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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 [sigma](C-C) = 0.005 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 13.0
Details
Open access

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

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-H...O hydrogen bonds and Br...Br 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, H.-K., Arshad, S., Garudachari, B., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2836.]); Fun, Loh et al. (2011[Fun, H.-K., Loh, W.-S., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o1597.]); Fun, Ooi et al. (2011[Fun, H.-K., Ooi, C. W., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3119.]); Fun, Shahani et al. (2011[Fun, H.-K., Shahani, T., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3154.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13BrO3

  • Mr = 333.17

  • Triclinic, [P \overline 1]

  • a = 4.7977 (3) Å

  • b = 10.9951 (7) Å

  • c = 14.1645 (8) Å

  • [alpha] = 74.829 (5)°

  • [beta] = 87.758 (5)°

  • [gamma] = 79.327 (5)°

  • V = 708.64 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.335, Tmax = 1.000

  • 7924 measured reflections

  • 2501 independent reflections

  • 1768 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.05

  • 2501 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O10i 0.93 2.44 3.198 (4) 139
C9-H92...O7ii 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[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.]); 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.  [CrossRef] [ISI] [details]
Fun, H.-K., Arshad, S., Garudachari, B., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2836.  [CSD] [CrossRef] [details]
Fun, H.-K., Loh, W.-S., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o1597.  [CSD] [CrossRef] [details]
Fun, H.-K., Ooi, C. W., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3119.  [CSD] [CrossRef] [details]
Fun, H.-K., Shahani, T., Garudachari, B., Isloor, A. M. & Satyanarayan, M. N. (2011). Acta Cryst. E67, o3154.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3465  [ doi:10.1107/S1600536812046995 ]

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