nonpolar and racemic-alternating (N/Ra, ⑥), (vii) polar and racemic-random (P/Rr, ⑦), and (viii) nonpolar and racemic-random (N/Rr, ⑧). If we thoroughly examine all the substances that have been reported, molecular assemblies with similar symmetries to these eight kinds might be recorded for each of them. However, the impact of symmetry on physical properties cannot be discussed if their molecular structures are significantly different. If these molecular assemblies can be individually prepared by minimizing the modification of their molecular structures, it provides design guidelines to enhance properties/phenomena, such as CISS and BPVE. The present study demonstrated that seven of the eight structures could be individually synthesized by changing the size and position of halogens. Furthermore, the revealed self-assembling rule of bowl-shaped molecules and molecular dynamics (MD) simulations were combined to propose a simple method to predict these assembled structures.