#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012075.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_2012075
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  846
_journal_page_last  847
_publ_section_title
;
Amarisolide monohydrate, a 2-(\b-glucosyl)neoclerodane
;
loop_
_publ_author_name
  "Toscano, Rub\'en A."
  'Maldonado, Emma'
  'Ortega, Alfredo'
  "C\'ardenas, Jorge"
_chemical_name_common  'Amarisolide Monohydrate'
_chemical_formula_moiety  'C26 H36 O9, H2 O'
_chemical_formula_sum  'C26 H38 O10'
_chemical_formula_weight  510.56
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z'
_cell_length_a  16.997(2)
_cell_length_b  8.4410(10)
_cell_length_c  17.7630(10)
_cell_angle_alpha  90.00
_cell_angle_beta  92.570(10)
_cell_angle_gamma  90.00
_cell_volume  2545.9(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.332
_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
  C1  -.11391(19)  .8218(4)  .72558(19)  .0348(7) Uani d . 1 . . C
  H1A  -.093(2)  .721(5)  .726(2)  .042 Uiso d . 1 . . H
  H1B  -.165(2)  .821(5)  .701(2)  .042 Uiso d . 1 . . H
  O1  .01980(11)  .9002(5)  .71008(11)  .0319(4) Uani d . 1 . . O
  C2  -.05927(18)  .9216(5)  .67860(17)  .0325(6) Uani d . 1 . . C
  H2  -.065(2)  .883(5)  .629(2)  .039 Uiso d . 1 . . H
  C3  -.08540(18) 1.0927(5)  .67841(18)  .0331(6) Uani d . 1 . . C
  H3  -.079(2) 1.153(5)  .637(2)  .040 Uiso d . 1 . . H
  C4  -.12961(17) 1.1475(5)  .73207(18)  .0319(6) Uani d . 1 . . C
  C5  -.15668(16) 1.0596(5)  .80000(16)  .0289(6) Uani d . 1 . . C
  C6  -.1352(2) 1.1448(5)  .87479(19)  .0358(6) Uani d . 1 . . C
  H6A  -.159(2) 1.243(5)  .872(2)  .043 Uiso d . 1 . . H
  H6B  -.080(2) 1.152(5)  .881(2)  .043 Uiso d . 1 . . H
  C7  -.1626(2) 1.0471(6)  .9408(2)  .0415(7) Uani d . 1 . . C
  H7A  -.148(2) 1.087(5)  .987(2)  .050 Uiso d . 1 . . H
  H7B  -.219(3) 1.044(5)  .943(2)  .050 Uiso d . 1 . . H
  C8  -.13108(19)  .8771(6)  .94405(18)  .0368(7) Uani d . 1 . . C
  H8  -.073(2)  .882(5)  .952(2)  .044 Uiso d . 1 . . H
  C9  -.14606(17)  .7859(5)  .86838(18)  .0329(6) Uani d . 1 . . C
  C10  -.11778(16)  .8949(5)  .80456(16)  .0279(5) Uani d . 1 . . C
  H10  -.064(2)  .917(4)  .8216(19)  .034 Uiso d . 1 . . H
  C11  -.09875(19)  .6282(5)  .8697(2)  .0391(7) Uani d . 1 . . C
  H11A  -.112(2)  .570(5)  .820(2)  .047 Uiso d . 1 . . H
  H11B  -.116(2)  .567(5)  .910(2)  .047 Uiso d . 1 . . H
  C12  -.0086(2)  .6386(6)  .8778(3)  .0450(8) Uani d . 1 . . C
  H12A  .009(3)  .710(6)  .849(3)  .054 Uiso d . 1 . . H
  H12B  .014(2)  .675(5)  .932(3)  .054 Uiso d . 1 . . H
  C13  .02846(19)  .4789(6)  .8653(2)  .0386(7) Uani d . 1 . . C
  C14  .0578(2)  .3792(6)  .9171(2)  .0446(8) Uani d . 1 . . C
  H14  .065(2)  .378(5)  .970(3)  .053 Uiso d . 1 . . H
  O2  .08138(15)  .2392(5)  .88526(17)  .0537(7) Uani d . 1 . . O
  C15  .0662(2)  .2569(7)  .8106(3)  .0589(11) Uani d . 1 . . C
  H15  .079(3)  .177(6)  .778(3)  .071 Uiso d . 1 . . H
  C16  .0343(2)  .3982(7)  .7958(2)  .0541(10) Uani d . 1 . . C
  H16  .013(3)  .442(6)  .752(3)  .065 Uiso d . 1 . . H
  C17  -.1642(3)  .7952(8) 1.0130(3)  .0592(11) Uani d . 1 . . C
  H17A  -.151(3)  .852(6) 1.058(3)  .071 Uiso d . 1 . . H
  H17B  -.143(3)  .690(6) 1.019(3)  .071 Uiso d . 1 . . H
  H17C  -.221(3)  .799(6) 1.004(3)  .071 Uiso d . 1 . . H
  C18  -.18463(19) 1.2830(6)  .7201(2)  .0403(7) Uani d . 1 . . C
  O3  -.25275(14) 1.2418(5)  .75057(16)  .0505(7) Uani d . 1 . . O
  O4  -.17743(16) 1.4068(5)  .68721(17)  .0535(7) Uani d . 1 . . O
  C19  -.24644(19) 1.0798(6)  .7824(2)  .0415(8) Uani d . 1 . . C
  H19A  -.281(2) 1.081(5)  .827(2)  .050 Uiso d . 1 . . H
  H19B  -.267(2) 1.004(5)  .746(2)  .050 Uiso d . 1 . . H
  C20  -.2330(2)  .7394(6)  .8554(3)  .0470(8) Uani d . 1 . . C
  H20A  -.245(3)  .653(6)  .891(3)  .056 Uiso d . 1 . . H
  H20B  -.268(3)  .835(5)  .859(2)  .056 Uiso d . 1 . . H
  H20C  -.242(3)  .693(5)  .806(3)  .056 Uiso d . 1 . . H
  C1'  .08205(17)  .9169(5)  .66194(16)  .0284(6) Uani d . 1 . . C
  H1'  .131(2)  .907(4)  .692(2)  .034 Uiso d . 1 . . H
  O1'  .07877(13) 1.0727(4)  .63111(12)  .0317(5) Uani d . 1 . . O
  C2'  .08243(17)  .7950(5)  .59811(17)  .0280(6) Uani d . 1 . . C
  H2'  .038(2)  .808(4)  .565(2)  .034 Uiso d . 1 . . H
  O2'  .08767(15)  .6400(5)  .62838(15)  .0404(5) Uani d D 1 . . O
  H2'A  .043(2)  .608(5)  .626(2)  .049 Uiso d D 1 . . H
  C3'  .15345(17)  .8274(5)  .55074(17)  .0284(6) Uani d . 1 . . C
  H3'  .205(2)  .808(4)  .578(2)  .034 Uiso d . 1 . . H
  O3'  .15344(15)  .7251(5)  .48691(14)  .0397(5) Uani d D 1 . . O
  H3'A  .194(2)  .668(5)  .496(2)  .048 Uiso d D 1 . . H
  C4'  .15037(18)  .9984(5)  .52306(17)  .0299(6) Uani d . 1 . . C
  H4'  .100(2) 1.007(5)  .488(2)  .036 Uiso d . 1 . . H
  O4'  .21887(17) 1.0369(5)  .48350(16)  .0479(7) Uani d D 1 . . O
  H4'A  .224(3)  .973(5)  .456(2)  .057 Uiso d D 1 . . H
  C5'  .14655(18) 1.1116(5)  .58916(17)  .0288(6) Uani d . 1 . . C
  H5'  .191(2) 1.095(4)  .619(2)  .035 Uiso d . 1 . . H
  C6'  .1390(2) 1.2835(5)  .5646(2)  .0374(7) Uani d . 1 . . C
  H6'A  .081(2) 1.310(5)  .555(2)  .045 Uiso d . 1 . . H
  H6'B  .163(2) 1.298(5)  .515(2)  .045 Uiso d . 1 . . H
  O6'  .18419(15) 1.3826(5)  .61404(15)  .0439(6) Uani d D 1 . . O
  H6'  .161(2) 1.472(5)  .620(2)  .053 Uiso d D 1 . . H
  O5  .44562(18) 1.0097(5)  .5972(2)  .0594(8) Uani d D 1 . . O
  H5A  .427(3) 1.068(6)  .571(3)  .071 Uiso d D 1 . . H
  H5B  .417(3)  .965(6)  .618(3)  .071 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  .0323(15)  .0314(15)  .0410(17)  -.0021(12)  .0033(13)  -.0042(13)
  O1  .0291(9)  .0391(11)  .0278(10)  .0048(9)  .0040(8)  .0014(9)
  C2  .0335(14)  .0387(16)  .0254(13)  .0030(12)  .0034(11)  -.0043(12)
  C3  .0329(15)  .0350(15)  .0314(14)  .0042(12)  .0016(12)  .0068(13)
  C4  .0297(13)  .0278(13)  .0381(16)  .0022(12)  .0002(12)  .0049(13)
  C5  .0250(12)  .0283(13)  .0337(14)  .0010(10)  .0049(11)  -.0005(12)
  C6  .0381(16)  .0298(14)  .0402(17)  .0004(13)  .0082(13)  -.0041(14)
  C7  .0411(18)  .0473(18)  .0370(17)  .0010(15)  .0125(14)  -.0056(15)
  C8  .0329(15)  .0439(18)  .0343(15)  .0029(13)  .0086(12)  .0047(14)
  C9  .0263(13)  .0324(14)  .0404(16)  -.0031(11)  .0056(11)  .0034(13)
  C10  .0229(12)  .0277(13)  .0332(14)  -.0019(10)  .0019(10)  -.0013(12)
  C11  .0350(15)  .0315(15)  .051(2)  .0017(13)  .0064(14)  .0071(15)
  C12  .0333(16)  .0337(16)  .067(3)  .0013(14)  -.0034(16)  .0014(17)
  C13  .0317(15)  .0404(17)  .0440(18)  .0003(13)  .0053(13)  .0015(14)
  C14  .0452(18)  .047(2)  .0421(18)  .0094(15)  .0050(15)  -.0020(16)
  O2  .0432(13)  .0437(14)  .0743(19)  .0119(12)  .0034(13)  -.0013(14)
  C15  .045(2)  .066(3)  .066(3)  .0082(19)  .0021(18)  -.027(2)
  C16  .051(2)  .073(3)  .0381(18)  .004(2)  .0014(16)  -.002(2)
  C17  .064(3)  .067(3)  .048(2)  .010(2)  .020(2)  .018(2)
  C18  .0356(15)  .0400(17)  .0453(19)  .0076(14)  .0027(13)  .0019(15)
  O3  .0311(11)  .0497(14)  .0709(18)  .0123(11)  .0049(11)  .0092(14)
  O4  .0505(14)  .0426(14)  .0675(17)  .0100(12)  .0040(13)  .0159(14)
  C19  .0297(15)  .0389(17)  .056(2)  .0052(13)  .0025(14)  .0040(16)
  C20  .0281(14)  .047(2)  .066(2)  -.0101(14)  .0073(15)  .0078(19)
  C1'  .0302(13)  .0276(13)  .0276(13)  .0036(11)  .0039(11)  .0006(11)
  O1'  .0351(11)  .0228(9)  .0381(11)  .0032(8)  .0095(9)  -.0012(9)
  C2'  .0301(13)  .0241(13)  .0302(14)  .0031(11)  .0059(11)  -.0006(11)
  O2'  .0417(12)  .0243(10)  .0563(15)  .0031(10)  .0134(11)  .0039(10)
  C3'  .0290(13)  .0239(13)  .0328(14)  -.0004(10)  .0055(11)  -.0056(11)
  O3'  .0451(12)  .0343(11)  .0402(13)  .0049(10)  .0084(10)  -.0120(10)
  C4'  .0352(15)  .0223(12)  .0330(15)  -.0031(11)  .0092(12)  -.0002(11)
  O4'  .0547(15)  .0369(13)  .0545(16)  -.0077(11)  .0302(12)  -.0103(11)
  C5'  .0315(14)  .0224(13)  .0327(14)  .0022(10)  .0036(11)  -.0025(11)
  C6'  .0472(18)  .0231(14)  .0423(18)  .0008(13)  .0051(15)  .0038(13)
  O6'  .0483(14)  .0228(10)  .0610(16)  -.0004(10)  .0063(11)  -.0073(11)
  O5  .0452(16)  .0571(19)  .076(2)  -.0060(13)  .0001(14)  .0126(16)
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 . 1.529(4) ?
  C1 C10 . 1.537(4) ?
  C1 H1A .  .92(4) ?
  C1 H1B .  .95(4) ?
  O1 C1' . 1.397(3) ?
  O1 C2 . 1.444(4) ?
  C2 C3 . 1.511(4) ?
  C2 H2 .  .93(4) ?
  C3 C4 . 1.323(4) ?
  C3 H3 .  .90(4) ?
  C4 C18 . 1.487(4) ?
  C4 C5 . 1.506(4) ?
  C5 C10 . 1.540(4) ?
  C5 C6 . 1.540(4) ?
  C5 C19 . 1.553(4) ?
  C6 C7 . 1.523(5) ?
  C6 H6A .  .93(4) ?
  C6 H6B .  .94(4) ?
  C7 C8 . 1.532(5) ?
  C7 H7A .  .91(4) ?
  C7 H7B .  .96(4) ?
  C8 C17 . 1.534(5) ?
  C8 C9 . 1.560(5) ?
  C8 H8 .  .99(4) ?
  C9 C20 . 1.537(4) ?
  C9 C10 . 1.553(4) ?
  C9 C11 . 1.554(4) ?
  C10 H10 .  .98(4) ?
  C11 C12 . 1.535(5) ?
  C11 H11A . 1.03(4) ?
  C11 H11B .  .93(4) ?
  C12 C13 . 1.508(5) ?
  C12 H12A .  .86(5) ?
  C12 H12B . 1.06(5) ?
  C13 C14 . 1.327(5) ?
  C13 C16 . 1.418(5) ?
  C14 O2 . 1.378(5) ?
  C14 H14 .  .95(4) ?
  O2 C15 . 1.349(5) ?
  C15 C16 . 1.332(7) ?
  C15 H15 .  .92(5) ?
  C16 H16 .  .92(5) ?
  C17 H17A .  .94(5) ?
  C17 H17B .  .96(5) ?
  C17 H17C .  .97(5) ?
  C18 O4 . 1.206(4) ?
  C18 O3 . 1.346(4) ?
  O3 C19 . 1.482(5) ?
  C19 H19A . 1.01(4) ?
  C19 H19B .  .96(4) ?
  C20 H20A .  .99(5) ?
  C20 H20B . 1.00(5) ?
  C20 H20C .  .97(5) ?
  C1' O1' . 1.425(3) ?
  C1' C2' . 1.531(4) ?
  C1' H1' .  .98(4) ?
  O1' C5' . 1.438(3) ?
  C2' O2' . 1.416(4) ?
  C2' C3' . 1.527(4) ?
  C2' H2' .  .95(4) ?
  O2' H2'A .  .80(4) ?
  C3' O3' . 1.425(4) ?
  C3' C4' . 1.526(4) ?
  C3' H3' .  .99(4) ?
  O3' H3'A .  .85(3) ?
  C4' O4' . 1.424(4) ?
  C4' C5' . 1.517(4) ?
  C4' H4' . 1.05(4) ?
  O4' H4'A .  .74(4) ?
  C5' C6' . 1.519(4) ?
  C5' H5' .  .91(4) ?
  C6' O6' . 1.415(4) ?
  C6' H6'A . 1.01(4) ?
  C6' H6'B .  .99(4) ?
  O6' H6' .  .86(4) ?
  O5 H5A .  .73(4) ?
  O5 H5B .  .72(4) ?