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Acta Cryst. (2007). E63, m2657-m2658
https://doi.org/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 CoII 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 CoII 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048088/pk2050sup1.cif
Contains datablocks global, I

hkl

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 [sigma](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 HBIDC2– anions. Each of the CoII 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 CoII ions are bridged by two HBIDC2– ligands to form a M2L2 type 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).

Refinement top

The C-bound H atoms were placed in calculated positions (C–H = 0.93 Å) and refined in the riding-model approximation with Uiso(H) = 1.2 Ueq(C). The N-bound H atoms were found in a difference Fourier map, but were placed in calculated positions (C–H = 0.86 Å) and refined in the riding-model approximation with Uiso(H) = 1.2 Ueq(N). The H atoms of the coordinated water molecules and solvent water molecules were located in a difference Fourier map, and refined using a riding model with Usio(H) = 1.5 Ueq(O). The water molecule O94 is disordered over two positions; the occupancies of O94 and O94' refined to 0.84 and 0.16, respectively (O94' is only refined isotropically). Only one of the H atoms of solvent water molecule O95 could be found in a difference Fourier map because of its close proximity (ca 2.08 Å) to the disordered O94'.

Structure description 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 HBIDC2– anions. Each of the CoII 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 CoII ions are bridged by two HBIDC2– ligands to form a M2L2 type 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.

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
[Figure 1] 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)
[Figure 2] 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]·5H2OF(000) = 1568
Mr = 760.35Dx = 1.759 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16539 reflections
a = 13.4210 (2) Åθ = 2.0–25.4°
b = 9.1096 (2) ŵ = 1.26 mm−1
c = 23.8185 (4) ÅT = 200 K
β = 99.5191 (6)°Plate, purple
V = 2871.95 (9) Å30.30 × 0.18 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		5249 independent reflections
Radiation source: sealed tube4216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −16→16
Tmin = 0.776, Tmax = 0.905k = −10→8
22168 measured reflectionsl = −28→28
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0316P)2 + 5.0966P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040(Δ/σ)max = 0.001
wR(F2) = 0.103Δρmax = 0.72 e Å−3
S = 1.10Δρmin = −0.41 e Å−3
5249 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
412 parametersExtinction coefficient: 0.0011 (2)
0 restraints
Crystal data top
[Co2(C9H4N2O4)2(H2O)8]·5H2OV = 2871.95 (9) Å3
Mr = 760.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.4210 (2) ŵ = 1.26 mm−1
b = 9.1096 (2) ÅT = 200 K
c = 23.8185 (4) Å0.30 × 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)
Tmin = 0.776, Tmax = 0.905Rint = 0.032
22168 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.10Δρmax = 0.72 e Å−3
5249 reflectionsΔρmin = −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(-rmin× 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
xyzUiso*/UeqOcc. (<1)
Co10.41028 (3)0.65075 (4)0.836342 (16)0.01866 (14)
Co21.08333 (3)−0.16005 (4)0.658602 (16)0.01864 (14)
N10.6294 (2)0.2084 (3)1.10033 (10)0.0222 (6)
N20.64479 (19)−0.0092 (3)1.06047 (11)0.0232 (6)
H20.654−0.10221.05780.028*
N30.8847 (2)0.3124 (3)0.40404 (10)0.0217 (6)
N40.86074 (19)0.5298 (3)0.44314 (10)0.0215 (6)
H40.8490.62220.44550.026*
O10.47640 (15)0.4841 (2)0.88915 (8)0.0202 (5)
O20.62779 (17)0.5805 (2)0.92141 (10)0.0295 (5)
O30.59954 (16)0.2945 (2)0.83126 (9)0.0235 (5)
O40.5648 (2)0.0581 (3)0.83878 (9)0.0385 (6)
O51.01958 (15)0.0059 (2)0.60354 (8)0.0200 (5)
O60.85409 (16)−0.0311 (2)0.59619 (10)0.0272 (5)
O70.92964 (19)0.2287 (3)0.67434 (9)0.0336 (6)
O80.9010 (2)0.4670 (2)0.66411 (9)0.0340 (6)
O810.34490 (16)0.7930 (2)0.77188 (9)0.0261 (5)
H81A0.37230.78690.74180.039*
H81B0.28430.76570.76270.039*
O820.44968 (18)0.5094 (3)0.77371 (9)0.0322 (6)
H82A0.49510.44710.78590.048*
H82B0.44810.52320.73810.048*
O830.27314 (16)0.5386 (3)0.83000 (10)0.0306 (5)
H83A0.27820.44930.82480.046*
H83B0.23040.55410.85220.046*
O840.55289 (15)0.7614 (2)0.83995 (9)0.0245 (5)
H84A0.5840.71890.86940.037*
H84B0.55490.85320.84570.037*
O851.14099 (16)−0.2984 (2)0.72871 (9)0.0240 (5)
H85A1.1462−0.39090.72560.036*
H85B1.1212−0.27710.75960.036*
O861.06101 (18)−0.0035 (3)0.72108 (9)0.0336 (6)
H86A1.0698−0.01140.75620.05*
H86B1.0240.06480.7070.05*
O870.93868 (16)−0.2432 (2)0.66332 (9)0.0265 (5)
H87A0.8983−0.19370.63990.04*
H87B0.9264−0.33360.65750.04*
O881.22080 (16)−0.0591 (2)0.65935 (9)0.0268 (5)
H88A1.23940.01760.67790.04*
H88B1.2743−0.10560.65570.04*
O910.7014 (2)0.6817 (3)0.77346 (12)0.0492 (8)
H91A0.68870.70110.73810.074*
H91B0.65290.70540.79110.074*
O920.8534 (2)0.8892 (3)0.76493 (11)0.0534 (8)
H92A0.82010.82540.78120.08*
H92B0.8940.83980.74850.08*
O930.8302 (2)0.8185 (3)0.42952 (15)0.0599 (9)
H93A0.78010.87840.42520.09*
H93B0.87780.86150.41620.09*
O940.7031 (3)0.7871 (3)0.53038 (15)0.0499 (14)0.840 (8)
H94A0.69280.80930.49580.075*0.840 (8)
H94B0.75020.83920.54760.075*0.840 (8)
O94'0.6714 (12)0.8013 (18)0.5717 (8)0.038 (6)*0.160 (8)
O950.6591 (3)0.7469 (4)0.65546 (15)0.0719 (10)
H95A0.60350.80220.64580.108*
C10.5651 (2)0.4767 (3)0.91659 (12)0.0191 (7)
C20.5928 (2)0.3377 (3)0.94980 (13)0.0183 (6)
C30.6041 (2)0.3530 (3)1.00843 (13)0.0208 (7)
H30.60190.4451.02510.025*
C40.6190 (2)0.2267 (3)1.04167 (12)0.0197 (7)
C50.6450 (2)0.0662 (3)1.10842 (13)0.0239 (7)
H50.65520.02271.14430.029*
C60.6271 (2)0.0893 (3)1.01577 (13)0.0189 (7)
C70.6167 (2)0.0728 (3)0.95744 (13)0.0214 (7)
H70.6219−0.0190.94110.026*
C80.5983 (2)0.1984 (3)0.92389 (12)0.0184 (6)
C90.5866 (2)0.1816 (3)0.85997 (13)0.0213 (7)
C100.9289 (2)0.0441 (3)0.58849 (12)0.0183 (7)
C110.9106 (2)0.1849 (3)0.55483 (12)0.0177 (6)
C120.9058 (2)0.1699 (3)0.49677 (13)0.0196 (7)
H120.91260.07810.48080.024*
C130.8906 (2)0.2943 (3)0.46267 (12)0.0187 (6)
C140.8668 (2)0.4547 (3)0.39564 (13)0.0237 (7)
H140.85910.49830.35990.028*
C150.8770 (2)0.4308 (3)0.48777 (13)0.0185 (7)
C160.8824 (2)0.4477 (3)0.54609 (12)0.0191 (7)
H160.87380.53930.56180.023*
C170.9008 (2)0.3246 (3)0.58027 (12)0.0189 (7)
C180.9107 (2)0.3408 (3)0.64404 (13)0.0210 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0225 (2)0.0194 (2)0.0143 (2)0.00200 (17)0.00370 (17)0.00148 (17)
Co20.0228 (2)0.0182 (2)0.0151 (2)0.00204 (17)0.00394 (17)0.00131 (17)
N10.0294 (14)0.0225 (14)0.0147 (13)0.0035 (12)0.0033 (11)0.0005 (11)
N20.0312 (15)0.0180 (13)0.0213 (14)0.0038 (11)0.0068 (12)0.0026 (11)
N30.0293 (14)0.0218 (14)0.0146 (13)0.0026 (11)0.0053 (11)0.0029 (11)
N40.0288 (14)0.0173 (13)0.0180 (14)0.0029 (11)0.0026 (11)0.0020 (11)
O10.0218 (11)0.0201 (11)0.0182 (11)0.0012 (9)0.0018 (9)0.0033 (9)
O20.0313 (13)0.0216 (12)0.0330 (13)−0.0045 (10)−0.0024 (10)0.0076 (10)
O30.0314 (12)0.0221 (12)0.0180 (11)−0.0017 (10)0.0073 (9)0.0001 (10)
O40.0743 (19)0.0210 (13)0.0193 (12)−0.0099 (12)0.0050 (12)−0.0027 (10)
O50.0209 (11)0.0211 (11)0.0182 (11)0.0030 (9)0.0038 (9)0.0043 (9)
O60.0232 (12)0.0232 (12)0.0347 (13)−0.0012 (10)0.0032 (10)0.0095 (10)
O70.0611 (17)0.0240 (13)0.0177 (12)0.0165 (12)0.0123 (11)0.0057 (10)
O80.0635 (17)0.0201 (12)0.0184 (12)−0.0012 (12)0.0068 (11)−0.0024 (10)
O810.0270 (12)0.0352 (13)0.0162 (11)0.0034 (10)0.0035 (9)0.0044 (10)
O820.0465 (15)0.0324 (13)0.0175 (12)0.0148 (11)0.0046 (10)0.0012 (10)
O830.0257 (12)0.0360 (14)0.0313 (13)−0.0021 (10)0.0084 (10)−0.0041 (11)
O840.0279 (12)0.0194 (11)0.0254 (12)−0.0008 (9)0.0016 (10)0.0058 (9)
O850.0330 (12)0.0231 (12)0.0171 (11)0.0056 (10)0.0077 (10)0.0023 (9)
O860.0490 (15)0.0325 (13)0.0183 (12)0.0157 (12)0.0021 (11)−0.0024 (10)
O870.0286 (12)0.0202 (12)0.0302 (13)−0.0010 (10)0.0036 (10)0.0063 (10)
O880.0227 (12)0.0233 (12)0.0345 (13)0.0003 (9)0.0052 (10)−0.0006 (10)
O910.0509 (17)0.0457 (17)0.0576 (18)0.0134 (14)0.0278 (14)0.0186 (14)
O920.070 (2)0.0516 (18)0.0443 (17)−0.0194 (16)0.0270 (15)−0.0080 (14)
O930.0347 (15)0.0281 (15)0.120 (3)0.0071 (12)0.0217 (17)0.0268 (16)
O940.067 (2)0.0368 (19)0.040 (2)−0.0193 (17)−0.0086 (18)0.0133 (16)
O950.073 (2)0.059 (2)0.079 (2)0.0141 (18)−0.0002 (19)−0.0172 (18)
C10.0250 (17)0.0194 (16)0.0139 (15)0.0009 (13)0.0065 (13)0.0004 (12)
C20.0180 (15)0.0166 (15)0.0202 (16)0.0007 (12)0.0031 (13)0.0031 (13)
C30.0260 (16)0.0180 (16)0.0185 (16)0.0006 (13)0.0038 (13)−0.0011 (13)
C40.0225 (16)0.0219 (16)0.0147 (15)0.0012 (13)0.0030 (12)0.0016 (13)
C50.0311 (18)0.0237 (17)0.0176 (16)0.0044 (14)0.0066 (14)0.0051 (14)
C60.0221 (16)0.0170 (16)0.0178 (16)0.0015 (12)0.0039 (13)0.0020 (13)
C70.0262 (17)0.0184 (16)0.0200 (16)0.0001 (13)0.0052 (13)−0.0015 (13)
C80.0183 (15)0.0204 (16)0.0173 (15)0.0000 (12)0.0055 (12)−0.0003 (13)
C90.0245 (16)0.0210 (17)0.0188 (16)0.0004 (13)0.0048 (13)0.0012 (14)
C100.0264 (17)0.0183 (16)0.0110 (14)0.0016 (13)0.0052 (13)−0.0022 (12)
C110.0155 (14)0.0197 (16)0.0184 (16)0.0015 (12)0.0042 (12)0.0000 (13)
C120.0263 (16)0.0158 (15)0.0173 (15)0.0023 (13)0.0053 (13)−0.0003 (12)
C130.0202 (15)0.0200 (16)0.0161 (15)0.0016 (13)0.0037 (12)0.0011 (13)
C140.0323 (18)0.0225 (17)0.0163 (16)0.0004 (14)0.0042 (14)0.0033 (14)
C150.0182 (15)0.0186 (16)0.0179 (16)−0.0001 (12)0.0010 (12)0.0035 (13)
C160.0210 (15)0.0168 (15)0.0195 (16)0.0009 (13)0.0029 (13)−0.0028 (13)
C170.0187 (15)0.0215 (16)0.0160 (15)0.0006 (12)0.0017 (12)0.0003 (13)
C180.0220 (16)0.0228 (18)0.0191 (16)−0.0011 (13)0.0056 (13)−0.0003 (14)
Geometric parameters (Å, º) top
Co1—O12.075 (2)O85—H85A0.8492
Co1—O812.088 (2)O85—H85B0.8453
Co1—O832.089 (2)O86—H86A0.8289
Co1—O822.103 (2)O86—H86B0.8315
Co1—N1i2.114 (3)O87—H87A0.8418
Co1—O842.152 (2)O87—H87B0.8463
Co2—O882.059 (2)O88—H88A0.8427
Co2—O52.090 (2)O88—H88B0.8502
Co2—O872.104 (2)O91—H91A0.85
Co2—O862.118 (2)O91—H91B0.8579
Co2—N3ii2.133 (3)O92—H92A0.8623
Co2—O852.133 (2)O92—H92B0.8503
N1—C51.322 (4)O93—H93A0.859
N1—C41.391 (4)O93—H93B0.8553
N1—Co1i2.114 (3)O94—O94'1.142 (18)
N2—C51.332 (4)O94—H94A0.8377
N2—C61.383 (4)O94—H94B0.8405
N2—H20.86O95—H95A0.8987
N3—C141.328 (4)C1—C21.507 (4)
N3—C131.395 (4)C2—C31.386 (4)
N3—Co2ii2.133 (3)C2—C81.419 (4)
N4—C141.336 (4)C3—C41.392 (4)
N4—C151.383 (4)C3—H30.93
N4—H40.86C4—C61.408 (4)
O1—C11.261 (4)C5—H50.93
O2—C11.258 (4)C6—C71.381 (4)
O3—C91.262 (4)C7—C81.394 (4)
O4—C91.248 (4)C7—H70.93
O5—C101.259 (4)C8—C91.512 (4)
O6—C101.254 (4)C10—C111.511 (4)
O7—C181.252 (4)C11—C121.380 (4)
O8—C181.260 (4)C11—C171.425 (4)
O81—H81A0.8597C12—C131.390 (4)
O81—H81B0.8436C12—H120.93
O82—H82A0.8483C13—C151.405 (4)
O82—H82B0.8541C14—H140.93
O83—H83A0.8276C15—C161.387 (4)
O83—H83B0.8533C16—C171.384 (4)
O84—H84A0.8491C16—H160.93
O84—H84B0.8475C17—C181.510 (4)
O1—Co1—O81170.17 (9)Co2—O87—H87B119.9
O1—Co1—O8388.25 (9)H87A—O87—H87B109.1
O81—Co1—O8389.55 (9)Co2—O88—H88A124.2
O1—Co1—O8281.36 (8)Co2—O88—H88B123.1
O81—Co1—O8289.00 (9)H88A—O88—H88B106.6
O83—Co1—O8288.35 (9)H91A—O91—H91B113
O1—Co1—N1i98.29 (9)H92A—O92—H92B105.6
O81—Co1—N1i91.34 (9)H93A—O93—H93B106.4
O83—Co1—N1i91.46 (10)H94A—O94—H94B109.4
O82—Co1—N1i179.61 (10)O2—C1—O1124.5 (3)
O1—Co1—O8491.72 (8)O2—C1—C2118.7 (3)
O81—Co1—O8490.09 (8)O1—C1—C2116.5 (3)
O83—Co1—O84177.69 (9)C3—C2—C8121.5 (3)
O82—Co1—O8489.36 (9)C3—C2—C1114.9 (3)
N1i—Co1—O8490.83 (9)C8—C2—C1123.4 (3)
O88—Co2—O587.45 (8)C2—C3—C4118.1 (3)
O88—Co2—O87173.57 (9)C2—C3—H3120.9
O5—Co2—O8790.48 (8)C4—C3—H3120.9
O88—Co2—O8685.63 (9)N1—C4—C3130.6 (3)
O5—Co2—O8682.13 (8)N1—C4—C6109.4 (3)
O87—Co2—O8688.05 (9)C3—C4—C6120.0 (3)
O88—Co2—N3ii90.76 (9)N1—C5—N2113.7 (3)
O5—Co2—N3ii98.09 (9)N1—C5—H5123.1
O87—Co2—N3ii95.57 (9)N2—C5—H5123.1
O86—Co2—N3ii176.37 (10)C7—C6—N2132.8 (3)
O88—Co2—O8592.79 (8)C7—C6—C4122.4 (3)
O5—Co2—O85167.66 (8)N2—C6—C4104.8 (3)
O87—Co2—O8587.93 (8)C6—C7—C8117.8 (3)
O86—Co2—O8585.59 (9)C6—C7—H7121.1
N3ii—Co2—O8594.25 (9)C8—C7—H7121.1
C5—N1—C4104.5 (3)C7—C8—C2120.1 (3)
C5—N1—Co1i122.9 (2)C7—C8—C9118.3 (3)
C4—N1—Co1i130.5 (2)C2—C8—C9121.6 (3)
C5—N2—C6107.6 (3)O4—C9—O3124.0 (3)
C5—N2—H2126.2O4—C9—C8118.5 (3)
C6—N2—H2126.2O3—C9—C8117.6 (3)
C14—N3—C13104.2 (3)O6—C10—O5124.5 (3)
C14—N3—Co2ii125.6 (2)O6—C10—C11118.5 (3)
C13—N3—Co2ii129.7 (2)O5—C10—C11116.8 (3)
C14—N4—C15107.1 (3)C12—C11—C17121.5 (3)
C14—N4—H4126.5C12—C11—C10115.1 (3)
C15—N4—H4126.5C17—C11—C10123.4 (3)
C1—O1—Co1128.73 (19)C11—C12—C13118.9 (3)
C10—O5—Co2130.89 (19)C11—C12—H12120.5
Co1—O81—H81A112.8C13—C12—H12120.5
Co1—O81—H81B106.1C12—C13—N3131.3 (3)
H81A—O81—H81B106.9C12—C13—C15119.3 (3)
Co1—O82—H82A114.7N3—C13—C15109.4 (3)
Co1—O82—H82B130.3N3—C14—N4114.0 (3)
H82A—O82—H82B109.7N3—C14—H14123
Co1—O83—H83A113.5N4—C14—H14123
Co1—O83—H83B123.3N4—C15—C16132.3 (3)
H83A—O83—H83B109.6N4—C15—C13105.4 (3)
Co1—O84—H84A97.6C16—C15—C13122.4 (3)
Co1—O84—H84B118.2C17—C16—C15118.3 (3)
H84A—O84—H84B108.6C17—C16—H16120.8
Co2—O85—H85A122.9C15—C16—H16120.8
Co2—O85—H85B114.9C16—C17—C11119.6 (3)
H85A—O85—H85B110.2C16—C17—C18119.3 (3)
Co2—O86—H86A129.6C11—C17—C18121.1 (3)
Co2—O86—H86B111.4O7—C18—O8123.3 (3)
H86A—O86—H86B116.6O7—C18—C17118.4 (3)
Co2—O87—H87A105.7O8—C18—C17118.3 (3)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O94iii0.861.962.779 (4)159
N4—H4···O930.861.842.673 (4)164
O81—H81A···O3iv0.861.842.683 (3)166
O81—H81B···O85v0.842.052.883 (3)172
O82—H82A···O30.852.142.974 (3)169
O82—H82B···O4iv0.851.842.691 (3)176
O83—H83A···O95vi0.832.052.812 (4)153
O83—H83B···O6iv0.851.962.721 (3)147
O84—H84A···O20.851.82.616 (3)162
O84—H84B···O4vii0.851.882.708 (3)165
O85—H85A···O92viii0.852.022.850 (4)167
O85—H85B···O7ix0.851.822.649 (3)168
O86—H86A···O8ix0.831.882.711 (3)176
O86—H86B···O70.832.032.859 (3)178
O87—H87A···O60.841.852.642 (3)156
O87—H87B···O8x0.851.862.689 (3)166
O88—H88A···O91ix0.841.982.813 (3)173
O88—H88B···O3ix0.851.92.732 (3)165
O91—H91A···O950.851.992.836 (4)180
O91—H91B···O840.861.982.837 (3)174
O92—H92A···O910.862.052.813 (4)148
O92—H92B···O87vii0.852.343.089 (4)148
O93—H93A···O2xi0.862.072.844 (3)151
O93—H93A···O88xii0.862.63.045 (4)114
O93—H93B···O5xii0.861.952.788 (3)168
O94—H94A···O2xi0.842.12.889 (4)158
O94—H94A···O930.842.623.180 (5)126
O94—H94B···O6vii0.842.042.873 (4)174
O95—H95A···O1iv0.92.072.910 (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
Mr760.35
Crystal system, space groupMonoclinic, 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)
Z4
Radiation typeMo Kα
µ (mm−1)1.26
Crystal size (mm)0.30 × 0.18 × 0.08
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.776, 0.905
No. of measured, independent and
observed [I > 2σ(I)] reflections		22168, 5249, 4216
Rint0.032
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.103, 1.10
No. of reflections5249
No. of parameters412
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (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···AD—HH···AD···AD—H···A
N2—H2···O94i0.861.962.779 (4)159
N4—H4···O930.861.842.673 (4)164
O81—H81A···O3ii0.861.842.683 (3)166
O81—H81B···O85iii0.842.052.883 (3)172
O82—H82A···O30.852.142.974 (3)169
O82—H82B···O4ii0.851.842.691 (3)176
O83—H83A···O95iv0.832.052.812 (4)153
O83—H83B···O6ii0.851.962.721 (3)147
O84—H84A···O20.851.82.616 (3)162
O84—H84B···O4v0.851.882.708 (3)165
O85—H85A···O92vi0.852.022.850 (4)167
O85—H85B···O7vii0.851.822.649 (3)168
O86—H86A···O8vii0.831.882.711 (3)176
O86—H86B···O70.832.032.859 (3)178
O87—H87A···O60.841.852.642 (3)156
O87—H87B···O8viii0.851.862.689 (3)166
O88—H88A···O91vii0.841.982.813 (3)173
O88—H88B···O3vii0.851.92.732 (3)165
O91—H91A···O950.851.992.836 (4)180
O91—H91B···O840.861.982.837 (3)174
O92—H92A···O910.862.052.813 (4)148
O92—H92B···O87v0.852.343.089 (4)148
O93—H93A···O2ix0.862.072.844 (3)151
O93—H93A···O88x0.862.63.045 (4)114
O93—H93B···O5x0.861.952.788 (3)168
O94—H94A···O2ix0.842.12.889 (4)158
O94—H94A···O930.842.623.180 (5)126
O94—H94B···O6v0.842.042.873 (4)174
O95—H95A···O1ii0.92.072.910 (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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