Crystal structure, Hirshfeld surface analysis, inter-action energy and DFT studies of 4-[(4-allyl-2-meth-oxy-phen-oxy)meth-yl]-1-(4-meth-oxy-phen-yl)-1H-1,2,3-triazole.

ABSTRACT: In the title mol-ecule, C₂₀H₂₁N₃O₃, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C-H_Mthphn⋯O_Mthphn (Mthphn = meth-oxy-phen-yl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C-H⋯π(ring) inter-actions, together with π-π stacking inter-actions [centroid-to-centroid distance = 3.7318 (10) Å] 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%) inter-actions. Computational chemistry reveals that the C-H_Mthphn⋯O_Mthphn hydrogen bond energy is 47.1 kJ mol^-1. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level, is compared with the experimentally determined mol-ecular structure. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

SUBMITTER: Taia A 

PROVIDER: S-EPMC7273996 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature