2-(2-Methyl-1,3-dioxolan-2-yl)-1,1-diphenyl­ethanol

Arnold, D.P.; McMurtrie, J.C.

doi:10.1107/S1600536809053227

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o225

doi:10.1107/S1600536809053227

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2-(2-Methyl-1,3-dioxolan-2-yl)-1,1-diphenylethanol

Dennis P. Arnold ^a and John C. McMurtrie ^a ^*

^aChemistry, Queensland University of Technology, 2 George St, Brisbane, Queensland 4001, Australia
^*Correspondence e-mail: j.mcmurtrie@qut.edu.au

(Received 9 December 2009; accepted 10 December 2009; online 24 December 2009)

The molecules of the title compound, C₁₈H₂₀O₃, display an intramolecular O—H⋯O hydrogen bond between the hydroxy donor and a ketal O-atom acceptor. In the crystal, intermolecular C—H⋯π interactions connect adjacent molecules into chains parallel to the b axis.

Related literature

For the preparation of the title compound, see: Paulson et al. (1973 ).

Experimental

Crystal data

C₁₈H₂₀O₃
M_r = 284.34
Monoclinic, P 2₁ /c
a = 5.7961 (4) Å
b = 8.8271 (7) Å
c = 29.754 (2) Å
β = 92.150 (7)°
V = 1521.26 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.68 × 0.35 × 0.09 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.974, T_max = 1.000
5871 measured reflections
3407 independent reflections
2458 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.100
S = 1.03
3407 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O⋯O2	0.94 (1)	1.81 (1)	2.6820 (12)	153 (1)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053227/jh2121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053227/jh2121Isup2.hkl

checkCIF report

Comment top

The molecular stucture of the title compound, (I), is illustrated in Fig. 1. There is an intramolecular hydrogen bond between the hydroxy moiety and one of the ketal oxygen atoms (O3—H1O···O2, oxygen-oxygen distance 2.6820 (12) Å, O—H···O angle 153 (1)°). The presence of the hydrogen bond results in a loss of the average mirror symmetry and as a result the molecular conformer is chiral at C2. Both hands of the conformer are present in the structure as implied by the centrosymmetric space symmetry. The ¹H NMR spectrum (room temperature) is indicative of the average conformation indicating that rearrangement in the solution state is rapid on the NMR timescale.

The molecules of (I) are arranged in chains that propagate parallel to the b axis via intermolecular CH···π interactions as illustrated in Fig. 2 (C15—H15_edge···C13—C18_plane distance 2.96 Å). Interestingly, these are the only significant aryl-aryl interactions. The aliphatic components of the molecule including the methyl, methylene and ketal groups, completely occupy the space between the two phenyl rings (highlighted in Fig. 2) in which π interactions would be expected to occur. Adjacent chains are connected by weakly interacting aliphatic-CH···π interactions in addition to the omnipresent van der Waals forces.

Related literature top

For the preparation of the title compound, see: Paulson et al. (1973).

Experimental top

The title compound was prepared by the procedure reported by Paulson et al. (1973). Large crystalline plates were obtained from methanol/water by vapour diffusion. NMR ¹H (300 MHz, CDCl₃) 7.53 (m, 4H, ortho-H), 7.30 (m, 4H, meta-H), 7.18 (tt, 2H, para-H), 5.39 (s, 1H, OH), 3.9–3.6 (symmetrical multiplets, AA'BB', 4H, ketal ring H), 2.84 (s, 2H, CH₂), 1.07 (s, 3H, CH₃).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. ORTEP depiction of the molecular structure with atom numbering scheme. Ellipsoids are drawn at the 40% probability level. The intramolecular hydrogen bond (O3—H···O2) is indicated by a dashed line.
	Fig. 2. Crystal packing detail viewed parallel to the a axis. CH···π (edge to face) interactions propagate parallel to the b axis (black arrows). The arrangement of the aliphatic components (methyl green, ethylene orange and ketal blue) between four phenyl rings is indicated.

2-(2-Methyl-1,3-dioxolan-2-yl)-1,1-diphenylethanol top

Crystal data top

C₁₈H₂₀O₃	F(000) = 608
M_r = 284.34	D_x = 1.241 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.7961 (4) Å	Cell parameters from 2617 reflections
b = 8.8271 (7) Å	θ = 3.4–28.6°
c = 29.754 (2) Å	µ = 0.08 mm⁻¹
β = 92.150 (7)°	T = 173 K
V = 1521.26 (19) Å³	Plate, colourless
Z = 4	0.68 × 0.35 × 0.09 mm

Data collection top

Oxford Diffraction Gemini diffractometer	3407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2458 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 16.0774 pixels mm^-1	θ_max = 28.7°, θ_min = 3.5°
ω scans	h = −4→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −11→10
T_min = 0.974, T_max = 1.000	l = −37→37
5871 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0523P)²] where P = (F_o² + 2F_c²)/3
3407 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₂₀O₃	V = 1521.26 (19) Å³
M_r = 284.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7961 (4) Å	µ = 0.08 mm⁻¹
b = 8.8271 (7) Å	T = 173 K
c = 29.754 (2) Å	0.68 × 0.35 × 0.09 mm
β = 92.150 (7)°

Data collection top

Oxford Diffraction Gemini diffractometer	3407 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	2458 reflections with I > 2σ(I)
T_min = 0.974, T_max = 1.000	R_int = 0.017
5871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
3407 reflections	Δρ_min = −0.19 e Å⁻³
194 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.9148 (2)	0.35245 (18)	0.06596 (5)	0.0381 (4)
H1A	0.9150	0.2620	0.0468	0.057*
H1B	1.0740	0.3862	0.0720	0.057*
H1C	0.8270	0.4333	0.0506	0.057*
C2	0.8042 (2)	0.31506 (15)	0.10991 (4)	0.0276 (3)
C3	0.7536 (3)	0.10241 (17)	0.15222 (6)	0.0450 (4)
H3A	0.7242	0.1454	0.1822	0.054*
H3B	0.8023	−0.0046	0.1558	0.054*
C4	0.5432 (3)	0.11605 (17)	0.12092 (6)	0.0465 (4)
H4A	0.5403	0.0347	0.0980	0.056*
H4B	0.3994	0.1112	0.1378	0.056*
C5	0.8041 (2)	0.44391 (13)	0.14479 (4)	0.0214 (3)
H5A	0.9611	0.4883	0.1463	0.026*
H5B	0.7780	0.3976	0.1745	0.026*
C6	0.63093 (18)	0.57549 (14)	0.13839 (4)	0.0193 (3)
C7	0.6771 (2)	0.67148 (14)	0.09647 (4)	0.0213 (3)
C8	0.8846 (2)	0.74953 (15)	0.09357 (4)	0.0300 (3)
H8	0.9982	0.7406	0.1173	0.036*
C9	0.9288 (2)	0.83969 (17)	0.05699 (5)	0.0387 (4)
H9	1.0708	0.8931	0.0559	0.046*
C10	0.7661 (3)	0.85235 (18)	0.02188 (5)	0.0402 (4)
H10	0.7960	0.9139	−0.0034	0.048*
C11	0.5610 (3)	0.77505 (18)	0.02399 (5)	0.0410 (4)
H11	0.4495	0.7829	−0.0001	0.049*
C12	0.5150 (2)	0.68539 (15)	0.06104 (4)	0.0306 (3)
H12	0.3719	0.6333	0.0622	0.037*
C13	0.6400 (2)	0.68055 (13)	0.17969 (4)	0.0208 (3)
C14	0.4531 (2)	0.77607 (15)	0.18647 (5)	0.0318 (3)
H14	0.3254	0.7752	0.1655	0.038*
C15	0.4502 (3)	0.87249 (17)	0.22329 (5)	0.0413 (4)
H15	0.3211	0.9368	0.2273	0.050*
C16	0.6344 (3)	0.87537 (17)	0.25425 (5)	0.0391 (4)
H16	0.6322	0.9406	0.2796	0.047*
C17	0.8203 (3)	0.78268 (16)	0.24777 (5)	0.0388 (4)
H17	0.9478	0.7846	0.2688	0.047*
C18	0.8250 (2)	0.68578 (15)	0.21082 (4)	0.0289 (3)
H18	0.9556	0.6228	0.2069	0.035*
O1	0.92307 (16)	0.18920 (10)	0.12962 (3)	0.0369 (3)
O2	0.56966 (15)	0.26253 (10)	0.10043 (3)	0.0344 (2)
O3	0.39885 (13)	0.51655 (10)	0.13579 (3)	0.0244 (2)
H1O	0.409 (2)	0.4207 (11)	0.1220 (4)	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0378 (8)	0.0446 (9)	0.0321 (8)	0.0005 (7)	0.0053 (6)	−0.0139 (7)
C2	0.0236 (6)	0.0255 (7)	0.0335 (7)	0.0007 (6)	−0.0033 (5)	−0.0071 (6)
C3	0.0514 (10)	0.0226 (8)	0.0614 (10)	−0.0015 (7)	0.0062 (8)	−0.0012 (7)
C4	0.0409 (9)	0.0264 (8)	0.0726 (12)	−0.0062 (7)	0.0069 (8)	−0.0054 (8)
C5	0.0208 (6)	0.0232 (7)	0.0199 (6)	−0.0019 (5)	−0.0009 (5)	−0.0005 (5)
C6	0.0166 (6)	0.0227 (6)	0.0188 (6)	−0.0030 (5)	0.0002 (5)	0.0006 (5)
C7	0.0229 (6)	0.0222 (6)	0.0190 (6)	0.0022 (5)	0.0023 (5)	−0.0001 (5)
C8	0.0259 (7)	0.0365 (8)	0.0275 (7)	−0.0024 (6)	0.0009 (5)	0.0066 (6)
C9	0.0338 (8)	0.0415 (9)	0.0414 (8)	−0.0036 (7)	0.0099 (6)	0.0131 (7)
C10	0.0485 (9)	0.0439 (9)	0.0291 (7)	0.0100 (7)	0.0122 (7)	0.0169 (7)
C11	0.0451 (9)	0.0525 (10)	0.0248 (7)	0.0059 (8)	−0.0052 (6)	0.0090 (7)
C12	0.0299 (7)	0.0352 (8)	0.0265 (7)	0.0000 (6)	−0.0039 (5)	0.0030 (6)
C13	0.0235 (6)	0.0196 (6)	0.0194 (6)	−0.0038 (5)	0.0036 (5)	0.0014 (5)
C14	0.0269 (7)	0.0347 (8)	0.0340 (7)	0.0012 (6)	0.0028 (6)	−0.0068 (6)
C15	0.0371 (8)	0.0392 (8)	0.0487 (9)	0.0027 (7)	0.0148 (7)	−0.0157 (8)
C16	0.0486 (9)	0.0384 (8)	0.0311 (8)	−0.0096 (7)	0.0112 (7)	−0.0133 (7)
C17	0.0465 (9)	0.0411 (9)	0.0281 (7)	−0.0070 (7)	−0.0071 (6)	−0.0071 (7)
C18	0.0312 (7)	0.0279 (7)	0.0273 (7)	0.0007 (6)	−0.0027 (5)	−0.0023 (6)
O1	0.0331 (5)	0.0252 (5)	0.0521 (6)	0.0051 (4)	−0.0017 (5)	−0.0042 (5)
O2	0.0286 (5)	0.0299 (5)	0.0443 (6)	−0.0050 (4)	−0.0044 (4)	−0.0100 (5)
O3	0.0187 (4)	0.0257 (5)	0.0288 (5)	−0.0043 (4)	0.0015 (3)	−0.0015 (4)

Geometric parameters (Å, º) top

C1—C2	1.5145 (18)	C8—C9	1.3802 (18)
C1—H1A	0.9800	C8—H8	0.9500
C1—H1B	0.9800	C9—C10	1.385 (2)
C1—H1C	0.9800	C9—H9	0.9500
C2—O1	1.4222 (16)	C10—C11	1.374 (2)
C2—O2	1.4539 (15)	C10—H10	0.9500
C2—C5	1.5396 (17)	C11—C12	1.3912 (19)
C3—O1	1.4330 (17)	C11—H11	0.9500
C3—C4	1.511 (2)	C12—H12	0.9500
C3—H3A	0.9900	C13—C18	1.3914 (18)
C3—H3B	0.9900	C13—C14	1.3932 (17)
C4—O2	1.4402 (17)	C14—C15	1.3879 (19)
C4—H4A	0.9900	C14—H14	0.9500
C4—H4B	0.9900	C15—C16	1.384 (2)
C5—C6	1.5422 (17)	C15—H15	0.9500
C5—H5A	0.9900	C16—C17	1.372 (2)
C5—H5B	0.9900	C16—H16	0.9500
C6—O3	1.4416 (13)	C17—C18	1.3940 (18)
C6—C13	1.5387 (16)	C17—H17	0.9500
C6—C7	1.5398 (16)	C18—H18	0.9500
C7—C12	1.3908 (18)	O3—H1O	0.943 (8)
C7—C8	1.3914 (17)

C2—C1—H1A	109.5	C8—C7—C6	119.97 (11)
C2—C1—H1B	109.5	C9—C8—C7	121.39 (13)
H1A—C1—H1B	109.5	C9—C8—H8	119.3
C2—C1—H1C	109.5	C7—C8—H8	119.3
H1A—C1—H1C	109.5	C8—C9—C10	119.99 (13)
H1B—C1—H1C	109.5	C8—C9—H9	120.0
O1—C2—O2	105.42 (10)	C10—C9—H9	120.0
O1—C2—C1	108.18 (10)	C11—C10—C9	119.42 (13)
O2—C2—C1	108.96 (11)	C11—C10—H10	120.3
O1—C2—C5	108.16 (10)	C9—C10—H10	120.3
O2—C2—C5	110.03 (10)	C10—C11—C12	120.71 (13)
C1—C2—C5	115.59 (11)	C10—C11—H11	119.6
O1—C3—C4	102.69 (13)	C12—C11—H11	119.6
O1—C3—H3A	111.2	C7—C12—C11	120.43 (13)
C4—C3—H3A	111.2	C7—C12—H12	119.8
O1—C3—H3B	111.2	C11—C12—H12	119.8
C4—C3—H3B	111.2	C18—C13—C14	117.86 (12)
H3A—C3—H3B	109.1	C18—C13—C6	123.64 (11)
O2—C4—C3	103.66 (11)	C14—C13—C6	118.50 (11)
O2—C4—H4A	111.0	C15—C14—C13	121.21 (13)
C3—C4—H4A	111.0	C15—C14—H14	119.4
O2—C4—H4B	111.0	C13—C14—H14	119.4
C3—C4—H4B	111.0	C16—C15—C14	120.30 (13)
H4A—C4—H4B	109.0	C16—C15—H15	119.8
C2—C5—C6	119.34 (10)	C14—C15—H15	119.8
C2—C5—H5A	107.5	C17—C16—C15	119.07 (13)
C6—C5—H5A	107.5	C17—C16—H16	120.5
C2—C5—H5B	107.5	C15—C16—H16	120.5
C6—C5—H5B	107.5	C16—C17—C18	121.00 (13)
H5A—C5—H5B	107.0	C16—C17—H17	119.5
O3—C6—C13	105.32 (8)	C18—C17—H17	119.5
O3—C6—C7	110.19 (9)	C13—C18—C17	120.55 (12)
C13—C6—C7	108.27 (10)	C13—C18—H18	119.7
O3—C6—C5	109.66 (10)	C17—C18—H18	119.7
C13—C6—C5	110.67 (9)	C2—O1—C3	106.33 (10)
C7—C6—C5	112.48 (9)	C4—O2—C2	108.53 (10)
C12—C7—C8	118.05 (11)	C6—O3—H1O	105.7 (8)
C12—C7—C6	121.97 (11)

O1—C3—C4—O2	−30.56 (14)	C7—C6—C13—C18	−104.24 (13)
O1—C2—C5—C6	−162.39 (10)	C5—C6—C13—C18	19.46 (15)
O2—C2—C5—C6	−47.72 (14)	O3—C6—C13—C14	−42.13 (14)
C1—C2—C5—C6	76.20 (14)	C7—C6—C13—C14	75.73 (13)
C2—C5—C6—O3	57.28 (13)	C5—C6—C13—C14	−160.56 (10)
C2—C5—C6—C13	173.04 (10)	C18—C13—C14—C15	−0.58 (19)
C2—C5—C6—C7	−65.72 (14)	C6—C13—C14—C15	179.44 (12)
O3—C6—C7—C12	−4.07 (16)	C13—C14—C15—C16	−0.1 (2)
C13—C6—C7—C12	−118.77 (13)	C14—C15—C16—C17	0.6 (2)
C5—C6—C7—C12	118.62 (12)	C15—C16—C17—C18	−0.4 (2)
O3—C6—C7—C8	174.87 (10)	C14—C13—C18—C17	0.75 (19)
C13—C6—C7—C8	60.17 (14)	C6—C13—C18—C17	−179.28 (11)
C5—C6—C7—C8	−62.43 (15)	C16—C17—C18—C13	−0.3 (2)
C12—C7—C8—C9	0.7 (2)	O2—C2—O1—C3	−29.34 (13)
C6—C7—C8—C9	−178.28 (12)	C1—C2—O1—C3	−145.78 (11)
C7—C8—C9—C10	−0.8 (2)	C5—C2—O1—C3	88.33 (12)
C8—C9—C10—C11	0.3 (2)	C4—C3—O1—C2	37.24 (14)
C9—C10—C11—C12	0.4 (2)	C3—C4—O2—C2	13.39 (14)
C8—C7—C12—C11	0.0 (2)	O1—C2—O2—C4	9.01 (13)
C6—C7—C12—C11	178.97 (12)	C1—C2—O2—C4	124.92 (12)
C10—C11—C12—C7	−0.6 (2)	C5—C2—O2—C4	−107.39 (12)
O3—C6—C13—C18	137.90 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O2	0.94 (1)	1.81 (1)	2.6820 (12)	153 (1)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀O₃
M_r	284.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	5.7961 (4), 8.8271 (7), 29.754 (2)
β (°)	92.150 (7)
V (Å³)	1521.26 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.68 × 0.35 × 0.09

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.974, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5871, 3407, 2458
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.03
No. of reflections	3407
No. of parameters	194
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O2	0.943 (8)	1.808 (10)	2.6820 (12)	152.8 (12)

Acknowledgements

The authors gratefully acknowledge the Applied Chemistry Cluster, Faculty of Science and Technology, Queensland University of Technology, for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Paulson, D. R., Hartwig, A. L. & Moran, G. F. (1973). J. Chem. Ed. 50, 216–217. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar