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Volume 69 
Part 8 
Page o1331  
August 2013  

Received 22 July 2013
Accepted 23 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.067
wR = 0.180
Data-to-parameter ratio = 15.7
Details
Open access

N'-(4-Ethylcyclohexylidene)-5-fluoro-3-phenyl-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

The title compound, C23H24FN3O, crystallizes with two independent molecules (I and II) in the asymmetric unit. These pairs of molecules are linked to each other as N-H...O dimers with an R22(10) motif. Furthermore, the crystal structure also exhibits C-H...[pi] interactions. The atoms of the ethyl group in molecule I are disordered over two sites with an occupancy ratio of 0.817 (6):0.183 (6).

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.]). For similar structures, see: Çelikesir et al. (2013a[Çelikesir, S. T., Akkurt, M., Üstündag, G. C. & Büyükgüngör, O. (2013a). Acta Cryst. E69, o1202.],b[Çelikesir, S. T., Akkurt, M., Üstündag, G. C., Çapan, G. & Büyükgüngör, O. (2013b). Acta Cryst. E69, o1211-o1212.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24FN3O

  • Mr = 377.45

  • Triclinic, [P \overline 1]

  • a = 11.8121 (5) Å

  • b = 13.3802 (5) Å

  • c = 15.5693 (6) Å

  • [alpha] = 114.328 (3)°

  • [beta] = 95.642 (3)°

  • [gamma] = 110.434 (3)°

  • V = 2014.85 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.55 × 0.48 × 0.37 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 = 0.955, Tmax = 0.969

  • 30678 measured reflections

  • 8272 independent reflections

  • 5564 reflections with I > 2[sigma](I)

  • Rint = 0.108

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.180

  • S = 1.02

  • 8272 reflections

  • 528 parameters

  • 8 restraints

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8-C13, N4/C24/C29/C30/C37 and C31-C36 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2 0.85 (3) 2.00 (3) 2.836 (3) 168 (3)
N4-H4N...O1 0.85 (3) 2.08 (3) 2.887 (3) 160 (2)
C9-H9...Cg1i 0.93 2.81 3.636 (3) 149
C17-H17A...Cg3 0.97 2.87 3.820 (3) 165
C40-H40A...Cg7 0.97 2.79 3.727 (4) 163
C40-H40B...Cg5ii 0.97 2.65 3.595 (4) 163
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+2.

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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5346 ).


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

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Çelikesir, S. T., Akkurt, M., Üstündag, G. C. & Büyükgüngör, O. (2013a). Acta Cryst. E69, o1202.  [CrossRef] [IUCr Journals]
Çelikesir, S. T., Akkurt, M., Üstündag, G. C., Çapan, G. & Büyükgüngör, O. (2013b). Acta Cryst. E69, o1211-o1212.  [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]
Göktas, F., Vanderlinden, E., Naesens, L., Cesur, N. & Cesur, Z. (2012). Bioorg. Med. Chem. 20, 7155-7159.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o1331  [ doi:10.1107/S1600536813020394 ]

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