69 Dart steering column issues

Head of the bolt is in a 3 sided box. 2 walls are taller, 3rd wall has a ramp. So with nuts on enough to hold the bolt from turning between the 2 taller walls, Put the collar on. As you tighten the nuts, the ramp carries the bolt head toward and into the slot. Hard to tell if you have distorted the part/pushed slot(s) away but one shown doesn't look exactly round.