Bis[2-bromo-4-(2-hy­droxy­eth­yl)phenol] monohydrate

Zhu, J.; Yang, W.; Wang, L.; Wang, K.; Hu, Y.

doi:10.1107/S160053681101066X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1109

doi:10.1107/S160053681101066X

Open

access

Bis[2-bromo-4-(2-hydroxyethyl)phenol] monohydrate

Jing Zhu,^a Wen-ge Yang,^a ^* Lu-lu Wang,^a Kai Wang ^a and Yong-hong Hu ^b

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

(Received 17 February 2011; accepted 22 March 2011; online 13 April 2011)

In the title compound, 2C₈H₉BrO₂·H₂O, the O—C—C—C torsion angles for the hydroxyethyl group and the Br—C—C—O torsion angles involving bromo and phenol groups are 61.7 (11) and 0.7 (12)°, respectively, in one independent molecule and 61.5 (11) and 0.2 (11)°, respectively, in the other. In the crystal, molecules are linked through O—H⋯O and O—H⋯Br hydrogen bonds, forming a polymeric chain.

Related literature

For synthesis of the title compound and background information, see: Bovicelli et al. (2007 ). For a related structure, see: Mewett et al. (2009 ).

Experimental

Crystal data

2C₈H₉BrO₂·H₂O
M_r = 452.14
Monoclinic, C c
a = 5.9790 (12) Å
b = 18.396 (4) Å
c = 16.801 (3) Å
β = 98.83 (3)°
V = 1826.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 4.46 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (ψ-scans; North et al., 1968 ) T_min = 0.469, T_max = 0.664
3585 measured reflections
1827 independent reflections
1302 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.095
S = 1.01
1827 reflections
208 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), 746 Friedel pairs
Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWA⋯Br1	0.89	2.86	3.537 (8)	134
OW—HWA⋯O2	0.89	2.00	2.820 (10)	151
O1—H1A⋯O4	0.82	1.84	2.633 (9)	163
OW—HWB⋯O1ⁱ	0.88	2.07	2.745 (10)	133
O2—H2A⋯Br1	0.85	2.56	3.026 (6)	115
O2—H2A⋯OW	0.85	2.18	2.820 (9)	131
O3—H3A⋯O2ⁱⁱ	0.82	1.80	2.592 (9)	162
O4—H4B⋯Br2	0.85	2.57	3.039 (7)	116
O4—H4B⋯OWⁱⁱⁱ	0.85	2.21	2.804 (10)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); 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); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101066X/pv2391sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101066X/pv2391Isup2.hkl

checkCIF report

Comment top

The title compound is used as the key intermediate in the synthesis of hydroxytyrosol (Bovicelli et al., 2007). As a part of our studies on the synthesis of hydroxytyrosol we report herein the crystal structure of the title compound.

In the molecules of the title compound, (Fig. 1), the bond lengths and angles agree very well with the corresponding bond lengths and angles reporeted in a structure containing the title compound as its fragment (Mewett et al., 2009).

In the crystal structure, O—H···O and O—H···Br type hydrogen bonding interactions (Table 1) link the molecules into ribbons extended along the a-axis (Fig. 2). The two molecules of the title compound in the asymmetric unit are identical. The torsion angles O1/C1/C2/C3 and C1/C2/C3/C8 are 61.7 (12) and -100.6 (11)°, respectively, in one molecule. The corresponding torion angles in the other molecule are 61.5 (11) and -101.5 (11)° (for O3/C9/C10/C11 and C9/C10/C11/C12, respectively).

Related literature top

For synthesis of the title compound and background information, see: Bovicelli et al. (2007). For a related structure, see: Mewett et al. (2009).

Experimental top

To a solution of 4-hydroxyphenethyl alcohol (217.4 mmol, 30 g) and NaBr (217.4 mmol, 22.17 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 6:4), 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. The combined organic solutions were washed with water (300 ml), dried over anhydrous Na₂SO₄ (100 g), and evaporated. The monobrominated product, obtained in almost quantitative yield (47.1 g), appeared to be spectroscopically pure, white solid (Bovicelli et al., 2007). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.
	Fig. 2. A practical packing diagram of the title compound. Hydron bonds are shown as dashed lines.

