data_2202148
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o344
_journal_page_last  o346
_publ_section_title
;
2-Hydroxycyclohexene-1-carboxylic acid: the enol isomer of
2-oxocyclohexane-1-carboxylic acid
;
loop_
_publ_author_name
  'Kresge, A. Jerry'
  'Lough, Alan J.'
  'Zhu, Yu'
_chemical_formula_moiety  'C7 H10 O3'
_chemical_formula_sum  'C7 H10 O3'
_chemical_formula_iupac  'C7 H10 O3'
_chemical_formula_weight  142.15
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C c'
_symmetry_space_group_name_Hall  'C -2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y, z+1/2'
  'x+1/2, y+1/2, z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  11.1360(4)
_cell_length_b  11.1049(3)
_cell_length_c  22.8774(9)
_cell_angle_alpha  90.00
_cell_angle_beta  91.9072(12)
_cell_angle_gamma  90.00
_cell_volume  2827.55(17)
_cell_formula_units_Z  16
_cell_measurement_temperature  150.0(10)
_exptl_crystal_density_diffrn  1.336
_diffrn_ambient_temperature  150.0(10)
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
  O1A 0.5025(2) 0.4443(2) 0.99826(11) 0.0384(6) Uani d . 1 . . O
  H1A 0.4503 0.4572 0.9716 0.058 Uiso calc R 1 . . H
  O2A 0.3979(2) 0.4165(2) 0.89731(11) 0.0403(6) Uani d . 1 . . O
  O3A 0.4585(3) 0.2646(2) 0.84107(11) 0.0443(7) Uani d . 1 . . O
  H3A 0.4025 0.2917 0.8194 0.066 Uiso calc R 1 . . H
  C1A 0.5592(3) 0.2919(3) 0.93167(14) 0.0327(7) Uani d . 1 . . C
  C2A 0.5721(3) 0.3514(3) 0.98299(14) 0.0319(7) Uani d . 1 . . C
  C3A 0.6637(4) 0.3198(3) 1.02951(16) 0.0412(8) Uani d . 1 . . C
  H3AA 0.7046 0.3944 1.0430 0.049 Uiso calc R 1 . . H
  H3AB 0.6221 0.2853 1.0633 0.049 Uiso calc R 1 . . H
  C4A 0.7558(4) 0.2324(5) 1.01036(19) 0.0592(12) Uani d . 1 . . C
  H4AA 0.8175 0.2757 0.9884 0.071 Uiso calc R 1 . . H
  H4AB 0.7960 0.1955 1.0452 0.071 Uiso calc R 1 . . H
  C5A 0.7025(4) 0.1365(4) 0.9731(2) 0.0618(12) Uani d . 1 . . C
  H5AA 0.6443 0.0904 0.9960 0.074 Uiso calc R 1 . . H
  H5AB 0.7668 0.0804 0.9617 0.074 Uiso calc R 1 . . H
  C6A 0.6381(4) 0.1853(4) 0.91744(17) 0.0433(9) Uani d . 1 . . C
  H6AA 0.6984 0.2102 0.8890 0.052 Uiso calc R 1 . . H
  H6AB 0.5881 0.1208 0.8993 0.052 Uiso calc R 1 . . H
  C7A 0.4671(3) 0.3288(3) 0.88942(14) 0.0351(8) Uani d . 1 . . C
  O1B 0.2544(2) -0.2838(2) 0.66286(11) 0.0400(6) Uani d . 1 . . O
  H1B 0.2419 -0.2345 0.6898 0.060 Uiso calc R 1 . . H
  O2B 0.2888(2) -0.1846(2) 0.76381(11) 0.0384(6) Uani d . 1 . . O
  O3B 0.4427(2) -0.2498(3) 0.82081(11) 0.0449(7) Uani d . 1 . . O
  H3B 0.4164 -0.1956 0.8425 0.067 Uiso calc R 1 . . H
  C1B 0.4111(3) -0.3451(3) 0.73005(14) 0.0328(7) Uani d . 1 . . C
  C2B 0.3481(3) -0.3553(3) 0.67850(15) 0.0315(7) Uani d . 1 . . C
  C3B 0.3760(4) -0.4448(3) 0.63269(15) 0.0396(8) Uani d . 1 . . C
  H3BA 0.4086 -0.4020 0.5987 0.048 Uiso calc R 1 . . H
  H3BB 0.3006 -0.4850 0.6194 0.048 Uiso calc R 1 . . H
  C4B 0.4649(4) -0.5396(4) 0.65305(18) 0.0563(11) Uani d . 1 . . C
  H4BA 0.4229 -0.6017 0.6757 0.068 Uiso calc R 1 . . H
  H4BB 0.4992 -0.5792 0.6186 0.068 Uiso calc R 1 . . H
  C5B 0.5633(4) -0.4871(4) 0.6898(2) 0.0577(11) Uani d . 1 . . C
  H5BA 0.6074 -0.4275 0.6665 0.069 Uiso calc R 1 . . H
  H5BB 0.6204 -0.5517 0.7017 0.069 Uiso calc R 1 . . H
  C6B 0.5172(4) -0.4254(3) 0.74483(17) 0.0412(9) Uani d . 1 . . C
  H6BA 0.4933 -0.4875 0.7732 0.049 Uiso calc R 1 . . H
  H6BB 0.5826 -0.3768 0.7633 0.049 Uiso calc R 1 . . H
  C7B 0.3754(3) -0.2552(3) 0.77191(14) 0.0343(8) Uani d . 1 . . C
  O1C 0.1713(2) 0.3068(2) 0.66833(11) 0.0423(6) Uani d . 1 A 1 O
  H1C 0.2215 0.2906 0.6955 0.063 Uiso calc R 1 A 1 H
  O2C 0.2761(2) 0.3325(2) 0.76997(11) 0.0384(6) Uani d . 1 . . O
  O3C 0.2192(3) 0.4868(2) 0.82564(11) 0.0443(7) Uani d . 1 . . O
  H3C 0.2743 0.4591 0.8477 0.066 Uiso calc R 1 . . H
  C1C 0.1165(3) 0.4595(3) 0.73599(14) 0.0317(7) Uani d . 1 . . C
  C2C 0.1048(3) 0.4018(3) 0.68371(14) 0.0337(7) Uani d . 1 A . C
  C3C 0.0160(4) 0.4388(3) 0.63633(17) 0.0438(9) Uani d D 1 A 1 C
  H3CA -0.0520 0.3813 0.6351 0.053 Uiso calc PR 0.762(7) B 1 H
  H3CB 0.0550 0.4354 0.5981 0.053 Uiso calc PR 0.762(7) B 1 H
  C3C* 0.0160(4) 0.4388(3) 0.63633(17) 0.0438(9) Uani d PD 0.00 A 2 C
  H3CC -0.0202 0.3655 0.6185 0.053 Uiso calc PR 0.238(7) B 2 H
  H3CD 0.0593 0.4817 0.6055 0.053 Uiso calc PR 0.238(7) B 2 H
  C4C -0.0320(5) 0.5663(4) 0.6461(2) 0.0442(13) Uani d PDU 0.762(7) A 1 C
  H4CA 0.0314 0.6260 0.6380 0.053 Uiso calc PR 0.762(7) B 1 H
  H4CB -0.1013 0.5817 0.6190 0.053 Uiso calc PR 0.762(7) B 1 H
  C5C -0.0709(4) 0.5801(6) 0.7092(2) 0.0461(15) Uani d PDU 0.762(7) A 1 C
  H5CA -0.1068 0.6607 0.7147 0.055 Uiso calc PR 0.762(7) B 1 H
  H5CB -0.1323 0.5187 0.7178 0.055 Uiso calc PR 0.762(7) B 1 H
  C4C* -0.0847(9) 0.5200(14) 0.6577(7) 0.0439(17) Uani d PDU 0.238(7) A 2 C
  H4CC -0.1286 0.5574 0.6240 0.053 Uiso calc PR 0.238(7) B 2 H
  H4CD -0.1423 0.4725 0.6803 0.053 Uiso calc PR 0.238(7) B 2 H
  C5C* -0.0255(17) 0.6168(12) 0.6964(5) 0.0454(19) Uani d PDU 0.238(7) A 2 C
  H5CC 0.0336 0.6616 0.6733 0.054 Uiso calc PR 0.238(7) B 2 H
  H5CD -0.0876 0.6747 0.7085 0.054 Uiso calc PR 0.238(7) B 2 H
  C6C 0.0380(4) 0.5647(3) 0.75087(16) 0.0388(9) Uani d D 1 A 1 C
  H6CA 0.0867 0.6392 0.7503 0.047 Uiso calc PR 0.762(7) B 1 H
  H6CB 0.0097 0.5540 0.7911 0.047 Uiso calc PR 0.762(7) B 1 H
  C6C* 0.0380(4) 0.5647(3) 0.75087(16) 0.0388(9) Uani d PD 0.00 A 2 C
  H6CC 0.0878 0.6280 0.7701 0.047 Uiso calc PR 0.238(7) B 2 H
  H6CD -0.0228 0.5383 0.7788 0.047 Uiso calc PR 0.238(7) B 2 H
  C7C 0.2094(3) 0.4203(3) 0.77745(14) 0.0333(7) Uani d . 1 A . C
  O1D 0.4100(2) 0.0251(2) 0.99417(11) 0.0418(6) Uani d . 1 C 1 O
  H1D 0.4245 -0.0236 0.9672 0.063 Uiso calc R 1 C 1 H
  O2D 0.3796(2) -0.0729(2) 0.89199(11) 0.0405(6) Uani d . 1 . . O
  O3D 0.2241(3) -0.0106(2) 0.83577(11) 0.0442(7) Uani d . 1 . . O
  H3D 0.2506 -0.0647 0.8141 0.066 Uiso calc R 1 . . H
  C1D 0.2553(3) 0.0860(3) 0.92558(14) 0.0308(7) Uani d . 1 . . C
  C2D 0.3145(3) 0.0939(3) 0.97808(14) 0.0326(7) Uani d . 1 C . C
  C3D 0.2811(4) 0.1792(4) 1.02524(17) 0.0436(9) Uani d D 1 C 1 C
  H3DA 0.3395 0.2464 1.0271 0.052 Uiso calc PR 0.661(6) D 1 H
  H3DB 0.2850 0.1370 1.0634 0.052 Uiso calc PR 0.661(6) D 1 H
  C3D* 0.2811(4) 0.1792(4) 1.02524(17) 0.0436(9) Uani d PD 0.00 C 2 C
  H3DC 0.3553 0.2128 1.0439 0.052 Uiso calc PR 0.339(6) D 2 H
  H3DD 0.2379 0.1345 1.0555 0.052 Uiso calc PR 0.339(6) D 2 H
  C4D 0.1529(4) 0.2304(5) 1.0141(2) 0.0426(14) Uani d PDU 0.661(6) C 1 C
  H4DA 0.0926 0.1670 1.0212 0.051 Uiso calc PR 0.661(6) D 1 H
  H4DB 0.1388 0.2978 1.0414 0.051 Uiso calc PR 0.661(6) D 1 H
  C5D 0.1395(6) 0.2746(5) 0.9512(2) 0.0419(15) Uani d PDU 0.661(6) C 1 C
  H5DA 0.2033 0.3339 0.9431 0.050 Uiso calc PR 0.661(6) D 1 H
  H5DB 0.0606 0.3143 0.9448 0.050 Uiso calc PR 0.661(6) D 1 H
  C5D* 0.1008(8) 0.2264(11) 0.9649(3) 0.0412(17) Uani d PDU 0.339(6) C 2 C
  H5DC 0.0415 0.2889 0.9529 0.049 Uiso calc PR 0.339(6) D 2 H
  H5DD 0.0590 0.1655 0.9884 0.049 Uiso calc PR 0.339(6) D 2 H
  C4D* 0.2010(9) 0.2840(7) 1.0023(5) 0.0419(17) Uani d PDU 0.339(6) C 2 C
  H4DC 0.1672 0.3291 1.0353 0.050 Uiso calc PR 0.339(6) D 2 H
  H4DD 0.2482 0.3404 0.9786 0.050 Uiso calc PR 0.339(6) D 2 H
  C6D 0.1496(3) 0.1660(3) 0.91009(16) 0.0378(8) Uani d D 1 C 1 C
  H6DA 0.0749 0.1179 0.9115 0.045 Uiso calc PR 0.661(6) D 1 H
  H6DB 0.1571 0.1953 0.8695 0.045 Uiso calc PR 0.661(6) D 1 H
  C6D* 0.1496(3) 0.1660(3) 0.91009(16) 0.0378(8) Uani d PD 0.00 C 2 C
  H6DC 0.0852 0.1174 0.8907 0.045 Uiso calc PR 0.339(6) D 2 H
  H6DD 0.1745 0.2287 0.8822 0.045 Uiso calc PR 0.339(6) D 2 H
  C7D 0.2915(3) -0.0040(3) 0.88395(14) 0.0332(7) Uani d . 1 C . C
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
  O1A 0.0465(14) 0.0384(13) 0.0299(12) 0.0081(12) -0.0028(10) -0.0049(10)
  O2A 0.0443(15) 0.0430(14) 0.0330(13) 0.0133(13) -0.0054(11) -0.0069(11)
  O3A 0.0492(16) 0.0508(15) 0.0322(14) 0.0160(13) -0.0080(11) -0.0128(11)
  C1A 0.0352(18) 0.0354(17) 0.0274(16) 0.0049(15) 0.0000(14) -0.0001(13)
  C2A 0.0325(18) 0.0316(16) 0.0315(17) -0.0050(15) 0.0020(14) 0.0007(13)
  C3A 0.048(2) 0.0455(19) 0.0297(18) -0.0004(18) -0.0046(15) 0.0029(15)
  C4A 0.052(3) 0.078(3) 0.048(2) 0.019(2) -0.0076(19) 0.001(2)
  C5A 0.059(3) 0.058(3) 0.067(3) 0.025(2) -0.016(2) -0.007(2)
  C6A 0.040(2) 0.047(2) 0.043(2) 0.0077(18) -0.0030(17) -0.0047(17)
  C7A 0.040(2) 0.0352(17) 0.0304(16) 0.0039(16) 0.0004(14) -0.0035(14)
  O1B 0.0408(14) 0.0489(14) 0.0298(11) 0.0114(12) -0.0053(10) -0.0009(10)
  O2B 0.0404(15) 0.0430(13) 0.0314(13) 0.0129(12) -0.0073(10) -0.0044(10)
  O3B 0.0463(15) 0.0552(16) 0.0324(13) 0.0199(13) -0.0102(11) -0.0074(11)
  C1B 0.0363(19) 0.0343(16) 0.0276(16) 0.0062(15) 0.0004(14) 0.0006(13)
  C2B 0.0325(18) 0.0322(16) 0.0299(16) 0.0008(15) 0.0014(13) 0.0018(13)
  C3B 0.044(2) 0.0458(19) 0.0294(17) 0.0019(17) 0.0025(15) -0.0026(15)
  C4B 0.076(3) 0.053(2) 0.041(2) 0.021(2) 0.000(2) -0.0079(18)
  C5B 0.058(3) 0.055(2) 0.060(2) 0.022(2) -0.008(2) -0.015(2)
