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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...

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Autores principales: Manawar, Rohit B., Pashavan, Chandankumar T., Shah, Manish K., Jotani, Mukesh M., 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/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).
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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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