Syntheses, Crystal Structures, and Antimicrobial Activities of N′-(5-Hydroxy-2-nitrobenzylidene)-4-dimethylaminobenzohydrazide Methanol Solvate and 2-Fluoro-N′-(5-hydroxy-2-nitrobenzylidene)benzohydrazide

Two new hydrazone compounds, N'-(5-hydroxy-2-nitrobenzylidene)-4-dimethylaminobenzohydrazide methanol solvate (1) and 2-fluoro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide (2), have been synthesized and characterized by elemental analysis, IR spectra, H-1 NMR, and single-crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P2(1)/c with a = 11.571(3), b = 12.420(3), c = 12.360(2) angstrom, beta = 97.495(2)degrees, V = 1761.1(7) angstrom(3), Z = 4, R = 0.0735 and wR = 0.1344. Compound 2 crystallizes in the triclinic space group P (1) over bar with a = 7.551(3), b = 8.254(3), c = 11.365(2) angstrom, alpha = 79.352(2), beta = 76.154(2), gamma = 71.624(2)degrees, V = 648.2(4) angstrom(3), Z = 2, R = 0.0393 and wR = 0.1008. The hydrazone molecules of the compounds display E configurations with respect to the C=N double bonds. In the crystal structure of 1, the hydrazone molecules are linked by methanol molecules through N-H center dot center dot center dot O, O-H center dot center dot center dot N and O-H center dot center dot center dot O hydrogen bonds, forming chains running along the c axis. In the crystal structure of 2, molecules are linked through N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds, forming ribbons running along the b axis. The preliminary antimicrobial activities were studied.