#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2010627.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_2010627
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  199
_journal_page_last  200
_publ_section_title
;
2\b-Hydroxy-4'-demethyldesoxypodophyllotoxin
;
loop_
_publ_author_name
  'Du Boulay, Douglas'
  'Shaari, Khozirah'
  'Skelton, Brian W.'
  'Waterman, Peter G.'
  'White, Allan H.'
_chemical_formula_sum  'C21 H20 O8'
_chemical_formula_weight  400.38
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P 1'
_symmetry_space_group_name_Hall  p_1
loop_
_symmetry_equiv_pos_as_xyz
  +x,+y,+z
_cell_length_a  7.8540(10)
_cell_length_b  9.3840(10)
_cell_length_c  13.230(2)
_cell_angle_alpha  101.563(2)
_cell_angle_beta  103.699(2)
_cell_angle_gamma  90.184(2)
_cell_volume  926.8(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  300
_exptl_crystal_density_diffrn  1.435
_diffrn_ambient_temperature  293
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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
  C11 .00000 .50000 .00000 .0332(17) Uani ? ? 1.00000 ? ?
  C12 -.1608(6) .5670(5) .0330(4) .0319(17) Uani ? ? 1.00000 ? ?
  C11' -.1443(6) .5769(5) .1521(3) .0319(16) Uani ? ? 1.00000 ? ?
  C12' .0113(6) .6204(5) .2275(4) .0373(18) Uani ? ? 1.00000 ? ?
  C13' .0275(6) .6217(5) .3340(3) .0354(17) Uani ? ? 1.00000 ? ?
  O13' .1786(5) .6592(4) .4120(3) .0603(15) Uani ? ? 1.00000 ? ?
  C131' .3026(7) .7542(6) .3935(4) .054(2) Uani ? ? 1.00000 ? ?
  C14' -.1164(6) .5730(5) .3664(4) .0371(17) Uani ? ? 1.00000 ? ?
  O14' -.0961(5) .5716(5) .4720(3) .0568(16) Uani ? ? 1.00000 ? ?
  C15' -.2700(6) .5300(5) .2924(4) .0380(18) Uani ? ? 1.00000 ? ?
  O15' -.4016(5) .4855(5) .3340(3) .0597(15) Uani ? ? 1.00000 ? ?
  C151' -.5537(7) .4118(7) .2605(5) .074(3) Uani ? ? 1.00000 ? ?
  C16' -.2865(6) .5302(5) .1866(4) .0362(19) Uani ? ? 1.00000 ? ?
  C13 -.1875(6) .7130(5) -.0030(3) .0317(16) Uani ? ? 1.00000 ? ?
  O13 -.2507(5) .6885(4) -.1165(3) .0410(13) Uani ? ? 1.00000 ? ?
  C14 -.3114(6) .8197(5) .0419(3) .038(2) Uani ? ? 1.00000 ? ?
  O14 -.4438(5) .7960(4) .0690(3) .0566(15) Uani ? ? 1.00000 ? ?
  O15 -.2573(5) .9572(4) .0424(3) .0464(14) Uani ? ? 1.00000 ? ?
  C16 -.0896(7) .9531(5) .0081(4) .040(2) Uani ? ? 1.00000 ? ?
  C17 -.0218(6) .8080(5) .0270(4) .0324(17) Uani ? ? 1.00000 ? ?
  C18 .1140(7) .7386(5) -.0292(4) .0371(19) Uani ? ? 1.00000 ? ?
  C19 .1333(5) .5807(5) -.0205(3) .0337(17) Uani ? ? 1.00000 ? ?
  C110 .2862(6) .5138(5) -.0396(4) .038(2) Uani ? ? 1.00000 ? ?
  C111 .2960(6) .3694(5) -.0414(3) .040(2) Uani ? ? 1.00000 ? ?
  O111 .4311(5) .2814(5) -.0634(3) .0555(15) Uani ? ? 1.00000 ? ?
  C112 .1636(7) .2866(5) -.0260(4) .040(2) Uani ? ? 1.00000 ? ?
  O112 .2049(5) .1430(4) -.0375(3) .0629(17) Uani ? ? 1.00000 ? ?
  C113 .0177(6) .3480(5) -.0023(3) .043(2) Uani ? ? 1.00000 ? ?
  C114 .3846(8) .1413(6) -.0462(5) .062(3) Uani ? ? 1.00000 ? ?
  C21 .2539(5) .1847(5) .6569(3) .0335(18) Uani ? ? 1.00000 ? ?
  C22 .4146(6) .2327(5) .6215(4) .0313(17) Uani ? ? 1.00000 ? ?
  C21' .3969(6) .1735(5) .5033(3) .0338(17) Uani ? ? 1.00000 ? ?
  C22' .2419(6) .1754(5) .4276(4) .0359(18) Uani ? ? 1.00000 ? ?
  C23' .2253(6) .1179(5) .3214(3) .0364(18) Uani ? ? 1.00000 ? ?
  O23' .0757(5) .1117(4) .2434(3) .0544(15) Uani ? ? 1.00000 ? ?
  C231' -.0490(7) .2179(6) .2600(4) .052(2) Uani ? ? 1.00000 ? ?
  C24' .3696(6) .0518(5) .2883(4) .0379(18) Uani ? ? 1.00000 ? ?
  O24' .3483(6) -.0081(5) .1829(3) .0559(18) Uani ? ? 1.00000 ? ?
  C25' .5247(6) .0498(5) .3626(4) .0382(19) Uani ? ? 1.00000 ? ?
  O25' .6559(5) -.0162(5) .3216(3) .0564(15) Uani ? ? 1.00000 ? ?
  C251' .8064(8) -.0524(7) .3919(5) .075(3) Uani ? ? 1.00000 ? ?
  C26' .5398(6) .1094(5) .4693(4) .0363(18) Uani ? ? 1.00000 ? ?
  C23 .4421(6) .3984(5) .6569(4) .0341(17) Uani ? ? 1.00000 ? ?
  O23 .5183(5) .4348(4) .7714(3) .0390(13) Uani ? ? 1.00000 ? ?
  C24 .5678(6) .4783(5) .6132(3) .038(2) Uani ? ? 1.00000 ? ?
  O24 .6971(5) .4382(4) .5831(3) .0552(15) Uani ? ? 1.00000 ? ?
  O25 .5141(5) .6164(4) .6139(3) .0490(14) Uani ? ? 1.00000 ? ?
  C26 .3455(7) .6335(5) .6472(4) .044(2) Uani ? ? 1.00000 ? ?
  C27 .2761(6) .4774(5) .6285(4) .0328(18) Uani ? ? 1.00000 ? ?
  C28 .1397(6) .4424(5) .6838(4) .036(2) Uani ? ? 1.00000 ? ?
  C29 .1261(6) .2796(5) .6814(4) .0336(17) Uani ? ? 1.00000 ? ?
  C210 -.0229(6) .2251(6) .7060(4) .043(2) Uani ? ? 1.00000 ? ?
  C211 -.0387(6) .0819(6) .7055(4) .044(2) Uani ? ? 1.00000 ? ?
  O211 -.1730(5) .0048(5) .7270(3) .0616(16) Uani ? ? 1.00000 ? ?
  C212 .0908(7) -.0112(6) .6841(4) .044(2) Uani ? ? 1.00000 ? ?
  O212 .0460(6) -.1506(5) .6928(3) .0652(16) Uani ? ? 1.00000 ? ?
  C213 .2352(6) .0362(5) .6578(3) .043(2) Uani ? ? 1.00000 ? ?
  C214 -.1379(7) -.1454(6) .6938(5) .063(3) Uani ? ? 1.00000 ? ?
  H12 -.273(4) .505(3) -.005(2) .030(8) Uiso ? ? 1.00000 ? ?
  H12' .106(4) .645(3) .207(2) .023(8) Uiso ? ? 1.00000 ? ?
  H131'a .277(7) .863(6) .433(5) .18(3) Uiso ? ? 1.00000 ? ?
  H131'b .406(5) .763(4) .454(3) .068(12) Uiso ? ? 1.00000 ? ?
  H131'c .364(5) .708(4) .330(3) .098(15) Uiso ? ? 1.00000 ? ?
  H14' -.201(8) .525(6) .473(5) .20(3) Uiso ? ? 1.00000 ? ?
  H151'a -.630(5) .377(4) .305(3) .068(11) Uiso ? ? 1.00000 ? ?
  H151'b -.613(6) .483(5) .219(4) .101(17) Uiso ? ? 1.00000 ? ?
  H151'c -.486(5) .313(4) .221(3) .091(14) Uiso ? ? 1.00000 ? ?
  H16' -.366(4) .496(3) .144(3) .037(11) Uiso ? ? 1.00000 ? ?
  H13 -.319(4) .608(3) -.138(2) .037(10) Uiso ? ? 1.00000 ? ?
  H16a -.017(4) 1.046(3) .052(2) .029(8) Uiso ? ? 1.00000 ? ?
  H16b -.125(3) .961(3) -.074(2) .027(8) Uiso ? ? 1.00000 ? ?
  H17 .023(3) .820(2) .104(2) .013(7) Uiso ? ? 1.00000 ? ?
  H18a .069(4) .733(3) -.116(2) .048(9) Uiso ? ? 1.00000 ? ?
  H18b .219(4) .790(3)  .000(2) .048(11) Uiso ? ? 1.00000 ? ?
  H110 .377(4) .569(3) -.049(2) .038(10) Uiso ? ? 1.00000 ? ?
  H113 -.093(5) .282(4) .015(3) .084(13) Uiso ? ? 1.00000 ? ?
  H114a .395(6) .073(5) -.096(4) .10(2) Uiso ? ? 1.00000 ? ?
  H114b .478(6) .125(4) .031(4) .111(16) Uiso ? ? 1.00000 ? ?
  H22 .509(4) .183(3) .652(2) .046(10) Uiso ? ? 1.00000 ? ?
  H22' .159(3) .209(3) .451(2) .012(8) Uiso ? ? 1.00000 ? ?
  H231'a -.128(5) .201(4) .191(3) .077(14) Uiso ? ? 1.00000 ? ?
  H231'b -.078(5) .205(4) .335(4) .107(16) Uiso ? ? 1.00000 ? ?
  H231'c -.004(5) .323(4) .286(3) .082(14) Uiso ? ? 1.00000 ? ?
  H24' .431(5) -.032(5) .179(4) .08(2) Uiso ? ? 1.00000 ? ?
  H251'a .760(6) -.111(5) .434(4) .12(2) Uiso ? ? 1.00000 ? ?
  H251'b .921(7) -.081(5) .358(4) .14(2) Uiso ? ? 1.00000 ? ?
  H251'c .856(5) .038(4) .442(3) .051(12) Uiso ? ? 1.00000 ? ?
  H26' .643(3) .102(3) .520(2) .024(8) Uiso ? ? 1.00000 ? ?
  H23 .486(6) .368(5) .795(4) .12(2) Uiso ? ? 1.00000 ? ?
  H26a .277(4) .701(4) .605(3) .066(12) Uiso ? ? 1.00000 ? ?
  H26b .380(3) .688(3) .726(2) .032(8) Uiso ? ? 1.00000 ? ?
  H27 .234(3) .446(3) .552(2) .029(8) Uiso ? ? 1.00000 ? ?
  H28a .169(4) .490(3) .761(2) .049(10) Uiso ? ? 1.00000 ? ?
  H28b .014(4) .473(3) .654(2) .040(9) Uiso ? ? 1.00000 ? ?
  H210 -.103(4) .283(3) .718(2) .021(9) Uiso ? ? 1.00000 ? ?
  H213 .328(4) -.031(4) .643(3) .051(11) Uiso ? ? 1.00000 ? ?
  H214a -.196(4) -.180(4) .608(3) .068(12) Uiso ? ? 1.00000 ? ?
  H214b -.162(5) -.201(4) .747(3) .084(14) Uiso ? ? 1.00000 ? ?
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
  C11 .032(2) .038(2) .029(2) .0022(18) .0098(16) .0084(16)
  C12 .029(2) .031(2) .035(2) -.0010(17) .0050(16) .0042(15)
  C11' .035(2) .031(2) .030(2) .0037(16) .0091(16) .0065(15)
  C12' .031(2) .041(2) .041(2) -.0022(18) .0122(18) .0144(17)
  C13' .037(2) .038(2) .032(2) -.0045(17) .0029(17) .0101(16)
  O13' .0515(17) .084(2) .0453(17) -.0275(15) -.0043(13) .0290(14)
  C131' .045(3) .068(3) .049(3) -.018(2) .003(2) .012(2)
  C14' .043(2) .037(2) .032(2) .0022(17) .0134(18) .0119(16)
  O14' .0553(19) .076(2) .0386(17) -.0100(16) .0102(13) .0185(13)
  C15' .034(2) .043(2) .037(2) -.0004(18) .0120(18) .0138(17)
  O15' .0363(16) .092(2) .0510(16) -.0089(15) .0150(13) .0252(15)
  C151' .054(3) .086(4) .082(4) -.013(3) .032(3) .027(3)
  C16' .026(2) .044(2) .039(2) -.0030(18) .0048(19) .0087(18)
  C13 .032(2) .034(2) .030(2) .0000(16) .0067(15) .0048(15)
  O13 .0506(16) .0375(16) .0349(15) -.0089(13) -.0001(12) .0078(12)
  C14 .037(2) .042(3) .035(2) .008(2) -.0001(17) .0042(17)
  O14 .0386(16) .0534(18) .078(2) .0075(13) .0245(15) .0112(14)
  O15 .0444(17) .0318(16) .0631(18) .0032(13) .0127(13) .0059(12)
  C16 .046(3) .035(2) .040(2) -.0035(19) .008(2) .0083(17)
  C17 .034(2) .029(2) .035(2) -.0028(16) .0065(17) .0066(15)
  C18 .035(2) .030(2) .046(2) -.0059(18) .0122(18) .0074(16)
  C19 .037(2) .037(2) .0268(19) -.0030(17) .0067(16) .0043(15)
  C110 .033(2) .044(3) .035(2) -.004(2) .0108(17) .0055(17)
  C111 .038(2) .049(3) .032(2) .011(2) .0087(17) .0072(17)
  O111 .0458(16) .0507(18) .0700(19) .0144(14) .0228(14) .0103(14)
  C112 .043(2) .037(2) .040(2) .009(2) .0123(18) .0125(17)
  O112 .061(2) .0408(18) .087(2) .0134(14) .0314(17) .0200(14)
  C113 .050(3) .039(2) .039(2) -.001(2) .0089(18) .0157(17)
  C114 .063(3) .049(3) .075(3) .021(3) .025(3) .017(3)
  C21 .032(2) .041(2) .027(2) -.0072(18) .0073(16) .0034(16)
  C22 .029(2) .029(2) .036(2) -.0007(17) .0038(16) .0072(16)
  C21' .036(2) .034(2) .032(2) -.0050(17) .0118(16) .0059(15)
  C22' .027(2) .036(2) .044(2) .0045(18) .014(2) -.0001(17)
  C23' .037(2) .037(2) .035(2) .0052(18) .0020(18) .0042(17)
  O23' .0500(17) .071(2) .0427(16) .0235(15) -.0075(13) -.0112(12)
  C231' .056(3) .055(3) .046(3) .019(2) -.002(2) .000(2)
  C24' .045(2) .036(2) .032(2) -.0013(18) .0088(18) .0016(16)
  O24' .055(2) .072(2) .0401(19) .0159(18) .0109(15) -.0023(13)
  C25' .033(2) .038(2) .043(2) .0014(17) .0157(19) .0044(17)
  O25' .0403(16) .080(2) .0488(17) .0125(15) .0125(13) -.0013(14)
  C251' .052(3) .080(4) .091(4) .025(3) .026(3) .020(3)
  C26' .028(2) .043(2) .038(2) .0023(17) .0057(18) .0064(17)
  C23 .034(2) .038(2) .031(2) -.0048(17) .0077(16) .0073(15)
  O23 .0436(15) .0419(16) .0314(14) -.0079(12) .0034(11) .0051(11)
  C24 .040(2) .043(3) .030(2) -.011(2) -.0031(17) .0100(17)
  O24 .0368(16) .064(2) .0648(19) -.0029(14) .0218(14) .0206(14)
  O25 .0479(16) .0387(17) .0603(18) -.0063(13) .0155(13) .0157(13)
  C26 .049(3) .038(2) .044(3)  .000(2) .008(2) .008(2)
  C27 .036(2) .030(2) .032(2) -.0062(16) .0027(17) .0074(16)
  C28 .035(2) .037(2) .037(2) .0026(18) .0065(18) .0080(17)
  C29 .033(2) .038(2) .030(2) -.0019(18) .0018(16) .0096(15)
  C210 .031(2) .050(3) .048(2) .007(2) .0127(19) .015(2)
  C211 .041(2) .055(3) .036(2) -.011(2) .0089(18) .0150(19)
  O211 .0467(17) .068(2) .070(2) -.0152(15) .0201(14) .0235(15)
  C212 .055(3) .039(2) .037(2) -.013(2) .009(2) .0074(17)
  O212 .073(2) .0416(17) .081(2) -.0120(14) .0276(17) .0180(14)
  C213 .047(2) .035(2) .047(2)  .000(2) .019(2) .0076(17)
  C214 .067(3) .055(3) .067(3) -.025(2) .011(3) .019(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C11 C12 . . 1.529(5) ?
  C11 C19 . . 1.399(5) ?
  C11 C113 . . 1.429(5) ?
  C12 C11' . . 1.534(6) ?
  C12 C13 . . 1.537(7) ?
  C12 H12 . . 1.02(3) ?
  C11' C12' . . 1.383(6) ?
  C11' C16' . . 1.402(8) ?
  C12' C13' . . 1.382(7) ?
  C12' H12' . . .89(3) ?
  C13' O13' . . 1.367(5) ?
  C13' C14' . . 1.405(7) ?
  O13' C131' . . 1.413(8) ?
  C131' H131'a . . 1.09(6) ?
  C131' H131'b . . .98(3) ?
  C131' H131'c . . 1.08(5) ?
  C14' O14' . . 1.370(6) ?
  C14' C15' . . 1.362(6) ?
  O14' H14' . . .94(6) ?
  C15' O15' . . 1.381(7) ?
  C15' C16' . . 1.375(7) ?
  O15' C151' . . 1.424(6) ?
  C151' H151'a . . 1.02(4) ?
  C151' H151'b . . 1.00(5) ?
  C151' H151'c . . 1.16(4) ?
  C16' H16' . . .76(3) ?
  C13 O13 . . 1.436(6) ?
  C13 C14 . . 1.531(7) ?
  C13 C17 . . 1.501(6) ?
  O13 H13 . . .88(3) ?
  C14 O14 . . 1.211(7) ?
  C14 O15 . . 1.355(6) ?
  O15 C16 . . 1.490(7) ?
  C16 C17 . . 1.509(7) ?
  C16 H16a . . 1.03(3) ?
  C16 H16b . . 1.07(3) ?
  C17 C18 . . 1.517(7) ?
  C17 H17 . . .98(3) ?
  C18 C19 . . 1.514(7) ?
  C18 H18a . . 1.11(3) ?
  C18 H18b . . .92(3) ?
  C19 C110 . . 1.409(7) ?
  C110 C111 . . 1.353(7) ?
  C110 H110 . . .93(3) ?
  C111 O111 . . 1.396(6) ?
  C111 C112 . . 1.374(7) ?
  O111 C114 . . 1.439(8) ?
  C112 O112 . . 1.374(6) ?
  C112 C113 . . 1.358(7) ?
  O112 C114 . . 1.443(8) ?
  C113 H113 . . 1.16(4) ?
  C114 H114a . . .84(4) ?
  C114 H114b . . 1.15(4) ?
  C21 C22 . . 1.542(7) ?
  C21 C29 . . 1.396(7) ?
  C21 C213 . . 1.403(7) ?
  C22 C21' . . 1.523(6) ?
  C22 C23 . . 1.531(6) ?
  C22 H22 . . .93(3) ?
  C21' C22' . . 1.384(6) ?
  C21' C26' . . 1.400(7) ?
  C22' C23' . . 1.376(6) ?
  C22' H22' . . .82(3) ?
  C23' O23' . . 1.360(5) ?
  C23' C24' . . 1.411(7) ?
  O23' C231' . . 1.421(7) ?
  C231' H231'a . . .95(4) ?
  C231' H231'b . . 1.10(5) ?
  C231' H231'c . . 1.01(4) ?
  C24' O24' . . 1.364(6) ?
  C24' C25' . . 1.376(6) ?
  O24' H24' . . .70(4) ?
  C25' O25' . . 1.369(7) ?
  C25' C26' . . 1.387(7) ?
  O25' C251' . . 1.409(7) ?
  C251' H251'a . . .98(6) ?
  C251' H251'b . . 1.11(6) ?
  C251' H251'c . . .98(3) ?
  C26' H26' . . .93(3) ?
  C23 O23 . . 1.460(6) ?
  C23 C24 . . 1.520(8) ?
  C23 C27 . . 1.509(6) ?
  O23 H23 . . .82(5) ?
  C24 O24 . . 1.211(7) ?
  C24 O25 . . 1.363(6) ?
  O25 C26 . . 1.491(7) ?
  C26 C27 . . 1.513(7) ?
  C26 H26a . . 1.00(4) ?
  C26 H26b . . 1.03(3) ?
  C27 C28 . . 1.501(8) ?
  C27 H27 . . .97(3) ?
  C28 C29 . . 1.525(7) ?
  C28 H28a . . 1.00(3) ?
  C28 H28b . . 1.03(3) ?
  C29 C210 . . 1.407(7) ?
  C210 C211 . . 1.347(8) ?
  C210 H210 . . .86(3) ?
  C211 O211 . . 1.392(7) ?
  C211 C212 . . 1.386(7) ?
  O211 C214 . . 1.438(7) ?
  C212 O212 . . 1.387(7) ?
  C212 C213 . . 1.361(8) ?
  O212 C214 . . 1.448(8) ?
  C213 H213 . . .99(3) ?
  C214 H214a . . 1.09(4) ?
  C214 H214b . . 1.01(4) ?