Dichlorido{4-cyclo­hexyl-1-[1-(2-pyridyl-κN)ethyl­idene]thio­semicarbazidato-κ2 N 1,S}methyl­tin(IV)

Md Abdus Salam; Md Abu Affan; Mustaffa Shamsuddin; Seik Weng Ng

doi:10.1107/S1600536810014443

. 2010 Apr 24;66(Pt 5):m570. doi: 10.1107/S1600536810014443

Dichlorido{4-cyclohexyl-1-[1-(2-pyridyl-κN)ethylidene]thiosemicarbazidato-κ² N ¹,S}methyltin(IV)

Md Abdus Salam ^a, Md Abu Affan ^a, Mustaffa Shamsuddin ^a, Seik Weng Ng ^b,^*

PMCID: PMC2979086 PMID: 21579051

Abstract

The monodeprotonated Schiff base ligand in the title compound, [Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂], N,N′,S-chelates to the Sn atom, which is six-coordinated in an octahedral environment. The three coordinating atoms along with the methyl C atom comprise a square plane, above and below which are positioned the Cl atoms. The amino group is a hydrogen-bond donor to a Cl atom of an adjacent molecule, the hydrogen bond giving rise to a helical chain extending parallel to [100].

Related literature

For the crystal structures of other metal derivatives of the Schiff base, see: Joseph et al. (2004 ▶); Kovala-Demertzi et al. (2007 ▶).

Experimental

Crystal data

[Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂]
M _r = 480.02
Orthorhombic,
a = 9.2016 (5) Å
b = 12.2434 (7) Å
c = 17.4544 (10) Å
V = 1966.39 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.633, T _max = 0.730
18838 measured reflections
4498 independent reflections
4223 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.021
wR(F ²) = 0.054
S = 1.02
4498 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ▶), 1493 Friedel pairs
Flack parameter: −0.020 (17)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014443/bt5250sup1.cif

e-66-0m570-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014443/bt5250Isup2.hkl

e-66-0m570-Isup2.hkl^{(220.4KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Sn1—C1	2.136 (3)
Sn1—N1	2.269 (2)
Sn1—N2	2.224 (2)
Sn1—S1	2.4814 (7)
Sn1—Cl1	2.4960 (7)
Sn1—Cl2	2.4701 (8)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl1ⁱ	0.86 (1)	2.36 (1)	3.219 (3)	177 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank MOSTI (grant No. 06-01-09-SF0046), Universiti Malaysia Sarawak and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The mono-deprotonated anion of 2-acetylpyridine 4-cyclohexyl thiosemicarbazone is a ligand that N,N',S-binds to metal atoms (Joseph et al., 2004). Whereas similar ligands have been complexed with diorganotin and triorganotin systems, the monoorganotin analogues have not been so extensively studied. The mono-deprotonated Schiff-base ligand in SnCl₂(CH₃)(C₁₄H₁₉N₄S) N,N',S-chelates to the tin atom, which is six-coordinate in an octahedral environment (Scheme I, Fig. 1). The three coordinating atoms along with the methyl carbon comprise a square plane, above and below which are positioned the chlorine atoms.

Experimental

2-Acetylpyridine 4-cyclohexyl thiosemicarbazone was synthesized by using a literature method (Joseph et al., 2004). The compound (0.28 g, 1 mmol) was dissolved in dry methanol (10 ml) in a Schlenk apparatus under a nitrogen atmosphere. Methyltin trichoride (0.24 g, 1 mmol) dissolved in methanol (10 ml) was added. The mixture was heated for an hour. The solvent was removed and the yellow compound recrystallized from chloroform/methanol (1:1) in 70% yield, m.p. 551-553 K.