N-(2-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

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

doi:10.1107/S1600536812048684

Volume 68
Part 12
Page o3497
December 2012

Received 16 November 2012
Accepted 27 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.110
Data-to-parameter ratio = 14.9
Details

N-(2-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 70.60 (11)°. An intramolecular N-HCl contact occurs. In the crystal, molecules form inversion dimers via pairs of N-HO hydrogen bonds.

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. (2005) and of N-chloroarylamides, see: Gowda & Shetty (2004); Gowda & Weiss (1994); Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001); Allen et al. (1998); Bernstein et al. (1995); Etter (1990).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M_r = 312.72
Monoclinic, P 2₁ /n
a = 9.2762 (9) Å
b = 12.981 (1) Å
c = 11.970 (1) Å
= 110.97 (1)°
V = 1345.9 (2) Å³
Z = 4
Mo K radiation
= 0.45 mm^-1
T = 293 K
0.42 × 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 = 0.833, T_max = 0.956
5256 measured reflections
2748 independent reflections
2019 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.110
S = 1.16
2748 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.84 (2)	2.20 (2)	3.003 (3)	159 (3)
N1-H1NCl1	0.84 (2)	2.56 (3)	2.984 (3)	112 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: BT6858 ).

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

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Allen, F. H., Raithby, P. R., Shields, G. P. & Taylor, R. (1998). Chem. Commun. pp. 1043-1044.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2766.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
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