4-(4-Carb­oxy-1,3-thia­zol-2-yl)pyridinium 3-carb­oxy-4-hydroxy­benzene­sulfonate dihydrate

Zhong-Xiang Du; Jun-Xia Li

doi:10.1107/S1600536808030924

. 2008 Sep 30;64(Pt 10):o2044. doi: 10.1107/S1600536808030924

4-(4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate

Zhong-Xiang Du ^a,^*, Jun-Xia Li ^a

PMCID: PMC2959449 PMID: 21201236

Abstract

In the crystal structure of the title compound, C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O, an H atom from the 5-sulfosalicylic acid is transferred to the pyridyl N atom, forming a salt. The dihedral angle between the thiazole and pyridinium rings is 5.909 (5)°. The crystal packing is determined by O—H⋯O and N—H⋯O hydrogen bonds involving water molecules.

Related literature

For related structures, see: Chen et al. (2007 ▶); Ellsworth et al. (2006 ▶); Su et al. (2004 ▶).

Experimental

Crystal data

C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O
M _r = 460.43
Triclinic,
a = 8.6234 (14) Å
b = 10.6065 (17) Å
c = 10.7979 (17) Å
α = 97.799 (2)°
β = 94.479 (2)°
γ = 99.885 (2)°
V = 958.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 291 (2) K
0.44 × 0.29 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.867, T _max = 0.924
7016 measured reflections
3494 independent reflections
3095 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.092
S = 1.03
3494 reflections
275 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536808030924/kp2193sup1.cif

e-64-o2044-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030924/kp2193Isup2.hkl

e-64-o2044-Isup2.hkl^{(171.3KB, 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
O1—H1⋯O2	0.82	1.88	2.599 (2)	146
O3—H3⋯O9	0.82	1.71	2.5269 (17)	171
O8—H8⋯O4ⁱ	0.82	1.89	2.6979 (18)	171
O9—H1W⋯O6ⁱⁱ	0.84	1.93	2.753 (2)	165
O9—H2W⋯O5ⁱⁱⁱ	0.83	1.89	2.713 (2)	172
O10—H3W⋯O2	0.81	2.32	2.9001 (19)	129
O10—H4W⋯O7^iv	0.81	2.27	2.835 (2)	128
N2—H2D⋯O10^v	0.86	1.86	2.689 (2)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20471026) and the Natural Science Foundation of Henan Province (No. 0311021200).

supplementary crystallographic information

Comment

2-(4-Pyridyl)thiazole-4-carboxylic acid (HPTCA), which is an asymmetric, chelating ligand, has been studied in recent years. Five of its transition metal complexes (Chen et al., 2007; Ellsworth et al., 2006; Su et al., 2004) were reported. In this paper we describe its salt with 5-sulfosalicylic acid (H₃SSA), (I).

The crystal structure of the title molecule comprises 2-(4-pyridylomium)thiazole-4-carboxylic acid, a 5-sulfosalicylic acid anion and two water molecules (Fig.1). The H atom of the 5-sulfosalicylic acid is transferred to the pyridyl N-atom of 2-(4-pyridyl)thiazole-4-carboxylic acid, thus forming a salt. The dihedral angle between the thiazole and pyridinium rings is 5.909 (5)°. The N—H and O—H groups are involved in intra- and intermolecular hydrogen bonds with water molecules generating the 3-dimensional hydrogen bond network (Table 1 and Fig. 2).

Experimental

The ligand HPTCA (1 mmol, 0.21 g) and H₃SSA.2H₂O (1 mmol, 0.25 g) were dissolved in solvent mixture of water and methanol (20 mL, v/v 1:1). To this solution, Cu(CH₃COO)₂.4H₂O (1 mmol, 0.26 g) was added and the resulting mixture was stirred and refluxed at 353 K for 3 h, then cooled to room temperature. After filtration and evaporation in air for five days, colourless claviform-shaped crystals were obtained in a yield of 43%. Analysis, found (%): C, 41.75; H, 3.51; N, 6.02; S,13.87. C₁₆H₁₆N₂O₁₀S₂ requires (%): C,41.70; H,3.47; N,6.08; S,13.90. (The elemental analysis indicates that the copper(II) is not coordinated by the ligands) (CCDC number 685021)