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Volume 68 
Part 1 
Page o240  
January 2012  

Received 17 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.091
Data-to-parameter ratio = 21.9
Details
Open access

5-Bromo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

In the title compound, C11H8BrNO2, the nine-membered fused-ring is nearly planar [maximum deviation = 0.022 (2) Å] and the allyl group is arched over the nine-membered fused-ring at a dihedral angle of 89.2 (1)°. Weak intermolecular C-H...O hydrogen bonding is present in the crystal structure.

Related literature

For a related molecule, see: Abdel-Hamid et al. (2009[Abdel-Hamid, M. K., Bremner, J. B., Coates, J., Keller, P. A., Miländer, C., Torkamani, Y. S., Skelton, B. W., White, A. H. & Willis, A. C. (2009). Tetrahedron Lett. 50, 6947-6950.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8BrNO2

  • Mr = 266.09

  • Orthorhombic, P c c n

  • a = 31.3411 (5) Å

  • b = 7.8995 (1) Å

  • c = 8.2716 (1) Å

  • V = 2047.87 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.99 mm-1

  • T = 293 K

  • 0.17 × 0.14 × 0.13 mm

Data collection
  • Bruker APEX DUO diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.550, Tmax = 0.625

  • 50850 measured reflections

  • 2983 independent reflections

  • 2345 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.091

  • S = 1.06

  • 2983 reflections

  • 136 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.93 2.41 3.273 (2) 154
C11-H11A...O2ii 0.93 2.46 3.358 (3) 163
Symmetry codes: (i) x, y-1, z; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5413 ).


Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Abdel-Hamid, M. K., Bremner, J. B., Coates, J., Keller, P. A., Miländer, C., Torkamani, Y. S., Skelton, B. W., White, A. H. & Willis, A. C. (2009). Tetrahedron Lett. 50, 6947-6950.  [ChemPort]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o240  [ doi:10.1107/S160053681105447X ]

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