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Volume 69 
Part 8 
Pages o1211-o1212  
August 2013  

Received 1 July 2013
Accepted 3 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.144
Data-to-parameter ratio = 17.5
Details
Open access

5-Fluoro-N'-(4-methylcyclohexylidene)-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, C22H22FN3O, crystallized with two independent molecules (A and B) in the asymmetric unit; these are linked by a pair of N-H...O hydrogen bonds, forming a pseudo-centrosymmetric dimer with an R22(10) motif. In addition, a number of C-H...[pi] interactions are also observed. The 1H-indole ring systems in molecules A and B are essentially planar [maximum deviations of 0.019 (2) and 0.014 (2) Å, respectively] and make dihedral angles of 77.64 (10) and 69.50 (9)°, respectively, with thephenyl rings.

Related literature

For the synthesis and characterization of some bioactive indole derivatives, 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.]); Zhang et al. (2004[Zhang, H. Z., Drewe, J., Tseng, B., Kasibhatla, S. & Cai, S. X. (2004). Bioorg. Med. Chem. 12, 3649-3655.]). 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
  • C22H22FN3O

  • Mr = 363.43

  • Triclinic, [P \overline 1]

  • a = 11.6630 (6) Å

  • b = 13.5320 (7) Å

  • c = 14.7754 (8) Å

  • [alpha] = 112.967 (4)°

  • [beta] = 95.936 (4)°

  • [gamma] = 111.385 (4)°

  • V = 1915.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.68 × 0.52 × 0.33 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 = 0.948, Tmax = 0.972

  • 26097 measured reflections

  • 8702 independent reflections

  • 5714 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.144

  • S = 1.03

  • 8702 reflections

  • 496 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg6 and Cg8 are the centroids of the 1H-pyrrole and benzene rings of the 1H-indole ring system of molecule A, the phenyl ring of molecule A, the 1H-pyrrole ring of the 1H-indole ring system of molecule B and the phenyl ring of molecule B, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.86 2.15 2.895 (2) 145
N4-H4...O1 0.86 2.04 2.811 (2) 149
C17-H17A...Cg1i 0.97 2.66 3.594 (3) 163
C17-H17B...Cg3 0.97 2.74 3.685 (3) 164
C31-H31...Cg6ii 0.93 2.87 3.658 (2) 144
C35-H35...Cg2iii 0.93 2.96 3.627 (3) 130
C39-H39B...Cg8 0.97 2.72 3.667 (3) 164
C42-H42A...Cg1iv 0.97 2.99 3.848 (3) 148
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z.

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: SJ5341 ).


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

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]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
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.
Zhang, H. Z., Drewe, J., Tseng, B., Kasibhatla, S. & Cai, S. X. (2004). Bioorg. Med. Chem. 12, 3649-3655.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1211-o1212   [ doi:10.1107/S1600536813018436 ]

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