2-(4-Bromo­phen­yl)-2-oxoethyl 4-chloro­benzoate

Hoong-Kun Fun; Chin Sing Yeap; B Garudachari; Arun M Isloor; M N Satyanarayan

doi:10.1107/S1600536811022963

. 2011 Jun 18;67(Pt 7):o1723. doi: 10.1107/S1600536811022963

2-(4-Bromophenyl)-2-oxoethyl 4-chlorobenzoate

Hoong-Kun Fun ^a,^*,^‡, Chin Sing Yeap ^a,^§, B Garudachari ^b, Arun M Isloor ^b, M N Satyanarayan ^c

PMCID: PMC3151903 PMID: 21837113

Abstract

The asymmetric unit of the title compound, C₁₅H₁₀BrClO₃, consists of three crystallographically independent molecules. The dihedral angles between the benzene rings in the three molecules are 68.8 (2), 0.7 (3) and 66.1 (2)°. In the crystal, the three independent molecules are interconnected by C—H⋯O hydrogen bonds, leading to isolated trimers.

Related literature

For background to phenacyl benzoate derivatives, see: Huang et al. (1996 ▶); Gandhi et al. (1995 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶,c ▶). For the preparation, see: Kelly & Howard (1932 ▶).

Experimental

Crystal data

C₁₅H₁₀BrClO₃
M _r = 353.59
Monoclinic,
a = 17.1061 (11) Å
b = 5.3062 (4) Å
c = 24.0376 (16) Å
β = 101.502 (1)°
V = 2138.0 (3) Å³
Z = 6
Mo Kα radiation
μ = 3.07 mm⁻¹
T = 297 K
0.41 × 0.19 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.364, T _max = 0.657
18463 measured reflections
8890 independent reflections
5931 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.142
S = 1.04
8890 reflections
541 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ▶), 3590 Friedel pairs
Flack parameter: 0.065 (10)

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/S1600536811022963/rz2606sup1.cif

e-67-o1723-sup1.cif^{(31.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022963/rz2606Isup2.hkl

e-67-o1723-Isup2.hkl^{(434.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022963/rz2606Isup3.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
C5A—H5AA⋯O3B	0.93	2.59	3.227 (7)	126
C5B—H5BA⋯O1A	0.93	2.48	3.217 (7)	136
C15B—H15B⋯O1C	0.93	2.59	3.254 (7)	129

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Acknowledgments

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160. AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the ’Young scientist’ award. GB thanks the Department of Information Technology, New Delhi, India, for financial support.

supplementary crystallographic information

Comment

Phenacyl benzoates derivatives are very important in identification of organic acids (Rather & Reid, 1919). These compounds undergo photolysis in neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006) and find applications in the field of synthetic chemistry for the synthesis of oxazoles, imidazoles (Huang et al., 1996), benzoxazepine (Gandhi et al., 1995). We hereby report the crystal structure of 2-(4-bromophenyl)-2-oxoethyl 4-chlorobenzoate of potential commercial importance.

The asymmetric unit of title compound consists of three crystallographically independent molecules, A, B and C (Fig. 1). The dihedral angles between the two terminal phenyl rings for each molecules being 68.8 (2), 0.7 (3) and 66.1 (2)°, respectively, show that molecule A and C are in similar conformation. The geometic parameters are comparable to those previously reported structures (Fun et al., 2011a,b,c). The three independent molecules are interconnected by C5A—H5AA···O3B, C5B—H5BA···O1A and C15B—H15B···O1C hydrogen bonds (Fig. 1, Table 1). In the crystal structure, the molecules are arranged into columns (Fig. 2) parallel to the b axis.

Experimental

A mixture of 4-chlorobenzoic acid (1.0 g, 0.0063 mol) sodium carbonate (0.744 g, 0.0070 mol) and 2-bromo-1-phenylethanon (1.94 g, 0.0070 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-chlorobenzoate separated. The compound was collected by filtration and re-crystallized from ethanol. Yield: 2.18 g, 96.88%, M. p.: 400–401 K (Kelly & Howard, 1983).