2482
H.-D. Yin et al. / Journal of Organometallic Chemistry 689 (2004) 2480–2485
Table 2
Crystallographic data of compounds 1 and 2
(CDCl3):
d
172.95(CH‚N),
172.71(COO),
74.34(‚NCH), 169.68, 138.20, 137.65, 136.60, 135.79,
130.82, 130.67, 128.93, 123.05, 117.26(Ar–C), 34.87,
19.03, 18.49(Pr-i). 119Sn NMR d À348.53. IR (KBr,
cmÀ1): 1671, 1331(CO2), 1613(C‚N), 586, 541(Sn–O),
446(Sn–C), 419(Sn–N).
Compound
1
2
Empirical formula
Formula weight
Temperature (K)
C26H32N2O3Sn
539.23
298(2)
C20H31NO3Sn
452.15
298(2)
˚
Wavelength (A)
0.71073
Triclinic
0.71073
Orthorhombic
P2(1)2(1)2(1)
[(PhCH2)2Sn(Sal-T)] (5): Yield: 73%, m.p. 202–204
ꢁC. Anal. Found: C, 63.50; H, 4.72; N, 4.77; Sn,
19.47%. Calc. for C32H28N2O3Sn: C, 63.29; H, 4.65;
N, 4.61; Sn, 19.54. 1H NMR (CDCl3): 8.18(1H, s,
CH‚N), 7.97(1H, s, N–H), 6.85–7.84(19H, m, aromat-
ic-H), 4.25(1H, d, J=9.4 Hz, CHAr), 3.77(1H, d, J=9.4
Hz, CHAr), 3.11(1H, q, J=10.0 Hz, NCHCO), 3.01(4H,
Crystal system
Space group
Unit cell dimensions
ꢀ
P1
˚
a (A)
10.299(4)
11.332(4)
12.444(4)
101.812(5)
1236(8)
2
9.199(19)
10.01(2)
23.45(5)
90
˚
b (A)
˚
c (A)
b (ꢁ)
Volume (A )
3
˚
2155(8)
4
1.394
t, J=78.5 Hz, CH2Sn). 13C NMR (CDCl3):
d
Z
173.91(CH‚N), 172.06(COO), 68.59(‚NCH), 32.04-
(CH2Ar), 30.87(CH2Sn), 169.35, 138.27, 137.70,
136.81, 136.47, 135.50, 131.02, 130.10, 128.72, 126.52,
124.23, 122.58, 122.47, 118.74, 117.65, 116.72, 115.73,
109.57(Ar–C). 119Sn NMR d À348.05. IR (KBr,
cmÀ1): 3425(N–H), 1653, 1333(CO2), 1605(C‚N), 582,
547 (Sn–O), 448(Sn–C), 424(Sn–N).
[(PhCH2)2Sn(Sal-V)] (6): Yield: 77%, m.p. 178–179
ꢁC. Anal. Found: C, 60.25; H, 5.18; N, 2.73; Sn,
22.69%. Calc. for C26H27NO3Sn: C, 60.03; H, 5.23; N,
2.69; Sn, 22.82. 1H NMR (CDCl3): 8.18(1H, s, CH‚N),
N), 7.03–7.92(14H, m, aromatic-H), 3.97(1H, d, J=5.0
Hz, NCHCO), 2.99(4H, t, J=80.2 Hz, CH2Sn),
2.36(1H, m, CHMe2), 0.96(3H, d, J=6.6 Hz, CH3),
0.86(3H, d, J=6.6 Hz, CH3). 13C NMR (CDCl3): d
Calculated density
(Mg/m3)
F(000)
1.449
552
928
Crystal size (mm)
Scan range h (ꢁ)
Limiting indices
0.38·0.32·0.26
1.76–25.03
À126h610;
À136k612;
À146l614
6530/4312/0.0211
0.989
0.42·0.25·0.19
1.74–25.02
À106h69;
À116k611;
À266l627
10885/3737/0.0382
0.959
Total/unique/Rint
Goodness-of-fit on F2
R1/wR2
0.0373/0.0847
1.062
0.0380/0.0806
1.202
l (mmÀ1
max/qmin (e A
)
À3
˚
q
)
0.601/À0.592
0.981/À0.614
CH2Sn), 2.34(1H, m, CHMe2), 0.94(3H, d, J=6.4 Hz,
CH3), 0.85(3H, d, J=6.4 Hz, CH3). 13C NMR (CDCl3):
173.46(CH‚N),
172.88(COO),
74.85(‚NCH),
d
173.32(CH‚N), 172.24(COO), 74.57(‚NCH),
30.18(CH2Sn), 169.65, 137.80, 135.62, 135.32, 134.23,
130.28, 129.15, 123.01, 117.42, 117.38(Ar–C), 34.92,
19.52, 18.63(Pr-i). 119Sn NMR d À334.03. IR (KBr,
cmÀ1): 1663, 1341(CO2), 1610(C‚N), 581, 547(Sn–O),
457(Sn–C), 417(Sn–N).
30.24(CH2Sn), 169.72, 168.89, 146.42, 135.98, 135.64,
130.02, 122.69, 120.11, 117.51, 117.42(Ar–C), 34.72,
19.21, 18.63(Pr-i). 119Sn NMR d À321.75. IR (KBr,
cmÀ1): 1661, 1330(CO2), 1613(C‚N), 590, 551(Sn–O),
457(Sn–C), 423(Sn–N).
[(4-ClC6H4CH2)2Sn(Sal-T)] (7): Yield: 73%, m.p.
233–235 ꢁC. Anal. Found: C, 556.98; H, 4.00; N, 4.09;
Sn, 17.61%. Calc. for C32H26N2O3Cl2Sn: C, 56.84; H,
2.4. X-ray crystallography
1
3.88; N, 4.14; Sn, 17.55. H NMR (CDCl3): 8.13(1H,
Crystallographic data and refinement details are given
in Table 2. All X-ray crystallographic data were collected
on a Bruker SMART CCD 1000 diffractometer. A crite-
rion of observability was used for the solution and refine-
ment. The structure was solved by direct method and
differential Fourier map using SHELXL-97 program, and
refined by full-matrix least-squares on F2. All non-hydro-
gen atoms were refined anisotropically. Position of hy-
drogen atoms were calculated and refined isotropically.
s, CH‚N), 7.94(1H, s, N–H), 6.55–7.90(17H, m, aro-
matic-H), 4.21(1H, d, J=11.4 Hz, CHAr), 3.82(1H, d,
J=11.4 Hz, CHAr), 3.16(1H, q, J=9.6 Hz, NCHCO),
2.98(4H, t, J=76.2 Hz, CH2Sn). 13C NMR (CDCl3): d
173.80(CH‚N),
172.11(COO),
68.64(‚NCH),
32.12(CH2Ar), 30.55(CH2Sn), 169.82, 168.43, 148.57,
137.63, 136.21, 134.30, 130.02, 126.49, 125.01, 124.37,
124.25, 123.02, 121.87, 120.47, 119.01, 117.13, 116.65,
111.30(Ar–C). 119Sn NMR d À337.65. IR (KBr,
cmÀ1): 3436(N–H), 1653, 1336(CO2), 1607(C‚N), 589,
546 (Sn–O), 441(Sn–C), 422(Sn–N).
3. Results and discussion
[(4-ClC6H4CH2)2Sn(Sal-V)] (8): Yield: 76%, m.p.
209–210 ꢁC. Anal. Found: C, 53.24; H, 4.30; N, 2.34;
Sn, 20.25%. Calc. for C26H25NO3Cl2Sn: C, 53.01; H,
4.28; N, 2.38; Sn, 20.15. H NMR (CDCl3): 8.20(1H,
s, CH‚N), 6.84–7.92(12H, m, aromatic-H), 3.92(1H,
d, J=5.0 Hz, NCHCO), 2.96(4H, t, J=77.8 Hz,
3.1. IR data
1
The assignment of IR bands of diorganotin(IV) com-
pounds 1–8 has been determined by comparison with