Issue 21, 2016

Polymorphism in an 18-membered macrocycle: an energetic and topological approach to understand the supramolecular structure

Abstract

The synthesis, crystallization, and theoretical calculations (energetic dimers and QTAIM analyses) of three polymorphs of 3,12-dihydrotetrabenzo[d,h,m,q]-[1–3, 10–12]hexaazacyclooctadeca-1,10-dien-5,14-diyne are reported. The supramolecular cluster approach is proposed for understanding the formation and stabilization of crystal arrangements of the polymorphs. The results show that the π⋯π-interactions were responsible for the crystal packing of the three polymorphs and that they are in a determined energetic region. The energetic difference between the more stable and less stable polymorphs is around 8 kcal mol−1, indicating that if, probably other polymorphs will be formed, all of them will be in the same energetic region. The results confirmed that the first molecular coordination sphere (supramolecular cluster) is the smallest portion of the crystal that represents all necessary energy information for understanding the intermolecular interactions in the entire crystal.

Graphical abstract: Polymorphism in an 18-membered macrocycle: an energetic and topological approach to understand the supramolecular structure

Supplementary files

Article information

Article type
Paper
Submitted
30 Oct 2015
Accepted
20 Apr 2016
First published
22 Apr 2016

CrystEngComm, 2016,18, 3866-3876

Polymorphism in an 18-membered macrocycle: an energetic and topological approach to understand the supramolecular structure

M. A. P. Martins, M. Hörner, J. Beck, A. Z. Tier, A. L. Belladona, A. R. Meyer, N. Zanatta, H. G. Bonacorso and C. P. Frizzo, CrystEngComm, 2016, 18, 3866 DOI: 10.1039/C5CE02123E

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