2-[(2-Carboxy­phen­yl)sulfan­yl]acetic acid

Cai-Hong Zhan; Ling-Xian Chen; Yun-Long Feng

doi:10.1107/S1600536809034126

. 2009 Sep 5;65(Pt 10):o2315. doi: 10.1107/S1600536809034126

2-[(2-Carboxyphenyl)sulfanyl]acetic acid

Cai-Hong Zhan ^a, Ling-Xian Chen ^a, Yun-Long Feng ^a,^*

PMCID: PMC2970427 PMID: 21577786

Abstract

The title compound, C₉H₈O₄S, affords a zigzig chain in the crystal structure by intermolecular O—H⋯O hydrogen bonds. The molecular geometry suggests that extensive but not uniform π-electron delocalization is present in the benzene ring and extends over the exocyclic C—S and C—C bonds.

Related literature

For background to the coordination chemistry of rigid carboxylate system, see: Sagatys et al. (2003 ▶); Sokolov et al. (2001 ▶).

Experimental

Crystal data

C₉H₈O₄S
M _r = 212.22
Triclinic,
a = 5.1786 (5) Å
b = 9.2973 (9) Å
c = 10.4776 (11) Å
α = 69.980 (4)°
β = 81.959 (6)°
γ = 79.732 (6)°
V = 464.69 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.33 × 0.24 × 0.15 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.910, T _max = 0.952
6609 measured reflections
2110 independent reflections
1941 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.222
S = 1.19
2110 reflections
133 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809034126/at2858sup1.cif

e-65-o2315-sup1.cif^{(14KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034126/at2858Isup2.hkl

e-65-o2315-Isup2.hkl^{(103.8KB, 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
O2—H2⋯O1ⁱ	0.86 (7)	1.92 (5)	2.687 (6)	149 (8)
O3—H3⋯O4ⁱⁱ	0.85 (2)	1.80 (5)	2.634 (4)	167 (6)

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

supplementary crystallographic information

Comment

Thioacetatebenzoic acid (I) is an interesting ligand from a structural point of view since it can display a wide range of coordination patterns with metal ions. The ligand (I) belongs to dicarboxylic acids. The characteristic coordination chemistry of the rigid carboxylate system may facilitate the formation of inorganic-organic materials with high thermal stability and form large channels, while the peculiar coordination chemistry of the flexible carboxylate system employed in the self-assembly reaction has versatile coordination behavior and may be favorable for the formation of the helical structure (Sagatys et al., 2003; Sokolov et al., 2001). As shown in Fig.1, the bond lengths within the benzene ring exhibit the expected pattern with C—C bonds (1.368 (8)–1.399 (6) Å) between the single and double bonds. And the bond distance of C1—C7 (1.476 (5) Å) and S1—C6 (1.768 (4) Å) also fall between the double and single bonds. All these interatomic distances suggest that extensive but not uniform π electron delocalization is present in the benzene ring and extends over the exocyclic C—S and C—C bonds. The torsion angle of C6—S1—C8—C9 is -71.7 (4)°. O—H···O hydrogen bonds link independent molecules to form a zigzig chain.

Experimental

To an aqueous solution of 2-thiobenzoic acid (1.54 g, 10.0 mmol) and NaOH (0.80 g, 20.0 mmol) were sequentially added the aqueous solution of chloroactic acid (2.835 g, 30.0 mmol) and NaOH (1.400 g, 35.0 mmol). After stirring for 4 h at 353 K under nitrogen atmosphere, the mixture was cooled to room temperature slowly. Adjusted the pH to 2 by adding 1.0 mol/L HCl, the pink deposit appeared rapidly. The solids were filtered and washed with water. The single crystals suitable for X-ray diffraction were obtained by the recrystallization of sieved solid in the ethanol.