[Journal logo]

Volume 69 
Part 2 
Page o222  
February 2013  

Received 6 January 2013
Accepted 7 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.075
Data-to-parameter ratio = 16.6
Details
Open access

N-(4,4'-Dibromo-[1,1'-biphenyl]-2-yl)benzamide

aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India,bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, and cOrganic Materials Lab, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Correspondence e-mail: vasuki.arasi@yahoo.com

In the title compound, C19H13Br2NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14)°. The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15)°. There are no significant intermolecular interactions in the crystal structure.

Related literature

For applications of the title compound, see: Libman & Slack (1951[Libman, D. D. & Slack, R. (1951). J. Chem. Soc. pp. 2588-2590.]); Mandadapu et al. (2009[Mandadapu, A. K., Saifuddin, M., Agarwal, P. K. & Kundu, B. (2009). Org. Biomol. Chem. 7, 2796-2803.]); Youn & Bihn (2009[Youn, S. W. & Bihn, J. H. (2009). Tetrahedron Lett. 50, 4598-4601.]); Yulan et al. (2010[Yulan, C., Fenghong, L. & Zhishan, B. (2010). Macromolecules, 43, 1349-1355.]). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008[Zhu, L., Patel, M. & Zhang, M. (2008). Tetrahedron Lett. 49, 2734-2737.]). For related structures, see: Li & Cui (2011[Li, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.]); Kus et al. (2009[Kus, P., Zemanek, A. & Jones, P. G. (2009). Acta Cryst. E65, o1327.]); Hammond et al. (2009[Hammond, N., Carvalho, P., Wu, Y. & Avery, M. A. (2009). Acta Cryst. E65, o1052-o1053.]); Gowda et al. (2010[Gowda, B. T., Tokarcík, M., Rodrigues, V. Z., Kozísek, J. & Fuess, H. (2010). Acta Cryst. E66, o1897.]); Novina et al. (2012[Novina, J. J., Vasuki, G., Kumar, S. & Thomas, K. R. J. (2012). Acta Cryst. E68, o319.]).

[Scheme 1]

Experimental

Crystal data
  • C19H13Br2NO

  • Mr = 431.12

  • Monoclinic, P 21 /c

  • a = 9.0188 (5) Å

  • b = 11.6415 (9) Å

  • c = 16.0068 (12) Å

  • [beta] = 100.737 (2)°

  • V = 1651.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.91 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.238, Tmax = 0.374

  • 16420 measured reflections

  • 3453 independent reflections

  • 2302 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.075

  • S = 1.01

  • 3453 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2551 ).


Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IIT Madras, Chennai, for the data collection.

References

Bruker (2004). APEX2, SAINT and XPREP, Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gowda, B. T., Tokarcík, M., Rodrigues, V. Z., Kozísek, J. & Fuess, H. (2010). Acta Cryst. E66, o1897.  [CSD] [CrossRef] [details]
Hammond, N., Carvalho, P., Wu, Y. & Avery, M. A. (2009). Acta Cryst. E65, o1052-o1053.  [CSD] [CrossRef] [ChemPort] [details]
Kus, P., Zemanek, A. & Jones, P. G. (2009). Acta Cryst. E65, o1327.  [CSD] [CrossRef] [details]
Li, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.  [CSD] [CrossRef] [details]
Libman, D. D. & Slack, R. (1951). J. Chem. Soc. pp. 2588-2590.  [CrossRef]
Mandadapu, A. K., Saifuddin, M., Agarwal, P. K. & Kundu, B. (2009). Org. Biomol. Chem. 7, 2796-2803.  [CrossRef] [PubMed] [ChemPort]
Novina, J. J., Vasuki, G., Kumar, S. & Thomas, K. R. J. (2012). Acta Cryst. E68, o319.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Youn, S. W. & Bihn, J. H. (2009). Tetrahedron Lett. 50, 4598-4601.  [ISI] [CrossRef] [ChemPort]
Yulan, C., Fenghong, L. & Zhishan, B. (2010). Macromolecules, 43, 1349-1355.
Zhu, L., Patel, M. & Zhang, M. (2008). Tetrahedron Lett. 49, 2734-2737.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o222  [ doi:10.1107/S1600536813000597 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.