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The crystal structure of the  p - tert -butylcalix[8]arene–chloroform 1:8 clathrate (C 88 H 112 O 8  · 8 CHCl 3 : P 1̅,  a  = 13.886(2) Å,  b  = 21.891(4) Å,  c  = 21.930(4) Å,  α  = 64.00(2)°,  β  = 78.97(2)°,  γ  = 88.75(2)°,  Z  = 2) features a strong CH/ π  interaction of one chloroform molecule with the  π  system of one phenol ring of the calix[8]arene moiety; the seven other chloroform molecules occupy interstitial places in the crystal lattice of a highly solvated macrocyclic system ( c  = 0.566 mol dm –3 ). A thermogravimetric analysis also shows that one solvent molecule is bound more tightly than the others. The observed binding motif is presumably based on a subtle interplay between favourable interactions (CH/ π  and to some extent Cl/ π ) and induced fit between host and guest.

A CH/π interaction at a highly solvated macrocycle in the solid state — the p - tert -butylcalix[8]arene–chloroform 1:8 clathrate