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

Abdoh, M.M.M.; Madan Kumar, S.; Vinay Kumar, K.S.; Manjunath, B.C.; Sadashiva, M.P.; Lokanath, N.K.

doi:10.1107/S1600536812048908

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 (C-C) = 0.003 Å
R = 0.026
wR = 0.067
Data-to-parameter ratio = 7.3
Details

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

M. M. M. Abdoh,^a S. Madan Kumar,^b K. S. Vinay Kumar,^c B. C. Manjunath,^b M. P. Sadashiva ^c and N. K. Lokanath ^b ^*

^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). 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). For biochemical background, see: Sadashiva et al. (2005).

Experimental

Crystal data

C₁₇H₁₃N
M_r = 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 radiation
= 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(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.067
S = 1.09
1199 reflections
164 parameters
1 restraint
H-atom parameters constrained
_max = 0.08 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C10-H10Cg2ⁱ	0.95	2.75	3.659 (2)	160
C18-H18Cg1ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); 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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yousuf, S., Khan, M., Fazal, S., Butt, M. & Basha, F. Z. (2012). Acta Cryst. E68, o1101.

organic compounds