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3-Methyl­ideneoxolane-2,5-dione

The title compound (itaconic anhydride), C(5)H(4)O(3), consists of a five-membered carbon–oxygen ring in a flat envelope conformation (the unsubstituted C atom being the flap) with three exocyclic double bonds to two O atoms and one C atom. In contrast to the bond lengths, which are very similar to...

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Detalles Bibliográficos
Autores principales: Beginn, Uwe, Frosinn, Martin, Reichelt, Martin, Reuter, Hans
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588448/
https://www.ncbi.nlm.nih.gov/pubmed/23476519
http://dx.doi.org/10.1107/S1600536813002924
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author Beginn, Uwe
Frosinn, Martin
Reichelt, Martin
Reuter, Hans
author_facet Beginn, Uwe
Frosinn, Martin
Reichelt, Martin
Reuter, Hans
author_sort Beginn, Uwe
collection PubMed
description The title compound (itaconic anhydride), C(5)H(4)O(3), consists of a five-membered carbon–oxygen ring in a flat envelope conformation (the unsubstituted C atom being the flap) with three exocyclic double bonds to two O atoms and one C atom. In contrast to the bond lengths, which are very similar to those in itaconic acid in its pure form or in adducts with other mol­ecules, the bond angles differ significantly because of the effect of ring closure giving rise to strong distortions at the C atoms involved in the exocyclic double bonds. In the crystal, C—H⋯O inter­actions link the mol­ecules, forming an extended three-dimensional network.
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spelling pubmed-35884482013-03-08 3-Methyl­ideneoxolane-2,5-dione Beginn, Uwe Frosinn, Martin Reichelt, Martin Reuter, Hans Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (itaconic anhydride), C(5)H(4)O(3), consists of a five-membered carbon–oxygen ring in a flat envelope conformation (the unsubstituted C atom being the flap) with three exocyclic double bonds to two O atoms and one C atom. In contrast to the bond lengths, which are very similar to those in itaconic acid in its pure form or in adducts with other mol­ecules, the bond angles differ significantly because of the effect of ring closure giving rise to strong distortions at the C atoms involved in the exocyclic double bonds. In the crystal, C—H⋯O inter­actions link the mol­ecules, forming an extended three-dimensional network. International Union of Crystallography 2013-02-02 /pmc/articles/PMC3588448/ /pubmed/23476519 http://dx.doi.org/10.1107/S1600536813002924 Text en © Beginn et al. 2013 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
Beginn, Uwe
Frosinn, Martin
Reichelt, Martin
Reuter, Hans
3-Methyl­ideneoxolane-2,5-dione
title 3-Methyl­ideneoxolane-2,5-dione
title_full 3-Methyl­ideneoxolane-2,5-dione
title_fullStr 3-Methyl­ideneoxolane-2,5-dione
title_full_unstemmed 3-Methyl­ideneoxolane-2,5-dione
title_short 3-Methyl­ideneoxolane-2,5-dione
title_sort 3-methyl­ideneoxolane-2,5-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588448/
https://www.ncbi.nlm.nih.gov/pubmed/23476519
http://dx.doi.org/10.1107/S1600536813002924
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