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Volume 68 
Part 1 
Page o26  
January 2012  

Received 28 November 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.035
wR = 0.108
Data-to-parameter ratio = 12.1
Details
Open access

N-(4-Bromophenyl)-3,5-dinitrobenzamide

aChemistry Department, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan,bNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan, and cDepartment of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
Correspondence e-mail: sohail262001@yahoo.com

The title molecule, C13H8BrN3O5, is slightly twisted, with the dihedral angle between the two benzene rings being 5.9 (1)°. In the crystal, N-H...O hydrogen bonds link the molecules into one-dimensional chains running along [101]. Further stabilization of the crystal structure is provided by [pi]-[pi] interactions [shortest centroid-centroid distance = 3.6467 (17) Å].

Related literature

For background to the biological activity of N-substituted benzamides, their use in synthesis and for related structures, see: Saeed et al. (2011a[Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011a). Acta Cryst. E67, o279.],b[Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011b). Acta Cryst. E67, o1194.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8BrN3O5

  • Mr = 366.13

  • Monoclinic, P 21 /n

  • a = 7.1273 (2) Å

  • b = 26.6676 (7) Å

  • c = 7.5428 (2) Å

  • [beta] = 101.652 (2)°

  • V = 1404.10 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.96 mm-1

  • T = 296 K

  • 0.56 × 0.34 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.288, Tmax = 0.471

  • 18250 measured reflections

  • 2476 independent reflections

  • 2007 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.108

  • S = 1.10

  • 2476 reflections

  • 204 parameters

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.93 (3) 1.93 (3) 2.818 (3) 159 (3)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: 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: TK5029 ).


Acknowledgements

Dr Wesley T.-K. Chan, Professor Z.-Y. Zhou and the Hong Kong Polytechnic University are sincerely thanked for helping to collect the X-ray data.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011a). Acta Cryst. E67, o279.  [CSD] [CrossRef] [details]
Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011b). Acta Cryst. E67, o1194.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o26  [ doi:10.1107/S1600536811051464 ]

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