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Volume 69 
Part 4 
Page o473  
April 2013  

Received 18 February 2013
Accepted 25 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.025
wR = 0.061
Data-to-parameter ratio = 15.2
Details
Open access

3-Bromochroman-4-one

aSchool of Chemistry and Physics, University of Kwazulu-Natal, Private Bag X54001, Durban 4000, South Africa,bDiscipline of Pharmaceutical Science, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa, and cSchool of Engineering, University of KwaZulu-Natal, Durban 4041, South Africa
Correspondence e-mail: koorbanally@ukzn.ac.za

The heterocyclic ring of the title compound, C9H7BrO2, obtained by bromination of 4-chromanone with copper bromide, adopts a half-chair conformation. The supramolecular structure is governed by a weak C-H...O hydrogen bond. There is also [pi]-[pi] stacking between symmetry-related benzene rings; the centroid-centroid distance is 3.9464 (18), the perpendicular distance between the rings is 3.4703 (11) and the offset is 1.879 Å.

Related literature

For similar structures, see: Schollmeyer et al. (2005[Schollmeyer, D., Kammerer, B., Peifer, C. & Laufer, S. (2005). Acta Cryst. E61, o868-o869.]); Piel et al. (2011[Piel, I., Steinmetz, M., Hirano, K., Fröhlich, R., Grimme, S. & Glorius, F. (2011). Angew. Chem. Int. Ed. 50, 4983-4987.]); Betz et al. (2011[Betz, R., McCleland, C. & Marchand, H. (2011). Acta Cryst. E67, o1151.]). For synthesis involving chromanone intermediates, see: Simas et al. (2002[Simas, A. B. C., Furtado, L. F. O. & Costa, P. R. R. (2002). Tetrahedron Lett. 43, 6893-6895.]); Zhang et al. (2008[Zhang, L., Zhang, W.-G., Kang, J., Bao, K., Dai, Y. & Yao, X.-S. (2008). J. Asian Nat. Prod. Res. 10, 909-913.]). For the biological activity of chromanone derivatives, see: Cho et al. (1996[Cho, H., Katoh, S., Sayama, S., Murakami, K., Nakanishi, H., Kajimoto, Y., Ueno, H., Kawasaki, H., Aisaka, K. & Uchida, I. (1996). J. Med. Chem. 39, 3797-3805.]); Xu et al. (1998[Xu, Z.-Q., Buckheit Jnr, R. W., Stup, T. L., Flavin, M. T., Khilevich, A., Rizzo, J. D., Lin, L. & Zembower, D. E. (1998). Bioorg. Med. Chem. Lett. 8, 2179-2184.]); Shaikh et al. (2012[Shaikh, M. M., Kruger, H. G., Bodenstein, J., Smith, P. & du Toit, K. (2012). Nat. Prod. Res. 26, 1473-1483.], 2013a[Shaikh, M. M., Kruger, H. G., Smith, P., Bodenstein, J. & du Toit, K. (2013a). J. Pharm. Res. 6, 21-25.],b[Shaikh, M. M., Kruger, H. G., Smith, P., Munro, O. Q., Bodenstein, J. & du Toit, K. (2013b). J. Pharm. Res. 6, 1-5.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7BrO2

  • Mr = 227.06

  • Monoclinic, P 21 /c

  • a = 10.0846 (7) Å

  • b = 7.9104 (6) Å

  • c = 10.9330 (8) Å

  • [beta] = 110.164 (2)°

  • V = 818.71 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.97 mm-1

  • T = 173 K

  • 0.16 × 0.12 × 0.12 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.504, Tmax = 0.587

  • 5434 measured reflections

  • 1659 independent reflections

  • 1392 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.061

  • S = 1.05

  • 1659 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...O2i 0.99 2.44 3.311 (3) 146
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2082 ).


Acknowledgements

We thank the University of KwaZulu-Natal, the National Research Foundation (NRF) and the South African Research Chairs initiative of the Department of Science and Technology for financial support and Ms Hong Su for the data collection.

References

Betz, R., McCleland, C. & Marchand, H. (2011). Acta Cryst. E67, o1151.  [CSD] [CrossRef] [details]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, H., Katoh, S., Sayama, S., Murakami, K., Nakanishi, H., Kajimoto, Y., Ueno, H., Kawasaki, H., Aisaka, K. & Uchida, I. (1996). J. Med. Chem. 39, 3797-3805.  [CrossRef] [ChemPort] [PubMed] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Piel, I., Steinmetz, M., Hirano, K., Fröhlich, R., Grimme, S. & Glorius, F. (2011). Angew. Chem. Int. Ed. 50, 4983-4987.  [ISI] [CSD] [CrossRef] [ChemPort]
Schollmeyer, D., Kammerer, B., Peifer, C. & Laufer, S. (2005). Acta Cryst. E61, o868-o869.  [CSD] [CrossRef] [details]
Shaikh, M. M., Kruger, H. G., Bodenstein, J., Smith, P. & du Toit, K. (2012). Nat. Prod. Res. 26, 1473-1483.  [ISI] [CrossRef] [ChemPort] [PubMed]
Shaikh, M. M., Kruger, H. G., Smith, P., Bodenstein, J. & du Toit, K. (2013a). J. Pharm. Res. 6, 21-25.
Shaikh, M. M., Kruger, H. G., Smith, P., Munro, O. Q., Bodenstein, J. & du Toit, K. (2013b). J. Pharm. Res. 6, 1-5.
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simas, A. B. C., Furtado, L. F. O. & Costa, P. R. R. (2002). Tetrahedron Lett. 43, 6893-6895.  [ISI] [CrossRef] [ChemPort]
Xu, Z.-Q., Buckheit Jnr, R. W., Stup, T. L., Flavin, M. T., Khilevich, A., Rizzo, J. D., Lin, L. & Zembower, D. E. (1998). Bioorg. Med. Chem. Lett. 8, 2179-2184.  [ChemPort] [PubMed]
Zhang, L., Zhang, W.-G., Kang, J., Bao, K., Dai, Y. & Yao, X.-S. (2008). J. Asian Nat. Prod. Res. 10, 909-913.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o473  [ doi:10.1107/S1600536813005394 ]

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