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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1103.
Published online 2009 April 25. doi:  10.1107/S1600536809014408
PMCID: PMC2977781

2,3-Dichloro­benzene-1,4-diol

Abstract

The achiral title compound, C6H4Cl2O2, crystallizes with O—H(...)O hydrogen bonding linking mol­ecules into layers. Between layers there are chains of Cl(...)Cl(...)Cl inter­actions with alternating distances of 3.274 (2) and 3.742 (2) Å. Augmenting this arrangement there are also C—H(...)Cl (2.97 and 3.17 Å) and Cl(...)π (shortest distances 3.40 and 3.54 Å) inter­actions.

Related literature

For the structures of related dichloronaphthalenediols, see: Ahn et al. (1995 [triangle], 1996 [triangle]). For the preparation of the title compound, see: Beddoes et al. (1981 [triangle]).

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Object name is e-65-o1103-scheme1.jpg

Experimental

Crystal data

  • C6H4Cl2O2
  • M r = 179.0
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1103-efi1.jpg
  • a = 4.831 (1) Å
  • b = 11.347 (2) Å
  • c = 12.962 (3) Å
  • β = 105.94 (1)°
  • V = 683.2 (2) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 8.02 mm−1
  • T = 294 K
  • 0.15 × 0.15 × 0.06 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: analytical (de Meulenaer & Tompa, 1965 [triangle]) T min = 0.33, T max = 0.63
  • 1449 measured reflections
  • 1290 independent reflections
  • 1187 reflections with I > 2σ(I)
  • R int = 0.041
  • 1 standard reflections frequency: 30 min intensity decay: 21%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.050
  • S = 1.87
  • 1290 reflections
  • 92 parameters
  • H-atom parameters not refined
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: CAD-4 Manual (Schagen et al., 1989 [triangle]); cell refinement: CAD-4 Manual; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: RAELS (Rae, 2000 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and CrystalMaker (CrystalMaker Software, 2005 [triangle]); software used to prepare material for publication: local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014408/bv2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014408/bv2117Isup2.hkl

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

Acknowledgments

This research was supported by the Australian Research Council.

supplementary crystallographic information

Comment

Crystal structures of related dichloronaphthalenediols have been previously reported by us (Ahn et al., 1995, 1996). In the title compound (Fig 1), each molecule participates in four hydrogen bonds, two as donor and two as acceptor, creating a layer structure in the ac plane with O1-H1O1···O2-H1O2···O1-H1O1··· chains parallel to a (Fig 2, Table 1). Aromatic offset face-face stacking at a distance of 3.5 Å takes place within the layer. Chains of Cl1···Cl1···Cl1 interactions (alternating distances 3.274 (2) and 3.742 (2) Å) which also run parallel to a link the layers into a three-dimensional array. In addition there are C5H···Cl2 and C6H···Cl2 (2.97 and 3.17 Å) and Cl2···π interactions (shortest distances 3.40 and 3.54 Å).

Experimental

2,3-Dichlorobenzene-1,4-diol was prepared as described (Beddoes et al., 1981). 1H NMR (300 MHz, d6-DMSO) δ 6.79 (s, 2H), 9.71 (s, 2H, –OH); 13C NMR (75 MHz, d6-DMSO) δ 115.1 (CH), 119.2 (C), 147.1 (C). X-ray quality solvent-free crystals were obtained from benzene solution.

Refinement

H atoms attached to C were included at calculated positions (C—H = 1.0 Å). The hydroxy hydrogen atoms were located on a difference map, and were then fixed at a position along the OH vector with O—H = 1.0 Å. All hydrogen atoms were refined with isotropic thermal parameters equivalent to those of the atom to which they were bonded.

Figures

Fig. 1.
A molecule of the title compound, showing atom labelling. Thermal ellipsoids are drawn at the 50% level.
Fig. 2.
A hydrogen bonded layer. Each molecule participates in two donor and two acceptor hydrogen bonds which are represented as dashed lines.

Crystal data

C6H4Cl2O2F(000) = 360.0
Mr = 179.0Dx = 1.74 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 4.831 (1) ÅCell parameters from 10 reflections
b = 11.347 (2) Åθ = 25–30°
c = 12.962 (3) ŵ = 8.02 mm1
β = 105.94 (1)°T = 294 K
V = 683.2 (2) Å3Tabular, colourless
Z = 40.15 × 0.15 × 0.06 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.041
ω–2θ scansθmax = 70°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)h = −5→0
Tmin = 0.33, Tmax = 0.63k = −13→0
1449 measured reflectionsl = −15→15
1290 independent reflections1 standard reflections every 30 min
1187 reflections with I > 2σ(I) intensity decay: 21%

Refinement

Refinement on F0 restraints
R[F2 > 2σ(F2)] = 0.034H-atom parameters not refined
wR(F2) = 0.050w = 1/[σ2(F) + 0.0004F2]
S = 1.87(Δ/σ)max = 0.008
1290 reflectionsΔρmax = 0.42 e Å3
92 parametersΔρmin = −0.31 e Å3

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

xyzUiso*/Ueq
Cl10.78228 (10)0.11149 (4)0.49607 (4)0.0444 (2)
Cl20.54566 (11)0.00422 (4)0.26478 (4)0.0439 (2)
O10.4715 (3)0.3170 (1)0.5364 (1)0.0463 (4)
O20.0408 (3)0.1224 (1)0.1331 (1)0.0404 (4)
C10.3548 (4)0.2698 (2)0.4364 (2)0.0340 (4)
C20.4868 (4)0.1726 (2)0.4063 (1)0.0328 (4)
C30.3797 (4)0.1238 (2)0.3049 (2)0.0319 (4)
C40.1366 (4)0.1719 (2)0.2334 (1)0.0334 (4)
C50.0028 (4)0.2679 (2)0.2647 (2)0.0363 (4)
C60.1126 (4)0.3174 (2)0.3651 (2)0.0363 (4)
H1O10.31960.35780.56220.046
H1O2−0.16190.14990.10260.040
HC5−0.17450.30180.21430.036
HC60.01680.38790.38640.036

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0340 (3)0.0503 (3)0.0427 (3)0.0103 (2)−0.0001 (2)0.0039 (2)
Cl20.0407 (3)0.0389 (3)0.0521 (4)0.0050 (2)0.0128 (2)−0.0066 (2)
O10.0360 (8)0.0620 (9)0.0367 (7)0.0060 (6)0.0030 (6)−0.0131 (7)
O20.0365 (7)0.0492 (8)0.0324 (7)−0.0001 (6)0.0044 (6)−0.0040 (6)
C10.0291 (9)0.0403 (9)0.0316 (9)−0.0004 (7)0.0068 (7)−0.0004 (7)
C20.0251 (8)0.0374 (9)0.0352 (9)0.0018 (7)0.0072 (7)0.0040 (7)
C30.0281 (9)0.0318 (8)0.037 (1)0.0001 (6)0.0101 (7)0.0009 (7)
C40.0302 (9)0.0386 (9)0.0306 (9)−0.0049 (7)0.0070 (7)0.0018 (7)
C50.0314 (9)0.040 (1)0.036 (1)0.0038 (7)0.0061 (7)0.0051 (8)
C60.031 (1)0.039 (1)0.039 (1)0.0056 (7)0.0097 (8)0.0020 (8)

Geometric parameters (Å, °)

Cl1—C21.721 (2)C1—C61.386 (2)
Cl2—C31.727 (2)C2—C31.389 (3)
O1—C11.372 (2)C3—C41.392 (3)
O1—H1O11.000C4—C51.383 (3)
O2—C41.374 (2)C5—C61.383 (3)
O2—H1O21.000C5—HC51.000
C1—C21.383 (3)C6—HC61.000
C1—O1—H1O1110.4C2—C3—C4120.1 (2)
C4—O2—H1O2106.6O2—C4—C3118.2 (2)
O1—C1—C2118.4 (2)O2—C4—C5122.4 (2)
O1—C1—C6122.1 (2)C3—C4—C5119.4 (2)
C2—C1—C6119.5 (2)C4—C5—C6120.4 (2)
Cl1—C2—C1119.5 (1)C4—C5—HC5119.8
Cl1—C2—C3120.3 (1)C6—C5—HC5119.8
C1—C2—C3120.3 (2)C1—C6—C5120.3 (2)
Cl2—C3—C2121.0 (1)C1—C6—HC6119.8
Cl2—C3—C4118.9 (1)C5—C6—HC6119.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O1···O2i1.001.842.794 (2)158
O2—H1O2···O1ii1.001.782.778 (2)172

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2117).

References

  • Ahn, P. D., Bishop, R., Craig, D. C. & Scudder, M. L. (1995). J. Incl. Phenom. Mol. Rec. Chem.20, 267–276.
  • Ahn, P. D., Bishop, R., Craig, D. C. & Scudder, M. L. (1996). J. Incl. Phenom. Mol. Rec. Chem.23, 313–327.
  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Beddoes, R. L., Bruce, J. M., Finch, H., Heelam, L. M. J., Hunt, I. D. & Mills, O. S. (1981). J. Chem. Soc. Perkin Trans. 1, pp. 2670–2676.
  • CrystalMaker Software (2005). CrystalMaker CrystalMaker Software, Yarnton, England. www.CrystalMaker.co.uk.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Meulenaer, J. de & Tompa, H. (1965). Acta Cryst.19, 1014–1018.
  • Rae, A. D. (2000). RAELS Australian National University, Canberra, Australia.
  • Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual Enraf–Nonius, Delft, The Netherlands.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography