#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012227.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_2012227
loop_
_publ_author_name
'Linden, Anthony'
'Lee, C. Kuan'
'Muhammad Sofian, A. S.'
_publ_section_title
;
3-O-Acetyl-4-deoxy-4-iodo-\b-D-fructofuranosyl
2,3,6-tri-O-acetyl-4-chloro-4-deoxy-\a-D-glucopyranoside
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              1098
_journal_page_last               1100
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H28 Cl I O13'
_chemical_formula_moiety         'C20 H28 Cl I O13'
_chemical_formula_sum            'C20 H28 Cl I O13'
_chemical_formula_weight         638.77
_chemical_melting_point          386.5(5)
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.84070(10)
_cell_length_b                   10.55620(10)
_cell_length_c                   28.2974(4)
_cell_measurement_temperature    160.0(10)
_cell_volume                     2640.83(5)
_diffrn_ambient_temperature      160.0(10)
_exptl_crystal_density_diffrn    1.607
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '386-387' was changed to '386.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2012227
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'
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
I9 .345310(18) -.00019(2) .117719(8) .04514(8) Uani d . 1 . . I
Cl4 .61005(9) .70258(7) .12970(3) .04115(18) Uani d . 1 . . Cl
O1 .79842(19) .28133(15) .12348(6) .0210(3) Uani d . 1 . . O
O2 1.0626(2) .40409(17) .15045(6) .0253(4) Uani d . 1 . . O
O3 .9374(2) .64732(17) .16176(7) .0281(4) Uani d . 1 . . O
O5 .7776(2) .40937(17) .05674(6) .0239(4) Uani d . 1 . . O
O6 .6474(2) .62336(17) .01006(7) .0323(4) Uani d . 1 . . O
O8 .6134(2) .17177(18) .18231(6) .0260(4) Uani d . 1 . . O
O10 .7893(2) .10889(17) .07114(6) .0249(4) Uani d . 1 . . O
O11 .5706(3) .2274(2) .01008(9) .0458(6) Uani d . 1 . . O
H11 .6544 .2639 .0134 .069 Uiso calc R 1 . . H
O12 .9657(2) -.03530(16) .13177(7) .0291(4) Uani d . 1 . . O
H12 .9363 -.0570 .1047 .044 Uiso calc R 1 . . H
O13 1.2614(3) .4352(3) .10247(9) .0597(8) Uani d . 1 . . O
O15 .8306(4) .6113(2) .23280(8) .0549(7) Uani d . 1 . . O
O17 .4456(3) .6479(2) -.03649(8) .0407(5) Uani d . 1 . . O
O19 .7482(4) .0556(3) .23337(9) .0727(10) Uani d . 1 . . O
C1 .8785(3) .3539(2) .08984(8) .0212(5) Uani d . 1 . . C
H1 .9523 .2985 .0728 .025 Uiso calc R 1 . . H
C2 .9635(3) .4583(2) .11584(9) .0227(4) Uani d . 1 . . C
H2 1.0243 .5085 .0927 .027 Uiso calc R 1 . . H
C3 .8530(3) .5456(2) .14094(9) .0235(5) Uani d . 1 . . C
H3 .7954 .4982 .1657 .028 Uiso calc R 1 . . H
C4 .7463(3) .5983(2) .10387(9) .0254(5) Uani d . 1 . . C
H4 .8071 .6474 .0804 .030 Uiso calc R 1 . . H
C5 .6652(3) .4908(3) .07776(8) .0250(5) Uani d . 1 . . C
H5 .6048 .4407 .1010 .030 Uiso calc R 1 . . H
C6 .5624(3) .5342(2) .03854(11) .0305(6) Uani d . 1 . . C
H61 .5300 .4611 .0191 .037 Uiso calc R 1 . . H
H62 .4712 .5755 .0518 .037 Uiso calc R 1 . . H
C7 .8045(3) .1469(2) .11888(9) .0201(4) Uani d . 1 . . C
C8 .6627(3) .0960(2) .14373(9) .0228(5) Uani d . 1 . . C
H8 .6784 .0063 .1540 .027 Uiso calc R 1 . . H
C9 .5483(3) .1024(2) .10397(10) .0265(5) Uani d . 1 . . C
H9 .5220 .1932 .0981 .032 Uiso calc R 1 . . H
C10 .6410(3) .0542(2) .06261(9) .0285(5) Uani d . 1 . . C
H10 .6478 -.0403 .0641 .034 Uiso calc R 1 . . H
C11 .5911(4) .0946(3) .01352(11) .0396(7) Uani d . 1 . . C
H111 .6681 .0675 -.0098 .048 Uiso calc R 1 . . H
H112 .4949 .0516 .0056 .048 Uiso calc R 1 . . H
C12 .9560(3) .0981(2) .13621(9) .0225(5) Uani d . 1 . . C
H121 1.0381 .1380 .1177 .027 Uiso calc R 1 . . H
H122 .9698 .1221 .1698 .027 Uiso calc R 1 . . H
C13 1.2120(3) .4003(3) .13954(10) .0300(6) Uani d . 1 . . C
C14 1.3006(3) .3465(3) .17968(11) .0369(7) Uani d . 1 . . C
H141 1.4079 .3430 .1711 .055 Uiso calc R 1 . . H
H142 1.2642 .2608 .1867 .055 Uiso calc R 1 . . H
H143 1.2878 .4002 .2076 .055 Uiso calc R 1 . . H
C15 .9139(4) .6726(3) .20857(10) .0335(6) Uani d . 1 . . C
C16 .9999(4) .7875(3) .22339(11) .0417(7) Uani d . 1 . . C
H161 .9394 .8633 .2170 .063 Uiso calc R 1 . . H
H162 1.0950 .7920 .2057 .063 Uiso calc R 1 . . H
H163 1.0219 .7826 .2573 .063 Uiso calc R 1 . . H
C17 .5737(3) .6743(2) -.02664(10) .0281(6) Uani d . 1 . . C
C18 .6719(4) .7686(3) -.05203(11) .0373(7) Uani d . 1 . . C
H181 .6368 .7779 -.0847 .056 Uiso calc R 1 . . H
H182 .7769 .7388 -.0520 .056 Uiso calc R 1 . . H
H183 .6662 .8507 -.0359 .056 Uiso calc R 1 . . H
C19 .6580(4) .1383(4) .22614(10) .0455(8) Uani d . 1 . . C
C20 .5860(5) .2208(6) .26226(13) .0789(16) Uani d . 1 . . C
H201 .4768 .2048 .2629 .118 Uiso calc R 1 . . H
H202 .6044 .3098 .2543 .118 Uiso calc R 1 . . H
H203 .6292 .2021 .2934 .118 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
I9 .01993(8) .03466(10) .08082(16) -.00201(10) -.00215(8) -.01151(12)
Cl4 .0390(4) .0344(3) .0501(4) .0169(3) .0073(3) -.0037(3)
O1 .0238(8) .0161(7) .0230(8) .0030(6) .0060(7) .0034(6)
O2 .0222(8) .0277(9) .0260(9) .0037(7) -.0005(7) .0052(7)
O3 .0354(10) .0218(8) .0271(9) .0002(7) .0022(8) .0000(7)
O5 .0252(9) .0222(8) .0242(9) .0051(7) -.0001(7) .0035(7)
O6 .0312(10) .0277(9) .0379(10) -.0024(9) -.0106(9) .0131(8)
O8 .0233(8) .0340(9) .0207(8) .0032(7) .0040(7) .0037(7)
O10 .0270(9) .0270(9) .0207(8) .0038(7) -.0014(7) -.0016(7)
O11 .0604(16) .0326(11) .0443(13) .0090(11) -.0257(12) -.0032(10)
O12 .0309(9) .0219(9) .0345(10) .0089(7) -.0040(8) .0002(7)
O13 .0259(11) .103(2) .0504(14) .0114(12) .0101(10) .0262(14)
O15 .080(2) .0542(14) .0301(11) -.0186(15) .0169(13) -.0050(10)
O17 .0367(12) .0485(13) .0369(11) .0053(10) -.0140(9) .0013(10)
O19 .084(2) .094(2) .0401(14) .0432(18) .0041(14) .0258(14)
C1 .0212(11) .0204(10) .0219(11) .0029(9) .0046(9) .0057(9)
C2 .0222(10) .0220(9) .0239(11) .0028(8) .0019(10) .0055(9)
C3 .0250(11) .0203(9) .0251(11) -.0006(9) .0034(10) .0031(9)
C4 .0241(12) .0212(11) .0309(13) .0048(9) .0046(10) .0033(10)
C5 .0216(9) .0239(11) .0294(12) .0065(13) .0037(9) .0058(10)
C6 .0237(12) .0247(12) .0430(15) .0003(9) -.0017(11) .0094(10)
C7 .0216(10) .0178(9) .0208(10) .0019(8) .0021(9) -.0006(9)
C8 .0202(10) .0202(10) .0281(12) .0024(9) .0016(10) .0032(9)
C9 .0189(11) .0214(11) .0391(14) .0010(9) -.0055(10) -.0024(10)
C10 .0296(13) .0246(11) .0311(13) .0054(11) -.0098(11) -.0051(10)
C11 .055(2) .0302(14) .0337(15) .0074(14) -.0185(14) -.0069(12)
C12 .0212(11) .0194(11) .0268(12) .0037(9) -.0021(10) .0014(9)
C13 .0235(12) .0324(14) .0340(14) .0035(11) -.0013(11) -.0038(12)
C14 .0300(14) .0398(16) .0408(16) .0082(12) -.0086(13) -.0035(13)
C15 .0440(17) .0302(14) .0263(13) .0053(12) -.0008(12) .0016(11)
C16 .061(2) .0345(15) .0297(15) -.0009(15) -.0066(14) -.0024(12)
C17 .0368(15) .0205(11) .0272(13) .0074(10) -.0079(11) -.0021(10)
C18 .0527(19) .0242(13) .0349(15) .0014(13) -.0049(14) .0051(11)
C19 .0413(17) .070(2) .0253(14) .0147(18) .0078(14) .0116(14)
C20 .057(2) .154(5) .0258(17) .040(3) .0066(16) -.009(2)
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
I9 C9 . 2.132(3) ?
Cl4 C4 . 1.787(3) ?
O1 C1 . 1.413(3) yes
O1 C7 . 1.426(3) yes
O2 C13 . 1.357(3) ?
O2 C2 . 1.433(3) ?
O3 C15 . 1.367(3) ?
O3 C3 . 1.434(3) ?
O5 C1 . 1.420(3) yes
O5 C5 . 1.442(3) yes
O6 C17 . 1.339(3) ?
O6 C6 . 1.450(3) ?
O8 C19 . 1.348(3) ?
O8 C8 . 1.422(3) ?
O10 C7 . 1.416(3) yes
O10 C10 . 1.453(3) yes
O11 C11 . 1.417(4) ?
O11 H11 . .8400 ?
O12 C12 . 1.416(3) ?
O12 H12 . .8400 ?
O13 C13 . 1.194(4) ?
O15 C15 . 1.196(4) ?
O17 C17 . 1.199(4) ?
O19 C19 . 1.200(4) ?
C1 C2 . 1.523(3) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.519(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.517(4) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.532(4) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.506(4) ?
C5 H5 . 1.0000 ?
C6 H61 . .9900 ?
C6 H62 . .9900 ?
C7 C12 . 1.516(3) ?
C7 C8 . 1.535(3) ?
C8 C9 . 1.514(4) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.517(4) ?
C9 H9 . 1.0000 ?
C10 C11 . 1.519(4) ?
C10 H10 . 1.0000 ?
C11 H111 . .9900 ?
C11 H112 . .9900 ?
C12 H121 . .9900 ?
C12 H122 . .9900 ?
C13 C14 . 1.492(4) ?
C14 H141 . .9800 ?
C14 H142 . .9800 ?
C14 H143 . .9800 ?
C15 C16 . 1.492(4) ?
C16 H161 . .9800 ?
C16 H162 . .9800 ?
C16 H163 . .9800 ?
C17 C18 . 1.504(4) ?
C18 H181 . .9800 ?
C18 H182 . .9800 ?
C18 H183 . .9800 ?
C19 C20 . 1.486(5) ?
C20 H201 . .9800 ?
C20 H202 . .9800 ?
C20 H203 . .9800 ?