Title of article :
Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of 4-[(4-allyl-2-methoxyphenoxy)methyl]-1-(4-methoxyphenyl)-1H-1,2,3-triazole
Author/Authors :
Taia, Abdelmaoujoud Laboratory of Molecular Chemistry - Department of Chemistry - Faculty of Sciences Semlalia - University of Cadi Ayyad, Morocco , Essabera, Mohamed Laboratory of Molecular Chemistry - Department of Chemistry - Faculty of Sciences Semlalia - University of Cadi Ayyad, Morocco , Aatif, Abdeljalil Laboratory of Molecular Chemistry - Department of Chemistry - Faculty of Sciences Semlalia - University of Cadi Ayyad, Morocco , Chkirate, Karim Laboratoire de Chimie Organique Heterocyclique URAC 21 - Pôle de Competence Pharmacochimie, Morocco , Hökelek, Tuncer Department of Physics - Hacettepe University, Turkey , Mague, Joel T. Department of Chemistry - Tulane University, USA , Sebbar, Nada Kheira Laboratoire de Chimie Organique Heterocyclique URAC 21 - Pôle de Competence Pharmacochimie, Morocco
Abstract :
In the title molecule, C20H21N3O3, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C—HMthphn⋯OMthphn (Mthphn = methoxyphenyl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C—H⋯π(ring) interactions, together with π–π stacking interactions [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%) interactions. Computational chemistry reveals that the C—HMthphn⋯OMthphn 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 molecular structure. The HOMO–LUMO behaviour was elucidated to determine the energy gap.
Keywords :
crystal structure , π-stacking , C—H⋯π(ring) interaction , hydrogen bonding , triazole
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
