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Acta Cryst. (2008). E64, m1316    [ doi:10.1107/S1600536808030043 ]

[mu]-3-Thienylmalonato-[kappa]2O1:O3-bis[triphenyltin(IV)]

M. Yang, H. Yin, D. Wang, L. Quan and L. Cui

Abstract top

The title compound, [Sn2(C6H5)6(C7H4O4S)], contains two molecules with similar conformations in the asymmetric unit. In each molecule, the Sn atoms adopt a distorted tetrahedral geometry arising from three C atoms of three phenyl rings and one O atom from the bridging 3-thienylmalonato ligand. The molecules lie about inversion centers with the ligands facing each other, with C...O distances of 3.417 (10) and 3.475 (10) Å.

Comment top

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). Bi- or multidentate ligands containing O– or S-donors are often used to coordinate to tin centers. 3-Thiophenemalonic acid is a good bridging ligand that can be used to generate unexpected and interesting coordination polymers. We have therefore, synthesized the title compound, (I), and present its crystal structure in this article.

The asymmetric unit of the title compound, (I), contains two independent molecules (Fig. 1) with similar conformations wherein each 3-thiophenemalonicate is bonded to two triphenyl tin moities in a bidentate fashion. Each molecule consists of six phenyl and one (3-thiophenemalonicate) groups bonded to two tin atoms, where the bond lengths and angles are within normal ranges (Allen et al., 1987). Each tin atom is bonded to three phenyl carbon atoms and an oxygen atom derived from the monodentate carboxyl group, thus, displaying a distorted tetrahedral geometry. The Sn—O distances in (I) lie in the range 2.042 (5) - 2.068 (5) Å and are close to the corresponding distances reported in organotin carboxylates (Yip et al., 2007). Both the molecules in (I) lie about inversion centers with the ligands facing each other with C···O distances 3.417 (10) and 3.475 (10) Å (Table 1).

Related literature top

For biological activities of self-assembled organotin derivatives of carboxylic acid ligands, see: Gielen et al. (1988). For organotin carboxylates, see: Yip et al. (2007). For bond-length data, see: Allen et al. (1987); For related literature, see: Win et al. (2007).

Experimental top

The reaction was carried out under nitrogen atmosphere. 3-Thiophenemalonic acid (1 mmol) and sodium ethoxide (2.2 mmol) were added to a solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (2 mmol) was then added to the reaction mixture that was stirred for 12 h at 298 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 and 0.98 Å for aryl and methine H-atoms, respectively, and Uiso(H) = 1.2Ueq(C). The final difference map showed the highest peak at 1.34 e Å-3 at a distance of 0.88 Å from Sn1 atom and was deemed meaningless.

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme; H atoms have been omitted for clarity. Displacement ellipsoids have been drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). H atoms have been omitted for clarity.
µ-3-Thienylmalonato-κ2O1:O3-bis[triphenyltin(IV)] top
Crystal data top
[Sn2(C6H5)6(C7H4O4S)]F(000) = 3520
Mr = 884.14Dx = 1.517 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7272 reflections
a = 11.7260 (13) Åθ = 2.2–25.3°
b = 21.905 (2) ŵ = 1.39 mm−1
c = 30.194 (3) ÅT = 298 K
β = 93.542 (2)°Block, colorless
V = 7740.9 (15) Å30.28 × 0.12 × 0.09 mm
Z = 8
Data collection top
Siemens SMART CCD area-detector
diffractometer		13563 independent reflections
Radiation source: fine-focus sealed tube7274 reflections with I > 2σ(I)
graphiteRint = 0.060
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.698, Tmax = 0.886k = −26→22
38418 measured reflectionsl = −35→35
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0258P)2 + 39.3987P]
where P = (Fo2 + 2Fc2)/3
13563 reflections(Δ/σ)max = 0.001
901 parametersΔρmax = 1.34 e Å−3
0 restraintsΔρmin = −0.97 e Å−3
Crystal data top
[Sn2(C6H5)6(C7H4O4S)]V = 7740.9 (15) Å3
Mr = 884.14Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.7260 (13) ŵ = 1.39 mm−1
b = 21.905 (2) ÅT = 298 K
c = 30.194 (3) Å0.28 × 0.12 × 0.09 mm
β = 93.542 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer		13563 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7274 reflections with I > 2σ(I)
Tmin = 0.698, Tmax = 0.886Rint = 0.060
38418 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0258P)2 + 39.3987P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131Δρmax = 1.34 e Å−3
S = 1.00Δρmin = −0.97 e Å−3
13563 reflectionsAbsolute structure: ?
901 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

Experimental. (yield 79%; m.p. 457–459 K). Analysis calculated (%) for C43H34O4SSn2 (Mr = 884.14): C, 58.36; H, 3.85. found: C, 58.39; H, 3.91.

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
Sn10.39291 (5)0.30434 (3)0.61869 (2)0.05001 (18)
Sn20.41501 (5)0.03143 (3)0.64260 (2)0.04940 (18)
Sn30.10235 (5)0.32048 (3)0.853860 (19)0.04442 (16)
Sn40.10269 (5)0.04933 (3)0.88023 (2)0.05154 (18)
O10.3586 (5)0.2391 (3)0.66425 (18)0.0508 (15)
O20.5313 (5)0.2599 (3)0.69523 (19)0.0593 (17)
O30.4656 (5)0.1078 (2)0.67798 (18)0.0515 (15)
O40.3042 (5)0.0936 (3)0.7099 (2)0.0593 (17)
O50.0474 (5)0.2441 (2)0.81836 (18)0.0503 (15)
O60.2080 (5)0.2566 (3)0.7854 (2)0.0599 (17)
O70.1441 (5)0.1130 (2)0.83390 (19)0.0537 (15)
O8−0.0279 (5)0.0942 (3)0.80156 (19)0.0584 (16)
S10.5913 (2)0.17744 (13)0.84609 (9)0.0750 (8)
S2−0.0752 (3)0.17549 (15)0.64976 (9)0.0894 (10)
C10.4773 (8)0.1876 (4)0.8099 (3)0.053 (2)
H10.40560.19930.81840.063*
C20.5009 (7)0.1769 (4)0.7671 (3)0.045 (2)
C30.6167 (7)0.1589 (4)0.7647 (3)0.054 (2)
H30.64920.14870.73840.065*
C40.6769 (7)0.1581 (4)0.8065 (3)0.054 (2)
H40.75380.14810.81140.065*
C50.4419 (8)0.2319 (4)0.6948 (3)0.043 (2)
C60.4124 (7)0.1840 (4)0.7290 (2)0.042 (2)
H60.34120.19700.74150.051*
C70.3878 (8)0.1243 (4)0.7051 (3)0.044 (2)
C80.4121 (8)0.3911 (4)0.6478 (3)0.053 (2)
C90.5083 (8)0.4063 (4)0.6741 (3)0.065 (3)
H90.56360.37660.68070.078*
C100.5245 (9)0.4650 (4)0.6912 (3)0.065 (3)
H100.59040.47450.70860.078*
C110.4423 (9)0.5087 (5)0.6822 (3)0.069 (3)
H110.45150.54760.69420.082*
C120.3465 (9)0.4951 (5)0.6555 (3)0.071 (3)
H120.29130.52480.64890.085*
C130.3332 (8)0.4365 (5)0.6385 (3)0.066 (3)
H130.26870.42760.62010.080*
C140.2416 (7)0.2975 (4)0.5780 (3)0.054 (2)
C150.1361 (9)0.3088 (5)0.5937 (3)0.079 (3)
H150.13210.31700.62380.095*
C160.0358 (9)0.3085 (6)0.5673 (4)0.095 (4)
H16−0.03370.31590.57950.114*
C170.0401 (9)0.2973 (5)0.5232 (4)0.084 (3)
H17−0.02650.29850.50480.101*
C180.1410 (10)0.2844 (5)0.5060 (3)0.082 (3)
H180.14400.27610.47590.098*
C190.2405 (9)0.2838 (5)0.5337 (3)0.071 (3)
H190.30900.27370.52160.086*
C200.5382 (8)0.2743 (5)0.5870 (3)0.062 (3)
C210.6127 (9)0.3166 (6)0.5715 (3)0.080 (3)
H210.59620.35790.57410.096*
C220.7099 (11)0.2995 (7)0.5524 (4)0.095 (4)
H220.75810.32870.54130.114*
C230.7352 (11)0.2401 (8)0.5499 (4)0.099 (4)
H230.80220.22860.53710.119*
C240.5664 (10)0.2138 (6)0.5845 (4)0.086 (3)
H240.51900.18430.59560.103*
C250.6672 (11)0.1966 (6)0.5651 (4)0.099 (4)
H250.68650.15560.56270.119*
C260.3880 (9)−0.0466 (4)0.6816 (3)0.062 (3)
C270.2886 (11)−0.0522 (5)0.7042 (3)0.079 (3)
H270.2365−0.02010.70370.095*
C280.2664 (11)−0.1052 (6)0.7274 (4)0.090 (4)
H280.2008−0.10880.74300.108*
C290.3427 (14)−0.1514 (6)0.7268 (4)0.096 (4)
H290.3270−0.18720.74180.115*
C300.4383 (13)−0.1485 (5)0.7060 (4)0.094 (4)
H300.4885−0.18140.70710.113*
C310.4644 (10)−0.0952 (5)0.6820 (4)0.084 (4)
H310.5311−0.09280.66690.101*
C320.5612 (8)0.0244 (5)0.6053 (3)0.065 (3)
C330.6702 (9)0.0344 (5)0.6222 (3)0.076 (3)
H330.68170.04500.65200.091*
C340.7640 (10)0.0294 (5)0.5969 (4)0.086 (3)
H340.83650.03750.60990.103*
C350.7529 (11)0.0136 (6)0.5551 (4)0.100 (4)
H350.81510.01400.53740.119*
C360.6488 (12)−0.0032 (7)0.5385 (4)0.111 (5)
H360.6412−0.02000.51020.133*
C370.5521 (11)0.0036 (6)0.5624 (4)0.104 (4)
H370.4806−0.00610.54920.124*
C380.2677 (8)0.0548 (4)0.6027 (3)0.061 (3)
C390.1886 (10)0.0093 (5)0.5918 (4)0.087 (4)
H390.2013−0.03010.60240.105*
C400.0909 (10)0.0220 (6)0.5654 (4)0.103 (4)
H400.0401−0.00920.55710.124*
C410.0691 (10)0.0800 (6)0.5517 (4)0.101 (4)
H410.00210.08850.53480.121*
C420.1414 (11)0.1242 (6)0.5621 (4)0.106 (4)
H420.12580.16370.55200.127*
C430.2423 (10)0.1123 (5)0.5883 (4)0.095 (4)
H430.29230.14420.59580.114*
C44−0.1627 (8)0.1929 (4)0.6886 (3)0.060 (3)
H44−0.23970.20240.68350.072*
C45−0.1034 (8)0.1912 (4)0.7308 (3)0.058 (2)
H45−0.13690.20100.75700.070*
C460.0129 (7)0.1731 (4)0.7290 (3)0.046 (2)
C470.0377 (8)0.1639 (4)0.6870 (3)0.061 (3)
H470.10980.15230.67890.073*
C480.1238 (8)0.2275 (4)0.7913 (3)0.046 (2)
C490.0963 (7)0.1663 (3)0.7679 (2)0.0404 (19)
H490.16770.15170.75640.048*
C500.0639 (8)0.1212 (4)0.8024 (3)0.047 (2)
C510.2515 (8)0.2955 (4)0.8928 (3)0.052 (2)
C520.2867 (8)0.2356 (4)0.8996 (3)0.059 (3)
H520.24330.20420.88630.071*
C530.3825 (9)0.2215 (5)0.9249 (3)0.072 (3)
H530.40460.18090.92820.086*
C540.4463 (9)0.2658 (6)0.9454 (4)0.081 (3)
H540.51110.25570.96320.097*
C550.4152 (10)0.3253 (6)0.9398 (4)0.092 (4)
H550.45920.35590.95360.110*
C560.3172 (10)0.3405 (5)0.9133 (4)0.083 (3)
H560.29640.38120.90950.099*
C57−0.0445 (8)0.3288 (4)0.8908 (3)0.055 (2)
C58−0.0347 (9)0.3431 (5)0.9352 (3)0.074 (3)
H580.03710.34850.94950.089*
C59−0.1323 (10)0.3495 (5)0.9589 (4)0.089 (4)
H59−0.12510.35900.98900.106*
C60−0.2371 (10)0.3421 (5)0.9387 (4)0.075 (3)
H60−0.30160.34760.95460.090*
C61−0.2486 (8)0.3268 (4)0.8960 (3)0.065 (3)
H61−0.32090.32080.88230.078*
C62−0.1539 (8)0.3201 (4)0.8726 (3)0.061 (3)
H62−0.16350.30920.84280.073*
C630.1263 (8)0.3989 (4)0.8153 (3)0.053 (2)
C640.0494 (9)0.4468 (4)0.8156 (3)0.069 (3)
H64−0.01650.44320.83110.083*
C650.0715 (11)0.5012 (5)0.7924 (4)0.083 (4)
H650.01970.53340.79200.100*
C660.1685 (12)0.5059 (5)0.7709 (4)0.085 (4)
H660.18280.54190.75590.102*
C670.2468 (10)0.4594 (5)0.7705 (3)0.080 (3)
H670.31360.46390.75570.096*
C680.2243 (9)0.4058 (4)0.7924 (3)0.066 (3)
H680.27590.37370.79180.079*
C690.2540 (8)0.0566 (4)0.9221 (3)0.053 (2)
C700.3611 (9)0.0471 (4)0.9062 (3)0.068 (3)
H700.36640.03790.87640.082*
C710.4600 (10)0.0507 (5)0.9332 (4)0.081 (3)
H710.53070.04330.92190.097*
C720.4522 (10)0.0654 (5)0.9767 (4)0.075 (3)
H720.51860.06900.99510.089*
C730.3510 (10)0.0746 (5)0.9936 (3)0.073 (3)
H730.34760.08401.02350.087*
C740.2491 (9)0.0702 (4)0.9664 (3)0.068 (3)
H740.17890.07650.97830.082*
C75−0.0419 (8)0.0825 (4)0.9111 (3)0.056 (2)
C76−0.1048 (9)0.0454 (5)0.9364 (3)0.077 (3)
H76−0.08230.00510.94090.092*
C77−0.2021 (10)0.0667 (6)0.9558 (4)0.085 (3)
H77−0.24390.04090.97320.102*
C78−0.2353 (9)0.1261 (5)0.9489 (4)0.077 (3)
H78−0.30080.14070.96120.092*
C79−0.1733 (9)0.1631 (5)0.9244 (3)0.069 (3)
H79−0.19510.20370.92050.083*
C80−0.0795 (8)0.1423 (4)0.9055 (3)0.060 (3)
H80−0.03890.16870.88820.072*
C810.0827 (8)−0.0379 (4)0.8509 (3)0.054 (2)
C820.1691 (9)−0.0810 (4)0.8576 (3)0.068 (3)
H820.2363−0.07170.87410.082*
C830.1517 (10)−0.1390 (5)0.8386 (4)0.075 (3)
H830.2079−0.16870.84290.090*
C840.0546 (10)−0.1522 (4)0.8141 (3)0.070 (3)
H840.0451−0.19080.80150.085*
C85−0.0295 (9)−0.1097 (4)0.8077 (3)0.067 (3)
H85−0.0967−0.11920.79120.081*
C86−0.0144 (9)−0.0527 (4)0.8258 (3)0.061 (3)
H86−0.0713−0.02350.82090.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0461 (4)0.0518 (4)0.0514 (4)−0.0034 (3)−0.0022 (3)0.0055 (3)
Sn20.0507 (4)0.0455 (4)0.0509 (4)0.0031 (3)−0.0063 (3)−0.0037 (3)
Sn30.0490 (4)0.0388 (3)0.0452 (3)−0.0016 (3)0.0008 (3)0.0009 (3)
Sn40.0538 (4)0.0426 (4)0.0575 (4)0.0015 (3)−0.0018 (3)0.0045 (3)
O10.047 (4)0.059 (4)0.045 (4)−0.001 (3)−0.003 (3)0.007 (3)
O20.060 (4)0.059 (4)0.059 (4)−0.015 (3)−0.001 (3)0.012 (3)
O30.049 (4)0.053 (4)0.053 (4)−0.004 (3)0.005 (3)−0.009 (3)
O40.050 (4)0.051 (4)0.078 (4)−0.013 (3)0.012 (3)−0.004 (3)
O50.048 (4)0.047 (4)0.056 (4)−0.002 (3)0.012 (3)−0.003 (3)
O60.055 (4)0.057 (4)0.069 (4)−0.016 (3)0.011 (3)−0.007 (3)
O70.053 (4)0.051 (4)0.056 (4)0.001 (3)−0.009 (3)0.009 (3)
O80.057 (4)0.055 (4)0.062 (4)−0.015 (3)−0.005 (3)0.010 (3)
S10.081 (2)0.083 (2)0.0584 (16)−0.0057 (16)−0.0113 (15)0.0023 (15)
S20.101 (2)0.103 (2)0.0601 (18)−0.0093 (19)−0.0237 (17)−0.0006 (17)
C10.051 (6)0.059 (6)0.048 (5)−0.004 (5)0.000 (4)0.004 (5)
C20.046 (5)0.043 (5)0.044 (5)−0.007 (4)0.002 (4)0.000 (4)
C30.046 (6)0.066 (6)0.050 (6)−0.003 (5)0.007 (5)0.006 (5)
C40.041 (5)0.061 (6)0.061 (6)−0.003 (4)0.001 (5)0.016 (5)
C50.047 (6)0.040 (5)0.040 (5)−0.004 (4)0.001 (4)−0.002 (4)
C60.036 (5)0.052 (5)0.038 (5)−0.003 (4)−0.001 (4)0.000 (4)
C70.043 (6)0.045 (5)0.043 (5)−0.002 (4)−0.003 (4)0.001 (4)
C80.044 (6)0.062 (6)0.053 (6)0.001 (5)−0.002 (5)0.005 (5)
C90.064 (7)0.057 (7)0.073 (7)0.000 (5)−0.010 (6)0.005 (5)
C100.073 (7)0.056 (7)0.063 (6)−0.011 (6)−0.009 (5)0.004 (5)
C110.080 (8)0.058 (7)0.068 (7)−0.005 (6)0.004 (6)0.003 (5)
C120.072 (8)0.060 (7)0.080 (8)0.013 (6)−0.001 (6)0.007 (6)
C130.063 (7)0.068 (7)0.066 (7)0.002 (5)−0.011 (5)0.010 (6)
C140.039 (6)0.078 (7)0.044 (5)0.000 (5)0.003 (4)0.008 (5)
C150.060 (7)0.125 (10)0.052 (6)−0.002 (7)−0.002 (6)−0.014 (6)
C160.052 (7)0.146 (12)0.086 (9)0.008 (7)−0.003 (7)−0.013 (8)
C170.052 (7)0.130 (10)0.068 (8)−0.005 (7)−0.012 (6)0.007 (7)
C180.074 (8)0.122 (10)0.048 (6)−0.010 (7)−0.003 (6)0.005 (6)
C190.055 (7)0.100 (8)0.059 (7)−0.007 (6)0.005 (5)−0.001 (6)
C200.050 (6)0.080 (8)0.056 (6)0.000 (6)−0.001 (5)0.006 (6)
C210.057 (7)0.102 (9)0.081 (8)0.002 (7)0.010 (6)0.013 (7)
C220.069 (9)0.128 (12)0.088 (9)−0.010 (8)0.011 (7)0.016 (9)
C230.068 (9)0.133 (13)0.098 (10)0.007 (9)0.019 (7)0.003 (10)
C240.071 (8)0.100 (10)0.090 (9)0.003 (7)0.024 (7)0.003 (7)
C250.083 (9)0.106 (10)0.112 (10)0.018 (8)0.021 (8)0.004 (8)
C260.070 (7)0.043 (6)0.069 (7)0.002 (5)−0.026 (6)−0.001 (5)
C270.099 (10)0.061 (7)0.074 (8)−0.015 (6)−0.028 (7)0.011 (6)
C280.112 (11)0.076 (9)0.078 (8)−0.019 (8)−0.029 (7)0.011 (7)
C290.120 (12)0.068 (9)0.094 (10)−0.021 (9)−0.044 (9)0.014 (7)
C300.109 (11)0.064 (8)0.103 (11)0.009 (8)−0.046 (9)0.006 (7)
C310.094 (9)0.065 (8)0.089 (8)0.001 (7)−0.041 (7)−0.003 (7)
C320.060 (7)0.082 (7)0.051 (6)0.009 (5)−0.010 (5)−0.020 (5)
C330.059 (7)0.103 (9)0.064 (7)0.007 (6)−0.005 (6)−0.014 (6)
C340.058 (7)0.117 (10)0.082 (8)0.002 (7)0.000 (7)−0.014 (8)
C350.076 (10)0.135 (12)0.088 (10)0.003 (8)0.009 (8)−0.027 (9)
C360.091 (11)0.171 (14)0.071 (8)0.012 (10)0.008 (8)−0.033 (9)
C370.072 (9)0.157 (13)0.081 (9)0.011 (8)−0.004 (7)−0.029 (8)
C380.057 (6)0.059 (6)0.065 (6)−0.002 (5)−0.017 (5)0.001 (5)
C390.079 (9)0.077 (8)0.101 (9)−0.004 (6)−0.028 (7)0.012 (7)
C400.086 (10)0.097 (10)0.121 (11)−0.014 (8)−0.037 (8)0.014 (9)
C410.077 (9)0.100 (10)0.121 (11)0.000 (8)−0.043 (8)0.021 (9)
C420.096 (10)0.085 (9)0.130 (12)−0.003 (8)−0.039 (9)0.029 (8)
C430.086 (9)0.083 (9)0.110 (10)−0.010 (7)−0.039 (8)0.020 (7)
C440.040 (5)0.074 (7)0.066 (6)−0.012 (5)−0.002 (5)0.016 (5)
C450.054 (6)0.066 (6)0.054 (6)−0.011 (5)0.000 (5)0.011 (5)
C460.046 (5)0.050 (5)0.042 (5)−0.006 (4)0.002 (4)0.003 (4)
C470.065 (7)0.072 (7)0.044 (6)−0.004 (5)−0.009 (5)−0.006 (5)
C480.043 (6)0.046 (5)0.050 (6)−0.001 (4)−0.004 (4)0.006 (4)
C490.041 (5)0.041 (5)0.040 (5)−0.004 (4)0.001 (4)−0.003 (4)
C500.049 (6)0.042 (5)0.048 (6)−0.002 (4)0.005 (5)−0.005 (4)
C510.052 (6)0.057 (6)0.047 (5)−0.003 (5)−0.004 (4)0.004 (5)
C520.060 (7)0.058 (6)0.059 (6)−0.002 (5)−0.004 (5)0.010 (5)
C530.066 (7)0.073 (7)0.075 (7)0.008 (6)−0.009 (6)0.014 (6)
C540.067 (8)0.091 (9)0.082 (8)0.005 (7)−0.014 (6)0.025 (7)
C550.081 (9)0.083 (9)0.107 (10)−0.019 (7)−0.030 (7)0.002 (7)
C560.079 (8)0.069 (7)0.097 (9)−0.009 (6)−0.023 (7)0.008 (7)
C570.057 (6)0.055 (6)0.053 (6)0.000 (5)−0.001 (5)−0.002 (5)
C580.053 (7)0.103 (9)0.066 (7)−0.011 (6)−0.002 (6)−0.015 (6)
C590.074 (9)0.121 (10)0.071 (8)−0.009 (7)0.012 (7)−0.018 (7)
C600.060 (8)0.090 (8)0.079 (8)0.002 (6)0.018 (6)−0.007 (7)
C610.053 (7)0.073 (7)0.068 (7)0.004 (5)−0.002 (6)0.001 (6)
C620.057 (7)0.075 (7)0.050 (6)0.002 (5)−0.002 (5)0.000 (5)
C630.063 (7)0.041 (5)0.054 (6)−0.007 (5)−0.014 (5)0.005 (4)
C640.081 (8)0.050 (6)0.075 (7)0.002 (5)−0.011 (6)0.006 (5)
C650.101 (10)0.052 (7)0.094 (9)0.002 (6)−0.023 (8)0.009 (6)
C660.106 (11)0.060 (8)0.087 (9)−0.022 (7)−0.024 (8)0.024 (6)
C670.085 (8)0.072 (8)0.080 (8)−0.022 (7)−0.009 (6)0.019 (6)
C680.066 (7)0.059 (6)0.071 (7)−0.015 (5)−0.008 (6)0.020 (5)
C690.056 (6)0.050 (6)0.051 (6)0.012 (4)−0.003 (5)0.010 (5)
C700.070 (7)0.077 (7)0.057 (6)0.014 (6)−0.003 (6)−0.008 (5)
C710.072 (8)0.084 (8)0.086 (9)0.018 (6)−0.009 (7)−0.002 (7)
C720.074 (8)0.075 (7)0.071 (8)0.011 (6)−0.026 (7)0.006 (6)
C730.086 (9)0.076 (7)0.054 (7)0.007 (6)−0.011 (6)0.005 (5)
C740.071 (7)0.073 (7)0.061 (7)0.009 (6)0.001 (6)0.010 (6)
C750.056 (6)0.055 (6)0.054 (6)0.000 (5)−0.007 (5)0.003 (5)
C760.076 (8)0.066 (7)0.090 (8)0.002 (6)0.018 (7)0.017 (6)
C770.074 (8)0.087 (9)0.096 (9)−0.010 (7)0.026 (7)0.019 (7)
C780.065 (8)0.086 (9)0.081 (8)0.008 (6)0.010 (6)−0.003 (7)
C790.066 (7)0.068 (7)0.072 (7)0.011 (6)0.000 (6)0.002 (6)
C800.061 (7)0.052 (6)0.066 (6)0.001 (5)0.002 (5)0.002 (5)
C810.059 (6)0.037 (5)0.067 (6)0.000 (5)0.002 (5)0.011 (5)
C820.064 (7)0.061 (7)0.079 (7)0.005 (5)−0.006 (6)0.005 (6)
C830.082 (8)0.053 (7)0.089 (8)0.010 (6)0.001 (7)0.002 (6)
C840.087 (9)0.046 (6)0.078 (8)−0.004 (6)0.002 (7)0.002 (5)
C850.077 (8)0.052 (6)0.070 (7)−0.005 (6)−0.015 (6)0.005 (5)
C860.073 (7)0.047 (6)0.063 (6)0.006 (5)−0.002 (6)0.012 (5)
Geometric parameters (Å, °) top
Sn1—O12.042 (5)C36—C371.391 (15)
Sn1—C82.099 (9)C36—H360.9300
Sn1—C142.100 (9)C37—H370.9300
Sn1—C202.110 (10)C38—C431.360 (13)
Sn2—O32.053 (5)C38—C391.388 (13)
Sn2—C382.107 (9)C39—C401.383 (14)
Sn2—C262.111 (10)C39—H390.9300
Sn2—C322.114 (10)C40—C411.354 (15)
Sn3—O52.068 (5)C40—H400.9300
Sn3—C632.105 (9)C41—C421.313 (15)
Sn3—C572.116 (9)C41—H410.9300
Sn3—C512.119 (9)C42—C431.407 (14)
Sn4—O72.055 (6)C42—H420.9300
Sn4—C812.113 (9)C43—H430.9300
Sn4—C752.113 (9)C44—C451.412 (11)
Sn4—C692.120 (9)C44—H440.9300
O1—C51.311 (9)C45—C461.424 (11)
O2—C51.214 (9)C45—H450.9300
O3—C71.313 (9)C46—C471.334 (11)
O4—C71.205 (9)C46—C491.488 (10)
O5—C481.302 (10)C47—H470.9300
O6—C481.198 (9)C48—C491.539 (11)
O7—C501.308 (9)C49—C501.501 (11)
O8—C501.227 (9)C49—H490.9800
S1—C41.662 (9)C51—C561.374 (12)
S1—C11.688 (9)C51—C521.386 (12)
S2—C441.651 (10)C52—C531.355 (12)
S2—C471.703 (9)C52—H520.9300
C1—C21.357 (11)C53—C541.352 (13)
C1—H10.9300C53—H530.9300
C2—C31.421 (11)C54—C551.360 (14)
C2—C61.511 (10)C54—H540.9300
C3—C41.409 (11)C55—C561.399 (13)
C3—H30.9300C55—H550.9300
C4—H40.9300C56—H560.9300
C5—C61.525 (11)C57—C581.376 (12)
C6—C71.512 (11)C57—C621.377 (12)
C6—H60.9800C58—C591.394 (13)
C8—C131.376 (12)C58—H580.9300
C8—C91.381 (11)C59—C601.347 (13)
C9—C101.395 (12)C59—H590.9300
C9—H90.9300C60—C611.328 (13)
C10—C111.374 (13)C60—H600.9300
C10—H100.9300C61—C621.362 (12)
C11—C121.375 (13)C61—H610.9300
C11—H110.9300C62—H620.9300
C12—C131.387 (12)C63—C641.383 (12)
C12—H120.9300C63—C681.385 (12)
C13—H130.9300C64—C651.415 (13)
C14—C191.371 (12)C64—H640.9300
C14—C151.374 (12)C65—C661.348 (15)
C15—C161.380 (13)C65—H650.9300
C15—H150.9300C66—C671.372 (15)
C16—C171.359 (14)C66—H660.9300
C16—H160.9300C67—C681.381 (12)
C17—C181.351 (14)C67—H670.9300
C17—H170.9300C68—H680.9300
C18—C191.393 (13)C69—C741.375 (12)
C18—H180.9300C69—C701.387 (12)
C19—H190.9300C70—C711.377 (13)
C20—C241.368 (13)C70—H700.9300
C20—C211.375 (13)C71—C721.361 (14)
C21—C221.362 (14)C71—H710.9300
C21—H210.9300C72—C731.335 (13)
C22—C231.338 (16)C72—H720.9300
C22—H220.9300C73—C741.411 (13)
C23—C251.342 (16)C73—H730.9300
C23—H230.9300C74—H740.9300
C24—C251.403 (15)C75—C761.364 (12)
C24—H240.9300C75—C801.387 (11)
C25—H250.9300C76—C771.395 (14)
C26—C311.390 (13)C76—H760.9300
C26—C271.392 (14)C77—C781.371 (14)
C27—C281.389 (14)C77—H770.9300
C27—H270.9300C78—C791.343 (13)
C28—C291.352 (16)C78—H780.9300
C28—H280.9300C79—C801.351 (12)
C29—C301.318 (16)C79—H790.9300
C29—H290.9300C80—H800.9300
C30—C311.417 (15)C81—C861.367 (12)
C30—H300.9300C81—C821.390 (12)
C31—H310.9300C82—C831.403 (12)
C32—C331.364 (12)C82—H820.9300
C32—C371.369 (13)C83—C841.350 (13)
C33—C341.382 (13)C83—H830.9300
C33—H330.9300C84—C851.363 (13)
C34—C351.308 (14)C84—H840.9300
C34—H340.9300C85—C861.368 (12)
C35—C361.341 (15)C85—H850.9300
C35—H350.9300C86—H860.9300
O1—Sn1—C8111.8 (3)C40—C39—C38120.7 (11)
O1—Sn1—C1498.6 (3)C40—C39—H39119.7
C8—Sn1—C14112.0 (4)C38—C39—H39119.7
O1—Sn1—C20106.6 (3)C41—C40—C39119.9 (12)
C8—Sn1—C20113.8 (4)C41—C40—H40120.0
C14—Sn1—C20112.9 (4)C39—C40—H40120.0
O3—Sn2—C38107.4 (3)C42—C41—C40120.9 (12)
O3—Sn2—C26114.7 (3)C42—C41—H41119.6
C38—Sn2—C26111.7 (4)C40—C41—H41119.6
O3—Sn2—C3296.8 (3)C41—C42—C43120.3 (12)
C38—Sn2—C32112.1 (4)C41—C42—H42119.8
C26—Sn2—C32113.1 (4)C43—C42—H42119.8
O5—Sn3—C63114.9 (3)C38—C43—C42120.8 (11)
O5—Sn3—C5796.0 (3)C38—C43—H43119.6
C63—Sn3—C57111.2 (4)C42—C43—H43119.6
O5—Sn3—C51107.4 (3)C45—C44—S2109.9 (7)
C63—Sn3—C51112.6 (4)C45—C44—H44125.0
C57—Sn3—C51113.6 (3)S2—C44—H44125.0
O7—Sn4—C81110.7 (3)C44—C45—C46113.2 (8)
O7—Sn4—C75107.2 (3)C44—C45—H45123.4
C81—Sn4—C75115.1 (4)C46—C45—H45123.4
O7—Sn4—C6997.5 (3)C47—C46—C45110.0 (8)
C81—Sn4—C69112.6 (3)C47—C46—C49124.3 (8)
C75—Sn4—C69112.1 (3)C45—C46—C49125.7 (8)
C5—O1—Sn1112.9 (5)C46—C47—S2113.6 (8)
C7—O3—Sn2111.0 (5)C46—C47—H47123.2
C48—O5—Sn3110.3 (5)S2—C47—H47123.2
C50—O7—Sn4113.5 (5)O6—C48—O5123.4 (8)
C4—S1—C193.3 (4)O6—C48—C49123.1 (8)
C44—S2—C4793.3 (5)O5—C48—C49113.5 (7)
C2—C1—S1113.1 (7)C46—C49—C50115.6 (7)
C2—C1—H1123.4C46—C49—C48112.5 (7)
S1—C1—H1123.4C50—C49—C48108.1 (6)
C1—C2—C3110.4 (8)C46—C49—H49106.7
C1—C2—C6122.5 (8)C50—C49—H49106.7
C3—C2—C6127.1 (8)C48—C49—H49106.7
C4—C3—C2112.6 (8)O8—C50—O7122.6 (8)
C4—C3—H3123.7O8—C50—C49124.2 (8)
C2—C3—H3123.7O7—C50—C49113.2 (7)
C3—C4—S1110.5 (7)C56—C51—C52117.4 (9)
C3—C4—H4124.8C56—C51—Sn3119.0 (7)
S1—C4—H4124.8C52—C51—Sn3123.7 (7)
O2—C5—O1123.5 (8)C53—C52—C51121.8 (9)
O2—C5—C6124.9 (8)C53—C52—H52119.1
O1—C5—C6111.6 (7)C51—C52—H52119.1
C2—C6—C7112.2 (7)C54—C53—C52120.7 (10)
C2—C6—C5114.4 (7)C54—C53—H53119.6
C7—C6—C5108.4 (6)C52—C53—H53119.6
C2—C6—H6107.2C53—C54—C55119.6 (10)
C7—C6—H6107.2C53—C54—H54120.2
C5—C6—H6107.2C55—C54—H54120.2
O4—C7—O3121.6 (8)C54—C55—C56120.2 (11)
O4—C7—C6123.8 (8)C54—C55—H55119.9
O3—C7—C6114.6 (7)C56—C55—H55119.9
C13—C8—C9117.3 (9)C51—C56—C55120.2 (10)
C13—C8—Sn1121.0 (7)C51—C56—H56119.9
C9—C8—Sn1121.5 (7)C55—C56—H56119.9
C8—C9—C10121.6 (9)C58—C57—C62116.1 (9)
C8—C9—H9119.2C58—C57—Sn3120.8 (7)
C10—C9—H9119.2C62—C57—Sn3123.1 (7)
C11—C10—C9119.4 (9)C57—C58—C59120.2 (10)
C11—C10—H10120.3C57—C58—H58119.9
C9—C10—H10120.3C59—C58—H58119.9
C10—C11—C12120.2 (10)C60—C59—C58120.6 (11)
C10—C11—H11119.9C60—C59—H59119.7
C12—C11—H11119.9C58—C59—H59119.7
C11—C12—C13119.1 (10)C61—C60—C59120.3 (11)
C11—C12—H12120.4C61—C60—H60119.8
C13—C12—H12120.4C59—C60—H60119.8
C8—C13—C12122.3 (9)C60—C61—C62119.6 (10)
C8—C13—H13118.8C60—C61—H61120.2
C12—C13—H13118.8C62—C61—H61120.2
C19—C14—C15115.0 (9)C61—C62—C57123.2 (9)
C19—C14—Sn1122.9 (7)C61—C62—H62118.4
C15—C14—Sn1122.1 (7)C57—C62—H62118.4
C14—C15—C16123.5 (10)C64—C63—C68118.9 (9)
C14—C15—H15118.2C64—C63—Sn3120.3 (8)
C16—C15—H15118.2C68—C63—Sn3120.5 (7)
C17—C16—C15119.1 (11)C63—C64—C65119.7 (11)
C17—C16—H16120.4C63—C64—H64120.2
C15—C16—H16120.4C65—C64—H64120.2
C18—C17—C16120.0 (10)C66—C65—C64119.2 (11)
C18—C17—H17120.0C66—C65—H65120.4
C16—C17—H17120.0C64—C65—H65120.4
C17—C18—C19119.5 (10)C65—C66—C67122.2 (11)
C17—C18—H18120.2C65—C66—H66118.9
C19—C18—H18120.2C67—C66—H66118.9
C14—C19—C18122.7 (10)C66—C67—C68118.6 (11)
C14—C19—H19118.6C66—C67—H67120.7
C18—C19—H19118.6C68—C67—H67120.7
C24—C20—C21118.2 (10)C67—C68—C63121.4 (10)
C24—C20—Sn1122.1 (8)C67—C68—H68119.3
C21—C20—Sn1119.4 (9)C63—C68—H68119.3
C22—C21—C20121.6 (12)C74—C69—C70117.4 (9)
C22—C21—H21119.2C74—C69—Sn4120.8 (7)
C20—C21—H21119.2C70—C69—Sn4121.7 (7)
C23—C22—C21119.1 (13)C71—C70—C69122.3 (10)
C23—C22—H22120.4C71—C70—H70118.8
C21—C22—H22120.4C69—C70—H70118.8
C22—C23—C25122.2 (13)C72—C71—C70118.7 (11)
C22—C23—H23118.9C72—C71—H71120.6
C25—C23—H23118.9C70—C71—H71120.6
C20—C24—C25119.8 (11)C73—C72—C71121.2 (11)
C20—C24—H24120.1C73—C72—H72119.4
C25—C24—H24120.1C71—C72—H72119.4
C23—C25—C24119.0 (13)C72—C73—C74120.6 (10)
C23—C25—H25120.5C72—C73—H73119.7
C24—C25—H25120.5C74—C73—H73119.7
C31—C26—C27119.2 (10)C69—C74—C73119.8 (10)
C31—C26—Sn2120.4 (9)C69—C74—H74120.1
C27—C26—Sn2120.2 (7)C73—C74—H74120.1
C28—C27—C26120.6 (12)C76—C75—C80116.8 (9)
C28—C27—H27119.7C76—C75—Sn4121.3 (7)
C26—C27—H27119.7C80—C75—Sn4121.9 (7)
C29—C28—C27118.3 (13)C75—C76—C77121.5 (10)
C29—C28—H28120.9C75—C76—H76119.2
C27—C28—H28120.9C77—C76—H76119.2
C30—C29—C28123.7 (13)C78—C77—C76119.0 (10)
C30—C29—H29118.2C78—C77—H77120.5
C28—C29—H29118.2C76—C77—H77120.5
C29—C30—C31119.9 (13)C79—C78—C77120.0 (11)
C29—C30—H30120.0C79—C78—H78120.0
C31—C30—H30120.0C77—C78—H78120.0
C26—C31—C30118.4 (12)C78—C79—C80120.8 (10)
C26—C31—H31120.8C78—C79—H79119.6
C30—C31—H31120.8C80—C79—H79119.6
C33—C32—C37115.1 (10)C79—C80—C75121.9 (10)
C33—C32—Sn2124.0 (7)C79—C80—H80119.0
C37—C32—Sn2120.6 (8)C75—C80—H80119.0
C32—C33—C34122.7 (10)C86—C81—C82119.5 (9)
C32—C33—H33118.7C86—C81—Sn4121.0 (7)
C34—C33—H33118.7C82—C81—Sn4119.5 (7)
C35—C34—C33121.2 (11)C81—C82—C83118.0 (9)
C35—C34—H34119.4C81—C82—H82121.0
C33—C34—H34119.4C83—C82—H82121.0
C34—C35—C36117.9 (13)C84—C83—C82121.0 (10)
C34—C35—H35121.1C84—C83—H83119.5
C36—C35—H35121.1C82—C83—H83119.5
C35—C36—C37121.9 (12)C83—C84—C85120.6 (10)
C35—C36—H36119.0C83—C84—H84119.7
C37—C36—H36119.0C85—C84—H84119.7
C32—C37—C36120.5 (11)C84—C85—C86119.4 (10)
C32—C37—H37119.7C84—C85—H85120.3
C36—C37—H37119.7C86—C85—H85120.3
C43—C38—C39117.4 (9)C81—C86—C85121.4 (9)
C43—C38—Sn2124.3 (8)C81—C86—H86119.3
C39—C38—Sn2118.3 (8)C85—C86—H86119.3
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O60.982.483.417 (10)160
C49—H49···O40.982.543.475 (10)160
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O60.982.483.417 (10)160
C49—H49···O40.982.543.475 (10)160
Acknowledgements top

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

references
References top

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