Crystal structure and Hirshfeld analysis of diethyl (2 E,2' E)-3,3'-[1-(8-phenyl-isoquinolin-1-yl)-1 H-indole-2,7-di-yl]diacrylate

Abstract

The mol-ecule of title compound, C₃₃H₂₈N₂O₄, comprises an indole unit (A), an iso-quinoline moiety (B) and a benzene ring (C). The dihedral angles between these groups are A/B = 57.47 (1), A/C = 18.48 (1) and B/C = 57.97 (1) °. The ethyl acrylate group at the 2-position is nearly co-planar with the indole unit [3.81 (2)°], while that at the 7-position is distinctly non-coplanar [52.64 (1)°]. Intra-molecular π-π inter-actions between the indole unit and benzene ring help to establish the clip-shaped conformation of the mol-ecule. In the crystal, the mol-ecules are assembled into two-dimensional layers via C-H⋯O hydrogen bonds, π-π and C-H⋯π inter-actions. Hirshfeld surface analysis illustrates that the greatest contributions are from H⋯H (63.2%), C⋯H/H⋯C (15.4%) and O⋯H/H⋯O (14.8%) contacts. The terminal C₂H₅ group of one of the ethyl acrylate side chains is disordered over two positions of equal occupancy.

Keywords: Hirshfeld analysis; crystal structure; indole; isoquinolin; weak inter­actions.