N-(2-Chloro­phenyl­sulfon­yl)acetamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811012785

Volume 67
Part 5
Page o1097
May 2011

Received 16 March 2011
Accepted 6 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.057
wR = 0.099
Data-to-parameter ratio = 16.0
Details

N-(2-Chlorophenylsulfonyl)acetamide

K. Shakuntala,^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 title compound, C₈H₈ClNO₃S, contains two independent molecules in which the C-S-N-C torsion angles are -71.7 (3) and 61.2 (3)°. The benzene rings and the SO₂-NH-CO-C segments form dihedral angles of 80.2 (1) and 88.1 (2)° in the two independent molecules. In the crystal, intermolecular N-HO hydrogen bonds link the molecules into chains in the b-axis direction.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see; Maren (1976). For its ability to form hydrogen bonds in the solid state, see; Yang & Guillory (1972). For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-(substituted phenylsulfonyl)-substituted amides, see: Gowda et al. (2010).

Experimental

Crystal data

C₈H₈ClNO₃S
M_r = 233.66
Monoclinic, P 2₁ /n
a = 11.215 (2) Å
b = 9.393 (2) Å
c = 19.655 (3) Å
= 98.61 (2)°
V = 2047.2 (6) Å³
Z = 8
Mo K radiation
= 0.56 mm^-1
T = 293 K
0.16 × 0.16 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with 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 = 0.916, T_max = 0.978
8327 measured reflections
4168 independent reflections
1942 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.099
S = 0.95
4168 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.85 (2)	2.03 (2)	2.848 (4)	162 (3)
N2-H2NO6ⁱⁱ	0.84 (2)	1.96 (2)	2.788 (4)	172 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: VM2086 ).

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1284.
Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.
Maren, T. H. (1976). Annu. Rev. Pharmacol Toxicol. 16, 309-327.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yang, S. S. & Guillory, J. K. (1972). J. Pharm. Sci. 61, 26-40.

organic compounds