catena-Poly[[(2,2-bipyridine)cobalt(II)]-μ-imidazole-4,5-dicarboxyl­ato]

Hao, L.-J.; Bao, Z.-M.; Yu, T.-L.

doi:10.1107/S1600536807027699

Retracted: catena-Poly[[(2,2-bipyridine)cobalt(II)]-μ-imidazole-4,5-dicarboxylato]

In the title complex, [Co(C₅HN₂O₄)(C₁₀H₈N₂)]_n, the asymmetric unit contains two crystallographically independent monomer units with similar geometry. The Co^II cations are coordinated octahedrally by two carboxylate O atoms and by four N atoms, two of which belong to the 2,2-bipyridine ligand and two to different imidazole rings. The connectivity between the metal cations and the imidazole-4,5-carboxylate units gives rise to one-dimensional zigzag chains parallel to [010].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027699/wm2118sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027699/wm2118Isup2.hkl Contains datablock I

CCDC reference: 1148882

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.032
wR factor = 0.104
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.58
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co2         (2)       1.60

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Hybrid organic-inorganic materials are important materials because of their application in catalysis, as optical materials, membranes, and in sorption (Church & Halvorson, 1959; Chung et al., 1971), as well as in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Herein, we report a new compound, catena-poly[(2,2-bipyridine)(imidazole-4,5-dicarboxylate)cobalt(II)], (I).

In the structure of compound (I), the asymmetric unit contains two crystallographically independent molecules with nearly the same geometry. As shown in Fig. 1, the Co^II cations exhibit a distorted octahedral coordination sphere, made up of two carboxylate oxygen atoms and four nitrogen atoms, two of which belong to the 2,2-bipyridine ligand and the other two to the imidazole ring. The Co—O and Co—N bond lengths are in the usual ranges with 2.1569 (18) to 2.2562 (19) and 2.077 (2) to 2.271 (2) Å, respectively. The two carboxylate groups of the imidazole-4,5-dicarboxylate ligand coordinate in a monodentate fashion to the Co^II ions, whereby the connectivity between the cations and the ligands gives rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2-bipyridine ligands are situated in the space between the chains.

Related literature top

For studies and reviews on inorganic–organic hybrid materials, see Church & Halvorson (1959); Chung et al. (1971); Pocker & Fong (1980); Scapin et al. (1997); Okabe & Oya (2000); Serre et al. (2005).

Experimental top

All chemicals were purchased from Acros Co. Ltd. Compound (I) was obtained under hydrothermal conditions by reaction of cobalt sulfate (0.5 mmol), imidazole-4,5-dicarboxylic acid (0.5 mmol), 2,2-bipyridine (0.5 mmol) and KOH (1 mmol) in 20 ml distilled water. The mixture was heated in a 30 ml autoclave at 453 K for 3 d. Red crystals were obtained in a yield of approximately 25%. Analysis calculated for C₁₅H₉N₄CoO₄: C 48.96, H 2.47, N 15.23, Co 15.95%_wt; found: C 48.98, H 2.51, N 15.27, Co 16.08%_wt.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The two crystallographically independent molecules in (I), showing 30% probability displacement ellipsoids. [Symmetry codes: (i) -x + 1, y + 1/2, -z + 3/2].
	Fig. 2. A zigzag chain extending palallel to [010] in (I).

catena-Poly[[(2,2-bipyridine)cobalt(II)]-µ-imidazole-4,5-dicarboxylato] top

Crystal data top

[Co(C₅HN₂O₄)(C₁₀H₈N₂)]	F(000) = 1488
M_r = 368.19	D_x = 1.711 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5547 reflections
a = 20.5002 (10) Å	θ = 2.3–26.1°
b = 9.6500 (5) Å	µ = 1.23 mm⁻¹
c = 14.7623 (7) Å	T = 293 K
β = 101.801 (1)°	Cube, red
V = 2858.7 (2) Å³	0.10 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker APEX II CCD area-detector diffractometer	5563 independent reflections
Radiation source: fine-focus sealed tube	4855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→20
T_min = 0.887, T_max = 0.887	k = −11→10
15047 measured reflections	l = −17→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.039P)² + 0.9045P] where P = (F_o² + 2F_c²)/3
5563 reflections	(Δ/σ)_max = 0.001
433 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Co(C₅HN₂O₄)(C₁₀H₈N₂)]	V = 2858.7 (2) Å³
M_r = 368.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.5002 (10) Å	µ = 1.23 mm⁻¹
b = 9.6500 (5) Å	T = 293 K
c = 14.7623 (7) Å	0.10 × 0.10 × 0.10 mm
β = 101.801 (1)°

Data collection top

Bruker APEX II CCD area-detector diffractometer	5563 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4855 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.887	R_int = 0.027
15047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.00	Δρ_max = 0.54 e Å⁻³
5563 reflections	Δρ_min = −0.35 e Å⁻³
433 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
Co1	0.899411 (13)	−0.02479 (3)	0.214401 (19)	0.01403 (10)
Co2	0.597903 (14)	0.09584 (3)	0.81973 (2)	0.01626 (10)
N1	0.94287 (10)	−0.2240 (2)	0.23760 (13)	0.0241 (4)
O1	0.91439 (9)	−0.00358 (18)	0.07122 (12)	0.0264 (4)
O3	0.89860 (9)	−0.05143 (19)	0.35923 (12)	0.0292 (4)
O7	0.61837 (9)	0.0776 (2)	0.67573 (13)	0.0326 (4)
O5	0.56793 (9)	0.1364 (2)	0.95260 (13)	0.0325 (4)
N5	0.54592 (10)	0.2810 (2)	0.79047 (14)	0.0262 (5)
N2	0.98575 (11)	0.0964 (2)	0.23543 (14)	0.0244 (5)
N6	0.52456 (10)	−0.0428 (2)	0.75854 (14)	0.0258 (5)
N7	0.66335 (11)	−0.0778 (2)	0.87713 (15)	0.0276 (5)
N8	0.69413 (10)	0.1864 (2)	0.85720 (14)	0.0273 (5)
N3	0.84013 (11)	0.1734 (2)	0.17796 (15)	0.0292 (5)
N4	0.79750 (11)	−0.0866 (2)	0.17980 (15)	0.0274 (5)
C25	0.72862 (13)	−0.0456 (3)	0.90105 (17)	0.0268 (5)
C26	0.74592 (13)	0.1016 (3)	0.88752 (17)	0.0259 (5)
C27	0.81097 (13)	0.1492 (3)	0.90555 (18)	0.0316 (6)
H27	0.8461	0.0881	0.9249	0.038*
O8	0.58403 (10)	−0.0419 (2)	0.54499 (13)	0.0335 (4)
O4	0.94588 (10)	−0.1818 (2)	0.47970 (12)	0.0368 (5)
O6	0.49477 (10)	0.2666 (2)	1.00903 (12)	0.0345 (4)
O2	0.96716 (9)	0.13600 (19)	−0.01065 (11)	0.0286 (4)
C4	0.93289 (12)	−0.1533 (3)	0.39434 (17)	0.0262 (5)
C17	0.51348 (12)	0.3156 (3)	0.85967 (17)	0.0251 (5)
C20	0.47894 (12)	−0.1313 (3)	0.77887 (17)	0.0263 (5)
H20	0.4658	−0.1319	0.8355	0.032*
C24	0.77644 (13)	−0.1446 (3)	0.93791 (18)	0.0313 (6)
H24	0.8213	−0.1207	0.9542	0.038*
C1	0.95748 (12)	0.0865 (2)	0.06645 (17)	0.0234 (5)
C18	0.52989 (12)	−0.0767 (3)	0.67016 (17)	0.0241 (5)
C5	0.97688 (12)	−0.3213 (3)	0.20100 (16)	0.0245 (5)
H5	0.9747	−0.3305	0.1377	0.029*
C30	0.70633 (13)	0.3206 (3)	0.84595 (18)	0.0301 (6)
H30	0.6705	0.3795	0.8250	0.036*
C2	0.99722 (12)	0.1434 (3)	0.15254 (16)	0.0232 (5)
C3	0.95937 (12)	−0.2470 (2)	0.33094 (16)	0.0231 (5)
C28	0.82316 (14)	0.2885 (3)	0.89459 (19)	0.0339 (6)
H28	0.8665	0.3228	0.9075	0.041*
C16	0.52682 (12)	0.2342 (3)	0.94635 (17)	0.0270 (5)
C19	0.58001 (13)	−0.0072 (3)	0.62809 (18)	0.0270 (5)
C15	0.77793 (14)	−0.2154 (3)	0.19535 (19)	0.0326 (6)
H15	0.8103	−0.2803	0.2198	0.039*
C11	0.75122 (13)	0.0084 (3)	0.14536 (17)	0.0280 (6)
C10	0.77552 (13)	0.1525 (3)	0.13920 (17)	0.0282 (5)
C29	0.76973 (14)	0.3755 (3)	0.86409 (18)	0.0312 (6)
H29	0.7764	0.4696	0.8559	0.037*
C12	0.68375 (14)	−0.0266 (3)	0.1226 (2)	0.0392 (7)
H12	0.6522	0.0392	0.0968	0.047*
C6	0.86422 (15)	0.3021 (3)	0.1792 (2)	0.0358 (6)
H6	0.9087	0.3171	0.2063	0.043*
C22	0.68865 (14)	−0.3107 (3)	0.92572 (19)	0.0352 (6)
H22	0.6738	−0.4000	0.9337	0.042*
C9	0.73395 (15)	0.2603 (3)	0.10184 (19)	0.0369 (6)
H9	0.6893	0.2438	0.0761	0.044*
C23	0.75606 (14)	−0.2780 (3)	0.94960 (19)	0.0348 (6)
H23	0.7871	−0.3459	0.9733	0.042*
C14	0.71227 (14)	−0.2561 (3)	0.1769 (2)	0.0402 (7)
H14	0.7003	−0.3459	0.1896	0.048*
C21	0.64446 (14)	−0.2074 (3)	0.89001 (19)	0.0337 (6)
H21	0.5994	−0.2290	0.8741	0.040*
C8	0.75973 (17)	0.3918 (3)	0.1035 (2)	0.0445 (8)
H8A	0.7326	0.4655	0.0787	0.053*
C13	0.66438 (15)	−0.1595 (4)	0.1388 (2)	0.0464 (8)
H13	0.6196	−0.1842	0.1243	0.056*
C7	0.82565 (17)	0.4142 (3)	0.1418 (2)	0.0432 (7)
H7	0.8440	0.5024	0.1428	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01135 (17)	0.01285 (17)	0.01726 (17)	0.00016 (10)	0.00146 (12)	0.00298 (11)
Co2	0.01115 (17)	0.01302 (17)	0.02239 (18)	0.00011 (10)	−0.00177 (12)	−0.00095 (11)
N1	0.0253 (11)	0.0242 (11)	0.0222 (10)	0.0010 (8)	0.0032 (8)	0.0019 (8)
O1	0.0249 (9)	0.0274 (9)	0.0260 (9)	−0.0046 (7)	0.0033 (7)	−0.0023 (7)
O3	0.0312 (10)	0.0270 (9)	0.0299 (9)	0.0081 (8)	0.0076 (8)	0.0014 (8)
O7	0.0272 (10)	0.0338 (10)	0.0371 (10)	−0.0060 (8)	0.0073 (8)	−0.0015 (8)
O5	0.0315 (10)	0.0313 (10)	0.0326 (9)	0.0040 (8)	0.0015 (8)	0.0056 (8)
N5	0.0257 (11)	0.0272 (11)	0.0248 (10)	0.0004 (9)	0.0034 (8)	−0.0005 (9)
N2	0.0261 (11)	0.0242 (11)	0.0221 (10)	−0.0011 (8)	0.0031 (8)	0.0000 (8)
N6	0.0218 (11)	0.0278 (12)	0.0265 (10)	0.0006 (9)	0.0019 (8)	−0.0011 (9)
N7	0.0244 (11)	0.0260 (11)	0.0317 (11)	−0.0010 (9)	0.0041 (9)	0.0023 (9)
N8	0.0251 (11)	0.0271 (11)	0.0281 (11)	−0.0012 (9)	0.0017 (9)	−0.0004 (9)
N3	0.0285 (12)	0.0278 (12)	0.0320 (11)	0.0036 (9)	0.0074 (9)	0.0009 (9)
N4	0.0244 (11)	0.0313 (12)	0.0266 (11)	0.0001 (9)	0.0053 (9)	0.0014 (9)
C25	0.0252 (13)	0.0288 (14)	0.0251 (12)	−0.0005 (10)	0.0023 (10)	−0.0006 (10)
C26	0.0249 (13)	0.0283 (14)	0.0234 (12)	0.0009 (10)	0.0023 (10)	−0.0003 (10)
C27	0.0277 (14)	0.0314 (14)	0.0341 (14)	0.0005 (11)	0.0027 (11)	0.0048 (11)
O8	0.0340 (11)	0.0371 (11)	0.0316 (10)	−0.0005 (8)	0.0121 (8)	−0.0006 (8)
O4	0.0481 (12)	0.0397 (11)	0.0233 (9)	0.0145 (9)	0.0090 (8)	0.0014 (8)
O6	0.0380 (11)	0.0374 (11)	0.0288 (9)	0.0010 (9)	0.0089 (8)	0.0036 (8)
O2	0.0311 (10)	0.0309 (9)	0.0227 (8)	−0.0025 (8)	0.0033 (7)	−0.0005 (7)
C4	0.0253 (13)	0.0265 (13)	0.0264 (12)	0.0010 (10)	0.0046 (10)	0.0002 (10)
C17	0.0219 (12)	0.0266 (13)	0.0258 (12)	−0.0021 (10)	0.0024 (10)	−0.0006 (10)
C20	0.0237 (13)	0.0281 (13)	0.0267 (12)	−0.0020 (10)	0.0040 (10)	0.0000 (10)
C24	0.0256 (14)	0.0338 (15)	0.0324 (13)	0.0025 (11)	0.0010 (11)	−0.0001 (11)
C1	0.0220 (12)	0.0228 (12)	0.0255 (12)	0.0021 (10)	0.0049 (10)	0.0000 (9)
C18	0.0213 (12)	0.0244 (12)	0.0255 (12)	0.0039 (10)	0.0024 (10)	0.0006 (10)
C5	0.0270 (13)	0.0264 (13)	0.0197 (11)	0.0010 (10)	0.0039 (9)	0.0005 (10)
C30	0.0306 (14)	0.0248 (13)	0.0339 (13)	0.0008 (11)	0.0042 (11)	0.0029 (11)
C2	0.0222 (12)	0.0236 (12)	0.0230 (11)	0.0021 (10)	0.0027 (9)	0.0005 (10)
C3	0.0219 (12)	0.0232 (12)	0.0237 (11)	−0.0010 (10)	0.0039 (9)	0.0005 (10)
C28	0.0273 (14)	0.0386 (16)	0.0348 (14)	−0.0076 (12)	0.0037 (11)	0.0022 (12)
C16	0.0247 (13)	0.0261 (13)	0.0282 (12)	−0.0032 (10)	0.0005 (10)	0.0003 (10)
C19	0.0243 (13)	0.0261 (13)	0.0302 (13)	0.0041 (10)	0.0043 (10)	0.0012 (10)
C15	0.0315 (14)	0.0288 (14)	0.0362 (14)	−0.0030 (11)	0.0036 (11)	0.0004 (11)
C11	0.0249 (13)	0.0349 (14)	0.0230 (12)	0.0040 (11)	0.0021 (10)	−0.0011 (10)
C10	0.0267 (13)	0.0350 (14)	0.0240 (12)	0.0061 (11)	0.0077 (10)	0.0036 (11)
C29	0.0353 (15)	0.0261 (13)	0.0311 (13)	−0.0067 (11)	0.0045 (11)	0.0029 (11)
C12	0.0253 (14)	0.0472 (18)	0.0426 (16)	0.0040 (12)	0.0013 (12)	−0.0010 (13)
C6	0.0366 (16)	0.0295 (14)	0.0440 (16)	0.0029 (12)	0.0141 (13)	0.0015 (12)
C22	0.0387 (16)	0.0246 (13)	0.0412 (15)	−0.0010 (12)	0.0056 (12)	0.0045 (12)
C9	0.0328 (15)	0.0417 (17)	0.0364 (15)	0.0109 (13)	0.0072 (12)	0.0073 (13)
C23	0.0353 (15)	0.0281 (14)	0.0386 (15)	0.0085 (12)	0.0018 (12)	0.0047 (12)
C14	0.0359 (16)	0.0388 (16)	0.0448 (16)	−0.0091 (13)	0.0060 (13)	−0.0024 (13)
C21	0.0279 (14)	0.0326 (15)	0.0398 (15)	−0.0042 (11)	0.0051 (11)	0.0019 (12)
C8	0.0463 (19)	0.0386 (18)	0.0511 (18)	0.0192 (14)	0.0160 (15)	0.0123 (14)
C13	0.0246 (15)	0.056 (2)	0.0560 (19)	−0.0085 (14)	0.0023 (13)	−0.0086 (16)
C7	0.051 (2)	0.0271 (15)	0.0553 (19)	0.0068 (13)	0.0197 (16)	0.0043 (13)

Geometric parameters (Å, º) top

Co1—N2	2.091 (2)	C4—C3	1.482 (3)
Co1—N1	2.117 (2)	C17—C18ⁱ	1.380 (4)
Co1—N4	2.132 (2)	C17—C16	1.479 (3)
Co1—O3	2.1569 (18)	C20—N5ⁱⁱⁱ	1.345 (3)
Co1—O1	2.2067 (18)	C20—H20	0.9300
Co1—N3	2.271 (2)	C24—C23	1.375 (4)
Co2—N6	2.077 (2)	C24—H24	0.9300
Co2—N5	2.080 (2)	C1—C2	1.469 (3)
Co2—N8	2.125 (2)	C18—C17ⁱⁱⁱ	1.380 (4)
Co2—N7	2.205 (2)	C18—C19	1.467 (4)
Co2—O5	2.2071 (19)	C5—N2^iv	1.344 (3)
Co2—O7	2.2562 (19)	C5—H5	0.9300
N1—C5	1.347 (3)	C30—C29	1.378 (4)
N1—C3	1.368 (3)	C30—H30	0.9300
O1—C1	1.252 (3)	C2—C3ⁱⁱ	1.371 (3)
O3—C4	1.257 (3)	C3—C2^iv	1.371 (3)
O7—C19	1.248 (3)	C28—C29	1.381 (4)
O5—C16	1.257 (3)	C28—H28	0.9300
N5—C20ⁱ	1.345 (3)	C15—C14	1.375 (4)
N5—C17	1.369 (3)	C15—H15	0.9300
N2—C5ⁱⁱ	1.344 (3)	C11—C12	1.396 (4)
N2—C2	1.370 (3)	C11—C10	1.486 (4)
N6—C20	1.345 (3)	C10—C9	1.386 (4)
N6—C18	1.371 (3)	C29—H29	0.9300
N7—C21	1.334 (3)	C12—C13	1.378 (4)
N7—C25	1.348 (3)	C12—H12	0.9300
N8—C30	1.335 (3)	C6—C7	1.386 (4)
N8—C26	1.343 (3)	C6—H6	0.9300
N3—C6	1.335 (4)	C22—C21	1.377 (4)
N3—C10	1.346 (3)	C22—C23	1.391 (4)
N4—C15	1.341 (3)	C22—H22	0.9300
N4—C11	1.342 (3)	C9—C8	1.373 (4)
C25—C24	1.397 (4)	C9—H9	0.9300
C25—C26	1.488 (4)	C23—H23	0.9300
C26—C27	1.384 (4)	C14—C13	1.387 (4)
C27—C28	1.383 (4)	C14—H14	0.9300
C27—H27	0.9300	C21—H21	0.9300
O8—C19	1.290 (3)	C8—C7	1.371 (5)
O4—C4	1.264 (3)	C8—H8A	0.9300
O6—C16	1.278 (3)	C13—H13	0.9300
O2—C1	1.286 (3)	C7—H7	0.9300

N2—Co1—N1	99.69 (8)	N5ⁱⁱⁱ—C20—H20	123.1
N2—Co1—N4	161.87 (8)	N6—C20—H20	123.1
N1—Co1—N4	98.29 (8)	C23—C24—C25	118.8 (3)
N2—Co1—O3	95.59 (8)	C23—C24—H24	120.6
N1—Co1—O3	79.61 (7)	C25—C24—H24	120.6
N4—Co1—O3	89.90 (7)	O1—C1—O2	123.1 (2)
N2—Co1—O1	79.10 (7)	O1—C1—C2	118.9 (2)
N1—Co1—O1	95.90 (7)	O2—C1—C2	117.9 (2)
N4—Co1—O1	96.78 (7)	N6—C18—C17ⁱⁱⁱ	108.2 (2)
O3—Co1—O1	172.46 (7)	N6—C18—C19	119.5 (2)
N2—Co1—N3	87.70 (8)	C17ⁱⁱⁱ—C18—C19	132.1 (2)
N1—Co1—N3	171.99 (8)	N2^iv—C5—N1	113.6 (2)
N4—Co1—N3	74.22 (8)	N2^iv—C5—H5	123.2
O3—Co1—N3	102.88 (7)	N1—C5—H5	123.2
O1—Co1—N3	82.39 (7)	N8—C30—C29	122.8 (3)
N6—Co2—N5	99.70 (8)	N8—C30—H30	118.6
N6—Co2—N8	158.35 (8)	C29—C30—H30	118.6
N5—Co2—N8	96.30 (8)	N2—C2—C3ⁱⁱ	108.7 (2)
N6—Co2—N7	90.40 (8)	N2—C2—C1	118.9 (2)
N5—Co2—N7	168.06 (8)	C3ⁱⁱ—C2—C1	131.8 (2)
N8—Co2—N7	75.70 (8)	N1—C3—C2^iv	108.8 (2)
N6—Co2—O5	101.08 (8)	N1—C3—C4	119.3 (2)
N5—Co2—O5	78.96 (7)	C2^iv—C3—C4	131.8 (2)
N8—Co2—O5	96.21 (8)	C29—C28—C27	118.6 (3)
N7—Co2—O5	92.93 (7)	C29—C28—H28	120.7
N6—Co2—O7	78.32 (7)	C27—C28—H28	120.7
N5—Co2—O7	93.30 (7)	O5—C16—O6	124.5 (2)
N8—Co2—O7	86.32 (7)	O5—C16—C17	117.7 (2)
N7—Co2—O7	94.99 (8)	O6—C16—C17	117.7 (2)
O5—Co2—O7	172.05 (7)	O7—C19—O8	123.4 (2)
C5—N1—C3	104.4 (2)	O7—C19—C18	118.5 (2)
C5—N1—Co1	143.46 (17)	O8—C19—C18	118.0 (2)
C3—N1—Co1	108.64 (16)	N4—C15—C14	123.1 (3)
C1—O1—Co1	110.88 (15)	N4—C15—H15	118.5
C4—O3—Co1	112.63 (16)	C14—C15—H15	118.5
C19—O7—Co2	111.41 (17)	N4—C11—C12	121.0 (3)
C16—O5—Co2	111.86 (16)	N4—C11—C10	116.2 (2)
C20ⁱ—N5—C17	104.3 (2)	C12—C11—C10	122.6 (2)
C20ⁱ—N5—Co2	142.80 (17)	N3—C10—C9	121.9 (3)
C17—N5—Co2	111.18 (16)	N3—C10—C11	115.3 (2)
C5ⁱⁱ—N2—C2	104.5 (2)	C9—C10—C11	122.7 (2)
C5ⁱⁱ—N2—Co1	141.16 (18)	C28—C29—C30	118.9 (3)
C2—N2—Co1	110.34 (15)	C28—C29—H29	120.6
C20—N6—C18	104.8 (2)	C30—C29—H29	120.6
C20—N6—Co2	141.90 (18)	C13—C12—C11	119.3 (3)
C18—N6—Co2	112.09 (17)	C13—C12—H12	120.3
C21—N7—C25	118.7 (2)	C11—C12—H12	120.3
C21—N7—Co2	126.56 (18)	N3—C6—C7	122.8 (3)
C25—N7—Co2	114.77 (17)	N3—C6—H6	118.6
C30—N8—C26	118.5 (2)	C7—C6—H6	118.6
C30—N8—Co2	123.64 (18)	C21—C22—C23	118.3 (3)
C26—N8—Co2	117.67 (17)	C21—C22—H22	120.8
C6—N3—C10	118.3 (2)	C23—C22—H22	120.8
C6—N3—Co1	126.98 (19)	C8—C9—C10	118.9 (3)
C10—N3—Co1	113.98 (17)	C8—C9—H9	120.5
C15—N4—C11	119.0 (2)	C10—C9—H9	120.5
C15—N4—Co1	122.09 (18)	C24—C23—C22	119.5 (3)
C11—N4—Co1	118.81 (18)	C24—C23—H23	120.3
N7—C25—C24	121.6 (2)	C22—C23—H23	120.3
N7—C25—C26	115.8 (2)	C15—C14—C13	118.1 (3)
C24—C25—C26	122.5 (2)	C15—C14—H14	120.9
N8—C26—C27	121.8 (2)	C13—C14—H14	120.9
N8—C26—C25	115.7 (2)	N7—C21—C22	123.1 (3)
C27—C26—C25	122.6 (2)	N7—C21—H21	118.5
C28—C27—C26	119.4 (3)	C22—C21—H21	118.5
C28—C27—H27	120.3	C7—C8—C9	119.7 (3)
C26—C27—H27	120.3	C7—C8—H8A	120.1
O3—C4—O4	124.5 (2)	C9—C8—H8A	120.1
O3—C4—C3	117.6 (2)	C12—C13—C14	119.4 (3)
O4—C4—C3	117.9 (2)	C12—C13—H13	120.3
N5—C17—C18ⁱ	109.0 (2)	C14—C13—H13	120.3
N5—C17—C16	118.9 (2)	C8—C7—C6	118.4 (3)
C18ⁱ—C17—C16	132.0 (2)	C8—C7—H7	120.8
N5ⁱⁱⁱ—C20—N6	113.7 (2)	C6—C7—H7	120.8

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₅HN₂O₄)(C₁₀H₈N₂)]
M_r	368.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.5002 (10), 9.6500 (5), 14.7623 (7)
β (°)	101.801 (1)
V (Å³)	2858.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.887, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	15047, 5563, 4855
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.104, 1.00
No. of reflections	5563
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.35

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1999), SHELXTL.

Selected bond lengths (Å) top

Co1—N2	2.091 (2)	Co2—N6	2.077 (2)
Co1—N1	2.117 (2)	Co2—N5	2.080 (2)
Co1—N4	2.132 (2)	Co2—N8	2.125 (2)
Co1—O3	2.1569 (18)	Co2—N7	2.205 (2)
Co1—O1	2.2067 (18)	Co2—O5	2.2071 (19)
Co1—N3	2.271 (2)	Co2—O7	2.2562 (19)

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Retracted: catena-Poly[[(2,2-bipyridine)cobalt(II)]-μ-imidazole-4,5-dicarboxyl­ato]

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: catena-Poly[[(2,2-bipyridine)cobalt(II)]-μ-imidazole-4,5-dicarboxylato]