Crystal structure of ethyl (1RS,6SR)-4-(2-methyl-1H-imidazol-4-yl)-2-oxo-6-(2,3,5-trichlorophenyl)cyclohex-3-ene-1-carboxylate

Abstract

The title compound, C19H17Cl3N2O3, has been prepared in a cyclocondensation reaction between 2,3,5-trichlorobenzaldehye and 4-acetyl-2-methyl-1H-imidazole. The cyclohexenone ring adopts an envelope conformation with the C atom substituted by the trichlorophenyl ring as the flap. The mutually trans ester and aryl substituents both occupy equatorial sites. In the crystal, a combination of N—H...O and C—H...N hydrogen bonds links the molecules into ribbons of edge-fused centrosymmetric rings, which enclose R22(14) and R44(16) alternate ring motifs, propagating along the b-axis direction.

Keywords

• crystal structure
• cyclocondensation reaction
• molecular stereochemistry
• molecular conformation
• hydrogen bonding