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Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol
Each of the title dis-symmetric di-Schiff base compounds, C(15)H(12)Cl(2)N(2)O(2) (I) and C(14)H(9)BrCl(2)N(2)O (II), features a central azo-N—N bond connecting two imine groups, each with an E-configuration. One imine bond in each molecule connects to a 2,6-dichlorobenzene substituent while the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7274017/ https://www.ncbi.nlm.nih.gov/pubmed/32523754 http://dx.doi.org/10.1107/S2056989020006416 |
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author | Manawar, Rohit B. Pashavan, Chandankumar T. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Manawar, Rohit B. Pashavan, Chandankumar T. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Manawar, Rohit B. |
collection | PubMed |
description | Each of the title dis-symmetric di-Schiff base compounds, C(15)H(12)Cl(2)N(2)O(2) (I) and C(14)H(9)BrCl(2)N(2)O (II), features a central azo-N—N bond connecting two imine groups, each with an E-configuration. One imine bond in each molecule connects to a 2,6-dichlorobenzene substituent while the other links a 2-hydroxyl-3-methoxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each molecule features an intramolecular hydroxyl-O—H⋯N(imine) hydrogen bond. The C—N—N—C torsion angles of −151.0 (3)° for (I) and 177.8 (6)° (II) indicates a significant twist in the former. The common feature of the molecular packing is the formation of supramolecular chains. In (I), the linear chains are aligned along the a-axis direction and the molecules are linked by methoxy-C—H⋯O(methoxy) and chlorobenzene-C—Cl⋯π(chlorobenzene) interactions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br⋯O [3.132 (4) Å] secondary bonding interactions. In each crystal, the chains pack without directional interactions between them. The non-covalent interactions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to the identified intermolecular interactions in each of (I) and (II). |
format | Online Article Text |
id | pubmed-7274017 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-72740172020-06-09 Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol Manawar, Rohit B. Pashavan, Chandankumar T. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications Each of the title dis-symmetric di-Schiff base compounds, C(15)H(12)Cl(2)N(2)O(2) (I) and C(14)H(9)BrCl(2)N(2)O (II), features a central azo-N—N bond connecting two imine groups, each with an E-configuration. One imine bond in each molecule connects to a 2,6-dichlorobenzene substituent while the other links a 2-hydroxyl-3-methoxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each molecule features an intramolecular hydroxyl-O—H⋯N(imine) hydrogen bond. The C—N—N—C torsion angles of −151.0 (3)° for (I) and 177.8 (6)° (II) indicates a significant twist in the former. The common feature of the molecular packing is the formation of supramolecular chains. In (I), the linear chains are aligned along the a-axis direction and the molecules are linked by methoxy-C—H⋯O(methoxy) and chlorobenzene-C—Cl⋯π(chlorobenzene) interactions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br⋯O [3.132 (4) Å] secondary bonding interactions. In each crystal, the chains pack without directional interactions between them. The non-covalent interactions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to the identified intermolecular interactions in each of (I) and (II). International Union of Crystallography 2020-05-19 /pmc/articles/PMC7274017/ /pubmed/32523754 http://dx.doi.org/10.1107/S2056989020006416 Text en © Manawar 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 Manawar, Rohit B. Pashavan, Chandankumar T. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title | Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title_full | Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title_fullStr | Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title_full_unstemmed | Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title_short | Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
title_sort | crystal structures of two dis-symmetric di-schiff base compounds: 2-({(e)-2-[(e)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(e)-2-[(e)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7274017/ https://www.ncbi.nlm.nih.gov/pubmed/32523754 http://dx.doi.org/10.1107/S2056989020006416 |
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