Crystal structure, Hirshfeld surface analysis, calculations of crystal voids, interaction energy and energy frameworks as well as density functional theory (DFT) calculations of 3-[2-(morpholin-4-yl)ethyl]-5,5-diphenylimidazolidine-2,4-dione

Abstract

In the title molecule, C21H23N3O3, the imidazolidine ring slightly deviates from planarity and the morpholine ring exhibits the chair conformation. In the crystal, N—H...O and C—H...O hydrogen bonds form helical chains of molecules extending parallel to the c axis that are connected by C—H...π(ring) interactions. A Hirshfeld surface analysis reveals that the most important contributions for the crystal packing are from H...H (55.2%), H...C/C...H (22.6%) and H...O/O...H (20.5%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 236.78 Å3 and 12.71%, respectively. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the nearly equal electrostatic and dispersion energy contributions. The DFT-optimized molecular structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state. Moreover, the HOMO–LUMO behaviour was elucidated to determine the energy gap.

Keywords

• crystal structure
• imidazolidinedione
• hydrogen bond
• c—h...π(ring) interaction