This is a bolt and nut tightening simulation

I would like to consider the phenomenon of tightening and loosening progressing when the bolt is rotated ±90 degrees in a bolt and nut tightening structure. For this reason, I would like to reproduce the tightening and loosening of a simple bolt and nut.
I would like to reproduce the process of rotating the bolt and entering the nut.
Please let me know how I should set it up.

I want to fix the nut and rotate the bolt to simulate how the bolt moves.
I changed the project but it’s not working.
What should I do? Please advise.