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Volume 69 
Part 4 
Page o550  
April 2013  

Received 9 March 2013
Accepted 12 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.128
Data-to-parameter ratio = 17.6
Details
Open access

4-(6-Benzyl-7-oxo-1,2,3,4,5,5a,5a1,6,7,7a,8,12b-dodecahydrobenzo[f]cycloocta[cd]isoindol-8-yl)benzonitrile

aSchool of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, People's Republic of China
Correspondence e-mail: yiminhu@yahoo.cn

In the title compound, C31H30N2O, the cis-fused cyclohexene and cyclooctane rings adopt boat and boat-chair conformations, respectively. The essentially planar five-membered N-heterocyclic ring [r.m.s. deviation = 0.017 (1) Å] is cis- and trans-fused, respectively, with the cyclohexene and cyclooctane rings. In the crystal, molecules are linked into inversion dimers through pairs of weak C-H...O interactions.

Related literature

For the atom economy and environmental benefits of using a domino reaction to construct a structurally complicated molecule, see: Zhao et al. (2012[Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113-2116.]). For palladium-catalysed coupling reactions, see: Hu et al. (2009[Hu, Y.-M., Ouyang, Y., Qu, Y., Hu, Q. & Yao, H. (2009). Chem. Commun. pp. 4575-4577.], 2010[Hu, Y.-M., Lin, X.-G., Zhu, T., Wan, J., Sun, Y.-J., Zhao, Q. S. & Yu, T. (2010). Synthesis, 42, 3467-3473.]). For the use of condensed heterocyclic compounds as synthetic building blocks, pharmacophores and electroluminescent materials, see: Rixson et al. (2012[Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. pp. 544-558.]). For reactions of aryl halides with olefins, see: Yu & Hu (2012[Yu, T. & Hu, Y. (2012). Acta Cryst. E68, o1184.]); Wang & Hu (2011[Wang, H. & Hu, Y. (2011). Acta Cryst. E67, o919.]).

[Scheme 1]

Experimental

Crystal data
  • C31H30N2O

  • Mr = 446.57

  • Monoclinic, P 21 /c

  • a = 10.0270 (11) Å

  • b = 11.2196 (13) Å

  • c = 21.445 (2) Å

  • [beta] = 102.912 (1)°

  • V = 2351.5 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 291 K

  • 0.26 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.985

  • 19941 measured reflections

  • 5413 independent reflections

  • 4118 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.128

  • S = 1.04

  • 5413 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C29-H29...O1i 0.93 2.58 3.301 (2) 134
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5255 ).


Acknowledgements

We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support of this work.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hu, Y.-M., Lin, X.-G., Zhu, T., Wan, J., Sun, Y.-J., Zhao, Q. S. & Yu, T. (2010). Synthesis, 42, 3467-3473.  [ISI] [CrossRef]
Hu, Y.-M., Ouyang, Y., Qu, Y., Hu, Q. & Yao, H. (2009). Chem. Commun. pp. 4575-4577.  [CSD] [CrossRef]
Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. pp. 544-558.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, H. & Hu, Y. (2011). Acta Cryst. E67, o919.  [CSD] [CrossRef] [details]
Yu, T. & Hu, Y. (2012). Acta Cryst. E68, o1184.  [CSD] [CrossRef] [details]
Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113-2116.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o550  [ doi:10.1107/S1600536813006880 ]

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