Crystal structures of six salts from nicotinamide and organic acids by classical H-bonds and other noncovalent forces

Cocrystallization of the widely used nicotinamide (Vitamin B3), with an array of organic acids gave a total of six anhydrous and hydrous multicomponent salts (nicotinamide)(:) (o-nitrobenzoic acid)(2) [(HL) center dot (onba(-)) center dot (Honba), onba = o-nitrobenzoate, Honba = o-nitrobenzoic acid] (1), (nicotinamide)(:) (2,3-dibromo-butanedioic acid) [(HL+) center dot (Hdba(-)), Hdba(-) = hydrogen 2,3-dibromo-butanedioate] (2), (nicotinamide)(2): (alpha-ketoglutaric acid)(2): H2O [(HL+)(2) center dot (Hkga(-))(2) center dot H2O, Hkga(-) = hydrogen alpha-ketoglutarate] (3), (nicotinamide): (3-nitrophthalic acid)(2) [(HL+) center dot (Hnpta(-)) center dot (H(2)npta), Hnpta(-) = hydrogen 3-nitrophthalate, H(2)npta = 3-nitrophthalic acid] (4), (nicotinamide): (butane-1,2,3,4-tetracarboxylic acid) [(HL+) (H(3)bta(-)), H(3)bta(-) = trihydrogen butane-1,2,3,4-tetracarboxylate] (5) and (nicotinamide)(2): (naphthalene-1,5-disulfonic acid) [(HL)(2)(2)(+) center dot (nds(2-)), nds(2-) = naphthalene-1,5-disulfonate] (6), which have been characterised by XRD technique, IR and EA, the melting points were also reported. Their structural and supramolecular aspects are deeply analyzed.The result tells that in all salts the aryl N in L is the only protonated site, the crystal packing is woven by the strong N-H center dot center dot center dot O, N-H center dot center dot center dot N, O-H center dot center dot center dot N and O-H center dot center dot center dot O H-bonds. The CONH2 dimers were existed in 1-3 by a pair of N-H center dot center dot center dot O H-bonds. Further view of the crystal packing told that a different series of additional CH center dot center dot center dot O/CH2 center dot center dot center dot O, CH center dot center dot center dot S, O center dot center dot center dot C, Br center dot center dot center dot C, Br center dot center dot center dot O, O center dot center dot center dot O, O center dot center dot center dot N, O center dot center dot center dot pi, pi center dot center dot center dot C, CH center dot center dot center dot pi and pi center dot center dot center dot pi contacts contribute to the stabilization and expansion of the total high-dimensional (2D-3D) motifs. For the delicate balance of the various weak nonbonding interactions these structures contained homo/hetero supramolecular synthons or both, and the common R21(7)/R22(8) graph sets have been enclosed in all salts due to the interplay of H-bonds and non-covalent contacts. (C) 2022 Elsevier B.V. All rights reserved.