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Volume 67 
Part 3 
Page o546  
March 2011  

Received 25 January 2011
Accepted 27 January 2011
Online 2 February 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.043
wR = 0.100
Data-to-parameter ratio = 18.6
Details
Open access

2,3-Dibromo-3-(5-nitro-2-furyl)-1-phenylpropan-1-one

Tara Shahani,a Hoong-Kun Fun,a*+ Nithinchandrab and Balakrishna Kallurayab

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C13H9Br2NO4, the phenyl and 2-nitrofuran rings are linked by a 2,3-dibromopropanal group, six atoms of which, including a furyl C atom, are disordered over two positions with a site-occupancy ratio of 0.733 (11):0.267 (11). The dihedral angle between the furan [maximum deviation = 0.028 (4) Å] and phenyl rings in the major component is 16.9 (3)°. In the minor component, the corresponding values are 0.87 (4) Å and 23.3 (5)°. In the crystal, intermolecular C-H...O hydrogen bonds link the molecules into two-dimensional arrays parallel to the ab plane.

Related literature

For the biological activity of sydnones, see: Holla et al. (1986[Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1986). Curr. Sci. 55, 73-76.], 1987[Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1987). Curr. Sci. 56, 236-238.], 1992[Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1992). Rev. Roum. Chim. 37, 1159-1164.]); Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.]). For related structures, see: Fun et al. (2010[Fun, H.-K., Shahani, T., Nithinchandra & Kalluraya, B. (2010). Acta Cryst. E66, o2818-o2819.], 2011[Fun, H.-K., Shahani, T., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o79.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9Br2NO4

  • Mr = 403.03

  • Triclinic, [P \overline 1]

  • a = 8.6939 (7) Å

  • b = 8.7834 (8) Å

  • c = 10.4722 (9) Å

  • [alpha] = 89.334 (2)°

  • [beta] = 69.846 (2)°

  • [gamma] = 68.114 (2)°

  • V = 690.32 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 5.88 mm-1

  • T = 100 K

  • 0.28 × 0.18 × 0.08 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.292, Tmax = 0.644

  • 10644 measured reflections

  • 4015 independent reflections

  • 3390 reflections with I > 2[sigma](I)

  • Rint = 0.030
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.100

  • S = 1.33

  • 4015 reflections

  • 216 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9A-H9AA...O1i 0.98 2.25 3.098 (6) 145
C4-H4A...O4ii 0.93 2.46 3.200 (6) 136
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5095 ).

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fun, H.-K., Shahani, T., Nithinchandra & Kalluraya, B. (2010). Acta Cryst. E66, o2818-o2819.
Fun, H.-K., Shahani, T., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o79.
Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1986). Curr. Sci. 55, 73-76.  [ChemPort]
Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1987). Curr. Sci. 56, 236-238.  [ChemPort]
Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1992). Rev. Roum. Chim. 37, 1159-1164.  [ChemPort]
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.  [ISI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2011). E67, o546  [ doi:10.1107/S1600536811003552 ]

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