Synthesis and Crystal and Molecular Structure of 3,5-Dihydroxy-1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,5-dihydro-2-pyrrolone

Abstract

The reaction between methyl 2-diphenylmethylenehydrazino-4-oxo-4-p-tolyl-2-butenic ether and oxalyl chloride gave 1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione, which adds water to yield substituted 3,5-dihydroxy-2,5-dihydro-2-pyrrolone. The crystal and molecular structure of pyrrolone and the inter- and intramolecular hydrogen bonds in its crystals and solutions were investigated by IR spectroscopy and XRD analysis. The crystals of C27H22N2O6 are triclinic with cell dimensions a = 9.8540(10), b = 10.0880(10), c = 13.982(2) A, α = 69.820(10), β = 110.57(10), γ = 91.350(10)°, V = 1213.8(2) A3, M = 470.47, dcalc = 1.287 g/cm3, Z = 2, space group P1. The data were collected on a KM-4 (KUMA DIFFRACTION) diffractometer, 3781 reflections with I> 2 σ (I). Direct methods, hydrogen atoms localized, least-squares refinement (in an anisotropic approximation for non-hydrogen atoms), R = 0.0454. The crystal is built from the centrosymmetric dimer associates of molecules bonded by strong (2.64 A) intermolecular hydrogen bonds (IMHB) of O–H...O type. The dimer associates are linked by weaker (2.82 A) centrosymmetric IMHB, forming an infinite chain of hydrogen-bonded molecules.