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

Maamri, K.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S160053681105447X

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 (C-C) = 0.002 Å
R = 0.029
wR = 0.091
Data-to-parameter ratio = 21.9
Details

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

Khalil Maamri,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^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-HO hydrogen bonding is present in the crystal structure.

Related literature

For a related molecule, see: Abdel-Hamid et al. (2009).

Experimental

Crystal data

C₁₁H₈BrNO₂
M_r = 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 radiation
= 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) T_min = 0.550, T_max = 0.625
50850 measured reflections
2983 independent reflections
2345 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.091
S = 1.06
2983 reflections
136 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.63 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.93	2.41	3.273 (2)	154
C11-H11AO2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References