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Volume 69 
Part 8 
Page o1202  
August 2013  

Received 1 July 2013
Accepted 2 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.092
Data-to-parameter ratio = 17.0
Details
Open access

5-Fluoro-3-phenyl-N'-(4-propylcyclohexylidene)-1H-indole-2-carbohydrazide

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, C24H26FN3O, the cyclohexane ring adopts a chair conformation; the propyl substituent is in an equatorial orientation and the bond-angle sum at the C atom bonded to the carbohydrazide N atom is 360.0°. The dihedral angle between the 1H-indole ring system and the phenyl ring is 82.77 (13)°. A weak intramolecular C-H...[pi] contact occurs. In the crystal, pairs of molecules related by a crystallographic twofold axis are linked by bifurcated N-H...(O,N) hydrogen bonds; a C-H...O interaction occurs between the same pair. The dimers are linked by C-H...F and C-H...[pi] interactions, generating a three-dimensional network.

Related literature

For the design and synthesis of indolylhydrazones and their cyclization products, spirothiazolidinones, as potential antituberculosis and anticancer agents, see: Akkurt et al. (2010[Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.], 2013[Akkurt, M., Zopun, M., Çapan, G. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1137.]); Cihan-Üstündag & Çapan (2012[Cihan-Üstündag, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26FN3O

  • Mr = 391.48

  • Tetragonal, [I \overline 4]

  • a = 22.6986 (11) Å

  • c = 8.4480 (5) Å

  • V = 4352.6 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.63 × 0.46 × 0.28 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.957, Tmax = 0.978

  • 15640 measured reflections

  • 4531 independent reflections

  • 3430 reflections with I > 2[sigma](I)

  • Rint = 0.066

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

  • wR(F2) = 0.092

  • S = 1.03

  • 4531 reflections

  • 267 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the 1H-pyrrole (N1/C1/C6/C7/C14), benzene (C1-C6) and phenyl (C8-C13) rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.50 3.048 (4) 123
N1-H1...N3i 0.86 2.32 3.170 (3) 168
C2-H2...O1i 0.93 2.51 3.112 (4) 123
C5-H5...F1ii 0.93 2.52 3.383 (3) 154
C3-H3...Cg3iii 0.93 2.82 3.708 (3) 160
C11-H11...Cg1iv 0.93 2.89 3.683 (3) 144
C17-H17A...Cg2v 0.97 2.81 3.571 (3) 136
C17-H17B...Cg3 0.97 2.90 3.810 (4) 157
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) y+1, -x+1, -z+1; (iii) -y+1, x-1, -z+1; (iv) y+1, -x+1, -z; (v) x, y, z-1.

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: HB7101 ).


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 Unit of Istanbul University (project No. T-471/25062004).

References

Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.  [CrossRef] [IUCr Journals]
Akkurt, M., Zopun, M., Çapan, G. & Büyükgüngör, O. (2013). Acta Cryst. E69, o1137.  [CrossRef] [IUCr Journals]
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]
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.


Acta Cryst (2013). E69, o1202  [ doi:10.1107/S1600536813018333 ]

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