Imino-Diels-Alder Adducts. Part XIII. Polymorphism in Pyrano [3,2-c] Quinolines

Abstract

Crystallization by slow evaporation of methanol solution of 5-(4-nitrophenyl)-3,4,4a5,6,10b-hexahydro-2H-pyrano[3,2-c] quinoline, yields two polymorphs. Rectangle plate-like crystals have a triclinic (P $\ifmmode\expandafter\bar\else\expandafter\=\fi{1}$) structure, with one molecule in the asymmetric unit, a = 8.2299(5) Å, b = 9.7774(6) Å, c = 11.0047(7) Å, α = 65.718(1)°, β = 75.699(1)° and γ = 71.617(1)°, while, long needle-like crystals exhibit a monoclinic (C2/c) crystal structure in which two independent molecules comprise the asymmetric unit, a = 32.285(3) Å, b = 9.4045(7) Å, c = 22.804(2) Å and β = 114.965(1)°. The crystal structures reveal the molecule in both the polymorphs as an endo-Imino-Diels-Alder cycloadduct isomer. The stereochemistry of the pyran ring in both the polymorphs is exo to the quinoline ring formed in the cycloaddition step. The molecules are linked by N–H···O hydrogen bonds into centrosymmetric dimers forming R₂ ²(18) rings in the triclinic form, while they are arranged to form a helical chain in the monoclinic form.

Index abstract

Crystallization by slow evaporation of methanol solution of 5-(4-nitrophenyl)-3,4,4a5,6,10b-hexahydro-2H-pyrano[3,2-c] quinoline, yields two polymorphs. The crystal structures reveal the molecule in both the polymorphs as an endo-Imino-Diels-Alder cycloadduct isomer. The stereochemistry of the pyran ring in both the polymorphs is exo to the quinoline ring formed in the cycloaddition step. The molecules are linked by N–H···O hydrogen bonds into centrosymmetric dimers forming R₂ ²(18) rings in the triclinic form, while they are arranged to form a helical chain in the monoclinic form.