Synthesis, Crystal Structure and Antibacterial Activity of 5-Bromonicotinic Acid [1-(4-Chlorophenyl)methylidene]hydrazide Monohydrate Methanol Solvate

Abstract

The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, 1H NMR and X-ray single crystal determination. The compound crystallizes in the triclinic space group P − 1 with unit cell dimensions a = 6.9360(14) A, b = 10.070(2) A, c = 12.267(3) A, α = 84.39(3)°, β = 86.10(3)°, γ = 80.50(3)°, V = 839.8(3) Ǻ3, Z = 2, R 1 = 0.0724, and wR 2 = 0.1720. X-ray structure determination reveals that the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity. The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, 1H NMR and X-ray single crystal determination. The molecule of the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity.