Crystal structure, hirshfeld surface analysis and inter-action energy and dft studies of 5,5-diphenyl-1,3-bis-(prop-2-yn-1-yl)imidazolidine-2,4-dione - Université de Lille Accéder directement au contenu
Article Dans Une Revue Acta crystallographica Section E : Crystallographic communications [2015-...] Année : 2019

Crystal structure, hirshfeld surface analysis and inter-action energy and dft studies of 5,5-diphenyl-1,3-bis-(prop-2-yn-1-yl)imidazolidine-2,4-dione

Ismail Ghandour
  • Fonction : Auteur
Abdelouahed Bouayad
  • Fonction : Auteur
Tuncer Hokelek
  • Fonction : Auteur
Amal Haoudi
  • Fonction : Auteur
Youssef Kandri Rodi
  • Fonction : Auteur

Résumé

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)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, inter-molecular C-HProp⋯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-HPhen⋯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 H⋯H (43.3%), H⋯C/C⋯H (37.8%) and H⋯O/O⋯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-HProp⋯OImdzln 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 mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

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Matériaux
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hal-04442625 , version 1 (06-02-2024)

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Ismail Ghandour, Abdelouahed Bouayad, Tuncer Hokelek, Amal Haoudi, Frederic Capet, et al.. Crystal structure, hirshfeld surface analysis and inter-action energy and dft studies of 5,5-diphenyl-1,3-bis-(prop-2-yn-1-yl)imidazolidine-2,4-dione. Acta crystallographica Section E : Crystallographic communications [2015-..], 2019, Acta crystallographica Section E : Crystallographic communications [2015-..], 75, pp.951-956. ⟨10.1107/S2056989019007801⟩. ⟨hal-04442625⟩
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