Crystal structure of (Z)-3-allyl-5-(4-chloro­benzyl­idene)-2-sulfanyl­idene-1,3-thia­zolidin-4-one

Rahhal El Ajlaoui; El Mostapha Rakib; Souad Mojahidi; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S2056989015022689

. 2015 Dec 6;71(Pt 12):o1012. doi: 10.1107/S2056989015022689

Crystal structure of (Z)-3-allyl-5-(4-chlorobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one

Rahhal El Ajlaoui ^a,^*, El Mostapha Rakib ^a, Souad Mojahidi ^a, Mohamed Saadi ^b, Lahcen El Ammari ^b

PMCID: PMC4719951 PMID: 26870470

Abstract

In the title compound, C₁₃H₁₀ClNOS₂, the dihedral angle between the rhodanine (r.m.s. deviation = 0.008 Å) and 4-chlorobenzylidene rings is 1.79 (11)°. The allyl group attached to the N atom, which lies almost perpendicular to the rhodanine ring, is disordered over two orientations in a 0.519 (13):0.481 (13) ratio. A short intramolecular C—H⋯S interaction closes an S(6) ring. In the crystal, molecules are linked by π–π stacking interactions [centroid–centroid separation = 3.600 (15) Å], generating inversion dimers.

Keywords: crystal structure; rhodanine-based molecules; pharmacological activity; biological activity; 1,3-thiazolidin-4-one

Related literature

For a related structure and background to the pharmacological and biological activities of rhodanine-based molecules, see: El Ajlaoui et al. (2015 ▸).

Experimental

Crystal data

C₁₃H₁₀ClNOS₂
M _r = 295.79
Triclinic,
a = 7.6197 (8) Å
b = 7.9849 (7) Å
c = 13.0624 (14) Å
α = 77.600 (5)°
β = 77.996 (5)°
γ = 61.954 (4)°
V = 679.76 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 296 K
0.37 × 0.25 × 0.21 mm

Data collection

Bruker X8 APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.656, T _max = 0.746
24189 measured reflections
3249 independent reflections
2199 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.144
S = 1.04
3249 reflections
182 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸) and ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022689/hb7551sup1.cif

e-71-o1012-sup1.cif^{(841.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022689/hb7551Isup2.hkl

e-71-o1012-Isup2.hkl^{(259.4KB, hkl)}

Click here for additional data file.^{(4.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015022689/hb7551Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015022689/hb7551fig1.tif

Plot of the molecule of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.^{(1.8MB, tif)}

. DOI: 10.1107/S2056989015022689/hb7551fig2.tif

Crystal packing for the title compound showing hydrogen bonds as dashed lines between inversion-related molecules.

CCDC reference: 1439050

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯S1	0.93	2.55	3.254 (3)	133

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Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.

supplementary crystallographic information

S1. Comment

As part of our ongoing studies of rhodanine derivatives, we now describe the title compound.

The molecule of the title compound is build up from a rhodanine ring (S1–N1–C8–C9–C10) linked to an disordered allyl group (48%/52%) (C11–C12AC12B–C13AC13B) and at the nitrogen atom and to a 4-chlorobenzylidene ring system (C1 to C6) as shown in Fig.1. The mean plane through the rhodanine ring is almost perpendicular to the allyl group and makes a dihedral angle of 1.79 (11)° with the 4-chlorobenzylidene ring system. Nearly the same structure is observed by El Ajlaoui et al. 2015 in (Z)-3-Allyl-5-(4-methyl-benzylidene)-2- thioxothiazolidin-4-one.

The cohesion of the crystal structure is ensured by π—π interaction between molecules forming inversion dimers as shown in Fig.2.

S2. Experimental

To a solution of 3-allylrhodanine (1.15 mmol, 0.2 g) in 10 ml of THF, (4-chlorobenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide (1.38 mmol) was added. The mixture was refluxed for 8 h, monitored by TLC, the reaction completed and a yellow spot (TLC Rf = 0.3, using hexane/ethyl acetate 1:9) was generated cleanly. The solvent was evaporated in vacuo. The crude product was purified on silica gel using hexane: ethyl acetate (1/9) as eluent. The title compound was recrystallized from ethanol (Yield: 72%, m.p.: 371 K).