trans-4-tert-Butyl-1-methyl­cyclo­hexa­nol hemihydrate

The title compound, C₁₁H₂₂O·0.5H₂O, is a hemihydrate of trans-4-tert-butyl-1-methyl­cyclo­hexa­nol, containing one water and two organic mol­ecules in the asymmetric unit. Crystals were obtained from an NMR sample by very slow evaporation of the solvent. In the solid state, the title compound forms a double-layered structure with the organic and water mol­ecules connected by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.074
• wR factor = 0.146
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The asymmetric unit of the title compound (I) is presented in Fig. 1. The hydroxyl groups of the trans-1-methyl-4-tert-butylcyclohexanol and the water molecules are connected with each other via an extensive hydrogen bonding network. The water molecule plays the role of a hydrogen bonded bridge between three of the organic molecules and an additional O—H···H bridge is formed between the alcohol units of two of the organic molecules (Table 1). From a supramolecular point of view the crystalline assembly of (I) can be best described as being double-layered (Fig 2.) with the hydroxyl ends of the cyclohexanol moieties and

the water molecules forming a hydrogen bonded hydrophilic layer and the t-butyl ends the other hydrophobic layer.

Related literature

For related literature, see: Grignard (1900).

For related literature, see: Houlihan (1962).

S2. Experimental

trans-1-Methyl-4-tert-butylcyclohexanol was obtained by the well known Grignard method (Grignard, 1900) from 4-tert-butylcyclohexanone with methylmagnesium iodide. The synthetic procedure and the separation of the isomers was performed according to conditions previously described (Houlihan, 1962). Crystals of (I) grew in an NMR sample tube from which all solvent (CDCl₃) has evaporated. The water present in the crystal structure has most probably originated from moisture in the NMR solvent.

S3. Refinement

All H atoms were visible in electron density maps but were ultimately placed in idealized positions, except O—H and methyl H's, and allowed to ride on their parent atoms at C—H distances of 0.99 (methylene), and 1.00 Å (methine) with U_iso(H) = 1.2 times U_eq(C). Methyl H's were allowed to rotate to best fit the experimental electron density at a C—H distance of 0.98 Å with U_iso(H) = 1.5 times U_eq(C). H's attached to O were found in the electron density map and were fixed to an O—H distance of 0.84 Å with U_iso(H) = 1.5 times U_eq(O). The crystals of (I) were rather thin plates and showed a weak scattering power resulting in a large number of reflections with low intensities.

Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

Figures

	Fig. 1. View of the asymmetric unit of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. Packing diagram of (I) showing the layered structure, viewed along the c axis. Dotted lines indicate O—H···H hydrogen bonds.

trans-4-tert-Butyl-1-methylcyclohexanol hemihydrate

Crystal data

C11H22O·0.5H2O	F(000) = 808
Mr = 179.30	Dx = 1.039 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 129292 reflections
a = 18.3462 (14) Å	θ = 0.4–27.9°
b = 10.2347 (5) Å	µ = 0.07 mm^−1
c = 12.3661 (9) Å	T = 173 K
β = 99.049 (3)°	Plate, colourless
V = 2293.1 (3) Å^3	0.40 × 0.35 × 0.05 mm
Z = 8

Data collection

Bruker Kappa-APEXII diffractometer	2783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
Detector resolution: 9 pixels mm^-1	h = −21→21
φ and ω scans	k = −12→12
14932 measured reflections	l = −14→14
4033 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 1.3597P] where P = (Fo^2 + 2Fc^2)/3
4033 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.18 e Å^−3
4 restraints	Δρmin = −0.18 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.03005 (9)	0.68552 (16)	0.06583 (14)	0.0316 (4)
H1	−0.0023 (13)	0.731 (2)	0.091 (2)	0.047*
O21	0.06949 (10)	0.33358 (17)	0.34636 (14)	0.0339 (5)
H21	0.0570 (16)	0.357 (3)	0.2816 (15)	0.051*
O32	0.01989 (12)	0.42567 (18)	0.14125 (16)	0.0432 (5)
H32A	0.0244 (17)	0.5047 (18)	0.128 (3)	0.065*
H32B	0.0080 (17)	0.384 (3)	0.0812 (18)	0.065*
C1	0.10166 (13)	0.7489 (2)	0.0834 (2)	0.0283 (6)
C2	0.15369 (13)	0.6563 (2)	0.0371 (2)	0.0321 (6)
H2A	0.1393	0.6513	−0.0434	0.038*
H2B	0.1485	0.5677	0.0673	0.038*
C3	0.23430 (14)	0.6985 (2)	0.0635 (2)	0.0315 (6)
H3A	0.2406	0.7829	0.0271	0.038*
H3B	0.2656	0.6329	0.0340	0.038*
C4	0.25983 (13)	0.7131 (2)	0.1867 (2)	0.0288 (6)
H4	0.2527	0.6258	0.2198	0.035*
C5	0.20753 (14)	0.8072 (3)	0.2325 (2)	0.0363 (7)
H5A	0.2217	0.8128	0.3130	0.044*
H5B	0.2128	0.8954	0.2018	0.044*
C6	0.12703 (14)	0.7644 (3)	0.2057 (2)	0.0336 (6)
H6A	0.1208	0.6801	0.2425	0.040*
H6B	0.0955	0.8299	0.2348	0.040*
C7	0.09359 (16)	0.8792 (3)	0.0237 (2)	0.0463 (8)
H7A	0.0757	0.8644	−0.0543	0.069*
H7B	0.1416	0.9231	0.0321	0.069*
H7C	0.0583	0.9341	0.0547	0.069*
C8	0.34265 (14)	0.7475 (2)	0.2197 (2)	0.0314 (6)
C9	0.36226 (15)	0.7486 (3)	0.3444 (2)	0.0473 (8)
H9A	0.3471	0.6658	0.3738	0.071*
H9B	0.3366	0.8210	0.3741	0.071*
H9C	0.4157	0.7597	0.3652	0.071*
C10	0.36147 (16)	0.8816 (3)	0.1754 (2)	0.0462 (8)
H10A	0.3509	0.8808	0.0952	0.069*
H10B	0.4139	0.9004	0.1992	0.069*
H10C	0.3315	0.9491	0.2036	0.069*
C11	0.39106 (15)	0.6440 (3)	0.1758 (2)	0.0450 (8)
H11A	0.3850	0.6501	0.0958	0.068*
H11B	0.3761	0.5568	0.1967	0.068*
H11C	0.4429	0.6590	0.2068	0.068*
C21	0.14062 (13)	0.2723 (2)	0.3483 (2)	0.0285 (6)
C22	0.19398 (13)	0.3706 (2)	0.3113 (2)	0.0308 (6)
H22A	0.1898	0.4544	0.3500	0.037*
H22B	0.1796	0.3869	0.2319	0.037*
C23	0.27437 (14)	0.3250 (2)	0.3330 (2)	0.0327 (6)
H23A	0.3064	0.3946	0.3107	0.039*
H23B	0.2799	0.2468	0.2878	0.039*
C24	0.29976 (14)	0.2918 (2)	0.4539 (2)	0.0293 (6)
H24	0.2931	0.3731	0.4960	0.035*
C25	0.24681 (14)	0.1906 (3)	0.4889 (2)	0.0361 (7)
H25A	0.2511	0.1082	0.4485	0.043*
H25B	0.2611	0.1721	0.5680	0.043*
C26	0.16676 (14)	0.2369 (3)	0.4675 (2)	0.0338 (6)
H26A	0.1347	0.1671	0.4893	0.041*
H26B	0.1616	0.3143	0.5137	0.041*
