(S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine

The title chiral imine, C17H15NS, has been obtained via a direct synthesis route. The imine group displays the common E configuration, and is almost coplanar with the thiophene heterocycle; the dihedral angle between the C=N—C group and the thiophene ring is 5.1 (8)°. In contrast, the naphthyl group makes an angle of 83.79 (13)° with the thiophene ring. The observed solid-state molecular conformation is suitable for the use of this molecule as an N,S-bidentate Schiff base ligand. The molecular packing features double C—H...π interactions between naphthyl groups of neighboring molecules, which form chains in the [100] direction. The crystal structure is further stabilized by a short C—H...π contact involving the methyl group and one ring of a naphthyl group. The resulting two-dimensional network is completed by a weak intermolecular C—H(imine)...π(thiophene) interaction.

Abstract licence: CC BY

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