N-(3,4-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809010459

Volume 65
Part 4
Page o877
April 2009

Received 7 March 2009
Accepted 21 March 2009
Online 28 March 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.127
Data-to-parameter ratio = 16.6
Details

N-(3,4-Dimethylphenyl)-4-methylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
Correspondence e-mail: gowdabt@yahoo.com

In the crystal structure of the title compound, C₁₅H₁₇NO₂S, the conformations of the N-C bond in the C-SO₂-NH-C segment are trans and gauche, respectively, with respect to the S=O bonds. The molecule is bent at the S atom with a C-SO₂-NH-C torsion angle of -61.8 (2)°. Furthermore, the conformation of the N-H bond and the 3-methyl group in the aniline benzene ring are nearly anti to each other. The dihedral angle between the benzene rings is 47.8 (1)°. In the crystal, N-HO hydrogen bonds link the molecules into chains.

Related literature

For the preparation of the compound, see: Shetty & Gowda (2005). For related structures, see: Gelbrich et al. (2007); Gowda et al. (2008a,b; 2009); Perlovich et al. (2006)

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Monoclinic, P 2₁ /c
a = 9.2528 (7) Å
b = 15.329 (1) Å
c = 10.4469 (7) Å
= 102.558 (7)°
V = 1446.30 (17) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 299 K
0.45 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.907, T_max = 0.929
10438 measured reflections
2902 independent reflections
2360 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.127
S = 1.06
2902 reflections
175 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.86	2.42	2.963 (2)	122
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2240 ).

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. (2008a). Acta Cryst. E64, o1691.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o2190.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o366.
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.
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds