3-(3-Methyl­phen­yl)-2-thioxo-1,3-thia­zolidin-4-one

Durre Shahwar; M Nawaz Tahir; Asma Yasmeen; Naeem Ahmad; Muhammad Akmal Khan

doi:10.1107/S1600536809045863

. 2009 Nov 7;65(Pt 12):o3016. doi: 10.1107/S1600536809045863

3-(3-Methylphenyl)-2-thioxo-1,3-thiazolidin-4-one

Durre Shahwar ^a, M Nawaz Tahir ^b,^a,^*, Asma Yasmeen ^a, Naeem Ahmad ^a, Muhammad Akmal Khan ^a

PMCID: PMC2972004 PMID: 21578753

Abstract

In the title compound, C₁₀H₉NOS₂, the dihedral angle between the rhodanine (2-thioxo-1,3-thiazolidin-4-one) and 3-methylphenyl rings is 83.30 (3)°. The H atoms of the methyl group are disordered over two set of sites with an occupancy ratio of 0.58 (3):0.42 (3). In the crystal, the molecules interact by way of C—H⋯π and C=O⋯π interactions.

Related literature

For related structures, see: Shahwar et al. (2009a ▶,b ▶,c ▶,d ▶,e ▶). graphic file with name e-65-o3016-scheme1.jpg

Experimental

Crystal data

C₁₀H₉NOS₂
M _r = 223.3
Monoclinic,
a = 8.0775 (3) Å
b = 6.4058 (2) Å
c = 21.4715 (7) Å
β = 106.068 (2)°
V = 1067.59 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.849, T _max = 0.897
11841 measured reflections
2666 independent reflections
2116 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.087
S = 1.03
2666 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045863/hb5208sup1.cif

e-65-o3016-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045863/hb5208Isup2.hkl

e-65-o3016-Isup2.hkl^{(128.3KB, 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
C8—H8B⋯Cg2ⁱ	0.97	2.59	3.5219 (17)	162
C7—O1⋯Cg1ⁱ	1.20 (1)	2.94 (1)	4.1070 (16)	164 (1)

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Symmetry code: (i) Inline graphic . Cg1 and Cg2 are the centroids of the S1/C8/C7/N1/C9 and C1—C6 rings, respectively.

Acknowledgments

DS is grateful to Government College University, Lahore, for providing funds under the GCU funded Research Projects Programme.

supplementary crystallographic information

Comment

We have reported the synthesis and crystal structures of various rhodanine derivatives such as (II) (5Z)-5-(2-Hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a), (III) (5E)-5-(4-Hydroxy-3-methoxybenzylidene)-2-thioxo-1, 3-thiazolidin-4-one methanol monosolvate (Shahwar et al., 2009b), (IV) (5Z)-5-(2-Hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one methanol hemisolvate (Shahwar et al., 2009c), (V) 3-(2-Methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009d) and (VI) 3-Cyclohexyl-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009e). The purpose of synthesis of differet rhodanine derivatives is to study the biological activities. The title compound (I, Fig. 1) is being reported in this context.

In (I), the 3-methylphenyl A (C1–C6/C10) and the rhodanine group B (N1/C7/C8/S1/C9/O1/S2) are planar with maximum r. m. s. deviations of 0.0068 and 0.0171 Å respectively, from their mean square planes. The dihedral angle between A/B is 83.30 (3)°. The H-atoms of the methyl moiety are disordered over two set of sites with occupancy ratio of 0.58 (3):0.42 (3) in the monomers. There exist C–H···π and C==O···π interactions (Table 1) which stabilize the molecules.

Experimental

The title compound was prepared by a three step reaction procedure. In the first step meta toluidine aniline (10.7 g, 0.1 mol) and triethylamine (50.5 g, 0.5 mol) were stirred in ethanol (20 ml) followed by dropwise addition of CS₂ (15.2 g, 0.2 mol) while keeping the flask in an ice bath. The precipitate obtained were filtered off and washed with diethyl ether.

In second step, a solution of sodium chloroacetate (11.6 g, 0.1 mol) and chloroacetic acid (18.9 g, 0.2 mol) was prepared in 50 ml distilled water. To this solution the precipitates obtained in first step were added gradually and stirred at 273 K. This mixture was stirred untill it turned light yellow.

In third step the yellow mixture was mixed in 140 ml hot (363–368 K) hydrochloric acid (6 N) and stirred for five minutes to obtain colorless crystalline precipitates. These precipitates were recrystalized in chloroform to get light yellow prisms of (I).