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S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis


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


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.

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Additional Metadata

Item Type: Article
Divisions: Faculty of Science
DOI Number: https://doi.org/10.1107/S2056989018001330
Publisher: International Union of Crystallography
Keywords: Crystal structure; Di­thio­carbazate ester; Hydrogen bonding; Hirshfeld surface analysis
Depositing User: Ms. Nida Hidayati Ghazali
Date Deposited: 02 Dec 2021 07:12
Last Modified: 02 Dec 2021 07:12
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1107/S2056989018001330
URI: http://psasir.upm.edu.my/id/eprint/73830
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