(E)-4-Methoxy-2-[3-(trifluoromethyl)phenyliminomethyl]phenol

Abstract

The title compound, C15H12F3NO2, adopts the phenol–imine tautomeric form, with the H atom attached to oxygen rather than to nitro­gen. There are two independent mol­ecules aligned nearly parallel in the asymmetric unit with their trifloramethyl groups pointing in opposite directions. The dihedral angles between the aromatic rings are 40.43 (1)° in the first mol­ecule and 36.12 (1)° in the second. Strong intra­molecular O—H⋯N hydrogen bonding generates S(6) ring motifs. Weak inter­molecular C—H⋯O hydrogen bonds link the independent mol­ecules separately into sheets normal to [010]. In addition, C—H⋯π inter­actions are also observed. The F atoms of the trifluoro­methyl groups are disordered over two sets of sites with refined site occupancies of 0.59 (2)/0.41 (2) and 0.62 (3)/0.38 (3), respectively.

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

“…Out of the relevant structures, three most closely related crystal structures are compared with the crystal structure of MFIP . Reference codes are DUJNUS (containing a 4-methoxy-substituted phenyl ring), 19 FUGWEK (containing a 4-hydroxy-substituted phenyl ring), 20 and YIFLEF (containing a 4-methyl-substituted phenyl ring). 21 Like in MFIP , the molecular configuration of the relevant structures is stabilized by intra-molecular H-bonding (O–H···N).…”