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

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

doi:10.1107/S1600536812042845

Volume 68
Part 11
Page o3188
November 2012

Received 11 October 2012
Accepted 13 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.062
wR = 0.164
Data-to-parameter ratio = 15.3
Details

N-(2,3-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

There are two independent molecules in the asymmetric unit of the title compound, C₁₄H₁₄N₂O₄S. The N-H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The molecules are twisted at the S-N bonds with torsion angles of -60.4 (3) and 58.8 (3)° in the two molecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both molecules are involved in an intramolecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N-HO(S) hydrogen bonds link like molecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (1994); Saeed et al. (2010); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Triclinic, $[P \overline 1]$
a = 8.0248 (9) Å
b = 12.633 (1) Å
c = 14.711 (1) Å
= 88.205 (9)°
= 80.818 (9)°
= 82.323 (9)°
V = 1459.0 (2) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 293 K
0.44 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer 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 = 0.902, T_max = 0.945
10389 measured reflections
5936 independent reflections
3935 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.164
S = 1.02
5936 reflections
389 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.73 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO5ⁱ	0.83 (2)	2.36 (3)	3.056 (4)	142 (3)
N1-H1NO7	0.83 (2)	2.45 (3)	3.011 (4)	126 (3)
N3-H3NO3	0.85 (2)	2.40 (3)	3.012 (4)	129 (3)
N3-H3NO1ⁱⁱ	0.85 (2)	2.41 (3)	3.070 (4)	135 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -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: SJ5271 ).

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

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Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds