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Volume 65 
Part 2 
Page o366  
February 2009  

Received 15 January 2009
Accepted 16 January 2009
Online 23 January 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.094
Data-to-parameter ratio = 15.5
Details
Open access

N-(2,3-Dimethylphenyl)benzenesulfonamide

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, C14H15NO2S, the amino H atom is trans to one of the O atoms of the SO2 group. Furthermore, the N-H bond is anti to the ortho- and meta-methyl groups of the aromatic ring. The two aromatic rings are tilted relative to each other by 64.8 (1)°. The molecules form zigzag chains along the a axis via intermolecular N-H...O hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]); Gowda et al. (2008a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.],b[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692.],c[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64, o2190.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15NO2S

  • Mr = 261.33

  • Orthorhombic, P 21 21 21

  • a = 6.3969 (5) Å

  • b = 8.8767 (6) Å

  • c = 23.082 (2) Å

  • V = 1310.67 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 299 (2) K

  • 0.50 × 0.30 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]) Tmin = 0.889, Tmax = 0.958

  • 5869 measured reflections

  • 2611 independent reflections

  • 2200 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.094

  • S = 1.07

  • 2611 reflections

  • 168 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1060 Friedel pairs

  • Flack parameter: -0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.84 (3) 2.10 (3) 2.936 (2) 176 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CrysAlis CCD (Oxford Diffraction, 2004[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]); data reduction: CrysAlis RED; 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, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2853 ).


Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.  [ISI] [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.  [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692.  [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64, o2190.  [CSD] [CrossRef] [details]
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.  [ChemPort]
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2009). E65, o366  [ doi:10.1107/S1600536809002098 ]

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