2,6-Dibromo-4-(2-hy­droxy­eth­yl)phenol

Lu, D.; Chai, H.; Ling, X.; Chen, J.; Wang, J.

doi:10.1107/S1600536811046538

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3263-o3264

https://doi.org/10.1107/S1600536811046538

Open

access

2,6-Dibromo-4-(2-hydroxyethyl)phenol

Ding-qiang Lu,^a ^* Hong Chai,^a Xiu-quan Ling,^a Jia Chen ^a and Jia-li Wang ^b

^aState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wangzhe_guilai@126.com

(Received 1 November 2011; accepted 4 November 2011; online 12 November 2011)

The title compound, C₈H₈Br₂O₂, crystallized with two independent molecules (A and B) in the asymmetric unit. They differ in the conformation of the 2-hydroxyethyl chain with the C—C—C—O torsion angle being −68.0 (12)° in molecule A and 172.2 (9)° in molecule B. In the crystal, the A molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers, while the B molecules are linked via an O—H⋯O hydrogen bond, forming a polymeric chain propagating in [010]. In addition, there are O—H⋯O and O—H⋯Br hydrogen bonds, and Br⋯Br [3.599 (2) Å] and π–π interactions [centroid–centroid distances = 3.581 (6) and 3.931 (6) Å], leading to the formation of a two-dimensional network parallel to (001).

Related literature

For background and further synthetic details, see: Guerard et al. (2009 ); Bovicelli et al. (2007 ). For standard bond-length data, see: Allen et al. (1987 ). For a related structure, see: Zhu et al. (2011 )

Experimental

Crystal data

C₈H₈Br₂O₂
M_r = 295.94
Triclinic, $[P \overline 1]$
a = 8.5740 (17) Å
b = 9.845 (2) Å
c = 11.392 (2) Å
α = 86.08 (3)°
β = 75.79 (3)°
γ = 87.39 (3)°
V = 929.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 8.68 mm⁻¹
T = 293 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 = 0.276, T_max = 0.478
3664 measured reflections
3416 independent reflections
1874 reflections with I > 2σ(I)
R_int = 0.087
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.161
S = 1.00
3416 reflections
217 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.82	1.93	2.665 (11)	149
O4—H4O⋯O3ⁱⁱ	0.85	2.09	2.837 (9)	146
O2—H2O⋯O4ⁱⁱⁱ	0.82	2.09	2.896 (10)	168
O3—H3O⋯Br2^iv	0.85	2.55	3.291 (7)	147
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) x+1, y-1, z-1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046538/su2342sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046538/su2342Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046538/su2342Isup3.cml

checkCIF report

Comment top

The title compound is used as a key intermediate in drug synthesis, and has been synthesized following a procedure described previously by (Bovicelli et al., 2007). We report herein on its synthesis and crystal structure.

The title compound crystallized with two independent molecules (A & B) in the asymmetric unit (Fig. 1). They differ significantly in conformation, as may be seen from the torsion angles in the 2-hydroxyethyl chain. For molecule A the torsion angles C1—C6—C7—C8 and C6—C7—C8—O2 are -56.6 (14) and -68.0 (13)°, respectively, while the corresponding torsion angles C13—C14—C15—C16 and C14—C15—C16—O4 in molecule B are -82.6 (12) and 172.2 (9)°, respectively. The bond lengths (Allen et al., 1987) and bond angles are otherwise within normal ranges.

In the crystal, the A molecules are linked via O—H···O hydrogen bonds to form inversion dimers, while the B molecules are linked via an O—H···O hydrogen bond to form a polymer chain propagating in [010], see Fig. 2. In the crystal, there are other O—H···O and O—H···Br hydrogen bonds (Table 1), and weak π···π stacking interactions involving the aromatic rings with their inversion related rings. The centroid-centroid distances are 3.931 (6) Å for Cg1···Cg1ⁱ [Cg1 is the centroid of ring (C1—C6); symmetry code (i) -x + 1, -y + 1, -z + 2] and 3.581 (6) Å for Cg2···Cg2ⁱⁱ [Cg2 is the centroid of ring (C9—C14); symmetry code (ii) -x + 2, -y, -z + 1]. There is also a short Br1···Br4ⁱⁱⁱ interaction present [3.599 (2) Å; symmetry code: (iii) -x + 1, -y, -z + 2]. These interactions result in the formation of two-dimensional networks lieing parallel to the ab plane (Fig. 3).

Related literature top

For background and further synthetic details, see: Guerard et al. (2009); Bovicelli et al. (2007). For standard bond-length data, see: Allen et al. (1987). For a related structure, see: Zhu et al. (2011)

Experimental top

The title compound was synthesized using a slightly modified version of the procedure reported on by (Bovicelli et al., 2007), using twice the quantity of NaBr. To a solution of 4-hydroxyphenethyl alcohol (217.4 mmol, 30 g) and NaBr (434.8 mmol, 44.34 g) in acetone (600 ml), a solution of oxone (200 g) in water (1 L) was added dropwise at 263 K within 3 h. The progress of the reaction was monitored by thin-layer chromatography (TLC, hexane/ethyl acetate 3:2), and when the reaction was over (complete consumption of the substrate), AcOEt (500 ml) was added to the mixture. The organic layer was separated, and the aqueous phase was extracted with two 300 mL portions of AcOEt (300 ml). The combined organic solutions were washed with water (300 ml), dried over anhydrous Na₂SO₄(white power,100 g), and evaporated. The product obtained in almost quantitative yield (59.7 g), appeared to be spectroscopically pure: white solid. Crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow evaporation of an acetone solution at room temperature.

Structure description top

For background and further synthetic details, see: Guerard et al. (2009); Bovicelli et al. (2007). For standard bond-length data, see: Allen et al. (1987). For a related structure, see: Zhu et al. (2011)

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the two indpendent molecules (A and B) of the title compound, with the atom numbering scheme and displacement ellipsoids drawn at 30% probability levels.
	Fig. 2. A view along the a axis of the hydrogen bonded inversion dimers of A molecules and the polymer chain of B molecules of the title compound [hydrogen bonds are shown as dashed cyan lines; see Table 1 for details; symmetry codes: (i) -x + 1, -y + 1, -z + 2; (ii) x, y + 1, z; (iii) x, y - 1, z].
	Fig. 3. A perspective view along the b axis of the crystal packing of the title compound, showing the O—H···O and O—H···Br hydrogen bonds as dashed lines (see Table 1 for details).

2,6-Dibromo-4-(2-hydroxyethyl)phenol top

Crystal data top

C₈H₈Br₂O₂	Z = 4
M_r = 295.94	F(000) = 568
Triclinic, P1	D_x = 2.115 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5740 (17) Å	Cell parameters from 25 reflections
b = 9.845 (2) Å	θ = 10–13°
c = 11.392 (2) Å	µ = 8.68 mm⁻¹
α = 86.08 (3)°	T = 293 K
β = 75.79 (3)°	Block, colourless
γ = 87.39 (3)°	0.20 × 0.10 × 0.10 mm
V = 929.6 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.087
Graphite monochromator	θ_max = 25.4°, θ_min = 1.9°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.276, T_max = 0.478	l = −13→13
3664 measured reflections	3 standard reflections every 200 reflections
3416 independent reflections	intensity decay: 1%

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.072P)²] where P = (F_o² + 2F_c²)/3
3416 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.63 e Å⁻³
1 restraint	Δρ_min = −0.72 e Å⁻³

Crystal data top

C₈H₈Br₂O₂	γ = 87.39 (3)°
M_r = 295.94	V = 929.6 (3) Å³
Triclinic, P1	Z = 4
a = 8.5740 (17) Å	Mo Kα radiation
b = 9.845 (2) Å	µ = 8.68 mm⁻¹
c = 11.392 (2) Å	T = 293 K
α = 86.08 (3)°	0.20 × 0.10 × 0.10 mm
β = 75.79 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1874 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.087
T_min = 0.276, T_max = 0.478	3 standard reflections every 200 reflections
3664 measured reflections	intensity decay: 1%
3416 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	Δρ_max = 0.63 e Å⁻³
3416 reflections	Δρ_min = −0.72 e Å⁻³
217 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.68665 (14)	0.22580 (14)	1.16796 (12)	0.0661 (5)
Br2	0.15646 (15)	0.59523 (13)	1.18207 (12)	0.0703 (5)
O1	0.4403 (9)	0.4472 (8)	1.2658 (7)	0.070 (3)
O2	0.4818 (9)	0.3052 (8)	0.6910 (7)	0.066 (3)
C1	0.4707 (12)	0.2251 (11)	1.0171 (9)	0.050 (4)
C2	0.5035 (11)	0.2892 (9)	1.1125 (9)	0.043 (3)
C3	0.4101 (13)	0.3990 (10)	1.1676 (9)	0.049 (4)
C4	0.2875 (12)	0.4483 (10)	1.1133 (9)	0.050 (3)
C5	0.2490 (12)	0.3861 (10)	1.0200 (9)	0.050 (4)
C6	0.3404 (13)	0.2735 (11)	0.9689 (10)	0.053 (4)
C7	0.2967 (12)	0.1977 (12)	0.8703 (9)	0.056 (4)
C8	0.4333 (12)	0.1821 (9)	0.7602 (9)	0.049 (3)
Br3	1.12544 (15)	−0.02904 (13)	0.15184 (12)	0.0742 (5)
Br4	0.64211 (13)	−0.12778 (11)	0.58132 (10)	0.0558 (4)
O3	0.8985 (8)	−0.1939 (6)	0.3477 (6)	0.049 (2)
O4	0.7207 (8)	0.5766 (7)	0.4611 (6)	0.056 (3)
C9	0.9903 (11)	0.1713 (10)	0.3173 (9)	0.046 (4)
C10	0.9906 (11)	0.0338 (10)	0.2919 (9)	0.045 (3)
C11	0.8926 (11)	−0.0623 (9)	0.3728 (9)	0.039 (3)
C12	0.7878 (10)	−0.0124 (9)	0.4787 (9)	0.036 (3)
C13	0.7884 (11)	0.1234 (10)	0.5006 (10)	0.048 (3)
C14	0.8884 (11)	0.2154 (10)	0.4232 (10)	0.047 (3)
C15	0.8832 (12)	0.3638 (11)	0.4564 (10)	0.052 (4)
C16	0.7456 (13)	0.4450 (10)	0.4198 (11)	0.059 (4)
H1	0.53400	0.15080	0.98510	0.0600*
H1O	0.46340	0.52760	1.25190	0.1050*
H2O	0.41630	0.32850	0.65120	0.0990*
H5	0.16160	0.41900	0.99050	0.0600*
H7A	0.26060	0.10790	0.90340	0.0670*
H7B	0.20760	0.24600	0.84580	0.0670*
H8A	0.52520	0.14080	0.78600	0.0580*
H8B	0.40200	0.11990	0.70820	0.0580*
H3O	0.96250	−0.21940	0.28290	0.0590*
H4O	0.80520	0.62110	0.43080	0.0840*
H9	1.05730	0.23190	0.26410	0.0560*
H13	0.71880	0.15470	0.57020	0.0580*
H15A	0.87040	0.36660	0.54320	0.0620*
H15B	0.98440	0.40530	0.41600	0.0620*
H16A	0.64730	0.39530	0.45080	0.0710*
H16C	0.76670	0.45120	0.33200	0.0710*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0559 (7)	0.0740 (9)	0.0707 (8)	0.0040 (6)	−0.0190 (6)	−0.0112 (6)
Br2	0.0754 (9)	0.0556 (8)	0.0731 (9)	0.0157 (6)	−0.0043 (6)	−0.0185 (6)
O1	0.079 (6)	0.067 (6)	0.062 (5)	−0.009 (4)	−0.010 (4)	−0.010 (4)
O2	0.074 (5)	0.066 (5)	0.056 (5)	−0.011 (4)	−0.010 (4)	−0.015 (4)
C1	0.043 (6)	0.055 (7)	0.041 (6)	−0.001 (5)	0.013 (5)	−0.012 (5)
C2	0.045 (6)	0.034 (5)	0.050 (6)	−0.003 (4)	−0.009 (5)	−0.016 (4)
C3	0.062 (7)	0.038 (6)	0.047 (6)	−0.007 (5)	−0.007 (5)	−0.016 (5)
C4	0.049 (6)	0.045 (6)	0.046 (6)	0.006 (5)	0.003 (5)	0.011 (5)
C5	0.042 (6)	0.051 (7)	0.052 (7)	0.008 (5)	−0.003 (5)	−0.010 (5)
C6	0.049 (6)	0.054 (7)	0.057 (7)	−0.003 (5)	−0.010 (5)	−0.018 (5)
C7	0.052 (6)	0.065 (8)	0.049 (7)	−0.004 (6)	−0.003 (5)	−0.023 (5)
C8	0.062 (7)	0.032 (5)	0.051 (6)	−0.002 (5)	−0.009 (5)	−0.012 (4)
Br3	0.0710 (8)	0.0624 (8)	0.0702 (9)	0.0004 (6)	0.0217 (6)	−0.0141 (6)
Br4	0.0524 (7)	0.0416 (6)	0.0638 (7)	−0.0090 (5)	0.0075 (5)	−0.0094 (5)
O3	0.055 (4)	0.037 (4)	0.046 (4)	0.004 (3)	0.008 (3)	−0.016 (3)
O4	0.056 (5)	0.044 (4)	0.065 (5)	0.000 (4)	−0.004 (4)	−0.017 (4)
C9	0.040 (6)	0.035 (6)	0.056 (7)	0.000 (5)	0.000 (5)	0.011 (5)
C10	0.038 (5)	0.048 (6)	0.046 (6)	−0.007 (5)	0.001 (4)	−0.012 (5)
C11	0.043 (5)	0.024 (5)	0.051 (6)	0.002 (4)	−0.013 (4)	−0.017 (4)
C12	0.033 (5)	0.024 (5)	0.051 (6)	−0.001 (4)	−0.007 (4)	−0.010 (4)
C13	0.030 (5)	0.045 (6)	0.063 (7)	0.010 (5)	0.002 (5)	−0.012 (5)
C14	0.039 (5)	0.045 (5)	0.061 (7)	0.003 (5)	−0.016 (5)	−0.015 (5)
C15	0.043 (6)	0.052 (6)	0.062 (7)	0.005 (5)	−0.012 (5)	−0.015 (5)
C16	0.061 (7)	0.038 (6)	0.071 (8)	0.007 (5)	−0.002 (6)	−0.016 (5)

Geometric parameters (Å, º) top

Br1—C2	1.897 (10)	C1—H1	0.9300
Br2—C4	1.882 (10)	C5—H5	0.9300
Br3—C10	1.852 (10)	C7—H7B	0.9700
Br4—C12	1.857 (9)	C7—H7A	0.9700
O1—C3	1.330 (13)	C8—H8B	0.9700
O2—C8	1.420 (12)	C8—H8A	0.9700
O1—H1O	0.8200	C9—C10	1.403 (14)
O2—H2O	0.8200	C9—C14	1.388 (15)
O3—C11	1.342 (11)	C10—C11	1.423 (14)
O4—C16	1.398 (12)	C11—C12	1.419 (14)
O3—H3O	0.8500	C12—C13	1.377 (13)
O4—H4O	0.8500	C13—C14	1.387 (15)
C1—C2	1.385 (14)	C14—C15	1.530 (15)
C1—C6	1.412 (15)	C15—C16	1.522 (16)
C2—C3	1.404 (14)	C9—H9	0.9300
C3—C4	1.398 (15)	C13—H13	0.9300
C4—C5	1.376 (14)	C15—H15A	0.9700
C5—C6	1.403 (15)	C15—H15B	0.9700
C6—C7	1.518 (15)	C16—H16A	0.9700
C7—C8	1.502 (14)	C16—H16C	0.9700

C3—O1—H1O	109.00	C7—C8—H8B	109.00
C8—O2—H2O	109.00	O2—C8—H8A	109.00
C11—O3—H3O	119.00	C10—C9—C14	118.9 (9)
C16—O4—H4O	108.00	C9—C10—C11	122.0 (9)
C2—C1—C6	119.4 (10)	Br3—C10—C11	117.8 (7)
C1—C2—C3	123.3 (9)	Br3—C10—C9	120.2 (7)
Br1—C2—C1	117.5 (7)	O3—C11—C12	122.1 (8)
Br1—C2—C3	119.2 (7)	O3—C11—C10	120.7 (9)
O1—C3—C2	119.7 (10)	C10—C11—C12	117.2 (8)
C2—C3—C4	115.5 (9)	Br4—C12—C13	120.5 (8)
O1—C3—C4	124.8 (9)	Br4—C12—C11	119.9 (7)
Br2—C4—C3	118.1 (7)	C11—C12—C13	119.6 (9)
Br2—C4—C5	118.8 (8)	C12—C13—C14	122.8 (10)
C3—C4—C5	122.9 (9)	C9—C14—C15	121.4 (9)
C4—C5—C6	120.6 (10)	C9—C14—C13	119.5 (9)
C1—C6—C5	118.1 (10)	C13—C14—C15	119.1 (9)
C5—C6—C7	122.1 (10)	C14—C15—C16	111.6 (9)
C1—C6—C7	119.6 (10)	O4—C16—C15	114.7 (9)
C6—C7—C8	113.7 (9)	C10—C9—H9	121.00
O2—C8—C7	115.0 (8)	C14—C9—H9	121.00
C2—C1—H1	120.00	C12—C13—H13	119.00
C6—C1—H1	120.00	C14—C13—H13	119.00
C6—C5—H5	120.00	C14—C15—H15A	109.00
C4—C5—H5	120.00	C14—C15—H15B	109.00
C6—C7—H7A	109.00	C16—C15—H15A	109.00
C8—C7—H7B	109.00	C16—C15—H15B	109.00
C6—C7—H7B	109.00	H15A—C15—H15B	108.00
C8—C7—H7A	109.00	O4—C16—H16A	109.00
H7A—C7—H7B	108.00	O4—C16—H16C	109.00
O2—C8—H8B	109.00	C15—C16—H16A	109.00
C7—C8—H8A	109.00	C15—C16—H16C	109.00
H8A—C8—H8B	108.00	H16A—C16—H16C	108.00

C6—C1—C2—Br1	−176.8 (8)	C14—C9—C10—Br3	−179.8 (8)
C6—C1—C2—C3	2.0 (16)	C14—C9—C10—C11	−1.6 (15)
C2—C1—C6—C5	0.2 (15)	C10—C9—C14—C13	−0.7 (15)
C2—C1—C6—C7	−175.8 (9)	C10—C9—C14—C15	179.6 (9)
Br1—C2—C3—O1	−7.3 (13)	Br3—C10—C11—O3	0.0 (13)
Br1—C2—C3—C4	173.7 (7)	Br3—C10—C11—C12	−178.9 (7)
C1—C2—C3—O1	173.9 (10)	C9—C10—C11—O3	−178.2 (9)
C1—C2—C3—C4	−5.1 (15)	C9—C10—C11—C12	2.9 (14)
O1—C3—C4—Br2	0.9 (14)	O3—C11—C12—Br4	−4.8 (13)
O1—C3—C4—C5	−172.6 (10)	O3—C11—C12—C13	179.2 (9)
C2—C3—C4—Br2	179.8 (7)	C10—C11—C12—Br4	174.2 (7)
C2—C3—C4—C5	6.3 (15)	C10—C11—C12—C13	−1.9 (14)
Br2—C4—C5—C6	−177.9 (8)	Br4—C12—C13—C14	−176.3 (8)
C3—C4—C5—C6	−4.5 (16)	C11—C12—C13—C14	−0.2 (15)
C4—C5—C6—C1	0.9 (16)	C12—C13—C14—C9	1.6 (16)
C4—C5—C6—C7	176.8 (10)	C12—C13—C14—C15	−178.7 (9)
C1—C6—C7—C8	−56.6 (13)	C9—C14—C15—C16	97.1 (12)
C5—C6—C7—C8	127.6 (11)	C13—C14—C15—C16	−82.6 (12)
C6—C7—C8—O2	−68.0 (12)	C14—C15—C16—O4	172.2 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.82	1.93	2.665 (11)	149
O4—H4O···O3ⁱⁱ	0.85	2.09	2.837 (9)	146
O2—H2O···O4ⁱⁱⁱ	0.82	2.09	2.896 (10)	168
O3—H3O···Br2^iv	0.85	2.55	3.291 (7)	147

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

Experimental details

Crystal data
Chemical formula	C₈H₈Br₂O₂
M_r	295.94
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5740 (17), 9.845 (2), 11.392 (2)
α, β, γ (°)	86.08 (3), 75.79 (3), 87.39 (3)
V (Å³)	929.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.68
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.276, 0.478
No. of measured, independent and observed [I > 2σ(I)] reflections	3664, 3416, 1874
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.161, 1.00
No. of reflections	3416
No. of parameters	217
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.72

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.82	1.93	2.665 (11)	149
O4—H4O···O3ⁱⁱ	0.85	2.09	2.837 (9)	146
O2—H2O···O4ⁱⁱⁱ	0.82	2.09	2.896 (10)	168
O3—H3O···Br2^iv	0.85	2.55	3.291 (7)	147

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

Acknowledgements

This research work was supported financially by the Department of Science and Technology of Jiangsu Province (BE200830457) and the `863' project (2007 A A02Z211) from the Ministry of Science and Technology, China.

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. CSD CrossRef Web of Science Google Scholar
Bovicelli, P., Antonioletti, R., Mancini, S., Causio, S., Borioni, G., Ammendola, S. & Barontini, M. (2007). Synth. Commun. 37, 4245–4252. Web of Science CrossRef CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Guerard, K. C., Sabot, C., Racicot, L. & Canesi, S. (2009). J. Org. Chem. 74, 2039–2045. Web of Science PubMed CAS Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, J., Yang, W., Wang, L., Wang, K. & Hu, Y. (2011). Acta Cryst. E67, o1109. Web of Science CSD CrossRef IUCr Journals Google Scholar