Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexahydrobenzo[h]cinnolin-2-yl)propionic acid

• Main Authors: Fiorella Meneghetti, Daniela Masciocchi, Arianna Gelain, Stefania Villa
• Format: Article
• Language: English
• Published: International Union of Crystallography 2014-10-01
• Series: Acta Crystallographica Section E
• Subjects: crystal structure; pyridazinone moiety; stat3 inhibitor
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536814019850

The asymmetric unit of the title compound, C15H16N2O3, contains two independent molecules, which present a different conformation of the carboxylic acid side chain [C—C—C—OH torsion angles = 65.3 (7) and −170.1 (5)°]. In both molecules, the dihydropyridazinone ring adopts a geometry intermediate between a twisted-boat and a half-chair conformation, while the central six-membered ring is almost in a half-boat conformation. In the crystal, molecules are linked by O—H...Ok (k = ketone) hydrogen bonds, generating [01-1] chains. Aromatic π–π stacking contacts between the benzene and the dihydropyridazinone rings [centroid–centroid distance [3.879 (9) Å] are also observed.