Fluconazolium picrate

Authors:

• Grzegorz Edward Dutkiewicz,
• C.S. Chidan Kumar,
• H.S. Yathirajan,
• B. Narayana,
• Maciej Kubicki

Abstract

The title compound, C₁₃H₁₃F₂N ₆O⁺·C₆H₂N₃O ₇^-, is the first structurally characterized salt of the cation of fluconazole [systematic name 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4- triazol-1-yl)propan-2-ol], a synthetic anti-fungal agent. In the crystal, the components are linked by O - H⋯O hydrogen bonding between the hy-droxy group of the fluconazolium cation and the C=O(-) group of the picrate anion. This complex is additionally stabilized by secondary, but relatively short, C - H⋯O interactions. The dimers thus formed are connected by N - H⋯N cation-cation hydrogen bonds into helices running along [010]. Neighboring helices of opposite handedness are joined by weak anion-anion C - H⋯O(nitro) interactions. In the cation, the mean planes of the three rings are approximately, within ca 25°, parallel to the central C - O bond. In the picrate anion two nitro groups, in turn, are almost coplanar with the ring plane [forming dihedral angles of 6.5 (2) and 3.8 (2)°] while the third nitro group is significantly twisted [by 46.79 (13)°].