Syntheses, crystal structures and antimicrobial studies of two new semicarbazone derivatives

Abstract

Two new derivatives of semicarbazone, (E)-2-(hexan-2-ylidene) hydrazinecarboxamide and (E)-2-(heptan-2-ylidene)hydrazinecarboxamide were synthesized and characterized by IR and 1H NMR. Their crystal structures were characterized by X-ray diffraction method. Compound (I) crystallizes in triclinic P 1 ?, a = 6.7679(7) Å, b = 7.1912(8) Å, c = 9.9969(11) Å, ? = 108.824(2), ? = 99.398(3), ? = 92.680(2), V = 451.75(8) Å3, Z = 2, R <inf>1</inf> = 0.043 and wR <inf>2</inf> = 0.140. Compound (II) crystallizes in triclinic P 1 ?, a = 6.7192(6) Å, b = 7.2094(6) Å, c = 11.2842(11) Å, ? = 103.303(2), ? = 106.198(2), ? = 91.219(1), V = 508.70(8) Å3, Z = 2, R <inf>1</inf> = 0.044 and wR <inf>2</inf> = 0.133. Their molecules adopt a L-shape conformation with C atom in C=N double bond acting as the junction point. The C=O double bond indicate the existence of semicarbazone group in keto-like form for both compounds in their solid state. In the crystal, the carbonyl O atom for both derivatives acts as a common acceptor in the intermolecular bifurcated N-H·O hydrogen bonding which linked the molecules into one-dimensional supramolecular ribbons. Antimicrobial studies by serial dilution method showed both compounds exhibit antibacterial property. Graphical Abstract: Two new semicarbazone derivatives are characterized by IR, 1H NMR and single crystal X-ray diffraction methods and their antibacterial activity was further investigated by screening against four different bacterial strains.[Figure not available: see fulltext.] © 2013 Springer Science+Business Media New York.