2-(4-Chloro­phen­yl)-2-oxoethyl 4-methyl­benzoate

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

doi:10.1107/S1600536811042851

. 2011 Oct 22;67(Pt 11):o3030. doi: 10.1107/S1600536811042851

2-(4-Chlorophenyl)-2-oxoethyl 4-methylbenzoate

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

PMCID: PMC3247425 PMID: 22220043

Abstract

In the title compound, C₁₆H₁₃ClO₃, the dihedral angle between the benzene rings is 80.74 (8)°. In the crystal, C—H⋯O hydrogen bonds link the molecules to form C(11) chains propagating in [010].

Related literature

For a related structure and background references to phenacyl benzoates, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₃ClO₃
M _r = 288.71
Monoclinic,
a = 5.9132 (4) Å
b = 8.5044 (6) Å
c = 27.8767 (18) Å
β = 95.880 (1)°
V = 1394.49 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 297 K
0.51 × 0.30 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.871, T _max = 0.983
21275 measured reflections
4070 independent reflections
2628 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.144
S = 1.05
4070 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.20 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, PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042851/hb6454sup1.cif

e-67-o3030-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042851/hb6454Isup2.hkl

e-67-o3030-Isup2.hkl^{(199.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042851/hb6454Isup3.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
C16—H16C⋯O1ⁱ	0.96	2.46	3.383 (2)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of the post of Research Officer under the Research University Grant (No. 1001/PFIZIK/811160). AMI thanks Professor Sandeep Sanchethi, Director of the National Institute of Technology-Karnataka, India for providing the research facilities. AMI 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 studies of phenacyl benzoates (Fun et al., 2011), we now report the synthesis and sturcture of the title compound, (I).

In the title compound (Fig. 1), the dihedral angle formed between the chloro-substituted (C1–C6) and the methyl-substituted (C10–C15) benzene rings is 80.74 (8)°. Bond lengths and angles are within the normal ranges and are comparable to a related structure (Fun et al., 2011).

In the crystal (Fig. 2), intermolecular C16—H16C···O1 hydrogen bonds (Table 1) link the molecules to form chains along the b axis.

Experimental

A mixture of 4-methylbenzoic acid (1.0 g, 0.0073 mol), potassium carbonate (1.10 g, 0.0080 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.70 g, 0.0073 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of the title compound began to separate out. They were collected by filtration and recrystallized from ethanol to yield colourless plates of (I). Yield: 1.95 g, 92.8%. M. p: 405–406 K.