N-(2,6-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536810014571

Volume 66
Part 5
Page o1168
May 2010

Received 8 April 2010
Accepted 20 April 2010
Online 24 April 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.042
wR = 0.116
Data-to-parameter ratio = 14.5
Details

N-(2,6-Dimethylphenyl)-4-methylbenzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b 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 title compound, C₁₅H₁₇NO₂S, the molecule is bent at the S atom, the C-SO₂-NH-C torsion angle being 88.0 (2)°. The dihedral angle between the two aromatic rings is 49.8 (1)°. In the crystal, molecules are linked into zigzag chains parallel to the a axis via N-HO hydrogen bonds.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005). For our study of the effect of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2008, 2009, 2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Monoclinic, P 2₁ /n
a = 5.1412 (5) Å
b = 17.310 (2) Å
c = 16.429 (2) Å
= 96.65 (1)°
V = 1452.2 (3) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 299 K
0.46 × 0.32 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector.
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.906, T_max = 0.970
7741 measured reflections
2580 independent reflections
2090 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.116
S = 1.04
2580 reflections
178 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.85 (1)	2.20 (1)	3.040 (2)	169 (2)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2025 ).

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o144.
Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
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.
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds