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In the crystals prepared from racemic axially chiral 3-(ortho-halophenyl)-2-methylquinazolin-4-one derivatives, the formation of intermolecular halogen bonding (C[double bond, length as m-dash]O⋯X) between the carbonyl oxygen and ortho-halogen atom (X = Cl, Br, I) was found, while in the crystals prepared from their optically pure forms, such halogen bonding was not detected.

Graphical abstract: Chirality-dependent halogen bonds in axially chiral quinazolin-4-one derivatives bearing ortho-halophenyl groups

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