Literature DB >> 22199772

2,6-Dibromo-4-(2-hy-droxy-eth-yl)phenol.

Ding-Qiang Lu, Hong Chai, Xiu-Quan Ling, Jia Chen, Jia-Li Wang.   

Abstract

The title compound, C(8)H(8)Br(2)O(2), crystallized with two independent mol-ecules (A and B) in the asymmetric unit. They differ in the conformation of the 2-hy-droxy-ethyl chain with the C-C-C-O torsion angle being -68.0 (12)° in mol-ecule A and 172.2 (9)° in mol-ecule B. In the crystal, the A mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers, while the B mol-ecules 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 inter-actions [centroid-centroid distances = 3.581 (6) and 3.931 (6) Å], leading to the formation of a two-dimensional network parallel to (001).

Entities:  

Year:  2011        PMID： 22199772      PMCID： PMC3238923          DOI： 10.1107/S1600536811046538

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 295.94 Triclinic, 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[F 2 > 2σ(F 2)] = 0.067 wR(F 2) = 0.161 S = 1.00 3416 reflections 217 parameters 1 restraint H-atom parameters constrained Δρmax = 0.63 e Å−3 Δρmin = −0.72 e Å−3 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046538/su2342sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046538/su2342Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811046538/su2342Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C8H8Br2O2Z = 4
Mr = 295.94F(000) = 568
Triclinic, P1Dx = 2.115 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5740 (17) ÅCell parameters from 25 reflections
b = 9.845 (2) Åθ = 10–13°
c = 11.392 (2) ŵ = 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
Enraf–Nonius CAD-4 diffractometer1874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.087
graphiteθmax = 25.4°, θmin = 1.9°
ω/2θ scansh = 0→10
Absorption correction: ψ scan (North et al., 1968)k = −11→11
Tmin = 0.276, Tmax = 0.478l = −13→13
3664 measured reflections3 standard reflections every 200 reflections
3416 independent reflections intensity decay: 1%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
3416 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.63 e Å−3
1 restraintΔρmin = −0.72 e Å−3
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.
xyzUiso*/Ueq
Br10.68665 (14)0.22580 (14)1.16796 (12)0.0661 (5)
Br20.15646 (15)0.59523 (13)1.18207 (12)0.0703 (5)
O10.4403 (9)0.4472 (8)1.2658 (7)0.070 (3)
O20.4818 (9)0.3052 (8)0.6910 (7)0.066 (3)
C10.4707 (12)0.2251 (11)1.0171 (9)0.050 (4)
C20.5035 (11)0.2892 (9)1.1125 (9)0.043 (3)
C30.4101 (13)0.3990 (10)1.1676 (9)0.049 (4)
C40.2875 (12)0.4483 (10)1.1133 (9)0.050 (3)
C50.2490 (12)0.3861 (10)1.0200 (9)0.050 (4)
C60.3404 (13)0.2735 (11)0.9689 (10)0.053 (4)
C70.2967 (12)0.1977 (12)0.8703 (9)0.056 (4)
C80.4333 (12)0.1821 (9)0.7602 (9)0.049 (3)
Br31.12544 (15)−0.02904 (13)0.15184 (12)0.0742 (5)
Br40.64211 (13)−0.12778 (11)0.58132 (10)0.0558 (4)
O30.8985 (8)−0.1939 (6)0.3477 (6)0.049 (2)
O40.7207 (8)0.5766 (7)0.4611 (6)0.056 (3)
C90.9903 (11)0.1713 (10)0.3173 (9)0.046 (4)
C100.9906 (11)0.0338 (10)0.2919 (9)0.045 (3)
C110.8926 (11)−0.0623 (9)0.3728 (9)0.039 (3)
C120.7878 (10)−0.0124 (9)0.4787 (9)0.036 (3)
C130.7884 (11)0.1234 (10)0.5006 (10)0.048 (3)
C140.8884 (11)0.2154 (10)0.4232 (10)0.047 (3)
C150.8832 (12)0.3638 (11)0.4564 (10)0.052 (4)
C160.7456 (13)0.4450 (10)0.4198 (11)0.059 (4)
H10.534000.150800.985100.0600*
H1O0.463400.527601.251900.1050*
H2O0.416300.328500.651200.0990*
H50.161600.419000.990500.0600*
H7A0.260600.107900.903400.0670*
H7B0.207600.246000.845800.0670*
H8A0.525200.140800.786000.0580*
H8B0.402000.119900.708200.0580*
H3O0.96250−0.219400.282900.0590*
H4O0.805200.621100.430800.0840*
H91.057300.231900.264100.0560*
H130.718800.154700.570200.0580*
H15A0.870400.366600.543200.0620*
H15B0.984400.405300.416000.0620*
H16A0.647300.395300.450800.0710*
H16C0.766700.451200.332000.0710*
U11U22U33U12U13U23
Br10.0559 (7)0.0740 (9)0.0707 (8)0.0040 (6)−0.0190 (6)−0.0112 (6)
Br20.0754 (9)0.0556 (8)0.0731 (9)0.0157 (6)−0.0043 (6)−0.0185 (6)
O10.079 (6)0.067 (6)0.062 (5)−0.009 (4)−0.010 (4)−0.010 (4)
O20.074 (5)0.066 (5)0.056 (5)−0.011 (4)−0.010 (4)−0.015 (4)
C10.043 (6)0.055 (7)0.041 (6)−0.001 (5)0.013 (5)−0.012 (5)
C20.045 (6)0.034 (5)0.050 (6)−0.003 (4)−0.009 (5)−0.016 (4)
C30.062 (7)0.038 (6)0.047 (6)−0.007 (5)−0.007 (5)−0.016 (5)
C40.049 (6)0.045 (6)0.046 (6)0.006 (5)0.003 (5)0.011 (5)
C50.042 (6)0.051 (7)0.052 (7)0.008 (5)−0.003 (5)−0.010 (5)
C60.049 (6)0.054 (7)0.057 (7)−0.003 (5)−0.010 (5)−0.018 (5)
C70.052 (6)0.065 (8)0.049 (7)−0.004 (6)−0.003 (5)−0.023 (5)
C80.062 (7)0.032 (5)0.051 (6)−0.002 (5)−0.009 (5)−0.012 (4)
Br30.0710 (8)0.0624 (8)0.0702 (9)0.0004 (6)0.0217 (6)−0.0141 (6)
Br40.0524 (7)0.0416 (6)0.0638 (7)−0.0090 (5)0.0075 (5)−0.0094 (5)
O30.055 (4)0.037 (4)0.046 (4)0.004 (3)0.008 (3)−0.016 (3)
O40.056 (5)0.044 (4)0.065 (5)0.000 (4)−0.004 (4)−0.017 (4)
C90.040 (6)0.035 (6)0.056 (7)0.000 (5)0.000 (5)0.011 (5)
C100.038 (5)0.048 (6)0.046 (6)−0.007 (5)0.001 (4)−0.012 (5)
C110.043 (5)0.024 (5)0.051 (6)0.002 (4)−0.013 (4)−0.017 (4)
C120.033 (5)0.024 (5)0.051 (6)−0.001 (4)−0.007 (4)−0.010 (4)
C130.030 (5)0.045 (6)0.063 (7)0.010 (5)0.002 (5)−0.012 (5)
C140.039 (5)0.045 (5)0.061 (7)0.003 (5)−0.016 (5)−0.015 (5)
C150.043 (6)0.052 (6)0.062 (7)0.005 (5)−0.012 (5)−0.015 (5)
C160.061 (7)0.038 (6)0.071 (8)0.007 (5)−0.002 (6)−0.016 (5)
Br1—C21.897 (10)C1—H10.9300
Br2—C41.882 (10)C5—H50.9300
Br3—C101.852 (10)C7—H7B0.9700
Br4—C121.857 (9)C7—H7A0.9700
O1—C31.330 (13)C8—H8B0.9700
O2—C81.420 (12)C8—H8A0.9700
O1—H1O0.8200C9—C101.403 (14)
O2—H2O0.8200C9—C141.388 (15)
