2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclo-pent-2-en-1-yl-idene}-N-phenylhydrazinecarbo-thio-amide.

Abstract

The hydro-chloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenyl-thio-semicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenyl-thio-semicarbazone). Concerning the hydrogen bonding, an N-H⋯N intra-molecular inter-action is observed, forming a ring with graph-set motif S(5). In the crystal, the mol-ecules are connected into centrosymmetric dimers by pairs of N-H⋯S and C-H⋯S inter-actions, forming rings of graph-set motifs R 2 2(8) and R 2 1(7), with the sulfur atoms acting as double acceptors. The thio-semicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0376 (9) Å (the r.m.s.d. amounts to 0.0234 Å). The mol-ecule is substantially twisted as indicated by the dihedral angle between the thio-semicarbazone fragment and the phenyl ring, which amounts to 56.1 (5)°, and because of the jasmone fragment, which bears a chain with sp 3-hybridized carbon atoms in the structure. The Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are: H⋯H (65.3%), H⋯C/C⋯H (16.2%), H⋯S/S⋯H (10.9%) and H⋯N/N⋯H (5.5%).