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

Novina, J.J.; Vasuki, G.; Baheti, A.; Thomas, K.R.J.

doi:10.1107/S1600536813000597

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 (C-C) = 0.004 Å
R = 0.033
wR = 0.075
Data-to-parameter ratio = 16.6
Details

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

J. Josephine Novina,^a G. Vasuki,^b ^* Abhishek Baheti ^c and K. R. Justin Thomas ^c

^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); Mandadapu et al. (2009); Youn & Bihn (2009); Yulan et al. (2010). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008). For related structures, see: Li & Cui (2011); Kus et al. (2009); Hammond et al. (2009); Gowda et al. (2010); Novina et al. (2012).

Experimental

Crystal data

C₁₉H₁₃Br₂NO
M_r = 431.12
Monoclinic, P 2₁ /c
a = 9.0188 (5) Å
b = 11.6415 (9) Å
c = 16.0068 (12) Å
= 100.737 (2)°
V = 1651.2 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.238, T_max = 0.374
16420 measured reflections
3453 independent reflections
2302 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.075
S = 1.01
3453 reflections
208 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.49 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

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

organic compounds