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3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid
The title molecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydropyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviat...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977273/ https://www.ncbi.nlm.nih.gov/pubmed/21583459 http://dx.doi.org/10.1107/S1600536809024945 |
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author | Wu, De-Hong Hu, Ling |
author_facet | Wu, De-Hong Hu, Ling |
author_sort | Wu, De-Hong |
collection | PubMed |
description | The title molecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydropyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong intermolecular hydrogen bonds. N—H⋯O interactions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain. |
format | Text |
id | pubmed-2977273 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29772732010-12-30 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid Wu, De-Hong Hu, Ling Acta Crystallogr Sect E Struct Rep Online Organic Papers The title molecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydropyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong intermolecular hydrogen bonds. N—H⋯O interactions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain. International Union of Crystallography 2009-07-04 /pmc/articles/PMC2977273/ /pubmed/21583459 http://dx.doi.org/10.1107/S1600536809024945 Text en © Wu and Hu 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 Wu, De-Hong Hu, Ling 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title | 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title_full | 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title_fullStr | 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title_full_unstemmed | 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title_short | 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
title_sort | 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977273/ https://www.ncbi.nlm.nih.gov/pubmed/21583459 http://dx.doi.org/10.1107/S1600536809024945 |
work_keys_str_mv | AT wudehong 35bisethoxycarbonyl26dimethyl14dihydropyridine4carboxylicacid AT huling 35bisethoxycarbonyl26dimethyl14dihydropyridine4carboxylicacid |