Crystal structure ofN-ethyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, one of them being disordered over the methyl group. The mol­ecules are linked by weak H⋯S inter­actions into chains with graph-set motifs C(4) along [100] and and (10) rings. The Hirshfeld surface calculation suggests that the most important contribution for the crystal structure are the H⋯H inter­actions (64.20%).

(2E)-N-Methyl-2-[1-(4-methylcyclohex-3-en-1-yl)ethylidene]hydrazinecarbothioamide

“…1 and Table 1). The bond lengths and angles of the title compound are normal and agree with those values reported in other methyl-hydrazinecarbothioamide structures (Gangadharan et al, 2015;de Oliveira et al, 2017;Tayamon et al, 2012). In both molecules, the thiosemicarbazone groups adopts an extended conformation, as shown by the torsion angles S1-C2-N2- N3 [175.83 (14) , molecule A] and S2-C13-N5-N6 [À171.21 (15) , molecule B].…”

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

“…4 To the best of our knowledge and from using database tools such as SciFinder (Chemical Abstracts Service, 2023) and the Cambridge Structural Database (CSD; Groom et al, 2016), only the crystal structure of the non-substituted cis-jasmone thiosemicarbazone has been reported (Orsoni et al, 2020). The terminal group of the thiosemicarbazones plays an essential role in the intermolecular interactions and the supramolecular arrangement, e.g., the non-substituted form, which shows the NH 2 terminal group, leads to the building of mono-periodic hydrogen-bonded ribbons, while a phenyl ring attached to the terminal nitrogen atom leads to the formation of discrete dimeric units (Oliveira et al, 2017). This molecular architecture is specially observed for compounds with a nonpolar organic periphery and therefore, the tetralone 4-phenylthiosemicarbazone derivative (Oliveira et al, 2014) was chosen for comparison with the title compound.…”

A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

“…For a comparison of selected geometric parameters of the �-and �-modifications of cis-jasmone thiosemicarbazone, see Table 2. The crystal structures of non-substituted thiosemicarbazones attached to non-polar organic groups have been studied by our group, such as the structures of the (À )-menthone (Oliveira et al, 2014) and the tetralone thiosemicarbazone derivatives (Oliveira et al, 2012(Oliveira et al, , 2017. In the structure of the (À )-menthone thiosemicarbazone, the molecules are linked by N-H� � �S intermolecular interactions, forming rings with graph-set motif R 2 2 (8), into mono-periodic hydrogen-bonded ribbons along [100].…”

“…The starting materials are commercially available and were used without further purification. The synthesis of cis-jasmone thiosemicarbazone was adapted from previously reported procedures (Freund & Schander, 1902;Oliveira et al, 2017;Orsoni et al, 2020). The mixture of ethanolic solutions of cisjasmone (8 mmol in 50 ml) and thiosemicarbazide (8 mmol in 50 ml), was catalysed with HCl and refluxed for 8 h. After cooling, the precipitated product was filtered off and washed with cold ethanol.…”