3-[(5-Chloro-2-hy­droxy­benzyl­idene)amino]-2-sulfanyl­idene-1,3-thia­zolidin-4-one

Hakan Dal

doi:10.1107/S1600536813016577

. 2013 Jun 19;69(Pt 7):o1128. doi: 10.1107/S1600536813016577

3-[(5-Chloro-2-hydroxybenzylidene)amino]-2-sulfanylidene-1,3-thiazolidin-4-one

Hakan Dal ^a,^*

PMCID: PMC3770396 PMID: 24046681

Abstract

In the title compound, C₁₀H₇ClN₂O₂S₂, the mean plane of the thioxothiazolidine ring [maximum deviation = 0.032 (2) Å] is inclined to the benzene ring by 12.25 (4)°. There is a strong intramolecular O—H⋯N hydrogen bond present. In the crystal, molecules are linked via pairs of C—H⋯Cl hydrogen bonds, forming inversion dimers.

Related literature

For general background to the chemistry, and pharmacological and biological activity of rhodanine and its derivatives, see: Raper (1985 ▶); Contello et al. (1994 ▶); Villain-Guillot et al. (2007 ▶); Yan et al. (2007 ▶); Kletzien et al. (1992 ▶).

Experimental

Crystal data

C₁₀H₇ClN₂O₂S₂
M _r = 286.77
Monoclinic,
a = 9.8506 (3) Å
b = 10.0936 (3) Å
c = 12.1096 (4) Å
β = 110.409 (2)°
V = 1128.45 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.37 × 0.26 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.783, T _max = 0.927
10564 measured reflections
2816 independent reflections
2427 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.081
S = 1.09
2816 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016577/su2611sup1.cif

e-69-o1128-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016577/su2611Isup2.hkl

e-69-o1128-Isup2.hkl^{(135.4KB, hkl)}

Click here for additional data file.^{(4.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016577/su2611Isup3.cml

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⋯N2	0.75 (2)	1.97 (2)	2.6291 (19)	147 (3)
C9—H9B⋯Cl1ⁱ	0.99	2.81	3.7860 (19)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author is indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer.

supplementary crystallographic information

Comment

Rhodanine and its derivatives are used in a variety of applications ranging from industry to biochemistry and coordination chemistry. They have wide industrial applications as brightening additives in silver electroplating, intermediates in the syntheses of dyes, extreme-pressure lubricants and antioxidants as well as pharmacological (Contello et al., 1994), and biological activities including antibacterial (Villain-Guillot et al., 2007), antiviral (Yan et al., 2007) and antidiabetical (Kletzien et al., 1992). The interesting aspect of the chemistry of these compounds is their electron donating power to metal ions, which make them strong ligands in coordination compounds (Raper, 1985). herein we report on the crystal structure of the title rhodanine derivative.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. Ring B (S1/N1/C8–C10) is planar to within 0.032 (2) Å and is inclined to the benzene ring A (C1–C6) at a dihedral angle of 12.25 (4)°. Atoms Cl1, O2 and C7 are -0.0272 (4), -0.047 (2) and 0.052 (2) Å out of the plane of ring A, while atoms O1, S2 and N2 are 0.112 (2), -0.0327 (5) and 0.024 (2) Å displaced from the mean plane of ring B. The presence of the intramolecular O—H···N hydrogen bond (Table 1) forms a non-planar six-membered ring (O2/N2/H2/C5–C7), and contributes to the stabilization of the molecule.

In the crystal, molecules are linked via a pair of C-H···Cl hydrogen bonds forming inversion dimers (Table 1).

Experimental

The title compound was prepared by the reaction of 2-hydroxy-5-chlorophenyl (0.63 g, 4 mmol) and N-amino rhodanine (0.50 g, 4 mmol) in methanol (50 ml) at room temperature. After stirring for 6 h, a fluffy yellow precipitate was obtained. The resulting crude solid was collected by filtration, dried and then purified by repeated recrystallization using methanol as solvent; yielding yellow block-like crystals.