239's have the round hole in center position in my experience.
The so-called "raised" manifold pad came out in 1941, at or near the time the plug holes in pan rail used through '40 disappeared.
Just from pics and bore, I would call this a '38 or '39-40 (lots of differnces in '38) 221 bored out to 239 size. If you investigate further, look for the core holes/bulges at pan rail, then look at where cylinder barrel approaches the trapezoid hole. On an original 239 you will see that the cylinder is ridiculously thick (you can measure it with some finagling) and that cylider comes almost to hole, while a bored 221 cylinder will be fairly thin like a modern casting.
Oops...obviously you have the core holes. I was focussed entirely on the deck picture.