Systematic coformer contribution to cocrystal stabilization: energy and packing trends

Polycyclic aromatic compounds such as acridine and phenazine are popular molecular partners used in cocrystal synthesis. The intermolecular interactions occurring between coformers and their molecular partners dominate the cocrystal packing energy, but coformer self-interactions might participate wi...

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Bibliographic Details
Published in:CrystEngComm 2020-11, Vol.22 (43), p.7341-7349
Main Authors: Mazzeo, Paolo P, Canossa, Stefano, Carraro, Claudia, Pelagatti, Paolo, Bacchi, Alessia
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Crystallography
Stabilization
Statistical analysis
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Summary:Polycyclic aromatic compounds such as acridine and phenazine are popular molecular partners used in cocrystal synthesis. The intermolecular interactions occurring between coformers and their molecular partners dominate the cocrystal packing energy, but coformer self-interactions might participate with a constant non-negligible contribution to the overall packing energy stabilization. Two new acridine-based cocrystals have been mechanochemically synthesized, then fully characterized via DSC and SCXRD analyses. A statistical analysis in the CSD has been performed to evaluate the recurrent π-π stacking orientation of polycyclic coformers in all deposited acridine-based cocrystals, then extended to phenazine-base analogs. Packing energy calculations were performed on a selected cocrystal subset to quantify the contribution of the π-π interaction to the overall stabilization energy. CSD data mining and energy calculations show that coformer self-interactions might significantly contribute to the packing energy stabilization of cocrystals.
ISSN:1466-8033
1466-8033
DOI:10.1039/d0ce00291g