#------------------------------------------------------------------------------
#$Date: 2009-11-16 02:43:51 +0100 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009115.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_2009115
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1905
_journal_page_last  1908
_publ_section_title
;
(+-)-3-Benzoylbicyclo[2.2.1]heptane-2-carboxylic acid:  structures and
hydrogen-bonding patterns of the diendo and the 2-endo-3-exo isomers
;
_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
  'Brunskill, Andrew P. J.'
  'Lalancette*, Roger A.'
  'Thompson, Hugh W.'
_chemical_formula_sum  'C15 H16 O3'
_chemical_formula_weight  244.28
_chemical_melting_point  451
_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  9.866(2)
_cell_length_b  6.010(3)
_cell_length_c  21.697(5)
_cell_angle_alpha  90.00
_cell_angle_beta  99.580(10)
_cell_angle_gamma  90.00
_cell_volume  1268.6(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.279
_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  .2954(2)  .5079(3)  .85762(9)  .0598(6) Uani d . 1 . . O
  O2  .3405(2)  .4078(4) 1.00062(9)  .0641(6) Uani d . 1 . . O
  O3  .4966(2)  .2743(4)  .94631(9)  .0661(7) Uani d . 1 . . O
  H3  .550(3)  .393(6)  .9648(15)  .080 Uiso d . 1 . . H
  C1  .1346(3)  .0838(5)  .94577(14)  .0530(8) Uani d . 1 . . C
  C2  .2777(3)  .1079(5)  .92746(12)  .0467(7) Uani d . 1 . . C
  C3  .2468(3)  .1202(5)  .85414(11)  .0451(7) Uani d . 1 . . C
  C4  .0892(3)  .0716(5)  .84119(14)  .0564(8) Uani d . 1 . . C
  C5  .0093(3)  .2761(6)  .85661(14)  .0639(9) Uani d . 1 . . C
  C6  .0475(3)  .2906(5)  .92868(14)  .0613(9) Uani d . 1 . . C
  C7  .0724(3)  -.0832(5)  .89547(15)  .0639(9) Uani d . 1 . . C
  C8  .3721(3)  .2821(5)  .96061(12)  .0513(8) Uani d . 1 . . C
  C9  .2831(3)  .3377(5)  .82634(12)  .0433(7) Uani d . 1 . . C
  C10  .3035(3)  .3467(5)  .75936(11)  .0409(7) Uani d . 1 . . C
  C11  .2716(3)  .1720(5)  .71790(12)  .0526(8) Uani d . 1 . . C
  C12  .2948(3)  .1896(6)  .65650(13)  .0641(9) Uani d . 1 . . C
  C13  .3508(3)  .3799(6)  .63697(14)  .0622(9) Uani d . 1 . . C
  C14  .3831(3)  .5567(6)  .67777(13)  .0585(8) Uani d . 1 . . C
  C15  .3593(3)  .5395(5)  .73857(12)  .0494(8) Uani d . 1 . . C
  H1A  .1358  .0320  .9887  .053(4) Uiso calc R 1 . . H
  H2A  .3241  -.0349  .9376  .053(4) Uiso calc R 1 . . H
  H3A  .2954  -.0010  .8369  .053(4) Uiso calc R 1 . . H
  H4A  .0562  .0084  .7998  .053(4) Uiso calc R 1 . . H
  H5A  -.0888  .2557  .8437  .072(4) Uiso calc R 1 . . H
  H5B  .0382  .4085  .8368  .072(4) Uiso calc R 1 . . H
  H6A  .0995  .4247  .9413  .072(4) Uiso calc R 1 . . H
  H6B  -.0342  .2885  .9482  .072(4) Uiso calc R 1 . . H
  H7A  .1259  -.2188  .8959  .072(4) Uiso calc R 1 . . H
  H7B  -.0229  -.1180  .8971  .072(4) Uiso calc R 1 . . H
  H11A  .2344  .0418  .7312  .060(4) Uiso calc R 1 . . H
  H12A  .2722  .0721  .6288  .060(4) Uiso calc R 1 . . H
  H13A  .3672  .3907  .5961  .060(4) Uiso calc R 1 . . H
  H14A  .4206  .6863  .6643  .060(4) Uiso calc R 1 . . H
  H15B  .3809  .6584  .7659  .060(4) 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  .0881(16)  .0432(13)  .0520(12)  -.0132(12)  .0230(11)  -.0107(10)
  O2  .0623(13)  .0895(17)  .0439(11)  -.0138(13)  .0185(10)  -.0183(12)
  O3  .0476(13)  .0882(19)  .0633(13)  -.0068(13)  .0118(10)  -.0236(13)
  C1  .0585(18)  .0517(19)  .0522(17)  -.0097(17)  .0191(14)  .0054(15)
  C2  .0508(17)  .0424(18)  .0472(15)  .0020(15)  .0091(13)  .0057(14)
  C3  .0490(17)  .0432(18)  .0438(15)  -.0041(15)  .0093(13)  -.0064(13)
  C4  .0543(18)  .057(2)  .0564(17)  -.0139(17)  .0040(15)  -.0089(16)
  C5  .0432(17)  .065(2)  .082(2)  -.0025(17)  .0061(16)  .0070(19)
  C6  .0557(19)  .055(2)  .079(2)  -.0012(17)  .0277(17)  -.0013(18)
  C7  .058(2)  .0492(19)  .088(2)  -.0121(17)  .0246(17)  .0003(19)
  C8  .0502(18)  .066(2)  .0380(15)  .0015(17)  .0090(13)  .0049(16)
  C9  .0386(15)  .0458(18)  .0453(15)  -.0041(14)  .0063(12)  -.0042(15)
  C10  .0389(15)  .0445(17)  .0379(14)  .0010(14)  .0023(12)  -.0019(13)
  C11  .0560(18)  .056(2)  .0442(15)  -.0064(16)  .0042(13)  -.0017(15)
  C12  .074(2)  .073(2)  .0451(17)  -.007(2)  .0080(15)  -.0130(18)
  C13  .0571(19)  .091(3)  .0396(15)  .000(2)  .0112(14)  -.0016(19)
  C14  .0569(19)  .067(2)  .0531(18)  -.0066(18)  .0147(15)  .0089(18)
  C15  .0509(18)  .0521(19)  .0456(15)  -.0004(16)  .0089(14)  -.0036(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 C9 . 1.223(3) y
  O2 C8 . 1.229(3) y
  O3 C8 . 1.317(3) y
  O3 H3 .  .93(3) y
  C1 C6 . 1.521(4) ?
  C1 C7 . 1.534(4) ?
  C1 C2 . 1.537(4) ?
  C2 C8 . 1.502(4) ?
  C2 C3 . 1.571(3) ?
  C3 C9 . 1.507(4) ?
  C3 C4 . 1.561(4) ?
  C4 C5 . 1.527(4) ?
  C4 C7 . 1.531(4) ?
  C5 C6 . 1.549(4) ?
  C9 C10 . 1.501(4) ?
  C10 C11 . 1.384(4) ?
  C10 C15 . 1.390(4) ?
  C11 C12 . 1.393(4) ?
  C12 C13 . 1.368(4) ?
  C13 C14 . 1.386(4) ?
  C14 C15 . 1.382(4) ?