Synthesis and crystal structure of 3,5-di(2-propenyl)-6-phenyl-1,3,5- triazine-2,4-dione and 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5- triazine

Article abstract of DOI:10.1023/B:JOCC.0000014685.89020.15

The title compound 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione has been synthesized by the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to orthorhombic, space group Pbca with the following crystallographic parameters: a = 16.282(4) A, b = 8.888(2) A, c = 19.281(5) A, α = 90°, β = 90°, γ = 90°, μ = 0.088 mm^-1, V = 2790.1(13) A³, z = 8, Dx = 1.282 mg/m³, F(000) = 1136, T = 293(2) K, 2.11° ≤ θ ≤ 25.02°, the final R factor: R₁ = 0.0430, wR₂ = 0.0981. The X-ray results demonstrate that the reaction of 6-phenyl-1,3,5-triazine-2,4- dione with allyl bromide in the presence of N,N-dimethylformamide and potassium carbonate yields the N-alkylated product. The title compound 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine has been synthesized by a new reaction, in which the solvent N,N-dimethylformamide involves. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to triclinic, space group P-1 with the following crystallographic parameters: a = 7.977(2) A, b = 10.394(3) A, c = 10.837(3) A, α = 111.774(5)°, β = 104.050(5)°, γ = 99.446(5)°, μ = 0.093 mm^-1, V = 776.6(4) A³, z = 2, Dx = 1.293 mg/m³, F(000) = 320, T = 293(2) K, 2.14° ≤ θ ≤ 25.03°, the final R factor: R ₁ = 0.0582, wR₂ = 0.1399. The distance of N(4)-C(2) (1.339 A) is much shorter than the length of normal C-N (1.47 A) and very close to that of C=N (1.33 A), which is indicative of the significant double bond character.

Full text of DOI:10.1023/B:JOCC.0000014685.89020.15

C
Journal of Chemical Crystallography, Vol. 34, No. 1, January 2004 ( 2004)
Synthesis and crystal structure of
3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione
and 2-dimethylamino-4-ethoxycarbonylmethoxy-6-
phenyl-1,3,5-triazine
Wang Qing-Min,(1) Liu Gang,(1) Shao Rui-Lian,(1) and Huang Run-Qiu(1)
Received April 21, 2003
The title compound 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione has been synthe-
sized by the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide. Its structure
was determined by X-ray single crystal diffraction. The crystal belongs to orthorhom-
˚
bic, space group Pbca with the following crystallographic parameters: a = 16.282(4) A,
b = 8.888(2) A, c = 19.281(5) A, = 90 , = 90 , = 90 , = 0.088 mm 1, V =
˚
˚
3
3
˚
2790.1(13) A , z = 8, Dx = 1.282 mg/m , F(000) = 1136, T = 293(2) K, 2.11
25.02 , the final R factor: R1 = 0.0430, wR2 = 0.0981. The X-ray results demonstrate
that the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide in the presence of
N,N-dimethylformamide and potassium carbonate yields the N-alkylated product. The title
compound 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine has been
synthesized by a new reaction, in which the solvent N,N-dimethylformamide involves.
Its structure was determined by X-ray single crystal diffraction. The crystal belongs to
˚
triclinic, space group P-1 with the following crystallographic parameters: a = 7.977(2) A,
˚
˚
b = 10.394(3) A, c = 10.837(3) A, = 111.774(5) , = 104.050(5) , = 99.446(5) ,
1
3
3
˚
= 0.093 mm , V = 776.6(4) A , z = 2, Dx = 1.293 mg/m , F(000) = 320, T =
293(2) K, 2.14
25.03 , the final R factor: R1 = 0.0582, wR2 = 0.1399. The dis-
---
˚
˚
---
tance of N(4) C(2) (1.339 A) is much shorter than the length of normal C N (1.47 A)
˚
---
and very close to that of C N (1.33 A), which is indicative of the significant double bond
---
character.
KEY WORDS: Synthesis; crystal structure; plant virucides; 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-
dione; 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine.
4
Introduction
1,3,5-Triazines have attracted considerable
activities.1
virucides,
Among these triazine plant
2,4-dioxohexahydro-1,3,5-triazinee
(DHT) and 1,5-diacetyl-2,4-dioxohexahydro-1,3,
5-triazinee (DADHT) have been commercialized
attention because of their marked antivirus
as plant virucides.5 However, there is a major
8
(1) State Key Laboratory of Elemento-Organic Chemistry, Institute of
Elemento-Organic Chemistry, Nankai University, Tianjin 300071,
People’s Republic of China.
To whom correspondence should be addressed; e-mail:
wang98h@263.net.
difficulty in using these plant virucides. They
have very low solubility in water and limited
solubility in common solvents, so application
of such triazines in water and as emulsible
31
C
1074-1542/04/0100-0031/0 2004 Plenum Publishing Corporation

32
Qing-Min, Gang, Rui-Lian, and Run-Qiu
(5 mmol) and allyl bromide (12 mmol) in N,N-
dimethylformamide (70 mL) was added potas-
sium carbonate at 50 C. Then the resulting mix-
ture was stirred at 50 C for 2 h, and cooled to
room temperature, then added water and toluene.
The water phase was extracted three times with
toluene. The organic phase was washed with wa-
ter, and dried with anhydrous magnesium sulfate
and filtered. The filtrate was concentrated and
chromatographed on a silica gel column using a
mixture of petroleum ether (60–90 C) and ethyl
acetate as the eluent. Finally, 3,5-di(2-propenyl)-
6-phenyl-1,3,5-triazine-2,4-dione (2) (1.09 g) was
obtained in 80.2% yield. m.p., 105–106 . Anal.
Calcd.(%) for C15H15N3O2: C, 66.91; H, 5.58;
N, 15.61. Found(%): C, 67.01; H, 5.51; N,
Scheme 1
concentrates is not ordinarily feasible. Therefore,
the discovery of new analogues of 1,3,5-triazine,
which might show similar or enhanced biological
activity and possess favorable characteristics,
could be significant. In a search for new plant
virucides, we designed to alkylate 6-phenyl-
1,3,5-triazine-2,4-dione (1) by reaction with allyl
bromide as shown in Scheme 1.
However, we found the following new reac-
tion of 6-phenyl-1,3,5-triazine-2,4-dione (1) with
ethyl bromoacetate as shown in Scheme 2.
1
15.58. H NMR (CDCl3, ppm): 4.41 (d, 2H,
CH2, 3 JHH = 5.2 Hz), 4.56 (d, 2H, CH2, 3 JHH
=
---
6.1 Hz), 4.96–5.50 (m, 4H, CH ), 5.71–5.96
---
2
(m, 2H, CH), 7.40-8.40 (m, 5H, Ph). All absorp-
tion bands in IR data of 3,5-di(2-propenyl)-6-
Experimental
phenyl-1,3,5-triazine-2,4-dione (2) appear as ex-
The melting point was determined with a
Thomas–Hoover melting point apparatus and is
uncorrected. IR spectra were recorded with a
Shimadzu-435 spectrometer. 1H NMR spectra
were recorded with a Bruker AC-P200 instrument,
tetramethylsilane being used as internal stan-
dard. Elemental analyses were carried out with
a Yanaco CHN Corder MT-3 elemental analyzer.
Mass spectra were recorded with an HP5988A
spectrometer using the EI method.
1
---
pected. 1722.8 cm (s) corresponds to C O
---
stretching absorption bands, 1639.5 cm 1 (s) cor-
---
responds to C N stretching absorption bands.
---
The EI-MS of 3,5-di(2-propenyl)-6-phenyl-1,3,5-
triazine-2,4-dione (2) gives the molecular ion
peaks (269, M) and those of the main fragments.
The colorless single crystal was cultured from a
mixture solution of ethyl acetate and petroleum
ether (1:3.V/V) by slow evaporation at room tem-
perature.
Synthesis of 3,5-di(2-propenyl)-6-phenyl-1,3,5-
triazine-2,4-dione (2)
Synthesis of 2-dimethylamino-4-ethoxycarbonyl-
methoxy-6-phenyl-1,3,5-triazine (3)
Under a nitrogen atmosphere, to a stirred
solution of 6-phenyl-1,3,5-triazine-2,4-dione (1)
Under a nitrogen atmosphere, to a stirred
solution of 6-phenyl-1,3,5-triazine-2,4-dione (1)
(5 mmol) and ethyl bromoacetate (12 mmol)
in N,N-dimethylformamide (70 mL) was added
potassium carbonate at 50 C. Then the resulting
mixture was stirred at 50˚C for 2 h, and cooled
to room temperature, then added water and
toluene. The water phase was extracted three
times with toluene. The organic phase was
washed with water, and dried with anhydrous
Scheme 2

Synthesis and crystal structure
33
magnesium sulfate and filtered. The filtrate
was concentrated and chromatographed on a
silica gel column using a mixture of petroleum
ether (60–90 C) and ethyl acetate as the
eluent. Finally, 2,4-diethoxycarbonylmethoxy-
6-phenyl-1,3,5-triazine and 2-dimethylamino-4-
ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine
(3) were obtained.
ether (1:3.V/V) by slow evaporation at room
temperature.
Crystal structure determinations and refinements
The crystal data, data collection, and re-
finement parameter for the structure 2 and 3 is
listed in Table 1. Data were collected with a
Bruker SMART 1000 CCD diffractometer, using
graphite monochromatized Mo K radiation ( =
2-dimethylamino-4-ethoxycarbonylmethoxy-
6-phenyl-1,3,5-triazine (3): m.p., 107–108 . Anal.
Calcd.(%) for C15H18N4O3: C, 59.60; H, 5.96;
˚
0.71073 A). All calculations were performed by
N, 18.54. Found(%): C, 59.26; H, 5.44; N,
usingtheSHELXTL-NTpackageandrefinedwith
full matrix least-square procedures on PCs. All
nonhydrogen atoms were refined anisotropically.
All hydrogen atoms were located from a differ-
ence Fourier map and were placed at calculated
positions refined with riding model position pa-
rameters isotropically.
3
18.41. NMR:
7.3 Hz), 3.15 (s, 3H, NCH3), 3.29 (s, 3H, NCH3),
4.21 (q, 2H, CO2CH2, JHH = 7.3 Hz), 4.88 (s,
1.22 (t, 3H, CH3, JHH
=
H
3
2H, OCH2), 7.41–8.42 (m, 5H, Ph). The col-
orless single crystal was cultured from a mix-
ture solution of ethyl acetate and petroleum
Table 1. Crystallographic Data and Structure Refinement for 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione (2) and
2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine (3)
Product 2
Product 3
Chemical formula
CCDC Deposit Number
Color
C15H15N3O2
CCDC-207881
Colorless
C15H18N4O3
CCDC-208080
Colorless
Crystal size (mm)
Crystal system
Space group
0.20 0.25 0.25
Orthorhombic
Pbca
0.20 0.25 0.30
Triclinic
P-1
˚
˚
Unit-cell dimensions
a = 16.282(4) A.
a = 7.977(2) A.
= 90
= 111.774(5)
˚
˚
b = 8.888(2) A.
b = 10.394(3) A.
= 90
= 104.050(5)
˚
˚
c = 19.281(5) A.
c = 10.837(3) A.
= 90
= 99.446(5)
776.6(4)
2
3
˚
Volume (A )
2790.1(13)
Z
8
Formula weight
Density (calc.) (mg/m3)
Absorption coefficient (mm
F(000)
269
1.282
0.088
1136
302.15
1.293
0.093
1
)
320
Diffractometer/scan
Radiation/wavelength
Temperature (K)
Bruker SMART/CCD area detector
˚
Mo K (graphite monochrom.)/0.71073 A
293
2
293
2
range for data collection (deg)
Reflections collected
2.11–25.02
10821
2.14–25.03
3225
Independent/observed reflections
Absorption correction
Refinement method
2463
SADABS
Full-matrix least-squares on F2
R1 = 0.0430, wR2 = 0.0981
0.260, 0.199
2718
Final R indices [I 2 (I)]
Largest diff. Peak and hole (e. A
R1 = 0.0582, wR2 = 0.1399
3
˚
)
0.285, 0.204

34
Qing-Min, Gang, Rui-Lian, and Run-Qiu
Table 2. Atomic Coordinates ( 104) and Thermal Parameters
2
˚
(A
103) of the Product 2
Atom
x
y
z
Ueq
N(1)
N(2)
N(3)
O(1)
O(2)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
6636(1)
5598(1)
6315(1)
7330(1)
5390(1)
6793(2)
6032(1)
5745(1)
7235(1)
7113(2)
6492(2)
6465(2)
7103(3)
7820(3)
5830(1)
5656(1)
5420(2)
5351(2)
5506(2)
5747(1)
619(2)
1607(2)
609(2)
1475(2)
471(2)
568(3)
1638(3)
505(3)
4367(1)
5087(1)
5406(1)
4711(1)
6130(1)
4823(1)
4518(1)
5576(1)
3801(1)
3204(1)
3094(2)
5905(1)
6423(2)
6453(2)
4027(1)
4304(1)
3884(2)
3179(2)
2896(2)
3319(1)
36(1)
45(1)
44(1)
61(1)
62(1)
41(1)
38(1)
45(1)
44(1)
54(1)
64(1)
63(1)
93(1)
141(2)
40(1)
53(1)
66(1)
69(1)
61(1)
51(1)
791(3)
259(3)
Fig. 1. Molecular structure of 3,5-di(2-propenyl)-6-phenyl-
1,3,5-triazine-2,4-dione (2).
1137(3)
1837(3)
1398(4)
1817(6)
2877(3)
4282(3)
5456(3)
5231(3)
3849(3)
2674(3)
Results and discussion
6-Phenyl-1,3,5-triazine-2,4-dione (1) un-
derwent reaction with allyl bromide to yield
3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-
Note. Ueq = (1/3)6i 6j Ui j ai aj ai aj .
1
dione (2).As the elemental analyses H NMR
and MS spectra data of the product 2 cannot
lengths and bond angles are listed in Tables 3
and 4.
6-Phenyl-1,3,5-triazine-2,4-dione (1) un-
derwent reaction with ethyl bromoacetate to
---
be used to verify the site of alkylation (N
or O-alkylation) definitely, we determined its
structure using the X-ray crystallography data.
Results demonstrate that the product 2 under
this condition is the N-alkylated product. The
molecular structure of the title compound 2
is shown in Fig. 1. The molecular packing of
the title compound 2 is shown in Fig. 2. The
atomic coordinates and thermal parameters for
nonhydrogen are listed in Table 2, the bond
Table 3. Selected Bond lengths ( ) of
the Product 2
---
N(1) C(2)
1.368(3)
1.396(3)
1.473(3)
1.306(3)
1.380(3)
1.369(3)
1.396(3)
1.475(3)
1.209(3)
1.213(3)
1.488(3)
1.496(4)
1.293(4)
1.493(4)
1.226(4)
1.383(3)
1.387(3)
1.376(4)
1.379(4)
1.367(4)
1.383(3)
---
N(1) C(1)
---
N(1) C(4)
---
N(2) C(2)
---
N(2) C(3)
---
N(3) C(1)
---
N(3) C(3)
---
N(3) C(7)
---
O(1) C(1)
---
O(2) C(3)
---
C(2) C(10)
---
C(4) C(5)
---
C(5) C(6)
---
C(7) C(8)
---
C(8) C(9)
---
C(10) C(15)
---
C(10) C(11)
---
C(11) C(12)
---
C(12) C(13)
---
C(13) C(14)
Fig. 2. The packing diagram of 3,5-di(2-propenyl)-6-phenyl-
1,3,5-triazine-2,4-dione (2).
---
C(14) C(15)

Synthesis and crystal structure
35
Table 4. Selected Bond Angles ( ) of the Product 2
---
---
---
---
C(2) N(1) C(1)
119.92(19)
124.41(19)
115.02(18)
119.8(2)
123.5(2)
117.5(2)
118.8(2)
122.7(2)
121.7(2)
115.6(2)
123.6(2)
115.5(2)
120.9(2)
122.4(2)
120.4(2)
117.2(2)
114.7(2)
127.3(3)
111.1(2)
127.9(4)
118.5(2)
123.5(2)
117.8(2)
120.9(3)
119.6(3)
120.5(3)
119.7(2)
120.8(3)
C(2) N(3) C(4)
--- ---
C(1) N(1) C(4)
--- ---
C(2) N(2) C(3)
--- ---
C(1) N(3) C(3)
--- ---
C(1) N(3) C(7)
--- ---
C(3) N(3) C(7)
--- ---
O(1) C(1) N(3)
--- ---
O(1) C(1) N(1)
--- ---
N(3) C(1) N(1)
--- ---
N(2) C(2) N(1)
--- ---
N(2) C(2) C(10)
--- ---
Fig. 3. Molecular Structure of 2-dimethylamino-4-
ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine (3).
N(1) C(2) C(10)
--- ---
O(2) C(3) N(2)
--- ---
O(2) C(3) N(3)
--- ---
N(2) C(3) N(3)
--- ---
in Table 5, the bond lengths and bond angles are
listed in Tables 6 and 7.
N(1) C(4) C(5)
--- ---
C(6) C(5) C(4)
--- ---
N(3) C(7) C(8)
--- ---
In the title compound 2, N(1), C(1), N(3),
C(3), N(2), andC(2)atomsarecoplanar, whichde-
fined the 1,3,5-triazine ring. C(10), C(11), C(12),
C(13), C(14), and C(15) are coplanar, which de-
fined the phenyl ring.
C(9) C(8) C(7)
--- ---
C(15) C(10) C(11)
--- ---
C(15) C(10) C(2)
--- ---
C(11) C(10) C(2)
--- ---
C(12) C(11) C(10)
--- ---
C(11) C(12) C(13)
--- ---
In the title compound 2, the bond
C(14) C(13) C(12)
--- ---
C(13) C(14) C(15)
--- ---
---
---
---
lengths of N(1) C(2), N(1) C(1), N(2) C(3),
C(14) C(15) C(10)
--- ---
N(3) C(1), and N(3) C(3) (1.368, 1.396, 1.380,
˚
1.369, 1.396 A, respectively) are shorter than nor-
˚
---
mal C N (1.47 A) and close to that of C N
---
˚
---
(1.33 A), which is indicative of the significant
---
9
yield 2,4-diethoxycarbonylmethoxy-6-phenyl-
1,3,5-triazine.At the same time, a small amount
of 2-dimethylamino-4-ethoxycarbonylmethoxy-
6-phenyl-1,3,5-triazine (3) was isolated as
byproduct. 2-Dimethylamino-4-ethoxycarbonyl-
methoxy-6-phenyl-1,3,5-triazine (3) was iden-
tified by IR and 1H NMR spectroscopy and
EI MS and elemental analyses. All absorption
bands in IR data of 2-dimethylamino-4-
double bond character. The N(2) C(2) bond dis-
tance is 1.306 A, slightly shorter than the nor-
mal C N bond distance. The bond lengths of
---
N(1) C(4) and N(3) C(7) (1.473, 1.475 A, re-
spectively) are normal.
˚
---
˚
---
---
ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine
1
(3) appear as expected.1065.4 cm
(s) cor-
---
responds to C O stretching absorption
bands. The EI-MS of 2-dimethylamino-4-
ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine
(3) gives the molecular ion peaks (302.15, M) and
those of the main fragments. The molecular struc-
ture of the title compound 3 is shown in Fig. 3.
The molecular packing of the title compound 3
is shown in Fig. 4. The atomic coordinates and
thermal parameters for nonhydrogen are listed
Fig. 4. The packing diagram of 2-dimethylamino-4-
ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine (3.)

36
Qing-Min, Gang, Rui-Lian, and Run-Qiu
Table 5. Atomic Coordinates ( 104) and Thermal Parameters
Table 7. Selected Bond Angles ( ) of the
Product 3
2
103) of the product 3
˚
(A
---
---
---
C(3) O(1) C(12)
116.4(2)
116.9(3)
114.9(3)
113.0(3)
112.8(3)
121.4(3)
121.3(3)
117.3(3)
125.6(3)
118.3(3)
116.1(3)
118.3(3)
116.9(3)
124.7(3)
129.0(3)
118.8(3)
112.3(3)
118.2(3)
121.2(3)
120.6(3)
119.8(3)
121.4(3)
119.1(3)
120.7(3)
120.9(3)
108.2(2)
125.5(3)
126.3(3)
108.2(3)
108.0(3)
Atom
x
y
z
Ueq
---
C(13) O(3) C(14)
--- ---
C(1) N(1) C(2)
--- ---
O(1)
O(2)
O(3)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
9984(3)
12170(3)
11818(3)
7070(3)
8245(3)
8854(3)
6469(4)
7888(4)
7274(4)
8965(4)
5403(5)
6653(5)
7755(4)
7139(5)
7063(5)
7572(5)
8182(4)
8268(4)
10212(4)
11531(4)
12994(5)
13128(5)
4558(2)
5479(3)
7694(2)
3142(3)
5044(3)
2772(3)
5345(3)
2346(3)
4486(3)
4128(3)
4854(4)
6818(3)
