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

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

doi:10.1107/S1600536810014418

. 2010 Apr 24;66(Pt 5):o1150. doi: 10.1107/S1600536810014418

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

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

PMCID: PMC2979129 PMID: 21579197

Abstract

In the title compound, C₁₆H₁₉NO₂S, the dihedral angle between the aromatic rings is 47.2 (2)°. The crystal structure features zigzag C(4) chains linked by N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our study on the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a ▶,b ▶); Nirmala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₆H₁₉NO₂S
M _r = 289.38
Monoclinic,
a = 9.732 (1) Å
b = 15.045 (2) Å
c = 10.425 (1) Å
β = 100.10 (1)°
V = 1502.8 (3) Å³
Z = 4
Cu Kα radiation
μ = 1.92 mm⁻¹
T = 299 K
0.45 × 0.38 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.479, T _max = 0.616
2858 measured reflections
2672 independent reflections
2265 reflections with I > 2σ(I)
R _int = 0.047
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.338
S = 1.59
2672 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.71 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/S1600536810014418/bt5248sup1.cif

e-66-o1150-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014418/bt5248Isup2.hkl

e-66-o1150-Isup2.hkl^{(131.2KB, 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⋯O2ⁱ	0.86	2.41	2.976 (4)	124

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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., 2010),in the present work, the structure of 2,4-dimethyl-N-(3,4-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). 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. The molecule in (I) is bent at the S- atom with the C—SO₂—NH—C torsion angle of 57.4 (3)°, compared to the values of 70.1 (2) and -66.0 (2)° in the two independent molecules of 2,4-dimethyl-N-(2,3-dimethylphenyl)benzenesulfonamide (II), 66.5 (2)° in 2,4-dimethyl-N-(2,4-dimethylphenyl)benzenesulfonamide (III) , 53.9 (2)° in 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (IV) and 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N- (phenyl)benzenesulfonamide (V).

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 47.2 (2)°, compared to the values of 41.5 (1) and 43.8 (1)° in the two molecules of (II), 41.0 (1)° in (III), 82.1 (1)° in (IV) and 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in (V),

The remaining bond parameters in (I) are similar to those observed in (II), (III), (IV), (V) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of molecules in (I) through N—H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Experimental

The solution of m-xylene (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-dimethylbenzenesulfonylchloride was treated with 3,4-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 solid 2,4-dimethyl-N- (3,4-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). Prism like yellow single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.