You need to explain the problem in more detail. I don't see what it sounds like you are trying to describe:
Describe each operation you are performing; every click, tool selection, etc.
In Illustrator,
dimensions of rotated bounding boxes do not reflect the measures of the rotated box. They uselessly reflect the mere vertical and horizontal bounds of the rotated box (like an invisible bounding box of a visible bounding box). Canvas, for example, handles this correctly, giving the user the choice between absolute and relative measures.
JET