Trichlorido(4-methyl­benz­yl)bis­(1H-pyrazole-κN 2)tin(IV)

Thy Chun Keng; Kong Mun Lo; Seik Weng Ng

doi:10.1107/S1600536811015698

. 2011 May 7;67(Pt 6):m659. doi: 10.1107/S1600536811015698

Trichlorido(4-methylbenzyl)bis(1H-pyrazole-κN ²)tin(IV)

Thy Chun Keng ^a, Kong Mun Lo ^a, Seik Weng Ng ^a,^*

PMCID: PMC3120481 PMID: 21754571

Abstract

The six-coordinate Sn^IV atom in the title compound, [Sn(C₈H₉)Cl₃(C₃H₄N₂)₂], shows an octahedral coordination. The N atoms of the N-heterocycle are cis to each other. The Sn—N bond that is trans to the Sn—C bond is shorter than the Sn—N bond trans to the Sn—Cl bond. Weak N—H⋯Cl hydrogen bonds link adjacent molecules, generating a double chain running along the c axis.

Related literature

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961 ▶). For the trichloridophenyltin–di(pyrazole) adduct, see: Casas et al. (1996 ▶).

Experimental

Crystal data

[Sn(C₈H₉)Cl₃(C₃H₄N₂)₂]
M _r = 466.36
Monoclinic,
a = 34.7322 (4) Å
b = 7.3709 (1) Å
c = 14.5760 (2) Å
β = 109.0535 (5)°
V = 3527.13 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.90 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.599, T _max = 0.702
16131 measured reflections
4053 independent reflections
3734 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.017
wR(F ²) = 0.044
S = 1.00
4053 reflections
208 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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/S1600536811015698/bt5524sup1.cif

e-67-0m659-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015698/bt5524Isup2.hkl

e-67-0m659-Isup2.hkl^{(198.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1ⁱ	0.87 (1)	2.56 (2)	3.265 (2)	139 (2)
N4—H4⋯Cl1ⁱⁱ	0.88 (1)	2.65 (2)	3.270 (2)	129 (2)

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

Acknowledgments

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Dibenzyltin dichloride and benzyltin trichloride can be synthesized by the direct action of benzyl chloride on stannous chloride; other ring-substituted analogs are similarly synthesized (Sisido et al., 1961). The title compound results from the reaction of di(4-methylbenzyl)tin dichloride with pyrazole to afford the pyrazole adduct of a monoorganotin trichloride. There are few examples of monororganotin chlorides forming adducts with N-heterocycles. Phenyltin trichloride forms a 1:2 adduct with pyrazole (Casas et al., 1996). The 4-methylbenzyl analog affords a similar 1:2 adduct. The six-coordinate Sn^IV atom in SnCl₃(C₈H₉)(C₃H₄N₂)₂ (Scheme I) shows octahedral coordination. The N atoms of the N-heterocycle are cis to each other and the three Cl atoms are coplanar (Fig. 1). The geometry can be described as being a mer-octahedron. The Sn–N bond that is trans to the Sn–C bond is shorter than the Sn–N bond trans to the Sn–Cl bond.

Experimental

Di(4-methylbenzyl)tin dichloride was synthesized by using a literature procedure (Sisido et al., 1961). The compound (0.4 g, 1 mmol) and pyrazole (0.136 g, 2 mmol) of pyrazole were dissolved in ethanol (100 ml) and the solution was heated for an hour. The solution was filtered and then set aside for the growth of colorless crystals.