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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 [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.149
Data-to-parameter ratio = 14.6
Details
Open access

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

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-H...S, C-H...F and C-H...O interactions. In the crystal, no significant intermolecular contacts were apparent.

Related literature

For general properties of thiazolidines, see: Botti et al. (1996[Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.]); Spiegelman (1998[Spiegelman, B. M. (1998). Diabetes, 47, 507-514.]); Day (1999[Day, C. (1999). Diabet. Med. 16, 179-192.]); Barreca et al. (2002[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.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18FNO3S2

  • Mr = 427.49

  • Monoclinic, P 21 /c

  • a = 7.657 (3) Å

  • b = 15.799 (5) Å

  • c = 17.425 (6) Å

  • [beta] = 95.641 (5)°

  • V = 2097.7 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 19651 measured reflections

  • 3838 independent reflections

  • 2429 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.149

  • S = 1.02

  • 3838 reflections

  • 262 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...F 0.98 2.35 2.740 (4) 103
C4-H4...O2 0.98 2.33 2.792 (4) 108
C15-H15...O2 0.93 2.53 2.884 (4) 103
C17-H17...S1 0.93 2.55 3.238 (3) 131

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Day, C. (1999). Diabet. Med. 16, 179-192.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Spiegelman, B. M. (1998). Diabetes, 47, 507-514.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o188  [ doi:10.1107/S1600536812051987 ]

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