Chloridobis(2-chloro­benz­yl)(quinolin-8-olato-κ2 N,O)tin(IV)

Thy Chun Keng; Kong Mun Lo; Seik Weng Ng

doi:10.1107/S160053681101573X

. 2011 May 7;67(Pt 6):m663. doi: 10.1107/S160053681101573X

Chloridobis(2-chlorobenzyl)(quinolin-8-olato-κ² N,O)tin(IV)

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

PMCID: PMC3120540 PMID: 21754575

Abstract

The Sn^IV atom in the three independent molecules of the title compound, [Sn(C₇H₆Cl)₂(C₉H₆NO)Cl], is N,O-chelated by the quinolin-8-olate anion and exists in a cis-C₂SnNOCl trigonal–bipyramidal geometry; the O atom of the anion and the two benzyl C atoms lie in the equatorial plane.

Related literature

For the direct synthesis of the organotin chloride reactant, see: Sisido et al. (1961 ▶). For related structures, see: Shi & Hu (1987 ▶); Vafaee et al. (2010 ▶).

Experimental

Crystal data

[Sn(C₇H₆Cl)₂(C₉H₆NO)Cl]
M _r = 549.42
Monoclinic,
a = 10.2504 (1) Å
b = 41.2573 (6) Å
c = 15.3882 (2) Å
β = 100.3433 (6)°
V = 6401.98 (14) Å³
Z = 12
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.692, T _max = 0.797
41105 measured reflections
14589 independent reflections
13128 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.086
S = 1.11
14589 reflections
784 parameters
H-atom parameters constrained
Δρ_max = 1.27 e Å⁻³
Δρ_min = −1.42 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT; data reduction: SAINT (Bruker, 2009 ▶); 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/S160053681101573X/bt5528sup1.cif

e-67-0m663-sup1.cif^{(43.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101573X/bt5528Isup2.hkl

e-67-0m663-Isup2.hkl^{(713.1KB, hkl)}

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

Acknowledgments

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

supplementary crystallographic information

Comment

8-Hydroxyquinoline forms a large number of derivatives with organotin systems; when the reaction is carried out with diorganotin dichlorides, in some cases only one chloride is displaced whereas in other cases both are displaced. No base is added to abstract the acid hydroxy proton. In the present study, the reaction of 8-hydroxyquinoline with bis(2-chlorobenzyl)tin dichloride affords SnCl(C₇H₆Cl)₂(C₉H₆NO) (Scheme I). The Sn^IV atom in the three independent molecules N,O-chelated by the quinolinato group and it exists in a cis-C₂SnNOCl trigonal bipyramidal geometry; the O atom lies in the equatorial plane and the Cl and N atoms comprise the axial sites (Figs. 1, 2, 3). The molecules are positioned such that two are disposed about a false-center of inversion (Fig. 2). There are no Sn···Cl contacts and the distortion of geometry from the idealized trigonal bipyramid is minimal (14.7% in the first molecule, 13.7% in the second and only 9.9% in the third).

In the diethytin derivative, an intermolecule Sn···Cl interaction raises the coordination number of Sn to six in the chain structure (Shi & Hu, 1987). On the other hand, the methylphenyltin derivative also has Sn in a six-coordinate environment, but the higher coordination number arises from bridging by the quinolinate ion that results in a dinuclear molecule (Vafaee et al., 2010).

Experimental

The diorganotin dichloride was synthesized by the direct reaction of 2-chlorobenzyl chloride and metallic tin according to a literature procedure (Sisido et al., 1961). The diorganotin dichloride (0.44 g, 1 mmol) and 8-hydroxyquinoline (0.15 g, 1 mmol) were dissolved in chloroform (50 ml) to give a yellow solution. The solution was filtered and the solvent allowed to evaporate to yield yellow crystals.