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

Saeed, S.; Rashid, N.; Hussain, R.; Wong, W.-T.

doi:10.1107/S1600536811051464

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 (C-C) = 0.004 Å
R = 0.035
wR = 0.108
Data-to-parameter ratio = 12.1
Details

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

Sohail Saeed,^a ^* Naghmana Rashid,^a Rizwan Hussain ^b and Wing-Tak Wong ^c

^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-HO 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,b).

Experimental

Crystal data

C₁₃H₈BrN₃O₅
M_r = 366.13
Monoclinic, P 2₁ /n
a = 7.1273 (2) Å
b = 26.6676 (7) Å
c = 7.5428 (2) Å
= 101.652 (2)°
V = 1404.10 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.288, T_max = 0.471
18250 measured reflections
2476 independent reflections
2007 reflections with I > 2(I)
R_int = 0.060

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); 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.
Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011a). Acta Cryst. E67, o279.
Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011b). Acta Cryst. E67, o1194.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds