ABSTRACT
The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10â (5) and 82.61â (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06â (5)°. In the crystal, inter-molecular C-HPropâ¯OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the mol-ecules into infinite chains along the b-axis direction. Two weak C-HPhenâ¯π inter-actions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Hâ¯H (43.3%), Hâ¯C/Câ¯H (37.8%) and Hâ¯O/Oâ¯H (18.0%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that the C-HPropâ¯OImdzln hydrogen-bond energy in the crystal is -40.7â kJâ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.