(5Z)-5-(2-Methyl­benzyl­idene)-3-phenyl-2-thioxo-1,3-thia­zolidin-4-one

Durre Shahwar; M Nawaz Tahir; Muhammad Asam Raza; Bushra Iqbal

doi:10.1107/S1600536809044304

. 2009 Oct 31;65(Pt 11):o2917. doi: 10.1107/S1600536809044304

(5Z)-5-(2-Methylbenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, Muhammad Asam Raza ^a, Bushra Iqbal ^a

PMCID: PMC2971373 PMID: 21578495

Abstract

In the title compound, C₁₇H₁₃NOS₂, the heterocyclic ring is oriented at a dihedral angle of 74.43 (5)° with respect to the anilinic benzene ring and at a dihedral angle of 17.31 (9)° with respect to phenyl ring. An intramolecular C—H⋯S interaction occurs, resulting in an S(6) ring. In the crystal, the packing is consolidated by C—H⋯π interactions and possible very weak aromatic π–π stacking [centroid–centroid separation = 4.025 (1) Å].

Related literature

For related structures, see: Linden et al. (1999 ▶); Shahwar et al. (2009a ▶,b ▶,c ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₇H₁₃NOS₂
M _r = 311.40
Monoclinic,
a = 9.8317 (4) Å
b = 16.6317 (6) Å
c = 9.3865 (4) Å
β = 93.541 (2)°
V = 1531.93 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.879, T _max = 0.941
17261 measured reflections
3807 independent reflections
2879 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.104
S = 1.01
3807 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044304/hb5181sup1.cif

e-65-o2917-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044304/hb5181Isup2.hkl

e-65-o2917-Isup2.hkl^{(182.9KB, 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
C16—H16⋯S1	0.93	2.52	3.2197 (19)	133
C17—H17C⋯CgCⁱ	0.96	2.72	3.569 (2)	148

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Symmetry code: (i) Inline graphic . CgC is the centroid of C11–C16 benzene ring.

Acknowledgments

DS is grateful to Government College University, Lahore, for providing funds under the GCU funded Research Projects Programme.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1), has been prepared and being reported in continuation of synthesizing various derivatives of rhodanine. In this context we have reported the crystal structure of (II) (5Z)-5-(2-Hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a), (III) (5Z)-5-(2-Hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one methanol hemisolvate (Shahwar et al., 2009b) and (IV) (5E)-5-(4-Hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin- 4-one methanol monosolvate (Shahwar et al., 2009c).

The crystal structure of (I) differs from (V) 3-Phenyl-5-(phenylmethylidene)-2-thioxo-1,3-thiazolidin-4-one (Linden et al., 1999) due to attachement of methyl group.

In (I) the heterocyclic ring A (N1/C7/S1/C8/C9), two benzene rings B (C1—C6) and C (C11–C16) are planar with maximum r. m. s. deviations of 0.0047, 0.0074 and 0.0046 Å respectively, from the respective mean square planes. The dihedral angles between A/B, A/C and B/C are 74.43 (5), 17.31 (9) and 59.19 (6)°, respectively. The intramolecular H-bondings of C—H···S (Table 1, Fig. 1) form S(6) ring motif (Bernstein et al., 1995). There exist π···π-interactions between adjacent molecules. The CgA···CgCⁱ and CgC···CgAⁱ [symmetry code: i = 2 - x, 1 - y, 1 - z] have centroid to centroid distance of 4.025 (1) Å, where CgA and CgC are the centroids of rings A and C, respectively. The C–H···π interactions (Table 1) also play role in stabilizing the molecules.

Experimental

3-Phenyl-2-thioxo-1,3-thiazolidin-4-one (0.419 g, 0.2 mol), 2-Methylbenzaldehyde (0.240 g, 0.2 mol) and K₂CO₃ (0.553 g, 0.4 mol) were dissolved in 10 ml distilled water at room temperature. The stirring was continued for 24 h and reaction was monitored by TLC. The precipitates were formed during neutalization of the reaction mixture with 5% HCl. The precipitates were filtered off and washed with saturated solution of NaCl. The crude material obtained was recrystalized in ethyl acetate to affoard yellow prisms of (I).