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Volume 69 
Part 3 
Page o416  
March 2013  

Received 22 December 2012
Accepted 27 January 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.004 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 18.1
Details
Open access

N,N'-Bis(4-bromophenyl)pyridine-2,6-dicarboxamide

aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan,bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and cNESCOM, PO Box 2216 Islamabad, Pakistan
Correspondence e-mail: humaira_siddiqi@yahoo.com

The molecule of the title compound, C19H13Br2N3O2, lies about a twofold rotation axis. The benzene ring makes dihedral angles of 8.9 (2) and 16.4 (2)° with the central pyridine ring and the second benzene ring, respectively. An intramolecular N-H...N contact occurs. In the crystal, molecules are connected by pairs of N-H...O hydrogen bonds into chains along the c axis.

Related literature

For related structures, see: Malone et al. (1997[Malone, J. F., Murray, C. M., Dolan, G. M., Docherty, R. & Lavery, A. J. (1997). Chem. Mater. 9, 2983-2989.]); Qi et al. (2003[Qi, J. Y., Yang, Q. Y., Lam, K. H., Zhou, Z. Y. & Chan, A. S. C. (2003). Acta Cryst. E59, o415-o416.]). For imide-amide polymers, see: Sun et al. (2006[Sun, S., Li, C., Zhang, L., Du, H. L. & Burnell-Gray, J. S. (2006). Eur. Polym. J. 42, 1643-1652.]); Zhong et al. (2002[Zhong, S., Li, C. & Xiao, X. (2002). J. Membr. Sci. 199, 53-58.]). For properties of polymers containing heterocyclic groups, see: Diakoumakos & Mikroyannidis (1994[Diakoumakos, C. D. & Mikroyannidis, J. A. (1994). Polymer, 35, 1986-1990.]); Hamciuc et al. (2001[Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287-293.]).

[Scheme 1]

Experimental

Crystal data
  • C19H13Br2N3O2

  • Mr = 475.14

  • Monoclinic, C 2/c

  • a = 9.550 (2) Å

  • b = 22.698 (5) Å

  • c = 8.748 (2) Å

  • [beta] = 107.511 (5)°

  • V = 1808.5 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.50 mm-1

  • T = 130 K

  • 0.21 × 0.12 × 0.11 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.452, Tmax = 0.637

  • 8520 measured reflections

  • 2159 independent reflections

  • 1695 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.105

  • S = 1.02

  • 2159 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.94 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2 0.88 2.23 2.673 (3) 111
N1-H1A...O1i 0.88 2.32 3.044 (3) 140
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2085 ).


Acknowledgements

Financial assistance for this project by the Higher Education Commission of Pakistan through the International Research Support Initiative Programe (IRSIP) is acknowledged by the authors.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Diakoumakos, C. D. & Mikroyannidis, J. A. (1994). Polymer, 35, 1986-1990.  [CrossRef] [ChemPort]
Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287-293.  [ISI] [CrossRef] [ChemPort]
Malone, J. F., Murray, C. M., Dolan, G. M., Docherty, R. & Lavery, A. J. (1997). Chem. Mater. 9, 2983-2989.  [ISI] [CrossRef] [ChemPort]
Qi, J. Y., Yang, Q. Y., Lam, K. H., Zhou, Z. Y. & Chan, A. S. C. (2003). Acta Cryst. E59, o415-o416.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, S., Li, C., Zhang, L., Du, H. L. & Burnell-Gray, J. S. (2006). Eur. Polym. J. 42, 1643-1652.  [ISI] [CrossRef] [ChemPort]
Zhong, S., Li, C. & Xiao, X. (2002). J. Membr. Sci. 199, 53-58.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o416  [ doi:10.1107/S1600536813002705 ]

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