2-Bromo-1-(3-nitro­phen­yl)ethanone

Jasinski, J.P.; Butcher, R.J.; Praveen, A.S.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810049585

Volume 67
Part 1
Pages o29-o30
January 2011

Received 23 November 2010
Accepted 26 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.011 Å
R = 0.090
wR = 0.248
Data-to-parameter ratio = 13.7
Details

2-Bromo-1-(3-nitrophenyl)ethanone

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b A. S. Praveen,^c H. S. Yathirajan ^c and B. Narayana ^d

^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: jjasinski@keene.edu

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, [pi] - [pi] 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.

Related literature

For the use of [alpha] -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).

Experimental

Crystal data

C₈H₆BrNO₃
M_r = 244.05
Triclinic, $[P \overline 1]$
a = 8.8259 (7) Å
b = 8.8651 (8) Å
c = 11.6775 (8) Å
= 74.691 (7)°
= 75.174 (7)°
= 78.681 (7)°
V = 843.76 (12) Å³
Z = 4
Cu K radiation
= 6.45 mm^-1
T = 123 K
0.75 × 0.62 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.066, T_max = 0.389
4708 measured reflections
3215 independent reflections
3023 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.090
wR(F²) = 0.248
S = 1.12
3215 reflections
235 parameters
H-atom parameters constrained
_max = 2.39 e Å^-3
_min = -1.83 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4A-H4AAO1Bⁱ	0.95	2.49	3.314 (10)	145
C5A-H5AABr2ⁱⁱ	0.95	3.04	3.849 (8)	144
C5A-H5AAO2Bⁱ	0.95	2.55	3.409 (11)	150
C6A-H6AAO3Bⁱⁱ	0.95	2.38	3.320 (10)	171
C4B-H4BAO1Aⁱⁱⁱ	0.95	2.56	3.420 (9)	150
C6B-H6BAO3A	0.95	2.35	3.278 (10)	165
Symmetry codes: (i) x-1, y+1, z-1; (ii) x-1, y+1, z; (iii) x, y, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 ).

Acknowledgements

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.

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.
Erian, A. W., Sherif, S. M. & Gaber, H. M. (2003). Molecules, 8, 793-865.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Gupta, M. P. & Prasad, S. M. (1971). Acta Cryst. B27, 1649-1653.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sim, G. A. (1986). Acta Cryst. C42, 1411-1413.
Sutherland, H. H., Hogg, J. H. C. & Williams, D. J. (1974). Acta Cryst. B30, 1562-1565.
Sutherland, H. H. & Hoy, T. G. (1968). Acta Cryst. B24, 1207-1213.
Sutherland, H. H. & Hoy, T. G. (1969). Acta Cryst. B25, 2385-2391.
Yathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o1334-o1335.
Young, D. W., Tollin, P. & Sutherland, H. H. (1968). Acta Cryst. B24, 161-167.

organic compounds