Formation of Self-Complementary Halogen-Bonded Dimers

Abstract

The X-ray structure of a series of iodo- and bromo-phenylethynylpyridines designed to form self-complementary dimers in the solid state are reported. The perfluoroiodo- and perfluorobromophenylethynyl derivatives, 3-[(2-bromo-3,4,5,6-tetrafluorophenyl)ethynyl]pyridine, 3-[(2,3,4,5-tetrafluoro-6-iodophenyl)ethynyl]pyridine, 2-[(3-bromo-2,4,5,6-tetrafluorophenyl)ethynyl]pyridine, and 2-[(2,4,6-trifluoro-3,5-diiodophenyl)ethynyl]pyridine, formed self-complementary halogen-bonded dimeric units in the solid state. In contrast, 3-[(2-bromo-4,5-difluorophenyl)ethynyl]pyridine formed a C"“H···N hydrogen-bonded dimer.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1021/cg501406w

Publication Date

2015

Journal Title

Crystal growth & design

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