The clathrate compounds of tri-o-thymotide have been prepared with chlorocyclohexane, bromocyclohexane and 2-chlorotetrahydropyran. The cage-type inclusion complex C₃₃H₃₆O₆ · ¹/₂ C₆H₁₁Cl (trigonal, P3₁21, α = 13.604(1), c = 30.605(1) Å, Z = 6) contains an axial-Cl chair and an axial-Cl boat conformation of the guest, distributed statistically in the ratio 2 ∶ 1 over the available sites. The observed conformations have been compared with conformers calculated by force field methods. IR spectra are consistent with the crystal structure results for the tri-o-thymotide/chlorocyclohexane clathrate. They further demonstrate the similar preferential inclusion of axial isomers of bromocyclohexane and 2-chlorotetrahydropyran.