Methyl 2-O-[beta]-L-fucopyranosyl [alpha]-D-glucopyran­oside monohydrate: a synchrotron study

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°.

S1. Comment

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 ϕ_H = -6° (being unusual since it was close to an eclipsed conformation) and ψ_H = 34°, whereas in F3G, the values are ϕ_H = -38° and ψ_H = 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 ϕ_H = -41° and ψ_H = -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

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).

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.5 U_eq(C,O) for the CH₃ and OH while it was set to 1.2 U_eq(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 U_iso(H) = 1.5U_eq(O). The absolute configuration of each sugar residue is known from the starting compounds used in the synthesis.

Computing details

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

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

Crystal data

C13H24O10·H2O	F(000) = 384
Mr = 358.34	Dx = 1.413 Mg m^−3
Monoclinic, P21	Synchrotron radiation, λ = 0.872 Å
Hall symbol: P 2yb	Cell parameters from 4040 reflections
a = 7.166 (2) Å	θ = 1.4–32.1°
b = 6.3924 (16) Å	µ = 0.20 mm^−1
c = 18.518 (4) Å	T = 100 K
β = 96.876 (12)°	Block, colourless
V = 842.1 (4) Å^3	0.12 × 0.06 × 0.03 mm
Z = 2

Data collection

Smart 1K CCD diffractometer	1751 independent reflections
Radiation source: Beamline I711, Maxlab	1726 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.073
Detector resolution: 10 pixels mm^-1	θmax = 32.1°, θmin = 1.4°
ω scan at different ϕ	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −7→7
Tmin = 0.97, Tmax = 0.99	l = −22→22
4040 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0958P)^2 + 0.2168P] where P = (Fo^2 + 2Fc^2)/3
1751 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.27 e Å^−3
4 restraints	Δρmin = −0.30 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C1F	0.6866 (4)	0.5242 (5)	0.82828 (13)	0.0164 (6)
H1F	0.7541	0.4015	0.8526	0.020*
C2F	0.5415 (4)	0.6075 (5)	0.87476 (14)	0.0166 (5)
H2F	0.4801	0.7343	0.8508	0.020*
O2F	0.3992 (3)	0.4550 (4)	0.88512 (10)	0.0202 (4)
H2FA	0.3120	0.4625	0.8506	0.030*
C3F	0.6442 (4)	0.6692 (5)	0.94856 (14)	0.0180 (6)
H3F	0.7049	0.5415	0.9721	0.022*
O3F	0.5090 (3)	0.7437 (4)	0.99226 (11)	0.0197 (5)
H3FA	0.5639	0.7908	1.0315	0.030*
C4F	0.7986 (4)	0.8299 (5)	0.93802 (14)	0.0195 (6)
H4F	0.8762	0.8521	0.9860	0.023*
O4F	0.7200 (3)	1.0270 (4)	0.91348 (11)	0.0234 (5)
H4FA	0.6418	1.0659	0.9411	0.035*
C5F	0.9283 (4)	0.7509 (5)	0.88367 (14)	0.0177 (6)
H5F	0.9979	0.6258	0.9052	0.021*
C6F	1.0709 (4)	0.9101 (5)	0.86421 (15)	0.0210 (6)
H6FA	1.1507	0.8466	0.8307	0.031*
H6FB	1.1491	0.9553	0.9085	0.031*
H6FC	1.0052	1.0312	0.8408	0.031*
O5F	0.8173 (3)	0.6873 (4)	0.81700 (10)	0.0187 (4)
C1G	0.5949 (3)	0.1173 (5)	0.70603 (14)	0.0155 (5)
H1G	0.6078	0.0400	0.7533	0.019*
O1G	0.4002 (3)	0.1525 (3)	0.68338 (10)	0.0180 (4)
C7G	0.2951 (4)	−0.0382 (5)	0.67637 (15)	0.0219 (6)
H7GA	0.1631	−0.0071	0.6597	0.033*
H7GB	0.3042	−0.1088	0.7236	0.033*
H7GC	0.3461	−0.1294	0.6410	0.033*
C2G	0.6966 (4)	0.3295 (4)	0.71767 (14)	0.0160 (5)
H2G	0.8231	0.3045	0.7454	0.019*
O2G	0.5932 (2)	0.4649 (3)	0.75958 (10)	0.0165 (4)
C3G	0.7239 (4)	0.4418 (5)	0.64713 (14)	0.0189 (6)
H3G	0.6020	0.5083	0.6274	0.023*
O3G	0.8626 (3)	0.6018 (4)	0.66041 (10)	0.0193 (4)
H3GA	0.8174	0.7032	0.6814	0.029*
C4G	0.7865 (4)	0.2958 (5)	0.58885 (14)	0.0177 (6)
H4G	0.9223	0.2598	0.6015	0.021*
O4G	0.7615 (3)	0.4042 (4)	0.52147 (10)	0.0200 (4)
H4GA	0.8594	0.3934	0.5009	0.030*
C5G	0.6690 (4)	0.0952 (5)	0.58384 (14)	0.0163 (5)
H5G	0.5347	0.1336	0.5687	0.020*
C6G	0.7281 (4)	−0.0631 (5)	0.53008 (14)	0.0193 (6)
H6GA	0.6467	−0.1883	0.5301	0.023*
H6GB	0.7102	−0.0020	0.4806	0.023*
O6G	0.9240 (3)	−0.1260 (3)	0.54754 (10)	0.0196 (4)
H6G	0.9322	−0.2163	0.5807	0.029*
O5G	0.6813 (3)	−0.0032 (3)	0.65409 (10)	0.0171 (4)
OW	0.1665 (3)	0.4184 (4)	0.75899 (11)	0.0250 (5)
HW1	0.081 (4)	0.506 (6)	0.7297 (15)	0.038*
HW2	0.239 (5)	0.353 (6)	0.7255 (14)	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1F	0.0177 (12)	0.0174 (14)	0.0134 (11)	−0.0042 (12)	−0.0007 (9)	−0.0012 (11)
C2F	0.0180 (11)	0.0162 (13)	0.0163 (11)	−0.0016 (11)	0.0051 (9)	0.0014 (10)
O2F	0.0200 (9)	0.0205 (11)	0.0203 (9)	−0.0034 (9)	0.0032 (7)	−0.0002 (8)
C3F	0.0196 (12)	0.0177 (13)	0.0179 (12)	0.0016 (11)	0.0073 (10)	−0.0010 (11)
O3F	0.0230 (9)	0.0206 (12)	0.0165 (9)	−0.0011 (8)	0.0070 (7)	−0.0016 (9)
C4F	0.0200 (12)	0.0182 (14)	0.0206 (13)	0.0040 (11)	0.0031 (10)	−0.0003 (12)
O4F	0.0285 (11)	0.0158 (11)	0.0281 (10)	0.0026 (9)	0.0118 (8)	0.0030 (8)
C5F	0.0190 (12)	0.0180 (14)	0.0162 (11)	−0.0005 (12)	0.0029 (10)	−0.0010 (12)
C6F	0.0202 (12)	0.0200 (15)	0.0237 (13)	−0.0022 (13)	0.0064 (10)	0.0000 (12)
O5F	0.0193 (9)	0.0194 (11)	0.0175 (9)	−0.0029 (9)	0.0032 (7)	−0.0013 (8)
C1G	0.0132 (11)	0.0155 (14)	0.0190 (11)	0.0008 (11)	0.0059 (9)	−0.0008 (11)
O1G	0.0161 (9)	0.0154 (11)	0.0224 (9)	0.0010 (8)	0.0014 (7)	−0.0015 (8)
C7G	0.0213 (13)	0.0212 (15)	0.0235 (13)	−0.0029 (12)	0.0031 (11)	−0.0018 (12)
C2G	0.0172 (11)	0.0124 (13)	0.0189 (12)	0.0004 (11)	0.0043 (9)	−0.0041 (11)
O2G	0.0193 (8)	0.0155 (10)	0.0154 (8)	0.0019 (8)	0.0046 (7)	−0.0033 (8)
C3G	0.0169 (12)	0.0223 (15)	0.0178 (12)	−0.0004 (12)	0.0034 (9)	−0.0008 (12)
O3G	0.0222 (9)	0.0158 (10)	0.0206 (9)	−0.0017 (8)	0.0059 (7)	−0.0031 (8)
C4G	0.0225 (13)	0.0127 (14)	0.0182 (12)	−0.0008 (11)	0.0040 (10)	−0.0004 (10)
O4G	0.0242 (10)	0.0198 (11)	0.0170 (9)	0.0014 (9)	0.0060 (7)	0.0032 (9)
C5G	0.0192 (11)	0.0161 (13)	0.0139 (11)	0.0024 (11)	0.0028 (9)	0.0002 (11)
C6G	0.0225 (13)	0.0179 (14)	0.0180 (12)	0.0021 (13)	0.0043 (10)	−0.0023 (12)
O6G	0.0221 (9)	0.0153 (11)	0.0221 (9)	0.0005 (8)	0.0058 (7)	0.0000 (8)
O5G	0.0206 (9)	0.0160 (10)	0.0151 (9)	0.0003 (8)	0.0034 (7)	−0.0014 (8)
OW	0.0188 (9)	0.0315 (13)	0.0246 (10)	0.0059 (10)	0.0017 (8)	−0.0016 (10)

Geometric parameters (Å, º)

C1F—O2G	1.416 (3)	O1G—C7G	1.430 (4)
C1F—O5F	1.434 (4)	C7G—H7GA	0.9800
C1F—C2F	1.523 (4)	C7G—H7GB	0.9800
C1F—H1F	1.0000	C7G—H7GC	0.9800
C2F—O2F	1.440 (3)	C2G—O2G	1.428 (3)
C2F—C3F	1.525 (4)	C2G—C3G	1.523 (4)
C2F—H2F	1.0000	C2G—H2G	1.0000
O2F—H2FA	0.8400	C3G—O3G	1.427 (4)
C3F—O3F	1.417 (3)	C3G—C4G	1.534 (4)
C3F—C4F	1.540 (4)	C3G—H3G	1.0000
C3F—H3F	1.0000	O3G—H3GA	0.8400
O3F—H3FA	0.8400	C4G—O4G	1.420 (3)
C4F—O4F	1.432 (4)	C4G—C5G	1.531 (4)
C4F—C5F	1.535 (4)	C4G—H4G	1.0000
C4F—H4F	1.0000	O4G—H4GA	0.8400
O4F—H4FA	0.8400	C5G—O5G	1.438 (3)
C5F—O5F	1.445 (3)	C5G—C6G	1.515 (4)
C5F—C6F	1.516 (4)	C5G—H5G	1.0000
C5F—H5F	1.0000	C6G—O6G	1.458 (3)
C6F—H6FA	0.9800	C6G—H6GA	0.9900
C6F—H6FB	0.9800	C6G—H6GB	0.9900
C6F—H6FC	0.9800	O6G—H6G	0.8400
C1G—O1G	1.426 (3)	OW—HW1	0.950 (10)
C1G—O5G	1.430 (3)	OW—HW2	0.950 (10)
C1G—C2G	1.543 (4)	H1f—H2g	2.19
C1G—H1G	1.0000
O2G—C1F—O5F	108.1 (2)	C2G—C1G—H1G	108.7
O2G—C1F—C2F	108.7 (2)	C1G—O1G—C7G	112.2 (2)
O5F—C1F—C2F	109.3 (2)	O1G—C7G—H7GA	109.5
O2G—C1F—H1F	110.3	O1G—C7G—H7GB	109.5
O5F—C1F—H1F	110.3	H7GA—C7G—H7GB	109.5
C2F—C1F—H1F	110.3	O1G—C7G—H7GC	109.5
O2F—C2F—C1F	112.4 (2)	H7GA—C7G—H7GC	109.5
O2F—C2F—C3F	109.2 (2)	H7GB—C7G—H7GC	109.5
C1F—C2F—C3F	107.9 (2)	O2G—C2G—C3G	108.0 (2)
O2F—C2F—H2F	109.1	O2G—C2G—C1G	110.0 (2)
C1F—C2F—H2F	109.1	C3G—C2G—C1G	113.7 (2)
C3F—C2F—H2F	109.1	O2G—C2G—H2G	108.4
C2F—O2F—H2FA	109.5	C3G—C2G—H2G	108.4
O3F—C3F—C2F	108.0 (2)	C1G—C2G—H2G	108.4
O3F—C3F—C4F	113.5 (3)	C1F—O2G—C2G	115.5 (2)
C2F—C3F—C4F	109.6 (2)	O3G—C3G—C2G	110.4 (2)
O3F—C3F—H3F	108.5	O3G—C3G—C4G	107.5 (2)
C2F—C3F—H3F	108.5	C2G—C3G—C4G	113.3 (3)
C4F—C3F—H3F	108.5	O3G—C3G—H3G	108.5
C3F—O3F—H3FA	109.5	C2G—C3G—H3G	108.5
O4F—C4F—C5F	109.1 (2)	C4G—C3G—H3G	108.5
O4F—C4F—C3F	111.5 (2)	C3G—O3G—H3GA	109.5
C5F—C4F—C3F	111.4 (2)	O4G—C4G—C5G	110.2 (2)
O4F—C4F—H4F	108.3	O4G—C4G—C3G	107.7 (2)
C5F—C4F—H4F	108.3	C5G—C4G—C3G	110.3 (2)
C3F—C4F—H4F	108.3	O4G—C4G—H4G	109.5
C4F—O4F—H4FA	109.5	C5G—C4G—H4G	109.5
O5F—C5F—C6F	107.7 (2)	C3G—C4G—H4G	109.5
O5F—C5F—C4F	109.8 (2)	C4G—O4G—H4GA	109.5
C6F—C5F—C4F	114.4 (3)	O5G—C5G—C6G	108.1 (2)
O5F—C5F—H5F	108.3	O5G—C5G—C4G	109.7 (2)
C6F—C5F—H5F	108.3	C6G—C5G—C4G	113.8 (2)
C4F—C5F—H5F	108.3	O5G—C5G—H5G	108.3
C5F—C6F—H6FA	109.5	C6G—C5G—H5G	108.3
C5F—C6F—H6FB	109.5	C4G—C5G—H5G	108.3
H6FA—C6F—H6FB	109.5	O6G—C6G—C5G	112.1 (2)
C5F—C6F—H6FC	109.5	O6G—C6G—H6GA	109.2
H6FA—C6F—H6FC	109.5	C5G—C6G—H6GA	109.2
H6FB—C6F—H6FC	109.5	O6G—C6G—H6GB	109.2
C1F—O5F—C5F	112.5 (2)	C5G—C6G—H6GB	109.2
O1G—C1G—O5G	112.0 (2)	H6GA—C6G—H6GB	107.9
O1G—C1G—C2G	109.4 (2)	C6G—O6G—H6G	109.5
O5G—C1G—C2G	109.41 (19)	C1G—O5G—C5G	112.8 (2)
O1G—C1G—H1G	108.7	HW1—OW—HW2	104.5 (14)
O5G—C1G—H1G	108.7
O2G—C1F—C2F—O2F	59.2 (3)	O5F—C1F—O2G—C2G	79.1 (3)
O5F—C1F—C2F—O2F	176.9 (2)	C2F—C1F—O2G—C2G	−162.4 (2)
O2G—C1F—C2F—C3F	179.6 (2)	C3G—C2G—O2G—C1F	−119.0 (2)
O5F—C1F—C2F—C3F	−62.6 (3)	C1G—C2G—O2G—C1F	116.5 (2)
O2F—C2F—C3F—O3F	−56.6 (3)	O2G—C2G—C3G—O3G	74.4 (3)
C1F—C2F—C3F—O3F	−179.1 (2)	C1G—C2G—C3G—O3G	−163.3 (2)
O2F—C2F—C3F—C4F	179.2 (2)	O2G—C2G—C3G—C4G	−165.0 (2)
C1F—C2F—C3F—C4F	56.7 (3)	C1G—C2G—C3G—C4G	−42.7 (3)
O3F—C3F—C4F—O4F	−51.6 (3)	O3G—C3G—C4G—O4G	−72.2 (3)
C2F—C3F—C4F—O4F	69.3 (3)	C2G—C3G—C4G—O4G	165.6 (2)
O3F—C3F—C4F—C5F	−173.7 (2)	O3G—C3G—C4G—C5G	167.5 (2)
C2F—C3F—C4F—C5F	−52.8 (3)	C2G—C3G—C4G—C5G	45.3 (3)
O4F—C4F—C5F—O5F	−71.0 (3)	O4G—C4G—C5G—O5G	−174.6 (2)
C3F—C4F—C5F—O5F	52.5 (3)	C3G—C4G—C5G—O5G	−55.8 (3)
O4F—C4F—C5F—C6F	50.2 (3)	O4G—C4G—C5G—C6G	64.1 (3)
C3F—C4F—C5F—C6F	173.7 (2)	C3G—C4G—C5G—C6G	−177.1 (2)
O2G—C1F—O5F—C5F	−176.6 (2)	O5G—C5G—C6G—O6G	−63.6 (3)
C2F—C1F—O5F—C5F	65.3 (3)	C4G—C5G—C6G—O6G	58.5 (3)
C6F—C5F—O5F—C1F	175.5 (2)	O1G—C1G—O5G—C5G	59.6 (3)
C4F—C5F—O5F—C1F	−59.3 (3)	C2G—C1G—O5G—C5G	−61.8 (3)
O5G—C1G—O1G—C7G	62.5 (3)	C6G—C5G—O5G—C1G	−168.7 (2)
C2G—C1G—O1G—C7G	−176.0 (2)	C4G—C5G—O5G—C1G	66.7 (3)
O1G—C1G—C2G—O2G	47.2 (3)	C1F—O2G—C2G—H2G	−1.8
O5G—C1G—C2G—O2G	170.2 (2)	H1F—C1F—O2G—C2G	−41.5
O1G—C1G—C2G—C3G	−74.0 (3)	C7G—O1G—C1G—H1G	−57.5
O5G—C1G—C2G—C3G	49.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2f—H2fA···OW	0.84	1.90	2.712 (3)	162
O3f—H3fA···O2f^i	0.84	1.86	2.657 (3)	158
O4f—H4fA···O3f^i	0.84	2.07	2.888 (3)	163
O3g—H3gA···O5g^ii	0.84	2.15	2.835 (3)	139
O3g—H3gA···O5f	0.84	2.51	3.006 (3)	118
O4g—H4gA···O6g^iii	0.84	1.89	2.728 (3)	178
O6g—H6g···O3g^iv	0.84	1.99	2.795 (3)	160
OW—HW1···O3g^v	0.95 (5)	2.00 (5)	2.915 (3)	161 (3)
OW—HW2···O1g	0.95 (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, y−1, z; (v) x−1, y, z.