2-Chloro-N-(2-methyl­benzo­yl)benzene­sulfonamide

Suchetan, P.A.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810015990

Volume 66
Part 6
Page o1281
June 2010

Received 29 April 2010
Accepted 30 April 2010
Online 8 May 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.041
wR = 0.110
Data-to-parameter ratio = 15.7
Details

2-Chloro-N-(2-methylbenzoyl)benzenesulfonamide

P. A. Suchetan,^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, C₁₄H₁₂ClNO₃S, the N-H bond is antiperiplanar to the C=O bond. The dihedral angle between the two aromatic rings is 78.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-HO(S) hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl sulfonamides and for related structures, see: Gowda et al. (2009, 2010a,b).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M_r = 309.76
Monoclinic, P 2₁ /n
a = 6.6086 (5) Å
b = 10.9621 (9) Å
c = 20.080 (2) Å
= 95.586 (8)°
V = 1447.8 (2) Å³
Z = 4
Mo K radiation
= 0.41 mm^-1
T = 299 K
0.34 × 0.32 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.872, T_max = 0.893
5395 measured reflections
2917 independent reflections
2592 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.110
S = 1.07
2917 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.84 (2)	2.11 (2)	2.937 (2)	172 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: BT5259 ).

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o794.
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o326.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds