2-(2-Benzyl­phen­yl)propan-2-ol

Richard Betz; Thomas Gerber; Eric Hosten; B P Siddaraju; Hemmige S Yathirajan; A R Ramesha

doi:10.1107/S1600536811047143

. 2011 Nov 12;67(Pt 12):o3302. doi: 10.1107/S1600536811047143

2-(2-Benzylphenyl)propan-2-ol

Richard Betz ^a,^*, Thomas Gerber ^a, Eric Hosten ^a, B P Siddaraju ^b, Hemmige S Yathirajan ^b, A R Ramesha ^c

PMCID: PMC3238955 PMID: 22199804

Abstract

There are two molecules in the asymmetric unit of the title compound, C₁₆H₁₈O, a tertiary alcohol featuring a 2-benzylphenyl substituent. Co-operative O—H⋯O hydrogen bonds connect the molecules into tetramers.

Related literature

For general background to the use of benzhydrols in pharmaceutical synthesis, see: Ohkuma et al. (2000 ▶). For related structures, see: Ferguson et al. (1995 ▶); Fun et al. (2010 ▶); Siddaraju et al. (2010 ▶, 2011 ▶); Zeng & Liu (2010 ▶); Gu et al. (2009 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₈O
M _r = 226.30
Monoclinic,
a = 12.2252 (3) Å
b = 17.2508 (4) Å
c = 16.7784 (3) Å
β = 132.549 (1)°
V = 2606.79 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.59 × 0.51 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.901, T _max = 1.000
24429 measured reflections
6480 independent reflections
5035 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.148
S = 1.05
6480 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047143/hg5130sup1.cif

e-67-o3302-sup1.cif^{(31.9KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811047143/hg5130Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047143/hg5130Isup3.hkl

e-67-o3302-Isup3.hkl^{(317.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047143/hg5130Isup4.cml

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
O1—H1⋯O2ⁱ	0.84	1.98	2.7997 (14)	166
O2—H2⋯O1	0.84	1.94	2.7486 (14)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

BPS thanks the University of Mysore for research facilities.

supplementary crystallographic information

Comment

2-(2-Benzylphenyl)propan-2-ol is used in synthetic organic chemistry for the preparation of many organic compounds including anthrone. Benzhydrols are widely used as intermediates for the synthesis of pharmaceuticals (Ohkuma et al., 2000). The crystal structures of 2-(5-bromo-2-methylphenyl)propan-2-ol (Zeng & Liu, 2010), 10,10-dimethylanthrone (Fun et al., 2010), (2-methylphenyl)(phenyl)methanol (Siddaraju et al., 2010), 9,9-dimethyl-9,10-dihydroanthracene (Siddaraju et al., 2011) and a N,N-dimethylamino-substituted analogue of the title compound (Gu et al., 2009) have been reported earlier. In view of the importance of the title compound, its crystal structure was determined.

The asymmetric unit contains two complete molecules. The least-squares planes defined by the carbon atoms of the different phenyl moieties in each molecule enclose angles of 82.58 (10)° and 88.66 (13)°, respectively (Fig. 1).

In the crystal, cooperative hydrogen bonds connect the molecules to discrete tetramers. The plane defined by the atoms of the participating hydroxyl groups is perpendicular to the crystallographic b axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the hydrogen bonds is DD on the unitary level and R⁴₄(8) on the binary level. The shortest intercentroid distance between two aromatic systems was measured at 4.9147 (14) Å and is observed between the two different phenyl rings of one of the molecules present in the asymmetric unit and its symmetry-generated equivalent (Fig. 2).

The packing of the title compound in the crystal is shown in Figure 3.

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. X-ray quality crystals were obtained by slow evaporation from toluene solution at room temperature.