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Volume 69 
Part 9 
Page o1444  
September 2013  

Received 6 August 2013
Accepted 9 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.011 Å
R = 0.065
wR = 0.133
Data-to-parameter ratio = 14.7
Details
Open access

1,4-Dibromo-2,5-di-p-toluoylbenzene

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: zhuhjnjut@hotmail.com

In the title compound, C22H16Br2O2, which has approximate non-crystallographic inversion symmetry, the dihedral angles between the central ring and the pendant rings are 89.1 (4) and 82.4 (3)°; the dihedral angle between the pendant rings is 12.1 (4)°. In the crystal, the packing is influenced by van der Waals forces and no aromatic [pi]-[pi] stacking is observed.

Related literature

For background to the applications of the title compound, see: Shimizu et al. (2011[Shimizu, M., Asai, Y., Takeda, Y., Yamatani, A. & Hiyama, T. (2011). Tetrahedron Lett. 52, 4084-4089.]). For further synthetic details, see: Chardonnens & Salamin (1968[Chardonnens, L. & Salamin, L. (1968). Helv. Chim. Acta, 51, 1095-1102.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16Br2O2

  • Mr = 472.17

  • Monoclinic, P 21 /n

  • a = 9.855 (2) Å

  • b = 12.064 (2) Å

  • c = 16.345 (3) Å

  • [beta] = 97.61 (3)°

  • V = 1926.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.22 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.486, Tmax = 0.678

  • 3664 measured reflections

  • 3452 independent reflections

  • 1518 reflections with I > 2[sigma](I)

  • Rint = 0.054

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.133

  • S = 1.00

  • 3452 reflections

  • 235 parameters

  • 48 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7121 ).


Acknowledgements

The authors thank the Center of Test and Analysis, Nanjing University, for the data collection.

References

Chardonnens, L. & Salamin, L. (1968). Helv. Chim. Acta, 51, 1095-1102.  [CrossRef]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shimizu, M., Asai, Y., Takeda, Y., Yamatani, A. & Hiyama, T. (2011). Tetrahedron Lett. 52, 4084-4089.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1444  [ doi:10.1107/S160053681302237X ]

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