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

Daouda B., Tuo N. T. , Kangah N. J. , HÖKELEK T. , Kodjo C. G. , Retailleau P., ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.798-809, 2020 (ESCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s2056989020005939
  • Sayfa Sayıları: ss.798-809


The asymmetric unit of the title compound, Ci7H14N20, 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 0 H" " "N hydrogen bonds may help to consolidate the molecular conformations. The two independent molecules are linked through an N H" " "0 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.