#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006136.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_2006136
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1997
_journal_volume 53
_journal_page_first  616
_journal_page_last  620
_publ_section_title
;
3-Acetonylbicyclo[6.3.0]undecane-2,6-dione, (I),
7-Acetonyl-4,4-dimethylbicyclo[6.3.0]undecane-2,6-dione, (II),
7,12-Dihydroxy-12-methyltetracyclo[8.2.1.0^1,5^.0^7,11^]tridecan-13-one
Monohydrate, (III), and
8,8-Dimethyltricyclo[9.3.0.0^2,6^]tetradec-5-ene-4,10-dione, (IV)
;
_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
 'Ohba, Shigeru'
 'Umehara, Misao'
_chemical_formula_moiety  'C14 H20 O3, H2 O'
_chemical_formula_sum  'C14 H22 O4'
_chemical_formula_weight  254.33
_chemical_melting_point  396-397'
_symmetry_cell_setting  'Monoclinic'
loop_
_symmetry_equiv_pos_as_xyz
 +x,+y,+z
 1/2-x,1/2+y,1/2-z
 -x,-y,-z
 1/2+x,1/2-y,1/2+z
_cell_length_a  8.115(2)
_cell_length_b  17.959(2)
_cell_length_c  9.034(2)
_cell_angle_alpha  90
_cell_angle_beta  94.71(2)
_cell_angle_gamma  90
_cell_volume  1312.1(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  '298'
_exptl_crystal_density_diffrn  1.287
_diffrn_ambient_temperature  299
_refine_ls_R_factor_obs   .0564
_refine_ls_wR_factor_obs   .0538
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_occupancy
 C1  .9320(3)  .81260(10)
 .1076(2)  .0410(10)
 Uij 1.000
 C2  .9797(3)  .82680(10)
 .2716(3)  .0450(10)
 Uij 1.000
 C3  .8870(3)  .89360(10)
 .3280(2)  .0390(10)
 Uij 1.000
 C4  .8756(3)  .8965(2)  .4970(3)  .0570(10)
 Uij 1.000
 C5  .7406(4)  .9541(2)  .5146(3)  .0690(10)
 Uij 1.000
 C6  .6119(3)  .93660(10)
 .3892(3)  .0490(10)
 Uij 1.000
 C7  .7021(2)  .90000(10)
 .2639(2)  .0310(10)
 Uij 1.000
 C8  .6989(3)  .94400(10)
 .1201(2)  .0390(10)
 Uij 1.000
 C9  .7143(3)  .89080(10)
 -.0099(2)  .0460(10)
  Uij 1.000
 C10  .8694(4)  .9020(2)  -.0934(3)  .0670(10)
   Uij 1.000
 C11 1.0064(3)  .87380(10)
  .0134(3)  .0560(10)
  Uij 1.000
 C12  .7406(3)  .81560(10)
  .0698(2)  .0370(10)
  Uij 1.000
 C13  .6372(2)  .82420(10)
  .2044(2)  .0370(10)
  Uij 1.000
 C14  .4524(3)  .8260(2)  .1585(4)  .0640(10)
  Uij 1.000
 O15  .6909(2) 1.01120(10)
  .1088(2)  .0570(10)
  Uij 1.000
 O16  .9994(2)  .74310(10)
  .0614(2)  .0590(10)
  Uij 1.000
 O17  .6708(2)  .76400(10)
  .3063(2)  .0490(10)
  Uij 1.000
 O18  .8159(3)  .63730(10)
  .1972(2)  .0820(10)
  Uij 1.000
 H2A 1.098(2)  .8360(10)
   .294(2)  .047(6) Uiso 1.000
 H2B  .951(2)  .7810(10)
   .324(2)  .038(6) Uiso 1.000
 H3  .938(2)  .9390(10)
  .299(2)  .031(5) Uiso 1.000
 H4A  .985(3)  .9080(10)
   .551(2)  .069(8) Uiso 1.000
 H4B  .842(2)  .8430(10)
   .527(2)  .048(7) Uiso 1.000
 H5A  .800(3) 1.007(2)  .493(3)  .090(10)
 Uiso 1.000
 H6A  .549(2)  .9800(10)
   .354(2)  .050(6) Uiso 1.000
 H6B  .526(3)  .9030(10)
   .419(2)  .059(7) Uiso 1.000
 H9  .611(2)  .8910(10)
  -.066(2)  .038(6) Uiso 1.000
 H10A  .860(3)  .8700(10)
 -.180(3)  .090(9) Uiso 1.000
 H10B  .881(3)  .9530(10)
 -.120(3)  .082(9) Uiso 1.000
 H11A 1.048(3)  .9200(10)
 .080(2)  .063(7) Uiso 1.000
 H11B 1.103(3)  .8540(10)
 -.033(2)  .061(7) Uiso 1.000
 H12  .709(2)  .7720(10)
   .009(2)  .035(5) Uiso 1.000
 H14A  .421(3)  .8690(10)
 .102(3)  .090(10)
  Uiso 1.000
 H14B  .420(3)  .7810(10)
 .100(3)  .089(9) Uiso 1.000
 H16  .959(3)  .7060(10)
   .100(3)  .070(9) Uiso 1.000
 H17  .620(3)  .7670(10)
   .375(3)  .070(9) Uiso 1.000
 H18A  .816(3)  .5970(10)
 .244(3)  .074(9) Uiso 1.000
 H18B  .757(3)  .6690(10)
 .235(3)  .080(10)
  Uiso 1.000
 H5B  .703(3)  .9480(10)
   .613(3)  .088(8) Uiso 1.000
 H14C  .394(2)  .8240(10)
 .250(2)  .054(7) Uiso 1.000
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
 C1  .0470(10)
  .0330(10)
  .0410(10)
  .0020(10)
  .0250(10)
  .0000(10)
 C2  .0290(10)
  .055(2)  .0480(10)
  .0070(10)
  .0110(10)
  -.0020(10)
 C3  .0390(10)
  .0410(10)
  .0350(10)
  .0010(10)
  .0070(10)
  -.0010(10)
 C4  .064(2)  .075(2)  .0320(10)
  .017(2)  -.0020(10)
   -.0060(10)
 C5  .082(2)  .085(2)  .036(2)  .027(2)  .0070(10)
  -.012(2)
 C6  .052(2)  .045(2)  .049(2)  .0140(10)
  .0230(10)
  -.0010(10)
 C7  .0340(10)
  .0300(10)
  .0280(10)
  .0030(10)
  .0110(10)
  .0020(10)
 C8  .0430(10)
  .0330(10)
  .0400(10)
  .0000(10)
  .0030(10)
  .0030(10)
 C9  .064(2)  .0420(10)
  .0330(10)
  -.0020(10)
   -.0030(10)
 .0020(10)
 C10  .110(2)  .052(2)  .0370(10)
   -.007(2)  .034(2)  .0040(10)
 C11  .073(2)  .0410(10)
   .052(2)  -.0060(10)
 .0390(10)
 -.0020(10)
 C12  .0510(10)
   .0300(10)
   .0290(10)
   -.0050(10)
 .0060(10)
 -.0050(10)
 C13  .0330(10)
   .0360(10)
   .0410(10)
   .0010(10)
   .0100(10)
   .0040(10)
 C14  .0340(10)
   .062(2)  .092(2)  -.0060(10)
 .0050(10)
 -.005(2)
 O15  .0880(10)
   .0320(10)
   .0510(10)
   .0030(10)
   .0090(10)
   .0060(10)
 O16  .0760(10)
   .0370(10)
   .0630(10)
   .0090(10)
   .0480(10)
   .0010(10)
 O17  .0590(10)
   .0340(10)
   .0560(10)
   .0070(10)
   .0360(10)
   .0130(10)
 O18  .110(2)  .0410(10)
   .096(2)  .0140(10)
   .0620(10)
   .0160(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
 C1 C2 . . 1.522(4) yes
 C1 C11 . . 1.543(4) yes
 C1 C12 . . 1.564(3) yes
 C1 O16 . . 1.437(3) yes
 C2 C3 . . 1.526(4) yes
 C3 C4 . . 1.538(4) yes
 C3 C7 . . 1.567(3) yes
 C4 C5 . . 1.524(5) yes
 C5 C6 . . 1.510(4) yes
 C6 C7 . . 1.545(4) yes
 C7 C8 . . 1.519(3) yes
 C7 C13 . . 1.539(3) yes
 C8 C9 . . 1.527(3) yes
 C8 O15 . . 1.213(3) yes
 C9 C10 . . 1.532(4) yes
 C9 C12 . . 1.536(3) yes
 C10 C11 . . 1.499(4) yes
 C12 C13 . . 1.541(3) yes
 C13 C14 . . 1.524(4) yes
 C13 O17 . . 1.433(3) yes
 C2 H2A . .  .97(2) ?
 C2 H2B . .  .981(19) ?
 C3 H3 . .  .967(18) ?
 C4 H4A . . 1.00(3) ?
 C4 H4B . . 1.04(2) ?
 C5 H5A . . 1.09(3) ?
 C5 H5B . .  .97(3) ?
 C6 H6A . .  .97(2) ?
 C6 H6B . .  .97(3) ?
 C9 H9 . .  .940(19) ?
 C10 H10A . .  .97(3) ?
 C10 H10B . .  .95(3) ?
 C11 H11A . . 1.06(3) ?
 C11 H11B . .  .99(3) ?
 C12 H12 . .  .974(18) ?
 C14 H14A . .  .95(3) ?
 C14 H14B . .  .99(3) ?
 C14 H14C . .  .99(3) ?
 O16 H16 . .  .83(3) ?
 O17 H17 . .  .77(3) ?
 O18 H18A . .  .84(3) ?
 O18 H18B . .  .84(3) ?
_cod_database_code 2006136