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

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Bis[2-(cyclo­pentyl­imino­meth­yl)-4-nitro­phenolato-κ2N2,O]cobalt(II)

aDepartment of Chemistry, Huainan Normal College, Huainan 232001, People's Republic of China
*Correspondence e-mail: xumaimai@126.com

(Received 11 January 2011; accepted 14 January 2011; online 22 January 2011)

In the title compound, [Co(C12H13N2O3)2], the CoII ion is situated on a twofold rotation axis and is coordinated by two N and two O atoms from two symmetry-related Schiff base 2-(cyclo­pentyl­imino­meth­yl)-4-nitro­phenolate ligands (L) in a distorted tetra­hedral geometry. The cyclo­pentyl ring in L is disordered over two conformations in a 0.640 (19):0.360 (19) ratio.

Related literature

For background to Schiff bases and their complexes, see: Salehzadeh et al. (2010[Salehzadeh, S., Golbedaghi, R. & Blackman, A. G. (2010). J. Coord. Chem. 63, 634-642.]). For cobalt(II/III) complexes with Schiff base ligands, see: Nejo et al. (2010[Nejo, A. A., Kolawole, G. A. & Nejo, A. O. (2010). J. Coord. Chem. 63, 4398-4410.]); Shahabadi et al. (2010[Shahabadi, N., Kashanian, S. & Darabi, F. (2010). Eur. J. Med. Chem. 45, 4239-4245.]). For the Schiff base complexes we have reported, see: Wei et al. (2008[Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008). Acta Cryst. E64, m859-m860.]); Wang et al. (2007[Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2007). Chin. J. Struct. Chem. 26, 1327-1331.]). For similar cobalt(II) complexes with Schiff bases, see: Bahron et al. (1994[Bahron, H., Larkworthy, L. F., Marecaux, A., Povey, D. C. & Smith, G. W. (1994). J. Chem. Crystallogr. 24, 145-150.]); Elerman et al. (1996[Elerman, Y., Kabak, M. & Tahir, M. N. (1996). Acta Cryst. C52, 2434-2436.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C12H13N2O3)2]

  • Mr = 525.42

  • Orthorhombic, F d d d

  • a = 18.057 (2) Å

  • b = 18.792 (2) Å

  • c = 30.070 (4) Å

  • V = 10203 (2) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.72 mm−1

  • T = 298 K

  • 0.17 × 0.13 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.888, Tmax = 0.919

  • 13092 measured reflections

  • 2381 independent reflections

  • 1143 reflections with I > 2σ(I)

  • Rint = 0.099

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.182

  • S = 0.92

  • 2381 reflections

  • 196 parameters

  • 66 restraints

  • H-atom parameters constrained

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The condensation reaction of aromatic carbaldehydes with primary amines has been shown to offer an easy and inexpensive way of forming a variety of polydentate Schiff base ligands (Salehzadeh et al., 2010). Cobalt(II/III) complexes with Schiff base ligands have been studied extensively due to their interesting structures and wide applications (Nejo et al., 2010; Shahabadi et al., 2010). As a continuation of our work on Schiff base complexes (Wei et al., 2008; Wang et al., 2007), the title mononuclear cobalt(II) complex (Fig. 1) is reported here.

The complex is located on a twofold rotational axis. The tetrahedral coordination sphere of CoII atom in the complex is formed by two imino N atoms and two phenolate O atoms from two Schiff base ligands. The coordinate bond distances are typical and comparable with the values in other similar cobalt(II) complexes with Schiff bases (Bahron et al., 1994; Elerman et al., 1996). The coordinate bond angles are in the range 96.06 (14)–123.0 (2)°, indicating a distorted tetrahedral geometry.

Related literature top

For background to Schiff bases and their complexes, see: Salehzadeh et al. (2010). For cobalt(II/III) complexes with Schiff base ligands, see: Nejo et al. (2010); Shahabadi et al. (2010). For the Schiff base complexes we have reported, see: Wei et al. (2008); Wang et al. (2007). For similar cobalt(II) complexes with Schiff bases, see: Bahron et al. (1994); Elerman et al. (1996).

Experimental top

The title complex was obtained by stirring of 5-nitrosalicylaldehyde (0.1 mmol, 16.7 mg), cyclopentylamine (0.1 mmol, 8.5 mg), and cobalt(II) acetate (0.1 mmol, 24.9 mg) in methanol (20 ml) for 30 min at room temperature. The reaction mixture was fitered. Brown block-shaped single crystals suitable for X-ray diffraction were formed from the filtrate after a few days.

