J Chem Crystallogr (2010) 40:428–431
429
without further purification. Escherichia coli, Pseudomo-
nas aeruginosa, Salmonella typhi and Staphylococcus
aureus were offered by College of Biological. Elemental
analyses were performed on a Perkin–Elmer 240C ele-
mental analyzer. Proton NMR spectra were obtained with a
Varian INOVA300 spectrometer, using tetramethylsilane
(TMS) as internal standard and CDCl3 as solvent. IR
spectra were measured on a TENSOR 27 (Bruker) FT-IR
spectrometer with KBr pellets in the range 4,000–
400 cm–1.
at R = 0.0680, and wR = 0.1605 (w = 1/[d2(Fo2) ?
(0.0157P)2 ? 0.0000P], P = (Fo2 ? 2F2c)/3), S = 1.020,
(D/r)max = 0.000. The largest peak in the final difference
-3
˚
Fourier map is 0.240 e A and the minimum peak is
-0.260 e A-3. Molecular graphics were drawn with the
˚
program package SHELXS-90 [11].
Antibacterial Activity Tests
Antibacterial tests were performed according to the litera-
ture [12, 13]. The media required for the preparation of test
organism inocula are made from pancreatic digest of casein
(15.0 g), papaic digest of soybean meal (5.0 g), sodium
chloride (5.0 g), agar (15.0 g) and water (1,000 mL). The
compound (I) 0.5 g was dissolved in 100 mL of Sodium
Chloride Injection. Several pieces of filter paper (the
diameter is 5 mm) were put into the solution and then
sterilized at 121 ꢁC for 20 min. Preparation of the bacteries
solution was according to Edition 2005 Pharmacopoeia of
PRC.
Synthesis of the Compound (I) and (II)
According to the previous work [7, 8], 2-(1,3-Dioxoiso-
indolin-2-yl)acetic acid and 2-(5-Amino-1,3-dioxoisoin-
dolin-2-yl)acetic acid was synthesized. The compound
N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid was
prepared according to the literature [9].
To a solution of 2-(5-Amino-1,3-dioxoisoindolin-2-
yl)acetic acid (5 mmol) in acetone (20 mL), maleic anhy-
dride (5 mmol) in acetone (20 mL) was added drop by
drop, the solution was stirred magnetically for 2 h at room
temperature. The product was filtered and dried. Yield
65.3%. Anal. Calcd. (%) for C14H10N2O7: C 52.83, H 3.14,
The medium (20 mL) was paced in Petri dishe with the
required number and hardened into a smooth base layer
with uniform depth. The bacteries medium (5 mL) was
added and the plate was tilted back and forth to spread the
inoculum enenly over the surface, and then allowed it to
harden. Four pieces of test paper were attached to the
surface of the medium in every dish, and the plates were
covered to avoid contamination. The plate was incubated at
35 ꢁC for 16 h. The diameter of each zone of growth,
inhibition to the nearest 0.1 mm, was measured and
recorded, and the averages of the three values were
calculated.
1
N 8.81. Found (%): C 52.02, H 3.24, N 8.75. H NMR
(CDCl3): 4.57 (m, 2H, –CH2–), 6.51 (d, 1H, = CH–), 6.80
(d, 1H, = CH–), 8.07–8.11 (d, 2H, ph-H), 8.51 (m, 1H,
ph-H). All absorption bands in the IR data of the compound
(I) appear as expected. m(cm-1): 3,408 cm-1 (O–H), 3,101
cm-1 (N–H), 1,743, 1,712 and 1,690 cm-1 (C=O), 1,511
cm-1 (N–C).
A 20 mg of the compound (I) was dissolved in 95%
ethanol–water (95%) of 20 mL. The single crystal suitable
for X-ray determination was obtained by evaporation at
room temperature from the solution after a week.
Results and Discussion
X-Ray Single Crystal Structure Determination
Synthesis Scheme of the Compound (I)
A light yellow crystal with dimensions of 0.38 mm 9
0.27 mm 9 0.09 mm was selected for X-ray diffraction.
The reflection data were collected on a Bruker Smart Apex II
CCD area diffractometer with graphite monochromatized
N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid (I)
was prepared by four steps in higher yield from 2-amino-
acetic acid and isobenzofuran-1,3-dione, the synthesis
process is shown in Scheme 1.
˚
Mo-Ka radiation (k = 0.71073 A) at 298 (2) K. A total of
7,878 reflections were collected in the range of 1.45 \
h \ 25.01 by using x scans mode. And a total of 2,703
observed reflections with I [ 2r(I) were used in structure
solution and refinement. 1,061 independent reflections and
Rint = 0.1307. LP corrections were applied to the data.
The structure was solved by direct methods using SHEL-
XL-97 [10] and expanded using Fourier techniques. All
non-hydrogen atoms and hydrogen atoms were refined
anisotropically and isotropically, respectively. The final
refinementbyfull-matrix least squares methodwas converged
Structural Description
The molecular structure of the title compound is shown in
Fig. 1 and the crystal packing of the compound is depicted
in Fig. 2. The selected bond lengths and angles are given in
Table 1.
As seen from Fig. 1, the asymmetric unit of the title
compound contains one N-(N-acetic acid-yl-phthalimide-
5-yl) maleamic acid molecule and two water molecules. One
of the two water molecules is disordered. The N-(N-acetic
123
Li, Jian
