3β,5α,6β-Trihy-droxy-androstan-17-one.

The title compound, C(19)H(30)O(4), is an androstan-17-one derivative synthesized from the dehydro-epiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)(3) (OTf is trifluoro-methane-sulfonate). The six-membered rings have a slightly flattened chair conformation, while the five-membered ring adopts a 14-α envelope conformation. All rings are trans fused. In the crystal, the mol-ecules are connected by O-H⋯O hydrogen bonds involving the hydroxyl and carbonyl groups, forming a three-dimensional network. A quantum mechanical ab initio Roothan Hartree-Fock calculation of the free mol-ecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values.

Related literature

For the synthesis of the title compound, see: Carvalho et al. (2010b ▶). For 3β,5α,6β-hy­droxy­lation pattern occurance in several natural products, see: Mizushina et al. (1999 ▶); Hata et al. (2002 ▶); Tanaka et al. (2002 ▶); Sun et al. (2006 ▶). For natural products as scaffolds for drug discovery, see: Li & Vederas (2009 ▶); Rosén et al. (2009 ▶). For angiotoxicity of 3β,5α,6β-trihy­droxy steroids, see: Imai et al. (1980 ▶); Peng et al. (1985 ▶). For the in vivo genesis of osteoporosis and atherosclerosis, see: Hongmei et al. (2005 ▶); Imai et al. (1980 ▶); Peng et al. (1985 ▶). For the cytotoxicity of steroids with a 3β,5α,6β-hy­droxy­lation motif against cancer cells, see: Aiello et al. (1995 ▶); Carvalho et al. (2010a ▶); El-Gamal et al. (2004 ▶). For the use of 3β,5α,6β-trihy­droxy steroids in the synthesis of Δ4-3,6-dione steroids. see: Tischler et al. (1988 ▶); Aiello et al. (1991 ▶); Pardo et al. (2000 ▶). For their use as mol­ecular probes for the study of aromatase inhibition, see: Numazawa & Tachibana (1994 ▶); Pérez-Ornelas et al. (2005 ▶); Nagaoka & Numazawa (2004 ▶). For the use of the title compound as an inter­mediate in the synthesis of the aromatase inhibitor androst-4-ene-3,6,17-trione, see: Ehrenstein (1939 ▶); Numazawa et al. (1987 ▶); Anthony et al. (1999 ▶). For related structures, see Anthony et al. (1999 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and 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

C19H30O4

M = 322.43

Orthorhombic,

a = 5.8132 (1) Å

b = 13.3880 (3) Å

c = 21.3298 (5) Å

V = 1660.04 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.23 × 0.13 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.937, T max = 1.00

40718 measured reflections

2276 independent reflections

1874 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

2276 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 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 datablocks global, I. DOI: 10.1107/S1600536811011706/bt5502sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011706/bt5502Isup2.hkl

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

C19H30O4	Dx = 1.290 Mg m−3
Mr = 322.43	Melting point: 574 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6253 reflections
a = 5.8132 (1) Å	θ = 3.1–30.3°
b = 13.3880 (3) Å	µ = 0.09 mm−1
c = 21.3298 (5) Å	T = 293 K
V = 1660.04 (6) Å3	Prism, colourless
Z = 4	0.23 × 0.13 × 0.13 mm
F(000) = 704

Bruker APEXII CCD area-detector diffractometer	2276 independent reflections
Radiation source: fine-focus sealed tube	1874 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→6
Tmin = 0.937, Tmax = 1.00	k = −17→17
40718 measured reflections	l = −27→25

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2093P] where P = (Fo2 + 2Fc2)/3
2276 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. IR (film) 3442, 3348, 2942, 2861, 1723, 1471, 1373, 1077, 1047, 1030, 1001, 960, 874 cm-1; 1H NMR (300 MHz, DMSO-d6) δ p.p.m. 0.77 (3H, s, 18-CH3), 1.04 (3H, s, 19-CH3), 2.36 (1H, dd, J=19.0, 8.2 Hz), 3.35 (1H, m, 6α-H), 3.74 (1H, s, OH), 3.78 (1H, m, 3α-H), 4.22 (1H, d, J=5.8 Hz, OH), 4.51 (1H, d, J=4.3 Hz, OH); 13C NMR (75 MHz, DMSO-d6)δ p.p.m. 13.4, 16.2, 20.0, 21.4 (CH2), 29.6, 31.0 (CH2), 31.5 (CH2), 32.0 (CH2), 33.3 (CH2), 35.3 (CH2), 37.9 (C-10), 40.8 (CH2), 44.8, 47.2 (C-13), 50.5, 65.6, 73.8, 74.3 (C-5), 220.0 (C-17); MS m/z (%): 321.3 (9) [M—H]+, 293.2 (20), 280.4 (23), 265.5 (100), 250.2 (13), 90.3 (54).

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	0.4447 (4)	0.39692 (11)	−0.03066 (6)	0.0551 (5)
H3	0.4176	0.4562	−0.0371	0.083*
O5	0.8749 (2)	0.26939 (10)	0.10844 (6)	0.0344 (3)
H5	0.8788	0.2198	0.0860	0.052*
O6	0.3172 (3)	0.20863 (13)	0.18197 (7)	0.0490 (4)
H6A	0.2372	0.2182	0.1509	0.074*
O17	1.1224 (3)	0.38845 (11)	0.44942 (6)	0.0396 (4)
C1	0.7513 (4)	0.47124 (14)	0.11921 (8)	0.0304 (4)
H1A	0.7555	0.5345	0.1414	0.036*
H1B	0.9085	0.4527	0.1093	0.036*
C2	0.6166 (4)	0.48453 (14)	0.05810 (8)	0.0358 (5)
H2A	0.4642	0.5098	0.0676	0.043*
H2B	0.6940	0.5334	0.0320	0.043*
C3	0.5956 (4)	0.38742 (14)	0.02260 (8)	0.0334 (5)
H3A	0.7485	0.3683	0.0075	0.040*
C4	0.5032 (4)	0.30359 (13)	0.06337 (8)	0.0298 (4)
H4A	0.5094	0.2414	0.0400	0.036*
H4B	0.3433	0.3170	0.0733	0.036*
C5	0.6392 (3)	0.29152 (13)	0.12470 (8)	0.0245 (4)
C6	0.5535 (4)	0.20277 (14)	0.16369 (9)	0.0326 (5)
H6	0.5743	0.1419	0.1388	0.039*
C7	0.6922 (4)	0.19194 (13)	0.22384 (8)	0.0333 (5)
H7A	0.8478	0.1718	0.2133	0.040*
H7B	0.6247	0.1395	0.2492	0.040*
C8	0.7015 (3)	0.28834 (13)	0.26229 (8)	0.0248 (4)
H8	0.5454	0.3049	0.2762	0.030*
C9	0.7942 (3)	0.37543 (13)	0.22212 (7)	0.0226 (4)
H9	0.9469	0.3549	0.2076	0.027*
C10	0.6459 (3)	0.39125 (12)	0.16226 (7)	0.0219 (4)
C11	0.8298 (4)	0.47172 (13)	0.26035 (8)	0.0332 (5)
H11A	0.9074	0.5205	0.2342	0.040*
H11B	0.6805	0.4989	0.2714	0.040*
C12	0.9702 (4)	0.45672 (14)	0.32058 (8)	0.0329 (5)
H12A	1.1280	0.4402	0.3100	0.039*
H12B	0.9712	0.5181	0.3448	0.039*
C13	0.8657 (3)	0.37305 (14)	0.35939 (8)	0.0267 (4)
C14	0.8548 (3)	0.27739 (13)	0.31973 (8)	0.0267 (4)
H14	1.0109	0.2665	0.3038	0.032*
C15	0.8117 (4)	0.19464 (15)	0.36767 (9)	0.0418 (5)
H15A	0.8561	0.1299	0.3512	0.050*
H15B	0.6513	0.1925	0.3801	0.050*
C16	0.9667 (5)	0.22585 (15)	0.42264 (10)	0.0460 (6)
H16A	0.8930	0.2110	0.4623	0.055*
H16B	1.1126	0.1908	0.4209	0.055*
C17	1.0028 (4)	0.33729 (15)	0.41549 (8)	0.0307 (4)
C18	0.6314 (4)	0.40438 (18)	0.38719 (9)	0.0436 (5)
H18A	0.6503	0.4641	0.4115	0.065*
H18B	0.5739	0.3519	0.4135	0.065*
H18C	0.5244	0.4166	0.3538	0.065*
C19	0.4042 (3)	0.42658 (15)	0.18101 (9)	0.0331 (5)
H19A	0.4118	0.4944	0.1955	0.050*
H19B	0.3460	0.3847	0.2139	0.050*
H19C	0.3038	0.4227	0.1454	0.050*

