S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2018
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| Online Access: | http://psasir.upm.edu.my/id/eprint/73830/ http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf |
| _version_ | 1848857372078899200 |
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| author | Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira Begum S. A. Jonita, Mukesh M. Tiekink, Edward R. T. |
| author_facet | Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira Begum S. A. Jonita, Mukesh M. Tiekink, Edward R. T. |
| author_sort | Omar, Siti Aminah |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intramolecular hydrazine-N—H...N(pyridyl) hydrogen bond that closes an S (6) loop. In the crystal, phenyl-C—H...S(thione), methylene-C—H...π(pyridyl), methylene- and phenyl-C—H...π(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-H...H(pyridyl) contact upon the molecular packing. |
| first_indexed | 2025-11-15T11:56:30Z |
| format | Article |
| id | upm-73830 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T11:56:30Z |
| publishDate | 2018 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-738302021-12-02T07:12:08Z http://psasir.upm.edu.my/id/eprint/73830/ S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira Begum S. A. Jonita, Mukesh M. Tiekink, Edward R. T. In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intramolecular hydrazine-N—H...N(pyridyl) hydrogen bond that closes an S (6) loop. In the crystal, phenyl-C—H...S(thione), methylene-C—H...π(pyridyl), methylene- and phenyl-C—H...π(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-H...H(pyridyl) contact upon the molecular packing. International Union of Crystallography 2018 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf Omar, Siti Aminah and Chah, Chee Keong and Ravoof, Thahira Begum S. A. and Jonita, Mukesh M. and Tiekink, Edward R. T. (2018) S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E: Crystallographic Communications, 74. art. no. pt. 2. 261 - 266. ISSN 2056-9890 https://journals.iucr.org/e/issues/2018/02/00/hb7730/ 10.1107/S2056989018001330 |
| spellingShingle | Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira Begum S. A. Jonita, Mukesh M. Tiekink, Edward R. T. S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title | S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title_full | S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title_fullStr | S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title_full_unstemmed | S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title_short | S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis |
| title_sort | s-benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and hirshfeld surface analysis |
| url | http://psasir.upm.edu.my/id/eprint/73830/ http://psasir.upm.edu.my/id/eprint/73830/ http://psasir.upm.edu.my/id/eprint/73830/ http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf |