#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011421.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_2011421
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1260
_journal_page_last  1262
_publ_section_title
;
5-Oxocyclooctanecarboxylic acid: hydrogen-bonding pattern and
conformational disorder in a medium-ring \e-keto acid
;
loop_
_publ_author_name
  'Lalancette, Roger A.'
  'Brunskill, Andrew P. J.'
  'Thompson, Hugh W.'
_chemical_formula_moiety  'C9 H14 O3'
_chemical_formula_sum  'C9 H14 O3'
_chemical_formula_weight  170.20
_chemical_melting_point  352
_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  6.7449(8)
_cell_length_b  9.8755(13)
_cell_length_c  13.878(2)
_cell_angle_alpha  81.586(10)
_cell_angle_beta  86.189(10)
_cell_angle_gamma  88.519(9)
_cell_volume  912.3(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.239
_diffrn_ambient_temperature  293(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  -.2589(4)  .1370(3)  .9205(2)  .0684(8) Uani d . 1 . . O
  O2  .0525(4)  .5523(2)  .60202(15)  .0562(7) Uani d . 1 . . O
  O3  -.0317(4)  .3413(2)  .58442(15)  .0557(7) Uani d . 1 . . O
  C1  .0104(5)  .3824(3)  .7450(2)  .0401(7) Uani d . 1 . . C
  C2  -.0450(5)  .4954(3)  .8074(2)  .0499(9) Uani d . 1 . . C
  C3  -.2091(6)  .4562(4)  .8862(2)  .0563(9) Uani d . 1 . . C
  C4  -.1578(6)  .3421(3)  .9685(2)  .0552(9) Uani d . 1 . . C
  C5  -.1196(5)  .2060(3)  .9342(2)  .0466(8) Uani d . 1 . . C
  C6  .0890(5)  .1548(3)  .9195(2)  .0509(9) Uani d . 1 . . C
  C7  .2412(5)  .2587(4)  .8724(2)  .0533(9) Uani d . 1 . . C
  C8  .2138(5)  .3128(4)  .7653(2)  .0536(9) Uani d . 1 . . C
  C9  .0122(5)  .4353(3)  .6371(2)  .0415(7) Uani d . 1 . . C
  O1'  .8575(5)  .8203(3)  .8392(2)  .0894(10) Uani d . 1 . . O
  O2'  .5155(5)  .6736(3)  .48547(19)  .0722(8) Uani d . 1 A . O
  O3'  .5734(4)  .5221(2)  .61585(18)  .0598(7) Uani d . 1 A . O
  C1'  .5959(5)  .7567(3)  .6315(2)  .0452(8) Uani d . 1 A . C
  C2'  .3959(6)  .7896(5)  .6818(4)  .0829(15) Uani d . 1 . . C
  C3'  .3931(9)  .8129(12)  .7828(5)  .064(3) Uani d P  .600(14) A 1 C
  C3''  .391(2)  .8942(18)  .7538(12)  .080(4) Uiso d P  .400(14) A 2 C
  C4'  .5299(7)  .8984(6)  .8227(4)  .0947(17) Uani d . 1 . . C
  C5'  .7456(5)  .8977(3)  .7941(2)  .0503(9) Uani d . 1 A . C
  C6'  .8205(7)  .9939(5)  .7098(3)  .0785(13) Uani d . 1 . . C
  C7'  .7417(18)  .9987(9)  .6111(5)  .061(2) Uani d P  .600(14) A 1 C
  C7''  .855(3)  .9423(17)  .6198(8)  .065(4) Uani d P  .400(14) A 2 C
  C8'  .6981(7)  .8786(4)  .5698(3)  .0710(12) Uani d . 1 . . C
  C9'  .5615(5)  .6450(3)  .5717(2)  .0469(8) Uani d . 1 . . C
  H1  -.0911  .3119  .7597  .048 Uiso calc R 1 . . H
  H3  -.0288  .3746  .5267  .084 Uiso calc R 1 . . H
  H2A  .0723  .5184  .8380  .060 Uiso calc R 1 . . H
  H2B  -.0871  .5765  .7651  .060 Uiso calc R 1 . . H
  H3A  -.3231  .4281  .8554  .068 Uiso calc R 1 . . H
  H3B  -.2488  .5372  .9151  .068 Uiso calc R 1 . . H
  H4A  -.0407  .3676  .9982  .066 Uiso calc R 1 . . H
  H4B  -.2667  .3335 1.0182  .066 Uiso calc R 1 . . H
  H6A  .0877  .0819  .8796  .061 Uiso calc R 1 . . H
  H6B  .1334  .1147  .9826  .061 Uiso calc R 1 . . H
  H7A  .3726  .2170  .8776  .064 Uiso calc R 1 . . H
  H7B  .2357  .3356  .9088  .064 Uiso calc R 1 . . H
  H8A  .2312  .2371  .7280  .064 Uiso calc R 1 . . H
  H8B  .3173  .3781  .7421  .064 Uiso calc R 1 . . H
  H1'  .6846  .7195  .6824  .080 Uiso calc R 1 . . H
  H2'  .4582  .6088  .4697  .080 Uiso calc PR  .34(6) . . H
  H3'  .5279  .4697  .5826  .080 Uiso calc PR  .66(6) . . H
  H2'A  .3406  .8707  .6441  .080 Uiso calc PR  .600(14) A 1 H
  H2'B  .3073  .7148  .6786  .080 Uiso calc PR  .600(14) A 1 H
  H2'C  .3390  .7038  .7131  .080 Uiso d PR  .400(14) A 2 H
  H2'D  .3090  .8275  .6312  .080 Uiso d PR  .400(14) A 2 H
  H3'A  .4025  .7230  .8213  .080 Uiso calc PR  .600(14) A 1 H
  H3'B  .2611  .8483  .7981  .080 Uiso calc PR  .600(14) A 1 H
  H3'C  .3918  .9838  .7145  .080 Uiso calc PR  .400(14) A 2 H
  H3'D  .2628  .8856  .7896  .080 Uiso calc PR  .400(14) A 2 H
  H4'A  .5163  .8747  .8931  .080 Uiso calc PR  .600(14) A 1 H
  H4'B  .4825  .9922  .8077  .080 Uiso calc PR  .600(14) A 1 H
  H4'C  .5081  .8232  .8754  .080 Uiso d PR  .400(14) A 2 H
  H4'D  .5018  .9818  .8506  .080 Uiso d PR  .400(14) A 2 H
  H6'A  .9627  .9775  .7022  .080 Uiso calc PR  .600(14) A 1 H
  H6'B  .8024 1.0850  .7276  .080 Uiso calc PR  .600(14) A 1 H
  H6'C  .7285 1.0713  .7018  .080 Uiso d PR  .400(14) A 2 H
  H6'D  .9462 1.0282  .7254  .080 Uiso d PR  .400(14) A 2 H
  H7'A  .6201 1.0533  .6115  .080 Uiso calc PR  .600(14) A 1 H
  H7'B  .8362 1.0504  .5651  .080 Uiso calc PR  .600(14) A 1 H
  H7'C  .9618  .8747  .6292  .080 Uiso calc PR  .400(14) A 2 H
  H7'D  .9085 1.0175  .5732  .080 Uiso calc PR  .400(14) A 2 H
  H8'A  .8228  .8449  .5426  .080 Uiso calc PR  .600(14) A 1 H
  H8'B  .6165  .9080  .5153  .080 Uiso calc PR  .600(14) A 1 H
  H8'C  .7619  .8481  .5118  .080 Uiso d PR  .400(14) A 2 H
  H8'D  .5972  .9463  .5486  .080 Uiso d PR  .400(14) A 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
  O1  .0707(18)  .0580(16)  .0773(18)  -.0179(13)  -.0075(14)  -.0081(13)
  O2  .0826(17)  .0489(14)  .0360(12)  -.0208(12)  -.0106(11)  .0038(10)
  O3  .0883(18)  .0438(13)  .0354(12)  -.0060(12)  -.0081(12)  -.0037(10)
  C1  .0513(19)  .0365(16)  .0313(15)  -.0038(13)  -.0047(13)  .0008(12)
  C2  .073(2)  .0360(17)  .0399(17)  -.0003(16)  -.0115(16)  .0002(13)
  C3  .072(2)  .051(2)  .0467(19)  .0091(18)  .0005(18)  -.0135(16)
  C4  .074(2)  .055(2)  .0362(17)  -.0046(18)  .0050(17)  -.0078(15)
  C5  .064(2)  .0436(18)  .0312(16)  -.0119(16)  -.0054(15)  .0017(13)
  C6  .069(2)  .0427(18)  .0396(18)  .0016(16)  -.0157(16)  .0031(14)
  C7  .053(2)  .056(2)  .0499(19)  .0026(16)  -.0177(16)  .0021(16)
  C8  .059(2)  .053(2)  .0458(19)  .0009(17)  -.0035(16)  .0026(15)
  C9  .0480(18)  .0419(18)  .0341(16)  -.0018(14)  -.0065(14)  -.0017(14)
  O1'  .125(3)  .0735(19)  .077(2)  .0298(18)  -.0466(19)  -.0234(16)
  O2'  .110(2)  .0559(16)  .0558(16)  -.0219(15)  -.0243(15)  -.0124(12)
  O3'  .0750(17)  .0439(14)  .0645(15)  -.0089(12)  -.0195(13)  -.0134(12)
  C1'  .0438(18)  .0430(18)  .0519(19)  -.0006(14)  -.0139(15)  -.0120(15)
  C2'  .046(2)  .102(3)  .116(4)  -.006(2)  .000(2)  -.071(3)
  C3'  .040(3)  .101(7)  .046(4)  -.014(4)  .011(3)  .000(4)
  C4'  .077(3)  .128(4)  .095(3)  -.026(3)  .020(3)  -.074(3)
  C5'  .062(2)  .0461(19)  .0476(19)  -.0047(17)  -.0105(17)  -.0190(16)
  C6'  .096(3)  .078(3)  .065(3)  -.040(2)  -.020(2)  -.010(2)
  C7'  .075(6)  .051(4)  .057(4)  -.018(4)  -.007(4)  -.005(3)
  C7''  .080(10)  .068(8)  .046(6)  -.039(7)  .005(6)  -.006(5)
  C8'  .103(3)  .052(2)  .059(2)  -.018(2)  -.021(2)  -.0037(18)
  C9'  .0454(19)  .046(2)  .052(2)  -.0046(15)  -.0092(15)  -.0125(15)
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 C5 . 1.216(4) ?
  O2 C9 . 1.216(4) y
  O3 C9 . 1.314(4) y
  C1 C9 . 1.512(4) ?
  C1 C2 . 1.534(4) ?
  C1 C8 . 1.542(5) ?
  C2 C3 . 1.519(5) ?
  C3 C4 . 1.533(5) ?
  C4 C5 . 1.501(5) ?
  C5 C6 . 1.494(5) ?
  C6 C7 . 1.518(5) ?
  C7 C8 . 1.525(4) ?
  O1' C5' . 1.200(4) ?
  O2' C9' . 1.247(4) y
  O3' C9' . 1.280(4) y
  C1' C9' . 1.505(4) ?
  C1' C8' . 1.523(5) ?
  C1' C2' . 1.527(5) ?
  C2' C3' . 1.453(7) ?
  C2' C3'' . 1.537(13) ?
  C3' C4' . 1.454(9) ?
  C3'' C4' . 1.385(13) ?
  C4' C5' . 1.483(5) ?
  C5' C6' . 1.465(5) ?
  C6' C7'' . 1.420(12) ?
  C6' C7' . 1.496(9) ?
  C7' C8' . 1.436(8) ?
  C7'' C8' . 1.505(13) ?
  O3 H3 .  .8200 ?
  C1 H1 .  .9800 ?
  C2 H2A .  .9700 ?
  C2 H2B .  .9700 ?
  C3 H3A .  .9700 ?
  C3 H3B .  .9700 ?
  C4 H4A .  .9700 ?
  C4 H4B .  .9700 ?
  C6 H6A .  .9700 ?
  C6 H6B .  .9700 ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C8 H8A .  .9700 ?
  C8 H8B .  .9700 ?
  O2' H2' .  .8200 ?
  O3' H3' .  .8200 ?
  C1' H1' .  .9800 ?
  C2' H2'A .  .9700 ?
  C2' H2'B .  .9700 ?
  C2' H2'C .  .9700 ?
  C2' H2'D .  .9700 ?
  C3' H3'A .  .9700 ?
  C3' H3'B .  .9700 ?
  C3' H4'C . 1.5613 ?
  C3'' H3'C .  .9700 ?
  C3'' H3'D .  .9700 ?
  C4' H4'A .  .9700 ?
  C4' H4'B .  .9700 ?
  C4' H4'C .  .9700 ?
  C4' H4'D .  .9702 ?
  C6' H6'A .  .9700 ?
  C6' H6'B .  .9700 ?
  C6' H6'C .  .9701 ?
  C6' H6'D .  .9700 ?
  C7' H6'C . 1.5334 ?
  C7' H7'A .  .9700 ?
  C7' H7'B .  .9700 ?
  C7' H8'D . 1.4961 ?
  C7'' H7'C .  .9700 ?
  C7'' H7'D .  .9700 ?
  C8' H8'A .  .9700 ?
  C8' H8'B .  .9700 ?
  C8' H8'C .  .9700 ?
  C8' H8'D .  .9700 ?