#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011436.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_2011436
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e479
_journal_page_last  e480
_publ_section_title
;
2,2'-Methylenebis(3-hydroxy-2-cyclohexen-1-one)
;
loop_
_publ_author_name
  'SethuSankar, K.'
  'Banumathi, S.'
  'Krishna, R.'
  'Velmurugan, D.'
_chemical_formula_sum  'C13 H16 O4'
_chemical_formula_weight  236.26
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
  '-x+1/2, -y, z+1/2'
  '-x, -y, -z'
  '-x-1/2, y-1/2, z'
  'x, -y-1/2, z-1/2'
  'x-1/2, y, -z-1/2'
_cell_length_a  9.9313(18)
_cell_length_b  10.3818(14)
_cell_length_c  23.253(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2397.5(6)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.309
_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  .01461(15)  .37135(13)  .07381(7)  .0597(5) Uani d . 1 . . O
  O2  .10450(18)  .29611(15)  .17239(7)  .0684(5) Uani d . 1 . . O
  H2  .0622  .3172  .1436  .103 Uiso calc R 1 . . H
  O3  -.21031(16)  -.01946(14)  .04335(7)  .0616(5) Uani d . 1 . . O
  H3  -.1828  -.0355  .0758  .092 Uiso calc R 1 . . H
  C1  -.11522(17)  .18421(17)  .06350(8)  .0422(5) Uani d . 1 . . C
  O4  -.11738(17)  -.09725(15)  .14432(7)  .0661(5) Uani d . 1 . . O
  C1'  -.02610(18)  .10732(18)  .16172(8)  .0473(5) Uani d . 1 . . C
  C6'  -.03227(19)  -.0280(2)  .16961(8)  .0510(5) Uani d . 1 . . C
  C6  -.16119(17)  .09093(18)  .02628(8)  .0459(5) Uani d . 1 . . C
  C2  -.04387(19)  .29085(17)  .04107(9)  .0466(5) Uani d . 1 . . C
  C7  -.13556(18)  .17381(19)  .12765(8)  .0472(5) Uani d . 1 . . C
  H7A  -.1463  .2602  .1429  .057 Uiso calc R 1 . . H
  H7B  -.2194  .1283  .1344  .057 Uiso calc R 1 . . H
  C2'  .0813(2)  .1751(2)  .18380(9)  .0536(5) Uani d . 1 . . C
  C3  -.0297(3)  .3098(2)  -.02241(9)  .0591(6) Uani d . 1 . . C
  H3A  .0551  .2733  -.0351  .071 Uiso calc R 1 . . H
  H3B  -.0284  .4013  -.0309  .071 Uiso calc R 1 . . H
  C4  -.1442(2)  .2468(2)  -.05494(9)  .0586(6) Uani d . 1 . . C
  H4A  -.1274  .2525  -.0960  .070 Uiso calc R 1 . . H
  H4B  -.2277  .2917  -.0467  .070 Uiso calc R 1 . . H
  C5  -.1575(2)  .1072(2)  -.03767(9)  .0551(5) Uani d . 1 . . C
  H5A  -.2394  .0720  -.0541  .066 Uiso calc R 1 . . H
  H5B  -.0820  .0590  -.0531  .066 Uiso calc R 1 . . H
  C4'  .1281(3)  -.0052(3)  .25192(11)  .0794(8) Uani d . 1 . . C
  H4'1  .2001  -.0486  .2724  .095 Uiso calc R 1 . . H
  H4'2  .0591  .0182  .2795  .095 Uiso calc R 1 . . H
  C5'  .0699(3)  -.0941(2)  .20758(10)  .0691(7) Uani d . 1 . . C
  H5'1  .1421  -.1278  .1838  .083 Uiso calc R 1 . . H
  H5'2  .0273  -.1664  .2268  .083 Uiso calc R 1 . . H
  C3'  .1823(3)  .1149(3)  .22326(12)  .0769(8) Uani d . 1 . . C
  H3'1  .2078  .1768  .2526  .092 Uiso calc R 1 . . H
  H3'2  .2625  .0930  .2015  .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  .0665(9)  .0484(8)  .0643(9)  -.0103(7)  -.0127(7)  .0033(6)
  O2  .0798(11)  .0648(10)  .0606(10)  -.0112(8)  -.0190(8)  -.0001(7)
  O3  .0608(9)  .0555(9)  .0685(9)  -.0158(7)  -.0083(7)  .0019(7)
  C1  .0351(8)  .0455(10)  .0461(10)  .0049(7)  -.0007(7)  -.0013(7)
  O4  .0646(9)  .0662(10)  .0676(10)  -.0134(7)  -.0009(8)  .0105(7)
  C1'  .0460(10)  .0572(11)  .0388(9)  .0024(8)  .0045(8)  .0002(8)
  C6'  .0492(11)  .0605(12)  .0435(10)  -.0025(9)  .0076(8)  .0061(8)
  C6  .0367(9)  .0469(10)  .0540(11)  .0013(8)  -.0025(8)  .0001(8)
  C2  .0427(9)  .0411(10)  .0559(11)  .0039(7)  -.0064(8)  .0008(8)
  C7  .0393(9)  .0531(11)  .0492(10)  .0041(8)  .0063(8)  -.0016(8)
  C2'  .0568(12)  .0601(12)  .0439(9)  -.0008(9)  -.0018(8)  -.0006(9)
  C3  .0675(14)  .0544(12)  .0555(12)  -.0041(10)  .0003(10)  .0081(9)
  C4  .0687(13)  .0604(13)  .0466(10)  .0069(11)  -.0093(10)  .0025(9)
  C5  .0567(12)  .0562(12)  .0524(11)  .0060(9)  -.0078(9)  -.0063(9)
  C4'  .0877(18)  .0935(19)  .0571(13)  -.0018(14)  -.0199(13)  .0212(13)
  C5'  .0796(16)  .0706(15)  .0572(13)  .0047(12)  -.0043(12)  .0153(11)
  C3'  .0733(16)  .0923(18)  .0650(14)  -.0108(14)  -.0251(13)  .0136(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 C2 . 1.271(2) yes
  O2 C2' . 1.304(3) yes
  O2 H2 .  .8200 ?
  O3 C6 . 1.307(2) yes
  O3 H3 .  .8200 ?
  C1 C6 . 1.377(3) ?
  C1 C2 . 1.414(3) ?
  C1 C7 . 1.509(2) ?
  O4 C6' . 1.256(2) yes
  C1' C2' . 1.377(3) ?
  C1' C6' . 1.418(3) ?
  C1' C7 . 1.512(3) ?
  C6' C5' . 1.510(3) ?
  C6 C5 . 1.497(3) ?
  C2 C3 . 1.496(3) ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C2' C3' . 1.496(3) ?
  C3 C4 . 1.515(3) ?
  C3 H3A .  .9700 ?
  C3 H3B .  .9700 ?
  C4 C5 . 1.510(3) ?
  C4 H4A .  .9700 ?
  C4 H4B .  .9700 ?
  C5 H5A .  .9700 ?
  C5 H5B .  .9700 ?
  C4' C5' . 1.500(4) ?
  C4' C3' . 1.513(4) ?
  C4' H4'1 .  .9700 ?
  C4' H4'2 .  .9700 ?
  C5' H5'1 .  .9700 ?
  C5' H5'2 .  .9700 ?
  C3' H3'1 .  .9700 ?
  C3' H3'2 .  .9700 ?