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) Å, b = 9.281(2) Å, c = 12.626(1) Å, α = 98.451(2)°, β = 98.630(2)°, γ = 100.025(2)°, V = 837.8(2) Å³, 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) Å, b = 13.389(2) Å, c = 16.693(2) Å, β = 99.754(2)°, V = 1648.7(4) Å³, 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.

Graphical 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 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.