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The structure of the title compound, C13H24O10·H2O, is stabilized by hydrogen bonds situated adjacent to the glycoside linkage. A direct intra­molecular hydrogen bond is present between the fucopyranosyl ring O atom and a glucopyrano­side OH group, and a bridging water mol­ecule mediates a hydrogen-bond-based inter­action from a fucopyranosyl OH group to the meth­oxy O atom. The conformation of the disaccharide is described by the glycosidic torsion angles [varphi]H = -41° and [psi]H = -2°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107059756/sf3069sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107059756/sf3069Isup2.hkl
Contains datablock I

CCDC reference: 681532

Comment top

Carbohydrates are often found as glycoconjugates in nature and they are involved in a multitude of different functions of significant importance in biomolecular systems (Carlsson et al., 2007). Elucidation of the three-dimensional structure of the carbohydrate part or of substructures of a larger oligosaccharide may reveal structural features including possible epitopes essential for molecular recognition events. We have previously reported the crystal structures of methyl 4-O-β-L-fucopyranosyl α-D-glucopyranoside (F4G) (Eriksson et al., 2000) and methyl 3-O-β-L-fucopyranosyl α-D-glucopyranoside (F3G) (Färnbäck et al., 2003) as a hemihydrate and a trihydrate, respectively, and we report here the title compound (F2G) as a monohydrate.

In F4G, the glycosidic torsion angles are ϕH = -6° (being unusual since it was close to an eclipsed conformation) and ψH = 34°, whereas in F3G, the values are ϕH = -38° and ψH = 18°. The hydroxymethyl group for the exocyclic torsion angle ω revealed the gt and gg conformations in F4G and F3G, respectively. Both conformations are favored by the gauche effect and in none of the compounds is a 1,3-syn-diaxial interaction to O4 present, consistent with the Hassel–Ottar effect (Jeffrey, 1990). Notably, both conformations are shifted slightly from the ideal gauche conformation, i.e. ω = 68° in the former and ω = -66° in the latter compound. In F3G, an intramolecular hydrogen bond was present, with O2g as the donor atom and O5f as the acceptor atom.

In the present study, the torsion angles at the glycosidic linkage of the title disaccharide F2G are ϕH = -41° and ψH = -2°. The exocyclic torsion angle ω is -64°, i.e. the gg conformation. The calculated Cremer & Pople (1975) parameters show that the fucose ring is close to the expected chair conformation, i.e. 1C4, and that the glucose ring has the anticipated 4C1 conformation. The parameters for the fucose ring are Q = 0.592 (3) Å, θ = 173.1 (3)° and ϕ = 256 (3)°, and those for the glucose ring Q = 0.544 (3) Å, θ = 12.1 (3)° and ϕ = 338 (2)°. An internal hydrogen bond is present, with atom O5f as the acceptor and atom O3g as the donor (cf. F3G where O5f is the acceptor and O2g the donor), adjacent to the glycosidic linkage (Fig. 1). On the other side, the water molecule present in the crystal structure confers additional structure to F2G. The water molecule is positioned in such a way that atom O2f acts as a donor with its hydroxy H atom pointing towards the water O atom, and both water H atoms act as donors, to atoms O1g and O3g, in a neighbouring molecule at (x + 1, y, z). Further details about the hydrogen bonding are shown in Fig. 2 and Table 2. Thus, the water molecule is present as a bridge between atoms O2f and O1g. Bridging water molecules of structural importance have been reported to be present in disaccharides using molecular dynamics simulations (Naidoo & Brady, 1999) and NMR spectroscopy (Sheng & van Halbeek, 1995). As a result of the intramolecular hydrogen-bonding pattern in the crystal structure of F2G, it is surmised that the disaccharide may be exceptionally well structured in aqueous solution, a matter that remains to be investigated.

Related literature top

For related literature, see: Baumann et al. (1991); Carlsson et al. (2007); Cremer & Pople (1975); Eriksson et al. (2000); Färnbäck et al. (2003); Flack (1983); Jeffrey (1990); Naidoo & Brady (1999); Sheng & van Halbeek (1995).

Experimental top

The synthesis of (I) was described by Baumann et al. (1991). Suitable crystals was grown with the sitting-drop technique, in which the solvent was allowed to evaporate. F2G was dissolved in water to a concentration of 375 mg ml-1 and mixed with an equal amount of 20% PEG 400 in water at ambient temperature. Crystals formed after a few days and were mounted in capillaries. Data were collected on beamline I711 at the Swedish synchrotron radiation facility, MAXLAB, Lund.

Refinement top

The hydrogen atoms were geometrically placed and constrained to ride on the parent atom. The C—H bond distances are 0.98 Å for CH3, 0.99 Å for CH2, 1.00 Å for CH. The O—H bond distance is 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. The value of the Flack parameter (Flack, 1983) was not meaningful due to the absence of significant anomalous scatterers, thus the data were merged using MERG 3 in SHELXL97. The H atoms of the water molecule were located from difference density map and the d(O—H) were restrained to retain the previously known geometry of the water molecule. The hydrogen atoms of the water molecule were given Uiso(H) = 1.5Ueq(O). The absolute configuration of each sugar residue is known from the starting compounds used in the synthesis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek,2003).

Figures top
[Figure 1]
Fig. 1. A view of the molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probablity level. H atoms are drawn as circles of arbitrary radii. Hydrogen bonds are shown as dotted lines.

Fig. 2. The water molecule mediates a hydrogen bond between two molecules.
Methyl 2-O-β-L-fucopyranosyl α-D-glucopyranoside monohydrate top
Crystal data top
C13H24O10·H2OF(000) = 384
Mr = 358.34Dx = 1.413 Mg m3
Monoclinic, P21Synchrotron radiation, λ = 0.872 Å
Hall symbol: P 2ybCell parameters from 4040 reflections
a = 7.166 (2) Åθ = 1.4–32.1°
b = 6.3924 (16) ŵ = 0.20 mm1
c = 18.518 (4) ÅT = 100 K
β = 96.876 (12)°Block, colourless
V = 842.1 (4) Å30.12 × 0.06 × 0.03 mm
Z = 2
Data collection top
Smart 1K CCD
diffractometer
1751 independent reflections
Radiation source: Beamline I711, Maxlab1726 reflections with I > 2σ(I)
Silicon monochromatorRint = 0.073
Detector resolution: 10 pixels mm-1θmax = 32.1°, θmin = 1.4°
ω scan at different ϕh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 77
Tmin = 0.97, Tmax = 0.99l = 2222
4040 measured 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0958P)2 + 0.2168P]
where P = (Fo2 + 2Fc2)/3
1751 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.27 e Å3
4 restraintsΔρmin = 0.30 e Å3
Crystal data top
C13H24O10·H2OV = 842.1 (4) Å3
Mr = 358.34Z = 2
Monoclinic, P21Synchrotron radiation, λ = 0.872 Å
a = 7.166 (2) ŵ = 0.20 mm1
b = 6.3924 (16) ÅT = 100 K
c = 18.518 (4) Å0.12 × 0.06 × 0.03 mm
β = 96.876 (12)°
Data collection top
Smart 1K CCD
diffractometer
1751 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
1726 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.99Rint = 0.073
4040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.27 e Å3
1751 reflectionsΔρmin = 0.30 e Å3
229 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
C1F0.6866 (4)0.5242 (5)0.82828 (13)0.0164 (6)
H1F0.75410.40150.85260.020*
C2F0.5415 (4)0.6075 (5)0.87476 (14)0.0166 (5)
H2F0.48010.73430.85080.020*
O2F0.3992 (3)0.4550 (4)0.88512 (10)0.0202 (4)
H2FA0.31200.46250.85060.030*
C3F0.6442 (4)0.6692 (5)0.94856 (14)0.0180 (6)
H3F0.70490.54150.97210.022*
O3F0.5090 (3)0.7437 (4)0.99226 (11)0.0197 (5)
H3FA0.56390.79081.03150.030*
C4F0.7986 (4)0.8299 (5)0.93802 (14)0.0195 (6)
H4F0.87620.85210.98600.023*
O4F0.7200 (3)1.0270 (4)0.91348 (11)0.0234 (5)
H4FA0.64181.06590.94110.035*
C5F0.9283 (4)0.7509 (5)0.88367 (14)0.0177 (6)
H5F0.99790.62580.90520.021*
C6F1.0709 (4)0.9101 (5)0.86421 (15)0.0210 (6)
H6FA1.15070.84660.83070.031*
H6FB1.14910.95530.90850.031*
H6FC1.00521.03120.84080.031*
O5F0.8173 (3)0.6873 (4)0.81700 (10)0.0187 (4)
C1G0.5949 (3)0.1173 (5)0.70603 (14)0.0155 (5)
H1G0.60780.04000.75330.019*
O1G0.4002 (3)0.1525 (3)0.68338 (10)0.0180 (4)
C7G0.2951 (4)0.0382 (5)0.67637 (15)0.0219 (6)
H7GA0.16310.00710.65970.033*
H7GB0.30420.10880.72360.033*
H7GC0.34610.12940.64100.033*
C2G0.6966 (4)0.3295 (4)0.71767 (14)0.0160 (5)
H2G0.82310.30450.74540.019*
O2G0.5932 (2)0.4649 (3)0.75958 (10)0.0165 (4)
C3G0.7239 (4)0.4418 (5)0.64713 (14)0.0189 (6)
H3G0.60200.50830.62740.023*
O3G0.8626 (3)0.6018 (4)0.66041 (10)0.0193 (4)
H3GA0.81740.70320.68140.029*
C4G0.7865 (4)0.2958 (5)0.58885 (14)0.0177 (6)
H4G0.92230.25980.60150.021*
O4G0.7615 (3)0.4042 (4)0.52147 (10)0.0200 (4)
H4GA0.85940.39340.50090.030*
C5G0.6690 (4)0.0952 (5)0.58384 (14)0.0163 (5)
H5G0.53470.13360.56870.020*
C6G0.7281 (4)0.0631 (5)0.53008 (14)0.0193 (6)
H6GA0.64670.18830.53010.023*
H6GB0.71020.00200.48060.023*
O6G0.9240 (3)0.1260 (3)0.54754 (10)0.0196 (4)
H6G0.93220.21630.58070.029*
O5G0.6813 (3)0.0032 (3)0.65409 (10)0.0171 (4)
OW0.1665 (3)0.4184 (4)0.75899 (11)0.0250 (5)
HW10.081 (4)0.506 (6)0.7297 (15)0.038*
HW20.239 (5)0.353 (6)0.7255 (14)0.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1F0.0177 (12)0.0174 (14)0.0134 (11)0.0042 (12)0.0007 (9)0.0012 (11)
C2F0.0180 (11)0.0162 (13)0.0163 (11)0.0016 (11)0.0051 (9)0.0014 (10)
O2F0.0200 (9)0.0205 (11)0.0203 (9)0.0034 (9)0.0032 (7)0.0002 (8)
C3F0.0196 (12)0.0177 (13)0.0179 (12)0.0016 (11)0.0073 (10)0.0010 (11)
O3F0.0230 (9)0.0206 (12)0.0165 (9)0.0011 (8)0.0070 (7)0.0016 (9)
C4F0.0200 (12)0.0182 (14)0.0206 (13)0.0040 (11)0.0031 (10)0.0003 (12)
O4F0.0285 (11)0.0158 (11)0.0281 (10)0.0026 (9)0.0118 (8)0.0030 (8)
C5F0.0190 (12)0.0180 (14)0.0162 (11)0.0005 (12)0.0029 (10)0.0010 (12)
C6F0.0202 (12)0.0200 (15)0.0237 (13)0.0022 (13)0.0064 (10)0.0000 (12)
O5F0.0193 (9)0.0194 (11)0.0175 (9)0.0029 (9)0.0032 (7)0.0013 (8)
C1G0.0132 (11)0.0155 (14)0.0190 (11)0.0008 (11)0.0059 (9)0.0008 (11)
O1G0.0161 (9)0.0154 (11)0.0224 (9)0.0010 (8)0.0014 (7)0.0015 (8)
C7G0.0213 (13)0.0212 (15)0.0235 (13)0.0029 (12)0.0031 (11)0.0018 (12)
C2G0.0172 (11)0.0124 (13)0.0189 (12)0.0004 (11)0.0043 (9)0.0041 (11)
O2G0.0193 (8)0.0155 (10)0.0154 (8)0.0019 (8)0.0046 (7)0.0033 (8)
C3G0.0169 (12)0.0223 (15)0.0178 (12)0.0004 (12)0.0034 (9)0.0008 (12)
O3G0.0222 (9)0.0158 (10)0.0206 (9)0.0017 (8)0.0059 (7)0.0031 (8)
C4G0.0225 (13)0.0127 (14)0.0182 (12)0.0008 (11)0.0040 (10)0.0004 (10)
O4G0.0242 (10)0.0198 (11)0.0170 (9)0.0014 (9)0.0060 (7)0.0032 (9)
C5G0.0192 (11)0.0161 (13)0.0139 (11)0.0024 (11)0.0028 (9)0.0002 (11)
C6G0.0225 (13)0.0179 (14)0.0180 (12)0.0021 (13)0.0043 (10)0.0023 (12)
O6G0.0221 (9)0.0153 (11)0.0221 (9)0.0005 (8)0.0058 (7)0.0000 (8)
O5G0.0206 (9)0.0160 (10)0.0151 (9)0.0003 (8)0.0034 (7)0.0014 (8)
OW0.0188 (9)0.0315 (13)0.0246 (10)0.0059 (10)0.0017 (8)0.0016 (10)
Geometric parameters (Å, º) top
C1F—O2G1.416 (3)O1G—C7G1.430 (4)
C1F—O5F1.434 (4)C7G—H7GA0.9800
C1F—C2F1.523 (4)C7G—H7GB0.9800
C1F—H1F1.0000C7G—H7GC0.9800
C2F—O2F1.440 (3)C2G—O2G1.428 (3)
C2F—C3F1.525 (4)C2G—C3G1.523 (4)
C2F—H2F1.0000C2G—H2G1.0000
O2F—H2FA0.8400C3G—O3G1.427 (4)
C3F—O3F1.417 (3)C3G—C4G1.534 (4)
C3F—C4F1.540 (4)C3G—H3G1.0000
C3F—H3F1.0000O3G—H3GA0.8400
O3F—H3FA0.8400C4G—O4G1.420 (3)
C4F—O4F1.432 (4)C4G—C5G1.531 (4)
C4F—C5F1.535 (4)C4G—H4G1.0000
C4F—H4F1.0000O4G—H4GA0.8400
O4F—H4FA0.8400C5G—O5G1.438 (3)
C5F—O5F1.445 (3)C5G—C6G1.515 (4)
C5F—C6F1.516 (4)C5G—H5G1.0000
C5F—H5F1.0000C6G—O6G1.458 (3)
C6F—H6FA0.9800C6G—H6GA0.9900
C6F—H6FB0.9800C6G—H6GB0.9900
C6F—H6FC0.9800O6G—H6G0.8400
C1G—O1G1.426 (3)OW—HW10.950 (10)
C1G—O5G1.430 (3)OW—HW20.950 (10)
C1G—C2G1.543 (4)H1f—H2g2.19
C1G—H1G1.0000
O2G—C1F—O5F108.1 (2)C2G—C1G—H1G108.7
O2G—C1F—C2F108.7 (2)C1G—O1G—C7G112.2 (2)
O5F—C1F—C2F109.3 (2)O1G—C7G—H7GA109.5
O2G—C1F—H1F110.3O1G—C7G—H7GB109.5
O5F—C1F—H1F110.3H7GA—C7G—H7GB109.5
C2F—C1F—H1F110.3O1G—C7G—H7GC109.5
O2F—C2F—C1F112.4 (2)H7GA—C7G—H7GC109.5
O2F—C2F—C3F109.2 (2)H7GB—C7G—H7GC109.5
C1F—C2F—C3F107.9 (2)O2G—C2G—C3G108.0 (2)
O2F—C2F—H2F109.1O2G—C2G—C1G110.0 (2)
C1F—C2F—H2F109.1C3G—C2G—C1G113.7 (2)
C3F—C2F—H2F109.1O2G—C2G—H2G108.4
C2F—O2F—H2FA109.5C3G—C2G—H2G108.4
O3F—C3F—C2F108.0 (2)C1G—C2G—H2G108.4
O3F—C3F—C4F113.5 (3)C1F—O2G—C2G115.5 (2)
C2F—C3F—C4F109.6 (2)O3G—C3G—C2G110.4 (2)
O3F—C3F—H3F108.5O3G—C3G—C4G107.5 (2)
C2F—C3F—H3F108.5C2G—C3G—C4G113.3 (3)
