Abstract
The title compound, C26H22N4O5 (systematic name: methyl 2-ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1H-1,3-benzodiazole-7-carboxylate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-ethoxy-1-{(2′-(N′-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl}-1H-benzo[d]imidazole-7-carboxylate with diphenyl carbonate. There are two independent molecules (A and B) with different conformations and an ethyl acetate solvent molecule in the asymmetric unit. In molecule A, the dihedral angle between the benzene ring and its attached oxadiazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corresponding dihedral angles in molecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C—O—C—Cm (m = methyl) torsion angles for the ethoxy side chains attached to the imidazole rings in molecules A and B are 93.9 (3) and −174.6 (3)°, respectively. In the crystal, the components are linked by N—H⋯N and C—H⋯O hydrogen bonds, generating a three-dimensional network. Aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.536 (3)Å] are also observed.
Highlights
The title compound, C26H22N4O5 (systematic name: methyl 2ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1H-1,3-benzodiazole-7-carboxylate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)2-ethoxy-1-{(20 -(N0 -hydroxycarbamimidoyl)-[1,10 -biphenyl]-4yl)methyl}-1H-benzo[d]imidazole-7-carboxylate with diphenyl carbonate
The C—O—C—Cm (m = methyl) torsion angles for the ethoxy side chains attached to the imidazole rings in molecules A and B are
The synthesis of azilsartan methyl ester has been descripted in many literatures (Kohara et al, 1996; Rádl et al, 2013), there was no particular work on the structural characterization involving crystal structure
Summary
The title compound, C26H22N4O5 (systematic name: methyl 2ethoxy-1-{4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]benzyl}-1H-1,3-benzodiazole-7-carboxylate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)2-ethoxy-1-{(20 -(N0 -hydroxycarbamimidoyl)-[1,10 -biphenyl]-4yl)methyl}-1H-benzo[d]imidazole-7-carboxylate with diphenyl carbonate. With different conformations and an ethyl acetate solvent molecule in the asymmetric unit. The corresponding dihedral angles in molecule B are 58.45 (18), 50.73 (16) and 85.37 (10) , respectively. The C—O—C—Cm (m = methyl) torsion angles for the ethoxy side chains attached to the imidazole rings in molecules A and B are
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