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Acta Cryst. (2007). E63, m1799    [ doi:10.1107/S1600536807025378 ]

Dibenzylbis(naphthalene-2-thiolato-[kappa]S)tin(IV)

M. N. Tahir, M. Danish, S. Ali, D. Ülkü and M. Mazhar

Abstract top

In the crystal structure of the title compound, [Sn(C7H7)2(C10H7S)2], the distorted tetrahedral coordination around the Sn atom consists of two benzyl C atoms and two S atoms of naphthalenethiolate groups. The bond angles in the coordination environment are in the range 102.27 (5)-116.63 (19)°. The average Sn-C and Sn-S bond lengths are 2.151 (4) and 2.4172 (13) Å, respectively. One of the naphthalenethiolate groups is disordered, with a relative occupancy ratio of 0.726 (8):0.274 (8).

Comment top

Relatively few crystal structures have been reported containing only Sn—S and Sn—C bonds such as triphenyltin p-tert-butylphenylsulfide (Clarke et al., 1973), (benzenethiolato-κS)triphenyltin(IV) and bis(benzenethiolato- κS)diphenylltin(IV) (Speziali et al., 1994), bis(O-cyclohexyl dithiocarbanato)dimethyltin(IV) (Mohamed-Ibrahim et al., 1996). The crystal structures of (naphthalenethiolato-S) triphenyltin(IV) and bis(naphthalenethiolato-S)dimethyltin(IV) (Kalsoom et al., 1997), have been published. The crystal structure of the title compound is determined to study the effect on coordination of Sn in the presence of two benzyl and two thionaphthyl groups simultaneously, which might help to understand the properties of such complexes. The coordination around Sn atom is distorted tetrahedral containing two benzyl C-atoms and two S-atoms of the thionaphthyl groups. The angles around Sn vary between 102.27 (5) and 116.63 (19)°. This distortion from the ideal value of 109.5° exists in related compounds mentioned above also, but the variation ranges are different. The Sn environment in the present compound resembles with bis(benzenethiolato-κS)diphenylltin(IV) and that of bis (naphthalenethiolato-S)dimethyltin(IV). It is observed that C—Sn—C bond angle is always larger than the S—Sn—S or C—Sn—S bond angles, however, in the present case it is smaller than the reported structures. The average Sn—C [2.151 (4) Å] and Sn—S [2.4172 (13) Å] bond lengths in the title compound are slightly larger than the corresponding values observed in the related compounds; 2.119 (7)Å and 2.414 (3)Å (Clarke et al., 1973), 2.127 (5)Å and 2.409 (2)Å (Speziali et al., 1994). The dihedral angle between the phenyl groups (C2—C7) and (C9—C14) is 48.5 (2)°. All the nephthyl groups are planar. The distance of S1 atom from the least square plane of C15—C24 is 0.237 (6) Å. The dihedral angle between the two nephthyl groups is 87.3 (3)°. One of the thionapthalene group is disordered with a percentage relative occupancy ratio of 72.6 (8) and 27.4 (8). The possible cause of disorder is the closest intra-molecular C8···C25a [3.49 (1) Å], C8···C25b[3.40 (2) Å] and inter-molecular S2···S2(−x, −y, 1 − z)[3.404 (2) Å] interactions. However, no possible hydrogen bond exists.

Related literature top

For related literature, see: Clarke et al. (1973); Mohamed-Ibrahim et al. (1996); Kalsoom et al. (1997); Speziali et al. (1994).

Experimental top

0.04 mole (6.4 g) of 2-thionaphthalene in 60 ml THF was added to 0.04 mole (4.4 ml) of triethylamine in a three necked flask fitted with reflux condenser under inert atmosphere. 0.02 mole (7.44 g) of dibenzyltin dichloride in 40 ml of THF was added dropwise with stirring. The reaction mixture was left for overnight stirring. The mixture was filtered and solvent was removed by rotary evaporator and crystallized in light petroleum ether (40–60°C).

Refinement top

Early stages of the refinement indicated that the C—C bond distances in one of the thionaphthyl group are extremly larger and hence a disorder exists. The disorder could be resolved by assuming that all C-atoms of the thionaphthyl group are splitted over two sites. The opening of the two groups with respect to S atom [C25A—S2—C25B] is 13.3 (5)°. The two groups seem to be rotated over S-atom but are coplaner. The occupancy factor of two groups is 72.6 (8) and 27.4 (8)%. The R and ωR values became smaller drastically when disorder was removed rather than refining thionapthyl group using constraints. However, disordered group of low occupancy factor was treated as similar to the non-disordered group. All the disordered atoms were treated isotropically. H-atoms were attached geometrically including the C-atoms of each fragment.

H atoms to the carbon atoms were bonded geometrically 0.930Å from the corresponding atoms of the rings, while the H-atoms of CH2 groups were fixed geometrically at a distance of 0.970Å from the respective C-atom. Thermal parameter of all H atoms was taken 1.2 times of the corresponding atoms and treated fixed. Riding model was used for all hydrogen atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 2005).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the title compound, (C6H5CH2)2Sn(C10H7S)2, with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
Dibenzylbis(naphthalene-2-thiolato-κS)tin(IV) top
Crystal data top
[Sn(C7H7)2(C10H7S)2]F000 = 1256
Mr = 619.44Dx = 1.428 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 22 reflections
a = 10.732 (2) Åθ = 9.9–18.0º
b = 27.497 (3) ŵ = 1.05 mm−1
c = 9.789 (2) ÅT = 295 K
β = 94.033 (3)ºPrismatic, colourless
V = 2881.6 (9) Å30.20 × 0.15 × 0.12 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4 diffractometerθmax = 25.7º
ω/2θ scansθmin = 2.2º
Absorption correction: ψ scan
(MolEN; Fair, 1990)		h = −13→13
Tmin = 0.909, Tmax = 0.999k = 0→33
5873 measured reflectionsl = 0→11
5435 independent reflections3 standard reflections
3312 reflections with I > 2σ(I) every 120 min
Rint = 0.024 intensity decay: −4.2%
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.083  w = 1/[σ2(Fo2) + (0.0418P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3312 reflectionsΔρmax = 0.45 e Å−3
325 parametersΔρmin = −0.35 e Å−3
25 restraints
Crystal data top
[Sn(C7H7)2(C10H7S)2]V = 2881.6 (9) Å3
Mr = 619.44Z = 4
Monoclinic, P21/cMo Kα
a = 10.732 (2) ŵ = 1.05 mm−1
b = 27.497 (3) ÅT = 295 K
c = 9.789 (2) Å0.20 × 0.15 × 0.12 mm
β = 94.033 (3)º
Data collection top
Enraf–Nonius CAD-4 diffractometer3312 reflections with I > 2σ(I)
Absorption correction: ψ scan
(MolEN; Fair, 1990)		Rint = 0.024
Tmin = 0.909, Tmax = 0.9993 standard reflections
5873 measured reflections every 120 min
5435 independent reflections intensity decay: −4.2%
Refinement top
R[F2 > 2σ(F2)] = 0.04425 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.03Δρmax = 0.45 e Å−3
3312 reflectionsΔρmin = −0.35 e Å−3
325 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn0.35025 (3)−0.023520 (11)0.26320 (3)0.04872 (12)
S10.52595 (13)−0.06857 (5)0.18903 (16)0.0709 (4)
S20.45085 (13)0.04396 (5)0.38622 (14)0.0659 (4)
C10.2498 (5)−0.0673 (2)0.4009 (5)0.0689 (14)
H1A0.2966−0.09700.42090.083*
H1B0.2448−0.04980.48630.083*
C20.1209 (5)−0.08051 (18)0.3464 (5)0.0555 (12)
C30.0950 (6)−0.1254 (2)0.2871 (6)0.0745 (15)
H30.1585−0.14810.28240.089*
C4−0.0240 (8)−0.1366 (3)0.2351 (7)0.105 (2)
H4−0.0408−0.16720.19770.126*
C5−0.1158 (7)−0.1036 (4)0.2382 (8)0.117 (3)
H5−0.1951−0.11170.20060.140*
C6−0.0969 (7)−0.0596 (4)0.2934 (8)0.107 (2)
H6−0.1621−0.03740.29570.129*
C70.0231 (6)−0.0478 (2)0.3478 (6)0.0808 (16)
H70.0376−0.01720.38590.097*
C80.2434 (5)0.00648 (16)0.0893 (5)0.0573 (13)
H8A0.16900.02180.12030.069*
H8B0.29250.03150.04850.069*
C90.2054 (4)−0.03060 (15)−0.0178 (4)0.0507 (11)
C100.2851 (5)−0.04268 (17)−0.1192 (5)0.0571 (12)
H100.3626−0.0277−0.12010.069*
C110.2499 (6)−0.0767 (2)−0.2180 (5)0.0725 (15)
H110.3038−0.0845−0.28500.087*
C120.1348 (6)−0.0990 (2)−0.2175 (6)0.0769 (16)
H120.1098−0.1213−0.28570.092*
C130.0583 (5)−0.08846 (19)−0.1170 (6)0.0714 (15)
H13−0.0181−0.1043−0.11490.086*
C140.0927 (4)−0.05428 (17)−0.0177 (5)0.0579 (12)
H140.0388−0.04720.05000.070*
C150.4715 (4)−0.12983 (16)0.1911 (5)0.0562 (12)
C160.3779 (4)−0.14643 (17)0.1036 (5)0.0593 (12)
H160.3346−0.12460.04540.071*
C170.3442 (5)−0.19616 (17)0.0983 (5)0.0602 (13)
C180.2485 (6)−0.2143 (2)0.0077 (6)0.0906 (19)
H180.2020−0.1927−0.04860.109*
C190.2218 (7)−0.2622 (2)−0.0001 (8)0.110 (2)
H190.1585−0.2733−0.06200.132*
C200.2888 (8)−0.2948 (2)0.0840 (8)0.110 (2)
H200.2700−0.32780.07850.132*
C210.3810 (8)−0.2791 (2)0.1739 (8)0.107 (2)
H210.4258−0.30140.22930.129*
C220.4108 (6)−0.22853 (19)0.1851 (6)0.0776 (16)
C230.5061 (7)−0.2104 (2)0.2758 (7)0.106 (2)
H230.5508−0.23170.33450.128*
C240.5346 (6)−0.1626 (2)0.2799 (6)0.0889 (18)
H240.5971−0.15140.34270.107*
C25A0.3499 (8)0.0918 (3)0.3350 (9)0.053 (2)*0.726 (8)
C26A0.3698 (7)0.1177 (3)0.2183 (8)0.051 (2)*0.726 (8)
H26A0.43600.10930.16670.061*0.726 (8)
C27A0.2909 (7)0.1571 (3)0.1751 (7)0.0528 (18)*0.726 (8)
C28A0.3107 (7)0.1835 (3)0.0545 (7)0.069 (2)*0.726 (8)
H28A0.37540.17480.00100.083*0.726 (8)
C29A0.2342 (8)0.2221 (3)0.0164 (9)0.084 (3)*0.726 (8)
H29A0.24550.2392−0.06370.100*0.726 (8)
C30A0.1432 (11)0.2346 (4)0.0968 (10)0.089 (3)*0.726 (8)
H30A0.09440.26150.07140.107*0.726 (8)
C31A0.1177 (9)0.2106 (3)0.2127 (9)0.084 (3)*0.726 (8)
H31A0.05160.21990.26340.101*0.726 (8)
C32A0.1972 (7)0.1701 (3)0.2543 (8)0.056 (2)*0.726 (8)
C33A0.1786 (7)0.1432 (3)0.3744 (8)0.074 (2)*0.726 (8)
H33A0.11360.15160.42780.089*0.726 (8)
C34A0.2553 (7)0.1050 (3)0.4129 (9)0.065 (2)*0.726 (8)
H34A0.24260.08800.49280.078*0.726 (8)
C25B0.3670 (14)0.0957 (6)0.2982 (17)0.030 (5)*0.274 (8)
C26B0.2631 (17)0.1157 (6)0.352 (2)0.066 (6)*0.274 (8)
H26B0.23390.10200.43070.079*0.274 (8)
C27B0.1990 (14)0.1567 (6)0.2912 (17)0.043 (5)*0.274 (8)
C28B0.0987 (17)0.1801 (7)0.335 (2)0.091 (8)*0.274 (8)
H28B0.06540.16950.41530.109*0.274 (8)
C29B0.046 (2)0.2174 (7)0.269 (2)0.094 (7)*0.274 (8)
H29B−0.02320.23240.30250.112*0.274 (8)
C30B0.0929 (16)0.2346 (6)0.1485 (17)0.050 (5)*0.274 (8)
H30B0.05300.26100.10500.060*0.274 (8)
C31B0.191 (2)0.2156 (8)0.093 (2)0.102 (10)*0.274 (8)
H31B0.22160.22740.01240.122*0.274 (8)
C32B0.2464 (16)0.1745 (6)0.1690 (16)0.055 (5)*0.274 (8)
C33B0.3470 (17)0.1525 (6)0.1171 (19)0.072 (6)*0.274 (8)
H33B0.37660.16450.03660.087*0.274 (8)
C34B0.4037 (17)0.1146 (6)0.1775 (17)0.048 (5)*0.274 (8)
H34B0.47060.10040.13700.057*0.274 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.05049 (19)0.04538 (17)0.04885 (18)−0.00717 (17)−0.00680 (12)0.00091 (16)
S10.0569 (8)0.0546 (8)0.1018 (11)−0.0056 (7)0.0095 (7)−0.0058 (7)
S20.0769 (9)0.0522 (7)0.0644 (8)−0.0066 (6)−0.0255 (7)−0.0037 (6)
C10.069 (4)0.084 (4)0.053 (3)−0.018 (3)0.000 (3)0.014 (3)
C20.053 (3)0.061 (3)0.053 (3)−0.006 (3)0.008 (2)0.008 (2)
C30.071 (4)0.066 (4)0.087 (4)−0.010 (3)0.009 (3)0.011 (3)
C40.109 (6)0.097 (5)0.108 (5)−0.050 (5)0.004 (5)0.006 (4)
C50.064 (5)0.159 (9)0.126 (7)−0.026 (5)0.000 (4)0.023 (6)
C60.068 (5)0.151 (7)0.107 (6)0.036 (5)0.029 (4)0.043 (5)
C70.088 (5)0.088 (4)0.068 (4)0.008 (4)0.015 (3)0.001 (3)
C80.073 (3)0.042 (3)0.054 (3)−0.005 (2)−0.015 (2)0.002 (2)
C90.058 (3)0.046 (3)0.046 (2)0.002 (2)−0.011 (2)0.009 (2)
C100.056 (3)0.062 (3)0.052 (3)−0.012 (2)−0.006 (2)0.009 (2)
C110.083 (4)0.083 (4)0.051 (3)0.006 (3)0.004 (3)0.005 (3)
C120.088 (4)0.076 (4)0.064 (3)−0.003 (3)−0.017 (3)−0.023 (3)
C130.063 (4)0.069 (3)0.080 (4)−0.011 (3)−0.011 (3)−0.015 (3)
C140.051 (3)0.062 (3)0.059 (3)0.002 (2)−0.001 (2)−0.005 (2)
C150.059 (3)0.045 (3)0.064 (3)0.000 (2)0.003 (2)−0.001 (2)
C160.058 (3)0.050 (3)0.069 (3)0.005 (2)−0.002 (3)0.008 (2)
C170.066 (3)0.052 (3)0.063 (3)0.001 (3)0.003 (3)−0.002 (2)
C180.098 (5)0.058 (4)0.111 (5)−0.006 (3)−0.023 (4)−0.005 (3)
C190.126 (6)0.068 (4)0.133 (6)−0.023 (4)−0.022 (5)−0.019 (4)
C200.148 (7)0.054 (4)0.130 (6)−0.021 (4)0.021 (5)−0.010 (4)
C210.152 (7)0.054 (4)0.114 (6)0.008 (4)−0.001 (5)0.021 (4)
C220.098 (5)0.053 (3)0.082 (4)0.006 (3)0.006 (3)0.009 (3)
C230.140 (6)0.066 (4)0.106 (5)0.016 (4)−0.040 (5)0.021 (4)
C240.092 (5)0.076 (4)0.094 (4)0.000 (3)−0.031 (3)0.005 (3)
Geometric parameters (Å, °) top
Sn—C82.149 (4)C20—C211.349 (9)
Sn—C12.153 (5)C20—H200.9300
Sn—S12.4103 (14)C21—C221.429 (8)
Sn—S22.4241 (12)C21—H210.9300
S1—C151.783 (5)C22—C231.398 (8)
S2—C25A1.754 (8)C23—C241.349 (7)
S2—C25B1.863 (15)C23—H230.9300
C1—C21.492 (6)C24—H240.9300
C1—H1A0.9700C25A—C34A1.362 (11)
C1—H1B0.9700C25A—C26A1.376 (11)
C2—C31.382 (7)C26A—C27A1.421 (10)
C2—C71.382 (7)C26A—H26A0.9300
C3—C41.376 (8)C27A—C32A1.361 (10)
C3—H30.9300C27A—C28A1.414 (9)
C4—C51.341 (10)C28A—C29A1.377 (10)
C4—H40.9300C28A—H28A0.9300
C5—C61.335 (11)C29A—C30A1.341 (13)
C5—H50.9300C29A—H29A0.9300
C6—C71.397 (9)C30A—C31A1.357 (12)
C6—H60.9300C30A—H30A0.9300
C7—H70.9300C31A—C32A1.444 (11)
C8—C91.499 (6)C31A—H31A0.9300
C8—H8A0.9700C32A—C33A1.414 (11)
C8—H8B0.9700C33A—C34A1.370 (10)
C9—C141.374 (6)C33A—H33A0.9300
C9—C101.394 (6)C34A—H34A0.9300
C10—C111.378 (7)C25B—C34B1.374 (17)
C10—H100.9300C25B—C26B1.380 (16)
C11—C121.381 (7)C26B—C27B1.429 (16)
C11—H110.9300C26B—H26B0.9300
C12—C131.356 (7)C27B—C28B1.351 (16)
C12—H120.9300C27B—C32B1.419 (16)
C13—C141.384 (6)C28B—C29B1.321 (17)
C13—H130.9300C28B—H28B0.9300
C14—H140.9300C29B—C30B1.395 (18)
C15—C161.353 (6)C29B—H29B0.9300
C15—C241.395 (6)C30B—C31B1.329 (18)
C16—C171.414 (6)C30B—H30B0.9300
C16—H160.9300C31B—C32B1.458 (17)
C17—C221.392 (7)C31B—H31B0.9300
C17—C181.401 (7)C32B—C33B1.367 (17)
C18—C191.350 (7)C33B—C34B1.323 (16)
C18—H180.9300C33B—H33B0.9300
C19—C201.383 (9)C34B—H34B0.9300
C19—H190.9300
C8—Sn—C1116.63 (19)C21—C20—H20119.7
C8—Sn—S1110.09 (14)C19—C20—H20119.7
C1—Sn—S1109.73 (16)C20—C21—C22120.8 (6)
C8—Sn—S2107.09 (12)C20—C21—H21119.6
C1—Sn—S2110.03 (14)C22—C21—H21119.6
S1—Sn—S2102.27 (5)C17—C22—C23118.7 (5)
C15—S1—Sn102.60 (16)C17—C22—C21118.2 (6)
C25A—S2—C25B13.2 (5)C23—C22—C21123.0 (6)
C25A—S2—Sn100.8 (3)C24—C23—C22121.4 (5)
C25B—S2—Sn99.9 (5)C24—C23—H23119.3
C2—C1—Sn113.8 (3)C22—C23—H23119.3
C2—C1—H1A108.8C23—C24—C15120.8 (5)
Sn—C1—H1A108.8C23—C24—H24119.6
C2—C1—H1B108.8C15—C24—H24119.6
Sn—C1—H1B108.8C34A—C25A—C26A119.4 (7)
H1A—C1—H1B107.7C34A—C25A—S2120.7 (7)
C3—C2—C7116.9 (5)C26A—C25A—S2119.8 (6)
C3—C2—C1121.4 (5)C25A—C26A—C27A121.2 (7)
C7—C2—C1121.6 (5)C25A—C26A—H26A119.4
C4—C3—C2120.7 (6)C27A—C26A—H26A119.4
C4—C3—H3119.7C32A—C27A—C28A120.1 (8)
C2—C3—H3119.7C32A—C27A—C26A118.6 (7)
C5—C4—C3120.2 (7)C28A—C27A—C26A121.3 (7)
C5—C4—H4119.9C29A—C28A—C27A120.0 (8)
C3—C4—H4119.9C29A—C28A—H28A120.0
C6—C5—C4122.1 (7)C27A—C28A—H28A120.0
C6—C5—H5118.9C30A—C29A—C28A118.9 (9)
C4—C5—H5118.9C30A—C29A—H29A120.5
C5—C6—C7118.3 (7)C28A—C29A—H29A120.5
C5—C6—H6120.9C29A—C30A—C31A124.3 (11)
C7—C6—H6120.9C29A—C30A—H30A117.8
C2—C7—C6121.7 (6)C31A—C30A—H30A117.8
C2—C7—H7119.1C30A—C31A—C32A117.4 (9)
C6—C7—H7119.1C30A—C31A—H31A121.3
C9—C8—Sn113.4 (3)C32A—C31A—H31A121.3
C9—C8—H8A108.9C27A—C32A—C33A119.3 (8)
Sn—C8—H8A108.9C27A—C32A—C31A119.2 (8)
C9—C8—H8B108.9C33A—C32A—C31A121.5 (7)
Sn—C8—H8B108.9C34A—C33A—C32A120.8 (8)
H8A—C8—H8B107.7C34A—C33A—H33A119.6
C14—C9—C10118.2 (4)C32A—C33A—H33A119.6
C14—C9—C8121.2 (4)C25A—C34A—C33A120.5 (8)
C10—C9—C8120.6 (4)C25A—C34A—H34A119.7
C11—C10—C9120.6 (5)C33A—C34A—H34A119.7
C11—C10—H10119.7C34B—C25B—C26B117.8 (15)
C9—C10—H10119.7C34B—C25B—S2121.9 (11)
C10—C11—C12120.0 (5)C26B—C25B—S2120.2 (12)
C10—C11—H11120.0C25B—C26B—C27B122.1 (15)
C12—C11—H11120.0C25B—C26B—H26B118.9
C13—C12—C11119.6 (5)C27B—C26B—H26B118.9
C13—C12—H12120.2C28B—C27B—C32B116.5 (14)
C11—C12—H12120.2C28B—C27B—C26B127.8 (15)
C12—C13—C14120.7 (5)C32B—C27B—C26B115.7 (13)
C12—C13—H13119.7C29B—C28B—C27B122.4 (17)
C14—C13—H13119.7C29B—C28B—H28B118.8
C9—C14—C13120.8 (5)C27B—C28B—H28B118.8
C9—C14—H14119.6C28B—C29B—C30B120.9 (18)
C13—C14—H14119.6C28B—C29B—H29B119.6
C16—C15—C24118.9 (4)C30B—C29B—H29B119.6
C16—C15—S1122.7 (4)C31B—C30B—C29B123.8 (17)
C24—C15—S1118.2 (4)C31B—C30B—H30B118.1
C15—C16—C17121.7 (4)C29B—C30B—H30B118.1
C15—C16—H16119.1C30B—C31B—C32B113.6 (17)
C17—C16—H16119.1C30B—C31B—H31B123.2
C22—C17—C18118.8 (5)C32B—C31B—H31B123.2
C22—C17—C16118.5 (5)C33B—C32B—C27B120.0 (14)
C18—C17—C16122.7 (5)C33B—C32B—C31B117.2 (15)
C19—C18—C17121.7 (6)C27B—C32B—C31B122.9 (15)
C19—C18—H18119.1C34B—C33B—C32B122.2 (17)
C17—C18—H18119.1C34B—C33B—H33B118.9
C18—C19—C20120.0 (6)C32B—C33B—H33B118.9
C18—C19—H19120.0C33B—C34B—C25B122.1 (16)
C20—C19—H19120.0C33B—C34B—H34B119.0
C21—C20—C19120.5 (6)C25B—C34B—H34B119.0
C8—Sn—S1—C15−98.8 (2)C21—C22—C23—C24177.5 (7)
C1—Sn—S1—C1530.9 (2)C22—C23—C24—C15−1.5 (11)
S2—Sn—S1—C15147.67 (17)C16—C15—C24—C232.3 (9)
C8—Sn—S2—C25A24.6 (3)S1—C15—C24—C23−173.0 (6)
C1—Sn—S2—C25A−103.0 (3)C25B—S2—C25A—C34A−178 (3)
S1—Sn—S2—C25A140.4 (3)Sn—S2—C25A—C34A94.4 (7)
C8—Sn—S2—C25B11.3 (5)C25B—S2—C25A—C26A−1(3)
C1—Sn—S2—C25B−116.4 (5)Sn—S2—C25A—C26A−88.7 (6)
S1—Sn—S2—C25B127.0 (5)C34A—C25A—C26A—C27A−2.1 (11)
C8—Sn—C1—C211.6 (5)S2—C25A—C26A—C27A−179.0 (6)
S1—Sn—C1—C2−114.4 (4)C25A—C26A—C27A—C32A2.4 (11)
S2—Sn—C1—C2133.8 (4)C25A—C26A—C27A—C28A−179.5 (7)
Sn—C1—C2—C398.9 (5)C32A—C27A—C28A—C29A−0.7 (11)
Sn—C1—C2—C7−78.5 (5)C26A—C27A—C28A—C29A−178.8 (7)
C7—C2—C3—C4−1.3 (8)C27A—C28A—C29A—C30A1.4 (12)
C1—C2—C3—C4−178.8 (5)C28A—C29A—C30A—C31A−2.3 (14)
C2—C3—C4—C51.7 (10)C29A—C30A—C31A—C32A2.4 (14)
C3—C4—C5—C6−1.5 (12)C28A—C27A—C32A—C33A179.9 (7)
C4—C5—C6—C70.9 (12)C26A—C27A—C32A—C33A−2.0 (10)
C3—C2—C7—C60.7 (8)C28A—C27A—C32A—C31A0.8 (11)
C1—C2—C7—C6178.2 (5)C26A—C27A—C32A—C31A179.0 (7)
C5—C6—C7—C2−0.5 (10)C30A—C31A—C32A—C27A−1.6 (12)
C1—Sn—C8—C9−72.7 (4)C30A—C31A—C32A—C33A179.4 (8)
S1—Sn—C8—C953.2 (4)C27A—C32A—C33A—C34A1.3 (11)
S2—Sn—C8—C9163.6 (3)C31A—C32A—C33A—C34A−179.7 (7)
Sn—C8—C9—C1492.3 (5)C26A—C25A—C34A—C33A1.3 (12)
Sn—C8—C9—C10−86.4 (4)S2—C25A—C34A—C33A178.2 (6)
C14—C9—C10—C111.4 (7)C32A—C33A—C34A—C25A−1.0 (11)
C8—C9—C10—C11−179.8 (4)C25A—S2—C25B—C34B−179 (4)
C9—C10—C11—C120.1 (7)Sn—S2—C25B—C34B−84.3 (14)
C10—C11—C12—C13−2.0 (8)C25A—S2—C25B—C26B−1(2)
C11—C12—C13—C142.2 (8)Sn—S2—C25B—C26B94.3 (14)
C10—C9—C14—C13−1.2 (7)C34B—C25B—C26B—C27B−4(3)
C8—C9—C14—C13180.0 (4)S2—C25B—C26B—C27B177.4 (15)
C12—C13—C14—C9−0.6 (8)C25B—C26B—C27B—C28B−178 (2)
Sn—S1—C15—C1667.4 (4)C25B—C26B—C27B—C32B2(3)
Sn—S1—C15—C24−117.5 (4)C32B—C27B—C28B—C29B0(3)
C24—C15—C16—C17−1.2 (8)C26B—C27B—C28B—C29B−179 (2)
S1—C15—C16—C17173.9 (4)C27B—C28B—C29B—C30B0(4)
C15—C16—C17—C22−0.6 (8)C28B—C29B—C30B—C31B0(3)
C15—C16—C17—C18−179.4 (5)C29B—C30B—C31B—C32B0(3)
C22—C17—C18—C19−1.9 (9)C28B—C27B—C32B—C33B−179.4 (19)
C16—C17—C18—C19176.8 (6)C26B—C27B—C32B—C33B0(2)
C17—C18—C19—C200.9 (12)C28B—C27B—C32B—C31B0(3)
C18—C19—C20—C21−0.2 (12)C26B—C27B—C32B—C31B179 (2)
C19—C20—C21—C220.6 (12)C30B—C31B—C32B—C33B179.2 (19)
C18—C17—C22—C23−179.8 (6)C30B—C31B—C32B—C27B0(3)
C16—C17—C22—C231.4 (8)C27B—C32B—C33B—C34B0(3)
C18—C17—C22—C212.3 (8)C31B—C32B—C33B—C34B−179 (2)
C16—C17—C22—C21−176.5 (5)C32B—C33B—C34B—C25B−2(3)
C20—C21—C22—C17−1.6 (10)C26B—C25B—C34B—C33B4(3)
C20—C21—C22—C23−179.5 (7)S2—C25B—C34B—C33B−177.7 (15)
C17—C22—C23—C24−0.3 (11)
Table 1
Selected geometric parameters (Å, °) top
Sn—C82.149 (4)Sn—S22.4241 (12)
Sn—C12.153 (5)S1—C151.783 (5)
Sn—S12.4103 (14)
C8—Sn—C1116.63 (19)S1—Sn—S2102.27 (5)
C8—Sn—S1110.09 (14)C15—S1—Sn102.60 (16)
C1—Sn—S1109.73 (16)C16—C15—S1122.7 (4)
C8—Sn—S2107.09 (12)C24—C15—S1118.2 (4)
C1—Sn—S2110.03 (14)
references
References top

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Enraf–Nonius (1992). CAD-4 EXPRESS. Version 1.1. Enraf–Nonius, Delft, The Netherlands.

Fair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Farrugia, L. J. (2005). WinGX. Version 1.70.01. Department of Chemistry, University of Glasgow, Scotland.

Kalsoom, A., Mazhar, M., Ali, S., Mahon, M. F., Molloy, K. C. & Chaudry, M. I. (1997). Appl. Organomet. Chem. 11, 47–55.

Mohamed-Ibrahim, M. I., Khor, C.-K., Fun, H.-K. & Sivakumar, K. (1996). Acta Cryst. C52, 845–846.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Speziali, N., Guimarães, B. G., Silva, R. M., Duarte, P. H. & Aguiar, S. R. (1994). Acta Cryst. C50, 1059–1062.