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The water content of the title compound, C13H24O10·3H2O, creates an extensive hydrogen-bonding pattern, with all the hydroxyl groups of the disaccharide acting as hydrogen-bond donors and acceptors. The water molecules are arranged in columns along the crystallographic b axis and form, together with one of the hydroxyl groups, infinite hydrogen-bonded chains. The conformation of the disaccharide is described by glycosidic torsion angles of -38 and 18°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103002865/tr1049sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103002865/tr1049Isup2.hkl
Contains datablock I

CCDC reference: 208035

Comment top

Carbohydrates are one of the most abundant types of molecules found in nature, and many oligo- and polysaccharides play important roles in biological systems (Varki et al., 1999). To understand the role of carbohydrates better, a detailed knowledge of their three-dimensional structure is required. The X-ray diffraction technique is unsurpassed for studying the three- dimensional structure of molecules, as long as suitable crystals can be grown, which has proven difficult for polyhydroxylated carbohydrates. A recent review (Peréz et al., 2000) states that until the year 2000 only 55 unsubstituted disaccharides had been crystallized and solved by X-ray diffraction and only two disaccharides containing fucose had been solved (Eriksson et al., 2000; Watt et al., 1996; Allen, 2002). Furthermore, three trisaccharides containing fucose were found in the Cambridge Strutural Database (Allen, 2002).

The conformation of disaccharide, (I), is described by the two torsion angles around the glycosidic linkage, ϕH (defined by H1f—C1f—O3g—C3g) and ψH (defined by C1f—O3g—C3g—H3g), where f and g denote the fucosyl and glucosyl residues, respectively (Fig. 1). The value of the ϕH torsion angle is mainly governed by the exo-anomeric effect, which predicts that a β-L sugar should have an ϕH angle of ~- 60°. The ψH torsion angle is set by steric interactions and is generally between −60 and 60°. For (I), ϕH is −37.7° and ψH is 18.2°. Thus, the glycosidic torsion angles are found in the expected regions. Selected torsion angles are given in Table 1. A grid search using a simplified molecular mechanics potential energy function found the global minimum at ϕH = −55° and ψH = −5° (Baumann et al., 1991). This conformation differs from the conformation found in the crystalline state by \sim20° at each of the glycosidic torsion angles. The exocyclic torsion angle for the glucose residue has an angle ωg (defined by O5g—C5g—C6g—O6g) of −66.4 (2)°, which describes a gauche–gauche conformation. The bond angle at the glycosidic linkage τ (defined by C1f–O3g–C3g) is 116.2 (2)°. The calculated Cremer & Pople (1975) puckering parameter shows that both pyranose rings in (I) are in the expected chair conformations, 1C4 for the fucosyl ring [Q = 0.583 (2) Å, θ = 172.6 (2)° and ϕ = 145 (2)°] and 4C1 chair for the glucose ring [Q = 0.578 (2) Å, θ = 4.9 (2)° and ϕ = 135 (2)°]. The mean C—C bond length is 1.53 Å, which is in agreement with the average bond length reported for carbohydrates (Peréz et al., 2000). The main packing feature in the structure is the hydrogen-bond network, where the water molecules give rise to a complex hydrogen-bonding scheme (see Table 2). An intra-molecular hydrogen bond, O2g—HO2g···O5f, is observed over the glycosidic linkage.

From an NMR study of disaccharide, (I), in water and aceton (85:15) obtained at 265 K it was concluded that a weak hydrogen bond is present between the two above-mentioned atoms. This conclusion was based on a large negative chemical shift difference, a small value of the J-coupling and a high temperature coefficient for HO2g (Ivarsson et al., 2000).

In total there are 11 inter-molecular hydrogen bonds in the range 2.68–3.07 Å. All hydroxyl groups act as hydrogen-bond donors, both to other hydroxyl groups and to water molecules. The water molecules are grouped together in a channel through the structure along the crystallographic b axis and form an infinite hydrogen-bonded chain, as depicted in Fig. 2, where the sequence donor acceptor is O6g OW1 OW2 OW3 O6gi. Several more hydrogen-bond clusters and chains are also present.

Experimental top

The synthesis of methyl 3-O-β-L-fucopyranosyl α-D-glucopyranoside was described previously (Baumann et al., 1991). Crystals suitable for single-crystal X-ray diffraction were grown at 295 K with the sitting-drop technique, in which the solvent was allowed to evaporate. Compound (I) was dissolved in water to a concentration of 375 mg ml-1 and mixed with an equal amount of 30% PEG-400 in water at ambient temperature. After approximately one week, the crystals were harvested and mounted in capillaries to avoid the loss of crystal water. Data were collected at ambient temperature on beamline I711 at the Swedish synchrotron radiation facility MAXLAB, Lund.

Refinement top

The initial electron-density map contained all non-H atoms including the three water O atoms. The water H atoms were located from difference electron-density maps, while the H atoms on the carbohydrate molecule were positioned geometrically. Restraints were applied to bond lengths and to the distance between the H atoms on the water molecules, to stabilize the structure during refinement. The O—H distance was set to 0.82 Å while the C—H distances were set to 0.98, 0.97 and 0.96 Å in the CH, CH2 and CH3 groups, respectively. All non-H atoms were refined with anistropic displacement parameters employing a rigid-bond restraint to Uij of the two bonded atoms (Rollett, 1970). The H atoms were allowed to ride on the coordinates of their parent atoms during the least-squares refinement. The Uiso(H) values were 1.5Ueq(C, O) for methyl and hydroxyl groups with Uiso(H) of 1.2Ueq(C) for all other atoms. H atoms in the hydroxyl groups were allowed to rotate around the X—C—O—H torsion angle during the refinment using the AFIX 147 instruction available in SHELXL97.

The absolute configuration of (I) is set by the components in the synthesis. As the value of the Flack parameter initially calculated was meaningless, the Friedel equivalents (1497) were included in the merging process (MERG 3 in SHELXL97).

Computing details top

Data collection: MARCCD control software (MAR, 2002); cell refinement: Twinsolve (Svensson, 2002); data reduction: Twinsolve; program(s) used to solve structure: SHELXD (Sheldrick & Schneider, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: PLATON (Spek, 2002).

Figures top
[Figure 1] Fig. 1. The molecular structure of the disaccharide (I), showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. H atoms are drawn as small spheres of arbitrary radii. An internal hydrogen bond, O2g—HO2g···O5f, is also shown (dashed). The water molecules are omitted.
[Figure 2] Fig. 2. A view of the hydrogen-bond scheme for the three water molecules. Hydrogen bonding is indicated by dashed lines. Some H atoms are removed for clarity. [Symmetry codes: (i) 0.5 − x, 1 − y, −0.5 + z; (ii) 1.5 − x, 1 − y, −0.5 + z; (iii) 0.5 + x, 1.5 − y, 1 − z; (iv) 2 − x, 0.5 + y, 0.5 − z.]
Methyl 3-O-β-L-fucopyranosyl α-D-glucopyranoside trihydrate top
Crystal data top
C13H24O10·3(H2O)F(000) = 848
Mr = 394.37Dx = 1.414 Mg m3
Orthorhombic, P212121Synchrotron radiation, λ = 0.8720 Å
Hall symbol: P 2ac 2abCell parameters from 882 reflections
a = 6.8638 (16) Åθ = 2.0–32.0°
b = 15.861 (4) ŵ = 0.21 mm1
c = 17.014 (7) ÅT = 293 K
V = 1852.2 (10) Å3Needle, colourless
Z = 40.35 × 0.1 × 0.1 mm
Data collection top
MAR-CCD area detector
diffractometer
2062 independent reflections
Radiation source: Beamline I-711, MaxLab, Lund, Sweden1811 reflections with I > 2σ(I)
Si monochromatorRint = 0.048
Detector resolution: 12.4 pixels mm-1θmax = 32.4°, θmin = 2.2°
Area detector, ϕ–scanh = 88
Absorption correction: numerical
X-RED (Stoe & Cie, 1997)
k = 1919
Tmin = 0.93, Tmax = 0.98l = 2020
25554 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.56 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
2062 reflections(Δ/σ)max < 0.001
259 parametersΔρmax = 0.16 e Å3
9 restraintsΔρmin = 0.15 e Å3
Crystal data top
C13H24O10·3(H2O)V = 1852.2 (10) Å3
Mr = 394.37Z = 4
Orthorhombic, P212121Synchrotron radiation, λ = 0.8720 Å
a = 6.8638 (16) ŵ = 0.21 mm1
b = 15.861 (4) ÅT = 293 K
c = 17.014 (7) Å0.35 × 0.1 × 0.1 mm
Data collection top
MAR-CCD area detector
diffractometer
2062 independent reflections
Absorption correction: numerical
X-RED (Stoe & Cie, 1997)
1811 reflections with I > 2σ(I)
Tmin = 0.93, Tmax = 0.98Rint = 0.048
25554 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0369 restraints
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.56Δρmax = 0.16 e Å3
2062 reflectionsΔρmin = 0.15 e Å3
259 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
O3G0.9331 (2)0.44658 (9)0.02578 (9)0.0289 (4)
O4G1.3310 (3)0.41662 (9)0.02105 (10)0.0351 (4)
HO4G1.26850.38100.04520.053*
O5G1.3118 (3)0.64758 (9)0.01916 (9)0.0350 (4)
O2F0.9148 (3)0.26488 (10)0.04291 (10)0.0393 (4)
HO2F0.94540.27540.00260.059*
O1G1.2541 (3)0.64770 (10)0.11662 (9)0.0387 (4)
O4F0.3564 (3)0.36405 (11)0.13598 (11)0.0408 (4)
HO4F0.38680.38100.09210.061*
O5F0.7235 (2)0.46018 (9)0.12954 (9)0.0328 (4)
O3F0.5650 (3)0.20878 (10)0.10776 (11)0.0400 (4)
HO3F0.46400.20140.13250.060*
C2G1.0048 (4)0.59850 (13)0.03282 (15)0.0324 (5)
H2G0.94580.60660.01910.039*