Bis[2-bromo-4-(2-hydroxyethyl)phenol] monohydrate top

Crystal data top

2C₈H₉BrO₂·H₂O	F(000) = 904
M_r = 452.14	D_x = 1.645 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 5.9790 (12) Å	θ = 9–13°
b = 18.396 (4) Å	µ = 4.46 mm⁻¹
c = 16.801 (3) Å	T = 293 K
β = 98.83 (3)°	Block, colorless
V = 1826.0 (6) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.3°, θ_min = 2.2°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (ψ-scans; North et al., 1968)	k = −22→22
T_min = 0.469, T_max = 0.664	l = −20→19
3585 measured reflections	3 standard reflections every 200 reflections
1827 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1827 reflections	Δρ_max = 0.32 e Å⁻³
208 parameters	Δρ_min = −0.45 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 746 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

2C₈H₉BrO₂·H₂O	V = 1826.0 (6) Å³
M_r = 452.14	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.9790 (12) Å	µ = 4.46 mm⁻¹
b = 18.396 (4) Å	T = 293 K
c = 16.801 (3) Å	0.20 × 0.10 × 0.10 mm
β = 98.83 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1302 reflections with I > 2σ(I)
Absorption correction: ψ scan (ψ-scans; North et al., 1968)	R_int = 0.045
T_min = 0.469, T_max = 0.664	3 standard reflections every 200 reflections
3585 measured reflections	intensity decay: 1%
1827 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.32 e Å⁻³
S = 1.01	Δρ_min = −0.45 e Å⁻³
1827 reflections	Absolute structure: Flack (1983), 746 Friedel pairs
208 parameters	Absolute structure parameter: 0.00 (2)
2 restraints

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
Br2	0.98869 (14)	0.25839 (6)	0.74826 (7)	0.0700 (4)
O3	0.7384 (12)	0.5738 (3)	0.6248 (4)	0.0621 (18)
H3A	0.8398	0.5653	0.5983	0.093*
O4	0.5409 (11)	0.2412 (3)	0.6368 (4)	0.0566 (17)
H4B	0.6442	0.2103	0.6523	0.068*
C9	0.827 (2)	0.5705 (6)	0.7086 (6)	0.060 (3)
H9A	0.8513	0.6194	0.7299	0.072*
H9B	0.9718	0.5455	0.7161	0.072*
C10	0.6614 (18)	0.5301 (5)	0.7535 (6)	0.061 (3)
H10A	0.7193	0.5299	0.8107	0.073*
H10B	0.5173	0.5554	0.7458	0.073*
C11	0.6262 (19)	0.4526 (5)	0.7238 (6)	0.053 (3)
C12	0.4362 (16)	0.4334 (5)	0.6716 (5)	0.048 (2)
H12A	0.3248	0.4680	0.6560	0.058*
C13	0.4082 (16)	0.3643 (5)	0.6423 (5)	0.051 (2)
H13A	0.2781	0.3530	0.6066	0.062*
C14	0.5678 (14)	0.3105 (5)	0.6643 (5)	0.044 (2)
C15	0.7609 (14)	0.3305 (5)	0.7164 (5)	0.042 (2)
C16	0.7941 (16)	0.3996 (5)	0.7461 (6)	0.052 (2)
H16A	0.9260	0.4113	0.7807	0.062*
OW	0.3419 (11)	0.6470 (4)	0.5757 (5)	0.074 (2)
HWA	0.2649	0.6129	0.5450	0.089*
HWB	0.3857	0.6750	0.5383	0.089*
Br1	0.34194 (14)	0.53555 (5)	0.40416 (7)	0.0640 (3)
O1	0.1966 (11)	0.2167 (3)	0.5222 (4)	0.064 (2)
H1A	0.3182	0.2261	0.5501	0.096*
C1	0.2190 (18)	0.2218 (6)	0.4413 (6)	0.054 (3)
H1B	0.2241	0.1734	0.4187	0.065*
H1C	0.3597	0.2463	0.4361	0.065*
O2	−0.0093 (10)	0.5504 (3)	0.5150 (4)	0.0542 (17)
H2A	0.0843	0.5814	0.5021	0.065*
C2	0.0224 (18)	0.2636 (5)	0.3950 (6)	0.058 (3)
H2B	0.0376	0.2644	0.3383	0.069*
H2C	−0.1178	0.2388	0.4002	0.069*
C3	0.0112 (17)	0.3401 (5)	0.4246 (5)	0.049 (2)
C4	0.1511 (15)	0.3940 (5)	0.4051 (5)	0.044 (2)
H4A	0.2537	0.3834	0.3703	0.053*
C5	0.1449 (15)	0.4620 (5)	0.4346 (5)	0.045 (2)
C6	−0.0025 (16)	0.4810 (5)	0.4867 (5)	0.044 (2)
C7	−0.1492 (16)	0.4280 (5)	0.5058 (5)	0.051 (2)
H7A	−0.2543	0.4396	0.5393	0.061*
C8	−0.1427 (15)	0.3594 (5)	0.4767 (6)	0.050 (2)
H8A	−0.2415	0.3246	0.4914	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0482 (5)	0.0791 (8)	0.0764 (7)	0.0122 (6)	−0.0106 (5)	0.0016 (7)
O3	0.073 (5)	0.066 (4)	0.054 (4)	0.009 (4)	0.032 (4)	0.004 (3)
O4	0.045 (4)	0.050 (4)	0.072 (4)	0.009 (4)	−0.002 (3)	−0.008 (4)
C9	0.070 (7)	0.047 (6)	0.066 (7)	−0.003 (5)	0.018 (6)	−0.007 (5)
C10	0.064 (7)	0.064 (7)	0.058 (6)	−0.005 (6)	0.019 (5)	−0.007 (5)
C11	0.065 (7)	0.058 (6)	0.039 (6)	−0.006 (6)	0.017 (5)	0.010 (5)
C12	0.038 (5)	0.060 (6)	0.046 (5)	0.001 (5)	0.002 (4)	−0.004 (5)
C13	0.033 (5)	0.062 (7)	0.057 (6)	0.002 (5)	0.001 (4)	−0.008 (5)
C14	0.035 (5)	0.056 (6)	0.040 (5)	−0.008 (4)	0.001 (4)	0.000 (4)
C15	0.032 (5)	0.051 (6)	0.043 (5)	0.002 (4)	0.004 (4)	0.009 (4)
C16	0.043 (6)	0.066 (7)	0.046 (6)	−0.009 (5)	0.005 (4)	−0.001 (5)
OW	0.059 (5)	0.071 (4)	0.095 (5)	−0.010 (4)	0.020 (4)	−0.024 (4)
Br1	0.0591 (6)	0.0682 (6)	0.0715 (7)	−0.0019 (6)	0.0322 (5)	0.0040 (6)
O1	0.054 (4)	0.067 (4)	0.062 (4)	−0.012 (4)	−0.020 (4)	0.005 (3)
C1	0.054 (7)	0.049 (6)	0.058 (7)	0.015 (5)	0.004 (5)	0.003 (5)
O2	0.043 (4)	0.050 (4)	0.074 (4)	−0.005 (3)	0.022 (3)	−0.002 (3)
C2	0.059 (7)	0.069 (7)	0.045 (6)	0.007 (6)	0.006 (5)	−0.009 (5)
C3	0.051 (6)	0.048 (6)	0.044 (6)	0.005 (5)	−0.008 (5)	−0.001 (5)
C4	0.041 (5)	0.053 (6)	0.039 (5)	−0.001 (5)	0.005 (4)	−0.001 (5)
C5	0.044 (5)	0.051 (5)	0.042 (5)	−0.004 (4)	0.009 (4)	0.006 (5)
C6	0.039 (5)	0.051 (7)	0.042 (5)	0.003 (5)	0.009 (4)	−0.002 (5)
C7	0.038 (5)	0.067 (7)	0.050 (5)	0.012 (5)	0.013 (4)	0.003 (5)
C8	0.037 (5)	0.053 (6)	0.059 (6)	0.001 (5)	0.007 (5)	0.001 (5)

Geometric parameters (Å, º) top

Br2—C15	1.918 (8)	OW—HWB	0.8827
O3—C9	1.428 (11)	Br1—C5	1.915 (9)
O3—H3A	0.8200	O1—C1	1.391 (12)
O4—C14	1.357 (11)	O1—H1A	0.8200
O4—H4B	0.8500	C1—C2	1.515 (14)
C9—C10	1.529 (14)	C1—H1B	0.9700
C9—H9A	0.9700	C1—H1C	0.9700
C9—H9B	0.9700	O2—C6	1.365 (10)
C10—C11	1.515 (13)	O2—H2A	0.8500
C10—H10A	0.9700	C2—C3	1.497 (12)
C10—H10B	0.9700	C2—H2B	0.9700
C11—C12	1.370 (14)	C2—H2C	0.9700
C11—C16	1.409 (14)	C3—C4	1.370 (12)
C12—C13	1.364 (12)	C3—C8	1.410 (13)
C12—H12A	0.9300	C4—C5	1.348 (11)
C13—C14	1.385 (12)	C4—H4A	0.9300
C13—H13A	0.9300	C5—C6	1.380 (12)
C14—C15	1.388 (11)	C6—C7	1.382 (12)
C15—C16	1.368 (12)	C7—C8	1.355 (12)
C16—H16A	0.9300	C7—H7A	0.9300
OW—HWA	0.8938	C8—H8A	0.9300

C9—O3—H3A	109.5	C1—O1—H1A	109.5
C14—O4—H4B	118.7	O1—C1—C2	110.7 (8)
O3—C9—C10	109.7 (8)	O1—C1—H1B	109.5
O3—C9—H9A	109.7	C2—C1—H1B	109.5
C10—C9—H9A	109.7	O1—C1—H1C	109.5
O3—C9—H9B	109.7	C2—C1—H1C	109.5
C10—C9—H9B	109.7	H1B—C1—H1C	108.1
H9A—C9—H9B	108.2	C6—O2—H2A	118.8
C11—C10—C9	111.3 (8)	C3—C2—C1	112.2 (8)
C11—C10—H10A	109.4	C3—C2—H2B	109.2
C9—C10—H10A	109.4	C1—C2—H2B	109.2
C11—C10—H10B	109.4	C3—C2—H2C	109.2
C9—C10—H10B	109.4	C1—C2—H2C	109.2
H10A—C10—H10B	108.0	H2B—C2—H2C	107.9
C12—C11—C16	118.6 (9)	C4—C3—C8	116.5 (8)
C12—C11—C10	120.8 (10)	C4—C3—C2	122.7 (9)
C16—C11—C10	120.5 (10)	C8—C3—C2	120.7 (9)
C13—C12—C11	121.0 (10)	C5—C4—C3	122.1 (9)
C13—C12—H12A	119.5	C5—C4—H4A	119.0
C11—C12—H12A	119.5	C3—C4—H4A	119.0
C12—C13—C14	121.9 (9)	C4—C5—C6	121.8 (8)
C12—C13—H13A	119.1	C4—C5—Br1	120.2 (6)
C14—C13—H13A	119.1	C6—C5—Br1	118.0 (7)
O4—C14—C13	122.7 (8)	O2—C6—C5	121.0 (8)
O4—C14—C15	120.5 (8)	O2—C6—C7	121.7 (8)
C13—C14—C15	116.8 (9)	C5—C6—C7	117.2 (8)
C16—C15—C14	122.5 (8)	C8—C7—C6	121.3 (9)
C16—C15—Br2	118.9 (7)	C8—C7—H7A	119.4
C14—C15—Br2	118.6 (7)	C6—C7—H7A	119.4
C15—C16—C11	119.2 (9)	C7—C8—C3	121.1 (9)
C15—C16—H16A	120.4	C7—C8—H8A	119.5
C11—C16—H16A	120.4	C3—C8—H8A	119.5
HWA—OW—HWB	100.5

O3—C9—C10—C11	61.5 (11)	O1—C1—C2—C3	61.7 (11)
C9—C10—C11—C12	−101.5 (11)	C1—C2—C3—C4	77.6 (11)
C9—C10—C11—C16	75.1 (12)	C1—C2—C3—C8	−100.6 (11)
C16—C11—C12—C13	0.7 (14)	C8—C3—C4—C5	0.8 (14)
C10—C11—C12—C13	177.4 (9)	C2—C3—C4—C5	−177.4 (8)
C11—C12—C13—C14	0.6 (15)	C3—C4—C5—C6	0.3 (14)
C12—C13—C14—O4	178.9 (9)	C3—C4—C5—Br1	−179.2 (7)
C12—C13—C14—C15	−1.3 (13)	C4—C5—C6—O2	−178.8 (8)
O4—C14—C15—C16	−179.4 (8)	Br1—C5—C6—O2	0.7 (12)
C13—C14—C15—C16	0.8 (13)	C4—C5—C6—C7	−1.8 (13)
O4—C14—C15—Br2	0.2 (11)	Br1—C5—C6—C7	177.7 (7)
C13—C14—C15—Br2	−179.6 (6)	O2—C6—C7—C8	179.3 (8)
C14—C15—C16—C11	0.5 (14)	C5—C6—C7—C8	2.3 (14)
Br2—C15—C16—C11	−179.2 (7)	C6—C7—C8—C3	−1.2 (14)
C12—C11—C16—C15	−1.2 (14)	C4—C3—C8—C7	−0.3 (14)
C10—C11—C16—C15	−177.9 (8)	C2—C3—C8—C7	177.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···Br1	0.89	2.86	3.537 (8)	134
OW—HWA···O2	0.89	2.00	2.820 (10)	151
O1—H1A···O4	0.82	1.84	2.633 (9)	163
OW—HWB···O1ⁱ	0.88	2.07	2.745 (10)	133
O2—H2A···Br1	0.85	2.56	3.026 (6)	115
O2—H2A···OW	0.85	2.18	2.820 (9)	131
O3—H3A···O2ⁱⁱ	0.82	1.80	2.592 (9)	162
O4—H4B···Br2	0.85	2.57	3.039 (7)	116
O4—H4B···OWⁱⁱⁱ	0.85	2.21	2.804 (10)	127

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

Experimental details

Crystal data
Chemical formula	2C₈H₉BrO₂·H₂O
M_r	452.14
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	5.9790 (12), 18.396 (4), 16.801 (3)
β (°)	98.83 (3)
V (Å³)	1826.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.46
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (ψ-scans; North et al., 1968)
T_min, T_max	0.469, 0.664
No. of measured, independent and observed [I > 2σ(I)] reflections	3585, 1827, 1302
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.095, 1.01
No. of reflections	1827
No. of parameters	208
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.45
Absolute structure	Flack (1983), 746 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···Br1	0.89	2.86	3.537 (8)	134
OW—HWA···O2	0.89	2.00	2.820 (10)	151
O1—H1A···O4	0.82	1.84	2.633 (9)	163
OW—HWB···O1ⁱ	0.88	2.07	2.745 (10)	133
O2—H2A···Br1	0.85	2.56	3.026 (6)	115
O2—H2A···OW	0.85	2.18	2.820 (9)	131
O3—H3A···O2ⁱⁱ	0.82	1.80	2.592 (9)	162
O4—H4B···Br2	0.85	2.57	3.039 (7)	116
O4—H4B···OWⁱⁱⁱ	0.85	2.21	2.804 (10)	127

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

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) of the Ministry of Science and Technology of China.

References

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 (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Mewett, K. N., Fernandez, S. P., Pasricha, A. K., Pong, A., Devenish, S. O., Hibbs, D. E., Chebib, M., Johnston, G. A. & Hanrahan, J. R. (2009). Bioorg. Med. Chem. 17, 7156–7173. Web of Science CrossRef PubMed CAS 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