Bis(5-methyl­pyrazine-2-carboxyl­ato)­diphenyl­tin(IV)

Zhongjun Gao

doi:10.1107/S1600536808016139

. 2008 Jun 7;64(Pt 7):m867. doi: 10.1107/S1600536808016139

Bis(5-methylpyrazine-2-carboxylato)diphenyltin(IV)

Zhongjun Gao ^a,^*

PMCID: PMC2961826 PMID: 21202741

Abstract

In the molecule of the title compound, [Sn(C₆H₅)₂(C₆H₅N₂O₂)₂], two O and one N atoms from the two 5-methylpyrazine-2-carboxylate ligands and one C atom of a phenyl group form a distorted square-planar arrangement in the equatorial plane around the Sn atom, while the distorted octahedral coordination is completed by an N atom of one of the 5-methylpyrazine-2-carboxylate ligands and a C atom of the other phenyl group in the axial positions. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Gielen et al. (1988 ▶). For related literature, see: Vollano et al. (1984 ▶); Ma et al. (2004 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₆H₅N₂O₂)₂]
M _r = 547.13
Monoclinic,
a = 12.030 (4) Å
b = 14.658 (5) Å
c = 13.409 (5) Å
β = 91.872 (4)°
V = 2363.2 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 298 (2) K
0.45 × 0.43 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.633, T _max = 0.824
12010 measured reflections
4166 independent reflections
2732 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.132
S = 1.05
4166 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.46 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016139/hk2458sup1.cif

e-64-0m867-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016139/hk2458Isup2.hkl

e-64-0m867-Isup2.hkl^{(204.2KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Sn1—O1	2.086 (4)
Sn1—O3	2.091 (4)
Sn1—C13	2.117 (5)
Sn1—C19	2.130 (6)
Sn1—N1	2.357 (4)
Sn1—N3	2.363 (5)

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O1—Sn1—O3	149.56 (15)
O1—Sn1—C13	97.14 (18)
O3—Sn1—C13	101.11 (18)
O1—Sn1—C19	101.5 (2)
O3—Sn1—C19	96.7 (2)
C13—Sn1—C19	105.6 (2)
O1—Sn1—N1	73.49 (15)
O3—Sn1—N1	82.40 (15)
C13—Sn1—N1	163.15 (18)
C19—Sn1—N1	90.17 (18)
O1—Sn1—N3	83.74 (16)
O3—Sn1—N3	73.16 (16)
C13—Sn1—N3	87.08 (18)
C19—Sn1—N3	165.3 (2)
N1—Sn1—N3	78.12 (15)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O2ⁱ	0.96	2.51	3.315 (3)	142
C14—H14⋯O2ⁱ	0.93	2.57	3.298 (3)	135

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Symmetry code: (i) Inline graphic .

Acknowledgments

We 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). 5-methylpyrazine-2-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 (Ma et al., 2004).

The molecule of the title compound, (I), (Fig. 1) consists of two phenyl and two (5-methylpyrazine-2-carboxylate) groups bonded to the Sn atom and has a monomeric structure. The two O and the one N atoms of the two 2-methylpyrazine -5-carboxylate ligands and the one C atom of the one phenyl group in the equatorial plane around the Sn atom form a distorted square-planar arrangement, while the distorted octahedral coordination is completed by the one N atom of the one 5-methylpyrazine-2-carboxylate ligand and the one C atom of the other phenyl group in the axial positions (Table 1 and Fig. 1). The Sn1-O1 [2.086 (4) Å] and Sn1-O3 [2.091 (4) Å] bonds are much shorter than the van der Waal's sum of 4.0 Å (Vollano et al., 1984).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, a mixture of diphenyltin dichloride (344 mg, 1.0 mmol), 5-methylpyrazine-2-carboxylic acid (276 mg, 2.0 mmol) and sodium ethoxide (136 mg, 2.0 mmol) in ethanol (80 ml) was heated under reflux for 12 h at 303 K. The resulting clear solution was evaporated under vacuum and the product recrystallized from a mixture of methanol to yield colorless, block-like crystals of (I) (yield; 377 mg, 69%, m.p. 459 K). Analysis, calculated for (I): C 52.68, H, 3.68; N 10.24%; found: C 52.96, H 3.87, N, 10.11%.