Crystal structure, Hirshfeld surface analysis, calculations of crystal voids, inter-action energy and energy frameworks as well as density functional theory (DFT) calculations of 3-[2-(morpholin-4-yl)eth-yl]-5,5-di-phenyl-imidazolidine-2,4-dione

Houda Lamssane; Amal Haoudi; Badr Eddine Kartah; Ahmed Mazzah; Joel T Mague; Tuncer Hökelek; Youssef Kandri Rodi; Nada Kheira Sebbar

doi:10.1107/S2056989024002445

Crystal structure, Hirshfeld surface analysis, calculations of crystal voids, inter-action energy and energy frameworks as well as density functional theory (DFT) calculations of 3-[2-(morpholin-4-yl)eth-yl]-5,5-di-phenyl-imidazolidine-2,4-dione

Acta Crystallogr E Crystallogr Commun. 2024 Mar 26;80(Pt 4):423-429. doi: 10.1107/S2056989024002445. eCollection 2024 Mar 1.

Authors

Houda Lamssane¹, Amal Haoudi¹, Badr Eddine Kartah², Ahmed Mazzah³, Joel T Mague⁴, Tuncer Hökelek⁵, Youssef Kandri Rodi¹, Nada Kheira Sebbar^{6

2}

Affiliations

¹ Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty Of Science And Technology, Road Immouzer, BP 2202 Fez, Morocco.
² Laboratory of Plant Chemistry, Organic and Bioorganic Synthesis, Faculty of Sciences, Mohammed V University in Rabat, 4 Avenue Ibn Battouta BP 1014 RP, Morocco.
³ Science and Technology of Lille USR 3290, Villeneuve d'ascq cedex, France.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁵ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁶ Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco.

Abstract

In the title mol-ecule, 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 mol-ecules extending parallel to the c axis that are connected by C-H⋯π(ring) inter-actions. 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%) inter-actions. 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 mol-ecular structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state. Moreover, the HOMO-LUMO behaviour was elucidated to determine the energy gap.

Keywords: C—H⋯π(ring) interaction; crystal structure; hydrogen bond; imidazolidinedione.

Grants and funding

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).