2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide
The hydrochloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenylthiosemicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenylthiosemicarbazone). Concerning the hydrogen bonding, an N—H...N intramolecular interaction is observed, forming a ring with gra...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-11-01
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| Series: | IUCrData |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2414314623009719 |
| _version_ | 1827595006349672448 |
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| author | Adriano Bof Oliveira Leandro Bresolin Johannes Beck Jörg Daniels |
| author_facet | Adriano Bof Oliveira Leandro Bresolin Johannes Beck Jörg Daniels |
| author_sort | Adriano Bof Oliveira |
| collection | DOAJ |
| description | The hydrochloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenylthiosemicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenylthiosemicarbazone). Concerning the hydrogen bonding, an N—H...N intramolecular interaction is observed, forming a ring with graph-set motif S(5). In the crystal, the molecules are connected into centrosymmetric dimers by pairs of N—H...S and C—H...S interactions, forming rings of graph-set motifs R22(8) and R21(7), with the sulfur atoms acting as double acceptors. The thiosemicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0376 (9) Å (the r.m.s.d. amounts to 0.0234 Å). The molecule is substantially twisted as indicated by the dihedral angle between the thiosemicarbazone fragment and the phenyl ring, which amounts to 56.1 (5)°, and because of the jasmone fragment, which bears a chain with sp3-hybridized carbon atoms in the structure. The Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are: H...H (65.3%), H...C/C...H (16.2%), H...S/S...H (10.9%) and H...N/N...H (5.5%). |
| first_indexed | 2024-03-09T02:45:34Z |
| format | Article |
| id | doaj.art-9e30695f57dd4fcdbff1a206e2fb714e |
| institution | Directory Open Access Journal |
| issn | 2414-3146 |
| language | English |
| last_indexed | 2024-03-09T02:45:34Z |
| publishDate | 2023-11-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | IUCrData |
| spelling | doaj.art-9e30695f57dd4fcdbff1a206e2fb714e2023-12-05T17:03:50ZengInternational Union of CrystallographyIUCrData2414-31462023-11-01811x23097110.1107/S2414314623009719bt41422-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamideAdriano Bof Oliveira0Leandro Bresolin1Johannes Beck2Jörg Daniels3Departamento 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, 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, GermanyThe hydrochloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenylthiosemicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenylthiosemicarbazone). Concerning the hydrogen bonding, an N—H...N intramolecular interaction is observed, forming a ring with graph-set motif S(5). In the crystal, the molecules are connected into centrosymmetric dimers by pairs of N—H...S and C—H...S interactions, forming rings of graph-set motifs R22(8) and R21(7), with the sulfur atoms acting as double acceptors. The thiosemicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0376 (9) Å (the r.m.s.d. amounts to 0.0234 Å). The molecule is substantially twisted as indicated by the dihedral angle between the thiosemicarbazone fragment and the phenyl ring, which amounts to 56.1 (5)°, and because of the jasmone fragment, which bears a chain with sp3-hybridized carbon atoms in the structure. The Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are: H...H (65.3%), H...C/C...H (16.2%), H...S/S...H (10.9%) and H...N/N...H (5.5%).http://scripts.iucr.org/cgi-bin/paper?S2414314623009719cis-jasmone4-phenylthiosemicarbazonethiosemicarbazonejasmonecrystal structurehirshfeld analysis. |
| spellingShingle | Adriano Bof Oliveira Leandro Bresolin Johannes Beck Jörg Daniels 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide IUCrData cis-jasmone 4-phenylthiosemicarbazone thiosemicarbazone jasmone crystal structure hirshfeld analysis. |
| title | 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide |
| title_full | 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide |
| title_fullStr | 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide |
| title_full_unstemmed | 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide |
| title_short | 2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-N-phenylhydrazinecarbothioamide |
| title_sort | 2 3 methyl 2 2z pent 2 en 1 yl cyclopent 2 en 1 ylidene n phenylhydrazinecarbothioamide |
| topic | cis-jasmone 4-phenylthiosemicarbazone thiosemicarbazone jasmone crystal structure hirshfeld analysis. |
| url | http://scripts.iucr.org/cgi-bin/paper?S2414314623009719 |
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