Abstract
Reaction of 4-formylantipyrine with N(4)-dimethylthiosemicarbazide and 3-piperidylthiosemicarbazide produces the N(4)-dimethylthiosemicarbazone (1), and the 3-piperidyl-thiosemicarbazone (2), respectively. Compound 1 is triclinic, space group P-1 with a = 6.329(1) Å, b = 11.699(1) Å, c = 11.943(1) Å, α = 65.83(1)°, β = 80.83(1)°, γ = 84.90(1)°, and V = 796.1(1) Å3 with Z = 2, for D calc = 1.324 g/cm3. Compound 2 is triclinic, space group P-1 with a = 6.784(1) Å, b = 10.485(2) Å, c = 13.462(3) Å, α = 102.05(2)°, β = 98.61(2)°, γ = 101.32(2)°, and V = 899.8(5) Å3 with Z = 2, for D calc = 1.319 g/cm3. Reaction of 4-aminoantipyrine with phenyl isothiocyanate produced N-antipyrine-N′-phenylthiourea (3). Compound 3 is monoclinic, space group P21/n with a = 6.863(7) Å, b = 15.361(3) Å, c = 16.332(5) Å, β = 90.35(6)°, and V = 1720.7(18) Å3 with Z = 4, for D calc = 1.306 g/cm3. Compounds 1 and 2 have intermolecular hydrogen bonding between the carbonyl oxygen of the antipyrine moiety and the NH hydrogen of the thiosemicarbazone moiety. In 3 the two unique molecules are held together as a dimer by interactions of the two thiourea NH's and the antipyrine moiety's\break oxygen.
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El-Sawaf, A.K., Hernández-Ortega, S., Valdés-Martínez, J. et al. Structural studies of N(4)-substituted thiosemicarbazones prepared from 4-formylantipyrine and a thiourea derived from 4-aminoantipyrine. Journal of Chemical Crystallography 33, 105–112 (2003). https://doi.org/10.1023/A:1023218724180
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DOI: https://doi.org/10.1023/A:1023218724180