Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hy­droxy­phen­yl)ethyl­idene]hydrazin-1-yl­idene}-4-oxo-3-phenyl-1,3-thia­zolidin-5-yl­idene)acetate

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536813025270

. 2013 Sep 18;69(Pt 10):o1553–o1554. doi: 10.1107/S1600536813025270

Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate

Shaaban K Mohamed ^a,^b, Joel T Mague ^c, Mehmet Akkurt ^d, Alaa A Hassan ^b, Mustafa R Albayati ^e,^*

PMCID: PMC3790417 PMID: 24098236

Abstract

In the title compound, C₂₀H₁₇N₃O₄S, all non-H atoms, except those of the phenyl ring, are approximately coplanar [maximum deviation = 0.2214 (1) Å], and the dihedral angle between their best plane and the benzene ring is 53.13 (1)°. A short intramolecular O⋯S contact of 2.838 (1) Å is formed between the ester carbonyl O atom and the S atom of the thiazolidine ring. In the crystal, molecules associated via O—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds form layers parallel to (010), with only C—H⋯O-type short contacts between the molecules in adjacent layers.

Related literature

For the biological activity of 4-thiazolidinones, see: Dayam et al. (2006 ▶); Srivastava et al. (2005 ▶), Look et al. (1996 ▶), Barreca et al. (2001 ▶); Diurno et al. (1992 ▶).

Experimental

Crystal data

C₂₀H₁₇N₃O₄S
M _r = 395.42
Monoclinic,
a = 9.5049 (9) Å
b = 20.656 (2) Å
c = 10.1364 (10) Å
β = 107.637 (1)°
V = 1896.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 150 K
0.19 × 0.11 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.82, T _max = 0.99
16907 measured reflections
4582 independent reflections
3740 reflections with i > 2σ(i)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.118
S = 1.06
4582 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (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) global, I. DOI: 10.1107/S1600536813025270/gk2589sup1.cif

e-69-o1553-sup1.cif^{(27.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025270/gk2589Isup2.hkl

e-69-o1553-Isup2.hkl^{(251.3KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813025270/gk2589Isup3.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
O4—H4O⋯O1ⁱ	0.84 (2)	1.96 (2)	2.7901 (16)	174.8 (19)
C8—H8⋯S1ⁱⁱ	0.95	2.82	3.7272 (17)	160
C10—H10⋯O4ⁱⁱⁱ	0.95	2.52	3.452 (2)	167
C19—H19⋯O1ⁱ	0.95	2.47	3.200 (2)	133

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

Acknowledgments

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

supplementary crystallographic information

1. Comment

Thiazolidinone scaffold compounds have received much attention from organic and medicinal chemists due to their therapeutic diversity coupled with their commercial viability. Recently, 4-thiazolidinones have exhibited many interesting bio-activity profiles such as anti-cancer (Dayam et al., 2006) and anti-mycobacterial agents (Srivastava et al., 2005), COX-1 inhibitors (Look et al. 1996), non-nucleoside inhibitors of HIV-RT (Barreca et al., 2001) and anti-histaminic agents (Diurno et al., 1992). In view of these properties the title compound has been synthesized among a series of other 4-thiazolidinones to investigate the relationship between their crystal structures and their antibacterial activity.

In the title compound (Fig. 1), all non-H atoms, except the phenyl group (C7–C12), are approximately coplanar, with the maximum deviations of -0.2214 (1) Å for C6, -0.2097 (1) Å for C14, 0.1651 (1) Å for O2 and -0.1009 (1) Å for O3, and the benzene ring (C7–C12) makes a dihedral angle of 53.13 (1)° with this plane. Molecular conformation is stabilized by a short intramolecular O···S contact of 2.838 (1) Å.

The title compound crystallizes in a layer structure with the layers parallel to the (010) plane (Fig. 2). Molecules within the layers are associated via O—H···O, C—H···O and C—H···S hydrogen bonding (Table 1, Fig. 2). One of the C—H···O contacts (C10—H10···O4) in Table 1 is between the layers. The interlayer regions are occupied by the N-phenyl and ester groups between which there are no significant interactions.

2. Experimental

A mixture of 283 mg (1 mmol) (2Z)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide and 142 mg (1 mmol) dimethyl but-2-ynedioate in 50 ml of ethanol was refluxed and monitored by TLC until completion of the reaction. The excess solvent was evaporated under vacuum and the solid obtained was recrystallized from ethanol to afford clear yellow plates (M.p. 541–543 K) of X-ray quality.