N-(3,5-Dichloro­phen­yl)-2-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536812048283

Volume 68
Part 12
Page o3482
December 2012

Received 21 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 15.1
Details

N-(3,5-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 C-S-N-C torsion angle is 49.34 (18)° and the dihedral angle between the benzene rings is 71.92 (10)°. The amide H atom exhibits bifurcated hydrogen bonding. The N-H bond is syn to the ortho-nitro group enabling the formation of an S(7) loop. In the crystal, pairs of N-HO(S) hydrogen bonds link the molecules into inversion dimers via R₂²(8) rings.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001).

Experimental

Crystal data

C₁₂H₈Cl₂N₂O₄S
M_r = 347.16
Triclinic, $[P \overline 1]$
a = 8.2823 (8) Å
b = 8.3436 (9) Å
c = 10.670 (1) Å
= 76.730 (8)°
= 89.298 (9)°
= 86.875 (9)°
V = 716.59 (12) Å³
Z = 2
Mo K radiation
= 0.61 mm^-1
T = 293 K
0.44 × 0.40 × 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
4766 measured reflections
2925 independent reflections
2600 reflections with I > 2(I)
R_int = 0.009

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.092
S = 1.04
2925 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.85 (2)	2.23 (2)	3.052 (2)	162 (2)
N1-H1NO3	0.85 (2)	2.44 (2)	2.940 (2)	118 (2)
Symmetry code: (i) -x, -y, -z+1.

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: TK5173 ).

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2823.
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.
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.
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