N-(3-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536812047496

Volume 68
Part 12
Page o3424
December 2012

Received 16 November 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.163
Data-to-parameter ratio = 13.2
Details

N-(3-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

There are two independent molecules in the asymmetric unit of the title compound, C₁₂H₉ClN₂O₄S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N-HO hydrogen bonds link the molecules into zigzag chains parallel to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylamides, see: Gowda & Shetty (2004); Gowda & Weiss (1994); Shetty & Gowda (2004).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M_r = 312.72
Monoclinic, P 2₁ /n
a = 14.3419 (8) Å
b = 7.7579 (4) Å
c = 23.895 (1) Å
= 90.345 (5)°
V = 2658.6 (2) Å³
Z = 8
Mo K radiation
= 0.46 mm^-1
T = 293 K
0.48 × 0.40 × 0.20 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 = 0.810, T_max = 0.914
9649 measured reflections
4839 independent reflections
3112 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.163
S = 1.05
4839 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.83 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3-H3NO4ⁱ	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)
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: BT6857 ).

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under UGC-BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its promotion of university research and scientific excellence programme.

References

Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2576.
Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.
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