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Volume 69 
Part 7 
Page o1137  
July 2013  

Received 17 June 2013
Accepted 18 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.129
Data-to-parameter ratio = 15.0
Details
Open access

5-Chloro-N'-cyclohexylidene-3-methyl-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, C16H18ClN3O, the cyclohexane ring adopts a distorted chair conformation. In the crystal, pairs of molecules are linked by N-H...O hydrogen bonds into inversion dimers, forming R22(10) ring motifs. These dimers are connected through C-H...N hydrogen bonds into chains along the a axis, forming layers parallel to (101).

Related literature

For the design, synthesis and characterization of some bioactive indole derivatives, see: Akkurt et al. (2009[Akkurt, M., Karaca, S., Cihan, G., Çapan, G. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1009-o1010.], 2010[Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.]); Cihan-Üstündag & Çapan (2012[Cihan-Üstündag, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.]); Güzel et al. (2006[Güzel, O., Terzioglu, N., Çapan, G. & Salman, A. (2006). Arkivoc, xii, 98-110.]); Kaynak et al. (2005[Kaynak, F. B., Öztürk, D., Özbey, S. & Çapan, G. (2005). J. Mol. Struct. 740, 213-221.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, 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
  • C16H18ClN3O

  • Mr = 303.78

  • Triclinic, [P \overline 1]

  • a = 5.2727 (5) Å

  • b = 9.7977 (9) Å

  • c = 15.2380 (15) Å

  • [alpha] = 102.229 (7)°

  • [beta] = 95.732 (8)°

  • [gamma] = 92.332 (7)°

  • V = 763.94 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 296 K

  • 0.76 × 0.36 × 0.02 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 = 0.831, Tmax = 0.995

  • 7177 measured reflections

  • 2929 independent reflections

  • 1684 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.129

  • S = 1.01

  • 2929 reflections

  • 195 parameters

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.03 2.826 (3) 153
C12-H12B...N3ii 0.97 2.59 3.476 (4) 152
Symmetry codes: (i) -x, -y, -z+1; (ii) 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: SJ5335 ).


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 in part by the Scientific Research Projects Coordination Unit of Istanbul University (project No. 20867).

References

Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o830.  [CrossRef] [IUCr Journals]
Akkurt, M., Karaca, S., Cihan, G., Çapan, G. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1009-o1010.  [CSD] [CrossRef] [ChemPort] [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]
Güzel, O., Terzioglu, N., Çapan, G. & Salman, A. (2006). Arkivoc, xii, 98-110.
Kaynak, F. B., Öztürk, D., Özbey, S. & Çapan, G. (2005). J. Mol. Struct. 740, 213-221.  [Web of Science] [CSD] [CrossRef] [ChemPort]
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, o1137  [ doi:10.1107/S1600536813016899 ]

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