2-[2-(Hydroxy­meth­yl)phen­yl]-1-phenyl­ethanol

P Manivel; Venkatesha R Hathwar; S Mohanaroopan; K Prabakaran; F Nawaz Khan

doi:10.1107/S1600536809003043

. 2009 Jan 28;65(Pt 2):o406. doi: 10.1107/S1600536809003043

2-[2-(Hydroxymethyl)phenyl]-1-phenylethanol

P Manivel ^a, Venkatesha R Hathwar ^b, S Mohanaroopan ^a, K Prabakaran ^a, F Nawaz Khan ^a,^*

PMCID: PMC2968234 PMID: 21581999

Abstract

The title compound, C₁₅H₁₆O₂, has a dihedral angle of 19.10 (5)° between the mean planes of the two benzene rings. There is an intramolecular O—H⋯O hydrogen bond and the C—C—C—C torsion angle across the bridge between the two rings is 173.13 (14)°. The molecules form intermolecular O—H⋯O hydrogen-bonded chains extending along the a axis. C—H⋯π contacts are also observed between molecules within the chains.

Related literature

For bond lengths in organic compounds, see: Allen et al. (1987 ▶). For general background, see: Azzena et al. (1996 ▶), and references therein; Barluenga et al. (1987 ▶); Shing et al. (1994 ▶); Lim & Hudson (2004 ▶); Tirodkar & Usgaonkar (1972 ▶); Odabaşoglu et al. (2007 ▶). For related crystal structures, see: Gałdecki et al. (1984 ▶); Hoyos-Guerrero et al. (1983 ▶).

Experimental

Crystal data

C₁₅H₁₆O₂
M _r = 228.28
Orthorhombic,
a = 8.550 (1) Å
b = 15.8676 (18) Å
c = 18.593 (2) Å
V = 2522.4 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 (2) K
0.33 × 0.30 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.941, T _max = 0.996
17664 measured reflections
2347 independent reflections
1618 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.100
S = 1.05
2347 reflections
218 parameters
All H-atom parameters refined
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003043/si2148sup1.cif

e-65-0o406-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003043/si2148Isup2.hkl

e-65-0o406-Isup2.hkl^{(113.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1ⁱ	0.86 (2)	1.89 (2)	2.745 (2)	170.5 (24)
O1—H1O⋯O2	0.93 (2)	1.78 (2)	2.706 (2)	173.6 (22)
C15—H15B⋯Cg2ⁱ	0.95 (2)	2.638 (18)	3.504 (2)	151.7 (14)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility setup under the IRHPA-DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thank the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

A wide range of diaryl diols have been prepared earlier from phthalane and readily available substituted benzaldehyde (Azzena et al., 1996). The diols in general can act as precursors of corresponding oxygen containing heterocyclic compounds by a dehydration process for e.g. benzodihydropyrans; benzoxepines have been prepared (Barluenga et al., 1987, Shing et al., 1987). The hydroxyl structural moiety was found in numerous pharmaceutically active compounds and therefore represents an interesting template for combinatorial as well as medicinal chemistry (Lim and Hudson, 2004). In particular phenylethanol derivatives have good antifungal properties (Tirodkar and Usgaonkar, 1972, Odabaşoglu et al., 2007, Gałdecki et al., 1984, Hoyos-Guerrero et al., 1983).

All the bond lengths are within normal ranges in the title compound (Fig. 1) (Allen et al., 1987). The tight conformation of the molecule is held by an O—H···O intramolecular hydrogen bond (Fig. 1) with C6—C7—C8—C9 torsional angle of 173.13 (14)°. Further, O—H···O and C—H···π (Fig. 2) intermolecular interactions stabilize the packing of the crystal structure and form chains running along the a axis. Cg2 is the centroid of the hydroxymethylphenyl ring C9 - C14 (Table 1).

Experimental

3-Phenylisocoumarin (1 eq.) was dissolved in 10 volumes of methanol, sodium borohydride (4 eq.) was added to it and stirred at 50° C under nitrogen atmosphere for 4 hrs. Then two more equivalents of NaBH₄ was further added and left overnight at 50° C for completion of the reaction. After TLC analysis, solvent methanol was removed, extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried with anhydrous Na₂SO₄, evaporated to yield the title compound, which was further purified by washing with petroleum ether. Single-crystals for the structure analysis were obtained by slow evaporation of the ethanol solution.