N-(3,4-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809010459

. 2009 Mar 28;65(Pt 4):o877. doi: 10.1107/S1600536809010459

N-(3,4-Dimethylphenyl)-4-methylbenzenesulfonamide

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

PMCID: PMC2969044 PMID: 21582588

Abstract

In the crystal structure of the title compound, C₁₅H₁₇NO₂S, the conformations of the N—C bond in the C—SO₂—NH—C segment are trans and gauche, respectively, with respect to the S=O bonds. The molecule is bent at the S atom with a C—SO₂—NH—C torsion angle of −61.8 (2)°. Furthermore, the conformation of the N—H bond and the 3-methyl group in the aniline benzene ring are nearly anti to each other. The dihedral angle between the benzene rings is 47.8 (1)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For the preparation of the compound, see: Shetty & Gowda (2005 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008a ▶,b ▶; 2009 ▶); Perlovich et al. (2006 ▶)

Experimental

Crystal data

C₁₅H₁₇NO₂S
M _r = 275.36
Monoclinic,
a = 9.2528 (7) Å
b = 15.329 (1) Å
c = 10.4469 (7) Å
β = 102.558 (7)°
V = 1446.30 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.45 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.907, T _max = 0.929
10438 measured reflections
2902 independent reflections
2360 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.127
S = 1.06
2902 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S1600536809010459/fl2240sup1.cif

e-65-0o877-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010459/fl2240Isup2.hkl

e-65-0o877-Isup2.hkl^{(142.5KB, 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	2.42	2.963 (2)	122

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As part of our study of substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008a; b; 2009), in the present work, the structure of 4-methyl-N-(3,4-dimethylphenyl)benzenesulfonamide (N34DMP4MBSA) has been determined. The conformations of the N—C bond in the C—SO₂—NH—C segment of the structure are "trans" and "gauche" with respect to the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -61.8 (2). The conformation of the N—H bond and the meta-methyl group in the anilino benzene ring are nearly anti to each other. The two benzene rings in the title compound are tilted relative to each other by 47.8 (1)°. The other bond parameters in N34DMP4MBSA are similar to those observed in N-(2,6-dimethylphenyl)-benzenesulfonamide (Gowda et al., 2008a), N-(2,3-dimethylphenyl)- benzenesulfonamide (Gowda et al., 2009), N-(3,5-dichlorophenyl)- benzenesulfonamide (Gowda et al., 2008b)) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The N—H···O hydrogen bonds (Table 1) pack the molecules into infinite chains in the direction of a- axis (Fig. 2).

Experimental

The solution of toluene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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-methylbenzenesulfonylchloride 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 cc). The resultant 4-methyl-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 (Shetty & Gowda, 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.