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

Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811040980

. 2011 Oct 8;67(Pt 11):o2893. doi: 10.1107/S1600536811040980

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

Vinola Z Rodrigues ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3247310 PMID: 22219928

Abstract

In the title compound, C₁₂H₇Cl₄NO₂S, the conformation of the N—C bond in the C—SO₂—NH—C segment is gauche with respect to the S=O bonds. Further, the N—H bond in the C—SO₂—NH—C segment is syn with respect to the ortho-Cl atoms in the aniline and sulfonyl benzene rings. The C—SO₂—NH—C torsion angle is −51.98 (18)°. The sulfonyl and aniline benzene rings are tilted by 67.7 (1)° relative to each other. An intramolecular N—H⋯Cl hydrogen bond occurs.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000 ▶), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶), on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Gowda et al. (2009 ▶); Shetty & Gowda (2005 ▶) and on N-(chloro)-arylsulfonamides, see: Gowda et al. (2003 ▶).

Experimental

Crystal data

C₁₂H₇Cl₄NO₂S
M _r = 371.05
Monoclinic,
a = 9.0756 (6) Å
b = 9.7406 (7) Å
c = 16.432 (1) Å
β = 98.157 (6)°
V = 1437.92 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 293 K
0.48 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.654, T _max = 0.699
5584 measured reflections
2929 independent reflections
2377 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.085
S = 1.06
2929 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 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 datablock(s) I, global. DOI: 10.1107/S1600536811040980/ds2148sup1.cif

e-67-o2893-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040980/ds2148Isup2.hkl

e-67-o2893-Isup2.hkl^{(143.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040980/ds2148Isup3.cml

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⋯Cl3	0.83 (2)	2.47 (2)	2.9526 (19)	118 (2)

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Acknowledgments

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS fellowship.

supplementary crystallographic information

Comment

The sulfonamide moiety is the constituent of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Gowda et al., 2009; Shetty & Gowda, 2005) and N-(chloro)-arylsulfonamides (Gowda et al., 2003), in the present work, the crystal structure of 2,4-Dichloro-N-(2,3-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1).

In (I), the conformations of the N—C bond in the C—SO₂—NH—C segment is gauche to the S═O bonds. Further, the N—H bond in the C—SO₂—NH—C segment is syn with respect to the ortho-Cl atoms in the anilino and sulfonyl benzene rings. The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -52.0 (2)°, compared to the value of -48.2 (2)° in 2,4-Dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide (II) (Gowda et al., 2009).

The sulfonyl and the aniline benzene rings are tilted relative to each other by 67.7 (1)°, compared to the value of 68.9 (1)° in (II).

The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

The crystal structure exhibits N—H···Cl intramolecular hydrogen bonding. Part of the crystal structure is shown in Fig. 2.

Experimental

The solution of 1,3-dichlorobenzene (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 2,4-dichlorobenzenesulfonylchloride 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 solid 2,4-dichloro-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 (Savitha & Gowda, 2006).

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