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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 [sigma](C-C) = 0.006 Å
R = 0.062
wR = 0.164
Data-to-parameter ratio = 15.3
Details
Open access

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

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-H...O(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[Alkan, C., Tek, Y. & Kahraman, D. (2011). Turk. J. Chem. 35, 769-777.]); Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]), of N-arylsulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2649.]); Gowda et al. (2002[Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.]) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14N2O4S

  • Mr = 306.33

  • Triclinic, [P \overline 1]

  • a = 8.0248 (9) Å

  • b = 12.633 (1) Å

  • c = 14.711 (1) Å

  • [alpha] = 88.205 (9)°

  • [beta] = 80.818 (9)°

  • [gamma] = 82.323 (9)°

  • V = 1459.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.902, Tmax = 0.945

  • 10389 measured reflections

  • 5936 independent reflections

  • 3935 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O5i 0.83 (2) 2.36 (3) 3.056 (4) 142 (3)
N1-H1N...O7 0.83 (2) 2.45 (3) 3.011 (4) 126 (3)
N3-H3N...O3 0.85 (2) 2.40 (3) 3.012 (4) 129 (3)
N3-H3N...O1ii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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

Alkan, C., Tek, Y. & Kahraman, D. (2011). Turk. J. Chem. 35, 769-777.  [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.  [CSD] [CrossRef] [details]
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2649.  [CSD] [CrossRef] [details]
Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.  [ChemPort]
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.  [ISI] [CrossRef] [ChemPort]
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.  [CSD] [CrossRef] [details]
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3188  [ doi:10.1107/S1600536812042845 ]

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