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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1639–o1640.
Published online 2008 July 31. doi:  10.1107/S1600536808021454
PMCID: PMC2962246

Methyl 3-O-α-d-mannopyranosyl β-d-glucopyran­oside tetra­hydrate

Abstract

The title compound, C13H24O11·4H2O, forms extended hydrogen-bonded networks. These are present between disaccharides, but not as inter-residue hydrogen bonds, as well as to water mol­ecules that in addition form an inter­molecular chain of hydrogen bonds. The conformation of the disaccharide is described by the glycosidic torsion angles ϕH = −34° and ψH = −5°. Macroscopically, the disaccharide was observed to be hygroscopic.

Related literature

For related literature, see: Cremer & Pople (1975 [triangle]); Eriksson & Widmalm (2005 [triangle]); Eriksson et al. (1997 [triangle], 2000 [triangle], 2002 [triangle]); Färnbäck et al. (2003 [triangle], 2008 [triangle]); Hassel & Ottar (1947 [triangle]); Huskens (2006 [triangle]); Jansson et al. (1990 [triangle]); Juaristi & Cuevas (1992 [triangle]); Odelius et al. (1995 [triangle]); Vishnyakov et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1639-scheme1.jpg

Experimental

Crystal data

  • C13H24O11·4H2O
  • M r = 428.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1639-efi1.jpg
  • a = 18.275 (3) Å
  • b = 7.7293 (12) Å
  • c = 13.910 (3) Å
  • β = 97.87 (2)°
  • V = 1946.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 291 (2) K
  • 0.40 × 0.30 × 0.15 mm

Data collection

  • Stoe IPDS diffractometer
  • Absorption correction: numerical (X-RED; Stoe & Cie, 1997 [triangle]) T min = 0.95, T max = 0.98
  • 8973 measured reflections
  • 2017 independent reflections
  • 1706 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.059
  • S = 0.99
  • 2017 reflections
  • 287 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: EXPOSE (Stoe & Cie, 1997 [triangle]); cell refinement: CELL (Stoe & Cie, 1997 [triangle]); data reduction: INTEGRATE (Stoe & Cie, 1997 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Bergerhoff, 1996 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021454/om2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021454/om2251Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

Carbohydrates in biological systems, in the case of N-linked glycans of glycoproteins the result of post-translational modifications, are of functional significance due to e.g. their influence on protein stability. Furthermore, highly specific epitopes are formed by oligosaccharides present as glycoconjugates. The information contents in carbohydrate structures are indeed very large as a consequence of the immense numbers of permutations possible by combining different linkages and anomeric configurations of the sugar residues. It is of particular importance that the often weak carbohydrate interactions function by resorting to multivalent interactions upon cell-cell recognition (Huskens, 2006).

The major degrees of freedom in an oligosaccharide are described by the torsion angles [var phi]H, ψH, and ω. For the title compound the two former are present at the glycosidic α-(1 → 3)-linkage with [var phi]H being defined by H1m—C1m—O3g—C3g and ψH by C1m—O3g—C3g—H3g. The ω torsion angle, defined by O5—C5—C6—O6, refers to the conformation of the hydroxymethyl group of each sugar residue. The structure is described as the exo-anomeric conformation with [var phi]H = -34°, which, as a result of stereoelectronic effects, is characteristic of sugars in a cyclic form (Fig. 1). For the title compound the presence of the endo-anomeric effect (Juaristi & Cuevas, 1992) is evident from the difference in C—O bond lengths at the anomeric positions of the α-D-Manp residue having the axial bond C1m—O3g = 1.409 (2) Å and the β-D-Glcp residue having the equatorial bond C1g—O1g = 1.402 (2) Å, i.e., the bond with the axial electronegative atom is longer than the corresponding equatorial one, in complete agreement with ab initio data of model compounds (Odelius et al., 1995). At the glycosidic linkage ψH = -5°, leading to an almost eclipsed conformation and as a result the inter-residue distance across the glycosidic linkage for the proton pair H1m—H3g becomes short, only 2.12 Å.

The conformations of the hydroxymethyl groups are described by one of the three rotamers, gauche-trans, gauche-gauche, or trans-gauche with respect to the orientation of C6—O6 to C5—O5 and to C5—C4, respectively. In the present case both the mannopyranosyl and the glucopyranosyl residues show the gg conformation for their hydroxymethyl groups with ω = -64.9 (2)° and ω = -69.7 (2)°, respectively. This conformation is one of the two anticipated rotamers for the monosaccharides in the title compound, since both have an equatorial hydroxyl group at C4, which precludes the tg rotamer as a result of a non-favorable 1,3-diaxial interaction known as the Hassel-Ottar effect (Hassel & Ottar, 1947).

The calculated Cremer & Pople (1975) parameters show that both the mannose and glucose rings are close to the expected chair conformation, i.e.4C1. The parameters for the mannose ring are [Q=0.555 (2) Å, θ=3.0 (2) ° and [var phi]=302 (3) °] and for the glucose ring [Q=0.575 (2) Å, θ=10.0 (2) ° and [var phi]=327 (1) °].

The title compound was quite hygroscopic. This fact is consistent with the relatively high water content in the crystal of the title disaccharide. In our previous structural studies on disaccharide crystals the number of water molecules ranged from zero to three per disaccharide (Eriksson et al. 1997, 2000, 2002, 2005; Färnbäck et al. 2003, 2008). All hydroxyl groups and all H atoms of the four water molecules are hydrogen bond donors and the structure is stabilized by an elaborate hydrogen bond network. The four water molecules can be considered as lying in channels along the b-direction between the sugar residues as shown in Fig. 2. Previous conformational studies on the title compound that focused on solution patterns in binary aqueous solvent mixtures indicated that an inter-residue hydrogen bond was present between O6m as the donor atom and O2g as the acceptor atom (Vishnyakov et al. 2000). This was possible when the ω torsion angle of the mannosyl residue had the gt conformation. However, in the present crystal structure the exo-cyclic hydroxymethyl groups of the glucosyl residue as well as that in the mannosyl residue have the gg conformation, the latter of which precludes the intra-molecular hydrogen bond. Further analysis of the hydrogen bonding patterns showed that O6m acts as a donor to OW3. The O6g atom, on the other hand, acts as a donor to OW1, which acts as a donor to OW2, continued in a donor-acceptor relationship to OW3, and in an analogous way to OW4. Finally, the latter water molecule acts as a donor to the acceptor O6g in another molecule. Thus, the water-mediated chain starts from one glucosyl residue and ends at a symmetry related glucosyl residue. Along the 'chain of water molecules' various atoms of the sugar residues act as hydrogen bond donors and acceptors. The close proximity of O2g in one molecule and O3m and O4m in a symmetry related molecule at distances of 3.140 (2) Å and 2.848 (2) Å, respectively, indicate that a bifurcated hydrogen bond is present with O2g as the donor atom. The triangle formed by the three oxygen atoms is almost isosceles with an O3mv—O2g—O4mv [symmetry code (v): -x + 1/2,y + 1/2,-z] angle of 56.09 (4)°.

Experimental

The synthesis of the title compound was described by Jansson et al. (1990). The disaccharide was crystallized by slow evaporation from a mixture of water, ethanol and acetonitrile (1:1:1) at ambient temperature. The absolute configuration of each sugar residue is known from the starting compounds used in the synthesis.

Refinement

The hydrogen atoms were geometrically placed and constrained to ride on the parent atom. The C—H bond distances are 0.96 Å for CH3, 0.97 Å for CH2, 0.98 Å for CH. The Uiso(H) = 1.5 Ueq(C) for the CH3 and 1.2 Ueq(C) for all other H atoms. Due to the abscence of significant anomalous scatterers, the value of the Flack parameter (Flack, 1983) was not meaningful, thus the 1707 Friedel equivalents were included in the merging process (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).

Figures

Fig. 1.
Molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. H atoms are shown as small spheres of arbitrary radii.
Fig. 2.
Crystal packing of the title compound, showing slightly more than one unit cell, viewed along the b axis direction. The water molecules between the sugar residues are situated in channels along the b-direction.

Crystal data

C13H24O11·4H2OF000 = 920
Mr = 428.39Dx = 1.462 Mg m3
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1641 reflections
a = 18.275 (3) Åθ = 2.3–25.9º
b = 7.7293 (12) ŵ = 0.14 mm1
c = 13.910 (3) ÅT = 291 (2) K
β = 97.87 (2)ºBlock, colourless
V = 1946.4 (6) Å30.40 × 0.30 × 0.15 mm
Z = 4

Data collection

Stoe IPDS diffractometer2017 independent reflections
Radiation source: fine-focus sealed tube1706 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
Detector resolution: 6 pixels mm-1θmax = 25.9º
T = 291(2) Kθmin = 2.3º
[var phi] scansh = −22→22
Absorption correction: numerical(X-RED; Stoe & Cie, 1997)k = −9→9
Tmin = 0.95, Tmax = 0.98l = −16→17
8973 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059  w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2017 reflectionsΔρmax = 0.13 e Å3
287 parametersΔρmin = −0.14 e Å3
9 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (9)

Special details

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)

xyzUiso*/Ueq
C1m0.16629 (10)0.4371 (3)0.18727 (14)0.0237 (4)
H1m0.15300.43740.25310.028*
C2m0.11852 (10)0.3031 (3)0.12731 (15)0.0253 (4)
H2m0.13120.18690.15250.030*
O2m0.04476 (7)0.3436 (2)0.14055 (11)0.0354 (4)
H2m10.01610.28290.10470.053*
C3m0.13077 (10)0.3138 (3)0.02186 (15)0.0231 (4)
H3m0.18120.27520.01690.028*
O3m0.08036 (8)0.2061 (2)−0.03918 (11)0.0297 (3)
H3m10.08740.1046−0.02340.044*
C4m0.12196 (11)0.4985 (3)−0.01623 (14)0.0246 (4)
H4m0.07030.5351−0.01930.030*
O4m0.14398 (9)0.5051 (2)−0.11052 (11)0.0390 (4)
H4m10.11210.5547−0.14780.059*
C5m0.17184 (10)0.6189 (3)0.05093 (14)0.0251 (4)
H5m0.22330.58380.05010.030*
O5m0.15526 (7)0.60426 (18)0.14856 (9)0.0244 (3)
C6m0.16458 (11)0.8075 (3)0.02356 (17)0.0312 (5)
H6m10.19700.87470.07050.037*
H6m20.18090.8234−0.03940.037*
O6m0.09124 (8)0.8723 (2)0.01954 (13)0.0393 (4)
H6m0.07690.85850.07240.059*
C1g0.41344 (10)0.5571 (3)0.33556 (15)0.0276 (5)
H1g0.39680.63840.38210.033*
O1g0.47702 (7)0.6210 (2)0.30165 (10)0.0340 (4)
C2g0.35400 (10)0.5359 (3)0.24839 (15)0.0288 (5)
H2g0.37430.47340.19670.035*
O2g0.32707 (8)0.6996 (2)0.21340 (13)0.0441 (4)
H2g10.35640.74310.18080.066*
C3g0.28842 (10)0.4364 (3)0.27749 (14)0.0244 (4)
H3g0.26090.51280.31590.029*
O3g0.24034 (6)0.38309 (19)0.19220 (10)0.0268 (3)
C4g0.31150 (10)0.2760 (3)0.33673 (14)0.0251 (4)
H4g0.33160.19050.29540.030*
O4g0.24809 (7)0.2055 (2)0.37211 (11)0.0330 (4)
H4g10.23830.11080.34700.050*
C5g0.37025 (10)0.3225 (3)0.42143 (15)0.0278 (4)
H5g0.35010.41010.46150.033*
O5g0.43192 (7)0.3957 (2)0.38142 (11)0.0310 (3)
C6g0.39763 (12)0.1712 (3)0.48482 (17)0.0400 (6)
H6g10.43980.20750.53040.048*
H6g20.35900.13480.52180.048*
O6g0.41839 (9)0.0293 (2)0.42994 (15)0.0498 (5)
H6g0.3866−0.04600.42730.075*
C70.53302 (12)0.6785 (4)0.37756 (18)0.0435 (6)
H710.51460.77450.41090.065*
H720.57600.71390.34990.065*
H730.54590.58570.42250.065*
OW10.19300 (11)0.2972 (3)0.53816 (17)0.0612 (5)
H110.2119 (18)0.274 (5)0.480 (2)0.092*
H120.2364 (15)0.320 (5)0.585 (2)0.092*
OW20.28912 (11)0.3894 (3)0.70793 (15)0.0564 (5)
H210.3355 (13)0.361 (5)0.737 (3)0.085*
H220.2615 (18)0.332 (5)0.747 (3)0.085*
OW30.44168 (10)0.3766 (3)0.78999 (16)0.0577 (5)
H310.4706 (19)0.463 (4)0.773 (3)0.086*
H320.4659 (19)0.275 (4)0.787 (3)0.086*
OW40.52138 (11)0.0800 (3)0.75157 (14)0.0540 (5)
H410.5331 (19)0.061 (5)0.6924 (19)0.081*
H420.4990 (18)−0.009 (4)0.776 (3)0.081*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C1m0.0207 (8)0.0279 (11)0.0223 (10)0.0007 (8)0.0020 (7)0.0011 (8)
C2m0.0215 (9)0.0253 (11)0.0285 (11)−0.0011 (8)0.0014 (8)0.0026 (9)
O2m0.0218 (6)0.0514 (10)0.0336 (8)−0.0102 (7)0.0067 (6)−0.0122 (7)
C3m0.0188 (8)0.0236 (10)0.0264 (10)0.0030 (8)0.0015 (7)−0.0035 (9)
O3m0.0329 (7)0.0208 (7)0.0322 (8)0.0033 (6)−0.0064 (6)−0.0024 (6)
C4m0.0258 (9)0.0262 (11)0.0218 (10)0.0034 (8)0.0026 (8)0.0008 (9)
O4m0.0518 (9)0.0410 (10)0.0261 (8)0.0069 (8)0.0118 (7)0.0037 (7)
C5m0.0227 (9)0.0258 (10)0.0273 (10)0.0015 (8)0.0049 (8)0.0029 (9)
O5m0.0255 (7)0.0238 (7)0.0236 (7)0.0009 (6)0.0023 (5)−0.0015 (6)
C6m0.0305 (10)0.0253 (11)0.0377 (12)−0.0014 (9)0.0045 (9)0.0040 (10)
O6m0.0382 (8)0.0271 (8)0.0528 (10)0.0086 (7)0.0070 (7)0.0084 (8)
C1g0.0230 (9)0.0328 (12)0.0277 (10)−0.0026 (8)0.0059 (8)0.0006 (9)
O1g0.0244 (7)0.0456 (9)0.0323 (8)−0.0101 (7)0.0056 (6)−0.0001 (7)
C2g0.0243 (9)0.0347 (12)0.0276 (11)−0.0026 (9)0.0046 (8)0.0048 (9)
O2g0.0347 (8)0.0448 (10)0.0522 (11)−0.0040 (8)0.0033 (7)0.0247 (9)
C3g0.0220 (9)0.0288 (11)0.0214 (10)−0.0010 (8)−0.0002 (7)−0.0002 (9)
O3g0.0202 (6)0.0349 (8)0.0238 (7)0.0044 (6)−0.0027 (5)−0.0025 (7)
C4g0.0218 (9)0.0272 (11)0.0263 (10)−0.0003 (8)0.0029 (7)0.0021 (9)
O4g0.0304 (7)0.0347 (9)0.0351 (9)−0.0087 (7)0.0082 (6)−0.0006 (8)
C5g0.0239 (9)0.0328 (11)0.0263 (10)−0.0007 (8)0.0023 (8)0.0020 (9)
O5g0.0213 (6)0.0361 (8)0.0348 (8)−0.0011 (6)0.0006 (6)0.0062 (7)
C6g0.0327 (11)0.0499 (16)0.0357 (13)0.0002 (10)−0.0017 (9)0.0120 (11)
O6g0.0454 (9)0.0424 (10)0.0628 (12)0.0112 (8)0.0112 (9)0.0138 (9)
C70.0316 (11)0.0531 (16)0.0444 (14)−0.0129 (11)0.0001 (9)−0.0019 (12)
OW10.0568 (11)0.0722 (14)0.0581 (13)−0.0008 (10)0.0205 (9)−0.0107 (12)
OW20.0614 (11)0.0459 (11)0.0601 (12)0.0062 (10)0.0014 (9)0.0157 (11)
OW30.0507 (10)0.0498 (12)0.0775 (14)−0.0013 (9)0.0270 (10)0.0152 (11)
OW40.0581 (11)0.0581 (13)0.0474 (11)−0.0042 (9)0.0128 (9)0.0088 (10)

Geometric parameters (Å, °)

C1m—O5m1.403 (2)C2g—C3g1.525 (3)
C1m—O3g1.409 (2)C2g—H2g0.9800
C1m—C2m1.527 (3)O2g—H2g10.8200
C1m—H1m0.9800C3g—O3g1.437 (2)
C2m—O2m1.420 (2)C3g—C4g1.516 (3)
C2m—C3m1.516 (3)C3g—H3g0.9800
C2m—H2m0.9800C4g—O4g1.428 (2)
O2m—H2m10.8200C4g—C5g1.524 (3)
C3m—O3m1.431 (2)C4g—H4g0.9800
C3m—C4m1.523 (3)O4g—H4g10.8200
C3m—H3m0.9800C5g—O5g1.439 (2)
O3m—H3m10.8200C5g—C6g1.508 (3)
C4m—O4m1.425 (2)C5g—H5g0.9800
C4m—C5m1.529 (3)C6g—O6g1.417 (3)
C4m—H4m0.9800C6g—H6g10.9700
O4m—H4m10.8200C6g—H6g20.9700
C5m—O5m1.436 (2)O6g—H6g0.8200
C5m—C6m1.508 (3)C7—H710.9600
C5m—H5m0.9800C7—H720.9600
C6m—O6m1.425 (3)C7—H730.9600
C6m—H6m10.9700OW1—H110.94 (2)
C6m—H6m20.9700OW1—H120.97 (2)
O6m—H6m0.8200OW2—H210.92 (2)
C1g—O1g1.402 (2)OW2—H220.90 (2)
C1g—O5g1.421 (3)OW3—H310.91 (2)
C1g—C2g1.522 (3)OW3—H320.90 (2)
C1g—H1g0.9800OW4—H410.89 (2)
O1g—C71.437 (3)OW4—H420.89 (2)
C2g—O2g1.419 (3)H1m—H3g2.12
O5m—C1m—O3g112.22 (16)C1g—O1g—C7113.67 (16)
O5m—C1m—C2m111.93 (15)O2g—C2g—C1g110.69 (18)
O3g—C1m—C2m107.40 (16)O2g—C2g—C3g107.01 (16)
O5m—C1m—H1m108.4C1g—C2g—C3g110.13 (17)
O3g—C1m—H1m108.4O2g—C2g—H2g109.7
C2m—C1m—H1m108.4C1g—C2g—H2g109.7
O2m—C2m—C3m112.45 (16)C3g—C2g—H2g109.7
O2m—C2m—C1m105.16 (16)C2g—O2g—H2g1109.5
C3m—C2m—C1m110.02 (15)O3g—C3g—C4g107.92 (16)
O2m—C2m—H2m109.7O3g—C3g—C2g109.85 (16)
C3m—C2m—H2m109.7C4g—C3g—C2g112.73 (16)
C1m—C2m—H2m109.7O3g—C3g—H3g108.8
C2m—O2m—H2m1109.5C4g—C3g—H3g108.8
O3m—C3m—C2m111.96 (16)C2g—C3g—H3g108.8
O3m—C3m—C4m108.06 (15)C1m—O3g—C3g115.46 (15)
C2m—C3m—C4m111.41 (16)O4g—C4g—C3g108.71 (15)
O3m—C3m—H3m108.4O4g—C4g—C5g110.03 (16)
C2m—C3m—H3m108.4C3g—C4g—C5g109.96 (16)
C4m—C3m—H3m108.4O4g—C4g—H4g109.4
C3m—O3m—H3m1109.5C3g—C4g—H4g109.4
O4m—C4m—C3m108.92 (16)C5g—C4g—H4g109.4
O4m—C4m—C5m108.71 (16)C4g—O4g—H4g1109.5
C3m—C4m—C5m109.40 (15)O5g—C5g—C6g108.43 (16)
O4m—C4m—H4m109.9O5g—C5g—C4g107.44 (16)
C3m—C4m—H4m109.9C6g—C5g—C4g114.28 (18)
C5m—C4m—H4m109.9O5g—C5g—H5g108.9
C4m—O4m—H4m1109.5C6g—C5g—H5g108.9
O5m—C5m—C6m107.01 (16)C4g—C5g—H5g108.9
O5m—C5m—C4m110.16 (15)C1g—O5g—C5g111.60 (14)
C6m—C5m—C4m114.19 (17)O6g—C6g—C5g112.14 (19)
O5m—C5m—H5m108.4O6g—C6g—H6g1109.2
C6m—C5m—H5m108.4C5g—C6g—H6g1109.2
C4m—C5m—H5m108.4O6g—C6g—H6g2109.2
C1m—O5m—C5m113.43 (15)C5g—C6g—H6g2109.2
O6m—C6m—C5m113.55 (17)H6g1—C6g—H6g2107.9
O6m—C6m—H6m1108.9C6g—O6g—H6g109.5
C5m—C6m—H6m1108.9O1g—C7—H71109.5
O6m—C6m—H6m2108.9O1g—C7—H72109.5
C5m—C6m—H6m2108.9H71—C7—H72109.5
H6m1—C6m—H6m2107.7O1g—C7—H73109.5
C6m—O6m—H6m109.5H71—C7—H73109.5
O1g—C1g—O5g107.66 (15)H72—C7—H73109.5
O1g—C1g—C2g107.69 (16)H11—OW1—H12105 (3)
O5g—C1g—C2g111.29 (17)H21—OW2—H22100 (3)
O1g—C1g—H1g110.0H31—OW3—H32109 (3)
O5g—C1g—H1g110.0H41—OW4—H42114 (4)
C2g—C1g—H1g110.0
O5m—C1m—C2m—O2m−67.68 (19)O1g—C1g—C2g—C3g169.66 (17)
O3g—C1m—C2m—O2m168.72 (15)O5g—C1g—C2g—C3g51.9 (2)
O5m—C1m—C2m—C3m53.6 (2)O2g—C2g—C3g—O3g72.5 (2)
O3g—C1m—C2m—C3m−70.0 (2)C1g—C2g—C3g—O3g−167.17 (16)
O2m—C2m—C3m—O3m−55.7 (2)O2g—C2g—C3g—C4g−167.15 (17)
C1m—C2m—C3m—O3m−172.58 (15)C1g—C2g—C3g—C4g−46.8 (2)
O2m—C2m—C3m—C4m65.4 (2)O5m—C1m—O3g—C3g85.18 (19)
C1m—C2m—C3m—C4m−51.4 (2)C2m—C1m—O3g—C3g−151.40 (15)
O3m—C3m—C4m—O4m−64.6 (2)C4g—C3g—O3g—C1m112.63 (18)
C2m—C3m—C4m—O4m172.00 (15)C2g—C3g—O3g—C1m−124.11 (18)
O3m—C3m—C4m—C5m176.70 (14)O3g—C3g—C4g—O4g−66.67 (19)
C2m—C3m—C4m—C5m53.31 (19)C2g—C3g—C4g—O4g171.85 (17)
O4m—C4m—C5m—O5m−175.11 (16)O3g—C3g—C4g—C5g172.82 (14)
C3m—C4m—C5m—O5m−56.29 (19)C2g—C3g—C4g—C5g51.3 (2)
O4m—C4m—C5m—C6m64.5 (2)O4g—C4g—C5g—O5g−178.89 (16)
C3m—C4m—C5m—C6m−176.72 (17)C3g—C4g—C5g—O5g−59.2 (2)
O3g—C1m—O5m—C5m61.40 (19)O4g—C4g—C5g—C6g60.8 (2)
C2m—C1m—O5m—C5m−59.44 (19)C3g—C4g—C5g—C6g−179.52 (18)
C6m—C5m—O5m—C1m−174.57 (16)O1g—C1g—O5g—C5g178.17 (15)
C4m—C5m—O5m—C1m60.76 (18)C2g—C1g—O5g—C5g−64.0 (2)
O5m—C5m—C6m—O6m−64.9 (2)C6g—C5g—O5g—C1g−169.21 (17)
C4m—C5m—C6m—O6m57.2 (2)C4g—C5g—O5g—C1g66.8 (2)
O5g—C1g—O1g—C7−71.2 (2)O5g—C5g—C6g—O6g−69.7 (2)
C2g—C1g—O1g—C7168.7 (2)C4g—C5g—C6g—O6g50.1 (2)
O1g—C1g—C2g—O2g−72.2 (2)H1m—C1m—O3g—C3g−34
O5g—C1g—C2g—O2g170.02 (16)C1m—O3g—C3g—H3g−5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2m—H2m1···O3mi0.821.962.732 (2)156
O3m—H3m1···O6mii0.821.892.705 (2)172
O4m—H4m1···OW4iii0.822.032.803 (2)158
O6m—H6m···OW3iv0.822.002.796 (2)166
O2g—H2g1···O4mv0.822.252.848 (2)130
O2g—H2g1···O3mv0.822.433.140 (2)145
O4g—H4g1···OW2vi0.821.912.733 (2)177
O6g—H6g···OW1vi0.822.002.794 (2)162
OW1—H11···O4g0.94 (2)1.80 (2)2.736 (2)174 (4)
OW1—H12···OW20.97 (2)1.92 (3)2.834 (2)156 (2)
OW2—H21···OW30.92 (2)1.98 (2)2.866 (2)161 (4)
OW2—H22···O2gvi0.90 (3)2.06 (3)2.915 (2)159 (4)
OW3—H31···O1gvii0.91 (3)1.94 (3)2.814 (2)163 (4)
OW3—H32···OW40.90 (2)1.92 (2)2.807 (2)167 (4)
OW4—H41···O6gvii0.89 (2)2.04 (2)2.916 (2)168 (3)
OW4—H42···O2mvi0.89 (2)1.88 (3)2.747 (2)163 (4)

Symmetry codes: (i) −x, y, −z; (ii) x, y−1, z; (iii) x−1/2, y+1/2, z−1; (iv) −x+1/2, y+1/2, −z+1; (v) −x+1/2, y+1/2, −z; (vi) −x+1/2, y−1/2, −z+1; (vii) −x+1, y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2251).

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