Bis[2-(cyclo-pentyl-imino-meth-yl)-4-nitro-phenolato-κN,O]cobalt(II).

In the title compound, [Co(C(12)H(13)N(2)O(3))(2)], the Co(II) 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-(cyclo-pentyl-imino-meth-yl)-4-nitro-phenolate ligands (L) in a distorted tetra-hedral geometry. The cyclo-pentyl 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 ▶). 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

Crystal data

[Co(C12H13N2O3)2]

M = 525.42

Orthorhombic,

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 ▶) T min = 0.888, T max = 0.919

13092 measured reflections

2381 independent reflections

1143 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 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 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002194/cv5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002194/cv5039Isup2.hkl

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

[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	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

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