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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...

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Autores principales: Jotani, Mukesh M., Baldaniya, Bharat B., Jasinski, Jerry P.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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AT jasinskijerryp ethyl2z23methoxybenzylidene7methyl3oxo5phenyl23dihydro5h13thiazolo32apyrimidine6carboxylate