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.

Frédéric Capet,Catherine Renard,Tuncer Hökelek,Youssef Kandri Rodi,Ismail Ghandour,Abdelouahed Bouayad,Amal Haoudi

doi:10.1107/s2056989019007801

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 79.10 (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.

Highlights

In the crystal, C—HPropÁ Á ÁOImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds (Table 1 and Fig. 2) link the molecules into infinite chains along the b-axis direction
Pyrazolones are an important class of heterocyclic compounds that occur in many drugs and their derivatives have long been of interest to medicinal chemists for their wide range of biological activities (Pawar & Patil, 1994), including antibacterial, antidiabetic, immunosuppressive agents, and substances displaying hypoglycemic, antiviral and antineoplastic actions (Pathak & Bahel, 1980; Naik & Malik, 2010; Srivalli et al, 2011)
The title molecule consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties (Fig. 1)

Summary

Chemical context

Pyrazolones are an important class of heterocyclic compounds that occur in many drugs and their derivatives have long been of interest to medicinal chemists for their wide range of biological activities (Pawar & Patil, 1994), including antibacterial, antidiabetic, immunosuppressive agents, and substances displaying hypoglycemic, antiviral and antineoplastic actions (Pathak & Bahel, 1980; Naik & Malik, 2010; Srivalli et al, 2011) Their pharmaceutical applications include use as a non-steroidal anti-inflammatory agent in the treatment of arthritis and other musculoskeletal and joint disorders (Amir & Kumar, 2005), and as analgesic, antipyretic (Badawey & El-Ashmawey, 1998) and hypoglycemic agents (Das et al, 2008). Symmetry codes: (vi) Àx þ 1; y þ 12; Àz þ 1; (vii) Àx; y À 12; Àz; (viii) Àx þ 1; y þ 12; Àz

Supramolecular features

Structural commentary

Hirshfeld surface analysis

Interaction energy calculations

DFT calculations

Database survey

Findings

Refinement