Abstract
The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 3-chloro-4-methyl-aniline, and crystallizes in the monoclinic space group P21/c. The 3-chloro-benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (43.8%) and C⋯H/H⋯C (26.7%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is provided.
Highlights
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from HÁ Á ÁH (43.8%) and CÁ Á ÁH/HÁ Á ÁC (26.7%) interactions
Schiff bases are employed as catalyst carriers (Grigoras et al, 2001), thermo-stable materials (Vanco et al, 2004), metal–cation complexing agents and in biological systems (Taggi et al, 2002)
The present work is a part of an ongoing structural study of Schiff bases and their utilization in the synthesis of quinoxaline derivatives (Faizi et al, 2018), fluorescence sensors (Faizi et al, 2016; Mukherjee et al, 2018; Kumar et al, 2017, 2018) and non-linear optical properties (Faizi et al, 2020)
Summary
Schiff bases contain the azomethine moiety (–RCH N–R0) and are prepared by condensation reactions between amines and active carbonyl compounds. Schiff base ligands are potentially capable of forming stable complexes by coordination of metal ions with their nitrogen atoms as donors (Ebrahimipour et al, 2012). They are important for their photochromic properties and have applications in various fields such as the measurement and control of radiation intensities in imaging systems, optical computers, electronics, optoelectronics and photonics (Iwan et al, 2007). We report on the synthesis (from 2-hydroxy-5methylbenzaldehyde and 3-chloro-4-methylaniline), crystal structure, Hirshfeld surface analysis and DFT computational calculations of the title compound, (I). Symmetry codes: (i) Àx þ 1; Ày þ 1; Àz þ 1; (ii) Àx; Ày þ 2; Àz
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