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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 [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.108
Data-to-parameter ratio = 15.7
Details
Open access

N-(2,5-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

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-H...Osulfonamide 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[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o3188.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14N2O4S

  • Mr = 306.33

  • Triclinic, [P \overline 1]

  • a = 8.1987 (7) Å

  • b = 9.6729 (9) Å

  • c = 9.9328 (9) Å

  • [alpha] = 84.386 (9)°

  • [beta] = 72.096 (8)°

  • [gamma] = 89.239 (9)°

  • V = 745.86 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.921, Tmax = 0.964

  • 4954 measured reflections

  • 3027 independent reflections

  • 2629 reflections with I > 2[sigma](I)

  • Rint = 0.011

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 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[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: 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.  [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]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
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, o3426  [ doi:10.1107/S1600536812047630 ]

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