#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011008.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_2011008
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  711
_journal_page_last  713
_publ_section_title
;
New limonoids from Harrisonia perforata (Blanco) Merr.
;
loop_
_publ_author_name
  "Chiaroni, Ang\`ele"
  "Riche, Claude"
  "Khuong-Huu, Qui"
  "Nguyen-Ngoc, Hanh"
  "Nguyen-Viet, Kinh"
  "Khuong-Huu, Fran\,coise"
_chemical_name_common  'Haperforine B1'
_chemical_formula_sum  'C27 H32 O9'
_chemical_formula_weight  500.53
_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+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  12.216(4)
_cell_length_b  12.463(5)
_cell_length_c  16.781(7)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2554.9(17)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.301
_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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C1  .0596(3)  .0522(2)  .1814(2)  .0393(7) Uani d . 1 . C
  C2  .0238(3)  .1355(3)  .1232(2)  .0448(8) Uani d . 1 . C
  H2  .0486  .2052  .1310  .054 Uiso calc R 1 . H
  C3  -.0409(3)  .1173(3)  .0609(2)  .0427(7) Uani d . 1 . C
  C4  -.0764(3)  .2090(3)  .0070(2)  .0495(8) Uani d . 1 . C
  C5  -.2185(4)  .0890(4)  -.0459(2)  .0654(11) Uani d . 1 . C
  C6  -.1524(4)  -.0003(4)  -.0205(3)  .0687(12) Uani d . 1 . C
  H6  -.1654  -.0677  -.0423  .082 Uiso calc R 1 . H
  C7  -.0732(4)  .0107(3)  .0334(2)  .0567(10) Uani d . 1 . C
  H7  -.0382  -.0497  .0537  .068 Uiso calc R 1 . H
  C8  .1694(2)  .0694(2)  .2253(2)  .0332(6) Uani d . 1 . C
  C9  .2135(3)  -.0419(2)  .2518(2)  .0373(7) Uani d . 1 . C
  H9  .1539  -.0800  .2788  .045 Uiso calc R 1 . H
  C10  .2522(3)  -.1117(3)  .1818(2)  .0555(9) Uani d . 1 . C
  H10  .3275  -.0899  .1697  .067 Uiso calc R 1 . H
  C11  .3086(3)  -.0301(2)  .3113(2)  .0447(8) Uani d . 1 . C
  H11A  .3269  -.1006  .3320  .054 Uiso calc R 1 . H
  H11B  .3722  -.0033  .2830  .054 Uiso calc R 1 . H
  C12  .2851(3)  .0437(2)  .3808(2)  .0435(8) Uani d . 1 . C
  H12A  .3510  .0508  .4126  .052 Uiso calc R 1 . H
  H12B  .2294  .0111  .4141  .052 Uiso calc R 1 . H
  C13  .2462(3)  .1566(2)  .3560(2)  .0370(7) Uani d . 1 . C
  C14  .1466(2)  .1366(2)  .3015(2)  .0302(6) Uani d . 1 . C
  C15  .0341(3)  .1297(2)  .3362(2)  .0384(7) Uani d . 1 . C
  H15  -.0148  .0812  .3073  .046 Uiso calc R 1 . H
  C16  -.0005(3)  .1508(3)  .4200(2)  .0447(8) Uani d . 1 . C
  C17  .3415(3)  .2205(3)  .3173(2)  .0406(7) Uani d . 1 . C
  C18  .2210(3)  .2221(3)  .4325(2)  .0469(8) Uani d . 1 . C
  H18A  .1966  .2927  .4179  .056 Uiso calc R 1 . H
  H18B  .2861  .2276  .4643  .056 Uiso calc R 1 . H
  H18C  .1647  .1867  .4625  .056 Uiso calc R 1 . H
  C19  .2559(5)  -.2296(3)  .2035(3)  .089(2) Uani d . 1 . C
  H19A  .2803  -.2704  .1583  .107 Uiso calc R 1 . H
  H19B  .1841  -.2531  .2188  .107 Uiso calc R 1 . H
  H19C  .3057  -.2400  .2471  .107 Uiso calc R 1 . H
  C20  .3264(3)  .3311(3)  .2884(2)  .0402(7) Uani d . 1 . C
  C21  .2381(3)  .3964(3)  .2856(3)  .0558(10) Uani d . 1 . C
  H21  .1677  .3759  .3003  .067 Uiso calc R 1 . H
  C22  .4146(3)  .3953(3)  .2594(2)  .0517(9) Uani d . 1 . C
  H22  .4869  .3733  .2533  .062 Uiso calc R 1 . H
  C23  .3755(4)  .4915(3)  .2427(3)  .0619(11) Uani d . 1 . C
  H23  .4165  .5484  .2229  .074 Uiso calc R 1 . H
  C28  -.0912(5)  .3139(3)  .0502(3)  .0765(14) Uani d . 1 . C
  H28A  -.1410  .3041  .0939  .092 Uiso calc R 1 . H
  H28B  -.1203  .3665  .0142  .092 Uiso calc R 1 . H
  H28C  -.0218  .3379  .0702  .092 Uiso calc R 1 . H
  C29  .0011(4)  .2205(4)  -.0620(2)  .0668(11) Uani d . 1 . C
  H29A  .0089  .1525  -.0884  .080 Uiso calc R 1 . H
  H29B  .0712  .2438  -.0429  .080 Uiso calc R 1 . H
  H29C  -.0273  .2724  -.0989  .080 Uiso calc R 1 . H
  C30  .2491(3)  .1279(3)  .1690(2)  .0421(7) Uani d . 1 . C
  H30A  .3177  .1391  .1956  .051 Uiso calc R 1 . H
  H30B  .2185  .1960  .1540  .051 Uiso calc R 1 . H
  H30C  .2607  .0852  .1221  .051 Uiso calc R 1 . H
  C31  -.0265(4)  .0677(4)  .5448(2)  .0664(11) Uani d . 1 . C
  H31A  -.0126  .0005  .5709  .080 Uiso calc R 1 . H
  H31B  -.1038  .0816  .5446  .080 Uiso calc R 1 . H
  H31C  .0105  .1243  .5728  .080 Uiso calc R 1 . H
  O1  .0010(2)  -.0229(2)  .19693(15)  .0531(6) Uani d . 1 . O
  O4  -.1860(2)  .1882(2)  -.0261(2)  .0660(8) Uani d . 1 . O
  O7  -.3039(3)  .0793(4)  -.0824(2)  .0964(12) Uani d . 1 . O
  O10  .1900(3)  -.0965(2)  .11050(15)  .0639(7) Uani d . 1 . O
  HO10  .1324  -.1300  .11372  .077 Uiso calc R 1 . H
  O14  .0676(2)  .2218(2)  .29068(13)  .0397(5) Uani d . 1 . O
  O16  -.0422(2)  .2327(2)  .4432(2)  .0601(7) Uani d . 1 . O
  O16'  .0131(2)  .0629(2)  .46411(14)  .0504(6) Uani d . 1 . O
  O17  .4332(2)  .1828(2)  .3173(2)  .0582(7) Uani d . 1 . O
  O21  .2651(2)  .4948(2)  .2589(2)  .0685(8) Uani d . 1 . O
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  .041(2)  .043(2)  .034(2)  -.0027(14)  -.0045(15)  -.0004(13)
  C2  .053(2)  .041(2)  .041(2)  -.0009(15)  -.008(2)  .0019(13)
  C3  .051(2)  .046(2)  .031(2)  .0026(15)  -.004(2)  .0019(14)
  C4  .053(2)  .047(2)  .048(2)  .007(2)  -.008(2)  .002(2)
  C5  .057(2)  .086(3)  .053(2)  -.009(2)  -.005(2)  .011(2)
  C6  .088(3)  .062(2)  .056(2)  -.020(2)  -.025(2)  .002(2)
  C7  .077(3)  .049(2)  .044(2)  -.002(2)  -.015(2)  .002(2)
  C8  .0352(14)  .0333(13)  .0313(15)  -.0009(11)  -.0008(14)  -.0013(12)
  C9  .0359(15)  .0344(15)  .042(2)  .0020(12)  .0006(14)  .0005(13)
  C10  .055(2)  .046(2)  .065(2)  .003(2)  .004(2)  -.017(2)
  C11  .039(2)  .0404(15)  .054(2)  .0051(13)  -.008(2)  .0029(14)
  C12  .044(2)  .040(2)  .047(2)  .0021(14)  -.008(2)  .0057(14)
  C13  .0366(15)  .0377(14)  .037(2)  -.0019(13)  -.0053(14)  .0023(13)
  C14  .0279(12)  .0307(12)  .032(2)  -.0005(11)  -.0004(13)  .0008(11)
  C15  .0350(14)  .0383(15)  .042(2)  .0005(12)  .0029(14)  -.0014(13)
  C16  .042(2)  .042(2)  .050(2)  .0033(15)  .003(2)  .0005(14)
  C17  .0360(15)  .044(2)  .042(2)  -.0023(13)  -.0009(15)  -.0059(14)
  C18  .050(2)  .051(2)  .039(2)  -.010(2)  -.004(2)  -.0059(15)
  C19  .116(4)  .048(2)  .102(4)  .026(3)  -.027(4)  -.023(2)
  C20  .038(2)  .043(2)  .039(2)  -.0077(13)  .0006(14)  -.0022(14)
  C21  .050(2)  .037(2)  .081(3)  -.0021(15)  .006(2)  .006(2)
  C22  .046(2)  .057(2)  .052(2)  -.012(2)  .003(2)  .001(2)
  C23  .064(2)  .055(2)  .066(3)  -.018(2)  .006(2)  .008(2)
  C28  .106(4)  .051(2)  .072(3)  .024(2)  -.018(3)  -.004(2)
  C29  .076(3)  .074(3)  .051(2)  .003(2)  .002(2)  .018(2)
  C30  .046(2)  .047(2)  .034(2)  -.0084(14)  .006(2)  .0021(13)
  C31  .082(3)  .073(2)  .044(2)  .006(2)  .016(2)  .007(2)
  O1  .0506(13)  .0567(13)  .0521(14)  -.0171(11)  -.0092(13)  .0090(12)
  O4  .058(2)  .069(2)  .071(2)  .0086(14)  -.0160(15)  .0051(15)
  O7  .067(2)  .134(3)  .088(2)  -.021(2)  -.030(2)  .018(2)
  O10  .085(2)  .0597(15)  .0475(14)  -.0137(15)  .004(2)  -.0097(12)
  O14  .0389(11)  .0360(10)  .0441(12)  .0073(9)  .0013(10)  .0034(9)
  O16  .069(2)  .0582(14)  .0536(15)  .0233(14)  .0154(14)  -.0015(12)
  O16'  .0587(14)  .0461(12)  .0463(13)  .0029(11)  .0134(13)  .0031(10)
  O17  .0327(11)  .0545(14)  .088(2)  .0006(10)  -.0012(13)  -.0017(14)
  O21  .067(2)  .0425(12)  .096(2)  -.0025(12)  .007(2)  .0121(14)
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 O1 . 1.207(4) ?
  C1 C2 . 1.490(4) ?
  C1 C8 . 1.547(4) ?
  C2 C3 . 1.330(5) ?
  C3 C7 . 1.460(5) ?
  C3 C4 . 1.521(5) ?
  C4 O4 . 1.472(5) ?
  C4 C29 . 1.503(6) ?
  C4 C28 . 1.506(5) ?
  C5 O7 . 1.216(5) ?
  C5 O4 . 1.340(5) ?
  C5 C6 . 1.440(6) ?
  C6 C7 . 1.332(6) ?
  C8 C30 . 1.540(4) ?
  C8 C14 . 1.553(4) ?
  C8 C9 . 1.553(4) ?
  C9 C10 . 1.537(5) ?
  C9 C11 . 1.538(4) ?
  C10 O10 . 1.429(5) ?
  C10 C19 . 1.515(6) ?
  C11 C12 . 1.513(5) ?
  C12 C13 . 1.541(4) ?
  C13 C14 . 1.543(4) ?
  C13 C18 . 1.552(5) ?
  C13 C17 . 1.554(4) ?
  C14 O14 . 1.446(3) ?
  C14 C15 . 1.494(4) ?
  C15 O14 . 1.438(4) ?
  C15 C16 . 1.492(5) ?
  C16 O16 . 1.206(4) ?
  C16 O16' . 1.332(4) ?
  C17 O17 . 1.215(4) ?
  C17 C20 . 1.473(5) ?
  C20 C21 . 1.351(5) ?
  C20 C22 . 1.429(5) ?
  C21 O21 . 1.347(4) ?
  C22 C23 . 1.320(6) ?
  C23 O21 . 1.377(5) ?
  C31 O16' . 1.439(5) ?