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1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide

In the title resonance conformer, C(15)H(12)ClNO(4), the central C–N bond [1.297 (2) Å] has considerable double-bond character and the N–O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the mol­ecule, with both benze...

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Autores principales: Skakle, Janet M. S., Tiekink, Edward R. T., Wardell, James L., Wardell, Solange M. S. V.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980074/
https://www.ncbi.nlm.nih.gov/pubmed/21580149
http://dx.doi.org/10.1107/S160053680905137X
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author Skakle, Janet M. S.
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author_facet Skakle, Janet M. S.
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author_sort Skakle, Janet M. S.
collection PubMed
description In the title resonance conformer, C(15)H(12)ClNO(4), the central C–N bond [1.297 (2) Å] has considerable double-bond character and the N–O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the mol­ecule, with both benzene rings twisted out of the central C–C–N–C plane [the dihedral angle formed between the rings = 81.99 (8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of the benzene ring to which it is connected [C—C—O—C torsion angle = −78.42 (17)°]. The most prominent inter­molecular inter­actions involve the carboxylic acid the N(+)–O(−) residues with the O—H⋯O hydrogen bonds leading to helical supra­molecular chains along the b axis. These chains are connected into layers via C–H⋯O(carbon­yl) inter­actions and the layers are consolidated into the crystal structure by C–H⋯Cl contacts.
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spelling pubmed-29800742010-12-30 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide Skakle, Janet M. S. Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title resonance conformer, C(15)H(12)ClNO(4), the central C–N bond [1.297 (2) Å] has considerable double-bond character and the N–O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the mol­ecule, with both benzene rings twisted out of the central C–C–N–C plane [the dihedral angle formed between the rings = 81.99 (8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of the benzene ring to which it is connected [C—C—O—C torsion angle = −78.42 (17)°]. The most prominent inter­molecular inter­actions involve the carboxylic acid the N(+)–O(−) residues with the O—H⋯O hydrogen bonds leading to helical supra­molecular chains along the b axis. These chains are connected into layers via C–H⋯O(carbon­yl) inter­actions and the layers are consolidated into the crystal structure by C–H⋯Cl contacts. International Union of Crystallography 2009-12-04 /pmc/articles/PMC2980074/ /pubmed/21580149 http://dx.doi.org/10.1107/S160053680905137X Text en © Skakle et al. 2010 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 Organic Papers
Skakle, Janet M. S.
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title_full 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title_fullStr 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title_full_unstemmed 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title_short 1-[2-(Carboxy­meth­oxy)phen­yl]-N-(4-chloro­phen­yl)methanimine oxide
title_sort 1-[2-(carboxy­meth­oxy)phen­yl]-n-(4-chloro­phen­yl)methanimine oxide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980074/
https://www.ncbi.nlm.nih.gov/pubmed/21580149
http://dx.doi.org/10.1107/S160053680905137X
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