catena-Poly[[(2,2′-bipyridine-κ2N,N′)cobalt(II)]-μ-oxalato-κ4O1,O2:O1′,O2′]

Li, P.-Z.; Xu, Q.

doi:10.1107/S1600536809012690

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m508

doi:10.1107/S1600536809012690

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catena-Poly[[(2,2′-bipyridine-κ²N,N′)cobalt(II)]-μ-oxalato-κ⁴O¹,O²:O^1′,O^2′]

Pei-Zhou Li ^a and Qiang Xu ^a ^*

^aNational Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, and Graduate School of Engineering, Kobe University, Nada Ku, Kobe, Hyogo 657-8501, Japan
^*Correspondence e-mail: q.xu@aist.go.jp

(Received 24 March 2009; accepted 3 April 2009; online 10 April 2009)

In the one-dimensional title coordination polymer, [Co(C₂O₄)(C₁₀H₈N₂)]_n, the Co^II atom is coordinated in a distorted octahedral geometry by two N atoms from one 2,2′-bipyridine ligand and four O atoms belonging to two chelating oxalate ligands. Two neighboring Co centers are bridged by an oxalate ligand, forming a one-dimensional chain structure.

Related literature

For general background to metal–oxalate compounds, see: Coronado et al. (2001 ); Decurtins et al. (1994 ). For related structures, see: Fun et al. (1999 ); Lin et al. (2006 ).

Experimental

Crystal data

[Co(C₂O₄)(C₁₀H₈N₂)]
M_r = 303.13
Orthorhombic, P n a 2₁
a = 9.2333 (18) Å
b = 9.2163 (18) Å
c = 14.101 (3) Å
V = 1199.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 293 K
0.16 × 0.14 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.800, T_max = 0.892
10848 measured reflections
2692 independent reflections
1887 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.136
S = 1.09
2692 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.90 e Å⁻³
Absolute structure: Flack (1983 ); 1283 Friedel pairs
Flack parameter: 0.03 (4)

Table 1
Selected bond lengths (Å)

Co1—O1	2.076 (4)
Co1—O4ⁱ	2.095 (4)
Co1—O2ⁱ	2.126 (4)
Co1—N2	2.139 (5)
Co1—O3	2.142 (4)
Co1—N1	2.146 (5)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012690/hy2191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012690/hy2191Isup2.hkl

checkCIF report

Comment top

The self-assembly of coordination polymers has attracted considerable attention in the past decade. This arises mainly for their various intriguing topological structures and their potential applications in material chemistry. Much research has been carried out on metal–oxalate compounds due to their interesting magnetic and optical properties (Coronado et al., 2001; Decurtins et al., 1994). Herein, we present the structure of the title complex, [Co(C₂O₄)(C₁₀H₈N₂)]_n, which is isomorphous to the zinc(II) complex reported by Lin et al. (2006) and to the iron(II) complex reported by Fun et al. (1999).

The title compound is an infinite one-dimensional coordination polymer. The Co^II atom is coordinated by two N atoms from one 2,2'-bipyridine ligand and four O atoms that belong to two oxalate dianions (Table 1) in a distorted octahedral geometry, as shown in Fig. 1. Two neighboring Co centers are bridged by an oxalate ligand, forming a one-dimensional chain structure, as shown in Fig. 2.

Related literature top

For general background to metal–oxalate compounds, see: Coronado et al. (2001); Decurtins et al. (1994). For related structures, see: Fun et al. (1999); Lin et al. (2006).

Experimental top

The brown plate-like single crystals of the title compound were obtained by a solvothermal reaction of cobalt chloride hexahydrate (CoCl₂.6H₂O, 0.5 mmol), sodium oxalate [Na₂(C₂O₄), 1 mmol] and 2,2'-bipyridine (C₁₀H₈N₂, 0.5 mmol) in a solution of CH₃OH and H₂O (8 ml, volume ratio, 1:1) at 423 K for 24 h.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, extended to show the Co coordination. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) x-1/2, -y+5/2, z.]
	Fig. 2. The one-dimensional chian structure of the title compound.

catena-Poly[[(2,2'-bipyridine-κ²N,N')cobalt(II)]- µ-oxalato-κ⁴O¹,O²:O^1',O^2'] top

Crystal data top

[Co(C₂O₄)(C₁₀H₈N₂)]	F(000) = 612
M_r = 303.13	D_x = 1.678 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2143 reflections
a = 9.2333 (18) Å	θ = 3.4–26.5°
b = 9.2163 (18) Å	µ = 1.44 mm⁻¹
c = 14.101 (3) Å	T = 293 K
V = 1199.9 (4) Å³	Plate, brown
Z = 4	0.16 × 0.14 × 0.08 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2692 independent reflections
Radiation source: rotating anode	1887 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
T_min = 0.800, T_max = 0.892	k = −11→11
10848 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0501P)² + 1.1682P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2692 reflections	Δρ_max = 0.38 e Å⁻³
172 parameters	Δρ_min = −0.90 e Å⁻³
1 restraint	Absolute structure: Flack (1983); 1283 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (4)

Crystal data top

[Co(C₂O₄)(C₁₀H₈N₂)]	V = 1199.9 (4) Å³
M_r = 303.13	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.2333 (18) Å	µ = 1.44 mm⁻¹
b = 9.2163 (18) Å	T = 293 K
c = 14.101 (3) Å	0.16 × 0.14 × 0.08 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2692 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1887 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.892	R_int = 0.064
10848 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.136	Δρ_max = 0.38 e Å⁻³
S = 1.09	Δρ_min = −0.90 e Å⁻³
2692 reflections	Absolute structure: Flack (1983); 1283 Friedel pairs
172 parameters	Absolute structure parameter: 0.03 (4)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.5044 (5)	1.2574 (5)	0.3939 (3)	0.0580 (13)
O4	0.4266 (4)	1.3874 (4)	0.2309 (3)	0.0507 (10)
C12	0.3425 (7)	1.2932 (7)	0.2640 (4)	0.0463 (14)
Co1	0.11792 (7)	1.08924 (7)	0.30925 (11)	0.0484 (2)
C11	0.3876 (6)	1.2177 (7)	0.3569 (4)	0.0441 (13)
O1	0.3038 (5)	1.1224 (4)	0.3891 (3)	0.0504 (10)
O3	0.2237 (5)	1.2560 (5)	0.2294 (3)	0.0543 (12)
C5	0.1633 (8)	0.7791 (7)	0.2550 (5)	0.0494 (15)
C6	0.0832 (8)	0.7718 (7)	0.3458 (5)	0.0519 (16)
N1	0.1983 (6)	0.9123 (6)	0.2254 (4)	0.0482 (12)
N2	0.0502 (6)	0.9010 (5)	0.3861 (4)	0.0485 (12)
C1	0.2749 (8)	0.9265 (8)	0.1462 (5)	0.0628 (18)
H1	0.3012	1.0189	0.1262	0.075*
C10	−0.0191 (8)	0.9026 (8)	0.4686 (5)	0.0630 (17)
H10	−0.0402	0.9916	0.4964	0.076*
C4	0.2031 (9)	0.6552 (8)	0.2047 (6)	0.066 (2)
H4	0.1776	0.5634	0.2264	0.079*
C9	−0.0611 (9)	0.7770 (9)	0.5146 (5)	0.074 (2)
H9	−0.1083	0.7819	0.5728	0.088*
C7	0.0401 (9)	0.6451 (8)	0.3887 (6)	0.069 (2)
H7	0.0604	0.5569	0.3596	0.083*
C2	0.3166 (9)	0.8083 (11)	0.0928 (6)	0.078 (2)
H2	0.3686	0.8209	0.0369	0.094*
C8	−0.0327 (10)	0.6461 (9)	0.4741 (6)	0.078 (2)
H8	−0.0615	0.5601	0.5031	0.094*
C3	0.2799 (10)	0.6717 (9)	0.1236 (6)	0.080 (2)
H3	0.3077	0.5907	0.0888	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.058 (3)	0.056 (3)	0.060 (3)	−0.010 (2)	−0.018 (3)	0.017 (2)
O4	0.057 (2)	0.046 (2)	0.049 (2)	−0.0021 (19)	−0.005 (2)	0.0123 (19)
C12	0.059 (3)	0.035 (3)	0.045 (3)	0.008 (3)	−0.003 (3)	0.002 (3)
Co1	0.0518 (4)	0.0394 (3)	0.0541 (4)	0.0005 (4)	−0.0009 (5)	−0.0032 (5)
C11	0.058 (4)	0.034 (3)	0.040 (3)	0.004 (3)	−0.007 (3)	0.001 (2)
O1	0.060 (2)	0.043 (2)	0.048 (2)	−0.0009 (19)	−0.007 (2)	0.0121 (19)
O3	0.058 (3)	0.055 (3)	0.050 (3)	−0.009 (2)	−0.014 (2)	0.009 (2)
C5	0.054 (3)	0.040 (3)	0.054 (4)	0.007 (3)	−0.004 (4)	0.000 (3)
C6	0.066 (4)	0.038 (3)	0.052 (4)	−0.007 (3)	−0.015 (4)	0.005 (3)
N1	0.057 (3)	0.044 (3)	0.044 (3)	0.006 (2)	0.005 (2)	−0.003 (2)
N2	0.053 (3)	0.046 (3)	0.046 (3)	−0.002 (2)	0.007 (3)	−0.003 (2)
C1	0.073 (4)	0.064 (4)	0.051 (4)	0.009 (4)	0.011 (4)	−0.001 (3)
C10	0.073 (4)	0.054 (4)	0.062 (4)	−0.011 (3)	0.006 (4)	−0.006 (3)
C4	0.080 (5)	0.046 (4)	0.073 (5)	0.008 (3)	−0.003 (4)	−0.013 (3)
C9	0.089 (5)	0.082 (5)	0.050 (4)	−0.023 (4)	0.013 (4)	0.004 (4)
C7	0.086 (5)	0.051 (4)	0.070 (5)	−0.013 (4)	0.006 (4)	−0.007 (4)
C2	0.083 (5)	0.090 (6)	0.062 (5)	0.015 (5)	0.022 (5)	−0.010 (4)
C8	0.102 (6)	0.062 (5)	0.071 (5)	−0.023 (4)	0.000 (5)	0.009 (4)
C3	0.094 (6)	0.063 (5)	0.082 (6)	0.027 (4)	0.006 (5)	−0.024 (4)

Geometric parameters (Å, º) top

O2—C11	1.252 (7)	C6—C7	1.374 (10)
O2—Co1ⁱ	2.126 (4)	N1—C1	1.328 (8)
O4—C12	1.254 (7)	N2—C10	1.327 (9)
O4—Co1ⁱ	2.095 (4)	C1—C2	1.379 (10)
C12—O3	1.248 (7)	C1—H1	0.9300
C12—C11	1.541 (6)	C10—C9	1.383 (10)
Co1—O1	2.076 (4)	C10—H10	0.9300
Co1—O4ⁱⁱ	2.095 (4)	C4—C3	1.355 (12)
Co1—O2ⁱⁱ	2.126 (4)	C4—H4	0.9300
Co1—N2	2.139 (5)	C9—C8	1.360 (11)
Co1—O3	2.142 (4)	C9—H9	0.9300
Co1—N1	2.146 (5)	C7—C8	1.379 (11)
C11—O1	1.256 (7)	C7—H7	0.9300
C5—N1	1.336 (8)	C2—C3	1.375 (12)
C5—C4	1.393 (10)	C2—H2	0.9300
C5—C6	1.480 (8)	C8—H8	0.9300
C6—N2	1.354 (8)	C3—H3	0.9300

C11—O2—Co1ⁱ	112.6 (4)	C1—N1—C5	118.7 (6)
C12—O4—Co1ⁱ	113.4 (4)	C1—N1—Co1	124.9 (5)
O3—C12—O4	126.0 (6)	C5—N1—Co1	116.3 (4)
O3—C12—C11	116.5 (5)	C10—N2—C6	119.1 (6)
O4—C12—C11	117.5 (5)	C10—N2—Co1	125.1 (5)
O1—Co1—O4ⁱⁱ	165.57 (14)	C6—N2—Co1	115.8 (4)
O1—Co1—O2ⁱⁱ	90.30 (17)	N1—C1—C2	122.1 (7)
O4ⁱⁱ—Co1—O2ⁱⁱ	79.14 (16)	N1—C1—H1	119.0
O1—Co1—N2	94.94 (18)	C2—C1—H1	119.0
O4ⁱⁱ—Co1—N2	95.99 (19)	N2—C10—C9	122.5 (7)
O2ⁱⁱ—Co1—N2	96.4 (2)	N2—C10—H10	118.8
O1—Co1—O3	78.61 (16)	C9—C10—H10	118.8
O4ⁱⁱ—Co1—O3	91.91 (17)	C3—C4—C5	118.4 (7)
O2ⁱⁱ—Co1—O3	92.47 (16)	C3—C4—H4	120.8
N2—Co1—O3	169.12 (18)	C5—C4—H4	120.8
O1—Co1—N1	97.18 (19)	C8—C9—C10	119.4 (8)
O4ⁱⁱ—Co1—N1	94.55 (18)	C8—C9—H9	120.3
O2ⁱⁱ—Co1—N1	169.92 (18)	C10—C9—H9	120.3
N2—Co1—N1	76.34 (17)	C6—C7—C8	121.3 (8)
O3—Co1—N1	95.6 (2)	C6—C7—H7	119.3
O2—C11—O1	125.7 (6)	C8—C7—H7	119.3
O2—C11—C12	117.1 (5)	C3—C2—C1	118.8 (8)
O1—C11—C12	117.2 (5)	C3—C2—H2	120.6
C11—O1—Co1	114.6 (4)	C1—C2—H2	120.6
C12—O3—Co1	113.1 (4)	C9—C8—C7	117.8 (7)
N1—C5—C4	122.0 (7)	C9—C8—H8	121.1
N1—C5—C6	115.6 (6)	C7—C8—H8	121.1
C4—C5—C6	122.3 (7)	C4—C3—C2	119.9 (7)
N2—C6—C7	119.8 (7)	C4—C3—H3	120.1
N2—C6—C5	115.8 (6)	C2—C3—H3	120.1
C7—C6—C5	124.3 (7)

