N-(R-nitrophenylsulfonamido)benzoic acids: Synthesis, crystal structures, and Hirshfeld surface study

Four N-(R-nitrophenylsulfonamido)benzoic acids (NO2-SBA) [o -ABA: HL1 and HL2, m -ABA: HL4 and HL5] were synthesized and characterized by elemental analysis, spectroscopic methods and powder and single crystal X-ray diffraction techniques. The combined NMR and X-ray techniques confirmed the intramolecular N1-H1N & sdot;& sdot;& sdot;O2 hydrogen bond in HL1 and HL2. All crystal structures presented a molecular dimer of the carboxylic moiety of NO2-SB. The interconnections in the crystal structures were analyzed using Hirshfeld surfaces and showed that the O & sdot;& sdot;& sdot;H/H & sdot;& sdot;& sdot;O were the major intermolecular interactions for all crystal structures.