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Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline

The hydrated and anhydrous 1:2 cocrystals of oxyresveratrol (4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol; OXY; C(14)H(12)O(4)) and proline [(S)-pyrrolidine-2-carb­oxy­lic acid; PRO; C(5)H(9)NO(2)], namely, 4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol bis­[(S)-pyrrolidin-...

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Autores principales: Ouiyangkul, Passaporn, Saithong, Saowanit, Tantishaiyakul, Vimon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472756/
https://www.ncbi.nlm.nih.gov/pubmed/32939313
http://dx.doi.org/10.1107/S2056989020011536
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author Ouiyangkul, Passaporn
Saithong, Saowanit
Tantishaiyakul, Vimon
author_facet Ouiyangkul, Passaporn
Saithong, Saowanit
Tantishaiyakul, Vimon
author_sort Ouiyangkul, Passaporn
collection PubMed
description The hydrated and anhydrous 1:2 cocrystals of oxyresveratrol (4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol; OXY; C(14)H(12)O(4)) and proline [(S)-pyrrolidine-2-carb­oxy­lic acid; PRO; C(5)H(9)NO(2)], namely, 4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol bis­[(S)-pyrrolidin-1-ium-2-carboxyl­ate] monohydrate, C(14)H(12)O(4)·2C(5)H(9)NO(2)·H(2)O, and the anhydrous form, C(14)H(12)O(4)·2C(5)H(9)NO(2), were obtained by crystallization at different temperatures. Both of them crystallize with ortho­rhom­bic (P2(1)2(1)2(1)) symmetry. The structures display N—H⋯O and O—H⋯O hydrogen-bonding inter­actions between PRO and PRO, OXY and OXY, and OXY and PRO. In the hydrated cocrystal, these types of contacts are also observed between the OXY, PRO and water mol­ecules. A combination of these inter­actions leads to a three-dimensional supra­molecular assembly in each case. Hirshfeld surfaces were used to gain further insight into the inter­molecular inter­actions in the packing, including the relative percentage contributions of the significant inter­molecular H⋯H and H⋯O/O⋯H contacts.
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spelling pubmed-74727562020-09-15 Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline Ouiyangkul, Passaporn Saithong, Saowanit Tantishaiyakul, Vimon Acta Crystallogr E Crystallogr Commun Research Communications The hydrated and anhydrous 1:2 cocrystals of oxyresveratrol (4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol; OXY; C(14)H(12)O(4)) and proline [(S)-pyrrolidine-2-carb­oxy­lic acid; PRO; C(5)H(9)NO(2)], namely, 4-[(E)-2-(3,5-di­hydroxy­phen­yl)ethen­yl]benzene-1,3-diol bis­[(S)-pyrrolidin-1-ium-2-carboxyl­ate] monohydrate, C(14)H(12)O(4)·2C(5)H(9)NO(2)·H(2)O, and the anhydrous form, C(14)H(12)O(4)·2C(5)H(9)NO(2), were obtained by crystallization at different temperatures. Both of them crystallize with ortho­rhom­bic (P2(1)2(1)2(1)) symmetry. The structures display N—H⋯O and O—H⋯O hydrogen-bonding inter­actions between PRO and PRO, OXY and OXY, and OXY and PRO. In the hydrated cocrystal, these types of contacts are also observed between the OXY, PRO and water mol­ecules. A combination of these inter­actions leads to a three-dimensional supra­molecular assembly in each case. Hirshfeld surfaces were used to gain further insight into the inter­molecular inter­actions in the packing, including the relative percentage contributions of the significant inter­molecular H⋯H and H⋯O/O⋯H contacts. International Union of Crystallography 2020-08-28 /pmc/articles/PMC7472756/ /pubmed/32939313 http://dx.doi.org/10.1107/S2056989020011536 Text en © Ouiyangkul et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Ouiyangkul, Passaporn
Saithong, Saowanit
Tantishaiyakul, Vimon
Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title_full Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title_fullStr Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title_full_unstemmed Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title_short Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
title_sort syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472756/
https://www.ncbi.nlm.nih.gov/pubmed/32939313
http://dx.doi.org/10.1107/S2056989020011536
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