Abstract
The title compound, 19 H,79 H-3,5,9,11-tetra-oxa-1,7(2,7)-difluorena-4,10(1,3)-dibenzena-cyclo-dodeca-phane-19,79-dione (fluorenonophane), exists as a solvate with chloro-benzene, C42H28O6·C6H5Cl. The fluorenonophane contains two fluorenone fragments linked by two m-substituted benzene fragments. Some decrease in its macrocyclic cavity leads to a stacking inter-action between the tricyclic fluorenone fragments. In the crystal, the fluorenonophane and chloro-benzene mol-ecules are linked by weak C-H⋯π(ring) inter-actions and C-H⋯Cl hydrogen bonds. The Cl atom of chloro-benzene does not form a halogen bond. A Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the inter-molecular contacts found in the crystal structure.
Highlights
The title compound, 19H,79H-3,5,9,11-tetraoxa-1,7(2,7)-difluorena-4,10(1,3)dibenzenacyclododecaphane-19,79-dione, exists as a solvate with chlorobenzene, C42H28O6ÁC6H5Cl
The fluorenonophane contains two fluorenone fragments linked by two m-substituted benzene fragments
The fluorenonophane and chlorobenzene molecules are linked by weak C—HÁ Á Á(ring) interactions and C—HÁ Á ÁCl hydrogen bonds
Summary
Discovered at the end of the last century, the ability of cyclophanes to form inclusion complexes makes them the central class of synthetic receptors in molecular recognition processes (Diederich, 1991). Particular attention has been paid to the possibility of cationic cyclophanes with box geometries being involved in strong donor–acceptor interactions leading to the formation of ‘guest–host’ complexes with different guests (Dale et al, 2016; Barnes et al, 2013; Gong et al, 2010). X-ray diffraction analysis of this cyclophane revealed the box geometry with an open intramolecular cavity and the formation of inclusion complexes with DMF and nitrobenzene (Simonov et al, 2006). The other fluorenonophane obtained by our group, 2, differs from the previous one in the position of the methylene groups, which are located directly at the benzene fragment in 1 or fluorenone in 2. Continuing our research in this area, we have obtained fluorenonophane 3 with a different position of attachment of the benzene rings compared to 2 (m- and p-isomers, respectively) and studied its complexation with chlorobenzene
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