N-(2,5-Dimethyl­phen­yl)-2-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536812047630

Volume 68
Part 12
Page o3426
December 2012

Received 16 November 2012
Accepted 20 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.042
wR = 0.108
Data-to-parameter ratio = 15.7
Details

N-(2,5-Dimethylphenyl)-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 crystal structure of the title compound, C₁₄H₁₄N₂O₄S, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The molecule is twisted at the S-N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N-HO_sulfonamide hydrogen bonds link the molecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Triclinic, $[P \overline 1]$
a = 8.1987 (7) Å
b = 9.6729 (9) Å
c = 9.9328 (9) Å
= 84.386 (9)°
= 72.096 (8)°
= 89.239 (9)°
V = 745.86 (12) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 293 K
0.36 × 0.24 × 0.16 mm

Data collection

Oxford Diffraction Xcaliburdiffractometer with 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 = 0.921, T_max = 0.964
4954 measured reflections
3027 independent reflections
2629 reflections with I > 2(I)
R_int = 0.011

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.108
S = 1.14
3027 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.82 (2)	2.27 (2)	3.023 (2)	152 (2)
Symmetry code: (i) -x, -y, -z+2.

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: RZ5026 ).

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.

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.
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