4-Hydr­oxy-4,4-diphenyl­butan-2-one

Dennis P Arnold; John C McMurtrie

doi:10.1107/S1600536808020886

. 2008 Jul 12;64(Pt 8):o1465. doi: 10.1107/S1600536808020886

4-Hydroxy-4,4-diphenylbutan-2-one

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

PMCID: PMC2962095 PMID: 21203179

Abstract

The molecules of the title compound, C₁₆H₁₆O₂, display an intramolecular O—H⋯O hydrogen bond between the hydroxyl donor and the ketone acceptor. Intermolecular C—H⋯π interactions connect adjacent molecules into chains that propagate parallel to the ac diagonal. The chains are arranged in sheets, and molecules in adjacent sheets interact via intermolecular O—H⋯O hydrogen bonds.

Related literature

For related literature, see: Rivett (1980 ▶); Paulson et al. (1973 ▶).

Experimental

Crystal data

C₁₆H₁₆O₂
M _r = 240.29
Monoclinic,
a = 9.8619 (2) Å
b = 9.2015 (2) Å
c = 14.3720 (3) Å
β = 102.098 (2)°
V = 1275.21 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 (2) K
0.35 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.933, T _max = 0.984
7361 measured reflections
2935 independent reflections
2144 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.066
S = 1.01
2935 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 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 ▶) and CrystalMaker (CrystalMaker, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020886/hg2422sup1.cif

e-64-o1465-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020886/hg2422Isup2.hkl

e-64-o1465-Isup2.hkl^{(144.1KB, 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
O2—H2O⋯O1	0.910 (12)	2.016 (12)	2.7636 (12)	138.5 (11)
O2—H2O⋯O1ⁱ	0.910 (12)	2.385 (13)	3.0530 (12)	130.3 (10)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the Synthesis and Molecular Recognition Program, Faculty of Science, 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 hydroxyl moiety and the ketone oxygen. The molecules are arranged in chains that propagate parallel to the ac diagonal via intermolecular CH···π interactions. There are two such interactions; the aromatic ring comprising C5—C10 is the CH donor and the ring comprising C11—C16 is the acceptor in both cases. Geometric parameters for the two interactions are as follows; C6—H6···C11—C16_plane distance 2.731 Å with C5—C10_plane···C11—C16_plane dihedral angle 78.67° and C8—H8···C11—C16_plane distance 2.947 Å with C5—C10_plane···C11—C16_plane dihedral angle 83.52°. The chains stack to form two-dimensional sheets in the crystal structure (Fig. 2). Intermolecular hydrogen bonds connect pairs of molecules from contiguous two-dimensional sheets. The pairwise intermolecular H-bond interactions and the intramolecular H-bond interactions are illustrated in Fig. 3.

Experimental

The title compound was prepared according to the procedure described by Rivett (1980) which is an adaptation of the method reported earlier by Paulson et al. (1973). Large colourless prismatic crystals of the compound were obtained by crystallization from an evaporating dichloromethane/methanol solution.