N-(2,6-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536810014571

. 2010 Apr 24;66(Pt 5):o1168. doi: 10.1107/S1600536810014571

N-(2,6-Dimethylphenyl)-4-methylbenzenesulfonamide

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

PMCID: PMC2979196 PMID: 21579210

Abstract

In the title compound, C₁₅H₁₇NO₂S, the molecule is bent at the S atom, the C—SO₂—NH—C torsion angle being 88.0 (2)°. The dihedral angle between the two aromatic rings is 49.8 (1)°. In the crystal, molecules are linked into zigzag chains parallel to the a axis via N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study of the effect of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M _r = 275.36
Monoclinic,
a = 5.1412 (5) Å
b = 17.310 (2) Å
c = 16.429 (2) Å
β = 96.65 (1)°
V = 1452.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.46 × 0.32 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector.
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.906, T _max = 0.970
7741 measured reflections
2580 independent reflections
2090 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.116
S = 1.04
2580 reflections
178 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.36 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/S1600536810014571/vm2025sup1.cif

e-66-o1168-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014571/vm2025Isup2.hkl

e-66-o1168-Isup2.hkl^{(126.7KB, 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	0.85 (1)	2.20 (1)	3.040 (2)	169 (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., 2008, 2009, 2010), the structure of N-(2,6-dimethylphenyl)-4-methylbenzenesulfonamide (I) has been determined. The molecule is bent at the S atom (Fig. 1) with the C1—SO₂—NH—C7 torsion angle of 88.0 (2)°, compared to the values of -51.6 (3)° in N-(phenyl)4-methylbenzenesulfonamide (II) (Gowda et al., 2009), -78.7 (2)° in N-(2,6-dimethylphenyl)- benzenesulfonamide (III) (Gowda et al., 2008) and -61.0 (2)° in N-(2,5-dimethylphenyl)-4-methylbenzenesulfonamide (IV), -61.8 (2)° in N-(3,4-dimethylphenyl)-4-methylbenzenesulfonamide (V) and 56.8 (2)° in N-(3,5-dimethylphenyl)-4-methylbenzenesulfonamide (VI)(Gowda et al., 2010).

The two benzene rings in (I) are tilted relative to each other by 49.8 (1)°, compared to the values of 68.4 (1)° in (II), 44.9 (1)° in (III), 49.4 (1)° in (IV), 47.8 (1)° in (V) and 53.9 (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, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into infinite zig-zag chains running parallel to the a-axis. Part of the crystal structure is shown in Fig. 2.

Experimental

4-Methylbenzenesulfonylchloride was obtained by treating the solution of toluene (10 ml) in chloroform (40 ml) with chlorosulfonic acid (25 ml) by the procedure reported earlier (Gowda et al., 2010). 4-Methylbenzenesulfonylchloride was then treated with 2,6-dimethylaniline in the stoichiometric ratio to obtain N-(2,6-dimethylphenyl)- 4-methylbenzenesulfonamide. The latter was recrystallized to constant melting point (110 °C) from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Shetty & Gowda, 2005).

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