5-{(2S,3R,4S,5S,6R)-3,4-Dihydr-oxy-6-hydroxy-meth-yl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydr-oxy-6-methyl-tetra-hydro-pyran-2-yloxy]tetra-hydro-pyran-2-yloxy}--7-hydr-oxy-2-(4-hydroxy-phen-yl)chromen-4-one monohydrate.

In the title compound, C(27)H(30)O(14)·H(2)O, the hydroxy-phenyl ring makes a dihedral angle of 20.05 (11)° with the chromenone ring system. The crystal structure is stabilized by intra- and inter-molecular O-H⋯O hydrogen bonds. The absolute configuration was assigned on the basis of an analagous structure.

Related literature

For related literature, see: Li et al. (2007 ▶).

Experimental

Crystal data

C27H30O14·H2O

M = 596.53

Orthorhombic,

a = 7.2392 (14) Å

b = 9.832 (2) Å

c = 36.782 (7) Å

V = 2618.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 113 (2) K

0.08 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.990, T max = 0.995

20457 measured reflections

3332 independent reflections

2875 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.05

3332 reflections

410 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2005 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027839/bt2776sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027839/bt2776Isup2.hkl

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

C27H30O14·H2O	F(000) = 1256
Mr = 596.53	Dx = 1.513 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5367 reflections
a = 7.2392 (14) Å	θ = 2.1–27.1°
b = 9.832 (2) Å	µ = 0.13 mm−1
c = 36.782 (7) Å	T = 113 K
V = 2618.1 (9) Å3	Block, white
Z = 4	0.08 × 0.06 × 0.04 mm

Rigaku Saturn CCD area-detector diffractometer	3332 independent reflections
Radiation source: rotating anode	2875 reflections with I > 2σ(I)
confocal	Rint = 0.090
ω scans	θmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −9→9
Tmin = 0.990, Tmax = 0.995	k = −12→12
20457 measured reflections	l = −30→47

