4-Chloro-N-(2-chloro­phen­yl)-2-methyl­benzene­sulfonamide

B Thimme Gowda; Sabine Foro; P G Nirmala; K S Babitha; Hartmut Fuess

doi:10.1107/S1600536809007880

. 2009 Mar 11;65(Pt 4):o717. doi: 10.1107/S1600536809007880

4-Chloro-N-(2-chlorophenyl)-2-methylbenzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, P G Nirmala ^a, K S Babitha ^a, Hartmut Fuess ^b

PMCID: PMC2968972 PMID: 21582453

Abstract

In the crystal structure of the title compound, C₁₃H₁₁Cl₂NO₂S, the conformations of the N—C bond in the C—SO₂—NH—C segment are trans and gauche with respect to the S=O bonds. The C—S(O₂)—N(H)—C torsion angle is 74.8 (4)°, indicating that the molecule is bent at the S atom. In the crystal structure, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur. An intramolecular N—H⋯Cl interaction is also present.

Related literature

For related structures of N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007 ▶); Gowda et al. (2009a ▶,b ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₃H₁₁Cl₂NO₂S
M _r = 316.19
Triclinic,
a = 8.089 (2) Å
b = 8.096 (2) Å
c = 10.946 (3) Å
α = 96.00 (1)°
β = 97.11 (2)°
γ = 105.67 (2)°
V = 677.7 (3) Å³
Z = 2
Cu Kα radiation
μ = 5.73 mm⁻¹
T = 299 K
0.45 × 0.33 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.150, T _max = 0.640
2684 measured reflections
2414 independent reflections
1932 reflections with I > 2σ(I)
R _int = 0.037
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.236
S = 1.05
2414 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.67 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/S1600536809007880/tk2384sup1.cif

e-65-0o717-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007880/tk2384Isup2.hkl

e-65-0o717-Isup2.hkl^{(118.6KB, 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⋯O2ⁱ	0.88 (5)	2.17 (5)	2.994 (5)	157 (4)
N1—H1N⋯Cl2	0.88 (5)	2.67 (5)	3.011 (4)	104 (4)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al. 2008a,b, 2009), the structure of 2-methyl-4-chloro-N-(2-chlorophenyl)benzenesulfonamide (I) has been determined. The conformations of the N—C bond in the C—S(O₂)—N(H)—C segment are trans and gauche with respect to the S=O bonds (Fig. 1). The torsion angle of C1—S1—N1—C1 is 74.8 (4)°, indicating the molecule is bent at the S1 atom. The two benzene rings are tilted relative to each other by 45.5 (2)°, compared with the values of 86.6 (2)° (molecule 1) and 83.0 (2)° (molecule 2), in the two independent molecules of 2-methyl-4-chloro-N-(phenyl)-benzenesulfonamide (II) (Gowda et al., 2009). Bond distance parameters in (I) are similar to those observed in (II), 2,4-dimethyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2008b) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal structure comprises the packing of centrosymmetric molecules connected via N—H···O hydrogen bonds (Table 1 & Fig. 2).

Experimental

m-Chlorotoluene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of HCl 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 2-methyl-4-chlorobenzenesulfonylchloride was treated with 2-chloroaniline in a 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 solid 2-methyl-4-chloro-N-(2-chlorophenyl)-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. The single crystals used in X-ray diffraction studies were grown from an ethanolic solution by slow evaporation at room temperature.