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Acta Cryst. (2010). E66, m354    [ doi:10.1107/S1600536810007415 ]

Bis(N-isopropyl-N-methyldithiocarbamato-[kappa]2S,S')diphenyltin(IV)

A. F. Muthalib, I. Baba, Y. Farina and S. W. Ng

Abstract top

The dithiocarbamate anions in the title compound, [Sn(C6H5)2(C5H10NS2)2], chelate to the SnIV atom, which is six-coordinated in a skew-trapezoidal-bipyramidal geometry. The molecule lies across a twofold rotation axis.

Related literature top

For other diphenyltin bis(dithiocarbamate) compounds, see: Alcock et al. (1992); Farina et al. (2001a,b); Hook et al. (1994). For a discussion of the geometry of tin in diorganotin bischelates, see: Ng et al. (1987).

Experimental top

Diphenyltin dichloride (10 mmol), isopropylmethylamine (10 mmol) and carbon disulfide (10 mmol) were reacted in ethanol (50 ml) at 277 K to produce a white solid. The mixture was stirred for 1 h. The solid was collected and recrystallized from ethanol.

Refinement top

H atoms were placed in calculated positions (C–H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2-1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of [Sn(C6H5)2(C5H10NS2)2] at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. Unlabelled atoms are related to labelled atoms by the symmetry operation (1 - x, y, 1/2 - z).
Bis(N-isopropyl-N-methyldithiocarbamato- κ2S,S')diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C5H10NS2)2]F(000) = 1160
Mr = 569.41Dx = 1.493 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 6898 reflections
a = 18.8797 (10) Åθ = 2.4–28.3°
b = 9.2067 (5) ŵ = 1.35 mm−1
c = 14.5694 (8) ÅT = 293 K
V = 2532.4 (2) Å3Block, colourless
Z = 40.35 × 0.35 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer		2785 independent reflections
Radiation source: fine-focus sealed tube2291 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −22→22
Tmin = 0.649, Tmax = 0.774k = −11→11
15127 measured reflectionsl = −13→18
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.044P)2 + 2.0829P]
where P = (Fo2 + 2Fc2)/3
2785 reflections(Δ/σ)max = 0.001
135 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
[Sn(C6H5)2(C5H10NS2)2]V = 2532.4 (2) Å3
Mr = 569.41Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 18.8797 (10) ŵ = 1.35 mm−1
b = 9.2067 (5) ÅT = 293 K
c = 14.5694 (8) Å0.35 × 0.35 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer		2785 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2291 reflections with I > 2σ(I)
Tmin = 0.649, Tmax = 0.774Rint = 0.022
15127 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.29 e Å−3
S = 1.10Δρmin = −0.30 e Å−3
2785 reflectionsAbsolute structure: ?
135 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.71348 (3)0.25000.03365 (10)
S10.44810 (4)0.65957 (8)0.41039 (4)0.04395 (18)
S20.40918 (5)0.48826 (9)0.24740 (4)0.04373 (19)
N10.36739 (12)0.4240 (3)0.41754 (14)0.0388 (5)
C10.42071 (15)0.8630 (3)0.19862 (19)0.0404 (6)
C20.44326 (19)0.9844 (4)0.1519 (3)0.0648 (10)
H20.49110.99450.13820.078*
C30.3962 (2)1.0925 (4)0.1246 (3)0.0802 (12)
H30.41281.17450.09410.096*
C40.3258 (2)1.0776 (4)0.1429 (3)0.0722 (11)
H40.29431.15050.12580.087*
C50.3015 (2)0.9560 (4)0.1861 (3)0.0692 (10)
H50.25330.94480.19690.083*
C60.34853 (18)0.8492 (4)0.2139 (2)0.0544 (8)
H60.33140.76680.24340.065*
C70.40355 (14)0.5130 (3)0.36386 (17)0.0356 (5)
C80.36473 (18)0.4480 (4)0.51766 (19)0.0518 (8)
H8A0.40880.48890.53790.078*
H8B0.35680.35710.54820.078*
H8C0.32680.51370.53190.078*
C90.33678 (18)0.2865 (3)0.3824 (2)0.0486 (7)
H90.33240.29580.31560.058*
C100.2637 (2)0.2584 (5)0.4203 (3)0.0784 (12)
H10A0.24250.17870.38800.118*
H10B0.23510.34370.41280.118*
H10C0.26720.23500.48440.118*
C110.3871 (3)0.1643 (5)0.4012 (4)0.1013 (17)
H11A0.37230.07950.36810.152*
H11B0.38750.14360.46580.152*
H11C0.43390.19160.38180.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03059 (17)0.03725 (15)0.03310 (15)0.0000.00153 (9)0.000
S10.0463 (4)0.0523 (4)0.0332 (3)−0.0086 (3)0.0028 (3)−0.0052 (3)
S20.0555 (5)0.0467 (4)0.0290 (3)−0.0106 (3)0.0052 (3)−0.0015 (3)
N10.0427 (13)0.0454 (12)0.0282 (10)−0.0041 (10)0.0043 (9)0.0025 (9)
C10.0377 (16)0.0452 (14)0.0383 (14)−0.0004 (11)−0.0031 (11)−0.0004 (11)
C20.050 (2)0.063 (2)0.082 (2)−0.0027 (17)−0.0015 (18)0.0269 (19)
C30.085 (3)0.062 (2)0.093 (3)0.006 (2)−0.007 (2)0.037 (2)
C40.072 (3)0.072 (2)0.073 (2)0.029 (2)−0.021 (2)0.0082 (19)
C50.042 (2)0.082 (3)0.084 (3)0.0168 (18)−0.0038 (18)0.008 (2)
C60.0450 (19)0.0591 (19)0.0591 (19)0.0038 (15)0.0025 (15)0.0092 (16)
C70.0346 (14)0.0408 (13)0.0315 (12)0.0029 (11)0.0014 (10)0.0024 (10)
C80.057 (2)0.0659 (19)0.0327 (13)−0.0092 (16)0.0060 (13)0.0025 (13)
C90.060 (2)0.0449 (16)0.0413 (15)−0.0084 (13)0.0040 (14)0.0043 (12)
C100.058 (3)0.090 (3)0.087 (3)−0.026 (2)0.004 (2)0.004 (2)
C110.103 (4)0.052 (2)0.148 (5)0.016 (2)−0.014 (3)−0.014 (3)
Geometric parameters (Å, °) top
Sn1—C1i2.167 (3)C4—C51.364 (6)
Sn1—C12.167 (3)C4—H40.93
Sn1—S1i2.5820 (7)C5—C61.386 (5)
Sn1—S12.5820 (7)C5—H50.93
Sn1—S22.6910 (8)C6—H60.93
Sn1—S2i2.6909 (8)C8—H8A0.96
S1—C71.728 (3)C8—H8B0.96
S2—C71.715 (3)C8—H8C0.96
N1—C71.323 (3)C9—C101.508 (5)
N1—C81.476 (3)C9—C111.498 (5)
N1—C91.483 (4)C9—H90.98
C1—C21.376 (4)C10—H10A0.96
C1—C61.387 (4)C10—H10B0.96
C2—C31.392 (5)C10—H10C0.96
C2—H20.93C11—H11A0.96
C3—C41.362 (6)C11—H11B0.96
C3—H30.93C11—H11C0.96
C1i—Sn1—C1101.13 (15)C4—C5—H5119.9
C1i—Sn1—S1i99.94 (8)C6—C5—H5119.9
C1—Sn1—S1i94.10 (7)C1—C6—C5121.1 (3)
C1i—Sn1—S194.10 (7)C1—C6—H6119.4
C1—Sn1—S199.94 (8)C5—C6—H6119.4
S1i—Sn1—S1157.84 (4)N1—C7—S2122.3 (2)
C1i—Sn1—S2159.15 (7)N1—C7—S1120.20 (19)
C1—Sn1—S292.55 (8)S2—C7—S1117.49 (15)
S1i—Sn1—S294.64 (2)N1—C8—H8A109.5
S1—Sn1—S267.84 (2)N1—C8—H8B109.5
C1i—Sn1—S2i92.55 (8)H8A—C8—H8B109.5
C1—Sn1—S2i159.15 (7)N1—C8—H8C109.5
S1i—Sn1—S2i67.84 (2)H8A—C8—H8C109.5
S1—Sn1—S2i94.64 (2)H8B—C8—H8C109.5
S2—Sn1—S2i79.19 (4)N1—C9—C10112.1 (3)
C7—S1—Sn188.84 (9)N1—C9—C11109.3 (3)
C7—S2—Sn185.58 (10)C10—C9—C11112.6 (3)
C7—N1—C8120.6 (2)N1—C9—H9107.5
C7—N1—C9121.7 (2)C10—C9—H9107.5
C8—N1—C9117.1 (2)C11—C9—H9107.5
C2—C1—C6117.3 (3)C9—C10—H10A109.5
C2—C1—Sn1118.2 (2)C9—C10—H10B109.5
C6—C1—Sn1124.4 (2)H10A—C10—H10B109.5
C1—C2—C3121.7 (3)C9—C10—H10C109.5
C1—C2—H2119.2H10A—C10—H10C109.5
C3—C2—H2119.2H10B—C10—H10C109.5
C4—C3—C2119.6 (4)C9—C11—H11A109.5
C4—C3—H3120.2C9—C11—H11B109.5
C2—C3—H3120.2H11A—C11—H11B109.5
C3—C4—C5120.1 (3)C9—C11—H11C109.5
C3—C4—H4120.0H11A—C11—H11C109.5
C5—C4—H4120.0H11B—C11—H11C109.5
C4—C5—C6120.2 (3)
C1i—Sn1—S1—C7−166.32 (12)C6—C1—C2—C32.9 (6)
C1—Sn1—S1—C791.61 (12)Sn1—C1—C2—C3−173.6 (3)
S1i—Sn1—S1—C7−36.91 (9)C1—C2—C3—C4−1.2 (7)
S2—Sn1—S1—C72.91 (9)C2—C3—C4—C5−1.3 (7)
S2i—Sn1—S1—C7−73.43 (9)C3—C4—C5—C61.9 (6)
C1i—Sn1—S2—C728.6 (2)C2—C1—C6—C5−2.2 (5)
C1—Sn1—S2—C7−102.64 (12)Sn1—C1—C6—C5174.0 (3)
S1i—Sn1—S2—C7163.03 (9)C4—C5—C6—C1−0.1 (6)
S1—Sn1—S2—C7−2.94 (9)C8—N1—C7—S2179.1 (2)
S2i—Sn1—S2—C796.66 (9)C9—N1—C7—S27.8 (4)
C1i—Sn1—C1—C241.2 (2)C8—N1—C7—S1−0.2 (4)
S1i—Sn1—C1—C2−59.7 (3)C9—N1—C7—S1−171.5 (2)
S1—Sn1—C1—C2137.5 (3)Sn1—S2—C7—N1−174.7 (2)
S2—Sn1—C1—C2−154.6 (3)Sn1—S2—C7—S14.59 (14)
S2i—Sn1—C1—C2−88.8 (3)Sn1—S1—C7—N1174.6 (2)
C1i—Sn1—C1—C6−135.0 (3)Sn1—S1—C7—S2−4.77 (15)
S1i—Sn1—C1—C6124.0 (3)C7—N1—C9—C10−139.3 (3)
S1—Sn1—C1—C6−38.8 (3)C8—N1—C9—C1049.2 (4)
S2—Sn1—C1—C629.2 (3)C7—N1—C9—C1195.2 (4)
S2i—Sn1—C1—C694.9 (3)C8—N1—C9—C11−76.4 (4)
Symmetry codes: (i) −x+1, y, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Sn1—C12.167 (3)Sn1—S22.6910 (8)
Sn1—S12.5820 (7)
Acknowledgements top

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08-27-111 and 06-01-02-SF0539) and the University of Malaya for supporting this study.

references
References top

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Westrip, S. P. (2010). publCIF. In preparation.