(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone

Mitsui, R.; Nakaema, K.; Noguchi, K.; Yonezawa, N.

doi:10.1107/S1600536808039603

(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone

R. Mitsui, K. Nakaema, K. Noguchi and N. Yonezawa

The title compound, C₁₈H₁₃ClO₃, has an intramolecular O—H

O=C hydrogen bond between the carbonyl group and the hydroxy substituent on the naphthalene ring system. The angle between the C=O bond plane and the naphthalene ring system is relatively small [20.96 (8)°]. The angle between the benzene ring and the carbonyl group is rather large [35.65 (9)°] compared to that in an analogous compound [3.43 (11)°] having a methoxy group instead of a hydroxy substituent.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808039603/su2069sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808039603/su2069Isup2.hkl Contains datablock I

CCDC reference: 712579

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R factor = 0.033
wR factor = 0.096
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   123.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     --  C18     ..       5.21 su

Author Response: Assigned atomic sites was correct. And the molecular structure of the title compound has been confirmed by \^1\^H and \^13\^C NMR spectra, IR spectrum, and elemental analysis, as described in _publ_section_exptl_prep section.


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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

Comment top

Recently, we have reported on the crystal structure of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene, (I) [Mitsui et al., 2008]. As a part of our ongoing studies on the synthesis and crystal structure analyses of aroylated naphthalene derivatives, we prepared and analysed the crystal structure of the title compound, (II). Compound (II) was prepared by regioselective demethylation reaction of compound (I) with aluminium trichloride.

The molecular structure of compound (II) is illustrated in Fig. 1. In analogous aroylated naphthalenes, for example compound (I) shown in Fig. 2, the C═O bond plane is almost perpendicular to the mean plane of the naphthalene ring (Nakaema et al., 2007, 2008; Mitsui et al., 2008). In contrast, the angle between the C═O bond and the naphthalene ring in compound (II) is considerably smaller, i.e. 20.96 (8)°. This is apparently caused by the intramolecular O—H···O═C hydrogen bond, which forms a six-membered ring including the carbonyl group and an edge of the naphthalene ring (Fig. 1 and Table 1).

In compound (I) the C═O bond and the benzene ring are almost coplanar with a dihedral angle of 3.43 (11)°. In compound (II) the mean plane of the benzene ring is twisted away from the C═O bond by 35.65 (9)°. This is presumably caused by the release of the rather large steric repulsion between the benzene ring and the naphthalene ring brought about by the small angle of the C═O bond plane and the naphthalene ring. The dihedral angle between the naphthalene ring (C1—C10) and the benzene ring (C12—C17) is 58.10 (6)°.

In the crystal structure the molecular packing of (II) is mainly stabilized by van der Waals interactions. The naphthalene rings interact with the phenyl rings [C5···C13 = 3.363 (2) Å] and the carbonyl groups [H6···O1 = 2.70 Å] along the a-axis. They also interact with the methyl groups [H3···C18 = 2.79 Å] and aroyl groups [H6···Cl1 = 2.88 Å] along the c-axis (Fig. 3). On the other hand, the naphthalene rings also interact with the methyl groups [C6···H18B = 2.81 Å, C7···H18B = 2.70 Å] and the phenyl rings [C6···H17 = 2.88 Å, C7···H17 = 2.79 Å] along the b-axis. The naphthalene rings are almost perpendicular to the phenyl rings of the adjacent molecules along the b-axis. In addition, the hydroxy groups interact with the phenyl rings [O2···H14 = 2.71 Å] along the b-axis (Fig. 4).

Related literature top

For the structures of closely related compounds, see: Nakaema et al. (2007, 2008); Mitsui et al. (2008).

Experimental top

To a solution of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (33 mg, 0.10 mmol) in CH₂Cl₂ (1.0 ml) was added AlCl₃ (67 mg, 0.50 mmol). The reaction mixture was refluxed for 30 min giving a dark red solution, which was then poured into H₂O (5 ml) and CHCl₃ (3 ml). The aqueous layer was extracted with CHCl₃ (3 × 5 ml). The combined organic layers were washed with brine (3 × 10 ml), and dried over MgSO₄ overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexane to give compound (II) as yellow platelets (m.p. 391–391.5 K, yield 23 mg, 75%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 11.35 (s, 1H), 7.85 (d, 1H), 7.63 (d, 1H), 7.58 (d, 2H), 7.40 (d, 2H), 7.07 (d, 1H), 6.91 (dd, 1H), 6.58 (d, 1H), 3.37 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 199.1, 162.6, 158.2, 138.8, 138.7, 136.5, 133.8, 130.7, 130.2, 128.9, 123.7, 116.4, 115.8, 113.4, 106.5, 54.5; IR (KBr): 3434, 1623, 1583, 1513, 1214, 843.

Anal. Calcd for C₁₈H₁₃ClO₃: C 69.13, H 4.19. Found: C 69.11, H 4.09.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (II), showing 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular structure of compound (I) [Mitsui et al., 2008], showing 50% probability displacement ellipsoids.
	Fig. 3. A partial crystal packing diagram of compound (II), viewed down the b-axis (the intermolecular C—H···O and C—H···π interactions are shown as dashed lines).
	Fig. 4. A partial crystal packing diagram of compound (II), viewed down the c-axis (the intermolecular C—H···O and C—H···π interactions are shown as dashed lines).

(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone top

Crystal data top

C₁₈H₁₃ClO₃	D_x = 1.425 Mg m⁻³
M_r = 312.73	Melting point = 391.0–391.5 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 42602 reflections
a = 17.8030 (3) Å	θ = 3.4–68.2°
b = 8.68121 (10) Å	µ = 2.41 mm⁻¹
c = 18.8683 (3) Å	T = 123 K
V = 2916.14 (8) Å³	Plate, yellow
Z = 8	0.60 × 0.15 × 0.05 mm
F(000) = 1296

Data collection top

Rigaku R-AXIS RAPID diffractometer	2669 independent reflections
Radiation source: rotating anode	2347 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.7°
ω scans	h = −21→21
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −10→10
T_min = 0.485, T_max = 0.886	l = −22→22
49864 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: dfimap
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0544P)² + 0.6658P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2669 reflections	Δρ_max = 0.17 e Å⁻³
205 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00062 (11)

Crystal data top

C₁₈H₁₃ClO₃	V = 2916.14 (8) Å³
M_r = 312.73	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 17.8030 (3) Å	µ = 2.41 mm⁻¹
b = 8.68121 (10) Å	T = 123 K
c = 18.8683 (3) Å	0.60 × 0.15 × 0.05 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2669 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2347 reflections with I > 2σ(I)
T_min = 0.485, T_max = 0.886	R_int = 0.033
49864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.17 e Å⁻³
2669 reflections	Δρ_min = −0.25 e Å⁻³
205 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.05110 (2)	0.23154 (6)	0.500766 (19)	0.05295 (17)
O1	0.04658 (5)	0.08073 (14)	0.17181 (6)	0.0439 (3)
O2	0.12423 (7)	0.21814 (15)	0.07692 (6)	0.0485 (3)
H2	0.0840 (13)	0.163 (3)	0.0974 (11)	0.070 (7)*
O3	0.29872 (6)	0.03670 (13)	0.41875 (6)	0.0474 (3)
C1	0.16824 (8)	0.17285 (16)	0.19660 (7)	0.0299 (3)
C2	0.17846 (9)	0.22425 (17)	0.12659 (8)	0.0373 (3)
C3	0.24694 (10)	0.28979 (18)	0.10428 (8)	0.0432 (4)
H3	0.2518	0.3289	0.0575	0.052*
C4	0.30589 (9)	0.29694 (18)	0.14974 (9)	0.0415 (4)
H4	0.3514	0.3439	0.1347	0.050*
C5	0.36473 (8)	0.23357 (18)	0.26380 (10)	0.0419 (4)
H5	0.4104	0.2779	0.2476	0.050*
C6	0.36219 (8)	0.16956 (18)	0.32922 (9)	0.0433 (4)
H6	0.4052	0.1714	0.3590	0.052*
C7	0.29510 (8)	0.10024 (17)	0.35260 (8)	0.0368 (3)
C8	0.23210 (7)	0.09796 (16)	0.31021 (7)	0.0312 (3)
H8	0.1880	0.0473	0.3262	0.037*
C9	0.23251 (7)	0.17038 (15)	0.24311 (7)	0.0293 (3)
C10	0.30113 (7)	0.23607 (16)	0.21894 (9)	0.0341 (3)
C11	0.09175 (7)	0.12732 (16)	0.21759 (8)	0.0325 (3)
C12	0.06218 (7)	0.14707 (16)	0.29105 (8)	0.0304 (3)
C13	0.00695 (8)	0.04620 (17)	0.31572 (8)	0.0354 (3)
H13	−0.0079	−0.0389	0.2873	0.042*
C14	−0.02637 (8)	0.06910 (18)	0.38113 (8)	0.0389 (4)
H14	−0.0630	−0.0011	0.3984	0.047*
C15	−0.00543 (8)	0.19623 (18)	0.42098 (8)	0.0364 (3)
C16	0.04883 (8)	0.29823 (17)	0.39772 (8)	0.0346 (3)
H16	0.0626	0.3846	0.4258	0.041*
C17	0.08296 (8)	0.27253 (16)	0.33264 (8)	0.0320 (3)
H17	0.1208	0.3411	0.3163	0.038*
C18	0.23232 (12)	−0.0353 (2)	0.44536 (9)	0.0560 (5)
H18A	0.2422	−0.0770	0.4927	0.067*
H18B	0.2174	−0.1192	0.4135	0.067*
H18C	0.1918	0.0407	0.4481	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0399 (3)	0.0813 (4)	0.0376 (2)	−0.0016 (2)	0.00670 (15)	0.00181 (19)
O1	0.0292 (6)	0.0561 (7)	0.0463 (6)	−0.0002 (5)	−0.0077 (4)	−0.0137 (5)
O2	0.0513 (7)	0.0577 (8)	0.0364 (6)	0.0083 (6)	−0.0084 (5)	−0.0005 (5)
O3	0.0542 (7)	0.0414 (6)	0.0466 (6)	0.0105 (5)	−0.0200 (5)	−0.0052 (5)
C1	0.0286 (7)	0.0260 (7)	0.0351 (7)	0.0025 (5)	−0.0004 (5)	−0.0043 (5)
C2	0.0416 (8)	0.0317 (8)	0.0385 (8)	0.0069 (6)	−0.0016 (6)	−0.0048 (6)
C3	0.0554 (9)	0.0328 (9)	0.0413 (8)	0.0008 (7)	0.0116 (8)	0.0006 (7)
C4	0.0395 (8)	0.0313 (8)	0.0536 (10)	−0.0038 (6)	0.0153 (7)	−0.0075 (7)
C5	0.0245 (7)	0.0363 (8)	0.0649 (10)	−0.0006 (6)	0.0027 (7)	−0.0195 (7)
C6	0.0268 (7)	0.0396 (9)	0.0635 (11)	0.0073 (6)	−0.0130 (7)	−0.0200 (8)
C7	0.0368 (8)	0.0295 (8)	0.0441 (8)	0.0104 (6)	−0.0112 (6)	−0.0111 (6)
C8	0.0274 (7)	0.0263 (7)	0.0398 (7)	0.0028 (5)	−0.0033 (5)	−0.0053 (6)
C9	0.0253 (7)	0.0237 (7)	0.0388 (7)	0.0025 (5)	0.0001 (5)	−0.0074 (5)
C10	0.0276 (7)	0.0267 (7)	0.0482 (9)	0.0006 (5)	0.0051 (6)	−0.0102 (6)
C11	0.0264 (7)	0.0290 (7)	0.0422 (8)	0.0029 (6)	−0.0056 (6)	−0.0043 (6)
C12	0.0213 (6)	0.0298 (7)	0.0402 (7)	0.0025 (5)	−0.0033 (5)	−0.0007 (6)
C13	0.0263 (7)	0.0305 (8)	0.0493 (8)	0.0003 (6)	−0.0043 (6)	−0.0018 (6)
C14	0.0274 (7)	0.0392 (9)	0.0502 (9)	−0.0027 (6)	−0.0010 (6)	0.0097 (7)
C15	0.0281 (7)	0.0448 (9)	0.0363 (7)	0.0057 (6)	0.0007 (6)	0.0059 (6)
C16	0.0312 (7)	0.0342 (8)	0.0383 (8)	0.0026 (6)	−0.0017 (6)	−0.0028 (6)
C17	0.0258 (7)	0.0298 (7)	0.0405 (8)	0.0001 (5)	−0.0008 (6)	0.0000 (6)
C18	0.0896 (14)	0.0381 (9)	0.0402 (9)	−0.0063 (9)	−0.0156 (9)	0.0008 (7)

Geometric parameters (Å, º) top

Cl1—C15	1.7381 (15)	C7—C8	1.3778 (19)
O1—C11	1.2476 (17)	C8—C9	1.414 (2)
O2—C2	1.3466 (19)	C8—H8	0.9500
O2—H2	0.94 (2)	C9—C10	1.4233 (19)
O3—C7	1.3661 (19)	C11—C12	1.493 (2)
O3—C18	1.429 (2)	C12—C17	1.392 (2)
C1—C2	1.406 (2)	C12—C13	1.397 (2)
C1—C9	1.4422 (19)	C13—C14	1.384 (2)
C1—C11	1.4722 (19)	C13—H13	0.9500
C2—C3	1.410 (2)	C14—C15	1.387 (2)
C3—C4	1.357 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.382 (2)
C4—C10	1.411 (2)	C16—C17	1.388 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.354 (3)	C17—H17	0.9500
C5—C10	1.414 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.408 (2)	C18—H18C	0.9800
C6—H6	0.9500

C2—O2—H2	106.3 (13)	C4—C10—C9	119.88 (14)
C7—O3—C18	117.31 (12)	C5—C10—C9	119.30 (15)
C2—C1—C9	118.28 (13)	O1—C11—C1	119.80 (13)
C2—C1—C11	117.23 (13)	O1—C11—C12	116.93 (12)
C9—C1—C11	124.48 (12)	C1—C11—C12	123.04 (12)
O2—C2—C1	123.27 (15)	C17—C12—C13	119.32 (13)
O2—C2—C3	115.35 (14)	C17—C12—C11	121.30 (13)
C1—C2—C3	121.36 (14)	C13—C12—C11	119.07 (13)
C4—C3—C2	119.91 (15)	C14—C13—C12	120.60 (14)
C4—C3—H3	120.0	C14—C13—H13	119.7
C2—C3—H3	120.0	C12—C13—H13	119.7
C3—C4—C10	121.42 (14)	C13—C14—C15	118.87 (14)
C3—C4—H4	119.3	C13—C14—H14	120.6
C10—C4—H4	119.3	C15—C14—H14	120.6
C6—C5—C10	121.68 (15)	C16—C15—C14	121.71 (14)
C6—C5—H5	119.2	C16—C15—Cl1	119.28 (12)
C10—C5—H5	119.2	C14—C15—Cl1	118.97 (12)
C5—C6—C7	119.28 (14)	C15—C16—C17	118.95 (14)
C5—C6—H6	120.4	C15—C16—H16	120.5
C7—C6—H6	120.4	C17—C16—H16	120.5
O3—C7—C8	124.26 (14)	C16—C17—C12	120.53 (13)
O3—C7—C6	114.75 (13)	C16—C17—H17	119.7
C8—C7—C6	120.98 (15)	C12—C17—H17	119.7
C7—C8—C9	120.61 (13)	O3—C18—H18A	109.5
C7—C8—H8	119.7	O3—C18—H18B	109.5
C9—C8—H8	119.7	H18A—C18—H18B	109.5
C8—C9—C10	118.02 (13)	O3—C18—H18C	109.5
C8—C9—C1	123.19 (12)	H18A—C18—H18C	109.5
C10—C9—C1	118.68 (13)	H18B—C18—H18C	109.5
C4—C10—C5	120.77 (14)

C9—C1—C2—O2	173.72 (13)	C6—C5—C10—C9	0.3 (2)
C11—C1—C2—O2	−7.2 (2)	C8—C9—C10—C4	174.23 (12)
C9—C1—C2—C3	−7.8 (2)	C1—C9—C10—C4	−2.23 (19)
C11—C1—C2—C3	171.28 (13)	C8—C9—C10—C5	−3.14 (19)
O2—C2—C3—C4	−177.98 (14)	C1—C9—C10—C5	−179.59 (12)
C1—C2—C3—C4	3.4 (2)	C2—C1—C11—O1	26.3 (2)
C2—C3—C4—C10	1.8 (2)	C9—C1—C11—O1	−154.68 (14)
C10—C5—C6—C7	1.6 (2)	C2—C1—C11—C12	−148.00 (14)
C18—O3—C7—C8	−0.5 (2)	C9—C1—C11—C12	31.0 (2)
C18—O3—C7—C6	179.99 (13)	O1—C11—C12—C17	−139.55 (14)
C5—C6—C7—O3	178.89 (13)	C1—C11—C12—C17	34.9 (2)
C5—C6—C7—C8	−0.6 (2)	O1—C11—C12—C13	33.95 (19)
O3—C7—C8—C9	178.21 (12)	C1—C11—C12—C13	−151.57 (13)
C6—C7—C8—C9	−2.4 (2)	C17—C12—C13—C14	−0.7 (2)
C7—C8—C9—C10	4.17 (19)	C11—C12—C13—C14	−174.37 (13)
C7—C8—C9—C1	−179.55 (13)	C12—C13—C14—C15	1.7 (2)
C2—C1—C9—C8	−169.18 (13)	C13—C14—C15—C16	−1.4 (2)
C11—C1—C9—C8	11.8 (2)	C13—C14—C15—Cl1	176.26 (11)
C2—C1—C9—C10	7.07 (19)	C14—C15—C16—C17	0.2 (2)
C11—C1—C9—C10	−171.92 (13)	Cl1—C15—C16—C17	−177.50 (11)
C3—C4—C10—C5	175.05 (14)	C15—C16—C17—C12	0.8 (2)
C3—C4—C10—C9	−2.3 (2)	C13—C12—C17—C16	−0.5 (2)
C6—C5—C10—C4	−177.05 (14)	C11—C12—C17—C16	172.96 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.94 (2)	1.71 (2)	2.5573 (16)	148 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃ClO₃
M_r	312.73
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	123
a, b, c (Å)	17.8030 (3), 8.68121 (10), 18.8683 (3)
V (Å³)	2916.14 (8)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.60 × 0.15 × 0.05

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.485, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	49864, 2669, 2347
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.08
No. of reflections	2669
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.25

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.94 (2)	1.71 (2)	2.5573 (16)	148 (2)

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