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. 2017 Jan 31;8(4):2640–2651. doi: 10.1039/c6sc05196k

Fig. 2. (a) Comparison of the ‘parent’ CC3-R and CC13 cage structures with the scrambled 33:133-R mixture; only the relative positional isomers of cyclohexane and dimethyl vertices are shown; the additional positional isomerism of the dimethyl vertices is not represented here. Cyclohexane vertices are highlighted in red, dimethyl vertices highlighted in green; hydrogens omitted for clarity; (b) analytical HPLC traces showing the product distribution formed from scrambling a 1 : 1 mixture of (R,R)-cyclohexanediamine (CC3-R) with 1,2-diamino-2-methylpropane (CC13); the positional isomers are not resolved under these separation conditions, and hence 7 peaks are observed; (c) powder X-ray diffraction pattern of the scrambled cage 33:133-R showing a modest degree of crystallinity; (d) scanning electron micrographs show that the sample lacks the degree of geometric order that would be expected in a highly crystalline sample; (e) comparison of the solubility of CC3-R, CC13, and the scrambled 33:133-R cage mixture in chloroform and in hexachloropropene (PCP), showing that scrambling has increased the cage solubility.

Fig. 2