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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m890.
Published online 2008 June 7. doi:  10.1107/S1600536808016899
PMCID: PMC2961700

Diaqua­bis[2-(benzyl­oxy)acetato]cobalt(II)

Abstract

In the mononuclear title complex, [Co(C9H9O3)2(H2O)2], each CoII atom is located on an inversion center and is hexa­coordinated by four O atoms from two benzyl­oxyacetate ligands [Co—O bond lengths = 2.0487 (9) and 2.1090 (9) Å] and two water mol­ecules [Co—O bond length = 2.0873 (9) Å] in a distorted octa­hedral geometry. In the crystal structure, inter­molecular hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance between phenyl rings = 3.692 (2) Å] link the mol­ecules into a supra­molecular structure.

Related literature

For the crystal structure of a similar CuII complex of benzyl­oxyacetate, see: Sun et al. (2008 [triangle]).

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Object name is e-64-0m890-scheme1.jpg

Experimental

Crystal data

  • [Co(C9H9O3)2(H2O)2]
  • M r = 425.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m890-efi1.jpg
  • a = 11.4968 (1) Å
  • b = 7.1557 (1) Å
  • c = 12.0054 (1) Å
  • β = 109.708 (1)°
  • V = 929.80 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.97 mm−1
  • T = 296 (2) K
  • 0.32 × 0.26 × 0.18 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.743, T max = 0.835
  • 7958 measured reflections
  • 2126 independent reflections
  • 1904 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.066
  • S = 1.07
  • 2115 reflections
  • 131 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.23 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016899/lx2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016899/lx2056Isup2.hkl

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

Acknowledgments

The authors thank the Guangdong Ocean University Project (No. 0612178 and No. 0612179) and Zhanjiang City Technology Tender Project (No. 0810014) for supporting this work.

supplementary crystallographic information

Comment

Recently, we have reported the crystal structure of the complex of benzyloxyacetate, [Cu(C9H9O3)2.2(H2O)], (Sun et al., 2008). Here we report the crystal structure of the title mononuclear complex of benzyloxyacetate, [Co(C9H9O3)2.2(H2O)], (Fig. 1).

The structure of the title compound is similar to that of the Cu(II) complex (Sun et al., 2008). The Co atom lies on an inversion center and displays an octahedral geometry defined by two carboxylate O atoms and two benzyloxy O atoms from two benzyloxyacetate ligands, and two water molecules, respectively. The Co—O and Co—Ow bond lengths are 2.0487 (9), 2.1090 (9) and 2.0873 (9) Å, respectively. The characteristic C—O(carboxylate) bond lengths suggest electron localization of the carboxylate groups of the anionic ligands. The molecular packing is stabilized by intermolecular O—H···O hydrogen bond interactions (Table 1). The crystal packing (Fig. 2) is further stabilized by aromatic π—π stacking interaction between the benzene ring from neighbouring molecules. The Cg···Cgii distance is 3.692 (2) Å (Cg is the centroids of the C4-C9 benzene ring, symmetry code as in Fig. 2).

Experimental

The ligand, benzyloxyacetic acid was commercially available and used without further purification. The title complex was prepared by the addition of Cobalt diacetate trihydrate (2.38 g, 10 mmol) to a hot aqueous solution of benzyloxyacetic acid (1.66 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Pink prismatic crystals separated from the filtered solution after several days. C&H analysis. Calc. for C18H22CoO8: C 50.83, H 5.21%. Found: C 50.81, H 5.22%.

Refinement

The H atoms were placed in calculated positions, with C—H = 0.93 or 0.97 Å, and Uiso(H) = 1.2Ueq(C), and were refined in the riding-model approximation. The H atoms of the water molecule were was located in a difference Fourier map and refined with O—H = 0.85Å and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure of (I) with 30% probability ellipsoids. [Symmetry code: (i) -x, -y+1, -z+1.]
Fig. 2.
π—π interaction (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (ii) -x+1, -y+1, -z+1; (iii) x+1, y , z; (iv) -x+2, -y+1, -z+1; (v) x+2, y, z.]

