2-Bromo-1-(4-methoxy-phen-yl)ethanone.

The title compound, C(9)H(9)BrO(2), prepared by the reaction of 4-methoxy-acetophenone and cupric bromide, , is approximately planar (r.m.s. deviation 0.0008 Å). In the crystal, weak inter-molecular aromatic C-H⋯O(carbon-yl) hydrogen-bonding inter-actions result in a one-dimensional chain structure.

Related literature

For background to hydrazone compounds, see: Domiano et al. (1984 ▶); Li et al. (1988 ▶); Sadik et al. (2004 ▶). For background to thia­zole compounds, see: Shinagawa et al. (1997 ▶); Shivarama et al.(2003 ▶); Dinçer et al. (2005 ▶); Zhang et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H9BrO2

M = 229.06

Monoclinic,

a = 7.7360 (15) Å

b = 12.441 (3) Å

c = 10.048 (2) Å

β = 111.42 (3)°

V = 900.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 4.52 mm−1

T = 305 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.465, T max = 0.661

1634 measured reflections

1634 independent reflections

924 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: 9%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.116

S = 1.01

1634 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.53 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033303/zs2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033303/zs2006Isup2.hkl

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

C9H9BrO2	F(000) = 456
Mr = 229.06	Dx = 1.690 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27 reflections
a = 7.7360 (15) Å	θ = 1–25°
b = 12.441 (3) Å	µ = 4.52 mm−1
c = 10.048 (2) Å	T = 305 K
β = 111.42 (3)°	Block, colorless
V = 900.3 (4) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	924 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 2.7°
ω/2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.465, Tmax = 0.661	l = 0→12
1634 measured reflections	3 standard reflections every 200 reflections
1634 independent reflections	intensity decay: 9%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
1634 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Br	0.20597 (10)	0.66539 (6)	0.07859 (7)	0.0717 (3)
O1	0.3621 (7)	0.8754 (4)	0.2083 (5)	0.0848 (15)
C1	0.1809 (8)	0.8016 (5)	−0.0164 (6)	0.0576 (17)
H1A	0.2308	0.7957	−0.0918	0.069*
H1B	0.0500	0.8190	−0.0608	0.069*
O2	0.2187 (6)	1.3075 (4)	−0.1487 (5)	0.0689 (13)
C2	0.2781 (8)	0.8917 (5)	0.0820 (6)	0.0534 (16)
C3	0.2657 (7)	0.9994 (5)	0.0181 (6)	0.0478 (14)
C4	0.1597 (8)	1.0221 (5)	−0.1242 (6)	0.0593 (17)
H4A	0.0957	0.9671	−0.1849	0.071*
C5	0.1493 (9)	1.1250 (5)	−0.1751 (7)	0.0633 (18)
H5A	0.0780	1.1390	−0.2703	0.076*
C6	0.2432 (8)	1.2086 (5)	−0.0870 (7)	0.0538 (16)
C7	0.3497 (8)	1.1859 (5)	0.0560 (7)	0.0600 (17)
H7A	0.4138	1.2406	0.1172	0.072*
C8	0.3586 (8)	1.0831 (5)	0.1051 (6)	0.0564 (16)
H8A	0.4297	1.0688	0.2003	0.068*
C9	0.2906 (10)	1.3980 (6)	−0.0610 (8)	0.083 (2)
H9A	0.2625	1.4618	−0.1186	0.124*
H9B	0.4227	1.3908	−0.0151	0.124*
H9C	0.2353	1.4028	0.0102	0.124*

	U11	U22	U33	U12	U13	U23
Br	0.0721 (5)	0.0588 (5)	0.0722 (5)	0.0064 (4)	0.0121 (3)	0.0076 (4)
O1	0.104 (4)	0.067 (3)	0.050 (3)	0.002 (3)	−0.011 (3)	0.003 (2)
C1	0.054 (4)	0.060 (4)	0.050 (3)	0.002 (3)	0.008 (3)	−0.003 (3)
O2	0.079 (3)	0.054 (3)	0.070 (3)	−0.007 (2)	0.021 (2)	−0.002 (2)
C2	0.042 (3)	0.060 (4)	0.049 (4)	0.007 (3)	0.006 (3)	−0.005 (3)
C3	0.036 (3)	0.050 (4)	0.053 (4)	−0.001 (3)	0.011 (3)	−0.003 (3)
C4	0.060 (4)	0.056 (4)	0.049 (3)	−0.002 (3)	0.005 (3)	−0.012 (3)
C5	0.067 (4)	0.059 (4)	0.052 (4)	0.005 (4)	0.007 (3)	0.000 (3)
C6	0.047 (4)	0.056 (4)	0.058 (4)	−0.004 (3)	0.018 (3)	−0.007 (3)
C7	0.054 (4)	0.062 (5)	0.058 (4)	−0.011 (3)	0.013 (3)	−0.010 (3)
C8	0.044 (4)	0.064 (4)	0.049 (3)	−0.004 (3)	0.001 (3)	−0.005 (3)
C9	0.087 (5)	0.063 (5)	0.096 (5)	−0.012 (4)	0.031 (4)	−0.004 (4)

Br—C1	1.920 (6)	C4—H4A	0.9300
O1—C2	1.213 (6)	C5—C6	1.387 (8)
C1—C2	1.502 (8)	C5—H5A	0.9300
C1—H1A	0.9700	C6—C7	1.400 (8)
C1—H1B	0.9700	C7—C8	1.363 (8)
O2—C6	1.359 (7)	C7—H7A	0.9300
O2—C9	1.412 (8)	C8—H8A	0.9300
C2—C3	1.474 (8)	C9—H9A	0.9600
C3—C8	1.380 (7)	C9—H9B	0.9600
C3—C4	1.393 (8)	C9—H9C	0.9600
C4—C5	1.370 (8)
C2—C1—Br	113.3 (4)	C4—C5—H5A	119.4
C2—C1—H1A	108.9	C6—C5—H5A	119.4
Br—C1—H1A	108.9	O2—C6—C5	115.8 (5)
C2—C1—H1B	108.9	O2—C6—C7	125.6 (6)
Br—C1—H1B	108.9	C5—C6—C7	118.6 (6)
H1A—C1—H1B	107.7	C8—C7—C6	119.6 (6)
C6—O2—C9	118.7 (5)	C8—C7—H7A	120.2
O1—C2—C3	122.1 (6)	C6—C7—H7A	120.2
O1—C2—C1	120.8 (6)	C7—C8—C3	122.2 (6)
C3—C2—C1	117.0 (5)	C7—C8—H8A	118.9
C8—C3—C4	118.2 (6)	C3—C8—H8A	118.9
C8—C3—C2	118.3 (5)	O2—C9—H9A	109.5
C4—C3—C2	123.4 (6)	O2—C9—H9B	109.5
C5—C4—C3	120.3 (6)	H9A—C9—H9B	109.5
C5—C4—H4A	119.9	O2—C9—H9C	109.5
C3—C4—H4A	119.9	H9A—C9—H9C	109.5
C4—C5—C6	121.2 (6)	H9B—C9—H9C	109.5
Br—C1—C2—O1	0.0 (8)	C9—O2—C6—C5	172.0 (6)
Br—C1—C2—C3	−179.8 (4)	C9—O2—C6—C7	−6.3 (9)
O1—C2—C3—C8	2.2 (9)	C4—C5—C6—O2	−178.5 (6)
C1—C2—C3—C8	−178.0 (5)	C4—C5—C6—C7	0.0 (9)
O1—C2—C3—C4	−175.3 (6)	O2—C6—C7—C8	178.3 (6)
C1—C2—C3—C4	4.5 (9)	C5—C6—C7—C8	0.0 (9)
C8—C3—C4—C5	0.1 (9)	C6—C7—C8—C3	0.0 (9)
C2—C3—C4—C5	177.6 (6)	C4—C3—C8—C7	−0.1 (9)
C3—C4—C5—C6	0.0 (10)	C2—C3—C8—C7	−177.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.93	2.47	2.780 (8)	100
C7—H7A···O1i	0.93	2.58	3.505 (7)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1i	0.93	2.58	3.505 (7)	171

Symmetry code: (i) .