4-(5-Bromo-2-hydroxy-phen-yl)but-3-ene-2-one.

The molecule of the title compound, C(10)H(9)BrO(2), a doubly conjugated unsaturated ketone, is almost planar (r.m.s. deviation of the non-H atoms = 0.039 Å). In the crystal structure, two mol-ecules are linked across a centre of inversion to form a hydrogen-bonded dimer by way of two O-H⋯O links.

Related literature

The reactivity of doubly conjugated unsaturated ketones has been known for a long time; see: Buck & Heilbron (1922 ▶); Marvel et al. (1953 ▶). Their utility is discussed by Trost & Fleming (1991 ▶).

Experimental

Crystal data

C10H9BrO2

M = 241.08

Triclinic,

a = 5.8619 (2) Å

b = 7.7495 (2) Å

c = 10.9601 (3) Å

α = 106.432 (2)°

β = 104.548 (2)°

γ = 94.468 (2)°

V = 456.25 (2) Å3

Z = 2

Mo Kα radiation

μ = 4.47 mm−1

T = 123 K

0.40 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.268, T max = 0.916

3659 measured reflections

2040 independent reflections

1797 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.074

S = 1.04

2040 reflections

123 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009386/bt2898sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009386/bt2898Isup2.hkl

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

C10H9BrO2	Z = 2
Mr = 241.08	F(000) = 240
Triclinic, P1	Dx = 1.755 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8619 (2) Å	Cell parameters from 1830 reflections
b = 7.7495 (2) Å	θ = 2.8–28.1°
c = 10.9601 (3) Å	µ = 4.47 mm−1
α = 106.432 (2)°	T = 123 K
β = 104.548 (2)°	Plate, colorless
γ = 94.468 (2)°	0.40 × 0.10 × 0.02 mm
V = 456.25 (2) Å3

Bruker SMART APEX diffractometer	2040 independent reflections
Radiation source: fine-focus sealed tube	1797 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.268, Tmax = 0.916	k = −10→9
3659 measured reflections	l = −14→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0287P)2 + 0.4716P] where P = (Fo2 + 2Fc2)/3
2040 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.66 e Å−3
1 restraint	Δρmin = −0.58 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.69822 (5)	0.19383 (4)	−0.18504 (3)	0.02165 (11)
O1	0.3724 (4)	0.3898 (3)	0.3090 (2)	0.0231 (5)
H1	0.256 (4)	0.319 (4)	0.307 (4)	0.033 (11)*
O2	0.9820 (4)	0.8201 (3)	0.6596 (2)	0.0226 (5)
C1	0.4405 (5)	0.3456 (4)	0.1967 (3)	0.0173 (6)
C2	0.2974 (5)	0.2178 (4)	0.0796 (3)	0.0188 (6)
H2	0.1468	0.1611	0.0782	0.023*
C3	0.3699 (5)	0.1715 (4)	−0.0348 (3)	0.0192 (6)
H3	0.2722	0.0828	−0.1138	0.023*
C4	0.5894 (5)	0.2583 (4)	−0.0309 (3)	0.0173 (6)
C5	0.7326 (5)	0.3867 (4)	0.0822 (3)	0.0168 (6)
H5	0.8812	0.4441	0.0815	0.020*
C6	0.6617 (5)	0.4341 (4)	0.1992 (3)	0.0166 (6)
C7	0.8291 (5)	0.5694 (4)	0.3152 (3)	0.0178 (6)
H7	0.9703	0.6173	0.3004	0.021*
C8	0.8136 (5)	0.6359 (4)	0.4390 (3)	0.0180 (6)
H8	0.6731	0.5958	0.4582	0.022*
C10	1.2237 (6)	0.8416 (4)	0.5192 (3)	0.0248 (7)
H10A	1.3292	0.9287	0.6014	0.037*
H10B	1.1786	0.9032	0.4521	0.037*
H10C	1.3071	0.7412	0.4868	0.037*
C9	1.0023 (5)	0.7671 (4)	0.5460 (3)	0.0177 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.02299 (17)	0.02469 (17)	0.01502 (15)	−0.00029 (11)	0.00787 (11)	0.00169 (11)
O1	0.0206 (11)	0.0277 (12)	0.0199 (11)	−0.0035 (9)	0.0101 (9)	0.0037 (9)
O2	0.0263 (12)	0.0215 (11)	0.0178 (10)	−0.0001 (9)	0.0082 (9)	0.0025 (9)
C1	0.0201 (15)	0.0182 (14)	0.0161 (14)	0.0048 (11)	0.0067 (12)	0.0073 (11)
C2	0.0198 (15)	0.0189 (14)	0.0195 (14)	0.0013 (12)	0.0071 (12)	0.0080 (12)
C3	0.0196 (15)	0.0188 (14)	0.0160 (14)	0.0021 (12)	0.0023 (12)	0.0035 (11)
C4	0.0213 (15)	0.0173 (14)	0.0165 (13)	0.0068 (12)	0.0099 (12)	0.0054 (11)
C5	0.0147 (14)	0.0193 (14)	0.0189 (14)	0.0032 (11)	0.0066 (11)	0.0079 (11)
C6	0.0179 (14)	0.0157 (14)	0.0158 (13)	0.0031 (11)	0.0047 (11)	0.0047 (11)
C7	0.0157 (14)	0.0193 (14)	0.0189 (14)	0.0026 (11)	0.0043 (12)	0.0074 (12)
C8	0.0153 (14)	0.0181 (14)	0.0205 (14)	0.0011 (11)	0.0057 (12)	0.0056 (12)
C10	0.0215 (16)	0.0251 (16)	0.0223 (15)	−0.0054 (13)	0.0070 (13)	0.0005 (13)
C9	0.0205 (15)	0.0150 (14)	0.0179 (14)	0.0025 (11)	0.0059 (12)	0.0056 (11)

Br1—C4	1.903 (3)	C5—C6	1.406 (4)
O1—C1	1.350 (3)	C5—H5	0.9500
O1—H1	0.834 (10)	C6—C7	1.461 (4)
O2—C9	1.235 (3)	C7—C8	1.338 (4)
C1—C2	1.394 (4)	C7—H7	0.9500
C1—C6	1.409 (4)	C8—C9	1.460 (4)
C2—C3	1.385 (4)	C8—H8	0.9500
C2—H2	0.9500	C10—C9	1.508 (4)
C3—C4	1.390 (4)	C10—H10A	0.9800
C3—H3	0.9500	C10—H10B	0.9800
C4—C5	1.371 (4)	C10—H10C	0.9800
C1—O1—H1	114 (3)	C5—C6—C7	116.5 (3)
O1—C1—C2	121.9 (3)	C1—C6—C7	125.4 (3)
O1—C1—C6	118.3 (3)	C8—C7—C6	129.8 (3)
C2—C1—C6	119.8 (3)	C8—C7—H7	115.1
C3—C2—C1	121.5 (3)	C6—C7—H7	115.1
C3—C2—H2	119.2	C7—C8—C9	123.1 (3)
C1—C2—H2	119.2	C7—C8—H8	118.5
C2—C3—C4	118.2 (3)	C9—C8—H8	118.5
C2—C3—H3	120.9	C9—C10—H10A	109.5
C4—C3—H3	120.9	C9—C10—H10B	109.5
C5—C4—C3	121.6 (3)	H10A—C10—H10B	109.5
C5—C4—Br1	119.0 (2)	C9—C10—H10C	109.5
C3—C4—Br1	119.3 (2)	H10A—C10—H10C	109.5
C4—C5—C6	120.7 (3)	H10B—C10—H10C	109.5
C4—C5—H5	119.6	O2—C9—C8	120.5 (3)
C6—C5—H5	119.6	O2—C9—C10	119.0 (3)
C5—C6—C1	118.1 (3)	C8—C9—C10	120.5 (3)
O1—C1—C2—C3	−179.2 (2)	O1—C1—C6—C5	179.6 (2)
C6—C1—C2—C3	1.6 (4)	C2—C1—C6—C5	−1.2 (4)
C1—C2—C3—C4	−1.0 (4)	O1—C1—C6—C7	1.2 (4)
C2—C3—C4—C5	0.0 (4)	C2—C1—C6—C7	−179.5 (3)
C2—C3—C4—Br1	178.5 (2)	C5—C6—C7—C8	−177.8 (3)
C3—C4—C5—C6	0.4 (4)	C1—C6—C7—C8	0.6 (5)
Br1—C4—C5—C6	−178.10 (19)	C6—C7—C8—C9	177.6 (3)
C4—C5—C6—C1	0.2 (4)	C7—C8—C9—O2	−177.8 (3)
C4—C5—C6—C7	178.7 (2)	C7—C8—C9—C10	2.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.83 (1)	1.87 (1)	2.689 (3)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.83 (1)	1.87 (1)	2.689 (3)	168 (4)

Symmetry code: (i) .