Crystal structure and DFT study of (E)-N-[2-(1H-indol-3-yl)eth­yl]-1-(anthracen-9-yl)methanimine

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 = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intra-molecular C-H⋯N inter-action present, and a C-H⋯π inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecular N-H⋯π inter-action, linking mol-ecules to form chains along the b-axis direction. There are also C-H⋯π inter-actions 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/6-311 G(d,p) level, is compared with the experimentally determined mol-ecular structure in the solid state.