4-Methyl-N-[(2-oxo-1,3-thia­zolidin-3-yl)carbon­yl]benzene­sulfonamide

Qing-Wu Chen; Jian-Quan Weng; Cheng-Xia Tan; De-Long Shen

doi:10.1107/S1600536810014467

. 2010 Apr 24;66(Pt 5):o1159. doi: 10.1107/S1600536810014467

4-Methyl-N-[(2-oxo-1,3-thiazolidin-3-yl)carbonyl]benzenesulfonamide

Qing-Wu Chen ^a, Jian-Quan Weng ^a, Cheng-Xia Tan ^a, De-Long Shen ^a,^*

PMCID: PMC2979287 PMID: 21579203

Abstract

The asymmetric unit of the title compound, C₁₁H₁₂N₂O₄S₂, contains two independent molecules with similar dihedral angles of 76.7 (1) and 77.3 (1)° between the mean planes of the five- and six-membered rings. In both molecules, the amino groups are involved in intramolecular N—H⋯O hydrogen bonds. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into ribbons extended along the a axis.

Related literature

For a related structure, see: Gowda et al. (2010 ▶). For details of the synthesis, see: Chen & Shen (2008 ▶). For the biological activity of related compounds, see: Fujimoto & Shimizu (1978 ▶); Liu et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C₁₁H₁₂N₂O₄S₂
M _r = 300.35
Triclinic,
a = 9.5560 (4) Å
b = 9.6722 (4) Å
c = 14.6352 (6) Å
α = 88.7232 (10)°
β = 86.3267 (11)°
γ = 76.5399 (11)°
V = 1312.80 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.39 × 0.36 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.825, T _max = 0.943
13020 measured reflections
5941 independent reflections
4475 reflections with F ² > 2σ(F ²)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.153
S = 1.00
5941 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014467/cv2707sup1.cif

e-66-o1159-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014467/cv2707Isup2.hkl

e-66-o1159-Isup2.hkl^{(290.8KB, 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
N12—H12⋯O11	0.86	2.00	2.665 (3)	134
N32—H32⋯O31	0.86	1.91	2.608 (3)	137
C33—H332⋯O11	0.97	2.40	3.352 (3)	166
C11—H112⋯O33ⁱ	0.96	2.55	3.500 (4)	170
C32—H321⋯O12ⁱⁱ	0.97	2.60	3.384 (3)	138

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

Acknowledgments

This work was funded by the National Natural Science Foundation (grant No. 30900959), the Natural Science Foundation of Zhejiang Province (grant No. Y3080096) and the Zhejiang University of Technology Research Fund (grant No. X 1017104).

supplementary crystallographic information

Comment

2-Thiazolidione derivatives are known as fungicides, insecticides and plant growth regulators (Chen et al. 2008; Fujimoto et al. 1978). Meanwhile, many pesticides contain amide fragments (Liu et al. 2007; Liu et al. 2009) . Herewith we present the title compound (I) - a new thiazolidione derivative synthesized by the reaction of 2-thiazolidione and 4-methyl-benzenesulfonylisocyanate.

In (I) (Fig. 1), the carboxamide moiety is nearly coplanar with the thiazole ring [dihedral angle 7.2 (2)°]. The C4-O12 bond length of 1.202 (3) Å is normal for C=O double bond. The conformation of C—SO₂—NH—C(O) fragment is similar to that observed in N-Benzoyl-2-chlorobenzenesulfonamide (Gowda et al., 2010). Amino groups in two independent molecules are involved in intramolecular N—H···O hydrogen bonds (Table 1). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into ribbons extended along the axis a.

Experimental

The title compound was synthesized according to Chen et al. (2008). 2-Thiazolidiones (1.03 g, 0.01 mol) and 4-methyl- benzenesulfonylisocyanate (1.97 g,0.01 mol) were dissolved in anhydrous acetone(15 ml)with stirring. The mixture was then stirred at room temperature for 15 h. The solution was evaporated in a rotary evaporator at 30 degree under reduced pressure till 1.5 g of solide residue were obtained. This was washed three times with water and dried. Colourless single crystals suitable for crystallographic analysis were obtained by slow evaporation of an acetone-petroleum ether (1:20 v/v) solution.