metal-organic compounds
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
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 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 see: Bahron et al. (1994); Elerman et al. (1996).
and their complexes, see: SalehzadehExperimental
Crystal data
|
Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811002194/cv5039sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811002194/cv5039Isup2.hkl
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.
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).
Data collection: SMART (Bruker, 2007); cell
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).[Co(C12H13N2O3)2] | Dx = 1.368 Mg m−3 |
Mr = 525.42 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fddd | Cell parameters from 1748 reflections |
a = 18.057 (2) Å | θ = 2.3–24.5° |
b = 18.792 (2) Å | µ = 0.72 mm−1 |
c = 30.070 (4) Å | T = 298 K |
V = 10203 (2) Å3 | Block, brown |
Z = 16 | 0.17 × 0.13 × 0.12 mm |
F(000) = 4368 |
Bruker SMART CCD area-detector diffractometer | 2381 independent reflections |
Radiation source: fine-focus sealed tube | 1143 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −21→18 |
Tmin = 0.888, Tmax = 0.919 | k = −20→22 |
13092 measured reflections | l = −29→36 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-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 parameters | Δρmax = 0.67 e Å−3 |
66 restraints | Δρmin = −0.29 e Å−3 |
[Co(C12H13N2O3)2] | V = 10203 (2) Å3 |
Mr = 525.42 | Z = 16 |
Orthorhombic, Fddd | Mo Kα radiation |
a = 18.057 (2) Å | µ = 0.72 mm−1 |
b = 18.792 (2) Å | T = 298 K |
c = 30.070 (4) Å | 0.17 × 0.13 × 0.12 mm |
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 = 0.919 | Rint = 0.099 |
13092 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 66 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.67 e Å−3 |
2381 reflections | Δρmin = −0.29 e Å−3 |
196 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co1 | 0.3750 | 0.8750 | 0.69805 (4) | 0.0616 (4) | |
N1 | 0.4685 (2) | 0.8513 (2) | 0.66652 (14) | 0.0627 (11) | |
N2 | 0.5105 (3) | 0.5346 (2) | 0.69096 (17) | 0.0724 (13) | |
O1 | 0.36714 (17) | 0.78730 (16) | 0.72938 (12) | 0.0692 (10) | |
O2 | 0.4809 (2) | 0.47999 (19) | 0.70349 (16) | 0.0979 (14) | |
O3 | 0.5686 (3) | 0.53537 (19) | 0.66859 (15) | 0.0857 (12) | |
C1 | 0.4679 (3) | 0.7286 (2) | 0.69236 (16) | 0.0532 (12) | |
C2 | 0.4045 (3) | 0.7292 (2) | 0.71991 (18) | 0.0593 (13) | |
C3 | 0.3787 (3) | 0.6643 (3) | 0.73778 (18) | 0.0673 (14) | |
H3 | 0.3373 | 0.6643 | 0.7562 | 0.081* | |
C4 | 0.4134 (3) | 0.6022 (3) | 0.72853 (19) | 0.0686 (15) | |
H4 | 0.3952 | 0.5599 | 0.7403 | 0.082* | |
C5 | 0.4751 (3) | 0.6013 (2) | 0.70195 (18) | 0.0603 (14) | |
C6 | 0.5035 (3) | 0.6637 (3) | 0.68422 (16) | 0.0601 (13) | |
H6 | 0.5462 | 0.6624 | 0.6669 | 0.072* | |
C7 | 0.4979 (3) | 0.7890 (2) | 0.67028 (17) | 0.0625 (14) | |
H7 | 0.5439 | 0.7829 | 0.6570 | 0.075* | |
C8 | 0.5093 (3) | 0.9036 (2) | 0.63903 (19) | 0.0792 (18) | 0.360 (19) |
H8A | 0.5478 | 0.8772 | 0.6231 | 0.095* | 0.360 (19) |
C9 | 0.4576 (10) | 0.9360 (6) | 0.6035 (5) | 0.058 (6) | 0.360 (19) |
H9A | 0.4097 | 0.9126 | 0.6038 | 0.069* | 0.360 (19) |
H9B | 0.4790 | 0.9313 | 0.5741 | 0.069* | 0.360 (19) |
C10 | 0.4500 (11) | 1.0153 (7) | 0.6166 (8) | 0.105 (8) | 0.360 (19) |
H10A | 0.4142 | 1.0219 | 0.6402 | 0.127* | 0.360 (19) |
H10B | 0.4363 | 1.0445 | 0.5913 | 0.127* | 0.360 (19) |
C11 | 0.5309 (11) | 1.0318 (8) | 0.6328 (8) | 0.084 (8) | 0.360 (19) |
H11A | 0.5651 | 1.0349 | 0.6080 | 0.101* | 0.360 (19) |
H11B | 0.5329 | 1.0758 | 0.6497 | 0.101* | 0.360 (19) |
C12 | 0.5479 (14) | 0.9666 (7) | 0.6625 (8) | 0.065 (8) | 0.360 (19) |
H12A | 0.6009 | 0.9585 | 0.6645 | 0.078* | 0.360 (19) |
H12B | 0.5282 | 0.9733 | 0.6922 | 0.078* | 0.360 (19) |
C8' | 0.5093 (3) | 0.9036 (2) | 0.63903 (19) | 0.0792 (18) | 0.640 (19) |
H8'A | 0.5543 | 0.8822 | 0.6267 | 0.095* | 0.640 (19) |
C9' | 0.4605 (12) | 0.9347 (7) | 0.6014 (6) | 0.184 (12) | 0.640 (19) |
H9'A | 0.4088 | 0.9361 | 0.6102 | 0.220* | 0.640 (19) |
H9'B | 0.4651 | 0.9068 | 0.5744 | 0.220* | 0.640 (19) |
C10' | 0.4914 (9) | 1.0109 (6) | 0.5946 (4) | 0.109 (5) | 0.640 (19) |
H10C | 0.4549 | 1.0420 | 0.5811 | 0.131* | 0.640 (19) |
H10D | 0.5359 | 1.0106 | 0.5765 | 0.131* | 0.640 (19) |
C11' | 0.5087 (10) | 1.0337 (5) | 0.6438 (4) | 0.104 (6) | 0.640 (19) |
H11C | 0.5496 | 1.0671 | 0.6444 | 0.124* | 0.640 (19) |
H11D | 0.4657 | 1.0563 | 0.6569 | 0.124* | 0.640 (19) |
C12' | 0.5288 (9) | 0.9665 (5) | 0.6696 (4) | 0.075 (5) | 0.640 (19) |
H12C | 0.5007 | 0.9639 | 0.6971 | 0.090* | 0.640 (19) |
H12D | 0.5811 | 0.9662 | 0.6768 | 0.090* | 0.640 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0590 (6) | 0.0357 (5) | 0.0903 (8) | 0.0076 (4) | 0.000 | 0.000 |
N1 | 0.062 (3) | 0.041 (2) | 0.086 (3) | 0.0031 (19) | 0.002 (2) | 0.006 (2) |
N2 | 0.080 (3) | 0.040 (3) | 0.097 (4) | 0.007 (2) | −0.019 (3) | 0.001 (3) |
O1 | 0.073 (2) | 0.0385 (19) | 0.097 (3) | 0.0136 (17) | 0.015 (2) | 0.0044 (17) |
O2 | 0.100 (3) | 0.038 (2) | 0.155 (4) | 0.007 (2) | −0.010 (3) | 0.001 (2) |
O3 | 0.097 (3) | 0.060 (2) | 0.100 (3) | 0.026 (2) | −0.008 (3) | −0.005 (2) |
C1 | 0.051 (3) | 0.038 (3) | 0.070 (3) | 0.006 (2) | −0.003 (3) | −0.003 (2) |
C2 | 0.063 (3) | 0.042 (3) | 0.073 (3) | 0.007 (2) | −0.014 (3) | 0.002 (2) |
C3 | 0.069 (3) | 0.044 (3) | 0.089 (4) | 0.002 (3) | 0.011 (3) | 0.008 (3) |
C4 | 0.073 (4) | 0.040 (3) | 0.093 (4) | −0.002 (3) | −0.003 (3) | 0.014 (3) |
C5 | 0.065 (3) | 0.036 (3) | 0.080 (4) | 0.009 (2) | −0.014 (3) | −0.002 (2) |
C6 | 0.057 (3) | 0.047 (3) | 0.077 (4) | 0.012 (2) | −0.008 (3) | −0.004 (2) |
C7 | 0.055 (3) | 0.044 (3) | 0.088 (4) | 0.003 (2) | 0.007 (3) | 0.002 (3) |
C8 | 0.071 (4) | 0.048 (3) | 0.119 (5) | 0.004 (3) | 0.024 (3) | 0.014 (3) |
C9 | 0.076 (10) | 0.050 (8) | 0.048 (8) | −0.032 (6) | −0.013 (7) | 0.022 (6) |
C10 | 0.101 (11) | 0.111 (11) | 0.104 (12) | 0.025 (8) | 0.000 (9) | 0.008 (8) |
C11 | 0.089 (11) | 0.062 (10) | 0.100 (12) | 0.003 (7) | 0.014 (9) | −0.009 (8) |
C12 | 0.059 (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) |
Co1—O1i | 1.904 (3) | C8—H8A | 0.9800 |
Co1—O1 | 1.904 (3) | C9—C10 | 1.548 (10) |
Co1—N1i | 1.987 (4) | C9—H9A | 0.9700 |
Co1—N1 | 1.987 (4) | C9—H9B | 0.9700 |
N1—C7 | 1.291 (5) | C10—C11 | 1.571 (10) |
N1—C8 | 1.480 (6) | C10—H10A | 0.9700 |
N2—O2 | 1.217 (5) | C10—H10B | 0.9700 |
N2—O3 | 1.248 (6) | C11—C12 | 1.549 (10) |
N2—C5 | 1.444 (6) | C11—H11A | 0.9700 |
O1—C2 | 1.314 (5) | C11—H11B | 0.9700 |
C1—C6 | 1.401 (6) | C12—H12A | 0.9700 |
C1—C2 | 1.413 (7) | C12—H12B | 0.9700 |
C1—C7 | 1.422 (6) | C9'—C10' | 1.551 (9) |
C2—C3 | 1.411 (6) | C9'—H9'A | 0.9700 |
C3—C4 | 1.353 (7) | C9'—H9'B | 0.9700 |
C3—H3 | 0.9300 | C10'—C11' | 1.569 (9) |
C4—C5 | 1.371 (7) | C10'—H10C | 0.9700 |
C4—H4 | 0.9300 | C10'—H10D | 0.9700 |
C5—C6 | 1.387 (7) | C11'—C12' | 1.527 (8) |
C6—H6 | 0.9300 | C11'—H11C | 0.9700 |
C7—H7 | 0.9300 | C11'—H11D | 0.9700 |
C8—C9 | 1.544 (9) | C12'—H12C | 0.9700 |
C8—C12 | 1.545 (10) | C12'—H12D | 0.9700 |
O1i—Co1—O1 | 120.7 (2) | C8—C9—H9A | 110.8 |
O1i—Co1—N1i | 96.06 (14) | C10—C9—H9A | 110.8 |
O1—Co1—N1i | 111.50 (16) | C8—C9—H9B | 110.8 |
O1i—Co1—N1 | 111.50 (16) | C10—C9—H9B | 110.8 |
O1—Co1—N1 | 96.06 (14) | H9A—C9—H9B | 108.8 |
N1i—Co1—N1 | 123.0 (2) | C9—C10—C11 | 100.8 (10) |
C7—N1—C8 | 116.5 (4) | C9—C10—H10A | 111.6 |
C7—N1—Co1 | 120.7 (3) | C11—C10—H10A | 111.6 |
C8—N1—Co1 | 122.7 (3) | C9—C10—H10B | 111.6 |
O2—N2—O3 | 123.0 (5) | C11—C10—H10B | 111.6 |
O2—N2—C5 | 117.9 (5) | H10A—C10—H10B | 109.4 |
O3—N2—C5 | 119.1 (5) | C12—C11—C10 | 101.9 (10) |
C2—O1—Co1 | 125.0 (3) | C12—C11—H11A | 111.4 |
C6—C1—C2 | 118.8 (5) | C10—C11—H11A | 111.4 |
C6—C1—C7 | 116.0 (5) | C12—C11—H11B | 111.4 |
C2—C1—C7 | 125.1 (4) | C10—C11—H11B | 111.4 |
O1—C2—C3 | 117.8 (5) | H11A—C11—H11B | 109.3 |
O1—C2—C1 | 123.3 (4) | C8—C12—C11 | 104.7 (9) |
C3—C2—C1 | 118.9 (4) | C8—C12—H12A | 110.8 |
C4—C3—C2 | 121.0 (5) | C11—C12—H12A | 110.8 |
C4—C3—H3 | 119.5 | C8—C12—H12B | 110.8 |
C2—C3—H3 | 119.5 | C11—C12—H12B | 110.8 |
C3—C4—C5 | 120.4 (5) | H12A—C12—H12B | 108.9 |
C3—C4—H4 | 119.8 | C10'—C9'—H9'A | 111.0 |
C5—C4—H4 | 119.8 | C10'—C9'—H9'B | 111.0 |
C4—C5—C6 | 120.9 (4) | H9'A—C9'—H9'B | 109.0 |
C4—C5—N2 | 120.3 (5) | C9'—C10'—C11' | 101.5 (9) |
C6—C5—N2 | 118.8 (5) | C9'—C10'—H10C | 111.5 |
C5—C6—C1 | 120.0 (5) | C11'—C10'—H10C | 111.5 |
C5—C6—H6 | 120.0 | C9'—C10'—H10D | 111.5 |
C1—C6—H6 | 120.0 | C11'—C10'—H10D | 111.5 |
N1—C7—C1 | 127.5 (5) | H10C—C10'—H10D | 109.3 |
N1—C7—H7 | 116.2 | C12'—C11'—C10' | 107.5 (8) |
C1—C7—H7 | 116.2 | C12'—C11'—H11C | 110.2 |
N1—C8—C9 | 110.3 (8) | C10'—C11'—H11C | 110.2 |
N1—C8—C12 | 118.6 (11) | C12'—C11'—H11D | 110.2 |
C9—C8—C12 | 106.7 (8) | C10'—C11'—H11D | 110.2 |
N1—C8—H8A | 106.9 | H11C—C11'—H11D | 108.5 |
C9—C8—H8A | 106.9 | C11'—C12'—H12C | 110.5 |
C12—C8—H8A | 106.9 | C11'—C12'—H12D | 110.5 |
C8—C9—C10 | 104.9 (8) | H12C—C12'—H12D | 108.7 |
Symmetry code: (i) −x+3/4, −y+7/4, z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C12H13N2O3)2] |
Mr | 525.42 |
Crystal system, space group | Orthorhombic, Fddd |
Temperature (K) | 298 |
a, b, c (Å) | 18.057 (2), 18.792 (2), 30.070 (4) |
V (Å3) | 10203 (2) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.17 × 0.13 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.888, 0.919 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13092, 2381, 1143 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.182, 0.92 |
No. of reflections | 2381 |
No. of parameters | 196 |
No. of restraints | 66 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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
Bahron, H., Larkworthy, L. F., Marecaux, A., Povey, D. C. & Smith, G. W. (1994). J. Chem. Crystallogr. 24, 145–150. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Elerman, Y., Kabak, M. & Tahir, M. N. (1996). Acta Cryst. C52, 2434–2436. CSD CrossRef Web of Science IUCr Journals Google Scholar
Nejo, A. A., Kolawole, G. A. & Nejo, A. O. (2010). J. Coord. Chem. 63, 4398–4410. Web of Science CrossRef CAS Google Scholar
Salehzadeh, S., Golbedaghi, R. & Blackman, A. G. (2010). J. Coord. Chem. 63, 634–642. Web of Science CrossRef CAS Google Scholar
Shahabadi, N., Kashanian, S. & Darabi, F. (2010). Eur. J. Med. Chem. 45, 4239–4245. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2007). Chin. J. Struct. Chem. 26, 1327–1331. CAS Google Scholar
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008). Acta Cryst. E64, m859–m860. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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.