metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Bis(2-hy­droxy­imino­methyl-6-meth­oxy­phenolato-κ2O1,N)cobalt(II)

aKey Laboratory of Non-Ferrous Metal Materials and Processing Technology, Department of Materials and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
*Correspondence e-mail: zsh720108@163.com

(Received 10 November 2008; accepted 24 November 2008; online 29 November 2008)

In the title compound, [Co(C8H8NO3)2], the CoII atom lies on a centre of inversion and is coordinated in a slightly distorted square-planar geometry by two N and two O atoms from the 2-hydroxy­imino­methyl-6-methoxy­phenolate ligands. Intra­molecular O—H⋯O hydrogen bonds are formed and the complexes form stacks along the b axis, with an inter­planar separation of 3.332 (1) Å between complexes. Pairs of C—H⋯O contacts are formed between complexes in neighbouring stacks.

Related literature

For recent related literature concerning Schiff-base compounds, see: Gupta & Sutar (2008[Gupta, K. C. & Sutar, A. K. (2008). Coord. Chem. Rev. 252, 1420-1450.]); Sreenivasulu et al. (2005[Sreenivasulu, B., Vetrichelvan, M., Zhao, F., Gao, S. & Vittal, J. J. (2005). Eur. J. Inorg. Chem. pp. 4635-4645.]); Zhang et al. (2008[Zhang, S. H., Jiang, Y. M. & Liu, Z. M. (2008). J. Coord. Chem. 61, 1927-1934.]); Raptopoulou et al. (2006[Raptopoulou, C. P., Boudalis, A. K., Sanakis, Y., Psycharis, V., Clemente-Juan, J. M., Fardis, M., Diamantopoulos, G. & Papavassiliou, G. (2006). Inorg. Chem. 45, 2317-2326.]); Milios et al. (2006[Milios, C. J., Vinslava, A., Whittaker, A. G., Parsons, S., Wernsdorfer, W., Christou, G., Perlepes, S. P. & Brechin, E. K. (2006). Inorg. Chem. 45, 5272-5274.]); Yang et al. (2007[Yang, C. I., Wernsdorfer, W., Lee, G. H. & Tsai, H. L. (2007). J. Am. Chem. Soc. 129, 456-457.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C8H8NO3)2]

  • Mr = 391.24

  • Monoclinic, P 21 /n

  • a = 8.4254 (19) Å

  • b = 4.9111 (11) Å

  • c = 18.951 (4) Å

  • β = 95.375 (3)°

  • V = 780.7 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.14 mm−1

  • T = 293 (2) K

  • 0.22 × 0.18 × 0.14 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: none

  • 4577 measured reflections

  • 1433 independent reflections

  • 1216 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.065

  • S = 1.04

  • 1433 reflections

  • 117 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.82 1.91 2.5336 (19) 132
C7—H7⋯O2ii 0.93 2.48 3.321 (2) 150
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART 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

Schiff-base complexes have been studied for many years (Gupta & Sutar, 2008; Sreenivasulu et al., 2005; Zhang et al., 2008) and have aroused increasing interest because of their antiviral, anticancer, catalytic and fluorescent properties. Most model studies of metal complexes of Schiff-base ligands containing salicylaldehyde derivatives and oxime have focused on the binding mode of the ligands (Raptopoulou et al., 2006; Milios et al., 2006; Yang et al., 2007). The crystal structures of the complexes demonstrate that the Schiff-base ligands act in a bidentate, tridentate or mu^5^:eta^1^:etaî^:eta^3^ mode, coordinating through the phenolato O, imine N, or oxime O atoms. Our research group is interested in the Schiff-base derived from 2-hydroxy-3-methoxy-benzaldehyde and hydroxylammonium chloride.

Related literature top

For recent related literature concerning Schiff-base compounds, see: Gupta & Sutar (2008); Sreenivasulu et al. (2005); Zhang et al. (2008); Raptopoulou et al. (2006); Milios et al. (2006); Yang et al. (2007).

Experimental top

A solution of (0.152 g, 1.0 mmol) 2-hydroxy-3-methoxy-benzaldehyde oxime and (0.056 g, 1 mmol) potassium hydroxide in 20 ml absolute methanol was added slowly to a solution of CoNO3.6H2O (0.145 g, 0.5 mmol) in methanol. The mixture was stirred for 1 h at room temperature to give a red solution which was filtered and the filtrate was left to stand at room temperature. Red block crystals suitable for were obtained by slow evaporation Yield: 80.1 % (based on Co). Elemental analysis calculated: C 49.12, H 4.12, N 7.16 %; found: C 48.99, H 4.21, N 7.22 %.

Refinement top

H atoms were positioned geometrically and refined with a riding model, with distances 0.96 (CH3) or 0.93 Å (aromatic ring), and with Uiso(H) = 1.2 Ueq(aromatic ring) or Uiso(H) = 1.5 Ueq(CH3), and with O–H distance 0.82 Å and Uiso(H) = 1.5 Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. Molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms. Dashed lines denote O—H···O hydrogen bonds. Symmetry code (A): -x, 1 - y, -z.
[Figure 2] Fig. 2. Packing diagram viewed down the b axis. Dasehd lines denote C—H···O contacts.
Bis(2-hydroxyiminomethyl-6-methoxyphenolato-κ2O1,N)cobalt(II) top
Crystal data top
[Co(C8H8NO3)2]F(000) = 402
Mr = 391.24Dx = 1.664 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4577 reflections
a = 8.4254 (19) Åθ = 2.6–25.5°
b = 4.9111 (11) ŵ = 1.14 mm1
c = 18.951 (4) ÅT = 293 K
β = 95.375 (3)°Block, red
V = 780.7 (3) Å30.22 × 0.18 × 0.14 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
1216 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.5°, θmin = 2.6°
ϕ and ω scansh = 1010
4577 measured reflectionsk = 55
1433 independent reflectionsl = 2222
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0303P)2 + 0.2885P]
where P = (Fo2 + 2Fc2)/3
1433 reflections(Δ/σ)max < 0.001
117 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
[Co(C8H8NO3)2]V = 780.7 (3) Å3
Mr = 391.24Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.4254 (19) ŵ = 1.14 mm1
b = 4.9111 (11) ÅT = 293 K
c = 18.951 (4) Å0.22 × 0.18 × 0.14 mm
β = 95.375 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1216 reflections with I > 2σ(I)
4577 measured reflectionsRint = 0.021
1433 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.065H-atom parameters constrained
S = 1.04Δρmax = 0.23 e Å3
1433 reflectionsΔρmin = 0.17 e Å3
117 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 > 2sigma(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
Co10.00000.50000.00000.03262 (15)
C10.1093 (2)0.0793 (4)0.09770 (10)0.0353 (4)
C20.0701 (2)0.1107 (4)0.14960 (10)0.0377 (5)
C30.1851 (3)0.2781 (4)0.18262 (11)0.0448 (5)
H30.15810.40280.21640.054*
C40.3423 (3)0.2610 (4)0.16538 (11)0.0477 (6)
H40.41960.37440.18800.057*
C50.3837 (3)0.0794 (4)0.11564 (11)0.0429 (5)
H50.48890.06960.10480.052*
C60.2676 (2)0.0939 (4)0.08055 (10)0.0361 (4)
C70.3153 (2)0.2796 (4)0.02809 (10)0.0386 (5)
H70.42170.27990.01870.046*
C80.1391 (3)0.3153 (5)0.20761 (12)0.0535 (6)
H8A0.10900.48970.19020.080*
H8B0.25290.30740.20770.080*
H8C0.09030.28980.25500.080*
N10.21926 (19)0.4465 (3)0.00691 (8)0.0363 (4)
O10.00708 (15)0.2354 (3)0.06754 (7)0.0387 (3)
O20.29495 (16)0.6086 (3)0.05443 (8)0.0487 (4)
H20.23010.71430.07440.073*
O30.08737 (17)0.1063 (3)0.16291 (8)0.0494 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0291 (2)0.0337 (2)0.0348 (2)0.00160 (15)0.00146 (15)0.00203 (16)
C10.0385 (11)0.0311 (10)0.0354 (11)0.0001 (8)0.0005 (9)0.0038 (8)
C20.0415 (11)0.0352 (10)0.0362 (11)0.0016 (9)0.0025 (9)0.0015 (9)
C30.0566 (14)0.0375 (11)0.0392 (11)0.0009 (10)0.0007 (10)0.0040 (9)
C40.0503 (13)0.0425 (12)0.0478 (13)0.0103 (10)0.0080 (10)0.0001 (10)
C50.0384 (11)0.0455 (12)0.0436 (12)0.0057 (9)0.0030 (9)0.0045 (10)
C60.0360 (10)0.0350 (10)0.0364 (11)0.0010 (8)0.0017 (8)0.0043 (8)
C70.0286 (10)0.0438 (11)0.0429 (11)0.0001 (9)0.0016 (8)0.0041 (9)
C80.0591 (14)0.0510 (14)0.0524 (13)0.0079 (11)0.0160 (11)0.0078 (11)
N10.0327 (9)0.0410 (10)0.0352 (9)0.0053 (7)0.0040 (7)0.0019 (7)
O10.0332 (7)0.0397 (8)0.0434 (8)0.0005 (6)0.0044 (6)0.0083 (6)
O20.0346 (8)0.0598 (10)0.0523 (9)0.0032 (7)0.0070 (7)0.0185 (8)
O30.0452 (9)0.0493 (8)0.0547 (9)0.0010 (7)0.0105 (7)0.0153 (8)
Geometric parameters (Å, º) top
Co1—O11.8290 (13)C4—H40.930
Co1—O1i1.8290 (13)C5—C61.414 (3)
Co1—N11.8826 (17)C5—H50.930
Co1—N1i1.8826 (17)C6—C71.434 (3)
C1—O11.331 (2)C7—N11.290 (2)
C1—C61.404 (3)C7—H70.930
C1—C21.417 (3)C8—O31.425 (2)
C2—O31.374 (2)C8—H8A0.960
C2—C31.376 (3)C8—H8B0.960
C3—C41.396 (3)C8—H8C0.960
C3—H30.930N1—O21.400 (2)
C4—C51.367 (3)O2—H20.820
O1—Co1—O1i180.00 (8)C6—C5—H5119.8
O1—Co1—N192.64 (6)C1—C6—C5119.37 (19)
O1i—Co1—N187.36 (6)C1—C6—C7121.78 (18)
O1—Co1—N1i87.36 (6)C5—C6—C7118.86 (18)
O1i—Co1—N1i92.64 (6)N1—C7—C6123.89 (18)
N1—Co1—N1i180.00 (13)N1—C7—H7118.1
O1—C1—C6123.29 (18)C6—C7—H7118.1
O1—C1—C2117.87 (18)O3—C8—H8A109.5
C6—C1—C2118.84 (17)O3—C8—H8B109.5
O3—C2—C3125.24 (19)H8A—C8—H8B109.5
O3—C2—C1114.13 (17)O3—C8—H8C109.5
C3—C2—C1120.62 (19)H8A—C8—H8C109.5
C2—C3—C4120.0 (2)H8B—C8—H8C109.5
C2—C3—H3120.0C7—N1—O2112.97 (16)
C4—C3—H3120.0C7—N1—Co1128.68 (14)
C5—C4—C3120.65 (19)O2—N1—Co1118.33 (12)
C5—C4—H4119.7C1—O1—Co1129.71 (13)
C3—C4—H4119.7N1—O2—H2109.5
C4—C5—C6120.5 (2)C2—O3—C8116.90 (17)
C4—C5—H5119.8
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.912.5336 (19)132
C7—H7···O2ii0.932.483.321 (2)150
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Co(C8H8NO3)2]
Mr391.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)8.4254 (19), 4.9111 (11), 18.951 (4)
β (°) 95.375 (3)
V3)780.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.14
Crystal size (mm)0.22 × 0.18 × 0.14
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4577, 1433, 1216
Rint0.021
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.065, 1.04
No. of reflections1433
No. of parameters117
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.912.5336 (19)131.8
C7—H7···O2ii0.932.483.321 (2)150.3
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

Acknowledgements

This work is financially supported by the Young Science Foundation of Guangxi Province of China (grant No. 0832085)

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGupta, K. C. & Sutar, A. K. (2008). Coord. Chem. Rev. 252, 1420–1450.  Web of Science CrossRef CAS Google Scholar
First citationMilios, C. J., Vinslava, A., Whittaker, A. G., Parsons, S., Wernsdorfer, W., Christou, G., Perlepes, S. P. & Brechin, E. K. (2006). Inorg. Chem. 45, 5272–5274.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationRaptopoulou, C. P., Boudalis, A. K., Sanakis, Y., Psycharis, V., Clemente-Juan, J. M., Fardis, M., Diamantopoulos, G. & Papavassiliou, G. (2006). Inorg. Chem. 45, 2317–2326.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSreenivasulu, B., Vetrichelvan, M., Zhao, F., Gao, S. & Vittal, J. J. (2005). Eur. J. Inorg. Chem. pp. 4635–4645.  Web of Science CSD CrossRef Google Scholar
First citationYang, C. I., Wernsdorfer, W., Lee, G. H. & Tsai, H. L. (2007). J. Am. Chem. Soc. 129, 456–457.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationZhang, S. H., Jiang, Y. M. & Liu, Z. M. (2008). J. Coord. Chem. 61, 1927–1934.  Web of Science CSD CrossRef CAS Google Scholar

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