2,5-Dichloro­anilinium 4-chloro­benzene­sulfonate

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811010518

. 2011 Mar 26;67(Pt 4):o967. doi: 10.1107/S1600536811010518

2,5-Dichloroanilinium 4-chlorobenzenesulfonate

K Shakuntala ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3099771 PMID: 21754230

Abstract

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 ▶). 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,
a = 9.792 (1) Å
b = 6.802 (1) Å
c = 10.879 (1) Å
β = 94.26 (1)°
V = 722.60 (15) Å³
Z = 2
Mo Kα radiation
μ = 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 ▶) T _min = 0.745, T _max = 0.834
2700 measured reflections
1603 independent reflections
1439 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.107
S = 1.02
1603 reflections
124 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010518/bt5496sup1.cif

e-67-0o967-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010518/bt5496Isup2.hkl

e-67-0o967-Isup2.hkl^{(79KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

The amine and sulfonate moieties are important constituents of many important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2004a, 2004b, 2007), in the present work, the crystal structure of 2,5-dichloroanilinium, 4-chlorobenzenesulfonate (I) has been determined (Fig. 1). The title compound showed interesting H-bonding in its crystal structure (Fig. 2). It forms the structure through N—H···O(S) hydrogen bonding. Three H-atoms of the positively charged NH₃ group have three O atoms of the negatively charged sulfonate anion as acceptors, with each oxygen forming H-bonding with three H-atoms, one each from three positively charged NH₃ groups.

The crystal packing of (I) through N1—H11N···O1, N1—H11aN···O1a and N1—H12N···O2 hydrogen bonding (Table 1) is shown in Fig.2.

Experimental

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 2,5-dichloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant title compound (I) was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol.

Prism like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.