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Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thio-phen-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1H)-one from synchrotron X-ray diffraction.

ABSTRACT: The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) - products of the three-component reaction between benzyl-amine, isatoic anhydride and furyl- or thienyl-acrolein - are isostructural and form isomorphous racemic crystals. The tetra-hydro-pyrimidine 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 tetra-hydro-pyrimidine ring, apparently, due to steric reasons. In the crystals, mol-ecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong inter-molecular N-H?O hydrogen bonds.

SUBMITTER: Toze FAA 

PROVIDER: S-EPMC5778476 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Crystal structure of 3-benzyl-2-[(<i>E</i>)-2-(furan-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1<i>H</i>)-one and 3-benzyl-2-[(<i>E</i>)-2-(thio-phen-2-yl)ethen-yl]-2,3-di-hydro-quinazolin-4(1<i>H</i>)-one from synchrotron X-ray diffraction.

Toze Flavien A A FAA   Zaytsev Vladimir P VP   Chervyakova Lala V LV   Kvyatkovskaya Elisaveta A EA   Dorovatovskii Pavel V PV   Khrustalev Victor N VN  

Acta crystallographica. Section E, Crystallographic communications 20180101 Pt 1

The chiral title compounds, C<sub>21</sub>H<sub>18</sub>N<sub>2</sub>O<sub>2</sub>, (I), and C<sub>21</sub>H<sub>18</sub>N<sub>2</sub>OS, (II) - products of the three-component reaction between benzyl-amine, isatoic anhydride and furyl- or thienyl-acrolein - are isostructural and form isomorphous racemic crystals. The tetra-hydro-pyrimidine 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)],  ...[more]

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