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Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate
The title compound (systematic name: 4,7-methano-2,2′-spirobi[1,3-benzodioxole]), C(14)H(14)O(4), is an asymmetric spiro ester of orthocarbonic acid and two diols, viz. the aromatic benzene-1,2-diol and the aliphatic vicinal norbornane-exo-cis-2,3-diol. The orthocarbonate molecule is close to havi...
Autores principales: | , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960339/ https://www.ncbi.nlm.nih.gov/pubmed/21201427 http://dx.doi.org/10.1107/S1600536807063660 |
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author | Betz, Richard Klüfers, Peter |
author_facet | Betz, Richard Klüfers, Peter |
author_sort | Betz, Richard |
collection | PubMed |
description | The title compound (systematic name: 4,7-methano-2,2′-spirobi[1,3-benzodioxole]), C(14)H(14)O(4), is an asymmetric spiro ester of orthocarbonic acid and two diols, viz. the aromatic benzene-1,2-diol and the aliphatic vicinal norbornane-exo-cis-2,3-diol. The orthocarbonate molecule is close to having non-crystallographic C (s) symmetry. The five-membered ring stemming from the aliphatic diol has an envelope conformation. C—O bonds including the spiro-C atom span an approximately 0.07 Å range, but are within 0.02 Å of the respective distances in a density functional theory calculation, i.e. the distance difference is not caused by packing forces. Accordingly, the crystal packing is characterized by weak C—H⋯O and C—H⋯π interactions. |
format | Text |
id | pubmed-2960339 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29603392010-12-30 Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate Betz, Richard Klüfers, Peter Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (systematic name: 4,7-methano-2,2′-spirobi[1,3-benzodioxole]), C(14)H(14)O(4), is an asymmetric spiro ester of orthocarbonic acid and two diols, viz. the aromatic benzene-1,2-diol and the aliphatic vicinal norbornane-exo-cis-2,3-diol. The orthocarbonate molecule is close to having non-crystallographic C (s) symmetry. The five-membered ring stemming from the aliphatic diol has an envelope conformation. C—O bonds including the spiro-C atom span an approximately 0.07 Å range, but are within 0.02 Å of the respective distances in a density functional theory calculation, i.e. the distance difference is not caused by packing forces. Accordingly, the crystal packing is characterized by weak C—H⋯O and C—H⋯π interactions. International Union of Crystallography 2008-01-09 /pmc/articles/PMC2960339/ /pubmed/21201427 http://dx.doi.org/10.1107/S1600536807063660 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html. |
spellingShingle | Organic Papers Betz, Richard Klüfers, Peter Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title | Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title_full | Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title_fullStr | Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title_full_unstemmed | Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title_short | Norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
title_sort | norbornane-exo-cis-2,3-diyl 1′,2′-phenylene orthocarbonate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960339/ https://www.ncbi.nlm.nih.gov/pubmed/21201427 http://dx.doi.org/10.1107/S1600536807063660 |
work_keys_str_mv | AT betzrichard norbornaneexocis23diyl12phenyleneorthocarbonate AT kluferspeter norbornaneexocis23diyl12phenyleneorthocarbonate |