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Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate
In the title compound, C(22)H(17)BrN(2)O(4)S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positione...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344184/ https://www.ncbi.nlm.nih.gov/pubmed/22606187 http://dx.doi.org/10.1107/S1600536812013311 |
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author | Nagarajaiah, H. Fathima, Nikhath Begum, Noor Shahina |
author_facet | Nagarajaiah, H. Fathima, Nikhath Begum, Noor Shahina |
author_sort | Nagarajaiah, H. |
collection | PubMed |
description | In the title compound, C(22)H(17)BrN(2)O(4)S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The methoxycarbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O—H⋯N and C—H⋯S interactions result in sheets along the c axis. The supramolecular assembly is stabilized by π–π stacking interactions between the 2-bromobenzylidene and thiazolopyrimidine rings [centroid–centroid distance = 3.632 (1) Å]. In addition, C—H⋯π interactions are also observed in the crystal structure. |
format | Online Article Text |
id | pubmed-3344184 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33441842012-05-17 Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate Nagarajaiah, H. Fathima, Nikhath Begum, Noor Shahina Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(22)H(17)BrN(2)O(4)S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The methoxycarbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O—H⋯N and C—H⋯S interactions result in sheets along the c axis. The supramolecular assembly is stabilized by π–π stacking interactions between the 2-bromobenzylidene and thiazolopyrimidine rings [centroid–centroid distance = 3.632 (1) Å]. In addition, C—H⋯π interactions are also observed in the crystal structure. International Union of Crystallography 2012-03-31 /pmc/articles/PMC3344184/ /pubmed/22606187 http://dx.doi.org/10.1107/S1600536812013311 Text en © Nagarajaiah et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Nagarajaiah, H. Fathima, Nikhath Begum, Noor Shahina Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title | Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_full | Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_fullStr | Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_full_unstemmed | Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_short | Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_sort | methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5h-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344184/ https://www.ncbi.nlm.nih.gov/pubmed/22606187 http://dx.doi.org/10.1107/S1600536812013311 |
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