4-Chloro-N-(3,5-dichloro­phenyl)benzene­sulfonamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S160053681101470X

. 2011 Apr 29;67(Pt 5):o1219. doi: 10.1107/S160053681101470X

4-Chloro-N-(3,5-dichlorophenyl)benzenesulfonamide

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

PMCID: PMC3089164 PMID: 21754517

Abstract

In the title compound, C₁₂H₈Cl₃NO₂S, the dihedral angle between the aromatic rings is 87.9 (1)° and the C—S—N—C torsion angle is 77.8 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For hydrogen-bonding preferences of sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004 ▶); on the structures of N-(aryl)arylsulfonamides, see: Shakuntala et al. (2011a ▶,b ▶); and on the oxidative strengths of N-chloro-N-arylsulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C₁₂H₈Cl₃NO₂S
M _r = 336.60
Triclinic,
a = 4.935 (1) Å
b = 11.630 (2) Å
c = 13.115 (2) Å
α = 113.52 (2)°
β = 90.49 (1)°
γ = 96.50 (1)°
V = 684.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 293 K
0.32 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.780, T _max = 0.923
4440 measured reflections
2785 independent reflections
2236 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.086
S = 1.03
2785 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.33 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/S160053681101470X/bq2298sup1.cif

e-67-o1219-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101470X/bq2298Isup2.hkl

e-67-o1219-Isup2.hkl^{(136.7KB, 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—H1N⋯O2ⁱ	0.84 (2)	2.08 (2)	2.917 (2)	170 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically important compounds. As a part of studying the substituent effects on the structures and other aspects of this class of compounds (Gowda & Kumar, 2003; Gowda et al., 2004; Shakuntala et al., 2011a,b), in the present work, the crystal structure of 4-chloro-N-(3,5-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is twisted at the S atom with the C—SO₂—NH—C torsion angle of 77.8 (2)°, compared to the values of -58.4 (3)° in 4-chloro-N-(3-chlorophenyl)benzenesulfonamide (II) (Shakuntala et al., 2011b) and -56.7 (2)° in 4-chloro-N-(2,3-dichlorophenyl)-benzenesulfonamide (III) (Shakuntala et al., 2011a). The conformation of the N—H bond is anti to one of the meta-chloro group in the anilino benzene ring and syn to the other.

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 87.9 (1)°, compared to the values of 77.1 (1)° in (II) and 56.5 (1)° in (III).

Intermolecular N—H···O(S) hydrogen bonding interactions generate inversion related dimers which are further packed via van der Waals interactions in the crystal structure (Fig. 2).

Experimental

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was added 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 3,5-dichloroaniline in the stoichiometric ratio and boiled for 15 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(3,5-dichlorophenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The compound was characterized by FT–IR and NMR spectra.

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