Syntheses, Characterization and Crystal Structures of Two Isostructural Hydrazone Compounds N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-4-chlorobenzohydrazide Methanol Solvate and N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-chlorobenzohydrazide Methanol Solvate

Abstract

Reactions of 4-chlorobenzohydrazide with 3-bromo-5-chloro-2-hydroxybenzaldehyde and 3,5-dichloro-2-hydroxybenzaldehyde, respectively, afforded two isostructural hydrazone compounds, C14H9BrCl2N2O2·CH3OH (1) and C14H9Cl3N2O2·CH3OH (2). Both compounds were structurally characterized by X-ray determination. Compound 1 crystallizes in the triclinic space group P − 1 with unit cell dimensions a = 7.462(1) A, b = 9.281(2) A, c = 12.626(1) A, α = 98.451(2)°, β = 98.630(2)°, γ = 100.025(2)°, V = 837.8(2) A3, Z = 2, R 1 = 0.0394 and wR 2 = 0.0967. Compound 2 crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 7.485(1) A, b = 13.389(2) A, c = 16.693(2) A, β = 99.754(2)°, V = 1648.7(4) A3, Z = 4, R 1 = 0.0375 and wR 2 = 0.0900. X-ray structural determination revealed that each compound consists of a hydrazone molecule and a methanol molecule of crystallization. In the crystal structures of both compounds, the adjacent molecules are linked by methanol molecules through N–H···O and O–H···O hydrogen bonds, forming dimers. Reactions of 4-chlorobenzohydrazide with 3-bromo-5-chloro-2-hydroxybenzaldehyde and 3,5-dichloro-2-hydroxybenzaldehyde, respectively, afforded two isostructural hydrazone compounds, C14H9BrCl2N2O2·CH3OH and C14H9Cl3N2O2·CH3OH. Both compounds were structurally characterized by X-ray crystallography. Each compound consists of a hydrazone molecule and a methanol molecule of crystallization.