Halogen bonding in a series of Br(CF2) n Br–DABCO adducts (n = 4, 6, 8)
- 6 October 2017
- journal article
- research article
- Published by International Union of Crystallography (IUCr) in Acta Crystallographica Section C Structural Chemistry
- Vol. 73 (11), 874-879
- https://doi.org/10.1107/s2053229617013663
Abstract
Halogen bonding (XB) is a highly-directional class of intermolecular interactions that has been used as a powerful tool to drive the design of crystals in the solid phase. To date, the majority of XB donors have been iodine-containing compounds, with many fewer involving brominated analogues. We report the formation of adducts in the vapour phase from a series of dibromoperfluoroalkyl compounds, BrCF2(CF2) n CF2Br (n = 2, 4, 6), and 1,4-diazabicyclo[2.2.2]octane (DABCO). Single-crystal X-ray diffraction studies of the colourless crystals identified 1,4-diazabicyclo[2.2.2]octane–1,4-dibromoperfluorobutane (1/1), C4Br2F8·C6H12N2, (I), 1,4-diazabicyclo[2.2.2]octane–1,6-dibromoperfluorohexane (1/1), C6Br2F12·C6H12N2, (II), and 1,4-diazabicyclo[2.2.2]octane–1,8-dibromoperfluorooctane (1/1), C8Br2F16·C6H12N2, (III), each of which displays a one-dimensional halogen-bonded network. All three adducts exhibit N...Br distances less than the sum of the van der Waals radii, with butane analogue (I) showing the shortest N...Br halogen-bond distances yet reported between a bromoperfluorocarbon and a nitrogen base [2.809 (3) and 2.818 (3) Å], which are 0.58 and 0.59 Å shorter than the sum of the van der Waals radii.Keywords
This publication has 32 references indexed in Scilit:
- Halogen-bonded adduct of 1,2-dibromo-1,1,2,2-tetrafluoroethane and 1,4-diazabicyclo[2.2.2]octaneActa Crystallographica Section C Structural Chemistry, 2015
- Stabilizing volatile liquid chemicals using co-crystallizationChemical Communications, 2015
- Establishing a Hierarchy of Halogen Bonding by Engineering Crystals without DisorderCrystal Growth & Design, 2013
- Crystal engineering: A brief overviewJournal of Chemical Sciences, 2010
- Halogen bonding: a general route in anion recognition and coordinationChemical Society Reviews, 2010
- New software for searching the Cambridge Structural Database and visualizing crystal structuresActa crystallographica Section B, Structural science, crystal engineering and materials, 2002
- The N⋯I Intermolecular Interaction as a General Protocol for the Formation of Perfluorocarbon–Hydrocarbon Supramolecular Architectures 1Tetrahedron, 2000
- Perfluorocarbon-hydrocarbon self-assembly. Part 6:1 α,ω-Diiodoperfluoroalkanes as pseudohalogens in supramolecular synthesisTetrahedron Letters, 1999
- Charge-transfer interactions of amines with tetrahalomethanes. X-ray crystal structures of the donor-acceptor complexes of quinuclidine and diazabicyclo [2.2.2]octane with carbon tetrabromideThe Journal of Organic Chemistry, 1987
- van der Waals Volumes and RadiiThe Journal of Physical Chemistry, 1964