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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...

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Autores principales: Paulus, Georgiana, Kwong, Huey Chong, Crouse, Karen A., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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