Cross-cyclophane twin donors, in which long axes of TTF units are fixed in a cross orientation by four ethylenedithio (x-CPTD (II)) and four trimethylenedithio (x-CPTD (III)) chains, were designed and prepared. Although the donor ability of x-CPTD (II) was low due to a heavy bending of the donor units, that of x-CPTD (III) was the same as BEDT-TTF. The crystal structures of a charge transfer complex, x-CPTD (III) ·TCNQ, and an ion radical salt, x-CPTD (III)·Br (1,1,2-TCE)2, revealed that x-CPTD (III) has an ability to construct characteristic self-assembled structures, recognizing a size and a shape of acceptors or counter ions. The almost isotropic conducting property (σr,t//a = 1.0 × 10−2 S · cm−1, σr,t//a= 5.5 × 10−3 S · cm−1) of the ion radical salt was interpreted based on the unique molecular structure of x-CFTD (III).