The Synthesis and Crystal Determination of 3-Hydroxy-4-(4-methoxyphenyl)-5-(2-nitrophenyl)furan-2(5H)-one

Abstract

The title compound, C₁₇H₁₃NO₆, was synthesized and structurally characterized by elemental analysis, MS, ¹H NMR and single crystal X-ray diffraction. It crystallizes in monoclinic system space group C 2/c with a = 27.981(6) Å, b = 12.996(3) Å, c = 8.0900(16) Å, β = 91.06(3)°, V = 2941.4(10) Å³, Z = 8, R ₁ = 0.0675, wR ₂ = 0.1626, and T = 298(2) K. The X-ray structure determination revealed that the center furanone ring is nearly coplanar with p-methoxybenzene ring and forms a dihedral angle of 87.2(1)° with the nitrobenzene ring. O–H···O Intermolecular hydrogen bonds link pairs of molecules into centrosymmetric dimers, making a graph set motif of R ²₂ (10). The dimers are further assembled into a chain of edge-fused R ⁴₄ (34) rings running along the [001] direction. The final three-dimensional supramolecular architecture is stabilized by weak π–π interactions.

Graphical Abstract

The dimers were assembled into a chain of edge-fused R ⁴₄ (34) rings running along the [001] direction and a co-chain is formed with an “x” pattern of the cross section.