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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 dihedr...

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Autores principales: Omar, Siti Aminah, Chah, Chee Keong, Ravoof, Thahira B. S. A., Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5956350/
https://www.ncbi.nlm.nih.gov/pubmed/29850067
http://dx.doi.org/10.1107/S2056989018001330
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author Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira B. S. A.
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_facet Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira B. S. A.
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_sort Omar, Siti Aminah
collection PubMed
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.
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spelling pubmed-59563502018-05-30 S-Benzyl 3-[1-(6-methyl­pyridin-2-yl)ethyl­idene]di­thio­carbazate: crystal structure and Hirshfeld surface analysis Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira B. S. A. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications 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 2018-01-31 /pmc/articles/PMC5956350/ /pubmed/29850067 http://dx.doi.org/10.1107/S2056989018001330 Text en © Omar et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira B. S. A.
Jotani, 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5956350/
https://www.ncbi.nlm.nih.gov/pubmed/29850067
http://dx.doi.org/10.1107/S2056989018001330
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