H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 435–440
437
Table 1
Crystal date and details of structure refinement for {[nBu2Sn(LH)]2O}2
(1) and Ph3Sn(LH) (5)
2.3.5. Ph3Sn(LH) (5)
Orange crystals 0.513, yield 87%. M.p. 125–127 ꢁC.
Anal. Calc. for C32H25NO3Sn: C, 65.12; H, 4.27; N,
2.37; Sn, 20.11. Found: C, 65.09; H, 4.28; N, 2.35; Sn,
20.09%. 1H NMR (CDCl3): 13.01 (1H, s, Ar–OH),
8.62(1H, s, N@CAH), 8.20(2H, d, H(a)), 7.81(6H, t,
SnPh–H,), 7.51(2H, d, H(b)), 6.94–7.47(13H, m, Ar–H
& SnPh–H);119Sn NMR (CDCl3): À204.7; IR (KBr):
m(OH), 3428 cmÀ1, m(C@N), 1620 cmÀ1, mas(COO),
Complex
1
5
Empirical formula
Formula weight
Crystal size (mm)
Crystal system
C88H112N4O14Sn4
1924.58
C32H 25NO3Sn
590.22
0.39 · 0.34 · 0.27
Triclinic
0.42 · 0.35 · 0.09
Monoclinic
P21/c
ꢀ
Space group
Unit cell dimensions
P1
1598 cmÀ1, ms(COO), 1408 cmÀ1; m(Sn–C), 563 cmÀ1
m(Sn–O), 442 cmÀ1
,
˚
a (A)
12.352(9)
12.875(10)
15.267(11)
102.559(11)
1.358
6.8950(14)
46.350(3)
8.7250(17)
95.472(3)
1.412
˚
b (A)
.
˚
c (A)
b (ꢁ)
Dcalc density (mg/m3)
F(000)
2.3.6. Cy3Sn(LH) (6)
Orange crystals 0.441 g, yield 73%. M.p. 117–119 ꢁC.
Anal. Calc. for C32H40NO3Sn: C, 63.49; H, 6.66; N,
2.31; Sn, 19.61. Found: C, 63.47; H, 6.69; N, 2.35; Sn,
19.59%. 1H NMR (CDCl3): 13.08 (1H, s, Ar–OH),
8.62(1H, s, N@CAH), 8.12(2H, d, H(a)), 7.43(2H, d,
H(b)), 6.93–7.30(4H, m, Ar–H), 1.35–1.97(30H, m,
SnCy–H);119Sn NMR (CDCl3): À207.2; IR (KBr):
m(OH), 3393 cmÀ1, m(C@N), 1624 cmÀ1, mas(COO),
980
1192
Scan range h (ꢁ)
Total/unique/Rint
Goodness-of-fit on F2
R1/wR2
1.59–25.02
11959/8128/0.0238
0.963
1.76–25.03
10364/3922/0.1001
1.017
0.0471/0.1085
1.107
0.0748/0.1602
0.953
l (mmÀ1
max/qmin (e A
)
À3
˚
q
)
0.897/À0.480
0.699/À1.335
(CDCl3): À207.7; IR (KBr): m(OH), 3408 cmÀ1
,
m(C@N), 1614 cmÀ1, mas(COO), 1598 cmÀ1, ms(COO),
1595 cmÀ1, ms(COO), 1414 cmÀ1; m(Sn–C), 533 cmÀ1
m(Sn–O), 430 cmÀ1
,
1411 cmÀ1; m(Sn–C), 562 cmÀ1, m(Sn–O), 460 cmÀ1
.
.
2.3.10. (4-Cl-PhCH2)3Sn(LH) (10)
2.3.7. Bz3Sn(LH) (7)
Orange crystals 0.617 g, yield 84%. M.p. 124–126 ꢁC.
Anal. Calc. for C35H28Cl3NO3Sn: C, 57.14; H, 3.84; N,
1.90; Sn, 16.14. Found: C, 57.15; H, 3.83; N, 1.93; Sn,
16.12%. 1H NMR (CDCl3): 12.92 (1H, s, Ar–OH),
8.66(1H, s, N@CAH), 8.06(2H, d, H(a)), 7.44(2H, d,
H(b)), 6.77–7.42(16H, m, Ar–H & Ph–H), 2.70(6H, t,
SnCH2, JSn–H = 67.61);119Sn NMR (CDCl3): À208.2;
Orange crystals 0.480 g, yield 76%. M.p. 123–125 ꢁC.
Anal. Calc. for C35H31NO3Sn: C, 66.48; H, 4.94; N,
2.22; Sn, 18.77. Found: C, 66.46; H, 4.91; N, 2.25; Sn,
18.76%. 1H NMR (CDCl3): 13.03 (1H, s, Ar–OH),
8.66(1H, s, N@CAH), 8.08(2H, d, H(a)), 7.42(2H, d,
H(b)), 6.81–7.38(19H, m, Ar–H & Ph–H), 2.69(6H, t,
SnCH2, JSn–H = 69.63);119Sn NMR (CDCl3): À210.3;
IR (KBr): m(OH), 3420 cmÀ1, m(C@N), 1620 cmÀ1
,
IR (KBr): m(OH), 3387 cmÀ1, m(C@N), 1608 cmÀ1
,
mas(COO), 1601 cmÀ1, ms(COO), 1418 cmÀ1; m(Sn–O),
mas(COO), 1596 cmÀ1, ms(COO), 1402 cmÀ1; m(Sn–C),
528 cmÀ1, m(Sn–O), 455 cmÀ1
557 cmÀ1, m(Sn–C), 451 cmÀ1
.
.
2.4. X-ray crystallography
2.3.8. (2-Cl-PhCH2)3Sn(LH) (8)
Orange crystals 0.632 g, yield 86%. M.p. 119–121 ꢁC.
Anal. Calc. for C35H28Cl3NO3Sn: C, 57.14; H, 3.84; N,
1.90; Sn, 16.14. Found: C, 57.12; H, 3.86; N, 1.91; Sn,
16.11%. 1H NMR (CDCl3): 13.03 (1H, s, Ar–OH),
8.66(1H, s, N@CAH), 8.05(2H, d, H(a)), 7.45(2H, d,
H(b)), 6.75–7.41(16H, m, Ar–H & Ph–H), 2.79(6H, t,
SnCH2, J Sn–H = 68.75); 119Sn NMR (CDCl3): À205.8;
X-ray crystallographic data for the complexes 1 and 5
were collected on a Bruker smart-1000 CCD diffractom-
˚
eter at 293(2) K using Mo Ka radiations (0.71073 A).
The structures were solved by direct method and differ-
ence Fourier map using SHELXL-97 program, and
refined by full-matrix least-squares on F2. All non-hy-
drogen atoms were refined anisotropically. Hydrogen
atoms were located at calculated positions and refined
isotropically. Further details are given in Table 1.
IR (KBr): m(OH), 3431 cmÀ1, m(C@N), 1618 cmÀ1
,
mas(COO), 1597 cmÀ1, ms(COO), 1398 cmÀ1; m(Sn–C),
563 cmÀ1, m(Sn–O), 458 cmÀ1
.
2.3.9. (4-F-PhCH2)3Sn(LH) (9)
3. Results and discussion
Orange crystals 0.528 g, yield 77%. M.p. 127–129
ꢁC. Anal. Calc. for C35H28F3NO3Sn: C, 61.25; H,
4.11; N, 2.04; Sn, 17.30. Found: C, 61.24; H, 4.13;
N, 2.06; Sn, 17.27%. 1H NMR (CDCl3): 12.98 (1H,
s, Ar–OH), 8.66(1H, s, N@CAH), 8.06(2H, d, H(a)),
7.43(2H, d, H(b)), 6.61–7.36(16H, m, Ar–H & Ph–
H), 2.69(6H, t, SnCH2, JSn–H = 71.45);119Sn NMR
3.1. Crystal structures
The ORTEP drawings of complexes 1 and 5 are
shown in Figs. 1 and 2. The selected bond lengths and
angles are listed in Tables 2 and 3.