Cyclo­pentyl­diphen­yl(4-thio­semi­carbazonopenta­noato-κO)tin(IV)

Kong Mun Lo; Seik Weng Ng

doi:10.1107/S1600536808011112

. 2008 Apr 26;64(Pt 5):m722–m723. doi: 10.1107/S1600536808011112

Cyclopentyldiphenyl(4-thiosemicarbazonopentanoato-κO)tin(IV)

Kong Mun Lo ^a, Seik Weng Ng ^a,^*

PMCID: PMC2961090 PMID: 21202248

Abstract

The Sn atom in the title compound, [Sn(C₅H₉)(C₆H₅)₂(C₆H₁₀N₃O₂S)], exists within a tetrahedral geometry. The –NH₂ group forms a weak hydrogen bond across a center of inversion to the S atom of an adjacent molecule, as well as another weaker hydrogen (across another center of inversion) to the Sn-bound O atom of another molecule. The hydrogen-bonded layer structure is consolidated by a strong hydrogen bond between the –NH– group and the uncoordinated O atom of a third molecule.

Related literature

For the antibacterial and antifungal applications of cyclopentyldiphenyltin carboxylates, see: Koshy et al. (2001 ▶). For the crystal structures of cyclopentyldiphenyltin derivatives, see: Lo & Ng (2004 ▶); Lo et al. (1999 ▶); Teo et al. (2004 ▶). For the synthesis of levulinic acid thiosemicarbazone, see: Ng (1992 ▶). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991 ▶, 1994 ▶).

Experimental

Crystal data

[Sn(C₅H₉)(C₆H₅)₂(C₆H₁₀N₃O₂S)]
M _r = 530.24
Triclinic,
a = 9.5780 (1) Å
b = 10.2375 (1) Å
c = 13.4205 (1) Å
α = 86.901 (1)°
β = 83.370 (1)°
γ = 63.667 (1)°
V = 1171.50 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 100 (2) K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.779, T _max = 0.889
15020 measured reflections
5350 independent reflections
5186 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.078
S = 1.03
5350 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 1.99 e Å⁻³
Δρ_min = −0.91 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011112/tk2255sup1.cif

e-64-0m722-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011112/tk2255Isup2.hkl

e-64-0m722-Isup2.hkl^{(261.9KB, hkl)}

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

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

Sn1—O1	2.063 (2)
Sn1—C1	2.131 (3)
Sn1—C6	2.125 (2)
Sn1—C12	2.134 (2)

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O1—Sn1—C1	112.7 (1)
O1—Sn1—C6	108.6 (1)
O1—Sn1—C12	95.9 (1)
C1—Sn1—C6	116.5 (1)
C1—Sn1—C12	112.1 (1)
C6—Sn1—C12	109.2 (1)
Sn1—O1—C18	109.3 (1)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O2ⁱ	0.88	2.12	2.975 (3)	163
N3—H3n1⋯O1ⁱⁱ	0.88	2.43	3.121 (3)	136
N3—H3n2⋯S1ⁱⁱⁱ	0.88	2.54	3.389 (2)	161

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the University of Malaya for funding this study (FR155/2007 A) and also for the purchase of the diffractometer.

supplementary crystallographic information

Comment

Triorganotin carboxylates having two different organyl substituents possess ehanced anti-bacterial and anti-fungal properties compared with the symmetrical compounds (Koshy et al., 2001). The synthesis of cyclopentyldiphenyltin hydroxide, which is the principal reagent that condenses readily with carboxylic acids, is a multi-step synthesis. Previous studies have characterized a few cyclopentyldiphenyltin derivatives (Lo & Ng, 2004; Lo et al., 1999; Teo et al., 2004). In the reaction with levulinic acid thiosemicarbazone (Ng, 1992), the organotin hydroxide yields a four-coordinate compound (I) (Fig. 1 & Table 1). The tin atom exists in a tetrahedral geometry; adjacent molecules are linked by hydrogen bonds into a layer structure, Table 2.

Experimental

Levulinic acid thiosemicarbazone was synthesized from the reaction of levulinic acid and thiosemicarbazide (Ng, 1992). Cyclopentyldiphenyltin hydroxide was sythesized by using a multistep reaction, starting from the Grignard reaction of cyclopentylmagnesium bromide on triphenyltin chloride. One phenyl radical was then cleaved by iodine in DMF; the resulting iodide was then hydrolyzed with sodium hydroxide in acetone to give the mixed triorganotin hydroxide (Lo et al., 1999). The thiosemicarbazone (1.1 g, 5 mmol) and triorganotin hydroxide (2 g, 5 mmol) were dissolved in hot ethanol (50 ml). The clear solution was filtered and colorless crystals separated from the cool solution after a day (yield: 75%).