Crystal data

[Co(C9H9O3)2(H2O)2]F000 = 442
Mr = 425.29Dx = 1.519 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7958 reflections
a = 11.4968 (1) Åθ = 1.9–27.5º
b = 7.1557 (1) ŵ = 0.97 mm1
c = 12.0054 (1) ÅT = 296 (2) K
β = 109.708 (1)ºPrism, pink
V = 929.80 (2) Å30.32 × 0.26 × 0.18 mm
Z = 2

Data collection

Bruker P4 diffractometer2126 independent reflections
Radiation source: fine-focus sealed tube1904 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
Detector resolution: 10.000 pixels mm-1θmax = 27.5º
T = 296(2) Kθmin = 1.9º
ω scansh = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)k = −9→8
Tmin = 0.743, Tmax = 0.835l = −15→15
7958 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066  w = 1/[σ2(Fo2) + (0.0357P)2 + 0.2056P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2115 reflectionsΔρmax = 0.27 e Å3
131 parametersΔρmin = −0.23 e Å3
3 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Co10.00000.50000.50000.02597 (10)
O1W−0.07843 (9)0.62124 (13)0.33323 (8)0.0367 (2)
O1−0.04160 (8)0.73017 (12)0.58087 (8)0.0344 (2)
O20.02557 (13)1.00099 (11)0.66922 (10)0.0431 (3)
O30.15775 (8)0.66897 (13)0.52873 (8)0.0349 (2)
C10.03731 (12)0.85740 (17)0.61469 (10)0.0309 (3)
C20.15726 (12)0.83967 (19)0.58941 (12)0.0363 (3)
C30.24243 (12)0.6638 (2)0.46413 (12)0.0395 (3)
C40.37510 (12)0.66780 (18)0.54400 (12)0.0339 (3)
C50.46331 (15)0.7544 (2)0.50689 (15)0.0433 (3)
C60.58642 (15)0.7538 (2)0.57881 (19)0.0553 (4)
C70.62120 (15)0.6693 (2)0.68845 (17)0.0549 (4)
C80.53398 (15)0.5825 (3)0.72509 (15)0.0523 (4)
C90.41170 (14)0.5813 (2)0.65364 (13)0.0433 (3)
H2A0.16590.94410.54130.044*
H2B0.22640.84200.66310.044*
H3A0.22690.77010.41100.047*
H3B0.22790.55120.41650.047*
H50.44000.81320.43350.052*
H60.64560.81050.55310.066*
H70.70350.67110.73730.066*
H80.55750.52410.79860.063*
H90.35330.52190.67920.052*
H1W1−0.0549 (19)0.573 (2)0.2805 (15)0.065*
H1W2−0.0696 (19)0.7387 (13)0.3341 (17)0.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.02885 (15)0.01952 (14)0.03148 (15)−0.00140 (8)0.01273 (10)−0.00332 (8)
O1W0.0462 (5)0.0281 (5)0.0367 (5)0.0011 (4)0.0153 (4)0.0015 (4)
O10.0407 (5)0.0245 (4)0.0436 (5)−0.0009 (4)0.0216 (4)−0.0046 (4)
O20.0696 (7)0.0230 (5)0.0448 (6)−0.0019 (4)0.0299 (5)−0.0070 (4)
O30.0326 (4)0.0299 (5)0.0470 (5)−0.0057 (4)0.0197 (4)−0.0106 (4)
C10.0446 (7)0.0220 (6)0.0275 (5)0.0022 (5)0.0139 (5)0.0011 (5)
C20.0383 (7)0.0265 (6)0.0434 (7)−0.0058 (5)0.0126 (6)−0.0080 (5)
C30.0362 (7)0.0477 (8)0.0386 (7)−0.0027 (6)0.0178 (5)−0.0039 (6)
C40.0347 (6)0.0295 (6)0.0409 (7)−0.0001 (5)0.0170 (5)−0.0025 (5)
C50.0432 (7)0.0376 (8)0.0559 (9)−0.0003 (6)0.0258 (7)0.0035 (6)
C60.0400 (8)0.0425 (9)0.0919 (13)−0.0059 (7)0.0333 (8)−0.0052 (9)
C70.0360 (7)0.0473 (9)0.0726 (11)0.0065 (7)0.0068 (7)−0.0131 (8)
C80.0505 (9)0.0526 (10)0.0488 (8)0.0164 (8)0.0101 (7)0.0011 (7)
C90.0440 (8)0.0403 (8)0.0491 (8)0.0040 (6)0.0202 (6)0.0056 (7)

Geometric parameters (Å, °)

Co1—O12.0487 (9)C3—C41.503 (2)
Co1—O32.1090 (9)C3—H3A0.9700
Co1—O1W2.0873 (9)C3—H3B0.9700
O1—C11.252 (2)C4—C51.384 (2)
O2—C11.250 (2)C4—C91.385 (2)
Co1—O1i2.0487 (9)C5—C61.387 (2)
Co1—O3i2.1090 (9)C5—H50.9300
Co1—O1Wi2.0873 (9)C6—C71.380 (3)
O3—C21.423 (2)C6—H60.9300
O3—C31.435 (2)C7—C81.372 (3)
O1W—H1W10.84 (2)C7—H70.9300
O1W—H1W20.846 (9)C8—C91.378 (2)
C1—C21.514 (2)C8—H80.9300
C2—H2A0.9700C9—H90.9300
C2—H2B0.9700
O1—Co1—O1i180.0C1—C2—H2B109.7
O1—Co1—O377.70 (3)C2—O3—C3114.77 (10)
O1—Co1—O3i102.30 (3)C2—O3—Co1115.10 (7)
O1—Co1—O1W91.49 (4)C3—O3—Co1126.84 (8)
O1—Co1—O1Wi88.51 (4)C4—C3—H3A109.1
O3i—Co1—O3180.00 (7)C4—C3—H3B109.1
O1W—Co1—O3i90.68 (4)C4—C5—C6120.18 (15)
O1W—Co1—O389.32 (4)C4—C5—H5119.9
O1Wi—Co1—O1W180.0C4—C9—H9119.7
Co1—O1W—H1W1114.1 (14)C5—C4—C9119.03 (13)
Co1—O1W—H1W2112.9 (13)C5—C4—C3119.94 (13)
O1i—Co1—O3102.30 (3)C5—C6—H6119.9
O1i—Co1—O3i77.70 (3)C6—C5—H5119.9
O1i—Co1—O1Wi91.49 (4)C6—C7—H7120.1
O1i—Co1—O1W88.51 (4)C7—C8—C9120.38 (16)
O1Wi—Co1—O3i89.32 (4)C7—C8—H8119.8
O1Wi—Co1—O390.68 (4)C7—C6—C5120.12 (15)
O1—C1—C2118.90 (11)C7—C6—H6119.9
O2—C1—O1124.96 (13)C8—C7—C6119.76 (15)
O2—C1—C2116.14 (12)C8—C7—H7120.1
O3—C2—C1109.61 (10)C8—C9—C4120.52 (15)
O3—C2—H2A109.7C8—C9—H9119.7
O3—C2—H2B109.7C9—C4—C3121.01 (12)
O3—C3—C4112.47 (11)C9—C8—H8119.8
O3—C3—H3A109.1H1W1—O1W—H1W2110.4 (14)
O3—C3—H3B109.1H2A—C2—H2B108.2
C1—O1—Co1118.60 (8)H3A—C3—H3B107.8
C1—C2—H2A109.7
O1Wi—Co1—O1—C188.19 (9)Co1—O3—C2—C1−1.77 (13)
O1W—Co1—O1—C1−91.81 (9)O2—C1—C2—O3179.19 (11)
O3i—Co1—O1—C1177.16 (9)O1—C1—C2—O3−0.56 (17)
O3—Co1—O1—C1−2.84 (9)C2—O3—C3—C467.25 (15)
O1—Co1—O3—C22.39 (9)C1—O3—C3—C490.21 (17)
O1i—C1—O3—C2−177.45 (11)O3—C3—C4—C5−147.57 (13)
O1Wi—Co1—O3—C2−85.93 (9)O3—C3—C4—C934.23 (19)
O1W—Co1—O3—C294.07 (9)C9—C4—C5—C60.1 (2)
O1—Co1—O3—C3−155.88 (11)C3—C4—C5—C6−178.14 (14)
O1i—Co1—O3—C324.12 (11)C4—C5—C6—C7−1.0 (2)
O1Wi—Co1—O3—C3115.79 (11)C5—C6—C7—C81.3 (3)
O1W—Co1—O3—C3−64.21 (11)C6—C7—C8—C9−0.8 (3)
Co1—O1—C1—O2−176.97 (10)C7—C8—C9—C4−0.1 (3)
Co1—O1—C1—C22.76 (15)C5—C4—C9—C80.4 (2)
C3—O3—C2—C1159.19 (11)C3—C4—C9—C8178.66 (14)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O2ii0.84 (2)1.94 (1)2.768 (2)169 (2)
O1W—H1W2···O2iii0.846 (9)1.94 (1)2.773 (1)171 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2056).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2000). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, S.-L., Chen, C.-L., Gu, C.-S., Song, W.-D. & Hao, X.-M. (2008). Acta Cryst. E64, m691. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography