Synthesis, characterization, crystal and molecular structure analysis of 2,6-dimethyl-3-acetyl-5-carbomethoxy-4-phenyl-1,4-dihydropyridine

The synthesis of a novel unsymmetrical dihydropyridine, bearing carboxy methyl and carbomethoxy groups at C(3) and C(5), respectively, has been achieved by applying the modified Hantzsch-type condensation, which involves the Michael addition of Knoevenagel adduct with an enamine. The product obtained was characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The title compound C17H19NO3 crystallizes in Monoclinic crystal class in space group P2(1)/c with cell parameters a = 9.9130(12) angstrom, b = 7.3320(5) angstrom, c = 22.018(3) angstrom, beta = 109.637(3)degrees, V = 1507.2(3) angstrom(3) and Z = 4. The final residual factor R-1 = 0.0642. The structure exhibits both intra and inter-molecular hydrogen bonding of the type C-H center dot center dot center dot O and N-H center dot center dot center dot O. The pyridine ring gives boat conformation