N-(2,3-Dimethyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809002098

. 2009 Jan 23;65(Pt 2):o366. doi: 10.1107/S1600536809002098

N-(2,3-Dimethylphenyl)benzenesulfonamide

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

PMCID: PMC2968343 PMID: 21581964

Abstract

In the crystal structure of the title compound, C₁₄H₁₅NO₂S, the amino H atom is trans to one of the O atoms of the SO₂ group. Furthermore, the N—H bond is anti to the ortho- and meta-methyl groups of the aromatic ring. The two aromatic rings are tilted relative to each other by 64.8 (1)°. The molecules form zigzag chains along the a axis via intermolecular N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₄H₁₅NO₂S
M _r = 261.33
Orthorhombic,
a = 6.3969 (5) Å
b = 8.8767 (6) Å
c = 23.082 (2) Å
V = 1310.67 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 299 (2) K
0.50 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.889, T _max = 0.958
5869 measured reflections
2611 independent reflections
2200 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.094
S = 1.07
2611 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 1060 Friedel pairs
Flack parameter: −0.04 (9)

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/S1600536809002098/bt2853sup1.cif

e-65-0o366-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002098/bt2853Isup2.hkl

e-65-0o366-Isup2.hkl^{(128.3KB, 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	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)

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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

In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008a, 2008b, 2008c), the structure of N-(2,3-dimethylphenyl)-benzenesulfonamide has been determined. The amino H atom is trans to one of the O atoms of the SO₂ group (Fig. 1), similar to that observed in N-(2,6-dimethylphenyl)- benzenesulfonamide (Gowda et al., 2008a), N-(2-methylphenyl)-benzenesulfonamide (Gowda et al., 2008b) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007; Gowda et al., 2008c). The two benzene rings are tilted relative to each other by 64.8 (1)°, compared with the values of 44.9 (1)° in N-(2,6-dimethylphenyl)- benzenesulfonamide and 61.5 (1)° in N-(2-methylphenyl)-benzenesulfonamide. The other bond parameters of the title compound are similar to those observed in other N-(aryl)-sulfonamides. The crystal packing is stabilized by intermolecular N—H···O hydrogen bonds forming zigzag chains along the a axis (Table 1, Fig. 2).

Experimental

The solution of benzene (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 benzenesulfonylchloride was treated with 2,3-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 solid N-(2,3-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 (Gowda et al., 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.