3-[2-Cyclo­propyl-1-(2-fluoro­phen­yl)-2-oxoeth­yl]-5-(4-methyl­sulfanyl­benzyl­idene)-1,3-thia­zolidine-2,4-dione

Suresh, J.; Venkateshan, M.; Ponnuchamy, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536812051987

Volume 69
Part 2
Page o188
February 2013

Received 26 December 2012
Accepted 28 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.149
Data-to-parameter ratio = 14.6
Details

3-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5-(4-methylsulfanylbenzylidene)-1,3-thiazolidine-2,4-dione

J. Suresh,^a M. Venkateshan,^a S. Ponnuchamy,^b R. Ranjith Kumar ^c and P. L. Nilantha Lakshman ^d ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India,^bOrchid Chemicals & Pharmaceuticals Ltd, R&D Center, Chennai 600 119, India,^cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C₂₂H₁₈FNO₃S₂, the five-membered thiazolidine ring is planar (r.m.s. deviation = 0.003 Å) and forms dihedral angles of 70.2 (3), 73.16 (17) and 10.32 (14)° with the cyclopropane, fluorobenzene and methylthiobenzene rings, respectively. The sum of the bond angles around the thiazolidine ring N atom (359.6°) indicates sp² hybridization. The molecular structure features intramolecular C-HS, C-HF and C-HO interactions. In the crystal, no significant intermolecular contacts were apparent.

Related literature

For general properties of thiazolidines, see: Botti et al. (1996); Spiegelman (1998); Day (1999); Barreca et al. (2002).

Experimental

Crystal data

C₂₂H₁₈FNO₃S₂
M_r = 427.49
Monoclinic, P 2₁ /c
a = 7.657 (3) Å
b = 15.799 (5) Å
c = 17.425 (6) Å
= 95.641 (5)°
V = 2097.7 (13) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 293 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.974
19651 measured reflections
3838 independent reflections
2429 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.149
S = 1.02
3838 reflections
262 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4F	0.98	2.35	2.740 (4)	103
C4-H4O2	0.98	2.33	2.792 (4)	108
C15-H15O2	0.93	2.53	2.884 (4)	103
C17-H17S1	0.93	2.55	3.238 (3)	131

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5185 ).

Acknowledgements

SP thanks the management, Orchid Chemicals & Pharmaceuticals Ltd, Chennai, for providing laboratory facilities. JS thanks the UGC for the FIST support. JS and MV thank the management of The Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No·SR/FT/CS-073/2009).

References

Barreca, M. L., Balzarini, J., Chimirri, A., De Clercq, E., De Luca, L., Holtje, H. D., Holtje, M., Monforte, A. M., Monforte, P., Pannecouque, C., Rao, A. & Zappala, M. (2002). J. Med. Chem. 45, 5410-5413.
Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Day, C. (1999). Diabet. Med. 16, 179-192.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Spiegelman, B. M. (1998). Diabetes, 47, 507-514.

organic compounds