N-(4-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812049070

Volume 69
Part 1
Page o7
January 2013

Received 27 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.041
wR = 0.092
Data-to-parameter ratio = 8.5
Details

N-(4-Chlorophenyl)-4-nitrobenzenesulfonamide

U. Chaithanya,^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, C₁₂H₉ClN₂O₄S, the dihedral angle between the benzene rings is 31.4 (2)°. In the crystal, N-HO hydrogen bonds link the molecules into C(4) chains running along the a-axis direction.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2003) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M_r = 312.72
Monoclinic, C c
a = 5.0881 (4) Å
b = 13.0313 (9) Å
c = 19.886 (2) Å
= 94.194 (7)°
V = 1315.00 (19) Å³
Z = 4
Mo K radiation
= 0.46 mm^-1
T = 293 K
0.46 × 0.24 × 0.12 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 = 0.815, T_max = 0.947
2432 measured reflections
1557 independent reflections
1432 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.092
S = 1.13
1557 reflections
184 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.29 e Å^-3
Absolute structure: Flack (1983), 203 Friedel pairs
Flack parameter: -0.02 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.85 (2)	2.16 (2)	3.007 (4)	173 (5)
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 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: BT6873 ).

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. 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

Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2872.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gowda, B. T., Damodara, N. & Jyothi, K. (2005). Int. J. Chem. Kinet. 37, 572-582.
Gowda, B. T., D'Souza, J. D. & Kumar, B. H. A. (2003). Z. Naturforsch. Teil A, 58, 51-56.
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds