[Journal logo]

Volume 69 
Part 5 
Page o652  
May 2013  

Received 10 March 2013
Accepted 28 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.006 Å
R = 0.052
wR = 0.095
Data-to-parameter ratio = 15.2
Details
Open access

2-(4-Methylphenyl)-3-oxo-4-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-6-carbonitrile

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, C26H22N2O, one phenyl ring, one five-membered N-heterocyclic ring and one six-membered carbocyclic ring make up the hexahydrobenzo[f]isoindole core. Another phenyl group is attached to the heterocyclic N atom as a substituent. The non-aromatic five- and six-membered rings both exhibit boat conformations. In the crystal, weak C-H...O and C-H...N interactions establish the observed three-dimensional structure. The crystal studied was refined as an inversion twin.

Related literature

For background to domino reactions, see Zhao et al. (2012[Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113-2116.]) and for palladium-catalyzed domino reactions, see Hu et al. (2009[Hu, Y.-M., Yu, C.-L., Ren, D., Hu, Q., Zhang, L.-D. & Cheng, D. (2009). Angew. Chem. Int. Ed. 48, 5448-5451.], 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 wide variety of active pharmaceutical ingredients, natural products and other complex organic molecules economically accessible, 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.]). For benzo[f]isoindol-1-one derivatives as effective intermediates, see: Rixson et al. (2012[Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. 23, 544-558.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N2O

  • Mr = 378.45

  • Orthorhombic, P c a 21

  • a = 25.005 (6) Å

  • b = 5.5023 (14) Å

  • c = 14.790 (4) Å

  • V = 2034.9 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 291 K

  • 0.28 × 0.24 × 0.22 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 = 0.972, Tmax = 0.983

  • 14617 measured reflections

  • 4001 independent reflections

  • 2187 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.095

  • S = 1.03

  • 4001 reflections

  • 264 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C25-H25...O1i 0.93 2.69 3.577 (6) 159
C4-H4...N2ii 0.93 2.62 3.329 (6) 134
C21-H21...O1iii 0.93 2.58 3.498 (5) 169
Symmetry codes: (i) [-x+1, -y+2, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+2, z]; (iii) x, y+1, z.

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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2425 ).


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., Yu, C.-L., Ren, D., Hu, Q., Zhang, L.-D. & Cheng, D. (2009). Angew. Chem. Int. Ed. 48, 5448-5451.  [ISI] [CSD] [CrossRef] [ChemPort]
Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. 23, 544-558.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [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, o652  [ doi:10.1107/S1600536813008568 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.