#------------------------------------------------------------------------------
#$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013149.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_2013149
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o167
_journal_page_last  o170
_publ_section_title
;
The epimeric 9-oxobicyclo[3.3.1]nonane-3-carboxylic acids: hydrogen-bonding
patterns of the endo acid and the lactol of the exo acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Papadakis, Markos M.'
  'Pavon, Jorge A.'
  'Lalancette, Roger A.'
  'Thompson, Hugh W.'
_chemical_name_common
;
 9-oxobicyclo[3.3.1]nonane-3\b-carboxylic acid lactol
;
_chemical_formula_moiety  'C10 H14 O3'
_chemical_formula_sum  'C10 H14 O3'
_chemical_formula_weight  182.21
_chemical_melting_point  422
_symmetry_cell_setting  'Monoclinic'
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  7.331(4)
_cell_length_b  9.288(7)
_cell_length_c  12.669(7)
_cell_angle_alpha  90
_cell_angle_beta  92.64(2)
_cell_angle_gamma  90
_cell_volume  861.7(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.404
_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 0.35127(14) 0.06409(11) 0.71666(8) 0.0429(3) Uani d . 1 . . O
  O2 -0.13911(15) 0.32101(12) 0.79250(8) 0.0480(3) Uani d . 1 . . O
  O3 0.10111(13) 0.19328(10) 0.75595(7) 0.0364(3) Uani d . 1 . . O
  C1 0.14628(18) 0.14322(15) 0.57177(10) 0.0342(3) Uani d . 1 . . C
  C2 0.0128(2) 0.26741(16) 0.54614(11) 0.0402(4) Uani d . 1 . . C
  C3 0.0237(2) 0.37789(16) 0.63548(11) 0.0400(4) Uani d . 1 . . C
  C4 0.2183(2) 0.43584(16) 0.64863(13) 0.0461(4) Uani d . 1 . . C
  C5 0.3523(2) 0.31150(15) 0.67261(12) 0.0392(4) Uani d . 1 . . C
  C6 0.4967(2) 0.29299(18) 0.59060(13) 0.0475(4) Uani d . 1 . . C
  C7 0.4154(2) 0.25132(18) 0.48297(13) 0.0495(4) Uani d . 1 . . C
  C8 0.2886(2) 0.12282(17) 0.48902(12) 0.0437(4) Uani d . 1 . . C
  C9 0.24365(18) 0.17374(14) 0.67771(10) 0.0325(3) Uani d . 1 . . C
  C10 -0.0165(2) 0.29918(14) 0.73416(11) 0.0359(3) Uani d . 1 . . C
  H1 0.282(3) -0.020(2) 0.7123(17) 0.080 Uiso d . 1 . . H
  H1A 0.0764 0.0538 0.5773 0.041 Uiso calc R 1 . . H
  H2B 0.0435 0.3129 0.4804 0.048 Uiso calc R 1 . . H
  H2A -0.1107 0.2302 0.5377 0.048 Uiso calc R 1 . . H
  H3A -0.0638 0.4563 0.6220 0.048 Uiso calc R 1 . . H
  H4B 0.2259 0.5051 0.7060 0.055 Uiso calc R 1 . . H
  H4A 0.2507 0.4845 0.5844 0.055 Uiso calc R 1 . . H
  H5A 0.4140 0.3284 0.7418 0.047 Uiso calc R 1 . . H
  H6B 0.5635 0.3825 0.5845 0.057 Uiso calc R 1 . . H
  H6A 0.5827 0.2194 0.6147 0.057 Uiso calc R 1 . . H
  H7B 0.5131 0.2284 0.4367 0.059 Uiso calc R 1 . . H
  H7A 0.3481 0.3325 0.4527 0.059 Uiso calc R 1 . . H
  H8B 0.3601 0.0374 0.5061 0.052 Uiso calc R 1 . . H
  H8A 0.2270 0.1079 0.4205 0.052 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 0.0378(6) 0.0403(6) 0.0501(6) 0.0054(5) -0.0051(5) 0.0091(5)
  O2 0.0510(6) 0.0466(7) 0.0478(6) 0.0049(5) 0.0156(5) -0.0033(5)
  O3 0.0402(6) 0.0362(6) 0.0331(5) 0.0014(4) 0.0043(4) 0.0043(4)
  C1 0.0324(7) 0.0335(7) 0.0365(8) -0.0013(6) -0.0006(6) -0.0024(6)
  C2 0.0369(8) 0.0487(9) 0.0349(7) 0.0061(7) -0.0001(6) 0.0024(6)
  C3 0.0450(8) 0.0331(8) 0.0421(8) 0.0095(6) 0.0040(6) 0.0046(6)
  C4 0.0572(10) 0.0333(8) 0.0484(9) -0.0048(7) 0.0091(7) 0.0007(7)
  C5 0.0394(8) 0.0398(8) 0.0378(8) -0.0082(6) -0.0031(6) -0.0014(6)
  C6 0.0369(8) 0.0519(9) 0.0538(9) -0.0098(7) 0.0057(7) 0.0034(8)
  C7 0.0435(9) 0.0618(11) 0.0441(9) 0.0002(8) 0.0117(7) 0.0022(8)
  C8 0.0407(8) 0.0521(9) 0.0383(8) 0.0064(7) 0.0026(6) -0.0080(7)
  C9 0.0316(7) 0.0339(7) 0.0320(7) 0.0023(6) 0.0009(5) 0.0025(6)
  C10 0.0396(8) 0.0313(7) 0.0369(8) 0.0000(6) 0.0016(6) -0.0046(6)
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 C9 . 1.3665(17) ?
  O2 C10 . 1.2067(18) ?
  O3 C10 . 1.3287(18) ?
  O3 C9 . 1.4842(17) ?
  C1 C9 . 1.518(2) ?
  C1 C8 . 1.524(2) ?
  C1 C2 . 1.538(2) ?
  C2 C3 . 1.527(2) ?
  C3 C10 . 1.489(2) ?
  C3 C4 . 1.527(2) ?
  C4 C5 . 1.537(2) ?
  C5 C9 . 1.510(2) ?
  C5 C6 . 1.527(2) ?
  C6 C7 . 1.513(2) ?
  C7 C8 . 1.517(2) ?
  O1 H1 . 0.93(2) ?
  C1 H1A . 0.9800 ?
  C2 H2B . 0.9700 ?
  C2 H2A . 0.9700 ?
  C3 H3A . 0.9800 ?
  C4 H4B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C5 H5A . 0.9800 ?
  C6 H6B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C7 H7A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C8 H8A . 0.9700 ?