Abstract
The crystal structure of 1,4-dihydro-6-methyl-5-N,N-diethylcarbamoyl-4-phenyl-2(3H)-pyrimidinethione, C16 H 21 N 3OS (1), is monoclinic, space group P21/n, a = 6.818(1), b = 13.211(2), c = 18.807(3) Å, β = 99.53(1)°, V = 1670.6(4) Å3, Z = 4 and d cal = 1.206 Mg/m3, R = 0.042 (wR = 0.119) for 190 parameters and 2560 observations with I ≥ 2σ(I) and 1,4-dihydro-6-methyl-5-N-methyl carbamoyl-4-(2′-nitrophenyl)-2(3H)-pyrimidinethione hemihydrate, C13 H 14N4O3S ⋅ 0.5H2O, (2), is triclinic, space group P1, a = 7.513(1), b = 14.381(2), c = 15.506(2)Å, α = 114.95(2), β = 98.11(1), γ = 93.55(1)°, V = 1490.0(3) Å3, Z = 4 and d cal = 1.406 Mg/m3, R = 0.062 (wR = 0.165) for 388 parameters and 3094 observations with I ≥ 2σ(I).
The compound 2 crystallized having two molecules in the asymmetric unit, which can be regarded as monohydrated dimers, and forming a hydrate. The conformation of the central heterocyclic ring (1,4-dihydropyrimidine) in both compounds was found to be close to a half-chair conformation. The 2-nitrophenyl substituent in 2 is in the axial synperiplanar orientation. In both compounds, the conformation of the 3-substituted carbamoyl group appears to be influenced by hydrogen bonding with anticlinal orientation observed for carbonyl groups serving as hydrogen bonding acceptors.
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Mohan, K.C., Ravikumar, K., Shetty, M.M. et al. Crystal and molecular structures of 1,4-dihydro-6-methyl-5-N,N-diethylcarbamoyl-4-phenyl-2(3H)-pyrimidinethione (1) and 1,4-dihydro-6-methyl-5-N-methyl carbamoyl-4-(2′-nitrophenyl)-2(3H)-pyrimidinethione hemihydrate (2). Journal of Chemical Crystallography 33, 113–121 (2003). https://doi.org/10.1023/A:1023270708250
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DOI: https://doi.org/10.1023/A:1023270708250