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

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811016321

. 2011 May 7;67(Pt 6):o1328. doi: 10.1107/S1600536811016321

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

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

PMCID: PMC3120438 PMID: 21754725

Abstract

In the title compound, C₁₄H₁₄ClNO₂S, the two aromatic rings are tilted relative to each other by 34.7 (1)°. In the crystal, the molecules form zigzag chains along the c axis via intermolecular N—H⋯O hydrogen bonds.

Related literature

For hydrogen bonding modes 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: Gowda et al. (2009 ▶); Shakuntala et al. (2011 ▶) and on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M _r = 295.77
Monoclinic,
a = 4.9926 (6) Å
b = 22.296 (3) Å
c = 12.793 (2) Å
β = 90.11 (1)°
V = 1424.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 293 K
0.40 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.853, T _max = 0.960
5341 measured reflections
2669 independent reflections
1882 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.116
S = 1.07
2669 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.40 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/S1600536811016321/bt5537sup1.cif

e-67-o1328-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016321/bt5537Isup2.hkl

e-67-o1328-Isup2.hkl^{(131.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016321/bt5537Isup3.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⋯O2ⁱ	0.86	2.46	2.893 (3)	112

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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

The sulfonamide moiety is a constituent of many biologically important compounds. The hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2004, 2007, 2009; Shakuntala et al., 2011), in the present work, the crystal structure of 4-chloro-N-(2,3-dimethylphenyl)-benzenesulfonamide, (I), has been determined (Fig. 1). In the title compound, the amino H atom is trans to one of the O atoms of the SO₂ group. Furthermore, the N—H bond is syn to the ortho- and meta-methyl groups of the aromatic ring, in contrast to the anti conformation observed between the N—H bond, and the ortho- and meta-methyl groups in N-(2,3-dimethylphenyl)-benzenesulfonamide (II) (Gowda et al., 2009). The molecule is twisted at the S atom with the C—SO₂—NH—C torsion angle of -70.3 (3)°, compared to the values of 71.0 (2)° in (II), and -53.8 (3)° and -63.4 (3)° in the two independent molecules of 4-chloro-N-(phenyl)-benzenesulfonamide (III) (Shakuntala et al., 2011).

The sulfonyl and the anilino benzene rings are tilted relative to each other by 34.7 (1)° in (I), compared to the values of 64.8 (1)° in (II), and 69.1 (1)° and 82.6 (1)° in the two independent molecules of (III).

The packing of molecules in the title compound via intermolecular N—H···O hydrogen bonds (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 2,3-dimethylaniline 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-dimethylphenyl)-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 recording its infrared and NMR spectra.

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