8-Hy­droxy-2-methyl­quinolinium tetra­chlorido(pyrazine-2-carboxyl­ato-κ2 N 1,O 2)stannate(IV) methanol monosolvate

Marzieh Vafaee; Ezzatollah Najafi; Mostafa M Amini; Seik Weng Ng

doi:10.1107/S1600536811032296

. 2011 Aug 17;67(Pt 9):m1246. doi: 10.1107/S1600536811032296

8-Hydroxy-2-methylquinolinium tetrachlorido(pyrazine-2-carboxylato-κ² N ¹,O ²)stannate(IV) methanol monosolvate

Marzieh Vafaee ^a, Ezzatollah Najafi ^a, Mostafa M Amini ^a, Seik Weng Ng ^b,^c,^*

PMCID: PMC3200866 PMID: 22064808

Abstract

In the title solvated salt, (C₁₀H₁₀NO)[SnCl₄(C₅H₃N₂O₂)]·CH₃OH, the Sn^IV atom is chelated by the N,O-bidentate pyrazine-2-carboxylate ligand and four chloride ions, and shows a distorted octahedral SnNOCl₄ coordination at the metal atom. The 8-hydroxy-2-methylquinolinium cation and the anion are linked to the methanol molecules by O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, generating a linear chain running along [1 Inline graphic 0]. There are two independent ion pairs and solvent molecules in the asymmetric unit. The crystal studied was a non-merohedral twin with a 41.8 (1)% twin component.

Related literature

For another ammonium tetrachlorido(pyrazine-2-carboxylato)stannate(IV), see: Najafi et al. (2011 ▶).

Experimental

Crystal data

(C₁₀H₁₀NO)[SnCl₄(C₅H₃N₂O₂)]·CH₄O
M _r = 575.82
Triclinic,
a = 6.8392 (2) Å
b = 16.9759 (8) Å
c = 17.6637 (10) Å
α = 90.337 (4)°
β = 94.429 (4)°
γ = 92.232 (3)°
V = 2043.03 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.661, T _max = 0.840
11717 measured reflections
11717 independent reflections
10323 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.116
S = 1.08
11717 reflections
514 parameters
H-atom parameters constrained
Δρ_max = 1.47 e Å⁻³
Δρ_min = −1.44 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) global, I. DOI: 10.1107/S1600536811032296/zs2137sup1.cif

e-67-m1246-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032296/zs2137Isup2.hkl

e-67-m1246-Isup2.hkl^{(572.8KB, 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
O5—H5o⋯O7	0.84	1.84	2.661 (5)	167
O7—H7o⋯N2	0.84	2.05	2.871 (5)	165
O6—H6o⋯O8	0.84	1.82	2.649 (5)	171
O8—H8o⋯N4	0.84	2.10	2.924 (5)	168
N5—H5n⋯O4	0.88	1.88	2.731 (5)	163
N6—H6n⋯O2ⁱ	0.88	1.98	2.838 (5)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

In a recent study, we reacted stannic chloride with pyrazine-2-carboxylic acid in methanol, the reaction yielding the tetrachlorido(pyrazine-2-carbxoylato)stannate anion, whose charge was balanced by a 3-methoxycarbonyl-1-methylpyrazinium cation (Najafi et al., 2011). The cation was derived from the original carboxylic acid which was simultaneously esterified and N-methylated. A similar synthesis but with 2-methyl-8-hydroxyquinoline in methanol medium yielded the solvated title salt (Scheme I, Fig. 1). The less sterically crowded carboxylate ligand engages in chelation, and the more crowded quinoline ligand is protonated. The Sn^IV atom shows distorted octahedral SnNOCl₄ coordination. The cation and anion are linked to the methanol molecules by O–H···O and N–H···O hydrogen bonds (Table 1). There are two independent ion-pairs and solvent molecules. The crystal studied is a non-merohedral twin with a 41.8 (1)% twin component.

Experimental

Stannic chloride pentahydrate (0.35 g, 1 mmol), pyrazine-2-carboxylic acid (0.13 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.