In this study we used molecular dynamics simulations to investigate the structural changes in nanoscopically thin n-octane films confined between smooth solid surfaces as a result of a) increasing solid-methylene unit affinity and b) increasing pressure. Increasing solid-methylene unit energetic affinity resulted in the solidification of the film at a critical value. A similar transition is observed at a critical value of pressure. Bulk n-octane was a liquid in both cases. The transition was signaled by an abrupt increase in the intermolecular order and was facilitated by a precipitous extension of the octane molecules, which adopted almost fully extended configurations. A discontinuous jump in the film density at the critical values of solid affinity and pressure was evident. The characteristics of the transitions showed that it was a mild first order transition from a highly ordered liquid to a poorly organized solid.