Co1ⁱ—O4—C12—O3	−178.1 (5)	O3—Co1—N1—C1	−5.9 (6)
Co1ⁱ—O4—C12—C11	3.1 (6)	O1—Co1—N1—C5	97.1 (5)
Co1ⁱ—O2—C11—O1	175.8 (5)	O4ⁱⁱ—Co1—N1—C5	−91.3 (5)
Co1ⁱ—O2—C11—C12	−4.6 (6)	O2ⁱⁱ—Co1—N1—C5	−40.5 (14)
O3—C12—C11—O2	−177.8 (7)	N2—Co1—N1—C5	3.7 (5)
O4—C12—C11—O2	1.1 (7)	O3—Co1—N1—C5	176.3 (5)
O3—C12—C11—O1	1.8 (7)	C7—C6—N2—C10	2.4 (10)
O4—C12—C11—O1	−179.2 (6)	C5—C6—N2—C10	−178.7 (5)
O2—C11—O1—Co1	178.8 (5)	C7—C6—N2—Co1	−178.0 (6)
C12—C11—O1—Co1	−0.8 (6)	C5—C6—N2—Co1	0.9 (7)
O4ⁱⁱ—Co1—O1—C11	−49.8 (10)	O1—Co1—N2—C10	81.0 (6)
O2ⁱⁱ—Co1—O1—C11	−92.5 (4)	O4ⁱⁱ—Co1—N2—C10	−89.6 (5)
N2—Co1—O1—C11	171.1 (4)	O2ⁱⁱ—Co1—N2—C10	−9.9 (6)
O3—Co1—O1—C11	0.0 (4)	O3—Co1—N2—C10	134.1 (10)
N1—Co1—O1—C11	94.3 (4)	N1—Co1—N2—C10	177.2 (5)
O4—C12—O3—Co1	179.4 (5)	O1—Co1—N2—C6	−98.6 (5)
C11—C12—O3—Co1	−1.8 (6)	O4ⁱⁱ—Co1—N2—C6	90.9 (5)
O1—Co1—O3—C12	1.1 (4)	O2ⁱⁱ—Co1—N2—C6	170.6 (5)
O4ⁱⁱ—Co1—O3—C12	170.1 (4)	O3—Co1—N2—C6	−45.5 (13)
O2ⁱⁱ—Co1—O3—C12	90.9 (4)	N1—Co1—N2—C6	−2.4 (5)
N2—Co1—O3—C12	−53.3 (13)	C5—N1—C1—C2	1.4 (11)
N1—Co1—O3—C12	−95.1 (5)	Co1—N1—C1—C2	−176.3 (6)
N1—C5—C6—N2	2.4 (7)	C6—N2—C10—C9	−1.0 (10)
C4—C5—C6—N2	−179.2 (8)	Co1—N2—C10—C9	179.5 (6)
N1—C5—C6—C7	−178.8 (8)	N1—C5—C4—C3	0.2 (11)
C4—C5—C6—C7	−0.3 (9)	C6—C5—C4—C3	−178.2 (7)
C4—C5—N1—C1	−0.9 (10)	N2—C10—C9—C8	−0.9 (12)
C6—C5—N1—C1	177.6 (6)	N2—C6—C7—C8	−2.1 (12)
C4—C5—N1—Co1	177.1 (5)	C5—C6—C7—C8	179.1 (7)
C6—C5—N1—Co1	−4.5 (7)	N1—C1—C2—C3	−1.3 (12)
O1—Co1—N1—C1	−85.1 (6)	C10—C9—C8—C7	1.2 (13)
O4ⁱⁱ—Co1—N1—C1	86.5 (6)	C6—C7—C8—C9	0.2 (13)
O2ⁱⁱ—Co1—N1—C1	137.3 (11)	C5—C4—C3—C2	0.0 (12)
N2—Co1—N1—C1	−178.4 (6)	C1—C2—C3—C4	0.5 (13)

Symmetry codes: (i) x+1/2, −y+5/2, z; (ii) x−1/2, −y+5/2, z.

Experimental details

Crystal data
Chemical formula	[Co(C₂O₄)(C₁₀H₈N₂)]
M_r	303.13
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	9.2333 (18), 9.2163 (18), 14.101 (3)
V (Å³)	1199.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.16 × 0.14 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.800, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	10848, 2692, 1887
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.136, 1.09
No. of reflections	2692
No. of parameters	172
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.90
Absolute structure	Flack (1983); 1283 Friedel pairs
Absolute structure parameter	0.03 (4)

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Co1—O1	2.076 (4)	Co1—N2	2.139 (5)
Co1—O4ⁱ	2.095 (4)	Co1—O3	2.142 (4)
Co1—O2ⁱ	2.126 (4)	Co1—N1	2.146 (5)

Symmetry code: (i) x−1/2, −y+5/2, z.

Acknowledgements

We thank AIST and Kobe University for financial support.

References

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