Mapping Out the Molecular Interplay in Monohalobenzene Inclusion Complexes of<i>p</i>-H-calix[5]arene Using Hirshfeld Surfaces

Thomas E. Clark; Mohamed Makha; Alexandre N. Sobolev; Colin L. Raston

doi:10.1021/cg070632y

Abstract

Solid-state inclusion complexes of p-H-calix[5]arene with fluoro-, chloro-, bromo-, and iodobenzene have been structurally authenticated using X-ray diffraction data with a detailed analysis of the Hirshfeld surfaces facilitating an understanding of the type and nature of intermolecular interactions in the supermolecules and extended structures. All but the iodobenzene complexes are isostructural forming columnar arrays involving three crystallographically related 1:1 host–guest supermolecules (halobenzene∩calix[5]arene); three halobenzene molecules from different supermolecules are associated via C−H···X interactions for hydrogen atoms ortho to the halogen atoms, effectively creating a larger cavity from close proximity of three calix[5]arenes. The iodobenzene inclusion complex has sheets of calixarenes rather than columns in the extended packing, presumably due to the increased size of iodine circumventing the formation of the aforementioned interplay of three halobenzene molecules.

Keywords

IodobenzeneChemistryCrystallographyIsostructuralMoleculeIntermolecular forceHalogenSupramolecular chemistryCalixareneHydrogen bondInclusion (mineral)StereochemistryCrystal structureOrganic chemistryMineralogy

Affiliated Institutions

The University of Western Australia AU

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Publication Info

Year: 2008
Type: article
Volume: 8
Issue: 3
Pages: 890-896
Citations: 33
Access: Closed

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APA Style

                            
                                
                                    Thomas E. Clark, 
                                
                                    Mohamed Makha, 
                                
                                    Alexandre N. Sobolev
                                
                                et al.
                            
                            (2008). 
                            Mapping Out the Molecular Interplay in Monohalobenzene Inclusion Complexes of<i>p</i>-H-calix[5]arene Using Hirshfeld Surfaces. 
                            Crystal Growth & Design
                            , 8
                            (3)
                            , 890-896.
                            https://doi.org/10.1021/cg070632y
                        

Identifiers

DOI: 10.1021/cg070632y