(1 R,3 S)-3-(1 H -Benzo[ d ]imidazol-2-yl)-1,2,2-tri­methyl­cyclo­pentane-1-carb­oxy­lic acid as a new anti-diabetic active pharmaceutical ingredient

Abstract

The chiral title compound, C 16 H 20 N 2 O 2, which can be used for producing active pharmaceutical ingredients for treatment of type 2 pancreatic diabetes and other pathologies dependent on insulin resistance, was prepared from (1R,3S)-camphoric acid and o-phenyl­enedi­amine. It crystallized from an ethanol solution in the chiral monoclinic P2 1 space group. The five-membered ring adopts a twisted conformation with the methyl-substituted C atoms displaced by -0.273 (5) and 0.407 (5) Å from the mean plane through the other three atoms. In the crystal, mol­ecules are linked by O - H⋯N hydrogen bonds, forming chains along the a-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyze the inter­molecular contacts present in the crystal.