I had a similar issue on getting the bolt in place on my truck. I opened up the hole just a little to allow the bolt to drop in. When I got the truck it had a hex head bolt with part of the head ground away to allow it to clear the timing cover.
Kevin 1951 Chevy 3100 work truck Follow this saga in Project Journal Photos 1929 Ford pickup restored from the ground up. | 1929 Ford Special Coupe (First car) Busting rust since the mid-60's If you're smart enough to take it apart, you darn well better be smart enough to put it back together.