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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 [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 13.3
Details
Open access

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

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[Bakker, R. A., Wieland, K., Timmerman, H. & Leurs, R. (2000). Eur. J. Pharmacol. 387, R5-R7.]); Bielory & Ghafoor (2005[Bielory, L. & Ghafoor, S. (2005). Curr. Opin. Allergy Clin. Immunol. 5, 437-440.]); Schmutz et al. (1967[Schmutz, J., Hunziker, F. & Kunzle, F. (1967). Helv. Chim. Acta, 50, 245-248.]). For a similar structure, see: Li et al. (2006[Li, Q.-B., Yang, W.-C., Han, Y.-J. & Zhao, X.-J. (2006). Acta Cryst. E62, o3021-o3022.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10N2

  • Mr = 218.25

  • Triclinic, [P \overline 1]

  • a = 10.125 (2) Å

  • b = 10.275 (2) Å

  • c = 12.749 (3) Å

  • [alpha] = 105.96 (3)°

  • [beta] = 99.18 (2)°

  • [gamma] = 109.04 (3)°

  • V = 1159.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.989, Tmax = 0.993

  • 12026 measured reflections

  • 4084 independent reflections

  • 3382 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.03

  • 4084 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]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.

Cg1...Cg1i 3.673 (4)
Cg2...Cg2ii 3.793 (4)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
Bielory, L. & Ghafoor, S. (2005). Curr. Opin. Allergy Clin. Immunol. 5, 437-440.  [PubMed] [ChemPort]
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.  [CSD] [CrossRef] [details]
Schmutz, J., Hunziker, F. & Kunzle, F. (1967). Helv. Chim. Acta, 50, 245-248.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2008). E64, o2126  [ doi:10.1107/S1600536808033072 ]

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