2,5-Dichloro­anilinium 4-chloro­benzene­sulfonate

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811010518

Volume 67
Part 4
Page o967
April 2011

Received 20 March 2011
Accepted 21 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 12.9
Details

2,5-Dichloroanilinium 4-chlorobenzenesulfonate

K. Shakuntala,^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 crystal of the title compound, C₆H₆Cl₂N⁺·C₆H₄ClO₃S^-, the 2,5-dichloroanilinium cations and 4-chlorobenzenesulfonate anions are located on a crystallographic mirror plane and are connected by N-HO hydrogen bonds. In the crystal, the connectivity of the hydrogen bonds leads to double chains propagating in [010].

Related literature

For the effect of substituents on the oxidative strengths of N-chloro, N-arylsulfonamides, see: Gowda et al. (2004a). For their effect on the structures of N-(aryl)-amides, see: Gowda et al. (2004b) and of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007).

Experimental

Crystal data

C₆H₆Cl₂N⁺·C₆H₄ClO₃S^-
M_r = 354.62
Monoclinic, P 2₁ /m
a = 9.792 (1) Å
b = 6.802 (1) Å
c = 10.879 (1) Å
= 94.26 (1)°
V = 722.60 (15) Å³
Z = 2
Mo K radiation
= 0.78 mm^-1
T = 293 K
0.40 × 0.34 × 0.24 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 = 0.745, T_max = 0.834
2700 measured reflections
1603 independent reflections
1439 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.107
S = 1.02
1603 reflections
124 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H11NO1ⁱ	0.88 (2)	1.85 (2)	2.730 (2)	176 (2)
N1-H12NO2ⁱⁱ	0.89 (2)	1.88 (2)	2.753 (3)	170 (3)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y, 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 RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: BT5496 ).

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi for the award of a research fellowship under its faculty improvement program.

References

Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.
Gowda, B. T. & Shetty, M. (2004a). J. Phys. Org. Chem. 17, 848-864.
Gowda, B. T., Svoboda, I. & Fuess, H. (2004b). Z. Naturforsch. Teil A, 55, 845-852.
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.

organic compounds