N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]-cyclopent-2-en-1-ylidene}hydrazinecarbothioamide
N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]-cyclopent-2-en-1-ylidene}hydrazinecarbothioamide
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09.01.2024Publisher
IUCrPublisher Location
Chester, EnglandMetadata
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Citable Link (Handle URI) 
https://hdl.handle.net/20.500.11811/14326
Abstract
The equimolar and hydrochloric acid-catalysed reaction between cis-jasmone and 4-methylthiosemicarbazide in ethanolic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methylthiosemicarbazone). Two molecules 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 thiosemicarbazone 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 molecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The molecules are not planar, since the jasmone groups have a chain with sp3-hybridized carbon atoms and, in addition, the thiosemicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each molecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the molecules are connected through pairs of N—H⋅⋅⋅S and C—H⋅⋅⋅S interactions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R22(8) and R21(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%) interactions [considering the two crystallographically independent molecules and only the disordered atoms with the highest s.o.f. for the evaluation].
Subjects
thiosemicarbazone, cis-jasmone, methylthiosemicarbazone derivative, centrosymmetric dimers, crystal structure, Hirshfeld analysis
Classification (DDC)
540 ChemiePublished in
IUCrData, 2024, volume 9, part 1, x240013, pp. 1-6First Publication
https://doi.org/10.1107/S2414314624000130Bof de Oliveira, Adriano; Bresolin, Leandro; Beck, Johannes; Daniels, Jörg: N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]-cyclopent-2-en-1-ylidene}hydrazinecarbothioamide. In: IUCrData. 2024, volume 9, part 1, x240013, 1-6.
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14326
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14326
@article{handle:20.500.11811/14326,
author = {{Adriano Bof de Oliveira} and {Leandro Bresolin} and {Johannes Beck} and {Jörg Daniels}},
title = {N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]-cyclopent-2-en-1-ylidene}hydrazinecarbothioamide},
publisher = {IUCr},
year = 2024,
month = jan,
journal = {IUCrData},
volume = 2024, volume 9,
number = part 1, x240013,
pages = 1--6,
note = {The equimolar and hydrochloric acid-catalysed reaction between cis-jasmone and 4-methylthiosemicarbazide in ethanolic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methylthiosemicarbazone). Two molecules 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 thiosemicarbazone 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 molecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The molecules are not planar, since the jasmone groups have a chain with sp3-hybridized carbon atoms and, in addition, the thiosemicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each molecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the molecules are connected through pairs of N—H⋅⋅⋅S and C—H⋅⋅⋅S interactions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R22(8) and R21(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%) interactions [considering the two crystallographically independent molecules and only the disordered atoms with the highest s.o.f. for the evaluation].},
url = {https://hdl.handle.net/20.500.11811/14326}
}
author = {{Adriano Bof de Oliveira} and {Leandro Bresolin} and {Johannes Beck} and {Jörg Daniels}},
title = {N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]-cyclopent-2-en-1-ylidene}hydrazinecarbothioamide},
publisher = {IUCr},
year = 2024,
month = jan,
journal = {IUCrData},
volume = 2024, volume 9,
number = part 1, x240013,
pages = 1--6,
note = {The equimolar and hydrochloric acid-catalysed reaction between cis-jasmone and 4-methylthiosemicarbazide in ethanolic solution yields the title compound, C13H21N3S (common name: cis-jasmone 4-methylthiosemicarbazone). Two molecules 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 thiosemicarbazone 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 molecule and 0.0052 (14) Å (r.m.s.d. = 0.0031 Å) for the disordered one. The molecules are not planar, since the jasmone groups have a chain with sp3-hybridized carbon atoms and, in addition, the thiosemicarbazone fragments are attached to the respective carbon five-membered rings and the dihedral angles between them for each molecule amount to 8.9 (1) and 6.3 (1)°. In the crystal, the molecules are connected through pairs of N—H⋅⋅⋅S and C—H⋅⋅⋅S interactions into crystallographically independent centrosymmetric dimers, in which rings of graph-set motifs R22(8) and R21(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%) interactions [considering the two crystallographically independent molecules and only the disordered atoms with the highest s.o.f. for the evaluation].},
url = {https://hdl.handle.net/20.500.11811/14326}
}
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