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Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate

In the title compound, C(10)H(14)Cl(3)NO(5), the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy­droxy­methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra­molecular hydrogen bonds (O—...

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Autores principales: Oishi, Takeshi, Yasushima, Daichi, Yuasa, Kihiro, Sato, Takaaki, Chida, Noritaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778842/
https://www.ncbi.nlm.nih.gov/pubmed/27006804
http://dx.doi.org/10.1107/S2056989016002474
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author Oishi, Takeshi
Yasushima, Daichi
Yuasa, Kihiro
Sato, Takaaki
Chida, Noritaka
author_facet Oishi, Takeshi
Yasushima, Daichi
Yuasa, Kihiro
Sato, Takaaki
Chida, Noritaka
author_sort Oishi, Takeshi
collection PubMed
description In the title compound, C(10)H(14)Cl(3)NO(5), the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy­droxy­methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra­molecular hydrogen bonds (O—H⋯N and N—H⋯O) between the hy­droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl­prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol­ecules are connected into a dimer by an O—H⋯O hydrogen bond. The dimers are further linked by N—H⋯O, C—H⋯N and C—H⋯O inter­actions, extending a sheet structure parallel to ([Image: see text]01).
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spelling pubmed-47788422016-03-22 Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate Oishi, Takeshi Yasushima, Daichi Yuasa, Kihiro Sato, Takaaki Chida, Noritaka Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(10)H(14)Cl(3)NO(5), the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy­droxy­methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra­molecular hydrogen bonds (O—H⋯N and N—H⋯O) between the hy­droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl­prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol­ecules are connected into a dimer by an O—H⋯O hydrogen bond. The dimers are further linked by N—H⋯O, C—H⋯N and C—H⋯O inter­actions, extending a sheet structure parallel to ([Image: see text]01). International Union of Crystallography 2016-02-17 /pmc/articles/PMC4778842/ /pubmed/27006804 http://dx.doi.org/10.1107/S2056989016002474 Text en © Oishi et al. 2016 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 Research Communications
Oishi, Takeshi
Yasushima, Daichi
Yuasa, Kihiro
Sato, Takaaki
Chida, Noritaka
Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title_full Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title_fullStr Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title_full_unstemmed Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title_short Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
title_sort crystal structure of (+)-methyl (e)-3-[(2s,4s,5r)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778842/
https://www.ncbi.nlm.nih.gov/pubmed/27006804
http://dx.doi.org/10.1107/S2056989016002474
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