C4F—C3F—H3F108.5O3G—C3G—H3G108.5
C3F—O3F—H3FA109.5C2G—C3G—H3G108.5
O4F—C4F—C5F109.1 (2)C4G—C3G—H3G108.5
O4F—C4F—C3F111.5 (2)C3G—O3G—H3GA109.5
C5F—C4F—C3F111.4 (2)O4G—C4G—C5G110.2 (2)
O4F—C4F—H4F108.3O4G—C4G—C3G107.7 (2)
C5F—C4F—H4F108.3C5G—C4G—C3G110.3 (2)
C3F—C4F—H4F108.3O4G—C4G—H4G109.5
C4F—O4F—H4FA109.5C5G—C4G—H4G109.5
O5F—C5F—C6F107.7 (2)C3G—C4G—H4G109.5
O5F—C5F—C4F109.8 (2)C4G—O4G—H4GA109.5
C6F—C5F—C4F114.4 (3)O5G—C5G—C6G108.1 (2)
O5F—C5F—H5F108.3O5G—C5G—C4G109.7 (2)
C6F—C5F—H5F108.3C6G—C5G—C4G113.8 (2)
C4F—C5F—H5F108.3O5G—C5G—H5G108.3
C5F—C6F—H6FA109.5C6G—C5G—H5G108.3
C5F—C6F—H6FB109.5C4G—C5G—H5G108.3
H6FA—C6F—H6FB109.5O6G—C6G—C5G112.1 (2)
C5F—C6F—H6FC109.5O6G—C6G—H6GA109.2
H6FA—C6F—H6FC109.5C5G—C6G—H6GA109.2
H6FB—C6F—H6FC109.5O6G—C6G—H6GB109.2
C1F—O5F—C5F112.5 (2)C5G—C6G—H6GB109.2
O1G—C1G—O5G112.0 (2)H6GA—C6G—H6GB107.9
O1G—C1G—C2G109.4 (2)C6G—O6G—H6G109.5
O5G—C1G—C2G109.41 (19)C1G—O5G—C5G112.8 (2)
O1G—C1G—H1G108.7HW1—OW—HW2104.5 (14)
O5G—C1G—H1G108.7
O2G—C1F—C2F—O2F59.2 (3)O5F—C1F—O2G—C2G79.1 (3)
O5F—C1F—C2F—O2F176.9 (2)C2F—C1F—O2G—C2G162.4 (2)
O2G—C1F—C2F—C3F179.6 (2)C3G—C2G—O2G—C1F119.0 (2)
O5F—C1F—C2F—C3F62.6 (3)C1G—C2G—O2G—C1F116.5 (2)
O2F—C2F—C3F—O3F56.6 (3)O2G—C2G—C3G—O3G74.4 (3)
C1F—C2F—C3F—O3F179.1 (2)C1G—C2G—C3G—O3G163.3 (2)
O2F—C2F—C3F—C4F179.2 (2)O2G—C2G—C3G—C4G165.0 (2)
C1F—C2F—C3F—C4F56.7 (3)C1G—C2G—C3G—C4G42.7 (3)
O3F—C3F—C4F—O4F51.6 (3)O3G—C3G—C4G—O4G72.2 (3)
C2F—C3F—C4F—O4F69.3 (3)C2G—C3G—C4G—O4G165.6 (2)
O3F—C3F—C4F—C5F173.7 (2)O3G—C3G—C4G—C5G167.5 (2)
C2F—C3F—C4F—C5F52.8 (3)C2G—C3G—C4G—C5G45.3 (3)
O4F—C4F—C5F—O5F71.0 (3)O4G—C4G—C5G—O5G174.6 (2)
C3F—C4F—C5F—O5F52.5 (3)C3G—C4G—C5G—O5G55.8 (3)
O4F—C4F—C5F—C6F50.2 (3)O4G—C4G—C5G—C6G64.1 (3)
C3F—C4F—C5F—C6F173.7 (2)C3G—C4G—C5G—C6G177.1 (2)
O2G—C1F—O5F—C5F176.6 (2)O5G—C5G—C6G—O6G63.6 (3)
C2F—C1F—O5F—C5F65.3 (3)C4G—C5G—C6G—O6G58.5 (3)
C6F—C5F—O5F—C1F175.5 (2)O1G—C1G—O5G—C5G59.6 (3)
C4F—C5F—O5F—C1F59.3 (3)C2G—C1G—O5G—C5G61.8 (3)
O5G—C1G—O1G—C7G62.5 (3)C6G—C5G—O5G—C1G168.7 (2)
C2G—C1G—O1G—C7G176.0 (2)C4G—C5G—O5G—C1G66.7 (3)
O1G—C1G—C2G—O2G47.2 (3)C1F—O2G—C2G—H2G1.8
O5G—C1G—C2G—O2G170.2 (2)H1F—C1F—O2G—C2G41.5
O1G—C1G—C2G—C3G74.0 (3)C7G—O1G—C1G—H1G57.5
O5G—C1G—C2G—C3G49.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2f—H2fA···OW0.841.902.712 (3)162
O3f—H3fA···O2fi0.841.862.657 (3)158
O4f—H4fA···O3fi0.842.072.888 (3)163
O3g—H3gA···O5gii0.842.152.835 (3)139
O3g—H3gA···O5f0.842.513.006 (3)118
O4g—H4gA···O6giii0.841.892.728 (3)178
O6g—H6g···O3giv0.841.992.795 (3)160
OW—HW1···O3gv0.95 (5)2.00 (5)2.915 (3)161 (3)
OW—HW2···O1g0.95 (5)1.95 (5)2.866 (3)161 (3)
Symmetry codes: (i) x+1, y+1/2, z+2; (ii) x, y+1, z; (iii) x+2, y+1/2, z+1; (iv) x, y1, z; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC13H24O10·H2O
Mr358.34
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)7.166 (2), 6.3924 (16), 18.518 (4)
β (°) 96.876 (12)
V3)842.1 (4)
Z2
Radiation typeSynchrotron, λ = 0.872 Å
µ (mm1)0.20
Crystal size (mm)0.12 × 0.06 × 0.03
Data collection
DiffractometerSmart 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.97, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
4040, 1751, 1726
Rint0.073
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.07
No. of reflections1751
No. of parameters229
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Diamond (Bergerhoff, 1996), PLATON (Spek,2003).

Selected geometric parameters (Å, º) top
H1f—H2g2.19
O5G—C1G—O1G—C7G62.5 (3)O5G—C5G—C6G—O6G63.6 (3)
C2G—C1G—O1G—C7G176.0 (2)C1F—O2G—C2G—H2G1.8
O5F—C1F—O2G—C2G79.1 (3)H1F—C1F—O2G—C2G41.5
C3G—C2G—O2G—C1F119.0 (2)C7G—O1G—C1G—H1G57.5
C1G—C2G—O2G—C1F116.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2f—H2fA···OW0.841.9032.712 (3)162
O3f—H3fA···O2fi0.841.8592.657 (3)158
O4f—H4fA···O3fi0.842.0742.888 (3)163
O3g—H3gA···O5gii0.842.1472.835 (3)139
O3g—H3gA···O5f0.842.5143.006 (3)118
O4g—H4gA···O6giii0.841.8882.728 (3)178
O6g—H6g···O3giv0.841.9892.795 (3)160
OW—HW1···O3gv0.95 (5)2.00 (5)2.915 (3)161 (3)
OW—HW2···O1g0.95 (5)1.95 (5)2.866 (3)161 (3)
Symmetry codes: (i) x+1, y+1/2, z+2; (ii) x, y+1, z; (iii) x+2, y+1/2, z+1; (iv) x, y1, z; (v) x1, y, z.
 

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