An Acetonitrile-Solvated Coсrystal of Piroxicam and Succinic Acid with Co-Existing Zwitterionic and Non-Ionized Piroxicam Molecules Full article
| Journal |
Acta Crystallographica Section C
, E-ISSN: 2053-2296 |
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| Output data | Year: 2019, Volume: 75, Number: 1, Pages: 29-37 Pages count : 9 DOI: 10.1107/S2053229618016911 | ||||||||
| Tags | piroxicam; succinic acid; crystal structure; cocrystal; solvate | ||||||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Russian Foundation for Basic Research | 17-33-50146 |
Abstract:
This work reports a new acetonitrile (ACN)-solvated cocrystal of piroxicam (PRX) and succinic acid (SA), 2C15H13N3O4S0.5C4H6O4C2H3N or PRX:SA:ACN (4:1:2), which adopts the triclinic space group P1. The outcome of crystallization from ACN solution can be controlled by varying only the PRX:SA ratio, with a higher PRX:SA ratio in solution unexpectedly favouring a lower stoichiometric ratio in the solid product. In the new solvate, zwitterionic (Z) and non-ionized (NI) PRX molecules co-exist in the asymmetric unit. In contrast, the nonsolvated PRX–SA cocrystal contains only NI-type PRX molecules. The ACN molecule entrapped in PRX–SAACN does not form any hydrogen bonds with the surrounding molecules. In the solvated cocrystal, Z-type molecules form dimers linked by intermolecular N—HO hydrogen bonds, whereas every pair of NI-type molecules is linked to SA via N—HO and O—HN hydrogen bonds. Thermogravimetry and differential scanning calorimetry suggest that thermal desolvation of the solvate sample occurs at 148 C, and is followed by recrystallization, presumably of a multicomponent PRX–SA structure. Vibrational spectra (IR and Raman spectroscopy) of PRX–SAACN ACN and PRX–SA are also used to demonstrate the ability of spectroscopic techniques to distinguish between NI- and Z-type PRX molecules in the solid state. Hence, vibrational spectroscopy can be used to distinguish the PRX–SA cocrystal and its ACN solvate
Cite:
Liu X.
, Michalchuk A.A.L.
, Pulham C.R.
, Boldyreva E.V.
An Acetonitrile-Solvated Coсrystal of Piroxicam and Succinic Acid with Co-Existing Zwitterionic and Non-Ionized Piroxicam Molecules
Acta Crystallographica Section C. 2019. V.75. N1. P.29-37. DOI: 10.1107/S2053229618016911 WOS Scopus РИНЦ AN PMID OpenAlex
An Acetonitrile-Solvated Coсrystal of Piroxicam and Succinic Acid with Co-Existing Zwitterionic and Non-Ionized Piroxicam Molecules
Acta Crystallographica Section C. 2019. V.75. N1. P.29-37. DOI: 10.1107/S2053229618016911 WOS Scopus РИНЦ AN PMID OpenAlex
Dates:
| Submitted: | Oct 5, 2018 |
| Accepted: | Nov 28, 2018 |
| Published print: | Jan 1, 2019 |
| Published online: | Jan 1, 2019 |
Identifiers:
| Web of science: | WOS:000454742800005 |
| Scopus: | 2-s2.0-85058039915 |
| Elibrary: | 38655398 |
| Chemical Abstracts: | 2019:13968 |
| PMID: | 30601128 |
| OpenAlex: | W2902878414 |