Ethyl 5-[(1H-benzoimidazol-2-yl)aminocarbonyl]-4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydropyridine-3-carboxylate–ethanol–methanol (4/2/1)

Svetlana V Shishkina,Andrei A Tkach,Igor V Ukrainets,Oleg V Shishkin,Lina A Grinevich

doi:10.1107/s1600536809026816

Svetlana V Shishkina, Andrei A Tkach + Show 3 more

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https://doi.org/10.1107/s1600536809026816

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Abstract

The asymmetric unit of the title compound, 4C20H22N4O5·2C2H6O·CH4O, contains two pyridine-3-carboxylate molecules, one ethanol molecule and one methanol molecule disordered about in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in both independent molecules are planar within 0.03 Å due to the formation of intramolecular O—H⋯O and N—H⋯O hydrogen bonds. The formation of these latter interactions also causes the redistribution of the electron density within the hydroxypyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. In the crystal phase, the pyridine-3-carboxylate molecules form layers parallel to (010), which are interlinked through hydrogen bonds mediated by the bridging solvate molecules. A terminal ethyl group in one of the molecules is disordered over two sites of equally occupancy.

Highlights

The asymmetric unit of the title compound, 4C20H22N4O52C2H6OCH4O, contains two pyridine-3-carboxylate molecules, one ethanol molecule and one methanol molecule disordered about in a centre of symmetry
The pyridine-3carboxylate molecules form layers parallel to (010), which are interlinked through hydrogen bonds mediated by the bridging solvate molecules
N-acylic derivatives of 2-aminobenzoimidazole are considered as potential antithyroid drugs (Ukrainets et al, 1993), for what the structures of these compounds are of particular interest

Summary

Data collection

The pyridinone ring, the carbamide group and the bicyclic fragment in both independent molecules are planar within 0.03 Å due to the formation of intramolecular O—H O and N—H O hydrogen bonds. The formation of these latter interactions causes the redistribution of the electron density within the hydroxypyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. The pyridine-3carboxylate molecules form layers parallel to (010), which are interlinked through hydrogen bonds mediated by the bridging solvate molecules. A terminal ethyl group in one of the molecules is disordered over two sites of occupancy

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