catena-Poly[[diaqua­cobalt(II)]-μ-4,4′-[1,4-phenyl­enebis(­oxy)]dibutano­ato-κ4O,O′:O′′,O′′′]

Zhao, Y.-Y.

doi:10.1107/S1600536810053742

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m138

doi:10.1107/S1600536810053742

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catena-Poly[[diaquacobalt(II)]-μ-4,4′-[1,4-phenylenebis(oxy)]dibutanoato-κ⁴O,O′:O′′,O′′′]

Ying-Ying Zhao ^a

^aCollege of Chemistry and Chemical Engineering, Bohai University, 121013 Jinzhou, Liaoning, People's Republic of China

(Received 3 December 2010; accepted 22 December 2010; online 8 January 2011)

In the title coordination polymer, [Co(C₁₄H₁₆O₆)(H₂O)₂]_n, the Co^II ion, situated on a twofold rotation axis, is coordinated by four O atoms from two 4,4′-[1,4-phenylenebis(oxy)]dibutanoate (L) ligands and two water molecules in a highly distorted octahedral geometry. Each L ligand is situated on an inversion center and bridges two Co^II atoms, forming a zigzag polymeric chain propagating in [10 $[\overline{1}]$ ]. Intermolecular O—H⋯O hydrogen bonds further consolidate the crystal packing.

Related literature

For related structures, see: Dai et al. (2009 ); Zhu et al. (2008 ); Li et al. (2010 ). For the synthesis of 4,4′-[1,4-phenylenebis(oxy)]dibutanoic acid, see: Zhang et al. (2009 ).

Experimental

Crystal data

[Co(C₁₄H₁₆O₆)(H₂O)₂]
M_r = 375.23
Monoclinic, C 2/c
a = 28.835 (4) Å
b = 5.4057 (8) Å
c = 10.6425 (16) Å
β = 98.126 (2)°
V = 1642.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.829, T_max = 0.900
5204 measured reflections
1459 independent reflections
1343 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.080
S = 1.00
1459 reflections
105 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H9⋯O2ⁱ	0.85	1.88	2.7335 (19)	176
O4—H8⋯O1ⁱⁱ	0.85	1.89	2.740 (2)	175
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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 global, I. DOI: 10.1107/S1600536810053742/cv5012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053742/cv5012Isup2.hkl

checkCIF report

Comment top

Benzene-1,4-dioxydiacetic acid is an important biologically active compound commonly used in herbicides and plant-growth agents. Two phenoxyacetate groups have versatile bonding modes to metal ions and easily forms complexes (Dai et al., 2009; Zhu et al., 2008; Li et al., 2010). Benzene-1,4-dioxydibutanoic acid is an interesting dicarboxylate ligand. To our knowledge, there have been no reports about its coordination compounds. Recently, we obtained the title cobalt polymer (I), and its crystal structure is reported here.

In the structure of (I), each cobalt(II) atom is coordinated by four oxygen atoms from two benzene-1,4-dioxydibutyrate ligands and two water molecules, displaing highly distorted octahedral geometry (Fig. 1). Each ligand situated on an inversion center bridges two cobalt(II) centers to form polymeric zigzag chain propagated in direction [10–1] (Fig. 2). Intermolecular O—H···O hydrogen bonds (Table 1) consolidate further the crystal packing.

Related literature top

For related structures, see: Dai et al. (2009); Zhu et al. (2008); Li et al. (2010). For the synthesis of 4,4'-[1,4-phenylenebis(oxy)]dibutanoic acid, see: Zhang et al. (2009).

Experimental top

The ligand was prepared according to the literature method (Zhang et al., 2009). A mixture of CoSO4 (0.5 mmol), benzene-1,4-dioxydiacetic acid (0.5 mmol), NaOH (1 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated at 423 K for three days and then cooled to room temperature. Single crystals were obtained after washing with water and drying in air.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. A portion of the crystal structure of (I) showing the atomic labeling and 30% probability displacement ellopsoids [symmetry codes: (A) -x, y, -z + 3/2; (B) -x + 1/2, -y + 5/2, -z + 1].
	Fig. 2. A portion ot the crystal packing of (I) showing the polymeric one-dimensional zigzag chain.

catena-Poly[[diaquacobalt(II)]-µ-4,4'-[1,4- phenylenebis(oxy)]dibutanoato-κ⁴O,O':O'',O'''] top

Crystal data top

[Co(C₁₄H₁₆O₆)(H₂O)₂]	F(000) = 780
M_r = 375.23	D_x = 1.518 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2107 reflections
a = 28.835 (4) Å	θ = 2.9–27.0°
b = 5.4057 (8) Å	µ = 1.08 mm⁻¹
c = 10.6425 (16) Å	T = 296 K
β = 98.126 (2)°	Acicular, red
V = 1642.2 (4) Å³	0.18 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1459 independent reflections
Radiation source: fine-focus sealed tube	1343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→34
T_min = 0.829, T_max = 0.900	k = −4→6
5204 measured reflections	l = −12→12

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0516P)² + 0.6799P] where P = (F_o² + 2F_c²)/3
1459 reflections	(Δ/σ)_max < 0.001
105 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Co(C₁₄H₁₆O₆)(H₂O)₂]	V = 1642.2 (4) Å³
M_r = 375.23	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.835 (4) Å	µ = 1.08 mm⁻¹
b = 5.4057 (8) Å	T = 296 K
c = 10.6425 (16) Å	0.18 × 0.16 × 0.10 mm
β = 98.126 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1459 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1343 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.900	R_int = 0.032
5204 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
1459 reflections	Δρ_min = −0.25 e Å⁻³
105 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Co1	0.0000	0.16787 (6)	0.7500	0.02397 (16)
O1	0.05242 (5)	0.4611 (3)	0.74548 (12)	0.0332 (3)
O2	0.03451 (5)	0.2091 (3)	0.58828 (13)	0.0399 (4)
O3	0.18305 (5)	1.0014 (3)	0.61283 (14)	0.0458 (4)
O4	0.04626 (5)	−0.0762 (3)	0.84698 (12)	0.0322 (3)
H8	0.0494	−0.2161	0.8127	0.048*
H9	0.0419	−0.1122	0.9221	0.048*
C1	0.05869 (7)	0.3883 (4)	0.63762 (18)	0.0280 (4)
C2	0.09363 (8)	0.5074 (5)	0.5643 (2)	0.0425 (6)
H2A	0.1135	0.3785	0.5375	0.051*
H2B	0.0766	0.5807	0.4882	0.051*
C3	0.12459 (8)	0.7026 (4)	0.6324 (2)	0.0374 (5)
H3A	0.1437	0.6303	0.7056	0.045*
H3B	0.1054	0.8315	0.6622	0.045*
C4	0.15584 (7)	0.8131 (4)	0.5448 (2)	0.0357 (5)
H4A	0.1761	0.6868	0.5174	0.043*
H4B	0.1371	0.8823	0.4703	0.043*
C5	0.21584 (7)	1.1201 (4)	0.55206 (19)	0.0338 (5)
C6	0.24618 (8)	1.2756 (5)	0.6269 (2)	0.0413 (6)
H6	0.2437	1.2927	0.7126	0.050*
C7	0.28037 (8)	1.4066 (4)	0.5754 (2)	0.0391 (5)
H7	0.3006	1.5115	0.6262	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0283 (2)	0.0205 (2)	0.0252 (2)	0.000	0.01100 (15)	0.000
O1	0.0445 (8)	0.0282 (8)	0.0301 (8)	−0.0084 (6)	0.0157 (6)	−0.0030 (6)
O2	0.0489 (9)	0.0464 (10)	0.0268 (8)	−0.0265 (8)	0.0139 (7)	−0.0082 (7)
O3	0.0502 (9)	0.0547 (11)	0.0350 (8)	−0.0326 (8)	0.0147 (7)	−0.0047 (7)
O4	0.0425 (8)	0.0297 (8)	0.0260 (7)	0.0093 (6)	0.0100 (6)	0.0018 (6)
C1	0.0286 (10)	0.0300 (11)	0.0259 (10)	−0.0043 (8)	0.0060 (8)	0.0024 (8)
C2	0.0476 (12)	0.0487 (15)	0.0343 (12)	−0.0212 (11)	0.0163 (10)	−0.0041 (10)
C3	0.0386 (12)	0.0432 (14)	0.0316 (11)	−0.0174 (10)	0.0097 (9)	−0.0016 (10)
C4	0.0356 (12)	0.0390 (14)	0.0333 (12)	−0.0125 (10)	0.0076 (9)	0.0007 (9)
C5	0.0338 (11)	0.0372 (13)	0.0308 (11)	−0.0119 (9)	0.0062 (9)	0.0047 (9)
C6	0.0492 (13)	0.0499 (14)	0.0258 (11)	−0.0216 (11)	0.0084 (10)	−0.0015 (10)
C7	0.0410 (12)	0.0446 (13)	0.0314 (11)	−0.0206 (11)	0.0039 (9)	−0.0022 (10)

