1-[(4S)-4-Benzyl-2-thioxo-1,3-thia­zol­idin-3-yl]propan-1-oneILS Publication No. ILS-MCO-0904.

Gade, N.R.; Manjula, Y.; Iqbal, J.; Vishweshwar, P.

doi:10.1107/S1600536809030104

Volume 65
Part 9
Page o2159
September 2009

Received 22 July 2009
Accepted 29 July 2009
Online 15 August 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.048
Data-to-parameter ratio = 16.1
Details

1-[(4S)-4-Benzyl-2-thioxo-1,3-thiazolidin-3-yl]propan-1-one¹

Narendar Reddy Gade,^a Y. Manjula,^b Javed Iqbal ^a ^* and Peddy Vishweshwar ^b ^*

^aInstitute of Life Sciences, Hyderabad Central University Campus, Gachibowli, Hyderabad 500 046, India, and ^bDepartment of Analytical Research, Discovery Research, Dr Reddy's Laboratories Ltd, Miyapur, Hyderabad 500 049, India
Correspondence e-mail: jiqbal@ilsresearch.org, peddy_vishu@yahoo.co.in

The analysis of the title chiral auxiliary compound, C₁₃H₁₅NOS₂, has enabled the determination of the absolute configuration at the benzyl-bearing ring C atom as S. In the crystal structure, molecules aggregate into helical chains along the b axis via C-HO contacts.

Related literature

For background to the use of N-acyl thiazolidinethiones as versatile chiral auxiliaries for asymmetric aldol reactions, see: Crimmins & Chaudhary (2000); Crimmins et al. (2005); Crimmins & Haley (2006); Crimmins & Dechert (2009). For the synthesis, see: McKennon & Meyer (1993); Delaunay et al. (1995); Lu et al. (2009).

Experimental

Crystal data

C₁₃H₁₅NOS₂
M_r = 265.39
Monoclinic, P 2₁
a = 8.850 (6) Å
b = 7.189 (5) Å
c = 10.595 (7) Å
= 95.537 (6)°
V = 670.9 (8) Å³
Z = 2
Mo K radiation
= 0.38 mm^-1
T = 298 K
0.50 × 0.40 × 0.20 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998) T_min = 0.831, T_max = 0.925
7301 measured reflections
2734 independent reflections
2361 reflections with F² > 2(F²)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.048
S = 0.86
2734 reflections
170 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 1138 Friedel pairs
Flack parameter: -0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9O1ⁱ	0.95	2.55	3.408 (4)	150
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Pflugrath, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: X-SEED (Barbour et al., 2001); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2514 ).

Acknowledgements

NRG thanks the Institute of Life Sciences for allowing him to pursue this work as part of his PhD thesis.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Crimmins, M. T. & Chaudhary, K. (2000). Org. Lett. 2, 775-777.
Crimmins, M. T., Christie, H. S., Chaudhary, K. & Long, A. (2005). J. Am. Chem. Soc. 127, 13810-13812.
Crimmins, M. T. & Dechert, A.-M. R. (2009). Org. Lett. 11, 1635-1638.
Crimmins, M. T. & Haley, M. W. (2006). Org. Lett. 8, 4223-4225.
Delaunay, D., Toupet, L. & Le Corre, M. J. (1995). Org. Chem. 60, 6604-6607.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan.
Lu, C., Nie, J., Yang, G. & Chen, Z. (2009). Can. J. Chem. 87, 30-32.
McKennon, M. J. & Meyer, A. I. (1993). J. Org. Chem. 58, 3568-3571.
Molecular Structure Corporation & Rigaku (2006). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Pflugrath, J. W. (1999). Acta Cryst. D55, 1718-1725.

organic compounds

1-[(4S)-4-Benzyl-2-thioxo-1,3-thiazolidin-3-yl]propan-1-one1