N-(3-Chloro­phen­yl)benzene­sulfonamide

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536808026895

Volume 64
Part 9
Page o1825
September 2008

Received 16 August 2008
Accepted 20 August 2008
Online 23 August 2008

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R = 0.036
wR = 0.094
Data-to-parameter ratio = 14.1
Details

N-(3-Chlorophenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b K. S. Babitha ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, 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, C₁₂H₁₀ClNO₂S, the N-H bond is trans to one of the S=O bonds. The two aromatic rings form a dihedral angle of 65.4 (1)°, compared with a value of 49.1 (1)° in N-(2-chlorophenyl)-benzenesulfonamide. The molecules are connected by intermolecular N-HO hydrogen bonds into chains running along the b axis.

Related literature

For related literature, see: Gelbrich et al. (2007); Gowda et al. (2005, 2008a,b); Perlovich et al. (2006).

Experimental

Crystal data

C₁₂H₁₀ClNO₂S
M_r = 267.72
Tetragonal, P 4₃ 2₁ 2
a = 8.8357 (7) Å
c = 32.081 (5) Å
V = 2504.6 (5) Å³
Z = 8
Cu K radiation
= 4.18 mm^-1
T = 299 (2) K
0.38 × 0.35 × 0.33 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.222, T_max = 0.251
5004 measured reflections
2232 independent reflections
2054 reflections with I > 2(I)
R_int = 0.071
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.094
S = 1.10
2232 reflections
158 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.21 e Å^-3
Absolute structure: Flack (1983), 840 Friedel pairs
Flack parameter: -0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.88 (1)	2.029 (13)	2.875 (2)	162 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 4}}]$ .

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2659 ).

Acknowledgements

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

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds