Intermolecular Interactions Drive the Unusual Co-Crystallization of Different Calix[4]arene Conformations

Dominic Taylor; Irene Ling; Filipe Vilela; Scott J. Dalgarno

doi:10.3390/cryst12020250

Intermolecular Interactions Drive the Unusual Co-Crystallization of Different Calix[4]arene Conformations

Dominic Taylor, Irene Ling, Filipe Vilela, Scott J. Dalgarno

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Abstract

Crystallization of 5,17-dibromo-11,27,23,25-tetraone-26,28-dipropoxycalix[4]arene results in the rare observation of two different calix[4]arene conformations (partial cone and 1,3-alternate) co-crystallized within the same single crystal X-ray structure. Analysis using ¹ H and ¹³ C NMR spectroscopy revealed that only a single conformation (the cone) was present in solution, and in contrast to the structures of other reported calix[4]arenes and calix[4]quinones, both conformations of the compound present in this crystal structure have a “pinched” shape, drastically reducing Br-Br separation and associated cavity sizes.

Original language	English
Article number	250
Journal	Crystals
Volume	12
Issue number	2
DOIs	https://doi.org/10.3390/cryst12020250
Publication status	Published - 12 Feb 2022

Keywords

Calix[4]quinone
Conformation
Crystal structure

ASJC Scopus subject areas

Chemical Engineering(all)
Materials Science(all)
Condensed Matter Physics
Inorganic Chemistry

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title = "Intermolecular Interactions Drive the Unusual Co-Crystallization of Different Calix[4]arene Conformations",

abstract = "Crystallization of 5,17-dibromo-11,27,23,25-tetraone-26,28-dipropoxycalix[4]arene results in the rare observation of two different calix[4]arene conformations (partial cone and 1,3-alternate) co-crystallized within the same single crystal X-ray structure. Analysis using 1 H and 13 C NMR spectroscopy revealed that only a single conformation (the cone) was present in solution, and in contrast to the structures of other reported calix[4]arenes and calix[4]quinones, both conformations of the compound present in this crystal structure have a “pinched” shape, drastically reducing Br-Br separation and associated cavity sizes. ",

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N2 - Crystallization of 5,17-dibromo-11,27,23,25-tetraone-26,28-dipropoxycalix[4]arene results in the rare observation of two different calix[4]arene conformations (partial cone and 1,3-alternate) co-crystallized within the same single crystal X-ray structure. Analysis using 1 H and 13 C NMR spectroscopy revealed that only a single conformation (the cone) was present in solution, and in contrast to the structures of other reported calix[4]arenes and calix[4]quinones, both conformations of the compound present in this crystal structure have a “pinched” shape, drastically reducing Br-Br separation and associated cavity sizes.

AB - Crystallization of 5,17-dibromo-11,27,23,25-tetraone-26,28-dipropoxycalix[4]arene results in the rare observation of two different calix[4]arene conformations (partial cone and 1,3-alternate) co-crystallized within the same single crystal X-ray structure. Analysis using 1 H and 13 C NMR spectroscopy revealed that only a single conformation (the cone) was present in solution, and in contrast to the structures of other reported calix[4]arenes and calix[4]quinones, both conformations of the compound present in this crystal structure have a “pinched” shape, drastically reducing Br-Br separation and associated cavity sizes.

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Intermolecular Interactions Drive the Unusual Co-Crystallization of Different Calix[4]arene Conformations

Abstract

Keywords

ASJC Scopus subject areas

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