Bis(benzoato-κ2O,O′)(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)cobalt(II)

Zhao, P.-Z.; Xuan, X.-P.; Tang, Q.-H.

doi:10.1107/S1600536807068080

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m327

doi:10.1107/S1600536807068080

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Bis(benzoato-κ²O,O′)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)cobalt(II)

Pei-Zheng Zhao,^a ^* Xiao-Peng Xuan ^a and Qing-Hu Tang ^a

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China
^*Correspondence e-mail: pz_zhao@hotmail.com

(Received 14 November 2007; accepted 21 December 2007; online 9 January 2008)

In the title compound, [Co(C₇H₅O₂)₂(C₁₄H₁₂N₂)], the Co^II ion is located on a twofold rotation axis and is chelated by a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and two benzoate anions in a distorted octahedral geometry. The crystal packing is stabilized by π–π interactions between parallel dmphen ligands of neighbouring molecules, with a face-to-face distance of 3.411 (2) Å.

Related literature

For background information on cobalt coordination chemistry, see: Wang et al. (1996 ); Wall et al. (1999 ); Naing et al. (1995 ). For related structures, see: Wu et al. (2003 ); Su et al. (2005 ); Ding et al. (2006 ); Ren et al. (2007 ); Zhong et al. (2006 ); Li et al. (2007 ).

Experimental

Crystal data

[Co(C₇H₅O₂)₂(C₁₄H₁₂N₂)]
M_r = 509.41
Monoclinic, C 2/c
a = 17.632 (3) Å
b = 14.410 (2) Å
c = 9.5282 (15) Å
β = 90.796 (2)°
V = 2420.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 293 (2) K
0.30 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.805, T_max = 0.856
8882 measured reflections
2253 independent reflections
1840 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.111
S = 1.06
2253 reflections
180 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.114 (2)
Co1—O1	2.159 (2)
Co1—O2	2.154 (2)

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068080/xu2376sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068080/xu2376Isup2.hkl

checkCIF report

Comment top

Metal-phenanthroline complexes and their detivatives have attracted much attention because of their peculiar features during recent decades (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). A number of Co(II) complexes have been synthesized and structures determined (Wu et al., 2003; Su et al., 2005; Ding et al., 2006; Ren et al., 2007; Zhong et al., 2006; Li et al., 2007). The title complex, (I), was recently prepared and its crystal structure is reported here.

Each Co^II ion is located on a twofold rotation axis and six-coordinated by two N atoms from a dmphen ligand and four carbonyl O atoms from two benzoate ligands (Fig. 1) with a distorted octahedral geometry (Table 1).

In the crystal structure, molecules are linked into a one dimensional network by π-π interactions between the dmphen ring systems (Fig. 2). These intermolecular interaction occur between the parallel rings within offset face-to-face packing. The face-to-face distance of neighboring parallel rings is 3.411 (2) Å.

Related literature top

For background information on cobalt coordination chemistry, see: Wang et al. (1996); Wall et al. (1999); Naing et al. (1995). For related structures, see: Wu et al. (2003); Su et al. (2005); Ding et al. (2006); Ren et al. (2007); Zhong et al. (2006); Li et al. (2007).

Experimental top

Sodium benzoate (0.1455 g, 1 mmol) and Co(NO₃)₂^.6H₂O (0.1456 g, 0.5 mmol) were dissolved in distilled water (15 ml). This solution was added to a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C₁₄H₁₂N₂^.0.5H₂O, 0.1090 g, 0.5 mmol) in ethanol (10 ml). The mixture was refluxed for 4 h. After cooling to room temperature the mixture was filtered. Brown single crystals were obtained by slow evaporation at room temperature after 1 d.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of the title complex with 30% probability displacement ellipsoids, one disordered component has been omitted for clarity. Symmetry code: (A) -x + 1, y, -z + 3/2.
	Fig. 2. The π-π interaction between the dmphen rings of neighboring molecules in the crystal structure.

Bis(benzoato-κ²O,O')(2,9-dimethyl-1,10-phenanthroline-κ²N,N')cobalt(II) top

Crystal data top

[Co(C₇H₅O₂)₂(C₁₄H₁₂N₂)]	F(000) = 1052
M_r = 509.41	D_x = 1.398 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2433 reflections
a = 17.632 (3) Å	θ = 2.3–22.5°
b = 14.410 (2) Å	µ = 0.75 mm⁻¹
c = 9.5282 (15) Å	T = 293 K
β = 90.796 (2)°	Block, brown
V = 2420.6 (7) Å³	0.30 × 0.22 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2253 independent reflections
Radiation source: fine-focus sealed tube	1840 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −21→21
T_min = 0.805, T_max = 0.856	k = −17→17
8882 measured reflections	l = −11→11

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0507P)² + 2.0726P] where P = (F_o² + 2F_c²)/3
2253 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Co(C₇H₅O₂)₂(C₁₄H₁₂N₂)]	V = 2420.6 (7) Å³
M_r = 509.41	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.632 (3) Å	µ = 0.75 mm⁻¹
b = 14.410 (2) Å	T = 293 K
c = 9.5282 (15) Å	0.30 × 0.22 × 0.22 mm
β = 90.796 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2253 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1840 reflections with I > 2σ(I)
T_min = 0.805, T_max = 0.856	R_int = 0.026
8882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
2253 reflections	Δρ_min = −0.37 e Å⁻³
180 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.5000	0.76395 (3)	0.7500	0.0542 (2)
C1	0.63842 (19)	0.7820 (2)	0.9976 (4)	0.0839 (10)
H1A	0.5975	0.7472	1.0373	0.126*
H1B	0.6776	0.7906	1.0673	0.126*
H1C	0.6585	0.7488	0.9191	0.126*
C2	0.60968 (14)	0.8746 (2)	0.9496 (3)	0.0593 (7)
C3	0.63991 (16)	0.9577 (2)	1.0038 (3)	0.0678 (8)
H3	0.6782	0.9552	1.0719	0.081*
C4	0.61443 (17)	1.0410 (2)	0.9589 (3)	0.0651 (8)
H4	0.6345	1.0953	0.9966	0.078*
C5	0.55731 (15)	1.04513 (18)	0.8547 (3)	0.0560 (6)
C6	0.52910 (13)	0.96006 (17)	0.8040 (2)	0.0471 (6)
C7	0.52756 (18)	1.1299 (2)	0.8001 (3)	0.0693 (8)
H7	0.5463	1.1861	0.8338	0.083*
C8	0.57021 (17)	0.68233 (18)	0.5604 (3)	0.0602 (7)
C9	0.6070 (2)	0.6373 (2)	0.4415 (3)	0.054 (4)	0.452 (14)
C10	0.68276 (16)	0.6552 (3)	0.4177 (4)	0.066 (3)	0.452 (14)
H10	0.7095	0.6954	0.4766	0.079*	0.452 (14)
C11	0.71880 (15)	0.6135 (3)	0.3065 (4)	0.078 (6)	0.452 (14)
H11	0.7698	0.6255	0.2905	0.094*	0.452 (14)
C12	0.6791 (3)	0.5537 (4)	0.2190 (5)	0.096 (4)	0.452 (14)
H12	0.7034	0.5256	0.1441	0.115*	0.452 (14)
C13	0.6034 (3)	0.5358 (6)	0.2427 (7)	0.111 (4)	0.452 (14)
H13	0.5767	0.4956	0.1838	0.133*	0.452 (14)
C14	0.5674 (3)	0.5776 (6)	0.3540 (6)	0.084 (3)	0.452 (14)
H14	0.5164	0.5655	0.3700	0.100*	0.452 (14)
C9'	0.6177 (2)	0.63122 (19)	0.4495 (3)	0.056 (3)	0.548 (14)
C10'	0.68099 (17)	0.6701 (2)	0.3936 (5)	0.064 (3)	0.548 (14)
H10'	0.6970	0.7284	0.4236	0.077*	0.548 (14)
C11'	0.72124 (15)	0.6236 (2)	0.2934 (4)	0.083 (5)	0.548 (14)
H11'	0.7643	0.6505	0.2553	0.100*	0.548 (14)
C12'	0.6981 (3)	0.5377 (2)	0.2495 (5)	0.084 (3)	0.548 (14)
H12'	0.7257	0.5059	0.1823	0.101*	0.548 (14)
C13'	0.6347 (5)	0.4987 (3)	0.3043 (9)	0.090 (3)	0.548 (14)
H13'	0.6185	0.4407	0.2734	0.108*	0.548 (14)
C14'	0.5949 (4)	0.5449 (3)	0.4048 (7)	0.072 (2)	0.548 (14)
H14'	0.5521	0.5177	0.4431	0.087*	0.548 (14)
N1	0.55395 (11)	0.87653 (14)	0.8526 (2)	0.0496 (5)
O1	0.60107 (14)	0.74637 (15)	0.6274 (3)	0.0847 (5)
O2	0.50361 (13)	0.65984 (16)	0.5879 (2)	0.0847 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0625 (3)	0.0494 (3)	0.0509 (3)	0.000	0.0041 (2)	0.000
C1	0.076 (2)	0.098 (3)	0.077 (2)	0.0292 (18)	−0.0178 (17)	0.0002 (18)
C2	0.0486 (14)	0.0791 (19)	0.0502 (15)	0.0093 (13)	0.0026 (11)	−0.0044 (13)
C3	0.0521 (16)	0.098 (2)	0.0530 (16)	−0.0035 (15)	−0.0033 (12)	−0.0160 (15)
C4	0.0679 (18)	0.075 (2)	0.0522 (16)	−0.0159 (15)	0.0081 (13)	−0.0161 (14)
C5	0.0638 (16)	0.0613 (16)	0.0433 (13)	−0.0074 (12)	0.0138 (12)	−0.0070 (11)
C6	0.0506 (14)	0.0547 (14)	0.0363 (12)	0.0007 (11)	0.0101 (10)	−0.0017 (10)
C7	0.099 (2)	0.0540 (16)	0.0549 (17)	−0.0078 (14)	0.0167 (14)	−0.0058 (12)
C8	0.0749 (18)	0.0479 (15)	0.0579 (16)	−0.0033 (13)	0.0010 (14)	0.0031 (12)
C9	0.059 (5)	0.049 (7)	0.055 (7)	0.002 (5)	0.015 (5)	0.007 (5)
C10	0.066 (8)	0.075 (6)	0.056 (5)	−0.008 (5)	−0.008 (5)	−0.001 (4)
C11	0.051 (9)	0.105 (12)	0.079 (10)	0.001 (8)	0.001 (7)	0.006 (10)
C12	0.096 (7)	0.120 (9)	0.072 (6)	0.012 (6)	0.010 (5)	−0.035 (5)
C13	0.103 (7)	0.129 (9)	0.103 (7)	−0.024 (7)	0.017 (6)	−0.059 (7)
C14	0.074 (5)	0.089 (6)	0.088 (6)	−0.014 (5)	0.013 (5)	−0.034 (5)
C9'	0.062 (5)	0.058 (6)	0.047 (6)	−0.003 (4)	−0.004 (4)	−0.006 (4)
C10'	0.062 (6)	0.059 (4)	0.073 (4)	0.000 (4)	0.004 (4)	0.009 (4)
C11'	0.071 (9)	0.099 (9)	0.080 (9)	0.007 (7)	0.028 (7)	0.012 (8)
C12'	0.076 (4)	0.110 (6)	0.067 (4)	0.015 (5)	0.016 (4)	−0.010 (5)
C13'	0.097 (6)	0.086 (5)	0.086 (5)	−0.018 (4)	0.010 (4)	−0.039 (4)
C14'	0.068 (4)	0.073 (4)	0.077 (4)	−0.020 (3)	0.016 (4)	−0.014 (3)
N1	0.0488 (12)	0.0589 (13)	0.0412 (11)	0.0050 (9)	0.0029 (9)	−0.0033 (9)
O1	0.0876 (11)	0.0800 (11)	0.0870 (11)	−0.0088 (8)	0.0221 (9)	−0.0209 (8)
O2	0.0876 (11)	0.0800 (11)	0.0870 (11)	−0.0088 (8)	0.0221 (9)	−0.0209 (8)

Geometric parameters (Å, º) top

Co1—N1	2.114 (2)	C8—C9	1.465 (4)
Co1—N1ⁱ	2.114 (2)	C8—C9'	1.544 (4)
Co1—O1	2.159 (2)	C9—C10	1.3816 (16)
Co1—O1ⁱ	2.159 (2)	C9—C14	1.3816 (16)
Co1—O2ⁱ	2.154 (2)	C10—C11	1.3815 (16)
Co1—O2	2.154 (2)	C10—H10	0.9300
Co1—C8ⁱ	2.498 (3)	C11—C12	1.3816 (16)
C1—C2	1.497 (4)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.3816 (16)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.3816 (16)
C2—N1	1.339 (3)	C13—H13	0.9300
C2—C3	1.406 (4)	C14—H14	0.9300
C3—C4	1.349 (4)	C9'—C10'	1.3643 (16)
C3—H3	0.9300	C9'—C14'	1.3726 (16)
C4—C5	1.406 (4)	C10'—C11'	1.3726 (16)
C4—H4	0.9300	C10'—H10'	0.9300
C5—C6	1.406 (3)	C11'—C12'	1.3660 (16)
C5—C7	1.425 (4)	C11'—H11'	0.9300
C6—N1	1.360 (3)	C12'—C13'	1.3619 (15)
C6—C6ⁱ	1.444 (5)	C12'—H12'	0.9300
C7—C7ⁱ	1.353 (6)	C13'—C14'	1.3685 (16)
C7—H7	0.9300	C13'—H13'	0.9300
C8—O1	1.243 (3)	C14'—H14'	0.9300
C8—O2	1.249 (3)

