4-Chloro-N-(2,3-dichloro­phen­yl)benzene­sulfonamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536810053638

. 2010 Dec 24;67(Pt 1):o232. doi: 10.1107/S1600536810053638

4-Chloro-N-(2,3-dichlorophenyl)benzenesulfonamide

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

PMCID: PMC3050220 PMID: 21522732

Abstract

In the title compound, C₁₂H₈Cl₃NO₂S, the two aromatic rings are tilted relative to each other by 56.5 (1)°. The crystal structure features centrosymmetric dimers in which molecules are linked by N—H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010 ▶); Nirmala et al. (2010 ▶); Shakuntala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₈Cl₃NO₂S
M _r = 336.60
Monoclinic,
a = 7.224 (1) Å
b = 14.975 (2) Å
c = 13.170 (2) Å
β = 97.16 (1)°
V = 1413.6 (3) Å³
Z = 4
Cu Kα radiation
μ = 7.23 mm⁻¹
T = 299 K
0.38 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.170, T _max = 0.326
2767 measured reflections
2516 independent reflections
2277 reflections with I > 2σ(I)
R _int = 0.062
3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.137
S = 1.15
2516 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536810053638/bt5445sup1.cif

e-67-0o232-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053638/bt5445Isup2.hkl

e-67-0o232-Isup2.hkl^{(123.6KB, 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⋯O1ⁱ	0.86 (2)	2.11 (2)	2.944 (3)	163 (3)

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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 program.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2010; Nirmala et al., 2010; Shakuntala et al., 2010), in the present work, the structure of 4-chloro-N-(2,3-dichlorophenyl)-benzenesulfonamide (I) has been determined. The conformation of the N—C bond in the C—SO₂—NH—C segment of the structure has gauche torsions with respect to the S═ O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -56.7 (2)°, compared to the values of 65.4 (2) and -61.7 (2) in the two molecules of N-(2,3-dichlorophenyl)- 4-methylbenzenesulfonamide (II) (Shakuntala et al., 2010). The conformations of the N—H bond and the ortho-chloro group in the anilino benzene ring are syn to each other.

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 56.5 (1)°, compared to the values of 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2) in (II).

The other bond parameters in (I) are similar to those observed in (II), N-(2,3-dichlorophenyl)-2,4-dimethylbenzenesulfonamide (Nirmala et al., 2010), N-(3,4-dimethylphenyl)-4-chlorobenzene- sulfonamide (Gowda et al., 2010) and other aryl sulfonamides, (Perlovich et al., 2006; Gelbrich et al., 2007).

The structure shows N—H···O intermolecular H-bonding (Table 1). The crystal packing 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 2,3-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 4-chloro-N-(2,3-dichlorophenyl)- benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared 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.