868(3)
2471(2)
5129(2)
5680(2)
1581(3)
769(3)
47(1)
61(1)
51(1)
39(1)
40(1)
42(1)
44(1)
36(1)
37(1)
38(1)
57(1)
53(1)
40(1)
50(1)
60(1)
58(1)
51(1)
44(1)
43(1)
41(1)
61(1)
74(1)
C(3) N(2) C(2)
--- ---
C(3) N(3) C(1)
--- ---
C(2) N(4) C(5)
--- ---
C(2) N(4) C(4)
--- ---
C(5) N(4) C(4)
--- ---
302(3)
N(1) C(1) N(3)
--- ---
1068(3)
1063(3)
627(3)
1114(3)
2546(3)
101(4)
2044(3)
3496(3)
4388(4)
3873(4)
2446(4)
1536(3)
3422(3)
4822(3)
7114(3)
7883(4)
N(1) C(1) C(6)
--- ---
N(3) C(1) C(6)
--- ---
N(4) C(2) N(1)
--- ---
N(4) C(2) N(2)
--- ---
N(1) C(2) N(2)
--- ---
N(2) C(3) N(3)
--- ---
N(2) C(3) O(1)
--- ---
416(3)
968(4)
N(3) C(3) O(1)
--- ---
C(7) C(6) C(11)
--- ---
1917(4)
1479(3)
110(3)
6011(3)
6324(4)
8200(4)
9749(4)
C(7) C(6) C(1)
--- ---
C(11) C(6) C(1)
--- ---
C(8) C(7) C(6)
--- ---
C(9) C(8) C(7)
--- ---
C(10) C(9) C(8)
--- ---
C(9) C(10) C(11)
--- ---
C(10) C(11) C(6)
--- ---
O(1) C(12) C(13)
--- ---
Note. Ueq = (1/3)6i 6j Ui j ai aj ai aj .
O(2) C(13) O(3)
--- ---
O(2) C(13) C(12)
--- ---
O(3) C(13) C(12)
--- ---
O(3) C(14) C(15)
˚
Table 6. Selected Bond Lengths (A)
of the Product 3
---
O(1) C(3)
1.354(3)
1.428(3)
1.193(3)
1.324(4)
1.448(4)
1.331(3)
1.348(4)
1.309(3)
1.364(4)
1.331(4)
1.351(4)
1.339(4)
1.458(3)
1.463(4)
1.477(4)
1.392(4)
1.395(4)
1.386(4)
1.371(4)
1.369(4)
1.377(4)
1.504(4)
1.484(4)
In the title compound 3, N(1), C(1), N(3),
C(3), N(2), and C(2) atoms are coplanar, which
defined the 1,3,5-triazine ring. C(6), C(7), C(8),
C(9), C(10), and C(11) are coplanar, which de-
---
O(1) C(12)
---
O(2) C(13)
---
O(3) C(13)
---
O(3) C(14)
---
N(1) C(1)
---
fined the phenyl ring. The distance of N(4) C(2)
---
N(1) C(2)
˚
(1.339 A) is much shorter than the length of nor-
mal C N (1.47 A) and very close to that of C N
(1.33 A), which is indicative of the significant
---
N(2) C(3)
˚
---
---
---
---
N(2) C(2)
---
9
N(3) C(3)
˚
---
N(3) C(1)
double bond character.
---
N(4) C(2)
---
N(4) C(5)
---
N(4) C(4)
Acknowledgment
---
C(1) C(6)
---
C(6) C(7)
This work was supported by the National
Natural Science Foundation of China (20002003).
---
C(6) C(11)
---
C(7) C(8)
---
C(8) C(9)
---
C(9) C(10)
References
---
C(10) C(11)
---
C(12) C(13)
1. Qu, F.Q.; Xiao, C.H.; Xu, X.J. J. Wuhan Univ. (Nat. Sci. ed.)
1999, 45(2), 143–146.
---
C(14) C(15)

Synthesis and crystal structure
37
2. Li, Z.G.; Huang, R.Q. Zhiwu Baohu 1999, 3, 37.
3. Schuster, G.; Heinisch, L.; Schulze, W. Phytopathol. Z 1984,
111(2), 97.
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219–226.
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Kramer, W.; Schmidt, H.; Steinke, U.; Steinke, W.; Voigt, D.;
Schuster, G. Ger (East) DD 1986, 233, 482.
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412–420.
8. Schuster, G.; Huber, S. Biochem. Physiol. Pflanzen 1991, 187,
429–438.
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book, 3rd ed.; The Chemical Society of Japan: Maruzen, Tokyo,
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