(2-{[1,1-Bis(hy­droxy­meth­yl)-2-oxidoeth­yl]imino­meth­yl}-4-chloro­phenolato-κ3 O,N,O′)dibutyl­tin(IV)

See Mun Lee; Hapipah Mohd Ali; Kong Mun Lo

doi:10.1107/S1600536810021872

. 2010 Jun 16;66(Pt 7):m793. doi: 10.1107/S1600536810021872

(2-{[1,1-Bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-4-chlorophenolato-κ³ O,N,O′)dibutyltin(IV)

See Mun Lee ^a, Hapipah Mohd Ali ^a, Kong Mun Lo ^a,^*

PMCID: PMC3006995 PMID: 21587717

Abstract

In the title compound, [Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)], the Schiff base ligand chelates to the Sn^IV atom through the two deprotonated hydroxy groups, as well as through the N atom, to confer an overall cis-C₂SnNO₂ trigonal-bipyramidal geometry at the Sn^IV atom [C—Sn—C = 129.92 (9)°]. The remaining methylenehydroxy groups engage in O—H⋯O hydrogen bonding with the O atoms of adjacent molecules, leading to infinite supramolecular chains propagating in [001].

Related literature

For related structures, see Reisi et al. (2010 ▶); Ng (2008 ▶).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)]
M _r = 535.04
Monoclinic,
a = 18.8326 (9) Å
b = 13.3811 (7) Å
c = 16.5768 (8) Å
β = 91.385 (3)°
V = 4176.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.365, T _max = 0.786
19535 measured reflections
4785 independent reflections
4229 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.022
wR(F ²) = 0.052
S = 1.02
4785 reflections
239 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.38 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: pubCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021872/xu2772sup1.cif

e-66-0m793-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021872/xu2772Isup2.hkl

e-66-0m793-Isup2.hkl^{(234.5KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Sn1—N1	2.2108 (17)
Sn1—O1	2.1203 (15)
Sn1—O2	2.1049 (14)
Sn1—C12	2.139 (2)
Sn1—C16	2.129 (2)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84	1.77	2.608 (2)	174
O4—H4⋯O3ⁱⁱ	0.84	1.93	2.733 (2)	160

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

Acknowledgments

We thank the University of Malaya (grant Nos. PS342/2009 C and RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

The Schiff base derived from the condensation of 5-bromosalicylaldehyde and tris(hydroxymethyl)methylamine is deprotonated with respect to the phenoxy hydrogen atom and one of the methylenehydroxyl hydrogen atom. The ligand coordinates to the dibutyltin fragment through this doubly deprotonated oxygen atoms and the imine nitrogen (Fig. 1).

The tin atom is in a cis-trigonal bipyramidal geometry with a C—Sn—C angle of 129.92 (9)°. The two deprotonated oxygen atoms occupied the axial sites with a O—Sn—O angle of 155.60 (6)°, indicating a distortion in the trigonal bipyramidal geometry at the Sn atom. Adjacent molecules are linked by hydrogen bonds to form an infinite polymeric chain (Fig. 2).

Experimental

The Schiff base, 4-bromo-2-tris[(hydroxymethyl)methylimino]phenol was prepared from tris(hydroxymethyl)aminomethane and 5-bromosalicylaldehyde in absolute ethanol. The compound (0.30 g, 0.1 mmol) and dibutyltin oxide (0.25 g, 1.0 mmol) were heated in 50 ml of toluene in a Dean-Stark apparatus for 8 h. The solution was left for crystallizaton for a week during which yellow crystals were obtained.