Crystal Structure and DFT Study of (E)-N-[2-(1 H-indol-3-yl)eth-yl]-1-(anthracen-9-yl)methanimine

Abstract

The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016Å) makes a dihedral angle of 63.56(8)° with the anthracene ring (r.m.s. deviation = 0.023Å). There is a short intramolecular C-H⋯N interaction present, and a C-H⋯π interaction involving the two ring systems. In the crystal, the indole H atom forms an intermolecular N-H⋯π interaction, linking molecules to form chains along the b-axis direction. There are also C-H⋯π interactions present, involving the central and terminal rings of the anthracene unit, linking the chains to form an overall two-dimensional layered structure, with the layers parallel to the bc plane. The density functional theory (DFT) optimized structure, at the B3LYP/6-311G(d,p) level, is compared with the experimentally determined molecular structure in the solid state. © Faizi et al. 2017.