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Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination
In a previous study, the X-ray structure of the title compound, C(9)H(12)N(2)O(7)P(2)·H(2)O, was reported [Takeuchi et al., (1998 ▸). Chem. Pharm. Bull. 46, 1703–1709], but neither atomic coordinates nor details of the geometry were published. The structure has been redetermined with high precision...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4331878/ https://www.ncbi.nlm.nih.gov/pubmed/25705449 http://dx.doi.org/10.1107/S2056989014026863 |
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author | Airoldi, Annalisa Bettoni, Piergiorgio Donnola, Monica Calestani, Gianluca Rizzoli, Corrado |
author_facet | Airoldi, Annalisa Bettoni, Piergiorgio Donnola, Monica Calestani, Gianluca Rizzoli, Corrado |
author_sort | Airoldi, Annalisa |
collection | PubMed |
description | In a previous study, the X-ray structure of the title compound, C(9)H(12)N(2)O(7)P(2)·H(2)O, was reported [Takeuchi et al., (1998 ▸). Chem. Pharm. Bull. 46, 1703–1709], but neither atomic coordinates nor details of the geometry were published. The structure has been redetermined with high precision as its detailed knowledge is essential to elucidate the presumed polymorphism of minodronic acid monohydrate at room temperature. The molecule crystallizes in a zwitterionic form with cationic imidazolium[1,2a]pyridine and anionic phosphonate groups. The dihedral angle formed by the planes of the pyridine and imidazole rings is 3.55 (9)°. A short intramolecular C—H⋯O contact is present. In the crystal, molecules are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds and π–π interactions [centroid-to-centroid distance = 3.5822 (11) Å], forming a three-dimensional structure. |
format | Online Article Text |
id | pubmed-4331878 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-43318782015-02-20 Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination Airoldi, Annalisa Bettoni, Piergiorgio Donnola, Monica Calestani, Gianluca Rizzoli, Corrado Acta Crystallogr E Crystallogr Commun Research Communications In a previous study, the X-ray structure of the title compound, C(9)H(12)N(2)O(7)P(2)·H(2)O, was reported [Takeuchi et al., (1998 ▸). Chem. Pharm. Bull. 46, 1703–1709], but neither atomic coordinates nor details of the geometry were published. The structure has been redetermined with high precision as its detailed knowledge is essential to elucidate the presumed polymorphism of minodronic acid monohydrate at room temperature. The molecule crystallizes in a zwitterionic form with cationic imidazolium[1,2a]pyridine and anionic phosphonate groups. The dihedral angle formed by the planes of the pyridine and imidazole rings is 3.55 (9)°. A short intramolecular C—H⋯O contact is present. In the crystal, molecules are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds and π–π interactions [centroid-to-centroid distance = 3.5822 (11) Å], forming a three-dimensional structure. International Union of Crystallography 2015-01-01 /pmc/articles/PMC4331878/ /pubmed/25705449 http://dx.doi.org/10.1107/S2056989014026863 Text en © Airoldi et al. 2015 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 Airoldi, Annalisa Bettoni, Piergiorgio Donnola, Monica Calestani, Gianluca Rizzoli, Corrado Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title | Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title_full | Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title_fullStr | Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title_full_unstemmed | Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title_short | Crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
title_sort | crystal structure of zwitterionic 3-(2-hydroxy-2-phosphonato-2-phosphonoethyl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4331878/ https://www.ncbi.nlm.nih.gov/pubmed/25705449 http://dx.doi.org/10.1107/S2056989014026863 |
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