The data doesn't allow via Chesterfield fares to be validated that way, though of course there are cheaper fares that are, along with the Any Permitted fare. There is nothing written on the ticket to say you should go a particular route south of Chesterfield
In practice, XC staff are likely to check the ticket before Derby anyway and are unlikely to mind. As for West Midlands Trains, if you are lucky enough to get on one that's running, be able to board it and actually have a ticket check I would be surprised, and again can't see them having an issue with it.
But journey planners can't give you a reservation unless you buy the cheaper or more expensive fares.