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#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008347.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_2008347
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  563
_journal_page_last  566
_publ_section_title
;
(+-)-3-Oxo-1,2,3,9,10,10a-hexahydrophenanthrene-10a-carboxylic acid:
catemeric hydrogen bonding in a \d-keto acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Miller, Alan J.'
  'Brunskill, Andrew P. J.'
  'Lalancette^*^, Roger A.'
  'Thompson, Hugh W.'
_chemical_name_common
;
(+/-)-10a-Carboxy-1,9,10,10a-tetrahydrophenanthren-3(2H)-one
;
_chemical_formula_moiety  'C15 H14 O3'
_chemical_formula_sum  'C15 H14 O3'
_chemical_formula_structural  'C15 H14 O3'
_chemical_formula_analytical  'C15 H14 O3'
_chemical_formula_weight  242.26
_chemical_melting_point  'Decomposes above 420 K'
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  9.305(2)
_cell_length_b  12.780(3)
_cell_length_c  10.444(3)
_cell_angle_alpha  90.00
_cell_angle_beta  101.79(2)
_cell_angle_gamma  90.00
_cell_volume  1215.8(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.324
_exptl_crystal_density_meas  1.320(10)
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.059
_refine_ls_wR_factor_obs  0.109
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.1885(3) 0.0330(2) 0.0409(2) 0.0840(8) Uani d . 1 . O
  O2 0.3141(2) 0.2787(2) 0.3544(2) 0.0755(7) Uani d . 1 . O
  O3 0.1421(3) 0.3689(2) 0.4247(2) 0.0725(7) Uani d . 1 . O
  H3 0.209(3) 0.420(2) 0.429(3) 0.080 Uiso calc R 1 . H
  C1 -0.0041(3) 0.2103(2) 0.2120(3) 0.0583(8) Uani d . 1 . C
  C2 0.0869(4) 0.1864(2) 0.1104(3) 0.0590(9) Uani d . 1 . C
  C3 0.1546(3) 0.0809(2) 0.1317(3) 0.0548(8) Uani d . 1 . C
  C4 0.1863(3) 0.0388(2) 0.2637(3) 0.0517(8) Uani d . 1 . C
  C4A 0.1646(3) 0.0921(2) 0.3680(3) 0.0426(7) Uani d . 1 . C
  C4B 0.2198(3) 0.0547(2) 0.5035(3) 0.0467(7) Uani d . 1 . C
  C5 0.3296(3) -0.0222(2) 0.5293(3) 0.0559(8) Uani d . 1 . C
  C6 0.3868(4) -0.0558(3) 0.6548(3) 0.0712(10) Uani d . 1 . C
  C7 0.3337(4) -0.0134(3) 0.7569(3) 0.0829(13) Uani d . 1 . C
  C8 0.2258(5) 0.0612(3) 0.7335(3) 0.0760(11) Uani d . 1 . C
  C8A 0.1683(4) 0.0977(2) 0.6086(3) 0.0580(9) Uani d . 1 . C
  C9 0.0542(4) 0.1822(3) 0.5884(3) 0.0722(10) Uani d . 1 . C
  C10A 0.0834(3) 0.1952(2) 0.3533(3) 0.0440(7) Uani d . 1 . C
  C10 -0.0232(3) 0.1968(3) 0.4477(3) 0.0622(9) Uani d . 1 . C
  C11 0.1940(3) 0.2833(2) 0.3810(3) 0.0474(7) Uani d . 1 . C
  H1A -0.0893 0.1648 0.1976 0.074(4) Uiso calc R 1 . H
  H1B -0.0387 0.2819 0.2011 0.074(4) Uiso calc R 1 . H
  H2A 0.0248 0.1898 0.0237 0.074(4) Uiso calc R 1 . H
  H2B 0.1634 0.2387 0.1153 0.074(4) Uiso calc R 1 . H
  H4A 0.2237 -0.0287 0.2761 0.071(4) Uiso calc R 1 . H
  H5A 0.3647 -0.0512 0.4600 0.071(4) Uiso calc R 1 . H
  H6A 0.4602 -0.1063 0.6701 0.071(4) Uiso calc R 1 . H
  H7A 0.3712 -0.0354 0.8420 0.071(4) Uiso calc R 1 . H
  H8A 0.1900 0.0881 0.8036 0.071(4) Uiso calc R 1 . H
  H9A 0.1007 0.2477 0.6206 0.074(4) Uiso calc R 1 . H
  H9B -0.0183 0.1660 0.6402 0.074(4) Uiso calc R 1 . H
  H10A -0.0752 0.2630 0.4391 0.074(4) Uiso calc R 1 . H
  H10B -0.0951 0.1415 0.4238 0.074(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 0.143(2) 0.071(2) 0.0444(12) 0.043(2) 0.0338(14) 0.0086(11)
  O2 0.0588(14) 0.076(2) 0.094(2) -0.0180(13) 0.0219(13) -0.0053(13)
  O3 0.097(2) 0.0472(13) 0.084(2) -0.0206(13) 0.0430(15) -0.0155(12)
  C1 0.050(2) 0.055(2) 0.064(2) 0.006(2) -0.002(2) -0.007(2)
  C2 0.076(2) 0.054(2) 0.042(2) 0.011(2) 0.000(2) -0.0008(14)
  C3 0.069(2) 0.053(2) 0.043(2) 0.010(2) 0.012(2) 0.0012(15)
  C4 0.068(2) 0.042(2) 0.045(2) 0.009(2) 0.0134(15) 0.0041(13)
  C4A 0.0424(15) 0.043(2) 0.044(2) -0.0087(13) 0.0135(13) 0.0006(13)
  C4B 0.047(2) 0.053(2) 0.042(2) -0.0157(15) 0.0130(13) 0.0007(14)
  C5 0.047(2) 0.071(2) 0.050(2) -0.011(2) 0.0117(15) 0.014(2)
  C6 0.058(2) 0.094(3) 0.059(2) -0.016(2) 0.006(2) 0.029(2)
  C7 0.095(3) 0.106(3) 0.043(2) -0.046(3) 0.002(2) 0.021(2)
  C8 0.110(3) 0.078(3) 0.046(2) -0.038(3) 0.029(2) -0.004(2)
  C8A 0.076(2) 0.055(2) 0.050(2) -0.027(2) 0.030(2) -0.004(2)
  C9 0.103(3) 0.057(2) 0.073(2) -0.017(2) 0.057(2) -0.011(2)
  C10A 0.043(2) 0.041(2) 0.050(2) -0.0057(14) 0.0135(13) -0.0054(13)
  C10 0.055(2) 0.056(2) 0.085(2) -0.008(2) 0.037(2) -0.010(2)
  C11 0.056(2) 0.046(2) 0.042(2) -0.010(2) 0.0146(14) -0.0032(13)
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 C3 . 1.223(3) Y
  O2 C11 . 1.207(3) Y
  O3 C11 . 1.315(3) Y
  O3 H3 . 0.90(3) ?
  C1 C2 . 1.517(4) ?
  C1 C10A . 1.545(4) ?
  C2 C3 . 1.486(4) ?
  C3 C4 . 1.452(4) ?
  C4 C4A . 1.335(4) ?
  C4A C4B . 1.482(4) ?
  C4A C10A . 1.511(4) ?
  C4B C8A . 1.398(4) ?
  C4B C5 . 1.403(4) ?
  C5 C6 . 1.378(4) ?
  C6 C7 . 1.375(5) ?
  C7 C8 . 1.369(5) ?
  C8 C8A . 1.386(4) ?
  C8A C9 . 1.499(4) ?
  C9 C10 . 1.510(4) ?
  C10A C11 . 1.513(4) ?
  C10A C10 . 1.535(4) ?
_cod_database_code 2008347