11H-Dibenzo[b,e]azepine-6-carbonitrile

Fan, G.-D.; Xiao, Y.-L.; You, G.-R.; Duan, G.-Y.

doi:10.1107/S1600536808033072

Volume 64
Part 11
Page o2126
November 2008

Received 5 October 2008
Accepted 13 October 2008
Online 18 October 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 13.3
Details

11H-Dibenzo[b,e]azepine-6-carbonitrile

Guo-Dong Fan,^a Yu-Liang Xiao,^b Gui-Rong You ^b and Gui-Yun Duan ^b ^*

^aCollege of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, People's Republic of China, and ^bCollege of Pharmaceutical Sciences, Taishan Medical College, Tai'an 271016, People's Republic of China
Correspondence e-mail: duanguiyun@yahoo.cn

The title compound, C₁₅H₁₀N₂, crystallizes with two independent molecules in the asymmetric unit. The two benzene rings make dihedral angles of 60.32 (2) and 61.35 (3)°. The crystal packing is stabilized by weak [pi] - [pi] stacking interactions [centroid-to-centroid distances = 3.673 (4) and 3.793 (4) Å].

Related literature

For discussions of the biological activity of the title compound, see: Bakker et al. (2000); Bielory & Ghafoor (2005); Schmutz et al. (1967). For a similar structure, see: Li et al. (2006).

Experimental

Crystal data

C₁₅H₁₀N₂
M_r = 218.25
Triclinic, $[P \overline 1]$
a = 10.125 (2) Å
b = 10.275 (2) Å
c = 12.749 (3) Å
= 105.96 (3)°
= 99.18 (2)°
= 109.04 (3)°
V = 1159.2 (6) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.989, T_max = 0.993
12026 measured reflections
4084 independent reflections
3382 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
4084 reflections
308 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.13 e Å^-3

Table 1
Selected interatomic distances (Å)

Cg1 is the centroid of the ring C8-C13 and Cg2 is the centroid of the ring C23-C28.

Cg1Cg1ⁱ	3.673 (4)
Cg2Cg2ⁱⁱ	3.793 (4)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2271 ).

References

Bakker, R. A., Wieland, K., Timmerman, H. & Leurs, R. (2000). Eur. J. Pharmacol. 387, R5-R7.
Bielory, L. & Ghafoor, S. (2005). Curr. Opin. Allergy Clin. Immunol. 5, 437-440.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin.
Li, Q.-B., Yang, W.-C., Han, Y.-J. & Zhao, X.-J. (2006). Acta Cryst. E62, o3021-o3022.
Schmutz, J., Hunziker, F. & Kunzle, F. (1967). Helv. Chim. Acta, 50, 245-248.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

11H-Dibenzo[b,e]azepine-6-carbonitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

References