Crystal and Molecular Structures of N-(5-Chloro-2-hydroxy-phenyl)-acetamide and Its Co-crystal with 3,5-Dinitrobenzoic Acid

Two crystalline compounds N -(5-chloro-2-hydroxy-phenyl)-acetamide [L] (1) , and ( N -(5-chloro-2-hydroxy-phenyl)-acetamide): (3,5-dinitrobenzoic acid) [(L) · (3,5-Hdns), 3,5-Hdns = 3,5-dinitrobenzoic acid] (2) were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. Compound 1 crystallizes in the monoclinic, space group C2/c, with a = 9.9833(7) Å, b = 10.7789(8) Å, c = 16.1622(14) Å, β = 92.8010(10)°, V = 1737.1(2) Å 3 , Z = 8. Compound 2 crystallizes in the monoclinic, space group C2/c, with a = 32.818(3) Å, b = 6.9900(5) Å, c = 14.8431(12) Å, β = 90.5340(10)°, V = 3404.8(5) Å 3 , Z = 8. Both supramolecular architectures of the compounds 1 – 2 involve N–H···O/O–H···O/C–H···O hydrogen bonds as well as other non-covalent association. The role of these non-covalent interactions in the crystal packing is ascertained. These weak interactions combined, the compounds displayed 1D–3D structures. Graphical Abstract The crystal structures of the N -(5-chloro-2-hydroxy-phenyl)-acetamide and its co-crystal with 3,5-dinitrobenzoic acid show the classical hydrogen bonding as well as CH–O, CH 3 –O, and π···π interactions, giving higher dimensional networks.