Methyl α-l-rhamnosyl-(1→2)[α-l-rhamnosyl-(1→3)]-α-l-rhamnoside penta-hydrate: synchrotron study.

The title hydrate, C(19)H(34)O(13)·5H(2)O, contains a vicinally disubstituted tris-accharide in which the two terminal rhamnosyl sugar groups are positioned adjacent to each other. The conformation of the tris-accharide is described by the glycosidic torsion angles ϕ2 = 48 (1)°, ψ2 = -29 (1)°, ϕ3 = 44 (1)° and ψ3 = 4 (1)°, whereas the ψ2 torsion angle represents a conformation from the major state in solution, the ψ3 torsion angle conformation may have been caught near a potential energy saddle-point when compared to its solution structure, in which at least two but probably three conformational states are populated. Extensive inter-molecular O-H⋯O hydrogen bonding is present in the crystal and a water-containing channel is formed along the b-axis direction.

Related literature

For a description of l-rhamnose as part of polysaccharides, see: Marie et al. (1998 ▶); Perry & MacLean (2000 ▶). For a description of the conformational dynamics of the title tris­accharide, see: Eklund et al. (2005 ▶); Jonsson et al. (2011 ▶). For a description of the puckering analysis of the residues, see: Cremer & Pople (1975 ▶). For further background to l-rhamnose, see: Ansaruzzaman et al. (1996 ▶); Varki et al. (1999) ▶; Kulber-Kielb et al. (2007 ▶); Lindberg (1998 ▶); Säwén et al. (2010 ▶).

Experimental

Crystal data

C19H34O13·5H2O

M = 560.54

Monoclinic,

a = 19.345 (3) Å

b = 6.4870 (13) Å

c = 21.145 (3) Å

β = 97.617 (14)°

V = 2630.0 (8) Å3

Z = 4

Synchrotron radiation

λ = 0.8970 Å

μ = 0.22 mm−1

T = 100 K

0.20 × 0.05 × 0.01 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.97, T max = 0.99

17172 measured reflections

2906 independent reflections

2655 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.07

2906 reflections

376 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027390/hb6841sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027390/hb6841Isup2.hkl

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

C19H34O13·5H2O	F(000) = 1208
Mr = 560.54	Dx = 1.416 Mg m−3
Monoclinic, C2	Synchrotron radiation, λ = 0.8970 Å
Hall symbol: C 2y	Cell parameters from 963 reflections
a = 19.345 (3) Å	θ = 2.5–39.8°
b = 6.4870 (13) Å	µ = 0.22 mm−1
c = 21.145 (3) Å	T = 100 K
β = 97.617 (14)°	Plate, colourless
V = 2630.0 (8) Å3	0.20 × 0.05 × 0.01 mm
Z = 4

Bruker SMART 1K CCD diffractometer	2906 independent reflections
Radiation source: Beamline I711, Maxlab	2655 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.046
Detector resolution: 10 pixels mm-1	θmax = 34.1°, θmin = 2.5°
ω scan at different φ	h = −23→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −8→8
Tmin = 0.97, Tmax = 0.99	l = −23→26
17172 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
2906 reflections	(Δ/σ)max < 0.001
376 parameters	Δρmax = 0.56 e Å−3
16 restraints	Δρmin = −0.29 e Å−3

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
OW1	0.93266 (10)	−0.3863 (3)	0.46456 (9)	0.0236 (4)
H101	0.9098 (15)	−0.456 (4)	0.4905 (12)	0.035*
H102	0.9424 (17)	−0.474 (4)	0.4352 (12)	0.035*
OW2	0.55372 (9)	−0.3755 (3)	0.25876 (10)	0.0244 (4)
H201	0.5191 (11)	−0.458 (4)	0.2626 (15)	0.037*
H202	0.5911 (10)	−0.422 (5)	0.2816 (14)	0.037*
OW3	0.93523 (9)	0.2971 (3)	0.37476 (9)	0.0213 (4)
H301	0.9740 (11)	0.225 (5)	0.3809 (13)	0.032*
H302	0.9301 (15)	0.339 (5)	0.3350 (8)	0.032*
OW4	0.85929 (11)	−0.0490 (3)	0.41056 (10)	0.0321 (5)
H401	0.8879 (15)	0.052 (4)	0.4032 (17)	0.048*
H402	0.8891 (14)	−0.133 (4)	0.4327 (16)	0.048*
OW5	1.04589 (10)	0.0556 (3)	0.43863 (9)	0.0271 (4)
H501	1.0791 (14)	0.144 (5)	0.4484 (14)	0.041*
H502	1.0265 (15)	0.022 (5)	0.4722 (11)	0.041*
C11	0.85217 (11)	−0.0103 (3)	0.23565 (11)	0.0109 (5)
H11	0.8527	0.0985	0.2692	0.013*
C12	0.88270 (11)	−0.2061 (3)	0.26740 (11)	0.0116 (5)
H12	0.8528	−0.2573	0.2992	0.014*
C13	0.88938 (12)	−0.3693 (3)	0.21708 (11)	0.0126 (5)
H13	0.8419	−0.4074	0.1957	0.015*
C14	0.93200 (12)	−0.2870 (3)	0.16795 (11)	0.0116 (5)
H14	0.9806	−0.2587	0.1886	0.014*
C15	0.89936 (12)	−0.0874 (4)	0.13897 (11)	0.0121 (5)
H15	0.8521	−0.1181	0.1157	0.014*
O15	0.89286 (8)	0.0599 (2)	0.18944 (7)	0.0107 (3)
O12	0.94950 (8)	−0.1441 (2)	0.29873 (8)	0.0133 (4)
H12A	0.9670	−0.2405	0.3221	0.020*
O13	0.92191 (9)	−0.5475 (3)	0.24839 (8)	0.0174 (4)
H13A	0.9233	−0.6427	0.2217	0.026*
O14	0.93366 (8)	−0.4346 (3)	0.11879 (8)	0.0155 (4)
H14A	0.9728	−0.4926	0.1230	0.023*
C16	0.94325 (14)	0.0139 (4)	0.09399 (12)	0.0192 (5)
H16A	0.9205	0.1412	0.0771	0.029*
H16B	0.9485	−0.0801	0.0586	0.029*
H16C	0.9893	0.0465	0.1169	0.029*
C21	0.74537 (12)	0.1967 (4)	0.12541 (11)	0.0135 (5)
H21	0.7951	0.1923	0.1173	0.016*
C22	0.74289 (11)	0.1369 (3)	0.19460 (11)	0.0109 (5)
H22	0.7628	0.2513	0.2231	0.013*
O22	0.78200 (8)	−0.0481 (2)	0.21047 (7)	0.0106 (3)
C23	0.66745 (11)	0.0994 (3)	0.20516 (11)	0.0105 (5)
H23	0.6417	0.2329	0.1986	0.013*
C24	0.63267 (11)	−0.0554 (4)	0.15733 (11)	0.0120 (5)
H24	0.6584	−0.1893	0.1615	0.014*
C25	0.63456 (12)	0.0347 (4)	0.09175 (11)	0.0147 (5)
H25	0.6115	0.1730	0.0896	0.018*
O23	0.66298 (8)	0.0302 (2)	0.26878 (7)	0.0111 (3)
O24	0.56178 (8)	−0.0859 (3)	0.16682 (8)	0.0151 (4)
H24A	0.5600	−0.1706	0.1966	0.023*
O25	0.70645 (8)	0.0599 (3)	0.08206 (8)	0.0150 (4)
C26	0.59920 (13)	−0.0981 (5)	0.03875 (12)	0.0228 (6)
H26A	0.6034	−0.0334	−0.0024	0.034*
H26B	0.5498	−0.1132	0.0436	0.034*
H26C	0.6213	−0.2342	0.0406	0.034*
O27	0.72203 (9)	0.4015 (2)	0.11823 (8)	0.0160 (4)
C27	0.74020 (15)	0.4932 (5)	0.06129 (14)	0.0277 (6)
H27A	0.7895	0.4660	0.0581	0.042*
H27B	0.7324	0.6423	0.0625	0.042*
H27C	0.7112	0.4341	0.0242	0.042*
C31	0.62082 (12)	0.1575 (4)	0.30105 (11)	0.0110 (5)
H31	0.5776	0.1923	0.2715	0.013*
C32	0.60030 (11)	0.0409 (4)	0.35762 (10)	0.0110 (5)
H32	0.5808	−0.0956	0.3422	0.013*
C33	0.66440 (12)	0.0023 (3)	0.40588 (11)	0.0106 (5)
H33	0.6966	−0.0894	0.3854	0.013*
C34	0.70281 (12)	0.2040 (3)	0.42416 (11)	0.0108 (5)
H34	0.6719	0.2960	0.4460	0.013*
C35	0.72015 (12)	0.3104 (3)	0.36380 (11)	0.0111 (5)
H35	0.7515	0.2194	0.3422	0.013*
O35	0.65577 (8)	0.3437 (2)	0.32144 (7)	0.0117 (3)
O32	0.54699 (8)	0.1518 (3)	0.38395 (8)	0.0126 (3)
H32A	0.5645	0.2558	0.4037	0.019*
O33	0.64458 (8)	−0.1032 (2)	0.45946 (8)	0.0133 (4)
H33A	0.6805	−0.1388	0.4838	0.020*
O34	0.76396 (8)	0.1594 (3)	0.46677 (8)	0.0157 (4)
H34A	0.7898	0.0805	0.4488	0.024*
C36	0.75423 (13)	0.5176 (4)	0.37637 (12)	0.0187 (5)
H36A	0.7546	0.5910	0.3359	0.028*
H36B	0.8023	0.4985	0.3969	0.028*
H36C	0.7281	0.5980	0.4044	0.028*

	U11	U22	U33	U12	U13	U23
OW1	0.0248 (10)	0.0236 (10)	0.0246 (10)	0.0013 (8)	0.0114 (8)	−0.0030 (8)
OW2	0.0130 (9)	0.0193 (9)	0.0394 (12)	−0.0022 (8)	−0.0019 (8)	0.0144 (8)
OW3	0.0211 (10)	0.0208 (9)	0.0218 (10)	−0.0004 (8)	0.0019 (8)	−0.0010 (8)
OW4	0.0354 (12)	0.0274 (11)	0.0349 (12)	−0.0050 (10)	0.0102 (10)	0.0050 (9)
OW5	0.0270 (11)	0.0176 (9)	0.0343 (11)	−0.0025 (8)	−0.0046 (9)	0.0022 (9)
C11	0.0078 (11)	0.0104 (10)	0.0138 (11)	−0.0012 (9)	−0.0008 (9)	−0.0032 (9)
C12	0.0066 (11)	0.0135 (11)	0.0143 (12)	−0.0022 (9)	0.0000 (9)	−0.0007 (9)
C13	0.0112 (11)	0.0085 (10)	0.0171 (12)	−0.0003 (9)	−0.0018 (9)	0.0011 (9)
C14	0.0086 (11)	0.0113 (10)	0.0139 (11)	0.0015 (9)	−0.0025 (9)	−0.0015 (9)
C15	0.0108 (11)	0.0108 (10)	0.0140 (12)	−0.0002 (9)	−0.0006 (9)	−0.0005 (9)
O15	0.0098 (8)	0.0089 (7)	0.0133 (8)	0.0001 (6)	0.0020 (6)	−0.0003 (7)
O12	0.0097 (8)	0.0133 (8)	0.0149 (9)	0.0010 (7)	−0.0055 (6)	0.0006 (7)
O13	0.0251 (9)	0.0082 (8)	0.0185 (9)	0.0040 (7)	0.0017 (7)	0.0012 (7)
O14	0.0131 (8)	0.0163 (8)	0.0164 (9)	0.0063 (7)	−0.0006 (7)	−0.0047 (7)
C16	0.0241 (14)	0.0176 (12)	0.0172 (13)	0.0002 (10)	0.0075 (10)	0.0026 (10)
C21	0.0104 (12)	0.0126 (11)	0.0179 (12)	0.0031 (9)	0.0032 (9)	0.0022 (10)
C22	0.0080 (11)	0.0083 (10)	0.0161 (12)	0.0034 (9)	0.0009 (9)	−0.0015 (9)
O22	0.0055 (8)	0.0099 (7)	0.0156 (8)	0.0017 (6)	−0.0012 (6)	0.0010 (6)
C23	0.0092 (11)	0.0120 (11)	0.0100 (11)	0.0023 (9)	0.0003 (8)	0.0011 (9)
C24	0.0054 (10)	0.0154 (11)	0.0154 (11)	0.0028 (9)	0.0014 (9)	−0.0010 (10)
C25	0.0100 (11)	0.0196 (12)	0.0139 (12)	0.0027 (10)	−0.0010 (9)	0.0000 (10)
O23	0.0088 (8)	0.0131 (8)	0.0113 (8)	0.0038 (6)	0.0016 (6)	0.0013 (7)
O24	0.0084 (8)	0.0199 (9)	0.0167 (9)	−0.0017 (7)	0.0007 (6)	0.0043 (7)
O25	0.0124 (8)	0.0204 (9)	0.0123 (8)	0.0013 (7)	0.0018 (6)	−0.0015 (7)
C26	0.0146 (13)	0.0365 (15)	0.0163 (13)	−0.0014 (11)	−0.0014 (10)	−0.0060 (12)
O27	0.0161 (9)	0.0126 (8)	0.0199 (9)	0.0052 (7)	0.0050 (7)	0.0070 (7)
C27	0.0283 (15)	0.0270 (14)	0.0291 (15)	0.0056 (12)	0.0082 (12)	0.0162 (12)
C31	0.0073 (10)	0.0126 (10)	0.0128 (11)	0.0009 (9)	−0.0004 (8)	−0.0017 (9)
C32	0.0092 (11)	0.0102 (10)	0.0131 (11)	−0.0006 (9)	−0.0004 (9)	−0.0008 (9)
C33	0.0118 (11)	0.0079 (10)	0.0124 (11)	0.0010 (9)	0.0030 (9)	0.0017 (9)
C34	0.0101 (11)	0.0097 (10)	0.0123 (11)	0.0004 (9)	−0.0003 (9)	−0.0017 (9)
C35	0.0074 (11)	0.0118 (11)	0.0137 (12)	0.0013 (9)	−0.0005 (9)	−0.0012 (9)
O35	0.0111 (8)	0.0106 (7)	0.0125 (8)	0.0002 (6)	−0.0015 (6)	0.0001 (6)
O32	0.0087 (8)	0.0153 (8)	0.0142 (8)	0.0009 (7)	0.0029 (6)	0.0009 (7)
O33	0.0105 (8)	0.0141 (8)	0.0142 (8)	0.0013 (7)	−0.0024 (6)	0.0036 (7)
O34	0.0103 (8)	0.0193 (9)	0.0165 (9)	0.0017 (7)	−0.0022 (7)	0.0008 (7)
C36	0.0204 (13)	0.0152 (12)	0.0201 (13)	−0.0065 (10)	0.0006 (10)	−0.0002 (10)

OW1—H101	0.875 (15)	C23—O23	1.432 (3)
OW1—H102	0.879 (15)	C23—C24	1.517 (3)
OW2—H201	0.871 (15)	C23—H23	1.0000
OW2—H202	0.869 (15)	C24—O24	1.426 (3)
OW3—H301	0.878 (14)	C24—C25	1.510 (3)
OW3—H302	0.877 (14)	C24—H24	1.0000
OW4—H401	0.883 (15)	C25—O25	1.442 (3)
OW4—H402	0.883 (15)	C25—C26	1.504 (3)
OW5—H501	0.867 (15)	C25—H25	1.0000
OW5—H502	0.873 (14)	O23—C31	1.400 (3)
C11—O15	1.409 (3)	O24—H24A	0.8400
C11—O22	1.412 (3)	C26—H26A	0.9800
C11—C12	1.519 (3)	C26—H26B	0.9800
C11—H11	1.0000	C26—H26C	0.9800
C12—O12	1.429 (3)	O27—C27	1.428 (3)
C12—C13	1.519 (3)	C27—H27A	0.9800
C12—H12	1.0000	C27—H27B	0.9800
C13—O13	1.435 (3)	C27—H27C	0.9800
C13—C14	1.507 (3)	C31—O35	1.423 (3)
C13—H13	1.0000	C31—C32	1.512 (3)
C14—O14	1.417 (3)	C31—H31	1.0000
C14—C15	1.532 (3)	C32—O32	1.429 (3)
C14—H14	1.0000	C32—C33	1.519 (3)
C15—O15	1.451 (3)	C32—H32	1.0000
C15—C16	1.507 (3)	C33—O33	1.419 (3)
C15—H15	1.0000	C33—C34	1.529 (3)
O12—H12A	0.8400	C33—H33	1.0000
O13—H13A	0.8400	C34—O34	1.419 (3)
O14—H14A	0.8400	C34—C35	1.527 (3)
C16—H16A	0.9800	C34—H34	1.0000
C16—H16B	0.9800	C35—O35	1.451 (3)
C16—H16C	0.9800	C35—C36	1.505 (3)
C21—O27	1.405 (3)	C35—H35	1.0000
C21—O25	1.419 (3)	O32—H32A	0.8400
C21—C22	1.521 (3)	O33—H33A	0.8400
C21—H21	1.0000	O34—H34A	0.8400
C22—O22	1.434 (3)	C36—H36A	0.9800
C22—C23	1.525 (3)	C36—H36B	0.9800
C22—H22	1.0000	C36—H36C	0.9800
H101—OW1—H102	106 (2)	C25—C24—C23	107.07 (19)
H201—OW2—H202	109 (2)	O24—C24—H24	110.2
H301—OW3—H302	107 (2)	C25—C24—H24	110.2
H401—OW4—H402	100 (2)	C23—C24—H24	110.2
H501—OW5—H502	111 (2)	O25—C25—C26	108.12 (19)
O15—C11—O22	113.08 (18)	O25—C25—C24	108.40 (17)
O15—C11—C12	110.89 (18)	C26—C25—C24	113.5 (2)
O22—C11—C12	108.63 (17)	O25—C25—H25	108.9
O15—C11—H11	108.0	C26—C25—H25	108.9
O22—C11—H11	108.0	C24—C25—H25	108.9
C12—C11—H11	108.0	C31—O23—C23	112.64 (17)
O12—C12—C13	111.41 (18)	C24—O24—H24A	109.5
O12—C12—C11	104.15 (17)	C21—O25—C25	114.75 (17)
C13—C12—C11	109.73 (18)	C25—C26—H26A	109.5
O12—C12—H12	110.5	C25—C26—H26B	109.5
C13—C12—H12	110.5	H26A—C26—H26B	109.5
C11—C12—H12	110.5	C25—C26—H26C	109.5
O13—C13—C14	110.90 (19)	H26A—C26—H26C	109.5
O13—C13—C12	108.14 (18)	H26B—C26—H26C	109.5
C14—C13—C12	109.94 (19)	C21—O27—C27	111.92 (19)
O13—C13—H13	109.3	O27—C27—H27A	109.5
C14—C13—H13	109.3	O27—C27—H27B	109.5
C12—C13—H13	109.3	H27A—C27—H27B	109.5
O14—C14—C13	109.53 (18)	O27—C27—H27C	109.5
O14—C14—C15	109.00 (18)	H27A—C27—H27C	109.5
C13—C14—C15	109.94 (19)	H27B—C27—H27C	109.5
O14—C14—H14	109.5	O23—C31—O35	111.35 (18)
C13—C14—H14	109.5	O23—C31—C32	108.77 (18)
C15—C14—H14	109.5	O35—C31—C32	110.42 (18)
O15—C15—C16	106.72 (19)	O23—C31—H31	108.7
O15—C15—C14	109.51 (17)	O35—C31—H31	108.7
C16—C15—C14	112.6 (2)	C32—C31—H31	108.7
O15—C15—H15	109.3	O32—C32—C31	109.59 (18)
C16—C15—H15	109.3	O32—C32—C33	112.85 (18)
C14—C15—H15	109.3	C31—C32—C33	109.72 (18)
C11—O15—C15	114.07 (17)	O32—C32—H32	108.2
C12—O12—H12A	109.5	C31—C32—H32	108.2
C13—O13—H13A	109.5	C33—C32—H32	108.2
C14—O14—H14A	109.5	O33—C33—C32	109.45 (18)
C15—C16—H16A	109.5	O33—C33—C34	112.62 (18)
C15—C16—H16B	109.5	C32—C33—C34	110.77 (18)
H16A—C16—H16B	109.5	O33—C33—H33	107.9
C15—C16—H16C	109.5	C32—C33—H33	107.9
H16A—C16—H16C	109.5	C34—C33—H33	107.9
H16B—C16—H16C	109.5	O34—C34—C35	111.48 (18)
O27—C21—O25	112.73 (18)	O34—C34—C33	108.79 (18)
O27—C21—C22	107.14 (19)	C35—C34—C33	109.19 (17)
O25—C21—C22	112.34 (19)	O34—C34—H34	109.1
O27—C21—H21	108.2	C35—C34—H34	109.1
O25—C21—H21	108.2	C33—C34—H34	109.1
C22—C21—H21	108.2	O35—C35—C36	107.24 (18)
O22—C22—C21	110.84 (18)	O35—C35—C34	108.53 (18)
O22—C22—C23	108.53 (17)	C36—C35—C34	113.29 (19)
C21—C22—C23	109.54 (18)	O35—C35—H35	109.2
O22—C22—H22	109.3	C36—C35—H35	109.2
C21—C22—H22	109.3	C34—C35—H35	109.2
C23—C22—H22	109.3	C31—O35—C35	113.29 (16)
C11—O22—C22	113.20 (16)	C32—O32—H32A	109.5
O23—C23—C24	110.01 (18)	C33—O33—H33A	109.5
O23—C23—C22	111.45 (17)	C34—O34—H34A	109.5
C24—C23—C22	110.88 (18)	C35—C36—H36A	109.5
O23—C23—H23	108.1	C35—C36—H36B	109.5
C24—C23—H23	108.1	H36A—C36—H36B	109.5
C22—C23—H23	108.1	C35—C36—H36C	109.5
O24—C24—C25	108.90 (17)	H36A—C36—H36C	109.5
O24—C24—C23	110.37 (18)	H36B—C36—H36C	109.5
O15—C11—C12—O12	63.1 (2)	C22—C23—C24—C25	−60.4 (2)
O22—C11—C12—O12	−172.08 (17)	O24—C24—C25—O25	−178.52 (18)
O15—C11—C12—C13	−56.3 (2)	C23—C24—C25—O25	62.1 (2)
O22—C11—C12—C13	68.6 (2)	O24—C24—C25—C26	−58.4 (3)
O12—C12—C13—O13	62.0 (2)	C23—C24—C25—C26	−177.72 (19)
C11—C12—C13—O13	176.82 (17)	C24—C23—O23—C31	−113.6 (2)
O12—C12—C13—C14	−59.2 (2)	C22—C23—O23—C31	122.95 (19)
C11—C12—C13—C14	55.6 (2)	O27—C21—O25—C25	−65.9 (2)
O13—C13—C14—O14	64.7 (2)	C22—C21—O25—C25	55.2 (2)
C12—C13—C14—O14	−175.75 (17)	C26—C25—O25—C21	174.83 (19)
O13—C13—C14—C15	−175.54 (17)	C24—C25—O25—C21	−61.7 (2)
C12—C13—C14—C15	−56.0 (2)	O25—C21—O27—C27	−72.3 (2)
O14—C14—C15—O15	176.01 (17)	C22—C21—O27—C27	163.6 (2)
C13—C14—C15—O15	55.9 (2)	C23—O23—C31—O35	−76.1 (2)
O14—C14—C15—C16	−65.4 (2)	C23—O23—C31—C32	162.03 (16)
C13—C14—C15—C16	174.51 (19)	O23—C31—C32—O32	−169.04 (17)
O22—C11—O15—C15	−63.2 (2)	O35—C31—C32—O32	68.5 (2)
C12—C11—O15—C15	59.1 (2)	O23—C31—C32—C33	66.5 (2)
C16—C15—O15—C11	179.25 (18)	O35—C31—C32—C33	−55.9 (2)
C14—C15—O15—C11	−58.6 (2)	O32—C32—C33—O33	56.2 (2)
O27—C21—C22—O22	−165.21 (16)	C31—C32—C33—O33	178.75 (18)
O25—C21—C22—O22	70.5 (2)	O32—C32—C33—C34	−68.5 (2)
O27—C21—C22—C23	75.1 (2)	C31—C32—C33—C34	54.0 (2)
O25—C21—C22—C23	−49.3 (2)	O33—C33—C34—O34	59.9 (2)
O15—C11—O22—C22	−72.0 (2)	C32—C33—C34—O34	−177.17 (18)
C12—C11—O22—C22	164.44 (18)	O33—C33—C34—C35	−178.26 (18)
C21—C22—O22—C11	91.8 (2)	C32—C33—C34—C35	−55.3 (2)
C23—C22—O22—C11	−147.87 (18)	O34—C34—C35—O35	177.68 (17)
O22—C22—C23—O23	55.3 (2)	C33—C34—C35—O35	57.5 (2)
C21—C22—C23—O23	176.42 (18)	O34—C34—C35—C36	−63.3 (2)
O22—C22—C23—C24	−67.6 (2)	C33—C34—C35—C36	176.44 (19)
C21—C22—C23—C24	53.5 (2)	O23—C31—O35—C35	−59.2 (2)
O23—C23—C24—O24	57.5 (2)	C32—C31—O35—C35	61.8 (2)
C22—C23—C24—O24	−178.80 (17)	C36—C35—O35—C31	174.92 (19)
O23—C23—C24—C25	175.84 (17)	C34—C35—O35—C31	−62.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—H101···O33i	0.88 (3)	1.85 (3)	2.726 (2)	176 (2)
OW1—H102···OW3ii	0.88 (3)	1.95 (3)	2.802 (2)	162 (2)
OW1—H102···O32iii	0.88 (3)	2.55 (3)	2.976 (2)	110 (2)
OW2—H201···O12iv	0.88 (3)	2.03 (3)	2.875 (2)	163 (2)
OW2—H202···O35ii	0.87 (3)	2.08 (3)	2.877 (2)	153 (2)
OW3—H301···OW5	0.88 (3)	2.04 (3)	2.845 (2)	151 (2)
OW3—H302···O13v	0.88 (3)	1.96 (3)	2.836 (2)	176 (2)
OW4—H401···OW3	0.88 (3)	1.97 (3)	2.840 (2)	168 (2)
OW4—H402···OW1	0.88 (3)	1.92 (3)	2.771 (2)	160 (2)
OW5—H501···O33vi	0.87 (3)	2.07 (3)	2.918 (2)	168 (2)
OW5—H502···OW5vii	0.87 (3)	2.50 (3)	3.333 (2)	159 (2)
O12—H12A···O32iii	0.84	2.01	2.767 (2)	149
O13—H13A···O15ii	0.84	2.10	2.858 (2)	149
O14—H14A···O24iii	0.84	1.95	2.733 (2)	157
O24—H24A···OW2	0.84	1.88	2.722 (2)	176
O32—H32A···OW5viii	0.84	2.13	2.864 (2)	146
O33—H33A···O34i	0.84	1.91	2.684 (2)	152
O34—H34A···OW4	0.84	1.86	2.687 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW1—H101⋯O33i	0.88 (3)	1.85 (3)	2.726 (2)	176 (2)
OW1—H102⋯OW3ii	0.88 (3)	1.95 (3)	2.802 (2)	162 (2)
OW1—H102⋯O32iii	0.88 (3)	2.55 (3)	2.976 (2)	110 (2)
OW2—H201⋯O12iv	0.88 (3)	2.03 (3)	2.875 (2)	163 (2)
OW2—H202⋯O35ii	0.87 (3)	2.08 (3)	2.877 (2)	153 (2)
OW3—H301⋯OW5	0.88 (3)	2.04 (3)	2.845 (2)	151 (2)
OW3—H302⋯O13v	0.88 (3)	1.96 (3)	2.836 (2)	176 (2)
OW4—H401⋯OW3	0.88 (3)	1.97 (3)	2.840 (2)	168 (2)
OW4—H402⋯OW1	0.88 (3)	1.92 (3)	2.771 (2)	160 (2)
OW5—H501⋯O33vi	0.87 (3)	2.07 (3)	2.918 (2)	168 (2)
OW5—H502⋯OW5vii	0.87 (3)	2.50 (3)	3.333 (2)	159 (2)
O12—H12A⋯O32iii	0.84	2.01	2.767 (2)	149
O13—H13A⋯O15ii	0.84	2.10	2.858 (2)	149
O14—H14A⋯O24iii	0.84	1.95	2.733 (2)	157
O24—H24A⋯OW2	0.84	1.88	2.722 (2)	176
O32—H32A⋯OW5viii	0.84	2.13	2.864 (2)	146
O33—H33A⋯O34i	0.84	1.91	2.684 (2)	152
O34—H34A⋯OW4	0.84	1.86	2.687 (2)	168

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