#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013987.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_2013987
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o408
_journal_page_last  o410
_publ_section_title
;
(-)-Parasantonic acid and its enol lactone, (+)-parasantonide:
observation of the rare acid-to-acid catemeric hydrogen-bonding mode in a
\g,\e-diketocarboxylic acid
;
loop_
_publ_author_name
  'Zinczuk, Juan'
  'Ruveda, Edmundo A.'
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_name_common  '(+)-parasantonide'
_chemical_formula_moiety  'C15 H18 O3'
_chemical_formula_sum  'C15 H18 O3'
_chemical_formula_iupac  'C15 H18 O3'
_chemical_formula_weight  246.29
_chemical_melting_point  376
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  8.562(2)
_cell_length_b  11.656(3)
_cell_length_c  13.275(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1324.8(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.235
_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 0.8794(3) 0.4348(2) 0.2972(2) 0.0540(8) Uani d . 1 . . O
  O2 0.5827(4) 0.2070(3) 0.5513(2) 0.0686(9) Uani d . 1 . . O
  O3 1.1011(4) 0.4217(3) 0.2096(3) 0.0923(12) Uani d . 1 . . O
  C1 0.7504(4) 0.2659(3) 0.2405(3) 0.0357(9) Uani d . 1 . . C
  C2 0.6469(4) 0.2992(4) 0.1505(3) 0.0464(11) Uani d . 1 . . C
  H2A 0.6586 0.2450 0.0955 0.056 Uiso calc R 1 . . H
  H2B 0.6720 0.3756 0.1264 0.056 Uiso calc R 1 . . H
  C3 0.4802(4) 0.2949(4) 0.1947(3) 0.0491(11) Uani d . 1 . . C
  H3A 0.4429 0.3716 0.2097 0.059 Uiso calc R 1 . . H
  H3B 0.4087 0.2591 0.1475 0.059 Uiso calc R 1 . . H
  C3A 0.4932(4) 0.2231(3) 0.2920(3) 0.0403(9) Uani d . 1 . . C
  C4 0.5140(4) 0.2950(3) 0.3884(3) 0.0409(10) Uani d . 1 . . C
  H4A 0.4147 0.3242 0.4147 0.049 Uiso calc R 1 . . H
  C5 0.5931(5) 0.2108(4) 0.4603(3) 0.0465(10) Uani d . 1 . . C
  C5A 0.6590(4) 0.1673(3) 0.2862(3) 0.0382(10) Uani d . 1 . . C
  H51A 0.6591 0.1002 0.2417 0.046 Uiso calc R 1 . . H
  C6 0.6976(5) 0.1334(3) 0.3952(3) 0.0460(11) Uani d . 1 . . C
  H6A 0.8071 0.1468 0.4099 0.055 Uiso calc R 1 . . H
  H6B 0.6741 0.0531 0.4070 0.055 Uiso calc R 1 . . H
  C7 0.6378(5) 0.3876(3) 0.3799(3) 0.0395(10) Uani d . 1 . . C
  C8 0.7486(4) 0.3656(3) 0.3130(3) 0.0382(10) Uani d . 1 . . C
  C9 0.9263(4) 0.2561(4) 0.2193(3) 0.0514(12) Uani d . 1 . . C
  H9A 0.9711 0.2070 0.2718 0.062 Uiso calc R 1 . . H
  C10 0.9834(5) 0.3763(4) 0.2383(4) 0.0589(13) Uani d . 1 . . C
  C11 0.9774(5) 0.2072(4) 0.1179(3) 0.0746(15) Uani d . 1 . . C
  H11A 1.0894 0.2062 0.1145 0.112 Uiso calc R 1 . . H
  H11B 0.9368 0.2541 0.0646 0.112 Uiso calc R 1 . . H
  H11C 0.9383 0.1304 0.1110 0.112 Uiso calc R 1 . . H
  C12 0.6355(6) 0.4862(3) 0.4533(3) 0.0598(13) Uani d . 1 . . C
  H12A 0.7314 0.5284 0.4481 0.090 Uiso calc R 1 . . H
  H12B 0.6244 0.4571 0.5206 0.090 Uiso calc R 1 . . H
  H12C 0.5493 0.5358 0.4380 0.090 Uiso calc R 1 . . H
  C13 0.3592(5) 0.1379(4) 0.3058(3) 0.0616(12) Uani d . 1 . . C
  H13A 0.2625 0.1790 0.3122 0.092 Uiso calc R 1 . . H
  H13B 0.3768 0.0932 0.3655 0.092 Uiso calc R 1 . . H
  H13C 0.3540 0.0880 0.2484 0.092 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 0.0413(16) 0.0524(17) 0.0682(19) -0.0119(16) -0.0001(17) 0.0085(17)
  O2 0.089(2) 0.085(2) 0.0313(18) -0.010(2) 0.0112(17) -0.0008(19)
  O3 0.056(2) 0.108(3) 0.113(3) -0.025(2) 0.025(2) 0.023(3)
  C1 0.0309(18) 0.041(2) 0.035(2) 0.004(2) 0.0023(18) 0.0029(19)
  C2 0.051(3) 0.053(3) 0.035(2) 0.006(3) 0.001(2) -0.002(2)
  C3 0.043(2) 0.062(3) 0.042(2) 0.001(2) -0.011(2) -0.009(2)
  C3A 0.038(2) 0.042(2) 0.041(2) -0.013(2) 0.004(2) -0.005(2)
  C4 0.038(2) 0.045(2) 0.040(2) 0.004(2) 0.0075(19) -0.008(2)
  C5 0.050(3) 0.048(3) 0.042(2) -0.017(2) 0.002(2) -0.003(2)
  C5A 0.047(2) 0.034(2) 0.033(2) 0.003(2) 0.000(2) -0.005(2)
  C6 0.059(3) 0.042(2) 0.037(2) 0.001(2) 0.004(2) 0.006(2)
  C7 0.042(2) 0.036(2) 0.039(2) 0.000(2) -0.004(2) 0.000(2)
  C8 0.033(2) 0.036(2) 0.045(3) -0.004(2) -0.008(2) 0.006(2)
  C9 0.042(2) 0.066(3) 0.046(3) 0.011(2) 0.006(2) 0.014(3)
  C10 0.038(2) 0.073(3) 0.065(3) -0.002(3) 0.008(2) 0.023(3)
  C11 0.065(3) 0.100(4) 0.059(3) 0.024(3) 0.020(3) 0.006(3)
  C12 0.077(3) 0.054(3) 0.048(3) -0.002(3) 0.000(3) -0.009(2)
  C13 0.052(3) 0.068(3) 0.065(3) -0.018(3) -0.001(3) -0.010(3)
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 C10 . 1.367(5) ?
  O1 C8 . 1.396(4) ?
  O2 C5 . 1.212(5) ?
  O3 C10 . 1.200(5) ?
  C1 C8 . 1.509(5) ?
  C1 C5A . 1.518(5) ?
  C1 C9 . 1.536(5) ?
  C1 C2 . 1.538(5) ?
  C2 C3 . 1.544(5) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C3A . 1.544(5) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C3A C13 . 1.528(5) ?
  C3A C4 . 1.540(5) ?
  C3A C5A . 1.563(5) ?
  C4 C7 . 1.517(5) ?
  C4 C5 . 1.527(5) ?
  C4 H4A . 0.9800 ?
  C5 C6 . 1.536(5) ?
  C5A C6 . 1.536(5) ?
  C5A H51A . 0.9800 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 C8 . 1.324(5) ?
  C7 C12 . 1.507(5) ?
  C9 C10 . 1.506(6) ?
  C9 C11 . 1.525(5) ?
  C9 H9A . 0.9800 ?
  C11 H11A . 0.9600 ?
  C11 H11B . 0.9600 ?
  C11 H11C . 0.9600 ?
  C12 H12A . 0.9600 ?
  C12 H12B . 0.9600 ?
  C12 H12C . 0.9600 ?
  C13 H13A . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13C . 0.9600 ?