N-(2,3-Dichloro­phen­yl)-2-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812048076

Volume 69
Part 1
Page o76
January 2013

Received 21 November 2012
Accepted 22 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 15.1
Details

N-(2,3-Dichlorophenyl)-2-nitrobenzenesulfonamide

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₂H₈Cl₂N₂O₄S, the N-C bond in the C-SO₂-NH-C segment has gauche torsions with respect to the S=O bonds. Further, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The molecule is twisted at the S-N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intramolecular bifurcated N-H(O,O) hydrogen bond. In the crystal, pairs of N-HO(S) hydrogen bonds link the molecules into inversion dimers with R₂²(8) motifs.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).

Experimental

Crystal data

C₁₂H₈Cl₂N₂O₄S
M_r = 347.16
Monoclinic, P 2₁ /n
a = 8.2197 (5) Å
b = 15.863 (1) Å
c = 11.0108 (6) Å
= 93.450 (6)°
V = 1433.09 (15) Å³
Z = 4
Mo K radiation
= 0.61 mm^-1
T = 293 K
0.44 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.774, T_max = 0.847
5760 measured reflections
2923 independent reflections
2304 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.092
S = 1.01
2923 reflections
193 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.83 (2)	2.48 (2)	3.136 (2)	137 (2)
N1-H1NO3	0.83 (2)	2.51 (2)	3.065 (3)	125 (2)
Symmetry code: (i) -x, -y+2, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5027 ).

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its Promotion of University Research and Scientific Excellence Programme.

References

Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o3188.
Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds