#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012567.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_2012567
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o199
_journal_page_last  o200
_publ_section_title
;
The antiinflammatory triterpenoid methyl
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate
;
loop_
_publ_author_name
  'Bore, Lothar'
  'Honda, Tadashi'
  'Gribble, Gordon W.'
  'Lork, Enno'
  'Jasinski, Jerry P.'
_chemical_formula_moiety  'C32 H43 N O4 , C H4 O , H2 O'
_chemical_formula_sum  'C33 H49 N O6'
_chemical_formula_weight  555.73
_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  6.5370(10)
_cell_length_b  8.9500(10)
_cell_length_c  51.128(9)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2991.3(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.234
_diffrn_ambient_temperature  173(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
  C1  .3942(7)  .6932(5)  .55329(9)  .0238(10) Uani d . 1 . . C
  H1  .4240  .7952  .5567  .022(9) Uiso calc R 1 . . H
  C2  .3391(8)  .6534(5)  .52930(9)  .0250(10) Uani d . 1 . . C
  C31  .3352(8)  .7630(6)  .50822(9)  .0277(11) Uani d . 1 . . C
  N1  .3273(8)  .8501(5)  .49208(9)  .0423(12) Uani d . 1 . . N
  C3  .2974(7)  .4954(5)  .52152(9)  .0230(10) Uani d . 1 . . C
  O1  .2931(7)  .4608(4)  .49854(7)  .0373(9) Uani d . 1 . . O
  C4  .2601(8)  .3822(5)  .54307(9)  .0247(10) Uani d . 1 . . C
  C23  .4204(9)  .2547(6)  .54065(10)  .0322(12) Uani d . 1 . . C
  H23A  .4050  .2052  .5237  .051(4) Uiso calc R 1 . . H
  H23B  .3988  .1818  .5547  .051(4) Uiso calc R 1 . . H
  H23C  .5584  .2966  .5421  .051(4) Uiso calc R 1 . . H
  C24  .0474(8)  .3145(6)  .53706(10)  .0288(11) Uani d . 1 . . C
  H24A  -.0519  .3952  .5345  .051(4) Uiso calc R 1 . . H
  H24B  .0039  .2517  .5517  .051(4) Uiso calc R 1 . . H
  H24C  .0556  .2537  .5211  .051(4) Uiso calc R 1 . . H
  C5  .2516(7)  .4571(5)  .57041(9)  .0199(9) Uani d . 1 . . C
  H5  .1164  .5092  .5709  .025(8) Uiso calc R 1 . . H
  C6  .2450(8)  .3469(5)  .59324(9)  .0241(10) Uani d . 1 . . C
  H6A  .1520  .2630  .5890  .035(4) Uiso calc R 1 . . H
  H6B  .3833  .3055  .5964  .035(4) Uiso calc R 1 . . H
  C7  .1706(7)  .4259(5)  .61749(8)  .0218(9) Uani d . 1 . . C
  H7A  .1693  .3537  .6322  .035(4) Uiso calc R 1 . . H
  H7B  .0280  .4590  .6146  .035(4) Uiso calc R 1 . . H
  C8  .3001(7)  .5622(5)  .62551(9)  .0205(9) Uani d . 1 . . C
  C26  .4940(8)  .4978(5)  .63931(9)  .0251(10) Uani d . 1 . . C
  H26A  .4550  .4539  .6561  .051(4) Uiso calc R 1 . . H
  H26B  .5930  .5783  .6422  .051(4) Uiso calc R 1 . . H
  H26C  .5558  .4207  .6282  .051(4) Uiso calc R 1 . . H
  C9  .3776(7)  .6550(5)  .60232(9)  .0195(9) Uani d . 1 . . C
  C10  .4113(7)  .5815(5)  .57540(8)  .0198(9) Uani d . 1 . . C
  C25  .6381(7)  .5274(6)  .57426(10)  .0254(10) Uani d . 1 . . C
  H25A  .6732  .5007  .5562  .051(4) Uiso calc R 1 . . H
  H25B  .6549  .4398  .5856  .051(4) Uiso calc R 1 . . H
  H25C  .7285  .6076  .5803  .051(4) Uiso calc R 1 . . H
  C11  .4363(8)  .7980(5)  .60653(9)  .0240(10) Uani d . 1 . . C
  H11  .4921  .8525  .5923  .022(9) Uiso calc R 1 . . H
  C12  .4185(8)  .8738(5)  .63200(10)  .0254(10) Uani d . 1 . . C
  O2  .4933(7)  .9987(4)  .63521(7)  .0377(10) Uani d . 1 . . O
  C13  .3190(7)  .7913(5)  .65438(8)  .0191(9) Uani d . 1 . . C
  H13  .4330  .7340  .6627  .025(8) Uiso calc R 1 . . H
  C14  .1723(7)  .6702(5)  .64380(8)  .0183(9) Uani d . 1 . . C
  C27  -.0043(7)  .7412(5)  .62779(9)  .0230(9) Uani d . 1 . . C
  H27A  -.0392  .6757  .6131  .018(12) Uiso calc R 1 . . H
  H27B  .0392  .8388  .6211  .06(2) Uiso calc R 1 . . H
  H27C  -.1243  .7539  .6391  .018(12) Uiso calc R 1 . . H
  C15  .0803(7)  .5836(5)  .66707(8)  .0203(9) Uani d . 1 . . C
  H15A  -.0331  .5204  .6606  .035(4) Uiso calc R 1 . . H
  H15B  .1864  .5165  .6743  .035(4) Uiso calc R 1 . . H
  C16  -.0004(8)  .6837(5)  .68901(9)  .0200(9) Uani d . 1 . . C
  H16A  -.0479  .6201  .7036  .035(4) Uiso calc R 1 . . H
  H16B  -.1195  .7409  .6825  .035(4) Uiso calc R 1 . . H
  C17  .1614(8)  .7936(5)  .69927(9)  .0203(9) Uani d . 1 . . C
  C28  .3407(8)  .7139(5)  .71142(9)  .0250(10) Uani d . 1 . . C
  O3  .5145(6)  .7599(5)  .71185(8)  .0425(10) Uani d . 1 . . O
  O4  .2893(6)  .5841(4)  .72319(7)  .0335(9) Uani d . 1 . . O
  C32  .4562(9)  .5074(6)  .73594(11)  .0387(13) Uani d . 1 . . C
  H32A  .5592  .4795  .7229  .051(4) Uiso calc R 1 . . H
  H32B  .4044  .4172  .7446  .051(4) Uiso calc R 1 . . H
  H32C  .5182  .5735  .7490  .051(4) Uiso calc R 1 . . H
  C18  .2363(7)  .8934(5)  .67645(8)  .0203(9) Uani d . 1 . . C
  H18  .3559  .9514  .6832  .025(8) Uiso calc R 1 . . H
  C19  .0741(8) 1.0088(5)  .66814(9)  .0239(10) Uani d . 1 . . C
  H19A  .1318 1.0724  .6541  .035(4) Uiso calc R 1 . . H
  H19B  -.0453  .9553  .6608  .035(4) Uiso calc R 1 . . H
  C20  .0012(9) 1.1094(5)  .69057(10)  .0289(11) Uani d . 1 . . C
  C29  .1734(10) 1.2096(5)  .70056(11)  .0361(13) Uani d . 1 . . C
  H29A  .2343 1.2638  .6858  .051(4) Uiso calc R 1 . . H
  H29B  .2782 1.1482  .7090  .051(4) Uiso calc R 1 . . H
  H29C  .1181 1.2813  .7132  .051(4) Uiso calc R 1 . . H
  C30  -.1728(9) 1.2069(6)  .68053(12)  .0389(13) Uani d . 1 . . C
  H30A  -.2239 1.2698  .6948  .051(4) Uiso calc R 1 . . H
  H30B  -.2838 1.1432  .6741  .051(4) Uiso calc R 1 . . H
  H30C  -.1228 1.2703  .6663  .051(4) Uiso calc R 1 . . H
  C21  -.0803(8) 1.0101(5)  .71273(10)  .0294(11) Uani d . 1 . . C
  H21A  -.1170 1.0742  .7278  .035(4) Uiso calc R 1 . . H
  H21B  -.2065  .9597  .7067  .035(4) Uiso calc R 1 . . H
  C22  .0729(8)  .8914(5)  .72185(9)  .0258(10) Uani d . 1 . . C
  H22A  .0046  .8252  .7347  .035(4) Uiso calc R 1 . . H
  H22B  .1875  .9418  .7309  .035(4) Uiso calc R 1 . . H
  O5  .2585(7)  .5234(5)  .44415(8)  .0416(10) Uani d . 1 . . O
  H5A  .2385  .4983  .4598  .035(16) Uiso calc R 1 . . H
  C100  .4549(11)  .5940(7)  .44189(13)  .0506(17) Uani d . 1 . . C
  H100  .5129  .5729  .4246  .051(4) Uiso calc R 1 . . H
  H101  .5465  .5551  .4555  .051(4) Uiso calc R 1 . . H
  H102  .4394  .7022  .4441  .051(4) Uiso calc R 1 . . H
  O6  .2574(8)  .3281(5)  .39864(10)  .0533(12) Uani d D 1 . . O
  H6C  .206(10)  .384(6)  .3865(10)  .06(2) Uiso d D 1 . . H
  H6D  .238(13)  .379(7)  .4127(8)  .06(2) Uiso d D 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
  C1  .022(2)  .019(2)  .031(2)  .000(2)  .003(2)  -.0003(19)
  C2  .025(2)  .021(2)  .029(2)  .001(2)  .003(2)  .0006(19)
  C31  .024(2)  .029(2)  .030(2)  -.004(2)  -.007(2)  .001(2)
  N1  .045(3)  .037(2)  .045(3)  -.012(3)  -.009(2)  .010(2)
  C3  .021(2)  .022(2)  .026(2)  .002(2)  .0001(19)  -.0031(19)
  O1  .048(2)  .0307(19)  .0332(19)  -.003(2)  -.0005(19)  -.0043(15)
  C4  .025(2)  .019(2)  .030(2)  -.001(2)  .002(2)  -.0034(19)
  C23  .035(3)  .026(2)  .035(3)  .009(3)  .001(2)  -.005(2)
  C24  .027(3)  .027(2)  .032(3)  -.001(2)  -.005(2)  -.003(2)
  C5  .0157(19)  .0157(19)  .028(2)  -.0011(19)  .0010(18)  -.0002(17)
  C6  .028(2)  .0161(19)  .029(2)  -.006(2)  .002(2)  -.0010(18)
  C7  .024(2)  .018(2)  .023(2)  -.005(2)  .0015(19)  .0019(18)
  C8  .017(2)  .0172(19)  .027(2)  -.0040(19)  .0021(18)  -.0004(18)
  C26  .022(2)  .022(2)  .031(2)  .000(2)  .001(2)  .001(2)
  C9  .014(2)  .0173(19)  .027(2)  -.0015(18)  -.0015(18)  -.0012(19)
  C10  .019(2)  .020(2)  .020(2)  -.002(2)  -.0013(18)  -.0020(18)
  C25  .016(2)  .030(2)  .030(2)  .000(2)  .0043(19)  .001(2)
  C11  .027(2)  .024(2)  .021(2)  -.011(2)  .008(2)  .0033(18)
  C12  .022(2)  .020(2)  .034(3)  -.007(2)  .003(2)  -.002(2)
  O2  .045(2)  .0264(17)  .042(2)  -.020(2)  .0110(19)  -.0097(16)
  C13  .019(2)  .0157(19)  .023(2)  -.0026(19)  .0021(18)  -.0017(17)
  C14  .018(2)  .0137(19)  .024(2)  -.0018(18)  -.0016(18)  -.0003(17)
  C27  .018(2)  .019(2)  .031(2)  .000(2)  .002(2)  .0006(19)
  C15  .020(2)  .0143(18)  .027(2)  -.0037(19)  -.001(2)  .0006(18)
  C16  .020(2)  .0162(19)  .024(2)  .000(2)  .002(2)  .0010(17)
  C17  .022(2)  .0188(19)  .020(2)  -.005(2)  .0004(19)  -.0003(18)
  C28  .025(2)  .027(2)  .023(2)  -.003(2)  .002(2)  .001(2)
  O3  .0248(19)  .043(2)  .060(3)  -.008(2)  -.0093(19)  .012(2)
  O4  .0300(19)  .0288(17)  .0415(19)  -.0013(18)  -.0062(17)  .0130(16)
  C32  .036(3)  .037(3)  .043(3)  .012(3)  -.008(3)  .008(3)
  C18  .020(2)  .0144(19)  .026(2)  -.0049(19)  .0032(19)  -.0023(17)
  C19  .026(2)  .0158(19)  .030(2)  -.001(2)  -.001(2)  -.0003(19)
  C20  .032(3)  .019(2)  .036(3)  -.004(2)  .000(2)  -.004(2)
  C29  .043(3)  .019(2)  .047(3)  -.008(3)  -.001(3)  -.008(2)
  C30  .037(3)  .024(2)  .056(3)  .006(3)  -.004(3)  -.002(2)
  C21  .030(2)  .019(2)  .039(3)  -.002(2)  .008(2)  -.007(2)
  C22  .028(2)  .022(2)  .027(2)  -.003(2)  .005(2)  -.0028(19)
  O5  .044(2)  .042(2)  .039(2)  -.007(2)  -.0018(19)  .0029(19)
  C100  .059(4)  .038(3)  .054(4)  -.011(4)  .006(3)  .006(3)
  O6  .057(3)  .040(2)  .062(3)  .015(2)  -.014(3)  .002(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
  C1 C2 . 1.327(7) ?
  C1 C10 . 1.513(6) ?
  C1 H1 .  .9500 ?
  C2 C31 . 1.457(7) ?
  C2 C3 . 1.495(6) ?
  C31 N1 . 1.137(7) ?
  C3 O1 . 1.215(6) ?
  C3 C4 . 1.516(7) ?
  C4 C24 . 1.548(7) ?
  C4 C5 . 1.551(6) ?
  C4 C23 . 1.554(7) ?
  C23 H23A .  .9800 ?
  C23 H23B .  .9800 ?
  C23 H23C .  .9800 ?
  C24 H24A .  .9800 ?
  C24 H24B .  .9800 ?
  C24 H24C .  .9800 ?
  C5 C6 . 1.529(6) ?
  C5 C10 . 1.548(6) ?
  C5 H5 . 1.0000 ?
  C6 C7 . 1.508(6) ?
  C6 H6A .  .9900 ?
  C6 H6B .  .9900 ?
  C7 C8 . 1.541(6) ?
  C7 H7A .  .9900 ?
  C7 H7B .  .9900 ?
  C8 C9 . 1.534(6) ?
  C8 C26 . 1.561(7) ?
  C8 C14 . 1.583(6) ?
  C26 H26A .  .9800 ?
  C26 H26B .  .9800 ?
  C26 H26C .  .9800 ?
  C9 C11 . 1.353(6) ?
  C9 C10 . 1.541(6) ?
  C10 C25 . 1.561(6) ?
  C25 H25A .  .9800 ?
  C25 H25B .  .9800 ?
  C25 H25C .  .9800 ?
  C11 C12 . 1.473(6) ?
  C11 H11 .  .9500 ?
  C12 O2 . 1.231(5) ?
  C12 C13 . 1.510(6) ?
  C13 C14 . 1.545(6) ?
  C13 C18 . 1.549(6) ?
  C13 H13 . 1.0000 ?
  C14 C15 . 1.541(6) ?
  C14 C27 . 1.551(6) ?
  C27 H27A .  .9800 ?
  C27 H27B .  .9800 ?
  C27 H27C .  .9800 ?
  C15 C16 . 1.530(6) ?
  C15 H15A .  .9900 ?
  C15 H15B .  .9900 ?
  C16 C17 . 1.536(6) ?
  C16 H16A .  .9900 ?
  C16 H16B .  .9900 ?
  C17 C28 . 1.506(7) ?
  C17 C18 . 1.549(6) ?
  C17 C22 . 1.560(6) ?
  C28 O3 . 1.209(6) ?
  C28 O4 . 1.351(6) ?
  O4 C32 . 1.444(6) ?
  C32 H32A .  .9800 ?
  C32 H32B .  .9800 ?
  C32 H32C .  .9800 ?
  C18 C19 . 1.540(6) ?
  C18 H18 . 1.0000 ?
  C19 C20 . 1.534(7) ?
  C19 H19A .  .9900 ?
  C19 H19B .  .9900 ?
  C20 C30 . 1.523(8) ?
  C20 C29 . 1.528(8) ?
  C20 C21 . 1.535(7) ?
  C29 H29A .  .9800 ?
  C29 H29B .  .9800 ?
  C29 H29C .  .9800 ?
  C30 H30A .  .9800 ?
  C30 H30B .  .9800 ?
  C30 H30C .  .9800 ?
  C21 C22 . 1.533(7) ?
  C21 H21A .  .9900 ?
  C21 H21B .  .9900 ?
  C22 H22A .  .9900 ?
  C22 H22B .  .9900 ?
  O5 C100 . 1.436(8) ?
  O5 H5A .  .8400 ?
  C100 H100 .  .9800 ?
  C100 H101 .  .9800 ?
  C100 H102 .  .9800 ?
  O6 H6C .  .87(5) ?
  O6 H6D .  .86(5) ?