Recently, the introduction of three or more fluorine (F) atoms at the α-positions of subphthalocyanine (SubPc), a bowl-shaped π-conjugated molecule, forms polar structures with trigonal lattices (① and ⑦, Figure ) while introducing F at the β-positions of SubPc forms nonpolar structures (② and ⑧). In the present study, similar SubPc derivatives were synthesized, where chlorine (Cl), bromine (Br), and iodine (I) is introduced in place of F (Supporting Information Part S2 and S3), while analyzing the crystal structures of these derivatives. The synthesized eight SubPc derivatives all possess chiral C3-symmetry (Figure ). We prepared and characterized 16 crystals with their enantiomers and racemic mixtures. The racemic mixtures afford the crystals of the corresponding racemates, indicating no chiral resolution. Note that the four F-based SubPc crystals in this study have been reported in our previous study. The space groups of 16 crystal structures are summarized in Table (the details are presented in Table and Figures S25S36). The obtained crystal structures are classified into eight assemblies in Figure and illustrated in Figure (The schematic illustrations of R3m and C2 are included in Supplementary, since R3 and R3m, and P21 and C2 are similar). Figure shows that SubPc stacks straight across all crystals. A limited number of structures form one-dimensional (1D) assemblies in crystal structures among the reported bowl-shaped π-conjugated molecules. Moreover, even fewer cases exhibit straight stacking. On the other hand, if bowl-shaped molecules stack in a zigzag manner, material properties would be differentiated depending on their zigzag manners. Hence, the straight-stacked bowls simplify the quantitative discussion of the effects of symmetry elements, such as chirality and polarity, on the physical properties of crystals.