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3-(2-Acetamido­phen­yl)sydnone

Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C(10)H(9)N(3)O(3), the aromatic substitutent is 2-acetamido­phenyl. The two planar ring fragme...

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Detalles Bibliográficos
Autores principales: Grossie, David A., Turnbull, Kenneth, Felix-Balderrama, Sandra, Raghavapuram, Shravanthi
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968512/
https://www.ncbi.nlm.nih.gov/pubmed/21582213
http://dx.doi.org/10.1107/S1600536809005066
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author Grossie, David A.
Turnbull, Kenneth
Felix-Balderrama, Sandra
Raghavapuram, Shravanthi
author_facet Grossie, David A.
Turnbull, Kenneth
Felix-Balderrama, Sandra
Raghavapuram, Shravanthi
author_sort Grossie, David A.
collection PubMed
description Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C(10)H(9)N(3)O(3), the aromatic substitutent is 2-acetamido­phenyl. The two planar ring fragments are twisted relative to one another, with a inter­planar angle of 63.13 (5)°. The mol­ecules are packed into the unit cell via π–π inter­actions between the phenyl rings [inter­planar separation = 3.4182 (4) Å] and between the sydnone rings [inter­planar separation = 3.2095 (4) Å]. N—H⋯O and C—H⋯O hydrogen bonding is also found inter­nally and externally to the mol­ecule.
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spelling pubmed-29685122010-12-30 3-(2-Acetamido­phen­yl)sydnone Grossie, David A. Turnbull, Kenneth Felix-Balderrama, Sandra Raghavapuram, Shravanthi Acta Crystallogr Sect E Struct Rep Online Organic Papers Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C(10)H(9)N(3)O(3), the aromatic substitutent is 2-acetamido­phenyl. The two planar ring fragments are twisted relative to one another, with a inter­planar angle of 63.13 (5)°. The mol­ecules are packed into the unit cell via π–π inter­actions between the phenyl rings [inter­planar separation = 3.4182 (4) Å] and between the sydnone rings [inter­planar separation = 3.2095 (4) Å]. N—H⋯O and C—H⋯O hydrogen bonding is also found inter­nally and externally to the mol­ecule. International Union of Crystallography 2009-02-21 /pmc/articles/PMC2968512/ /pubmed/21582213 http://dx.doi.org/10.1107/S1600536809005066 Text en © Grossie et al. 2009 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
Grossie, David A.
Turnbull, Kenneth
Felix-Balderrama, Sandra
Raghavapuram, Shravanthi
3-(2-Acetamido­phen­yl)sydnone
title 3-(2-Acetamido­phen­yl)sydnone
title_full 3-(2-Acetamido­phen­yl)sydnone
title_fullStr 3-(2-Acetamido­phen­yl)sydnone
title_full_unstemmed 3-(2-Acetamido­phen­yl)sydnone
title_short 3-(2-Acetamido­phen­yl)sydnone
title_sort 3-(2-acetamido­phen­yl)sydnone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968512/
https://www.ncbi.nlm.nih.gov/pubmed/21582213
http://dx.doi.org/10.1107/S1600536809005066
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