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Volume 69 
Part 9 
Page m497  
September 2013  

Received 7 August 2013
Accepted 9 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.022
wR = 0.062
Data-to-parameter ratio = 16.9
Details
Open access

Triphenyl(pyrrolidine-1-carbodithioato-[kappa]S)tin(IV)

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
Correspondence e-mail: m.siraj09@yahoo.com

In the title compound, [Sn(C6H5)3(C5H8NS2)], the SnIV atom adopts a distorted SnC3S tetrahedral coordination geometry [spread of bond angles = 94.43 (7)-120.74 (7)°]. A short intramolecular Sn...S contact [3.0270 (9) Å] occurs and two intramolecular C-H...S interactions help to establish the conformation. Three of the methylene groups of the pyrrolidine-1-carbodithioate ligand are disordered over two sets of sites of equal occupancy. In the crystal, very weak C-H...S interactions link the molecules into a three-dimensional network, with both S atoms acting as acceptors.

Related literature

For background to the structures and applications of organotin compounds, see: Abbas et al. (2013[Abbas, S. M., Sirajuddin, M., Ali, S., Hussain, S. T., Shah, F. A. & Meetsma, A. (2013). J. Chem. Soc. Pak. 35, 859-867.]); Pellerito & Nagy (2002[Pellerito, L. & Nagy, L. (2002). Coord. Chem. Rev. 224, 111-150.]); Ronconi et al. (2005[Ronconi, L., Maccato, C., Barreca, D., Saini, R., Zancato, M. & Fregona, D. (2005). Polyhedron, 24, 521-531.]); Shahzadi et al. (2006[Shahzadi, S., Ali, S., Bhatti, M. H., Fettouhi, M. & Athar, M. (2006). J. Organomet. Chem. 691, 1797-1802.], 2008[Shahzadi, S., Ali, S. & Fettouhi, M. (2008). J. Chem. Crystallogr. 38, 273-278.]); Sirajuddin et al. (2012[Sirajuddin, M., Ali, S., Haider, A., Shah, N. A., Shah, A. & Khan, M. R. (2012). Polyhedron, 40, 19-31.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)3(C5H8NS2)]

  • Mr = 496.23

  • Monoclinic, P 21 /c

  • a = 12.3467 (4) Å

  • b = 10.3227 (3) Å

  • c = 17.0611 (6) Å

  • [beta] = 90.864 (2)°

  • V = 2174.21 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.38 mm-1

  • T = 296 K

  • 0.32 × 0.26 × 0.24 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.667, Tmax = 0.734

  • 16466 measured reflections

  • 4265 independent reflections

  • 3567 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.062

  • S = 1.01

  • 4265 reflections

  • 253 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Selected bond lengths (Å)

Sn1-C6 2.160 (2)
Sn1-C12 2.134 (2)
Sn1-C18 2.149 (2)
Sn1-S1 2.4710 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...S1 0.93 2.75 3.384 (3) 127
C23-H23...S2 0.93 2.77 3.424 (3) 129
C2-H2B...S2i 0.97 2.96 3.759 (3) 141
C5-H5B...S1ii 0.97 2.98 3.750 (3) 137
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: SHELXL2012 (Sheldrick, 2012[Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7122 ).


Acknowledgements

The authors acknowledge the Quaid-i-Azam University Islamabad Pakistan for providing the research facilites as well as University Research Fund (URF) for financial support.

References

Abbas, S. M., Sirajuddin, M., Ali, S., Hussain, S. T., Shah, F. A. & Meetsma, A. (2013). J. Chem. Soc. Pak. 35, 859-867.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Pellerito, L. & Nagy, L. (2002). Coord. Chem. Rev. 224, 111-150.  [ISI] [CrossRef] [ChemPort]
Ronconi, L., Maccato, C., Barreca, D., Saini, R., Zancato, M. & Fregona, D. (2005). Polyhedron, 24, 521-531.  [ISI] [CrossRef] [ChemPort]
Shahzadi, S., Ali, S., Bhatti, M. H., Fettouhi, M. & Athar, M. (2006). J. Organomet. Chem. 691, 1797-1802.  [CSD] [CrossRef] [ChemPort]
Shahzadi, S., Ali, S. & Fettouhi, M. (2008). J. Chem. Crystallogr. 38, 273-278.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.
Sirajuddin, M., Ali, S., Haider, A., Shah, N. A., Shah, A. & Khan, M. R. (2012). Polyhedron, 40, 19-31.  [ISI] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m497  [ doi:10.1107/S1600536813022472 ]

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