Refinement top

Hydrogen atoms were positioned geometrically and refined using the riding-model approximation, with C—H = 0.93–0.98 Å, and Uiso(H) = 1.2Ueq(C). The cyclohexyl ring is disordered over two sites with occupancies of 0.360 (2) and 0.640 (2).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the atomic numbering and 30% probability displacement ellipsoids. Unlabeled atoms are related with the labeled ones by symmetry operation (3/4 - x, 7/4 - y, z). Only major parts of the disordered cyclopentyl rings are shown.
Bis[2-(cyclopentyliminomethyl)-4-nitrophenolato- κ2N2,O]cobalt(II) top
Crystal data top
[Co(C12H13N2O3)2]Dx = 1.368 Mg m3
Mr = 525.42Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, FdddCell parameters from 1748 reflections
a = 18.057 (2) Åθ = 2.3–24.5°
b = 18.792 (2) ŵ = 0.72 mm1
c = 30.070 (4) ÅT = 298 K
V = 10203 (2) Å3Block, brown
Z = 160.17 × 0.13 × 0.12 mm
F(000) = 4368
Data collection top
Bruker SMART CCD area-detector
diffractometer
2381 independent reflections
Radiation source: fine-focus sealed tube1143 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2118
Tmin = 0.888, Tmax = 0.919k = 2022
13092 measured reflectionsl = 2936
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.1016P)2]
where P = (Fo2 + 2Fc2)/3
2381 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.67 e Å3
66 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Co(C12H13N2O3)2]V = 10203 (2) Å3
Mr = 525.42Z = 16
Orthorhombic, FdddMo Kα radiation
a = 18.057 (2) ŵ = 0.72 mm1
b = 18.792 (2) ÅT = 298 K
c = 30.070 (4) Å0.17 × 0.13 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2381 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1143 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.919Rint = 0.099
13092 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05466 restraints
wR(F2) = 0.182H-atom parameters constrained
S = 0.92Δρmax = 0.67 e Å3
2381 reflectionsΔρmin = 0.29 e Å3
196 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*/UeqOcc. (<1)
Co10.37500.87500.69805 (4)0.0616 (4)
N10.4685 (2)0.8513 (2)0.66652 (14)0.0627 (11)
N20.5105 (3)0.5346 (2)0.69096 (17)0.0724 (13)
O10.36714 (17)0.78730 (16)0.72938 (12)0.0692 (10)
O20.4809 (2)0.47999 (19)0.70349 (16)0.0979 (14)
O30.5686 (3)0.53537 (19)0.66859 (15)0.0857 (12)
C10.4679 (3)0.7286 (2)0.69236 (16)0.0532 (12)
C20.4045 (3)0.7292 (2)0.71991 (18)0.0593 (13)
C30.3787 (3)0.6643 (3)0.73778 (18)0.0673 (14)
H30.33730.66430.75620.081*
C40.4134 (3)0.6022 (3)0.72853 (19)0.0686 (15)
H40.39520.55990.74030.082*
C50.4751 (3)0.6013 (2)0.70195 (18)0.0603 (14)
C60.5035 (3)0.6637 (3)0.68422 (16)0.0601 (13)
H60.54620.66240.66690.072*
C70.4979 (3)0.7890 (2)0.67028 (17)0.0625 (14)
H70.54390.78290.65700.075*
C80.5093 (3)0.9036 (2)0.63903 (19)0.0792 (18)0.360 (19)
H8A0.54780.87720.62310.095*0.360 (19)
C90.4576 (10)0.9360 (6)0.6035 (5)0.058 (6)0.360 (19)
H9A0.40970.91260.60380.069*0.360 (19)
H9B0.47900.93130.57410.069*0.360 (19)
C100.4500 (11)1.0153 (7)0.6166 (8)0.105 (8)0.360 (19)
H10A0.41421.02190.64020.127*0.360 (19)
H10B0.43631.04450.59130.127*0.360 (19)
C110.5309 (11)1.0318 (8)0.6328 (8)0.084 (8)0.360 (19)
H11A0.56511.03490.60800.101*0.360 (19)
H11B0.53291.07580.64970.101*0.360 (19)
C120.5479 (14)0.9666 (7)0.6625 (8)0.065 (8)0.360 (19)
H12A0.60090.95850.66450.078*0.360 (19)
H12B0.52820.97330.69220.078*0.360 (19)
C8'0.5093 (3)0.9036 (2)0.63903 (19)0.0792 (18)0.640 (19)
H8'A0.55430.88220.62670.095*0.640 (19)
C9'0.4605 (12)0.9347 (7)0.6014 (6)0.184 (12)0.640 (19)
H9'A0.40880.93610.61020.220*0.640 (19)
H9'B0.46510.90680.57440.220*0.640 (19)
C10'0.4914 (9)1.0109 (6)0.5946 (4)0.109 (5)0.640 (19)
H10C0.45491.04200.58110.131*0.640 (19)
H10D0.53591.01060.57650.131*0.640 (19)
C11'0.5087 (10)1.0337 (5)0.6438 (4)0.104 (6)0.640 (19)
H11C0.54961.06710.64440.124*0.640 (19)
H11D0.46571.05630.65690.124*0.640 (19)
C12'0.5288 (9)0.9665 (5)0.6696 (4)0.075 (5)0.640 (19)
H12C0.50070.96390.69710.090*0.640 (19)
H12D0.58110.96620.67680.090*0.640 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0590 (6)0.0357 (5)0.0903 (8)0.0076 (4)0.0000.000
N10.062 (3)0.041 (2)0.086 (3)0.0031 (19)0.002 (2)0.006 (2)
N20.080 (3)0.040 (3)0.097 (4)0.007 (2)0.019 (3)0.001 (3)
O10.073 (2)0.0385 (19)0.097 (3)0.0136 (17)0.015 (2)0.0044 (17)
O20.100 (3)0.038 (2)0.155 (4)0.007 (2)0.010 (3)0.001 (2)
O30.097 (3)0.060 (2)0.100 (3)0.026 (2)0.008 (3)0.005 (2)
C10.051 (3)0.038 (3)0.070 (3)0.006 (2)0.003 (3)0.003 (2)
C20.063 (3)0.042 (3)0.073 (3)0.007 (2)0.014 (3)0.002 (2)
C30.069 (3)0.044 (3)0.089 (4)0.002 (3)0.011 (3)0.008 (3)
C40.073 (4)0.040 (3)0.093 (4)0.002 (3)0.003 (3)0.014 (3)
C50.065 (3)0.036 (3)0.080 (4)0.009 (2)0.014 (3)0.002 (2)
C60.057 (3)0.047 (3)0.077 (4)0.012 (2)0.008 (3)0.004 (2)
C70.055 (3)0.044 (3)0.088 (4)0.003 (2)0.007 (3)0.002 (3)
C80.071 (4)0.048 (3)0.119 (5)0.004 (3)0.024 (3)0.014 (3)
C90.076 (10)0.050 (8)0.048 (8)0.032 (6)0.013 (7)0.022 (6)
C100.101 (11)0.111 (11)0.104 (12)0.025 (8)0.000 (9)0.008 (8)
C110.089 (11)0.062 (10)0.100 (12)0.003 (7)0.014 (9)0.009 (8)
C120.059 (11)0.052 (10)0.083 (11)0.004 (7)0.017 (8)0.001 (7)
C8'0.071 (4)0.048 (3)0.119 (5)0.004 (3)0.024 (3)0.014 (3)
C9'0.189 (14)0.174 (14)0.188 (14)0.040 (9)0.001 (9)0.020 (9)
C10'0.110 (8)0.093 (7)0.126 (9)0.011 (6)0.001 (7)0.037 (6)
C11'0.120 (10)0.067 (7)0.125 (9)0.008 (6)0.024 (8)0.015 (6)
C12'0.054 (7)0.067 (7)0.105 (8)0.022 (5)0.003 (6)0.011 (5)
Geometric parameters (Å, º) top
Co1—O1i1.904 (3)C8—H8A0.9800
Co1—O11.904 (3)C9—C101.548 (10)
Co1—N1i1.987 (4)C9—H9A0.9700
Co1—N11.987 (4)C9—H9B0.9700
N1—C71.291 (5)C10—C111.571 (10)
