2-Bromo-4-nitro­aniline

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Shafiq, M.

doi:10.1107/S1600536809004073

Volume 65
Part 3
Page o480
March 2009

Received 1 February 2009
Accepted 3 February 2009
Online 6 February 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.008 Å
R = 0.039
wR = 0.092
Data-to-parameter ratio = 15.4
Details

2-Bromo-4-nitroaniline

Muhammad Nadeem Arshad,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan ^a and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the molecule of the title compound, C₆H₅BrN₂O₂, the dihedral angle between the nitro group and the aromatic ring is 4.57 (4)°. An intramolecular N-HBr interaction results in the formation of a planar five-membered ring, which is oriented with respect to the aromatic ring at a dihedral angle of 1.64 (6)°. In the crystal structure, intermolecular N-HN and N-HO hydrogen bonds link the molecules.

Related literature

For related structures, see: Arshad et al. (2008, 2009); McPhail & Sim (1965); McWilliam et al. (2001); Krishna Mohan et al. (2004).

Experimental

Crystal data

C₆H₅BrN₂O₂
M_r = 217.03
Orthorhombic, P n a 2₁
a = 11.098 (3) Å
b = 16.763 (4) Å
c = 3.9540 (9) Å
V = 735.6 (3) Å³
Z = 4
Mo K radiation
= 5.53 mm^-1
T = 296 (2) K
0.26 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.450, T_max = 0.578
4932 measured reflections
1542 independent reflections
986 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.092
S = 1.00
1542 reflections
100 parameters
1 restraint
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.62 e Å^-3
Absolute structure: Flack (1983), 469 Friedel pairs
Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN1ⁱ	0.86	2.32	3.158 (7)	167.00
N1-H1BBr1	0.86	2.68	3.095 (5)	111.00
N1-H1BO2ⁱⁱ	0.86	2.32	3.049 (7)	143.00
Symmetry codes: (i) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2621 ).

Acknowledgements

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholarship under the Indigenous PhD Program (PIN 042-120607-PS2-183).

References

Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045.
Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009). Acta Cryst. E65, o230.
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Krishna Mohan, K. V. V., Narender, N., Srinivasu, P., Kulkarni, S. J. & Raghavan, K. V. (2004). Synth. Commun. 34, 2143-2152.
McPhail, A. T. & Sim, G. A. (1965). J. Chem. Soc. pp. 227-236.
McWilliam, S. A., Skakle, J. M. S., Low, J. N., Wardell, J. L., Garden, S. J., Pinto, A. C., Torres, J. C. & Glidewell, C. (2001). Acta Cryst. C57, 942-945.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds