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Crystal Packing of a Series of 1,2,3,4-Substituted Phenoxazine and Dibenzodioxin Heterocycles

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    Crystal Packing of a Series of 1,2,3,4-Substituted Phenoxazine and Dibenzodioxin Heterocycles
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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2019, 19, 12, 7298–7307
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    https://doi.org/10.1021/acs.cgd.9b01184
    Published October 31, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Understanding and control of weak intermolecular interactions, including π-interactions, is an element toward the strategic design of supramolecular materials. In this work, we describe an approach to promoting cofacial π-stacking in the solid state by preparing polycyclic aromatic compounds that bear complementary electron-rich and electron-poor rings. Specifically, we describe the synthesis and single crystal structures of a series of six dissymmetric systems (three dibenzo-p-dioxins and three phenoxazines) comprised of one electron-rich and one electron-deficient ring. In all cases, anti-co-facial π–π interactions were observed, but no significant C–H···π interactions. These observations were compared with similar structures in the Cambridge Structural Database, and it was found that the presence of bulky substituents, lattice solvent, and stronger intermolecular interactions interfere with efficient π-stacking. Both qualitative and quantitative evaluations of the newly reported structures, and database examples, are included.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.9b01184.

    • Synthetic procedures, NMR, and additional views of X-ray crystallographic structures (PDF)

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    CCDC 1945954–1945959 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 9 publications.

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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2019, 19, 12, 7298–7307
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.9b01184
    Published October 31, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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