2-(4-Bromo­phen­yl)-2-oxoethyl 4-hy­droxy­benzoate

Hoong-Kun Fun; Wan-Sin Loh; B Garudachari; Arun M Isloor; M N Satyanarayana

doi:10.1107/S1600536811040311

. 2011 Oct 5;67(Pt 11):o2854. doi: 10.1107/S1600536811040311

2-(4-Bromophenyl)-2-oxoethyl 4-hydroxybenzoate

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, B Garudachari ^b, Arun M Isloor ^b, M N Satyanarayana ^c

PMCID: PMC3247591 PMID: 22219896

Abstract

In the title compound, C₁₅H₁₁BrO₄, the dihedral angle between the aromatic rings is 66.77 (8)°. In the crystal, O—H⋯O, C—H⋯Br and C—H⋯O hydrogen bonds link the molecules, forming layers lying parallel to (101). The crystal packing is further consolidated by C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.5476 (7) Å].

Related literature

For a related structure and background references to phenacyl benzoates, see: Fun et al. (2011 ▶). For the synthesis, see: Lund & Langvad (1932 ▶). For a related structure, see: Jin et al. (2008 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₁BrO₄
M _r = 335.15
Monoclinic,
a = 6.2917 (2) Å
b = 7.7893 (2) Å
c = 26.7497 (8) Å
β = 98.234 (2)°
V = 1297.43 (7) Å³
Z = 4
Mo Kα radiation
μ = 3.18 mm⁻¹
T = 100 K
0.56 × 0.27 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.267, T _max = 0.535
15470 measured reflections
4700 independent reflections
3640 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.086
S = 1.04
4700 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040311/hb6429sup1.cif

e-67-o2854-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040311/hb6429Isup2.hkl

e-67-o2854-Isup2.hkl^{(230.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040311/hb6429Isup3.cml

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

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

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O2ⁱ	0.83	1.97	2.7961 (19)	177
C12—H12A⋯Br1ⁱⁱ	0.95	2.90	3.7938 (18)	158
C14—H14A⋯O2ⁱ	0.95	2.52	3.198 (2)	129
C15—H15A⋯Cg2ⁱ	0.95	2.86	3.6181 (18)	137

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. AMI thanks Professor Sandeep Sanchethi, Director of the National Institute of Technology–Karnataka, India, for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award. MNS thanks the Department of Information Technology, Government of India, for financial support.

supplementary crystallographic information

Comment

As part of our ongoing structural studies of phenacyl benzoates (Fun et al., 2011), we now report the crystal structure of the title compound.

In the title compound (Fig. 1), the dihedral angle formed between the bromo-substituted (C1–C6) and hydroxy-substituted (C10–C15) benzene rings is 66.77 (8)°. Bond lengths and angles are within the normal ranges and are comparable to the related structure (Jin et al., 2008).

In the crystal (Fig. 2), O4—H1O4···O2, C12—H12A···Br1 and C14—H14A···O2 hydrogen bonds (Table 1) link the molecules to form layers parallel to the (101) plane. The crystal packing is further consolidated by C—H···π interactions involving the centroid of the hydroxy-substituted benzene ring (Cg2; Table 1) and π–π interactions (Table 1) involving the centroids of the substituted benzene rings with the distance of Cg1···Cg2 being 3.5476 (7) Å. Cg 1 is the centroid of the bromo-substituted benzene ring.

Experimental

A mixture of 4-hydroxybenzoic acid (1.0 g, 0.0072 mol), potassium carbonate (1.09 g, 0.0079 mol) and 2-bromo-1-(4-bromophenyl)ethanone (2.0 g, 0.0072 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-bromophenyl)-2-oxoethyl 4-hydroxybenzoate began to separate out. It was collected by filtration and recrystallized from ethanol to yield colourless blocks. Yield: 2.1 g, 86.7%. M. p.: 464–465 K (Lund & Langvad, 1932).