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-HMthphn⋯OMthphn (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-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 mol-ecular structure. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
Abdelmaoujoud Taia,a* Mohamed Essaber,a Abdeljalil Aatif,a Karim Chkirate,b Tuncer Hokelek,c Joel T
C— HMthphnÁ Á ÁOMthphn (Mthphn = methoxyphenyl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C—HÁ Á Á(ring) interactions, together with – 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 HÁ Á ÁH (48.7%) and HÁ Á ÁC/CÁ Á ÁH (23.3%) interactions
Summary
Clove essential oil is extracted from cloves, which come from a tree belonging to the Myrtaceae family (Chang & Miau, 1984), originating from the Moluccas in Indonesia. 1,2,3-triazoles are known by their diverse biological activities being used as antileishmania (Teixeira et al, 2018), antimicrobial (Glowacka et al, 2019) or antiviral (Bankowska, et al, 2014) agents In this context, we have synthesized the title compound, (I), through cycloaddition reaction of 1-azido4-methoxybenzene with 4-allyl-2-methoxy-1-(prop-2-ynyloxy). 3. Supramolecular features In the crystal structure, (100) layers are formed by C— HMthphnÁ Á ÁOMthphn (Mthphn = methoxyphenyl) hydrogen bonds (Table 1, Fig. 2). Supramolecular features In the crystal structure, (100) layers are formed by C— HMthphnÁ Á ÁOMthphn (Mthphn = methoxyphenyl) hydrogen bonds (Table 1, Fig. 2) These are stacked along the a axis. Through C6—H6Á Á ÁCg3(x, À12 À y, À12 + z) interactions (Table 1) as well as through —- stacking interactions between inversion-related C rings [Cg3Á Á ÁCg3(1 À x, Ày, 1 À z] with a centroid-to-centroid distance of 3.7318 (10) A (Fig. 3)
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