N-(3-Chloro­benzo­yl)-3-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536811054857

Volume 68
Part 1
Page o244
January 2012

Received 19 December 2011
Accepted 20 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.105
Data-to-parameter ratio = 14.1
Details

N-(3-Chlorobenzoyl)-3-nitrobenzenesulfonamide

P. A. Suchetan,^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

In the title compound, C₁₃H₉ClN₂O₅S, the dihedral angle between the two benzene rings is 83.5 (1)°. In the crystal, molecules are linked via N-HO(S) hydrogen bonds into helical chains running along the b axis.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2004), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), onN-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983).

Experimental

Crystal data

C₁₃H₉ClN₂O₅S
M_r = 340.73
Monoclinic, P 2₁ /c
a = 11.891 (2) Å
b = 5.0577 (6) Å
c = 23.488 (3) Å
= 90.43 (1)°
V = 1412.6 (3) Å³
Z = 4
Mo K radiation
= 0.44 mm^-1
T = 293 K
0.46 × 0.20 × 0.10 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 = 0.822, T_max = 0.957
4873 measured reflections
2840 independent reflections
2204 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.105
S = 1.20
2840 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.82 (2)	2.29 (2)	3.100 (3)	169 (3)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: BT5758 ).

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi for a special grant under the UGC-BSR one-time grant to faculty.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.
Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.
Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.
Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.
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., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3515.

organic compounds