Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione


Ghandour I., Bouayad A., HÖKELEK T. , Haoudi A., Capet F., Renard C., ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.75, ss.951-962, 2019 (ESCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 75
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1107/s2056989019007801
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Sayfa Sayıları: ss.951-962

Özet

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 79.10 (5) and 82.61 (5)degrees with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)degrees. In the crystal, intermolecular C-H-Prop center dot center dot center dot O-Imdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Two weak C-H-Phen center dot center dot center dot pi interactions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (43.3%), H center dot center dot center dot C/C center dot center dot center dot H (37.8%) and H center dot center dot center dot O/O center dot center dot center dot H (18.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that the C-H-Prop center dot center dot center dot O-Imdzln hydrogen-bond energy in the crystal is -40.7 kJ mol(-1). Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.