Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl-phen-yl)imino]-meth-yl}-4-methyl-phenol

Md Serajul Haque Faizi; Emine Berrin Cinar; Alev Sema Aydin; Erbil Agar; Necmi Dege; Ashraf Mashrai

doi:10.1107/S2056989020009421

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl-phen-yl)imino]-meth-yl}-4-methyl-phenol

Acta Crystallogr E Crystallogr Commun. 2020 Jul 21;76(Pt 8):1320-1324. doi: 10.1107/S2056989020009421. eCollection 2020 Aug 1.

Authors

Md Serajul Haque Faizi¹, Emine Berrin Cinar², Alev Sema Aydin², Erbil Agar³, Necmi Dege², Ashraf Mashrai⁴

Affiliations

¹ PG Department of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, Bihar 842001, India.
² Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey.
³ Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey.
⁴ Department of Pharmacy, University of Science and Technology, Ibb Branch, Ibb, Yemen.

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.

Keywords: 2-hydroxy-5-methylbenzaldehyde; 3-chloro-4-methylaniline; Schiff base; crystal structure.

Grants and funding

This work was funded by University Grants Commission grant . Université Sidi Mohamed Ben Abdallah (Morocco) grant . University of Science and Technology, Ibb Branch (Yemen) grant .