Bis((benzo-18-crown-6)-4,5-ylmethyl)-1,3,4,6- diphenylglycoluril: The First Representative of a New Class of Bis(crown ethers) and the Synthesis and Crystal Structure of Its Complex with Sodium Picrate

A statistical Monte Carlo computer simulation has shown that the use of a diphenylglycoluril fragment as a rigid linker should give bis(crown ethers) with identically oriented benzocrown rings located closely in space. The syntheses of the first representative of this series, bis[(benzo-18-crown-6)-4,5-ylmethyl]-1,3,4,6-diphenylglycoluril and its complex with sodium picrate have been described. The crystal structure of the complex has been determined by X-ray diffraction: space group \(P\bar 1\), a = 13.976(3) A, b = 16.723(3) A, c = 20.578(4) A, α = 98.74(2)°, β = 106.19(3)°, γ = 114.07(3)°. The complex represents a new type of coordination polymer formed by a combination of coordination and hydrogen bonds and stacking, which are favored by the U-shaped conformation of diphenylglycoluril.