Mapping out the diversity of interplay of O-alkylated calix[4]arenes

O-Alkylated calix[4]arenes with varying chain lengths, corresponding to C_nH_2n+1 where n = 12, 14 or 16, compounds 1–3 respectively, show that the arrangement of the molecules in the solid state has a profound dependence on n, with n = 12 and n = 16 resulting in an interdigitated bilayer arrangement, and n = 14 resulting in a head-to-head bilayer structure. Preliminary data collected also suggest that n = 12 is the lower limit for efficient packing, below which the packing is dominated by the calix[4]arene moiety.