carboxylic acid:
hydrogen bonding in a tricyclic \d-keto acid
;
loop_
_publ_author_name
  'Papadakis, Markos M.'
  'Martins, Sonia P.'
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_formula_moiety  'C13 H18 O3'
_chemical_formula_sum  'C13 H18 O3'
_chemical_formula_iupac  'C13 H18 O3'
_chemical_formula_weight  222.27
_chemical_melting_point  416
_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  12.832(4)
_cell_length_b  7.961(3)
_cell_length_c  11.809(4)
_cell_angle_alpha  90.00
_cell_angle_beta  99.79(2)
_cell_angle_gamma  90.00
_cell_volume  1188.8(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.242
_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 0.12497(14) 0.4104(3) 1.09881(14) 0.0874(6) Uani d . 1 . . O
  O2 0.38247(10) 0.07214(18) 1.02304(11) 0.0552(4) Uani d . 1 . . O
  O3 0.44970(11) 0.08608(18) 0.86133(12) 0.0533(4) Uani d . 1 . . O
  C1 0.28654(13) 0.3970(2) 0.87176(14) 0.0371(4) Uani d . 1 . . C
  C2 0.39291(14) 0.4661(2) 0.84855(17) 0.0450(5) Uani d . 1 . . C
  C3 0.39529(17) 0.6587(3) 0.84045(19) 0.0574(6) Uani d . 1 . . C
  C4 0.30510(19) 0.7220(3) 0.7498(2) 0.0663(6) Uani d . 1 . . C
  C5 0.19840(18) 0.6609(3) 0.77377(19) 0.0622(6) Uani d . 1 . . C
  C6 0.19450(14) 0.4688(2) 0.78163(16) 0.0453(5) Uani d . 1 . . C
  C7 0.08695(15) 0.4020(3) 0.80629(18) 0.0595(6) Uani d . 1 . . C
  C8 0.10278(14) 0.2847(3) 0.91054(18) 0.0574(6) Uani d . 1 . . C
  C9 0.17441(15) 0.1368(3) 0.88968(19) 0.0540(5) Uani d . 1 . . C
  C10 0.27888(13) 0.2023(2) 0.85609(15) 0.0392(4) Uani d . 1 . . C
  C11 0.26769(14) 0.4411(3) 0.99350(15) 0.0467(5) Uani d . 1 . . C
  C12 0.16025(16) 0.3818(3) 1.01151(17) 0.0546(6) Uani d . 1 . . C
  C13 0.37436(13) 0.1135(2) 0.92161(15) 0.0390(4) Uani d . 1 . . C
  H3 0.503(2) 0.025(4) 0.905(3) 0.100(9) Uiso d . 1 . . H
  H2A 0.4486 0.4297 0.9097 0.054 Uiso calc R 1 . . H
  H2B 0.4075 0.4188 0.7772 0.054 Uiso calc R 1 . . H
  H3A 0.3892 0.7070 0.9144 0.069 Uiso calc R 1 . . H
  H3B 0.4623 0.6943 0.8208 0.069 Uiso calc R 1 . . H
  H4A 0.3153 0.6828 0.6747 0.080 Uiso calc R 1 . . H
  H4B 0.3058 0.8439 0.7489 0.080 Uiso calc R 1 . . H
  H5A 0.1430 0.6991 0.7129 0.075 Uiso calc R 1 . . H
  H5B 0.1852 0.7092 0.8454 0.075 Uiso calc R 1 . . H
  H6 0.2036 0.4246 0.7065 0.054 Uiso calc R 1 . . H
  H7A 0.0428 0.4959 0.8205 0.071 Uiso calc R 1 . . H
  H7B 0.0509 0.3419 0.7395 0.071 Uiso calc R 1 . . H
  H8 0.0346 0.2439 0.9262 0.069 Uiso calc R 1 . . H
  H9A 0.1378 0.0663 0.8286 0.065 Uiso calc R 1 . . H
  H9B 0.1903 0.0693 0.9588 0.065 Uiso calc R 1 . . H
  H10 0.2764 0.1782 0.7743 0.047 Uiso calc R 1 . . H
  H11A 0.3218 0.3886 1.0498 0.056 Uiso calc R 1 . . H
  H11B 0.2728 0.5617 1.0045 0.056 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 0.0752(11) 0.1378(18) 0.0559(9) 0.0190(11) 0.0309(8) 0.0022(11)
  O2 0.0485(8) 0.0684(10) 0.0497(8) 0.0191(7) 0.0116(6) 0.0152(7)
  O3 0.0483(8) 0.0601(9) 0.0542(8) 0.0208(7) 0.0165(7) 0.0105(7)
  C1 0.0340(9) 0.0402(10) 0.0363(9) 0.0062(8) 0.0037(7) -0.0036(8)
  C2 0.0423(10) 0.0423(11) 0.0499(11) 0.0035(8) 0.0068(8) -0.0003(9)
  C3 0.0649(13) 0.0434(12) 0.0643(13) -0.0040(10) 0.0121(11) 0.0012(10)
  C4 0.0899(17) 0.0404(12) 0.0681(14) 0.0077(12) 0.0116(12) 0.0075(11)
  C5 0.0707(14) 0.0526(13) 0.0594(13) 0.0253(11) 0.0000(11) 0.0041(11)
  C6 0.0438(10) 0.0508(12) 0.0394(10) 0.0156(9) 0.0023(8) -0.0009(9)
  C7 0.0376(10) 0.0816(16) 0.0560(12) 0.0178(10) -0.0015(9) 0.0020(12)
  C8 0.0298(9) 0.0814(16) 0.0623(12) 0.0042(10) 0.0114(9) 0.0073(12)
  C9 0.0392(10) 0.0577(13) 0.0631(12) -0.0068(9) 0.0025(9) 0.0034(11)
  C10 0.0367(9) 0.0405(10) 0.0393(9) 0.0041(8) 0.0032(7) -0.0018(8)
  C11 0.0473(11) 0.0524(12) 0.0396(10) 0.0118(9) 0.0052(8) -0.0031(9)
  C12 0.0497(11) 0.0722(15) 0.0442(11) 0.0208(10) 0.0146(9) 0.0084(10)
  C13 0.0390(9) 0.0327(9) 0.0457(10) 0.0035(8) 0.0080(8) -0.0005(8)
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 C12 . 1.216(2) ?
  O2 C13 . 1.229(2) y
  O3 C13 . 1.313(2) y
  C1 C11 . 1.538(2) ?
  C1 C2 . 1.539(2) ?
  C1 C6 . 1.558(2) ?
  C1 C10 . 1.562(3) ?
  C2 C3 . 1.537(3) ?
  C3 C4 . 1.522(3) ?
  C4 C5 . 1.524(3) ?
  C5 C6 . 1.533(3) ?
  C6 C7 . 1.552(3) ?
  C7 C8 . 1.531(3) ?
  C8 C12 . 1.505(3) ?
  C8 C9 . 1.539(3) ?
  C9 C10 . 1.552(3) ?
  C10 C13 . 1.509(2) ?
  C11 C12 . 1.506(3) ?
  O3 H3 . 0.92(3) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6 . 0.9800 ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 H8 . 0.9800 ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 H10 . 0.9800 ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?