(Pyridin-4-yl)methylN′-(3-phenylallylidene)hydrazinecarbodithioate

Abstract

In the title compound, C16H15N3S2, the central C2N2S2 residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the mol­ecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supra­molecular chains along [1-10] are stabilized by N—H⋯N(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C—H⋯π(pyridine) inter­actions.

Conjugation of a New Series of Dithiocarbazate Schiff Base Copper(II) Complexes with Vectors Selected to Enhance Antibacterial Activity

“…The Schiff bases are in the thione form with CS bond distances ranging from 1.6617(11) to 1.682(3) Å. The bond lengths were intermediate between a C–S single bond and a CS double bond possibly due to the extensive conjugation over the CN–N–C chain and other intermolecular interactions. , The N–N bond distance varied from 1.3797(7) to 1.3941(13) Å in the Schiff bases, showing that the bond was shorter than a single bond, also indicating significant π-delocalization along the dithiocarbazate moiety. − Trans–cis isomerism was exhibited in all the Schiff bases around the -SC(S)NH- moiety. It was observed that the methyl levulinate/levulinic acid chain was trans with respect to the terminal thione S atom about the C–N bond while the S-methyl/S-benzyl group was cis with respect to the terminal thione S atom about the C–S bond.…”

“…The bond lengths were intermediate between a C−S single bond and a CS double bond possibly due to the extensive conjugation over the CN−N−C chain and other intermolecular interactions. 51,52 The N−N bond distance varied from 1.3797 (7) to 1.3941(13) Å in the Schiff bases, showing that the bond was shorter than a single bond, also indicating significant π-delocalization along the dithiocarbazate moiety. 51−53 Trans−cis isomerism was exhibited in all the Schiff bases around the -SC(S)NH-moiety.…”

Crystal structure of 2-{[2-(3-phenylallylidene)hydrazin-1-yl]thiocarbonylsulfanylmethyl}pyridinium chloride

“…For general background to related Schiff bases formed between S-substituted dithiocarbazates and cinnamaldehyde, see: Low et al (2013). For the biological activity of similar sulfur/nitrogen-containing Schiff base derivatives, see: Khoo et al (2014).…”