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

ABSTRACT:

SUBMITTER: Oliveira A

PROVIDER: S-EPMC10833128 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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

Project description:The equimolar and hydro-chloric acid-catalysed reaction between cis-jasmone and 4-methyl-thio-semicarbazide in ethano-lic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methyl-thio-semicarbazone). Two mol-ecules with all atoms in general positions are present in the asymmetric unit. In one of them, the carbon chain is disordered [site occupancy ratio = 0.821 (3):0.179 (3)]. The thio-semicarbazone entities [N-N-C(=S)-N] are approximately planar, with the maximum deviation from the mean plane through the selected atoms being -0.0115 (16) Å (r.m.s.d. = 0.0078 Å) for the non-disordered mol-ecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The mol-ecules are not planar, since the jasmone groups have a chain with sp 3-hybridized carbon atoms and, in addition, the thio-semicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each mol-ecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the mol-ecules are connected through pairs of N-H⋯S and C-H⋯S inter-actions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R 2 2(8) and R 2 1(7) are observed. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are from H⋯H (70.6%), H⋯S/S⋯H (16.7%), H⋯C/C⋯H (7.5%) and H⋯N/N⋯H (4.9%) inter-actions [considering the two crystallographically independent mol-ecules and only the disordered atoms with the highest s.o.f. for the evaluation].

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A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclo-pent-2-en-1-yl-idene}hydrazinecarbo-thio-amide.

Project description:A second crystalline modification of the title compound, C12H19N3S [common name: cis-jasmone thio-semicarbazone] was crystallized from tetra-hydro-furane at room temperature. There is one crystallographic independent mol-ecule in the asymmetric unit, showing disorder in the cis-jasmone chain [site-occupancy ratio = 0.590 (14):0.410 (14)]. The thio-semicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0463 (14) Å [r.m.s.d. = 0.0324 Å], while for the five-membered ring of the jasmone fragment, the maximum deviation from the mean plane through the carbon atoms amounts to 0.0465 (15) Å [r.m.s.d. = 0.0338 Å]. The mol-ecule is not planar due to the dihedral angle between these two fragments, which is 8.93 (1)°, and due to the sp 3-hybridized carbon atoms in the jasmone fragment chain. In the crystal, the mol-ecules are connected by N-H⋯S and C-H⋯S inter-actions, with graph-set motifs R 2 2(8) and R 2 1(7), building mono-periodic hydrogen-bonded ribbons along [010]. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are H⋯H (67.8%), H⋯S/S⋯H (15.0%), H⋯C/C⋯H (8.5%) and H⋯N/N⋯H (5.6%) [only non-disordered atoms and those with the highest s.o.f. were considered]. This work reports the second crystalline modification of the cis-jasmone thio-semicarbazone structure, the first one being published recently [Orsoni et al. (2020 ▸). Int. J. Mol. Sci. 21, 8681-8697] with the crystals obtained in ethanol at 273 K.

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4-(5-{2-[5-(4-Cyano-phen-yl)-3-methyl-thio-phen-2-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl}-4-methyl-thio-phen-2-yl)benzo-nitrile chloro-form hemisolvate.

Project description:The crystal structure of the title compound, C29H16F6N2S2·0.5CHCl3, consists of mol-ecules with disordered perfluoro-cyclo-pentene rings [occupancy ratio 0.685 (3):0.315 (3)] and close F⋯F contacts (in the range 2.45-2.73 Å) between mol-ecules. The short contacts are associated with the disorder. The dihedral angle between thiophene rings is 57.44 (8)°. The 5-(4-cyano-phen-yl)-3-methyl-2-thienyl groups of adjacent mol-ecules are parallel, leading to zigzag chains of mol-ecules along [101]. The dihedral angles between each thiophene ring and its adjacent cyanobenzene ring are 8.9 (2) and 7.15 (10)°.

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