2-(4-Chloro­phen­yl)-2-oxoethyl 3-(trifluoro­meth­yl)benzoate

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

doi:10.1107/S1600536811020629

. 2011 Jun 11;67(Pt 7):o1597. doi: 10.1107/S1600536811020629

2-(4-Chlorophenyl)-2-oxoethyl 3-(trifluoromethyl)benzoate

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

PMCID: PMC3152104 PMID: 21837005

Abstract

In the title compound, C₁₆H₁₀ClF₃O₃, the two benzene rings are slightly twisted from each other, with a dihedral angle of 15.50 (8)° between the planes. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a layer parallel to the bc plane.

Related literature

For the background and applications of phenacyl benzoates, see: Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₀ClF₃O₃
M _r = 342.69
Monoclinic,
a = 14.3036 (7) Å
b = 12.1335 (6) Å
c = 8.5464 (4) Å
β = 101.444 (1)°
V = 1453.76 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.28 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.919, T _max = 0.966
15629 measured reflections
3822 independent reflections
2963 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.121
S = 1.04
3822 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.33 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/S1600536811020629/is2720sup1.cif

e-67-o1597-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020629/is2720Isup2.hkl

e-67-o1597-Isup2.hkl^{(187.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020629/is2720Isup3.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
C1—H1A⋯O1ⁱ	0.95	2.53	3.205 (2)	128
C4—H4A⋯O3ⁱⁱ	0.95	2.53	3.289 (2)	137
C8—H8A⋯O3ⁱⁱⁱ	0.99	2.48	3.474 (2)	177

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

Acknowledgments

H-KF and W-SL thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). W-SL also thanks the Malaysian government and USM for the award of a Research Fellowship. AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a ‘Young Scientist’ award. BG thanks the Department of Information Technology, New Delhi, India, for the financial support.

supplementary crystallographic information

Comment

Phenacyl benzoates derivatives are very important in 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 hereby report the crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-(trifluoromethyl) benzoate of potential commercial importance.

In the title compound (Fig. 1), the chlorophenyl (C1–C6/CL1) group is slightly twisted away from the benzene ring (C10–C15) with a dihedral angle of 15.50 (8)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

In the crystal packing (Fig. 2), intermolecular C1—H1A···O1ⁱ, C4—H4A···O3ⁱⁱ and C8—H8A···O3ⁱⁱⁱ hydrogen bonds (Table 1) link the molecules into a layer parallel to the bc plane.

Experimental

A mixture of 3-(trifluoromethyl)benzoic acid (1.0 g, 0.0052 mol), potassium carbonate (0.80 g, 0.0057 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.21 g, 0.0052 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals, 2-(4-chlorophenyl)-2-oxoethyl 3-(trifluoromethyl)benzoate begin to separate. It was collected by filtration and recrystallized from ethanol. Yield: 1.60 g, 88.88%, m.p.: 387–388 K.