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Synthesis, Crystal Structure and Antibacterial Activity of N'-(2,4-Dichlorobenzylidene)-4-methylbenzohydrazide

Shaoyun Song1,2, Xianping Liu2, Daohang He2,* and Yongchuang Zhu3

1State Key Laboratory of Biocontrol, School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, P.R. China

2School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P.R. China

3Guangdong Research Institute of Petrochemical Industry, Guangdong Open Laboratory of Chemical Engineering, Guangzhou 510665, P.R. China

*Corresponding author: E-mail: cehdh@scut.edu.cn
Abstract

A Schiff base compound, N'-(2,4-dichlorobenzylidene)-4-methylbenzohydrazide (C15H12N2OCl2) has been synthesized by the condensation of 4-methylbenzohydrazide and 2,4-dichloro benzaldehyde in an ethanol solution. The Schiff base was characterized by 1H NMR, MS and single crystal X-ray diffraction. The crystal structure and antibacterial activity of the compound are reported herein. The crystal belongs to the triclinic system, space group P`1 with a = 6.9796 (4), b = 11.5134 (6), c = 12.5679 (7) Å, a = 115.274(1)°, b = 97.009 (1)°, g = 94.578 (1)°, Z = 2, V = 896.60 (9) Å, Dc = 1.375 g/cm3, Mr = 371.25, l(Moka) = 0.71073 Å, μ = 0.379 mm-1, F (000) = 388. The final R = 0.0344, wR = 0.0984 for 2955 observed reflections with I >2s (I). The two benzene rings are nearly coplanar with the dihedral angle 1.56°. Three classical intermolecular hydrogen bonds exist in the crystal. The compound molecules are connected through hydrogen bonds to generate a two-dimensional network. The results of preliminary biological activity assay showed that the title compound exhibited good antibacterial activity against Staphylococcus aureus and Escherichia coli.
Keywords

Schiff base, Crystal structure, Antibacterial activity.
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