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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages o3180-o3181
doi:10.1107/S1600536812041992

Methyl 3-O-α-L-fuco­pyranosyl β-D-gluco­pyran­oside tetra­hydrate

Lars Erikssona* and Göran Widmalmb

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

(Received 19 September 2012; accepted 7 October 2012; online 20 October 2012)

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 φH = 51.1 (1)° and ψH = 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

  • β = 100.1180 (18)°

  • V = 943.75 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 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 > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(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

  • Δρmax = 0.44 e Å−3

  • Δρmin = −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.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041992/is5198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041992/is5198Isup2.hkl

checkCIF report


Comment top

Many polysaccharides are built of repeating units of oligosaccharides often having four or five sugar residues in their repeats. They may also carry substituents such as O-acetyl groups and/or pyruvic acids as for the Klebsiella capsular polysaccharides (CPS) termed S-53 and K1, respectively (Jansson et al., 1988; Erbing et al., 1976). The CPS of Klebsiella K1 contains a repeating unit consisting of → 4)-β-D-GlcpA-(2,3-Pyr)-(1→ 4)-α-L-Fucp-(1→ 3)-β-D-Glcp-(1→ (Erbing et al., 1976). More recently the CPS S-53 from Klebsiella pneumoniae ATCC 31488 (Jansson et al., 1988) was investigated, which, in addition, contained O-acetyl groups at positions 2 and 3 of the fucosyl residue. The disaccharide structural element is also present in the CPS produced by the thermophilic cynaobacterium Mastigocladus laminosus (Gloaguen et al., 1999) and the exopolysaccharide from Enterobacter amnigenus (Cescutti et al., 2005). The three-dimensional structure of the title compound, as a methyl glycoside model compound, represents an important part in these polysaccharides and may be used as a suitable starting point in modeling of the polymeric structures.

The major degrees of freedom in an oligosaccharide are the torsion angles ϕH, ψH, and ω. For the title compound (I) the two former are present at the glycosidic α-(1 → 3)-linkage. Furthermore, for the glucose residue the ϕH torsion angle is also important. The ω torsion angle describes the conformation of the hydroxymethyl group in the glucose residue. In the title compound both of the ϕH torsion angles in the structure are described by the exo-anomeric conformation with ϕH = 51.1 (1)° for the fucose residue and ϕH = 45.3 (1)° for the glucose residue (Fig. 1). The torsion angle conformation of ψH = 25.8 (1)°.

The conformation of the hydroxymethyl group is described by one of the three rotamers, gauche-trans, gauche-gauche, or trans-gauche with respect to the conformation of C6–O6 to C5–O5 and to C5–C4, respectively. In the present case the glucose residue has the gt conformation with ω = 77.02 (9)°, i.e., shifted away somewhat from a canonical gauche conformation. Extensive water-water hydrogen bonding was observed (Table 1) for the four water molecules present in the crystal. Partial occupancy was observed for one of the water molecules, in a 3:1 relative ratio between OW4A and OW4B, with a distance of 0.90 Å in between the disordered water molecules.

The calculated Cremer & Pople (1975) parameters for the two different rings are: ring O5f → C5f [Q=0.5682 (9) Å, θ=172.92 (9) ° and ϕ=58.2 (7) °], ring O5g → C5g [Q=0.5822 (9) Å, θ=6.17 (9) ° and ϕ=279.5 (8) °]; consequently, the conformation of both rings can be described as chair-forms.

The crystal structure of methyl 3-O-α-L-fucopyranosyl α-D-galactopyranoside was recently determined (Eriksson & Widmalm, 2012), but in contrast to the title compound it did not crystallize as a hydrate. Two stereochemical differences are present between the compounds: firstly at the reducing end where the O-methyl group is located equatorially (β-configuration) in the title compound but axially (α-configuration) in methyl 3-O-α-L-fucopyranosyl α-D-galactopyranoside; secondly, and more interesting, the configuration at the C4 atom of the hexopyranose residue is different, equatorial in the title compound but axial in the previously investigated disaccharide, i.e., from gluco- to galacto-configuration. For the ϕH dihedral angle the conformation at the glycosidic linkage is almost identical with ϕH = 51° herein and ϕH = 55° in methyl 3-O-α-L-fucopyranosyl α-D-galactopyranoside. However, the conformation at the ψH dihedral angle differs significantly with ψH = 26° herein, compared to ψH = -24° in the previously determined compound, i.e., a difference of 50°. Whether the difference of ca 25° from an eclipsed conformation at the ψH dihedral angle represents an intrinsic difference at the glycosidic linkage between 3-O-substituted glucose and galactose residues, or is just due to packing/hydration effects, remains to be elucidated. We note that in water solution the 13C NMR glycosylation shifts (ΔδC), i.e., differences in chemical shifts between the disaccharide and its constituent monosaccharides, for both the C1 and C3 atoms at the glycosidic linkage are lower by ca 1 p.p.m. in the title compound (ΔδC ~7.2 p.p.m.) compared to those in methyl 3-O-α-L-fucopyranosyl α-D-galactopyranoside (ΔδC ~8.3 p.p.m.) (Baumann et al., 1988). These 13C NMR chemical shift differences may be related to different conformational preferences at the ψH dihedral angle.

Related literature top

For a background to capsular polysaccharides (CPS), see: Jansson et al. (1988); Erbing et al. (1976); Gloaguen et al. (1999); Cescutti et al. (2005). For details of the puckering analysis, see: Cremer & Pople (1975). For the synthesis, see: Baumann et al. (1988). For a related structure, see: Eriksson & Widmalm (2012).

Experimental top

The synthesis of the title compound was described by Baumann et al. (1988) in which the fucose and glucose residues have the L and D absolute configurations, respectively. The compound was crystallized by slow evaporation of a mixture of water and ethanol (1:1) at ambient temperature.

