N-(2-Methyl­phen­yl)benzene­sulfonamide

B Thimme Gowda; Sabine Foro; K S Babitha; Hartmut Fuess

doi:10.1107/S1600536808024562

. 2008 Aug 6;64(Pt 9):o1692. doi: 10.1107/S1600536808024562

N-(2-Methylphenyl)benzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, K S Babitha ^a, Hartmut Fuess ^b

PMCID: PMC2960504 PMID: 21201681

Abstract

In the title compound, C₁₃H₁₃NO₂S, the conformation of the N—H bond is anti to the ortho-methyl group on the aniline ring, in contrast to the syn conformation observed with respect to the ortho-chloro group in N-(2-chlorophenyl)benzenesulfonamide. The dihedral angle between the two benzene rings is 61.5 (1)°. Molecules are linked into chains running along the a axis by N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al., 2007 ▶; Gowda et al. (2005 ▶, 2007a ▶,b ▶, 2008 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₃H₁₃NO₂S
M _r = 247.30
Orthorhombic,
a = 6.4840 (6) Å
b = 8.6124 (8) Å
c = 21.915 (2) Å
V = 1223.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 299 (2) K
0.50 × 0.50 × 0.45 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.884, T _max = 0.895
4256 measured reflections
2347 independent reflections
2164 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.07
2347 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ▶), 883 Friedel pairs
Flack parameter: 0.02 (10)

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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024562/ci2650sup1.cif

e-64-o1692-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024562/ci2650Isup2.hkl

e-64-o1692-Isup2.hkl^{(115.4KB, 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	0.82 (3)	2.11 (3)	2.926 (3)	178 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of N-(aryl)-sulfonamides the structure of N-(2-methylphenyl)-benzenesulfonamide (N2MPBSA) has been determined (Gowda et al., 2007a,b, 2008). The conformations of the N—H and S═O bonds of the SO₂—NH—C group are trans to each other (Fig. 1). Further, the conformation of the N—H bond is anti to the ortho-methyl group in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho-chloro group in N-(2-chlorophenyl)-benzenesulfonamide (N2CPBSA) (Perlovich et al., 2006). The two benzene rings are rotated relative to each other by 61.5 (1)° compared to the value of 49.1 (1)° in N2CPBSA. The other bond parameters in N2MPBSA are similar to those in N2CPBSA and other N-(aryl)-sulfonamides (Gelbrich et al., 2007; Gowda et al., 2007a,b, 2008).

In the crystal structure of N2MPBSA (Fig. 1), the molecules are linked into chains running along the a axis by N—H···O hydrogen bonds (Table 1).

Experimental

A solution of benzene (10 ml) in chloroform (40 ml) was treated dropwise 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 benzenesulfonylchloride was treated with o-toluidine in the stoichiometric ratio and boiled for 10 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2-methylphenyl)-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 (Gowda et al., 2005). Single crystals of the title compound used for X-ray diffraction studies were grown by slow evaporation of an ethanolic solution at room temperature.