A mixture of 1-ferrocenyl-3-(2-nitrophenyl)-2-propenone (0.09 g, 0.24 mmol), 80%
hydrazine hydrate (0.264 g, 5.28 mmol) and glacial acetic acid (10 ml) was
refluxed under nitrogen atmosphere for 5 h. TLC indicated the formation of the
reaction product. It was poured into ice-water to give dark orange solid. The
participate was separated by filtration and washed with water. The solid
product was dried at room temperature. Single crystals of the title compound
suitable for X-ray measurements were obtained by recrystallization from
methanol at room temperature (yield 50.5%; m.p. 425–426 K). IR (KBr, cm-1):
1653 (C?O), 1601 (C?C), 1574 (C?N), 1527 (asym N?O), 1333 (sym
N?O), 1107 (C—N). 1H-NMR (CDCl3, p.p.m.): 2.33 (s, 1H, CH3), 2.89 (dd,
1H, pyrazoline H4), 3.84 (dd, 1H, pyrazoline H4), 4.04 (s, 5H, ferrocene),
4.36 (s, 2H, ferrocene), 4.53 (s, 1H, ferrocene), 4.60 (s, 1H, ferrocene),
6.03 (dd, 1H, pyrazoline H5), 7.23–8.05 (m, 4H, aromatic). 13C-NMR
(CDCl3, p.p.m.): 21.75 (CH3), 43.83 (C4), 56.52 (C5), 67.30, 67.78 (C2',
C5'), 69.46 (C6'–C10'), 70.61, 71.10 (C3', C4'), 74.86 (C1'), 125.56 (C8),
126.37 (C9), 128.50 (C11), 134.28 (C10), 137.33 (C6), 147.08 (C7), 156.63
(C3), 168.30 (C?O).
H atoms were positioned geometrically and refined as riding atoms, with C—H =
0.93 (aromatic), 0.98 (CH) and 0.97 Å (CH2) and with Uiso(H) =
1.2Ueq(C). H atoms of the methyl group (C11) show rotational disorder
from a difference Fourier map. These H atoms were refined as riding atoms,
with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C).
Hydrogen-bond geometry (Å, °)
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x+1/2, y, −z+3/2.