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ISSN: 2056-9890

Methyl 3-O-α-L-fuco­pyranosyl α-D-gal­acto­pyran­oside: a synchrotron study

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

(Received 15 December 2011; accepted 18 January 2012; online 31 January 2012)

The title compound, C13H24O10 is the methyl glycoside of a structural element α-L-Fucp-(1→ 3)-α-D-Galp making up two thirds of the repeating unit in the capsular polysaccharide of Klebsiella K63. The conformation of the title compound is described by the glycosidic torsion angles φH = 55 (1)° and ψH = −24 (1)°. The hy­droxy­methyl group in the galactose residue is present in the gauchetrans conformation. In the crystal, O—H⋯O hydrogen bonds connect the disaccharide units into chains along the a-axis direction and further hydrogen bonds cross-link the chains.

Related literature

The capsular polysaccharide (CPS) of Klebsiella K63 contains a repeating unit consisting of → 3)-α-D-GalpA–(1 → 3)-α-L-Fucp-(1 → 3)-α-D-Galp-(1 →, see: Joseleau & Marais (1979[Joseleau, J.-P. & Marais, M.-R. (1979). Carbohydr. Res. 77, 183-190.]). For an investigation of the CPS S-156 from Klebsiella pneumoniae ATCC 316 46, see: Johansson et al. (1994[Johansson, A., Jansson, P.-E. & Widmalm, G. (1994). Carbohydr. Res. 253, 317-322.]) and of the CPS from Klebsiella pneumoniae I-1507, see: Guetta et al. (2003[Guetta, O., Mazeau, K., Auzely, R., Milas, M. & Rinaudo, M. (2003). Biomacromolecules, 4, 1362-1371.]). For a fiber X-ray diffraction study of the Klebsiella K63 CPS, see: Elloway et al. (1980[Elloway, H. F., Isaac, D. H. & Atkins, E. T. D. (1980). Fiber Diffraction Methods, ACS Symposium Series, 141, 429-458.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H24O10

  • Mr = 340.32

  • Orthorhombic, P 21 21 21

  • a = 4.78478 (11) Å

  • b = 15.7859 (5) Å

  • c = 19.4401 (5) Å

  • V = 1468.36 (7) Å3

  • Z = 4

  • Synchrotron radiation

  • λ = 0.907 Å

  • μ = 0.13 mm−1

  • T = 100 K

  • 0.03 × 0.01 × 0.01 mm

Data collection
  • Marresearch MARCCD 165 diffractometer

  • 7469 measured reflections

  • 1162 independent reflections

  • 975 reflections with I > 2σ(I)

  • Rint = 0.117

  • θmax = 30.1°

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.177

  • S = 1.09

  • 1162 reflections

  • 216 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3f—H3f1⋯O6gi 0.84 1.93 2.772 (7) 177
O4f—H4f1⋯O3fii 0.84 2.04 2.880 (7) 175
O2g—H2g1⋯O2giii 0.84 1.92 2.680 (7) 149
O4g—H4g1⋯O5fiv 0.84 2.08 2.827 (6) 149
O6g—H6g⋯O3fv 0.84 2.02 2.822 (7) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) x+1, y, z; (v) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: MARCCD (Marresearch, 2010[Marresearch (2010). MARCCD. Marresearch GmbH, Norderstedt, Germany.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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


Comment top

Analysis of carbohydrate structure forms the basis of further studies related to interaction with other molecules and their function in different environments. Presently, the structural studies are often divided into the determination of the primary structure, i.e., sugar residues and substituents including their absolute configuration, ring form, anomeric configuration and sequential arrangement of the constituent components. Subsequently, in the second part the three-dimensional structure is determined, often by NMR spectroscopy but also with X-ray diffraction (XRD) techniques when crystals of suitable quality and sufficient size are available.

Polysaccharides are often built of repeating units of oligosaccharides having two to seven sugar residues in their repeats. To understand the physicochemical properties and immunological specificity of the polymers it is essential to obtain information on their structures, both the primary and the three-dimensional structures.

The capsular polysaccharide (CPS) of Klebsiella K63 contains a repeating unit consisting of 3)-α-D-GalpA– (1 3)-α-L-Fucp-(1 3)-α-D-Galp-(1 (Joseleau et al., 1979). More recently the CPS S-156 from Klebsiella pneumoniae ATCC 316 46 (Johansson et al., 1994) and the CPS from Klebsiella pneumoniae I-1507 (Guetta et al., 2003) were investigated. Their backbone structures were identical to that of the CPS from Klebsiella K63, i.e., trisaccharide repeating units, except for stoichiometric O-acetylation at O4 of the galacturonic acid.

The physicochemical effects of O-deacetylation were investigated for 'Fucogel', i.e., the CPS from strain I-1507 and revealed that the presence of the O-acetyl groups decreases the local stiffness of the polymer and lowers the rigidity of the polysaccharide as well as shortens the persistence length. The structural element α-L-Fucp-(13)-α-D-Galp makes up two thirds of the repeating unit in these polysaccharides and the title compound is the methyl glycoside thereof.

The torsion angles ϕH, ψH, and ω describe the major degrees of freedom in an oligosaccharide and for the title compound (I) the two former are present at the glycosidic α-(1 3)-linkage. In addition, for the galactose residue the ϕH torsion angle is also of interest. The ω torsion angle refers to the conformation of the hydroxymethyl group in the galactose residue. Both of the ϕH torsion angles in the structure are described by the exo-anomeric conformation with ϕH = 55 (1)° for the fucose residue and ϕH = -53 (1)° for the galactose residue (Fig. 1). The ψH torsion angle may in solution populate more that one conformational state (see below); for title compound (I) ψH = -24 (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 galactose residue has the gt conformation with ω = 70 (1)°, shifted away slightly from an ideal gauche conformation.

The Cremer-Pople parameters for the title compound are Q=0.525 (7) Å, θ=176.4 (8)° and ϕ=142 (10)° for the ring O5f C5f and Q=0.556 (7) Å, θ=1.8 (7)° and ϕ=288 (14)° for the ring O5g C5g; thus the conformation of both rings can be described as C-forms.

In the study of Fucogel the conformational space of the constituent disaccharides were investigated by molecular mechanics and Ramachandran maps. Two low energy regions were identified from the adiabatic map of α-L-Fucp-(1 3)-α-D-Galp with essentially equal potential energy at their minima being (i) ϕO5 = 279.6° and ψC4 = 140.4° and (ii) ϕO5 = 260.2° and ψC4 = 70.2°, in which the former torsion angle is defined by O5f—C1f—O3g—C3g and the latter by C1g—O3g—C3g—C4g. Interresidue hydrogen bonding was not present for these two conformations although it was identified for a significantly higher-energy conformation.

The conformation of the title compound I and the corresponding glycosidic torsion angles in the polysaccharide are indeed quite similar. The resemblance of the crystal structure and the two low-energy minima of the adiabatic map suggests that torsion angle information from XRD data may be suitable as starting points for molecular modeling of oligo- and polysaccharides.

Interestingly, a fiber X-ray diffraction study of the Klebsiella K63 CPS shows that it forms an extended 2-fold helix (Elloway et al., 1980).

Related literature top

The capsular polysaccharide (CPS) of Klebsiella K63 contains a repeating unit consisting of 3)-α-D-GalpA–(1 3)-α-L-Fucp-(1 3)-α-D-Galp-(1 , see: Joseleau et al. (1979). For an investigation of the CPS S-156 from Klebsiella pneumoniae ATCC 316 46, see: Johansson et al. (1994) and of the CPS from Klebsiella pneumoniae I-1507, see: Guetta et al. (2003). For a fiber X-ray diffraction study of the Klebsiella K63 CPS, see: Elloway et al. (1980). For the synthesis, see: Baumann et al. (1988).

Experimental top

The synthesis of (I) was described by Baumann et al. (1988) in which the fucose and galactose 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

The hydrogen atoms were refined in riding mode with Uiso(H) = 1.5Ueq(X), where X = C or O. The coverage at 0.8 Å resolution = 0.738 but already at 0.9 Å resolution the coverage has increased to 0.922 and at 1.0 Å resolution the coverage ~0.995. The refinement with reflection data up to 1.0 Å resolution converged at R1 = 0.0466. It should be noted that the reflection data diminishes at high resolution as shown in Fig 2; thus the low coverage to 0.8 or 0.9 Å is of minor importance.

Computing details top

Data collection: MARCCD (Marresearch, 2010); cell refinement: CrysAlis RED (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. Molecular structure of I showing 50% probability displacement ellipsoids. The atom-label suffixes refer to the fucose(f) and galactose (g) residues. H atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. Reconstructed view of the H0L plane of reciprocal space
Methyl 3-O-α-L-fucopyranosyl α-D-galactopyranoside top
Crystal data top
C13H24O10Z = 4
Mr = 340.32F(000) = 728
Orthorhombic, P212121Dx = 1.539 Mg m3
Hall symbol: P 2ac 2abSynchrotron radiation, λ = 0.907 Å
a = 4.78478 (11) ŵ = 0.13 mm1
b = 15.7859 (5) ÅT = 100 K
c = 19.4401 (5) ÅPrism, colorless
V = 1468.36 (7) Å30.03 × 0.01 × 0.01 mm
Data collection top
Marresearch MARCCD 165
diffractometer
975 reflections with I > 2σ(I)
Radiation source: I911, MaxlabRint = 0.117
Si(111) monochromatorθmax = 30.1°, θmin = 3.1°
Detector resolution: 0.0806 pixels mm-1h = 55
ϕ scansk = 1717
7469 measured reflectionsl = 2020
1162 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1211P)2 + 0.7072P]
where P = (Fo2 + 2Fc2)/3
1162 reflections(Δ/σ)max < 0.001
216 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C13H24O10V = 1468.36 (7) Å3
Mr = 340.32Z = 4
Orthorhombic, P212121Synchrotron radiation, λ = 0.907 Å
a = 4.78478 (11) ŵ = 0.13 mm1
b = 15.7859 (5) ÅT = 100 K
c = 19.4401 (5) Å0.03 × 0.01 × 0.01 mm
Data collection top
Marresearch MARCCD 165
diffractometer
975 reflections with I > 2σ(I)
7469 measured reflectionsRint = 0.117
1162 independent reflectionsθmax = 30.1°
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.177H-atom parameters constrained
S = 1.09Δρmax = 0.30 e Å3
1162 reflectionsΔρmin = 0.27 e Å3
216 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*/Ueq
C1F0.2242 (15)0.5346 (4)0.5260 (3)0.0359 (16)
H1F0.09170.58020.51140.054*
C2F0.3048 (14)0.4827 (5)0.4636 (3)0.0409 (17)
H2F0.12700.46330.44160.061*
C3F0.4713 (14)0.4025 (4)0.4827 (3)0.0394 (17)
H3F0.65770.42170.49990.059*
C4F0.3298 (15)0.3548 (5)0.5419 (3)0.0382 (17)
H4F0.45710.30890.55850.057*
C5F0.2588 (15)0.4126 (4)0.6012 (3)0.0403 (17)
H5F0.43680.43470.62140.060*
O5F0.0941 (9)0.4845 (3)0.5765 (2)0.0393 (12)
C6F0.0937 (17)0.3710 (5)0.6571 (3)0.0465 (19)
H6F10.05330.41240.69330.070*
H6F20.20170.32400.67640.070*
H6F30.08220.34940.63810.070*
O2F0.4489 (10)0.5325 (3)0.4138 (2)0.0430 (13)
H2F10.56240.56480.43380.065*
O3F0.5214 (11)0.3485 (3)0.4262 (2)0.0458 (13)
H3F10.37250.34170.40400.069*
O4F0.0806 (9)0.3171 (3)0.5133 (3)0.0430 (13)
H4F10.05320.26970.53160.065*
C1G0.6262 (16)0.7690 (5)0.6550 (3)0.0400 (17)
H1G0.77960.81130.64870.060*
C2G0.6339 (14)0.7069 (4)0.5935 (3)0.0371 (17)
H2G0.82640.68230.59090.056*
C3G0.4279 (14)0.6336 (4)0.6047 (3)0.0362 (16)
H3G0.23210.65540.60170.054*
C4G0.4759 (15)0.5952 (5)0.6746 (4)0.0406 (18)
H4G0.32890.55140.68310.061*
C5G0.4618 (15)0.6608 (4)0.7312 (4)0.0420 (18)
H5G0.27010.68600.73280.063*
C6G0.5295 (18)0.6222 (5)0.7996 (3)0.0463 (19)
H6G10.41760.57000.80590.069*
H6G20.72950.60620.80060.069*
O1G0.3648 (10)0.8128 (3)0.6509 (2)0.0434 (13)
O2G0.5808 (10)0.7497 (3)0.5311 (2)0.0436 (13)
H2G10.70440.73700.50220.065*
O3G0.4759 (10)0.5731 (3)0.5507 (2)0.0412 (12)
O4G0.7492 (10)0.5552 (3)0.6797 (2)0.0444 (13)
H4G10.79040.53290.64180.067*
O5G0.6680 (10)0.7279 (3)0.7175 (2)0.0418 (13)
O6G0.4725 (10)0.6796 (3)0.8553 (2)0.0446 (13)
H6G0.59700.67480.88550.067*
C70.3647 (18)0.8825 (5)0.6975 (3)0.049 (2)
H7A0.38420.86150.74470.073*
H7B0.18850.91370.69310.073*
H7C0.52130.92020.68670.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1F0.026 (3)0.053 (4)0.029 (3)0.002 (3)0.004 (3)0.006 (3)
C2F0.021 (3)0.061 (4)0.041 (4)0.004 (3)0.012 (3)0.005 (4)
C3F0.025 (3)0.058 (4)0.035 (4)0.001 (4)0.003 (3)0.007 (3)
C4F0.028 (4)0.051 (4)0.035 (4)0.004 (3)0.007 (3)0.005 (3)
C5F0.024 (3)0.054 (4)0.044 (4)0.005 (4)0.003 (3)0.006 (3)
O5F0.023 (2)0.057 (3)0.038 (3)0.000 (2)0.002 (2)0.002 (2)
C6F0.038 (4)0.062 (5)0.040 (4)0.007 (4)0.001 (3)0.000 (4)
O2F0.030 (3)0.061 (3)0.038 (2)0.004 (2)0.004 (2)0.000 (2)
O3F0.026 (3)0.067 (3)0.044 (3)0.000 (3)0.002 (2)0.001 (2)
O4F0.023 (3)0.058 (3)0.048 (3)0.005 (2)0.000 (2)0.001 (2)
C1G0.036 (4)0.051 (4)0.032 (4)0.005 (4)0.001 (3)0.007 (3)
C2G0.020 (3)0.059 (4)0.032 (3)0.006 (3)0.001 (3)0.000 (3)
C3G0.020 (3)0.049 (4)0.040 (4)0.001 (3)0.012 (3)0.003 (3)
C4G0.021 (3)0.051 (4)0.050 (4)0.005 (3)0.007 (3)0.000 (4)
C5G0.025 (4)0.059 (5)0.043 (4)0.002 (4)0.002 (3)0.002 (3)
C6G0.047 (5)0.055 (4)0.037 (4)0.006 (4)0.002 (4)0.004 (4)
O1G0.029 (3)0.059 (3)0.042 (3)0.006 (3)0.006 (2)0.006 (2)
O2G0.023 (3)0.071 (3)0.038 (2)0.008 (3)0.002 (2)0.008 (3)
O3G0.025 (3)0.058 (3)0.041 (3)0.000 (2)0.009 (2)0.002 (2)
O4G0.031 (3)0.063 (3)0.040 (3)0.010 (3)0.003 (2)0.006 (2)
O5G0.028 (3)0.061 (3)0.037 (3)0.005 (2)0.002 (2)0.000 (2)
O6G0.029 (3)0.069 (3)0.036 (3)0.003 (3)0.002 (2)0.004 (3)
C70.042 (4)0.068 (5)0.036 (4)0.010 (4)0.008 (3)0.004 (4)
Geometric parameters (Å, º) top
C1F—O5F1.406 (8)C1G—C2G1.546 (9)
C1F—O3G1.432 (8)C1G—H1G1.0000
C1F—C2F1.515 (9)C2G—O2G1.414 (8)
C1F—H1F1.0000C2G—C3G1.535 (9)
C2F—O2F1.425 (8)C2G—H2G1.0000
C2F—C3F1.541 (10)C3G—O3G1.438 (8)
C2F—H2F1.0000C3G—C4G1.505 (9)
C3F—O3F1.411 (8)C3G—H3G1.0000
C3F—C4F1.532 (10)C4G—O4G1.456 (9)
C3F—H3F1.0000C4G—C5G1.513 (10)
C4F—O4F1.444 (8)C4G—H4G1.0000
C4F—C5F1.509 (9)C5G—O5G1.471 (8)
C4F—H4F1.0000C5G—C6G1.498 (10)
C5F—O5F1.462 (8)C5G—H5G1.0000
C5F—C6F1.495 (10)C6G—O6G1.437 (8)
C5F—H5F1.0000C6G—H6G10.9900
C6F—H6F10.9800C6G—H6G20.9900
C6F—H6F20.9800O1G—C71.424 (8)
C6F—H6F30.9800O2G—H2G10.8400
O2F—H2F10.8400O4G—H4G10.8400
O3F—H3F10.8400O6G—H6G0.8400
O4F—H4F10.8400C7—H7A0.9800
C1G—O5G1.392 (8)C7—H7B0.9800
C1G—O1G1.431 (9)C7—H7C0.9800
O5F—C1F—O3G112.2 (5)O1G—C1G—H1G108.2
O5F—C1F—C2F111.6 (5)C2G—C1G—H1G108.2
O3G—C1F—C2F106.5 (5)O2G—C2G—C3G111.5 (5)
O5F—C1F—H1F108.8O2G—C2G—C1G110.9 (5)
O3G—C1F—H1F108.8C3G—C2G—C1G110.7 (5)
C2F—C1F—H1F108.8O2G—C2G—H2G107.9
O2F—C2F—C1F111.7 (6)C3G—C2G—H2G107.9
O2F—C2F—C3F111.5 (5)C1G—C2G—H2G107.9
C1F—C2F—C3F112.5 (5)O3G—C3G—C4G111.5 (5)
O2F—C2F—H2F106.9O3G—C3G—C2G107.1 (5)
C1F—C2F—H2F106.9C4G—C3G—C2G109.5 (5)
C3F—C2F—H2F106.9O3G—C3G—H3G109.6
O3F—C3F—C4F111.3 (6)C4G—C3G—H3G109.6
O3F—C3F—C2F113.4 (5)C2G—C3G—H3G109.6
C4F—C3F—C2F110.9 (6)O4G—C4G—C3G111.9 (6)
O3F—C3F—H3F107.0O4G—C4G—C5G106.7 (6)
C4F—C3F—H3F107.0C3G—C4G—C5G112.0 (6)
C2F—C3F—H3F107.0O4G—C4G—H4G108.7
O4F—C4F—C5F110.9 (6)C3G—C4G—H4G108.7
O4F—C4F—C3F106.1 (5)C5G—C4G—H4G108.7
C5F—C4F—C3F112.1 (6)O5G—C5G—C6G108.0 (6)
O4F—C4F—H4F109.2O5G—C5G—C4G109.2 (6)
C5F—C4F—H4F109.2C6G—C5G—C4G111.0 (6)
C3F—C4F—H4F109.2O5G—C5G—H5G109.5
O5F—C5F—C6F107.1 (6)C6G—C5G—H5G109.5
O5F—C5F—C4F109.8 (5)C4G—C5G—H5G109.5
C6F—C5F—C4F114.1 (6)O6G—C6G—C5G111.7 (6)
O5F—C5F—H5F108.5O6G—C6G—H6G1109.3
C6F—C5F—H5F108.5C5G—C6G—H6G1109.3
C4F—C5F—H5F108.5O6G—C6G—H6G2109.3
C1F—O5F—C5F115.3 (5)C5G—C6G—H6G2109.3
C5F—C6F—H6F1109.5H6G1—C6G—H6G2107.9
C5F—C6F—H6F2109.5C7—O1G—C1G109.8 (5)
H6F1—C6F—H6F2109.5C2G—O2G—H2G1109.5
C5F—C6F—H6F3109.5C1F—O3G—C3G113.1 (5)
H6F1—C6F—H6F3109.5C4G—O4G—H4G1109.5
H6F2—C6F—H6F3109.5C1G—O5G—C5G113.4 (5)
C2F—O2F—H2F1109.5C6G—O6G—H6G109.5
C3F—O3F—H3F1109.5O1G—C7—H7A109.5
C4F—O4F—H4F1109.5O1G—C7—H7B109.5
O5G—C1G—O1G113.5 (5)H7A—C7—H7B109.5
O5G—C1G—C2G112.0 (5)O1G—C7—H7C109.5
O1G—C1G—C2G106.6 (5)H7A—C7—H7C109.5
O5G—C1G—H1G108.2H7B—C7—H7C109.5
O5F—C1F—C2F—O2F177.1 (5)O2G—C2G—C3G—O3G64.1 (6)
O3G—C1F—C2F—O2F54.4 (7)C1G—C2G—C3G—O3G172.1 (5)
O5F—C1F—C2F—C3F50.8 (7)O2G—C2G—C3G—C4G174.9 (5)
O3G—C1F—C2F—C3F71.9 (7)C1G—C2G—C3G—C4G51.0 (7)
O2F—C2F—C3F—O3F60.3 (8)O3G—C3G—C4G—O4G53.0 (7)
C1F—C2F—C3F—O3F173.3 (6)C2G—C3G—C4G—O4G65.3 (7)
O2F—C2F—C3F—C4F173.7 (5)O3G—C3G—C4G—C5G172.8 (6)
C1F—C2F—C3F—C4F47.3 (7)C2G—C3G—C4G—C5G54.4 (7)
O3F—C3F—C4F—O4F55.3 (7)O4G—C4G—C5G—O5G65.6 (6)
C2F—C3F—C4F—O4F71.8 (6)C3G—C4G—C5G—O5G57.1 (7)
O3F—C3F—C4F—C5F176.6 (6)O4G—C4G—C5G—C6G53.3 (8)
C2F—C3F—C4F—C5F49.5 (7)C3G—C4G—C5G—C6G176.1 (6)
O4F—C4F—C5F—O5F64.9 (7)O5G—C5G—C6G—O6G69.9 (7)
C3F—C4F—C5F—O5F53.6 (7)C4G—C5G—C6G—O6G170.4 (6)
O4F—C4F—C5F—C6F55.4 (8)O5G—C1G—O1G—C767.5 (7)
C3F—C4F—C5F—C6F173.9 (6)C2G—C1G—O1G—C7168.6 (5)
O3G—C1F—O5F—C5F61.8 (6)O5F—C1F—O3G—C3G65.4 (7)
C2F—C1F—O5F—C5F57.6 (7)C2F—C1F—O3G—C3G172.3 (5)
C6F—C5F—O5F—C1F176.5 (5)C4G—C3G—O3G—C1F97.7 (6)
C4F—C5F—O5F—C1F59.0 (7)C2G—C3G—O3G—C1F142.5 (5)
O5G—C1G—C2G—O2G177.9 (5)O1G—C1G—O5G—C5G62.6 (7)
O1G—C1G—C2G—O2G53.1 (7)C2G—C1G—O5G—C5G58.2 (7)
O5G—C1G—C2G—C3G53.6 (7)C6G—C5G—O5G—C1G179.8 (5)
O1G—C1G—C2G—C3G71.1 (6)C4G—C5G—O5G—C1G59.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3f—H3f1···O6gi0.841.932.772 (7)177
O4f—H4f1···O3fii0.842.042.880 (7)175
O2g—H2g1···O2giii0.841.922.680 (7)149
O4g—H4g1···O5fiv0.842.082.827 (6)149
O6g—H6g···O3fv0.842.022.822 (7)158
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x1/2, y+1/2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x+1, y, z; (v) x+3/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H24O10
Mr340.32
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)4.78478 (11), 15.7859 (5), 19.4401 (5)
V3)1468.36 (7)
Z4
Radiation typeSynchrotron, λ = 0.907 Å
µ (mm1)0.13
Crystal size (mm)0.03 × 0.01 × 0.01
Data collection
DiffractometerMarresearch MARCCD 165
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7469, 1162, 975
Rint0.117
θmax (°)30.1
(sin θ/λ)max1)0.553
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.177, 1.09
No. of reflections1162
No. of parameters216
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: MARCCD (Marresearch, 2010), 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
O3f—H3f1···O6gi0.841.932.772 (7)177
O4f—H4f1···O3fii0.842.042.880 (7)175
O2g—H2g1···O2giii0.841.922.680 (7)149
O4g—H4g1···O5fiv0.842.082.827 (6)149
O6g—H6g···O3fv0.842.022.822 (7)158
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x1/2, y+1/2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x+1, y, z; (v) x+3/2, y+1, z+1/2.
 

Acknowledgements

This work was supported by a grant from the Swedish Research Council and by the Faculty of Natural Sciences at Stockholm University

References

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