(Z)-3-Benzyl-2-[(2-phenyl­cyclo­hex-2-en­yl)imino]-1,3-thia­zolidin-4-one

Chin Wei Ooi; Hoong-Kun Fun; Ching Kheng Quah; Murugan Sathishkumar; Alagusundaram Ponnuswamy

doi:10.1107/S1600536812033211

. 2012 Jul 28;68(Pt 8):o2563–o2564. doi: 10.1107/S1600536812033211

(Z)-3-Benzyl-2-[(2-phenylcyclohex-2-enyl)imino]-1,3-thiazolidin-4-one

Chin Wei Ooi ^a, Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Murugan Sathishkumar ^b, Alagusundaram Ponnuswamy ^b

PMCID: PMC3415005 PMID: 22904992

Abstract

The title compound, C₂₂H₂₂N₂OS, exists in a Z configuration with respect to the N=C bond. The cyclohexene ring adopts a distorted sofa conformation. The thiazolidine ring is essentially planar, with a maximum deviation of 0.030 (2) Å, and forms dihedral angles of 76.66 (6) and 74.55 (6)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 71.55 (7)°. In the crystal, a C—H⋯π interaction is observed.

Related literature

For the bioactivity of thiazolidin-4-one derivatives, see: Previtera et al. (1994 ▶); Sharma et al. (2000 ▶); Kato, Ozaki & Tamura (1999 ▶); Kato, Ozaki & Ohi (1999 ▶); Tanabe et al. (1991 ▶); Rawal et al. (2005 ▶); Voss et al. (2003 ▶). For related structures, see: Fun et al. (2011 ▶); Ooi et al. (2012a ▶,b ▶,c ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₂H₂₂N₂OS
M _r = 362.48
Monoclinic,
a = 12.8400 (2) Å
b = 8.9261 (1) Å
c = 17.9634 (3) Å
β = 118.476 (1)°
V = 1809.72 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.39 × 0.32 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.929, T _max = 0.960
22263 measured reflections
6670 independent reflections
4979 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.115
S = 1.03
6670 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL ; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033211/is5168sup1.cif

e-68-o2563-sup1.cif^{(28.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033211/is5168Isup2.hkl

e-68-o2563-Isup2.hkl^{(326.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812033211/is5168Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg1	0.93	2.97	3.7662 (15)	143

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Acknowledgments

CWO, HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Thiazolidin-4-one derivatives are known to exhibit diverse bioactivities such as anti-histaminic (Previtera et al., 1994), anti-microbial (Sharma et al., 2000; Kato, Ozaki & Tamura, 1999), PAF antagonist (Tanabe et al., 1991), cardioprotective (Kato, Ozaki & Ohi, 1999), anti HIV (Rawal et al., 2005), and tumor necrosis factor-α antagonist activities (Voss et al., 2003).

The title compound (Fig. 1) exists in cis configuration with respect to the N1 ═C13 bond [N1 ═C13 = 1.2660 (15) Å]. The cyclohexene (C7–C12) ring adopts a distorted sofa conformation and the puckering parameters are Q = 0.5050 (15) Å, θ = 51.07 (16)° and φ = 201.6 (2)° (Cremer & Pople, 1975). The thiazolidine (S1/N2/C13–C15) ring is essentially planar with a maximum deviation of 0.030 (2) Å at atom C14 and forms dihedral angles of 76.66 (6) and 74.55 (6)°, respectively, with terminal benzene rings (C1–C6 & C17–C22). The dihedral angle between terminal benzene rings is 71.55 (7)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Fun et al., 2011; Ooi et al., 2012a,b,c).

In the crystal packing (Fig. 2), no significant intermolecular hydrogen bond interactions are observed. The crystal is stabilized by C22—H22A···Cg1 interactions (Table 1), involving the centroid of the benzene ring (C1–C6; Cg1).

Experimental

A mixture of 1-benzyl-3-(2-phenylcyclohex-2-enyl)thiourea (0.5 g, 2.3 mmol) and chloro acetylchloride (0.35 g, 4.6 mmol) was heated to reflux in 1,4-dioxane (10 ml) at 100°C for 5 h. The reaction mixture was washed with diluted sodium bicarbonate solution (25 ml) and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure and the resulting residue was subjected to column chromatography using silica gel (60–120 mesh) as the stationary phase and petroleum ether-ethyl acetate (90:10) as the mobile phase to give the pure product. Yield: 0.69 g (83%); M.p.: 132–133 °C. Crystals suitable for X-ray study were obtained by recrystallization in dichloromethane.