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Volume 69 
Part 6 
Page o926  
June 2013  

Received 9 March 2013
Accepted 23 April 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.140
Data-to-parameter ratio = 17.1
Details
Open access

2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one

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

The title compound, C19H19NO3S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C-C coupling reaction and C-H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methylene-methane bond, and the cyclohexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the molecule. In the crystal, the presence of C-H...[pi] interactions leads to inversion dimers.

Related literature

For palladium-catalysed intermolecular and intramolecular 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-catalysed coupling reactions, see: Meng et al. (2011[Meng, T.-J., Hu, Y.-M., Zhao, Q.-S., Yu, T. & Wang, S. (2011). Tetrahedron, 67, 8710-8716.]); Hu et al. (2011[Hu, Y.-M., Sun, Y.-J., Hu, J.-P., Zhu, T., Yu, T. & Zhao, Q.-S. (2011). Chem. Asian J. 6, 797-800.]). They have made a wide variety active pharmaceutical ingredients and complex organic molecules economically accessible, 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 physiological activity of benzo[f]isoindol-1-one derivatives, see: Pitchumani & Vijaikumar (2010[Pitchumani, K. & Vijaikumar, S. (2010). Indian J. Chem. 49, 469-474.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19NO3S

  • Mr = 341.41

  • Triclinic, [P \overline 1]

  • a = 6.4389 (8) Å

  • b = 8.4336 (11) Å

  • c = 15.4958 (12) Å

  • [alpha] = 89.312 (2)°

  • [beta] = 87.395 (3)°

  • [gamma] = 81.224 (2)°

  • V = 830.75 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 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 = 0.943, Tmax = 0.955

  • 7242 measured reflections

  • 3724 independent reflections

  • 1902 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.140

  • S = 1.00

  • 3724 reflections

  • 218 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C10-H10A...Cg1i 0.97 2.63 3.555 (3) 159
Symmetry code: (i) -x+1, -y, -z+2.

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: 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: BV2220 ).


Acknowledgements

We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support for 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., Sun, Y.-J., Hu, J.-P., Zhu, T., Yu, T. & Zhao, Q.-S. (2011). Chem. Asian J. 6, 797-800.  [CSD] [CrossRef] [ChemPort] [PubMed]
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]
Meng, T.-J., Hu, Y.-M., Zhao, Q.-S., Yu, T. & Wang, S. (2011). Tetrahedron, 67, 8710-8716.  [ISI] [CSD] [CrossRef] [ChemPort]
Pitchumani, K. & Vijaikumar, S. (2010). Indian J. Chem. 49, 469-474.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [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, o926  [ doi:10.1107/S1600536813011045 ]

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