Research Article: (E)-[({[(3-Methyl­phen­yl)meth­yl]sulfan­yl}methane­thio­yl)amino](1-phenyl­pentyl­idene)amine

Date Published: June 01, 2011

Publisher: International Union of Crystallography

Author(s): Georgiana Paulus, Karen A. Crouse, Mohamed Ibrahim Mohamed Tahir, Edward R. T. Tiekink.


In the structure of the title compound, C20H24N2S2, the central CN2S2 atoms are planar (r.m.s. deviation = 0.0205 Å) but both benzene rings are twisted out of this plane forming dihedral angles of 23.03 (6) and 84.75 (4)° (tol­yl); the n-butyl group occupies a position normal to the plane [N—C—C—C torsion angle = −84.33 (16)°]. The conformation of the imine bond [1.2888 (18) Å] is E. The syn arrangement of the thione S and amino H atoms enables the formation of N—H⋯S hydrogen bonds between centrosymmetrically related mol­ecules. These lead to eight-membered {⋯HNC=S}2 synthons which are further stabilized by proximate C—H⋯S interactions. The resulting dimeric aggregates are connected into a supra­molecular chain along the c axis by C—H⋯π(tol­yl) inter­actions.

Partial Text

For background on the coordination chemistry of hydrazine­carbodithio­ates, see: Ravoof et al. (2010 ▶). For related structures, see: Khoo et al. (2005 ▶); How et al. (2007 ▶).




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