N-(2,3-Dimethyl­phen­yl)benzene­sulfonamide

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536809002098

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 (C-C) = 0.004 Å
R = 0.034
wR = 0.094
Data-to-parameter ratio = 15.5
Details

N-(2,3-Dimethylphenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b K. S. Babitha ^a and Hartmut Fuess ^b

^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-HO hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al. (2007); Gowda et al. (2005); Gowda et al. (2008a,b,c); Perlovich et al. (2006).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 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 radiation
= 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 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.889, T_max = 0.958
5869 measured reflections
2611 independent reflections
2200 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(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
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3
Absolute structure: Flack (1983), 1060 Friedel pairs
Flack parameter: -0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); 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.
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64, o2190.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds