#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012082.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_2012082
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  841
_journal_page_last  843
_publ_section_title
;
(-)-Gibberic acid: hydrogen-bonding pattern of the
monohydrate of a nonracemic tetracyclic \d-keto acid derivative of
gibberellin A~3~
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_name_common  'gibberic acid monohydrate'
_chemical_formula_moiety  'C18 H20 O3 , H2 O'
_chemical_formula_sum  'C18 H22 O4'
_chemical_formula_weight  302.36
_chemical_melting_point  427
_symmetry_cell_setting  'monoclinic'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.841(3)
_cell_length_b  6.283(3)
_cell_length_c  14.646(4)
_cell_angle_alpha  90
_cell_angle_beta  103.45(2)
_cell_angle_gamma  90
_cell_volume  791.2(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.269
_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 1.0936(3)  -.0343(4)  .3644(2)  .0707(10) Uani d . 1 . . O
  O2  .5899(3)  .6755(4)  .34957(18)  .0556(8) Uani d . 1 . . O
  O3  .5610(3)  .3247(4)  .3671(2)  .0584(8) Uani d . 1 . . O
  O4  .5808(3)  .4101(5)  .5434(2)  .0644(9) Uani d . 1 . . O
  C1  .5423(4)  .7749(6)  .1311(2)  .0440(10) Uani d . 1 . . C
  C2  .5783(5)  .9092(6)  .0640(3)  .0551(12) Uani d . 1 . . C
  C3  .7099(5)  .8875(7)  .0311(3)  .0628(12) Uani d . 1 . . C
  C4  .8112(5)  .7238(6)  .0622(3)  .0551(11) Uani d . 1 . . C
  C4A  .7799(4)  .5848(6)  .1292(2)  .0454(10) Uani d . 1 . . C
  C4B  .8615(4)  .3826(6)  .1658(2)  .0487(10) Uani d . 1 . . C
  C5 1.0363(5)  .3533(9)  .1760(3)  .0722(13) Uani d . 1 . . C
  C6 1.1399(4)  .4105(7)  .2707(3)  .0631(13) Uani d . 1 . . C
  C7 1.0665(4)  .3534(6)  .3542(3)  .0459(10) Uani d . 1 . . C
  C8 1.0124(4)  .1230(6)  .3391(2)  .0507(11) Uani d . 1 . . C
  C9  .8410(4)  .1173(5)  .2930(3)  .0472(11) Uani d . 1 . . C
  C9A  .8090(4)  .3482(5)  .2585(2)  .0388(9) Uani d . 1 . . C
  C10  .6398(4)  .4323(5)  .2330(2)  .0376(9) Uani d . 1 . . C
  C10A  .6474(4)  .6118(5)  .1643(2)  .0371(9) Uani d . 1 . . C
  C11  .9141(4)  .4709(5)  .3389(2)  .0419(9) Uani d . 1 . . C
  C12  .5914(4)  .4945(7)  .3210(3)  .0436(10) Uani d . 1 . . C
  C13 1.1788(4)  .3904(7)  .4482(3)  .0653(13) Uani d . 1 . . C
  C14  .3936(4)  .8093(7)  .1631(3)  .0623(12) Uani d . 1 . . C
  H3  .5618  .3576  .4213  .067(14) Uiso calc R 1 . . H
  H4AA  .537(5)  .334(8)  .577(3)  .080 Uiso d . 1 . . H
  H4BB  .668(4)  .432(7)  .581(3)  .080 Uiso d . 1 . . H
  H2  .5098 1.0190  .0403  .066 Uiso calc R 1 . . H
  H3A  .7308  .9840  -.0125  .075 Uiso calc R 1 . . H
  H4B  .8112  .2700  .1231  .058 Uiso calc R 1 . . H
  H4  .8996  .7061  .0387  .066 Uiso calc R 1 . . H
  H5A 1.0552  .2056  .1629  .087 Uiso calc R 1 . . H
  H5B 1.0675  .4390  .1285  .087 Uiso calc R 1 . . H
  H6A 1.1612  .5621  .2720  .076 Uiso calc R 1 . . H
  H6B 1.2382  .3362  .2783  .076 Uiso calc R 1 . . H
  H9A  .7798  .0795  .3377  .057 Uiso calc R 1 . . H
  H9B  .8189  .0175  .2411  .057 Uiso calc R 1 . . H
  H10  .5706  .3201  .2007  .045 Uiso calc R 1 . . H
  H11A  .9257  .6179  .3216  .050 Uiso calc R 1 . . H
  H11B  .8731  .4673  .3949  .050 Uiso calc R 1 . . H
  H13A 1.2096  .5372  .4535  .098 Uiso calc R 1 . . H
  H13B 1.2689  .3022  .4529  .098 Uiso calc R 1 . . H
  H13C 1.1289  .3552  .4979  .098 Uiso calc R 1 . . H
  H14A  .4147  .8947  .2189  .093 Uiso calc R 1 . . H
  H14B  .3523  .6742  .1760  .093 Uiso calc R 1 . . H
  H14C  .3192  .8808  .1146  .093 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  .0552(18)  .0398(16)  .106(2)  .0082(15)  -.0038(16)  -.0003(16)
  O2  .0641(19)  .0575(17)  .0482(16)  .0078(16)  .0191(14)  -.0048(14)
  O3  .0651(19)  .0632(18)  .0514(18)  -.0035(17)  .0229(14)  .0102(16)
  O4  .0549(18)  .082(2)  .0570(19)  -.0117(18)  .0142(13)  .0098(16)
  C1  .053(2)  .042(2)  .0319(19)  -.004(2)  .0002(18)  .0000(18)
  C2  .074(3)  .043(2)  .042(2)  .003(2)  .000(2)  .010(2)
  C3  .091(3)  .056(3)  .040(2)  -.012(3)  .012(2)  .013(2)
  C4B  .049(2)  .054(2)  .043(2)  .003(2)  .0118(17)  -.002(2)
  C4  .066(3)  .055(2)  .049(3)  -.008(2)  .022(2)  .002(2)
  C4A  .055(2)  .045(2)  .036(2)  -.008(2)  .0092(18)  -.0019(19)
  C5  .063(3)  .092(3)  .070(3)  .003(3)  .033(2)  .005(3)
  C6  .053(2)  .065(3)  .075(3)  -.002(2)  .023(2)  -.001(3)
  C7  .038(2)  .0373(19)  .058(2)  -.005(2)  .0030(19)  -.004(2)
  C8  .053(3)  .043(2)  .053(3)  .001(2)  .008(2)  -.001(2)
  C9A  .041(2)  .0328(18)  .0421(19)  .0003(18)  .0085(17)  .0006(18)
  C9  .043(2)  .036(2)  .060(2)  -.0013(19)  .0051(19)  -.004(2)
  C10A  .042(2)  .037(2)  .0304(19)  -.005(2)  .0046(17)  -.0026(17)
  C10  .036(2)  .036(2)  .039(2)  -.0048(18)  .0064(16)  -.0038(17)
  C11  .045(2)  .0351(18)  .045(2)  .0019(19)  .0109(17)  -.0018(19)
  C12  .037(2)  .051(2)  .042(2)  -.001(2)  .0084(18)  .007(2)
  C13  .051(2)  .056(2)  .078(3)  -.002(2)  -.006(2)  -.007(2)
  C14  .059(3)  .061(3)  .063(3)  .013(2)  .006(2)  .006(2)
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 C8 . 1.227(4) ?
  O2 C12 . 1.213(5) Y
  O3 C12 . 1.323(4) Y
  C1 C2 . 1.388(5) ?
  C1 C10A . 1.393(5) ?
  C1 C14 . 1.511(5) ?
  C2 C3 . 1.365(5) ?
  C3 C4 . 1.370(5) ?
  C4 C4A . 1.389(5) ?
  C4A C10A . 1.394(5) ?
  C4B C4A . 1.498(5) ?
  C4B C5 . 1.528(5) ?
  C4B C9A . 1.549(5) ?
  C5 C6 . 1.516(5) ?
  C6 C7 . 1.555(5) ?
  C7 C11 . 1.507(5) ?
  C7 C13 . 1.517(4) ?
  C7 C8 . 1.525(5) ?
  C8 C9 . 1.510(5) ?
  C9A C11 . 1.529(4) ?
  C9A C9 . 1.541(5) ?
  C9A C10 . 1.547(5) ?
  C10 C12 . 1.501(5) ?
  C10A C10 . 1.524(5) ?
  O3 H3 .  .8200 ?
  O4 H4AA .  .84(5) ?
  O4 H4BB .  .85(4) ?
  C2 H2 .  .9300 ?
  C3 H3A .  .9300 ?
  C4B H4B .  .9800 ?
  C4 H4 .  .9300 ?
  C5 H5A .  .9700 ?
  C5 H5B .  .9700 ?
  C6 H6A .  .9700 ?
  C6 H6B .  .9700 ?
  C9 H9A .  .9700 ?
  C9 H9B .  .9700 ?
  C10 H10 .  .9800 ?
  C11 H11A .  .9700 ?
  C11 H11B .  .9700 ?
  C13 H13A .  .9600 ?
  C13 H13B .  .9600 ?
  C13 H13C .  .9600 ?
  C14 H14A .  .9600 ?
  C14 H14B .  .9600 ?
  C14 H14C .  .9600 ?