Symmetry is an important factor in material design. Generally, it is difficult to quantitively discuss symmetry-property relations. Two materials only with symmetry differences are requisite to verify whether polar or nonpolar chiral systems are advantageous for a specific property/phenomenon, such as chirality-induced spin selectivity. However, it is difficult to selectively prepare materials having different symmetries without changing other physical properties. The current study successfully prepared seven exceptionally similar crystals with different symmetries in terms of polarity, chirality, and enantiomer alignments, which affords ideal materials for the abovementioned studies. Furthermore, we revealed a universal guiding principle on the self-assembly pattern of bowl-shaped molecules to predict the resultant assembled structures with the help of molecular dynamics simulations.