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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 73; no. Pt 9; pp. 1329 - 1332
• Main Authors: Faizi, Md Serajul Haque, Dege, Necmi, Malinkin, Sergey, Sliva, Tetyana Yu
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01.09.2017
• Subjects: anthracene; crystal structure; C—H...π interactions; indole; methanamine; N—H...π interactions; Research Communications; Schiff base; tryptamine; Schiff base; anthracene; tryptamine; C—H⋯π inter­actions; indole; N—H⋯π inter­actions; crystal structure; methanamine
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989017011483

The title compound, C H N , ( ), 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 -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 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.