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Volume 69 
Part 6 
Page o877  
June 2013  

Received 22 April 2013
Accepted 4 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.041
wR = 0.105
Data-to-parameter ratio = 13.5
Details
Open access

6,8-Dibromo-3-nitro-2-phenyl-2H-chromene

aDepartment of Medicinal Chemistry, School of Pharmacy, Fourth Military Medical University, Changle Xilu 169, 710032 Xi-An, People's Republic of China
Correspondence e-mail: syzhang@fmmu.edu.cn

In the title compound, C15H9Br2NO3, the chromene unit is not quite planar (r.m.s. deviation from planarity = 0.0888 Å). The dihydropyran ring adopts an envelope conformation with the phenyl-substituted C atom fused to the dihydropyran ring as the flap. The dihedral angle between the plane defined by this C atom and the adjacent C and O atoms and the mean plane of the dihydropyran ring excluding the phenyl-substituted C atom is 25.1 (3)°. The dihedral angle between the mean plane of the chromene unit and the phenyl ring is 85.7 (1)°. The crystal structure features C-H...O hydrogen bonds and Br...O contacts [3.289 (3) Å] involving the nitro O atoms.

Related literature

For the preparation of analogs of the title compound, see: Yan et al. (2001[Yan, M. C., Jang, Y. J. & Yao, C. F. (2001). Tetrahedron Lett. 42, 2717-2721.]); Pateliya et al. (2009[Pateliya, M. H., Rama Raju, B., Kavala, V., Kuo, C.-W. & Yao, C.-F. (2009). Tetrahedron, 65, 5799-5804.]). For synthetic uses of the analogs and bioactive derivatives of the title compound, see: Furuta et al. (2007[Furuta, T., Hirooka, Y., Abe, A., Sugata, Y., Ueda, M., Murakami, K., Suzuki, T., Tanaka, K. & Kan, T. (2007). Bioorg. Med. Chem. Lett. 17, 3095-3098.]); Pateliya et al. (2009[Pateliya, M. H., Rama Raju, B., Kavala, V., Kuo, C.-W. & Yao, C.-F. (2009). Tetrahedron, 65, 5799-5804.]).

[Scheme 1]

Experimental

Crystal data
  • C15H9Br2NO3

  • Mr = 411.05

  • Triclinic, [P \overline 1]

  • a = 8.2249 (19) Å

  • b = 8.886 (2) Å

  • c = 10.814 (3) Å

  • [alpha] = 73.503 (4)°

  • [beta] = 75.633 (4)°

  • [gamma] = 79.579 (4)°

  • V = 728.8 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 5.57 mm-1

  • T = 296 K

  • 0.37 × 0.24 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.232, Tmax = 0.505

  • 3687 measured reflections

  • 2563 independent reflections

  • 1856 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.105

  • S = 1.04

  • 2563 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.61 3.404 144
C7-H7...O2i 0.93 2.47 3.265 143
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2545 ).


Acknowledgements

We thank the Natural Science Foundation of China (grant No. 21172262) for financial support.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Furuta, T., Hirooka, Y., Abe, A., Sugata, Y., Ueda, M., Murakami, K., Suzuki, T., Tanaka, K. & Kan, T. (2007). Bioorg. Med. Chem. Lett. 17, 3095-3098.  [CrossRef] [PubMed] [ChemPort]
Pateliya, M. H., Rama Raju, B., Kavala, V., Kuo, C.-W. & Yao, C.-F. (2009). Tetrahedron, 65, 5799-5804.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yan, M. C., Jang, Y. J. & Yao, C. F. (2001). Tetrahedron Lett. 42, 2717-2721.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o877  [ doi:10.1107/S160053681301221X ]

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