2,4-Dimethyl-N-phenyl­benzene­sulfonamide

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

doi:10.1107/S160053680900573X

Volume 65
Part 3
Page o576
March 2009

Received 16 January 2009
Accepted 18 February 2009
Online 21 February 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 7.6
Details

2,4-Dimethyl-N-phenylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a 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

The asymmetric unit of the crystal structure of the title compound, C₁₄H₁₅NO₂S, contains two molecules. The conformations of the N-C bonds in the C-SO₂-NH-C segments of the structure have trans and gauche torsion angles with the S=O bonds. Furthermore, the torsion angles of the C-SO₂-NH-C groups in the two molecules are 46.1 (3) (glide image of molecule 1) and 47.7 (3)° (molecule 2). The ortho-methyl groups in the sulfonyl benzene ring are oriented away from the S=O bonds. The two benzene rings are tilted relative to each other by 67.5 (1) and 72.9 (1)° in the two molecules. N-HO and C-HO hydrogen bonds pack the molecules into one-dimensional chains in different directions, resulting in a two-dimensional network.

Related literature

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

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Orthorhombic, P c a 2₁
a = 19.113 (3) Å
b = 8.9290 (8) Å
c = 15.781 (1) Å
V = 2693.2 (5) Å³
Z = 8
Cu K radiation
= 2.09 mm^-1
T = 299 K
0.50 × 0.43 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.401, T_max = 0.593
4916 measured reflections
2505 independent reflections
2421 reflections with I > 2(I)
R_int = 0.050
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.090
S = 1.09
2505 reflections
330 parameters
7 restraints
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), no Friedel pairs
Flack parameter: 0.008 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.86	2.41	3.164 (3)	147
N2-H2NO1ⁱⁱ	0.86	2.22	3.056 (3)	164
C11-H11O2ⁱⁱⁱ	0.93	2.50	3.227 (4)	135
C23-H23O4ⁱⁱⁱ	0.93	2.50	3.316 (4)	147
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+1, z]$ ; (iii) x, y+1, z.

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, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2115 ).

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.
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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
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. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds