Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol


Daouda B., Tuo N. T. , HÖKELEK T. , Jean-Baptiste K. N. , Guillaume K. C. , Claude K. A. L. , ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.605-616, 2020 (ESCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s2056989020004284
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Sayfa Sayıları: ss.605-616

Özet

The title compound, C18H16N2O2, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)degrees with respect to the best plane of the other five atoms. In the crystal, O-H-Phnl center dot center dot center dot NPrmdn and N-HPrmdn center dot center dot center dot O-Phnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C-H center dot center dot center dot pi interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (49.0%), H center dot center dot center dot C/C center dot center dot center dot H (35.8%) and H center dot center dot center dot O/O center dot center dot center dot H (12.0%) interactions. Hydrogen bonding and van derWaals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O-H-Phnl center dot center dot center dot N-Prmdn and N-H-Prmdn center dot center dot center dot O-Phnl hydrogen-bond energies are 58.4 and 38.0 kJ mol(-1), respectively. 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.