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Volume 66 
Part 5 
Page o1077  
May 2010  

Received 26 March 2010
Accepted 2 April 2010
Online 14 April 2010

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.076
wR = 0.210
Data-to-parameter ratio = 14.4
Details
Open access

9-Benzyl-9H-carbazole

Nesimi Uludag,a Murat Ates,a Baris Tercan,b Emel Ermisc and Tuncer Hökelekd*

aNamik Kemal University, Faculty of Arts and Sciences, Department of Chemistry, 59100 Tekirdag, Turkey,bKarabük University, Department of Physics, 78050 Karabük, Turkey,cAnadolu University, Faculty of Science, Department of Chemistry, 26470 Yenibaglar, Eskisehir, Turkey, and dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The asymmetric unit of the title compound, C19H15N, contains two crystallographically independent molecules. In both molecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7)°, respectively. In the crystal structure, weak C-H...[pi] interactions are observed involving the carbazole rings.

Related literature

For tetrahydrocarbazole systems present in the framework of a number of indole-type alkaloids of biological interest, see: Phillipson & Zenk (1980[Phillipson, J. D. & Zenk, M. H. (1980). Indole and Biogenetically Related Alkaloids, ch. 3. New York: Academic Press.]); Saxton (1983[Saxton, J. E. (1983). Editor. Heterocyclic Compounds, Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley.]); Abraham (1975[Abraham, D. J. (1975). The Catharanthus Alkaloids, edited by W. I. Taylor & N. R. Fransworth, chs. 7 and 8. New York: Marcel Decker.]). For related structures, see: Hökelek et al. (1994[Hökelek, T., Patir, S., Gülce, A. & Okay, G. (1994). Acta Cryst. C50, 450-453.], 1998[Hökelek, T., Gündüz, H., Patir, S. & Uludag, N. (1998). Acta Cryst. C54, 1297-1299.], 1999[Hökelek, T., Patir, S. & Uludag, N. (1999). Acta Cryst. C55, 114-116.], 2004[Hökelek, T., Uludag, N. & Patir, S. (2004). Acta Cryst. E60, o25-o27.], 2006[Hökelek, T., Uludag, N. & Patir, S. (2006). Acta Cryst. E62, o791-o793.]); Patir et al. (1997[Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.]); Hökelek & Patir (1999[Hökelek, T. & Patir, S. (1999). Acta Cryst. C55, 675-677.], 2002[Hökelek, T. & Patir, S. (2002). Acta Cryst. E58, o374-o376.]); Çaylak et al. (2007[Çaylak, N., Hökelek, T., Uludag, N. & Patir, S. (2007). Acta Cryst. E63, o3913-o3914.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C19H15N

  • Mr = 257.32

  • Monoclinic, P 21 /c

  • a = 14.9305 (4) Å

  • b = 5.5612 (2) Å

  • c = 32.7916 (8) Å

  • [beta] = 94.518 (3)°

  • V = 2714.27 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.27 × 0.15 × 0.14 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.990

  • 24870 measured reflections

  • 6816 independent reflections

  • 3384 reflections with I > 2[sigma](I)

  • Rint = 0.103
Refinement

  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.210

  • S = 1.03

  • 6816 reflections

  • 474 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...Cg1'i 0.97 (4) 2.940 (4) 3.636 (5) 129.46 (5)
C10'-H10C...Cg1'ii 0.98 (3) 2.787 (4) 3.700 (5) 154.92 (4)
C4'-H4'...Cg3i 0.99 (4) 2.706 (4) 3.554 (4) 144.36 (5)
Symmetry codes: (i) [-x, y-{{1\over 2}}, -z+{{1\over 2}}]; (ii) x, y+1, z. Cg1' and Cg3 are the centroids of the C1'-C4'/C4A'/C9A' and C5A/C5-C8/C8A rings, respectively.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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: XU2745 ).

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the X-ray diffractometer.

References

Abraham, D. J. (1975). The Catharanthus Alkaloids, edited by W. I. Taylor & N. R. Fransworth, chs. 7 and 8. New York: Marcel Decker.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.
Çaylak, N., Hökelek, T., Uludag, N. & Patir, S. (2007). Acta Cryst. E63, o3913-o3914.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hökelek, T., Gündüz, H., Patir, S. & Uludag, N. (1998). Acta Cryst. C54, 1297-1299.  [CrossRef] [details]
Hökelek, T. & Patir, S. (1999). Acta Cryst. C55, 675-677.  [CrossRef] [details]
Hökelek, T. & Patir, S. (2002). Acta Cryst. E58, o374-o376.  [CrossRef] [details]
Hökelek, T., Patir, S., Gülce, A. & Okay, G. (1994). Acta Cryst. C50, 450-453.  [CrossRef] [details]
Hökelek, T., Patir, S. & Uludag, N. (1999). Acta Cryst. C55, 114-116.  [CrossRef] [details]
Hökelek, T., Uludag, N. & Patir, S. (2004). Acta Cryst. E60, o25-o27.  [CrossRef] [details]
Hökelek, T., Uludag, N. & Patir, S. (2006). Acta Cryst. E62, o791-o793.  [CrossRef] [details]
Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.  [ChemPort]
Phillipson, J. D. & Zenk, M. H. (1980). Indole and Biogenetically Related Alkaloids, ch. 3. New York: Academic Press.
Saxton, J. E. (1983). Editor. Heterocyclic Compounds, Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1077  [ doi:10.1107/S1600536810012444 ]

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