The present investigation is focused on the macro and nanocrystals of 4-(4-chlorophenyl)-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-2,5(3H,6H)-dione (CPDMDHHBPHHD), its synthesis, and the various characterization and comparative studies performed to assess its applications. Nanocrystals were prepared by milling procedure and its evaluation and utility than macro-sized entitled crystals were thoroughly discussed. The single crystal XRD study reveals the macro-crystalline lattice parameters with the empirical formula as C 17 H 17 ClO 3 and a = 11.9005 Å, b = 5.7971 Å, c = 22.608 Å and β = 93.97°. The crystal system is monoclinic with space group P2 1 /n. The nanoform of entitled crystals specimen are of 16 nm of size. Characterization studies for macro-and nano-scaling such as dielectric, fluorescence (FL), photoconductivity, tribological study, and nano influx for filters were performed and reported. From the present study, it could be concluded that CPDM-DHHBPHHD crystals are known to be best for electronic filters, frequency doubling circuits, second harmonic generation (SHG) efficiency, and nano level influx value which is useful for opto-electronic applications.