2-(4-Methyl­phen­yl)-2-oxoethyl 3-bromo­benzoate

Khan, I.; Ibrar, A.; Korzański, A.; Kubicki, M.

doi:10.1107/S1600536812046995

Volume 68
Part 12
Page o3465
December 2012

Received 9 November 2012
Accepted 15 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 13.0
Details

2-(4-Methylphenyl)-2-oxoethyl 3-bromobenzoate

Imtiaz Khan,^a ^* Aliya Ibrar,^a Artur Korzanski ^b and Maciej Kubicki ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Correspondence e-mail: imtiaz_qau@yahoo.com

The molecule of the title compound, C₁₆H₁₃BrO₃, is built of two approximately planar fragments, viz. 3-bromobenzoate [maximum deviation = 0.055 (2) Å and 2-oxo-2-p-tolylethyl [maximum deviation = 0.042 (2) Å], inclined by 46.51 (7)°. In the crystal, weak C-HO hydrogen bonds and BrBr contacts [3.6491 (7) Å] connect the molecules into infinite layers parallel to (-221).

Related literature

For the structures of similar compounds, see: Fun, Arshad et al. (2011); Fun, Loh et al. (2011); Fun, Ooi et al. (2011); Fun, Shahani et al. (2011).

Experimental

Crystal data

C₁₆H₁₃BrO₃
M_r = 333.17
Triclinic, $[P \overline 1]$
a = 4.7977 (3) Å
b = 10.9951 (7) Å
c = 14.1645 (8) Å
= 74.829 (5)°
= 87.758 (5)°
= 79.327 (5)°
V = 708.64 (7) Å³
Z = 2
Mo K radiation
= 2.90 mm^-1
T = 295 K
0.25 × 0.2 × 0.08 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.335, T_max = 1.000
7924 measured reflections
2501 independent reflections
1768 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.106
S = 1.05
2501 reflections
192 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O10ⁱ	0.93	2.44	3.198 (4)	139
C9-H92O7ⁱⁱ	0.97	2.56	3.406 (4)	146
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5304 ).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Fun, H.-K., Arshad, S., Garudachari, B., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2836.
Fun, H.-K., Loh, W.-S., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o1597.
Fun, H.-K., Ooi, C. W., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3119.
Fun, H.-K., Shahani, T., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3154.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds