4-Benzyl-8-phenyl-1-thia-4-aza­spiro­[4.5]decan-3-one

Hoong-Kun Fun; Tze Shyang Chia; Poovan Shanmugavelan; Alagusundaram Ponnuswamy

doi:10.1107/S1600536812015358

. 2012 Apr 18;68(Pt 5):o1438. doi: 10.1107/S1600536812015358

4-Benzyl-8-phenyl-1-thia-4-azaspiro[4.5]decan-3-one

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Poovan Shanmugavelan ^b, Alagusundaram Ponnuswamy ^b

PMCID: PMC3344557 PMID: 22590319

Abstract

In the title compound, C₂₁H₂₃NOS, the thiazolidine ring adopts a twist conformation about one of its C—S bonds, while the cyclohexane ring has a chair conformation. The S and N atoms attached to the spiro C atom are in axial and equatorial orientations, respectively. The thiazolidine ring forms dihedral angles of 86.24 (14) and 31.82 (15)° with the directly attached and remote terminal benzene rings, respectively. The dihedral angle between the two terminal benzene rings is 86.74 (14)°. In the crystal, the only significant directional interaction is a weak C—H⋯π bond, which generates [010] chains.

Related literature

For the pharmacological activity of spirothiazolidin-4-ones, see: Singh et al. (2006 ▶); Kasimogullari & Cesur (2004 ▶); Dandia et al. (2004 ▶); Sahu et al. (2006 ▶). For a related structure, see: Akkurt et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₂₃NOS
M _r = 337.46
Monoclinic,
a = 9.8299 (9) Å
b = 15.3823 (14) Å
c = 12.0833 (10) Å
β = 108.717 (4)°
V = 1730.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.33 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.939, T _max = 0.973
10508 measured reflections
3534 independent reflections
2144 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.145
S = 1.01
3534 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.46 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/S1600536812015358/hb6732sup1.cif

e-68-o1438-sup1.cif^{(27.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015358/hb6732Isup2.hkl

e-68-o1438-Isup2.hkl^{(173.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015358/hb6732Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg1ⁱ	0.95	2.72	3.565 (3)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Spirothiazolidin-4-ones are well known to possess varied pharmacological activities such as anti-fungal (Singh et al., 2006), anti-mycobacterial (Kasimogullari & Cesur, 2004), anti-TB (Dandia et al., 2004), and anti-bacterial (Sahu et al., 2006) properties. As a part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

The asymmetric unit of (I) is shown in Fig. 1. The central thiazolidine ring (S1/N1/C8–C10) is twisted with deviations from the least-squares plane of 0.199 (1) and -0.211 (3) Å for atoms S1 and C10, respectively. The cyclohexane ring (C10–C15) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975), Q = 0.583 (3) Å, θ = 173.4 (3)° and φ = 347 (2)°. The thiazolidine ring forms dihedral angles of 86.24 (14) and 31.82 (15)° with the terminal C1–C6 and C16–C21 benzene rings, respectively. The dihedral angle between the two terminal benzene rings is 86.74 (14)°. Bond lengths and angles are comparable to a related structure (Akkurt et al., 2008).

The only significant intermolecular interaction in the crystal is a weak C—H···Cg1 interaction (Table 1) where Cg1 is the centroid of C1–C6 ring.

Experimental

A mixture of triphenyl phosphine (0.43 g, 1.1 mmol), benzyl azide (0.20 g, 1.0 mmol), 4-phenylcylohexanone (0.28 g, 1.0 mmol) and mercaptoacetic acid (0.15 g, 1.1 mmol) was heated to reflux in acetonitrile (5 ml) for 4 h. The reaction mixture was allowed to stand at room temperature. After the solvent has been evaporated, the residue was purified by column chromatography using silica gel as the stationary phase (60–120 mesh) and petroleum ether-ethyl acetate (93:7) as the mobile phase to afford the title compound. Yield: 0.48 g (95%); M.p.: 130–131 °C. Colourless crystals were obtained by recrystallization from ethanol solution.