C27	0.13090 (16)	0.1525 (3)	0.2747 (2)	0.0436 (7)
H27A	0.1109	0.1791	0.1997	0.065*
H27B	0.0967	0.0914	0.3015	0.065*
H27C	0.1788	0.1098	0.2754	0.065*
C28	0.38271 (14)	0.2548 (2)	0.4823 (2)	0.0319 (6)
C29	0.40368 (16)	0.2437 (3)	0.6070 (2)	0.0448 (7)
H29A	0.3933	0.3266	0.6411	0.067*
H29B	0.4564	0.2235	0.6256	0.067*
H29C	0.3748	0.1738	0.6340	0.067*
C30	0.40024 (15)	0.1249 (3)	0.4304 (2)	0.0428 (7)
H30A	0.3871	0.1308	0.3506	0.064*
H30B	0.3717	0.0546	0.4578	0.064*
H30C	0.4531	0.1061	0.4497	0.064*
C31	0.43134 (15)	0.3613 (3)	0.4435 (2)	0.0469 (8)
H31A	0.4177	0.4465	0.4706	0.070*
H31B	0.4241	0.3626	0.3633	0.070*
H31C	0.4833	0.3431	0.4719	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0240 (10)	0.0353 (10)	0.0356 (11)	−0.0002 (8)	0.0053 (8)	−0.0053 (8)
O21	0.0308 (11)	0.0400 (11)	0.0311 (11)	0.0045 (8)	0.0054 (9)	0.0041 (9)
O32	0.0560 (13)	0.0383 (11)	0.0325 (11)	−0.0040 (10)	−0.0015 (10)	0.0024 (9)
C1	0.0253 (14)	0.0288 (13)	0.0309 (15)	−0.0004 (11)	0.0045 (12)	−0.0014 (11)
C2	0.0304 (15)	0.0382 (15)	0.0276 (15)	−0.0015 (12)	0.0046 (11)	−0.0053 (12)
C3	0.0295 (15)	0.0372 (15)	0.0299 (15)	0.0014 (12)	0.0109 (12)	−0.0046 (12)
C4	0.0311 (15)	0.0281 (13)	0.0282 (15)	−0.0003 (11)	0.0081 (12)	0.0004 (11)
C5	0.0312 (16)	0.0475 (16)	0.0297 (15)	0.0029 (12)	0.0032 (12)	−0.0127 (13)
C6	0.0288 (15)	0.0417 (15)	0.0313 (16)	0.0034 (12)	0.0073 (12)	−0.0066 (12)
C7	0.0408 (18)	0.0415 (17)	0.055 (2)	0.0016 (13)	0.0027 (15)	0.0139 (14)
C8	0.0286 (15)	0.0374 (15)	0.0283 (15)	−0.0004 (11)	0.0050 (12)	−0.0011 (12)
C9	0.0326 (17)	0.071 (2)	0.0365 (18)	0.0012 (15)	0.0007 (14)	−0.0018 (15)
C10	0.0414 (18)	0.0430 (17)	0.0542 (19)	−0.0121 (14)	0.0079 (15)	−0.0030 (14)
C11	0.0314 (16)	0.0510 (18)	0.054 (2)	0.0048 (13)	0.0106 (14)	−0.0039 (15)
C21	0.0268 (14)	0.0286 (13)	0.0309 (15)	0.0023 (11)	0.0069 (12)	0.0017 (11)
C22	0.0316 (15)	0.0316 (14)	0.0296 (15)	0.0002 (11)	0.0059 (12)	0.0054 (11)
C23	0.0303 (15)	0.0345 (15)	0.0343 (16)	−0.0040 (11)	0.0078 (12)	0.0066 (12)
C24	0.0319 (15)	0.0278 (13)	0.0292 (15)	0.0002 (11)	0.0081 (12)	−0.0007 (11)
C25	0.0325 (16)	0.0414 (16)	0.0344 (16)	0.0010 (12)	0.0051 (12)	0.0107 (12)
C26	0.0316 (16)	0.0363 (15)	0.0347 (16)	−0.0031 (12)	0.0093 (12)	0.0087 (12)
C27	0.0409 (18)	0.0406 (16)	0.0488 (18)	−0.0009 (13)	0.0057 (14)	−0.0072 (14)
C28	0.0288 (15)	0.0348 (14)	0.0322 (15)	−0.0011 (11)	0.0048 (12)	0.0008 (12)
C29	0.0362 (17)	0.0556 (18)	0.0410 (18)	0.0036 (14)	0.0009 (14)	0.0038 (14)
C30	0.0385 (17)	0.0429 (16)	0.0471 (18)	0.0095 (13)	0.0067 (14)	−0.0014 (14)
C31	0.0337 (17)	0.0511 (18)	0.056 (2)	−0.0041 (14)	0.0063 (14)	0.0061 (15)

Geometric parameters (Å, º)

O1—C1	1.450 (3)	C11—H11A	0.9800
O1—H1	0.853 (17)	C11—H11B	0.9800
O21—C21	1.445 (3)	C11—H11C	0.9800
O21—H21	0.832 (17)	C21—C26	1.520 (3)
O32—H32A	0.831 (17)	C21—C27	1.521 (3)
O32—H32B	0.852 (17)	C21—C22	1.524 (3)
C1—C6	1.519 (3)	C22—C23	1.530 (3)
C1—C2	1.519 (3)	C22—H22A	0.9900
C1—C7	1.520 (3)	C22—H22B	0.9900
C2—C3	1.526 (3)	C23—C24	1.532 (3)
C2—H2A	0.9900	C23—H23A	0.9900
C2—H2B	0.9900	C23—H23B	0.9900
C3—C4	1.529 (3)	C24—C25	1.529 (3)
C3—H3A	0.9900	C24—C28	1.554 (3)
C3—H3B	0.9900	C24—H24	1.0000
C4—C5	1.530 (3)	C25—C26	1.526 (3)
C4—C8	1.551 (3)	C25—H25A	0.9900
C4—H4	1.0000	C25—H25B	0.9900
C5—C6	1.526 (3)	C26—H26A	0.9900
C5—H5A	0.9900	C26—H26B	0.9900
C5—H5B	0.9900	C27—H27A	0.9800
C6—H6A	0.9900	C27—H27B	0.9800
C6—H6B	0.9900	C27—H27C	0.9800
C7—H7A	0.9800	C28—C30	1.532 (4)
C7—H7B	0.9800	C28—C31	1.533 (4)
C7—H7C	0.9800	C28—C29	1.534 (4)
C8—C9	1.527 (4)	C29—H29A	0.9800
C8—C11	1.535 (3)	C29—H29B	0.9800
C8—C10	1.537 (4)	C29—H29C	0.9800
C9—H9A	0.9800	C30—H30A	0.9800
C9—H9B	0.9800	C30—H30B	0.9800
C9—H9C	0.9800	C30—H30C	0.9800
C10—H10A	0.9800	C31—H31A	0.9800
C10—H10B	0.9800	C31—H31B	0.9800
C10—H10C	0.9800	C31—H31C	0.9800
C1—O1—H1	111.5 (19)	H11B—C11—H11C	109.5
C21—O21—H21	105 (2)	O21—C21—C26	105.41 (19)
H32A—O32—H32B	109 (3)	O21—C21—C27	108.6 (2)
O1—C1—C6	108.9 (2)	C26—C21—C27	112.2 (2)
O1—C1—C2	105.84 (18)	O21—C21—C22	109.26 (19)
C6—C1—C2	109.1 (2)	C26—C21—C22	109.2 (2)
O1—C1—C7	107.6 (2)	C27—C21—C22	111.9 (2)
C6—C1—C7	112.5 (2)	C21—C22—C23	113.1 (2)
C2—C1—C7	112.6 (2)	C21—C22—H22A	109.0
C1—C2—C3	112.8 (2)	C23—C22—H22A	109.0
C1—C2—H2A	109.0	C21—C22—H22B	109.0
C3—C2—H2A	109.0	C23—C22—H22B	109.0
C1—C2—H2B	109.0	H22A—C22—H22B	107.8
C3—C2—H2B	109.0	C22—C23—C24	112.1 (2)
H2A—C2—H2B	107.8	C22—C23—H23A	109.2
C2—C3—C4	112.0 (2)	C24—C23—H23A	109.2
C2—C3—H3A	109.2	C22—C23—H23B	109.2
C4—C3—H3A	109.2	C24—C23—H23B	109.2
C2—C3—H3B	109.2	H23A—C23—H23B	107.9
C4—C3—H3B	109.2	C25—C24—C23	108.5 (2)
H3A—C3—H3B	107.9	C25—C24—C28	114.5 (2)
C3—C4—C5	108.6 (2)	C23—C24—C28	114.3 (2)
C3—C4—C8	114.7 (2)	C25—C24—H24	106.3
C5—C4—C8	113.9 (2)	C23—C24—H24	106.3
C3—C4—H4	106.3	C28—C24—H24	106.3
C5—C4—H4	106.3	C26—C25—C24	112.2 (2)
C8—C4—H4	106.3	C26—C25—H25A	109.2
C6—C5—C4	112.3 (2)	C24—C25—H25A	109.2
C6—C5—H5A	109.1	C26—C25—H25B	109.2
C4—C5—H5A	109.1	C24—C25—H25B	109.2
C6—C5—H5B	109.1	H25A—C25—H25B	107.9
C4—C5—H5B	109.1	C21—C26—C25	113.0 (2)
H5A—C5—H5B	107.9	C21—C26—H26A	109.0
C1—C6—C5	112.4 (2)	C25—C26—H26A	109.0
C1—C6—H6A	109.1	C21—C26—H26B	109.0
C5—C6—H6A	109.1	C25—C26—H26B	109.0
C1—C6—H6B	109.1	H26A—C26—H26B	107.8
C5—C6—H6B	109.1	C21—C27—H27A	109.5
H6A—C6—H6B	107.9	C21—C27—H27B	109.5
C1—C7—H7A	109.5	H27A—C27—H27B	109.5
C1—C7—H7B	109.5	C21—C27—H27C	109.5
H7A—C7—H7B	109.5	H27A—C27—H27C	109.5
C1—C7—H7C	109.5	H27B—C27—H27C	109.5
H7A—C7—H7C	109.5	C30—C28—C31	108.4 (2)
H7B—C7—H7C	109.5	C30—C28—C29	108.7 (2)
C9—C8—C11	107.7 (2)	C31—C28—C29	107.5 (2)
C9—C8—C10	108.8 (2)	C30—C28—C24	112.3 (2)
C11—C8—C10	108.4 (2)	C31—C28—C24	110.7 (2)
C9—C8—C4	109.4 (2)	C29—C28—C24	109.1 (2)
C11—C8—C4	110.3 (2)	C28—C29—H29A	109.5
C10—C8—C4	112.0 (2)	C28—C29—H29B	109.5
C8—C9—H9A	109.5	H29A—C29—H29B	109.5
C8—C9—H9B	109.5	C28—C29—H29C	109.5
H9A—C9—H9B	109.5	H29A—C29—H29C	109.5
C8—C9—H9C	109.5	H29B—C29—H29C	109.5
H9A—C9—H9C	109.5	C28—C30—H30A	109.5
H9B—C9—H9C	109.5	C28—C30—H30B	109.5
C8—C10—H10A	109.5	H30A—C30—H30B	109.5
C8—C10—H10B	109.5	C28—C30—H30C	109.5
H10A—C10—H10B	109.5	H30A—C30—H30C	109.5
C8—C10—H10C	109.5	H30B—C30—H30C	109.5
H10A—C10—H10C	109.5	C28—C31—H31A	109.5
H10B—C10—H10C	109.5	C28—C31—H31B	109.5
C8—C11—H11A	109.5	H31A—C31—H31B	109.5
C8—C11—H11B	109.5	C28—C31—H31C	109.5
H11A—C11—H11B	109.5	H31A—C31—H31C	109.5
C8—C11—H11C	109.5	H31B—C31—H31C	109.5
H11A—C11—H11C	109.5
O1—C1—C2—C3	−171.6 (2)	O21—C21—C22—C23	168.0 (2)
C6—C1—C2—C3	−54.6 (3)	C26—C21—C22—C23	53.2 (3)
C7—C1—C2—C3	71.0 (3)	C27—C21—C22—C23	−71.6 (3)
C1—C2—C3—C4	56.7 (3)	C21—C22—C23—C24	−56.1 (3)
C2—C3—C4—C5	−54.9 (3)	C22—C23—C24—C25	55.3 (3)
C2—C3—C4—C8	176.4 (2)	C22—C23—C24—C28	−175.6 (2)
C3—C4—C5—C6	55.2 (3)	C23—C24—C25—C26	−55.7 (3)
C8—C4—C5—C6	−175.6 (2)	C28—C24—C25—C26	175.3 (2)
O1—C1—C6—C5	169.57 (19)	O21—C21—C26—C25	−170.8 (2)
C2—C1—C6—C5	54.5 (3)	C27—C21—C26—C25	71.2 (3)
C7—C1—C6—C5	−71.2 (3)	C22—C21—C26—C25	−53.5 (3)
C4—C5—C6—C1	−56.9 (3)	C24—C25—C26—C21	56.9 (3)
C3—C4—C8—C9	−175.6 (2)	C25—C24—C28—C30	58.4 (3)
C5—C4—C8—C9	58.4 (3)	C23—C24—C28—C30	−67.7 (3)
C3—C4—C8—C11	−57.2 (3)	C25—C24—C28—C31	179.7 (2)
C5—C4—C8—C11	176.8 (2)	C23—C24—C28—C31	53.6 (3)
C3—C4—C8—C10	63.7 (3)	C25—C24—C28—C29	−62.2 (3)
C5—C4—C8—C10	−62.3 (3)	C23—C24—C28—C29	171.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···O32	0.83 (2)	1.90 (2)	2.725 (3)	172 (3)
O32—H32A···O1	0.83 (2)	2.01 (2)	2.834 (2)	169 (3)
O32—H32B···O1^i	0.85 (2)	1.98 (2)	2.820 (3)	170 (3)
O1—H1···O21^ii	0.85 (2)	1.87 (2)	2.727 (2)	177 (3)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y+1/2, −z+1/2.