Synthesis, crystal structure determination and Hirshfeld surface analysis of three new salt forms of creatinine with hydrobromic acid, 3‐aminobenzoic acid and 3,5‐dinitrobenzoic acid

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2022-08, Vol.78 (8), p.437-448
• Main Authors: Jeyaraman Selvaraj, Nirmalram, Sathya, Udhayasuriyan, Gomathi, Sundaramoorthy, Jegan Jennifer, Samson, Mathivathanan, Logesh, Abdul Razak, Ibrahim
• Format: Article
• Language: English
• Subjects: Acids; Anions; benzoate; bromide; Cations; comparative analysis; Creatinine; Crystal structure; Fungicides; Hirshfeld surface analysis; Hydrobromic acid; Hydrogen; Hydrogen bonds; intermolecular interactions; Kidney diseases; Kidneys; salt; Salts; Stability analysis; Structural stability; Surface analysis (chemical); Surface stability; two‐dimensional fingerprint plot
• ISSN: 2053-2296; 0108-2701; 2053-2296; 1600-5759
• DOI: 10.1107/S2053229622006684

Creatinine, a biologically important compound, is used to analyze kidney function and kidney diseases in the human body. The salt form of creatinine is used in the formation of drug materials like anti‐HIV, antifungal, antiprotozoal, antiviral and antitumour compounds. Here we report the solid‐state structures of three new crystalline salts, namely, creatininium (2‐amino‐1‐methyl‐4‐oxo‐4,5‐dihydro‐1H‐imidazol‐3‐ium) bromide, C4H8N3O+·Br−, (I), creatininium 3‐aminobenzoate, C4H8N3O+·C7H6NO2−, (II), and creatininium 3,5‐dinitrobenzoate, C4H8N3O+·C7H3N2O6−, (III). These salts have been synthesized and characterized by single‐crystal X‐ray diffraction and Hirshfeld surface analysis. The structural chemistry of salts (I)–(III) and their crystal packing are discussed in detail. The primary interaction between the creatinine cation and the acid anion in the three salts is N—H…Br/O hydrogen bonds. In salt (I), the creatinine cation and bromide anion are connected through a pair of N—H…Br hydrogen bonds forming R42(8) and R42(12) ring motifs. In salts (II) and (III), the creatinine cation interacts with the corresponding anion via a pair of N—H…O hydrogen bonds. The crystal structure is further stabilized by C—H…O and O—H…O hydrogen bonds with the ring motifs R22(8), R21(7) and R21(6). Furthermore, the crystal structures are stabilized by π–π, C—H…π, C—O…π and N—O…π stacking interactions. The contributions made by each hydrogen bond in maintaining the crystal structure stability has been quantified by Hirshfeld surface analysis. The solid‐state structures of three new crystalline salts of creatininium, namely, the bromide, 3‐aminobenzoate and 3,5‐dinitrobenzoate, have been characterized by single‐crystal X‐ray diffraction and Hirshfeld surface analysis. The structural chemistry of the salts and their crystal packing are discussed in detail.