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

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 CoII 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 CoII 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[Dai, Y. M., Tang, E., Huang, J. F., Yao, Y. G. & Huang, X. D. (2009). J. Mol. Struct. 918, 183-187.]); Zhu et al. (2008[Zhu, L., Zhu, H. & Sun, F. (2008). Acta Cryst. E64, m57.]); Li et al. (2010[Li, X. Y., Liu, C. B., Che, G. B., Wang, X. C., Li, C. X., Yan, Y. S. & Guan, Q. F. (2010). Inorg. Chim. Acta, 363, 1359-1366.]). For the synthesis of 4,4′-[1,4-phenyl­enebis(­oxy)]dibutanoic acid, see: Zhang et al. (2009[Zhang, T., Fan, H. L., Zhou, J. G. & Jin, Q. H. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 3056-3065.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C14H16O6)(H2O)2]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.829, Tmax = 0.900

  • 5204 measured reflections

  • 1459 independent reflections

  • 1343 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.080

  • S = 1.00

  • 1459 reflections

  • 105 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were placed in idealized positions (O—H = 0.85 Å and C—H = 0.93–0.97 Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

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
[Figure 1] 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].
[Figure 2] 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
Mr = 375.23Dx = 1.518 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2107 reflections
a = 28.835 (4) Åθ = 2.9–27.0°
b = 5.4057 (8) ŵ = 1.08 mm1
c = 10.6425 (16) ÅT = 296 K
β = 98.126 (2)°Acicular, red
V = 1642.2 (4) Å30.18 × 0.16 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1459 independent reflections
Radiation source: fine-focus sealed tube1343 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3434
Tmin = 0.829, Tmax = 0.900k = 46
5204 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0516P)2 + 0.6799P]
where P = (Fo2 + 2Fc2)/3
1459 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
[Co(C14H16O6)(H2O)2]V = 1642.2 (4) Å3
Mr = 375.23Z = 4
Monoclinic, C2/cMo Kα radiation
a = 28.835 (4) ŵ = 1.08 mm1
b = 5.4057 (8) ÅT = 296 K
c = 10.6425 (16) Å0.18 × 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)
Tmin = 0.829, Tmax = 0.900Rint = 0.032
5204 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.00Δρmax = 0.26 e Å3
1459 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
Co10.00000.16787 (6)0.75000.02397 (16)
O10.05242 (5)0.4611 (3)0.74548 (12)0.0332 (3)
O20.03451 (5)0.2091 (3)0.58828 (13)0.0399 (4)
O30.18305 (5)1.0014 (3)0.61283 (14)0.0458 (4)
O40.04626 (5)0.0762 (3)0.84698 (12)0.0322 (3)
H80.04940.21610.81270.048*
H90.04190.11220.92210.048*
C10.05869 (7)0.3883 (4)0.63762 (18)0.0280 (4)
C20.09363 (8)0.5074 (5)0.5643 (2)0.0425 (6)
H2A0.11350.37850.53750.051*
H2B0.07660.58070.48820.051*
C30.12459 (8)0.7026 (4)0.6324 (2)0.0374 (5)
H3A0.14370.63030.70560.045*
H3B0.10540.83150.66220.045*
C40.15584 (7)0.8131 (4)0.5448 (2)0.0357 (5)
H4A0.17610.68680.51740.043*
H4B0.13710.88230.47030.043*
C50.21584 (7)1.1201 (4)0.55206 (19)0.0338 (5)
C60.24618 (8)1.2756 (5)0.6269 (2)0.0413 (6)
H60.24371.29270.71260.050*
C70.28037 (8)1.4066 (4)0.5754 (2)0.0391 (5)
H70.30061.51150.62620.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0283 (2)0.0205 (2)0.0252 (2)0.0000.01100 (15)0.000
O10.0445 (8)0.0282 (8)0.0301 (8)0.0084 (6)0.0157 (6)0.0030 (6)
O20.0489 (9)0.0464 (10)0.0268 (8)0.0265 (8)0.0139 (7)0.0082 (7)
O30.0502 (9)0.0547 (11)0.0350 (8)0.0326 (8)0.0147 (7)0.0047 (7)
O40.0425 (8)0.0297 (8)0.0260 (7)0.0093 (6)0.0100 (6)0.0018 (6)
C10.0286 (10)0.0300 (11)0.0259 (10)0.0043 (8)0.0060 (8)0.0024 (8)
C20.0476 (12)0.0487 (15)0.0343 (12)0.0212 (11)0.0163 (10)0.0041 (10)
C30.0386 (12)0.0432 (14)0.0316 (11)0.0174 (10)0.0097 (9)0.0016 (10)
C40.0356 (12)0.0390 (14)0.0333 (12)0.0125 (10)0.0076 (9)0.0007 (9)
C50.0338 (11)0.0372 (13)0.0308 (11)0.0119 (9)0.0062 (9)0.0047 (9)
C60.0492 (13)0.0499 (14)0.0258 (11)0.0216 (11)0.0084 (10)0.0015 (10)
C70.0410 (12)0.0446 (13)0.0314 (11)0.0206 (11)0.0039 (9)0.0022 (10)
Geometric parameters (Å, º) top
Co1—O4i2.0485 (13)C2—H2A0.9700
Co1—O42.0485 (13)C2—H2B0.9700
Co1—O22.1181 (14)C3—C41.508 (3)
Co1—O2i2.1181 (14)C3—H3A0.9700
Co1—O1i2.1954 (13)C3—H3B0.9700
Co1—O12.1955 (14)C4—H4A0.9700
O1—C11.251 (2)C4—H4B0.9700
O2—C11.263 (2)C5—C61.382 (3)
O3—C51.377 (2)C5—C7ii1.384 (3)
O3—C41.420 (2)C6—C71.388 (3)
O4—H80.8499C6—H60.9300
O4—H90.8499C7—C5ii1.384 (3)
C1—C21.503 (3)C7—H70.9300
C2—C31.501 (3)
O4i—Co1—O499.80 (8)C1—C2—H2B108.2
O4i—Co1—O290.32 (5)H2A—C2—H2B107.3
O4—Co1—O297.47 (6)C2—C3—C4110.28 (18)
O4—Co1—O2i90.33 (5)C2—C3—H3A109.6
O2—Co1—O2i167.91 (9)C4—C3—H3A109.6
O4—Co1—O1i148.79 (5)C2—C3—H3B109.6
O2i—Co1—O1i60.14 (5)C4—C3—H3B109.6
O4i—Co1—O1148.79 (5)H3A—C3—H3B108.1
O4—Co1—O194.29 (6)O3—C4—C3107.70 (17)
O2—Co1—O160.15 (5)O3—C4—H4A110.2
O2i—Co1—O1110.23 (6)C3—C4—H4A110.2
O1i—Co1—O187.57 (8)O3—C4—H4B110.2
C5—O3—C4117.46 (16)C3—C4—H4B110.2
Co1—O4—H8117.3H4A—C4—H4B108.5
Co1—O4—H9116.6O3—C5—C6115.70 (19)
H8—O4—H9103.9O3—C5—C7ii124.50 (19)
O1—C1—O2118.67 (17)C6—C5—C7ii119.8 (2)
O1—C1—C2122.41 (18)C5—C6—C7120.7 (2)
O2—C1—C2118.92 (17)C5—C6—H6119.7
C3—C2—C1116.56 (18)C7—C6—H6119.7
C3—C2—H2A108.2C5ii—C7—C6119.5 (2)
C1—C2—H2A108.2C5ii—C7—H7120.2
C3—C2—H2B108.2C6—C7—H7120.2
O4i—Co1—O1—C121.60 (18)Co1—O1—C1—C2179.14 (19)
O4—Co1—O1—C195.34 (12)Co1—O2—C1—O11.4 (2)
O2—Co1—O1—C10.82 (12)Co1—O2—C1—C2179.07 (17)
O2i—Co1—O1—C1172.73 (12)O1—C1—C2—C36.2 (3)
O1i—Co1—O1—C1115.86 (13)O2—C1—C2—C3174.3 (2)
C1i—Co1—O1—C1143.01 (11)C1—C2—C3—C4177.1 (2)
O4i—Co1—O2—C1170.22 (13)C5—O3—C4—C3177.08 (19)
O4—Co1—O2—C189.86 (13)C2—C3—C4—O3178.05 (18)
O2i—Co1—O2—C139.90 (12)C4—O3—C5—C6170.9 (2)
O1i—Co1—O2—C175.53 (13)C4—O3—C5—C7ii9.4 (3)
O1—Co1—O2—C10.81 (12)O3—C5—C6—C7179.4 (2)
C1i—Co1—O2—C169.9 (2)C7ii—C5—C6—C70.3 (4)
Co1—O1—C1—O21.4 (2)C5—C6—C7—C5ii0.3 (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···AD—HH···AD···AD—H···A
O4—H9···O2iii0.851.882.7335 (19)176
O4—H8···O1iv0.851.892.740 (2)175
Symmetry codes: (iii) x, y, z+1/2; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formula[Co(C14H16O6)(H2O)2]
Mr375.23
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)28.835 (4), 5.4057 (8), 10.6425 (16)
β (°) 98.126 (2)
V3)1642.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.08
Crystal size (mm)0.18 × 0.16 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.829, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections
5204, 1459, 1343
Rint0.032
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.080, 1.00
No. of reflections1459
No. of parameters105
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O4—H9···O2i0.851.882.7335 (19)176
O4—H8···O1ii0.851.892.740 (2)175
Symmetry codes: (i) x, y, z+1/2; (ii) x, y1, z.
 

References

First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDai, Y. M., Tang, E., Huang, J. F., Yao, Y. G. & Huang, X. D. (2009). J. Mol. Struct. 918, 183–187.  CSD CrossRef CAS Google Scholar
First citationLi, X. Y., Liu, C. B., Che, G. B., Wang, X. C., Li, C. X., Yan, Y. S. & Guan, Q. F. (2010). Inorg. Chim. Acta, 363, 1359–1366.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, T., Fan, H. L., Zhou, J. G. & Jin, Q. H. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 3056–3065.  Web of Science CrossRef CAS Google Scholar
First citationZhu, L., Zhu, H. & Sun, F. (2008). Acta Cryst. E64, m57.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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