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

Liu, S.-Z.

doi:10.1107/S1600536810015977

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m621

https://doi.org/10.1107/S1600536810015977

Open

access

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

Shi-Zhu Liu ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China
^*Correspondence e-mail: liushizhu521@126.com

(Received 18 April 2010; accepted 30 April 2010; online 8 May 2010)

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 Zn^II atom is coordinated in a distorted tetrahedral environment by four O atoms from four 2,4-dichlorophenoxyacetate ligands. Each ligand bridges two Zn^II 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 ); Huang et al. (2008 ); Reineke et al. (1999 ); Xiong et al. (2002 ).

Experimental

Crystal data

[Zn(C₈H₅Cl₂O₃)₂]
M_r = 505.43
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.091
S = 0.94
3255 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cl2ⁱ	0.97	2.73	3.610 (3)	151
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015977/ci5084Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

[Zn(C₈H₅Cl₂O₃)₂]	Z = 2
M_r = 505.43	F(000) = 504
Triclinic, P1	D_x = 1.833 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7322 (10) Å	Cell parameters from 2642 reflections
b = 10.459 (2) Å	θ = 2.5–27.7°
c = 18.979 (4) Å	µ = 1.96 mm⁻¹
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 top

Bruker SMART APEXII CCD diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	2849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.617, T_max = 0.731	k = −12→8
4737 measured reflections	l = −22→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0663P)²] where P = (F_o² + 2F_c²)/3
3255 reflections	(Δ/σ)_max = 0.024
244 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Zn(C₈H₅Cl₂O₃)₂]	γ = 82.847 (3)°
M_r = 505.43	V = 915.8 (3) Å³
Triclinic, P1	Z = 2
a = 4.7322 (10) Å	Mo Kα radiation
b = 10.459 (2) Å	µ = 1.96 mm⁻¹
c = 18.979 (4) Å	T = 296 K
α = 79.340 (2)°	0.56 × 0.21 × 0.16 mm
β = 89.838 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3255 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2849 reflections with I > 2σ(I)
T_min = 0.617, T_max = 0.731	R_int = 0.021
4737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 0.94	Δρ_max = 0.34 e Å⁻³
3255 reflections	Δρ_min = −0.39 e Å⁻³
244 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Zn1	0.66929 (6)	0.53465 (3)	0.409892 (14)	0.02622 (12)
Cl2	0.46808 (18)	1.18539 (7)	0.33205 (4)	0.0500 (2)
Cl3	−0.18417 (19)	1.02366 (8)	0.14274 (4)	0.0538 (2)
O1	0.5602 (4)	0.69621 (17)	0.44411 (10)	0.0354 (4)
C2	0.2487 (7)	0.8626 (2)	0.48725 (14)	0.0368 (6)
H2A	0.0425	0.8686	0.4858	0.044*
H2B	0.3034	0.8854	0.5321	0.044*
C1	0.3707 (5)	0.7213 (2)	0.48733 (13)	0.0283 (5)
O2	0.3338 (4)	0.95654 (17)	0.43021 (10)	0.0381 (4)
C8	0.2572 (6)	1.0724 (2)	0.31164 (15)	0.0344 (6)
C3	0.2031 (6)	0.9673 (2)	0.36461 (14)	0.0336 (6)
C7	0.1426 (6)	1.0904 (3)	0.24305 (15)	0.0374 (6)
H7	0.1846	1.1593	0.2077	0.045*
C4	0.0218 (6)	0.8825 (3)	0.34807 (15)	0.0370 (6)
H4	−0.0198	0.8129	0.3830	0.044*
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	−0.2199	0.8429	0.2693	0.049*
O5	0.4663 (4)	0.5250 (2)	0.32238 (10)	0.0379 (4)
C9	0.2002 (5)	0.5268 (2)	0.32394 (13)	0.0285 (5)
C10	0.0513 (6)	0.4985 (3)	0.25952 (14)	0.0365 (6)
H10A	−0.0637	0.4283	0.2752	0.044*
H10B	−0.0762	0.5759	0.2383	0.044*
O6	0.2391 (4)	0.46218 (19)	0.20660 (10)	0.0394 (5)
C11	0.3544 (6)	0.5571 (3)	0.16035 (14)	0.0335 (6)
C12	0.5536 (6)	0.5123 (3)	0.11352 (14)	0.0371 (6)
C14	0.6058 (7)	0.7315 (3)	0.05874 (16)	0.0440 (7)
C15	0.4104 (7)	0.7786 (3)	0.10480 (18)	0.0481 (7)
H15	0.3623	0.8684	0.1018	0.058*
C13	0.6794 (7)	0.5995 (3)	0.06313 (15)	0.0457 (7)
H13	0.8135	0.5685	0.0323	0.055*
C16	0.2865 (7)	0.6908 (3)	0.15540 (17)	0.0452 (7)
H16	0.1552	0.7224	0.1866	0.054*
Cl5	0.6472 (2)	0.34585 (8)	0.11910 (5)	0.0616 (3)
Cl4	0.7620 (2)	0.84005 (10)	−0.00545 (5)	0.0660 (3)
O7	0.0604 (4)	0.54895 (18)	0.37772 (9)	0.0331 (4)
O8	0.2660 (4)	0.64018 (18)	0.53311 (11)	0.0449 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02447 (18)	0.02421 (18)	0.02907 (18)	−0.00534 (12)	0.00625 (12)	−0.00117 (12)
Cl2	0.0636 (5)	0.0330 (4)	0.0527 (5)	−0.0225 (4)	−0.0055 (4)	0.0049 (3)
Cl3	0.0667 (5)	0.0505 (5)	0.0438 (4)	−0.0079 (4)	−0.0080 (4)	−0.0074 (3)
O1	0.0368 (10)	0.0253 (9)	0.0450 (11)	−0.0078 (8)	0.0112 (9)	−0.0070 (8)
C2	0.0508 (17)	0.0239 (13)	0.0339 (14)	−0.0042 (12)	0.0067 (12)	−0.0011 (11)
C1	0.0325 (14)	0.0239 (12)	0.0274 (13)	−0.0053 (10)	−0.0012 (10)	−0.0002 (10)
O2	0.0522 (12)	0.0239 (9)	0.0361 (10)	−0.0091 (8)	0.0002 (9)	0.0025 (8)
C8	0.0348 (15)	0.0244 (13)	0.0427 (15)	−0.0077 (11)	0.0036 (12)	−0.0007 (11)
C3	0.0385 (15)	0.0225 (13)	0.0383 (14)	−0.0022 (11)	0.0054 (12)	−0.0030 (11)
C7	0.0443 (17)	0.0260 (13)	0.0390 (15)	−0.0049 (12)	0.0062 (12)	0.0018 (11)
C4	0.0425 (16)	0.0223 (13)	0.0433 (15)	−0.0063 (11)	0.0061 (12)	0.0026 (11)
C6	0.0412 (16)	0.0328 (14)	0.0388 (15)	0.0008 (12)	0.0007 (12)	−0.0063 (12)
C5	0.0425 (16)	0.0291 (14)	0.0518 (17)	−0.0075 (12)	0.0023 (13)	−0.0070 (12)
O5	0.0200 (9)	0.0564 (12)	0.0392 (10)	−0.0081 (8)	0.0039 (8)	−0.0116 (9)
C9	0.0257 (13)	0.0277 (13)	0.0306 (13)	−0.0048 (10)	0.0023 (10)	−0.0011 (10)
C10	0.0277 (14)	0.0499 (17)	0.0334 (14)	−0.0084 (12)	0.0027 (11)	−0.0091 (12)
O6	0.0429 (11)	0.0428 (11)	0.0352 (10)	−0.0103 (9)	0.0099 (8)	−0.0117 (9)
C11	0.0323 (14)	0.0419 (15)	0.0277 (13)	−0.0034 (12)	−0.0028 (11)	−0.0107 (11)
C12	0.0402 (16)	0.0382 (15)	0.0320 (14)	0.0038 (12)	0.0012 (11)	−0.0105 (12)
C14	0.0419 (17)	0.0481 (18)	0.0391 (16)	−0.0075 (14)	0.0001 (13)	0.0007 (13)
C15	0.0489 (18)	0.0373 (16)	0.0570 (19)	−0.0018 (14)	−0.0011 (15)	−0.0080 (14)
C13	0.0485 (18)	0.0522 (19)	0.0352 (15)	0.0003 (15)	0.0085 (13)	−0.0096 (14)
C16	0.0443 (17)	0.0421 (17)	0.0506 (17)	−0.0006 (14)	0.0137 (14)	−0.0152 (14)
Cl5	0.0829 (7)	0.0394 (4)	0.0605 (5)	0.0066 (4)	0.0191 (5)	−0.0135 (4)
Cl4	0.0775 (6)	0.0650 (6)	0.0514 (5)	−0.0220 (5)	0.0086 (4)	0.0081 (4)
O7	0.0256 (9)	0.0427 (11)	0.0335 (10)	−0.0108 (8)	0.0070 (8)	−0.0095 (8)
O8	0.0527 (13)	0.0266 (10)	0.0495 (12)	−0.0031 (9)	0.0156 (10)	0.0071 (9)

Geometric parameters (Å, º) top

Zn1—O1	1.9315 (18)	C5—H5	0.93
Zn1—O8ⁱ	1.9335 (18)	O5—C9	1.258 (3)
Zn1—O5	1.9458 (18)	C9—O7	1.256 (3)
Zn1—O7ⁱⁱ	1.9622 (18)	C9—C10	1.507 (3)
Cl2—C8	1.735 (3)	C10—O6	1.412 (3)
Cl3—C6	1.735 (3)	C10—H10A	0.97
O1—C1	1.250 (3)	C10—H10B	0.97
C2—O2	1.415 (3)	O6—C11	1.365 (3)
C2—C1	1.518 (3)	C11—C16	1.382 (4)
C2—H2A	0.97	C11—C12	1.392 (4)
C2—H2B	0.97	C12—C13	1.382 (4)
C1—O8	1.245 (3)	C12—Cl5	1.726 (3)
O2—C3	1.372 (3)	C14—C13	1.369 (4)
C8—C3	1.395 (4)	C14—C15	1.380 (5)
C8—C7	1.383 (4)	C14—Cl4	1.735 (3)
C3—C4	1.383 (4)	C15—C16	1.383 (4)
C7—C6	1.389 (4)	C15—H15	0.93
C7—H7	0.93	C13—H13	0.93
C4—C5	1.385 (4)	C16—H16	0.93
C4—H4	0.93	O7—Zn1ⁱⁱⁱ	1.9622 (17)
C6—C5	1.371 (4)	O8—Zn1ⁱ	1.9335 (18)

O1—Zn1—O8ⁱ	126.97 (8)	C6—C5—H5	120.1
O1—Zn1—O5	113.18 (8)	C4—C5—H5	120.1
O8ⁱ—Zn1—O5	107.88 (9)	C9—O5—Zn1	118.61 (16)
O1—Zn1—O7ⁱⁱ	103.55 (8)	O7—C9—O5	121.7 (2)
O8ⁱ—Zn1—O7ⁱⁱ	98.21 (8)	O7—C9—C10	120.3 (2)
O5—Zn1—O7ⁱⁱ	103.04 (7)	O5—C9—C10	118.0 (2)
C1—O1—Zn1	128.96 (17)	O6—C10—C9	113.7 (2)
O2—C2—C1	115.7 (2)	O6—C10—H10A	108.8
O2—C2—H2A	108.4	C9—C10—H10A	108.8
C1—C2—H2A	108.4	O6—C10—H10B	108.8
O2—C2—H2B	108.4	C9—C10—H10B	108.8
C1—C2—H2B	108.4	H10A—C10—H10B	107.7
H2A—C2—H2B	107.4	C11—O6—C10	119.4 (2)
O8—C1—O1	126.4 (2)	O6—C11—C16	125.9 (2)
O8—C1—C2	113.8 (2)	O6—C11—C12	115.7 (2)
O1—C1—C2	119.8 (2)	C16—C11—C12	118.4 (3)
C3—O2—C2	117.3 (2)	C13—C12—C11	120.8 (3)
C3—C8—C7	121.6 (2)	C13—C12—Cl5	119.6 (2)
C3—C8—Cl2	119.6 (2)	C11—C12—Cl5	119.6 (2)
C7—C8—Cl2	118.8 (2)	C13—C14—C15	120.7 (3)
O2—C3—C8	116.8 (2)	C13—C14—Cl4	119.3 (2)
O2—C3—C4	124.7 (2)	C15—C14—Cl4	120.0 (3)
C8—C3—C4	118.5 (3)	C16—C15—C14	119.4 (3)
C8—C7—C6	118.2 (3)	C16—C15—H15	120.3
C8—C7—H7	120.9	C14—C15—H15	120.3
C6—C7—H7	120.9	C14—C13—C12	119.7 (3)
C3—C4—C5	120.6 (3)	C14—C13—H13	120.2
C3—C4—H4	119.7	C12—C13—H13	120.2
C5—C4—H4	119.7	C15—C16—C11	121.1 (3)
C5—C6—C7	121.3 (3)	C15—C16—H16	119.5
C5—C6—Cl3	119.7 (2)	C11—C16—H16	119.5
C7—C6—Cl3	119.0 (2)	C9—O7—Zn1ⁱⁱⁱ	135.66 (16)
C6—C5—C4	119.8 (3)	C1—O8—Zn1ⁱ	144.34 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl2^iv	0.97	2.73	3.610 (3)	151

Symmetry code: (iv) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₅Cl₂O₃)₂]
M_r	505.43
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.7322 (10), 10.459 (2), 18.979 (4)
α, β, γ (°)	79.340 (2), 89.838 (2), 82.847 (3)
V (Å³)	915.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.56 × 0.21 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.617, 0.731
No. of measured, independent and observed [I > 2σ(I)] reflections	4737, 3255, 2849
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.091, 0.94
No. of reflections	3255
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.39

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl2ⁱ	0.97	2.73	3.610 (3)	151

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

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

References

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