Acta Crystallographica Section E: Crystallographic Communications (Jun 2020)

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)phenol

  • Ballo Daouda,
  • Nanou Tiéba Tuo,
  • Niameke Jean-Baptiste Kangah,
  • Tuncer Hökelek,
  • Charles Guillaume Kodjo,
  • Pascal Retailleau,
  • El Mokhtar Essassi

DOI
https://doi.org/10.1107/S2056989020005939
Journal volume & issue
Vol. 76, no. 6
pp. 798 – 802

Abstract

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The asymmetric unit of the title compound, C17H14N2O, contains two independent molecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intramolecular O—H...N hydrogen bonds may help to consolidate the molecular conformations. The two independent molecules are linked through an N—H...O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (52.9%) and H...C/C...H (39.5%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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