O3—C111.342 (11)C10—C111.423 (14)
O4—C161.398 (12)C11—C121.419 (14)
O3—H3O0.8500C12—C131.377 (13)
O4—H4O0.8500C13—C141.387 (15)
C1—C21.385 (14)C14—C151.530 (15)
C1—C61.412 (15)C15—C161.522 (16)
C2—C31.404 (14)C9—H90.9300
C3—C41.398 (15)C13—H130.9300
C4—C51.376 (14)C15—H15A0.9700
C5—C61.403 (15)C15—H15B0.9700
C6—C71.518 (15)C16—H16A0.9700
C7—C81.502 (14)C16—H16C0.9700
C3—O1—H1O109.00C7—C8—H8B109.00
C8—O2—H2O109.00O2—C8—H8A109.00
C11—O3—H3O119.00C10—C9—C14118.9 (9)
C16—O4—H4O108.00C9—C10—C11122.0 (9)
C2—C1—C6119.4 (10)Br3—C10—C11117.8 (7)
C1—C2—C3123.3 (9)Br3—C10—C9120.2 (7)
Br1—C2—C1117.5 (7)O3—C11—C12122.1 (8)
Br1—C2—C3119.2 (7)O3—C11—C10120.7 (9)
O1—C3—C2119.7 (10)C10—C11—C12117.2 (8)
C2—C3—C4115.5 (9)Br4—C12—C13120.5 (8)
O1—C3—C4124.8 (9)Br4—C12—C11119.9 (7)
Br2—C4—C3118.1 (7)C11—C12—C13119.6 (9)
Br2—C4—C5118.8 (8)C12—C13—C14122.8 (10)
C3—C4—C5122.9 (9)C9—C14—C15121.4 (9)
C4—C5—C6120.6 (10)C9—C14—C13119.5 (9)
C1—C6—C5118.1 (10)C13—C14—C15119.1 (9)
C5—C6—C7122.1 (10)C14—C15—C16111.6 (9)
C1—C6—C7119.6 (10)O4—C16—C15114.7 (9)
C6—C7—C8113.7 (9)C10—C9—H9121.00
O2—C8—C7115.0 (8)C14—C9—H9121.00
C2—C1—H1120.00C12—C13—H13119.00
C6—C1—H1120.00C14—C13—H13119.00
C6—C5—H5120.00C14—C15—H15A109.00
C4—C5—H5120.00C14—C15—H15B109.00
C6—C7—H7A109.00C16—C15—H15A109.00
C8—C7—H7B109.00C16—C15—H15B109.00
C6—C7—H7B109.00H15A—C15—H15B108.00
C8—C7—H7A109.00O4—C16—H16A109.00
H7A—C7—H7B108.00O4—C16—H16C109.00
O2—C8—H8B109.00C15—C16—H16A109.00
C7—C8—H8A109.00C15—C16—H16C109.00
H8A—C8—H8B108.00H16A—C16—H16C108.00
C6—C1—C2—Br1−176.8 (8)C14—C9—C10—Br3−179.8 (8)
C6—C1—C2—C32.0 (16)C14—C9—C10—C11−1.6 (15)
C2—C1—C6—C50.2 (15)C10—C9—C14—C13−0.7 (15)
C2—C1—C6—C7−175.8 (9)C10—C9—C14—C15179.6 (9)
Br1—C2—C3—O1−7.3 (13)Br3—C10—C11—O30.0 (13)
Br1—C2—C3—C4173.7 (7)Br3—C10—C11—C12−178.9 (7)
C1—C2—C3—O1173.9 (10)C9—C10—C11—O3−178.2 (9)
C1—C2—C3—C4−5.1 (15)C9—C10—C11—C122.9 (14)
O1—C3—C4—Br20.9 (14)O3—C11—C12—Br4−4.8 (13)
O1—C3—C4—C5−172.6 (10)O3—C11—C12—C13179.2 (9)
C2—C3—C4—Br2179.8 (7)C10—C11—C12—Br4174.2 (7)
C2—C3—C4—C56.3 (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—C10.9 (16)C12—C13—C14—C91.6 (16)
C4—C5—C6—C7176.8 (10)C12—C13—C14—C15−178.7 (9)
C1—C6—C7—C8−56.6 (13)C9—C14—C15—C1697.1 (12)
C5—C6—C7—C8127.6 (11)C13—C14—C15—C16−82.6 (12)
C6—C7—C8—O2−68.0 (12)C14—C15—C16—O4172.2 (9)
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.821.932.665 (11)149
O4—H4O···O3ii0.852.092.837 (9)146
O2—H2O···O4iii0.822.092.896 (10)168
O3—H3O···Br2iv0.852.553.291 (7)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1O⋯O2i0.821.932.665 (11)149
O4—H4O⋯O3ii0.852.092.837 (9)146
O2—H2O⋯O4iii0.822.092.896 (10)168
O3—H3O⋯Br2iv0.852.553.291 (7)147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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