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Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate
In the title compound, C(24)H(22)N(2)O(4)S, the central pyrimidine ring is significantly puckered, assuming a conformation intermediate between a boat and a screw boat. The nearly planar thiazole ring (r.m.s. deviation = 0.0258 Å) is fused with the pyriamidine ring, making a dihedral angle of 9.83...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983585/ https://www.ncbi.nlm.nih.gov/pubmed/21580360 http://dx.doi.org/10.1107/S1600536810004812 |
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author | Jotani, Mukesh M. Baldaniya, Bharat B. Jasinski, Jerry P. |
author_facet | Jotani, Mukesh M. Baldaniya, Bharat B. Jasinski, Jerry P. |
author_sort | Jotani, Mukesh M. |
collection | PubMed |
description | In the title compound, C(24)H(22)N(2)O(4)S, the central pyrimidine ring is significantly puckered, assuming a conformation intermediate between a boat and a screw boat. The nearly planar thiazole ring (r.m.s. deviation = 0.0258 Å) is fused with the pyriamidine ring, making a dihedral angle of 9.83 (7)°. The carboxyl group is in an extended conformation with an anti-periplanar orientation with respect to the dihydropyrimidine ring. The benzene ring linked at the chiral C atom is perpendicular to the pyrimidine ring [dihedral angle = 85.21 (8)°] whereas the phenyl ring is nearly coplanar, making a dihedral angle of 13.20 (8)°. An intramolecular C—H⋯S hydrogen bond is observed. The crystal packing is influenced by weak intermolecular C—H⋯π interactions and π–π stacking between the thiazole and phenyl rings [centroid–centroid distance = 3.9656 (10) Å], which stack the molecules along the c axis. |
format | Text |
id | pubmed-2983585 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29835852010-12-30 Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate Jotani, Mukesh M. Baldaniya, Bharat B. Jasinski, Jerry P. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(24)H(22)N(2)O(4)S, the central pyrimidine ring is significantly puckered, assuming a conformation intermediate between a boat and a screw boat. The nearly planar thiazole ring (r.m.s. deviation = 0.0258 Å) is fused with the pyriamidine ring, making a dihedral angle of 9.83 (7)°. The carboxyl group is in an extended conformation with an anti-periplanar orientation with respect to the dihydropyrimidine ring. The benzene ring linked at the chiral C atom is perpendicular to the pyrimidine ring [dihedral angle = 85.21 (8)°] whereas the phenyl ring is nearly coplanar, making a dihedral angle of 13.20 (8)°. An intramolecular C—H⋯S hydrogen bond is observed. The crystal packing is influenced by weak intermolecular C—H⋯π interactions and π–π stacking between the thiazole and phenyl rings [centroid–centroid distance = 3.9656 (10) Å], which stack the molecules along the c axis. International Union of Crystallography 2010-02-13 /pmc/articles/PMC2983585/ /pubmed/21580360 http://dx.doi.org/10.1107/S1600536810004812 Text en © Jotani et al. 2010 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 Jotani, Mukesh M. Baldaniya, Bharat B. Jasinski, Jerry P. Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title | Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_full | Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_fullStr | Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_full_unstemmed | Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_short | Ethyl (2Z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate |
title_sort | ethyl (2z)-2-(3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-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/PMC2983585/ https://www.ncbi.nlm.nih.gov/pubmed/21580360 http://dx.doi.org/10.1107/S1600536810004812 |
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