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2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis
The title dithiocarbazate ester, C(16)H(16)N(2)O(2)S(2), comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine)...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4910345/ https://www.ncbi.nlm.nih.gov/pubmed/27375879 http://dx.doi.org/10.1107/S2056989016004291 |
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author | Yusof, Enis Nadia Md Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
author_facet | Yusof, Enis Nadia Md Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
author_sort | Yusof, Enis Nadia Md |
collection | PubMed |
description | The title dithiocarbazate ester, C(16)H(16)N(2)O(2)S(2), comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H⋯S hydrogen bonds leading to eight-membered {⋯HNCS}(2) synthons in the crystal. These aggregates are connected by phenyl-C—H⋯O(hydroxy) interactions into a supramolecular layer in the bc plane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions. |
format | Online Article Text |
id | pubmed-4910345 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49103452016-07-01 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis Yusof, Enis Nadia Md Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. Acta Crystallogr E Crystallogr Commun Research Communications The title dithiocarbazate ester, C(16)H(16)N(2)O(2)S(2), comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H⋯S hydrogen bonds leading to eight-membered {⋯HNCS}(2) synthons in the crystal. These aggregates are connected by phenyl-C—H⋯O(hydroxy) interactions into a supramolecular layer in the bc plane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions. International Union of Crystallography 2016-03-18 /pmc/articles/PMC4910345/ /pubmed/27375879 http://dx.doi.org/10.1107/S2056989016004291 Text en © Yusof et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Yusof, Enis Nadia Md Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title_full | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title_fullStr | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title_short | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
title_sort | 2-[(1e)-({[(benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4910345/ https://www.ncbi.nlm.nih.gov/pubmed/27375879 http://dx.doi.org/10.1107/S2056989016004291 |
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