#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008891.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_2008891
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_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  'C10 H14 O3'
_chemical_formula_analytical  'C10 H14 O3'
_chemical_formula_weight  182.21
_chemical_melting_point  511
_symmetry_cell_setting  'triclinic'
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.0947(3)
_cell_length_b  11.8316(6)
_cell_length_c  12.1662(6)
_cell_angle_alpha  72.0130(10)
_cell_angle_beta  77.0190(10)
_cell_angle_gamma  86.5460(10)
_cell_volume  946.47(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  123(2)
_exptl_crystal_density_diffrn  1.279
_exptl_crystal_density_meas  1.260(10)
_diffrn_ambient_temperature  123(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
  O1D 1.1562(11) 0.5269(6) 0.3060(4) 0.0405(8) Uani d P 0.764(3) A 1 O
  O1L 1.184(4) 0.539(2) 0.298(2) 0.067(7) Uani d P 0.236(3) A 2 O
  O2D 0.8766(12) 0.4918(10) 0.1413(8) 0.0433(13) Uani d P 0.50 A 1 O
  O3D 1.0704(8) 0.6296(5) 0.0118(4) 0.0386(9) Uani d P 0.50 A 1 O
  O2L 1.1044(11) 0.6123(6) 0.0412(5) 0.0547(14) Uani d P 0.50 A 2 O
  O3L 0.8368(12) 0.4963(10) 0.1241(8) 0.0468(16) Uani d P 0.50 A 2 O
  C1D 0.9305(3) 0.6567(2) 0.19874(18) 0.0250(4) Uani d P 0.764(3) A 1 C
  C1L 0.8740(9) 0.6053(6) 0.2405(6) 0.0254(13) Uani d P 0.236(3) A 2 C
  C2D 1.0336(2) 0.60097(13) 0.30160(12) 0.0331(3) Uani d . 1 . . C
  C3D 0.9384(6) 0.6561(3) 0.3985(3) 0.0435(8) Uani d P 0.764(3) A 1 C
  C3L 0.9882(17) 0.6960(9) 0.3674(10) 0.036(2) Uani d P 0.236(3) A 2 C
  C4D 0.7898(2) 0.73940(13) 0.34132(12) 0.0341(3) Uani d . 1 . . C
  C5D 0.9069(3) 0.84495(18) 0.24468(19) 0.0403(5) Uani d P 0.764(3) A 1 C
  C5L 0.6502(9) 0.6287(6) 0.4155(5) 0.0333(14) Uani d P 0.236(3) A 2 C
  C6D 1.0131(4) 0.7864(2) 0.1492(2) 0.0334(5) Uani d P 0.764(3) A 1 C
  C6L 0.7161(11) 0.5359(6) 0.3470(6) 0.0302(14) Uani d P 0.236(3) A 2 C
  C7D 0.7205(3) 0.67074(16) 0.26714(14) 0.0279(4) Uani d P 0.764(3) A 1 C
  C7L 0.8096(8) 0.7361(5) 0.2139(5) 0.0269(14) Uani d P 0.236(3) A 2 C
  C8D 0.5945(2) 0.74497(14) 0.18485(13) 0.0382(3) Uani d . 1 . . C
  C9D 0.6186(4) 0.5536(2) 0.3445(2) 0.0411(5) Uani d P 0.764(3) A 1 C
  C9L 0.9554(12) 0.8261(7) 0.1264(7) 0.0326(16) Uani d P 0.236(3) A 2 C
