Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol

Abstract

The synthesis, characterization, and theoretical studies of the title compound has been reported in this study. The molecular structure has been characterized by room-temperature single-crystal X-ray diffraction study which reveals that it has an angular shape with intramolecular and intermolecular hydrogen bonding. Crystal data for the title compound, C27H22N2O2 (M =406.46 g/mol): monoclinic, space group C2/c (no. 15), a = 36.371(10) Å, b = 4.6031(12) Å, c = 12.192(3) Å, β = 94.972(6)°, V = 2033.5(9) Å3, Z = 4, T = 100 K, μ(MoKα) = 0.084 mm-1, Dcalc = 1.328 g/cm3, 8812 reflections measured (2.248° ≤ 2Θ ≤ 49.734°), 1773 unique (Rint = 0.0323, Rsigma = 0.0239) which were used in all calculations. The final R1 was 0.0411 (I > 2σ(I)) and wR2 was 0.1165 (all data). In crystal structure, the molecule exits in the enol form and is located on a two-fold axis of symmetry; where the central methylene carbon atom of the diphenylmethane moiety is displaced from the aromatic ring planes. The Hirshfeld surface analysis of the title compound shows that H···H, C···H, and O···H interactions of 53.3, 13.2, and 5.4%; respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. The HOMO-LUMO energy gap in the title compound is 2.9639 eV. Molecular electrostatic potential of the investigated compound has also been studied.