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

Md Serajul Haque Faizi,Alev Sema Aydin,Ashraf Mashrai,Necmi Dege,Erbil Agar,Onur Erman Dogan,Emine Berrin Cinar

doi:10.1107/s2056989020009615

Abstract

The title compound, C15H12F3NO, crystallizes with one mol-ecule in the asymmetric unit. The configuration of the C=N bond is E and there is an intra-molecular O-H⋯N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-tri-fluoro-methyl-phenyl rings is 44.77 (3)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C⋯H/H⋯C (29.2%), H⋯H (28.6%), F⋯H/H⋯F (25.6%), O⋯H/H⋯O (5.7%) and F⋯F (4.6%) 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 in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.

Highlights

Over the past 25 years, there has been extensive research on the synthesis and use of Schiff base compounds in organic and inorganic chemistry as they have important medicinal and pharmaceutical applications
We report here on the synthesis and crystal structure as well as the Hirshfeld surface analysis of the new compound, (I)
Supramolecular features In the crystal of (I), molecules are linked by intermolecular C—HÁ Á ÁO interactions, forming chains extending along the a-axis direction (Fig. 2 and Table 1)

Summary

Chemical context

Over the past 25 years, there has been extensive research on the synthesis and use of Schiff base compounds in organic and inorganic chemistry as they have important medicinal and pharmaceutical applications. The C10—O1 bond length [1.357 (8) A (experimental) and 1.342 A (calculated)] indicates singlebond character (Ozeryanskii et al, 2006), while the imine C8 N1 bond length [1.283 (8) A (experimental) and 1.290 A (calculated)] indicates double-bond character All these data support the existence of the phenol–imine tautomer for (I) in its crystalline state. The presence of C—HÁ Á ÁO interactions in the crystal is indicated by the pair of characteristic wings in the fingerprint plot delineated into CÁ Á ÁH/HÁ Á ÁC (Fig. 5b) contacts (29.2% contributions to the Hirshfeld surface). (4.6%; Fig. 5f) contacts, with smaller contributions from NÁ Á ÁH/H.ÁN (2.4%), OÁ Á ÁC/CÁ Á ÁO (2.2%), FÁ Á ÁC/CÁ Á ÁF (0.8%) and OÁ Á ÁN/NÁ Á ÁO (0.2%) contacts

DFT calculations

Database survey

Synthesis and crystallization

Findings

Refinement