Refinement top

All hydrogen atoms, except those on the water molecules, were geometrically placed and constrained to ride on the parent atom. The C—H bond distances were set to 0.98 Å for CH3, 0.99 Å for CH2, 1.00 Å for CH. The O—H bond distance was set to 0.84 Å for OH groups. The Uiso(H) = 1.5 Ueq(C, O) for the CH3 and OH, while it was set to 1.2 Ueq(C) for all other H atoms. One of the water positions, OW4 was disordered over two positions with the occupancy 0.748 (4) for OW4A and 0.252 (4) for OW4B. Using the non-merged dataset for refinement, the Flack parameter refined to x = 0.0 but the s.u. was estimated to 0.3. This low accuracy of x is a result of the absence of significant anomalous scattering effects, thus the value of the Flack parameter was not considered as meaningful, and the 2677 Friedel equivalents were included in the merging process (MERG 4 in SHELXL) for the final refinement. The absolute configuration of each sugar residue is known from the starting compounds used in the synthesis. The hydrogen atoms of the water molecule were located from difference density map, given Uiso(H) = 1.5Ueq(O) and in the refinement the d(O—H) and d(H..H) were restrained to retain the previously known geometry of the water molecule.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecule with atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level for non-H atoms.
Methyl 3-O-α-L-fucopyranosyl β-D-glucopyranoside tetrahydrate top
Crystal data top
C13H24O10·4H2OF(000) = 444
Mr = 412.39Dx = 1.451 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 26696 reflections
a = 9.6150 (2) Åθ = 3.9–41.0°
b = 7.1362 (1) ŵ = 0.13 mm−1
c = 13.9716 (2) ÅT = 100 K
β = 100.1180 (18)°Prism, colourless
V = 943.75 (3) Å30.15 × 0.05 × 0.03 mm
Z = 2
Data collection top
Oxford Xcalibur 3
diffractometer with Sapphire 3 CCD		4836 independent reflections
Radiation source: Enhance (Mo) X-ray Source4644 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 16.5467 pixels mm-1θmax = 36.3°, θmin = 4.0°
ω scans at different ϕh = −16→16
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		k = −11→6
Tmin = 0.976, Tmax = 0.996l = −23→23
37858 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0456P)2 + 0.0842P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4836 reflectionsΔρmax = 0.44 e Å−3
294 parametersΔρmin = −0.26 e Å−3
16 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (4)
Crystal data top
C13H24O10·4H2OV = 943.75 (3) Å3
Mr = 412.39Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.6150 (2) ŵ = 0.13 mm−1
b = 7.1362 (1) ÅT = 100 K
c = 13.9716 (2) Å0.15 × 0.05 × 0.03 mm
β = 100.1180 (18)°
Data collection top
Oxford Xcalibur 3
diffractometer with Sapphire 3 CCD		4836 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		4644 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.996Rint = 0.030
37858 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02816 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.44 e Å−3
4836 reflectionsΔρmin = −0.26 e Å−3
294 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1F0.06137 (8)0.74750 (12)0.36039 (6)0.00779 (13)
H1F−0.02060.80960.38260.009*
C2F0.12838 (8)0.60944 (12)0.43883 (6)0.00787 (13)
H2F0.14880.67940.50170.009*
C3F0.26863 (8)0.53512 (12)0.41753 (6)0.00798 (13)
H3F0.25040.46030.35610.010*
C4F0.36573 (8)0.69748 (13)0.40472 (6)0.00811 (13)
H4F0.45540.64740.38770.010*
C5F0.29166 (9)0.81952 (13)0.32155 (6)0.00935 (13)
H5F0.27190.74260.26080.011*
O5F0.15932 (7)0.88703 (10)0.34442 (5)0.00936 (11)
C6F0.37691 (10)0.98940 (15)0.30347 (7)0.01461 (16)
H6FA0.32431.06230.24950.022*
H6FB0.46720.94910.28690.022*
H6FC0.39451.06710.36220.022*
O2F0.03402 (7)0.46140 (10)0.45049 (5)0.00979 (11)
H2FA0.03020.38550.40410.015*
O3F0.33526 (7)0.41869 (11)0.49451 (5)0.01196 (12)
H3FA0.28290.32670.50040.018*
O4F0.39729 (7)0.80024 (11)0.49324 (5)0.01022 (11)
H4FA0.48230.83400.50240.015*
C1G−0.32791 (9)0.80214 (14)0.11858 (6)0.00982 (14)
H1G−0.32190.94200.12190.012*
C2G−0.23436 (8)0.71631 (13)0.20716 (6)0.00919 (13)
H2G−0.25430.57900.20960.011*
C3G−0.07891 (8)0.74567 (12)0.20083 (6)0.00806 (13)
H3G−0.05590.88220.20810.010*
C4G−0.04891 (8)0.67751 (13)0.10331 (6)0.00803 (13)
H4G−0.06820.53990.09710.010*
C5G−0.14732 (9)0.78118 (13)0.02294 (6)0.00859 (13)
H5G−0.13180.91920.03110.010*
O5G−0.28938 (6)0.73757 (11)0.03071 (4)0.01060 (11)
C6G−0.12642 (9)0.72355 (14)−0.07751 (6)0.01059 (14)
H6G1−0.02400.7129−0.07820.013*
H6G2−0.16920.5985−0.09270.013*
O7M−0.46601 (7)0.74456 (12)0.11844 (5)0.01356 (13)
C7M−0.56733 (10)0.8496 (2)0.05233 (8)0.0228 (2)
H71−0.55340.98370.06580.034*
H72−0.66290.81360.06050.034*
H73−0.55510.8234−0.01450.034*
O2G−0.27031 (8)0.80440 (12)0.29016 (5)0.01355 (13)
H2G1−0.26750.72540.33500.020*
O3G0.01081 (7)0.64343 (10)0.27542 (4)0.00823 (11)
O4G0.09313 (7)0.71213 (11)0.09408 (5)0.01101 (12)
H4G10.14390.62190.11780.017*
O6G−0.18739 (7)0.85281 (11)−0.15098 (5)0.01114 (12)
H6G−0.27580.8442−0.15960.017*
OW1−0.23629 (7)0.58785 (10)0.45089 (5)0.01226 (12)
H11−0.1538 (15)0.546 (3)0.4560 (12)0.018*
H12−0.2840 (16)0.500 (3)0.4666 (12)0.018*
OW20.02672 (8)0.22661 (11)0.29518 (5)0.01423 (13)
H210.0697 (18)0.276 (3)0.2567 (12)0.021*
H220.0714 (19)0.124 (2)0.3125 (13)0.021*
OW30.53751 (9)0.90725 (15)0.79144 (8)0.02575 (19)
H310.4671 (19)0.846 (3)0.7728 (15)0.039*
H320.511 (2)1.000 (3)0.8244 (15)0.039*
OW4A−0.28298 (13)1.20268 (19)0.26647 (12)0.0277 (4)0.748 (4)
H41A−0.297 (3)1.097 (3)0.288 (2)0.042*0.748 (4)
H42A−0.196 (2)1.217 (5)0.276 (2)0.042*0.748 (4)
OW4B−0.3277 (4)1.2108 (6)0.3181 (2)0.0192 (9)0.252 (4)
H41B−0.269 (7)1.128 (10)0.313 (6)0.029*0.252 (4)
H42B−0.307 (7)1.261 (10)0.371 (3)0.029*0.252 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1F0.0070 (3)0.0093 (3)0.0069 (3)0.0005 (3)0.0005 (2)0.0001 (2)
C2F0.0065 (3)0.0099 (3)0.0070 (3)0.0003 (2)0.0007 (2)0.0009 (2)
C3F0.0061 (3)0.0088 (3)0.0088 (3)0.0007 (2)0.0007 (2)0.0010 (3)
C4F0.0063 (3)0.0097 (3)0.0081 (3)−0.0002 (2)0.0009 (2)0.0001 (2)
C5F0.0080 (3)0.0111 (3)0.0090 (3)0.0001 (3)0.0015 (2)0.0014 (3)
O5F0.0076 (2)0.0089 (3)0.0114 (3)0.0000 (2)0.00116 (19)0.0009 (2)
C6F0.0130 (3)0.0144 (4)0.0165 (4)−0.0030 (3)0.0028 (3)0.0058 (3)
O2F0.0081 (2)0.0116 (3)0.0100 (2)−0.0015 (2)0.00258 (19)0.0013 (2)
O3F0.0076 (2)0.0121 (3)0.0152 (3)0.0007 (2)−0.0007 (2)0.0063 (2)
O4F0.0071 (2)0.0134 (3)0.0097 (2)−0.0020 (2)0.00025 (18)−0.0024 (2)
C1G0.0070 (3)0.0138 (3)0.0086 (3)0.0012 (3)0.0013 (2)0.0021 (3)
C2G0.0078 (3)0.0125 (3)0.0072 (3)0.0013 (3)0.0013 (2)0.0014 (3)
C3G0.0075 (3)0.0095 (3)0.0067 (3)0.0011 (3)0.0000 (2)0.0014 (3)
C4G0.0067 (3)0.0101 (3)0.0071 (3)0.0001 (2)0.0007 (2)0.0007 (2)
C5G0.0080 (3)0.0105 (3)0.0073 (3)−0.0002 (2)0.0012 (2)0.0004 (3)
O5G0.0069 (2)0.0165 (3)0.0081 (2)−0.0010 (2)0.00048 (18)−0.0002 (2)
C6G0.0121 (3)0.0125 (3)0.0070 (3)0.0010 (3)0.0012 (2)0.0007 (3)
O7M0.0058 (2)0.0206 (3)0.0140 (3)0.0013 (2)0.0009 (2)0.0068 (3)
C7M0.0092 (3)0.0371 (6)0.0211 (4)0.0065 (4)0.0002 (3)0.0131 (4)
O2G0.0137 (3)0.0198 (3)0.0079 (2)0.0055 (3)0.0039 (2)0.0018 (2)
O3G0.0086 (2)0.0092 (3)0.0059 (2)0.0017 (2)−0.00137 (18)−0.0001 (2)
O4G0.0066 (2)0.0156 (3)0.0111 (2)0.0003 (2)0.00206 (19)0.0016 (2)
O6G0.0108 (2)0.0142 (3)0.0076 (2)−0.0013 (2)−0.00058 (19)0.0023 (2)
OW10.0111 (3)0.0116 (3)0.0148 (3)0.0017 (2)0.0043 (2)0.0029 (2)
OW20.0165 (3)0.0106 (3)0.0163 (3)0.0008 (2)0.0047 (2)0.0010 (2)
OW30.0134 (3)0.0249 (4)0.0370 (5)0.0026 (3)−0.0009 (3)−0.0141 (4)
OW4A0.0169 (5)0.0176 (6)0.0475 (9)0.0016 (4)0.0029 (5)0.0056 (5)
OW4B0.0190 (14)0.0227 (17)0.0162 (14)0.0014 (12)0.0039 (11)−0.0007 (12)
Geometric parameters (Å, º) top
C1F—O3G1.4122 (10)C3G—H3G1.0000
C1F—O5F1.4149 (11)C4G—O4G1.4158 (10)
C1F—C2F1.5292 (11)C4G—C5G1.5265 (11)
C1F—H1F1.0000C4G—H4G1.0000
C2F—O2F1.4205 (11)C5G—O5G1.4236 (10)
C2F—C3F1.5261 (11)C5G—C6G1.5094 (12)
C2F—H2F1.0000C5G—H5G1.0000
C3F—O3F1.4197 (10)C6G—O6G1.4272 (11)
C3F—C4F1.5182 (12)C6G—H6G10.9900
C3F—H3F1.0000C6G—H6G20.9900
C4F—O4F1.4240 (11)O7M—C7M1.4311 (12)
C4F—C5F1.5248 (12)C7M—H710.9800
C4F—H4F1.0000C7M—H720.9800
C5F—O5F1.4479 (11)C7M—H730.9800
C5F—C6F1.5094 (13)O2G—H2G10.8400
C5F—H5F1.0000O4G—H4G10.8400
C6F—H6FA0.9800O6G—H6G0.8400
C6F—H6FB0.9800OW1—H110.839 (14)
C6F—H6FC0.9800OW1—H120.830 (15)
O2F—H2FA0.8400OW2—H210.814 (15)
O3F—H3FA0.8400OW2—H220.862 (15)
O4F—H4FA0.8400OW3—H310.810 (16)
C1G—O7M1.3896 (11)OW3—H320.868 (16)
C1G—O5G1.4200 (11)OW4A—OW4B0.904 (4)
C1G—C2G1.5247 (11)OW4A—H41A0.835 (19)
C1G—H1G1.0000OW4A—H42A0.826 (18)
C2G—O2G1.4143 (11)OW4A—H41B0.83 (9)
C2G—C3G1.5271 (11)OW4B—H41A0.98 (3)
C2G—H2G1.0000OW4B—H41B0.83 (2)
C3G—O3G1.4306 (10)OW4B—H42B0.81 (2)
C3G—C4G1.5213 (11)
O3G—C1F—O5F112.20 (6)O2G—C2G—C1G107.01 (7)
O3G—C1F—C2F107.64 (7)O2G—C2G—C3G111.67 (7)
O5F—C1F—C2F110.98 (6)C1G—C2G—C3G109.98 (7)
O3G—C1F—H1F108.6O2G—C2G—H2G109.4
O5F—C1F—H1F108.6C1G—C2G—H2G109.4
C2F—C1F—H1F108.6C3G—C2G—H2G109.4
O2F—C2F—C3F111.59 (7)O3G—C3G—C4G107.73 (7)
O2F—C2F—C1F111.36 (6)O3G—C3G—C2G111.03 (7)
C3F—C2F—C1F111.08 (7)C4G—C3G—C2G110.46 (7)
O2F—C2F—H2F107.5O3G—C3G—H3G109.2
C3F—C2F—H2F107.5C4G—C3G—H3G109.2
C1F—C2F—H2F107.5C2G—C3G—H3G109.2
O3F—C3F—C4F109.32 (6)O4G—C4G—C3G111.31 (7)
O3F—C3F—C2F110.63 (7)O4G—C4G—C5G109.37 (7)
C4F—C3F—C2F109.91 (7)C3G—C4G—C5G108.26 (7)
O3F—C3F—H3F109.0O4G—C4G—H4G109.3
C4F—C3F—H3F109.0C3G—C4G—H4G109.3
C2F—C3F—H3F109.0C5G—C4G—H4G109.3
O4F—C4F—C3F109.40 (7)O5G—C5G—C6G107.31 (7)
O4F—C4F—C5F111.56 (7)O5G—C5G—C4G108.48 (7)
C3F—C4F—C5F108.13 (6)C6G—C5G—C4G112.66 (7)
O4F—C4F—H4F109.2O5G—C5G—H5G109.4
C3F—C4F—H4F109.2C6G—C5G—H5G109.4
C5F—C4F—H4F109.2C4G—C5G—H5G109.4
O5F—C5F—C6F107.09 (7)C1G—O5G—C5G113.24 (6)
O5F—C5F—C4F109.44 (7)O6G—C6G—C5G112.81 (8)
C6F—C5F—C4F113.06 (7)O6G—C6G—H6G1109.0
O5F—C5F—H5F109.1C5G—C6G—H6G1109.0
C6F—C5F—H5F109.1O6G—C6G—H6G2109.0
C4F—C5F—H5F109.1C5G—C6G—H6G2109.0
C1F—O5F—C5F115.83 (7)H6G1—C6G—H6G2107.8
C5F—C6F—H6FA109.5C1G—O7M—C7M112.83 (8)
C5F—C6F—H6FB109.5O7M—C7M—H71109.5
H6FA—C6F—H6FB109.5O7M—C7M—H72109.5
C5F—C6F—H6FC109.5H71—C7M—H72109.5
H6FA—C6F—H6FC109.5O7M—C7M—H73109.5
H6FB—C6F—H6FC109.5H71—C7M—H73109.5
C2F—O2F—H2FA109.5H72—C7M—H73109.5
C3F—O3F—H3FA109.5C2G—O2G—H2G1109.5
C4F—O4F—H4FA109.5C1F—O3G—C3G114.75 (7)
O7M—C1G—O5G107.29 (7)C4G—O4G—H4G1109.5
O7M—C1G—C2G108.04 (7)C6G—O6G—H6G109.5
O5G—C1G—C2G111.41 (7)H11—OW1—H12105.3 (16)
O7M—C1G—H1G110.0H21—OW2—H22105.5 (16)
O5G—C1G—H1G110.0H31—OW3—H32106.1 (18)
C2G—C1G—H1G110.0
O3G—C1F—C2F—O2F−52.73 (8)O2G—C2G—C3G—O3G69.76 (9)
O5F—C1F—C2F—O2F−175.86 (7)C1G—C2G—C3G—O3G−171.59 (7)
O3G—C1F—C2F—C3F72.31 (8)O2G—C2G—C3G—C4G−170.80 (7)
O5F—C1F—C2F—C3F−50.82 (9)C1G—C2G—C3G—C4G−52.15 (10)
O2F—C2F—C3F—O3F−59.67 (9)O3G—C3G—C4G—O4G−61.52 (9)
C1F—C2F—C3F—O3F175.42 (7)C2G—C3G—C4G—O4G177.06 (7)
O2F—C2F—C3F—C4F179.51 (6)O3G—C3G—C4G—C5G178.25 (7)
C1F—C2F—C3F—C4F54.60 (9)C2G—C3G—C4G—C5G56.82 (9)
O3F—C3F—C4F—O4F−58.47 (8)O4G—C4G—C5G—O5G177.31 (7)
C2F—C3F—C4F—O4F63.14 (8)C3G—C4G—C5G—O5G−61.25 (9)
O3F—C3F—C4F—C5F179.85 (7)O4G—C4G—C5G—C6G58.65 (10)
C2F—C3F—C4F—C5F−58.54 (8)C3G—C4G—C5G—C6G−179.91 (7)
O4F—C4F—C5F—O5F−61.09 (9)O7M—C1G—O5G—C5G−177.77 (7)
C3F—C4F—C5F—O5F59.25 (9)C2G—C1G—O5G—C5G−59.71 (10)
O4F—C4F—C5F—C6F58.17 (9)C6G—C5G—O5G—C1G−173.98 (7)
C3F—C4F—C5F—C6F178.52 (7)C4G—C5G—O5G—C1G64.03 (9)
O3G—C1F—O5F—C5F−65.99 (9)O5G—C5G—C6G—O6G77.02 (9)
C2F—C1F—O5F—C5F54.48 (9)C4G—C5G—C6G—O6G−163.63 (7)
C6F—C5F—O5F—C1F177.74 (7)O5G—C1G—O7M—C7M−73.36 (11)
C4F—C5F—O5F—C1F−59.37 (9)C2G—C1G—O7M—C7M166.41 (9)
O7M—C1G—C2G—O2G−68.77 (9)O5F—C1F—O3G—C3G−69.16 (8)
O5G—C1G—C2G—O2G173.62 (7)C2F—C1F—O3G—C3G168.45 (6)
O7M—C1G—C2G—C3G169.75 (8)C4G—C3G—O3G—C1F144.26 (7)
O5G—C1G—C2G—C3G52.15 (10)C2G—C3G—O3G—C1F−94.67 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2F—H2FA···OW20.841.892.7326 (10)176
O3F—H3FA···O2F0.842.562.8696 (10)103
O3F—H3FA···OW1i0.841.922.7049 (10)156
O4F—H4FA···O3Fii0.841.852.6836 (10)172
O6G—H6G···OW3iii0.841.862.6546 (11)157
O2G—H2G1···OW10.841.872.6981 (10)168
O4G—H4G1···O6Giv0.842.002.7884 (11)155
OW1—H11···O2F0.84 (2)1.92 (2)2.7522 (10)172 (2)
OW1—H12···O4Fi0.83 (2)1.94 (2)2.7646 (10)178 (2)
OW2—H21···O6Giv0.81 (2)2.09 (2)2.8897 (10)170 (2)
OW2—H22···O5Fv0.86 (2)1.91 (2)2.7682 (11)176 (2)
OW3—H31···OW4Ai0.81 (2)2.04 (2)2.8424 (16)176 (2)
OW3—H32···O7Mvi0.87 (2)2.00 (2)2.8559 (13)169 (2)
OW4A—H41A···O2G0.83 (2)2.10 (2)2.8615 (16)151 (3)
OW4A—H42A···OW2vii0.83 (2)2.11 (2)2.9390 (15)174 (4)
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z−1; (iv) −x, y−1/2, −z; (v) x, y−1, z; (vi) −x, y+1/2, −z+1; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H24O10·4H2O
Mr412.39
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)9.6150 (2), 7.1362 (1), 13.9716 (2)
β (°) 100.1180 (18)
V (Å3)943.75 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.15 × 0.05 × 0.03
Data collection
DiffractometerOxford Xcalibur 3
diffractometer with Sapphire 3 CCD
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.976, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		37858, 4836, 4644
Rint0.030
(sin θ/λ)max (Å−1)0.833
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.073, 1.08
No. of reflections4836
No. of parameters294
No. of restraints16
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.44, −0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2F—H2FA···OW20.841.892.7326 (10)176
O3F—H3FA···O2F0.842.562.8696 (10)103
O3F—H3FA···OW1i0.841.922.7049 (10)156
O4F—H4FA···O3Fii0.841.852.6836 (10)172
O6G—H6G···OW3iii0.841.862.6546 (11)157
O2G—H2G1···OW10.841.872.6981 (10)168
O4G—H4G1···O6Giv0.842.002.7884 (11)155
OW1—H11···O2F0.84 (2)1.92 (2)2.7522 (10)172 (2)
OW1—H12···O4Fi0.83 (2)1.94 (2)2.7646 (10)178 (2)
OW2—H21···O6Giv0.81 (2)2.09 (2)2.8897 (10)170 (2)
OW2—H22···O5Fv0.86 (2)1.91 (2)2.7682 (11)176 (2)
OW3—H31···OW4Ai0.81 (2)2.04 (2)2.8424 (16)176 (2)
OW3—H32···O7Mvi0.87 (2)2.00 (2)2.8559 (13)169 (2)
OW4A—H41A···O2G0.83 (2)2.10 (2)2.8615 (16)151 (3)
OW4A—H42A···OW2vii0.83 (2)2.11 (2)2.9390 (15)174 (4)
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z−1; (iv) −x, y−1/2, −z; (v) x, y−1, z; (vi) −x, y+1/2, −z+1; (vii) x, y+1, z.
 

Acknowledgements

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

References

First citationBaumann, H., Jansson, P.-E. & Kenne, L. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 209–217.  CrossRef Web of Science Google Scholar
 First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationCescutti, P., Kallioinen, A., Impallomeni, G., Toffanin, R., Pollesello, P., Leisola, M. & Eerikäinen, T. (2005). Carbohydr. Res. 340, 439–447.  Web of Science CrossRef PubMed CAS Google Scholar
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 First citationJansson, P.-E., Lindberg, B. & Widmalm, G. (1988). Carbohydr. Res. 182, 166–168.  CrossRef CAS Web of Science Google Scholar
 First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages o3180-o3181
doi:10.1107/S1600536812041992
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