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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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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
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author Toze, Flavien A. A.
Zaytsev, Vladimir P.
Chervyakova, Lala V.
Kvyatkovskaya, Elisaveta A.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_facet Toze, Flavien A. A.
Zaytsev, Vladimir P.
Chervyakova, Lala V.
Kvyatkovskaya, Elisaveta A.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_sort Toze, Flavien A. A.
collection PubMed
description 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.
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spelling pubmed-57784762018-02-07 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 Toze, Flavien A. A. Zaytsev, Vladimir P. Chervyakova, Lala V. Kvyatkovskaya, Elisaveta A. Dorovatovskii, Pavel V. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2018-01-01 /pmc/articles/PMC5778476/ /pubmed/29416882 http://dx.doi.org/10.1107/S2056989017017479 Text en © Toze et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Toze, Flavien A. A.
Zaytsev, Vladimir P.
Chervyakova, Lala V.
Kvyatkovskaya, Elisaveta A.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5778476/
https://www.ncbi.nlm.nih.gov/pubmed/29416882
http://dx.doi.org/10.1107/S2056989017017479
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