Tris[(6S)-6-hy-droxy-4-epi-shikimic acid] monohydrate: an enanti-omerically pure hy-droxy-lated shikimic acid derived from methyl shikimate.

The title compound, 3C(7)H(10)O(6)·H(2)O, is the enanti-omerically pure product of a multi-step synthesis from the enanti-omerically pure natural shikimic acid. The asymmetric unit contains three mol-ecules of the acid and one mol-ecule of water. The cyclo-hexene rings of the acids have half-chair conformations. The carboxyl-ate, the four hydroxide groups and the additional water mol-ecule form a complex three-dimensional hydrogen-bonding network.

Related literature

A series of anti­tumor-active marine natural carbasugars has been isolated in the last two decades with a cyclo­hexene-1-carboxyl­ate core structure and four contiguous stereogenic centers (Numata et al., 1997 ▶). The relative configuration of these compounds, the pericosines, has been a matter of debate since the first reports on the isolation (Usami et al., 2008 ▶, 2009 ▶). By means of detailed NMR analysis of the natural compound pericosine D0 and comparison with the NMR data published for the 6-hy­droxy-5-epishikimic acid described herein, the absolute and relative configuration was established (Usami et al., 2006 ▶, 2011 ▶). This reveals the importance of this X-ray crystallographic determination that finally proves the assignments that resulted from spectroscopic analyses. For the synthesis, see: Griesbeck et al. (2007 ▶).

Experimental

Crystal data

3C7H10O6·H2O

M = 588.47

Monoclinic,

a = 11.2561 (17) Å

b = 7.7049 (11) Å

c = 13.9688 (14) Å

β = 91.672 (8)°

V = 1211.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.20 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

5629 measured reflections

2786 independent reflections

1399 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.102

S = 0.88

2786 reflections

371 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft 1998 ▶); cell refinement: DENZO (Otwinowski & Minor 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SCHAKAL99 (Keller 1999 ▶); software used to prepare material for publication: PLATON (Spek 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041256/gg2099sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041256/gg2099Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041256/gg2099Isup3.hkl

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

3C7H10O6·H2O	F(000) = 620
Mr = 588.47	Dx = 1.614 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5629 reflections
a = 11.2561 (17) Å	θ = 2.3–27.0°
b = 7.7049 (11) Å	µ = 0.15 mm−1
c = 13.9688 (14) Å	T = 100 K
β = 91.672 (8)°	Prism, colourless
V = 1211.0 (3) Å3	0.20 × 0.10 × 0.05 mm
Z = 2

Nonius KappaCCD diffractometer	1399 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.085
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −6→14
5629 measured reflections	k = −8→9
2786 independent reflections	l = −14→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3
2786 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.28 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	−0.3102 (4)	−0.2913 (5)	−0.2574 (2)	0.0246 (12)
O2	−0.3049 (4)	−0.4950 (5)	−0.3725 (2)	0.0237 (11)
H2	−0.2943	−0.5608	−0.3251	0.036*
O3	−0.4164 (4)	−0.2120 (5)	−0.6636 (2)	0.0235 (11)
H3	−0.4002	−0.1782	−0.7189	0.035*
O4	−0.3797 (4)	0.1684 (5)	−0.6388 (2)	0.0211 (11)
H4	−0.4069	0.2653	−0.6226	0.032*
O5	−0.2179 (4)	0.1329 (5)	−0.4720 (2)	0.0199 (11)
H5	−0.1998	0.1762	−0.5249	0.030*
O6	−0.4911 (4)	−0.0313 (5)	−0.3704 (2)	0.0226 (11)
H6	−0.5149	0.0667	−0.3527	0.034*
C1	−0.3322 (5)	−0.2021 (8)	−0.4214 (4)	0.0133 (14)
C2	−0.3220 (5)	−0.2449 (8)	−0.5113 (4)	0.0181 (16)
H2AA	−0.3016	−0.3617	−0.5251	0.022*
C3	−0.3400 (6)	−0.1242 (8)	−0.5937 (4)	0.0170 (15)
H3AA	−0.2616	−0.0992	−0.6227	0.020*
C4	−0.3972 (6)	0.0455 (8)	−0.5639 (4)	0.0195 (16)
H4AA	−0.4844	0.0266	−0.5567	0.023*
C5	−0.3437 (6)	0.1095 (8)	−0.4700 (4)	0.0167 (15)
H5AA	−0.3817	0.2224	−0.4532	0.020*
C6	−0.3652 (5)	−0.0227 (8)	−0.3891 (4)	0.0166 (15)
H6AA	−0.3188	0.0098	−0.3297	0.020*
C7	−0.3140 (5)	−0.3311 (8)	−0.3425 (4)	0.0175 (15)
O1A	0.3146 (4)	0.7830 (5)	0.2305 (3)	0.0250 (12)
O2A	0.2868 (4)	0.9807 (5)	0.1148 (2)	0.0272 (12)
H2A	0.2832	1.0478	0.1620	0.041*
O3A	0.4144 (4)	0.7044 (5)	−0.1699 (2)	0.0261 (12)
H3A	0.3921	0.6804	−0.2262	0.039*
O4A	0.3839 (4)	0.3234 (5)	−0.1463 (2)	0.0213 (11)
H4A	0.4305	0.2398	−0.1364	0.032*
O5A	0.2219 (4)	0.3483 (5)	0.0099 (2)	0.0235 (11)
H5A	0.2113	0.2508	−0.0159	0.035*
O6A	0.4887 (4)	0.5260 (5)	0.1274 (2)	0.0221 (11)
H6A	0.5103	0.4374	0.1584	0.033*
C1A	0.3275 (5)	0.6941 (8)	0.0687 (4)	0.0159 (15)
C2A	0.3199 (5)	0.7380 (8)	−0.0230 (4)	0.0186 (16)
H2A1	0.2996	0.8547	−0.0383	0.022*
C3A	0.3412 (6)	0.6154 (8)	−0.1043 (4)	0.0189 (16)
H3A1	0.2633	0.5876	−0.1371	0.023*
C4A	0.3988 (6)	0.4488 (7)	−0.0705 (3)	0.0175 (16)
H4A1	0.4857	0.4701	−0.0591	0.021*
C5A	0.3472 (6)	0.3813 (8)	0.0213 (3)	0.0186 (16)
H5A1	0.3884	0.2709	0.0399	0.022*
C6A	0.3646 (6)	0.5122 (7)	0.1018 (4)	0.0172 (15)
H6A1	0.3184	0.4767	0.1586	0.021*
C7A	0.3083 (6)	0.8202 (8)	0.1454 (4)	0.0187 (16)
O1B	−0.0345 (4)	−0.3888 (5)	−0.4150 (3)	0.0299 (12)
O2B	−0.0513 (4)	−0.4555 (5)	−0.2592 (3)	0.0285 (12)
H2B	−0.0715	−0.5529	−0.2813	0.043*
O3B	0.1426 (4)	0.0421 (5)	−0.0919 (2)	0.0225 (11)
H3B	0.1045	0.0246	−0.0419	0.034*
O4B	0.1501 (4)	0.3201 (5)	−0.2274 (2)	0.0251 (11)
H4B	0.2020	0.3209	−0.1830	0.038*
O5B	−0.0695 (4)	0.2162 (5)	−0.3176 (2)	0.0231 (11)
H5B	−0.1197	0.1992	−0.3623	0.035*
O6B	0.1309 (4)	−0.0858 (5)	−0.4331 (2)	0.0246 (12)
H6B	0.1225	−0.0478	−0.4893	0.037*
C1B	0.0130 (6)	−0.1703 (8)	−0.2996 (4)	0.0208 (16)
C2B	0.0253 (6)	−0.1288 (8)	−0.2070 (4)	0.0265 (18)
H2B1	0.0105	−0.2157	−0.1606	0.032*
C3B	0.0617 (6)	0.0501 (8)	−0.1727 (4)	0.0238 (17)
H3B1	−0.0107	0.1167	−0.1549	0.029*
C4B	0.1225 (6)	0.1430 (8)	−0.2535 (4)	0.0227 (17)
H4B1	0.1979	0.0807	−0.2679	0.027*
C5B	0.0418 (6)	0.1435 (8)	−0.3425 (4)	0.0198 (16)
H5B1	0.0782	0.2171	−0.3928	0.024*
C6B	0.0283 (6)	−0.0423 (8)	−0.3797 (4)	0.0242 (17)
H6B1	−0.0434	−0.0479	−0.4236	0.029*
C7B	−0.0249 (6)	−0.3495 (8)	−0.3313 (4)	0.0224 (17)
O1W	−0.0108 (6)	0.0088 (8)	0.0523 (4)	0.0444 (14)
H1W1	−0.071 (5)	−0.047 (10)	0.031 (5)	0.08 (4)*
H1W2	−0.003 (9)	−0.010 (15)	0.113 (2)	0.15 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.039 (3)	0.018 (3)	0.017 (2)	−0.003 (2)	0.004 (2)	−0.001 (2)
O2	0.040 (3)	0.012 (3)	0.019 (2)	0.000 (2)	−0.0037 (19)	0.0025 (19)
O3	0.039 (3)	0.016 (3)	0.016 (2)	−0.006 (2)	0.002 (2)	0.0002 (19)
O4	0.034 (3)	0.013 (3)	0.016 (2)	−0.001 (2)	0.0000 (19)	−0.0002 (19)
O5	0.021 (3)	0.020 (3)	0.019 (2)	−0.003 (2)	−0.0026 (19)	0.0009 (18)
O6	0.026 (3)	0.010 (3)	0.032 (2)	−0.003 (2)	0.006 (2)	0.000 (2)
C1	0.013 (4)	0.008 (4)	0.019 (3)	0.001 (3)	−0.003 (3)	−0.001 (3)
C2	0.017 (4)	0.009 (4)	0.028 (4)	−0.006 (3)	−0.001 (3)	0.001 (3)
C3	0.014 (4)	0.016 (4)	0.021 (3)	−0.005 (3)	−0.003 (3)	−0.004 (3)
C4	0.025 (4)	0.015 (4)	0.018 (3)	0.003 (3)	−0.002 (3)	0.006 (3)
C5	0.022 (5)	0.006 (3)	0.022 (3)	−0.003 (3)	0.002 (3)	0.003 (3)
C6	0.016 (4)	0.015 (4)	0.018 (3)	−0.004 (3)	0.000 (3)	−0.003 (3)
C7	0.007 (4)	0.017 (4)	0.029 (4)	0.003 (3)	0.001 (3)	0.005 (3)
O1A	0.033 (3)	0.023 (3)	0.019 (2)	0.002 (2)	0.002 (2)	0.002 (2)
O2A	0.049 (4)	0.011 (3)	0.022 (2)	0.005 (2)	0.000 (2)	−0.006 (2)
O3A	0.039 (3)	0.021 (3)	0.019 (2)	−0.008 (2)	0.000 (2)	0.002 (2)
O4A	0.024 (3)	0.020 (3)	0.020 (2)	0.002 (2)	−0.0007 (19)	−0.0047 (19)
O5A	0.022 (3)	0.019 (3)	0.029 (2)	−0.002 (2)	−0.001 (2)	−0.0075 (19)
O6A	0.027 (3)	0.013 (3)	0.026 (2)	−0.003 (2)	−0.0100 (19)	0.0020 (19)
C1A	0.013 (4)	0.019 (4)	0.016 (3)	−0.009 (3)	−0.002 (3)	0.001 (3)
C2A	0.016 (4)	0.016 (4)	0.024 (3)	0.001 (3)	0.002 (3)	0.003 (3)
C3A	0.021 (4)	0.018 (4)	0.018 (3)	−0.002 (3)	0.000 (3)	0.002 (3)
C4A	0.023 (5)	0.016 (4)	0.013 (3)	−0.002 (3)	−0.001 (3)	−0.008 (3)
C5A	0.016 (4)	0.019 (4)	0.020 (3)	0.005 (3)	−0.009 (3)	−0.002 (3)
C6A	0.023 (4)	0.008 (4)	0.021 (3)	−0.002 (3)	0.000 (3)	0.000 (3)
C7A	0.014 (4)	0.010 (4)	0.033 (4)	−0.002 (3)	0.006 (3)	0.002 (3)
O1B	0.047 (4)	0.023 (3)	0.020 (2)	−0.006 (2)	−0.001 (2)	−0.004 (2)
O2B	0.035 (3)	0.021 (3)	0.029 (2)	−0.004 (2)	0.001 (2)	−0.004 (2)
O3B	0.030 (3)	0.020 (3)	0.017 (2)	−0.003 (2)	−0.0082 (19)	−0.0005 (18)
O4B	0.035 (3)	0.016 (3)	0.024 (2)	−0.002 (2)	−0.0052 (19)	−0.001 (2)
O5B	0.024 (3)	0.018 (3)	0.027 (2)	0.000 (2)	−0.003 (2)	−0.001 (2)
O6B	0.030 (3)	0.024 (3)	0.021 (2)	0.002 (2)	0.007 (2)	0.0008 (19)
C1B	0.030 (5)	0.016 (4)	0.017 (3)	0.003 (3)	−0.003 (3)	0.000 (3)
C2B	0.034 (5)	0.023 (4)	0.022 (3)	−0.003 (4)	0.002 (3)	0.000 (3)
C3B	0.033 (5)	0.015 (4)	0.023 (3)	0.000 (3)	−0.004 (3)	−0.001 (3)
C4B	0.031 (5)	0.019 (4)	0.018 (3)	0.004 (3)	−0.001 (3)	−0.002 (3)
C5B	0.017 (4)	0.015 (4)	0.027 (3)	0.002 (3)	0.002 (3)	0.004 (3)
C6B	0.028 (5)	0.021 (4)	0.023 (3)	−0.003 (3)	0.001 (3)	−0.001 (3)
C7B	0.021 (5)	0.021 (4)	0.026 (4)	0.002 (3)	−0.001 (3)	0.004 (3)
O1W	0.048 (4)	0.053 (4)	0.032 (3)	−0.011 (3)	−0.001 (3)	−0.008 (3)

O1—C7	1.226 (6)	C1A—C6A	1.530 (8)
O2—C7	1.336 (7)	C2A—C3A	1.502 (8)
O2—H2	0.8400	C2A—H2A1	0.9500
O3—C3	1.449 (7)	C3A—C4A	1.508 (8)
O3—H3	0.8400	C3A—H3A1	1.0000
O4—C4	1.429 (6)	C4A—C5A	1.515 (7)
O4—H4	0.8400	C4A—H4A1	1.0000
O5—C5	1.429 (7)	C5A—C6A	1.518 (7)
O5—H5	0.8400	C5A—H5A1	1.0000
O6—C6	1.450 (6)	C6A—H6A1	1.0000
O6—H6	0.8400	O1B—C7B	1.210 (6)
C1—C2	1.307 (7)	O2B—C7B	1.337 (6)
C1—C7	1.494 (8)	O2B—H2B	0.8400
C1—C6	1.504 (8)	O3B—C3B	1.431 (7)
C2—C3	1.490 (8)	O3B—H3B	0.8400
C2—H2AA	0.9500	O4B—C4B	1.444 (7)
C3—C4	1.521 (8)	O4B—H4B	0.8400
C3—H3AA	1.0000	O5B—C5B	1.425 (7)
C4—C5	1.510 (7)	O5B—H5B	0.8400
C4—H4AA	1.0000	O6B—C6B	1.433 (6)
C5—C6	1.546 (7)	O6B—H6B	0.8400
C5—H5AA	1.0000	C1B—C2B	1.336 (7)
C6—H6AA	1.0000	C1B—C6B	1.506 (7)
O1A—C7A	1.223 (6)	C1B—C7B	1.507 (9)
O2A—C7A	1.329 (7)	C2B—C3B	1.512 (8)
O2A—H2A	0.8400	C2B—H2B1	0.9500
O3A—C3A	1.426 (6)	C3B—C4B	1.516 (8)
O3A—H3A	0.8400	C3B—H3B1	1.0000
O4A—C4A	1.440 (6)	C4B—C5B	1.519 (8)
O4A—H4A	0.8400	C4B—H4B1	1.0000
O5A—C5A	1.437 (7)	C5B—C6B	1.529 (8)
O5A—H5A	0.8400	C5B—H5B1	1.0000
O6A—C6A	1.436 (6)	C6B—H6B1	1.0000
O6A—H6A	0.8400	O1W—H1W1	0.85 (2)
C1A—C2A	1.324 (7)	O1W—H1W2	0.86 (2)
C1A—C7A	1.467 (8)
C7—O2—H2	109.5	O4A—C4A—H4A1	108.6
C3—O3—H3	109.5	C3A—C4A—H4A1	108.6
C4—O4—H4	109.5	C5A—C4A—H4A1	108.6
C5—O5—H5	109.5	O5A—C5A—C4A	111.5 (4)
C6—O6—H6	109.5	O5A—C5A—C6A	107.8 (5)
C2—C1—C7	121.8 (5)	C4A—C5A—C6A	110.7 (5)
C2—C1—C6	123.4 (5)	O5A—C5A—H5A1	108.9
C7—C1—C6	114.8 (5)	C4A—C5A—H5A1	108.9
C1—C2—C3	124.9 (6)	C6A—C5A—H5A1	108.9
C1—C2—H2AA	117.6	O6A—C6A—C5A	109.7 (5)
C3—C2—H2AA	117.6	O6A—C6A—C1A	105.3 (5)
O3—C3—C2	107.1 (5)	C5A—C6A—C1A	110.9 (4)
O3—C3—C4	109.7 (5)	O6A—C6A—H6A1	110.3
C2—C3—C4	112.0 (4)	C5A—C6A—H6A1	110.3
O3—C3—H3AA	109.3	C1A—C6A—H6A1	110.3
C2—C3—H3AA	109.3	O1A—C7A—O2A	122.4 (5)
C4—C3—H3AA	109.3	O1A—C7A—C1A	123.3 (6)
O4—C4—C5	111.1 (5)	O2A—C7A—C1A	114.3 (5)
O4—C4—C3	107.5 (4)	C7B—O2B—H2B	109.5
C5—C4—C3	110.9 (5)	C3B—O3B—H3B	109.5
O4—C4—H4AA	109.1	C4B—O4B—H4B	109.5
C5—C4—H4AA	109.1	C5B—O5B—H5B	109.5
C3—C4—H4AA	109.1	C6B—O6B—H6B	109.5
O5—C5—C4	113.2 (4)	C2B—C1B—C6B	123.5 (6)
O5—C5—C6	105.9 (5)	C2B—C1B—C7B	121.6 (6)
C4—C5—C6	110.7 (5)	C6B—C1B—C7B	114.8 (5)
O5—C5—H5AA	109.0	C1B—C2B—C3B	123.0 (6)
C4—C5—H5AA	109.0	C1B—C2B—H2B1	118.5
C6—C5—H5AA	109.0	C3B—C2B—H2B1	118.5
O6—C6—C1	105.3 (5)	O3B—C3B—C2B	111.8 (5)
O6—C6—C5	109.7 (5)	O3B—C3B—C4B	108.5 (5)
C1—C6—C5	109.9 (4)	C2B—C3B—C4B	108.6 (5)
O6—C6—H6AA	110.6	O3B—C3B—H3B1	109.3
C1—C6—H6AA	110.6	C2B—C3B—H3B1	109.3
C5—C6—H6AA	110.6	C4B—C3B—H3B1	109.3
O1—C7—O2	122.7 (5)	O4B—C4B—C3B	110.9 (4)
O1—C7—C1	123.3 (6)	O4B—C4B—C5B	108.9 (5)
O2—C7—C1	114.0 (5)	C3B—C4B—C5B	109.8 (5)
C7A—O2A—H2A	109.5	O4B—C4B—H4B1	109.1
C3A—O3A—H3A	109.5	C3B—C4B—H4B1	109.1
C4A—O4A—H4A	109.5	C5B—C4B—H4B1	109.1
C5A—O5A—H5A	109.5	O5B—C5B—C4B	108.1 (5)
C6A—O6A—H6A	109.5	O5B—C5B—C6B	111.8 (5)
C2A—C1A—C7A	122.0 (6)	C4B—C5B—C6B	109.1 (5)
C2A—C1A—C6A	122.4 (5)	O5B—C5B—H5B1	109.3
C7A—C1A—C6A	115.5 (5)	C4B—C5B—H5B1	109.3
C1A—C2A—C3A	124.3 (6)	C6B—C5B—H5B1	109.3
C1A—C2A—H2A1	117.9	O6B—C6B—C1B	110.2 (5)
C3A—C2A—H2A1	117.9	O6B—C6B—C5B	108.8 (5)
O3A—C3A—C2A	106.9 (5)	C1B—C6B—C5B	111.9 (4)
O3A—C3A—C4A	111.0 (5)	O6B—C6B—H6B1	108.6
C2A—C3A—C4A	112.0 (5)	C1B—C6B—H6B1	108.6
O3A—C3A—H3A1	108.9	C5B—C6B—H6B1	108.6
C2A—C3A—H3A1	108.9	O1B—C7B—O2B	124.0 (6)
C4A—C3A—H3A1	108.9	O1B—C7B—C1B	122.0 (6)
O4A—C4A—C3A	107.5 (4)	O2B—C7B—C1B	114.0 (5)
O4A—C4A—C5A	110.7 (5)	H1W1—O1W—H1W2	109 (8)
C3A—C4A—C5A	112.6 (5)
C7—C1—C2—C3	179.4 (6)	O5A—C5A—C6A—O6A	169.7 (4)
C6—C1—C2—C3	0.7 (10)	C4A—C5A—C6A—O6A	−68.1 (6)
C1—C2—C3—O3	−132.5 (6)	O5A—C5A—C6A—C1A	−74.4 (6)
C1—C2—C3—C4	−12.2 (9)	C4A—C5A—C6A—C1A	47.7 (7)
O3—C3—C4—O4	−77.6 (6)	C2A—C1A—C6A—O6A	98.2 (6)
C2—C3—C4—O4	163.7 (5)	C7A—C1A—C6A—O6A	−77.9 (6)
O3—C3—C4—C5	160.8 (5)	C2A—C1A—C6A—C5A	−20.4 (8)
C2—C3—C4—C5	42.0 (7)	C7A—C1A—C6A—C5A	163.5 (5)
O4—C4—C5—O5	−62.3 (6)	C2A—C1A—C7A—O1A	179.9 (6)
C3—C4—C5—O5	57.2 (6)	C6A—C1A—C7A—O1A	−4.0 (9)
O4—C4—C5—C6	178.9 (5)	C2A—C1A—C7A—O2A	−2.0 (9)
C3—C4—C5—C6	−61.6 (6)	C6A—C1A—C7A—O2A	174.2 (5)
C2—C1—C6—O6	99.4 (6)	C6B—C1B—C2B—C3B	−3.0 (11)
C7—C1—C6—O6	−79.5 (6)	C7B—C1B—C2B—C3B	−179.2 (6)
C2—C1—C6—C5	−18.7 (9)	C1B—C2B—C3B—O3B	−140.0 (6)
C7—C1—C6—C5	162.5 (5)	C1B—C2B—C3B—C4B	−20.4 (9)
O5—C5—C6—O6	169.9 (4)	O3B—C3B—C4B—O4B	−63.3 (6)
C4—C5—C6—O6	−67.0 (6)	C2B—C3B—C4B—O4B	175.1 (5)
O5—C5—C6—C1	−74.8 (6)	O3B—C3B—C4B—C5B	176.4 (5)
C4—C5—C6—C1	48.3 (7)	C2B—C3B—C4B—C5B	54.7 (7)
C2—C1—C7—O1	171.8 (6)	O4B—C4B—C5B—O5B	−67.1 (6)
C6—C1—C7—O1	−9.3 (9)	C3B—C4B—C5B—O5B	54.4 (6)
C2—C1—C7—O2	−9.7 (9)	O4B—C4B—C5B—C6B	171.1 (5)
C6—C1—C7—O2	169.2 (5)	C3B—C4B—C5B—C6B	−67.4 (6)
C7A—C1A—C2A—C3A	178.6 (6)	C2B—C1B—C6B—O6B	113.1 (7)
C6A—C1A—C2A—C3A	2.7 (10)	C7B—C1B—C6B—O6B	−70.4 (7)
C1A—C2A—C3A—O3A	−134.8 (6)	C2B—C1B—C6B—C5B	−8.1 (10)
C1A—C2A—C3A—C4A	−12.9 (9)	C7B—C1B—C6B—C5B	168.4 (5)
O3A—C3A—C4A—O4A	−77.0 (6)	O5B—C5B—C6B—O6B	160.3 (4)
C2A—C3A—C4A—O4A	163.5 (5)	C4B—C5B—C6B—O6B	−80.2 (6)
O3A—C3A—C4A—C5A	160.8 (5)	O5B—C5B—C6B—C1B	−77.7 (6)
C2A—C3A—C4A—C5A	41.3 (7)	C4B—C5B—C6B—C1B	41.8 (7)
O4A—C4A—C5A—O5A	−60.9 (6)	C2B—C1B—C7B—O1B	−178.8 (6)
C3A—C4A—C5A—O5A	59.4 (6)	C6B—C1B—C7B—O1B	4.6 (10)
O4A—C4A—C5A—C6A	179.1 (5)	C2B—C1B—C7B—O2B	3.9 (10)
C3A—C4A—C5A—C6A	−60.5 (7)	C6B—C1B—C7B—O2B	−172.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1Ai	0.84	1.81	2.624 (5)	164
O3—H3···O4Aii	0.84	1.90	2.705 (5)	161
O4—H4···O6iii	0.84	1.94	2.738 (6)	157
O5—H5···O6Biv	0.84	2.08	2.736 (5)	134
O6—H6···O3iii	0.84	1.89	2.718 (6)	169
O6A—H6A···O3Av	0.84	1.99	2.764 (6)	153
O4A—H4A···O6Av	0.84	1.88	2.712 (6)	168
O5B—H5B···O5	0.84	1.93	2.765 (5)	171
O5A—H5A···O3B	0.84	2.06	2.882 (5)	164
O2A—H2A···O1vi	0.84	1.84	2.664 (5)	167
O6B—H6B···O1Biv	0.84	2.05	2.801 (5)	149
O4B—H4B···O4A	0.84	2.10	2.835 (6)	147
O2B—H2B···O5Bvii	0.84	1.85	2.663 (6)	163
O3B—H3B···O1W	0.84	1.88	2.703 (6)	166
O3A—H3A···O4iv	0.84	1.89	2.705 (5)	163
O1W—H1W1···O5Aviii	0.85 (2)	1.95 (2)	2.794 (7)	173 (8)
O1W—H1W2···O2Bix	0.86 (2)	2.16 (5)	2.967 (6)	157 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1A i	0.84	1.81	2.624 (5)	164
O3—H3⋯O4A ii	0.84	1.90	2.705 (5)	161
O4—H4⋯O6iii	0.84	1.94	2.738 (6)	157
O5—H5⋯O6B iv	0.84	2.08	2.736 (5)	134
O6—H6⋯O3iii	0.84	1.89	2.718 (6)	169
O6A—H6A⋯O3A v	0.84	1.99	2.764 (6)	153
O4A—H4A⋯O6A v	0.84	1.88	2.712 (6)	168
O5B—H5B⋯O5	0.84	1.93	2.765 (5)	171
O5A—H5A⋯O3B	0.84	2.06	2.882 (5)	164
O2A—H2A⋯O1vi	0.84	1.84	2.664 (5)	167
O6B—H6B⋯O1B iv	0.84	2.05	2.801 (5)	149
O4B—H4B⋯O4A	0.84	2.10	2.835 (6)	147
O2B—H2B⋯O5B vii	0.84	1.85	2.663 (6)	163
O3B—H3B⋯O1W	0.84	1.88	2.703 (6)	166
O3A—H3A⋯O4iv	0.84	1.89	2.705 (5)	163
O1W—H1W1⋯O5A viii	0.85 (2)	1.95 (2)	2.794 (7)	173 (8)
O1W—H1W2⋯O2B ix	0.86 (2)	2.16 (5)	2.967 (6)	157 (11)

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