Awning windows
I'm afraid that your photos are a little too unclear. Can I see a better picture of the guides at the end of that operator? The hook and the rubber piece? I have a suspicion that they're both part of the same configuration.
Would you also happen to know who made your window?
Lastly, you mentioned a bar that the shoe attaches to. May I see that?
Thanks! Knowing that this is Andersen is a huge help. I suspected as much but a few details were uncertain, so that confirms it.
What you have here is an old and obsolete Andersen brand operator. they haven't made this in a long time. There are two modern versions that may replace it, however, as long as you don't mind doing a bit of handiwork. See our 39-389 and 39-390 for the two sizes available.
These are modern versions of your original operator, but the problem is they were designed for a modern window. As such, using them on an old window like yours won't be so simple. At minimum you're doing to need to remount the bar, redrill holes for the base, and very likely cut the wood sill trim to accommodate the new style base. Worst case scenario, you need a new sill trim entirely.
If you aren't familiar with this kind of project, I strongly recommend that you contact a local professional to do it for you. It's not easy, but we have had customers tell us that it worked after all that. It's going to be your best bet.
It's hard to say since the clips are damaged, but the 36-030 come to mind. We recommend comparing the specifications with an undamaged version to confirm.