Geometric parameters (Å, º) top

Co1—O4ⁱ	2.0485 (13)	C2—H2A	0.9700
Co1—O4	2.0485 (13)	C2—H2B	0.9700
Co1—O2	2.1181 (14)	C3—C4	1.508 (3)
Co1—O2ⁱ	2.1181 (14)	C3—H3A	0.9700
Co1—O1ⁱ	2.1954 (13)	C3—H3B	0.9700
Co1—O1	2.1955 (14)	C4—H4A	0.9700
O1—C1	1.251 (2)	C4—H4B	0.9700
O2—C1	1.263 (2)	C5—C6	1.382 (3)
O3—C5	1.377 (2)	C5—C7ⁱⁱ	1.384 (3)
O3—C4	1.420 (2)	C6—C7	1.388 (3)
O4—H8	0.8499	C6—H6	0.9300
O4—H9	0.8499	C7—C5ⁱⁱ	1.384 (3)
C1—C2	1.503 (3)	C7—H7	0.9300
C2—C3	1.501 (3)

O4ⁱ—Co1—O4	99.80 (8)	C1—C2—H2B	108.2
O4ⁱ—Co1—O2	90.32 (5)	H2A—C2—H2B	107.3
O4—Co1—O2	97.47 (6)	C2—C3—C4	110.28 (18)
O4—Co1—O2ⁱ	90.33 (5)	C2—C3—H3A	109.6
O2—Co1—O2ⁱ	167.91 (9)	C4—C3—H3A	109.6
O4—Co1—O1ⁱ	148.79 (5)	C2—C3—H3B	109.6
O2ⁱ—Co1—O1ⁱ	60.14 (5)	C4—C3—H3B	109.6
O4ⁱ—Co1—O1	148.79 (5)	H3A—C3—H3B	108.1
O4—Co1—O1	94.29 (6)	O3—C4—C3	107.70 (17)
O2—Co1—O1	60.15 (5)	O3—C4—H4A	110.2
O2ⁱ—Co1—O1	110.23 (6)	C3—C4—H4A	110.2
O1ⁱ—Co1—O1	87.57 (8)	O3—C4—H4B	110.2
C5—O3—C4	117.46 (16)	C3—C4—H4B	110.2
Co1—O4—H8	117.3	H4A—C4—H4B	108.5
Co1—O4—H9	116.6	O3—C5—C6	115.70 (19)
H8—O4—H9	103.9	O3—C5—C7ⁱⁱ	124.50 (19)
O1—C1—O2	118.67 (17)	C6—C5—C7ⁱⁱ	119.8 (2)
O1—C1—C2	122.41 (18)	C5—C6—C7	120.7 (2)
O2—C1—C2	118.92 (17)	C5—C6—H6	119.7
C3—C2—C1	116.56 (18)	C7—C6—H6	119.7
C3—C2—H2A	108.2	C5ⁱⁱ—C7—C6	119.5 (2)
C1—C2—H2A	108.2	C5ⁱⁱ—C7—H7	120.2
C3—C2—H2B	108.2	C6—C7—H7	120.2

O4ⁱ—Co1—O1—C1	−21.60 (18)	Co1—O1—C1—C2	−179.14 (19)
O4—Co1—O1—C1	95.34 (12)	Co1—O2—C1—O1	−1.4 (2)
O2—Co1—O1—C1	−0.82 (12)	Co1—O2—C1—C2	179.07 (17)
O2ⁱ—Co1—O1—C1	−172.73 (12)	O1—C1—C2—C3	6.2 (3)
O1ⁱ—Co1—O1—C1	−115.86 (13)	O2—C1—C2—C3	−174.3 (2)
C1ⁱ—Co1—O1—C1	−143.01 (11)	C1—C2—C3—C4	−177.1 (2)
O4ⁱ—Co1—O2—C1	170.22 (13)	C5—O3—C4—C3	177.08 (19)
O4—Co1—O2—C1	−89.86 (13)	C2—C3—C4—O3	178.05 (18)
O2ⁱ—Co1—O2—C1	39.90 (12)	C4—O3—C5—C6	−170.9 (2)
O1ⁱ—Co1—O2—C1	75.53 (13)	C4—O3—C5—C7ⁱⁱ	9.4 (3)
O1—Co1—O2—C1	0.81 (12)	O3—C5—C6—C7	−179.4 (2)
C1ⁱ—Co1—O2—C1	69.9 (2)	C7ⁱⁱ—C5—C6—C7	0.3 (4)
Co1—O1—C1—O2	1.4 (2)	C5—C6—C7—C5ⁱⁱ	−0.3 (4)

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, −y+5/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H9···O2ⁱⁱⁱ	0.85	1.88	2.7335 (19)	176
O4—H8···O1^iv	0.85	1.89	2.740 (2)	175

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₄H₁₆O₆)(H₂O)₂]
M_r	375.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	28.835 (4), 5.4057 (8), 10.6425 (16)
β (°)	98.126 (2)
V (Å³)	1642.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.18 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.829, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	5204, 1459, 1343
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.080, 1.00
No. of reflections	1459
No. of parameters	105
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O4—H9···O2ⁱ	0.85	1.88	2.7335 (19)	176
O4—H8···O1ⁱⁱ	0.85	1.89	2.740 (2)	175

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

References

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