  C6B 0.044(2) 0.040(2) 0.039(2) 0.0116(18) -0.0068(16) -0.0019(16)
  C7B 0.0353(19) 0.0372(17) 0.0300(17) 0.0014(16) -0.0034(14) 0.0017(13)
  O1C 0.0465(15) 0.0428(14) 0.0371(13) 0.0115(12) -0.0081(11) -0.0127(11)
  O2C 0.0445(14) 0.0380(13) 0.0321(13) 0.0119(13) -0.0069(11) -0.0079(11)
  O3C 0.0568(18) 0.0471(14) 0.0282(12) 0.0202(13) -0.0109(11) -0.0106(11)
  C1C 0.0347(18) 0.0301(16) 0.0303(17) 0.0023(15) 0.0002(14) -0.0024(13)
  C2C 0.0346(19) 0.0356(17) 0.0308(16) 0.0026(15) -0.0003(14) -0.0024(14)
  C3C 0.044(2) 0.051(2) 0.0354(19) 0.0043(18) -0.0107(16) -0.0040(16)
  C3C* 0.044(2) 0.051(2) 0.0354(19) 0.0043(18) -0.0107(16) -0.0040(16)
  C4C 0.047(3) 0.044(3) 0.040(3) 0.007(2) -0.012(2) -0.002(2)
  C5C 0.045(3) 0.042(3) 0.051(3) 0.016(3) -0.010(2) -0.007(2)
  C4C* 0.046(4) 0.045(4) 0.040(3) 0.007(3) -0.012(3) -0.002(3)
  C5C* 0.044(4) 0.041(4) 0.050(3) 0.015(3) -0.010(3) -0.006(3)
  C6C 0.038(2) 0.0384(19) 0.039(2) 0.0094(17) -0.0049(16) -0.0032(15)
  C6C* 0.038(2) 0.0384(19) 0.039(2) 0.0094(17) -0.0049(16) -0.0032(15)
  C7C 0.0389(19) 0.0335(16) 0.0275(16) 0.0032(16) 0.0024(14) -0.0013(13)
  O1D 0.0423(14) 0.0446(14) 0.0377(14) 0.0116(12) -0.0112(11) -0.0059(11)
  O2D 0.0375(15) 0.0477(14) 0.0359(14) 0.0126(13) -0.0064(11) -0.0068(11)
  O3D 0.0510(16) 0.0511(15) 0.0296(13) 0.0181(13) -0.0120(11) -0.0099(11)
  C1D 0.0315(17) 0.0321(16) 0.0286(16) 0.0010(15) -0.0019(13) -0.0017(13)
  C2D 0.0336(19) 0.0332(16) 0.0305(17) 0.0029(14) -0.0040(14) 0.0006(13)
  C3D 0.047(2) 0.046(2) 0.0374(19) 0.0060(18) -0.0064(16) -0.0092(16)
  C3D* 0.047(2) 0.046(2) 0.0374(19) 0.0060(18) -0.0064(16) -0.0092(16)
  C4D 0.047(4) 0.037(3) 0.044(3) 0.010(3) 0.001(3) -0.009(2)
  C5D 0.044(4) 0.034(3) 0.047(3) 0.014(3) -0.006(3) -0.006(2)
  C5D* 0.045(4) 0.032(4) 0.046(4) 0.013(3) -0.006(3) -0.005(3)
  C4D* 0.047(4) 0.035(4) 0.044(3) 0.010(3) 0.001(3) -0.008(3)
  C6D 0.036(2) 0.0425(19) 0.0340(18) 0.0085(17) -0.0039(15) -0.0030(15)
  C6D* 0.036(2) 0.0425(19) 0.0340(18) 0.0085(17) -0.0039(15) -0.0030(15)
  C7D 0.0325(18) 0.0389(17) 0.0279(16) 0.0054(15) -0.0030(13) -0.0027(14)
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
  O1A C2A . 1.344(4) ?
  O1A H1A . 0.8400 ?
  O2A C7A . 1.259(4) ?
  O3A C7A . 1.317(4) ?
  O3A H3A . 0.8400 ?
  C1A C2A . 1.350(4) ?
  C1A C7A . 1.445(5) ?
  C1A C6A . 1.516(5) ?
  C2A C3A . 1.491(5) ?
  C3A C4A . 1.489(6) ?
  C3A H3AA . 0.9900 ?
  C3A H3AB . 0.9900 ?
  C4A C5A . 1.476(6) ?
  C4A H4AA . 0.9900 ?
  C4A H4AB . 0.9900 ?
  C5A C6A . 1.539(6) ?
  C5A H5AA . 0.9900 ?
  C5A H5AB . 0.9900 ?
  C6A H6AA . 0.9900 ?
  C6A H6AB . 0.9900 ?
  O1B C2B . 1.349(4) ?
  O1B H1B . 0.8400 ?
  O2B C7B . 1.251(4) ?
  O3B C7B . 1.327(4) ?
  O3B H3B . 0.8400 ?
  C1B C2B . 1.357(5) ?
  C1B C7B . 1.448(5) ?
  C1B C6B . 1.511(5) ?
  C2B C3B . 1.485(5) ?
  C3B C4B . 1.508(6) ?
  C3B H3BA . 0.9900 ?
  C3B H3BB . 0.9900 ?
  C4B C5B . 1.479(6) ?
  C4B H4BA . 0.9900 ?
  C4B H4BB . 0.9900 ?
  C5B C6B . 1.536(6) ?
  C5B H5BA . 0.9900 ?
  C5B H5BB . 0.9900 ?
  C6B H6BA . 0.9900 ?
  C6B H6BB . 0.9900 ?
  O1C C2C . 1.343(4) ?
  O1C H1C . 0.8400 ?
  O2C C7C . 1.241(4) ?
  O3C C7C . 1.328(4) ?
  O3C H3C . 0.8400 ?
  C1C C2C . 1.359(4) ?
  C1C C7C . 1.447(5) ?
  C1C C6C . 1.505(5) ?
  C2C C3C . 1.500(5) ?
  C3C C4C . 1.533(6) ?
  C3C H3CA . 0.9900 ?
  C3C H3CB . 0.9900 ?
  C4C C5C . 1.528(6) ?
  C4C H4CA . 0.9900 ?
  C4C H4CB . 0.9900 ?
  C5C C6C . 1.527(6) ?
  C5C H5CA . 0.9900 ?
  C5C H5CB . 0.9900 ?
  C4C* C5C* . 1.528(6) ?
  C4C* H4CC . 0.9900 ?
  C4C* H4CD . 0.9900 ?
  C5C* H5CC . 0.9900 ?
  C5C* H5CD . 0.9900 ?
  C6C H6CA . 0.9900 ?
  C6C H6CB . 0.9900 ?
  O1D C2D . 1.350(4) ?
  O1D H1D . 0.8400 ?
  O2D C7D . 1.253(4) ?
  O3D C7D . 1.314(4) ?
  O3D H3D . 0.8400 ?
  C1D C2D . 1.353(4) ?
  C1D C7D . 1.448(4) ?
  C1D C6D . 1.507(5) ?
  C2D C3D . 1.492(5) ?
  C3D C4D . 1.550(6) ?
  C3D H3DA . 0.9900 ?
  C3D H3DB . 0.9900 ?
  C4D C5D . 1.524(6) ?
  C4D H4DA . 0.9900 ?
  C4D H4DB . 0.9900 ?
  C5D C6D . 1.536(5) ?
  C5D H5DA . 0.9900 ?
  C5D H5DB . 0.9900 ?
  C5D* C4D* . 1.524(6) ?
  C5D* H5DC . 0.9900 ?
  C5D* H5DD . 0.9900 ?
  C4D* H4DC . 0.9900 ?
  C4D* H4DD . 0.9900 ?
  C6D H6DA . 0.9900 ?
  C6D H6DB . 0.9900 ?