Methyl 3-O-α-l-fucopyranosyl β-d-glucopyran-oside tetra-hydrate.

The title compound, C(13)H(24)O(10)·4H(2)O, is the methyl glycoside of a disaccharide structural element present in the backbone of the capsular polysaccharide from Klebsiella K1, which contains only three sugars and a substituent in the polysaccharide repeating unit. The conformation of the title disaccharide is described by the glycosidic torsion angles ϕ(H) = 51.1 (1)° and ψ(H) = 25.8 (1)°. In the crystal, a number of O-H⋯O hydrogen bonds link the methyl glycoside and water mol-ecules, forming a three-dimensional network. One water mol-ecule is disordered over two positions with occupancies of 0.748 (4) and 0.252 (4).

Related literature

For a background to capsular polysaccharides (CPS), see: Jansson et al. (1988 ▶); Erbing et al. (1976 ▶); Gloaguen et al. (1999 ▶); Cescutti et al. (2005 ▶). For details of the puckering analysis, see: Cremer & Pople (1975 ▶). For the synthesis, see: Baumann et al. (1988 ▶). For a related structure, see: Eriksson & Widmalm (2012 ▶).

Experimental

Crystal data

C13H24O10·4H2O

M = 412.39

Monoclinic,

a = 9.6150 (2) Å

b = 7.1362 (1) Å

c = 13.9716 (2) Å

β = 100.1180 (18)°

V = 943.75 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.15 × 0.05 × 0.03 mm

Data collection

Oxford Xcalibur 3 diffractometer with Sapphire 3 CCD

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.976, T max = 0.996

37858 measured reflections

4836 independent reflections

4644 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.08

4836 reflections

294 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041992/is5198sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041992/is5198Isup2.hkl

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

C13H24O10·4H2O	F(000) = 444
Mr = 412.39	Dx = 1.451 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 26696 reflections
a = 9.6150 (2) Å	θ = 3.9–41.0°
b = 7.1362 (1) Å	µ = 0.13 mm−1
c = 13.9716 (2) Å	T = 100 K
β = 100.1180 (18)°	Prism, colourless
V = 943.75 (3) Å3	0.15 × 0.05 × 0.03 mm
Z = 2

