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Solid-State Dilution of Dihydroxybenzophenones with 4,13-Diaza-18-crown-6 for Photocrystallographic Studies

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Cavendish Laboratory, University of Cambridge, J. J. Thomson Avenue, Cambridge, CB3 0HE, U.K.
Department of Chemistry, University of New Brunswick, P.O. Box 4400, Fredericton, New Brunswick E3B 5A3, Canada
§ School of Biomedical, Biomolecular & Chemical Sciences, University of Western Australia, Crawley, Western Australia, Australia
Cite this: Cryst. Growth Des. 2012, 12, 5, 2277–2287
Publication Date (Web):March 20, 2012
Copyright © 2012 American Chemical Society

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    Abstract Image

    This work forms part of the ongoing drive toward identifying and developing suitable light sensitive substances for photocrystallographic studies. In order to investigate the solid-state dilution of the photoactive dihydroxybenzophenone, X-ray crystal structures of three dihydroxybenzophenone·4,13-diaza-18-crown-6 co-crystals are reported and analyzed. The dihydroxybenzophenone molecules within the co-crystal are compared to those observed in homomolecular dihydroxybenzophenone crystals in terms of their intermolecular contacts, bond geometry and conformation. Molecular volumes and void spaces were calculated using Voronoi–Dirichlet polyhedra and Hirshfeld surface-based space partitioning, demonstrating new ways to represent potential reaction cavities around a photoactive molecule and calculate their packing efficiency. In each case the conditions of solid-state dilution were met. The molecular conformations of the homomolecular environments are retained to varying degrees in the analogous co-crystals. Results show that the co-crystals studied are potentially suitable for photocrystallography. In particular, 2,4-dihydroxybenzophenone molecules in 4,13-diaza-18-crown-6·2(2,4-dihydroxybenzophenone) co-crystals exhibit high structural similarity to their homomolecular analogues suggesting its photochemical properties could be common to both environments.

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