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Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate

The title compound, C(17)H(27)O(8)P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond ang...

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Detalles Bibliográficos
Autores principales: Schubert, Moritz, Schollmeyer, Dieter, Waldvogel, Siegfried R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186086/
https://www.ncbi.nlm.nih.gov/pubmed/25309241
http://dx.doi.org/10.1107/S1600536814015803
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author Schubert, Moritz
Schollmeyer, Dieter
Waldvogel, Siegfried R.
author_facet Schubert, Moritz
Schollmeyer, Dieter
Waldvogel, Siegfried R.
author_sort Schubert, Moritz
collection PubMed
description The title compound, C(17)H(27)O(8)P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of the sp (3)-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the eth­oxy groups connected to the phospho­rous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three meth­oxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H⋯O=P hydrogen bonds generate R (2) (2)(14) loops. The chosen crystal was modelled as a non-merohedral twin.
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spelling pubmed-41860862014-10-12 Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate Schubert, Moritz Schollmeyer, Dieter Waldvogel, Siegfried R. Acta Crystallogr Sect E Struct Rep Online Data Reports The title compound, C(17)H(27)O(8)P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of the sp (3)-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the eth­oxy groups connected to the phospho­rous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three meth­oxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H⋯O=P hydrogen bonds generate R (2) (2)(14) loops. The chosen crystal was modelled as a non-merohedral twin. International Union of Crystallography 2014-08-01 /pmc/articles/PMC4186086/ /pubmed/25309241 http://dx.doi.org/10.1107/S1600536814015803 Text en © Schubert et al. 2014 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 Data Reports
Schubert, Moritz
Schollmeyer, Dieter
Waldvogel, Siegfried R.
Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title_full Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title_fullStr Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title_full_unstemmed Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title_short Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
title_sort crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186086/
https://www.ncbi.nlm.nih.gov/pubmed/25309241
http://dx.doi.org/10.1107/S1600536814015803
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