9
24
Zhang, Wang, Wang, and Wu
Scheme 1.
Other chemicals were of analytical reagent grade
and were used directly without further purifica-
tion. The infrared spectra were recorded as KBr
pellets on a Nicolet 170SX FT-IR spectropho-
tometer. The H NMR Spectra were recorded on
a Bruker Am-300 spectrometer with TMS as in-
appear. The precipitate was filtered and recrystal-
lized from ethanol, the product has melting point
of 468 K. Crystals of II suitable for X-ray anal-
ysis were obtained from slow evaporation from
ethanol after two days at room temperature. IR
(KBr) υ: 1750, 1644, 1615, 1440, 1369, 1326,
1
−
1 1
ternal reference and DMSO-d as solvent. The
1184, 1129, 959, 883 cm . H NMR(DMSO-d ,
6
6
crystal structures were determined using Siemens
P4 and Bruker Smart-1000 CCD Diffractometer
instruments.
300 MHz): 8.13 (1H, S, H---C ), 7.73 (1H, d, J =
2
8.8 Hz, H---C ), 7.17 (2H, d, J = 8.4 Hz, H---C
ꢁ
,
5
2
H---C
ꢁ
), 7.13 (1H, d, J = 2.3 Hz, H---C ), 6.87
6
8
For the preparation of I, daidzein (0.2 g) was
dissolved into acetone (50 ml) and a little an-
hydrous Na CO . Dimethyl sulfate (0.5 ml) was
(1H, dd, J = 8.8 Hz, J = 2.2 Hz, H---C ), 6.74
6
(2H, d, J = 8.4 Hz, H---C
ꢁ
, H---C
ꢁ
), 2.04(6H, s,
3
5
H---CH ).
2
3
3
added dropwise to the solution with vigorous stir-
ring. The mixture was stirred for 2.5 h at room
temperature and colorless precipitation began to
appear. The precipitate was filtered and washed
with water until the pH of the filtrate was 8. After
recrystallization from ethyl acetate, the product
has melting point of 431 K. Crystals of I suitable
for X-ray analysis were obtained from slow evap-
oration from ethyl acetate after three days at room
temperature. IR (KBr) υ: 2971, 2833, 1628, 1597,
X-ray crystal structure determination
The sample of I and II selected for
investigation had dimensions of 0.58 mm ×
0.56 mm × 0.48 mm and 0.37 mm × 0.29 mm ×
0.21 mm, respectively. The data were collected
with graphite monochromated Mo Kα radiation
˚
(λ = 0.71073 A). The structures were solved
1
8
508, 1436, 1293, 1248, 1204, 1118, 1029, 878,
using direct methods with SHELXTL software
−
1
−1
20
06, 542 cm . The peaks at 1628 cm belong
package and refined by full-matrix least-squares
19
to the ---C -- -- -- O vibration of the group of I and
the disappear of the peak at about 3450 cm
techniques. The non-hydrogen atoms were as-
signed anisotropic displacement parameters in the
refinement. The hydrogen atoms were treated us-
ing a riding model. The structures were refined on
−
1
means the hydroxyl groups were substituted by
the methoxyl groups.
For the preparation of II, daidzein (0.3 g)
was dissolved into anhydrous pyridine (20 ml).
Acetic anhydride (0.3 ml) was added dropwise
to the solution. The mixture was left to sit for
2
21
F using SHELX-97. The final R values (on F)
were 0.0356 of I and 0.0476 of II.
The crystal and refinement data are listed
in Table 1. Selected bond lengths, bond angles
and torsion angles are given in Tables 2 and 3,
respectively.
4
h at room temperature then poured the mix-
ture into water and white precipitation began to
Zhang, Zun-Ting
