Aquadi-n-but­yl(5-methyl­pyrazine-2-carboxyl­ato)tin(IV) methanol solvate

Zhongjun Gao

doi:10.1107/S1600536808016140

. 2008 Jun 7;64(Pt 7):m864. doi: 10.1107/S1600536808016140

Aquadi-n-butyl(5-methylpyrazine-2-carboxylato)tin(IV) methanol solvate

Zhongjun Gao ^a,^*

PMCID: PMC2961732 PMID: 21202739

Abstract

In the monomeric title compound, [Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₃OH, the Sn atom is seven-coordinate, displaying a distorted pentagonal bipyramidal SnC₂N₂O₃ geometry with the two C atoms in the axial sites. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the complex and solvent molecules into infinite chains.

Related literature

For general background, see: Gielen et al. (1988 ▶). For a related structure, see: Ma et al. (2004 ▶).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₄O
M _r = 557.21
Monoclinic,
a = 20.609 (5) Å
b = 17.119 (4) Å
c = 14.558 (3) Å
β = 98.178 (3)°
V = 5084 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 298 (2) K
0.58 × 0.56 × 0.49 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.582, T _max = 0.628
12959 measured reflections
4462 independent reflections
2981 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.122
S = 1.12
4462 reflections
289 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016140/hb2726sup1.cif

e-64-0m864-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016140/hb2726Isup2.hkl

e-64-0m864-Isup2.hkl^{(218.7KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Sn1—C17	2.103 (5)
Sn1—C13	2.107 (6)
Sn1—O1	2.161 (4)
Sn1—O3	2.167 (4)
Sn1—N1	2.481 (4)
Sn1—N3	2.635 (5)
Sn1—O5	2.770 (4)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O6	0.85	1.92	2.755 (6)	169
O5—H2⋯O1ⁱ	0.85	2.19	3.039 (5)	172
O6—H6⋯O4ⁱ	0.82	1.93	2.703 (6)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the financial support of the Science Foundation of Shandong.

supplementary crystallographic information

Comment

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). 2-Methylpyrazine-5-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.

The title compound, (I), consists of two butyl, two N,O-bidentate 2-methylpyrazine-5-carboxylate groups and a water molecule bonded to the Sn atom and has a monomeric structure. The Sn atom is seven-coordinate with a distorted pentagonal bipyramidal SnC₂N₂O₃ geometry (Table 1, Fig. 1). Around the central Sn atom, atoms C13 and C17 of the two butyl groups occupy the axial position, while O and N atoms lie in equatorial positions. The sum of the angles between the tin atom and the equatorial atoms is 360.4°. The axial bond angle C17—Sn1—C13 [161.6 (3)°] deviates from linearity by over 18°, which shows that these atoms have significant deviations from ideal pentagonal bipyramidal geometry. Otherwise, the bond lenghts and angles in (I) are similar to those in related structures (Ma et al., 2004).

In the crystal, strong intermolecular O—H···O hydrogen bonds (Table 2) between O atoms of the carboxyl groups, methanol and coordinate water molecules result in the formation of one-dimensional polymeric chains (Fig. 2).

Experimental

A mixture of dibutyltin dichloride (1.0 mmol, 0.304 g), 2-methylpyrazine-5-carboxylic acid (2.0 mmol, 0.276 g) and sodium ethoxide (0.136 g, 2.0 mmol) in ethanol (with 5% water) (80 ml) was heated under reflux for 8 h at 303 K. The resulting clear solution was evaporated under vacuum and the product recrystallized from a mixture of methanol to yield colourless, blocks of (I). Yield 0.452 g, 78%, m.p. 438 K, analysis, calculated for C₂₁H₃₄N₄O₆Sn: C 45.26, H, 6.15; N 10.05%; found: C 45.39, H 6.29, N, 10.12%.