Diaqua­bis­(4-carb­oxy-2-propyl-1H-imidazole-5-carboxyl­ato-κ2N3,O4)cobalt(II) N,N-dimethyl­formamide disolvate

Li, S.-J.; Ji, L.-L.; Song, W.-D.; Hu, S.-W.; Qin, P.-W.

doi:10.1107/S1600536810042054

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1443-m1444

https://doi.org/10.1107/S1600536810042054

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Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ²N³,O⁴)cobalt(II) N,N-dimethylformamide disolvate

Shi-Jie Li,^a Li-Li Ji,^a Wen-Dong Song,^b ^* Shi-Wei Hu ^a and Pei-Wen Qin ^c

^aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cCollege of Agriculture, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 4 October 2010; accepted 17 October 2010; online 23 October 2010)

In the title complex, [Co(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the Co^II cation (site symmetry $[\overline1]$ ) is six-coordinated by two 5-carboxy-2-propyl-1H-imidazole-4-carboxylate ligands and two water molecules in a distorted octahedral environment. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are linked by extensive O—H⋯O and N—H⋯O hydrogen bonding into sheets lying parallel to (21 $[\overline{1}]$ ).

Related literature

For our past work based on the 2-propyl-1H-imidazole-4,5-carboxylate (H₃pimda) ligand, see: Yan et al. (2010 ); Li et al. (2010a ,b ,c ,d ); Song et al. (2010 ); He et al. (2010 ); Fan et al. (2010 ). For Co complexes of a similar ligand, see: Lu et al. (2008 ); Wang et al. (2004 ).

Experimental

Crystal data

[Co(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r = 635.50
Triclinic, $[P \overline 1]$
a = 7.3325 (7) Å
b = 9.330 (1) Å
c = 11.2255 (12) Å
α = 76.930 (1)°
β = 87.564 (2)°
γ = 68.857 (1)°
V = 697.06 (12) Å³
Z = 1
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 298 K
0.28 × 0.16 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.831, T_max = 0.922
3602 measured reflections
2393 independent reflections
1785 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.120
S = 1.06
2393 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5D⋯O4ⁱ	0.83	2.12	2.946 (3)	174
O5—H5C⋯O4ⁱⁱ	0.83	1.94	2.773 (3)	175
O2—H2A⋯O3	0.82	1.66	2.478 (3)	177
N2—H2⋯O6ⁱⁱⁱ	0.86	1.84	2.685 (4)	166
Symmetry codes: (i) x-1, y+1, z; (ii) -x+1, -y, -z+1; (iii) x+1, y-1, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042054/jh2216sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042054/jh2216Isup2.hkl

checkCIF report

Comment top

Design of a metal-organic framework via deliberate selection of metals and multifunctional ligands is one of the most attractive topics because of the fascinating structural diversity and potential applications in catalysis, chirality, conductivity, luminescence, magnetism, sensors, nonlinear optics, and porosity. 2-propyl-1H-imidazole-4,5-carboxylate(H₃pimda) ligand as one derivative of H₃IDC with efficient N,O-donors has been used to obtain new metal-organic complexes by our research group, such as poly[diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-k³ N³, O⁴,O⁵)calcium(II)](Song et al., 2010), [diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-k²N³,O⁴) manganese(II)]N,N-dimethylformamide(Yan et al., 2010), [Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-k² N³,O⁴)nickle(II)]N,N-dimethylformamide disolvate(Li et al., 2010a), Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato- k²N³,O⁴)copper(II) N,N-dimethylformamide disolvate(He et al., 2010), Diaquabis(5-carboxy-2-propyl-1H-imidazole- 4-carboxylato-k²N³,O⁴)nickle(II) tetrahedrate(Fan et al., 2010), Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- k²N³,O⁴)-manganese(II) 3.5-hydrate(Li et al. 2010c), Diaquabis (5-carboxy-2-propyl-1H-imidazole-4-carboxylato-K²N³,O⁴)zinc(II) 3.5-hydrate(Li et al. 2010b), Diaquabis(5-carboxy-2-propyl-1H- imidazole-4-carboxylato-k²N³,O⁴)cadmium(II) 3.5-hydrate (Li et al. 2010d), In this paper, we will report the synthesis and structure of a new Co^II complex based the same ligand.

As illustrated in figure 1, the title complex molecule is isomorphous with Ni(II), Mn(II) and Cu(II) analogs (Li et al., 2010a,b,c,d; Yan et al., 2010; He et al., 2010), Similar structural description applies to the present isomorphous complex.the Co^II cation lying on the inversion center, is six-coordinated CoN₂O₄ in a slightly distorted octahedral geometry, constructed by the two pairs of N and O atoms from H₂pimda in the equatorial plane, and two coordinate water O atoms occipying the axial position. The Co—O bond lengths and Co—N bond lengths, all of which are within the range of those observed for other Co complexes based on the similar ligand (Lu et al., 2008; Wang et al., 2004). Each H₃pimda adopts bidentate coordination mode to chelate Co^II atom through imidazole N atom and O atom from the protonated carboxyl group, the complex molecules and dimethylformamide solvent molecules are linked by extensive O—H···O and N—H···O hydrogen bonds into a two-dimensional supramolecular network parallel to (001).

Related literature top

For our past work based on the 2-propyl-1H-imidazole-4,5-carboxylate (H₃pimda) ligand, see: Yan et al. (2010); Li et al. (2010a,b,c,d); Song et al. (2010); He et al. (2010); Fan et al. (2010). For Co complexes of a similar ligand, see: Lu et al. (2008); Wang et al. (2004).

Experimental top

A mixture of Co(NO3)₂ (0.5 mmol, 0.06 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid(0.5 mmol, 0.99 g) in 15 ml of DMF solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 413k for 3 days. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Structure description top

For our past work based on the 2-propyl-1H-imidazole-4,5-carboxylate (H₃pimda) ligand, see: Yan et al. (2010); Li et al. (2010a,b,c,d); Song et al. (2010); He et al. (2010); Fan et al. (2010). For Co complexes of a similar ligand, see: Lu et al. (2008); Wang et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. (Symmetry codes: (i)1 - x,1 - y,1 - z;)
	Fig. 2. A view of the infinite two-dimensional structure. (H atoms are omitted for clarity)

Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato- κ²N³,O⁴)cobalt(II) N,N-dimethylformamide disolvate top

Crystal data top

[Co(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	Z = 1
M_r = 635.50	F(000) = 333
Triclinic, P1	D_x = 1.514 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3325 (7) Å	Cell parameters from 1702 reflections
b = 9.330 (1) Å	θ = 2.5–25.9°
c = 11.2255 (12) Å	µ = 0.69 mm⁻¹
α = 76.930 (1)°	T = 298 K
β = 87.564 (2)°	Cubic, purple
γ = 68.857 (1)°	0.28 × 0.16 × 0.12 mm
V = 697.06 (12) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2393 independent reflections
Radiation source: fine-focus sealed tube	1785 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.831, T_max = 0.922	k = −11→10
3602 measured reflections	l = −13→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0593P)² + 0.0702P] where P = (F_o² + 2F_c²)/3
2393 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Co(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	γ = 68.857 (1)°
M_r = 635.50	V = 697.06 (12) Å³
Triclinic, P1	Z = 1
a = 7.3325 (7) Å	Mo Kα radiation
b = 9.330 (1) Å	µ = 0.69 mm⁻¹
c = 11.2255 (12) Å	T = 298 K
α = 76.930 (1)°	0.28 × 0.16 × 0.12 mm
β = 87.564 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2393 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1785 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.922	R_int = 0.025
3602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	Δρ_max = 0.37 e Å⁻³
2393 reflections	Δρ_min = −0.52 e Å⁻³
191 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	0.5000	0.5000	0.5000	0.0276 (2)
N1	0.6372 (4)	0.2538 (3)	0.5508 (2)	0.0262 (6)
N2	0.8031 (4)	−0.0015 (3)	0.6076 (2)	0.0299 (7)
H2	0.8735	−0.0911	0.6524	0.036*
N3	0.1217 (5)	0.4898 (4)	0.8633 (3)	0.0431 (8)
O1	0.4446 (3)	0.4305 (3)	0.3378 (2)	0.0342 (6)
O2	0.4995 (4)	0.2241 (3)	0.2558 (2)	0.0410 (6)
H2A	0.5618	0.1289	0.2735	0.061*
O3	0.6877 (4)	−0.0632 (3)	0.3176 (2)	0.0422 (6)
O4	0.8630 (4)	−0.2427 (3)	0.4793 (2)	0.0415 (6)
O5	0.2300 (3)	0.4898 (3)	0.5643 (2)	0.0393 (6)
H5C	0.2094	0.4117	0.5526	0.047*
H5D	0.1309	0.5698	0.5403	0.047*
O6	0.0385 (4)	0.7471 (3)	0.7696 (3)	0.0600 (8)
C1	0.5195 (5)	0.2858 (4)	0.3436 (3)	0.0300 (8)
C2	0.6307 (5)	0.1832 (4)	0.4565 (3)	0.0257 (7)
C3	0.7326 (5)	0.0238 (4)	0.4905 (3)	0.0274 (7)
C4	0.7665 (5)	−0.1054 (4)	0.4262 (3)	0.0325 (8)
C5	0.7426 (5)	0.1391 (4)	0.6406 (3)	0.0288 (8)
C6	0.7851 (6)	0.1544 (4)	0.7649 (3)	0.0380 (9)
H6A	0.7434	0.2655	0.7652	0.046*
H6B	0.9254	0.1081	0.7822	0.046*
C7	0.6851 (7)	0.0760 (5)	0.8653 (3)	0.0535 (11)
H7A	0.7339	−0.0364	0.8688	0.064*
H7B	0.5458	0.1168	0.8449	0.064*
C8	0.7158 (7)	0.1009 (6)	0.9906 (3)	0.0587 (12)
H8A	0.8492	0.0418	1.0192	0.088*
H8B	0.6301	0.0656	1.0467	0.088*
H8C	0.6876	0.2110	0.9853	0.088*
C9	0.0104 (6)	0.6217 (5)	0.7892 (4)	0.0482 (10)
H9	−0.0967	0.6196	0.7490	0.058*
C10	0.2965 (6)	0.4851 (5)	0.9218 (4)	0.0659 (13)
H10A	0.4092	0.4333	0.8796	0.099*
H10B	0.3077	0.4281	1.0055	0.099*
H10C	0.2887	0.5907	0.9190	0.099*
C11	0.0896 (9)	0.3443 (6)	0.8724 (5)	0.0855 (17)
H11A	−0.0306	0.3653	0.8290	0.128*
H11B	0.0817	0.2973	0.9570	0.128*
H11C	0.1962	0.2733	0.8375	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0338 (4)	0.0169 (4)	0.0301 (4)	−0.0063 (3)	−0.0011 (3)	−0.0059 (3)
N1	0.0333 (16)	0.0169 (15)	0.0287 (15)	−0.0088 (12)	−0.0018 (12)	−0.0059 (12)
N2	0.0349 (17)	0.0144 (14)	0.0346 (16)	−0.0038 (12)	−0.0030 (13)	−0.0019 (12)
N3	0.049 (2)	0.0271 (18)	0.0475 (19)	−0.0089 (16)	−0.0012 (16)	−0.0055 (15)
O1	0.0437 (15)	0.0207 (13)	0.0315 (13)	−0.0046 (11)	−0.0077 (11)	−0.0025 (10)
O2	0.0544 (18)	0.0285 (14)	0.0357 (14)	−0.0071 (13)	−0.0098 (12)	−0.0098 (12)
O3	0.0545 (17)	0.0317 (15)	0.0424 (16)	−0.0108 (13)	0.0002 (13)	−0.0197 (12)
O4	0.0462 (16)	0.0189 (14)	0.0572 (17)	−0.0063 (12)	−0.0018 (13)	−0.0125 (12)
O5	0.0390 (15)	0.0270 (14)	0.0549 (16)	−0.0118 (12)	0.0054 (12)	−0.0158 (12)
O6	0.066 (2)	0.0279 (16)	0.070 (2)	−0.0047 (14)	−0.0209 (16)	0.0049 (14)
C1	0.033 (2)	0.027 (2)	0.0322 (19)	−0.0115 (16)	0.0004 (15)	−0.0091 (16)
C2	0.0293 (18)	0.0177 (16)	0.0285 (17)	−0.0072 (14)	0.0001 (14)	−0.0043 (14)
C3	0.0319 (19)	0.0228 (18)	0.0295 (18)	−0.0119 (15)	0.0023 (15)	−0.0067 (14)
C4	0.030 (2)	0.025 (2)	0.045 (2)	−0.0092 (16)	0.0079 (17)	−0.0144 (17)
C5	0.034 (2)	0.0179 (18)	0.0322 (19)	−0.0084 (15)	−0.0024 (15)	−0.0016 (15)
C6	0.046 (2)	0.030 (2)	0.036 (2)	−0.0113 (17)	−0.0087 (17)	−0.0054 (16)
C7	0.068 (3)	0.061 (3)	0.040 (2)	−0.029 (2)	0.009 (2)	−0.019 (2)
C8	0.065 (3)	0.068 (3)	0.039 (2)	−0.019 (3)	0.006 (2)	−0.014 (2)
C9	0.043 (2)	0.050 (3)	0.048 (2)	−0.011 (2)	−0.0044 (19)	−0.012 (2)
C10	0.049 (3)	0.055 (3)	0.071 (3)	−0.004 (2)	−0.017 (2)	0.009 (2)
C11	0.126 (5)	0.045 (3)	0.094 (4)	−0.043 (3)	0.017 (4)	−0.016 (3)

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.098 (3)	O6—C9	1.230 (5)
Co1—N1	2.098 (3)	C1—C2	1.471 (5)
Co1—O5ⁱ	2.105 (2)	C2—C3	1.372 (4)
Co1—O5	2.105 (2)	C3—C4	1.482 (4)
Co1—O1ⁱ	2.165 (2)	C5—C6	1.491 (4)
Co1—O1	2.165 (2)	C6—C7	1.513 (5)
N1—C5	1.319 (4)	C6—H6A	0.9700
N1—C2	1.377 (4)	C6—H6B	0.9700
N2—C5	1.357 (4)	C7—C8	1.515 (5)
N2—C3	1.371 (4)	C7—H7A	0.9700
N2—H2	0.8600	C7—H7B	0.9700
N3—C9	1.320 (5)	C8—H8A	0.9600
N3—C11	1.440 (5)	C8—H8B	0.9600
N3—C10	1.447 (5)	C8—H8C	0.9600
O1—C1	1.248 (4)	C9—H9	0.9300
O2—C1	1.286 (4)	C10—H10A	0.9600
O2—H2A	0.8200	C10—H10B	0.9600
O3—C4	1.286 (4)	C10—H10C	0.9600
O4—C4	1.238 (4)	C11—H11A	0.9600
O5—H5C	0.8333	C11—H11B	0.9600
O5—H5D	0.8318	C11—H11C	0.9600

N1ⁱ—Co1—N1	180.0	O4—C4—C3	119.3 (3)
N1ⁱ—Co1—O5ⁱ	92.07 (10)	O3—C4—C3	115.5 (3)
N1—Co1—O5ⁱ	87.93 (10)	N1—C5—N2	110.7 (3)
N1ⁱ—Co1—O5	87.93 (10)	N1—C5—C6	126.4 (3)
N1—Co1—O5	92.07 (10)	N2—C5—C6	122.8 (3)
O5ⁱ—Co1—O5	180.0	C5—C6—C7	113.5 (3)
N1ⁱ—Co1—O1ⁱ	78.33 (9)	C5—C6—H6A	108.9
N1—Co1—O1ⁱ	101.67 (9)	C7—C6—H6A	108.9
O5ⁱ—Co1—O1ⁱ	88.69 (9)	C5—C6—H6B	108.9
O5—Co1—O1ⁱ	91.31 (9)	C7—C6—H6B	108.9
N1ⁱ—Co1—O1	101.67 (9)	H6A—C6—H6B	107.7
N1—Co1—O1	78.33 (9)	C6—C7—C8	113.8 (3)
O5ⁱ—Co1—O1	91.31 (9)	C6—C7—H7A	108.8
O5—Co1—O1	88.69 (9)	C8—C7—H7A	108.8
O1ⁱ—Co1—O1	180.0	C6—C7—H7B	108.8
C5—N1—C2	105.8 (3)	C8—C7—H7B	108.8
C5—N1—Co1	142.0 (2)	H7A—C7—H7B	107.7
C2—N1—Co1	111.9 (2)	C7—C8—H8A	109.5
C5—N2—C3	108.3 (3)	C7—C8—H8B	109.5
C5—N2—H2	125.8	H8A—C8—H8B	109.5
C3—N2—H2	125.8	C7—C8—H8C	109.5
C9—N3—C11	121.0 (4)	H8A—C8—H8C	109.5
C9—N3—C10	119.5 (3)	H8B—C8—H8C	109.5
C11—N3—C10	118.7 (4)	O6—C9—N3	124.5 (4)
C1—O1—Co1	114.2 (2)	O6—C9—H9	117.7
C1—O2—H2A	109.5	N3—C9—H9	117.7
Co1—O5—H5C	113.1	N3—C10—H10A	109.5
Co1—O5—H5D	116.9	N3—C10—H10B	109.5
H5C—O5—H5D	108.6	H10A—C10—H10B	109.5
O1—C1—O2	122.4 (3)	N3—C10—H10C	109.5
O1—C1—C2	118.2 (3)	H10A—C10—H10C	109.5
O2—C1—C2	119.5 (3)	H10B—C10—H10C	109.5
C3—C2—N1	110.3 (3)	N3—C11—H11A	109.5
C3—C2—C1	132.5 (3)	N3—C11—H11B	109.5
N1—C2—C1	117.2 (3)	H11A—C11—H11B	109.5
N2—C3—C2	104.9 (3)	N3—C11—H11C	109.5
N2—C3—C4	122.9 (3)	H11A—C11—H11C	109.5
C2—C3—C4	132.2 (3)	H11B—C11—H11C	109.5
O4—C4—O3	125.2 (3)

N1ⁱ—Co1—N1—C5	156 (25)	O1—C1—C2—N1	2.7 (5)
O5ⁱ—Co1—N1—C5	85.2 (4)	O2—C1—C2—N1	−175.9 (3)
O5—Co1—N1—C5	−94.8 (4)	C5—N2—C3—C2	0.4 (3)
O1ⁱ—Co1—N1—C5	−3.0 (4)	C5—N2—C3—C4	−178.4 (3)
O1—Co1—N1—C5	177.0 (4)	N1—C2—C3—N2	−0.5 (3)
N1ⁱ—Co1—N1—C2	−17 (25)	C1—C2—C3—N2	−179.6 (3)
O5ⁱ—Co1—N1—C2	−88.1 (2)	N1—C2—C3—C4	178.1 (3)
O5—Co1—N1—C2	91.9 (2)	C1—C2—C3—C4	−1.0 (6)
O1ⁱ—Co1—N1—C2	−176.3 (2)	N2—C3—C4—O4	−0.3 (5)
O1—Co1—N1—C2	3.7 (2)	C2—C3—C4—O4	−178.6 (3)
N1ⁱ—Co1—O1—C1	177.5 (2)	N2—C3—C4—O3	178.7 (3)
N1—Co1—O1—C1	−2.5 (2)	C2—C3—C4—O3	0.4 (5)
O5ⁱ—Co1—O1—C1	85.2 (2)	C2—N1—C5—N2	−0.1 (4)
O5—Co1—O1—C1	−94.8 (2)	Co1—N1—C5—N2	−173.7 (2)
O1ⁱ—Co1—O1—C1	26 (45)	C2—N1—C5—C6	−177.2 (3)
Co1—O1—C1—O2	179.3 (2)	Co1—N1—C5—C6	9.3 (6)
Co1—O1—C1—C2	0.7 (4)	C3—N2—C5—N1	−0.2 (4)
C5—N1—C2—C3	0.4 (4)	C3—N2—C5—C6	177.1 (3)
Co1—N1—C2—C3	176.1 (2)	N1—C5—C6—C7	110.9 (4)
C5—N1—C2—C1	179.6 (3)	N2—C5—C6—C7	−65.8 (5)
Co1—N1—C2—C1	−4.7 (3)	C5—C6—C7—C8	−175.9 (3)
O1—C1—C2—C3	−178.2 (3)	C11—N3—C9—O6	−174.1 (4)
O2—C1—C2—C3	3.2 (6)	C10—N3—C9—O6	−3.8 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5D···O4ⁱⁱ	0.83	2.12	2.946 (3)	174
O5—H5C···O4ⁱⁱⁱ	0.83	1.94	2.773 (3)	175
O2—H2A···O3	0.82	1.66	2.478 (3)	177
N2—H2···O6^iv	0.86	1.84	2.685 (4)	166

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

Experimental details

Crystal data
Chemical formula	[Co(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r	635.50
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3325 (7), 9.330 (1), 11.2255 (12)
α, β, γ (°)	76.930 (1), 87.564 (2), 68.857 (1)
V (Å³)	697.06 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.28 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.831, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	3602, 2393, 1785
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.120, 1.06
No. of reflections	2393
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.52

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5D···O4ⁱ	0.83	2.12	2.946 (3)	174.0
O5—H5C···O4ⁱⁱ	0.83	1.94	2.773 (3)	174.7
O2—H2A···O3	0.82	1.66	2.478 (3)	176.8
N2—H2···O6ⁱⁱⁱ	0.86	1.84	2.685 (4)	166.1

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

Acknowledgements

The work was supported by the Nonprofit Industry Foundation of the National Ocean Administration of China (grant No. 2000905021), the Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science comprehensive strategic cooperation project (grant No. 2009B091300121), the Guangdong Province key project in the field of social development [grant No. A2009011–007(c)], the Science and Technology Department of Guangdong Province Project (grant No. 00087061110314018) and the Guangdong Natural Science Fundation (No. 9252408801000002)

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, R.-Z., Li, S.-J., Song, W.-D., Miao, D.-L. & Hu, S.-W. (2010). Acta Cryst. E66, m897–m898. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
He, L.-Z., Li, S.-J., Song, W.-D. & Miao, D.-L. (2010). Acta Cryst. E66, m896. Web of Science CrossRef IUCr Journals Google Scholar
Li, S.-J., Dong, J.-J., Song, W.-D., Yan, J.-B. & Li, S.-H. (2010d). Acta Cryst. E66, m1175–m1176. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, S.-J., Miao, D.-L., Song, W.-D., Li, S.-H. & Yan, J.-B. (2010c). Acta Cryst. E66, m1096–m1097. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, S.-J., Song, W.-D., Li, S.-H., Dong, J.-J. & Yan, J.-B. (2010b). Acta Cryst. E66, m1094–m1095. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, S.-J., Yan, J.-B., Song, W.-D., Wang, H. & Miao, D.-L. (2010a). Acta Cryst. E66, m280. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lu, W. G., Gu, J. Z., Jiang, L., Tan, Y. M. & Lu, T. B. (2008). Cryst. Growth Des. 8, 192–199. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y.-L., Cao, R. & Bi, W.-H. (2004). Acta Cryst. C60, m609–m611. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99. Web of Science CSD CrossRef IUCr Journals Google Scholar

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