PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m354.
Published online 2010 March 3. doi:  10.1107/S1600536810007415
PMCID: PMC2983838

Bis(N-isopropyl-N-methyl­dithio­carbamato-κ2 S,S′)diphenyl­tin(IV)

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0m354-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H5)2(C5H10NS2)2]
  • M r = 569.41
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m354-efi1.jpg
  • a = 18.8797 (10) Å
  • b = 9.2067 (5) Å
  • c = 14.5694 (8) Å
  • V = 2532.4 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.35 mm−1
  • T = 293 K
  • 0.35 × 0.35 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.649, T max = 0.774
  • 15127 measured reflections
  • 2785 independent reflections
  • 2291 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.089
  • S = 1.10
  • 2785 reflections
  • 135 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007415/ci5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007415/ci5039Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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).

Figures

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).

Crystal data

[Sn(C6H5)2(C5H10NS2)2]F(000) = 1160
Mr = 569.41Dx = 1.493 Mg m3
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 mm1
c = 14.5694 (8) ÅT = 293 K
V = 2532.4 (2) Å3Block, colourless
Z = 40.35 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer2785 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

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 = 1.10w = 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 Å3
0 restraintsΔρmin = −0.30 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5039).

References

  • Alcock, N. W., Culver, J. & Roe, S. M. (1992). J. Chem. Soc. Dalton Trans. pp. 1477–1484.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farina, Y., Baba, I., Othman, A. H., Razak, I. A., Fun, H.-K. & Ng, S. W. (2001a). Acta Cryst. E57, m41–m42.
  • Farina, Y., Othman, A. H., Razak, I. A., Fun, H.-K., Ng, S. W. & Baba, I. (2001b). Acta Cryst. E57, m46–m47.
  • Hook, J. M., Linahan, B. M., Taylor, R. L., Tiekink, E. R. T., van Gorkom, L. & Webster, L. K. (1994). Main Group Met. Chem.17, 293–311.
  • Ng, S. W., Chen, W., Kumar Das, V. G. & Mak, T. C. W. (1987). J. Organomet. Chem.334, 295–305.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography