[Journal logo]

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 [sigma](C-C) = 0.005 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 12.9
Details
Open access

2,5-Dichloroanilinium 4-chlorobenzenesulfonate

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-H...O 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[Gowda, B. T. & Shetty, M. (2004a). J. Phys. Org. Chem. 17, 848-864.]). For their effect on the structures of N-(aryl)-amides, see: Gowda et al. (2004b[Gowda, B. T., Svoboda, I. & Fuess, H. (2004b). Z. Naturforsch. Teil A, 55, 845-852.]) and of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]).

[Scheme 1]

Experimental

Crystal data
  • C6H6Cl2N+·C6H4ClO3S-

  • Mr = 354.62

  • Monoclinic, P 21 /m

  • a = 9.792 (1) Å

  • b = 6.802 (1) Å

  • c = 10.879 (1) Å

  • [beta] = 94.26 (1)°

  • V = 722.60 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.745, Tmax = 0.834

  • 2700 measured reflections

  • 1603 independent reflections

  • 1439 reflections with I > 2[sigma](I)

  • Rint = 0.012

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H11N...O1i 0.88 (2) 1.85 (2) 2.730 (2) 176 (2)
N1-H12N...O2ii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CSD] [CrossRef] [details]
Gowda, B. T. & Shetty, M. (2004a). J. Phys. Org. Chem. 17, 848-864.  [ChemPort]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2011). E67, o967  [ doi:10.1107/S1600536811010518 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.