Diaqua­[5,5′-dicarb­oxy-2,2′-(ethane-1,2-di­yl)bis­(1H-imidazole-4-carboxyl­ato)]cobalt(II)

Wang, Y.; Gao, X.-L.

doi:10.1107/S1600536811019672

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m815

doi:10.1107/S1600536811019672

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Diaqua[5,5′-dicarboxy-2,2′-(ethane-1,2-diyl)bis(1H-imidazole-4-carboxylato)]cobalt(II)

Ying Wang ^a ^* and Xin-Lian Gao ^b

^aDepartment of Geriatrics, The First Affiliated Hospital, Zhengzhou University, Zhengzhou 450000, People's Republic of China, and ^bHenan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: 13623712409@139.com

(Received 4 May 2011; accepted 24 May 2011; online 28 May 2011)

In the title complex, [Co(C₁₂H₈N₄O₈)(H₂O)₂], the Co^II atom is coordinated by two N and two O atoms of the tetradentate 5,5′-dicarboxy-2,2′-(ethane-1,2-diyl)bis(1H-imidazole-4-carboxylate) anion. The slightly distorted octahedral coordination environment is completed by the O atoms of two water molecules in axial positions. An intramolecular O—H⋯O hydrogen bond between the carboxy and carboxylate groups stabilizes the molecular configuration. Adjacent molecules are linked through O—H⋯O and N—H⋯O hydrogen bonds between the carboxy/carboxylate groups, water molecules and imidazole fragments into a three-dimensional network.

Related literature

For background to complexes based on 1H-imidazole-4,5-dicarboxylic acid and its derivatives, see: Das et al. (2010 ); Sun et al. (2010 ); Zhang et al. (2010 ).

Experimental

Crystal data

[Co(C₁₂H₈N₄O₈)(H₂O)₂]
M_r = 431.19
Orthorhombic, F d d 2
a = 24.683 (5) Å
b = 27.885 (6) Å
c = 8.7340 (17) Å
V = 6012 (2) Å³
Z = 16
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 293 K
0.18 × 0.14 × 0.09 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.811, T_max = 0.899
7187 measured reflections
2693 independent reflections
2223 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.079
S = 1.01
2693 reflections
245 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983), 1126 Friedel pairs
Flack parameter: 0.20 (2)

Table 1
Selected bond lengths (Å)

Co1—O10	2.043 (4)
Co1—N3	2.044 (4)
Co1—N1	2.048 (4)
Co1—O9	2.118 (4)
Co1—O1	2.153 (3)
Co1—O5	2.168 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.85	1.65	2.461 (5)	157
O7—H7⋯O6	0.85	1.72	2.550 (5)	166
O10—H3W⋯O3ⁱ	0.85	2.18	2.799 (5)	129
N2—H2A⋯O6ⁱⁱ	0.86	2.16	2.904 (5)	145
N4—H4A⋯O5ⁱⁱⁱ	0.86	2.04	2.878 (5)	166
O9—H1W⋯O4^iv	0.85	1.89	2.730 (5)	170
O9—H2W⋯O7^v	0.85	2.06	2.834 (5)	150
O10—H4W⋯O8^vi	0.85	2.22	2.958 (5)	145
Symmetry codes: (i) x, y, z+1; (ii) $[-x+{\script{1\over 4}}, y+{\script{1\over 4}}, z-{\script{3\over 4}}]$ ; (iii) $[-x+{\script{1\over 4}}, y+{\script{1\over 4}}, z+{\script{1\over 4}}]$ ; (iv) $[x-{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{3\over 4}}]$ ; (v) x, y, z-1; (vi) $[x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z-{\script{3\over 4}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019672/wm2487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019672/wm2487Isup2.hkl

checkCIF report

Comment top

A large number of metal complexes constructed from the ligand 1H-imidazole-4,5-dicarboxylic acid or its derivatives have been reported. This ligand shows versatile binding modes and high binding capacity with almost all soft and hard metal ions (Das et al., 2010; Sun et al., 2010; Zhang et al., 2010). In order to further explore complexes with novel structures, we obtained the title complex [Co(H₄eidc)(H₂O)₂], (I), through the reaction of 2,2'-(ethane-1,2-diyl)bis(1H-imidazole-4,5-dicarboxylic acid (H₆eidc) with cobalt dichloride.

As shown in Figure 1, the Co(II) cation in (I) is hexacoordinated and features a slightly octahedral coordination environment. N1, O1, N3, O5 atoms from the tetradentate H₄eidc^2- anion coordinate to the cation in a chelating fashion and O9, O10 atoms from water molecules complete the coordination polyhedron. Atoms N1, N3, O1, O5 and Co are nearly co-planar (the mean deviation from the plane is 0.08 Å). The bond angle between the O atoms of the two water molecules and the metal is 171.87 (13) °. As shown in Figure 2, intramolecular O—H···O hydrogen bonds between the carboxyl/carboxylate groups stabilize the molecular configuration whereas O—H···O and N—H···O hydrogen bonds between the water molecules and carboxylate O atoms and between imidazole groups and carboxylate O atoms of adjacent molecules consolidate the crystal packing.

Related literature top

For background to complexes based on 1H-imidazole-4,5-dicarboxylic acid and its derivatives, see: Das et al. (2010); Sun et al. (2010); Zhang et al. (2010).

Experimental top

The ligand 2,2'-(ethane-1,2-diyl)bis(1H-imidazole-4,5-dicarboxylic acid (0.05 mmol) in methanol (4 ml) was added dropwise to a methanol solution (3 ml) of cobalt dichloride (0.05 mmol). The resulting solution was allowed to stand at room temperature. After four weeks red crystals with good quality were obtained from the filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of the title complex, showing the labelling of the atoms. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the crystal packing of the title complex, showing the three-dimensional structure stabilized by hydrogen bonds.

Diaqua[5,5'-dicarboxy-2,2'-(ethane-1,2-diyl)bis(1H-imidazole-4- carboxylato)]cobalt(II) top

Crystal data top

[Co(C₁₂H₈N₄O₈)(H₂O)₂]	F(000) = 3504
M_r = 431.19	D_x = 1.906 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	θ = 2.6–27.8°
a = 24.683 (5) Å	µ = 1.21 mm⁻¹
b = 27.885 (6) Å	T = 293 K
c = 8.7340 (17) Å	Prism, red
V = 6012 (2) Å³	0.18 × 0.14 × 0.09 mm
Z = 16

Data collection top

Rigaku Saturn CCD diffractometer	2693 independent reflections
Radiation source: fine-focus sealed tube	2223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 28.5714 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
ω scans	h = −30→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −31→33
T_min = 0.811, T_max = 0.899	l = −10→10
7187 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0302P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2693 reflections	Δρ_max = 0.37 e Å⁻³
245 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1126 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.20 (2)

Crystal data top

[Co(C₁₂H₈N₄O₈)(H₂O)₂]	V = 6012 (2) Å³
M_r = 431.19	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 24.683 (5) Å	µ = 1.21 mm⁻¹
b = 27.885 (6) Å	T = 293 K
c = 8.7340 (17) Å	0.18 × 0.14 × 0.09 mm

Data collection top

Rigaku Saturn CCD diffractometer	2693 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	2223 reflections with I > 2σ(I)
T_min = 0.811, T_max = 0.899	R_int = 0.046
7187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.079	Δρ_max = 0.37 e Å⁻³
S = 1.01	Δρ_min = −0.35 e Å⁻³
2693 reflections	Absolute structure: Flack (1983), 1126 Friedel pairs
245 parameters	Absolute structure parameter: 0.20 (2)
1 restraint

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	0.15380 (3)	0.073588 (18)	0.83795 (11)	0.02698 (17)
N1	0.17562 (18)	0.12247 (13)	0.6742 (5)	0.0234 (9)
N2	0.19660 (17)	0.17992 (13)	0.5122 (5)	0.0266 (11)
H2A	0.2014	0.2082	0.4751	0.032*
N3	0.13408 (17)	0.12246 (13)	1.0033 (5)	0.0246 (10)
N4	0.11839 (17)	0.17995 (13)	1.1637 (5)	0.0238 (11)
H4A	0.1174	0.2081	1.2039	0.029*
O1	0.18202 (16)	0.02761 (10)	0.6567 (4)	0.0338 (9)
O2	0.21834 (16)	0.02922 (12)	0.4193 (4)	0.0447 (11)
O3	0.24378 (15)	0.09236 (12)	0.2360 (4)	0.0375 (9)
H3	0.2268	0.0720	0.2902	0.045*
O4	0.24502 (15)	0.17202 (12)	0.2168 (4)	0.0381 (9)
O5	0.11949 (15)	0.02774 (11)	1.0134 (4)	0.0329 (9)
O6	0.07457 (15)	0.03203 (11)	1.2358 (4)	0.0366 (10)
O7	0.05925 (15)	0.09672 (12)	1.4375 (4)	0.0377 (10)
H7	0.0609	0.0725	1.3788	0.045*
O8	0.06967 (16)	0.17524 (12)	1.4593 (5)	0.0422 (10)
O9	0.07403 (15)	0.07148 (10)	0.7490 (4)	0.0338 (9)
H1W	0.0467	0.0730	0.8078	0.041*
H2W	0.0669	0.0888	0.6714	0.041*
O10	0.22935 (16)	0.06549 (14)	0.9300 (5)	0.0521 (12)
H3W	0.2464	0.0581	1.0112	0.062*
H4W	0.2547	0.0804	0.8846	0.062*
C1	0.1996 (2)	0.04938 (18)	0.5417 (6)	0.0318 (13)
C2	0.1972 (2)	0.10239 (16)	0.5440 (6)	0.0263 (12)
C3	0.2095 (2)	0.13797 (16)	0.4409 (5)	0.0229 (11)
C4	0.2348 (2)	0.13487 (19)	0.2884 (6)	0.0317 (13)
C5	0.1748 (2)	0.16963 (16)	0.6526 (6)	0.0236 (12)
C6	0.1512 (2)	0.20512 (18)	0.7602 (6)	0.0331 (14)
H6A	0.1122	0.2012	0.7587	0.040*
H6B	0.1590	0.2369	0.7208	0.040*
C7	0.1698 (2)	0.20335 (17)	0.9274 (6)	0.0300 (13)
H7A	0.2079	0.1949	0.9295	0.036*
H7B	0.1664	0.2352	0.9708	0.036*
C8	0.1398 (2)	0.16921 (17)	1.0263 (6)	0.0257 (12)
C9	0.09834 (19)	0.13883 (16)	1.2301 (6)	0.0244 (11)
C10	0.0749 (2)	0.13908 (18)	1.3862 (6)	0.0278 (12)
C11	0.1094 (2)	0.10327 (15)	1.1278 (5)	0.0216 (12)
C12	0.1005 (2)	0.05041 (17)	1.1266 (6)	0.0291 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0348 (4)	0.0239 (3)	0.0222 (3)	0.0011 (4)	0.0053 (3)	−0.0014 (3)
N1	0.031 (2)	0.020 (2)	0.019 (2)	0.0002 (18)	0.0058 (19)	0.0023 (17)
N2	0.031 (3)	0.025 (2)	0.024 (3)	−0.0094 (19)	0.008 (2)	0.005 (2)
N3	0.032 (3)	0.021 (2)	0.022 (2)	0.0027 (18)	−0.001 (2)	0.0001 (19)
N4	0.032 (3)	0.018 (2)	0.022 (3)	−0.0025 (18)	0.000 (2)	0.0005 (18)
O1	0.050 (3)	0.0237 (18)	0.027 (2)	−0.0017 (17)	0.0098 (19)	−0.0023 (17)
O2	0.067 (3)	0.039 (2)	0.028 (2)	0.0071 (19)	0.017 (2)	−0.0122 (18)
O3	0.044 (3)	0.048 (2)	0.021 (2)	0.0008 (18)	0.0092 (18)	−0.0042 (18)
O4	0.032 (2)	0.053 (2)	0.029 (2)	0.0013 (18)	0.0013 (19)	0.0115 (19)
O5	0.044 (3)	0.0230 (18)	0.032 (2)	−0.0022 (17)	0.001 (2)	−0.0014 (18)
O6	0.050 (3)	0.0273 (18)	0.032 (2)	−0.0022 (17)	0.0041 (19)	0.0078 (18)
O7	0.047 (3)	0.044 (2)	0.022 (2)	−0.0041 (19)	0.0046 (19)	−0.0017 (18)
O8	0.055 (3)	0.042 (2)	0.030 (2)	−0.0036 (18)	0.015 (2)	−0.0133 (19)
O9	0.032 (2)	0.0422 (19)	0.028 (2)	0.0034 (16)	0.0054 (17)	0.0032 (19)
O10	0.045 (3)	0.077 (3)	0.034 (3)	0.012 (2)	−0.005 (2)	−0.006 (2)
C1	0.035 (3)	0.034 (3)	0.027 (3)	0.001 (2)	−0.002 (2)	−0.011 (3)
C2	0.024 (3)	0.025 (3)	0.029 (3)	−0.001 (2)	0.004 (2)	−0.001 (2)
C3	0.025 (3)	0.028 (3)	0.016 (3)	0.000 (2)	0.001 (2)	−0.003 (2)
C4	0.027 (3)	0.046 (3)	0.023 (3)	0.006 (3)	−0.005 (2)	−0.002 (3)
C5	0.026 (3)	0.026 (3)	0.018 (3)	0.004 (2)	0.006 (2)	0.000 (2)
C6	0.044 (4)	0.025 (3)	0.030 (3)	0.006 (2)	0.016 (3)	0.003 (2)
C7	0.041 (4)	0.023 (3)	0.025 (3)	−0.008 (2)	0.004 (3)	0.000 (2)
C8	0.037 (3)	0.026 (3)	0.014 (3)	0.005 (2)	0.001 (2)	0.002 (2)
C9	0.030 (3)	0.023 (3)	0.020 (3)	0.001 (2)	−0.002 (2)	0.005 (2)
C10	0.023 (3)	0.035 (3)	0.025 (3)	−0.002 (2)	0.004 (2)	0.001 (3)
C11	0.032 (3)	0.019 (2)	0.014 (3)	0.000 (2)	0.001 (2)	0.004 (2)
C12	0.030 (3)	0.031 (3)	0.027 (4)	0.002 (2)	−0.002 (3)	0.002 (3)

Geometric parameters (Å, º) top

Co1—O10	2.043 (4)	O6—C12	1.258 (6)
Co1—N3	2.044 (4)	O7—C10	1.321 (6)
Co1—N1	2.048 (4)	O7—H7	0.8501
Co1—O9	2.118 (4)	O8—C10	1.200 (5)
Co1—O1	2.153 (3)	O9—H1W	0.8500
Co1—O5	2.168 (4)	O9—H2W	0.8498
N1—C5	1.329 (6)	O10—H3W	0.8501
N1—C2	1.375 (6)	O10—H4W	0.8499
N2—C3	1.363 (6)	C1—C2	1.479 (7)
N2—C5	1.370 (6)	C2—C3	1.374 (6)
N2—H2A	0.8600	C3—C4	1.474 (7)
N3—C8	1.327 (6)	C5—C6	1.484 (7)
N3—C11	1.357 (6)	C6—C7	1.532 (6)
N4—C8	1.345 (6)	C6—H6A	0.9700
N4—C9	1.377 (6)	C6—H6B	0.9700
N4—H4A	0.8600	C7—C8	1.484 (7)
O1—C1	1.252 (6)	C7—H7A	0.9700
O2—C1	1.293 (6)	C7—H7B	0.9700
O3—C4	1.290 (6)	C9—C11	1.362 (6)
O3—H3	0.8501	C9—C10	1.481 (7)
O4—C4	1.236 (6)	C11—C12	1.490 (6)
O5—C12	1.264 (6)

O10—Co1—N3	90.75 (16)	C3—C2—N1	109.5 (4)
O10—Co1—N1	96.21 (17)	C3—C2—C1	134.7 (5)
N3—Co1—N1	96.43 (12)	N1—C2—C1	115.7 (4)
O10—Co1—O9	171.87 (13)	N2—C3—C2	105.6 (4)
N3—Co1—O9	93.23 (14)	N2—C3—C4	124.2 (4)
N1—Co1—O9	90.39 (15)	C2—C3—C4	130.1 (5)
O10—Co1—O1	85.88 (15)	O4—C4—O3	123.8 (5)
N3—Co1—O1	173.42 (16)	O4—C4—C3	119.7 (5)
N1—Co1—O1	78.35 (15)	O3—C4—C3	116.6 (5)
O9—Co1—O1	90.83 (14)	N1—C5—N2	109.2 (4)
O10—Co1—O5	90.76 (16)	N1—C5—C6	125.2 (5)
N3—Co1—O5	78.52 (15)	N2—C5—C6	125.5 (4)
N1—Co1—O5	171.47 (16)	C5—C6—C7	117.7 (5)
O9—Co1—O5	83.09 (13)	C5—C6—H6A	107.9
O1—Co1—O5	107.14 (10)	C7—C6—H6A	107.9
C5—N1—C2	106.9 (4)	C5—C6—H6B	107.9
C5—N1—Co1	139.0 (4)	C7—C6—H6B	107.9
C2—N1—Co1	114.1 (3)	H6A—C6—H6B	107.2
C3—N2—C5	108.7 (4)	C8—C7—C6	115.2 (5)
C3—N2—H2A	125.6	C8—C7—H7A	108.5
C5—N2—H2A	125.6	C6—C7—H7A	108.5
C8—N3—C11	108.3 (4)	C8—C7—H7B	108.5
C8—N3—Co1	137.5 (4)	C6—C7—H7B	108.5
C11—N3—Co1	114.2 (3)	H7A—C7—H7B	107.5
C8—N4—C9	109.4 (4)	N3—C8—N4	108.2 (4)
C8—N4—H4A	125.3	N3—C8—C7	126.5 (5)
C9—N4—H4A	125.3	N4—C8—C7	125.0 (4)
C1—O1—Co1	114.4 (3)	C11—C9—N4	104.9 (4)
C4—O3—H3	109.4	C11—C9—C10	133.3 (5)
C12—O5—Co1	113.8 (3)	N4—C9—C10	121.6 (5)
C10—O7—H7	119.6	O8—C10—O7	122.7 (5)
Co1—O9—H1W	121.1	O8—C10—C9	122.4 (5)
Co1—O9—H2W	118.0	O7—C10—C9	115.0 (4)
H1W—O9—H2W	106.7	N3—C11—C9	109.2 (4)
Co1—O10—H3W	143.7	N3—C11—C12	116.8 (4)
Co1—O10—H4W	115.7	C9—C11—C12	134.0 (5)
H3W—O10—H4W	98.3	O6—C12—O5	125.3 (5)
O1—C1—O2	125.2 (5)	O6—C12—C11	118.2 (5)
O1—C1—C2	117.4 (4)	O5—C12—C11	116.5 (4)
O2—C1—C2	117.4 (5)

O10—Co1—N1—C5	−98.6 (6)	C2—C3—C4—O4	−176.2 (5)
N3—Co1—N1—C5	−7.2 (6)	N2—C3—C4—O3	−179.1 (4)
O9—Co1—N1—C5	86.1 (5)	C2—C3—C4—O3	5.5 (8)
O1—Co1—N1—C5	176.9 (6)	C2—N1—C5—N2	−1.4 (6)
O10—Co1—N1—C2	82.6 (3)	Co1—N1—C5—N2	179.8 (4)
N3—Co1—N1—C2	174.1 (3)	C2—N1—C5—C6	175.6 (5)
O9—Co1—N1—C2	−92.6 (3)	Co1—N1—C5—C6	−3.3 (9)
O1—Co1—N1—C2	−1.9 (3)	C3—N2—C5—N1	2.5 (6)
O10—Co1—N3—C8	85.1 (6)	C3—N2—C5—C6	−174.4 (5)
N1—Co1—N3—C8	−11.2 (6)	N1—C5—C6—C7	52.6 (8)
O9—Co1—N3—C8	−102.0 (5)	N2—C5—C6—C7	−131.0 (5)
O5—Co1—N3—C8	175.7 (6)	C5—C6—C7—C8	−85.6 (5)
O10—Co1—N3—C11	−92.9 (4)	C11—N3—C8—N4	−0.7 (6)
N1—Co1—N3—C11	170.8 (3)	Co1—N3—C8—N4	−178.7 (4)
O9—Co1—N3—C11	80.0 (3)	C11—N3—C8—C7	173.0 (5)
O5—Co1—N3—C11	−2.2 (3)	Co1—N3—C8—C7	−5.0 (9)
O10—Co1—O1—C1	−95.3 (4)	C9—N4—C8—N3	−0.1 (6)
N1—Co1—O1—C1	2.0 (4)	C9—N4—C8—C7	−173.9 (5)
O9—Co1—O1—C1	92.2 (4)	C6—C7—C8—N3	56.8 (8)
O5—Co1—O1—C1	175.2 (3)	C6—C7—C8—N4	−130.5 (5)
O10—Co1—O5—C12	95.0 (4)	C8—N4—C9—C11	0.9 (5)
N3—Co1—O5—C12	4.4 (4)	C8—N4—C9—C10	176.7 (5)
O9—Co1—O5—C12	−90.3 (4)	C11—C9—C10—O8	178.3 (5)
O1—Co1—O5—C12	−179.1 (3)	N4—C9—C10—O8	3.8 (8)
Co1—O1—C1—O2	−179.7 (4)	C11—C9—C10—O7	−3.0 (8)
Co1—O1—C1—C2	−1.7 (6)	N4—C9—C10—O7	−177.4 (4)
C5—N1—C2—C3	−0.2 (6)	C8—N3—C11—C9	1.2 (6)
Co1—N1—C2—C3	178.9 (3)	Co1—N3—C11—C9	179.8 (3)
C5—N1—C2—C1	−177.5 (4)	C8—N3—C11—C12	−178.4 (4)
Co1—N1—C2—C1	1.7 (5)	Co1—N3—C11—C12	0.2 (5)
O1—C1—C2—C3	−176.3 (6)	N4—C9—C11—N3	−1.3 (5)
O2—C1—C2—C3	1.9 (9)	C10—C9—C11—N3	−176.4 (5)
O1—C1—C2—N1	0.1 (7)	N4—C9—C11—C12	178.2 (5)
O2—C1—C2—N1	178.3 (5)	C10—C9—C11—C12	3.1 (10)
C5—N2—C3—C2	−2.5 (6)	Co1—O5—C12—O6	173.6 (4)
C5—N2—C3—C4	−178.9 (5)	Co1—O5—C12—C11	−5.6 (6)
N1—C2—C3—N2	1.7 (6)	N3—C11—C12—O6	−175.4 (5)
C1—C2—C3—N2	178.3 (5)	C9—C11—C12—O6	5.1 (8)
N1—C2—C3—C4	177.8 (5)	N3—C11—C12—O5	3.8 (7)
C1—C2—C3—C4	−5.7 (10)	C9—C11—C12—O5	−175.6 (5)
N2—C3—C4—O4	−0.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.85	1.65	2.461 (5)	157
O7—H7···O6	0.85	1.72	2.550 (5)	166
O10—H3W···O3ⁱ	0.85	2.18	2.799 (5)	129
N2—H2A···O6ⁱⁱ	0.86	2.16	2.904 (5)	145
N4—H4A···O5ⁱⁱⁱ	0.86	2.04	2.878 (5)	166
O9—H1W···O4^iv	0.85	1.89	2.730 (5)	170
O9—H2W···O7^v	0.85	2.06	2.834 (5)	150
O10—H4W···O8^vi	0.85	2.22	2.958 (5)	145

Symmetry codes: (i) x, y, z+1; (ii) −x+1/4, y+1/4, z−3/4; (iii) −x+1/4, y+1/4, z+1/4; (iv) x−1/4, −y+1/4, z+3/4; (v) x, y, z−1; (vi) x+1/4, −y+1/4, z−3/4.

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₈N₄O₈)(H₂O)₂]
M_r	431.19
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	24.683 (5), 27.885 (6), 8.7340 (17)
V (Å³)	6012 (2)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.18 × 0.14 × 0.09

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.811, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	7187, 2693, 2223
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.079, 1.01
No. of reflections	2693
No. of parameters	245
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.35
Absolute structure	Flack (1983), 1126 Friedel pairs
Absolute structure parameter	0.20 (2)

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O10	2.043 (4)	Co1—O9	2.118 (4)
Co1—N3	2.044 (4)	Co1—O1	2.153 (3)
Co1—N1	2.048 (4)	Co1—O5	2.168 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.85	1.65	2.461 (5)	157
O7—H7···O6	0.85	1.72	2.550 (5)	166
O10—H3W···O3ⁱ	0.85	2.18	2.799 (5)	129
N2—H2A···O6ⁱⁱ	0.86	2.16	2.904 (5)	145
N4—H4A···O5ⁱⁱⁱ	0.86	2.04	2.878 (5)	166
O9—H1W···O4^iv	0.85	1.89	2.730 (5)	170
O9—H2W···O7^v	0.85	2.06	2.834 (5)	150
O10—H4W···O8^vi	0.85	2.22	2.958 (5)	145

Symmetry codes: (i) x, y, z+1; (ii) −x+1/4, y+1/4, z−3/4; (iii) −x+1/4, y+1/4, z+1/4; (iv) x−1/4, −y+1/4, z+3/4; (v) x, y, z−1; (vi) x+1/4, −y+1/4, z−3/4.

References

Das, S., Saha, D., Bhaumik, C., Dutta, S. & Baitalik, S. (2010). Dalton Trans. pp. 4162–4169. CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-G., Guo, M.-Y., Xiong, G., Ding, F., Wang, L., Jiang, B., Zhu, M.-C., Gao, E.-J. & Verpoort, F. (2010). J. Coord. Chem. 63, 4188–4200. CrossRef CAS Google Scholar
Zhang, F.-W., Li, Z.-F., Ge, T.-Z., Yao, H.-C., Li, G., Lu, H.-J. & Zhu, Y.-Y. (2010). Inorg. Chem. 49, 3776–3788. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 67| Part 6| June 2011| Page m815

doi:10.1107/S1600536811019672

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­aqua­[5,5′-dicarb­­oxy-2,2′-(ethane-1,2-di­yl)bis­­(1H-imidazole-4-carboxyl­ato)]cobalt(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Diaqua[5,5′-dicarboxy-2,2′-(ethane-1,2-diyl)bis(1H-imidazole-4-carboxylato)]cobalt(II)