A series of binary cocrystals involving the ditopic hydrogen-and halogen-bond (H-and X-bond, respectively) donors resorcinol (res) and hydroquinone (hq), and 1,3-and 1,4-diiodotetrafluorobenzene (1,3-and 1,4-di-I-tFb), respectively, cocrystallized with one of the three symmetric bipyridines trans-1,2-bis(n-pyridyl)ethylene (n,n′-bpe, where n = n′ = 2, 3, 4) is reported. The structures of the six novel cocrystals, (1,3-di-I-tFb)•(3,3′-bpe), 4(res)•3(3,3′-bpe), (1,3-di-I-tFb)•(4,4′-bpe), 3(hq)• 2(2,2′-bpe), (1,4-di-I-tFb)•(3,3′-bpe), and (hq)•(3,3′-bpe), are described. The cocrystals comprise components that assemble by either O−H•••N and O−H•••O H-bonds (res and hq) or N•••I X-bonds (1,3-and 1,4-di-I-tFb).The work completes a series of 18 cocrystals involving either the three dihydroxybenzenes catechol (cat), res, and hq or the three diiodotetrafluorobenzenes (1,2-, 1,3-, and 1,4-di-I-tFb) as H-or X-bond donors, respectively, with each of the three structurally isomeric symmetric bipyridines n,n′bpe. Our study demonstrates the significant consequences that minimally subtle variations to molecular structure of coformers can have for stoichiometric formulations, molecular packing, and solid-state photoreactivity. The work also provides access to a completed series of symmetrically substituted rctt-tetrakis(n-pyridyl)cyclobutanes (where: n = 2, 3, or 4).