N-(3,5-Dimethyl­phen­yl)-2,4-dimethyl­benzene­sulfonamide

B Thimme Gowda; Sabine Foro; P G Nirmala; Hartmut Fuess

doi:10.1107/S1600536809050740

. 2009 Nov 28;65(Pt 12):o3275. doi: 10.1107/S1600536809050740

N-(3,5-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide

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

PMCID: PMC2972036 PMID: 21578969

Abstract

In the title compound, C₁₆H₁₉NO₂S, the molecule is twisted about the S—N bond, the C—S(O₂)—N(H)—C torsion angle being 53.9 (2)°. The dihedral angle between the two benzene rings is 82.1 (1)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our work on the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a ▶,b ▶); Nirmala et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶). graphic file with name e-65-o3275-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₉NO₂S
M _r = 289.38
Monoclinic,
a = 23.490 (2) Å
b = 8.1528 (6) Å
c = 16.544 (1) Å
β = 102.690 (8)°
V = 3090.9 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 299 K
0.40 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.921, T _max = 0.975
6232 measured reflections
2751 independent reflections
2009 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.118
S = 1.01
2751 reflections
188 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 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/S1600536809050740/tk2587sup1.cif

e-65-o3275-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050740/tk2587Isup2.hkl

e-65-o3275-Isup2.hkl^{(135.2KB, 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	0.84 (2)	2.10 (2)	2.945 (3)	176 (3)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b; Nirmala et al., 2009), in the present work, the structure of 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the S–O bond atom with the C1—SO₂—NH—C7 torsion angle being 53.9 (2)°, compared to the values of 46.1 (3)° and 47.7 (3)° in the two independent molecules of 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (II) (Gowda et al., 2009a), 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide (III) (Nirmala et al., 2009) and -69.7 (2)° in 2,4-dimethyl-N-(3,4-dichlorophenyl)benzenesulfonamide (IV) (Gowda et al., 2009b).

The two benzene rings in (I) are tilted relative to each other by 82.1 (1)°, compared to the values of 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of (II), 54.6 (1)° in (III) and 82.4 (1)° in (IV). The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of molecules in (I) is through pairs of N—H···O(S) hydrogen bonds (Table 1).

Experimental

The solution of m-xylene (10 cc) in chloroform (40 cc) was treated drop-wise with chlorosulfonic acid (25 ml) at 273 K. 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-dimethylbenzenesulfonylchloride was treated with a stoichiometric ratio of 3,4-dimethylaniline 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-dimethyl-N- (3,5-dimethylphenyl)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). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.