Ethyl (Z)-4′-(4-ethoxy-1-hydroxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphenyl]-3-carboxylate

Yoshinobu Ishikawa,Atsushi Ugai

doi:10.1107/s1600536813018503

Abstract

The 1,3-diketone group of the title compound, C21H20O6, exists in a keto–enol form stabilized by a strong intramolecular O—H⋯O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, molecules are packed in a layered structure parallel to the b axis through C—H⋯O and π–π interactions [centroid–centroid distance between stacked benzene rings = 3.868 (2) Å].

Highlights

The 1,3-diketone group of the title compound, C21H20O6, exists in a keto–enol form stabilized by a strong intramolecular O—H O hydrogen bond
Molecules are packed in a layered structure parallel to the b axis through C—
According to our inhibitor design targeting this metalloenzyme (Ishikawa et al 2011), we synthesized the title compound by Claisen condensation of ethyl 4′-acetyl-[1,1′-biphenyl]-3-carboxylate with diethyl oxalate in the presence of sodium ethoxide, which biphenyl derivatives are the synthetic intermediates of a final biphenyl diketo acid

Summary

Data collection

R factor = 0.040; wR factor = 0.104; data-to-parameter ratio = 16.4. H atoms treated by a mixture of independent and constrained refinement max = 0.25 e Å3. The 1,3-diketone group of the title compound, C21H20O6, exists in a keto–enol form stabilized by a strong intramolecular O—H O hydrogen bond. A planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5) and that between the benzene rings is 19.70 (5). Molecules are packed in a layered structure parallel to the b axis through C—. H O and – interactions [centroid–centroid distance between stacked benzene rings = 3.868 (2) Å]

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Crystal data

Yoshinobu Ishikawa and Atsushi Ugai

Special details