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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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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. |
format | Online Article Text |
id | pubmed-4186086 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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