(5Z)-5-(2-Hy­droxy­benzyl­idene)-3-(4-methyl­phen­yl)-2-sulfanyl­idene-1,3-thia­zolidin-4-one

Durre Shahwar; M Nawaz Tahir; Misbah Kashif; Afifa Saeed; Sana Bukhari

doi:10.1107/S1600536812021630

. 2012 May 19;68(Pt 6):o1818. doi: 10.1107/S1600536812021630

(5Z)-5-(2-Hydroxybenzylidene)-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, Misbah Kashif ^a, Afifa Saeed ^a, Sana Bukhari ^a

PMCID: PMC3379392 PMID: 22719590

Abstract

In the title compound, C₁₇H₁₃NO₂S₂, the dihedral angles between the 2-sulfanylidene-1,3-thiazolidin-4-one group and the pendant toluene and 2-hydroxybenzene rings are 74.62 (6) and 8.73 (12)°, respectively. An intramolecular C—H⋯S interaction occurs. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R ₂ ²(16) loops. This link is reinforced by a pair of C—H⋯O hydrogen bonds. The dimers are connected by weak C—H⋯S interactions.

Related literature

For related structures and further synthetic details, see: Shahwar et al. (2009a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1818-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₃NO₂S₂
M _r = 327.40
Monoclinic,
a = 13.8258 (6) Å
b = 5.4278 (3) Å
c = 21.0715 (9) Å
β = 101.857 (3)°
V = 1547.54 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.945, T _max = 0.965
10652 measured reflections
2801 independent reflections
1473 reflections with I > 2σ(I)
R _int = 0.069

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.101
S = 0.93
2801 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021630/hb6792sup1.cif

e-68-o1818-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021630/hb6792Isup2.hkl

e-68-o1818-Isup2.hkl^{(134.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021630/hb6792Isup3.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
O2—H2A⋯O1ⁱ	0.82	1.92	2.712 (3)	162
C6—H6⋯S2ⁱⁱ	0.93	2.84	3.736 (4)	163
C11—H11⋯O2ⁱ	0.93	2.38	3.294 (4)	167
C13—H13⋯S1	0.93	2.48	3.194 (3)	133

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

In the search for new enzyme inhibitors, a series of rohdanine derivatives were prepared and their crystal structures have been reported such as (5Z)-5-(2-hydroxybenzylidene)-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (5Z)-5-(2-methylbenzylidene)-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one (Shahwar et al., 2009b) which are related to the title compound, (I), (Fig. 1).

In (I), the toluene group A (C1–C7), group B (N1/C8/S1/C10/C9/O1/S2) of 2-sulfanylidene-1,3-thiazolidin-4-one and group C (C11–C17/O2) of 2-methylphenol are planar with r. m. s. deviation of 0.0246 Å, 0.0186 Å and 0.0175 Å, respectively. The dihedral angle between A/B, A/C and B/C is 74.62 (6), 70.16 (7) and 8.73 (12)°, respectively. The molecules are dimerized due to strong O—H···O type of H-bonding with R₂²(16) (Bernstein et al., 1995) ring motifs (Table 1, Fig. 2). R₂²(7) ring motifs are formed within the dimers when weak H-boding of C—H···O type is considered. The dimers are interlinked due to C—H···S type of H-bondings (Table 1, Fig. 2).

Experimental

3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one (0.419 g, 0.2 mol) (prepared according to the method: Shahwar et al. 2009a), 2-hydroxybenzaldehyde (0.244 g, 0.2 mol) and K₂CO₃ (0.553 g, 0.4 mol) were dissolved in distilled water (10 ml) and continuously stirred for 24 h. The mixture was neutralized with 5% HCl and the crude product obtained was recrysrallized in ethylacetate to get the yellow needles of (I).