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Tetra­kis(4-methyl-2-thien­yl)tin(IV)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 10 September 2008; accepted 10 October 2008; online 15 October 2008)

The mol­ecule of the title compound, [Sn(C5H5S)4], lies on a special position of [\overline{4}] site symmetry. The SnIV atom shows a slightly distorted tetra­hedral coordination.

Related literature

For the structure of tetra­kis(2-thien­yl)tin, see: Karipides et al. (1977[Karipides, A., Reed, A. T., Haller, D. A. & Hayes, F. (1977). Acta Cryst. B33, 950-951.]). For the synthesis, see: Kumar Das et al. (1987[Kumar Das, V. G., Lo, K. M. & Blunden, S. J. (1987). J. Organomet. Chem. 334, 307-322.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C5H5S)4]

  • Mr = 507.29

  • Tetragonal, [I \overline 4]

  • a = 11.6286 (9) Å

  • c = 7.5918 (6) Å

  • V = 1026.6 (1) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.65 mm−1

  • T = 100 (2) K

  • 0.30 × 0.25 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.637, Tmax = 0.852

  • 2948 measured reflections

  • 1151 independent reflections

  • 1149 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.012

  • wR(F2) = 0.028

  • S = 1.01

  • 1151 reflections

  • 58 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 513 Friedel pairs

  • Flack parameter: 0.005 (14)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of tetrakis(2-thienyl)tin, see: Karipides et al. (1977). For the synthesis, see: Kumar Das et al. (1987).

Experimental top

The title compound was synthesized as reported previously (Kumar Das et al., 1987). Single crystals were obtained upon recrystallization from chloroform.

Refinement top

H-atoms were placed in calculated positions (C-H = 0.95-0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of [Sn(C5H5S)4] at the 70% probability level. H atoms are drawn as spheres of arbitrary radii.
Tetrakis(4-methyl-2-thienyl)tin(IV) top
Crystal data top
[Sn(C5H5S)4]Dx = 1.641 Mg m3
Mr = 507.29Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4Cell parameters from 2958 reflections
Hall symbol: I -4θ = 2.5–28.3°
a = 11.6286 (9) ŵ = 1.65 mm1
c = 7.5918 (6) ÅT = 100 K
V = 1026.6 (1) Å3Prism, colourless
Z = 20.30 × 0.25 × 0.10 mm
F(000) = 508
Data collection top
Bruker SMART APEX
diffractometer
1151 independent reflections
Radiation source: fine-focus sealed tube1149 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1514
Tmin = 0.637, Tmax = 0.852k = 1513
2948 measured reflectionsl = 98
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.012H-atom parameters constrained
wR(F2) = 0.028 w = 1/[σ2(Fo2) + (0.0145P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
1151 reflectionsΔρmax = 0.45 e Å3
58 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), 513 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.005 (14)
Crystal data top
[Sn(C5H5S)4]Z = 2
Mr = 507.29Mo Kα radiation
Tetragonal, I4µ = 1.65 mm1
a = 11.6286 (9) ÅT = 100 K
c = 7.5918 (6) Å0.30 × 0.25 × 0.10 mm
V = 1026.6 (1) Å3
Data collection top
Bruker SMART APEX
diffractometer
1151 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1149 reflections with I > 2σ(I)
Tmin = 0.637, Tmax = 0.852Rint = 0.014
2948 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.012H-atom parameters constrained
wR(F2) = 0.028Δρmax = 0.45 e Å3
S = 1.01Δρmin = 0.21 e Å3
1151 reflectionsAbsolute structure: Flack (1983), 513 Friedel pairs
58 parametersAbsolute structure parameter: 0.005 (14)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.50000.50000.01202 (5)
S10.36597 (3)0.74692 (3)0.61422 (5)0.02012 (9)
C10.46144 (12)0.63979 (12)0.6694 (2)0.0140 (3)
C20.50206 (12)0.65832 (13)0.8364 (2)0.0134 (3)
H20.55620.60880.89140.016*
C30.45677 (14)0.75770 (14)0.9212 (2)0.0154 (3)
C40.38176 (14)0.81447 (13)0.8139 (2)0.0192 (3)
H40.34290.88320.84590.023*
C50.48542 (16)0.79485 (16)1.1056 (2)0.0206 (4)
H5A0.49190.87881.10970.031*
H5B0.55860.76021.14140.031*
H5C0.42440.76971.18590.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01360 (6)0.01360 (6)0.00885 (9)0.0000.0000.000
S10.0221 (2)0.0223 (2)0.0160 (2)0.00775 (16)0.00468 (16)0.00016 (16)
C10.0138 (7)0.0138 (7)0.0144 (8)0.0010 (5)0.0011 (6)0.0019 (6)
C20.0133 (6)0.0140 (7)0.0129 (8)0.0000 (5)0.0011 (6)0.0020 (6)
C30.0165 (8)0.0151 (8)0.0146 (8)0.0017 (6)0.0023 (6)0.0011 (6)
C40.0220 (8)0.0172 (8)0.0185 (9)0.0055 (6)0.0014 (7)0.0008 (7)
C50.0267 (9)0.0213 (9)0.0139 (9)0.0005 (7)0.0007 (7)0.0030 (7)
Geometric parameters (Å, º) top
Sn1—C1i2.1209 (15)C2—H20.95
Sn1—C12.1209 (15)C3—C41.364 (2)
Sn1—C1ii2.1209 (15)C3—C51.502 (2)
Sn1—C1iii2.1209 (15)C4—H40.95
S1—C41.7173 (16)C5—H5A0.98
S1—C11.7206 (15)C5—H5B0.98
C1—C21.370 (2)C5—H5C0.98
C2—C31.424 (2)
C1i—Sn1—C1111.58 (4)C4—C3—C2111.07 (15)
C1i—Sn1—C1ii105.32 (8)C4—C3—C5124.00 (16)
C1—Sn1—C1ii111.58 (4)C2—C3—C5124.92 (16)
C1i—Sn1—C1iii111.58 (4)C3—C4—S1111.98 (12)
C1—Sn1—C1iii105.32 (8)C3—C4—H4124.0
C1ii—Sn1—C1iii111.58 (4)S1—C4—H4124.0
C4—S1—C192.70 (8)C3—C5—H5A109.5
C2—C1—S1109.51 (12)C3—C5—H5B109.5
C2—C1—Sn1127.51 (11)H5A—C5—H5B109.5
S1—C1—Sn1122.93 (8)C3—C5—H5C109.5
C1—C2—C3114.74 (14)H5A—C5—H5C109.5
C1—C2—H2122.6H5B—C5—H5C109.5
C3—C2—H2122.6
C4—S1—C1—C20.03 (12)S1—C1—C2—C30.28 (17)
C4—S1—C1—Sn1177.81 (9)Sn1—C1—C2—C3177.37 (11)
C1i—Sn1—C1—C2149.39 (12)C1—C2—C3—C40.54 (19)
C1ii—Sn1—C1—C293.09 (10)C1—C2—C3—C5178.39 (14)
C1iii—Sn1—C1—C228.15 (11)C2—C3—C4—S10.54 (17)
C1i—Sn1—C1—S127.98 (10)C5—C3—C4—S1178.40 (12)
C1ii—Sn1—C1—S189.54 (12)C1—S1—C4—C30.34 (13)
C1iii—Sn1—C1—S1149.22 (11)
Symmetry codes: (i) y+1, x, z+1; (ii) y, x+1, z+1; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Sn(C5H5S)4]
Mr507.29
Crystal system, space groupTetragonal, I4
Temperature (K)100
a, c (Å)11.6286 (9), 7.5918 (6)
V3)1026.6 (1)
Z2
Radiation typeMo Kα
µ (mm1)1.65
Crystal size (mm)0.30 × 0.25 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.637, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
2948, 1151, 1149
Rint0.014
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.012, 0.028, 1.01
No. of reflections1151
No. of parameters58
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.21
Absolute structureFlack (1983), 513 Friedel pairs
Absolute structure parameter0.005 (14)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

 

Acknowledgements

The authors thank the University of Malaya for funding this study (grant No. FR155/2007A) and also for the purchase of the diffractometer.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKaripides, A., Reed, A. T., Haller, D. A. & Hayes, F. (1977). Acta Cryst. B33, 950–951.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationKumar Das, V. G., Lo, K. M. & Blunden, S. J. (1987). J. Organomet. Chem. 334, 307–322.  CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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