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

Chang, Y.; Zhang, K.-L.; Ng, S.W.

doi:10.1107/S1600536809037878

metal-organic compounds

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Volume 65| Part 10| October 2009| Page m1243

doi:10.1107/S1600536809037878

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

Yan Chang,^a Kou-Lin Zhang ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 September 2009; accepted 18 September 2009; online 26 September 2009)

In the title compound, [Co(C₂O₄)(C₁₀H₈N₂)]_n, the oxalate group chelates two adjacent metal atoms, resulting in a zigzag chain running along the a axis. The Co^II centre exists in an all cis-octahedral coordination geometry.

Related literature

The Mn(II), Fe(II), Ni(II), Cu(II) and Zn(II) analogs are isostructural; see: Deguenon et al. (1990 ); Fun et al. (1999 ); Lin et al. (2006 ); Luo et al. (2001 ); Yu et al. (2006 ).

Experimental

Crystal data

[Co(C₂O₄)(C₁₀H₈N₂)]
M_r = 303.13
Orthorhombic, P n a 2₁
a = 9.1275 (8) Å
b = 9.2323 (8) Å
c = 14.1929 (12) Å
V = 1196.00 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 293 K
0.36 × 0.25 × 0.18 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.624, T_max = 0.781
9371 measured reflections
2698 independent reflections
2456 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.068
S = 1.01
2698 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1277 Friedel pairs
Flack parameter: −0.02 (2)

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037878/bt5061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037878/bt5061Isup2.hkl

checkCIF report

Comment top

The oxalate group chelates two adjacent metal atoms in Co(C₁₀H₈N₂)(C₂O₄) resulting in a zigzag chain running along the a-axis of the orthorhombic unit cell. The cobalt atom exists in an all cis-octahedral coordination geometry.

Related literature top

The Mn(II), Fe(II), Ni(II), Cu(II) and Zn(II) analogs are isostructural; see: Deguenon et al. (1990); Fun et al. (1999); Lin et al. (2006); Luo et al. (2001); Yu et al. (2006).

Experimental top

An aqueous solution of 2M sodium hydroxide (0.2 ml) was added to a water/DMF (2:7 v/v) solution (9 ml) of cobalt(II) oxalate dihdyrate (0.01 g, 0.05 mmol) and 2,2'-bipyridine (0.01 g, 0.05 mmol). Pink blocks separated from the solution after several days in 30% yield. CH&N elemental analysis. Calculated for C₁₂H₈CoN₂O₄: C 47.55, H 2.66, N 9.24%. Found: C 47.27, H 2.94, N 9.40%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a section of the chain structure of Co(C₁₀H₈N₂)(C₂O₄) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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 = 1.683 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4493 reflections
a = 9.1275 (8) Å	θ = 2.6–26.1°
b = 9.2323 (8) Å	µ = 1.45 mm⁻¹
c = 14.1929 (12) Å	T = 293 K
V = 1196.00 (18) Å³	Prism, pink
Z = 4	0.36 × 0.25 × 0.18 mm

Data collection top

Bruker APEXII diffractometer	2698 independent reflections
Radiation source: fine-focus sealed tube	2456 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.624, T_max = 0.781	k = −11→11
9371 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)] = 0.026	H-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0436P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2698 reflections	Δρ_max = 0.17 e Å⁻³
172 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1277 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (2)

Crystal data top

[Co(C₂O₄)(C₁₀H₈N₂)]	V = 1196.00 (18) Å³
M_r = 303.13	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.1275 (8) Å	µ = 1.45 mm⁻¹
b = 9.2323 (8) Å	T = 293 K
c = 14.1929 (12) Å	0.36 × 0.25 × 0.18 mm

Data collection top

Bruker APEXII diffractometer	2698 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2456 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.781	R_int = 0.025
9371 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.17 e Å⁻³
S = 1.01	Δρ_min = −0.23 e Å⁻³
2698 reflections	Absolute structure: Flack (1983), 1277 Friedel pairs
172 parameters	Absolute structure parameter: −0.02 (2)
1 restraint

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

	x	y	z	U_iso*/U_eq
Co1	0.38104 (3)	0.58866 (2)	0.49966 (4)	0.03408 (9)
N1	0.3016 (2)	0.4155 (2)	0.41608 (15)	0.0413 (5)
N2	0.4481 (2)	0.40387 (19)	0.57666 (14)	0.0390 (4)
O1	0.27899 (18)	0.75569 (19)	0.42055 (11)	0.0445 (4)
O2	0.07533 (18)	0.88996 (17)	0.42286 (12)	0.0409 (4)
O3	0.19137 (17)	0.61940 (16)	0.57821 (11)	0.0389 (3)
O4	−0.00808 (15)	0.75786 (19)	0.58323 (12)	0.0449 (4)
C1	0.2256 (3)	0.4294 (3)	0.3354 (2)	0.0551 (7)
H1	0.1995	0.5218	0.3153	0.066*
C2	0.1847 (3)	0.3113 (4)	0.2810 (2)	0.0674 (8)
H2	0.1334	0.3240	0.2250	0.081*
C3	0.2216 (4)	0.1757 (4)	0.3117 (2)	0.0710 (9)
H3	0.1954	0.0948	0.2765	0.085*
C4	0.2974 (3)	0.1594 (3)	0.3946 (2)	0.0574 (7)
H4	0.3222	0.0675	0.4162	0.069*
C5	0.3367 (3)	0.2817 (3)	0.44589 (16)	0.0385 (5)
C6	0.4169 (3)	0.2747 (3)	0.53643 (18)	0.0390 (5)
C7	0.4574 (4)	0.1460 (3)	0.5795 (2)	0.0583 (7)
H7	0.4359	0.0578	0.5511	0.070*
C8	0.5303 (4)	0.1498 (4)	0.6653 (2)	0.0661 (8)
H8	0.5587	0.0642	0.6947	0.079*
C9	0.5598 (3)	0.2808 (4)	0.70638 (19)	0.0635 (8)
H9	0.6075	0.2857	0.7642	0.076*
C10	0.5172 (3)	0.4054 (3)	0.6601 (2)	0.0531 (7)
H110	0.5373	0.4944	0.6880	0.064*
C11	0.1593 (2)	0.7943 (2)	0.45489 (15)	0.0329 (4)
C12	0.1106 (2)	0.7173 (3)	0.54720 (15)	0.0329 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03270 (14)	0.03499 (14)	0.03454 (13)	−0.00016 (11)	0.00143 (14)	−0.00307 (16)
N1	0.0463 (11)	0.0436 (11)	0.0339 (10)	−0.0047 (8)	−0.0038 (8)	−0.0021 (8)
N2	0.0408 (11)	0.0406 (11)	0.0356 (10)	0.0037 (8)	−0.0018 (8)	−0.0021 (8)
O1	0.0411 (9)	0.0516 (10)	0.0409 (9)	0.0057 (7)	0.0145 (8)	0.0104 (8)
O2	0.0398 (8)	0.0430 (9)	0.0401 (9)	0.0032 (7)	0.0070 (7)	0.0130 (7)
O3	0.0377 (8)	0.0401 (8)	0.0388 (8)	0.0037 (7)	0.0054 (7)	0.0105 (7)
O4	0.0397 (9)	0.0536 (10)	0.0413 (9)	0.0093 (7)	0.0125 (8)	0.0179 (8)
C1	0.0618 (17)	0.0630 (17)	0.0404 (13)	−0.0075 (13)	−0.0131 (12)	−0.0006 (12)
C2	0.0740 (19)	0.085 (2)	0.0435 (15)	−0.0175 (17)	−0.0170 (14)	−0.0103 (14)
C3	0.082 (2)	0.069 (2)	0.0628 (18)	−0.0255 (17)	−0.0066 (16)	−0.0259 (16)
C4	0.0692 (18)	0.0465 (15)	0.0565 (16)	−0.0145 (13)	−0.0005 (14)	−0.0107 (12)
C5	0.0407 (11)	0.0403 (12)	0.0346 (12)	−0.0044 (11)	0.0034 (10)	−0.0051 (10)
C6	0.0429 (12)	0.0341 (11)	0.0402 (12)	0.0035 (10)	0.0077 (10)	−0.0023 (9)
C7	0.0777 (19)	0.0428 (14)	0.0544 (15)	0.0149 (14)	−0.0004 (15)	−0.0044 (13)
C8	0.086 (2)	0.0576 (17)	0.0546 (16)	0.0271 (16)	0.0024 (16)	0.0105 (15)
C9	0.0727 (18)	0.077 (2)	0.0406 (15)	0.0236 (16)	−0.0064 (13)	0.0052 (14)
C10	0.0622 (17)	0.0555 (16)	0.0416 (13)	0.0124 (12)	−0.0082 (13)	−0.0062 (11)
C11	0.0342 (10)	0.0332 (11)	0.0312 (10)	−0.0055 (10)	0.0024 (9)	0.0017 (9)
C12	0.0318 (11)	0.0349 (11)	0.0321 (11)	−0.0025 (9)	0.0030 (8)	0.0025 (9)

Geometric parameters (Å, º) top

Co1—O3	2.0786 (16)	C1—H1	0.9300
Co1—O2ⁱ	2.0909 (16)	C2—C3	1.367 (5)
Co1—O4ⁱ	2.1068 (16)	C2—H2	0.9300
Co1—N1	2.119 (2)	C3—C4	1.374 (5)
Co1—N2	2.1165 (19)	C3—H3	0.9300
Co1—O1	2.1228 (17)	C4—C5	1.391 (4)
N1—C1	1.344 (3)	C4—H4	0.9300
N1—C5	1.344 (3)	C5—C6	1.480 (3)
N2—C10	1.342 (3)	C6—C7	1.386 (4)
N2—C6	1.352 (3)	C7—C8	1.388 (4)
O1—C11	1.248 (3)	C7—H7	0.9300
O2—C11	1.255 (3)	C8—C9	1.369 (5)
O2—Co1ⁱⁱ	2.0909 (16)	C8—H8	0.9300
O3—C12	1.247 (3)	C9—C10	1.381 (4)
O4—C12	1.255 (2)	C9—H9	0.9300
O4—Co1ⁱⁱ	2.1068 (16)	C10—H110	0.9300
C1—C2	1.388 (4)	C11—C12	1.555 (2)

O3—Co1—O2ⁱ	166.68 (6)	C2—C3—C4	119.8 (3)
O3—Co1—O4ⁱ	90.36 (6)	C2—C3—H3	120.1
O2ⁱ—Co1—O4ⁱ	79.78 (6)	C4—C3—H3	120.1
O3—Co1—N1	96.78 (8)	C3—C4—C5	119.3 (3)
O2ⁱ—Co1—N1	94.00 (7)	C3—C4—H4	120.4
O4ⁱ—Co1—N1	170.80 (7)	C5—C4—H4	120.4
O3—Co1—N2	94.24 (7)	N1—C5—C4	121.3 (2)
O2ⁱ—Co1—N2	95.74 (7)	N1—C5—C6	115.6 (2)
O4ⁱ—Co1—N2	96.46 (8)	C4—C5—C6	123.1 (3)
N1—Co1—N2	77.29 (7)	N2—C6—C7	120.9 (3)
O3—Co1—O1	79.57 (6)	N2—C6—C5	115.6 (2)
O2ⁱ—Co1—O1	91.60 (7)	C7—C6—C5	123.5 (3)
O4ⁱ—Co1—O1	91.15 (7)	C8—C7—C6	119.6 (3)
N1—Co1—O1	95.83 (8)	C8—C7—H7	120.2
N2—Co1—O1	170.25 (7)	C6—C7—H7	120.2
C1—N1—C5	118.6 (2)	C9—C8—C7	119.3 (3)
C1—N1—Co1	125.54 (18)	C9—C8—H8	120.3
C5—N1—Co1	115.80 (17)	C7—C8—H8	120.3
C10—N2—C6	118.8 (2)	C8—C9—C10	118.6 (3)
C10—N2—Co1	125.67 (16)	C8—C9—H9	120.7
C6—N2—Co1	115.58 (17)	C10—C9—H9	120.7
C11—O1—Co1	112.63 (14)	N2—C10—C9	122.9 (3)
C11—O2—Co1ⁱⁱ	113.30 (14)	N2—C10—H110	118.5
C12—O3—Co1	113.72 (14)	C9—C10—H110	118.5
C12—O4—Co1ⁱⁱ	112.70 (15)	O1—C11—O2	126.4 (2)
N1—C1—C2	122.5 (3)	O1—C11—C12	116.67 (18)
N1—C1—H1	118.8	O2—C11—C12	116.88 (17)
C2—C1—H1	118.8	O3—C12—O4	125.7 (2)
C3—C2—C1	118.5 (3)	O3—C12—C11	117.35 (17)
C3—C2—H2	120.8	O4—C12—C11	116.98 (18)
C1—C2—H2	120.8

O3—Co1—N1—C1	86.2 (2)	C1—N1—C5—C6	−178.5 (2)
O2ⁱ—Co1—N1—C1	−86.0 (2)	Co1—N1—C5—C6	4.1 (3)
N2—Co1—N1—C1	179.0 (2)	C3—C4—C5—N1	0.2 (4)
O1—Co1—N1—C1	6.0 (2)	C3—C4—C5—C6	179.3 (3)
O3—Co1—N1—C5	−96.68 (18)	C10—N2—C6—C7	−1.1 (4)
O2ⁱ—Co1—N1—C5	91.16 (18)	Co1—N2—C6—C7	179.0 (2)
N2—Co1—N1—C5	−3.84 (18)	C10—N2—C6—C5	178.2 (2)
O1—Co1—N1—C5	−176.83 (18)	Co1—N2—C6—C5	−1.7 (3)
O3—Co1—N2—C10	−81.0 (2)	N1—C5—C6—N2	−1.6 (3)
O2ⁱ—Co1—N2—C10	90.2 (2)	C4—C5—C6—N2	179.2 (3)
O4ⁱ—Co1—N2—C10	9.8 (2)	N1—C5—C6—C7	177.7 (3)
N1—Co1—N2—C10	−177.0 (2)	C4—C5—C6—C7	−1.5 (4)
O3—Co1—N2—C6	98.92 (19)	N2—C6—C7—C8	0.4 (5)
O2ⁱ—Co1—N2—C6	−89.91 (18)	C5—C6—C7—C8	−178.9 (2)
O4ⁱ—Co1—N2—C6	−170.23 (18)	C6—C7—C8—C9	0.5 (5)
N1—Co1—N2—C6	2.91 (19)	C7—C8—C9—C10	−0.7 (5)
O3—Co1—O1—C11	0.09 (16)	C6—N2—C10—C9	0.9 (4)
O2ⁱ—Co1—O1—C11	−169.87 (16)	Co1—N2—C10—C9	−179.2 (2)
O4ⁱ—Co1—O1—C11	−90.06 (16)	C8—C9—C10—N2	0.0 (4)
N1—Co1—O1—C11	95.94 (17)	Co1—O1—C11—O2	−179.71 (19)
O2ⁱ—Co1—O3—C12	47.6 (4)	Co1—O1—C11—C12	1.1 (2)
O4ⁱ—Co1—O3—C12	89.55 (17)	Co1ⁱⁱ—O2—C11—O1	177.06 (19)
N1—Co1—O3—C12	−96.27 (17)	Co1ⁱⁱ—O2—C11—C12	−3.8 (2)
N2—Co1—O3—C12	−173.95 (17)	Co1—O3—C12—O4	−178.58 (19)
O1—Co1—O3—C12	−1.55 (16)	Co1—O3—C12—C11	2.6 (2)
C5—N1—C1—C2	−1.3 (4)	Co1ⁱⁱ—O4—C12—O3	−174.00 (19)
Co1—N1—C1—C2	175.8 (2)	Co1ⁱⁱ—O4—C12—C11	4.9 (2)
N1—C1—C2—C3	0.9 (5)	O1—C11—C12—O3	−2.6 (3)
C1—C2—C3—C4	0.0 (5)	O2—C11—C12—O3	178.2 (2)
C2—C3—C4—C5	−0.5 (5)	O1—C11—C12—O4	178.4 (2)
C1—N1—C5—C4	0.7 (4)	O2—C11—C12—O4	−0.8 (3)
Co1—N1—C5—C4	−176.7 (2)

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+3/2, 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)	9.1275 (8), 9.2323 (8), 14.1929 (12)
V (Å³)	1196.00 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.36 × 0.25 × 0.18

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.624, 0.781
No. of measured, independent and observed [I > 2σ(I)] reflections	9371, 2698, 2456
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.068, 1.01
No. of reflections	2698
No. of parameters	172
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23
Absolute structure	Flack (1983), 1277 Friedel pairs
Absolute structure parameter	−0.02 (2)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank Yangzhou University and the University of Malaya for supporting this study.

References

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