Crystal structure, Hirshfeld surface analysis, crystal voids, inter-action energy calculations and energy frameworks, and DFT calculations of 1-(4-methyl-benz-yl)in-do-line-2,3-dione

Nohaila Rharmili; Omar Abdellaoui; Fouad Ouazzani Chahdi; Joel T Mague; Tuncer Hökelek; Ahmed Mazzah; Youssef Kandri Rodi; Nada Kheira Sebbar

doi:10.1107/S2056989024000756

Crystal structure, Hirshfeld surface analysis, crystal voids, inter-action energy calculations and energy frameworks, and DFT calculations of 1-(4-methyl-benz-yl)in-do-line-2,3-dione

Acta Crystallogr E Crystallogr Commun. 2024 Jan 31;80(Pt 2):232-239. doi: 10.1107/S2056989024000756. eCollection 2024 Feb 1.

Authors

Nohaila Rharmili¹, Omar Abdellaoui¹, Fouad Ouazzani Chahdi¹, Joel T Mague², Tuncer Hökelek³, Ahmed Mazzah⁴, Youssef Kandri Rodi¹, Nada Kheira Sebbar^{5

6}

Affiliations

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

Abstract

The in-do-line portion of the title mol-ecule, C₁₆H₁₃NO₂, is planar. In the crystal, a layer structure is generated by C-H⋯O hydrogen bonds and C-H⋯π(ring), π-stacking and C=O⋯π(ring) inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.0%), H⋯C/C⋯H (25.0%) and H⋯O/O⋯H (22.8%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 120.52 Å³ and 9.64%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the dispersion energy contributions in the title compound. Moreover, the DFT-optimized structure at the B3LYP/6-311G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state.

Keywords: C=O⋯π(ring) interaction; C—H⋯π(ring) interaction; crystal structure; hydrogen bonds; indoline-2,3-dione; π-stacking.

Grants and funding

Funding for this research was provided by: Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).