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

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.

In the structure of the title compound, C 20 H 24 N 2 S 2 , the central CN 2 S 2 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 = À84.33 (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-HÁ Á ÁS hydrogen bonds between centrosymmetrically related molecules. These lead to eight-membered {Á Á ÁHNC S} 2 synthons which are further stabilized by proximate C-HÁ Á ÁS interactions. The resulting dimeric aggregates are connected into a supramolecular chain along the c axis by C-HÁ Á Á(tolyl) interactions. Experimental Crystal data C 20 Table 1 Hydrogen-bond geometry (Å , ).

Related literature
Cg1 is the centroid of the C14-C19 ring.

Comment
In continuing interest in the coordination chemistry of hydrazinecarbodithioate derivatives (Ravoof et al., 2010), structural studies on the precursor molecules have been undertaken (Khoo et al. 2005;How et al. 2007). In this connection, the title compound, (I), the product of the condensation reaction between 3-methylbenzyldithiocarbazate and valerophenone, was investigated.
The central CN 2 S 2 atoms in the molecular structure of (I), Fig. 1, are planar with a r.m.s. = 0.0205 Å. The adjacent residues are twisted out of this plane as seen in the values of the C1-N1-N2-C2 and C1-S2-C13-C14 torsion angles of 167.00 (12) and -163.64 (10) °, respectively. Further, the dihedral angles formed between the C3···C6 and C14···C19 benzene rings with the central plane are 23.03 (6) and 84.75 (4) °, respectively, indicating approximate co-planar and a perpendicular dispositions, respectively. Thus, the benzene rings are almost normal to each other, forming a dihedral angle between their respective least-squares planes of 80.13 (5) °. Finally, the n-butyl group, having an extended conformation, occupies a position approximately normal to the central plane with N2-C2-C9-C10 torsion angle being -84.33 (16) °.
The conformation about the N2═C2 bond [1.2888 (18) Å] is E. The thione-S1 and amino-H atoms are syn, a disposition that allows for the formation of N-H···S hydrogen bonds between centrosymmetrically related molecules, Table 1. These lead to eight-membered {···HNC═S} 2 synthons which are further stabilized by proximate C-H···S interactions, Table 1. The dimeric aggregates are connected into linear supramolecular chains along the c axis via C-H···π(C14···C19) contacts, Table   1 and Fig. 2. The chains pack into layers in the ac plane and their organic residues inter-digitate along the b axis, Fig. 3.

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2 to 1.5U equiv (C). The amino H-atom was refined with a distance restraint of N-H = 0.88±0.01 Å with U iso (H) = 1.2U eq (N).
supplementary materials sup-2 Figures Fig. 1. The molecular structure of of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.