2-(4-Bromo­phen­yl)-2-oxoethyl 2-meth­oxy­benzoate

Hoong-Kun Fun; Ching Kheng Quah; B Garudachari; Arun M Isloor; M N Satyanarayan

doi:10.1107/S1600536811023002

. 2011 Jun 18;67(Pt 7):o1724. doi: 10.1107/S1600536811023002

2-(4-Bromophenyl)-2-oxoethyl 2-methoxybenzoate

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, B Garudachari ^b, Arun M Isloor ^b, M N Satyanarayan ^c

PMCID: PMC3152007 PMID: 21837114

Abstract

In the title molecule, C₁₆H₁₃BrO₄, the dihedral angle between the benzene rings is 85.92 (10)°. In the crystal, molecules are linked into chains along [100] via weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background to and applications of phenacyl benzoate derivatives, see: Rather & Reid (1919 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₃BrO₄
M _r = 349.17
Orthorhombic,
a = 7.8424 (5) Å
b = 14.6799 (9) Å
c = 25.7677 (14) Å
V = 2966.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 2.78 mm⁻¹
T = 296 K
0.56 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.306, T _max = 0.733
19358 measured reflections
4731 independent reflections
2916 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.095
S = 1.00
4731 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 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/S1600536811023002/lh5263sup1.cif

e-67-o1724-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023002/lh5263Isup2.hkl

e-67-o1724-Isup2.hkl^{(231.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023002/lh5263Isup3.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
C2—H2A⋯O1ⁱ	0.93	2.45	3.360 (3)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 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 the identification of organic acids (Rather & Reid, 1919). They undergo photolysis in neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006). They find applications in the field of synthetic chemistry for the synthesis of oxazoles, imidazoles (Huang et al., 1996), benzoxazepine (Gandhi et al., 1995). We report herein the crystal structure of 2-(4-bromophenyl)-2-oxoethyl 2-methoxybenzoate which is potentially of commercial importance.

The molecular structure of the title compound is shown in Fig. 1. The benzene rings (C1-C6 and C10-C15) form a dihedral angle of 85.92 (10) ° . Bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal (Fig. 2), the molecules are linked into one-dimensional chains along [100] via weak intermolecular C2–H2A···O1ⁱ hydrogen bonds (Table 1).

Experimental

A mixture of 2-methoxybenzoic acid (1.00 g, 0.0065 mol) potassium carbonate (0.98 g, 0.0071 mol) and 2-bromo-1-(4-bromophenyl)ethanone (1.80 g, 0.0065 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle shaped crystals of 2-(4-bromophenyl)-2-oxoethyl 2-methoxybenzoate began to separate. These were collected by filtration and recrystallized from ethanol. Yield: 2.15 g, 93.8 %, m.p. : 388-389 K.