Androstane-3β,5α,6β,17β-tetrol tri-hydrate.

The title hydrated tetrol, C(19)H(32)O(4)·3H(2)O, was synthesized by stereoselective reduction of the compound 3β,5α,6β-trihy-droxy-androstan-17-one. All rings are fused trans. The organic mol-ecules are connected head-to-tail along the c axis via O-H⋯O hydrogen bonds. Layers of water mol-ecules in the ab plane inter-connect these chains. A quantum chemical ab initio Roothan Hartree-Fock calculation of the isolated mol-ecule gives values for the mol-ecular geometry close to experimentally determined ones, apart from the C-O bond lengths, whose calculated values are significantly smaller than the measured ones, probably a consequence of the involvement of the C-OH groups in the hydrogen-bonding network.

Related literature

For the synthesis of the title compound, see: Carvalho, Silva, Moreira et al. (2010 ▶); Carvalho, Silva & Sá e Melo (2010 ▶); Luche et al. (1978 ▶). For related structures, see: Andrade et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶); Altona et al. (1968 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the program GAMESS used to perform the quantum chemical calculations, see: Schmidt et al. (1993 ▶).

Experimental

Crystal data

C19H32O4·3H2O

M = 378.49

Triclinic,

a = 5.8420 (2) Å

b = 7.3366 (2) Å

c = 12.7922 (3) Å

α = 74.560 (1)°

β = 83.091 (1)°

γ = 68.930 (1)°

V = 492.97 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.30 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.973, T max = 0.982

14489 measured reflections

2222 independent reflections

2132 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.05

2222 reflections

259 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021349/bt5554sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021349/bt5554Isup2.hkl

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

C19H32O4·3H2O	Z = 1
Mr = 378.49	F(000) = 208
Triclinic, P1	Dx = 1.275 Mg m−3
Hall symbol: P 1	Melting point: 547 K
a = 5.8420 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3366 (2) Å	Cell parameters from 9795 reflections
c = 12.7922 (3) Å	θ = 3.1–27.9°
α = 74.560 (1)°	µ = 0.10 mm−1
β = 83.091 (1)°	T = 293 K
γ = 68.930 (1)°	Prism, colourless
V = 492.97 (2) Å3	0.40 × 0.30 × 0.24 mm

Bruker APEXII CCD area-detector diffractometer	2222 independent reflections
Radiation source: fine-focus sealed tube	2132 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→7
Tmin = 0.973, Tmax = 0.982	k = −9→9
14489 measured reflections	l = −16→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
2222 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 0.20 e Å−3
9 restraints	Δρmin = −0.18 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
O3	0.6825 (3)	0.6903 (2)	1.01710 (10)	0.0341 (3)
H3	0.5888	0.6824	1.0699	0.051*
O5	0.5070 (2)	0.4040 (2)	0.81009 (10)	0.0274 (3)
H5	0.5466	0.3118	0.8646	0.041*
O6	1.1265 (2)	0.3581 (2)	0.69231 (12)	0.0327 (3)
H6	1.1957	0.3562	0.7449	0.049*
O17	0.3382 (3)	0.6345 (2)	0.18191 (10)	0.0322 (3)
H17	0.2368	0.7464	0.1812	0.048*
C8	0.7075 (3)	0.4785 (2)	0.54354 (13)	0.0190 (3)
H8	0.8405	0.5298	0.5122	0.023*
C9	0.5052 (3)	0.6405 (2)	0.59165 (13)	0.0184 (3)
H9	0.3762	0.5836	0.6216	0.022*
C10	0.5997 (3)	0.6831 (2)	0.68858 (13)	0.0189 (3)
C4	0.7953 (3)	0.5133 (3)	0.87369 (14)	0.0235 (3)
H4A	0.8595	0.3850	0.9256	0.028*
H4B	0.9271	0.5678	0.8518	0.028*
C5	0.7073 (3)	0.4805 (2)	0.77394 (13)	0.0200 (3)
C11	0.3867 (3)	0.8294 (3)	0.50259 (14)	0.0265 (4)
H11A	0.5074	0.8931	0.4723	0.032*
H11B	0.2534	0.9239	0.5346	0.032*
C13	0.4866 (3)	0.6246 (2)	0.36183 (13)	0.0203 (3)
C14	0.5959 (3)	0.4377 (2)	0.45415 (13)	0.0209 (3)
H14	0.4580	0.3953	0.4884	0.025*
C1	0.3880 (3)	0.8233 (3)	0.74519 (14)	0.0283 (4)
H1A	0.3224	0.9529	0.6945	0.034*
H1B	0.2578	0.7667	0.7651	0.034*
C3	0.5877 (3)	0.6566 (3)	0.92717 (14)	0.0285 (4)
H3A	0.4634	0.5936	0.9554	0.034*
C6	0.9057 (3)	0.3161 (2)	0.72770 (14)	0.0233 (3)
H6A	0.9462	0.1899	0.7840	0.028*
C7	0.8106 (3)	0.2850 (2)	0.63067 (14)	0.0240 (3)
H7A	0.6831	0.2264	0.6555	0.029*
H7B	0.9434	0.1898	0.5988	0.029*
C2	0.4682 (4)	0.8545 (3)	0.84738 (15)	0.0326 (4)
H2A	0.5831	0.9268	0.8266	0.039*
H2B	0.3261	0.9360	0.8822	0.039*
C12	0.2867 (3)	0.7820 (3)	0.41083 (14)	0.0267 (4)
H12A	0.1527	0.7327	0.4392	0.032*
H12B	0.2230	0.9044	0.3547	0.032*
C18	0.6775 (3)	0.7118 (3)	0.29715 (15)	0.0293 (4)
H18A	0.7901	0.6159	0.2601	0.044*
H18B	0.7658	0.7405	0.3457	0.044*
H18C	0.5963	0.8335	0.2450	0.044*
C19	0.7914 (3)	0.7860 (3)	0.64653 (14)	0.0266 (4)
H19A	0.7130	0.9184	0.6024	0.040*
H19B	0.9156	0.7081	0.6040	0.040*
H19C	0.8654	0.7961	0.7069	0.040*
C17	0.3951 (3)	0.5244 (3)	0.29226 (14)	0.0262 (4)
H17A	0.2486	0.4975	0.3281	0.031*
C15	0.7529 (4)	0.2761 (3)	0.39465 (15)	0.0302 (4)
H15A	0.7737	0.1420	0.4394	0.036*
H15B	0.9131	0.2880	0.3739	0.036*
C16	0.6017 (4)	0.3220 (3)	0.29381 (17)	0.0376 (5)
H16A	0.7037	0.3314	0.2283	0.056*
H16B	0.5340	0.2169	0.2990	0.056*
OW1	0.6011 (4)	0.1107 (3)	1.01617 (15)	0.0493 (4)
HW11	0.607 (7)	−0.002 (3)	1.021 (3)	0.074*
HW12	0.468 (5)	0.163 (6)	1.045 (3)	0.074*
OW2	0.1512 (3)	0.3921 (3)	0.09832 (16)	0.0519 (4)
HW21	0.186 (7)	0.466 (5)	0.128 (3)	0.078*
HW22	0.042 (6)	0.488 (5)	0.067 (3)	0.078*
OW3	0.0382 (5)	1.0250 (4)	0.1259 (2)	0.0762 (7)
HW31	−0.074 (7)	1.048 (8)	0.088 (4)	0.114*
HW32	0.074 (9)	1.124 (6)	0.124 (4)	0.114*

	U11	U22	U33	U12	U13	U23
O3	0.0427 (8)	0.0482 (8)	0.0175 (6)	−0.0188 (7)	−0.0037 (5)	−0.0118 (6)
O5	0.0313 (7)	0.0332 (7)	0.0210 (6)	−0.0191 (6)	−0.0032 (5)	0.0002 (5)
O6	0.0222 (6)	0.0420 (8)	0.0344 (7)	−0.0078 (6)	−0.0039 (5)	−0.0129 (6)
O17	0.0371 (7)	0.0358 (7)	0.0209 (6)	−0.0056 (6)	−0.0087 (5)	−0.0087 (5)
C8	0.0199 (7)	0.0185 (8)	0.0183 (7)	−0.0047 (6)	−0.0020 (6)	−0.0058 (6)
C9	0.0200 (7)	0.0207 (8)	0.0148 (7)	−0.0058 (6)	−0.0022 (6)	−0.0055 (6)
C10	0.0209 (7)	0.0195 (8)	0.0160 (6)	−0.0053 (6)	−0.0032 (6)	−0.0047 (6)
C4	0.0259 (8)	0.0263 (9)	0.0183 (7)	−0.0089 (7)	−0.0057 (6)	−0.0033 (6)
C5	0.0220 (8)	0.0226 (8)	0.0174 (7)	−0.0103 (7)	−0.0022 (6)	−0.0037 (6)
C11	0.0323 (9)	0.0218 (8)	0.0200 (8)	0.0007 (7)	−0.0083 (7)	−0.0069 (7)
C13	0.0207 (7)	0.0232 (8)	0.0164 (7)	−0.0049 (6)	−0.0025 (6)	−0.0063 (6)
C14	0.0229 (8)	0.0214 (8)	0.0193 (7)	−0.0068 (7)	−0.0018 (6)	−0.0069 (6)
C1	0.0283 (9)	0.0310 (10)	0.0220 (8)	−0.0006 (8)	−0.0056 (7)	−0.0118 (7)
C3	0.0307 (9)	0.0420 (11)	0.0185 (8)	−0.0157 (8)	−0.0036 (7)	−0.0107 (7)
C6	0.0265 (9)	0.0190 (8)	0.0210 (7)	−0.0040 (7)	−0.0076 (6)	−0.0016 (6)
C7	0.0291 (9)	0.0182 (8)	0.0234 (8)	−0.0033 (7)	−0.0071 (6)	−0.0066 (6)
C2	0.0360 (10)	0.0354 (11)	0.0238 (8)	−0.0019 (8)	−0.0052 (8)	−0.0154 (8)
C12	0.0249 (8)	0.0302 (9)	0.0200 (8)	0.0007 (7)	−0.0065 (6)	−0.0092 (7)
C18	0.0314 (9)	0.0339 (10)	0.0243 (9)	−0.0149 (8)	−0.0006 (7)	−0.0050 (7)
C19	0.0348 (9)	0.0245 (9)	0.0245 (8)	−0.0157 (7)	−0.0044 (7)	−0.0033 (7)
C17	0.0288 (8)	0.0328 (10)	0.0198 (8)	−0.0113 (7)	−0.0026 (6)	−0.0089 (7)
C15	0.0393 (10)	0.0234 (9)	0.0251 (8)	−0.0024 (8)	−0.0064 (7)	−0.0104 (7)
C16	0.0535 (12)	0.0304 (10)	0.0286 (9)	−0.0064 (9)	−0.0088 (8)	−0.0145 (8)
OW1	0.0636 (11)	0.0451 (10)	0.0416 (9)	−0.0261 (9)	−0.0069 (8)	−0.0015 (7)
OW2	0.0525 (10)	0.0546 (11)	0.0552 (11)	−0.0203 (9)	−0.0148 (8)	−0.0151 (8)
OW3	0.0667 (14)	0.0515 (12)	0.107 (2)	−0.0064 (11)	−0.0284 (13)	−0.0217 (12)

O3—C3	1.4473 (18)	C1—C2	1.538 (2)
O3—H3	0.8200	C1—H1A	0.9700
O5—C5	1.4496 (19)	C1—H1B	0.9700
O5—H5	0.8200	C3—C2	1.513 (3)
O6—C6	1.426 (2)	C3—H3A	0.9800
O6—H6	0.8200	C6—C7	1.520 (2)
O17—C17	1.438 (2)	C6—H6A	0.9800
O17—H17	0.8200	C7—H7A	0.9700
C8—C14	1.5248 (19)	C7—H7B	0.9700
C8—C7	1.525 (2)	C2—H2A	0.9700
C8—C9	1.547 (2)	C2—H2B	0.9700
C8—H8	0.9800	C12—H12A	0.9700
C9—C11	1.535 (2)	C12—H12B	0.9700
C9—C10	1.5603 (18)	C18—H18A	0.9600
C9—H9	0.9800	C18—H18B	0.9600
C10—C19	1.537 (2)	C18—H18C	0.9600
C10—C1	1.542 (2)	C19—H19A	0.9600
C10—C5	1.557 (2)	C19—H19B	0.9600
C4—C3	1.520 (3)	C19—H19C	0.9600
C4—C5	1.537 (2)	C17—C16	1.537 (3)
C4—H4A	0.9700	C17—H17A	0.9800
C4—H4B	0.9700	C15—C16	1.545 (2)
C5—C6	1.535 (2)	C15—H15A	0.9700
C11—C12	1.539 (2)	C15—H15B	0.9700
C11—H11A	0.9700	C16—H16A	0.9700
C11—H11B	0.9700	C16—H16B	0.9700
C13—C12	1.527 (2)	OW1—HW11	0.802 (19)
C13—C18	1.532 (2)	OW1—HW12	0.820 (19)
C13—C17	1.537 (2)	OW2—HW21	0.825 (19)
C13—C14	1.540 (2)	OW2—HW22	0.809 (19)
C14—C15	1.535 (2)	OW3—HW31	0.81 (2)
C14—H14	0.9800	OW3—HW32	0.82 (2)
C3—O3—H3	109.5	O3—C3—H3A	108.6
C5—O5—H5	109.5	C2—C3—H3A	108.6
C6—O6—H6	109.5	C4—C3—H3A	108.6
C17—O17—H17	109.5	O6—C6—C7	106.88 (14)
C14—C8—C7	110.14 (12)	O6—C6—C5	114.35 (13)
C14—C8—C9	108.20 (12)	C7—C6—C5	110.36 (13)
C7—C8—C9	111.03 (13)	O6—C6—H6A	108.4
C14—C8—H8	109.1	C7—C6—H6A	108.4
C7—C8—H8	109.1	C5—C6—H6A	108.4
C9—C8—H8	109.1	C6—C7—C8	113.45 (13)
C11—C9—C8	111.15 (13)	C6—C7—H7A	108.9
C11—C9—C10	114.18 (13)	C8—C7—H7A	108.9
C8—C9—C10	111.71 (12)	C6—C7—H7B	108.9
C11—C9—H9	106.4	C8—C7—H7B	108.9
C8—C9—H9	106.4	H7A—C7—H7B	107.7
C10—C9—H9	106.4	C3—C2—C1	111.83 (15)
C19—C10—C1	108.27 (14)	C3—C2—H2A	109.2
C19—C10—C5	111.98 (13)	C1—C2—H2A	109.2
C1—C10—C5	107.37 (13)	C3—C2—H2B	109.2
C19—C10—C9	109.47 (13)	C1—C2—H2B	109.2
C1—C10—C9	111.07 (13)	H2A—C2—H2B	107.9
C5—C10—C9	108.69 (12)	C13—C12—C11	111.20 (14)
C3—C4—C5	111.29 (14)	C13—C12—H12A	109.4
C3—C4—H4A	109.4	C11—C12—H12A	109.4
C5—C4—H4A	109.4	C13—C12—H12B	109.4
C3—C4—H4B	109.4	C11—C12—H12B	109.4
C5—C4—H4B	109.4	H12A—C12—H12B	108.0
H4A—C4—H4B	108.0	C13—C18—H18A	109.5
O5—C5—C6	105.43 (13)	C13—C18—H18B	109.5
O5—C5—C4	107.34 (13)	H18A—C18—H18B	109.5
C6—C5—C4	111.83 (13)	C13—C18—H18C	109.5
O5—C5—C10	106.41 (12)	H18A—C18—H18C	109.5
C6—C5—C10	114.03 (12)	H18B—C18—H18C	109.5
C4—C5—C10	111.26 (12)	C10—C19—H19A	109.5
C9—C11—C12	112.56 (14)	C10—C19—H19B	109.5
C9—C11—H11A	109.1	H19A—C19—H19B	109.5
C12—C11—H11A	109.1	C10—C19—H19C	109.5
C9—C11—H11B	109.1	H19A—C19—H19C	109.5
C12—C11—H11B	109.1	H19B—C19—H19C	109.5
H11A—C11—H11B	107.8	O17—C17—C16	109.69 (14)
C12—C13—C18	110.92 (15)	O17—C17—C13	116.41 (15)
C12—C13—C17	115.43 (13)	C16—C17—C13	105.03 (14)
C18—C13—C17	109.95 (14)	O17—C17—H17A	108.5
C12—C13—C14	108.13 (13)	C16—C17—H17A	108.5
C18—C13—C14	113.66 (13)	C13—C17—H17A	108.5
C17—C13—C14	98.26 (13)	C14—C15—C16	103.10 (15)
C8—C14—C15	119.76 (14)	C14—C15—H15A	111.1
C8—C14—C13	114.15 (12)	C16—C15—H15A	111.1
C15—C14—C13	103.82 (13)	C14—C15—H15B	111.1
C8—C14—H14	106.0	C16—C15—H15B	111.1
C15—C14—H14	106.0	H15A—C15—H15B	109.1
C13—C14—H14	106.0	C17—C16—C15	105.92 (14)
C2—C1—C10	112.90 (14)	C17—C16—H16A	110.6
C2—C1—H1A	109.0	C15—C16—H16A	110.6
C10—C1—H1A	109.0	C17—C16—H16B	110.6
C2—C1—H1B	109.0	C15—C16—H16B	110.6
C10—C1—H1B	109.0	H16A—C16—H16B	108.7
H1A—C1—H1B	107.8	HW11—OW1—HW12	104 (4)
O3—C3—C2	110.35 (15)	HW21—OW2—HW22	90 (4)
O3—C3—C4	109.14 (14)	HW31—OW3—HW32	114 (6)
C2—C3—C4	111.63 (15)
C14—C8—C9—C11	−54.42 (17)	C19—C10—C1—C2	−64.85 (19)
C7—C8—C9—C11	−175.41 (13)	C5—C10—C1—C2	56.22 (19)
C14—C8—C9—C10	176.76 (13)	C9—C10—C1—C2	174.93 (15)
C7—C8—C9—C10	55.78 (17)	C5—C4—C3—O3	−177.17 (13)
C11—C9—C10—C19	−59.18 (19)	C5—C4—C3—C2	−54.92 (19)
C8—C9—C10—C19	68.02 (17)	O5—C5—C6—O6	−176.93 (13)
C11—C9—C10—C1	60.3 (2)	C4—C5—C6—O6	−60.60 (18)
C8—C9—C10—C1	−172.47 (13)	C10—C5—C6—O6	66.72 (16)
C11—C9—C10—C5	178.24 (14)	O5—C5—C6—C7	62.55 (17)
C8—C9—C10—C5	−54.57 (16)	C4—C5—C6—C7	178.88 (14)
C3—C4—C5—O5	−57.61 (18)	C10—C5—C6—C7	−53.80 (17)
C3—C4—C5—C6	−172.78 (14)	O6—C6—C7—C8	−71.50 (18)
C3—C4—C5—C10	58.43 (18)	C5—C6—C7—C8	53.39 (19)
C19—C10—C5—O5	177.61 (14)	C14—C8—C7—C6	−175.01 (14)
C1—C10—C5—O5	58.90 (15)	C9—C8—C7—C6	−55.17 (18)
C9—C10—C5—O5	−61.33 (15)	O3—C3—C2—C1	174.34 (15)
C19—C10—C5—C6	−66.61 (16)	C4—C3—C2—C1	52.8 (2)
C1—C10—C5—C6	174.68 (13)	C10—C1—C2—C3	−55.1 (2)
C9—C10—C5—C6	54.45 (16)	C18—C13—C12—C11	−69.96 (18)
C19—C10—C5—C4	61.00 (17)	C17—C13—C12—C11	164.15 (15)
C1—C10—C5—C4	−57.72 (16)	C14—C13—C12—C11	55.30 (19)
C9—C10—C5—C4	−177.94 (14)	C9—C11—C12—C13	−55.6 (2)
C8—C9—C11—C12	54.8 (2)	C12—C13—C17—O17	81.80 (19)
C10—C9—C11—C12	−177.68 (14)	C18—C13—C17—O17	−44.6 (2)
C7—C8—C14—C15	−56.0 (2)	C14—C13—C17—O17	−163.54 (14)
C9—C8—C14—C15	−177.54 (15)	C12—C13—C17—C16	−156.68 (16)
C7—C8—C14—C13	−179.93 (14)	C18—C13—C17—C16	76.94 (18)
C9—C8—C14—C13	58.54 (17)	C14—C13—C17—C16	−42.02 (17)
C12—C13—C14—C8	−59.23 (17)	C8—C14—C15—C16	−165.07 (15)
C18—C13—C14—C8	64.39 (18)	C13—C14—C15—C16	−36.31 (18)
C17—C13—C14—C8	−179.50 (13)	O17—C17—C16—C15	146.74 (16)
C12—C13—C14—C15	168.66 (14)	C13—C17—C16—C15	20.9 (2)
C18—C13—C14—C15	−67.72 (17)	C14—C15—C16—C17	9.3 (2)
C17—C13—C14—C15	48.38 (16)	C19—C10—C13—C18	2.85 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O17i	0.82	1.98	2.787 (2)	169.
O5—H5···OW1	0.82	2.08	2.891 (2)	170.
O6—H6···O5ii	0.82	2.26	2.9897 (16)	149.
O17—H17···OW3	0.82	1.94	2.718 (3)	159.
OW1—HW11···O3iii	0.80 (2)	2.15 (2)	2.944 (2)	170 (4)
OW1—HW12···OW2i	0.82 (2)	2.19 (2)	2.977 (3)	160 (4)
OW2—HW21···O17	0.83 (2)	2.05 (2)	2.862 (2)	168 (4)
OW2—HW22···O3iv	0.81 (2)	2.14 (2)	2.921 (2)	161 (4)
OW3—HW31···OW1v	0.81 (2)	2.05 (2)	2.850 (3)	169 (5)
OW3—HW32···OW2vi	0.82 (2)	2.11 (2)	2.921 (3)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O17i	0.82	1.98	2.787 (2)	169
O5—H5⋯OW1	0.82	2.08	2.891 (2)	170
O6—H6⋯O5ii	0.82	2.26	2.9897 (16)	149
O17—H17⋯OW3	0.82	1.94	2.718 (3)	159
OW1—HW11⋯O3iii	0.80 (2)	2.15 (2)	2.944 (2)	170 (4)
OW1—HW12⋯OW2i	0.82 (2)	2.19 (2)	2.977 (3)	160 (4)
OW2—HW21⋯O17	0.83 (2)	2.05 (2)	2.862 (2)	168 (4)
OW2—HW22⋯O3iv	0.81 (2)	2.14 (2)	2.921 (2)	161 (4)
OW3—HW31⋯OW1v	0.81 (2)	2.05 (2)	2.850 (3)	169 (5)
OW3—HW32⋯OW2vi	0.82 (2)	2.11 (2)	2.921 (3)	173 (5)

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