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Acta Cryst. (2007). E63, m2599    [ doi:10.1107/S1600536807046338 ]

[4-(2-Hydroxybenzylideneamino)benzenethiolato]triphenyltin(IV)

J. Du, J. Li, C. Ma and G. He

Abstract top

The title mononuclear Schiff base compound, [Sn(C6H5)3{SC6H4-4-N=C(H)C6H4-OH-2}], contains two essentially identical molecules in the asymmetric unit, each of which features a slightly distorted C3S tetrahedral geometry for the Sn atom.

Comment top

Recently, a number of Schiff-bases have been investigated in terms of their crystallography and coordination chemistry (Garnovski et al., 1993). During the last decade, Schiff-base complexes have been applied in catalytic reactions and biological systems (Anderson et al., 1997). Organotin complexes containing Schiff-bases have attracted much attention owing to their potential biological activities (Nath et al., 1997). The title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). Two independent molecules comprise the crystallographic asymmetric unit. In each of these, the central tin atom exists in a distorted tetrahedron defined by a C3S donor set. The geometric parameters are in good agreement with those found in (4,5-diphenyl-4-oxazoline-2-thiolato)triphenyltin (Li et al., 2007). The mean planes of the two benzene rings in (I) make a dihedral angle of 31.0 (5)° (molecule 1) and 31.3 (6)° (molecule 2) showing that the Schiff-base ligand adopts a non-planar conformation in each case.

Related literature top

For related literature, see: Anderson et al. (1997); Li et al. (2007); Garnovski et al. (1993); Nath et al. (1997).

Experimental top

The Schiff-base ligand was synthesized by the reaction of salicylaldehyde and 4-aminothiophenol in ethanol solution. Under an N2 atmosphere, the Schiff-base (0.229 g, 1 mmol) and (C6H5)3SnCl (0.385 g, 1 mmol) were added to a solution of dry benzene (30 ml) in a Schlenk flask and stirred under reflux conditions (353 K) for 12 h. The solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.503 g, 82%. m.p. 430–432 K.

Analysis found: C 64.32, H 4.45, N 2.38, O 2.75, S 5.50%; C19H19NOSSn requires: C 64.38, H 4.36, N 2.42, O 2.77, S 5.54%.

Refinement top

The H-atoms were included in the riding-model approximation with C—H = 0.93 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C-aromatic) and Uiso(H) = 1.5Ueq(O). The maximum and minimum residual electron denisty peaks were located 1.68 and 1.20 Å, respectively, from the O2 and Sn2 atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of one of the two independent molecules in (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of one of the two independent molecules in (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.
[4-(2-Hydroxybenzylideneamino)benzenethiolato]triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C13H10NOS)]Z = 4
Mr = 578.27F(000) = 1168
Triclinic, P1Dx = 1.447 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5561 (10) ÅCell parameters from 4515 reflections
b = 9.6073 (11) Åθ = 2.3–24.1°
c = 30.110 (3) ŵ = 1.07 mm−1
α = 92.064 (2)°T = 298 K
β = 95.430 (2)°Block, yellow
γ = 104.936 (3)°0.15 × 0.12 × 0.10 mm
V = 2653.8 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		9194 independent reflections
Radiation source: sealed tube6702 reflections with I > 2σ(I)
graphiteRint = 0.046
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.857, Tmax = 0.901k = −11→11
13756 measured reflectionsl = −35→24
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + 13.8664P]
where P = (Fo2 + 2Fc2)/3
9194 reflections(Δ/σ)max = 0.001
631 parametersΔρmax = 0.58 e Å−3
0 restraintsΔρmin = −1.26 e Å−3
Crystal data top
[Sn(C6H5)3(C13H10NOS)]γ = 104.936 (3)°
Mr = 578.27V = 2653.8 (5) Å3
Triclinic, P1Z = 4
a = 9.5561 (10) ÅMo Kα radiation
b = 9.6073 (11) ŵ = 1.07 mm−1
c = 30.110 (3) ÅT = 298 K
α = 92.064 (2)°0.15 × 0.12 × 0.10 mm
β = 95.430 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		9194 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6702 reflections with I > 2σ(I)
Tmin = 0.857, Tmax = 0.901Rint = 0.046
13756 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.064 w = 1/[σ2(Fo2) + 13.8664P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142Δρmax = 0.58 e Å−3
S = 1.00Δρmin = −1.26 e Å−3
9194 reflectionsAbsolute structure: ?
631 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.83590 (5)0.29973 (5)0.379460 (17)0.04023 (15)
Sn20.18962 (6)0.14815 (6)0.123781 (17)0.04579 (17)
N10.8033 (7)0.2038 (6)0.6046 (2)0.0445 (15)
N20.3049 (7)0.2040 (7)−0.0979 (2)0.0497 (16)
O10.9884 (6)0.3102 (7)0.6745 (2)0.0760 (18)
H10.95930.28910.64800.114*
O20.2069 (8)0.0204 (6)−0.1663 (2)0.082 (2)
H20.22700.0490−0.13990.123*
S10.6851 (2)0.0845 (2)0.40714 (7)0.0572 (6)
S20.4112 (2)0.3014 (3)0.10086 (7)0.0626 (6)
C10.7213 (8)0.1246 (7)0.4656 (2)0.0429 (18)
C20.8510 (9)0.1208 (8)0.4893 (3)0.053 (2)
H2A0.92350.09900.47400.063*
C30.8760 (8)0.1484 (8)0.5349 (3)0.051 (2)
H30.96540.14750.54980.061*
C40.7693 (8)0.1772 (7)0.5583 (3)0.0419 (17)
C50.6407 (8)0.1816 (8)0.5353 (3)0.051 (2)
H50.56790.20180.55080.062*
C60.6166 (8)0.1569 (8)0.4900 (3)0.051 (2)
H60.52830.16180.47520.061*
C70.7035 (9)0.1796 (8)0.6311 (3)0.051 (2)
H70.60750.13990.61910.061*
C80.7341 (9)0.2112 (8)0.6789 (3)0.0480 (19)
C90.8756 (9)0.2730 (8)0.6991 (3)0.052 (2)
C100.9019 (11)0.2999 (10)0.7448 (3)0.068 (2)
H100.99590.34200.75820.081*
C110.7879 (11)0.2639 (10)0.7704 (3)0.066 (2)
H110.80630.28300.80120.080*
C120.6478 (12)0.2006 (10)0.7521 (3)0.070 (3)
H120.57210.17620.77010.085*
C130.6225 (10)0.1743 (9)0.7064 (3)0.062 (2)
H130.52820.13080.69350.075*
C140.7899 (7)0.4815 (7)0.4112 (2)0.0368 (16)
C150.8120 (9)0.5105 (8)0.4571 (2)0.055 (2)
H150.85180.45120.47530.066*
C160.7750 (10)0.6266 (9)0.4756 (3)0.071 (3)
H160.78610.64330.50650.085*
C170.7216 (10)0.7190 (9)0.4491 (4)0.070 (3)
H170.69910.79920.46180.084*
C180.7028 (10)0.6922 (9)0.4055 (3)0.070 (3)
H180.66700.75490.38760.084*
C190.7343 (9)0.5744 (7)0.3855 (3)0.053 (2)
H190.71810.55760.35460.063*
C200.7698 (7)0.2763 (7)0.3100 (2)0.0404 (17)
C210.6255 (8)0.2188 (9)0.2936 (3)0.057 (2)
H210.55580.19190.31340.068*
C220.5833 (10)0.2009 (10)0.2481 (3)0.069 (3)
H220.48640.16020.23730.083*
C230.6877 (11)0.2443 (10)0.2189 (3)0.070 (3)
H230.66060.23300.18820.084*
C240.8268 (12)0.3024 (11)0.2345 (3)0.075 (3)
H240.89610.33170.21460.090*
C250.8690 (9)0.3195 (9)0.2807 (3)0.056 (2)
H250.96600.36100.29130.067*
C261.0586 (7)0.3039 (7)0.3935 (2)0.0353 (15)
C271.1091 (9)0.1821 (8)0.3947 (3)0.0479 (19)
H271.04300.09160.39050.058*
C281.2557 (9)0.1921 (9)0.4023 (3)0.060 (2)
H281.28730.10830.40300.072*
C291.3557 (9)0.3235 (10)0.4086 (3)0.058 (2)
H291.45450.32980.41460.070*
C301.3080 (9)0.4440 (9)0.4061 (3)0.064 (2)
H301.37480.53410.40870.077*
C311.1602 (9)0.4342 (8)0.3998 (3)0.054 (2)
H311.12930.51850.39990.065*
C320.3776 (8)0.2722 (8)0.0419 (3)0.0488 (19)
C330.3434 (10)0.3769 (10)0.0168 (3)0.064 (2)
H330.33510.46180.03090.077*
C340.3212 (10)0.3583 (9)−0.0289 (3)0.065 (2)
H340.30040.4320−0.04540.078*
C350.3290 (8)0.2332 (8)−0.0509 (3)0.0444 (18)
C360.3589 (9)0.1266 (8)−0.0257 (3)0.055 (2)
H360.36180.0397−0.03970.066*
C370.3850 (9)0.1462 (9)0.0206 (3)0.057 (2)
H370.40760.07360.03720.068*
C380.3319 (7)0.3032 (8)−0.1252 (3)0.049 (2)
H380.37010.3981−0.11370.058*
C390.3061 (8)0.2756 (9)−0.1726 (3)0.053 (2)
C400.2437 (9)0.1339 (9)−0.1923 (3)0.058 (2)
C410.2205 (11)0.1116 (10)−0.2381 (3)0.071 (3)
H410.17950.0190−0.25120.085*
C420.2583 (10)0.2268 (12)−0.2648 (3)0.073 (3)
H420.24350.2116−0.29570.087*
C430.3175 (11)0.3630 (12)−0.2456 (4)0.079 (3)
H430.34290.4402−0.26360.095*
C440.3394 (10)0.3865 (9)−0.2005 (3)0.067 (2)
H440.37810.4803−0.18820.080*
C450.0125 (8)0.1969 (7)0.0849 (3)0.0459 (18)
C46−0.0866 (10)0.2497 (9)0.1066 (3)0.070 (3)
H46−0.07720.25900.13770.084*
C47−0.1986 (10)0.2886 (9)0.0826 (3)0.071 (3)
H47−0.26270.32700.09740.085*
C48−0.2159 (10)0.2708 (10)0.0366 (3)0.072 (3)
H48−0.29300.29500.02040.086*
C49−0.1210 (9)0.2182 (11)0.0153 (3)0.074 (3)
H49−0.13190.2067−0.01570.089*
C50−0.0074 (9)0.1813 (10)0.0397 (3)0.060 (2)
H500.05720.14470.02460.072*
C510.2063 (8)0.2095 (8)0.1928 (2)0.0425 (17)
C520.2661 (9)0.3513 (9)0.2087 (3)0.053 (2)
H520.29550.42240.18880.064*
C530.2822 (10)0.3874 (10)0.2542 (3)0.070 (3)
H530.32170.48310.26460.084*
C540.2416 (11)0.2861 (12)0.2837 (3)0.071 (3)
H540.25220.31160.31410.086*
C550.1846 (11)0.1458 (11)0.2682 (3)0.074 (3)
H550.15790.07550.28850.088*
C560.1659 (9)0.1061 (9)0.2231 (3)0.058 (2)
H560.12630.00990.21310.070*
C570.1900 (7)−0.0722 (7)0.1137 (2)0.0440 (17)
C580.0583 (8)−0.1736 (8)0.1075 (3)0.062 (2)
H58−0.0271−0.14400.10740.074*
C590.0497 (10)−0.3186 (10)0.1016 (3)0.077 (3)
H59−0.0410−0.38530.09680.093*
C600.1745 (10)−0.3652 (10)0.1027 (3)0.069 (3)
H600.1690−0.46320.09970.083*
C610.3038 (11)−0.2672 (10)0.1081 (4)0.082 (3)
H610.3886−0.29750.10770.098*
C620.3137 (8)−0.1205 (9)0.1143 (3)0.069 (2)
H620.4047−0.05460.11900.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0453 (3)0.0343 (3)0.0401 (3)0.0108 (2)−0.0004 (2)−0.0004 (2)
Sn20.0435 (3)0.0486 (3)0.0428 (3)0.0098 (3)0.0006 (2)−0.0022 (2)
N10.051 (4)0.034 (3)0.049 (4)0.012 (3)0.003 (3)0.010 (3)
N20.044 (4)0.046 (4)0.060 (4)0.011 (3)0.010 (3)0.005 (3)
O10.049 (4)0.112 (5)0.056 (4)0.005 (3)0.000 (3)0.004 (4)
O20.136 (6)0.050 (4)0.058 (4)0.015 (4)0.024 (4)0.008 (3)
S10.0698 (14)0.0401 (11)0.0488 (12)−0.0052 (10)−0.0032 (10)0.0021 (9)
S20.0473 (12)0.0721 (15)0.0532 (13)−0.0083 (11)−0.0003 (10)−0.0045 (11)
C10.052 (5)0.026 (3)0.044 (4)−0.001 (3)0.000 (4)0.004 (3)
C20.053 (5)0.057 (5)0.052 (5)0.020 (4)0.009 (4)0.011 (4)
C30.041 (4)0.055 (5)0.054 (5)0.009 (4)−0.002 (4)0.009 (4)
C40.046 (4)0.026 (4)0.051 (5)0.004 (3)0.004 (4)0.002 (3)
C50.041 (5)0.059 (5)0.050 (5)0.008 (4)0.002 (4)−0.003 (4)
C60.041 (5)0.050 (5)0.060 (5)0.011 (4)−0.002 (4)0.009 (4)
C70.054 (5)0.033 (4)0.061 (5)0.005 (4)0.000 (4)−0.002 (4)
C80.053 (5)0.039 (4)0.054 (5)0.015 (4)0.005 (4)0.002 (4)
C90.053 (5)0.049 (5)0.051 (5)0.012 (4)0.003 (4)0.004 (4)
C100.068 (6)0.085 (7)0.053 (6)0.028 (5)−0.003 (5)0.005 (5)
C110.088 (7)0.065 (6)0.050 (5)0.027 (5)0.004 (5)0.002 (4)
C120.083 (7)0.069 (6)0.064 (6)0.021 (5)0.027 (5)0.013 (5)
C130.055 (5)0.065 (6)0.067 (6)0.013 (4)0.014 (5)0.014 (5)
C140.031 (4)0.032 (4)0.049 (4)0.009 (3)0.006 (3)0.006 (3)
C150.080 (6)0.037 (4)0.046 (5)0.015 (4)0.002 (4)−0.001 (4)
C160.084 (7)0.062 (6)0.059 (6)0.008 (5)0.015 (5)−0.020 (5)
C170.064 (6)0.047 (5)0.102 (8)0.019 (5)0.019 (6)−0.025 (5)
C180.073 (6)0.053 (5)0.089 (8)0.029 (5)0.004 (5)0.003 (5)
C190.059 (5)0.041 (4)0.059 (5)0.015 (4)0.002 (4)0.005 (4)
C200.050 (5)0.033 (4)0.042 (4)0.018 (3)0.006 (4)0.004 (3)
C210.049 (5)0.067 (5)0.053 (5)0.012 (4)0.002 (4)0.000 (4)
C220.063 (6)0.076 (6)0.062 (6)0.016 (5)−0.019 (5)−0.007 (5)
C230.099 (8)0.076 (6)0.038 (5)0.035 (6)−0.009 (5)−0.003 (5)
C240.088 (8)0.087 (7)0.053 (6)0.023 (6)0.019 (5)−0.003 (5)
C250.048 (5)0.059 (5)0.055 (5)0.006 (4)0.004 (4)−0.005 (4)
C260.043 (4)0.029 (3)0.035 (4)0.013 (3)0.000 (3)−0.002 (3)
C270.056 (5)0.033 (4)0.055 (5)0.011 (4)0.008 (4)0.008 (3)
C280.060 (6)0.051 (5)0.080 (6)0.035 (5)0.009 (5)0.021 (5)
C290.050 (5)0.077 (6)0.054 (5)0.028 (5)0.002 (4)0.012 (5)
C300.054 (5)0.046 (5)0.081 (7)−0.004 (4)−0.002 (5)−0.002 (4)
C310.052 (5)0.030 (4)0.080 (6)0.017 (4)−0.005 (4)−0.003 (4)
C320.038 (4)0.053 (5)0.053 (5)0.006 (4)0.012 (4)0.004 (4)
C330.081 (7)0.058 (5)0.051 (5)0.014 (5)0.006 (5)−0.004 (4)
C340.087 (7)0.048 (5)0.066 (6)0.026 (5)0.007 (5)0.005 (4)
C350.034 (4)0.047 (4)0.049 (5)0.005 (3)0.004 (3)−0.001 (4)
C360.065 (6)0.044 (4)0.061 (6)0.021 (4)0.018 (4)0.007 (4)
C370.062 (5)0.062 (5)0.057 (5)0.029 (4)0.018 (4)0.018 (4)
C380.032 (4)0.039 (4)0.070 (6)0.002 (3)0.003 (4)−0.002 (4)
C390.041 (5)0.051 (5)0.068 (6)0.011 (4)0.004 (4)0.008 (4)
C400.060 (5)0.061 (5)0.054 (5)0.017 (4)0.008 (4)0.010 (4)
C410.088 (7)0.064 (6)0.057 (6)0.016 (5)0.008 (5)−0.004 (5)
C420.072 (7)0.111 (9)0.048 (5)0.043 (6)0.008 (5)0.009 (6)
C430.073 (7)0.082 (7)0.075 (7)0.008 (6)−0.004 (6)0.026 (6)
C440.073 (6)0.051 (5)0.070 (7)0.007 (5)0.000 (5)0.010 (5)
C450.045 (4)0.040 (4)0.054 (5)0.009 (3)0.010 (4)0.008 (4)
C460.071 (6)0.063 (6)0.079 (7)0.022 (5)0.020 (5)0.003 (5)
C470.055 (6)0.054 (5)0.107 (9)0.018 (5)0.022 (6)0.005 (5)
C480.055 (6)0.064 (6)0.100 (8)0.026 (5)−0.013 (6)0.012 (6)
C490.063 (6)0.090 (7)0.059 (6)0.010 (5)−0.012 (5)0.000 (5)
C500.053 (5)0.082 (6)0.046 (5)0.025 (5)−0.001 (4)−0.012 (4)
C510.041 (4)0.044 (4)0.044 (4)0.014 (3)0.002 (3)0.003 (3)
C520.065 (5)0.054 (5)0.041 (5)0.019 (4)0.003 (4)0.001 (4)
C530.081 (7)0.065 (6)0.065 (6)0.023 (5)0.004 (5)−0.021 (5)
C540.076 (7)0.097 (8)0.050 (6)0.035 (6)0.018 (5)0.002 (6)
C550.097 (8)0.084 (7)0.052 (6)0.037 (6)0.025 (5)0.023 (5)
C560.071 (6)0.055 (5)0.051 (5)0.020 (4)0.009 (4)0.010 (4)
C570.037 (4)0.052 (4)0.043 (4)0.010 (3)0.007 (3)0.001 (3)
C580.043 (4)0.049 (5)0.095 (6)0.017 (4)0.003 (4)−0.005 (4)
C590.067 (6)0.064 (6)0.092 (8)0.009 (5)−0.003 (5)−0.011 (5)
C600.082 (7)0.054 (5)0.076 (7)0.022 (5)0.017 (5)0.006 (5)
C610.075 (7)0.081 (7)0.119 (9)0.059 (6)0.036 (6)0.033 (6)
C620.044 (5)0.078 (6)0.085 (6)0.017 (4)0.007 (4)0.016 (5)
Geometric parameters (Å, °) top
Sn1—S12.421 (2)C27—C281.376 (11)
Sn1—C142.124 (6)C27—H270.9300
Sn1—C202.113 (7)C28—C291.367 (12)
Sn1—C262.120 (7)C28—H280.9300
Sn2—S22.423 (2)C29—C301.351 (11)
Sn2—C452.127 (7)C29—H290.9300
Sn2—C512.120 (7)C30—C311.385 (11)
Sn2—C572.129 (7)C30—H300.9300
N1—C71.281 (9)C31—H310.9300
N1—C41.401 (9)C32—C331.366 (11)
N2—C381.273 (9)C32—C371.370 (11)
N2—C351.417 (10)C33—C341.370 (12)
O1—C91.345 (9)C33—H330.9300
O1—H10.8200C34—C351.375 (11)
O2—C401.358 (9)C34—H340.9300
O2—H20.8200C35—C361.369 (10)
S1—C11.771 (7)C36—C371.391 (11)
S2—C321.774 (8)C36—H360.9300
C1—C21.379 (10)C37—H370.9300
C1—C61.385 (10)C38—C391.429 (11)
C2—C31.374 (11)C38—H380.9300
C2—H2A0.9300C39—C441.372 (11)
C3—C41.372 (10)C39—C401.420 (11)
C3—H30.9300C40—C411.376 (12)
C4—C51.365 (10)C41—C421.383 (13)
C5—C61.363 (11)C41—H410.9300
C5—H50.9300C42—C431.367 (13)
C6—H60.9300C42—H420.9300
C7—C81.445 (11)C43—C441.355 (13)
C7—H70.9300C43—H430.9300
C8—C131.394 (11)C44—H440.9300
C8—C91.398 (11)C45—C501.356 (10)
C9—C101.379 (11)C45—C461.386 (8)
C10—C111.373 (12)C46—C471.374 (12)
C10—H100.9300C46—H460.9300
C11—C121.372 (13)C47—C481.377 (8)
C11—H110.9300C47—H470.9300
C12—C131.378 (12)C48—C491.346 (12)
C12—H120.9300C48—H480.9300
C13—H130.9300C49—C501.381 (8)
C14—C191.376 (9)C49—H490.9300
C14—C151.386 (7)C50—H500.9300
C15—C161.370 (11)C51—C561.378 (10)
C15—H150.9300C51—C521.383 (10)
C16—C171.376 (8)C52—C531.385 (11)
C16—H160.9300C52—H520.9300
C17—C181.314 (12)C53—C541.348 (13)
C17—H170.9300C53—H530.9300
C18—C191.377 (8)C54—C551.363 (13)
C18—H180.9300C54—H540.9300
C19—H190.9300C55—C561.380 (12)
C20—C251.353 (10)C55—H550.9300
C20—C211.382 (7)C56—H560.9300
C21—C221.382 (11)C57—C581.371 (7)
C21—H210.9300C57—C621.375 (7)
C22—C231.386 (8)C58—C591.378 (11)
C22—H220.9300C58—H580.9300
C23—C241.334 (13)C59—C601.376 (8)
C23—H230.9300C59—H590.9300
C24—C251.404 (8)C60—C611.339 (12)
C24—H240.9300C60—H600.9300
C25—H250.9300C61—C621.392 (8)
C26—C311.367 (10)C61—H610.9300
C26—C271.376 (9)C62—H620.9300
C20—Sn1—C26111.6 (3)C30—C29—C28118.6 (8)
C20—Sn1—C14112.9 (2)C30—C29—H29120.7
C26—Sn1—C14111.1 (2)C28—C29—H29120.7
S1—Sn1—C14107.92 (18)C29—C30—C31120.5 (8)
S1—Sn1—C20103.24 (19)C29—C30—H30119.8
S1—Sn1—C26109.69 (18)C31—C30—H30119.8
Sn1—S1—C1101.2 (2)C26—C31—C30121.6 (7)
C51—Sn2—C45114.2 (3)C26—C31—H31119.2
C51—Sn2—C57111.1 (3)C30—C31—H31119.2
C45—Sn2—C57112.0 (3)C33—C32—C37118.8 (8)
S2—Sn2—C45107.0 (2)C33—C32—S2119.8 (6)
S2—Sn2—C51102.5 (2)C37—C32—S2121.4 (6)
S2—Sn2—C57109.46 (18)C32—C33—C34120.7 (8)
Sn2—S2—C32101.1 (2)C32—C33—H33119.6
C7—N1—C4121.3 (7)C34—C33—H33119.6
C38—N2—C35122.5 (7)C33—C34—C35121.4 (8)
C9—O1—H1109.5C33—C34—H34119.3
C40—O2—H2109.5C35—C34—H34119.3
C2—C1—C6116.8 (7)C36—C35—C34117.8 (8)
C2—C1—S1122.5 (6)C36—C35—N2117.1 (7)
C6—C1—S1120.6 (6)C34—C35—N2125.1 (7)
C3—C2—C1121.9 (8)C35—C36—C37121.0 (8)
C3—C2—H2A119.1C35—C36—H36119.5
C1—C2—H2A119.1C37—C36—H36119.5
C4—C3—C2120.2 (7)C32—C37—C36120.2 (8)
C4—C3—H3119.9C32—C37—H37119.9
C2—C3—H3119.9C36—C37—H37119.9
C5—C4—C3118.5 (7)N2—C38—C39123.0 (7)
C5—C4—N1124.8 (7)N2—C38—H38118.5
C3—C4—N1116.7 (7)C39—C38—H38118.5
C6—C5—C4121.4 (8)C44—C39—C40118.0 (8)
C6—C5—H5119.3C44—C39—C38120.6 (8)
C4—C5—H5119.3C40—C39—C38121.4 (7)
C5—C6—C1121.2 (7)O2—C40—C41119.8 (8)
C5—C6—H6119.4O2—C40—C39120.4 (8)
C1—C6—H6119.4C41—C40—C39119.7 (8)
N1—C7—C8122.7 (8)C40—C41—C42120.0 (9)
N1—C7—H7118.6C40—C41—H41120.0
C8—C7—H7118.6C42—C41—H41120.0
C13—C8—C9118.0 (8)C43—C42—C41120.0 (9)
C13—C8—C7120.2 (8)C43—C42—H42120.0
C9—C8—C7121.7 (7)C41—C42—H42120.0
O1—C9—C10118.5 (8)C44—C43—C42120.5 (9)
O1—C9—C8121.0 (7)C44—C43—H43119.7
C10—C9—C8120.4 (8)C42—C43—H43119.7
C11—C10—C9119.3 (9)C43—C44—C39121.7 (9)
C11—C10—H10120.3C43—C44—H44119.1
C9—C10—H10120.3C39—C44—H44119.1
C12—C11—C10122.3 (9)C50—C45—C46117.9 (8)
C12—C11—H11118.9C50—C45—Sn2123.3 (5)
C10—C11—H11118.9C46—C45—Sn2118.9 (6)
C11—C12—C13118.0 (9)C47—C46—C45120.6 (9)
C11—C12—H12121.0C47—C46—H46119.7
C13—C12—H12121.0C45—C46—H46119.7
C12—C13—C8121.9 (9)C46—C47—C48120.0 (8)
C12—C13—H13119.1C46—C47—H47120.0
C8—C13—H13119.1C48—C47—H47120.0
C19—C14—C15118.0 (7)C49—C48—C47119.8 (8)
C19—C14—Sn1119.2 (5)C49—C48—H48120.1
C15—C14—Sn1122.8 (5)C47—C48—H48120.1
C16—C15—C14119.9 (7)C48—C49—C50119.8 (9)
C16—C15—H15120.1C48—C49—H49120.1
C14—C15—H15120.1C50—C49—H49120.1
C15—C16—C17120.9 (8)C45—C50—C49121.9 (8)
C15—C16—H16119.6C45—C50—H50119.1
C17—C16—H16119.6C49—C50—H50119.1
C18—C17—C16119.0 (8)C56—C51—C52118.8 (7)
C18—C17—H17120.5C56—C51—Sn2120.1 (6)
C16—C17—H17120.5C52—C51—Sn2121.0 (5)
C17—C18—C19122.1 (9)C51—C52—C53119.9 (8)
C17—C18—H18118.9C51—C52—H52120.1
C19—C18—H18118.9C53—C52—H52120.1
C14—C19—C18120.1 (8)C54—C53—C52121.2 (9)
C14—C19—H19120.0C54—C53—H53119.4
C18—C19—H19120.0C52—C53—H53119.4
C25—C20—C21118.7 (7)C53—C54—C55119.1 (9)
C25—C20—Sn1120.1 (5)C53—C54—H54120.5
C21—C20—Sn1121.2 (6)C55—C54—H54120.5
C20—C21—C22120.9 (8)C54—C55—C56121.3 (9)
C20—C21—H21119.5C54—C55—H55119.3
C22—C21—H21119.5C56—C55—H55119.3
C21—C22—C23119.0 (8)C51—C56—C55119.7 (8)
C21—C22—H22120.5C51—C56—H56120.1
C23—C22—H22120.5C55—C56—H56120.1
C24—C23—C22120.4 (8)C58—C57—C62117.6 (7)
C24—C23—H23119.8C58—C57—Sn2117.9 (5)
C22—C23—H23119.8C62—C57—Sn2124.5 (5)
C23—C24—C25120.3 (9)C57—C58—C59121.4 (7)
C23—C24—H24119.9C57—C58—H58119.3
C25—C24—H24119.9C59—C58—H58119.3
C20—C25—C24120.6 (8)C60—C59—C58120.4 (9)
C20—C25—H25119.7C60—C59—H59119.8
C24—C25—H25119.7C58—C59—H59119.8
C31—C26—C27117.2 (7)C61—C60—C59118.9 (9)
C31—C26—Sn1119.0 (5)C61—C60—H60120.6
C27—C26—Sn1123.8 (5)C59—C60—H60120.6
C28—C27—C26121.0 (7)C60—C61—C62121.1 (8)
C28—C27—H27119.5C60—C61—H61119.4
C26—C27—H27119.5C62—C61—H61119.4
C29—C28—C27121.0 (7)C57—C62—C61120.7 (8)
C29—C28—H28119.5C57—C62—H62119.7
C27—C28—H28119.5C61—C62—H62119.7
C20—Sn1—S1—C1−170.2 (3)C27—C26—C31—C301.7 (12)
C26—Sn1—S1—C170.7 (3)Sn1—C26—C31—C30−175.7 (7)
C14—Sn1—S1—C1−50.5 (3)C29—C30—C31—C26−3.7 (14)
C51—Sn2—S2—C32−169.5 (3)Sn2—S2—C32—C33105.7 (7)
C45—Sn2—S2—C32−49.1 (4)Sn2—S2—C32—C37−74.3 (7)
C57—Sn2—S2—C3272.4 (4)C37—C32—C33—C34−1.9 (13)
Sn1—S1—C1—C2−73.9 (6)S2—C32—C33—C34178.1 (7)
Sn1—S1—C1—C6108.2 (6)C32—C33—C34—C351.6 (14)
C6—C1—C2—C3−0.3 (11)C33—C34—C35—C360.4 (13)
S1—C1—C2—C3−178.2 (6)C33—C34—C35—N2178.8 (8)
C1—C2—C3—C41.7 (12)C38—N2—C35—C36−152.0 (7)
C2—C3—C4—C5−1.8 (11)C38—N2—C35—C3429.6 (12)
C2—C3—C4—N1179.8 (7)C34—C35—C36—C37−2.0 (12)
C7—N1—C4—C527.7 (11)N2—C35—C36—C37179.5 (7)
C7—N1—C4—C3−154.0 (7)C33—C32—C37—C360.4 (12)
C3—C4—C5—C60.5 (11)S2—C32—C37—C36−179.6 (6)
N1—C4—C5—C6178.8 (7)C35—C36—C37—C321.6 (12)
C4—C5—C6—C10.8 (12)C35—N2—C38—C39−179.1 (7)
C2—C1—C6—C5−0.9 (11)N2—C38—C39—C44−179.0 (8)
S1—C1—C6—C5177.0 (6)N2—C38—C39—C402.0 (12)
C4—N1—C7—C8−177.4 (6)C44—C39—C40—O2−179.1 (8)
N1—C7—C8—C13−176.0 (7)C38—C39—C40—O2−0.1 (12)
N1—C7—C8—C91.1 (12)C44—C39—C40—C411.0 (13)
C13—C8—C9—O1179.6 (7)C38—C39—C40—C41180.0 (8)
C7—C8—C9—O12.4 (12)O2—C40—C41—C42−179.8 (8)
C13—C8—C9—C10−1.8 (12)C39—C40—C41—C420.1 (14)
C7—C8—C9—C10−178.9 (8)C40—C41—C42—C43−0.6 (15)
O1—C9—C10—C11179.4 (8)C41—C42—C43—C44−0.1 (15)
C8—C9—C10—C110.7 (13)C42—C43—C44—C391.2 (16)
C9—C10—C11—C120.5 (14)C40—C39—C44—C43−1.7 (14)
C10—C11—C12—C13−0.6 (14)C38—C39—C44—C43179.3 (9)
C11—C12—C13—C8−0.6 (14)C51—Sn2—C45—C50172.4 (7)
C9—C8—C13—C121.7 (12)C57—Sn2—C45—C50−60.2 (7)
C7—C8—C13—C12178.9 (8)S2—Sn2—C45—C5059.7 (7)
C20—Sn1—C14—C19−5.1 (6)C51—Sn2—C45—C46−6.4 (7)
C26—Sn1—C14—C19121.1 (6)C57—Sn2—C45—C46121.0 (6)
S1—Sn1—C14—C19−118.6 (5)S2—Sn2—C45—C46−119.1 (6)
C20—Sn1—C14—C15174.1 (6)C50—C45—C46—C47−1.8 (13)
C26—Sn1—C14—C15−59.6 (7)Sn2—C45—C46—C47177.0 (7)
S1—Sn1—C14—C1560.7 (6)C45—C46—C47—C482.1 (14)
C19—C14—C15—C161.7 (12)C46—C47—C48—C49−1.5 (14)
Sn1—C14—C15—C16−177.6 (6)C47—C48—C49—C500.5 (15)
C14—C15—C16—C17−2.7 (14)C46—C45—C50—C490.9 (13)
C15—C16—C17—C181.8 (15)Sn2—C45—C50—C49−177.9 (7)
C16—C17—C18—C190.2 (15)C48—C49—C50—C45−0.2 (15)
C15—C14—C19—C180.2 (11)C45—Sn2—C51—C56105.5 (6)
Sn1—C14—C19—C18179.5 (6)C57—Sn2—C51—C56−22.4 (7)
C17—C18—C19—C14−1.2 (14)S2—Sn2—C51—C56−139.2 (6)
C26—Sn1—C20—C25−25.1 (7)C45—Sn2—C51—C52−78.8 (7)
C14—Sn1—C20—C25100.9 (6)C57—Sn2—C51—C52153.4 (6)
S1—Sn1—C20—C25−142.8 (6)S2—Sn2—C51—C5236.5 (6)
C26—Sn1—C20—C21155.8 (6)C56—C51—C52—C53−1.1 (12)
C14—Sn1—C20—C21−78.2 (6)Sn2—C51—C52—C53−176.9 (6)
S1—Sn1—C20—C2138.1 (6)C51—C52—C53—C540.6 (14)
C25—C20—C21—C222.3 (12)C52—C53—C54—C550.5 (15)
Sn1—C20—C21—C22−178.6 (6)C53—C54—C55—C56−1.0 (15)
C20—C21—C22—C23−1.4 (13)C52—C51—C56—C550.6 (12)
C21—C22—C23—C240.1 (14)Sn2—C51—C56—C55176.4 (7)
C22—C23—C24—C250.3 (15)C54—C55—C56—C510.5 (14)
C21—C20—C25—C24−1.9 (12)C51—Sn2—C57—C5892.6 (7)
Sn1—C20—C25—C24179.0 (7)C45—Sn2—C57—C58−36.4 (7)
C23—C24—C25—C200.6 (14)S2—Sn2—C57—C58−154.9 (6)
C20—Sn1—C26—C3195.4 (6)C51—Sn2—C57—C62−85.1 (7)
C14—Sn1—C26—C31−31.6 (7)C45—Sn2—C57—C62145.9 (7)
S1—Sn1—C26—C31−150.8 (6)S2—Sn2—C57—C6227.4 (8)
C20—Sn1—C26—C27−81.8 (6)C62—C57—C58—C59−1.0 (14)
C14—Sn1—C26—C27151.3 (6)Sn2—C57—C58—C59−178.8 (7)
S1—Sn1—C26—C2732.0 (6)C57—C58—C59—C601.4 (15)
C31—C26—C27—C280.1 (11)C58—C59—C60—C61−2.2 (16)
Sn1—C26—C27—C28177.4 (6)C59—C60—C61—C622.5 (16)
C26—C27—C28—C290.0 (13)C58—C57—C62—C611.3 (13)
C27—C28—C29—C30−1.9 (13)Sn2—C57—C62—C61178.9 (7)
C28—C29—C30—C313.7 (14)C60—C61—C62—C57−2.1 (16)
Table 1
Selected geometric parameters (Å, °) top
Sn1—S12.421 (2)Sn2—S22.423 (2)
Sn1—C142.124 (6)Sn2—C452.127 (7)
Sn1—C202.113 (7)Sn2—C512.120 (7)
Sn1—C262.120 (7)Sn2—C572.129 (7)
S1—Sn1—C14107.92 (18)S2—Sn2—C45107.0 (2)
S1—Sn1—C20103.24 (19)S2—Sn2—C51102.5 (2)
S1—Sn1—C26109.69 (18)S2—Sn2—C57109.46 (18)
Sn1—S1—C1101.2 (2)Sn2—S2—C32101.1 (2)
Acknowledgements top

The authors thank the Postgraduate Foundation of Taishan University (No. Y06–2–12) for financial support.

references
References top

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