	U11	U22	U33	U12	U13	U23
O3	0.0995 (15)	0.0344 (8)	0.0314 (8)	−0.0083 (10)	−0.0306 (9)	−0.0014 (6)
O5	0.0335 (7)	0.0368 (8)	0.0328 (7)	0.0077 (6)	0.0005 (6)	−0.0113 (6)
O6	0.0397 (8)	0.0592 (10)	0.0482 (8)	−0.0219 (9)	−0.0106 (7)	0.0154 (8)
O17	0.0437 (8)	0.0463 (8)	0.0289 (7)	0.0028 (8)	−0.0082 (7)	−0.0058 (6)
C1	0.0425 (11)	0.0251 (9)	0.0235 (9)	−0.0085 (9)	−0.0074 (8)	0.0012 (7)
C2	0.0548 (13)	0.0278 (9)	0.0247 (9)	−0.0095 (10)	−0.0092 (10)	0.0023 (8)
C3	0.0461 (12)	0.0328 (10)	0.0213 (9)	−0.0015 (10)	−0.0054 (9)	−0.0025 (8)
C4	0.0398 (10)	0.0236 (9)	0.0260 (9)	−0.0050 (9)	−0.0069 (8)	−0.0041 (7)
C5	0.0256 (9)	0.0230 (9)	0.0250 (8)	−0.0013 (8)	−0.0021 (7)	−0.0039 (7)
C6	0.0417 (11)	0.0227 (9)	0.0335 (10)	−0.0083 (9)	−0.0086 (9)	−0.0010 (8)
C7	0.0468 (12)	0.0202 (9)	0.0330 (10)	−0.0055 (9)	−0.0082 (9)	0.0033 (7)
C8	0.0257 (9)	0.0237 (8)	0.0251 (8)	−0.0010 (8)	−0.0020 (7)	0.0016 (7)
C9	0.0249 (9)	0.0215 (8)	0.0213 (8)	−0.0010 (7)	−0.0017 (7)	−0.0010 (7)
C10	0.0249 (9)	0.0193 (8)	0.0216 (8)	−0.0004 (7)	−0.0009 (7)	−0.0018 (7)
C11	0.0504 (13)	0.0231 (9)	0.0262 (9)	−0.0037 (9)	−0.0092 (9)	−0.0002 (7)
C12	0.0458 (12)	0.0289 (9)	0.0240 (9)	−0.0060 (9)	−0.0066 (9)	−0.0018 (7)
C13	0.0293 (9)	0.0294 (9)	0.0215 (8)	0.0035 (8)	−0.0006 (8)	−0.0011 (7)
C14	0.0287 (10)	0.0256 (9)	0.0258 (8)	0.0003 (8)	−0.0008 (8)	0.0008 (7)
C15	0.0570 (14)	0.0325 (11)	0.0359 (10)	−0.0053 (11)	−0.0098 (10)	0.0095 (9)
C16	0.0661 (16)	0.0387 (11)	0.0332 (10)	0.0014 (12)	−0.0136 (11)	0.0086 (9)
C17	0.0310 (10)	0.0391 (11)	0.0220 (9)	0.0048 (9)	0.0027 (8)	−0.0005 (8)
C18	0.0364 (11)	0.0598 (14)	0.0346 (10)	0.0160 (11)	0.0025 (10)	−0.0060 (10)
C19	0.0303 (11)	0.0382 (11)	0.0306 (9)	0.0076 (9)	−0.0034 (9)	−0.0043 (8)

O3—C3	1.441 (2)	C8—H8	0.9800
O3—H3	0.8200	C9—C11	1.539 (2)
O5—C5	1.444 (2)	C9—C10	1.555 (2)
O5—H5	0.8200	C9—H9	0.9800
O6—C6	1.430 (3)	C10—C19	1.535 (3)
O6—H6A	0.8200	C11—C12	1.535 (2)
O17—C17	1.215 (2)	C11—H11A	0.9700
C1—C2	1.531 (2)	C11—H11B	0.9700
C1—C10	1.538 (2)	C12—C13	1.520 (3)
C1—H1A	0.9700	C12—H12A	0.9700
C1—H1B	0.9700	C12—H12B	0.9700
C2—C3	1.510 (3)	C13—C17	1.515 (3)
C2—H2A	0.9700	C13—C14	1.536 (2)
C2—H2B	0.9700	C13—C18	1.543 (3)
C3—C4	1.518 (3)	C14—C15	1.528 (2)
C3—H3A	0.9800	C14—H14	0.9800
C4—C5	1.537 (2)	C15—C16	1.537 (3)
C4—H4A	0.9700	C15—H15A	0.9700
C4—H4B	0.9700	C15—H15B	0.9700
C5—C6	1.533 (3)	C16—C17	1.514 (3)
C5—C10	1.558 (2)	C16—H16A	0.9700
C6—C7	1.522 (3)	C16—H16B	0.9700
C6—H6	0.9800	C18—H18A	0.9600
C7—C8	1.530 (2)	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—H19A	0.9600
C8—C14	1.522 (2)	C19—H19B	0.9600
C8—C9	1.544 (2)	C19—H19C	0.9600
C3—O3—H3	109.5	C19—C10—C1	107.80 (16)
C5—O5—H5	109.5	C19—C10—C9	109.59 (14)
C6—O6—H6A	109.5	C1—C10—C9	111.35 (14)
C2—C1—C10	112.67 (15)	C19—C10—C5	112.05 (14)
C2—C1—H1A	109.1	C1—C10—C5	107.44 (13)
C10—C1—H1A	109.1	C9—C10—C5	108.61 (13)
C2—C1—H1B	109.1	C12—C11—C9	113.91 (15)
C10—C1—H1B	109.1	C12—C11—H11A	108.8
H1A—C1—H1B	107.8	C9—C11—H11A	108.8
C3—C2—C1	111.62 (15)	C12—C11—H11B	108.8
C3—C2—H2A	109.3	C9—C11—H11B	108.8
C1—C2—H2A	109.3	H11A—C11—H11B	107.7
C3—C2—H2B	109.3	C13—C12—C11	109.85 (16)
C1—C2—H2B	109.3	C13—C12—H12A	109.7
H2A—C2—H2B	108.0	C11—C12—H12A	109.7
O3—C3—C2	111.65 (16)	C13—C12—H12B	109.7
O3—C3—C4	107.56 (16)	C11—C12—H12B	109.7
C2—C3—C4	112.23 (14)	H12A—C12—H12B	108.2
O3—C3—H3A	108.4	C17—C13—C12	116.91 (17)
C2—C3—H3A	108.4	C17—C13—C14	101.13 (14)
C4—C3—H3A	108.4	C12—C13—C14	109.33 (14)
C3—C4—C5	112.54 (15)	C17—C13—C18	104.28 (15)
C3—C4—H4A	109.1	C12—C13—C18	111.22 (17)
C5—C4—H4A	109.1	C14—C13—C18	113.69 (16)
C3—C4—H4B	109.1	C8—C14—C15	120.83 (16)
C5—C4—H4B	109.1	C8—C14—C13	112.78 (14)
H4A—C4—H4B	107.8	C15—C14—C13	104.05 (14)
O5—C5—C6	106.23 (15)	C8—C14—H14	106.1
O5—C5—C4	107.77 (14)	C15—C14—H14	106.1
C6—C5—C4	112.08 (14)	C13—C14—H14	106.1
O5—C5—C10	106.01 (13)	C14—C15—C16	102.55 (16)
C6—C5—C10	113.17 (13)	C14—C15—H15A	111.3
C4—C5—C10	111.12 (14)	C16—C15—H15A	111.3
O6—C6—C7	106.51 (16)	C14—C15—H15B	111.3
O6—C6—C5	114.67 (17)	C16—C15—H15B	111.3
C7—C6—C5	111.02 (15)	H15A—C15—H15B	109.2
O6—C6—H6	108.1	C17—C16—C15	105.81 (17)
C7—C6—H6	108.1	C17—C16—H16A	110.6
C5—C6—H6	108.1	C15—C16—H16A	110.6
C6—C7—C8	112.96 (15)	C17—C16—H16B	110.6
C6—C7—H7A	109.0	C15—C16—H16B	110.6
C8—C7—H7A	109.0	H16A—C16—H16B	108.7
C6—C7—H7B	109.0	O17—C17—C16	125.09 (19)
C8—C7—H7B	109.0	O17—C17—C13	126.38 (17)
