3-(2H-1,3-Benzodioxol-5-ylmeth­yl)-2-(2-meth­oxy­phen­yl)-1,3-thia­zolidin-4-one

Victor Facchinetti; Claudia R B Gomes; Wilson Cunico; Solange M S V Wardell; James L Wardell; Edward R T Tiekink

doi:10.1107/S1600536811041262

. 2011 Oct 22;67(Pt 11):o2970–o2971. doi: 10.1107/S1600536811041262

3-(2H-1,3-Benzodioxol-5-ylmethyl)-2-(2-methoxyphenyl)-1,3-thiazolidin-4-one

Victor Facchinetti ^a, Claudia R B Gomes ^a, Wilson Cunico ^b, Solange M S V Wardell ^c, James L Wardell ^d,^‡, Edward R T Tiekink ^e,^*

PMCID: PMC3247375 PMID: 22219993

Abstract

The title molecule, C₁₈H₁₇NO₄S, features a 1,3-thiazolidine ring that is twisted about the S—C(methylene) bond. With reference to this ring, the 1,3-benzodioxole and benzene rings lie to either side and form dihedral angles of 69.72 (16) and 83.60 (14)°, respectively, with the central ring. Significant twisting in the molecule is confirmed by the dihedral angle of 79.91 (13)° formed between the outer rings. Linear supramolecular chains along the a-axis direction mediated by C—H⋯O interactions feature in the crystal packing.

Related literature

For background to the biological activity of thiazolidinones, see: Cunico et al. (2008a ▶); Solomon et al. (2007 ▶); Kavitha et al. (2006 ▶); Sharma et al. (2006 ▶); Ravichandran et al. (2009 ▶); Rao et al. (2004 ▶). For background to the synthesis, see: Cunico et al. (2008b ▶); Rawal et al. (2008 ▶), Gomes et al. (2010 ▶), Neuenfeldt et al. (2011 ▶). For related studies on the synthesis and biological evaluation of thiazolidinones, see: Cunico et al. (2006 ▶, 2007 ▶). For a thiazolidinone structure, see: Neuenfeldt et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₇NO₄S
M _r = 343.39
Monoclinic,
a = 6.8137 (3) Å
b = 12.5753 (7) Å
c = 18.5071 (9) Å
β = 91.825 (3)°
V = 1584.96 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 120 K
0.16 × 0.06 × 0.05 mm

Data collection

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.553, T _max = 0.746
21683 measured reflections
3625 independent reflections
1935 reflections with I > 2σ(I)
R _int = 0.159

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.180
S = 1.02
3625 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041262/hb6438sup1.cif

e-67-o2970-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041262/hb6438Isup2.hkl

e-67-o2970-Isup2.hkl^{(174.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041262/hb6438Isup3.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
C9—H9⋯O1ⁱ	0.95	2.36	3.302 (4)	170
C13—H13⋯O1ⁱⁱ	0.95	2.43	3.352 (4)	163

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

Acknowledgments

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

supplementary crystallographic information

Comment

Thiazolidinones constitute an important group of heterocyclic compounds (Cunico et al., 2008a), having valuable biological uses, for example, as anti-malarial (Solomon et al., 2007), anti-microbial (Kavitha et al., 2006), anti-inflammatory (Sharma et al., 2006), and anti-viral agents, especially as anti-HIV agents (Ravichandran et al., 2009; Rao et al., 2004). The main synthetic routes to 1,3-thiazolidin-4-ones involve three components (an aldehyde, an amine and mercaptoacetic acid), either in a one- or two-step process (Cunico et al., 2008a; Rawal et al., 2008), and also under ultrasound irradiation (Neuenfeldt et al., 2011). The structure of 1-thia-4-azaspiro[4.5]decan-3-one has been reported recently (Neuenfeldt et al., 2009). In continuation of our research on thiazolidinones, (Cunico et al., 2006; Cunico et al., 2007; Cunico et al., 2008b; Gomes et al., 2010; Neuenfeldt et al., 2011), we now wish to report the structure of 2-(2-methoxybenzaldehyde)-3-piperonyl-1,3-thiazolidin-4-one, (I), synthesized, as reported from piperonylamine, 2-methoxybenzaldehyde and mercaptoacetic acid under ultrasound irradiation (Neuenfeldt et al., 2011). The sample used in the structure determination was grown from its EtOH solution.

The thiazolidinyl ring in (I), Fig. 1, is twisted about the S1—C3 bond but, the deviations from co-planarity for the five atoms are not great, i.e. the maximum and minimum deviations are 0.109 (1) Å for atom S1 and -0.117 (4) Å for atom C3; the ketone-O1 atom lies 0.244 (2) Å out of the least-squares plane through the five-membered ring. The dioxole ring has an envelope conformation with the C15 atom being the flap atom. The r.m.s. deviation for the 13 non-hydrogen atoms comprising the 1,3-benzodioxole ring is 0.110 Å. With reference to the thiazolidinyl ring, the 1,3-benzodioxole and benzene rings lie to either side and form dihedral angles with this ring of 69.72 (16) and 83.60 (14)°, respectively. The outer rings form a dihedral angle of 79.91 (13)° with each other, indicating that the molecule is highly twisted.

The most prominent feature of the crystal packing is the formation of C—H···O interactions involving the bifurcated carbonyl-O1 atom, Table 1. These lead to linear supramolecular chains along the a axis, Fig. 2.

Experimental

The title compound was synthesized as described in the literature (Neuenfeldt et al., 2011) and crystals were obtained from its EtOH solution.