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The monosubstituted derivative 4-ethynyl[2.2]paracyclo­phane, C18H16, (I), and the four disubstituted isomers, 4,12-, (II), 4,13-, (III), 4,15-, (IV), and 4,16-diethynyl[2.2]paracyclo­phane, (V), all C20H16, show the usual distortions of the [2.2]paracyclo­phane framework. The crystal packing is analyzed in terms of C—H...π inter­actions, some with H...π as short as 2.47 Å, in which the cyclo­phane rings and/or the triple-bond systems may act as acceptors. For compounds (I) and (IV), the known `7,11'-type cyclo­phane packing is observed, with a herring-bone pattern of mol­ecules in a layer structure.

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In the title compound, C18H16, the [2.2]paracyclo­phane geometry is restrained to a considerable extent despite the introduction of the extra C=C bridge; typical paracyclo­phane features, such as the elongated C-C bridges, are still observed. However, the bridgehead atoms of the C=C bridge are forced into unusually close proximity [2.657 (3) Å], which in turn causes the rings to be rotated to an inter­planar angle of 13.7 (2)°. The packing involves hexa­gonally close-packed layers of mol­ecules parallel to the xy plane, corresponding to the known `7,11' pattern of paracyclo­phanes, but without significant short inter­molecular contacts.
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