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

Dennis P Arnold; John C McMurtrie

doi:10.1107/S1600536809053227

. 2009 Dec 24;66(Pt 1):o225. doi: 10.1107/S1600536809053227

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

Dennis P Arnold ^a, John C McMurtrie ^a,^*

PMCID: PMC2980271 PMID: 21580107

Abstract

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,
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 ▶) 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[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 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

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 ▶).

Supplementary Material

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

e-66-0o225-sup1.cif^{(19KB, cif)}

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

e-66-0o225-Isup2.hkl^{(167.1KB, hkl)}

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

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)

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Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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).