Fine-tuning of biaryl dihedral angles: Structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography

David J. Edwards, Robin G. Pritchard, Timothy W. Wallace

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    Abstract

    The homologous series of three-atom bridged biaryls comprising 5,7-dihydro-1 ,2,3,9,10,11-hexamethoxydibenzo-[c,e]oxepine, 6,7-dihydro-1,2,3,9, 10,11-hexamethoxy-6-methyl-5H-dibenzo[c,e]azepinium chloride, 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]thiepine, and the 6-oxide and 6,6-dioxide derivatives of the latter have been characterized by X-ray crystal structure analysis. Within this series the endocyclic and exocyclic biaryl dihedral angles vary over 10° ranges, reflecting the changing balance of intramolecular (steric, geometric) and intermolecular (crystal packing) forces, the former being potential control elements for fine-tuning the helicity of the biaryl system. © 2005 International Union of Crystallography Printed in Great Britain - all rights reserved.
    Original languageEnglish
    Pages (from-to)335-345
    Number of pages10
    JournalActa Crystallographica Section B: Structural Science
    Volume61
    Issue number3
    DOIs
    Publication statusPublished - Jun 2005

    Keywords

    • Bond angle (dihedral; fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by x-ray crystallog.); Crystal structure; Molecular structure (of dihydrohexamethoxydibenzooxepine, dihydrohexamethoxymethyldibenzoazepinium chloride, dihydrohexamethoxydibenzothiepine and its oxide and dioxide)

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