Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of 4-[(4-ally1-2methoxyphenoxy)methy1]-1-(4-methoxypheny1)-1H-1,2,3-triazole


Taia A., Essaber M., Aatif A., Chkirate K., HÖKELEK T. , Mague J. T. , ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.962-972, 2020 (Journal Indexed in ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 76
  • Publication Date: 2020
  • Doi Number: 10.1107/s2056989020006994
  • Title of Journal : ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Page Numbers: pp.962-972

Abstract

In the title molecule, C20H21N303, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)]. In the crystal, C HMthphif " "OMthphn (Mthphn = methoxyphenyl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C H" " -7r(ring) interactions, together with 7r rr stacking interactions [centroid-to-centroid distance = 3.7318 (10) A] between parallel phenyl rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H" " "H (48.7%) and H" " "C/C" " "H (23.3%) interactions. Computational chemistry reveals that the C HMthphn" "OMthphn hydrogen bond energy is 47.1 kJ mori. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level, is compared with the experimentally determined molecular structure. The HOMO LUMO behaviour was elucidated to determine the energy gap.