2,3-Diphenyl-1,3-thia­zolidin-4-one

Hemant P Yennawar; John Tierney; Lee J Silverberg

doi:10.1107/S1600536814015128

. 2014 Jul 2;70(Pt 8):o847. doi: 10.1107/S1600536814015128

2,3-Diphenyl-1,3-thiazolidin-4-one

Hemant P Yennawar ^a, John Tierney ^b, Lee J Silverberg ^c,^*

PMCID: PMC4158525 PMID: 25249899

Abstract

The title compound, C₁₅H₁₃NOS, is a chiral molecule crystallized as a racemate, with two molecules in the asymmetric unit. In each of the molecules, the five-membered thiazine ring has an envelope conformation, with the S atom forming the flap. In one molecule, the angle between the two phenyl-ring planes is 82.77 (7)°, while in the other it is 89.12 (6)°. In the crystal, molecules are linked into chains along the b-axis direction by C—H⋯O hydrogen bonds.

Keywords: crystal structure

Related literature

For the preparation of the title compound, see: Tierney (1989 ▶). For the crystal structure of a tin complex of the title compound, see: Smith et al. (1995 ▶). For the synthesis and crystal structures of related compounds, see: Yennawar & Silverberg (2013 ▶, 2014 ▶); Fun et al. (2011 ▶). For reviews on 1,3-thiazolidin-4-ones, see: Brown (1961 ▶); Singh et al. (1981 ▶); Metally et al. (2006 ▶); Abhishek et al. (2012 ▶).

Experimental

Crystal data

C₁₅H₁₃NOS
M _r = 255.32
Monoclinic,
a = 32.413 (13) Å
b = 6.196 (3) Å
c = 25.964 (11) Å
β = 100.258 (7)°
V = 5131 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.14 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.807, T _max = 0.981
23146 measured reflections
6334 independent reflections
5015 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.147
S = 1.01
6334 reflections
325 parameters
H-atom parameters not refined
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2001 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814015128/fy2114sup1.cif

e-70-0o847-sup1.cif^{(31.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015128/fy2114Isup2.hkl

e-70-0o847-Isup2.hkl^{(310.1KB, hkl)}

Click here for additional data file.^{(1.8KB, mol)}

Supporting information file. DOI: 10.1107/S1600536814015128/fy2114Isup3.mol

Click here for additional data file.^{(4.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015128/fy2114Isup4.cml

CCDC reference: 1010627

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
C15—H15⋯O1ⁱ	0.93	2.58	3.470 (2)	160
C1—H1⋯O1ⁱ	0.98	2.49	3.466 (2)	172
C16—H16⋯O2ⁱⁱ	0.98	2.34	3.301 (3)	168
C17—H17B⋯O2ⁱⁱⁱ	0.97	2.41	3.313 (3)	155

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

Acknowledgments

We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer.

supplementary crystallographic information

S1. Comment

We have recently reported the syntheses and crystal structures of 6,7-diphenyl-5-thia-7-azaspiro[2.6]nonan-8-one, a seven-membered heterocycle (Yennawar and Silverberg, 2013), and 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one, a similar six-membered heterocycle (Yennawar and Silverberg, 2014). We report here the crystal structure of 2,3-diphenyl-1,3-thiazolidin-4-one (Tierney, 1989), the analogous five-membered heterocycle. The crystal structure of a tin complex of the title compound has been previously reported (Smith et al., 1995), but the structure of the title compound has not. The crystal structure of similar compound 3-benzyl-2-phenyl-1,3-thiazolidin-4-one has been reported (Fun et al., 2011). The 1,3-thiazolidin-4-ones are an important class of compounds with a wide range of biological activity (Brown, 1961; Singh, et al., 1981; Metally et al., 2006; Abhishek et al., 2012).

S2. Experimental

A sample of the title compound, prepared according to Tierney (1989), was recrystallized from ethanol. R_f = 0.54 (50% EtOAc/hexanes). m.p.: 131–133°C (lit. 131–132°C). Crystals for X-ray crystallography were grown by slow evaporation from toluene.