3-[1-(4-Methyl-phen-ylsulfon-yl)-1,4-di-hydro-pyridin-4-yl]-1H-indole.

In the title compound, C(20)H(18)N(2)O(2)S, the indole mean plane and benzene ring form a dihedral angle of 65.0 (1)°. In the crystal structure, weak inter-molecular N-H⋯π and C-H⋯O inter-actions link the mol-ecules into ribbons propagated along [100].

In the title compound, C 20 H 18 N 2 O 2 S, the indole mean plane and benzene ring form a dihedral angle of 65.0 (1) . In the crystal structure, weak intermolecular N-HÁ Á Á and C-HÁ Á ÁO interactions link the molecules into ribbons propagated along [100].  Hydrogen-bond geometry (Å , ).

Related literature
Cg is the centroid of the C1-C6 ring.   et al. 1970et al. , Lavilla et al. 1997. Attempted N-tosylation of indole in pyridine gave a product which did not correspond to the expected N-tosylindole. Crystallization of this compound from acetonitrile yielded light pink crystals of a compound that by ESI-MS, 1 H and 13 C NMR data showed to contain indole, dihydropyridine and the tosyl group. Following studies on the nucleophilic addition of indole to pyridinium salts (Bennasar et al., 1990;Lavilla et al. 1997) the structure for the isolated compound was suggested to be 3-{1-[(4-Methylphenyl)sulfonil]-1,4-dihydropyridin-4-yl}-1H-indole (Scheme 1) and later confirmed by single-crystal X-ray diffraction ( Figure 1).

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S 0.43816 (8)