The shadow cast by the tower on the Gillette Building appears to actually be a gap between saw-toothed roofing in a kind of quadrangle behind the front block of the building, the whole area is in shadow. Agree it's a very low sun angle, looks like very long tree and house shadows around the tailplane and under the wing.
Google...
The tree shadows - if that's what they are! - look like they may be bare of leaves, late autumn, winter or maybe spring then!