C3G1.0846 (3)0.50807 (13)0.03752 (13)0.0262 (5)
H3G1.14580.49910.08890.031*
C4G1.2360 (4)0.49657 (13)0.02739 (13)0.0276 (5)
H4G1.17220.50090.07880.033*
O6G1.4397 (3)0.57012 (11)0.16448 (11)0.0474 (5)
HO6G1.40380.61900.17080.071*
C2F0.7699 (4)0.32358 (12)0.06852 (13)0.0277 (5)
H2F0.67770.33430.02570.033*
O2G0.8630 (3)0.61826 (11)0.09103 (13)0.0515 (5)
HO2G0.81190.57470.10670.077*
C3F0.6633 (4)0.28256 (13)0.13722 (13)0.0300 (5)
H3F0.76150.26380.17520.036*
C5G1.3957 (3)0.56388 (13)0.02115 (14)0.0297 (5)
H5G1.46990.55460.02730.036*
C5F0.6453 (4)0.42388 (14)0.20100 (13)0.0340 (5)
H5F0.75340.40750.23540.041*
C6G1.5349 (4)0.56251 (16)0.09051 (16)0.0401 (6)
H6G11.62730.60840.08490.048*
H6G21.60770.51010.08960.048*
C1G1.1747 (4)0.65996 (13)0.04117 (14)0.0342 (5)
H1G1.12440.71770.03760.041*
C1F0.8651 (3)0.40594 (13)0.09338 (13)0.0265 (5)
H1F0.97300.39500.12970.032*
C4F0.5276 (3)0.34505 (15)0.17948 (14)0.0311 (5)
H4F0.48630.31850.22880.037*
CM1.3942 (5)0.71000 (19)0.13900 (19)0.0569 (8)
H1M1.44280.69740.19060.085*
H2M1.33370.76460.13930.085*
H3M1.50010.70980.10220.085*
C6F0.5265 (5)0.49154 (19)0.24140 (19)0.0540 (8)
H6F10.60870.53890.25320.081*
H6F20.47280.46940.28920.081*
H6F30.42280.50930.20740.081*
OW11.3589 (5)0.73298 (12)0.19392 (13)0.0711 (8)
H1W11.346 (8)0.756 (2)0.2458 (9)0.107*
H2W11.380 (8)0.7801 (16)0.1598 (16)0.107*
OW21.3176 (3)0.81074 (13)0.34403 (13)0.0537 (5)
H1W21.401 (4)0.8551 (16)0.3269 (19)0.081*
H2W21.386 (4)0.7814 (19)0.3847 (17)0.081*
OW31.5566 (6)0.91571 (16)0.26618 (16)0.0927 (11)
H1W31.559 (9)0.9740 (10)0.280 (2)0.139*
H2W31.574 (9)0.913 (3)0.2108 (8)0.139*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O3G0.0305 (8)0.0270 (7)0.0290 (8)0.0070 (7)0.0009 (7)0.0010 (6)
O4G0.0358 (9)0.0251 (7)0.0443 (10)0.0008 (7)0.0034 (8)0.0040 (7)
O5G0.0449 (10)0.0231 (7)0.0371 (9)0.0040 (8)0.0048 (8)0.0027 (6)
O2F0.0481 (11)0.0269 (8)0.0429 (10)0.0054 (8)0.0140 (9)0.0013 (7)
O1G0.0467 (11)0.0340 (8)0.0353 (9)0.0072 (8)0.0027 (8)0.0056 (7)
O4F0.0262 (9)0.0491 (10)0.0471 (11)0.0020 (8)0.0017 (8)0.0101 (8)
O5F0.0332 (9)0.0268 (7)0.0383 (8)0.0022 (7)0.0078 (7)0.0039 (6)
O3F0.0434 (11)0.0286 (8)0.0479 (11)0.0117 (8)0.0046 (9)0.0013 (7)
C2G0.0319 (13)0.0254 (10)0.0399 (13)0.0025 (10)0.0008 (11)0.0027 (9)
C3G0.0284 (12)0.0218 (9)0.0284 (11)0.0044 (9)0.0017 (9)0.0018 (8)
C4G0.0294 (12)0.0246 (9)0.0286 (11)0.0003 (9)0.0012 (10)0.0015 (8)
O6G0.0692 (14)0.0379 (9)0.0351 (10)0.0016 (10)0.0098 (10)0.0017 (7)
C2F0.0286 (12)0.0248 (10)0.0298 (11)0.0002 (10)0.0011 (9)0.0019 (9)
O2G0.0449 (11)0.0295 (8)0.0799 (15)0.0004 (8)0.0242 (11)0.0107 (9)
C3F0.0298 (12)0.0249 (10)0.0355 (12)0.0021 (10)0.0030 (10)0.0015 (9)
C5G0.0317 (13)0.0253 (10)0.0320 (12)0.0027 (9)0.0030 (10)0.0008 (9)
C5F0.0347 (13)0.0381 (12)0.0293 (12)0.0011 (11)0.0025 (10)0.0052 (9)
C6G0.0358 (14)0.0357 (12)0.0486 (15)0.0058 (11)0.0081 (12)0.0029 (11)
C1G0.0410 (15)0.0233 (10)0.0384 (13)0.0006 (10)0.0031 (11)0.0005 (9)
C1F0.0264 (11)0.0266 (10)0.0265 (11)0.0004 (9)0.0037 (9)0.0019 (8)
C4F0.0277 (12)0.0352 (11)0.0306 (12)0.0023 (10)0.0001 (9)0.0075 (9)
CM0.066 (2)0.0476 (15)0.0576 (19)0.0182 (15)0.0123 (16)0.0127 (13)
C6F0.0563 (19)0.0499 (15)0.0558 (18)0.0019 (15)0.0195 (15)0.0152 (13)
OW20.0504 (13)0.0527 (11)0.0582 (12)0.0093 (10)0.0077 (10)0.0061 (9)
OW10.120 (2)0.0406 (10)0.0530 (13)0.0049 (13)0.0149 (15)0.0009 (9)
OW30.132 (3)0.0711 (15)0.0748 (18)0.0500 (18)0.0501 (19)0.0269 (13)
Geometric parameters (Å, º) top
O3G—C1F1.399 (3)C2F—C3F1.525 (3)
O3G—C3G1.440 (3)C2F—H2F0.9800
O4G—C4G1.430 (3)O2G—HO2G0.8200
O4G—HO4G0.8200C3F—C4F1.538 (3)
O5G—C1G1.406 (3)C3F—H3F0.9800
O5G—C5G1.447 (3)C5G—C6G1.519 (4)
O2F—C2F1.431 (3)C5G—H5G0.9800
O2F—HO2F0.8200C5F—C6F1.513 (3)
O1G—C1G1.408 (3)C5F—C4F1.533 (3)
O1G—CM1.430 (3)C5F—H5F0.9800
O4F—C4F1.421 (3)C6G—H6G10.9700
O4F—HO4F0.8200C6G—H6G20.9700
O5F—C1F1.436 (3)C1G—H1G0.9800
O5F—C5F1.449 (3)C1F—H1F0.9800
O3F—C3F1.441 (3)C4F—H4F0.9800
O3F—HO3F0.8200CM—H1M0.9600
C2G—O2G1.423 (3)CM—H2M0.9600
C2G—C1G1.527 (3)CM—H3M0.9600
C2G—C3G1.537 (3)C6F—H6F10.9600
C2G—H2G0.9800C6F—H6F20.9600
C3G—C4G1.528 (3)C6F—H6F30.9600
C3G—H3G0.9800OW2—H1W20.96 (2)
C4G—C5G1.534 (3)OW2—H2W20.96 (3)
C4G—H4G0.9800OW1—H1W10.95 (3)
O6G—C6G1.423 (4)OW1—H2W10.96 (3)
O6G—HO6G0.8200OW3—H1W30.95 (2)
C2F—C1F1.521 (3)OW3—H2W30.95 (12)
C1F—O3G—C3G116.05 (16)O5F—C5F—C6F107.4 (2)
C4G—O4G—HO4G109.5O5F—C5F—C4F108.61 (17)
C1G—O5G—C5G114.29 (16)C6F—C5F—C4F113.8 (2)
C2F—O2F—HO2F109.5O5F—C5F—H5F109.0
C1G—O1G—CM114.1 (2)C6F—C5F—H5F109.0
C4F—O4F—HO4F109.5C4F—C5F—H5F109.0
C1F—O5F—C5F111.86 (16)O6G—C6G—C5G113.4 (2)
C3F—O3F—HO3F109.5O6G—C6G—H6G1108.9
O2G—C2G—C1G108.48 (18)C5G—C6G—H6G1108.9
O2G—C2G—C3G114.37 (19)O6G—C6G—H6G2108.9
C1G—C2G—C3G108.59 (19)C5G—C6G—H6G2108.9
O2G—C2G—H2G108.4H6G1—C6G—H6G2107.7
C1G—C2G—H2G108.4O5G—C1G—O1G112.8 (2)
C3G—C2G—H2G108.4O5G—C1G—C2G110.74 (18)
O3G—C3G—C4G108.08 (16)O1G—C1G—C2G107.00 (18)
O3G—C3G—C2G111.57 (18)O5G—C1G—H1G108.7
C4G—C3G—C2G108.42 (18)O1G—C1G—H1G108.7
O3G—C3G—H3G109.6C2G—C1G—H1G108.7
C4G—C3G—H3G109.6O3G—C1F—O5F107.58 (16)
C2G—C3G—H3G109.6O3G—C1F—C2F108.10 (17)
O4G—C4G—C3G111.20 (16)O5F—C1F—C2F110.06 (18)
O4G—C4G—C5G106.61 (18)O3G—C1F—H1F110.3
C3G—C4G—C5G110.68 (17)O5F—C1F—H1F110.3
O4G—C4G—H4G109.4C2F—C1F—H1F110.3
C3G—C4G—H4G109.4O4F—C4F—C5F112.78 (19)
C5G—C4G—H4G109.4O4F—C4F—C3F113.2 (2)
C6G—O6G—HO6G109.5C5F—C4F—C3F108.54 (19)
O2F—C2F—C1F110.17 (19)O4F—C4F—H4F107.3
O2F—C2F—C3F106.82 (17)C5F—C4F—H4F107.3
C1F—C2F—C3F111.08 (17)C3F—C4F—H4F107.3
O2F—C2F—H2F109.6O1G—CM—H1M109.5
C1F—C2F—H2F109.6O1G—CM—H2M109.5
C3F—C2F—H2F109.6H1M—CM—H2M109.5
C2G—O2G—HO2G109.5O1G—CM—H3M109.5
O3F—C3F—C2F107.73 (18)H1M—CM—H3M109.5
O3F—C3F—C4F113.7 (2)H2M—CM—H3M109.5
C2F—C3F—C4F111.95 (17)C5F—C6F—H6F1109.5
O3F—C3F—H3F107.7C5F—C6F—H6F2109.5
C2F—C3F—H3F107.7H6F1—C6F—H6F2109.5
C4F—C3F—H3F107.7C5F—C6F—H6F3109.5
O5G—C5G—C6G106.36 (18)H6F1—C6F—H6F3109.5
O5G—C5G—C4G110.83 (18)H6F2—C6F—H6F3109.5
C6G—C5G—C4G112.70 (19)H1W2—OW2—H2W2106 (2)
O5G—C5G—H5G109.0H1W1—OW1—H2W1107 (2)
C6G—C5G—H5G109.0H1W3—OW3—H2W3107 (15)
C4G—C5G—H5G109.0
H1F—C1F—O3G—C3G37.76O4G—C4G—C5G—C6G66.6 (2)
C1F—O3G—C3G—C4G137.58 (18)C3G—C4G—C5G—C6G172.35 (19)
C3G—O3G—C1F—O5F82.7 (2)C1F—O5F—C5F—C6F170.2 (2)
CM—O1G—C1G—H1G52.79C1F—O5F—C5F—C4F66.3 (2)
C3G—O3G—C1F—C2F158.51 (17)C4G—C5G—C6G—O6G55.2 (3)
O5G—C1G—O1G—CM67.9 (3)C5G—O5G—C1G—O1G60.1 (2)
C1F—O3G—C3G—H3G18.22C5G—O5G—C1G—C2G59.7 (2)
C2G—C1G—O1G—CM170.1 (2)O2G—C2G—C1G—O5G175.17 (19)
C1F—O3G—C3G—C2G103.3 (2)C3G—C2G—C1G—O5G60.0 (2)
O5G—C5G—C6G—O6G66.5 (2)O2G—C2G—C1G—O1G61.6 (2)
O2G—C2G—C3G—O3G61.8 (3)C3G—C2G—C1G—O1G63.3 (2)
C1G—C2G—C3G—O3G176.86 (18)C5F—O5F—C1F—O3G179.39 (17)
O2G—C2G—C3G—C4G179.3 (2)C5F—O5F—C1F—C2F63.0 (2)
C1G—C2G—C3G—C4G58.0 (2)O2F—C2F—C1F—O3G71.0 (2)
O3G—C3G—C4G—O4G65.1 (2)C3F—C2F—C1F—O3G170.79 (18)
C2G—C3G—C4G—O4G173.81 (18)O2F—C2F—C1F—O5F171.72 (17)
O3G—C3G—C4G—C5G176.58 (17)C3F—C2F—C1F—O5F53.5 (2)
C2G—C3G—C4G—C5G55.5 (2)O5F—C5F—C4F—O4F67.2 (3)
O2F—C2F—C3F—O3F64.2 (2)C6F—C5F—C4F—O4F52.4 (3)
C1F—C2F—C3F—O3F175.65 (18)O5F—C5F—C4F—C3F59.0 (2)
O2F—C2F—C3F—C4F170.05 (18)C6F—C5F—C4F—C3F178.6 (2)
C1F—C2F—C3F—C4F49.9 (3)O3F—C3F—C4F—O4F48.8 (3)
C1G—O5G—C5G—C6G178.77 (19)C2F—C3F—C4F—O4F73.6 (2)
C1G—O5G—C5G—C4G56.0 (2)O3F—C3F—C4F—C5F174.79 (18)
O4G—C4G—C5G—O5G174.36 (17)C2F—C3F—C4F—C5F52.4 (2)
C3G—C4G—C5G—O5G53.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2G—HO2G···O5F0.821.952.763 (2)169
O6G—HO6G···OW10.821.882.689 (3)171
O4G—HO4G···O3Fi0.822.263.077 (3)173
O2F—HO2F···O3Fi0.821.992.794 (3)169
O3F—HO3F···OW2ii0.821.982.769 (3)160
O4F—HO4F···O4Giii0.822.042.804 (3)154
OW1—H1W1···OW20.96 (2)1.89 (2)2.850 (3)175 (3)
OW1—H2W1···O2Giv0.96 (3)2.00 (3)2.938 (3)168 (5)
OW2—H1W2···OW30.95 (3)1.77 (3)2.687 (4)160 (3)
OW2—H2W2···O2Fv0.96 (3)1.98 (3)2.918 (3)166 (3)
OW3—H1W3···O6Gvi0.95 (2)1.79 (2)2.719 (3)162 (3)
OW3—H2W3···O1Giv0.95 (2)2.24 (4)3.054 (4)143 (4)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+3/2, y+1, z+1/2; (iii) x1, y, z; (iv) x+1/2, y+3/2, z; (v) x+5/2, y+1, z1/2; (vi) x+3, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H24O10·3(H2O)
Mr394.37
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)6.8638 (16), 15.861 (4), 17.014 (7)
V3)1852.2 (10)
Z4
Radiation typeSynchrotron, λ = 0.8720 Å
µ (mm1)0.21
Crystal size (mm)0.35 × 0.1 × 0.1
Data collection
DiffractometerMAR-CCD area detector
diffractometer
Absorption correctionNumerical
X-RED (Stoe & Cie, 1997)
Tmin, Tmax0.93, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
25554, 2062, 1811
Rint0.048
(sin θ/λ)max1)0.614
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 1.56
No. of reflections2062
No. of parameters259
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.15

Computer programs: MARCCD control software (MAR, 2002), Twinsolve (Svensson, 2002), Twinsolve, SHELXD (Sheldrick & Schneider, 2001), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2000), PLATON (Spek, 2002).

Selected torsion angles (º) top
H1F—C1F—O3G—C3G37.76O5G—C1G—O1G—CM67.9 (3)
C1F—O3G—C3G—C4G137.58 (18)C1F—O3G—C3G—H3G18.22
C3G—O3G—C1F—O5F82.7 (2)C2G—C1G—O1G—CM170.1 (2)
CM—O1G—C1G—H1G52.79C1F—O3G—C3G—C2G103.3 (2)
C3G—O3G—C1F—C2F158.51 (17)O5G—C5G—C6G—O6G66.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2G—HO2G···O5F0.821.9542.763 (2)169
O6G—HO6G···OW10.821.8762.689 (3)171
O4G—HO4G···O3Fi0.822.2613.077 (3)173
O2F—HO2F···O3Fi0.821.9852.794 (3)169
O3F—HO3F···OW2ii0.821.9832.769 (3)160
O4F—HO4F···O4Giii0.822.0432.804 (3)154
OW1—H1W1···OW20.96 (2)1.89 (2)2.850 (3)175 (3)
OW1—H2W1···O2Giv0.96 (3)2.00 (3)2.938 (3)168 (5)
OW2—H1W2···OW30.95 (3)1.77 (3)2.687 (4)160 (3)
OW2—H2W2···O2Fv0.96 (3)1.98 (3)2.918 (3)166 (3)
OW3—H1W3···O6Gvi0.95 (2)1.79 (2)2.719 (3)162 (3)
OW3—H2W3···O1Giv0.95 (2)2.24 (4)3.054 (4)143 (4)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+3/2, y+1, z+1/2; (iii) x1, y, z; (iv) x+1/2, y+3/2, z; (v) x+5/2, y+1, z1/2; (vi) x+3, y+1/2, z1/2.
 

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