Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinyl­idene}-4-oxo-3-phenyl-1,3-thia­zolidin-5-yl­idene)ethano­ate

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

doi:10.1107/S1600536813021533

. 2013 Aug 10;69(Pt 9):o1401–o1402. doi: 10.1107/S1600536813021533

Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)ethanoate

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

PMCID: PMC3884445 PMID: 24427040

Abstract

The asymmetric unit of the title compound, C₂₁H₁₉N₃O₃S, contains two independent molecules. In one molecule, the 1,3-thiazolidine ring forms dihedral angles of 86.19 (8) and 8.37 (8)° with the phenyl and benzene rings, respectively. The corresponding dihedral angles in the other molecule are 69.60 (7) and 14.08 (7)°. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° in one molecule and 69.62 (8)° in the other. In the crystal, molecules pack in layers approximately parallel to (10-2). There are weak C—H⋯O hydrogen bonds within these layers. Further weak C—H⋯O hydrogen bonding occurs between the layers to form a three-dimensional network. A weak C—H⋯π interaction is also observed.

Related literature

For the synthesis and general applications of thiazolidines, see: Pandey et al. (2011 ▶); Barreca et al. (2002 ▶); Botti et al. (1996 ▶); Pfahl et al. (2003 ▶); Sayyed et al. (2006 ▶); Sharma et al. (2006 ▶); Babaoğlu et al. (2003 ▶); Çapan et al. (1999 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₁₉N₃O₃S
M _r = 393.46
Monoclinic,
a = 8.3713 (12) Å
b = 21.568 (3) Å
c = 21.591 (3) Å
β = 96.411 (2)°
V = 3873.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 150 K
0.19 × 0.19 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.81, T _max = 0.98
69242 measured reflections
9850 independent reflections
7890 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.112
S = 1.05
9850 reflections
511 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); 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, 2012 ▶) and DIAMOND (Brandenburg & Putz, 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/S1600536813021533/lh5636sup1.cif

e-69-o1401-sup1.cif^{(44.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021533/lh5636Isup2.hkl

e-69-o1401-Isup2.hkl^{(539.4KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021533/lh5636Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C36–C41 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O6ⁱ	0.95	2.56	3.4802 (19)	163
C6—H6B⋯O4ⁱ	0.98	2.52	3.465 (2)	163
C8—H8⋯O2ⁱⁱ	0.95	2.56	3.359 (2)	142
C12—H12⋯O4	0.95	2.43	3.302 (2)	152
C27—H27B⋯O1ⁱ	0.98	2.45	3.410 (2)	166
C30—H30⋯O5ⁱⁱⁱ	0.95	2.44	3.331 (2)	157
C32—H32⋯O1^iv	0.95	2.57	3.340 (2)	139
C33—H33⋯Cg ^v	0.95	2.58	3.4951 (19)	162

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

Acknowledgments

The use of X-ray crystallographic facilities at Tulane University, USA, is gratefully acknowledged, We thank Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

supplementary crystallographic information

1. Comment

Heterocyclic compounds such as thiazolidines have demonstrated widespread applications as pharmaceuticals (Pandey et al., 2011; Barreca et al., 2002) and materials (Botti et al., 1996). Thiazolidinone derivatives exhibit anticancer properties (Pfahl et al., 2003) as well as antibacterial (Sayyed et al., 2006), antimycobacterial (Babaoğlu et al., 2003), antimicrobial (Sharma et al., 2006) and antifungal (Çapan et al., 1999) activities. Therefore, we have synthesized the title compound (I) and determined its crystal structure.

The asymmetric unit of (I) is shown in Fig. 1. In one molecule, the 1,3-thiazolidine ring (S1/N1/C1–C3) forms dihedral angles of 86.19 (8) and 8.37 (8) °, respectively, with the phenyl ring (C7–C12) and the benzene ring (C15–C20). In the other molecule the corresponding angles between (S2/N4/C22-C24) are 69.60 (7) (C28-C33) and 14.08 (7)° (C36-C41), respectively. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° (C7-C12 and C15-C20) and 69.62 (8)° (C28-C33 and C26-C41). The differences in the dihedral angles may be due to the packing effects of neighbouring molecules. The bond lengths (Allen et al., 1987) and angles in each molecule are normal.

In the crystal, molecules are arranged in layers approximately parallel to (102) connected by weak C—H···O hydrogen bonds (Table 1, Fig. 2). Additional weak C—H···O hydrogen bonds occur between theses layers (Table 1, Fig. 2) forming a three-dimensional network. A weak intermolecular C—H···π interaction is also observed (Table 1).

2. Experimental

A mixture of 283 mg (1 mmol) (2E)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide and 142 mg (1 mmol) of dimethyl but-2-ynedioate in 50 ml methanol was refluxed for three hours. The excess solvent was evaporated under vacuum and the residual solid product was collected and recrystallized from ethanol to afford a clear yellow blocks (M.p. 527 – 529 K) suitable for X-ray diffraction.