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A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study
The title dithiocarbazate ester (I), C(18)H(18)N(2)S(2) [systematic name: (E)-4-methylbenzyl 2-[(E)-3-phenylallylidene]hydrazinecarbodithioate, comprises an almost planar central CN(2)S(2) residue [r.m.s. deviation = 0.0131 Å]. The methylene(tolyl-4) group forms a dihedral angle of 72.25 (4)...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382618/ https://www.ncbi.nlm.nih.gov/pubmed/28435717 http://dx.doi.org/10.1107/S2056989017003991 |
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author | Yusof, Enis Nadia Md Tahir, Mohamed I. M. Ravoof, Thahira B. S. A. Tan, Sang Loon Tiekink, Edward R. T. |
author_facet | Yusof, Enis Nadia Md Tahir, Mohamed I. M. Ravoof, Thahira B. S. A. Tan, Sang Loon Tiekink, Edward R. T. |
author_sort | Yusof, Enis Nadia Md |
collection | PubMed |
description | The title dithiocarbazate ester (I), C(18)H(18)N(2)S(2) [systematic name: (E)-4-methylbenzyl 2-[(E)-3-phenylallylidene]hydrazinecarbodithioate, comprises an almost planar central CN(2)S(2) residue [r.m.s. deviation = 0.0131 Å]. The methylene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the molecule approximates mirror symmetry with the 4-tolyl group bisected by the plane. The configuration about both double bonds in the N—N=C—C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thioamide synthons, {⋯HNCS}(2), are formed via N—H⋯S(thione) hydrogen bonds. Connections between the dimers via C—H⋯π interactions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an interaction profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N—H⋯S hydrogen bonds is about 0.94 kcal mol(−1) more stable than that in (I). |
format | Online Article Text |
id | pubmed-5382618 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-53826182017-04-21 A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study Yusof, Enis Nadia Md Tahir, Mohamed I. M. Ravoof, Thahira B. S. A. Tan, Sang Loon Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title dithiocarbazate ester (I), C(18)H(18)N(2)S(2) [systematic name: (E)-4-methylbenzyl 2-[(E)-3-phenylallylidene]hydrazinecarbodithioate, comprises an almost planar central CN(2)S(2) residue [r.m.s. deviation = 0.0131 Å]. The methylene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the molecule approximates mirror symmetry with the 4-tolyl group bisected by the plane. The configuration about both double bonds in the N—N=C—C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thioamide synthons, {⋯HNCS}(2), are formed via N—H⋯S(thione) hydrogen bonds. Connections between the dimers via C—H⋯π interactions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an interaction profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N—H⋯S hydrogen bonds is about 0.94 kcal mol(−1) more stable than that in (I). International Union of Crystallography 2017-03-21 /pmc/articles/PMC5382618/ /pubmed/28435717 http://dx.doi.org/10.1107/S2056989017003991 Text en © Yusof et al. 2017 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 Yusof, Enis Nadia Md Tahir, Mohamed I. M. Ravoof, Thahira B. S. A. Tan, Sang Loon Tiekink, Edward R. T. A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title | A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title_full | A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title_fullStr | A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title_full_unstemmed | A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title_short | A cinnamaldehyde Schiff base of S-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study |
title_sort | cinnamaldehyde schiff base of s-(4-methylbenzyl) dithiocarbazate: crystal structure, hirshfeld surface analysis and computational study |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382618/ https://www.ncbi.nlm.nih.gov/pubmed/28435717 http://dx.doi.org/10.1107/S2056989017003991 |
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