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., ...Daha Fazla

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

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 80
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1107/s2056989024000756
  • Dergi Adı: Acta Crystallographica Section E: Crystallographic Communications
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.232-239
  • Anahtar Kelimeler: C O. . .π(ring) interaction, crystal structure, C—H. . .π(ring) interaction, hydrogen bonds, indoline-2,3-dione, π-stacking
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.