#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200906.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_2200906
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2002
_journal_volume  58
_journal_page_first  o227
_journal_page_last  o228
_publ_section_title
;
Methyl (2'R,3'R)-2-azido-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-
\a-L-glucopyranoside
;
loop_
_publ_author_name
  'Barnes, John C.'
  'Brimacombe, John S.'
  'Connolly, Lisa M. C.'
  'Dix, Alexander P.'
_chemical_formula_moiety  'C13 H23 N3 O6'
_chemical_formula_sum  'C13 H23 N3 O6'
_chemical_formula_iupac  'C13 H23 N3 O6'
_chemical_formula_weight  317.34
_chemical_melting_point  '88-89'
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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  10.065(4)
_cell_length_b  10.512(16)
_cell_length_c  30.696(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3248(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.298
_diffrn_ambient_temperature  150(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
  C1A  .0398(4)  .5407(3)  .20823(13)  .0341(11) Uani d . 1 . . C
  H1A  -.0566  .5257  .2022  .044 Uiso calc R 1 . . H
  O1A  .1111(3)  .4259(2)  .20226(8)  .0364(7) Uani d . 1 . . O
  C2A  .0583(4)  .5759(3)  .25646(12)  .0270(10) Uani d . 1 . . C
  H2A  .0034  .6535  .2621  .035 Uiso calc R 1 . . H
  C3A  .2012(4)  .6119(3)  .26443(12)  .0238(10) Uani d . 1 . . C
  H3A  .2590  .5360  .2591  .031 Uiso calc R 1 . . H
  O3A  .2157(2)  .6518(2)  .30893(8)  .0268(6) Uani d . 1 . . O
  C4A  .2411(4)  .7167(3)  .23397(13)  .0240(10) Uani d . 1 . . C
  H4A  .1843  .7931  .2395  .031 Uiso calc R 1 . . H
  O4A  .3774(3)  .7486(2)  .24179(8)  .0289(7) Uani d . 1 . . O
  C5A  .2245(4)  .6745(3)  .18700(13)  .0296(10) Uani d . 1 . . C
  H5A  .2835  .5999  .1811  .039 Uiso calc R 1 . . H
  O5A  .0876(3)  .6385(2)  .18049(8)  .0338(7) Uani d . 1 . . O
  C6A  .2530(4)  .7788(3)  .15447(13)  .0430(12) Uani d . 1 . . C
  H6A1  .2340  .7479  .1250  .056 Uiso calc R 1 . . H
  H6A2  .3467  .8034  .1565  .056 Uiso calc R 1 . . H
  H6A3  .1968  .8526  .1608  .056 Uiso calc R 1 . . H
  C7A  .0778(5)  .3650(4)  .16192(14)  .0624(15) Uani d . 1 . . C
  H7A1  -.0187  .3546  .1600  .081 Uiso calc R 1 . . H
  H7A2  .1206  .2814  .1606  .081 Uiso calc R 1 . . H
  H7A3  .1089  .4175  .1376  .081 Uiso calc R 1 . . H
  N11A  .0057(4)  .4734(3)  .28472(11)  .0383(9) Uani d . 1 . . N
  N12A  .0863(4)  .3844(4)  .29113(12)  .0427(10) Uani d . 1 . . N
  N13A  .1521(4)  .2985(3)  .30025(15)  .0665(14) Uani d . 1 . . N
  C14A  .3525(4)  .6849(3)  .31841(13)  .0306(11) Uani d . 1 . . C
  O14A  .4356(3)  .5802(2)  .31104(9)  .0355(7) Uani d . 1 . . O
  C15A  .4140(4)  .4712(3)  .33933(14)  .0507(13) Uani d . 1 . . C
  H15A  .4595  .4850  .3672  .066 Uiso calc R 1 . . H
  H15B  .4494  .3945  .3254  .066 Uiso calc R 1 . . H
  H15C  .3186  .4605  .3445  .066 Uiso calc R 1 . . H
  C16A  .3507(4)  .7283(3)  .36519(11)  .0351(11) Uani d . 1 . . C
  H16A  .3087  .6629  .3833  .046 Uiso calc R 1 . . H
  H16B  .3003  .8077  .3675  .046 Uiso calc R 1 . . H
  H16C  .4420  .7424  .3752  .046 Uiso calc R 1 . . H
  C17A  .4024(4)  .7873(3)  .28585(12)  .0286(10) Uani d . 1 . . C
  O17A  .3261(2)  .8975(2)  .29593(9)  .0343(7) Uani d . 1 . . O
  C18A  .3519(5) 1.0064(3)  .26991(14)  .0487(13) Uani d . 1 . . C
  H18A  .4422 1.0370  .2757  .063 Uiso calc R 1 . . H
  H18B  .2879 1.0734  .2771  .063 Uiso calc R 1 . . H
  H18C  .3435  .9839  .2391  .063 Uiso calc R 1 . . H
  C19A  .5502(4)  .8097(3)  .28831(13)  .0361(11) Uani d . 1 . . C
  H19A  .5770  .8683  .2651  .047 Uiso calc R 1 . . H
  H19B  .5971  .7287  .2848  .047 Uiso calc R 1 . . H
  H19C  .5726  .8468  .3167  .047 Uiso calc R 1 . . H
  C1B  .2397(5)  .7960(4)  -.04450(13)  .0357(11) Uani d . 1 . . C
  H1B  .2619  .7050  -.0506  .046 Uiso calc R 1 . . H
  O1B  .3564(3)  .8691(2)  -.04779(9)  .0416(8) Uani d . 1 . . O
  C2B  .1932(4)  .8076(3)  .00278(12)  .0263(10) Uani d . 1 . . C
  H2B  .1130  .7522  .0059  .034 Uiso calc R 1 . . H
  C3B  .1481(4)  .9436(3)  .01098(12)  .0267(10) Uani d . 1 . . C
  H3B  .2251 1.0029  .0076  .035 Uiso calc R 1 . . H
  O3B  .0965(2)  .9526(2)  .05450(8)  .0277(7) Uani d . 1 . . O
  C4B  .0421(4)  .9775(3)  -.02095(13)  .0290(11) Uani d . 1 . . C
  H4B  -.0364  .9206  -.0165  .038 Uiso calc R 1 . . H
  O4B  .0033(3) 1.1076(2)  -.01350(9)  .0327(7) Uani d . 1 . . O
  C5B  .0916(4)  .9638(3)  -.06753(12)  .0343(11) Uani d . 1 . . C
  H5B  .1653 1.0257  -.0730  .045 Uiso calc R 1 . . H
  O5B  .1400(3)  .8349(2)  -.07305(8)  .0405(8) Uani d . 1 . . O
  C6B  -.0179(5)  .9828(4)  -.10106(13)  .0480(13) Uani d . 1 . . C
  H6B1  .0185  .9705  -.1304  .062 Uiso calc R 1 . . H
  H6B2  -.0537 1.0692  -.0985  .062 Uiso calc R 1 . . H
  H6B3  -.0890  .9209  -.0959  .062 Uiso calc R 1 . . H
  C7B  .4261(5)  .8501(4)  -.08829(13)  .0587(14) Uani d . 1 . . C
  H7B1  .4457  .7594  -.0920  .076 Uiso calc R 1 . . H
  H7B2  .5093  .8985  -.0879  .076 Uiso calc R 1 . . H
  H7B3  .3705  .8794  -.1125  .076 Uiso calc R 1 . . H
  N11B  .2933(4)  .7597(3)  .03366(11)  .0348(10) Uani d . 1 . . N
  N12B  .3825(4)  .8366(3)  .04247(11)  .0372(10) Uani d . 1 . . N
  N13B  .4718(4)  .8972(3)  .05397(13)  .0518(11) Uani d . 1 . . N
  C14B  .0498(4) 1.0773(3)  .06461(13)  .0303(11) Uani d . 1 . . C
  O14B  .1544(3) 1.1658(2)  .06267(9)  .0384(8) Uani d . 1 . . O
  C15B  .2679(4) 1.1405(4)  .09004(14)  .0477(13) Uani d . 1 . . C
  H15D  .2492 1.1693  .1198  .062 Uiso calc R 1 . . H
  H15E  .3455 1.1861  .0787  .062 Uiso calc R 1 . . H
  H15F  .2862 1.0489  .0902  .062 Uiso calc R 1 . . H
  C16B  -.0121(4) 1.0656(3)  .10942(12)  .0390(12) Uani d . 1 . . C
  H16D  .0548 1.0351  .1301  .051 Uiso calc R 1 . . H
  H16E  -.0862 1.0052  .1083  .051 Uiso calc R 1 . . H
  H16F  -.0449 1.1490  .1188  .051 Uiso calc R 1 . . H
  C17B  -.0511(4) 1.1240(3)  .02886(14)  .0338(11) Uani d . 1 . . C
  O17B  -.1647(3) 1.0467(2)  .03528(9)  .0385(8) Uani d . 1 . . O
  C18B  -.2718(4) 1.0732(4)  .00631(15)  .0577(15) Uani d . 1 . . C
  H18D  -.3093 1.1569  .0131  .075 Uiso calc R 1 . . H
  H18E  -.3406 1.0080  .0096  .075 Uiso calc R 1 . . H
  H18F  -.2391 1.0730  -.0238  .075 Uiso calc R 1 . . H
  C19B  -.0830(4) 1.2656(3)  .03333(14)  .0431(13) Uani d . 1 . . C
  H19D  -.1355 1.2935  .0082  .056 Uiso calc R 1 . . H
  H19E  .0000 1.3143  .0345  .056 Uiso calc R 1 . . H
  H19F  -.1337 1.2799  .0601  .056 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
  C1A  .031(3)  .038(3)  .033(3)  -.005(2)  .002(2)  -.005(2)
  O1A  .047(2)  .0307(16)  .0311(18)  .0026(13)  -.0013(16)  -.0123(13)
  C2A  .031(3)  .030(2)  .020(2)  -.0025(19)  .002(2)  -.0035(18)
  C3A  .026(3)  .026(2)  .019(2)  .0006(18)  -.001(2)  -.0068(18)
  O3A  .0250(18)  .0323(14)  .0232(17)  -.0047(12)  -.0028(14)  -.0020(12)
  C4A  .021(3)  .028(2)  .023(2)  .0004(18)  .000(2)  .0013(19)
  O4A  .0255(18)  .0384(15)  .0228(17)  -.0025(13)  -.0001(14)  -.0065(13)
  C5A  .026(3)  .030(2)  .033(3)  .001(2)  -.003(2)  .000(2)
  O5A  .0293(19)  .0425(17)  .0296(18)  .0021(14)  -.0044(15)  -.0004(13)
  C6A  .043(3)  .059(3)  .027(3)  .002(2)  .002(2)  .004(2)
  C7A  .076(4)  .058(3)  .053(4)  -.002(3)  -.005(3)  -.034(3)
  N11A  .036(2)  .039(2)  .040(3)  -.0089(19)  -.002(2)  -.0003(18)
  N12A  .040(3)  .045(3)  .043(3)  -.018(2)  .003(2)  .003(2)
  N13A  .063(3)  .045(2)  .092(4)  -.009(2)  -.006(3)  .022(2)
  C14A  .024(3)  .034(2)  .034(3)  .002(2)  -.003(2)  -.004(2)
  O14A  .0307(19)  .0412(17)  .0345(19)  .0038(13)  -.0030(15)  .0004(14)
  C15A  .054(3)  .048(3)  .050(3)  .003(2)  -.008(3)  .013(2)
  C16A  .040(3)  .045(2)  .020(3)  -.012(2)  -.005(2)  .000(2)
  C17A  .027(3)  .036(2)  .022(3)  -.003(2)  .003(2)  -.0033(19)
  O17A  .0399(19)  .0265(15)  .0366(19)  -.0002(13)  .0112(16)  -.0024(14)
  C18A  .067(4)  .027(2)  .052(3)  -.009(2)  .012(3)  -.002(2)
  C19A  .029(3)  .046(2)  .033(3)  -.006(2)  .007(2)  -.007(2)
  C1B  .048(3)  .032(2)  .027(3)  .004(2)  .003(3)  .001(2)
  O1B  .049(2)  .0420(17)  .0336(19)  -.0019(16)  .0181(17)  -.0024(14)
  C2B  .029(3)  .024(2)  .026(3)  -.0001(18)  .002(2)  -.0015(18)
  C3B  .036(3)  .023(2)  .021(3)  -.0029(19)  .001(2)  .0046(18)
  O3B  .0357(18)  .0260(15)  .0214(16)  .0057(12)  .0031(15)  -.0010(12)
  C4B  .035(3)  .021(2)  .031(3)  -.0023(19)  -.003(2)  .0021(18)
  O4B  .0394(19)  .0280(15)  .0309(19)  .0026(13)  .0007(15)  .0066(12)
  C5B  .045(3)  .031(2)  .028(3)  -.004(2)  -.001(2)  .0061(19)
  O5B  .066(2)  .0344(17)  .0212(18)  -.0049(16)  -.0056(17)  -.0014(13)
  C6B  .066(4)  .046(3)  .032(3)  -.015(2)  -.014(3)  .008(2)
  C7B  .075(4)  .065(3)  .036(3)  .005(3)  .024(3)  .003(2)
  N11B  .040(3)  .030(2)  .034(2)  .0043(18)  .005(2)  -.0008(17)
  N12B  .040(3)  .043(2)  .029(2)  .017(2)  .001(2)  -.0016(19)
  N13B  .043(3)  .060(3)  .052(3)  .007(2)  -.012(2)  -.002(2)
  C14B  .028(3)  .025(2)  .038(3)  .002(2)  .002(2)  -.002(2)
  O14B  .0315(19)  .0291(16)  .055(2)  -.0027(14)  -.0022(17)  -.0022(14)
  C15B  .040(3)  .055(3)  .048(3)  .006(2)  -.011(3)  -.015(2)
  C16B  .045(3)  .042(3)  .031(3)  .011(2)  .006(2)  -.005(2)
  C17B  .035(3)  .031(2)  .036(3)  .002(2)  .009(2)  .007(2)
  O17B  .0254(19)  .0363(16)  .054(2)  -.0024(14)  -.0008(16)  .0140(15)
  C18B  .029(3)  .063(3)  .082(4)  -.003(2)  -.016(3)  .019(3)
  C19B  .045(3)  .030(2)  .054(3)  .009(2)  .007(3)  .005(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
  C1A O1A . 1.416(4) ?
  C1A O5A . 1.419(4) ?
  C1A C2A . 1.537(5) ?
  O1A C7A . 1.434(4) ?
  C2A N11A . 1.481(5) ?
  C2A C3A . 1.507(5) ?
  C3A O3A . 1.436(4) ?
  C3A C4A . 1.500(5) ?
  O3A C14A . 1.449(4) ?
  C4A O4A . 1.432(4) ?
  C4A C5A . 1.518(5) ?
  O4A C17A . 1.435(4) ?
  C5A O5A . 1.443(4) ?
  C5A C6A . 1.510(5) ?
  N11A N12A . 1.254(5) ?
  N12A N13A . 1.154(4) ?
  C14A O14A . 1.400(4) ?
  C14A C16A . 1.507(5) ?
  C14A C17A . 1.553(5) ?
  O14A C15A . 1.454(4) ?
  C17A O17A . 1.423(4) ?
  C17A C19A . 1.509(5) ?
  O17A C18A . 1.420(4) ?
  C1B O5B . 1.394(5) ?
  C1B O1B . 1.407(5) ?
  C1B C2B . 1.530(5) ?
  O1B C7B . 1.441(4) ?
  C2B N11B . 1.472(5) ?
  C2B C3B . 1.521(5) ?
  C3B O3B . 1.436(4) ?
  C3B C4B . 1.492(5) ?
  O3B C14B . 1.426(4) ?
  C4B O4B . 1.441(4) ?
  C4B C5B . 1.521(5) ?
  O4B C17B . 1.421(4) ?
  C5B O5B . 1.450(4) ?
  C5B C6B . 1.521(5) ?
  N11B N12B . 1.238(4) ?
  N12B N13B . 1.157(5) ?
  C14B O14B . 1.406(4) ?
  C14B C16B . 1.515(5) ?
  C14B C17B . 1.574(5) ?
  O14B C15B . 1.443(4) ?
  C17B O17B . 1.416(4) ?
  C17B C19B . 1.530(5) ?
  O17B C18B . 1.425(4) ?