Pallipurath, AR orcid.org/0000-0002-9778-5160, Civati, F, Eziashi, M et al. (3 more authors) (2016) Tailoring Cocrystal and Salt Formation and Controlling the Crystal Habit of Diflunisal. Crystal Growth & Design, 16 (11). pp. 6468-6478. ISSN 1528-7483
Abstract
Crystal habit modification of the drug diflunisal that normally grows into extremely thin, long needles has been achieved by breaking the stacking effect with the help of coformers. Eight new cocrystals are reported, along with three crystal structures. In all cases, ortho F disorder, often a feature in diflunisal structures was absent due to the presence of CH···F interactions. Co-milling diflunisal with oxalic acid produced 1:1 and 2:1 cocrystals. In contrast, in solution crystallization, oxalic acid played the role of an additive resulting in the crystallization of diflunisal form I rather than form III. To rationalize cocrystal formation, a statistical analysis of the Cambridge Crystallographic Data Centre database for aromatic o-hydroxy carboxylic acids was carried out. All cocrystals of o-hydroxy carboxylic acids with the COOH dimer motif have an electron-withdrawing group on one of the acids. COOH···Nar motifs are formed preferentially over carboxylic homodimers in the presence of an Nar coformer.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemical & Process Engineering (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 18 Feb 2020 13:52 |
Last Modified: | 18 Feb 2020 13:52 |
Status: | Published |
Publisher: | American Chemical Society (ACS) |
Identification Number: | 10.1021/acs.cgd.6b01154 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:157235 |