Fluconazolium picrate.

ABSTRACT: The title compound, C(13)H(13)F(2)N(6)O(+)·C(6)H(2)N(3)O(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 inter-actions. 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) inter-actions. 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)°].

SUBMITTER: Dutkiewicz G 

PROVIDER: S-EPMC2983200 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature