By the looks of that last pic, I'm guessing sometime in the late 60s- One Penn is nowhere to be seen, neither is 1345 6th Avenue or the XYZ buildings.
"Build me to the heavens, and Life never stops"
"Live as if the world were as it should be, to show it what it can be"
"Prayers are fleeting and wars are forgotten, but what is built endures"
-Ambassador DeLenn, Babylon 5