4-Chloro-N-(2-chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810019057

Volume 66
Part 6
Page o1467
June 2010

Received 19 May 2010
Accepted 21 May 2010
Online 26 May 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.107
Data-to-parameter ratio = 15.4
Details

4-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^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

In the structure of the title compound, C₁₃H₉Cl₂NO₃S, the conformation of the N-H bond in the C-SO₂-NH-C(O) segment is anti to the C=O bond. The molecule is twisted at the S atom with a torsion angle of 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO₂-NH-C-O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, molecules are linked by pairs of N-HO hydrogen bonds, forming inversion dimers.

Related literature

For our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b,c).

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S
M_r = 330.17
Triclinic, $[P \overline 1]$
a = 6.3882 (9) Å
b = 10.311 (1) Å
c = 11.171 (1) Å
= 79.01 (1)°
= 74.47 (1)°
= 84.76 (1)°
V = 695.32 (13) Å³
Z = 2
Mo K radiation
= 0.62 mm^-1
T = 299 K
0.24 × 0.20 × 0.14 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 = 0.865, T_max = 0.918
4417 measured reflections
2825 independent reflections
2378 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.107
S = 1.06
2825 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.81 (2)	2.13 (2)	2.914 (2)	164 (2)
Symmetry code: (i) -x+1, -y, -z.

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: XU2765 ).

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. (2010). Acta Cryst. E66, o326.
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.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o766.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1040.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010c). Acta Cryst. E66, o1253.

organic compounds