The
X-ray structures of three potential molecular tweezers, C20H24N2O5 (1), C20H20N6O13 (2) and C28H32N2O13
(3), differing
only by the substituents on the terminal aromatic moieties, display three as yet unreported arrays. Hydrogen
bonding with co-crystallized water molecules as well as van der Waals interactions between terminal
aromatic moieties lead to specific packing patterns, namely: (i) a membrane-like architecture of associated molecular tapes in 1·2H2O, (ii) coupled right-handed and left-handed helices in 2·H2O and (iii) a stepped arrangement provided by a back-to-back pairing in (3)2·H2O. Molecular modelling of individual molecules in vacuo shows
that the most stable conformers of 1–3
intrinsically display attractive interactions between the terminal aromatic
groups, which stabilize a pseudocavity suitable for incorporation of a guest compound.
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