Bis[2-bromo-4-(2-hy-droxy-eth-yl)phenol] monohydrate.

In the title compound, 2C(8)H(9)BrO(2)·H(2)O, the O-C-C-C torsion angles for the hy-droxy-ethyl 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 mol-ecule and 61.5 (11) and 0.2 (11)°, respectively, in the other. In the crystal, mol-ecules 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 = 452.14

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.095

S = 1.01

1827 reflections

208 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), 746 Friedel pairs

Flack parameter: 0.00 (2)

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 ▶).

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

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

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

2C8H9BrO2·H2O	F(000) = 904
Mr = 452.14	Dx = 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

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

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(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1827 reflections	Δρmax = 0.32 e Å−3
208 parameters	Δρmin = −0.45 e Å−3
2 restraints	Absolute structure: Flack (1983), 746 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (2)

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
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*

	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)

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)

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

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) ; (ii) ; (iii) .