Co-crystal sustained by π-type halogen-bonding inter­actions between 1,4-di­iodo­perchloro­benzene and naphthalene

The formation and crystal structure of a co-crystal based upon 1,4-di­iodo­perchloro­benzene (C(6)I(2)Cl(4)) as the halogen-bond donor along with naphthalene (nap) as the acceptor is reported. The co-crystal [systematic name: 1,2,4,5-tetra­chloro-3,6-di­iodo­benzene–naphthalene, (C(6)I(2)Cl(4))·(nap)] generates a chevron-like structure that is held together primarily by π-type halogen bonds (i.e. C—I⋯π contacts) between the components. In addition, C(6)I(2)Cl(4) also inter­acts with the acceptor via C—Cl⋯π contacts that help stabilize the co-crystal. Within the solid, both aromatic components are found to engage in offset and homogeneous face-to-face π–π stacking inter­actions. Lastly, the halogen-bond donor C(6)I(2)Cl(4) is found to engage with neighboring donors by both Type I chlorine–chlorine and Type II iodine–chlorine contacts, which generates an extended structure.