Crystal structure, Hirshfeld surface analysis, crystal voids, interaction energy calculations and energy frameworks, and DFT calculations of 1-(4-methylbenzyl)indoline-2,3-dione

Rharmili N., Abdellaoui O., Chahdi F. O., Mague J. T., Hökelek T., Mazzah A., ...More

Acta Crystallographica Section E: Crystallographic Communications, vol.80, pp.232-239, 2024 (ESCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 80
  • Publication Date: 2024
  • Doi Number: 10.1107/s2056989024000756
  • Journal Name: Acta Crystallographica Section E: Crystallographic Communications
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.232-239
  • Keywords: C O. . .π(ring) interaction, crystal structure, C—H. . .π(ring) interaction, hydrogen bonds, indoline-2,3-dione, π-stacking
  • Hacettepe University Affiliated: Yes

Abstract

The indoline portion of the title molecule, 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) interactions. 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%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions 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/6-311-G(d,p) level is compared with the experimentally determined molecular structure in the solid state.