Diaqua-[5,5'-dicarb-oxy-2,2'-(ethane-1,2-di-yl)bis-(1H-imidazole-4-carboxyl-ato)]cobalt(II).

In the title complex, [Co(C(12)H(8)N(4)O(8))(H(2)O)(2)], the Co(II) atom is coordinated by two N and two O atoms of the tetra-dentate 5,5'-dicarb-oxy-2,2'-(ethane-1,2-di-yl)bis-(1H-imidazole-4-carboxy-l-ate) anion. The slightly distorted octa-hedral coordination environment is completed by the O atoms of two water mol-ecules in axial positions. An intra-molecular O-H⋯O hydrogen bond between the carb-oxy and carboxyl-ate groups stabilizes the mol-ecular configuration. Adjacent mol-ecules are linked through O-H⋯O and N-H⋯O hydrogen bonds between the carb-oxy/carboxyl-ate groups, water mol-ecules 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 = 431.19

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.079

S = 1.01

2693 reflections

245 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983) ▶, 1126 Friedel pairs

Flack parameter: 0.20 (2)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C12H8N4O8)(H2O)2]	F(000) = 3504
Mr = 431.19	Dx = 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

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

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(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2693 reflections	Δρmax = 0.37 e Å−3
245 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 1126 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.20 (2)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O4iv	0.85	1.89	2.730 (5)	170
O9—H2W···O7v	0.85	2.06	2.834 (5)	150
O10—H4W···O8vi	0.85	2.22	2.958 (5)	145

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⋯O4iv	0.85	1.89	2.730 (5)	170
O9—H2W⋯O7v	0.85	2.06	2.834 (5)	150
O10—H4W⋯O8vi	0.85	2.22	2.958 (5)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .