[Journal logo]

Volume 69 
Part 1 
Page o17  
January 2013  

Received 22 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 103 K
Mean [sigma](C-C) = 0.003 Å
R = 0.026
wR = 0.067
Data-to-parameter ratio = 7.3
Details
Open access

5-(Prop-2-yn-1-yl)-5H-dibenzo[b,f]azepine: orthorhombic polymorph

aDepartment of Physics, Faculty of Science, An Najah National University, Nabtus West Bank, Palestine,bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title orthorhombic polymorph (space group Iba2), C17H13N, the dihedral angle between the benzene rings is 55.99 (10)° and the azepine ring adopts a boat conformation. In the crystal, molecules are linked by C-H...[pi] contacts. The previously-reported polymorph [Yousuf et al. (2012[Yousuf, S., Khan, M., Fazal, S., Butt, M. & Basha, F. Z. (2012). Acta Cryst. E68, o1101.]). Acta Cryst. E68, o1101] crystallizes in the monoclinic system (space group P21/c) with two molecules in the asymmetric unit.

Related literature

For the previously-reported monoclinic polymorph, see: Yousuf et al. (2012[Yousuf, S., Khan, M., Fazal, S., Butt, M. & Basha, F. Z. (2012). Acta Cryst. E68, o1101.]). For biochemical background, see: Sadashiva et al. (2005[Sadashiva, M. P., Mallesha, H., KarunakaraMurthy, K. & Rangappa, K. S. (2005). Bioorg. Med. Chem. Lett. 15, 1811-1814.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13N

  • Mr = 231.28

  • Orthorhombic, I b a 2

  • a = 16.2444 (6) Å

  • b = 21.1700 (6) Å

  • c = 7.2399 (2) Å

  • V = 2489.76 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 103 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 10081 measured reflections

  • 1199 independent reflections

  • 1132 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.067

  • S = 1.09

  • 1199 reflections

  • 164 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.08 e Å-3

  • [Delta][rho]min = -0.10 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2/C3/C12-C15 and C6-C11 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10...Cg2i 0.95 2.75 3.659 (2) 160
C18-H18...Cg1ii 0.95 2.58 3.512 (2) 167
Symmetry codes: (i) [-x, y, z-{\script{1\over 2}}]; (ii) x, y, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6998 ).


Acknowledgements

SMK thanks UGC-BRS and University of Mysore for the award of a fellowship. MPS gratefully acknowledges financial support (grant No. 37-456/2009[SR]) from the University Grants Commission, New Delhi, India.

References

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.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sadashiva, M. P., Mallesha, H., KarunakaraMurthy, K. & Rangappa, K. S. (2005). Bioorg. Med. Chem. Lett. 15, 1811-1814.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yousuf, S., Khan, M., Fazal, S., Butt, M. & Basha, F. Z. (2012). Acta Cryst. E68, o1101.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o17  [ doi:10.1107/S1600536812048908 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.