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2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study
The complete molecule of the title hydrazine carbodithioate derivative, C(32)H(30)N(4)O(2)S(4), is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)° indicating an orthogonal relatio...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405575/ https://www.ncbi.nlm.nih.gov/pubmed/32844007 http://dx.doi.org/10.1107/S2056989020008762 |
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author | Paulus, Georgiana Kwong, Huey Chong Crouse, Karen A. Tiekink, Edward R. T. |
author_facet | Paulus, Georgiana Kwong, Huey Chong Crouse, Karen A. Tiekink, Edward R. T. |
author_sort | Paulus, Georgiana |
collection | PubMed |
description | The complete molecule of the title hydrazine carbodithioate derivative, C(32)H(30)N(4)O(2)S(4), is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN(2)C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = −166.57 (15)°]. An intramolecular hydroxyl-O—H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H⋯π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H⋯H contacts, which contribute 46.7% of all contacts followed by H⋯C/C⋯H contacts [25.5%] reflecting, in part, the C—H⋯π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H⋯H contacts in the inter-layer region. |
format | Online Article Text |
id | pubmed-7405575 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-74055752020-08-24 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study Paulus, Georgiana Kwong, Huey Chong Crouse, Karen A. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The complete molecule of the title hydrazine carbodithioate derivative, C(32)H(30)N(4)O(2)S(4), is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN(2)C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = −166.57 (15)°]. An intramolecular hydroxyl-O—H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H⋯π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H⋯H contacts, which contribute 46.7% of all contacts followed by H⋯C/C⋯H contacts [25.5%] reflecting, in part, the C—H⋯π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H⋯H contacts in the inter-layer region. International Union of Crystallography 2020-07-10 /pmc/articles/PMC7405575/ /pubmed/32844007 http://dx.doi.org/10.1107/S2056989020008762 Text en © Paulus et al. 2020 http://creativecommons.org/licenses/by/4.0/ 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/4.0/ |
spellingShingle | Research Communications Paulus, Georgiana Kwong, Huey Chong Crouse, Karen A. Tiekink, Edward R. T. 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title_full | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title_fullStr | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title_full_unstemmed | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title_short | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
title_sort | 2-[(1e)-[(z)-2-({[(1z)-[(e)-2-[(2-hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, hirshfeld surface analysis and computational study |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405575/ https://www.ncbi.nlm.nih.gov/pubmed/32844007 http://dx.doi.org/10.1107/S2056989020008762 |
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