This charting is from Bartrum's Gruffudd ap Cynan 5; https://www.geni.com/documents/view?doc_id=6000000173392536826. Bartrum is problematic here, as he has conflated 2 men named Gruffudd ap Cynan, which throws off his dating. You can see that he has both Cynwrig and Llewelyn in the same generation, 7. That would be OK if Llewelyn were 1230 and Cynwrig 1265. But that would push Dafydd Llwyd to around 1295. BUT...Darrell Wolcott would date Cynwrig at closer to 1255. But that would still make Dafydd Llwyd no earlier than 1285. We are pretty confident that Annes ferch Gwyn, wife of Dafydd Llwyd would fall near 1260, which should put Dafydd Llwyd at 1245/50.
What I suspect, at this point, is that this Dafydd Llwyd ap Cynwrig belongs as the son of an earlier Cynwrig ap Llewelyn in this extended family. Neither I, nor Private User, have started work on the Gruffudd ap Cynan series of charts. So for now, I think the best thing is to leave this alone and revisit it when we can get to that point, or we can get some clarification from Darrell Wolcott.