Can you send us your Skyline document and that .raw file?
In Skyline you can use the menu item:
File > Share
to create a .zip file containing your Skyline document and supporting files including extracted chromatograms.
Files which are less than 50MB can be attached to these support requests. That .raw file will probably be bigger than that, so you can upload it here:
https://skyline.ms/files.url
My guess is that there is something about that .raw file which is causing the crash.
If you're not sure which .raw file is causing the crash, you can send us all of the files from that folder.
Usually, if a .raw file is causing Skyline to crash, you would see the same sort of crash if you tried to use SeeMS.exe from ProteoWizard.
After we see your files we will probably be able to figure out what is going wrong.
-- Nick