Synthesis, crystal structure and Hirshfeld analysis of N-ethyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

The title compound (C14H23N3S, common name: cis-jasmone 4-ethylthiosemicarbazone) was synthesized by the equimolar reaction of cis-jasmone and 4-ethylthiosemicarbazide in ethanol facilitated by acid catalysis. There is one crystallographically independent molecule in the asymmetric unit, which shows disorder of the terminal ethyl group of the jasmone carbon chain [site-occupancy ratio = 0.911   (5):0.089   (5)]. The thiosemicarbazone entity [N — N — C(=S) — N] is approximately planar, with the maximum deviation of the mean plane through the N/N/C/S/N atoms being 0.0331   (8)   Å , while the maximum deviation of the mean plane through the five-membered ring of the jasmone fragment amounts to − 0.0337   (8)   Å . The dihedral angle between the two planes is 4.98   (7) ° . The molecule is not planar due to this structural feature and the sp3-hybridized atoms of the jasmone carbon chain. Additionally, one H...N intramolecular interaction is observed, with graph-set motif S(5). In the crystal, the molecules are connected through pairs of H...S interactions with R22(8) and R21(7) graph-set motifs into centrosymmetric dimers. The dimers are further connected by H...N interactions with graph-set motif R22(12), which are related by an inversion centre, forming a mono-periodic hydrogen-bonded ribbon parallel to the b-axis. The crystal structure and the supramolecular assembly of the title compound are compared with four known cis-jasmone thiosemicarbazone deriv...

Source: Acta Crystallographica Section E - April 9, 2024 Category: Chemistry Authors: Oliveira, A.B. de Beck, J. Daniels, J. Tags: thiosemicarbazone jasmone jasmone 4-ethylthiosemicarbazone H-bonded ribbon crystal structure Hirshfeld analysis research communications Source Type: research