5-(Prop-2-yn­yl)-5H-dibenzo[b,f]azepine

Yousuf, S.; Khan, M.; Fazal, S.; Butt, M.; Basha, F.Z.

doi:10.1107/S1600536812007866

Volume 68
Part 4
Page o1101
April 2012

Received 26 January 2012
Accepted 21 February 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.129
Data-to-parameter ratio = 14.3
Details

5-(Prop-2-ynyl)-5H-dibenzo[b,f]azepine

S. Yousuf,^a ^* M. Khan,^a S. Fazal,^a M. Butt ^a and F. Z. Basha ^a

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

The asymmetric unit of the title compound, C₁₇H₁₃N, contains two independent butterfly-shaped molecules. The seven-membered azepine rings both adopt a boat conformation. The dihedral angles between the benzene rings in the two molecules are 46.95 (11) and 52.21 (11)°.

Related literature

For the biological activities of iminostilbene, see: Kumar & Naik (2010); Balaure et al. (2009); Bhatt & Patel (2005); Fuenfschilling et al. (2005); Rosowsky et al. (2004); Brzozowski & Saczewski (2002); Kulkarni et al. (1991); Arya et al. (1977). For the crystal structures of the closely related compounds, see: Jayasankar et al. (2009); Nagaraj et al. (2005); Sadashiva et al. (2005).

Experimental

Crystal data

C₁₇H₁₃N
M_r = 231.28
Monoclinic, P 2₁ /c
a = 11.4406 (5) Å
b = 10.0256 (4) Å
c = 22.3155 (10) Å
= 92.910 (1)°
V = 2556.26 (19) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 273 K
0.36 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.975, T_max = 0.990
14791 measured reflections
4760 independent reflections
2894 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.129
S = 1.02
4760 reflections
333 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.13 e Å^-3
_min = -0.17 e Å^-3

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2705 ).

References

Arya, V. P., Grewal, R. S., Kaul, C. L., David, J., Shenoy, S. J. & Honkan, V. (1977). Indian J. Chem. Sect. B, 15, 148-153.
Balaure, P. C., Costea, I., Iordache, F., Draghichi, C. & Enache, C. (2009). Rev. Roum. Chem. 54, 935-942.
Bhatt, P. V. & Patel, P. M. (2005). Indian J. Chem. Sect. B, 44, 2082-2086.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Brzozowski, Z. & Saczewski, F. (2002). J. Med. Chem. 45, 430-437.
Fuenfschilling, P. C., Zangg, W., Beutler, U., Kaufmann, D., Lohse, O., Mutz, J.-P., Onken, U., Reber, J.-L. & Shenton, D. (2005). Org. Process Res. Dev. 9, 272-277.
Jayasankar, A., Reddy, L. S., Bethune, S. J. & Rodriguez-Hornedo, N. (2009). Cryst. Growth Des. 9, 889-897.
Kulkarni, G. H., Naik, R. H., Tandel, S. K. & Rajappa, S. (1991). Tetrahedron, 47, 1249-1256.
Kumar, H. V. & Naik, N. (2010). Eur. J. Med. Chem. 45, 2-10.
Nagaraj, B., Yathirajan, H. S. & Lynch, D. E. (2005). Acta Cryst. E61, o1757-o1759.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Rosowsky, A., Fu, H., Chan, D. C. & Queener, S. F. (2004). J. Med. Chem. 47, 2475-2485.
Sadashiva, M. P., Doreswamy, B. H., Basappa, Rangappa, K. S., Sridhar, M. A. & Prasad, J. (2005). J. Chem. Crystallogr. 35, 171-175.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds