Received 23 November 2010
aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: email@example.com
In the title compound, C8H6BrNO3, there are two molecules, A and B, in the asymmetric unit. The nitro and ethanone groups lie close to the plane of the benzene ring and the bromine atom is twisted slightly: the dihedral angles between the mean planes of the nitro and ethanone groups and the benzene ring are 4.6 (4) (A) and 2.8 (3) (B), and 0.8 (8) (A) and 5.5 (8)° (B), respectively. An extensive array of weak C-HO hydrogen bonds, - ring stacking [centroid-centroid distances = 3.710 (5) and 3.677 (5) Å] and short non-hydrogen BrO and OBr intermolecular interactions [3.16 (6)and 3.06 (8) Å] contribute to the crystal stability, forming a supermolecular three-dimensional network structure along 110. These interactions give rise to a variety of cyclic graph-set motifs and form interconnected sheets in the three-dimensional structure.
For the use of -haloketones in the synthesis of pharmaceuticals, see: Erian et al. (2003). For related structures, see: Gupta & Prasad (1971); Sim (1986); Sutherland & Hoy (1968, 1969); Sutherland et al. (1974); Yathirajan et al. (2007); Young et al. (1968). For cyclic graph-set motifs, see: Etter (1990). For reference bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008)); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5067 ).
ASP thanks the University of Mysore (UOM) for research facilities and HSY thanks UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
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