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Volume 69 
Part 8 
Page o1229  
August 2013  

Received 4 July 2013
Accepted 4 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.100
Data-to-parameter ratio = 17.1
Details
Open access

5-Fluoro-N-(2-methyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-3-phenyl-1H-indole-2-carboxamide

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C24H24FN3O2S, the 1,3-thiazolidine ring adopts an envelope conformation with the S atom as the flap, while the cyclohexane ring is in a chair conformation. In the crystal, molecules are linked by N-H...O and C-H...F hydrogen bonds, forming a three-dimensional network. The unit cell contains six voids of 57 Å3, but the residual electron density (highest peak = 0.23 e Å-3 and deepest hole = -0.19 e Å-3) in the difference Fourier map suggests no solvent molecule occupies this void.

Related literature

For the antitubercular and antiviral activity of variously substituted N-(1-thia-4-azaspiro[4.5]dec-4-yl)carboxamides, see: Cihan-Üstündag & Çapan (2012[Cihan-Üstündag, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.]); Göktas et al. (2012[Göktas, F., Vanderlinden, E., Naesens, L., Cesur, N. & Cesur, Z. (2012). Bioorg. Med. Chem. 20, 7155-7159.]); Güzel et al. (2006[Güzel, Ö., Ilhan, E. & Salman, A. (2006). Monatsh. Chem. 137, 795-801.]); Ulusoy (2002[Ulusoy, N. (2002). Arzneim.-Forsch. Drug. Res. 52, 565-571.]); Vanderlinden et al. (2010[Vanderlinden, E., Göktas, F., Cesur, Z., Froeyen, M., Reed, M. L., Russell, C. J., Cesur, N. & Naesens, L. (2010). J. Virol. 84, 4277-4288.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H24FN3O2S

  • Mr = 437.53

  • Hexagonal, P 65

  • a = 13.2082 (18) Å

  • c = 23.584 (4) Å

  • V = 3563.2 (13) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 296 K

  • 0.68 × 0.49 × 0.40 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.905, Tmax = 0.935

  • 37961 measured reflections

  • 4922 independent reflections

  • 3348 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.100

  • S = 0.96

  • 4922 reflections

  • 288 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2399 Freidel pairs

  • Flack parameter: -0.01 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.86 (3) 2.08 (3) 2.903 (4) 160 (2)
N2-H2A...O1ii 0.85 (2) 2.07 (2) 2.760 (3) 137 (2)
C10-H10A...F1iii 0.93 2.54 3.453 (5) 167
Symmetry codes: (i) [y+1, -x+y+1, z+{\script{1\over 6}}]; (ii) [x-y, x-1, z-{\script{1\over 6}}]; (iii) [-y, x-y-1, z-{\script{1\over 3}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2099 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Scientific Research Projects Coordination Unit of Istanbul University (project No. T-471/25062004).

References

Cihan-Üstündag, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.  [Web of Science] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Göktas, F., Vanderlinden, E., Naesens, L., Cesur, N. & Cesur, Z. (2012). Bioorg. Med. Chem. 20, 7155-7159.  [PubMed]
Güzel, Ö., Ilhan, E. & Salman, A. (2006). Monatsh. Chem. 137, 795-801.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Ulusoy, N. (2002). Arzneim.-Forsch. Drug. Res. 52, 565-571.  [ChemPort]
Vanderlinden, E., Göktas, F., Cesur, Z., Froeyen, M., Reed, M. L., Russell, C. J., Cesur, N. & Naesens, L. (2010). J. Virol. 84, 4277-4288.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1229  [ doi:10.1107/S1600536813018576 ]

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