5-(4-Hy­droxy-3-meth­oxy­benz­yl)-1,3-thia­zolidine-2,4-dione monohydrate

Li-Yan Xiong; Ting-Fang Wang; Li-Ping Zheng; Chuan Zhang; Feng-Chun Wang

doi:10.1107/S1600536810049895

. 2010 Dec 4;67(Pt 1):o16. doi: 10.1107/S1600536810049895

5-(4-Hydroxy-3-methoxybenzyl)-1,3-thiazolidine-2,4-dione monohydrate

Li-Yan Xiong ^a, Ting-Fang Wang ^b, Li-Ping Zheng ^b, Chuan Zhang ^a,^*, Feng-Chun Wang ^c

PMCID: PMC3050404 PMID: 21522666

Abstract

In the title compound, C₁₁H₁₁NO₄S·H₂O, the five-membered thiazolidine ring is nearly planar, with a maximum deviation of 0.010 (2) Å. The dihedral angle between the thiazolidine and benzene rings is 49.16 (9)°. Intermolecular O—H⋯O and N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the therapeutic and pharmacological properties of thiazolidinediones, see: Day (1999 ▶); Spiegelman (1998 ▶). For the synthesis of the title compound, see: Madhavan et al. (2002 ▶); Shoda et al. (1983 ▶). For related structures, see: Divjaković et al. (1991 ▶); Yathirajan et al. (2005 ▶).

Experimental

Crystal data

C₁₁H₁₁NO₄S·H₂O
M _r = 271.28
Monoclinic,
a = 10.684 (4) Å
b = 8.151 (3) Å
c = 14.747 (5) Å
β = 99.657 (4)°
V = 1266.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.960, T _max = 0.974
4985 measured reflections
2226 independent reflections
1902 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.119
S = 1.05
2226 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049895/xu5102sup1.cif

e-67-00o16-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049895/xu5102Isup2.hkl

e-67-00o16-Isup2.hkl^{(109.5KB, 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
N3—H3⋯O2ⁱ	0.86	2.03	2.886 (2)	174
O4—H4A⋯O5ⁱⁱ	0.82	1.87	2.685 (2)	171
O5—H5A⋯O3	0.82 (5)	2.19 (5)	2.962 (2)	156 (4)
O5—H5A⋯O4	0.82 (5)	2.37 (4)	2.947 (2)	127 (4)
O5—H5B⋯O1ⁱⁱⁱ	0.85 (3)	1.97 (3)	2.795 (3)	163 (3)

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

Acknowledgments

This study was supported by the Science and Technology Commission of Shanghai special purpose for modernization of traditional Chinese medicine in 2008 (No 08DZ1970802) and the National Basic Research Program of China (No 2006CB504100 and 2009CB521907).

supplementary crystallographic information

Comment

Thiazolidinediones (TZDs), which are known to sensitize tissues to insulin, have been developed and clinically used as antidiabetic agents. They have been shown to reduce plasma glucose, lipid, and insulin levels, and used for the treatment of type 2 diabetes (Day, 1999; Spiegelman, 1998). Prompted by the activity of TZDs, we have synthesized the title compound to study its crystal structure.

The asymmetric unit contains a 5-(4-hydroxy-3-methoxybenzyl)thiazolidine-2,4-dione molecule and a solvate water molecule (Fig. 1). The geometric parameter of the title compoundare to its related structures (Divjakovic et al., 1991; Yathirajan et al., 2005). The dihedral angle between the thiazolidinedione ring [S1/C2/N3/C4/C5] and the benzene ring [C7–C12] is 49.16 (9)°. In the crystal packing (Fig. 2), the molecules are linked via intermolecular N1—H1···O2 hydrogen bonds. In addition, the molecule is connected to the water molecule by O5—H5···O1, O5—H5···O4, O5—H5···O3 and O4—H4···O5 hydrogen bonds which generate a three dimensional network (Table 1).

Experimental

A mixture of 2,4-tThiazolidinedione (3.51 g, 0.03 mol), 4-hydroxy-3-methoxybenzaldehyde (4.56 g, 0.03 mol), acetic acid (0.18 g, 0.003 mol) and piperidine (0.26 g, 0.003 mol) in toluene (60 ml) was refluxed for 5 h with continuous removal of water. The reaction mixture was cooled to room temperature and the resultant crystalline compound was filtered and washed with water and dried to afford the (Z)-5-(4-hydroxy-3-methoxybenzylidene)thiazolidine-2,4-dione. Yield=7.33 g, 97.3%. To a solution of (Z)-5-(4-hydroxy-3-methoxybenzylidene) thiazolidine-2,4-dione (4 g, 0.016 mol) in 1,4-dioxane (400 ml), hydrogenated in the presence of 10% Pd/C (1.0 g) at 60 psi for 24 h. The mixture was filtered through a bed of Celite. The filtrate was evaporated under reduced pressure and purified by column chromatography using 50:1 CH₂Cl₂/MeOH to afford the title compound as yellowish solid. Yield = 1.96 g, 48.6% (Madhavan et al., 2002; Shoda et al., 1983). Crystallization of the product was carried out by dissolving the product in 10 ml a solvent mixture of MeOH and water (4:1) at room temperature.