(N-Butyl-N-phenyl­dithio­carbamato-κS)triphenyl­tin(IV)

Nurul Farahana Kamaludin; Ibrahim Baba; Normah Awang; Mohamed Ibrahim Mohamed Tahir; Edward R T Tiekink

doi:10.1107/S1600536811012426

. 2011 Apr 7;67(Pt 5):m555–m556. doi: 10.1107/S1600536811012426

(N-Butyl-N-phenyldithiocarbamato-κS)triphenyltin(IV)

Nurul Farahana Kamaludin ^a, Ibrahim Baba ^b,^‡, Normah Awang ^a, Mohamed Ibrahim Mohamed Tahir ^c, Edward R T Tiekink ^d,^*

PMCID: PMC3089335 PMID: 21754289

Abstract

The title compound, [Sn(C₆H₅)₃(C₁₁H₁₄NS₂)], features a tetrahedrally coordinated Sn atom, as the dithiocarbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetrahedral geometry about the metal atom are evident with the widest C—Sn—S angle being 117.26 (5)°. In the crystal, molecules are linked by C—H⋯S interactions, which generate helical supramolecular chains along the b axis.

Related literature

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008 ▶). For a recently reported related structure, see: Awang et al. (2010 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]
M _r = 574.34
Monoclinic,
a = 10.0488 (1) Å
b = 18.0008 (2) Å
c = 15.2054 (2) Å
β = 102.442 (1)°
V = 2685.85 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 150 K
0.24 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.781, T _max = 0.894
34109 measured reflections
6099 independent reflections
5277 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.060
S = 1.02
6099 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012426/hb5836sup1.cif

e-67-0m555-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012426/hb5836Isup2.hkl

e-67-0m555-Isup2.hkl^{(292.5KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Sn—S1	2.4772 (5)
Sn—S2	3.1048 (5)
Sn—C12	2.1286 (18)
Sn—C18	2.1380 (19)
Sn—C24	2.1521 (18)
S1—C1	1.758 (2)
S2—C1	1.675 (2)

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C12—Sn—C18	113.76 (7)
C12—Sn—C24	107.51 (7)
C18—Sn—C24	107.45 (7)
C12—Sn—S1	117.26 (5)
C18—Sn—S1	115.54 (5)
C24—Sn—S1	92.18 (5)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯S2ⁱ	0.95	2.83	3.612 (2)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08–27-111), the Ministry of Higher Education (UKM-ST-06-FRGS0092–2010), Universiti Putra Malaysia and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Their potential as anti-cancer agents, anti-microbials and insecticides, and as convenient synthetic precursors for tin sulfide nanoparticles, attract continued attention to organotin dithiocarbamates (Tiekink, 2008). As part of on-going of structural studies of triphenyltin(IV) dithiocarbamates (Awang et al., 2010), the analysis of the title compound, (I), was undertaken.

The molecular structure, Fig. 1, features Sn coordinated by the dithiocarbamate ligand and three ipso-C atoms of three benzene rings. The dithiocarbamte ligand coordinates essentially in a monodentate fashion, an assignment supported by the large disparity in the C—S bond distances, Table 1. The coordination geometry is based on a tetrahedron with the range of tetrahedral angles being 92.18 (5) to 117.26 (5) °. The wider angles are ascribed to the influence of the proximate S2 atom. The crystal packing of (I) features helical supramolecular chains along the b axis that is sustained by C—H···S interactions, Fig. 2 and Table 2.

Experimental

The title compound was prepared using an in situ method by the addition of carbon disulfide (0.01 mol) to an ethanolic solution of N-butylphenylamine (0.01 mol). The mixture was stirred for 1 h at 277 K. The solution was then added drop-wise to a solution of triphenyltin(IV) chloride (0.01 mol) in ethanol (20 ml). The mixture was stirred for 1 h. The white precipitate that formed was filtered, washed with cold ethanol and dried in a desiccator. Crystallization was carried out by using an ethanol:chloroform (1:1 v/v) mixture to yield colourless prisms of (I). Yield: 34%. M.pt. 374–375 K. Elemental analysis. Found (calculated) for C₂₉H₂₉NS₂Sn: C, 60.54 (60.64); H 5.08 (5.09); N 2.34 (2.44); S 11.31 (11.17); Sn 20.19 (20.66) %. UV (CHCl₃) λ_max 252 nm (L(π) →L(π*)). IR (KBr): ν(C—H) 2960 m; ν(C≐N) 1477 m; ν(N—C) 1139 s; ν(C≐S) 997 s; ν(Cd—S) 356 s cm^-1.