2,2-Dichloro-N-(phenyl­sulfon­yl)­acetamide

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

doi:10.1107/S1600536808021831

Volume 64
Part 8
Page o1522
August 2008

Received 11 July 2008
Accepted 13 July 2008
Online 19 July 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.006 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 15.7
Details

2,2-Dichloro-N-(phenylsulfonyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a B. P. Sowmya ^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 conformation of the N-H and C=O bonds in the title compound, C₈H₇Cl₂NO₃S, is trans. The benzene ring and the SO₂-NH-CO-C group form a dihedral angle of 79.75 (8)°. Molecules are connected via N-HO hydrogen bonds to form linear supramolecular chains.

Related literature

For related literature, see: Gowda et al. (2006, 2007, 2008a,b); Gowda, Foro, Nirmala et al. (2008).

Experimental

Crystal data

C₈H₇Cl₂NO₃S
M_r = 268.11
Orthorhombic, P b c a
a = 9.669 (1) Å
b = 10.462 (1) Å
c = 21.024 (2) Å
V = 2126.7 (4) Å³
Z = 8
Mo K radiation
= 0.79 mm^-1
T = 299 (2) K
0.48 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.689, T_max = 0.728
9241 measured reflections
2156 independent reflections
1729 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.127
S = 1.13
2156 reflections
137 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.86	2.00	2.844 (3)	166
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2284 ).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Gowda, B. T., Foro, S., Nirmala, P. G., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1492.
Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008a). Acta Cryst. E64, o1274.
Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008b). Acta Cryst. E64, o1410.
Gowda, B. T., Nayak, R., Kozísek, J., Tokarcík, M. & Fuess, H. (2007). Acta Cryst. E63, o2967.
Gowda, B. T., Paulus, H., Kozisek, J., Tokarcik, M. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 675-682.
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds