Bis(μ-1H-benzimidazole-5,6-dicarboxyl­ato)bis­[tetra­aqua­dicobalt(II)] penta­hydrate

Lo, Y.-L.; Wang, W.-C.; Lee, G.-A.; Liu, Y.-H.

doi:10.1107/S1600536807048088

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Bis(μ-1H-benzimidazole-5,6-dicarboxylato)bis[tetraaquadicobalt(II)] pentahydrate

Y.-L. Lo, W.-C. Wang, G.-A. Lee and Y.-H. Liu

The title compound, [Co₂(C₉H₄N₂O₄)₂(H₂O)₈]·5H₂O, contains two Co^II ions that are bridged by two 1H-benzimidazole-5,6-dicarboxylate ligands to form an M₂L₂ type complex (M = metal and L = ligand). There are two crystallographically distinct M₂L₂ units, each on an inversion centre, along with coordinated and uncoordinated water molecules, in the asymmetric unit. The Co^II ions are octahedral. Extensive hydrogen bonding exists between the complex and water molecules, and this helps to stabilize the crystal structure. One water molecule is disordered over two sites with occupancies 0.84:0.16.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048088/pk2050sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048088/pk2050Isup2.hkl Contains datablock I

CCDC reference: 667114

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
H-atom completeness 97%
Disorder in solvent or counterion
R factor = 0.040
wR factor = 0.103
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      17.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O94'
PLAT417_ALERT_2_C Short Inter D-H..H-D       H83A   ..  H95A    ..       2.11 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O1     ..  O94'    ..       2.86 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O6     ..  O94'    ..       2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H94A   ..  O93     ..       2.62 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C18 H34 Co2 N4 O21
            Atom count from the _atom_site data:  C18 H32.68 Co2 N4 O21
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C18 H34 Co2 N4 O21
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         72.00     72.00    0.00
           H        136.00    130.72    5.28
           Co         8.00      8.00    0.00
           N         16.00     16.00    0.00
           O         84.00     84.00    0.00

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

N-Heterocyclic carboxylic acids are recognized as efficient N,O-donors exhibiting versatile coordination modes and hydrogen bonding interactions. Examples on the basis of 1H-benzimidazole-5-carboxylic acid have been reported, which give rise to various coordination polymers and supramolecular architectures (Guo et al.2006; Liu et al. 2005). Here we report the crystal structure of the title compound, [Co₂(H₂O)₈(C₉H₄N₂O₄)₂].5H₂O, using a new family member of the N-heterocyclic carboxylic acids, 1H-benzimidazole-5,6-dicarboxylic acid (H₃BIDC).

The asymmetric unit consists of two 1H-benzimidazole-5,6-dicarboxylate (H₃BIDC) ligands, which are deprotonated to form HBIDC^2– anions. Each of the Co^II cations has an octahedral coordination environment, and is surrounded by four coordinated water molecules, one nitrogen atom of the benzimidazole ring, and one oxygen atom of the monodentate carboxylate group. Two Co^II ions are bridged by two HBIDC^2– ligands to form a M₂L₂type complex (M: metal, L: ligand). There are two crystallographically distinct M₂L₂ units in the asymmetric unit (Fig. 1). A unit-cell packing diagram is shown in Fig. 2. The N-bound H atoms of the benzimidazole ring, the O atoms of the uncoordinated carboxylate group, and coordinated water molecules serve as hydrogen bonding donors and acceptors. Extensive hydrogen bonding interactions (Table 2) were observed among the title compound and solvent water molecules in the solid-state, and these help stabilize the crystal structure.

Related literature top

Metal-organic coordination polymers using 1H-benzimidazole-5-carboxylic acid as a bridging ligand were reported by Guo et al. (2006) and Liu et al. (2005).

Experimental top

Purple crystals form within 4 days of layering a 2.0 ml me thanol solution of Co(NO₃)₂.6H₂O (0.1169 g, 0.40 mmol) through a 3.0 ml me thanol and 15 ml aqueous buffer layers onto a 10.0 ml aqueous solution containing 1H-benzimidazole-4,5-dicarboxylic acid (0.0415 g, 0.20 mmol) and KOH (4M, 0.4 ml).

Structure description top

Metal-organic coordination polymers using 1H-benzimidazole-5-carboxylic acid as a bridging ligand were reported by Guo et al. (2006) and Liu et al. (2005).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO-SMN (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The crystallographically distinct M₂L₂ units of the title compound with atom numbering scheme. Atomic displacement ellipsoids are drawn at the 50% probability level. (Symmetry code: (i) 1–x, 1–y, 2–z; (ii) 2–x, –y, 1–z)
	Fig. 2. A unit-cell packing diagram viewied down the b-axis. (Key: aqua sphere: solvent water molecules; pink sphere: Co; blue sphere: N; red sphere: O; gray sphere: C). H atoms are omitted for clarity.

Bis(µ-1H-benzimidazole-5,6-dicarboxylato)bis[tetraaquadicobalt(II)] pentahydrate top

Crystal data top

[Co₂(C₉H₄N₂O₄)₂(H₂O)₈]·5H₂O	F(000) = 1568
M_r = 760.35	D_x = 1.759 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16539 reflections
a = 13.4210 (2) Å	θ = 2.0–25.4°
b = 9.1096 (2) Å	µ = 1.26 mm⁻¹
c = 23.8185 (4) Å	T = 200 K
β = 99.5191 (6)°	Plate, purple
V = 2871.95 (9) Å³	0.30 × 0.18 × 0.08 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	5249 independent reflections
Radiation source: sealed tube	4216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 25.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
T_min = 0.776, T_max = 0.905	k = −10→8
22168 measured reflections	l = −28→28

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0316P)² + 5.0966P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.040	(Δ/σ)_max = 0.001
wR(F²) = 0.103	Δρ_max = 0.72 e Å⁻³
S = 1.10	Δρ_min = −0.41 e Å⁻³
5249 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
412 parameters	Extinction coefficient: 0.0011 (2)
0 restraints

Crystal data top

[Co₂(C₉H₄N₂O₄)₂(H₂O)₈]·5H₂O	V = 2871.95 (9) Å³
M_r = 760.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4210 (2) Å	µ = 1.26 mm⁻¹
b = 9.1096 (2) Å	T = 200 K
c = 23.8185 (4) Å	0.30 × 0.18 × 0.08 mm
β = 99.5191 (6)°

Data collection top

Nonius KappaCCD diffractometer	5249 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4216 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.905	R_int = 0.032
22168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.10	Δρ_max = 0.72 e Å⁻³
5249 reflections	Δρ_min = −0.41 e Å⁻³
412 parameters

Special details top

Experimental. Comment on transmission values: The program SADABS (Sheldrick, 2003) outputs the ratio of minimum to maximum apparent transmission (0.858265). We have set T(max) to the expected value, i.e. exp(-r_min× µ) and we calculate T(min) from the minimum to maximum apparent transmission given by SADABS.

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.41028 (3)	0.65075 (4)	0.836342 (16)	0.01866 (14)
Co2	1.08333 (3)	−0.16005 (4)	0.658602 (16)	0.01864 (14)
N1	0.6294 (2)	0.2084 (3)	1.10033 (10)	0.0222 (6)
N2	0.64479 (19)	−0.0092 (3)	1.06047 (11)	0.0232 (6)
H2	0.654	−0.1022	1.0578	0.028*
N3	0.8847 (2)	0.3124 (3)	0.40404 (10)	0.0217 (6)
N4	0.86074 (19)	0.5298 (3)	0.44314 (10)	0.0215 (6)
H4	0.849	0.6222	0.4455	0.026*
O1	0.47640 (15)	0.4841 (2)	0.88915 (8)	0.0202 (5)
O2	0.62779 (17)	0.5805 (2)	0.92141 (10)	0.0295 (5)
O3	0.59954 (16)	0.2945 (2)	0.83126 (9)	0.0235 (5)
O4	0.5648 (2)	0.0581 (3)	0.83878 (9)	0.0385 (6)
O5	1.01958 (15)	0.0059 (2)	0.60354 (8)	0.0200 (5)
O6	0.85409 (16)	−0.0311 (2)	0.59619 (10)	0.0272 (5)
O7	0.92964 (19)	0.2287 (3)	0.67434 (9)	0.0336 (6)
O8	0.9010 (2)	0.4670 (2)	0.66411 (9)	0.0340 (6)
O81	0.34490 (16)	0.7930 (2)	0.77188 (9)	0.0261 (5)
H81A	0.3723	0.7869	0.7418	0.039*
H81B	0.2843	0.7657	0.7627	0.039*
O82	0.44968 (18)	0.5094 (3)	0.77371 (9)	0.0322 (6)
H82A	0.4951	0.4471	0.7859	0.048*
H82B	0.4481	0.5232	0.7381	0.048*
O83	0.27314 (16)	0.5386 (3)	0.83000 (10)	0.0306 (5)
H83A	0.2782	0.4493	0.8248	0.046*
H83B	0.2304	0.5541	0.8522	0.046*
O84	0.55289 (15)	0.7614 (2)	0.83995 (9)	0.0245 (5)
H84A	0.584	0.7189	0.8694	0.037*
H84B	0.5549	0.8532	0.8457	0.037*
O85	1.14099 (16)	−0.2984 (2)	0.72871 (9)	0.0240 (5)
H85A	1.1462	−0.3909	0.7256	0.036*
H85B	1.1212	−0.2771	0.7596	0.036*
O86	1.06101 (18)	−0.0035 (3)	0.72108 (9)	0.0336 (6)
H86A	1.0698	−0.0114	0.7562	0.05*
H86B	1.024	0.0648	0.707	0.05*
O87	0.93868 (16)	−0.2432 (2)	0.66332 (9)	0.0265 (5)
H87A	0.8983	−0.1937	0.6399	0.04*
H87B	0.9264	−0.3336	0.6575	0.04*
O88	1.22080 (16)	−0.0591 (2)	0.65935 (9)	0.0268 (5)
H88A	1.2394	0.0176	0.6779	0.04*
H88B	1.2743	−0.1056	0.6557	0.04*
O91	0.7014 (2)	0.6817 (3)	0.77346 (12)	0.0492 (8)
H91A	0.6887	0.7011	0.7381	0.074*
H91B	0.6529	0.7054	0.7911	0.074*
O92	0.8534 (2)	0.8892 (3)	0.76493 (11)	0.0534 (8)
H92A	0.8201	0.8254	0.7812	0.08*
H92B	0.894	0.8398	0.7485	0.08*
O93	0.8302 (2)	0.8185 (3)	0.42952 (15)	0.0599 (9)
H93A	0.7801	0.8784	0.4252	0.09*
H93B	0.8778	0.8615	0.4162	0.09*
O94	0.7031 (3)	0.7871 (3)	0.53038 (15)	0.0499 (14)	0.840 (8)
H94A	0.6928	0.8093	0.4958	0.075*	0.840 (8)
H94B	0.7502	0.8392	0.5476	0.075*	0.840 (8)
O94'	0.6714 (12)	0.8013 (18)	0.5717 (8)	0.038 (6)*	0.160 (8)
O95	0.6591 (3)	0.7469 (4)	0.65546 (15)	0.0719 (10)
H95A	0.6035	0.8022	0.6458	0.108*
C1	0.5651 (2)	0.4767 (3)	0.91659 (12)	0.0191 (7)
C2	0.5928 (2)	0.3377 (3)	0.94980 (13)	0.0183 (6)
C3	0.6041 (2)	0.3530 (3)	1.00843 (13)	0.0208 (7)
H3	0.6019	0.445	1.0251	0.025*
C4	0.6190 (2)	0.2267 (3)	1.04167 (12)	0.0197 (7)
C5	0.6450 (2)	0.0662 (3)	1.10842 (13)	0.0239 (7)
H5	0.6552	0.0227	1.1443	0.029*
C6	0.6271 (2)	0.0893 (3)	1.01577 (13)	0.0189 (7)
C7	0.6167 (2)	0.0728 (3)	0.95744 (13)	0.0214 (7)
H7	0.6219	−0.019	0.9411	0.026*
C8	0.5983 (2)	0.1984 (3)	0.92389 (12)	0.0184 (6)
C9	0.5866 (2)	0.1816 (3)	0.85997 (13)	0.0213 (7)
C10	0.9289 (2)	0.0441 (3)	0.58849 (12)	0.0183 (7)
C11	0.9106 (2)	0.1849 (3)	0.55483 (12)	0.0177 (6)
C12	0.9058 (2)	0.1699 (3)	0.49677 (13)	0.0196 (7)
H12	0.9126	0.0781	0.4808	0.024*
C13	0.8906 (2)	0.2943 (3)	0.46267 (12)	0.0187 (6)
C14	0.8668 (2)	0.4547 (3)	0.39564 (13)	0.0237 (7)
H14	0.8591	0.4983	0.3599	0.028*
C15	0.8770 (2)	0.4308 (3)	0.48777 (13)	0.0185 (7)
C16	0.8824 (2)	0.4477 (3)	0.54609 (12)	0.0191 (7)
H16	0.8738	0.5393	0.5618	0.023*
C17	0.9008 (2)	0.3246 (3)	0.58027 (12)	0.0189 (7)
C18	0.9107 (2)	0.3408 (3)	0.64404 (13)	0.0210 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0225 (2)	0.0194 (2)	0.0143 (2)	0.00200 (17)	0.00370 (17)	0.00148 (17)
Co2	0.0228 (2)	0.0182 (2)	0.0151 (2)	0.00204 (17)	0.00394 (17)	0.00131 (17)
N1	0.0294 (14)	0.0225 (14)	0.0147 (13)	0.0035 (12)	0.0033 (11)	0.0005 (11)
N2	0.0312 (15)	0.0180 (13)	0.0213 (14)	0.0038 (11)	0.0068 (12)	0.0026 (11)
N3	0.0293 (14)	0.0218 (14)	0.0146 (13)	0.0026 (11)	0.0053 (11)	0.0029 (11)
N4	0.0288 (14)	0.0173 (13)	0.0180 (14)	0.0029 (11)	0.0026 (11)	0.0020 (11)
O1	0.0218 (11)	0.0201 (11)	0.0182 (11)	0.0012 (9)	0.0018 (9)	0.0033 (9)
O2	0.0313 (13)	0.0216 (12)	0.0330 (13)	−0.0045 (10)	−0.0024 (10)	0.0076 (10)
O3	0.0314 (12)	0.0221 (12)	0.0180 (11)	−0.0017 (10)	0.0073 (9)	0.0001 (10)
O4	0.0743 (19)	0.0210 (13)	0.0193 (12)	−0.0099 (12)	0.0050 (12)	−0.0027 (10)
O5	0.0209 (11)	0.0211 (11)	0.0182 (11)	0.0030 (9)	0.0038 (9)	0.0043 (9)
O6	0.0232 (12)	0.0232 (12)	0.0347 (13)	−0.0012 (10)	0.0032 (10)	0.0095 (10)
O7	0.0611 (17)	0.0240 (13)	0.0177 (12)	0.0165 (12)	0.0123 (11)	0.0057 (10)
O8	0.0635 (17)	0.0201 (12)	0.0184 (12)	−0.0012 (12)	0.0068 (11)	−0.0024 (10)
O81	0.0270 (12)	0.0352 (13)	0.0162 (11)	0.0034 (10)	0.0035 (9)	0.0044 (10)
O82	0.0465 (15)	0.0324 (13)	0.0175 (12)	0.0148 (11)	0.0046 (10)	0.0012 (10)
O83	0.0257 (12)	0.0360 (14)	0.0313 (13)	−0.0021 (10)	0.0084 (10)	−0.0041 (11)
O84	0.0279 (12)	0.0194 (11)	0.0254 (12)	−0.0008 (9)	0.0016 (10)	0.0058 (9)
O85	0.0330 (12)	0.0231 (12)	0.0171 (11)	0.0056 (10)	0.0077 (10)	0.0023 (9)
O86	0.0490 (15)	0.0325 (13)	0.0183 (12)	0.0157 (12)	0.0021 (11)	−0.0024 (10)
O87	0.0286 (12)	0.0202 (12)	0.0302 (13)	−0.0010 (10)	0.0036 (10)	0.0063 (10)
O88	0.0227 (12)	0.0233 (12)	0.0345 (13)	0.0003 (9)	0.0052 (10)	−0.0006 (10)
O91	0.0509 (17)	0.0457 (17)	0.0576 (18)	0.0134 (14)	0.0278 (14)	0.0186 (14)
O92	0.070 (2)	0.0516 (18)	0.0443 (17)	−0.0194 (16)	0.0270 (15)	−0.0080 (14)
O93	0.0347 (15)	0.0281 (15)	0.120 (3)	0.0071 (12)	0.0217 (17)	0.0268 (16)
O94	0.067 (2)	0.0368 (19)	0.040 (2)	−0.0193 (17)	−0.0086 (18)	0.0133 (16)
O95	0.073 (2)	0.059 (2)	0.079 (2)	0.0141 (18)	−0.0002 (19)	−0.0172 (18)
C1	0.0250 (17)	0.0194 (16)	0.0139 (15)	0.0009 (13)	0.0065 (13)	0.0004 (12)
C2	0.0180 (15)	0.0166 (15)	0.0202 (16)	0.0007 (12)	0.0031 (13)	0.0031 (13)
C3	0.0260 (16)	0.0180 (16)	0.0185 (16)	0.0006 (13)	0.0038 (13)	−0.0011 (13)
C4	0.0225 (16)	0.0219 (16)	0.0147 (15)	0.0012 (13)	0.0030 (12)	0.0016 (13)
C5	0.0311 (18)	0.0237 (17)	0.0176 (16)	0.0044 (14)	0.0066 (14)	0.0051 (14)
C6	0.0221 (16)	0.0170 (16)	0.0178 (16)	0.0015 (12)	0.0039 (13)	0.0020 (13)
C7	0.0262 (17)	0.0184 (16)	0.0200 (16)	0.0001 (13)	0.0052 (13)	−0.0015 (13)
C8	0.0183 (15)	0.0204 (16)	0.0173 (15)	0.0000 (12)	0.0055 (12)	−0.0003 (13)
C9	0.0245 (16)	0.0210 (17)	0.0188 (16)	0.0004 (13)	0.0048 (13)	0.0012 (14)
C10	0.0264 (17)	0.0183 (16)	0.0110 (14)	0.0016 (13)	0.0052 (13)	−0.0022 (12)
C11	0.0155 (14)	0.0197 (16)	0.0184 (16)	0.0015 (12)	0.0042 (12)	0.0000 (13)
C12	0.0263 (16)	0.0158 (15)	0.0173 (15)	0.0023 (13)	0.0053 (13)	−0.0003 (12)
C13	0.0202 (15)	0.0200 (16)	0.0161 (15)	0.0016 (13)	0.0037 (12)	0.0011 (13)
C14	0.0323 (18)	0.0225 (17)	0.0163 (16)	0.0004 (14)	0.0042 (14)	0.0033 (14)
C15	0.0182 (15)	0.0186 (16)	0.0179 (16)	−0.0001 (12)	0.0010 (12)	0.0035 (13)
C16	0.0210 (15)	0.0168 (15)	0.0195 (16)	0.0009 (13)	0.0029 (13)	−0.0028 (13)
C17	0.0187 (15)	0.0215 (16)	0.0160 (15)	0.0006 (12)	0.0017 (12)	0.0003 (13)
C18	0.0220 (16)	0.0228 (18)	0.0191 (16)	−0.0011 (13)	0.0056 (13)	−0.0003 (14)

Geometric parameters (Å, º) top

Co1—O1	2.075 (2)	O85—H85A	0.8492
Co1—O81	2.088 (2)	O85—H85B	0.8453
Co1—O83	2.089 (2)	O86—H86A	0.8289
Co1—O82	2.103 (2)	O86—H86B	0.8315
Co1—N1ⁱ	2.114 (3)	O87—H87A	0.8418
Co1—O84	2.152 (2)	O87—H87B	0.8463
Co2—O88	2.059 (2)	O88—H88A	0.8427
Co2—O5	2.090 (2)	O88—H88B	0.8502
Co2—O87	2.104 (2)	O91—H91A	0.85
Co2—O86	2.118 (2)	O91—H91B	0.8579
Co2—N3ⁱⁱ	2.133 (3)	O92—H92A	0.8623
Co2—O85	2.133 (2)	O92—H92B	0.8503
N1—C5	1.322 (4)	O93—H93A	0.859
N1—C4	1.391 (4)	O93—H93B	0.8553
N1—Co1ⁱ	2.114 (3)	O94—O94'	1.142 (18)
N2—C5	1.332 (4)	O94—H94A	0.8377
N2—C6	1.383 (4)	O94—H94B	0.8405
N2—H2	0.86	O95—H95A	0.8987
N3—C14	1.328 (4)	C1—C2	1.507 (4)
N3—C13	1.395 (4)	C2—C3	1.386 (4)
N3—Co2ⁱⁱ	2.133 (3)	C2—C8	1.419 (4)
N4—C14	1.336 (4)	C3—C4	1.392 (4)
N4—C15	1.383 (4)	C3—H3	0.93
N4—H4	0.86	C4—C6	1.408 (4)
O1—C1	1.261 (4)	C5—H5	0.93
O2—C1	1.258 (4)	C6—C7	1.381 (4)
O3—C9	1.262 (4)	C7—C8	1.394 (4)
O4—C9	1.248 (4)	C7—H7	0.93
O5—C10	1.259 (4)	C8—C9	1.512 (4)
O6—C10	1.254 (4)	C10—C11	1.511 (4)
O7—C18	1.252 (4)	C11—C12	1.380 (4)
O8—C18	1.260 (4)	C11—C17	1.425 (4)
O81—H81A	0.8597	C12—C13	1.390 (4)
O81—H81B	0.8436	C12—H12	0.93
O82—H82A	0.8483	C13—C15	1.405 (4)
O82—H82B	0.8541	C14—H14	0.93
O83—H83A	0.8276	C15—C16	1.387 (4)
O83—H83B	0.8533	C16—C17	1.384 (4)
O84—H84A	0.8491	C16—H16	0.93
O84—H84B	0.8475	C17—C18	1.510 (4)

O1—Co1—O81	170.17 (9)	Co2—O87—H87B	119.9
O1—Co1—O83	88.25 (9)	H87A—O87—H87B	109.1
O81—Co1—O83	89.55 (9)	Co2—O88—H88A	124.2
O1—Co1—O82	81.36 (8)	Co2—O88—H88B	123.1
O81—Co1—O82	89.00 (9)	H88A—O88—H88B	106.6
O83—Co1—O82	88.35 (9)	H91A—O91—H91B	113
O1—Co1—N1ⁱ	98.29 (9)	H92A—O92—H92B	105.6
O81—Co1—N1ⁱ	91.34 (9)	H93A—O93—H93B	106.4
O83—Co1—N1ⁱ	91.46 (10)	H94A—O94—H94B	109.4
O82—Co1—N1ⁱ	179.61 (10)	O2—C1—O1	124.5 (3)
O1—Co1—O84	91.72 (8)	O2—C1—C2	118.7 (3)
O81—Co1—O84	90.09 (8)	O1—C1—C2	116.5 (3)
O83—Co1—O84	177.69 (9)	C3—C2—C8	121.5 (3)
O82—Co1—O84	89.36 (9)	C3—C2—C1	114.9 (3)
N1ⁱ—Co1—O84	90.83 (9)	C8—C2—C1	123.4 (3)
O88—Co2—O5	87.45 (8)	C2—C3—C4	118.1 (3)
O88—Co2—O87	173.57 (9)	C2—C3—H3	120.9
O5—Co2—O87	90.48 (8)	C4—C3—H3	120.9
O88—Co2—O86	85.63 (9)	N1—C4—C3	130.6 (3)
O5—Co2—O86	82.13 (8)	N1—C4—C6	109.4 (3)
O87—Co2—O86	88.05 (9)	C3—C4—C6	120.0 (3)
O88—Co2—N3ⁱⁱ	90.76 (9)	N1—C5—N2	113.7 (3)
O5—Co2—N3ⁱⁱ	98.09 (9)	N1—C5—H5	123.1
O87—Co2—N3ⁱⁱ	95.57 (9)	N2—C5—H5	123.1
O86—Co2—N3ⁱⁱ	176.37 (10)	C7—C6—N2	132.8 (3)
O88—Co2—O85	92.79 (8)	C7—C6—C4	122.4 (3)
O5—Co2—O85	167.66 (8)	N2—C6—C4	104.8 (3)
O87—Co2—O85	87.93 (8)	C6—C7—C8	117.8 (3)
O86—Co2—O85	85.59 (9)	C6—C7—H7	121.1
N3ⁱⁱ—Co2—O85	94.25 (9)	C8—C7—H7	121.1
C5—N1—C4	104.5 (3)	C7—C8—C2	120.1 (3)
C5—N1—Co1ⁱ	122.9 (2)	C7—C8—C9	118.3 (3)
C4—N1—Co1ⁱ	130.5 (2)	C2—C8—C9	121.6 (3)
C5—N2—C6	107.6 (3)	O4—C9—O3	124.0 (3)
C5—N2—H2	126.2	O4—C9—C8	118.5 (3)
C6—N2—H2	126.2	O3—C9—C8	117.6 (3)
C14—N3—C13	104.2 (3)	O6—C10—O5	124.5 (3)
C14—N3—Co2ⁱⁱ	125.6 (2)	O6—C10—C11	118.5 (3)
C13—N3—Co2ⁱⁱ	129.7 (2)	O5—C10—C11	116.8 (3)
C14—N4—C15	107.1 (3)	C12—C11—C17	121.5 (3)
C14—N4—H4	126.5	C12—C11—C10	115.1 (3)
C15—N4—H4	126.5	C17—C11—C10	123.4 (3)
C1—O1—Co1	128.73 (19)	C11—C12—C13	118.9 (3)
C10—O5—Co2	130.89 (19)	C11—C12—H12	120.5
Co1—O81—H81A	112.8	C13—C12—H12	120.5
Co1—O81—H81B	106.1	C12—C13—N3	131.3 (3)
H81A—O81—H81B	106.9	C12—C13—C15	119.3 (3)
Co1—O82—H82A	114.7	N3—C13—C15	109.4 (3)
Co1—O82—H82B	130.3	N3—C14—N4	114.0 (3)
H82A—O82—H82B	109.7	N3—C14—H14	123
Co1—O83—H83A	113.5	N4—C14—H14	123
Co1—O83—H83B	123.3	N4—C15—C16	132.3 (3)
H83A—O83—H83B	109.6	N4—C15—C13	105.4 (3)
Co1—O84—H84A	97.6	C16—C15—C13	122.4 (3)
Co1—O84—H84B	118.2	C17—C16—C15	118.3 (3)
H84A—O84—H84B	108.6	C17—C16—H16	120.8
Co2—O85—H85A	122.9	C15—C16—H16	120.8
Co2—O85—H85B	114.9	C16—C17—C11	119.6 (3)
H85A—O85—H85B	110.2	C16—C17—C18	119.3 (3)
Co2—O86—H86A	129.6	C11—C17—C18	121.1 (3)
Co2—O86—H86B	111.4	O7—C18—O8	123.3 (3)
H86A—O86—H86B	116.6	O7—C18—C17	118.4 (3)
Co2—O87—H87A	105.7	O8—C18—C17	118.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O94ⁱⁱⁱ	0.86	1.96	2.779 (4)	159
N4—H4···O93	0.86	1.84	2.673 (4)	164
O81—H81A···O3^iv	0.86	1.84	2.683 (3)	166
O81—H81B···O85^v	0.84	2.05	2.883 (3)	172
O82—H82A···O3	0.85	2.14	2.974 (3)	169
O82—H82B···O4^iv	0.85	1.84	2.691 (3)	176
O83—H83A···O95^vi	0.83	2.05	2.812 (4)	153
O83—H83B···O6^iv	0.85	1.96	2.721 (3)	147
O84—H84A···O2	0.85	1.8	2.616 (3)	162
O84—H84B···O4^vii	0.85	1.88	2.708 (3)	165
O85—H85A···O92^viii	0.85	2.02	2.850 (4)	167
O85—H85B···O7^ix	0.85	1.82	2.649 (3)	168
O86—H86A···O8^ix	0.83	1.88	2.711 (3)	176
O86—H86B···O7	0.83	2.03	2.859 (3)	178
O87—H87A···O6	0.84	1.85	2.642 (3)	156
O87—H87B···O8^x	0.85	1.86	2.689 (3)	166
O88—H88A···O91^ix	0.84	1.98	2.813 (3)	173
O88—H88B···O3^ix	0.85	1.9	2.732 (3)	165
O91—H91A···O95	0.85	1.99	2.836 (4)	180
O91—H91B···O84	0.86	1.98	2.837 (3)	174
O92—H92A···O91	0.86	2.05	2.813 (4)	148
O92—H92B···O87^vii	0.85	2.34	3.089 (4)	148
O93—H93A···O2^xi	0.86	2.07	2.844 (3)	151
O93—H93A···O88^xii	0.86	2.6	3.045 (4)	114
O93—H93B···O5^xii	0.86	1.95	2.788 (3)	168
O94—H94A···O2^xi	0.84	2.1	2.889 (4)	158
O94—H94A···O93	0.84	2.62	3.180 (5)	126
O94—H94B···O6^vii	0.84	2.04	2.873 (4)	174
O95—H95A···O1^iv	0.9	2.07	2.910 (4)	155

Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+3/2; (v) x−1, y+1, z; (vi) −x+1, y−1/2, −z+3/2; (vii) x, y+1, z; (viii) −x+2, y−3/2, −z+3/2; (ix) −x+2, y−1/2, −z+3/2; (x) x, y−1, z; (xi) x, −y+3/2, z−1/2; (xii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Co₂(C₉H₄N₂O₄)₂(H₂O)₈]·5H₂O
M_r	760.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	13.4210 (2), 9.1096 (2), 23.8185 (4)
β (°)	99.5191 (6)
V (Å³)	2871.95 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.30 × 0.18 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.776, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	22168, 5249, 4216
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.10
No. of reflections	5249
No. of parameters	412
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.41

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor 1997), DENZO-SMN (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O94ⁱ	0.86	1.96	2.779 (4)	159
N4—H4···O93	0.86	1.84	2.673 (4)	164
O81—H81A···O3ⁱⁱ	0.86	1.84	2.683 (3)	166
O81—H81B···O85ⁱⁱⁱ	0.84	2.05	2.883 (3)	172
O82—H82A···O3	0.85	2.14	2.974 (3)	169
O82—H82B···O4ⁱⁱ	0.85	1.84	2.691 (3)	176
O83—H83A···O95^iv	0.83	2.05	2.812 (4)	153
O83—H83B···O6ⁱⁱ	0.85	1.96	2.721 (3)	147
O84—H84A···O2	0.85	1.8	2.616 (3)	162
O84—H84B···O4^v	0.85	1.88	2.708 (3)	165
O85—H85A···O92^vi	0.85	2.02	2.850 (4)	167
O85—H85B···O7^vii	0.85	1.82	2.649 (3)	168
O86—H86A···O8^vii	0.83	1.88	2.711 (3)	176
O86—H86B···O7	0.83	2.03	2.859 (3)	178
O87—H87A···O6	0.84	1.85	2.642 (3)	156
O87—H87B···O8^viii	0.85	1.86	2.689 (3)	166
O88—H88A···O91^vii	0.84	1.98	2.813 (3)	173
O88—H88B···O3^vii	0.85	1.9	2.732 (3)	165
O91—H91A···O95	0.85	1.99	2.836 (4)	180
O91—H91B···O84	0.86	1.98	2.837 (3)	174
O92—H92A···O91	0.86	2.05	2.813 (4)	148
O92—H92B···O87^v	0.85	2.34	3.089 (4)	148
O93—H93A···O2^ix	0.86	2.07	2.844 (3)	151
O93—H93A···O88^x	0.86	2.6	3.045 (4)	114
O93—H93B···O5^x	0.86	1.95	2.788 (3)	168
O94—H94A···O2^ix	0.84	2.1	2.889 (4)	158
O94—H94A···O93	0.84	2.62	3.180 (5)	126
O94—H94B···O6^v	0.84	2.04	2.873 (4)	174
O95—H95A···O1ⁱⁱ	0.9	2.07	2.910 (4)	155

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

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