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Issue 40, 2020
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A new supramolecular heterosynthon [C–I⋯O[double bond, length as m-dash]C(carboxylate)] at work: engineering copper acetate cocrystals

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Abstract

A carboxylate⋯iodine supramolecular heterosynthon can be reliably applied in cocrystal engineering, using metal carboxylates as building blocks. Analysis of the energy framework of the exemplary paddlewheel crystal [Cu(OAc)2MeOH]2 indicates a robust 1D chain and even 2D layer long-range synthon modules, which can be intactly transferred into cocrystals. However, this approach allows the identification of a “weak link” – i.e. layers where the C–H⋯O[double bond, length as m-dash]C hydrogen bonds between ([Cu(OAc)2(MeOH)]2)n polymeric chains will be subject to substitution by I⋯O[double bond, length as m-dash]C halogen bonds during interaction with halogen bond donor co-formers. In contrast to the O–H⋯O[double bond, length as m-dash]C/C–H⋯O[double bond, length as m-dash]C catemeric crystals of pure acetic acid, the crystal design exercise based on the I⋯O[double bond, length as m-dash]C(carboxyl) supramolecular synthon afforded a 1 : 1 cocrystal of 1,4-C6F4I2 and CH3COOH, where the discrete centrosymmetric dimers of acetic acid are stabilized by I⋯O[double bond, length as m-dash]C(carboxyl) halogen bonds.

Graphical abstract: A new supramolecular heterosynthon [C–I⋯O [[double bond, length as m-dash]] C(carboxylate)] at work: engineering copper acetate cocrystals

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Supplementary files

Article information


Submitted
28 Jul 2020
Accepted
31 Aug 2020
First published
01 Sep 2020

CrystEngComm, 2020,22, 6661-6673
Article type
Paper

A new supramolecular heterosynthon [C–I⋯O[double bond, length as m-dash]C(carboxylate)] at work: engineering copper acetate cocrystals

Y. V. Torubaev and I. V. Skabitsky, CrystEngComm, 2020, 22, 6661
DOI: 10.1039/D0CE01093F

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