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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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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. |
format | Text |
id | pubmed-2968512 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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