#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200749.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_2200749
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o1105
_journal_page_last  o1106
_publ_section_title
;
Denudatin A, a neolignan from Magnolia soulangiana
;
loop_
_publ_author_name
  'Song, Qi '
  'Fronczek, Frank R. '
  'Fischer, Nikolaus H. '
_chemical_name_common  'Denudatin A'
_chemical_formula_moiety  'C20 H20 O5'
_chemical_formula_sum  'C20 H20 O5'
_chemical_formula_iupac  'C20 H20 O5'
_chemical_formula_weight  340.36
_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  17.8678(17)
_cell_length_b  6.7905(18)
_cell_length_c  16.382(2)
_cell_angle_alpha  90
_cell_angle_beta  120.114(10)
_cell_angle_gamma  90
_cell_volume  1719.4(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.315
_diffrn_ambient_temperature  100
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  .67641(18)  .0531(5)  .6518(2)  .0387(7) Uani d . 1 . . O
  O2  .80453(17)  .2200(4)  .74401(18)  .0337(6) Uani d . 1 . . O
  O3  .28018(19)  .1076(5)  .0946(2)  .0406(7) Uani d . 1 . . O
  O4  .55930(16)  .3352(4)  .31577(17)  .0310(6) Uani d . 1 . . O
  C1  .6435(2)  .4419(6)  .4791(3)  .0249(7) Uani d . 1 . . C
  C2  .6220(2)  .2735(5)  .5134(3)  .0271(8) Uani d . 1 . . C
  H2  .5693  .2046  .4761  .032 Uiso calc R 1 . . H
  C3  .6807(2)  .2143(6)  .6026(3)  .0279(8) Uani d . 1 . . C
  C4  .7574(2)  .3153(6)  .6584(2)  .0277(8) Uani d . 1 . . C
  C5  .7785(2)  .4829(6)  .6281(3)  .0313(8) Uani d . 1 . . C
  H5  .8302  .5539  .6673  .038 Uiso calc R 1 . . H
  C6  .7196(2)  .5441(6)  .5359(3)  .0302(8) Uani d . 1 . . C
  H6  .7322  .6585  .5116  .036 Uiso calc R 1 . . H
  C7  .5849(2)  .5086(5)  .3790(2)  .0256(8) Uani d . 1 . . C
  H7  .6172  .6030  .3610  .031 Uiso calc R 1 . . H
  C8  .4983(2)  .6023(5)  .3569(3)  .0268(8) Uani d . 1 . . C
  H8  .4732  .5266  .3899  .032 Uiso calc R 1 . . H
  C9  .5092(2)  .8178(6)  .3876(3)  .0317(9) Uani d . 1 . . C
  H9A  .5476  .8262  .4561  .048 Uiso calc R 1 . . H
  H9B  .4526  .8736  .3706  .048 Uiso calc R 1 . . H
  H9C  .5344  .8919  .3559  .048 Uiso calc R 1 . . H
  C10  .7626(3)  .0321(6)  .7303(3)  .0359(9) Uani d . 1 . . C
  H10A  .7943  -.0705  .7169  .043 Uiso calc R 1 . . H
  H10B  .7609  -.0063  .7877  .043 Uiso calc R 1 . . H
  C1'  .2958(2)  .4395(6)  .1448(3)  .0285(8) Uani d . 1 . . C
  C2'  .3308(3)  .2401(6)  .1414(3)  .0306(8) Uani d . 1 . . C
  C3'  .4236(3)  .2069(6)  .1969(3)  .0318(8) Uani d . 1 . . C
  H3'  .4475  .0830  .1953  .038 Uiso calc R 1 . . H
  C4'  .4741(2)  .3518(6)  .2497(3)  .0273(8) Uani d . 1 . . C
  O5  .47960(16)  .6938(4)  .20825(18)  .0320(6) Uani d . 1 . . O
  C5'  .4452(2)  .5614(5)  .2505(3)  .0261(8) Uani d . 1 . . C
  C6'  .3485(2)  .5819(6)  .1995(2)  .0279(8) Uani d . 1 . . C
  H6'  .3240  .7006  .2063  .033 Uiso calc R 1 . . H
  C7'  .1989(2)  .4613(6)  .0821(3)  .0335(9) Uani d . 1 . . C
  H7'1  .1830  .4228  .0171  .040 Uiso calc R 1 . . H
  H7'2  .1700  .3684  .1041  .040 Uiso calc R 1 . . H
  C8'  .1649(2)  .6641(7)  .0795(3)  .0421(11) Uani d . 1 . . C
  H8'  .1893  .7707  .0632  .050 Uiso calc R 1 . . H
  C9'  .1032(3)  .7030(11)  .0983(4)  .073(2) Uani d . 1 . . C
  H9'1  .0775  .5994  .1148  .088 Uiso calc R 1 . . H
  H9'2  .0842  .8348  .0955  .088 Uiso calc R 1 . . H
  C10'  .4577(3)  .6498(7)  .1140(3)  .0400(10) Uani d . 1 . . C
  H10C  .4817  .5210  .1122  .060 Uiso calc R 1 . . H
  H10D  .4819  .7511  .0911  .060 Uiso calc R 1 . . H
  H10E  .3947  .6469  .0736  .060 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  .0362(14)  .0289(15)  .0473(16)  -.0063(12)  .0182(12)  .0093(13)
  O2  .0352(13)  .0239(14)  .0369(14)  .0001(12)  .0142(11)  .0026(12)
  O3  .0524(17)  .0230(15)  .0442(16)  -.0073(13)  .0226(14)  -.0067(13)
  O4  .0297(12)  .0192(13)  .0378(13)  .0088(11)  .0122(10)  -.0019(12)
  C1  .0233(15)  .0163(16)  .0358(18)  .0035(13)  .0154(14)  .0007(15)
  C2  .0251(16)  .0171(17)  .0389(19)  -.0036(14)  .0160(14)  -.0009(14)
  C3  .0333(18)  .0134(15)  .0418(19)  .0001(15)  .0225(15)  .0009(15)
  C4  .0278(17)  .0249(19)  .0315(17)  .0006(16)  .0156(14)  -.0039(16)
  C5  .0278(17)  .0200(18)  .041(2)  -.0059(14)  .0136(15)  -.0061(16)
  C6  .0291(17)  .0177(17)  .043(2)  -.0010(14)  .0172(15)  .0021(16)
  C7  .0248(15)  .0156(16)  .0337(18)  .0022(13)  .0126(14)  .0006(14)
  C8  .0248(16)  .0148(17)  .0376(19)  .0018(14)  .0132(14)  -.0014(15)
  C9  .0282(17)  .0156(17)  .041(2)  .0023(15)  .0100(15)  -.0052(16)
  C10  .039(2)  .025(2)  .045(2)  .0046(17)  .0211(17)  .0072(17)
  C1'  .0285(17)  .0226(18)  .0314(18)  -.0022(15)  .0128(14)  -.0019(16)
  C2'  .042(2)  .0199(18)  .0294(18)  -.0024(16)  .0172(15)  -.0027(15)
  C3'  .042(2)  .0174(17)  .0347(19)  .0046(16)  .0180(16)  -.0016(15)
  C4'  .0331(18)  .0164(17)  .0353(18)  .0059(14)  .0193(15)  .0035(15)
  O5  .0311(13)  .0211(14)  .0399(14)  -.0010(11)  .0149(11)  .0040(12)
  C5'  .0260(15)  .0143(16)  .0341(18)  -.0001(13)  .0122(14)  -.0020(14)
  C6'  .0259(16)  .0208(18)  .0317(17)  .0025(15)  .0105(14)  -.0021(15)
  C7'  .0320(19)  .029(2)  .0322(19)  -.0078(16)  .0105(15)  -.0022(17)
  C8'  .0254(18)  .038(3)  .043(2)  .0015(17)  .0030(16)  -.0118(19)
  C9'  .035(2)  .083(5)  .079(4)  .004(3)  .012(2)  -.038(4)
  C10'  .040(2)  .038(2)  .042(2)  .0111(19)  .0208(17)  .0122(19)
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 C3 . 1.384(5) ?
  O1 C10 . 1.435(5) ?
  O2 C4 . 1.382(4) ?
  O2 C10 . 1.439(5) ?
  O3 C2' . 1.233(5) yes
  O4 C4' . 1.359(4) ?
  O4 C7 . 1.481(4) ?
  C1 C6 . 1.389(5) ?
  C1 C2 . 1.409(5) ?
  C1 C7 . 1.506(5) ?
  C2 C3 . 1.363(5) ?
  C2 H2 .  .9500 ?
  C3 C4 . 1.389(5) ?
  C4 C5 . 1.368(6) ?
  C5 C6 . 1.402(5) ?
  C5 H5 .  .9500 ?
  C6 H6 .  .9500 ?
  C7 C8 . 1.539(5) ?
  C7 H7 . 1.0000 ?
  C8 C9 . 1.529(5) ?
  C8 C5' . 1.534(5) ?
  C8 H8 . 1.0000 ?
  C9 H9A .  .9800 ?
  C9 H9B .  .9800 ?
  C9 H9C .  .9800 ?
  C10 H10A .  .9900 ?
  C10 H10B .  .9900 ?
  C1' C6' . 1.333(5) yes
  C1' C2' . 1.505(5) ?
  C1' C7' . 1.512(5) ?
  C2' C3' . 1.454(5) ?
  C3' C4' . 1.322(5) yes
  C3' H3' .  .9500 ?
  C4' C5' . 1.516(5) ?
  O5 C10' . 1.422(5) ?
  O5 C5' . 1.447(5) ?
  C5' C6' . 1.502(5) ?
  C6' H6' .  .9500 ?
  C7' C8' . 1.497(6) ?
  C7' H7'1 .  .9900 ?
  C7' H7'2 .  .9900 ?
  C8' C9' . 1.312(7) yes
  C8' H8' .  .9500 ?
  C9' H9'1 .  .9500 ?
  C9' H9'2 .  .9500 ?
  C10' H10C .  .9800 ?
  C10' H10D .  .9800 ?
  C10' H10E .  .9800 ?