  C10D 0.9570(2) 0.58500(15) 0.11361(15) 0.0389(4) Uani d . 1 . . C
  H3D 1.0757 0.5833 -0.0291 0.058 Uiso calc PR 0.50 A 1 H
  H3L 0.8641 0.4758 0.0622 0.070 Uiso calc PR 0.50 A 2 H
  H3DC 1.0337 0.7007 0.4177 0.052 Uiso calc PR 0.764(3) A 1 H
  H3DD 0.8747 0.5947 0.4715 0.052 Uiso calc PR 0.764(3) A 1 H
  H3LE 0.9808 0.6607 0.4534 0.044 Uiso calc PR 0.236(3) A 2 H
  H3LF 1.0857 0.7611 0.3348 0.044 Uiso calc PR 0.236(3) A 2 H
  H4DB 0.6834 0.7635 0.3988 0.041 Uiso calc R 1 A 1 H
  H5DC 1.0004 0.8778 0.2765 0.048 Uiso calc PR 0.764(3) A 1 H
  H5DD 0.8202 0.9091 0.2119 0.048 Uiso calc PR 0.764(3) A 1 H
  H5LC 0.6676 0.5977 0.4980 0.040 Uiso calc PR 0.236(3) A 2 H
  H5LD 0.5130 0.6502 0.4164 0.040 Uiso calc PR 0.236(3) A 2 H
  H6DC 1.1550 0.7872 0.1415 0.040 Uiso calc PR 0.764(3) A 1 H
  H6DD 0.9828 0.8278 0.0711 0.040 Uiso calc PR 0.764(3) A 1 H
  H6LC 0.7701 0.4642 0.3968 0.036 Uiso calc PR 0.236(3) A 2 H
  H6LD 0.6074 0.5120 0.3200 0.036 Uiso calc PR 0.236(3) A 2 H
  H8DA 0.6618 0.8196 0.1360 0.057 Uiso calc PR 0.764(3) A 1 H
  H8DB 0.4716 0.7623 0.2322 0.057 Uiso calc PR 0.764(3) A 1 H
  H8DC 0.5693 0.7005 0.1336 0.057 Uiso calc PR 0.764(3) A 1 H
  H8DD 0.5114 0.6845 0.2443 0.057 Uiso d PR 0.236(3) A 2 H
  H8DE 0.6037 0.7344 0.1087 0.057 Uiso d PR 0.236(3) A 2 H
  H8DF 0.5419 0.8218 0.1843 0.057 Uiso d PR 0.236(3) A 2 H
  H9DD 0.7012 0.5071 0.3966 0.062 Uiso calc PR 0.764(3) A 1 H
  H9DE 0.5936 0.5084 0.2939 0.062 Uiso calc PR 0.764(3) A 1 H
  H9DF 0.4958 0.5701 0.3925 0.062 Uiso calc PR 0.764(3) A 1 H
  H9LD 0.9636 0.8212 0.0465 0.049 Uiso calc PR 0.236(3) A 2 H
  H9LE 1.0823 0.8095 0.1468 0.049 Uiso calc PR 0.236(3) A 2 H
  H9LF 0.9149 0.9060 0.1291 0.049 Uiso calc PR 0.236(3) A 2 H
  O1L' 0.3362(17) -0.0796(7) 0.3726(10) 0.049(2) Uani d P 0.540(3) B 1 O
  O1D' 0.305(2) -0.0770(8) 0.3783(11) 0.050(2) Uani d P 0.460(3) B 2 O
  O2L' 0.29271(18) 0.02288(11) 0.09922(12) 0.0534(3) Uani d . 1 B 1 O
  O3L' 0.59792(19) 0.06811(11) 0.07887(11) 0.0502(3) Uani d . 1 B 1 O
  C1L' 0.3136(4) 0.1162(2) 0.22812(19) 0.0228(5) Uani d P 0.540(3) B 1 C
  C1D' 0.4287(5) 0.1116(2) 0.2356(2) 0.0222(6) Uani d P 0.460(3) B 2 C
  C2L' 0.32032(19) 0.02753(12) 0.35113(11) 0.0295(3) Uani d . 1 . . C
  C3L' 0.2729(3) 0.10290(14) 0.43503(13) 0.0413(4) Uani d . 1 B . C
  C4L' 0.2643(7) 0.2281(8) 0.3528(7) 0.0295(11) Uani d P 0.540(3) B 1 C
  C4D' 0.3277(9) 0.2273(9) 0.3547(9) 0.0318(13) Uani d P 0.460(3) B 2 C
  C5L' 0.0644(3) 0.2289(2) 0.3233(2) 0.0311(6) Uani d P 0.540(3) B 1 C
  C5D' 0.5492(5) 0.2247(3) 0.3440(3) 0.0346(8) Uani d P 0.460(3) B 2 C
  C6L' 0.0940(4) 0.1480(3) 0.2416(2) 0.0282(6) Uani d P 0.540(3) B 1 C
  C6D' 0.6180(4) 0.1408(3) 0.2662(3) 0.0284(7) Uani d P 0.460(3) B 2 C
  C7L' 0.4077(5) 0.2290(2) 0.2348(2) 0.0250(6) Uani d P 0.540(3) B 1 C
  C7D' 0.3090(6) 0.2278(3) 0.2299(3) 0.0260(7) Uani d P 0.460(3) B 2 C
  C8L' 0.3969(2) 0.33838(12) 0.13094(12) 0.0334(3) Uani d . 1 . . C
  C9L' 0.6179(4) 0.2133(3) 0.2487(3) 0.0350(7) Uani d P 0.540(3) B 1 C
  C9D' 0.0975(5) 0.2152(5) 0.2236(4) 0.0442(10) Uani d P 0.460(3) B 2 C
  C10L' 0.4241(3) 0.06529(13) 0.12917(13) 0.0519(5) Uani d . 1 . . C
  H2L' 0.3420 -0.0068 0.0450 0.080 Uiso calc PR 0.50 B 1 H
  H3L' 0.6125 0.0318 0.0282 0.075 Uiso calc PR 0.50 B 1 H
  H3LA 0.1473 0.0787 0.4912 0.050 Uiso calc PR 0.540(3) B 1 H
  H3LB 0.3750 0.0964 0.4803 0.050 Uiso calc PR 0.540(3) B 1 H
  H3LC 0.3591 0.0792 0.4885 0.050 Uiso d PR 0.460(3) B 2 H
  H3LD 0.1419 0.0934 0.4799 0.050 Uiso d PR 0.460(3) B 2 H
  H4L 0.2864 0.2927 0.3857 0.035 Uiso calc PR 0.540(3) B 1 H
  H4DA 0.2587 0.2927 0.3830 0.038 Uiso calc PR 0.460(3) B 2 H
  H5LA 0.0279 0.3104 0.2815 0.037 Uiso calc PR 0.540(3) B 1 H
  H5LB -0.0365 0.1959 0.3958 0.037 Uiso calc PR 0.540(3) B 1 H
  H5DA 0.5822 0.1921 0.4226 0.042 Uiso calc PR 0.460(3) B 2 H
  H5DB 0.6073 0.3051 0.3048 0.042 Uiso calc PR 0.460(3) B 2 H
  H6LA 0.0637 0.1910 0.1639 0.034 Uiso calc PR 0.540(3) B 1 H
  H6LB 0.0118 0.0757 0.2787 0.034 Uiso calc PR 0.540(3) B 1 H
  H6DA 0.7137 0.1813 0.1936 0.034 Uiso calc PR 0.460(3) B 2 H
  H6DB 0.6763 0.0678 0.3107 0.034 Uiso calc PR 0.460(3) B 2 H
  H8LA 0.2631 0.3496 0.1209 0.050 Uiso calc PR 0.540(3) B 1 H
  H8LB 0.4803 0.3279 0.0588 0.050 Uiso calc PR 0.540(3) B 1 H
  H8LC 0.4403 0.4082 0.1459 0.050 Uiso calc PR 0.540(3) B 1 H
  H8LD 0.3810 0.3331 0.0564 0.050 Uiso d PR 0.460(3) B 2 H
  H8LE 0.5322 0.3435 0.1291 0.050 Uiso d PR 0.460(3) B 2 H
  H8LF 0.3328 0.4079 0.1452 0.050 Uiso d PR 0.460(3) B 2 H
  H9LA 0.6272 0.1429 0.3156 0.053 Uiso calc PR 0.540(3) B 1 H
  H9LB 0.6604 0.2837 0.2632 0.053 Uiso calc PR 0.540(3) B 1 H
  H9LC 0.7005 0.2033 0.1761 0.053 Uiso calc PR 0.540(3) B 1 H
  H9DA 0.0389 0.1447 0.2866 0.066 Uiso calc PR 0.460(3) B 2 H
  H9DB 0.0933 0.2070 0.1465 0.066 Uiso calc PR 0.460(3) B 2 H
  H9DC 0.0256 0.2859 0.2338 0.066 Uiso calc PR 0.460(3) B 2 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
  O1D 0.047(2) 0.0477(15) 0.0329(13) 0.0264(18) -0.0161(12) -0.0204(10)
  O1L 0.054(8) 0.074(9) 0.080(11) 0.007(5) -0.015(6) -0.037(7)
  O2D 0.041(3) 0.056(2) 0.036(3) 0.004(2) -0.0046(19) -0.0214(19)
  O3D 0.051(2) 0.0390(17) 0.026(2) -0.0031(16) 0.0023(15) -0.0170(14)
  O2L 0.071(3) 0.061(3) 0.049(3) 0.0174(19) -0.0202(19) -0.040(2)
  O3L 0.046(3) 0.067(3) 0.045(3) 0.010(2) -0.0133(18) -0.042(2)
  C1D 0.0302(9) 0.0272(10) 0.0194(9) 0.0034(8) -0.0026(7) -0.0120(8)
  C1L 0.031(3) 0.027(3) 0.018(3) -0.004(2) -0.002(2) -0.008(2)
  C2D 0.0404(7) 0.0364(7) 0.0266(6) 0.0076(6) -0.0089(5) -0.0156(5)
  C3D 0.057(2) 0.055(2) 0.0315(16) 0.0247(15) -0.0203(14) -0.0277(14)
  C3L 0.049(5) 0.036(5) 0.033(5) -0.002(3) -0.012(4) -0.019(4)
  C4D 0.0423(7) 0.0404(7) 0.0275(6) 0.0113(6) -0.0088(6) -0.0228(6)
  C5D 0.0506(12) 0.0359(10) 0.0472(11) 0.0072(8) -0.0161(9) -0.0285(9)
  C5L 0.037(3) 0.041(3) 0.022(3) -0.004(2) 0.003(2) -0.015(2)
  C6D 0.0379(13) 0.0297(13) 0.0366(12) -0.0004(9) -0.0054(9) -0.0177(10)
  C6L 0.031(3) 0.038(3) 0.025(3) 0.001(3) 0.000(3) -0.018(2)
  C7D 0.0321(9) 0.0323(9) 0.0201(8) 0.0052(8) -0.0020(7) -0.0128(7)
  C7L 0.030(3) 0.028(3) 0.023(3) -0.003(2) 0.001(2) -0.012(2)
  C8D 0.0427(8) 0.0435(8) 0.0366(7) 0.0148(6) -0.0150(6) -0.0219(6)
  C9D 0.0436(14) 0.0412(12) 0.0277(10) -0.0005(11) 0.0071(10) -0.0055(8)
  C9L 0.032(4) 0.025(4) 0.036(4) -0.009(3) 0.003(3) -0.009(3)
  C10D 0.0441(8) 0.0457(9) 0.0426(9) 0.0201(7) -0.0206(7) -0.0315(7)
  O1L' 0.077(3) 0.033(3) 0.033(3) 0.023(3) -0.013(2) -0.009(2)
  O1D' 0.090(5) 0.027(3) 0.032(3) -0.018(3) 0.002(3) -0.013(2)
  O2L' 0.0498(7) 0.0451(7) 0.0582(8) 0.0031(5) 0.0052(6) -0.0182(6)
  O3L' 0.0659(8) 0.0452(7) 0.0433(6) -0.0095(6) -0.0184(6) -0.0122(5)
  C1L' 0.0247(14) 0.0257(11) 0.0219(11) 0.0046(9) -0.0053(9) -0.0133(8)
  C1D' 0.0222(16) 0.0268(13) 0.0210(12) 0.0030(10) -0.0062(10) -0.0114(10)
  C2L' 0.0341(7) 0.0315(7) 0.0240(6) 0.0020(5) -0.0046(5) -0.0115(5)
  C3L' 0.0626(10) 0.0380(8) 0.0246(7) 0.0028(7) -0.0041(6) -0.0153(6)
  C4L' 0.035(3) 0.0327(16) 0.0264(16) 0.008(2) -0.007(2) -0.0181(12)
  C4D' 0.045(4) 0.0310(19) 0.0255(18) 0.008(3) -0.009(3) -0.0176(14)
  C5L' 0.0272(12) 0.0389(13) 0.0308(12) 0.0089(9) -0.0029(9) -0.0198(10)
  C5D' 0.0455(17) 0.0355(16) 0.0353(16) 0.0061(13) -0.0208(13) -0.0210(13)
  C6L' 0.0218(12) 0.0381(16) 0.0302(13) 0.0049(12) -0.0048(9) -0.0197(12)
  C6D' 0.0277(14) 0.0299(17) 0.0354(15) 0.0067(12) -0.0132(11) -0.0180(13)
  C7L' 0.0231(14) 0.0287(12) 0.0280(12) 0.0031(10) -0.0066(11) -0.0152(9)
  C7D' 0.0264(17) 0.0307(15) 0.0256(14) 0.0074(13) -0.0076(13) -0.0151(11)
  C8L' 0.0448(8) 0.0282(6) 0.0291(6) 0.0045(5) -0.0091(6) -0.0112(5)
  C9L' 0.0232(12) 0.048(2) 0.0441(15) 0.0041(12) -0.0117(10) -0.0263(14)
  C9D' 0.0291(17) 0.059(3) 0.060(2) 0.0193(19) -0.0194(16) -0.036(2)
  C10L' 0.1058(16) 0.0205(6) 0.0220(7) -0.0028(8) 0.0059(8) -0.0095(5)
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
  O1D C2D . 1.195(5) y
  O1L C2D . 1.26(2) y
  O2D C10D . 1.189(10) y
  O3D C10D . 1.288(6) y
  O2L C10D . 1.194(8) y
  O3L C10D . 1.350(10) y
  C1D C10D . 1.505(2) ?
  C1D C2D . 1.542(2) ?
  C1D C7D . 1.562(3) ?
  C1D C6D . 1.562(3) ?
  C1L C2D . 1.477(6) ?
  C1L C7L . 1.542(9) ?
  C1L C6L . 1.552(10) ?
  C1L C10D . 1.610(6) ?
  C2D C3D . 1.528(4) ?
  C2D C3L . 1.551(12) ?
  C3D C4D . 1.532(4) ?
  C3L C4D . 1.536(13) ?
  C4D C7L . 1.538(5) ?
  C4D C5D . 1.553(3) ?
  C4D C7D . 1.555(2) ?
  C4D C5L . 1.593(6) ?
  C5D C6D . 1.562(3) ?
  C5L C6L . 1.564(8) ?
  C7D C8D . 1.529(2) ?
  C7D C9D . 1.529(3) ?
  C7L C9L . 1.508(9) ?
  C7L C8D . 1.633(6) ?
  O1L' C2L' . 1.216(8) y
  O1D' C2L' . 1.183(9) y
  O2L' C10L' . 1.255(2) y
  O3L' C10L' . 1.245(2) y
  C1L' C10L' . 1.547(2) ?
  C1L' C2L' . 1.549(3) ?
  C1L' C7L' . 1.559(4) ?
  C1L' C6L' . 1.565(4) ?
  C1D' C2L' . 1.516(3) ?
  C1D' C6D' . 1.556(4) ?
  C1D' C10L' . 1.561(3) ?
  C1D' C7D' . 1.563(4) ?
  C2L' C3L' . 1.5239(18) ?
  C3L' C4D' . 1.511(10) ?
  C3L' C4L' . 1.517(9) ?
  C4L' C5L' . 1.538(5) ?
  C4L' C7L' . 1.559(8) ?
  C4D' C5D' . 1.547(7) ?
  C4D' C7D' . 1.551(9) ?
  C5L' C6L' . 1.554(4) ?
  C5D' C6D' . 1.560(4) ?
  C7L' C8L' . 1.517(3) ?
  C7L' C9L' . 1.532(4) ?
  C7D' C8L' . 1.529(3) ?
  C7D' C9D' . 1.538(6) ?