#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202181.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_2202181
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o771
_journal_page_last  o772
_publ_section_title
;
Trilobolide-6-O-isobutyrate, an eudesmanolide from Wedelia trilobata
;
loop_
_publ_author_name
  'Xue-Song Huang'
  'Ren-Wang Jiang'
  'Vincent Eng-Choon Ooi'
_chemical_name_common  'trilobolide-6-O-isobutyrate'
_chemical_formula_moiety  'C23 H32 O9'
_chemical_formula_sum  'C23 H32 O9'
_chemical_formula_iupac  'C23 H32 O9'
_chemical_formula_weight  452.49
_symmetry_cell_setting  hexagonal
_symmetry_space_group_name_H-M  'P 65'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-y, x-y, z+2/3'
  '-x+y, -x, z+1/3'
  '-x, -y, z+1/2'
  'y, -x+y, z+1/6'
  'x-y, x, z+5/6'
_cell_length_a  9.8368(8)
_cell_length_b  9.8368(8)
_cell_length_c  42.455(5)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  120
_cell_volume  3557.6(6)
_cell_formula_units_Z  6
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.267
_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
  O1 1.0229(4) 0.4731(4) 0.15271(7) 0.0534(8) Uani d . 1 . . O
  O2 0.7978(6) 0.3943(7) 0.17972(11) 0.0958(16) Uani d . 1 . . O
  O3 0.8361(4) 0.5346(4) 0.08709(7) 0.0448(7) Uani d . 1 . . O
  O4 0.8481(7) 0.6893(8) 0.12673(14) 0.122(2) Uani d . 1 . . O
  O5 0.8084(5) 0.0559(4) 0.05076(10) 0.0687(11) Uani d . 1 . . O
  H5A 0.8146 -0.0236 0.0484 0.08(2) Uiso calc R 1 . . H
  O6 1.1286(4) 0.3798(4) 0.02784(7) 0.0486(8) Uani d . 1 . . O
  O7 1.0525(5) 0.3461(6) -0.02266(8) 0.0718(11) Uani d . 1 . . O
  O8 1.0362(5) 0.7789(4) 0.05164(8) 0.0556(9) Uani d . 1 . . O
  O9 0.8391(7) 0.7867(5) 0.02710(11) 0.0889(15) Uani d . 1 . . O
  C1 0.9351(6) 0.3630(6) 0.12733(11) 0.0501(11) Uani d . 1 . . C
  H1A 0.8296 0.3499 0.1265 0.060 Uiso calc R 1 . . H
  C2 0.9204(7) 0.2058(6) 0.13451(12) 0.0619(14) Uani d . 1 . . C
  H2A 0.8634 0.1644 0.1541 0.074 Uiso calc R 1 . . H
  H2B 1.0238 0.2174 0.1368 0.074 Uiso calc R 1 . . H
  C3 0.8322(7) 0.0934(6) 0.10729(13) 0.0634(14) Uani d . 1 . . C
  H3A 0.8211 -0.0083 0.1119 0.076 Uiso calc R 1 . . H
  H3B 0.7277 0.0797 0.1059 0.076 Uiso calc R 1 . . H
  C4 0.9140(6) 0.1505(5) 0.07540(11) 0.0519(12) Uani d . 1 . . C
  C5 0.9342(5) 0.3163(5) 0.06973(10) 0.0412(10) Uani d . 1 . . C
  H5B 0.8265 0.2969 0.0710 0.049 Uiso calc R 1 . . H
  C6 0.9848(5) 0.3804(5) 0.03632(10) 0.0409(9) Uani d . 1 . . C
  H6A 0.9019 0.3098 0.0218 0.049 Uiso calc R 1 . . H
  C7 1.0154(6) 0.5468(5) 0.03049(11) 0.0449(10) Uani d . 1 . . C
  H7A 1.0960 0.5926 0.0141 0.054 Uiso calc R 1 . . H
  C8 1.0765(6) 0.6583(5) 0.05857(11) 0.0449(10) Uani d . 1 . . C
  H8A 1.1908 0.7060 0.0600 0.054 Uiso calc R 1 . . H
  C9 1.0026(5) 0.5819(5) 0.08962(10) 0.0412(10) Uani d . 1 . . C
  H9A 1.0509 0.6586 0.1067 0.049 Uiso calc R 1 . . H
  C10 1.0203(5) 0.4385(5) 0.09645(10) 0.0408(10) Uani d . 1 . . C
  C11 0.8805(6) 0.5655(6) 0.01966(11) 0.0540(12) Uani d . 1 . . C
  C12 0.9120(7) 0.7198(6) 0.03235(12) 0.0562(13) Uani d . 1 . . C
  C13 0.7620(9) 0.4789(9) 0.00149(15) 0.085(2) Uani d . 1 . . C
  H13A 0.6921 0.5125 -0.0041 0.102 Uiso calc R 1 . . H
  H13B 0.7469 0.3833 -0.0059 0.102 Uiso calc R 1 . . H
  C14 1.0630(7) 0.1371(7) 0.07467(14) 0.0659(15) Uani d . 1 . . C
  H14A 1.0356 0.0302 0.0785 0.099 Uiso calc R 1 . . H
  H14B 1.1345 0.2035 0.0906 0.099 Uiso calc R 1 . . H
  H14C 1.1120 0.1692 0.0544 0.099 Uiso calc R 1 . . H
  C15 1.1982(6) 0.4990(6) 0.09873(11) 0.0510(11) Uani d . 1 . . C
  H15A 1.2420 0.5723 0.1158 0.076 Uiso calc R 1 . . H
  H15B 1.2482 0.5501 0.0794 0.076 Uiso calc R 1 . . H
  H15C 1.2150 0.4122 0.1024 0.076 Uiso calc R 1 . . H
  C16 0.9365(8) 0.4699(8) 0.17795(13) 0.0657(14) Uani d . 1 . . C
  C17 1.0411(10) 0.5783(9) 0.20335(16) 0.087(2) Uani d . 1 . . C
  H17A 0.9782 0.5753 0.2209 0.131 Uiso calc R 1 . . H
  H17B 1.0986 0.6834 0.1953 0.131 Uiso calc R 1 . . H
  H17C 1.1133 0.5452 0.2101 0.131 Uiso calc R 1 . . H
  C18 0.7774(7) 0.6038(7) 0.10565(13) 0.0645(15) Uani d . 1 . . C
  C19 0.6121(8) 0.5561(10) 0.09579(19) 0.089(2) Uani d . 1 . . C
  H19A 0.5719 0.6066 0.1092 0.133 Uiso calc R 1 . . H
  H19B 0.5468 0.4442 0.0976 0.133 Uiso calc R 1 . . H
  H19C 0.6123 0.5870 0.0743 0.133 Uiso calc R 1 . . H
  C20 1.1473(6) 0.3604(7) -0.00316(12) 0.0548(12) Uani d . 1 . . C
  C21 1.2954(8) 0.3593(9) -0.00938(14) 0.0805(19) Uani d . 1 . . C
  H21A 1.3739 0.4137 0.0071 0.097 Uiso calc R 1 . . H
  C22 1.2545(19) 0.194(2) -0.0127(5) 0.221(8) Uiso d . 1 . . C
  H22A 1.2169 0.1408 0.0071 0.331 Uiso calc R 1 . . H
  H22B 1.3459 0.1892 -0.0190 0.331 Uiso calc R 1 . . H
  H22C 1.1741 0.1437 -0.0284 0.331 Uiso calc R 1 . . H
  C23 1.3581(19) 0.4185(17) -0.0409(4) 0.182(6) Uiso d . 1 . . C
  H23A 1.3908 0.5281 -0.0422 0.273 Uiso calc R 1 . . H
  H23B 1.2781 0.3617 -0.0564 0.273 Uiso calc R 1 . . H
  H23C 1.4463 0.4043 -0.0449 0.273 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 0.069(2) 0.063(2) 0.0340(16) 0.0379(18) -0.0070(15) -0.0044(14)
  O2 0.082(3) 0.132(4) 0.076(3) 0.055(3) 0.012(2) -0.018(3)
  O3 0.0487(17) 0.0510(18) 0.0449(16) 0.0325(15) -0.0010(13) -0.0038(13)
  O4 0.121(4) 0.164(6) 0.123(5) 0.102(4) -0.031(4) -0.086(4)
  O5 0.090(3) 0.0450(19) 0.078(3) 0.039(2) -0.025(2) -0.0193(18)
  O6 0.0532(18) 0.0615(19) 0.0426(17) 0.0373(16) -0.0063(14) -0.0113(14)
  O7 0.073(3) 0.110(3) 0.0447(19) 0.055(3) -0.0066(18) -0.014(2)
  O8 0.078(2) 0.0415(18) 0.0532(19) 0.0340(17) -0.0072(17) 0.0003(14)
  O9 0.141(4) 0.091(3) 0.078(3) 0.091(3) -0.034(3) -0.016(2)
  C1 0.065(3) 0.047(3) 0.039(2) 0.028(2) -0.005(2) -0.0015(19)
  C2 0.088(4) 0.054(3) 0.052(3) 0.041(3) 0.001(3) 0.011(2)
  C3 0.076(4) 0.044(3) 0.067(3) 0.027(3) -0.003(3) 0.008(2)
  C4 0.065(3) 0.040(2) 0.055(3) 0.029(2) -0.011(2) -0.007(2)
  C5 0.046(2) 0.039(2) 0.046(2) 0.027(2) -0.0029(18) -0.0043(18)
  C6 0.042(2) 0.044(2) 0.041(2) 0.025(2) -0.0068(18) -0.0043(17)
  C7 0.057(3) 0.044(2) 0.041(2) 0.031(2) 0.004(2) 0.0014(19)
  C8 0.048(2) 0.039(2) 0.050(2) 0.023(2) -0.0058(19) -0.0022(19)
  C9 0.047(2) 0.037(2) 0.041(2) 0.022(2) -0.0097(18) -0.0086(17)
  C10 0.050(3) 0.040(2) 0.036(2) 0.025(2) -0.0054(18) -0.0039(17)
  C11 0.075(3) 0.062(3) 0.043(2) 0.048(3) -0.012(2) -0.008(2)
  C12 0.084(4) 0.060(3) 0.047(3) 0.052(3) -0.007(2) 0.003(2)
  C13 0.119(6) 0.102(5) 0.072(4) 0.083(5) -0.052(4) -0.036(4)
  C14 0.095(4) 0.060(3) 0.067(3) 0.057(3) -0.014(3) -0.010(3)
  C15 0.059(3) 0.056(3) 0.047(2) 0.036(3) -0.012(2) -0.009(2)
  C16 0.082(4) 0.086(4) 0.047(3) 0.056(4) 0.003(3) -0.005(3)
  C17 0.114(5) 0.107(5) 0.059(4) 0.070(5) -0.017(3) -0.029(4)
  C18 0.077(4) 0.077(4) 0.059(3) 0.053(3) -0.002(3) -0.007(3)
  C19 0.077(4) 0.118(6) 0.095(5) 0.067(4) 0.014(4) 0.004(4)
  C20 0.059(3) 0.066(3) 0.047(3) 0.037(3) -0.002(2) -0.011(2)
  C21 0.080(4) 0.122(6) 0.061(3) 0.067(4) 0.001(3) -0.015(3)
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 C16 . 1.359(7) yes
  O1 C1 . 1.464(6) yes
  O2 C16 . 1.185(8) yes
  O3 C18 . 1.346(6) yes
  O3 C9 . 1.465(6) yes
  O4 C18 . 1.186(7) yes
  O5 C4 . 1.439(6) yes
  O5 H5A . 0.8200 ?
  O6 C20 . 1.355(6) yes
  O6 C6 . 1.463(5) yes
  O7 C20 . 1.201(6) yes
  O8 C12 . 1.338(6) yes
  O8 C8 . 1.456(5) yes
  O9 C12 . 1.211(6) yes
  C1 C2 . 1.510(7) ?
  C1 C10 . 1.533(7) ?
  C1 H1A . 0.9800 ?
  C2 C3 . 1.534(8) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C4 . 1.531(8) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 C14 . 1.536(8) ?
  C4 C5 . 1.560(6) ?
  C5 C6 . 1.531(6) ?
  C5 C10 . 1.559(6) ?
  C5 H5B . 0.9800 ?
  C6 C7 . 1.529(6) ?
  C6 H6A . 0.9800 ?
  C7 C11 . 1.500(7) ?
  C7 C8 . 1.525(6) ?
  C7 H7A . 0.9800 ?
  C8 C9 . 1.512(7) ?
  C8 H8A . 0.9800 ?
  C9 C10 . 1.534(6) ?
  C9 H9A . 0.9800 ?
  C10 C15 . 1.544(7) ?
  C11 C13 . 1.299(8) yes
  C11 C12 . 1.490(7) ?
  C13 H13A . 0.9300 ?
  C13 H13B . 0.9300 ?
  C14 H14A . 0.9600 ?
  C14 H14B . 0.9600 ?
  C14 H14C . 0.9600 ?
  C15 H15A . 0.9600 ?
  C15 H15B . 0.9600 ?
  C15 H15C . 0.9600 ?
  C16 C17 . 1.504(9) ?
  C17 H17A . 0.9600 ?
  C17 H17B . 0.9600 ?
  C17 H17C . 0.9600 ?
  C18 C19 . 1.509(9) ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  C20 C21 . 1.487(8) ?
  C21 C23 . 1.468(18) ?
  C21 C22 . 1.48(2) ?
  C21 H21A . 0.9800 ?
  C22 H22A . 0.9600 ?
  C22 H22B . 0.9600 ?
  C22 H22C . 0.9600 ?
  C23 H23A . 0.9600 ?
  C23 H23B . 0.9600 ?
  C23 H23C . 0.9600 ?