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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...

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Autores principales: Nagarajaiah, H., Fathima, Nikhath, Begum, Noor Shahina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
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.
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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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