2,4-Dimethyl-N-(4-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810049627

Volume 67
Part 1
Page o6
January 2011

Received 23 November 2010
Accepted 27 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.116
Data-to-parameter ratio = 14.9
Details

2,4-Dimethyl-N-(4-methylphenyl)benzenesulfonamide

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

^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 of the title compound, C₁₅H₁₇NO₂S, contains two independent molecules, which are twisted at the S-N bonds with C-SO₂-NH-C torsion angles of 48.3 (2) (molecule 1) and -75.7 (3)° (molecule 2). The dihedral angles between the benzene rings are 72.0 (1) (molecule 1) and 78.3 (1)° (molecule 2). The crystal structure features inversion dimers linked by pairs of N-HO hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (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 /c
a = 10.623 (1) Å
b = 10.770 (1) Å
c = 25.513 (2) Å
= 97.927 (6)°
V = 2891.0 (4) Å³
Z = 8
Mo K radiation
= 0.22 mm^-1
T = 299 K
0.40 × 0.30 × 0.20 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 = 0.917, T_max = 0.957
10876 measured reflections
5282 independent reflections
3743 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.116
S = 1.03
5282 reflections
355 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.85 (1)	2.15 (1)	2.991 (2)	169 (2)
N2-H2NO2ⁱⁱ	0.85 (1)	2.03 (1)	2.877 (2)	175 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: BQ2257 ).

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o576.
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3210.
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o989.
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.
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600-606.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds