2-Bromo-1-(4-hydroxy­phen­yl)ethanone

Qing, W.-X.; Zhang, W.

doi:10.1107/S1600536809043013

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2837

https://doi.org/10.1107/S1600536809043013

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2-Bromo-1-(4-hydroxyphenyl)ethanone

Wei-Xia Qing ^a ^* and Wei Zhang ^b

^aMedical College of Henan University, Henan University, Kaifeng 475004, People's Republic of China, and ^bDepartment of Pharmacy, Zhengzhou Railway Vocational and Technological College;, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: qingweixia2005@163.com

(Received 15 October 2009; accepted 19 October 2009; online 23 October 2009)

There are two molecules in the asymmetric unit of the title compound, C₈H₇BrO₂. In the crystal, they form independent chains propagating in [010] linked by O—H⋯O hydrogen bonds.

Related literature

For medicinal background, see: Kumar et al. (1997 ).

Experimental

Crystal data

C₈H₇BrO₂
M_r = 215.04
Monoclinic, P 2₁ /c
a = 8.6495 (15) Å
b = 15.052 (3) Å
c = 14.3562 (19) Å
β = 123.224 (7)°
V = 1563.5 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.20 mm⁻¹
T = 293 K
0.38 × 0.34 × 0.29 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.243, T_max = 0.314
7916 measured reflections
3064 independent reflections
1752 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.142
S = 1.03
3064 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	2.02	2.811 (6)	162
O4—H4⋯O3ⁱⁱ	0.82	2.00	2.776 (5)	158
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809043013/hb5143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043013/hb5143Isup2.hkl

checkCIF report

Comment top

The title compound, (I), 2-bromo-1-(4-hydroxyphenyl)ethanone is widely used in the synthesis of adrenaline-type drugs (e.g. Kumar et al., 1997). Herein, we report the crystal structure of the title compound (I).

As shown in Fig.1, the title compound (I) consists of an asymmetric organic molecule. The S(6) ring of C(1)/C(2)/C(3)/C(4)/C(5)/C(6) in (I) is an aromatic ring. In the structure, C(7)–O(1) [1.212 (7) Å] and C(15)–O(3) [1.203 (6) Å] is typical for a C==O double bond, whereas, the C(1)–O(2), and C(9)–O(4) bond distances are of 1.349 (7) and 1.355 (7) Å, respectively (Table 1), indicating two obviously C–O single bonds.

In the crystal structure, these molecules are linked into infinite one-dimensional chains by intermolecular O—H···O hydrogen bonds running along [010] direction (Fig. 2, Table 1).

Related literature top

For medicinal background, see: Kumar et al. (1997).

Experimental top

4-Hydroxyacetophenone (10 g, 73.4 mmol) was dissolved in chloroform (50 ml) at 338 K. With stirring, concentrated sulfuric acid (3.80 ml, 1.84 g/ml) was added in the solution. After stirring for 10 min, bromine (3.9 ml, 76.1 mmol) was added in reaction solution. After 5 h, the solution was quenched with water (60 ml), the layers were separated and the aqueous layer was extracted with chloroform, the combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (30 ml), dried (MgSO₄) and evaporated under reduced pressure to give the crude product. Then purification by short column chromatography (chloroform) and recrystallization from chloroform gave the compound (I) as orange blocks (12.79 g, 81%).

Structure description top

In the crystal structure, these molecules are linked into infinite one-dimensional chains by intermolecular O—H···O hydrogen bonds running along [010] direction (Fig. 2, Table 1).

For medicinal background, see: Kumar et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. One-dimensional structure of (I) along [010] direction, Hydrogen bonds are shown as dashed lines.

2-Bromo-1-(4-hydroxyphenyl)ethanone top

Crystal data top

C₈H₇BrO₂	F(000) = 848
M_r = 215.04	D_x = 1.827 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1628 reflections
a = 8.6495 (15) Å	θ = 2.7–23.1°
b = 15.052 (3) Å	µ = 5.20 mm⁻¹
c = 14.3562 (19) Å	T = 293 K
β = 123.224 (7)°	Block, orange
V = 1563.5 (5) Å³	0.38 × 0.34 × 0.29 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3064 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→10
T_min = 0.243, T_max = 0.314	k = −18→18
7916 measured reflections	l = −17→17

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0679P)² + 0.3873P] where P = (F_o² + 2F_c²)/3
3064 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

C₈H₇BrO₂	V = 1563.5 (5) Å³
M_r = 215.04	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6495 (15) Å	µ = 5.20 mm⁻¹
b = 15.052 (3) Å	T = 293 K
c = 14.3562 (19) Å	0.38 × 0.34 × 0.29 mm
β = 123.224 (7)°

Data collection top

Bruker SMART CCD diffractometer	3064 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1752 reflections with I > 2σ(I)
T_min = 0.243, T_max = 0.314	R_int = 0.058
7916 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
3064 reflections	Δρ_min = −0.79 e Å⁻³
199 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.93107 (10)	0.53760 (4)	0.71841 (6)	0.0609 (3)
O1	0.9475 (6)	0.3392 (2)	0.7394 (4)	0.0546 (12)
O2	0.2872 (6)	0.0898 (2)	0.4104 (3)	0.0546 (12)
H2	0.1818	0.1092	0.3705	0.082*
C1	0.4050 (9)	0.1575 (4)	0.4654 (5)	0.0412 (15)
C2	0.5763 (8)	0.1372 (4)	0.5584 (5)	0.0401 (15)
H2A	0.6070	0.0781	0.5797	0.048*
C3	0.7014 (8)	0.2024 (3)	0.6197 (5)	0.0371 (14)
H3A	0.8141	0.1872	0.6837	0.044*
C4	0.6631 (8)	0.2913 (3)	0.5878 (4)	0.0326 (13)
C5	0.4910 (9)	0.3105 (4)	0.4922 (5)	0.0426 (15)
H5A	0.4612	0.3693	0.4695	0.051*
C6	0.3633 (9)	0.2450 (4)	0.4300 (5)	0.0409 (15)
H6A	0.2509	0.2594	0.3653	0.049*
C7	0.7990 (9)	0.3582 (3)	0.6569 (5)	0.0375 (14)
C8	0.7466 (9)	0.4533 (3)	0.6211 (5)	0.0398 (15)
H8A	0.6330	0.4665	0.6167	0.048*
H8B	0.7223	0.4603	0.5470	0.048*
Br2	1.06321 (10)	0.28455 (5)	1.05320 (6)	0.0680 (3)
O3	0.6801 (6)	0.2668 (2)	0.8479 (3)	0.0446 (11)
O4	0.1884 (6)	0.5955 (2)	0.5816 (3)	0.0489 (11)
H4	0.2337	0.6450	0.5896	0.073*
C9	0.3201 (9)	0.5383 (4)	0.6552 (5)	0.0393 (15)
C10	0.2821 (9)	0.4486 (4)	0.6349 (5)	0.0456 (16)
H10A	0.1697	0.4297	0.5734	0.055*
C11	0.4103 (8)	0.3883 (4)	0.7055 (5)	0.0445 (16)
H11A	0.3822	0.3281	0.6922	0.053*
C12	0.5815 (8)	0.4134 (3)	0.7966 (4)	0.0310 (13)
C13	0.6156 (9)	0.5033 (4)	0.8149 (5)	0.0391 (14)
H13A	0.7271	0.5224	0.8770	0.047*
C14	0.4887 (9)	0.5657 (4)	0.7435 (5)	0.0388 (15)
H14A	0.5174	0.6259	0.7552	0.047*
C15	0.7123 (8)	0.3449 (4)	0.8668 (5)	0.0357 (14)
C16	0.8958 (8)	0.3773 (4)	0.9621 (5)	0.0430 (15)
H16A	0.8753	0.4158	1.0085	0.052*
H16B	0.9534	0.4126	0.9326	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0530 (5)	0.0346 (4)	0.0735 (5)	−0.0082 (3)	0.0209 (4)	−0.0036 (3)
O1	0.035 (3)	0.035 (2)	0.050 (3)	0.003 (2)	−0.005 (3)	0.000 (2)
O2	0.042 (3)	0.033 (2)	0.060 (3)	−0.009 (2)	0.010 (2)	−0.004 (2)
C1	0.044 (4)	0.038 (4)	0.043 (4)	−0.001 (3)	0.024 (4)	−0.003 (3)
C2	0.044 (4)	0.026 (3)	0.042 (4)	0.008 (3)	0.018 (4)	0.006 (3)
C3	0.032 (3)	0.027 (3)	0.040 (3)	0.007 (3)	0.012 (3)	0.005 (3)
C4	0.033 (3)	0.029 (3)	0.030 (3)	0.005 (3)	0.014 (3)	0.002 (2)
C5	0.045 (4)	0.026 (3)	0.047 (4)	0.007 (3)	0.019 (4)	0.005 (3)
C6	0.038 (4)	0.027 (3)	0.037 (3)	0.004 (3)	0.007 (3)	0.006 (3)
C7	0.043 (4)	0.028 (3)	0.039 (4)	−0.004 (3)	0.021 (4)	−0.005 (3)
C8	0.044 (4)	0.027 (3)	0.038 (3)	0.000 (3)	0.015 (3)	0.000 (2)
Br2	0.0486 (5)	0.0459 (4)	0.0771 (6)	0.0048 (3)	0.0138 (4)	0.0072 (3)
O3	0.052 (3)	0.018 (2)	0.047 (2)	−0.0043 (19)	0.017 (2)	0.0005 (17)
O4	0.043 (3)	0.027 (2)	0.057 (3)	0.005 (2)	0.015 (2)	0.0044 (19)
C9	0.045 (4)	0.035 (3)	0.040 (4)	0.000 (3)	0.025 (4)	−0.001 (3)
C10	0.039 (4)	0.032 (3)	0.050 (4)	−0.008 (3)	0.014 (3)	−0.005 (3)
C11	0.045 (4)	0.024 (3)	0.054 (4)	−0.005 (3)	0.021 (4)	−0.001 (3)
C12	0.036 (4)	0.023 (3)	0.029 (3)	−0.002 (3)	0.015 (3)	−0.002 (2)
C13	0.037 (4)	0.034 (3)	0.033 (3)	−0.001 (3)	0.010 (3)	−0.004 (3)
C14	0.043 (4)	0.022 (3)	0.041 (4)	−0.004 (3)	0.016 (4)	−0.009 (3)
C15	0.038 (4)	0.033 (3)	0.036 (3)	−0.002 (3)	0.020 (3)	0.001 (3)
C16	0.046 (4)	0.027 (3)	0.042 (4)	−0.003 (3)	0.016 (4)	0.001 (3)

Geometric parameters (Å, º) top

Br1—C8	1.915 (6)	Br2—C16	1.918 (6)
O1—C7	1.212 (7)	O3—C15	1.203 (6)
O2—C1	1.349 (7)	O4—C9	1.355 (7)
O2—H2	0.8200	O4—H4	0.8199
C1—C2	1.380 (8)	C9—C14	1.370 (9)
C1—C6	1.387 (8)	C9—C10	1.382 (8)
C2—C3	1.366 (8)	C10—C11	1.360 (8)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.395 (7)	C11—C12	1.387 (7)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.395 (8)	C12—C13	1.379 (8)
C4—C7	1.449 (8)	C12—C15	1.453 (7)
C5—C6	1.381 (8)	C13—C14	1.380 (8)
C5—H5A	0.9300	C13—H13A	0.9300
C6—H6A	0.9300	C14—H14A	0.9300
C7—C8	1.504 (7)	C15—C16	1.500 (8)
C8—H8A	0.9700	C16—H16A	0.9700
C8—H8B	0.9700	C16—H16B	0.9700

C1—O2—H2	109.5	C9—O4—H4	109.6
O2—C1—C2	117.7 (5)	O4—C9—C14	122.9 (5)
O2—C1—C6	122.8 (6)	O4—C9—C10	117.1 (6)
C2—C1—C6	119.4 (6)	C14—C9—C10	119.9 (6)
C3—C2—C1	121.0 (5)	C11—C10—C9	119.5 (6)
C3—C2—H2A	119.5	C11—C10—H10A	120.3
C1—C2—H2A	119.5	C9—C10—H10A	120.3
C2—C3—C4	121.1 (5)	C10—C11—C12	122.2 (5)
C2—C3—H3A	119.4	C10—C11—H11A	118.9
C4—C3—H3A	119.4	C12—C11—H11A	118.9
C5—C4—C3	117.1 (5)	C13—C12—C11	117.0 (5)
C5—C4—C7	123.9 (5)	C13—C12—C15	124.1 (5)
C3—C4—C7	119.0 (5)	C11—C12—C15	118.9 (5)
C6—C5—C4	122.2 (5)	C12—C13—C14	121.7 (6)
C6—C5—H5A	118.9	C12—C13—H13A	119.1
C4—C5—H5A	118.9	C14—C13—H13A	119.1
C5—C6—C1	119.0 (6)	C9—C14—C13	119.5 (5)
C5—C6—H6A	120.5	C9—C14—H14A	120.2
C1—C6—H6A	120.5	C13—C14—H14A	120.2
O1—C7—C4	122.2 (5)	O3—C15—C12	122.7 (5)
O1—C7—C8	121.2 (5)	O3—C15—C16	121.4 (5)
C4—C7—C8	116.6 (5)	C12—C15—C16	115.7 (5)
C7—C8—Br1	114.0 (4)	C15—C16—Br2	114.3 (4)
C7—C8—H8A	108.8	C15—C16—H16A	108.7
Br1—C8—H8A	108.8	Br2—C16—H16A	108.7
C7—C8—H8B	108.8	C15—C16—H16B	108.7
Br1—C8—H8B	108.8	Br2—C16—H16B	108.7
H8A—C8—H8B	107.6	H16A—C16—H16B	107.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.02	2.811 (6)	162
O4—H4···O3ⁱⁱ	0.82	2.00	2.776 (5)	158

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₇BrO₂
M_r	215.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.6495 (15), 15.052 (3), 14.3562 (19)
β (°)	123.224 (7)
V (Å³)	1563.5 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.20
Crystal size (mm)	0.38 × 0.34 × 0.29

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.243, 0.314
No. of measured, independent and observed [I > 2σ(I)] reflections	7916, 3064, 1752
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.142, 1.03
No. of reflections	3064
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.79

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.02	2.811 (6)	162
O4—H4···O3ⁱⁱ	0.82	2.00	2.776 (5)	158

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2.

References

Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Kumar, A., Rane, R. A., Ravindran, V. K. & Dike, S. Y. (1997). Synth. Commun. 27, 1133–1141. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page o2837

https://doi.org/10.1107/S1600536809043013

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