N-Benzoyl-2-chloro­benzene­sulfonamide

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

doi:10.1107/S1600536810008731

Volume 66
Part 4
Page o794
April 2010

Received 21 February 2010
Accepted 8 March 2010
Online 13 March 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R = 0.055
wR = 0.147
Data-to-parameter ratio = 12.6
Details

N-Benzoyl-2-chlorobenzenesulfonamide

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 crystal structure of the title compound, C₁₃H₁₀ClNO₃S, the conformation of the of the N-H bond in the C-SO₂-NH-C(O) segment is anti to the C=O bond. The dihedral angle between the two benzene rings is 73.3 (1)°. In the crystal, inversion dimers linked by pairs of N-HO hydrogen bonds occur.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009; 2010); Suchetan et al. (2010).

Experimental

Crystal data

C₁₃H₁₀ClNO₃S
M_r = 295.73
Triclinic, $[P \overline 1]$
a = 8.1087 (8) Å
b = 9.3057 (9) Å
c = 9.6592 (9) Å
= 74.841 (9)°
= 65.790 (8)°
= 78.077 (9)°
V = 637.52 (11) Å³
Z = 2
Cu K radiation
= 4.23 mm^-1
T = 299 K
0.55 × 0.50 × 0.45 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
3081 measured reflections
2210 independent reflections
2119 reflections with I > 2(I)
R_int = 0.026
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.147
S = 1.19
2210 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.68 e Å^-3
_min = -0.66 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.85 (1)	2.12 (1)	2.968 (3)	172 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); 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: NG2736 ).

Acknowledgements

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

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
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. (2010). Acta Cryst. E66, o326.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o327.

organic compounds