2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide

Abstract

The hydrochloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenylthiosemicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenylthiosemicarbazone). Concerning the hydrogen bonding, an N—H...N intramolecular interaction is observed, forming a ring with graph-set motif S(5). In the crystal, the molecules are connected into centrosymmetric dimers by pairs of N—H...S and C—H...S interactions, forming rings of graph-set motifs R 2 2(8) and R 2 1(7), with the sulfur atoms acting as double acceptors. The thiosemicarbazone 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 molecule is substantially twisted as indicated by the dihedral angle between the thiosemicarbazone 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%).