I'm a descendent of Jonathan Riley of Clay Co., IL who married Sarah Myers about 1840.They had a son named Rolla Jefferson Riley and several other children, including my ggrandfather, Jonathan Riley (a junior?).He married Mary E. Stonecipher.
The older Jonathan was almost certainly born in IN about 1820.I have leads as to his parents, but nothing sure.One possibility is a Jonathan Riley who was in IN in 1820.
The best possibility according to most people is William Riley who married Thirsey Brooks in 1823 in Orange Co., IN.
As you can see, dates don't match very well with your dates.I am relatively sure about what I have recorded in the first paragraph.If you can fit it with what you do know about your Jonathan for sure, I would love to correspond with you and share our efforts.My e-mail is email@example.com, or you can reply on this forum.