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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m621.
Published online 2010 May 8. doi:  10.1107/S1600536810015977
PMCID: PMC2979562

catena-Poly[zinc(II)-bis­[μ-2-(2,4-dichloro­phen­oxy)acetato]]

Abstract

The title polymeric compound, [Zn(C8H5Cl2O3)2]n, was prepared by reaction of zinc(II) chloride with 2,4-dichloro­phenoxy­acetic acid and sodium hydroxide under hydro­thermal conditions. The ZnII atom is coordinated in a distorted tetra­hedral environment by four O atoms from four 2,4-dichloro­phenoxy­acetate ligands. Each ligand bridges two ZnII atoms, forming a polymeric chain along the a axis. Adjacent chains are connected via C—H(...)Cl hydrogen bonds.

Related literature

For metal-organic coordination polymers, see: Qin et al. (2009 [triangle]); Huang et al. (2008 [triangle]); Reineke et al. (1999 [triangle]); Xiong et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m621-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H5Cl2O3)2]
  • M r = 505.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m621-efi1.jpg
  • a = 4.7322 (10) Å
  • b = 10.459 (2) Å
  • c = 18.979 (4) Å
  • α = 79.340 (2)°
  • β = 89.838 (2)°
  • γ = 82.847 (3)°
  • V = 915.8 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.96 mm−1
  • T = 296 K
  • 0.56 × 0.21 × 0.16 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.617, T max = 0.731
  • 4737 measured reflections
  • 3255 independent reflections
  • 2849 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.091
  • S = 0.94
  • 3255 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015977/ci5084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015977/ci5084Isup2.hkl

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

Acknowledgments

The author acknowledges South China Normal University for supporting this work.

supplementary crystallographic information

Experimental

A mixture of ZnCl2 (0.068 g, 0.5 mmol), H2O (6 ml), 2,4-dichlorophenoxyacetic acid (0.22 g, 1 mmol) was stirred vigorously for 10 min and then sodium hydroxide solution (1.0 mol/L) was added to adjust the pH value to 7.0. The mixture was then sealed in a 25 ml Teflon-lined stainless-steel autoclave. The autoclave was heated at 413 K for 3 d and then slowly cooled to room temperature at 6 K/h. The product was collected by filtration, washed with water and air-dried. Colourless needle-shaped crystals were obtained in ca. 42.3% yield based on Zn.

Refinement

H atoms were positioned geometrically [C–H = 0.93–0.97 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Part of a polymeric chain in the title compound. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (a) 1+x, y, z; (b) 1-x, 1-y, 1-z.
Fig. 2.
Part of the crystal packing, showing a polymeric chain viewed along the a axis. H atoms have been omitted for clarity.

Crystal data

[Zn(C8H5Cl2O3)2]Z = 2
Mr = 505.43F(000) = 504
Triclinic, P1Dx = 1.833 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.7322 (10) ÅCell parameters from 2642 reflections
b = 10.459 (2) Åθ = 2.5–27.7°
c = 18.979 (4) ŵ = 1.96 mm1
α = 79.340 (2)°T = 296 K
β = 89.838 (2)°Needle, colourless
γ = 82.847 (3)°0.56 × 0.21 × 0.16 mm
V = 915.8 (3) Å3

Data collection

Bruker SMART APEXII CCD diffractometer3255 independent reflections
Radiation source: fine-focus sealed tube2849 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.617, Tmax = 0.731k = −12→8
4737 measured reflectionsl = −22→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 0.94w = 1/[σ2(Fo2) + (0.0663P)2] where P = (Fo2 + 2Fc2)/3
3255 reflections(Δ/σ)max = 0.024
244 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.39 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
Zn10.66929 (6)0.53465 (3)0.409892 (14)0.02622 (12)
Cl20.46808 (18)1.18539 (7)0.33205 (4)0.0500 (2)
Cl3−0.18417 (19)1.02366 (8)0.14274 (4)0.0538 (2)
O10.5602 (4)0.69621 (17)0.44411 (10)0.0354 (4)
C20.2487 (7)0.8626 (2)0.48725 (14)0.0368 (6)
H2A0.04250.86860.48580.044*
H2B0.30340.88540.53210.044*
C10.3707 (5)0.7213 (2)0.48733 (13)0.0283 (5)
O20.3338 (4)0.95654 (17)0.43021 (10)0.0381 (4)
C80.2572 (6)1.0724 (2)0.31164 (15)0.0344 (6)
C30.2031 (6)0.9673 (2)0.36461 (14)0.0336 (6)
C70.1426 (6)1.0904 (3)0.24305 (15)0.0374 (6)
H70.18461.15930.20770.045*
C40.0218 (6)0.8825 (3)0.34807 (15)0.0370 (6)
H4−0.01980.81290.38300.044*
C6−0.0369 (6)1.0027 (3)0.22834 (15)0.0381 (6)
C5−0.0982 (6)0.9003 (3)0.27995 (16)0.0409 (7)
H5−0.21990.84290.26930.049*
O50.4663 (4)0.5250 (2)0.32238 (10)0.0379 (4)
C90.2002 (5)0.5268 (2)0.32394 (13)0.0285 (5)
C100.0513 (6)0.4985 (3)0.25952 (14)0.0365 (6)
H10A−0.06370.42830.27520.044*
H10B−0.07620.57590.23830.044*
O60.2391 (4)0.46218 (19)0.20660 (10)0.0394 (5)
C110.3544 (6)0.5571 (3)0.16035 (14)0.0335 (6)
C120.5536 (6)0.5123 (3)0.11352 (14)0.0371 (6)
C140.6058 (7)0.7315 (3)0.05874 (16)0.0440 (7)
C150.4104 (7)0.7786 (3)0.10480 (18)0.0481 (7)
H150.36230.86840.10180.058*
C130.6794 (7)0.5995 (3)0.06313 (15)0.0457 (7)
H130.81350.56850.03230.055*
C160.2865 (7)0.6908 (3)0.15540 (17)0.0452 (7)
H160.15520.72240.18660.054*
Cl50.6472 (2)0.34585 (8)0.11910 (5)0.0616 (3)
Cl40.7620 (2)0.84005 (10)−0.00545 (5)0.0660 (3)
O70.0604 (4)0.54895 (18)0.37772 (9)0.0331 (4)
O80.2660 (4)0.64018 (18)0.53311 (11)0.0449 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.02447 (18)0.02421 (18)0.02907 (18)−0.00534 (12)0.00625 (12)−0.00117 (12)
Cl20.0636 (5)0.0330 (4)0.0527 (5)−0.0225 (4)−0.0055 (4)0.0049 (3)
Cl30.0667 (5)0.0505 (5)0.0438 (4)−0.0079 (4)−0.0080 (4)−0.0074 (3)
O10.0368 (10)0.0253 (9)0.0450 (11)−0.0078 (8)0.0112 (9)−0.0070 (8)
C20.0508 (17)0.0239 (13)0.0339 (14)−0.0042 (12)0.0067 (12)−0.0011 (11)
C10.0325 (14)0.0239 (12)0.0274 (13)−0.0053 (10)−0.0012 (10)−0.0002 (10)
O20.0522 (12)0.0239 (9)0.0361 (10)−0.0091 (8)0.0002 (9)0.0025 (8)
C80.0348 (15)0.0244 (13)0.0427 (15)−0.0077 (11)0.0036 (12)−0.0007 (11)
C30.0385 (15)0.0225 (13)0.0383 (14)−0.0022 (11)0.0054 (12)−0.0030 (11)
C70.0443 (17)0.0260 (13)0.0390 (15)−0.0049 (12)0.0062 (12)0.0018 (11)
C40.0425 (16)0.0223 (13)0.0433 (15)−0.0063 (11)0.0061 (12)0.0026 (11)
C60.0412 (16)0.0328 (14)0.0388 (15)0.0008 (12)0.0007 (12)−0.0063 (12)
C50.0425 (16)0.0291 (14)0.0518 (17)−0.0075 (12)0.0023 (13)−0.0070 (12)
O50.0200 (9)0.0564 (12)0.0392 (10)−0.0081 (8)0.0039 (8)−0.0116 (9)
C90.0257 (13)0.0277 (13)0.0306 (13)−0.0048 (10)0.0023 (10)−0.0011 (10)
C100.0277 (14)0.0499 (17)0.0334 (14)−0.0084 (12)0.0027 (11)−0.0091 (12)
O60.0429 (11)0.0428 (11)0.0352 (10)−0.0103 (9)0.0099 (8)−0.0117 (9)
C110.0323 (14)0.0419 (15)0.0277 (13)−0.0034 (12)−0.0028 (11)−0.0107 (11)
C120.0402 (16)0.0382 (15)0.0320 (14)0.0038 (12)0.0012 (11)−0.0105 (12)
C140.0419 (17)0.0481 (18)0.0391 (16)−0.0075 (14)0.0001 (13)0.0007 (13)
C150.0489 (18)0.0373 (16)0.0570 (19)−0.0018 (14)−0.0011 (15)−0.0080 (14)
C130.0485 (18)0.0522 (19)0.0352 (15)0.0003 (15)0.0085 (13)−0.0096 (14)
C160.0443 (17)0.0421 (17)0.0506 (17)−0.0006 (14)0.0137 (14)−0.0152 (14)
Cl50.0829 (7)0.0394 (4)0.0605 (5)0.0066 (4)0.0191 (5)−0.0135 (4)
Cl40.0775 (6)0.0650 (6)0.0514 (5)−0.0220 (5)0.0086 (4)0.0081 (4)
O70.0256 (9)0.0427 (11)0.0335 (10)−0.0108 (8)0.0070 (8)−0.0095 (8)
O80.0527 (13)0.0266 (10)0.0495 (12)−0.0031 (9)0.0156 (10)0.0071 (9)

Geometric parameters (Å, °)

Zn1—O11.9315 (18)C5—H50.93
Zn1—O8i1.9335 (18)O5—C91.258 (3)
Zn1—O51.9458 (18)C9—O71.256 (3)
Zn1—O7ii1.9622 (18)C9—C101.507 (3)
Cl2—C81.735 (3)C10—O61.412 (3)
Cl3—C61.735 (3)C10—H10A0.97
O1—C11.250 (3)C10—H10B0.97
C2—O21.415 (3)O6—C111.365 (3)
C2—C11.518 (3)C11—C161.382 (4)
C2—H2A0.97C11—C121.392 (4)
C2—H2B0.97C12—C131.382 (4)
C1—O81.245 (3)C12—Cl51.726 (3)
O2—C31.372 (3)C14—C131.369 (4)
C8—C31.395 (4)C14—C151.380 (5)
C8—C71.383 (4)C14—Cl41.735 (3)
C3—C41.383 (4)C15—C161.383 (4)
C7—C61.389 (4)C15—H150.93
C7—H70.93C13—H130.93
C4—C51.385 (4)C16—H160.93
C4—H40.93O7—Zn1iii1.9622 (17)
C6—C51.371 (4)O8—Zn1i1.9335 (18)
O1—Zn1—O8i126.97 (8)C6—C5—H5120.1
O1—Zn1—O5113.18 (8)C4—C5—H5120.1
O8i—Zn1—O5107.88 (9)C9—O5—Zn1118.61 (16)
O1—Zn1—O7ii103.55 (8)O7—C9—O5121.7 (2)
O8i—Zn1—O7ii98.21 (8)O7—C9—C10120.3 (2)
O5—Zn1—O7ii103.04 (7)O5—C9—C10118.0 (2)
C1—O1—Zn1128.96 (17)O6—C10—C9113.7 (2)
O2—C2—C1115.7 (2)O6—C10—H10A108.8
O2—C2—H2A108.4C9—C10—H10A108.8
C1—C2—H2A108.4O6—C10—H10B108.8
O2—C2—H2B108.4C9—C10—H10B108.8
C1—C2—H2B108.4H10A—C10—H10B107.7
H2A—C2—H2B107.4C11—O6—C10119.4 (2)
O8—C1—O1126.4 (2)O6—C11—C16125.9 (2)
O8—C1—C2113.8 (2)O6—C11—C12115.7 (2)
O1—C1—C2119.8 (2)C16—C11—C12118.4 (3)
C3—O2—C2117.3 (2)C13—C12—C11120.8 (3)
C3—C8—C7121.6 (2)C13—C12—Cl5119.6 (2)
C3—C8—Cl2119.6 (2)C11—C12—Cl5119.6 (2)
C7—C8—Cl2118.8 (2)C13—C14—C15120.7 (3)
O2—C3—C8116.8 (2)C13—C14—Cl4119.3 (2)
O2—C3—C4124.7 (2)C15—C14—Cl4120.0 (3)
C8—C3—C4118.5 (3)C16—C15—C14119.4 (3)
C8—C7—C6118.2 (3)C16—C15—H15120.3
C8—C7—H7120.9C14—C15—H15120.3
C6—C7—H7120.9C14—C13—C12119.7 (3)
C3—C4—C5120.6 (3)C14—C13—H13120.2
C3—C4—H4119.7C12—C13—H13120.2
C5—C4—H4119.7C15—C16—C11121.1 (3)
C5—C6—C7121.3 (3)C15—C16—H16119.5
C5—C6—Cl3119.7 (2)C11—C16—H16119.5
C7—C6—Cl3119.0 (2)C9—O7—Zn1iii135.66 (16)
C6—C5—C4119.8 (3)C1—O8—Zn1i144.34 (19)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2B···Cl2iv0.972.733.610 (3)151

Symmetry codes: (iv) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5084).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc, Madison, Wisconsin, USA.
  • Huang, F.-P., Yu, Q., Bian, H. D. & Yan, S.-P. (2008). Polyhedron, 27, 3160–3166.
  • Qin, J., Ma, J.-P., Liu, L.-L., Huang, R.-Q. & Dong, Y.-B. (2009). Acta Cryst. C65, m66–m68. [PubMed]
  • Reineke, T. M., Eddaoudi, M., O’Keeffe, M. & Yaghi, O. M. (1999). Angew. Chem. Int. Ed.38, 2590–2594. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z. (2002). Angew. Chem. Int. Ed.41, 3800–3805. [PubMed]

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