4-Methyl-N-[(S)-1-phenylethyl]benzenesulfonamide

In the title compound, C15H17NO2S, the dihedral angle between the aromatic rings is 14.47 (8)°. The molecule is bent at the N atom, with a C—SO2—NH—C torsion angle of 79.06 (13)°. In the crystal structure, the sulfonamide groups are hydrogen bonded via N—H⋯O links, forming chains of molecules along the crystallographic b axis. π–π interactions [centroid–centroid distance = 3.81 (3) Å] also occur.

In the title compound, C 15 H 17 NO 2 S, the dihedral angle between the aromatic rings is 14.47 (8) . The molecule is bent at the N atom, with a C-SO2-NH-C torsion angle of 79.06 (13) . In the crystal structure, the sulfonamide groups are hydrogen bonded via N-HÁ Á ÁO links, forming chains of molecules along the crystallographic b axis.interactions [centroid-centroid distance = 3.81 (3) Å ] also occur.
The benzylic and allylic amines are useful alkylating agents for the formation of carbon-carbon and carbon-heteroatom bonds under lewis acid conditions and benzylic, allylic halides and the corresponding sulfonates are frequently employed as the alkylating agents. (Liu et al., 2009a). There are few reports for the preparation of diarylated derivatives and sulfinic acid (Liu et al., 2009b;Seong et al., 1998).
The benzene rings A(C1-C6) and B(C10-C15) are both nearly planar with the maximum r.m.s. deviation from the mean plane as 0.0067 (12)Å for C5 (Fig. 1). The para-substituent on the conformation of the benzene ring is nearly planar to the that of the other benzene ring, making a dihedral angle of 14.47 (8)°.
In the crystal, the molecules are linked in opposite directions with each other via N1-H16···O1 intermolecular interactions and π-π stacking interactions between the benzene rings (centroid to centroid distance = 3.81 (3)Å are also effective in crystal packing. (Fig. 2, Table 1).

Experimental
(S) 1-Phenyl ethyl amine (1 g, 8.2 mmol) was dissolved in toluene (20 ml) under nitrogene at room temperature. TsCl (1.87 g, 9.8 mmol) was added to this solution. After 5 minutes the white precipate was formed. After stirring 5 minutes diisopropyl ethyl amine (1.43 ml, 8.2 mmol) was added to the solution. The reaction mixture was stirred at room temperature for an additional 3.5 h. After 3.5 h no amine was detected by TLC. The solution washed two times with water and organic layer dried over MgSO 4 . Solvent evaporated. The crude mixture purified by column chromotography PE/EtOAc (1:1), gave the sup-2 title compound as a white crystalline solid (1.8 g, 79%). M.p. 87-89°C. Spectroskopic data identical with Lit. (Georgy et al., 2009).

Refinement
The H atom of the NH group was located in a difference map and refined freely. All other H atoms were positioned with idealized geometry using a riding model, with C-H = 0.93 Å (aromatic), 0.98 Å (methine) and 0.96 Å (methyl). All H atoms were refined with U iso =1.2U eq (parent atom). Fig. 1. An ORTEP view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.