Oxford Xcalibur 3 diffractometer with Sapphire 3 CCD	4836 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 16.5467 pixels mm-1	θmax = 36.3°, θmin = 4.0°
ω scans at different φ	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −11→6
Tmin = 0.976, Tmax = 0.996	l = −23→23
37858 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.0842P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
4836 reflections	Δρmax = 0.44 e Å−3
294 parameters	Δρmin = −0.26 e Å−3
16 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (4)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1F	0.06137 (8)	0.74750 (12)	0.36039 (6)	0.00779 (13)
H1F	−0.0206	0.8096	0.3826	0.009*
C2F	0.12838 (8)	0.60944 (12)	0.43883 (6)	0.00787 (13)
H2F	0.1488	0.6794	0.5017	0.009*
C3F	0.26863 (8)	0.53512 (12)	0.41753 (6)	0.00798 (13)
H3F	0.2504	0.4603	0.3561	0.010*
C4F	0.36573 (8)	0.69748 (13)	0.40472 (6)	0.00811 (13)
H4F	0.4554	0.6474	0.3877	0.010*
C5F	0.29166 (9)	0.81952 (13)	0.32155 (6)	0.00935 (13)
H5F	0.2719	0.7426	0.2608	0.011*
O5F	0.15932 (7)	0.88703 (10)	0.34442 (5)	0.00936 (11)
C6F	0.37691 (10)	0.98940 (15)	0.30347 (7)	0.01461 (16)
H6FA	0.3243	1.0623	0.2495	0.022*
H6FB	0.4672	0.9491	0.2869	0.022*
H6FC	0.3945	1.0671	0.3622	0.022*
O2F	0.03402 (7)	0.46140 (10)	0.45049 (5)	0.00979 (11)
H2FA	0.0302	0.3855	0.4041	0.015*
O3F	0.33526 (7)	0.41869 (11)	0.49451 (5)	0.01196 (12)
H3FA	0.2829	0.3267	0.5004	0.018*
O4F	0.39729 (7)	0.80024 (11)	0.49324 (5)	0.01022 (11)
H4FA	0.4823	0.8340	0.5024	0.015*
C1G	−0.32791 (9)	0.80214 (14)	0.11858 (6)	0.00982 (14)
H1G	−0.3219	0.9420	0.1219	0.012*
C2G	−0.23436 (8)	0.71631 (13)	0.20716 (6)	0.00919 (13)
H2G	−0.2543	0.5790	0.2096	0.011*
C3G	−0.07891 (8)	0.74567 (12)	0.20083 (6)	0.00806 (13)
H3G	−0.0559	0.8822	0.2081	0.010*
C4G	−0.04891 (8)	0.67751 (13)	0.10331 (6)	0.00803 (13)
H4G	−0.0682	0.5399	0.0971	0.010*
C5G	−0.14732 (9)	0.78118 (13)	0.02294 (6)	0.00859 (13)
H5G	−0.1318	0.9192	0.0311	0.010*
O5G	−0.28938 (6)	0.73757 (11)	0.03071 (4)	0.01060 (11)
C6G	−0.12642 (9)	0.72355 (14)	−0.07751 (6)	0.01059 (14)
H6G1	−0.0240	0.7129	−0.0782	0.013*
H6G2	−0.1692	0.5985	−0.0927	0.013*
O7M	−0.46601 (7)	0.74456 (12)	0.11844 (5)	0.01356 (13)
C7M	−0.56733 (10)	0.8496 (2)	0.05233 (8)	0.0228 (2)
H71	−0.5534	0.9837	0.0658	0.034*
H72	−0.6629	0.8136	0.0605	0.034*
H73	−0.5551	0.8234	−0.0145	0.034*
O2G	−0.27031 (8)	0.80440 (12)	0.29016 (5)	0.01355 (13)
H2G1	−0.2675	0.7254	0.3350	0.020*
O3G	0.01081 (7)	0.64343 (10)	0.27542 (4)	0.00823 (11)
O4G	0.09313 (7)	0.71213 (11)	0.09408 (5)	0.01101 (12)
H4G1	0.1439	0.6219	0.1178	0.017*
O6G	−0.18739 (7)	0.85281 (11)	−0.15098 (5)	0.01114 (12)
H6G	−0.2758	0.8442	−0.1596	0.017*
OW1	−0.23629 (7)	0.58785 (10)	0.45089 (5)	0.01226 (12)
H11	−0.1538 (15)	0.546 (3)	0.4560 (12)	0.018*
H12	−0.2840 (16)	0.500 (3)	0.4666 (12)	0.018*
OW2	0.02672 (8)	0.22661 (11)	0.29518 (5)	0.01423 (13)
H21	0.0697 (18)	0.276 (3)	0.2567 (12)	0.021*
H22	0.0714 (19)	0.124 (2)	0.3125 (13)	0.021*
OW3	0.53751 (9)	0.90725 (15)	0.79144 (8)	0.02575 (19)
H31	0.4671 (19)	0.846 (3)	0.7728 (15)	0.039*
H32	0.511 (2)	1.000 (3)	0.8244 (15)	0.039*
OW4A	−0.28298 (13)	1.20268 (19)	0.26647 (12)	0.0277 (4)	0.748 (4)
H41A	−0.297 (3)	1.097 (3)	0.288 (2)	0.042*	0.748 (4)
H42A	−0.196 (2)	1.217 (5)	0.276 (2)	0.042*	0.748 (4)
OW4B	−0.3277 (4)	1.2108 (6)	0.3181 (2)	0.0192 (9)	0.252 (4)
H41B	−0.269 (7)	1.128 (10)	0.313 (6)	0.029*	0.252 (4)
H42B	−0.307 (7)	1.261 (10)	0.371 (3)	0.029*	0.252 (4)

	U11	U22	U33	U12	U13	U23
C1F	0.0070 (3)	0.0093 (3)	0.0069 (3)	0.0005 (3)	0.0005 (2)	0.0001 (2)
C2F	0.0065 (3)	0.0099 (3)	0.0070 (3)	0.0003 (2)	0.0007 (2)	0.0009 (2)
C3F	0.0061 (3)	0.0088 (3)	0.0088 (3)	0.0007 (2)	0.0007 (2)	0.0010 (3)
C4F	0.0063 (3)	0.0097 (3)	0.0081 (3)	−0.0002 (2)	0.0009 (2)	0.0001 (2)
C5F	0.0080 (3)	0.0111 (3)	0.0090 (3)	0.0001 (3)	0.0015 (2)	0.0014 (3)
O5F	0.0076 (2)	0.0089 (3)	0.0114 (3)	0.0000 (2)	0.00116 (19)	0.0009 (2)
C6F	0.0130 (3)	0.0144 (4)	0.0165 (4)	−0.0030 (3)	0.0028 (3)	0.0058 (3)
O2F	0.0081 (2)	0.0116 (3)	0.0100 (2)	−0.0015 (2)	0.00258 (19)	0.0013 (2)
O3F	0.0076 (2)	0.0121 (3)	0.0152 (3)	0.0007 (2)	−0.0007 (2)	0.0063 (2)
O4F	0.0071 (2)	0.0134 (3)	0.0097 (2)	−0.0020 (2)	0.00025 (18)	−0.0024 (2)
C1G	0.0070 (3)	0.0138 (3)	0.0086 (3)	0.0012 (3)	0.0013 (2)	0.0021 (3)
C2G	0.0078 (3)	0.0125 (3)	0.0072 (3)	0.0013 (3)	0.0013 (2)	0.0014 (3)
C3G	0.0075 (3)	0.0095 (3)	0.0067 (3)	0.0011 (3)	0.0000 (2)	0.0014 (3)
C4G	0.0067 (3)	0.0101 (3)	0.0071 (3)	0.0001 (2)	0.0007 (2)	0.0007 (2)
C5G	0.0080 (3)	0.0105 (3)	0.0073 (3)	−0.0002 (2)	0.0012 (2)	0.0004 (3)
O5G	0.0069 (2)	0.0165 (3)	0.0081 (2)	−0.0010 (2)	0.00048 (18)	−0.0002 (2)
C6G	0.0121 (3)	0.0125 (3)	0.0070 (3)	0.0010 (3)	0.0012 (2)	0.0007 (3)
O7M	0.0058 (2)	0.0206 (3)	0.0140 (3)	0.0013 (2)	0.0009 (2)	0.0068 (3)
C7M	0.0092 (3)	0.0371 (6)	0.0211 (4)	0.0065 (4)	0.0002 (3)	0.0131 (4)
O2G	0.0137 (3)	0.0198 (3)	0.0079 (2)	0.0055 (3)	0.0039 (2)	0.0018 (2)
O3G	0.0086 (2)	0.0092 (3)	0.0059 (2)	0.0017 (2)	−0.00137 (18)	−0.0001 (2)
O4G	0.0066 (2)	0.0156 (3)	0.0111 (2)	0.0003 (2)	0.00206 (19)	0.0016 (2)
O6G	0.0108 (2)	0.0142 (3)	0.0076 (2)	−0.0013 (2)	−0.00058 (19)	0.0023 (2)
OW1	0.0111 (3)	0.0116 (3)	0.0148 (3)	0.0017 (2)	0.0043 (2)	0.0029 (2)
OW2	0.0165 (3)	0.0106 (3)	0.0163 (3)	0.0008 (2)	0.0047 (2)	0.0010 (2)
OW3	0.0134 (3)	0.0249 (4)	0.0370 (5)	0.0026 (3)	−0.0009 (3)	−0.0141 (4)
OW4A	0.0169 (5)	0.0176 (6)	0.0475 (9)	0.0016 (4)	0.0029 (5)	0.0056 (5)
OW4B	0.0190 (14)	0.0227 (17)	0.0162 (14)	0.0014 (12)	0.0039 (11)	−0.0007 (12)

C1F—O3G	1.4122 (10)	C3G—H3G	1.0000
C1F—O5F	1.4149 (11)	C4G—O4G	1.4158 (10)
C1F—C2F	1.5292 (11)	C4G—C5G	1.5265 (11)
C1F—H1F	1.0000	C4G—H4G	1.0000
C2F—O2F	1.4205 (11)	C5G—O5G	1.4236 (10)
C2F—C3F	1.5261 (11)	C5G—C6G	1.5094 (12)
C2F—H2F	1.0000	C5G—H5G	1.0000
C3F—O3F	1.4197 (10)	C6G—O6G	1.4272 (11)
C3F—C4F	1.5182 (12)	C6G—H6G1	0.9900
C3F—H3F	1.0000	C6G—H6G2	0.9900
C4F—O4F	1.4240 (11)	O7M—C7M	1.4311 (12)
C4F—C5F	1.5248 (12)	C7M—H71	0.9800
C4F—H4F	1.0000	C7M—H72	0.9800
C5F—O5F	1.4479 (11)	C7M—H73	0.9800
C5F—C6F	1.5094 (13)	O2G—H2G1	0.8400
C5F—H5F	1.0000	O4G—H4G1	0.8400
C6F—H6FA	0.9800	O6G—H6G	0.8400
C6F—H6FB	0.9800	OW1—H11	0.839 (14)
C6F—H6FC	0.9800	OW1—H12	0.830 (15)
O2F—H2FA	0.8400	OW2—H21	0.814 (15)
O3F—H3FA	0.8400	OW2—H22	0.862 (15)
O4F—H4FA	0.8400	OW3—H31	0.810 (16)
C1G—O7M	1.3896 (11)	OW3—H32	0.868 (16)
C1G—O5G	1.4200 (11)	OW4A—OW4B	0.904 (4)
C1G—C2G	1.5247 (11)	OW4A—H41A	0.835 (19)
C1G—H1G	1.0000	OW4A—H42A	0.826 (18)
C2G—O2G	1.4143 (11)	OW4A—H41B	0.83 (9)
C2G—C3G	1.5271 (11)	OW4B—H41A	0.98 (3)
C2G—H2G	1.0000	OW4B—H41B	0.83 (2)
C3G—O3G	1.4306 (10)	OW4B—H42B	0.81 (2)
C3G—C4G	1.5213 (11)
O3G—C1F—O5F	112.20 (6)	O2G—C2G—C1G	107.01 (7)
O3G—C1F—C2F	107.64 (7)	O2G—C2G—C3G	111.67 (7)
O5F—C1F—C2F	110.98 (6)	C1G—C2G—C3G	109.98 (7)
O3G—C1F—H1F	108.6	O2G—C2G—H2G	109.4
O5F—C1F—H1F	108.6	C1G—C2G—H2G	109.4
C2F—C1F—H1F	108.6	C3G—C2G—H2G	109.4
O2F—C2F—C3F	111.59 (7)	O3G—C3G—C4G	107.73 (7)
O2F—C2F—C1F	111.36 (6)	O3G—C3G—C2G	111.03 (7)
C3F—C2F—C1F	111.08 (7)	C4G—C3G—C2G	110.46 (7)
O2F—C2F—H2F	107.5	O3G—C3G—H3G	109.2
C3F—C2F—H2F	107.5	C4G—C3G—H3G	109.2
C1F—C2F—H2F	107.5	C2G—C3G—H3G	109.2
O3F—C3F—C4F	109.32 (6)	O4G—C4G—C3G	111.31 (7)
O3F—C3F—C2F	110.63 (7)	O4G—C4G—C5G	109.37 (7)
C4F—C3F—C2F	109.91 (7)	C3G—C4G—C5G	108.26 (7)
O3F—C3F—H3F	109.0	O4G—C4G—H4G	109.3
C4F—C3F—H3F	109.0	C3G—C4G—H4G	109.3
C2F—C3F—H3F	109.0	C5G—C4G—H4G	109.3
O4F—C4F—C3F	109.40 (7)	O5G—C5G—C6G	107.31 (7)
O4F—C4F—C5F	111.56 (7)	O5G—C5G—C4G	108.48 (7)
C3F—C4F—C5F	108.13 (6)	C6G—C5G—C4G	112.66 (7)
O4F—C4F—H4F	109.2	O5G—C5G—H5G	109.4
C3F—C4F—H4F	109.2	C6G—C5G—H5G	109.4
C5F—C4F—H4F	109.2	C4G—C5G—H5G	109.4
O5F—C5F—C6F	107.09 (7)	C1G—O5G—C5G	113.24 (6)
O5F—C5F—C4F	109.44 (7)	O6G—C6G—C5G	112.81 (8)
C6F—C5F—C4F	113.06 (7)	O6G—C6G—H6G1	109.0
O5F—C5F—H5F	109.1	C5G—C6G—H6G1	109.0
C6F—C5F—H5F	109.1	O6G—C6G—H6G2	109.0
C4F—C5F—H5F	109.1	C5G—C6G—H6G2	109.0
C1F—O5F—C5F	115.83 (7)	H6G1—C6G—H6G2	107.8
C5F—C6F—H6FA	109.5	C1G—O7M—C7M	112.83 (8)
C5F—C6F—H6FB	109.5	O7M—C7M—H71	109.5
H6FA—C6F—H6FB	109.5	O7M—C7M—H72	109.5
C5F—C6F—H6FC	109.5	H71—C7M—H72	109.5
H6FA—C6F—H6FC	109.5	O7M—C7M—H73	109.5
H6FB—C6F—H6FC	109.5	H71—C7M—H73	109.5
C2F—O2F—H2FA	109.5	H72—C7M—H73	109.5
C3F—O3F—H3FA	109.5	C2G—O2G—H2G1	109.5
C4F—O4F—H4FA	109.5	C1F—O3G—C3G	114.75 (7)
O7M—C1G—O5G	107.29 (7)	C4G—O4G—H4G1	109.5
O7M—C1G—C2G	108.04 (7)	C6G—O6G—H6G	109.5
O5G—C1G—C2G	111.41 (7)	H11—OW1—H12	105.3 (16)
O7M—C1G—H1G	110.0	H21—OW2—H22	105.5 (16)
O5G—C1G—H1G	110.0	H31—OW3—H32	106.1 (18)
C2G—C1G—H1G	110.0
O3G—C1F—C2F—O2F	−52.73 (8)	O2G—C2G—C3G—O3G	69.76 (9)
O5F—C1F—C2F—O2F	−175.86 (7)	C1G—C2G—C3G—O3G	−171.59 (7)
O3G—C1F—C2F—C3F	72.31 (8)	O2G—C2G—C3G—C4G	−170.80 (7)
O5F—C1F—C2F—C3F	−50.82 (9)	C1G—C2G—C3G—C4G	−52.15 (10)
O2F—C2F—C3F—O3F	−59.67 (9)	O3G—C3G—C4G—O4G	−61.52 (9)
C1F—C2F—C3F—O3F	175.42 (7)	C2G—C3G—C4G—O4G	177.06 (7)
O2F—C2F—C3F—C4F	179.51 (6)	O3G—C3G—C4G—C5G	178.25 (7)
C1F—C2F—C3F—C4F	54.60 (9)	C2G—C3G—C4G—C5G	56.82 (9)
O3F—C3F—C4F—O4F	−58.47 (8)	O4G—C4G—C5G—O5G	177.31 (7)
C2F—C3F—C4F—O4F	63.14 (8)	C3G—C4G—C5G—O5G	−61.25 (9)
O3F—C3F—C4F—C5F	179.85 (7)	O4G—C4G—C5G—C6G	58.65 (10)
C2F—C3F—C4F—C5F	−58.54 (8)	C3G—C4G—C5G—C6G	−179.91 (7)
O4F—C4F—C5F—O5F	−61.09 (9)	O7M—C1G—O5G—C5G	−177.77 (7)
C3F—C4F—C5F—O5F	59.25 (9)	C2G—C1G—O5G—C5G	−59.71 (10)
O4F—C4F—C5F—C6F	58.17 (9)	C6G—C5G—O5G—C1G	−173.98 (7)
C3F—C4F—C5F—C6F	178.52 (7)	C4G—C5G—O5G—C1G	64.03 (9)
O3G—C1F—O5F—C5F	−65.99 (9)	O5G—C5G—C6G—O6G	77.02 (9)
C2F—C1F—O5F—C5F	54.48 (9)	C4G—C5G—C6G—O6G	−163.63 (7)
C6F—C5F—O5F—C1F	177.74 (7)	O5G—C1G—O7M—C7M	−73.36 (11)
C4F—C5F—O5F—C1F	−59.37 (9)	C2G—C1G—O7M—C7M	166.41 (9)
O7M—C1G—C2G—O2G	−68.77 (9)	O5F—C1F—O3G—C3G	−69.16 (8)
O5G—C1G—C2G—O2G	173.62 (7)	C2F—C1F—O3G—C3G	168.45 (6)
O7M—C1G—C2G—C3G	169.75 (8)	C4G—C3G—O3G—C1F	144.26 (7)
O5G—C1G—C2G—C3G	52.15 (10)	C2G—C3G—O3G—C1F	−94.67 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2F—H2FA···OW2	0.84	1.89	2.7326 (10)	176
O3F—H3FA···O2F	0.84	2.56	2.8696 (10)	103
O3F—H3FA···OW1i	0.84	1.92	2.7049 (10)	156
O4F—H4FA···O3Fii	0.84	1.85	2.6836 (10)	172
O6G—H6G···OW3iii	0.84	1.86	2.6546 (11)	157
O2G—H2G1···OW1	0.84	1.87	2.6981 (10)	168
O4G—H4G1···O6Giv	0.84	2.00	2.7884 (11)	155
OW1—H11···O2F	0.84 (2)	1.92 (2)	2.7522 (10)	172 (2)
OW1—H12···O4Fi	0.83 (2)	1.94 (2)	2.7646 (10)	178 (2)
OW2—H21···O6Giv	0.81 (2)	2.09 (2)	2.8897 (10)	170 (2)
OW2—H22···O5Fv	0.86 (2)	1.91 (2)	2.7682 (11)	176 (2)
OW3—H31···OW4Ai	0.81 (2)	2.04 (2)	2.8424 (16)	176 (2)
OW3—H32···O7Mvi	0.87 (2)	2.00 (2)	2.8559 (13)	169 (2)
OW4A—H41A···O2G	0.83 (2)	2.10 (2)	2.8615 (16)	151 (3)
OW4A—H42A···OW2vii	0.83 (2)	2.11 (2)	2.9390 (15)	174 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2F—H2FA⋯OW2	0.84	1.89	2.7326 (10)	176
O3F—H3FA⋯O2F	0.84	2.56	2.8696 (10)	103
O3F—H3FA⋯OW1i	0.84	1.92	2.7049 (10)	156
O4F—H4FA⋯O3F ii	0.84	1.85	2.6836 (10)	172
O6G—H6G⋯OW3iii	0.84	1.86	2.6546 (11)	157
O2G—H2G1⋯OW1	0.84	1.87	2.6981 (10)	168
O4G—H4G1⋯O6G iv	0.84	2.00	2.7884 (11)	155
OW1—H11⋯O2F	0.84 (2)	1.92 (2)	2.7522 (10)	172 (2)
OW1—H12⋯O4F i	0.83 (2)	1.94 (2)	2.7646 (10)	178 (2)
OW2—H21⋯O6G iv	0.81 (2)	2.09 (2)	2.8897 (10)	170 (2)
OW2—H22⋯O5F v	0.86 (2)	1.91 (2)	2.7682 (11)	176 (2)
OW3—H31⋯OW4A i	0.81 (2)	2.04 (2)	2.8424 (16)	176 (2)
OW3—H32⋯O7M vi	0.87 (2)	2.00 (2)	2.8559 (13)	169 (2)
OW4A—H41A⋯O2G	0.83 (2)	2.10 (2)	2.8615 (16)	151 (3)
OW4A—H42A⋯OW2vii	0.83 (2)	2.11 (2)	2.9390 (15)	174 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .