The Crystal Structures of (Z)-Ethyl 2-(4-chlorophenyl)-3-(2,4-difluorophenyl-amino)acrylate and its Analogues

Abstract

The title compound, C₁₇H₁₄ClF₂NO₂, crystallizes in monoclinic space group P2₁/c with unit cell dimension of a = 16.276(3) Å, b = 7.5030(15) Å, c = 13.812(3) Å, α = 90°, β = 111.11(3)°, γ = 90° and Z = 4. The structure of the title compound reveals a Z configuration with respect to the C=C double bond in aminoacrylate fragment. The molecule is stabilized by intramolecular N–H···F and N–H···O hydrogen bonds. In the ethyl 2-aryl-3-arylaminoacrylates, electronic properties of the substituents in the aniline motif clearly affected the attached C–N bond length, and such effect is very little relative to Z-/E-configuration with respect to the C=C double bond.

Graphical Abstract

The Ar–N bond length in the crystals of ethyl 2-aryl-3-arylaminoacrylate is sensitive to the electronic property of the substituent in aniline motif. An electronic-donating group would lengthen the Ar–N bond.