N-(2,6-Dimethyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536808024653

. 2008 Aug 6;64(Pt 9):o1691. doi: 10.1107/S1600536808024653

N-(2,6-Dimethylphenyl)benzenesulfonamide

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

PMCID: PMC2960643 PMID: 21201680

Abstract

In the crystal structure of the title compound, C₁₄H₁₅NO₂S, the N—H bond is trans to one of the S=O double bonds, similar to what is observed in N-(2-methylphenyl)benzenesulfonamide and other aryl sulfonamides. The two aromatic rings enclose a dihedral angle of 44.9 (1)°. The molecules are connected by intermolecular N—H⋯O hydrogen bonds into chains running along the a axis. An intermolecular C—H⋯O hydrogen bond is also present.

Related literature

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

Experimental

Crystal data

C₁₄H₁₅NO₂S
M _r = 261.33
Monoclinic,
a = 5.2133 (7) Å
b = 17.971 (2) Å
c = 14.040 (1) Å
β = 91.681 (9)°
V = 1314.8 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.13 mm⁻¹
T = 299 (2) K
0.55 × 0.35 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2622 measured reflections
2340 independent reflections
2197 reflections with I > 2σ(I)
R _int = 0.071
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.134
S = 1.08
2340 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536808024653/bt2760sup1.cif

e-64-o1691-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024653/bt2760Isup2.hkl

e-64-o1691-Isup2.hkl^{(115KB, 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	0.86	2.55	3.179 (2)	131
C5—H5⋯O2ⁱⁱ	0.93	2.57	3.229 (3)	129

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Symmetry codes: (i) Inline graphic ; (ii) .

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, in the present work, the structure of N-(2,6-dimethylphenyl)-benzenesulfonamide (N26DMPBSA) has been determined (Gowda et al., 2005, 2008; Gowda, Babitha et al. 2007; Gowda, Foro et al. 2007). The the N—H bond is trans to one of the S—O double bonds (Fig. 1), similar to what is observed in N-(2-methylphenyl)-benzenesulfonamide (N2MPBSA)(Gowda et al., 2008) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007;). The two aromatic rings are rotated relative to each other by 44.9 (1)°, compared with the value of 61.5 (1)° in N2MPBSA. The other bond parameters in N26DMPBSA are similar to those observed in N2MPBSA and other N-(aryl)-sulfonamides (Gowda, Babitha et al., 2007; Gowda, Foro et al. 2007; Gowda et al. 2008; Perlovich et al., 2006; Gelbrich et al., 2007). The packing diagram of N26DMPBSA via intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) is shown in 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 2,6-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-(2,6-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.