Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization
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 str...
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doaj-8497579608094c828c33740c73308acf2020-11-24T21:22:58ZengInternational Union of CrystallographyIUCrJ2052-25252018-07-015449149610.1107/S2052252518007583ed5014Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerizationMichael A. Sinnwell0Jared N. Blad1Logan R. Thomas2Leonard R. MacGillivray3Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USADepartment of Chemistry, University of Iowa, Iowa City, Iowa 52242, USADepartment of Chemistry, University of Iowa, Iowa City, Iowa 52242, USADepartment of Chemistry, University of Iowa, Iowa City, Iowa 52242, USAHalogen 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.http://scripts.iucr.org/cgi-bin/paper?S2052252518007583solid-state reactivityhalogen bondsphotodimerizationsupramolecular chemistrysingle-crystal-to-single-crystal reactioncrystal engineeringco-crystalsorganic solid-state reactionsframework-structured solids and amorphous materialsmolecular crystals |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Michael A. Sinnwell Jared N. Blad Logan R. Thomas Leonard R. MacGillivray |
spellingShingle |
Michael A. Sinnwell Jared N. Blad Logan R. Thomas Leonard R. MacGillivray Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization IUCrJ solid-state reactivity halogen bonds photodimerization supramolecular chemistry single-crystal-to-single-crystal reaction crystal engineering co-crystals organic solid-state reactions framework-structured solids and amorphous materials molecular crystals |
author_facet |
Michael A. Sinnwell Jared N. Blad Logan R. Thomas Leonard R. MacGillivray |
author_sort |
Michael A. Sinnwell |
title |
Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
title_short |
Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
title_full |
Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
title_fullStr |
Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
title_full_unstemmed |
Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
title_sort |
structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization |
publisher |
International Union of Crystallography |
series |
IUCrJ |
issn |
2052-2525 |
publishDate |
2018-07-01 |
description |
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. |
topic |
solid-state reactivity halogen bonds photodimerization supramolecular chemistry single-crystal-to-single-crystal reaction crystal engineering co-crystals organic solid-state reactions framework-structured solids and amorphous materials molecular crystals |
url |
http://scripts.iucr.org/cgi-bin/paper?S2052252518007583 |
work_keys_str_mv |
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