Two different tautomeric forms, namely the
keto [1-phenyl-3-(propan-2-yl)-1,2-dihydro-pyrazol-5-one] and the
enol form, [1-phenyl-3-(propan-2-yl)-1
H-pyrazol-5-ol], C
12H
14N
2O·2C
12H
14N
2O, are present in the crystal in a 1:2 ratio. During crystallization, 1-phenyl-3-(propan-2-yl)-1,2-dihydro-pyrazol-5-one undergoes tautomerization to afford a corresponding
enol via proton transfer reaction. The compound crystallizes in the triclinic space group
P1 with the following unit-cell parameters:
a = 11.1593(3)Å,
b = 11.2247(3)Å,
c = 14.1140(4)Å,
α = 73.333(3)°,
β = 88.286(2)°,
γ = 82.767(2)°,
Z = 2. The crystal structure was solved by direct methods and refined by full-matrix least-squares procedures to a final
R-value of 0.0405 for 4611 observed reflections. The dihedral angles between the mean planes through the phenyl ring and the pyrazole ring are: 28.04(5)°, 47.38(5)° and 49.32(6)° for molecules I, IIA, IIB, respectively. The crystal structure is stabilized by intermolecular N-H…N, O-H…O, O-H…N, C-H…O and C-H…
π hydrogen bonds.
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