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Stable organic radicals have drawn attention as promising building blocks for multifunctional materials. In order to realize the tailored magnets based on molecular materials, it is necessary to investigate magneto-structural correlation of open-shell molecules. In the present chapter, we describe the magnetic property of dihydroquinoline N-oxyl-based radicals and benztriazynyl-based radicals to discuss the substituent effect on molecular packing and intermolecular magnetic interaction. Relatively large magnetic interactions were observed through π-π stacking for dihydroquinoline N-oxyl-based radicals. Spin transition behavior was demonstrated in benztriazynyl-based radical.