N1—Co1—N1ⁱ	79.73 (11)	O1—C8—C9	122.0 (3)
N1—Co1—O2ⁱ	102.73 (9)	O2—C8—C9	118.4 (3)
N1ⁱ—Co1—O2ⁱ	148.05 (8)	O1—C8—C9'	117.9 (3)
N1—Co1—O2	148.05 (8)	O2—C8—C9'	122.7 (3)
N1ⁱ—Co1—O2	102.73 (9)	C10—C9—C14	120.0
O2ⁱ—Co1—O2	91.74 (13)	C10—C9—C8	118.9 (2)
N1—Co1—O1	88.33 (8)	C14—C9—C8	121.1 (2)
N1ⁱ—Co1—O1	102.08 (9)	C11—C10—C9	120.0
O2ⁱ—Co1—O1	109.81 (9)	C11—C10—H10	120.0
O2—Co1—O1	59.85 (8)	C9—C10—H10	120.0
N1—Co1—O1ⁱ	102.08 (9)	C10—C11—C12	120.0
N1ⁱ—Co1—O1ⁱ	88.33 (8)	C10—C11—H11	120.0
O2ⁱ—Co1—O1ⁱ	59.85 (8)	C12—C11—H11	120.0
O2—Co1—O1ⁱ	109.81 (9)	C11—C12—C13	120.0
O1—Co1—O1ⁱ	166.53 (12)	C11—C12—H12	120.0
N1—Co1—C8ⁱ	104.54 (8)	C13—C12—H12	120.0
N1ⁱ—Co1—C8ⁱ	118.14 (8)	C12—C13—C14	120.0
O2ⁱ—Co1—C8ⁱ	30.01 (8)	C12—C13—H13	120.0
O2—Co1—C8ⁱ	102.14 (9)	C14—C13—H13	120.0
O1—Co1—C8ⁱ	139.20 (10)	C9—C14—C13	120.0
O1ⁱ—Co1—C8ⁱ	29.84 (8)	C9—C14—H14	120.0
C2—C1—H1A	109.5	C13—C14—H14	120.0
C2—C1—H1B	109.5	C10'—C9'—C14'	119.2
H1A—C1—H1B	109.5	C10'—C9'—C8	121.72 (19)
C2—C1—H1C	109.5	C14'—C9'—C8	119.06 (19)
H1A—C1—H1C	109.5	C9'—C10'—C11'	120.3
H1B—C1—H1C	109.5	C9'—C10'—H10'	119.8
N1—C2—C3	120.4 (3)	C11'—C10'—H10'	119.8
N1—C2—C1	118.1 (3)	C12'—C11'—C10'	120.0
C3—C2—C1	121.4 (3)	C12'—C11'—H11'	120.0
C4—C3—C2	121.2 (3)	C10'—C11'—H11'	120.0
C4—C3—H3	119.4	C13'—C12'—C11'	120.0
C2—C3—H3	119.4	C13'—C12'—H12'	120.0
C3—C4—C5	119.6 (3)	C11'—C12'—H12'	120.0
C3—C4—H4	120.2	C12'—C13'—C14'	119.9
C5—C4—H4	120.2	C12'—C13'—H13'	120.0
C4—C5—C6	116.9 (3)	C14'—C13'—H13'	120.0
C4—C5—C7	123.4 (3)	C13'—C14'—C9'	120.5
C6—C5—C7	119.7 (2)	C13'—C14'—H14'	119.8
N1—C6—C5	123.0 (2)	C9'—C14'—H14'	119.8
N1—C6—C6ⁱ	117.74 (13)	C2—N1—C6	118.9 (2)
C5—C6—C6ⁱ	119.30 (15)	C2—N1—Co1	128.61 (18)
C7ⁱ—C7—C5	120.99 (16)	C6—N1—Co1	112.39 (15)
C7ⁱ—C7—H7	119.5	C8—O1—Co1	90.36 (19)
C5—C7—H7	119.5	C8—O2—Co1	90.41 (17)
O1—C8—O2	119.4 (3)

N1—C2—C3—C4	−0.8 (4)	C3—C2—N1—C6	2.3 (4)
C1—C2—C3—C4	179.2 (3)	C1—C2—N1—C6	−177.6 (2)
C2—C3—C4—C5	−0.8 (4)	C3—C2—N1—Co1	178.41 (18)
C3—C4—C5—C6	0.8 (4)	C1—C2—N1—Co1	−1.5 (4)
C3—C4—C5—C7	−179.4 (3)	C5—C6—N1—C2	−2.4 (3)
C4—C5—C6—N1	0.9 (4)	C6ⁱ—C6—N1—C2	177.8 (2)
C7—C5—C6—N1	−179.0 (2)	C5—C6—N1—Co1	−179.10 (18)
C4—C5—C6—C6ⁱ	−179.4 (2)	C6ⁱ—C6—N1—Co1	1.2 (3)
C7—C5—C6—C6ⁱ	0.8 (4)	N1ⁱ—Co1—N1—C2	−176.7 (3)
C4—C5—C7—C7ⁱ	−179.9 (3)	O2ⁱ—Co1—N1—C2	35.9 (2)
C6—C5—C7—C7ⁱ	0.0 (5)	O2—Co1—N1—C2	−79.0 (3)
O1—C8—C9—C10	11.2 (5)	O1—Co1—N1—C2	−74.1 (2)
O2—C8—C9—C10	−174.2 (4)	O1ⁱ—Co1—N1—C2	97.3 (2)
C9'—C8—C9—C10	−49.13 (12)	C8ⁱ—Co1—N1—C2	66.7 (2)
O1—C8—C9—C14	−169.0 (5)	N1ⁱ—Co1—N1—C6	−0.41 (11)
O2—C8—C9—C14	5.7 (5)	O2ⁱ—Co1—N1—C6	−147.88 (16)
C9'—C8—C9—C14	130.70 (19)	O2—Co1—N1—C6	97.2 (2)
C14—C9—C10—C11	0.0	O1—Co1—N1—C6	102.19 (17)
C8—C9—C10—C11	179.8 (3)	O1ⁱ—Co1—N1—C6	−86.45 (17)
C9—C10—C11—C12	0.0	C8ⁱ—Co1—N1—C6	−117.03 (16)
C10—C11—C12—C13	0.0	O2—C8—O1—Co1	0.7 (3)
C11—C12—C13—C14	0.0	C9—C8—O1—Co1	175.3 (3)
C10—C9—C14—C13	0.0	C9'—C8—O1—Co1	−177.0 (2)
C8—C9—C14—C13	−179.8 (3)	N1—Co1—O1—C8	−177.35 (18)
C12—C13—C14—C9	0.0	N1ⁱ—Co1—O1—C8	−98.22 (18)
O1—C8—C9'—C10'	−20.3 (5)	O2ⁱ—Co1—O1—C8	79.71 (19)
O2—C8—C9'—C10'	162.1 (4)	O2—Co1—O1—C8	−0.39 (17)
C9—C8—C9'—C10'	103.27 (16)	O1ⁱ—Co1—O1—C8	41.69 (17)
O1—C8—C9'—C14'	160.6 (4)	C8ⁱ—Co1—O1—C8	72.1 (3)
O2—C8—C9'—C14'	−17.0 (5)	O1—C8—O2—Co1	−0.7 (3)
C9—C8—C9'—C14'	−75.85 (18)	C9—C8—O2—Co1	−175.5 (3)
C14'—C9'—C10'—C11'	0.3	C9'—C8—O2—Co1	176.9 (3)
C8—C9'—C10'—C11'	−178.9 (3)	N1—Co1—O2—C8	6.1 (3)
C9'—C10'—C11'—C12'	−0.3	N1ⁱ—Co1—O2—C8	97.09 (18)
C10'—C11'—C12'—C13'	0.6	O2ⁱ—Co1—O2—C8	−111.61 (19)
C11'—C12'—C13'—C14'	−1.0	O1—Co1—O2—C8	0.38 (17)
C12'—C13'—C14'—C9'	1.0	O1ⁱ—Co1—O2—C8	−170.06 (17)
C10'—C9'—C14'—C13'	−0.6	C8ⁱ—Co1—O2—C8	−140.01 (16)
C8—C9'—C14'—C13'	178.5 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Co(C₇H₅O₂)₂(C₁₄H₁₂N₂)]
M_r	509.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.632 (3), 14.410 (2), 9.5282 (15)
β (°)	90.796 (2)
V (Å³)	2420.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.30 × 0.22 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.805, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	8882, 2253, 1840
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.06
No. of reflections	2253
No. of parameters	180
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Bruker, 2001).

Selected bond lengths (Å) top

Co1—N1	2.114 (2)	Co1—O2	2.154 (2)
Co1—O1	2.159 (2)

Acknowledgements

Financial support from the Science Fund of Henan Province for Distinguished Young Scholars (grant No. 074100510005) is gratefully acknowledged.

References

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