A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide
A second crystalline modification of the title compound, C12H19N3S [common name: cis-jasmone thiosemicarbazone] was crystallized from tetrahydrofurane at room temperature. There is one crystallographic independent molecule in the asymmetric unit, showing disorder in the cis-jasmone chain [site-occup...
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International Union of Crystallography
2023-11-01
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2414314623010180 |
| _version_ | 1797403933463805952 |
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| author | Adriano Bof de Oliveira Leandro Bresolin Vanessa Carratu Gervini Johannes Beck Jörg Daniels |
| author_facet | Adriano Bof de Oliveira Leandro Bresolin Vanessa Carratu Gervini Johannes Beck Jörg Daniels |
| author_sort | Adriano Bof de Oliveira |
| collection | DOAJ |
| description | A second crystalline modification of the title compound, C12H19N3S [common name: cis-jasmone thiosemicarbazone] was crystallized from tetrahydrofurane at room temperature. There is one crystallographic independent molecule in the asymmetric unit, showing disorder in the cis-jasmone chain [site-occupancy ratio = 0.590 (14):0.410 (14)]. The thiosemicarbazone 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 molecule is not planar due to the dihedral angle between these two fragments, which is 8.93 (1)°, and due to the sp3-hybridized carbon atoms in the jasmone fragment chain. In the crystal, the molecules are connected by N—H...S and C—H...S interactions, with graph-set motifs R22(8) and R21(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 thiosemicarbazone 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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| issn | 2414-3146 |
| language | English |
| last_indexed | 2024-03-09T02:45:43Z |
| publishDate | 2023-11-01 |
| publisher | International Union of Crystallography |
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| spelling | doaj.art-caed76b8b5434ed1b252fa9f00c72e8d2023-12-05T17:03:50ZengInternational Union of CrystallographyIUCrData2414-31462023-11-01811x23101810.1107/S2414314623010180bt4143A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamideAdriano Bof de Oliveira0Leandro Bresolin1Vanessa Carratu Gervini2Johannes Beck3Jörg Daniels4Departamento de Química, Universidade Federal de Sergipe, Av. Marcelo Deda Chagas s/n, Campus Universitário, 49107-230 São Cristóvão-SE, BrazilEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-900 Rio Grande-RS, BrazilEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-900 Rio Grande-RS, BrazilInstitut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, GermanyInstitut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, GermanyA second crystalline modification of the title compound, C12H19N3S [common name: cis-jasmone thiosemicarbazone] was crystallized from tetrahydrofurane at room temperature. There is one crystallographic independent molecule in the asymmetric unit, showing disorder in the cis-jasmone chain [site-occupancy ratio = 0.590 (14):0.410 (14)]. The thiosemicarbazone 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 molecule is not planar due to the dihedral angle between these two fragments, which is 8.93 (1)°, and due to the sp3-hybridized carbon atoms in the jasmone fragment chain. In the crystal, the molecules are connected by N—H...S and C—H...S interactions, with graph-set motifs R22(8) and R21(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 thiosemicarbazone 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.http://scripts.iucr.org/cgi-bin/paper?S2414314623010180jasmone thiosemicarbazonethiosemicarbazonecis-jasmone derivativecrystalline modificationcrystal structurehirshfeld analysis |
| spellingShingle | Adriano Bof de Oliveira Leandro Bresolin Vanessa Carratu Gervini Johannes Beck Jörg Daniels A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide IUCrData jasmone thiosemicarbazone thiosemicarbazone cis-jasmone derivative crystalline modification crystal structure hirshfeld analysis |
| title | A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide |
| title_full | A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide |
| title_fullStr | A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide |
| title_full_unstemmed | A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide |
| title_short | A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide |
| title_sort | second crystalline modification of 2 3 methyl 2 2z pent 2 en 1 yl cyclopent 2 en 1 ylidene hydrazinecarbothioamide |
| topic | jasmone thiosemicarbazone thiosemicarbazone cis-jasmone derivative crystalline modification crystal structure hirshfeld analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2414314623010180 |
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