The difference between the SubPc derivatives in orange and white cells (Figure ) indicates a tendency for molecules with halogens at the α-and β-position to be classified as orange and white, respectively. Considering the fact that SubPc-3F(β)-based crystals are classified into orange, we concluded that the molecular shape is a major determining factor in the 2D packing of columns. Multiple 2D packing possibilities with similar energy levels arise as the cross-section of the SubPc column deviates from a circular shape. Such systems cannot converge to a single assembly, making it difficult to obtain single crystals. This assumption is supported by the fact that (M)SubPc-3Br(β) and (M)SubPc-3I(β) are differently packed despite the small differences in the halogen sizes. The most stable packing would change with a small alteration of molecular structures, due to the different packing patterns with similar thermodynamic stability. Although the above discussion is estimated from the results only with SubPcs, the obtained guiding principle is based on the molecular shapes and must be universal for all bowl-shaped π-conjugated molecules.