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Volume 69 
Part 8 
Page o1233  
August 2013  

Received 24 June 2013
Accepted 3 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 14.7
Details
Open access

5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)methyl]-5H-dibenzo[b,f]azepine

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C24H20N4, the azepine ring adopts a boat conformation and the dihedral angle between the benzene rings fused to it is 57.95 (8)°. The bond-angle sum at the azepine N atom is 346.6°, indicating a significant deviation from planarity. The triazole ring subtends a dihedral angle of 71.45 (10)° with the terminal phenyl group. A weak intramolecular C-H...Na (a = azepine) interaction occurs, which closes an S(6) ring.

Related literature

For a related structure and background to isoxazole derivatives, see: Abdoh et al. (2013[Abdoh, M. M. M., Madan Kumar, S., Vinay Kumar, K. S., Manjunath, B. C., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o17.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N4

  • Mr = 364.44

  • Monoclinic, P 21 /c

  • a = 9.4394 (10) Å

  • b = 22.206 (3) Å

  • c = 9.4330 (9) Å

  • [beta] = 107.172 (3)°

  • V = 1889.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.26 × 0.23 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 22703 measured reflections

  • 3711 independent reflections

  • 2982 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.01

  • 3711 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...N4 0.97 2.56 3.173 (2) 121

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7099 ).


Acknowledgements

We thank Professor T. N. Guru Row and Vijith Kumar, SSCU, IISc, Bangalore, India, for providing facilities for the data collection.

References

Abdoh, M. M. M., Madan Kumar, S., Vinay Kumar, K. S., Manjunath, B. C., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o17.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1233  [ doi:10.1107/S1600536813018412 ]

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