In this study, we report the preparation, conformational dynamics, and recognition characteristics of novel molecular capsule 1 comprising a bowl-shaped framework conjugated to a tris(2-pyridylmethyl)amine (TPA) lid. With the assistance of experiment (H-1 NMR spectroscopy) and theory (MM and DFT) we found that C-3 symmetric 1 is poorly preorganized with three pyridines at the rim adopting a propeller-like orientation and undergoing P-to-M (or vice versa) stereoisomerization (Delta G(double dagger) < 8 kcal/mol, VT H-1 NMR). Capsule 1 binds CH4, CH3Cl, CH2Cl2, CHCl3, and CCl4 with K-a < 7 M-1. Protonation of 1 with HCl, however, gives [1 center dot H]-Cl with the solid-state structure showing the TPA lid being "flattened" and the N+-H---Cl hydrogen-bonded group residing outside. Importantly, the P-to-M stereoisomerization would for [1 center dot H]-Cl occur with Delta G(double dagger) = 11 kcal/mol (VT H-1 NMR). Less dynamic and more preorganized [1 center dot H]-Cl binds CH4, CH3Cl, CH2Cl2, CHCl3, and CCl4 guests with a greater affinity (K-a = 100-400 M-1) than 1. The results of our studies suggest that the complexation of increasingly larger guests takes place in an induced-fit fashion, with [1 center dot H]-Cl (a) elongating along its vertical axis and concurrently potentially (b) twisting pyridines fromP into M (and vice versa) orientation. The addition of Et3N to [1 center dot H]-Cl subset of CH2Cl2 causes deprotonation of the capsule and the release of CH2Cl2 with the process being fully reversed after the addition of HCl. Allosteric capsule 1 with unique structural and dynamic characteristics is expected to, in the future, assist the construction of complex molecular machines and smart functional materials.