We examined the 40Ca + 238U reaction experimentally using the Mass-Angle Distribution (MAD) technique and within the Time Dependent Hartree Fock (TDHF) theory, using the TDHF3D code. A new, TDHF based approach has been developed to construct mass distributions as well. The results revealed that the orientation of the heavy deformed prolate nucleus plays a major role in the reaction outcome. It was found that aligned collisions lead to quasifission and short contact times of 5-10 zs, whilst anti-aligned collisions lead to longer contact times (> 23 zs). TDHF accurately predicted the presence of quasifission and the average mass splits in this reaction. The influence of shell effects around 208Pb in the calculated quasifission characteristics was observed in both experiment and theory.