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rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate

In the title compound, C(11)H(12)N(4)O(5), the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric inter­actions with the ortho substituents. The hydr­oxy group is involved in bifurcated hydrogen bonds. The first is an...

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Detalles Bibliográficos
Autores principales: Vallat, Olivier, Buciumas, Ana-Maria, Neier, Reinhard, Stoeckli-Evans, Helen
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968186/
https://www.ncbi.nlm.nih.gov/pubmed/21581990
http://dx.doi.org/10.1107/S1600536808043857
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author Vallat, Olivier
Buciumas, Ana-Maria
Neier, Reinhard
Stoeckli-Evans, Helen
author_facet Vallat, Olivier
Buciumas, Ana-Maria
Neier, Reinhard
Stoeckli-Evans, Helen
author_sort Vallat, Olivier
collection PubMed
description In the title compound, C(11)H(12)N(4)O(5), the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric inter­actions with the ortho substituents. The hydr­oxy group is involved in bifurcated hydrogen bonds. The first is an intra­molecular O—H⋯O hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boat-like hydrogen-bonded chelate ring. The second is an inter­molecular O—H⋯N hydrogen bond involving the first N atom of the azide group of a symmetry-related mol­ecule. In the crystal structure this leads to the formation of a polmer chain extending in the c-axis direction.
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spelling pubmed-29681862010-12-30 rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate Vallat, Olivier Buciumas, Ana-Maria Neier, Reinhard Stoeckli-Evans, Helen Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(11)H(12)N(4)O(5), the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric inter­actions with the ortho substituents. The hydr­oxy group is involved in bifurcated hydrogen bonds. The first is an intra­molecular O—H⋯O hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boat-like hydrogen-bonded chelate ring. The second is an inter­molecular O—H⋯N hydrogen bond involving the first N atom of the azide group of a symmetry-related mol­ecule. In the crystal structure this leads to the formation of a polmer chain extending in the c-axis direction. International Union of Crystallography 2009-01-28 /pmc/articles/PMC2968186/ /pubmed/21581990 http://dx.doi.org/10.1107/S1600536808043857 Text en © Vallat 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
Vallat, Olivier
Buciumas, Ana-Maria
Neier, Reinhard
Stoeckli-Evans, Helen
rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title_full rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title_fullStr rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title_full_unstemmed rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title_short rac-Methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
title_sort rac-methyl 4-azido-3-hydr­oxy-3-(2-nitro­phen­yl)butanoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968186/
https://www.ncbi.nlm.nih.gov/pubmed/21581990
http://dx.doi.org/10.1107/S1600536808043857
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