(2R,4R)-3-(tert-But­oxy­carbon­yl)-2-(3-chloro­phen­yl)-1,3-thia­zolidine-4-carb­oxy­lic acid monohydrate

Song, Z.-C.; Guo, Y.; Liu, W.-H.; Hu, L.-C.; Cai, S.-N.

doi:10.1107/S1600536810042133

Volume 66
Part 11
Page o2934
November 2010

Received 14 October 2010
Accepted 17 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.068
wR = 0.167
Data-to-parameter ratio = 15.3
Details

(2R,4R)-3-(tert-Butoxycarbonyl)-2-(3-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid monohydrate

Zhong-Cheng Song,^a ^* Ying Guo,^a Wen-Hong Liu,^a Li-Chun Hu ^a and Sheng-Nan Cai ^a

^aBioengineering Department, Zhejiang Traditional Chinese Medicine University, Hangzhou 310053, People's Republic of China
Correspondence e-mail: songzhongcheng@gmail.com

In the title compound, C₁₅H₁₈ClNO₄S·H₂O, the thiazolidine ring displays a half-chair conformation. In the crystal, the water molecules are linked to the organic acid molecules via intermolecular O-HO hydrogen bonds.

Related literature

For applications of thiazolidine derivatives, see: Kallen (1971); Seki et al. (2004); Song et al. (2009).

Experimental

Crystal data

C₁₅H₁₈ClNO₄S·H₂O
M_r = 361.83
Monoclinic, P 2₁
a = 8.2460 (16) Å
b = 5.9660 (12) Å
c = 18.132 (4) Å
= 99.81 (3)°
V = 879.0 (3) Å³
Z = 2
Mo K radiation
= 0.36 mm^-1
T = 293 K
0.20 × 0.17 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (ABSCOR; Higashi, 1995) T_min = 0.932, T_max = 0.948
3417 measured reflections
3182 independent reflections
2169 reflections with I > 2(I)
R_int = 0.080
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.167
S = 1.03
3182 reflections
208 parameters
1 restraint
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.28 e Å^-3
Absolute structure: Flack (1983), 1451 Friedel pairs
Flack parameter: -0.11 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2CO5ⁱ	0.82	1.80	2.620 (6)	177
O5-H5AO3ⁱⁱ	0.85	2.20	2.890 (5)	139
O5-H5BO3ⁱⁱⁱ	0.85	2.37	2.827 (5)	114
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5054 ).

Acknowledgements

This work was supported by Zhejiang Traditional Chinese Medicine University (Project 2009ZY06) and the Education Department of Zhejiang Province, China (Project 20071211).

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kallen, R. G. (1971). J. Am. Chem. Soc. 93, 6236-6248.
Seki, M., Hatsuda, M., Mori, Y., Yoshida, S. I., Yamada, S. I. & Shimizu, T. (2004). Chem. Eur. J. 10, 6102-6110.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, Z.-C., Ma, G.-Y., Lv, P.-C., Li, H.-Q., Xiao, Z.-P. & Zhu, H.-L. (2009). Eur. J. Med. Chem. 44, 3903-3908.

organic compounds