H7A—C7—H7B	107.8	C16—C17—C13	108.53 (17)
C14—C8—C7	111.77 (14)	C13—C18—H18A	109.5
C14—C8—C9	108.37 (14)	C13—C18—H18B	109.5
C7—C8—C9	110.60 (14)	H18A—C18—H18B	109.5
C14—C8—H8	108.7	C13—C18—H18C	109.5
C7—C8—H8	108.7	H18A—C18—H18C	109.5
C9—C8—H8	108.7	H18B—C18—H18C	109.5
C11—C9—C8	112.67 (13)	C10—C19—H19A	109.5
C11—C9—C10	113.30 (14)	C10—C19—H19B	109.5
C8—C9—C10	111.41 (14)	H19A—C19—H19B	109.5
C11—C9—H9	106.3	C10—C19—H19C	109.5
C8—C9—H9	106.3	H19A—C19—H19C	109.5
C10—C9—H9	106.3	H19B—C19—H19C	109.5
C10—C1—C2—C3	−56.4 (2)	O5—C5—C10—C1	59.79 (17)
C1—C2—C3—O3	172.65 (17)	C6—C5—C10—C1	175.84 (15)
C1—C2—C3—C4	51.8 (2)	C4—C5—C10—C1	−57.03 (19)
O3—C3—C4—C5	−175.47 (15)	O5—C5—C10—C9	−60.77 (17)
C2—C3—C4—C5	−52.3 (2)	C6—C5—C10—C9	55.28 (19)
C3—C4—C5—O5	−60.09 (19)	C4—C5—C10—C9	−177.60 (14)
C3—C4—C5—C6	−176.63 (16)	C8—C9—C11—C12	50.7 (2)
C3—C4—C5—C10	55.7 (2)	C10—C9—C11—C12	178.37 (16)
O5—C5—C6—O6	−177.18 (15)	C9—C11—C12—C13	−52.8 (2)
C4—C5—C6—O6	−59.7 (2)	C11—C12—C13—C17	170.85 (16)
C10—C5—C6—O6	66.9 (2)	C11—C12—C13—C14	56.8 (2)
O5—C5—C6—C7	62.06 (18)	C11—C12—C13—C18	−69.57 (19)
C4—C5—C6—C7	179.52 (15)	C7—C8—C14—C15	−55.8 (2)
C10—C5—C6—C7	−53.9 (2)	C9—C8—C14—C15	−177.90 (16)
O6—C6—C7—C8	−72.2 (2)	C7—C8—C14—C13	−179.62 (16)
C5—C6—C7—C8	53.2 (2)	C9—C8—C14—C13	58.24 (19)
C6—C7—C8—C14	−176.03 (16)	C17—C13—C14—C8	173.72 (15)
C6—C7—C8—C9	−55.2 (2)	C12—C13—C14—C8	−62.4 (2)
C14—C8—C9—C11	−51.4 (2)	C18—C13—C14—C8	62.6 (2)
C7—C8—C9—C11	−174.26 (16)	C17—C13—C14—C15	41.03 (18)
C14—C8—C9—C10	179.96 (14)	C12—C13—C14—C15	164.95 (17)
C7—C8—C9—C10	57.1 (2)	C18—C13—C14—C15	−70.1 (2)
C2—C1—C10—C19	−62.94 (19)	C8—C14—C15—C16	−168.04 (17)
C2—C1—C10—C9	176.82 (15)	C13—C14—C15—C16	−40.2 (2)
C2—C1—C10—C5	58.0 (2)	C14—C15—C16—C17	23.2 (2)
C11—C9—C10—C19	−62.1 (2)	C15—C16—C17—O17	−177.7 (2)
C8—C9—C10—C19	66.23 (18)	C15—C16—C17—C13	2.2 (2)
C11—C9—C10—C1	57.1 (2)	C12—C13—C17—O17	34.9 (3)
C8—C9—C10—C1	−174.59 (14)	C14—C13—C17—O17	153.5 (2)
C11—C9—C10—C5	175.23 (15)	C18—C13—C17—O17	−88.3 (2)
C8—C9—C10—C5	−56.48 (18)	C12—C13—C17—C16	−145.00 (19)
O5—C5—C10—C19	178.02 (15)	C14—C13—C17—C16	−26.4 (2)
C6—C5—C10—C19	−65.9 (2)	C18—C13—C17—C16	91.8 (2)
C4—C5—C10—C19	61.19 (19)	C19—C10—C13—C18	1.68 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O17i	0.82	2.11	2.931 (2)	175.
O5—H5···O3ii	0.82	1.99	2.8063 (19)	171.
O6—H6A···O5iii	0.82	2.39	3.120 (2)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O17i	0.82	2.11	2.931 (2)	175
O5—H5⋯O3ii	0.82	1.99	2.8063 (19)	171
O6—H6A⋯O5iii	0.82	2.39	3.120 (2)	148

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