#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008890.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_2008890
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1600
_journal_page_last  1605
_publ_section_title
;
(+)- and (+/-)-Ketopinic acid: hydrogen-bonding patterns in a \b-keto acid in
its enantiomeric and racemic forms and enantiomeric disordering in the racemate
;
loop_
_publ_author_name
  'Lalancette, Roger A.'
  'Cot\'e, Marie L.'
  'Smith III, William J.'
  'Thompson, Hugh W.'
  'Vanderhoff, Peggy A.'
  'Brunskill, Andrew P. J.'
  'Campana, Charles'
  'Burshtein, Izya'
  'Rose, John P.'
 '(+)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid'
_chemical_name_common  '(+)-ketopinic acid'
_chemical_formula_moiety  'C10 H14 O3'
_chemical_formula_sum  'C10 H14 O3'
_chemical_formula_structural  'C20 H28 O6'
_chemical_formula_analytical  'C10 H14 O3'
_chemical_formula_weight  182.21
_chemical_melting_point  .502E-305
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  7.3630(10)
_cell_length_b  11.2990(10)
_cell_length_c  23.502(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1955.2(4)
_cell_formula_units_Z  8
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.238
_diffrn_ambient_temperature  298(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 0.1899(6) 1.1483(3) 0.07413(15) 0.1234(16) Uani d . 1 . . O
  O2 0.1198(4) 0.8342(3) 0.06613(12) 0.0851(10) Uani d . 1 . . O
  O3 0.3865(4) 0.8946(3) 0.09592(11) 0.0718(9) Uani d . 1 . . O
  C1 0.2672(5) 0.9814(3) 0.01278(13) 0.0406(9) Uani d . 1 . . C
  C2 0.2096(7) 1.1082(3) 0.02763(19) 0.0726(13) Uani d . 1 . . C
  C3 0.1792(7) 1.1691(4) -0.02876(19) 0.0849(15) Uani d . 1 . . C
  C4 0.2237(6) 1.0727(4) -0.07162(17) 0.0618(11) Uani d . 1 . . C
  C5 0.4294(6) 1.0564(4) -0.07025(17) 0.0675(12) Uani d . 1 . . C
  C6 0.4615(5) 0.9999(4) -0.01183(15) 0.0579(11) Uani d . 1 . . C
  C7 0.1528(5) 0.9598(3) -0.04184(15) 0.0525(10) Uani d . 1 . . C
  C8 0.2011(6) 0.8460(4) -0.07227(17) 0.0772(13) Uani d . 1 . . C
  C9 -0.0534(5) 0.9623(5) -0.0317(2) 0.0941(17) Uani d . 1 . . C
  C10 0.2584(5) 0.8980(3) 0.06109(14) 0.0443(9) Uani d . 1 . . C
  H2 0.1304 0.7919 0.0943 0.062(13) Uiso calc PR 0.50 . . H
  H3 0.3646 0.8450 0.1204 0.062(13) Uiso calc PR 0.50 . . H
  H3A 0.2595 1.2366 -0.0332 0.078(4) Uiso calc R 1 . . H
  H3B 0.0543 1.1954 -0.0326 0.078(4) Uiso calc R 1 . . H
  H4A 0.1735 1.0860 -0.1097 0.072(9) Uiso calc R 1 . . H
  H5A 0.4916 1.1318 -0.0734 0.078(4) Uiso calc R 1 . . H
  H5B 0.4698 1.0047 -0.1007 0.078(4) Uiso calc R 1 . . H
  H6A 0.5323 1.0519 0.0124 0.078(4) Uiso calc R 1 . . H
  H6B 0.5247 0.9249 -0.0156 0.078(4) Uiso calc R 1 . . H
  H8A 0.3305 0.8407 -0.0763 0.117(5) Uiso calc R 1 . . H
  H8B 0.1456 0.8455 -0.1092 0.117(5) Uiso calc R 1 . . H
  H8C 0.1576 0.7798 -0.0506 0.117(5) Uiso calc R 1 . . H
  H9A -0.0826 1.0252 -0.0058 0.117(5) Uiso calc R 1 . . H
  H9B -0.0916 0.8882 -0.0157 0.117(5) Uiso calc R 1 . . H
  H9C -0.1149 0.9752 -0.0671 0.117(5) Uiso calc R 1 . . H
  O1' 0.2257(5) 0.7970(3) 0.30368(12) 0.0810(10) Uani d . 1 . . O
  O2' 0.3664(3) 0.74821(17) 0.18471(8) 0.0626(8) Uani d . 1 . . O
  O3' 0.0981(3) 0.69042(17) 0.15406(8) 0.0738(9) Uani d R 1 . . O
  C1' 0.1949(4) 0.6212(3) 0.24375(14) 0.0401(8) Uani d . 1 . . C
  C2' 0.2302(5) 0.6908(4) 0.29895(14) 0.0542(10) Uani d . 1 . . C
  C3' 0.2584(7) 0.5991(4) 0.34442(17) 0.0776(14) Uani d . 1 . . C
  C4' 0.2330(6) 0.4839(4) 0.31230(16) 0.0635(11) Uani d . 1 . . C
  C5' 0.0296(6) 0.4742(4) 0.29874(18) 0.0738(13) Uani d . 1 . . C
  C6' 0.0010(5) 0.5700(4) 0.25324(19) 0.0569(10) Uani d . 1 . . C
  C7' 0.3187(5) 0.5108(3) 0.25382(16) 0.0516(10) Uani d . 1 . . C
  C8' 0.5217(5) 0.5415(4) 0.2564(2) 0.0741(13) Uani d . 1 . . C
  C9' 0.2896(7) 0.4143(3) 0.20936(19) 0.0772(14) Uani d . 1 . . C
  C10' 0.2207(5) 0.6907(3) 0.19089(14) 0.0411(8) Uani d . 1 . . C
  H2' 0.3647 0.7828 0.1540 0.062(13) Uiso calc PR 0.50 . . H
  H3' 0.1288 0.7320 0.1271 0.062(13) Uiso calc PR 0.50 . . H
  H3'A 0.1694 0.6072 0.3746 0.078(4) Uiso calc R 1 . . H
  H3'B 0.3793 0.6045 0.3606 0.078(4) Uiso calc R 1 . . H
  H4'A 0.2839 0.4144 0.3315 0.072(9) Uiso calc R 1 . . H
  H5'A -0.0436 0.4898 0.3322 0.078(4) Uiso calc R 1 . . H
  H5'B -0.0004 0.3964 0.2841 0.078(4) Uiso calc R 1 . . H
  H6'A -0.0817 0.6307 0.2666 0.078(4) Uiso calc R 1 . . H
  H6'B -0.0468 0.5361 0.2184 0.078(4) Uiso calc R 1 . . H
  H8'A 0.5395 0.6082 0.2810 0.117(5) Uiso calc R 1 . . H
  H8'B 0.5644 0.5606 0.2189 0.117(5) Uiso calc R 1 . . H
  H8'C 0.5882 0.4748 0.2708 0.117(5) Uiso calc R 1 . . H
  H9'A 0.1619 0.4007 0.2045 0.117(5) Uiso calc R 1 . . H
  H9'B 0.3471 0.3425 0.2218 0.117(5) Uiso calc R 1 . . H
  H9'C 0.3417 0.4388 0.1738 0.117(5) 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 0.218(5) 0.065(2) 0.087(2) 0.028(3) 0.050(3) -0.0121(19)
  O2 0.088(2) 0.102(2) 0.0655(18) -0.044(2) -0.0230(17) 0.0369(18)
  O3 0.0625(18) 0.089(2) 0.0643(18) -0.0102(17) -0.0123(16) 0.0312(16)
  C1 0.042(2) 0.041(2) 0.0386(19) 0.0014(18) 0.0051(17) 0.0023(16)
  C2 0.097(4) 0.053(2) 0.068(3) 0.010(3) 0.029(3) -0.002(2)
  C3 0.100(4) 0.058(3) 0.097(4) 0.023(3) 0.019(3) 0.027(3)
  C4 0.064(3) 0.074(3) 0.047(2) 0.001(2) -0.001(2) 0.021(2)
  C5 0.073(3) 0.067(3) 0.063(3) -0.009(2) 0.019(2) 0.013(2)
  C6 0.048(2) 0.058(2) 0.067(3) -0.007(2) 0.008(2) 0.000(2)
  C7 0.049(2) 0.060(3) 0.048(2) -0.004(2) -0.0023(19) 0.012(2)
  C8 0.099(4) 0.075(3) 0.058(2) -0.029(3) -0.004(3) -0.006(2)
  C9 0.048(3) 0.137(5) 0.097(3) -0.009(3) -0.015(3) 0.050(3)
  C10 0.043(2) 0.044(2) 0.046(2) -0.0013(19) -0.0008(19) -0.0025(17)
  O1' 0.110(3) 0.0642(19) 0.0684(19) -0.005(2) 0.0003(18) -0.0187(16)
  O2' 0.0525(17) 0.0754(18) 0.0598(17) -0.0174(16) -0.0061(14) 0.0240(14)
  O3' 0.085(2) 0.073(2) 0.0631(17) -0.0316(17) -0.0323(17) 0.0231(16)
  C1' 0.0366(19) 0.042(2) 0.0419(19) -0.0021(16) 0.0001(16) -0.0033(17)
  C2' 0.049(2) 0.066(3) 0.047(2) -0.003(2) -0.001(2) -0.001(2)
  C3' 0.087(3) 0.106(4) 0.040(2) -0.014(3) -0.008(2) 0.006(2)
  C4' 0.068(3) 0.062(3) 0.061(3) -0.005(2) -0.005(2) 0.025(2)
  C5' 0.069(3) 0.082(3) 0.070(3) -0.014(3) 0.011(2) 0.019(3)
  C6' 0.042(2) 0.067(3) 0.061(2) -0.0075(19) 0.004(2) 0.001(2)
  C7' 0.052(2) 0.046(2) 0.057(2) 0.0028(18) 0.0001(19) 0.013(2)
  C8' 0.044(2) 0.078(3) 0.101(3) 0.011(2) -0.003(2) 0.022(3)
  C9' 0.098(4) 0.044(2) 0.090(3) 0.008(2) 0.008(3) -0.002(2)
  C10' 0.044(2) 0.0376(19) 0.0420(19) -0.0011(19) -0.0029(18) -0.0038(16)
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 C2 . 1.192(5) y
  O2 C10 . 1.255(4) y
  O3 C10 . 1.249(4) y
  C1 C10 . 1.477(4) ?
  C1 C2 . 1.534(5) ?
  C1 C7 . 1.555(5) ?
  C1 C6 . 1.558(5) ?
  C2 C3 . 1.510(6) ?
  C3 C4 . 1.520(5) ?
  C4 C5 . 1.525(5) ?
  C4 C7 . 1.546(5) ?
  C5 C6 . 1.533(5) ?
  C7 C8 . 1.513(5) ?
  C7 C9 . 1.537(5) ?
  O1' C2' . 1.205(4) y
  O2' C10' . 1.263(4) y
  O3' C10' . 1.251(4) y
  C1' C10' . 1.482(4) ?
  C1' C2' . 1.539(5) ?
  C1' C6' . 1.556(5) ?
  C1' C7' . 1.562(5) ?
  C2' C3' . 1.503(5) ?
  C3' C4' . 1.517(6) ?
  C4' C5' . 1.535(6) ?
  C4' C7' . 1.543(5) ?
  C5' C6' . 1.536(5) ?
  C7' C9' . 1.526(5) ?
  C7' C8' . 1.536(5) ?