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

Waris, G.; Siddiqi, H.M.; Flörke, U.; Hussain, R.; Butt, M.S.

doi:10.1107/S1600536813002705

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 (C-C) = 0.004 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 18.1
Details

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

Ghulam Waris,^a Humaira Masood Siddiqi,^a ^* Ulrich Flörke,^b Rizwan Hussain ^c and M. Saeed Butt ^a

^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-HN contact occurs. In the crystal, molecules are connected by pairs of N-HO hydrogen bonds into chains along the c axis.

Related literature

For related structures, see: Malone et al. (1997); Qi et al. (2003). For imide-amide polymers, see: Sun et al. (2006); Zhong et al. (2002). For properties of polymers containing heterocyclic groups, see: Diakoumakos & Mikroyannidis (1994); Hamciuc et al. (2001).

Experimental

Crystal data

C₁₉H₁₃Br₂N₃O₂
M_r = 475.14
Monoclinic, C 2/c
a = 9.550 (2) Å
b = 22.698 (5) Å
c = 8.748 (2) Å
= 107.511 (5)°
V = 1808.5 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.452, T_max = 0.637
8520 measured reflections
2159 independent reflections
1695 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.105
S = 1.02
2159 reflections
119 parameters
H-atom parameters constrained
_max = 0.94 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2	0.88	2.23	2.673 (3)	111
N1-H1AO1ⁱ	0.88	2.32	3.044 (3)	140
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287-293.
Malone, J. F., Murray, C. M., Dolan, G. M., Docherty, R. & Lavery, A. J. (1997). Chem. Mater. 9, 2983-2989.
Qi, J. Y., Yang, Q. Y., Lam, K. H., Zhou, Z. Y. & Chan, A. S. C. (2003). Acta Cryst. E59, o415-o416.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, S., Li, C., Zhang, L., Du, H. L. & Burnell-Gray, J. S. (2006). Eur. Polym. J. 42, 1643-1652.
Zhong, S., Li, C. & Xiao, X. (2002). J. Membr. Sci. 199, 53-58.

organic compounds