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.0488P] where P = (Fo2 + 2Fc2)/3
3332 reflections	(Δ/σ)max = 0.001
410 parameters	Δρmax = 0.31 e Å−3
10 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
O1	0.4843 (3)	0.7580 (2)	0.00818 (5)	0.0211 (5)
O2	0.5796 (3)	0.9238 (2)	0.10827 (5)	0.0185 (5)
O3	0.4249 (3)	0.3145 (2)	0.05153 (5)	0.0241 (5)
H3	0.407 (5)	0.268 (4)	0.0720 (8)	0.036*
O4	0.5902 (2)	0.6692 (2)	0.13500 (5)	0.0165 (4)
O5	0.4557 (2)	0.5220 (2)	0.17460 (5)	0.0170 (4)
O6	0.8762 (3)	0.5651 (2)	0.24894 (5)	0.0205 (4)
H6	0.909 (5)	0.502 (3)	0.2620 (8)	0.031*
O7	0.6098 (3)	0.3398 (2)	0.25491 (5)	0.0231 (5)
H7	0.622 (5)	0.364 (4)	0.2769 (7)	0.035*
O8	0.2114 (3)	0.2890 (2)	0.17453 (5)	0.0252 (5)
H8	0.140 (5)	0.342 (4)	0.1646 (9)	0.038*
O9	0.9173 (2)	0.6586 (2)	0.17330 (5)	0.0167 (4)
O10	0.9519 (2)	0.8722 (2)	0.20277 (5)	0.0163 (4)
O11	1.3189 (2)	0.8698 (2)	0.17022 (5)	0.0189 (5)
H11	1.403 (4)	0.862 (4)	0.1536 (7)	0.028*
O12	1.1740 (3)	0.8979 (2)	0.09786 (5)	0.0224 (5)
H12	1.155 (5)	0.981 (3)	0.0934 (9)	0.034*
O13	0.8811 (3)	1.0723 (2)	0.11859 (5)	0.0219 (5)
H13	0.779 (4)	1.029 (4)	0.1135 (9)	0.033*
O14	0.4369 (3)	1.1650 (2)	−0.12150 (5)	0.0212 (5)
H14	0.406 (5)	1.250 (3)	−0.1214 (9)	0.032*
O15	0.3844 (4)	0.1713 (3)	0.11315 (6)	0.0375 (6)
H15A	0.358 (6)	0.199 (5)	0.1329 (8)	0.056*
H15B	0.438 (6)	0.096 (3)	0.1150 (12)	0.056*
C2	0.5093 (4)	0.8935 (3)	0.01211 (7)	0.0173 (6)
C3	0.5473 (4)	0.9489 (3)	0.04519 (7)	0.0190 (6)
H3A	0.5692	1.0439	0.0469	0.023*
C4	0.5552 (3)	0.8674 (3)	0.07760 (7)	0.0159 (6)
C5	0.5377 (3)	0.6235 (3)	0.10095 (7)	0.0149 (6)
C6	0.4977 (4)	0.4896 (3)	0.09418 (7)	0.0168 (6)
H6A	0.4939	0.4261	0.1136	0.020*
C7	0.4621 (4)	0.4463 (3)	0.05842 (7)	0.0186 (6)
C8	0.4641 (4)	0.5371 (3)	0.02980 (7)	0.0199 (6)
H8A	0.4449	0.5074	0.0055	0.024*
C9	0.4948 (4)	0.6725 (3)	0.03761 (7)	0.0178 (6)
C13	0.5313 (4)	0.7231 (3)	0.07286 (7)	0.0146 (6)
C1''	0.6285 (4)	0.5673 (3)	0.16087 (7)	0.0150 (5)
H1''	0.6935	0.4899	0.1488	0.018*
C2''	0.7487 (3)	0.6234 (3)	0.19134 (7)	0.0154 (6)
H2''	0.6905	0.7053	0.2027	0.019*
C3''	0.7742 (4)	0.5101 (3)	0.21932 (7)	0.0167 (6)
H3''	0.8472	0.4347	0.2080	0.020*
C4''	0.5868 (4)	0.4542 (3)	0.23160 (7)	0.0167 (6)
H4''	0.5165	0.5270	0.2446	0.020*
C5''	0.4779 (4)	0.4074 (3)	0.19843 (7)	0.0158 (6)
H5''	0.5506	0.3357	0.1855	0.019*
C6''	0.2879 (4)	0.3529 (3)	0.20634 (7)	0.0203 (6)
H6''1	0.2948	0.2860	0.2264	0.024*
H6''2	0.2064	0.4283	0.2142	0.024*
C1'''	1.0404 (3)	0.7556 (3)	0.18874 (7)	0.0146 (5)
H1'''	1.1133	0.7111	0.2085	0.018*
C2'''	1.1695 (3)	0.7886 (3)	0.15686 (7)	0.0159 (6)
H2'''	1.2187	0.7025	0.1461	0.019*
C3'''	1.0581 (4)	0.8670 (3)	0.12806 (7)	0.0170 (6)
H3'''	0.9544	0.8080	0.1195	0.020*
C4'''	0.9774 (4)	0.9936 (3)	0.14530 (7)	0.0162 (6)
H4'''	1.0803	1.0497	0.1555	0.019*
C5'''	0.8485 (3)	0.9518 (3)	0.17625 (7)	0.0163 (6)
H5'''	0.7459	0.8949	0.1662	0.020*
C6'''	0.7673 (4)	1.0724 (4)	0.19609 (8)	0.0253 (7)
H6''3	0.7005	1.0407	0.2177	0.038*
H6''4	0.6819	1.1207	0.1800	0.038*
H6''5	0.8668	1.1339	0.2035	0.038*
C1'	0.4910 (4)	0.9672 (3)	−0.02252 (7)	0.0182 (6)
C2'	0.5075 (4)	0.8970 (3)	−0.05549 (7)	0.0192 (6)
H2'	0.5297	0.8018	−0.0555	0.023*
C3'	0.4916 (4)	0.9662 (3)	−0.08794 (7)	0.0190 (6)
H3'	0.5052	0.9185	−0.1102	0.023*
C4'	0.4559 (4)	1.1048 (3)	−0.08840 (7)	0.0179 (6)
C5'	0.4378 (4)	1.1761 (3)	−0.05556 (7)	0.0202 (6)
H5'	0.4134	1.2710	−0.0556	0.024*
C6'	0.4557 (4)	1.1065 (3)	−0.02315 (7)	0.0223 (6)
H6'	0.4439	1.1545	−0.0009	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0317 (11)	0.0152 (12)	0.0164 (9)	−0.0001 (9)	−0.0024 (8)	0.0025 (9)
O2	0.0233 (10)	0.0176 (13)	0.0144 (9)	−0.0028 (8)	−0.0018 (7)	−0.0026 (8)
O3	0.0339 (12)	0.0184 (14)	0.0201 (10)	−0.0024 (9)	−0.0012 (8)	−0.0014 (9)
O4	0.0217 (9)	0.0151 (12)	0.0126 (8)	−0.0015 (8)	−0.0021 (7)	0.0012 (8)
O5	0.0143 (8)	0.0181 (12)	0.0187 (9)	−0.0011 (8)	−0.0007 (7)	0.0047 (9)
O6	0.0237 (10)	0.0176 (12)	0.0203 (10)	−0.0044 (9)	−0.0101 (8)	0.0030 (9)
O7	0.0326 (11)	0.0202 (12)	0.0164 (9)	−0.0053 (10)	−0.0043 (8)	0.0068 (9)
O8	0.0251 (11)	0.0260 (14)	0.0246 (10)	−0.0073 (9)	−0.0074 (8)	0.0007 (10)
O9	0.0157 (9)	0.0172 (12)	0.0173 (9)	−0.0046 (8)	0.0012 (7)	−0.0033 (8)
O10	0.0179 (9)	0.0153 (12)	0.0157 (8)	0.0015 (8)	−0.0008 (7)	−0.0011 (8)
O11	0.0153 (9)	0.0239 (13)	0.0175 (9)	−0.0033 (8)	0.0003 (7)	−0.0034 (9)
O12	0.0237 (10)	0.0250 (14)	0.0184 (10)	−0.0009 (9)	0.0081 (7)	0.0021 (10)
O13	0.0227 (10)	0.0177 (13)	0.0253 (10)	−0.0020 (9)	−0.0050 (8)	0.0049 (9)
O14	0.0330 (11)	0.0170 (13)	0.0137 (9)	0.0016 (10)	−0.0006 (7)	0.0029 (9)
O15	0.0558 (16)	0.0267 (17)	0.0299 (12)	0.0115 (13)	0.0134 (11)	0.0070 (12)
C2	0.0202 (13)	0.0136 (16)	0.0182 (12)	−0.0012 (11)	0.0004 (9)	0.0007 (12)
C3	0.0242 (13)	0.0166 (17)	0.0162 (12)	−0.0025 (12)	−0.0006 (10)	0.0015 (11)
C4	0.0138 (11)	0.0179 (17)	0.0160 (12)	−0.0024 (11)	−0.0004 (9)	−0.0009 (11)
C5	0.0151 (11)	0.0162 (16)	0.0134 (11)	−0.0001 (11)	−0.0011 (9)	−0.0008 (11)
C6	0.0195 (13)	0.0152 (17)	0.0158 (13)	0.0021 (11)	−0.0011 (9)	0.0017 (12)
C7	0.0182 (12)	0.0164 (17)	0.0213 (13)	−0.0012 (11)	0.0003 (10)	−0.0029 (12)
C8	0.0267 (14)	0.0188 (18)	0.0144 (12)	0.0005 (12)	−0.0027 (10)	−0.0027 (11)
C9	0.0185 (13)	0.0200 (18)	0.0149 (12)	−0.0014 (11)	−0.0014 (9)	0.0024 (12)
C13	0.0171 (12)	0.0136 (16)	0.0132 (12)	−0.0003 (11)	−0.0008 (9)	0.0007 (11)
C1''	0.0172 (12)	0.0134 (15)	0.0143 (11)	−0.0002 (11)	−0.0005 (9)	0.0013 (11)
C2''	0.0155 (12)	0.0155 (17)	0.0153 (12)	−0.0021 (11)	0.0009 (9)	−0.0001 (11)
C3''	0.0189 (13)	0.0154 (17)	0.0160 (12)	−0.0011 (11)	−0.0039 (9)	−0.0017 (11)
C4''	0.0195 (12)	0.0155 (16)	0.0152 (12)	−0.0018 (11)	−0.0010 (9)	0.0017 (11)
C5''	0.0210 (13)	0.0121 (16)	0.0143 (12)	−0.0006 (11)	−0.0006 (9)	0.0025 (11)
C6''	0.0195 (12)	0.0228 (18)	0.0186 (13)	−0.0053 (13)	−0.0021 (9)	0.0022 (13)
C1'''	0.0147 (11)	0.0114 (15)	0.0178 (12)	−0.0007 (11)	−0.0007 (9)	−0.0048 (11)
C2'''	0.0144 (12)	0.0152 (16)	0.0180 (12)	−0.0025 (10)	−0.0013 (9)	−0.0028 (11)
C3'''	0.0166 (12)	0.0195 (17)	0.0150 (12)	−0.0038 (11)	0.0007 (9)	0.0019 (11)
C4'''	0.0177 (12)	0.0156 (17)	0.0152 (12)	−0.0002 (11)	−0.0028 (9)	0.0046 (11)
C5'''	0.0149 (12)	0.0163 (16)	0.0178 (12)	−0.0005 (11)	−0.0001 (9)	0.0009 (12)
C6'''	0.0255 (14)	0.025 (2)	0.0250 (14)	0.0081 (13)	0.0017 (11)	−0.0009 (13)
C1'	0.0202 (13)	0.0202 (18)	0.0142 (12)	0.0015 (12)	−0.0005 (9)	0.0013 (12)
C2'	0.0243 (14)	0.0163 (17)	0.0172 (13)	0.0023 (12)	−0.0004 (10)	−0.0006 (12)
C3'	0.0264 (14)	0.0153 (17)	0.0153 (12)	0.0019 (12)	0.0007 (10)	−0.0023 (11)
C4'	0.0192 (12)	0.0196 (17)	0.0149 (12)	−0.0013 (12)	0.0005 (9)	0.0018 (12)
C5'	0.0306 (15)	0.0114 (17)	0.0186 (13)	0.0010 (12)	0.0000 (11)	−0.0017 (12)
C6'	0.0328 (15)	0.0180 (18)	0.0159 (13)	0.0025 (13)	0.0010 (11)	−0.0031 (12)

O1—C2	1.352 (4)	C8—C9	1.379 (5)
O1—C9	1.373 (3)	C8—H8A	0.9500
O2—C4	1.269 (3)	C9—C13	1.414 (4)
O3—C7	1.347 (4)	C1''—C2''	1.522 (4)
O3—H3	0.89 (2)	C1''—H1''	1.0000
O4—C5	1.384 (3)	C2''—C3''	1.528 (4)
O4—C1''	1.409 (3)	C2''—H2''	1.0000
O5—C1''	1.420 (3)	C3''—C4''	1.532 (4)
O5—C5''	1.436 (3)	C3''—H3''	1.0000
O6—C3''	1.423 (3)	C4''—C5''	1.524 (3)
O6—H6	0.82 (2)	C4''—H4''	1.0000
O7—C4''	1.424 (4)	C5''—C6''	1.505 (4)
O7—H7	0.85 (2)	C5''—H5''	1.0000
O8—C6''	1.439 (3)	C6''—H6''1	0.9900
O8—H8	0.82 (2)	C6''—H6''2	0.9900
O9—C1'''	1.423 (3)	C1'''—C2'''	1.534 (4)
O9—C2''	1.432 (3)	C1'''—H1'''	1.0000
O10—C1'''	1.412 (3)	C2'''—C3'''	1.539 (4)
O10—C5'''	1.457 (3)	C2'''—H2'''	1.0000
O11—C2'''	1.431 (3)	C3'''—C4'''	1.514 (4)
O11—H11	0.86 (2)	C3'''—H3'''	1.0000
O12—C3'''	1.425 (3)	C4'''—C5'''	1.529 (4)
O12—H12	0.85 (3)	C4'''—H4'''	1.0000
O13—C4'''	1.432 (3)	C5'''—C6'''	1.511 (4)
O13—H13	0.87 (2)	C5'''—H5'''	1.0000
O14—C4'	1.360 (3)	C6'''—H6''3	0.9800
O14—H14	0.87 (3)	C6'''—H6''4	0.9800
O15—H15A	0.80 (3)	C6'''—H6''5	0.9800
O15—H15B	0.84 (3)	C1'—C6'	1.393 (5)
C2—C3	1.361 (4)	C1'—C2'	1.400 (4)
C2—C1'	1.472 (4)	C2'—C3'	1.379 (4)
C3—C4	1.437 (4)	C2'—H2'	0.9500
C3—H3A	0.9500	C3'—C4'	1.386 (4)
C4—C13	1.440 (4)	C3'—H3'	0.9500
C5—C6	1.371 (4)	C4'—C5'	1.403 (4)
C5—C13	1.424 (4)	C5'—C6'	1.381 (4)
C6—C7	1.406 (4)	C5'—H5'	0.9500
C6—H6A	0.9500	C6'—H6'	0.9500
C7—C8	1.381 (4)
C2—O1—C9	120.8 (2)	O5—C5''—C4''	108.0 (2)
C7—O3—H3	111 (2)	C6''—C5''—C4''	115.2 (2)
C5—O4—C1''	115.7 (2)	O5—C5''—H5''	108.8
C1''—O5—C5''	111.37 (19)	C6''—C5''—H5''	108.8
C3''—O6—H6	108 (3)	C4''—C5''—H5''	108.8
C4''—O7—H7	112 (3)	O8—C6''—C5''	110.5 (2)
C6''—O8—H8	109 (3)	O8—C6''—H6''1	109.6
C1'''—O9—C2''	120.72 (19)	C5''—C6''—H6''1	109.6
C1'''—O10—C5'''	115.13 (19)	O8—C6''—H6''2	109.6
C2'''—O11—H11	104 (2)	C5''—C6''—H6''2	109.6
C3'''—O12—H12	105 (3)	H6''1—C6''—H6''2	108.1
C4'''—O13—H13	107 (2)	O10—C1'''—O9	113.9 (2)
C4'—O14—H14	116 (2)	O10—C1'''—C2'''	112.6 (2)
H15A—O15—H15B	110 (4)	O9—C1'''—C2'''	102.6 (2)
O1—C2—C3	121.1 (3)	O10—C1'''—H1'''	109.2
O1—C2—C1'	112.4 (2)	O9—C1'''—H1'''	109.2
C3—C2—C1'	126.5 (3)	C2'''—C1'''—H1'''	109.2
C2—C3—C4	121.8 (3)	O11—C2'''—C1'''	108.4 (2)
C2—C3—H3A	119.1	O11—C2'''—C3'''	110.7 (2)
C4—C3—H3A	119.1	C1'''—C2'''—C3'''	108.2 (2)
O2—C4—C3	120.0 (3)	O11—C2'''—H2'''	109.8
O2—C4—C13	123.7 (2)	C1'''—C2'''—H2'''	109.8
C3—C4—C13	116.4 (2)	C3'''—C2'''—H2'''	109.8
C6—C5—O4	122.3 (2)	O12—C3'''—C4'''	112.2 (2)
C6—C5—C13	121.4 (2)	O12—C3'''—C2'''	109.6 (2)
O4—C5—C13	116.3 (2)	C4'''—C3'''—C2'''	109.0 (2)
C5—C6—C7	120.0 (3)	O12—C3'''—H3'''	108.7
C5—C6—H6A	120.0	C4'''—C3'''—H3'''	108.7
C7—C6—H6A	120.0	C2'''—C3'''—H3'''	108.7
O3—C7—C8	118.7 (2)	O13—C4'''—C3'''	110.2 (2)
O3—C7—C6	120.3 (3)	O13—C4'''—C5'''	111.0 (2)
C8—C7—C6	121.0 (3)	C3'''—C4'''—C5'''	109.0 (2)
C9—C8—C7	117.8 (3)	O13—C4'''—H4'''	108.9
C9—C8—H8A	121.1	C3'''—C4'''—H4'''	108.9
C7—C8—H8A	121.1	C5'''—C4'''—H4'''	108.9
O1—C9—C8	114.7 (2)	O10—C5'''—C6'''	107.3 (2)
O1—C9—C13	121.2 (3)	O10—C5'''—C4'''	109.2 (2)
C8—C9—C13	124.1 (3)	C6'''—C5'''—C4'''	112.7 (3)
C9—C13—C5	115.4 (3)	O10—C5'''—H5'''	109.2
C9—C13—C4	118.7 (2)	C6'''—C5'''—H5'''	109.2
C5—C13—C4	125.8 (2)	C4'''—C5'''—H5'''	109.2
O4—C1''—O5	106.9 (2)	C5'''—C6'''—H6''3	109.5
O4—C1''—C2''	110.6 (2)	C5'''—C6'''—H6''4	109.5
O5—C1''—C2''	110.8 (2)	H6''3—C6'''—H6''4	109.5
O4—C1''—H1''	109.5	C5'''—C6'''—H6''5	109.5
O5—C1''—H1''	109.5	H6''3—C6'''—H6''5	109.5
C2''—C1''—H1''	109.5	H6''4—C6'''—H6''5	109.5
O9—C2''—C1''	103.53 (19)	C6'—C1'—C2'	119.1 (3)
O9—C2''—C3''	112.7 (2)	C6'—C1'—C2	121.0 (2)
C1''—C2''—C3''	107.5 (2)	C2'—C1'—C2	119.9 (3)
O9—C2''—H2''	110.9	C3'—C2'—C1'	119.9 (3)
C1''—C2''—H2''	110.9	C3'—C2'—H2'	120.0
C3''—C2''—H2''	110.9	C1'—C2'—H2'	120.0
O6—C3''—C2''	107.5 (2)	C2'—C3'—C4'	120.7 (3)
O6—C3''—C4''	111.7 (2)	C2'—C3'—H3'	119.6
C2''—C3''—C4''	110.7 (2)	C4'—C3'—H3'	119.6
O6—C3''—H3''	109.0	O14—C4'—C3'	117.2 (2)
C2''—C3''—H3''	109.0	O14—C4'—C5'	122.9 (3)
C4''—C3''—H3''	109.0	C3'—C4'—C5'	119.9 (3)
O7—C4''—C5''	107.7 (2)	C6'—C5'—C4'	119.2 (3)
O7—C4''—C3''	110.9 (2)	C6'—C5'—H5'	120.4
C5''—C4''—C3''	109.3 (2)	C4'—C5'—H5'	120.4
O7—C4''—H4''	109.6	C5'—C6'—C1'	121.2 (3)
C5''—C4''—H4''	109.6	C5'—C6'—H6'	119.4
C3''—C4''—H4''	109.6	C1'—C6'—H6'	119.4
O5—C5''—C6''	107.1 (2)
C9—O1—C2—C3	0.7 (4)	O6—C3''—C4''—C5''	175.5 (2)
C9—O1—C2—C1'	−179.5 (2)	C2''—C3''—C4''—C5''	55.7 (3)
O1—C2—C3—C4	−2.6 (4)	C1''—O5—C5''—C6''	−170.6 (2)
C1'—C2—C3—C4	177.6 (2)	C1''—O5—C5''—C4''	64.7 (3)
C2—C3—C4—O2	−175.6 (3)	O7—C4''—C5''—O5	−179.4 (2)
C2—C3—C4—C13	3.5 (4)	C3''—C4''—C5''—O5	−58.9 (3)
C1''—O4—C5—C6	9.7 (3)	O7—C4''—C5''—C6''	60.8 (3)
C1''—O4—C5—C13	−169.0 (2)	C3''—C4''—C5''—C6''	−178.6 (3)
O4—C5—C6—C7	−174.0 (2)	O5—C5''—C6''—O8	70.4 (3)
C13—C5—C6—C7	4.6 (4)	C4''—C5''—C6''—O8	−169.4 (2)
C5—C6—C7—O3	179.2 (3)	C5'''—O10—C1'''—O9	−61.0 (3)
C5—C6—C7—C8	−1.0 (4)	C5'''—O10—C1'''—C2'''	55.4 (3)
O3—C7—C8—C9	177.3 (3)	C2''—O9—C1'''—O10	−43.8 (3)
C6—C7—C8—C9	−2.5 (4)	C2''—O9—C1'''—C2'''	−165.8 (2)
C2—O1—C9—C8	179.2 (2)	O10—C1'''—C2'''—O11	66.0 (3)
C2—O1—C9—C13	0.2 (4)	O9—C1'''—C2'''—O11	−171.1 (2)
C7—C8—C9—O1	−176.4 (2)	O10—C1'''—C2'''—C3'''	−54.2 (3)
C7—C8—C9—C13	2.5 (4)	O9—C1'''—C2'''—C3'''	68.7 (3)
O1—C9—C13—C5	179.7 (2)	O11—C2'''—C3'''—O12	62.0 (3)
C8—C9—C13—C5	0.9 (4)	C1'''—C2'''—C3'''—O12	−179.3 (2)
O1—C9—C13—C4	0.8 (4)	O11—C2'''—C3'''—C4'''	−61.2 (3)
C8—C9—C13—C4	−178.1 (3)	C1'''—C2'''—C3'''—C4'''	57.5 (3)
C6—C5—C13—C9	−4.5 (4)	O12—C3'''—C4'''—O13	55.4 (3)
O4—C5—C13—C9	174.2 (2)	C2'''—C3'''—C4'''—O13	176.9 (2)
C6—C5—C13—C4	174.4 (3)	O12—C3'''—C4'''—C5'''	177.5 (2)
O4—C5—C13—C4	−6.9 (4)	C2'''—C3'''—C4'''—C5'''	−61.0 (3)
O2—C4—C13—C9	176.5 (2)	C1'''—O10—C5'''—C6'''	−179.1 (2)
C3—C4—C13—C9	−2.5 (4)	C1'''—O10—C5'''—C4'''	−56.6 (3)
O2—C4—C13—C5	−2.3 (4)	O13—C4'''—C5'''—O10	−179.9 (2)
C3—C4—C13—C5	178.7 (2)	C3'''—C4'''—C5'''—O10	58.5 (3)
C5—O4—C1''—O5	−80.2 (3)	O13—C4'''—C5'''—C6'''	−60.8 (3)
C5—O4—C1''—C2''	159.1 (2)	C3'''—C4'''—C5'''—C6'''	177.7 (2)
C5''—O5—C1''—O4	173.8 (2)	O1—C2—C1'—C6'	160.3 (3)
C5''—O5—C1''—C2''	−65.7 (3)	C3—C2—C1'—C6'	−19.9 (4)
C1'''—O9—C2''—C1''	158.0 (2)	O1—C2—C1'—C2'	−19.2 (3)
C1'''—O9—C2''—C3''	−86.2 (3)	C3—C2—C1'—C2'	160.6 (3)
O4—C1''—C2''—O9	−64.0 (3)	C6'—C1'—C2'—C3'	0.9 (4)
O5—C1''—C2''—O9	177.7 (2)	C2—C1'—C2'—C3'	−179.6 (3)
O4—C1''—C2''—C3''	176.6 (2)	C1'—C2'—C3'—C4'	−1.1 (4)
O5—C1''—C2''—C3''	58.3 (3)	C2'—C3'—C4'—O14	−178.2 (2)
O9—C2''—C3''—O6	70.4 (3)	C2'—C3'—C4'—C5'	0.7 (4)
C1''—C2''—C3''—O6	−176.2 (2)	O14—C4'—C5'—C6'	178.8 (3)
O9—C2''—C3''—C4''	−167.4 (2)	C3'—C4'—C5'—C6'	0.0 (4)
C1''—C2''—C3''—C4''	−53.9 (3)	C4'—C5'—C6'—C1'	−0.2 (4)
O6—C3''—C4''—O7	−66.0 (3)	C2'—C1'—C6'—C5'	−0.3 (4)
C2''—C3''—C4''—O7	174.2 (2)	C2—C1'—C6'—C5'	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O15	0.89 (3)	1.80 (3)	2.684 (3)	177 (5)
O6—H6···O10i	0.82 (3)	2.08 (3)	2.881 (3)	166 (3)
O7—H7···O11i	0.85 (3)	1.99 (3)	2.817 (3)	164 (4)
O8—H8···O14ii	0.82 (4)	2.17 (3)	2.821 (3)	136 (3)
O11—H11···O2iii	0.87 (3)	2.19 (3)	3.006 (3)	158 (3)
O13—H13···O2	0.87 (3)	1.79 (3)	2.653 (3)	172 (3)
O14—H14···O13iv	0.87 (3)	1.76 (3)	2.617 (3)	170 (3)
O15—H15A···O8	0.80 (3)	2.06 (4)	2.829 (3)	161 (4)
O15—H15B···O2v	0.84 (3)	2.00 (3)	2.820 (4)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O15	0.89 (3)	1.80 (3)	2.684 (3)	177 (5)
O6—H6⋯O10i	0.82 (3)	2.08 (3)	2.881 (3)	166 (3)
O7—H7⋯O11i	0.85 (3)	1.99 (3)	2.817 (3)	164 (4)
O8—H8⋯O14ii	0.82 (4)	2.17 (3)	2.821 (3)	136 (3)
O11—H11⋯O2iii	0.87 (3)	2.19 (3)	3.006 (3)	158 (3)
O13—H13⋯O2	0.87 (3)	1.79 (3)	2.653 (3)	172 (3)
O14—H14⋯O13iv	0.87 (3)	1.76 (3)	2.617 (3)	170 (3)
O15—H15A⋯O8	0.80 (3)	2.06 (4)	2.829 (3)	161 (4)
O15—H15B⋯O2v	0.84 (3)	2.00 (3)	2.820 (4)	168 (4)

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