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Volume 66 
Part 11 
Pages m1389-m1390  
November 2010  

Received 20 September 2010
Accepted 5 October 2010
Online 13 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.034
wR = 0.061
Data-to-parameter ratio = 17.3
Details
Open access

Tris(2,4-dimethylbenzenethiolato)phenyltin(IV)

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
Correspondence e-mail: simonho@unam.mx, joseivan@unam.mx

In the title compound, [Sn(C6H5)(C8H9S)3], the Sn atom has an approximately tetrahedral SNCS3 geometry, with angles at this atom ranging from 105.13 (3) to 113.54 (9)°. The crystal packing does not involve any significant intermolecular interactions, although the benzene rings are involved in a number of weak intra- and intermolecular C-H...[pi] interactions.

Related literature

For background to the development of synthetic methods for highly substituted thiophenols with varying degrees of steric hindrance, see: Lloyd-Jones et al. (2008[Lloyd-Jones, G. C., Moseley, J. D. & Renny, J. S. (2008). Synthesis, pp. 661-689.]); Fleischer (2005[Fleischer, H. (2005). Coord. Chem. Rev. 249, 799-827.]); Huber et al. (1997[Huber, F., Schmiedgen, R., Schurmann, M., Barbieri, R., Ruisi, G. & Silvestri, A. (1997). Appl. Organomet. Chem. 11, 869-888.]); Estudiante-Negrete et al. (2007[Estudiante-Negrete, F., Redón, R., Hernández-Ortega, S., Toscano, R. A. & Morales-Morales, D. (2007). Inorg. Chim. Acta, 360, 1651-1660.]). For the synthesis of phenol derivatives, see: Flores-Figueroa et al. (2005[Flores-Figueroa, A., Arista-M, V., Talancón-Sánchez, D. & Castillo, I. (2005). J. Braz. Chem. Soc. 16, 397-403.]); Mondragón et al. (2010[Mondragón, A., Monsalvo, I., Regla, I. & Castillo, I. (2010). Tetrahedron Lett. 51, 767-770.]). For similar structures, see: Huber et al. (1997[Huber, F., Schmiedgen, R., Schurmann, M., Barbieri, R., Ruisi, G. & Silvestri, A. (1997). Appl. Organomet. Chem. 11, 869-888.]); Li et al. (2006[Li, Y.-X., Zhang, R.-F. & Ma, C.-L. (2006). Acta Cryst. E62, m957-m958.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)(C8H9S)3]

  • Mr = 607.43

  • Triclinic, [P \overline 1]

  • a = 9.2717 (7) Å

  • b = 10.6370 (8) Å

  • c = 15.6486 (11) Å

  • [alpha] = 93.420 (2)°

  • [beta] = 93.520 (1)°

  • [gamma] = 105.800 (1)°

  • V = 1477.51 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.09 mm-1

  • T = 298 K

  • 0.32 × 0.26 × 0.04 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.705, Tmax = 0.958

  • 12493 measured reflections

  • 5416 independent reflections

  • 4057 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.061

  • S = 0.86

  • 5416 reflections

  • 313 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15-C20 and C7-C12 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C12-H12...Cg1 0.93 2.72 3.557 (3) 149
C13-H13C...Cg2i 0.96 2.75 3.579 (3) 144
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2342 ).


Acknowledgements

The authors thank the Instituto Rcxaslan-CSIC, Spain for a license to use the Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Estudiante-Negrete, F., Redón, R., Hernández-Ortega, S., Toscano, R. A. & Morales-Morales, D. (2007). Inorg. Chim. Acta, 360, 1651-1660.  [ISI] [CSD] [CrossRef] [ChemPort]
Fleischer, H. (2005). Coord. Chem. Rev. 249, 799-827.  [ISI] [CrossRef] [ChemPort]
Flores-Figueroa, A., Arista-M, V., Talancón-Sánchez, D. & Castillo, I. (2005). J. Braz. Chem. Soc. 16, 397-403.  [CrossRef] [ChemPort]
Huber, F., Schmiedgen, R., Schurmann, M., Barbieri, R., Ruisi, G. & Silvestri, A. (1997). Appl. Organomet. Chem. 11, 869-888.  [CrossRef] [ChemPort]
Li, Y.-X., Zhang, R.-F. & Ma, C.-L. (2006). Acta Cryst. E62, m957-m958.  [CSD] [CrossRef] [details]
Lloyd-Jones, G. C., Moseley, J. D. & Renny, J. S. (2008). Synthesis, pp. 661-689.
Mondragón, A., Monsalvo, I., Regla, I. & Castillo, I. (2010). Tetrahedron Lett. 51, 767-770.
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, m1389-m1390   [ doi:10.1107/S1600536810039851 ]

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