data_2011605
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1507
_journal_page_last  1509
_publ_section_title
;
(+)-Gibberellin C: structure and hydrogen-bonding pattern of the
monohydrate of a nonracemic pentacyclic diterpenoid
;
loop_
_publ_author_name
  'Thompson, Hugh W.'
  'Brunskill, Andrew P. J.'
  'Lalancette, Roger A.'
_chemical_name_common  '(+)-Gibberellin C'
_chemical_formula_moiety  'C19 H24 O6 , H2 O'
_chemical_formula_sum  'C19 H26 O7'
_chemical_formula_weight  366.40
_chemical_melting_point  538
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
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  9.7300(10)
_cell_length_b  10.661(2)
_cell_length_c  17.898(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1856.6(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.311
_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  .1933(4)  .5707(4)  .7472(2)  .0553(11) Uani d . 1 . . O
  O2  .6888(5)  .2159(3)  .6040(2)  .0634(13) Uani d . 1 . . O
  O3  .7335(4)  .3052(4)  .71322(19)  .0582(12) Uani d . 1 . . O
  O4  .6641(5)  .7805(3)  .5551(2)  .0623(12) Uani d . 1 . . O
  O5  .5026(4)  .6364(3)  .5350(2)  .0441(10) Uani d . 1 . . O
  O6  .7986(4)  .4545(4)  .4036(2)  .0613(13) Uani d . 1 . . O
  O7  .5625(5)  .9829(4)  .6327(2)  .0606(13) Uani d . 1 . . O
  C1  .7299(5)  .5688(5)  .5151(3)  .0393(13) Uani d . 1 . . C
  C2  .7379(6)  .5687(5)  .4278(3)  .0462(14) Uani d . 1 . . C
  C3  .5957(6)  .5808(7)  .3913(3)  .0599(17) Uani d . 1 . . C
  C4  .4837(6)  .5000(6)  .4268(3)  .0524(16) Uani d . 1 . . C
  C4A  .4987(6)  .5019(5)  .5115(3)  .0390(13) Uani d . 1 . . C
  C4B  .3995(5)  .4296(5)  .5594(3)  .0369(13) Uani d . 1 . . C
  C5  .2464(6)  .4592(5)  .5609(3)  .0499(16) Uani d . 1 . . C
  C6  .1761(6)  .3734(5)  .6181(3)  .0506(16) Uani d . 1 . . C
  C7  .2514(6)  .3673(5)  .6942(3)  .0412(14) Uani d . 1 . . C
  C8  .2754(6)  .5030(6)  .7146(3)  .0419(15) Uani d . 1 . . C
  C9  .4152(5)  .5422(4)  .6864(3)  .0389(14) Uani d . 1 . . C
  C9A  .4648(5)  .4289(5)  .6385(3)  .0335(12) Uani d . 1 . . C
  C10  .6223(5)  .4298(5)  .6226(3)  .0337(12) Uani d . 1 . . C
  C10A  .6405(5)  .4583(4)  .5384(3)  .0345(14) Uani d . 1 . . C
  C11  .3996(6)  .3217(4)  .6827(3)  .0407(15) Uani d . 1 . . C
  C12  .6864(6)  .3052(5)  .6440(3)  .0382(13) Uani d . 1 . . C
  C13  .8710(5)  .5777(5)  .5499(3)  .0546(16) Uani d . 1 . . C
  C14  .6342(7)  .6739(5)  .5371(3)  .0444(15) Uani d . 1 . . C
  C15  .1690(7)  .2933(5)  .7509(3)  .0640(19) Uani d . 1 . . C
  H3  .7673  .2365  .7227  .087 Uiso calc R 1 . . H
  H6  .891(7)  .469(6)  .398(3)  .092 Uiso d . 1 . . H
  H7A  .577(7)  .905(6)  .605(3)  .091 Uiso d . 1 . . H
  H7B  .627(6) 1.044(6)  .622(4)  .091 Uiso d . 1 . . H
  H2  .7956  .6389  .4115  .055 Uiso calc R 1 . . H
  H3A  .5673  .6680  .3937  .072 Uiso calc R 1 . . H
  H3B  .6036  .5583  .3390  .072 Uiso calc R 1 . . H
  H4A  .3939  .5320  .4129  .063 Uiso calc R 1 . . H
  H4B  .4911  .4145  .4087  .063 Uiso calc R 1 . . H
  H4C  .4058  .3427  .5419  .044 Uiso calc R 1 . . H
  H5A  .2070  .4457  .5118  .060 Uiso calc R 1 . . H
  H5B  .2324  .5463  .5745  .060 Uiso calc R 1 . . H
  H6A  .1703  .2894  .5975  .061 Uiso calc R 1 . . H
  H6B  .0831  .4030  .6263  .061 Uiso calc R 1 . . H
  H9A  .4776  .5577  .7276  .047 Uiso calc R 1 . . H
  H9B  .4086  .6175  .6562  .047 Uiso calc R 1 . . H
  H10  .6654  .4969  .6519  .040 Uiso calc R 1 . . H
  H10A  .6685  .3824  .5115  .041 Uiso calc R 1 . . H
  H11A  .4458  .3094  .7302  .049 Uiso calc R 1 . . H
  H11B  .4019  .2439  .6546  .049 Uiso calc R 1 . . H
  H13A  .9253  .5071  .5345  .066 Uiso calc R 1 . . H
  H13B  .8626  .5780  .6033  .066 Uiso calc R 1 . . H
  H13C  .9147  .6538  .5338  .066 Uiso calc R 1 . . H
  H15A  .1659  .2067  .7363  .077 Uiso calc R 1 . . H
  H15B  .0772  .3260  .7533  .077 Uiso calc R 1 . . H
  H15C  .2116  .3003  .7991  .077 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  .052(3)  .051(2)  .062(2)  -.001(2)  .009(2)  -.028(2)
  O2  .102(4)  .034(2)  .055(2)  .020(3)  -.007(3)  -.004(2)
  O3  .071(3)  .050(2)  .054(2)  .010(2)  -.018(2)  .010(2)
  O4  .073(3)  .033(2)  .081(3)  -.001(2)  .010(3)  -.006(2)
  O5  .050(3)  .0337(19)  .049(2)  .007(2)  .006(2)  .0078(18)
  O6  .059(3)  .051(2)  .074(3)  .003(2)  .021(2)  -.009(2)
  O7  .064(3)  .053(2)  .065(3)  -.002(2)  -.002(3)  -.014(2)
  C1  .039(3)  .029(2)  .051(3)  .002(3)  .006(3)  .000(3)
  C2  .048(4)  .037(3)  .053(3)  .003(4)  .018(3)  .001(3)
  C3  .063(4)  .074(4)  .043(3)  -.002(4)  .002(3)  .005(4)
  C4  .052(4)  .061(4)  .044(3)  .007(4)  .004(3)  -.001(3)
  C4A  .045(3)  .034(3)  .038(3)  .002(3)  -.002(3)  .001(3)
  C4B  .037(3)  .035(3)  .039(3)  .004(3)  -.003(3)  -.002(3)
  C5  .053(4)  .060(4)  .037(3)  -.007(3)  -.008(3)  -.001(3)
  C6  .047(4)  .051(3)  .054(4)  -.003(3)  .000(3)  -.012(3)
  C7  .046(4)  .034(3)  .043(3)  -.009(3)  .009(3)  .004(3)
  C8  .051(4)  .045(3)  .031(3)  .001(3)  -.007(3)  -.010(3)
  C9  .042(4)  .037(3)  .038(3)  -.003(3)  -.002(3)  -.001(3)
  C9A  .036(3)  .029(2)  .036(3)  .002(3)  -.004(2)  .003(3)
  C10  .040(3)  .024(2)  .037(3)  .002(3)  -.008(2)  .001(3)
  C10A  .041(3)  .027(3)  .035(3)  .003(2)  .003(3)  -.005(2)
  C11  .056(4)  .024(3)  .042(3)  -.002(3)  -.004(3)  -.002(3)
  C12  .039(4)  .037(3)  .038(3)  .001(3)  -.003(3)  .006(3)
  C13  .054(4)  .044(3)  .065(4)  -.012(3)  .000(3)  .011(3)
  C14  .056(5)  .034(3)  .043(3)  -.003(3)  .009(3)  .006(3)
  C15  .073(5)  .054(4)  .065(4)  -.004(4)  .013(4)  -.011(4)
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 . 1.224(6) ?
  O2 C12 . 1.191(5) ?
  O3 C12 . 1.320(6) ?
  O4 C14 . 1.216(6) ?
  O5 C14 . 1.342(7) ?
  O5 C4A . 1.496(6) ?
  O6 C2 . 1.420(6) ?
  C1 C14 . 1.509(7) ?
  C1 C13 . 1.510(7) ?
  C1 C10A . 1.522(7) ?
  C1 C2 . 1.565(7) ?
  C2 C3 . 1.535(8) ?
  C3 C4 . 1.528(8) ?
  C4 C4A . 1.522(6) ?
  C4A C4B . 1.503(7) ?
  C4A C10A . 1.533(7) ?
  C4B C5 . 1.523(7) ?
  C4B C9A . 1.553(6) ?
  C5 C6 . 1.534(7) ?
  C6 C7 . 1.547(7) ?
  C7 C8 . 1.510(7) ?
  C7 C15 . 1.516(7) ?
  C7 C11 . 1.535(8) ?
  C8 C9 . 1.511(7) ?
  C9 C9A . 1.557(6) ?
  C9A C11 . 1.528(6) ?
  C9A C10 . 1.558(7) ?
  C10 C12 . 1.517(7) ?
  C10 C10A . 1.549(7) ?
  O3 H3 .  .8200 ?
  O6 H6 .  .92(7) ?
  O7 H7A .  .98(7) ?
  O7 H7B .  .92(7) ?
  C2 H2 .  .9800 ?
  C3 H3A .  .9700 ?
  C3 H3B .  .9700 ?
  C4 H4A .  .9700 ?
  C4 H4B .  .9700 ?
  C4B H4C .  .9800 ?
  C5 H5A .  .9700 ?
  C5 H5B .  .9700 ?
  C6 H6A .  .9700 ?
  C6 H6B .  .9700 ?
  C9 H9A .  .9700 ?
  C9 H9B .  .9700 ?
  C10 H10 .  .9800 ?
  C10A H10A .  .9800 ?
  C11 H11A .  .9700 ?
  C11 H11B .  .9700 ?
  C13 H13A .  .9600 ?
  C13 H13B .  .9600 ?
  C13 H13C .  .9600 ?
  C15 H15A .  .9600 ?
  C15 H15B .  .9600 ?
  C15 H15C .  .9600 ?