Cannot load mod_shib_22.so into server: The specified module could not be found

[Rod Widdowson]

I'd also observe that :

1) Oracle HTTP Server isn't necessarily Apache;  I'm pretty sure that means that this is unsupported.
2) Server 2008 is EOL even for extended support in less than 6 months

At this stage I'd stop digging and move onto a supported platform.

If you really are into extended self-flagellation you'll need to start looking at the dependencies (2008 is old enough that SxS may
not be a problem).  Depends.exe is your friend, but expect to spend a day on this to possibly no gain.

R