3-[5-(4-Fluoro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(4-methoxy­phen­yl)-1,3-thia­zolidin-4-one

Yin, L.-H.; Wan, R.; Han, F.; Wang, B.; Wang, J.-T.

doi:10.1107/S1600536808019089

Volume 64
Part 7
Page o1359
July 2008

Received 22 June 2008
Accepted 24 June 2008
Online 28 June 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R = 0.071
wR = 0.186
Data-to-parameter ratio = 13.6
Details

3-[5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one

Li-He Yin,^a Rong Wan,^a ^* Feng Han,^a Bin Wang ^a and Jin-Tang Wang ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: rwan@njut.edu.cn

The title compound, C₁₈H₁₄FN₃O₂S₂, was synthesized by the reaction of 5-(4-fluorophenyl)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol-2-amine and mercaptoacetic acid. The thiazolidinone ring adopts a twist conformation. The 4-methoxyphenyl ring is almost perpendicular to the thiadiazole ring, making a dihedral angle of 88.4 (3)°. The 4-fluorophenyl ring is nearly coplanar with the thiadiazole ring, the dihedral angle being 6.8 (3)°. The crystal structure involves C-HN, C-HO and C-HS hydrogen bonds.

Related literature

For related literature, see: Arun et al. (1999); Chen et al. (2000); Kidwai et al. (2000); Vicentini et al. (1998); Wasfy et al. (1996); Allen et al. (1987).

Experimental

Crystal data

C₁₈H₁₄FN₃O₂S₂
M_r = 387.44
Triclinic, $[P \overline 1]$
a = 6.4550 (13) Å
b = 8.9200 (18) Å
c = 16.483 (3) Å
= 75.78 (3)°
= 82.44 (3)°
= 71.11 (3)°
V = 869.0 (3) Å³
Z = 2
Mo K radiation
= 0.34 mm^-1
T = 298 (2) K
0.10 × 0.05 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.967, T_max = 0.984
3421 measured reflections
3120 independent reflections
2054 reflections with I > 2(I)
R_int = 0.023
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.186
S = 1.00
3120 reflections
229 parameters
48 restraints
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6AN1	0.93	2.60	2.917 (9)	101
C8-H8AO2ⁱ	0.98	2.52	3.233 (7)	129
C14-H14AS2	0.93	2.74	3.146 (6)	107
C18-H18AN3	0.93	2.57	2.881 (7)	100
Symmetry code: (i) x-1, y, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: AT2579 ).

Acknowledgements

The authors thank Professor Hua-Qin Wang of Nanjing University for carrying out the X-ray crystallographic analysis.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arun, K. P., Nag, V. L. & Panda, C. S. (1999). Indian J. Chem. Sect. B, 38, 998-1001.
Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312-5315.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Kidwai, M., Negi, N. & Misra, P. (2000). J. Indian Chem. Soc. 77, 46-48.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29-36.
Wasfy, A. A., Nassar, S. A. & Eissa, A. M. (1996). Indian J. Chem. Sect. B, 35, 1218-1220.

organic compounds