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)-1 H-1,2,3-triazole

Abdelmaoujoud Taia; Mohamed Essaber; Abdeljalil Aatif; Karim Chkirate; Tuncer Hökelek; Joel T Mague; Nada Kheira Sebbar

doi:10.1107/S2056989020006994

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)-1 H-1,2,3-triazole

Acta Crystallogr E Crystallogr Commun. 2020 May 29;76(Pt 6):962-966. doi: 10.1107/S2056989020006994. eCollection 2020 Jun 1.

Authors

Abdelmaoujoud Taia¹, Mohamed Essaber¹, Abdeljalil Aatif¹, Karim Chkirate², Tuncer Hökelek³, Joel T Mague⁴, Nada Kheira Sebbar^{2

5}

Affiliations

¹ Laboratory of Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, University of Cadi Ayyad, BP 2390, 40001 Marrakech, Morocco.
² Laboratoire de Chimie Organique Heterocyclique URAC 21, Pôle de Competence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁵ Laboratoire de Chimie Appliquée et Environnement, Equipe de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco.

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.

Keywords: C—H⋯π(ring) interaction; crystal structure; hydrogen bonding; triazole; π-stacking.

Grants and funding

This work was funded by Tulane University grant . Hacettepe University Scientific Research Project Unit grant 013 D04 602 004.