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Volume 68 
Part 11 
Pages o3180-o3181  
November 2012  

Received 19 September 2012
Accepted 7 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
Disorder in solvent or counterion
R = 0.028
wR = 0.073
Data-to-parameter ratio = 16.4
Details
Open access

Methyl 3-O-[alpha]-L-fucopyranosyl [beta]-D-glucopyranoside tetrahydrate

aDepartment of Material and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden, and bDepartment of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden
Correspondence e-mail: lars.eriksson@mmk.su.se

The title compound, C13H24O10·4H2O, is the methyl glycoside of a disaccharide structural element present in the backbone of the capsular polysaccharide from Klebsiella K1, which contains only three sugars and a substituent in the polysaccharide repeating unit. The conformation of the title disaccharide is described by the glycosidic torsion angles [varphi]H = 51.1 (1)° and [psi]H = 25.8 (1)°. In the crystal, a number of O-H...O hydrogen bonds link the methyl glycoside and water molecules, forming a three-dimensional network. One water molecule is disordered over two positions with occupancies of 0.748 (4) and 0.252 (4).

Related literature

For a background to capsular polysaccharides (CPS), see: Jansson et al. (1988[Jansson, P.-E., Lindberg, B. & Widmalm, G. (1988). Carbohydr. Res. 182, 166-168.]); Erbing et al. (1976[Erbing, C., Kenne, L., Lindberg, B., Lönngren, J. & Sutherland, I. W. (1976). Carbohydr. Res. 50, 115-120.]); Gloaguen et al. (1999[Gloaguen, V., Morvan, H., Hoffmann, L., Plancke, Y., Wieruszeski, J.-M., Lippens, G. & Strecker, G. (1999). Eur. J. Biochem. 266, 762-770.]); Cescutti et al. (2005[Cescutti, P., Kallioinen, A., Impallomeni, G., Toffanin, R., Pollesello, P., Leisola, M. & Eerikäinen, T. (2005). Carbohydr. Res. 340, 439-447.]). For details of the puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the synthesis, see: Baumann et al. (1988[Baumann, H., Jansson, P.-E. & Kenne, L. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 209-217.]). For a related structure, see: Eriksson & Widmalm (2012[Eriksson, L. & Widmalm, G. (2012). Acta Cryst. E68, o528.]).

[Scheme 1]

Experimental

Crystal data
  • C13H24O10·4H2O

  • Mr = 412.39

  • Monoclinic, P 21

  • a = 9.6150 (2) Å

  • b = 7.1362 (1) Å

  • c = 13.9716 (2) Å

  • [beta] = 100.1180 (18)°

  • V = 943.75 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.15 × 0.05 × 0.03 mm

Data collection
  • Oxford Xcalibur 3 diffractometer with Sapphire 3 CCD

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.976, Tmax = 0.996

  • 37858 measured reflections

  • 4836 independent reflections

  • 4644 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.073

  • S = 1.08

  • 4836 reflections

  • 294 parameters

  • 16 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2F-H2FA...OW2 0.84 1.89 2.7326 (10) 176
O3F-H3FA...O2F 0.84 2.56 2.8696 (10) 103
O3F-H3FA...OW1i 0.84 1.92 2.7049 (10) 156
O4F-H4FA...O3Fii 0.84 1.85 2.6836 (10) 172
O6G-H6G...OW3iii 0.84 1.86 2.6546 (11) 157
O2G-H2G1...OW1 0.84 1.87 2.6981 (10) 168
O4G-H4G1...O6Giv 0.84 2.00 2.7884 (11) 155
OW1-H11...O2F 0.84 (2) 1.92 (2) 2.7522 (10) 172 (2)
OW1-H12...O4Fi 0.83 (2) 1.94 (2) 2.7646 (10) 178 (2)
OW2-H21...O6Giv 0.81 (2) 2.09 (2) 2.8897 (10) 170 (2)
OW2-H22...O5Fv 0.86 (2) 1.91 (2) 2.7682 (11) 176 (2)
OW3-H31...OW4Ai 0.81 (2) 2.04 (2) 2.8424 (16) 176 (2)
OW3-H32...O7Mvi 0.87 (2) 2.00 (2) 2.8559 (13) 169 (2)
OW4A-H41A...O2G 0.83 (2) 2.10 (2) 2.8615 (16) 151 (3)
OW4A-H42A...OW2vii 0.83 (2) 2.11 (2) 2.9390 (15) 174 (4)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) x-1, y, z-1; (iv) [-x, y-{\script{1\over 2}}, -z]; (v) x, y-1, z; (vi) [-x, y+{\script{1\over 2}}, -z+1]; (vii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5198 ).


Acknowledgements

This work was supported by a grant from the Swedish Research Council (VR).

References

Baumann, H., Jansson, P.-E. & Kenne, L. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 209-217.  [CrossRef]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cescutti, P., Kallioinen, A., Impallomeni, G., Toffanin, R., Pollesello, P., Leisola, M. & Eerikäinen, T. (2005). Carbohydr. Res. 340, 439-447.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Erbing, C., Kenne, L., Lindberg, B., Lönngren, J. & Sutherland, I. W. (1976). Carbohydr. Res. 50, 115-120.  [CrossRef] [ChemPort] [PubMed] [ISI]
Eriksson, L. & Widmalm, G. (2012). Acta Cryst. E68, o528.  [CSD] [CrossRef] [details]
Gloaguen, V., Morvan, H., Hoffmann, L., Plancke, Y., Wieruszeski, J.-M., Lippens, G. & Strecker, G. (1999). Eur. J. Biochem. 266, 762-770.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jansson, P.-E., Lindberg, B. & Widmalm, G. (1988). Carbohydr. Res. 182, 166-168.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3180-o3181   [ doi:10.1107/S1600536812041992 ]

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