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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)...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
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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. |
format | Online Article Text |
id | pubmed-5778476 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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