N-(2,6-Dimethyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536808024653

Volume 64
Part 9
Page o1691
September 2008

Received 30 July 2008
Accepted 31 July 2008
Online 6 August 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 14.3
Details

N-(2,6-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 N-H bond is trans to one of the S=O double bonds, similar to what is observed in N-(2-methylphenyl)benzenesulfonamide and other aryl sulfonamides. The two aromatic rings enclose a dihedral angle of 44.9 (1)°. The molecules are connected by intermolecular N-HO hydrogen bonds into chains running along the a axis. An intermolecular C-HO hydrogen bond is also present.

Related literature

For related literature, see: Gelbrich et al. (2007); Gowda et al. (2005, 2008); Gowda, Babitha et al. (2007); Gowda, Foro et al. (2007); Perlovich et al. (2006).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Monoclinic, P 2₁ /n
a = 5.2133 (7) Å
b = 17.971 (2) Å
c = 14.040 (1) Å
= 91.681 (9)°
V = 1314.8 (2) Å³
Z = 4
Cu K radiation
= 2.13 mm^-1
T = 299 (2) K
0.55 × 0.35 × 0.33 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
2622 measured reflections
2340 independent reflections
2197 reflections with I > 2(I)
R_int = 0.071
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.134
S = 1.08
2340 reflections
164 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.86	2.55	3.179 (2)	131
C5-H5O2ⁱⁱ	0.93	2.57	3.229 (3)	129
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); 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: BT2760 ).

Acknowledgements

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

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Babitha, K. S., Tokarcík, M., Kozísek, J. & Fuess, H. (2007). Acta Cryst. E63, o3361.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1692.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o3325.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
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.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds