Abstract
The title compound, C23H20N2O3S, (I), crystallizes in the orthorhombic space group, Pna 2 1 , with cell parameters a = 18.7975(6), b = 12.5173(4), c = 8.4804(3) Å, Z = 4. The molecular structure consists of a central pyrimidine ring which is significantly puckered to assume a screw-boat conformation fused to a thiazole ring with benzyl, carboxylate, methyl, phenyl and oxy groups bonded around this fused-ring moiety. The dihedral angle between the mean planes of the thiazole, benzyl and phenyl groups and the mean plane of the pyrimidine ring is 6.1(4)°, 83.8(7)° and 6.8(4)°, respectively. The dihedral angle between the mean planes of the benzyl and phenyl rings is 88.3(5)° while between the mean planes of the phenyl and thiazole groups measures 12.6(6)°. In the absence of expected hydrogen bonding interactions, the crystal packing is influenced by a collective action of strong intramolecular C–H···S hydrogen bond interactions, close C–H···O intramolecular contacts and O–Cg π-ring interactions. A DFT molecular orbital calculation gives support to these observations.
Graphical Abstract
Crystal Structure of Ethyl (2Z, 5R)-2-benzylidene-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3] thiazolo [3,2-a] pyrimidine-6-carboxylate is reported and its geometric parameters described. In the absence of expected hydrogen bonding interactions, the crystal packing is influenced by strong intramolecular C–H···S hydrogen bond interactions, close C–H···O intramolecular contacts and O–Cg π-ring interactions. A DFT molecular orbital calculation gives support to these observations.
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Acknowledgments
The authors are thankful to Department of Science and Technology (DST), and SAIF, I.I.T. Madras, Chennai, India for the X-ray data collection. MMJ thanks the University Grant Commission (Western Regional Office), India for their support of Minor Research Project F. no. 47-254/07.
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Jotani, M.M., Baldaniya, B.B. & Jasinski, J.P. Crystal Structure of Ethyl (2Z, 5R)-2-benzylidene-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3] Thiazolo [3,2-a] Pyrimidine-6-carboxylate. J Chem Crystallogr 39, 898–901 (2009). https://doi.org/10.1007/s10870-009-9587-z
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DOI: https://doi.org/10.1007/s10870-009-9587-z