N-(4-Methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810002278

Volume 66
Part 2
Page o435
February 2010

Received 17 January 2010
Accepted 18 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 16.1
Details

N-(4-Methylphenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^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 title compound, C₁₃H₁₃NO₂S, contains two independent molecules. The dihedral angles between the aromatic rings in the two molecules are 78.0 (1) and 74.0 (1)°. In the crystal, intermolecular N-HO hydrogen bonds pack the molecules into a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005). For related structures, see: Gelbrich et al. (2007); Gowda et al. (2008, 2010); Perlovich et al. (2006).

Experimental

Crystal data

C₁₃H₁₃NO₂S
M_r = 247.30
Monoclinic, P 2₁ /c
a = 10.8963 (7) Å
b = 9.6981 (7) Å
c = 24.089 (2) Å
= 101.335 (6)°
V = 2495.9 (3) Å³
Z = 8
Mo K radiation
= 0.25 mm^-1
T = 299 K
0.48 × 0.36 × 0.36 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 = 0.890, T_max = 0.916
11057 measured reflections
5102 independent reflections
3835 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.115
S = 1.07
5102 reflections
317 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.86 (1)	2.09 (1)	2.924 (2)	166 (2)
N2-H2NO1	0.85 (1)	2.17 (1)	3.0056 (19)	168 (2)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: BT5173 ).

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, o1692.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o434.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds