The title Schiff base compound was synthesized via the condensation reaction of 1,2-diaminebenzene with 4-benzyloxy-2-hydroxybenzaldehyde. The molecule is V-shaped and possesses mirror symmetry; the mirror bisects the central benzene ring. There are two intramolecular O—H⋯N hydrogen bonds present forming S(6) ring motifs.
The title Schiff base compounds, (I) and (II), were synthesized via the condensation reaction of 2-amino-4-chlorophenol for (I), and 2-(2,3-dihydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benzyloxy-2-hydroxybenzaldehyde. In both compounds, there is an intramolecular hydrogen bond forming an S(6) ring motif; an O—H⋯O hydrogen bond in (I), but a charge-assisted N+—H⋯O− hydrogen bond in (II).
The synthesis and structures of (E)-2-{[(2-aminophenyl)imino]methyl}-5-(benzyloxy)phenol (I) and (Z)-3-benzyloxy-6-{[(5-chloro-2-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one (II) are reported. The crystal structures of the molecules are stabilized by N—H⋯O, O—H⋯O and C—H⋯π contacts. DFT calculations on the structure of (II) support the Keto–imine tautomeric form found in the solid state structure. The antioxident properties of both molecules are investigated.
In the title compound, C20H16N2O4, the molecule adopts an E conformation about the N=C bond. There is an intramolecular O—H⋯N hydrogen bond forming an S(6) ring motif. The nitrobenzene and benzyloxy rings are inclined to the central benzene ring by 4.34 (10) and 27.66 (11)°, respectively, and to one another by 31.40 (12)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [001]. Within the chains there are C—H⋯π interactions present. The chains are linked via π–π interactions [inter-centroid distance = 3.7048 (15) Å], forming slabs parallel to the bc plane.
The asymmetric unit of the title compound, C14H10N2O2, contains two independent molecules. In each molecule, the benzodioxole ring system displays an envelope conformation, with the methylene C atom located at the flap deviating by 0.081 (2) and 0.230 (2) Å from the mean plane formed by the other atoms. The dihedral angles between the benzoimidazole ring system (all atoms) and the benzodioxole benzene ring are 15.35 (6) and 10.99 (7)°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into chains running along the [101].
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