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Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethen­yl]-2,3-di­hydro­quinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thio­phen-2-yl)ethen­yl]-2,3-di­hydro­quinazolin-4(1H)-one from synchrotron X-ray diffraction

The chiral title compounds, C(21)H(18)N(2)O(2), (I), and C(21)H(18)N(2)OS, (II) – products of the three-component reaction between benzyl­amine, isatoic anhydride and furyl- or thienyl-acrolein – are isostructural and form isomorphous racemic crystals. The tetra­hydro­pyrimidine ring in (I) and (II)...

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Detalles Bibliográficos
Autores principales: Toze, Flavien A. A., Zaytsev, Vladimir P., Chervyakova, Lala V., Kvyatkovskaya, Elisaveta A., Dorovatovskii, Pavel V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5778476/
https://www.ncbi.nlm.nih.gov/pubmed/29416882
http://dx.doi.org/10.1107/S2056989017017479
Descripción
Sumario:The chiral title compounds, C(21)H(18)N(2)O(2), (I), and C(21)H(18)N(2)OS, (II) – products of the three-component reaction between benzyl­amine, isatoic anhydride and furyl- or thienyl-acrolein – are isostructural and form isomorphous racemic crystals. The tetra­hydro­pyrimidine ring in (I) and (II) adopts a sofa conformation. The amino N atom has a trigonal–pyramidal geometry [sum of the bond angles is 347.0° for both (I) and (II)], whereas the amido N atom is flat [sum of the bond angles is 359.3° for both (I) and (II)]. The furyl- and thienylethenyl substituents in (I) and (II) are planar and the conformation about the bridging C=C bond is E. These bulky fragments occupy the axial position at the quaternary C atom of the tetra­hydro­pyrimidine ring, apparently, due to steric reasons. In the crystals, mol­ecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong inter­molecular N—H⋯O hydrogen bonds.