N-(3,5-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809053057

. 2009 Dec 16;66(Pt 1):o144. doi: 10.1107/S1600536809053057

N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide

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

PMCID: PMC2980205 PMID: 21580035

Abstract

In the title compound, C₁₅H₁₇NO₂S, the dihedral angle between the two aromatic rings is 53.9 (1)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

Related literature

For preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2010 ▶); Nirmala et al. (2009a ▶,b ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M _r = 275.36
Triclinic,
a = 8.311 (1) Å
b = 8.521 (1) Å
c = 11.412 (1) Å
α = 99.86 (1)°
β = 97.62 (1)°
γ = 108.14 (1)°
V = 741.60 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.45 × 0.45 × 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 = 0.909, T _max = 0.919
4897 measured reflections
3025 independent reflections
2525 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.118
S = 1.06
3025 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 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/S1600536809053057/bt5135sup1.cif

e-66-0o144-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053057/bt5135Isup2.hkl

e-66-0o144-Isup2.hkl^{(148.4KB, 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	0.83 (2)	2.11 (2)	2.933 (2)	170 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In the present work, as part of a study of the effect of substituents on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2010; Nirmala et al., 2009a,b), the structure of N-(3,5-dimethylphenyl)4-methylbenzenesulfonamide (I) has been determined. The conformation of the N—C bond in the C1—SO₂—NH—C7 segment of the structure has gauche torsions with respect to the S═ O bonds (Fig. 1). Further, the conformation of the N—H bond is anti to one of the 3-methyl groups and syn to the other in the aniline benzene ring. The molecule is bent at the S atom with the C1—SO₂—NH—C7 torsion angle of 56.8 (2)°, compared to the values of -51.6 (3)° in N-(phenyl)4-methylbenzenesulfonamide (II) (Gowda et al., 2010), 56.7 (3)° in N-(3-methylphenyl)4-methylbenzenesulfonamide (III) (Nirmala et al., 2009a), 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide(IV)(Nirmala et al., 2009b) and -61.0 (2)° in N-(2,5-dimethylphenyl)4-methylbenzenesulfonamide (V) and -61.8 (2)° in N-(3,4-dimethylphenyl)4-methylbenzenesulfonamide (VI) (Gowda et al., 2010).

The two benzene rings in (I) are tilted relative to each other by 53.9 (1)° compared to the values of 68.4 (1)° in (II), 83.9 (1)° in (III), 54.6 (1)° in (IV), 49.4 (1)° in (V) and 47.8 (1)° in (VI). The other bond parameters are similar to those observed in (II), (III), (IV), (V), (VI) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into inversion-related dimers. Part of the crystal structure is shown in Fig. 2.

Experimental

The solution of toluene (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-methylbenzenesulfonylchloride was treated with 3,5-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 N-(3,5-dimethylphenyl)4-methylbenzenesulfonamide 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 a slow evaporation at room temperature.