Table of Contents
Journal of Crystallography
Volume 2014 (2014), Article ID 695701, 7 pages
Research Article

Synthesis and Molecular Structure of 4′,9′,4,9-Tetra-tert-butyl-1′,6′,1,6-tetramethoxy-2,5-dioxa[3.3]metabiphenylophane

Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan

Received 3 September 2014; Accepted 13 October 2014; Published 23 November 2014

Academic Editor: Takashi Mino

Copyright © 2014 Tetsuji Moriguchi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


A large calixarene-like metacyclophane, 4′,9′,4,9-tetra-tert-butyl-1′,6′,1,6-tetramethoxy-2,5-dioxa[3.3]metabiphenylophane, was synthesized by an intermolecular condensation reaction of its corresponding bischloromethyl-biphenyl and bishydroxymethyl-biphenyl precursors. After molecular characterization by 1H NMR spectroscopy and mass spectrometry, the compound generated single crystals by recrystallization from a dichloromethane/hexane mixture, facilitating an exact conformational determination via X-ray diffraction analysis. The crystal was found to belong to the monoclinic space group with cell parameters a = 19.908(2) Å, b = 9.7193(11) Å, c = 23.350(3) Å, β = 109.594(1)°, and  g/cm3 at 90 K. The compound adopted quite strained 1,2-alternate-like conformations because its biphenyl parts displayed large dihedral angles and rigidity. The crystal did not incorporate any solvent molecule but its molecular cavity and crystal space were effectively filled by the substituents.