catena-Poly[zinc(II)-bis-[μ-2-(2,4-dichloro-phen-oxy)acetato]].

The title polymeric compound, [Zn(C(8)H(5)Cl(2)O(3))(2)](n), was prepared by reaction of zinc(II) chloride with 2,4-dichloro-phenoxy-acetic acid and sodium hydroxide under hydro-thermal conditions. The Zn(II) atom is coordinated in a distorted tetra-hedral environment by four O atoms from four 2,4-dichloro-phenoxy-acetate 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 = 505.43

Triclinic,

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[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 ▶); 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.

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

[Zn(C8H5Cl2O3)2]	Z = 2
Mr = 505.43	F(000) = 504
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0663P)2] where P = (Fo2 + 2Fc2)/3
3255 reflections	(Δ/σ)max = 0.024
244 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl2iv	0.97	2.73	3.610 (3)	151

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) .