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Polymorphism in secondary squaramides: on the importance of π-interactions involving the four membered ring

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Abstract

We report the X-ray solid state structures of four new squaric acid derivatives, i.e. three polymorphs of 3,4-bis((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione (1a–c) and a co-crystal of compound 1 and resorcinol (2). All structures form interesting supramolecular assemblies in the solid state which have been analyzed using high level DFT calculations and molecular electrostatic potential (MEP) surface calculations. A combination of H-bonding and π–π stacking interactions of the cyclobutenedione rings are crucial for the formation of the supramolecular assemblies in the solid state. Moreover, unusual antiparallel CO⋯CO interactions observed in the X-ray structure of one of the polymorphs of 1 and the lp–π interactions between one oxygen atom of resorcinol and the squaramide ring in 2 have been characterized using Bader's theory of “atoms-in-molecules” (AIM).

Graphical abstract: Polymorphism in secondary squaramides: on the importance of π-interactions involving the four membered ring

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Publication details

The article was received on 08 Nov 2017, accepted on 30 Nov 2017 and first published on 01 Dec 2017


Article type: Paper
DOI: 10.1039/C7CE01945A
Citation: CrystEngComm, 2018, Advance Article
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    Polymorphism in secondary squaramides: on the importance of π-interactions involving the four membered ring

    R. Prohens, A. Portell, O. Vallcorba, M. Font-Bardia, A. Bauzá and A. Frontera, CrystEngComm, 2018, Advance Article , DOI: 10.1039/C7CE01945A

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