(Z)-N-{3-[1-(4-Chloro­phen­yl)eth­yl]thia­zolidin-2-yl­idene}cyanamide

Li, H.; Zhang, X.; Xu, L.

doi:10.1107/S1600536810029879

Volume 66
Part 8
Page o2171
August 2010

Received 16 July 2010
Accepted 27 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 19.5
Details

(Z)-N-{3-[1-(4-Chlorophenyl)ethyl]thiazolidin-2-ylidene}cyanamide

Hong-xin Li,^a Xiao-jun Zhang ^a and Liang-zhong Xu ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: nyhxpyjs@yahoo.com.cn

The title compound, C₁₂H₁₂ClN₃S, features a thiazolyl ring having an envelope conformation with the -CH₂- group bonded to the S atom forming the flap. The C=N double bond has a Z configuration. The crystal structure shows intermolecular C-HS hydrogen bonds.

Related literature

For the biological activity of thiazole componds, see: Hense et al. (2002). For a related structure, see: Cunico et al. (2007). For the synthesis, see: Jeschke et al. (2002).

Experimental

Crystal data

C₁₂H₁₂ClN₃S
M_r = 265.76
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8850 (12) Å
b = 7.5965 (15) Å
c = 28.273 (6) Å
V = 1264.0 (4) Å³
Z = 4
Mo K radiation
= 0.45 mm^-1
T = 113 K
0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.940, T_max = 0.957
9219 measured reflections
3019 independent reflections
2640 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.113
S = 1.06
3019 reflections
155 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.34 e Å^-3
Absolute structure: Flack (1983), 6200 Friedel pairs
Flack parameter: -0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10AS1ⁱ	0.97	2.87	3.799 (4)	160
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5002 ).

References

Cunico, W., Gomes, C. R. B., Wardell, S. M. S. V., Low, J. N. & Glidewell, C. (2007). Acta Cryst. C63, o411-o414.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hense, A., Fischer, A. & Gesing, E. R. (2002). WO Patent 2002096872.
Jeschke, P., Beck, M. E. & Kraemer, W. (2002). German Patent 10119423.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds