1-(5-Bromo-1-benzofuran-2-yl)ethanone.

The title compound, C(10)H(7)BrO(2), is approximately planar (r.m.s. deviation = 0.057 Å for the 13 non-H atoms). In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into C(5) chains propagating in [100].

Related literature

For general background to and the biological activity of benzofuran derivatives, see: Abdel-Aziz et al. (2009 ▶); Abdel-Aziz & Mekawey (2009 ▶); Bhovi et al. (2009 ▶); Abdel-Wahab et al. (2009 ▶); Csaba et al. (2003 ▶); Bevinakatti & Badiger (1982 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H7BrO2

M = 239.07

Orthorhombic,

a = 10.8301 (2) Å

b = 7.4630 (1) Å

c = 21.7213 (3) Å

V = 1755.62 (5) Å3

Z = 8

Mo Kα radiation

μ = 4.64 mm−1

T = 100 K

0.26 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.377, T max = 0.482

43601 measured reflections

3331 independent reflections

2689 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.058

S = 1.04

3331 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201985X/hb6772sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201985X/hb6772Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201985X/hb6772Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H7BrO2	F(000) = 944
Mr = 239.07	Dx = 1.809 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9929 reflections
a = 10.8301 (2) Å	θ = 2.7–33.1°
b = 7.4630 (1) Å	µ = 4.64 mm−1
c = 21.7213 (3) Å	T = 100 K
V = 1755.62 (5) Å3	Block, colourless
Z = 8	0.26 × 0.19 × 0.18 mm

Bruker SMART APEXII DUO CCD diffractometer	3331 independent reflections
Radiation source: fine-focus sealed tube	2689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 33.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.377, Tmax = 0.482	k = −11→10
43601 measured reflections	l = −33→33

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0251P)2 + 1.0553P] where P = (Fo2 + 2Fc2)/3
3331 reflections	(Δ/σ)max = 0.002
119 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.176439 (12)	0.162250 (19)	0.544115 (6)	0.01904 (5)
O1	0.36814 (9)	−0.10002 (14)	0.30247 (4)	0.01671 (18)
O2	0.36732 (9)	−0.25959 (15)	0.18927 (5)	0.0228 (2)
C1	0.33614 (11)	−0.03183 (18)	0.35866 (6)	0.0153 (2)
C2	0.41792 (12)	0.03133 (19)	0.40293 (6)	0.0177 (3)
H2A	0.5045	0.0339	0.3961	0.021*
C3	0.36627 (13)	0.09040 (19)	0.45760 (6)	0.0176 (2)
H3A	0.4182	0.1340	0.4895	0.021*
C4	0.23784 (12)	0.08646 (19)	0.46632 (6)	0.0163 (2)
C5	0.15642 (12)	0.02766 (19)	0.42185 (6)	0.0169 (2)
H5A	0.0697	0.0287	0.4285	0.020*
C6	0.20783 (12)	−0.03389 (18)	0.36629 (6)	0.0151 (2)
C7	0.15886 (12)	−0.10978 (19)	0.31084 (6)	0.0165 (2)
H7A	0.0743	−0.1294	0.3013	0.020*
C8	0.25797 (12)	−0.14821 (19)	0.27452 (6)	0.0161 (2)
C9	0.26702 (12)	−0.23368 (19)	0.21372 (6)	0.0171 (2)
C10	0.14699 (13)	−0.2835 (2)	0.18369 (7)	0.0214 (3)
H10D	0.1630	−0.3645	0.1491	0.032*
H10A	0.1059	−0.1750	0.1686	0.032*
H10B	0.0937	−0.3436	0.2138	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.02043 (7)	0.02101 (8)	0.01568 (7)	0.00053 (5)	0.00383 (5)	0.00000 (5)
O1	0.0123 (4)	0.0231 (5)	0.0147 (4)	−0.0003 (4)	0.0008 (3)	−0.0005 (4)
O2	0.0171 (4)	0.0314 (6)	0.0200 (5)	0.0005 (4)	0.0031 (4)	−0.0025 (4)
C1	0.0133 (5)	0.0173 (6)	0.0152 (5)	0.0004 (4)	0.0014 (4)	0.0025 (5)
C2	0.0133 (5)	0.0216 (7)	0.0180 (6)	0.0002 (5)	−0.0002 (5)	0.0007 (5)
C3	0.0157 (5)	0.0190 (6)	0.0183 (6)	0.0003 (5)	−0.0021 (5)	0.0011 (5)
C4	0.0179 (6)	0.0168 (6)	0.0141 (5)	0.0006 (5)	0.0029 (4)	0.0020 (5)
C5	0.0144 (6)	0.0182 (6)	0.0182 (6)	−0.0003 (5)	0.0019 (4)	0.0018 (5)
C6	0.0136 (5)	0.0168 (6)	0.0149 (5)	−0.0002 (5)	0.0008 (4)	0.0028 (5)
C7	0.0134 (5)	0.0192 (6)	0.0170 (6)	−0.0004 (5)	−0.0008 (4)	0.0022 (5)
C8	0.0132 (5)	0.0183 (6)	0.0167 (5)	−0.0005 (5)	−0.0008 (4)	0.0031 (5)
C9	0.0169 (6)	0.0178 (6)	0.0167 (6)	0.0002 (5)	−0.0003 (5)	0.0028 (5)
C10	0.0176 (6)	0.0277 (7)	0.0187 (6)	0.0001 (6)	−0.0028 (5)	−0.0001 (6)

Br1—C4	1.9020 (13)	C5—C6	1.4062 (18)
O1—C1	1.3669 (16)	C5—H5A	0.9500
O1—C8	1.3862 (16)	C6—C7	1.4327 (19)
O2—C9	1.2245 (17)	C7—C8	1.3626 (18)
C1—C2	1.3898 (18)	C7—H7A	0.9500
C1—C6	1.3995 (18)	C8—C9	1.4699 (19)
C2—C3	1.3847 (19)	C9—C10	1.5013 (19)
C2—H2A	0.9500	C10—H10D	0.9800
C3—C4	1.4041 (19)	C10—H10A	0.9800
C3—H3A	0.9500	C10—H10B	0.9800
C4—C5	1.3795 (19)
C1—O1—C8	105.63 (10)	C1—C6—C7	105.80 (11)
O1—C1—C2	125.63 (11)	C5—C6—C7	134.76 (12)
O1—C1—C6	110.70 (11)	C8—C7—C6	106.16 (11)
C2—C1—C6	123.67 (12)	C8—C7—H7A	126.9
C3—C2—C1	116.36 (12)	C6—C7—H7A	126.9
C3—C2—H2A	121.8	C7—C8—O1	111.71 (12)
C1—C2—H2A	121.8	C7—C8—C9	131.61 (12)
C2—C3—C4	120.61 (13)	O1—C8—C9	116.66 (11)
C2—C3—H3A	119.7	O2—C9—C8	121.15 (12)
C4—C3—H3A	119.7	O2—C9—C10	122.72 (13)
C5—C4—C3	123.05 (12)	C8—C9—C10	116.12 (12)
C5—C4—Br1	119.55 (10)	C9—C10—H10D	109.5
C3—C4—Br1	117.38 (10)	C9—C10—H10A	109.5
C4—C5—C6	116.86 (12)	H10D—C10—H10A	109.5
C4—C5—H5A	121.6	C9—C10—H10B	109.5
C6—C5—H5A	121.6	H10D—C10—H10B	109.5
C1—C6—C5	119.42 (12)	H10A—C10—H10B	109.5
C8—O1—C1—C2	179.08 (13)	C4—C5—C6—C1	−0.3 (2)
C8—O1—C1—C6	−0.81 (15)	C4—C5—C6—C7	177.41 (15)
O1—C1—C2—C3	−178.27 (13)	C1—C6—C7—C8	0.26 (15)
C6—C1—C2—C3	1.6 (2)	C5—C6—C7—C8	−177.71 (15)
C1—C2—C3—C4	−0.5 (2)	C6—C7—C8—O1	−0.78 (16)
C2—C3—C4—C5	−1.0 (2)	C6—C7—C8—C9	177.28 (14)
C2—C3—C4—Br1	177.76 (11)	C1—O1—C8—C7	1.00 (15)
C3—C4—C5—C6	1.4 (2)	C1—O1—C8—C9	−177.38 (12)
Br1—C4—C5—C6	−177.32 (10)	C7—C8—C9—O2	−178.33 (15)
O1—C1—C6—C5	178.69 (12)	O1—C8—C9—O2	−0.3 (2)
C2—C1—C6—C5	−1.2 (2)	C7—C8—C9—C10	2.6 (2)
O1—C1—C6—C7	0.35 (15)	O1—C8—C9—C10	−179.41 (12)
C2—C1—C6—C7	−179.53 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.95	2.45	3.3495 (16)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.95	2.45	3.3495 (16)	158

Symmetry code: (i) .