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Crystal structures of N-(2-chlorophenyl) acetamide (1) and phenyl (2-bromomethyl) benzoate (2) have been determined from laboratory X-ray powder diffraction data. In addition to intermolecular N–H···O and C–H···O hydrogen bonds, the crystal packing in (1) and (2) exhibits weak C–H···Cl/Br interactions, which facilitate formation of three-dimensional architectures. Hirshfeld surface analysis of compounds (1), (2), and a few related chloro- and bromo-phenyl derivatives retrieved from the CSD indicates that 83–97% of Hirshfeld surface areas in this class of compounds are due to H···H, H···π, H···O, and H···Cl/Br contacts.

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C–H···O and C–H···X (X = Cl/Br) hydrogen bond tuned supramolecular assembly: a combined X-ray powder diffraction and Hirshfeld surface analysis

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C–H···O and C–H···X (X = Cl/Br) hydrogen bond tuned supramolecular assembly: a combined X-ray powder diffraction and Hirshfeld surface analysis