Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

Michael A Sinnwell; Jared N Blad; Logan R Thomas; Leonard R MacGillivray

doi:10.1107/S2052252518007583

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Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

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Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

Michael A Sinnwell, Jared N Blad, Logan R Thomas and Leonard R MacGillivray

IUCrJ, Vol.5(Pt 4), pp.491-496

07/01/2018

DOI: 10.1107/S2052252518007583

PMCID: PMC6038960

PMID: 30002849

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Abstract

Halogen bonds have emerged as noncovalent forces that govern the assembly of molecules in organic solids with a degree of reliability akin to hydrogen bonds. Although the structure-directing roles of halogen bonds are often compared to hydrogen bonds, general knowledge concerning the fundamental structural behavior of halogen bonds has had limited opportunity to develop. Following an investigation of solid-state reactions involving organic syntheses and the development of photoresponsive materials, this work demonstrates the ability of the components of intermolecular N⋯I halogen bonding - a 'workhorse' interaction for the crystal engineer - to support a single-crystal-to-single-crystal [2+2] photodimerization. A comparison is provided of the geometric changes experienced by the halogen-bonded components in the single-crystal reaction to the current crystal landscape of N⋯I halogen bonds, as derived from the Cambridge Structural Database. Specifically, a linear-to-bent type of deformation of the halogen-bonded components was observed, which is expected to support the development of functional halogen-bonded materials containing molecules that can undergo movements in close-packed crystal environments.

single-crystal-to-single-crystal reaction

framework-structured solids and amorphous materials

halogen bonds

organic solid-state reactions

molecular crystals

photodimerization

crystal engineering

solid-state reactivity

supramolecular chemistry

co-crystals

Details

Title: Subtitle: Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization
Creators: Michael A Sinnwell - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
Jared N Blad - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
Logan R Thomas - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
Leonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
Resource Type: Journal article
Publication Details: IUCrJ, Vol.5(Pt 4), pp.491-496
DOI: 10.1107/S2052252518007583
PMID: 30002849
PMCID: PMC6038960
NLM abbreviation: IUCrJ
ISSN: 2052-2525
eISSN: 2052-2525
Grant note: DOI: 10.13039/100000086, name: National Science Foundation, Directorate for Mathematical and Physical Sciences, award: DMR-1708673
Language: English
Date published: 07/01/2018
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216595502771

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