N1—C81.480 (6)C10—H10A0.9700
N2—O21.217 (5)C10—H10B0.9700
N2—O31.248 (6)C11—C121.549 (10)
N2—C51.444 (6)C11—H11A0.9700
O1—C21.314 (5)C11—H11B0.9700
C1—C61.401 (6)C12—H12A0.9700
C1—C21.413 (7)C12—H12B0.9700
C1—C71.422 (6)C9'—C10'1.551 (9)
C2—C31.411 (6)C9'—H9'A0.9700
C3—C41.353 (7)C9'—H9'B0.9700
C3—H30.9300C10'—C11'1.569 (9)
C4—C51.371 (7)C10'—H10C0.9700
C4—H40.9300C10'—H10D0.9700
C5—C61.387 (7)C11'—C12'1.527 (8)
C6—H60.9300C11'—H11C0.9700
C7—H70.9300C11'—H11D0.9700
C8—C91.544 (9)C12'—H12C0.9700
C8—C121.545 (10)C12'—H12D0.9700
O1i—Co1—O1120.7 (2)C8—C9—H9A110.8
O1i—Co1—N1i96.06 (14)C10—C9—H9A110.8
O1—Co1—N1i111.50 (16)C8—C9—H9B110.8
O1i—Co1—N1111.50 (16)C10—C9—H9B110.8
O1—Co1—N196.06 (14)H9A—C9—H9B108.8
N1i—Co1—N1123.0 (2)C9—C10—C11100.8 (10)
C7—N1—C8116.5 (4)C9—C10—H10A111.6
C7—N1—Co1120.7 (3)C11—C10—H10A111.6
C8—N1—Co1122.7 (3)C9—C10—H10B111.6
O2—N2—O3123.0 (5)C11—C10—H10B111.6
O2—N2—C5117.9 (5)H10A—C10—H10B109.4
O3—N2—C5119.1 (5)C12—C11—C10101.9 (10)
C2—O1—Co1125.0 (3)C12—C11—H11A111.4
C6—C1—C2118.8 (5)C10—C11—H11A111.4
C6—C1—C7116.0 (5)C12—C11—H11B111.4
C2—C1—C7125.1 (4)C10—C11—H11B111.4
O1—C2—C3117.8 (5)H11A—C11—H11B109.3
O1—C2—C1123.3 (4)C8—C12—C11104.7 (9)
C3—C2—C1118.9 (4)C8—C12—H12A110.8
C4—C3—C2121.0 (5)C11—C12—H12A110.8
C4—C3—H3119.5C8—C12—H12B110.8
C2—C3—H3119.5C11—C12—H12B110.8
C3—C4—C5120.4 (5)H12A—C12—H12B108.9
C3—C4—H4119.8C10'—C9'—H9'A111.0
C5—C4—H4119.8C10'—C9'—H9'B111.0
C4—C5—C6120.9 (4)H9'A—C9'—H9'B109.0
C4—C5—N2120.3 (5)C9'—C10'—C11'101.5 (9)
C6—C5—N2118.8 (5)C9'—C10'—H10C111.5
C5—C6—C1120.0 (5)C11'—C10'—H10C111.5
C5—C6—H6120.0C9'—C10'—H10D111.5
C1—C6—H6120.0C11'—C10'—H10D111.5
N1—C7—C1127.5 (5)H10C—C10'—H10D109.3
N1—C7—H7116.2C12'—C11'—C10'107.5 (8)
C1—C7—H7116.2C12'—C11'—H11C110.2
N1—C8—C9110.3 (8)C10'—C11'—H11C110.2
N1—C8—C12118.6 (11)C12'—C11'—H11D110.2
C9—C8—C12106.7 (8)C10'—C11'—H11D110.2
N1—C8—H8A106.9H11C—C11'—H11D108.5
C9—C8—H8A106.9C11'—C12'—H12C110.5
C12—C8—H8A106.9C11'—C12'—H12D110.5
C8—C9—C10104.9 (8)H12C—C12'—H12D108.7
Symmetry code: (i) x+3/4, y+7/4, z.

Experimental details

Crystal data
Chemical formula[Co(C12H13N2O3)2]
Mr525.42
Crystal system, space groupOrthorhombic, Fddd
Temperature (K)298
a, b, c (Å)18.057 (2), 18.792 (2), 30.070 (4)
V3)10203 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.17 × 0.13 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.888, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
13092, 2381, 1143
Rint0.099
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.182, 0.92
No. of reflections2381
No. of parameters196
No. of restraints66
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We acknowledge Huainan Normal College for supporting this work.

References

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