Abstract

In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N—N bond is gauche [C—N—N—C = −117.48 (15)°]. Overall, the mol­ecule has the shape of the letter L. In the crystal packing, supra­molecular chains along the a axis are formed by N—H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phen­yl–tolyl C—H⋯π inter­actions; the layers stack along the c axis with no specific inter­actions between them.

Highlights

  • In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4) with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)

  • The chains are connected into layers by phenyl–tolyl C—H interactions; the layers stack along the c axis with no specific interactions between them

  • For the structure of the 2-tolyl analogue, which is superimposable upon the title compound with the exception of the tolyl rings, see: Tayamon et al (2012)

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Summary

Data collection

C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4) with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5). N bond is gauche [C—N—N—C = 117.48 (15) ]. The molecule has the shape of the letter L. Supramolecular chains along the a axis are formed by N—. H S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered { HNCS}2 and 10membered { HNNH S}2 synthons. The chains are connected into layers by phenyl–tolyl C—H interactions; the layers stack along the c axis with no specific interactions between them

Refinement
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