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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...

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Autores principales: Airoldi, Annalisa, Bettoni, Piergiorgio, Donnola, Monica, Calestani, Gianluca, Rizzoli, Corrado
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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.
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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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