Diaqua-bis(5-carb-oxy-2-methyl-1H-imidazole-4-carboxyl-ato-κN,O)cobalt(II) dimethyl-formamide disolvate.

In the title compound, [Co(C(6)H(5)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Co(II) ion lies on an inversion center and adopts a slightly distorted CoN(2)O(4) octa-hedral geometry binding two bidentate chelating 5-carb-oxy-2-methyl-1H-imidazole-4-carboxyl-ate (H(2)MIDA(-)) monoanionic ligands and two axial aqua ligands. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link neighboring mol-ecules, generating a two-dimensional framework containing eight-membered H(4)O(4) rings. In addition, the dimethyl-formamide solvent mol-ecules are hydrogen bonded to the two-dimensional framework via the NH groups of the H(2)MIDA(-) ligands.

Related literature

For background to N-heterocyclic carboxylic acids as ligands in coordination complexes, see: Gao et al. (2004 ▶); Shimizu et al. (2004 ▶); Zhang et al. (2006 ▶). For related structures, see: Liu et al. (2007 ▶); Nie et al. (2007 ▶); Zeng et al. (2008 ▶).

Experimental

Crystal data

[Co(C6H5N2O4)2(H2O)2]·2C3H7NO

M = 579.39

Triclinic,

a = 7.1979 (11) Å

b = 9.2180 (15) Å

c = 10.8659 (17) Å

α = 65.173 (2)°

β = 83.459 (2)°

γ = 68.254 (2)°

V = 607.02 (17) Å3

Z = 1

Mo Kα radiation

μ = 0.78 mm−1

T = 123 K

0.20 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.859, T max = 0.899

4588 measured reflections

2335 independent reflections

2176 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.06

2335 reflections

172 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012902/sj2611sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012902/sj2611Isup2.hkl

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

[Co(C6H5N2O4)2(H2O)2]·2C3H7NO	Z = 1
Mr = 579.39	F(000) = 301
Triclinic, P1	Dx = 1.585 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1979 (11) Å	Cell parameters from 3423 reflections
b = 9.2180 (15) Å	θ = 2.6–27.8°
c = 10.8659 (17) Å	µ = 0.78 mm−1
α = 65.173 (2)°	T = 123 K
β = 83.459 (2)°	Block, pink
γ = 68.254 (2)°	0.20 × 0.15 × 0.14 mm
V = 607.02 (17) Å3

Bruker SMART APEX area-detector diffractometer	2335 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.859, Tmax = 0.899	k = −11→11
4588 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2477P] where P = (Fo2 + 2Fc2)/3
2335 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.65 e Å−3
1 restraint	Δρmin = −0.49 e Å−3

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	0.0000	1.0000	0.5000	0.01688 (15)
O4	0.1583 (2)	0.97632 (18)	0.32480 (14)	0.0200 (3)
O1W	0.2666 (2)	0.96647 (18)	0.58550 (14)	0.0214 (3)
H1W2	0.3716	0.9017	0.5643	0.032*
H1W1	0.2857	1.0585	0.5685	0.032*
O3	0.3261 (2)	0.78687 (18)	0.23787 (14)	0.0220 (3)
O2	0.4205 (2)	0.47831 (19)	0.30617 (15)	0.0233 (3)
H2A	0.391 (4)	0.5850 (15)	0.288 (3)	0.035*
O1	0.3990 (2)	0.24920 (18)	0.48355 (16)	0.0241 (3)
O5	0.8297 (3)	−0.1528 (2)	0.20333 (17)	0.0343 (4)
N1	0.0922 (2)	0.7355 (2)	0.55599 (16)	0.0171 (4)
N2	0.1798 (2)	0.4572 (2)	0.62169 (17)	0.0181 (4)
H2	0.1932	0.3523	0.6713	0.022*
N3	0.6518 (3)	0.1293 (2)	0.08740 (18)	0.0296 (4)
C6	0.2260 (3)	0.8282 (3)	0.33158 (19)	0.0179 (4)
C5	0.1936 (3)	0.6909 (2)	0.4550 (2)	0.0174 (4)
C4	0.2493 (3)	0.5176 (2)	0.4945 (2)	0.0173 (4)
C3	0.3636 (3)	0.4049 (3)	0.4250 (2)	0.0194 (4)
C2	0.0862 (3)	0.5915 (2)	0.6556 (2)	0.0181 (4)
C1	−0.0105 (3)	0.5776 (3)	0.7860 (2)	0.0247 (5)
H1A	0.0882	0.5048	0.8597	0.037*
H1B	−0.1121	0.5297	0.7961	0.037*
H1C	−0.0703	0.6892	0.7866	0.037*
C7	0.4556 (5)	0.2630 (4)	0.0431 (3)	0.0559 (8)
H7A	0.3539	0.2136	0.0754	0.084*
H7B	0.4450	0.3176	−0.0543	0.084*
H7C	0.4384	0.3461	0.0788	0.084*
C8	0.8227 (5)	0.1820 (4)	0.0586 (3)	0.0480 (7)
H8A	0.8213	0.2500	−0.0369	0.072*
H8B	0.9434	0.0827	0.0854	0.072*
H8C	0.8175	0.2484	0.1081	0.072*
C9	0.6694 (4)	−0.0318 (3)	0.1589 (2)	0.0309 (5)
H9	0.5524	−0.0563	0.1773	0.037*

	U11	U22	U33	U12	U13	U23
Co1	0.0189 (2)	0.0105 (2)	0.0213 (2)	−0.00437 (16)	0.00295 (15)	−0.00778 (16)
O4	0.0233 (8)	0.0124 (7)	0.0237 (7)	−0.0055 (6)	0.0032 (5)	−0.0082 (6)
O1W	0.0208 (7)	0.0153 (7)	0.0301 (8)	−0.0054 (6)	0.0030 (6)	−0.0126 (6)
O3	0.0273 (8)	0.0180 (7)	0.0221 (7)	−0.0078 (6)	0.0063 (6)	−0.0110 (6)
O2	0.0279 (8)	0.0168 (7)	0.0297 (8)	−0.0076 (6)	0.0065 (6)	−0.0151 (7)
O1	0.0227 (8)	0.0146 (8)	0.0375 (8)	−0.0059 (6)	0.0044 (6)	−0.0144 (6)
O5	0.0393 (10)	0.0179 (8)	0.0395 (9)	−0.0122 (7)	0.0049 (7)	−0.0051 (7)
N1	0.0172 (9)	0.0136 (8)	0.0209 (8)	−0.0043 (7)	0.0028 (6)	−0.0087 (7)
N2	0.0200 (8)	0.0098 (8)	0.0240 (8)	−0.0056 (7)	0.0010 (6)	−0.0063 (7)
N3	0.0419 (11)	0.0206 (9)	0.0236 (9)	−0.0106 (8)	0.0034 (8)	−0.0076 (7)
C6	0.0152 (9)	0.0167 (10)	0.0228 (10)	−0.0060 (8)	0.0005 (7)	−0.0086 (8)
C5	0.0161 (9)	0.0155 (10)	0.0218 (9)	−0.0049 (8)	0.0017 (7)	−0.0094 (8)
C4	0.0163 (9)	0.0147 (10)	0.0227 (9)	−0.0057 (8)	0.0003 (7)	−0.0091 (8)
C3	0.0152 (9)	0.0160 (10)	0.0303 (10)	−0.0045 (8)	−0.0002 (8)	−0.0130 (9)
C2	0.0172 (10)	0.0128 (10)	0.0243 (10)	−0.0054 (8)	−0.0001 (7)	−0.0074 (8)
C1	0.0299 (11)	0.0205 (11)	0.0245 (10)	−0.0105 (9)	0.0045 (8)	−0.0096 (9)
C7	0.0534 (15)	0.0351 (15)	0.0471 (15)	0.0034 (13)	0.0177 (13)	−0.0078 (12)
C8	0.0650 (16)	0.0353 (14)	0.0426 (14)	−0.0331 (13)	−0.0161 (13)	0.0028 (12)
C9	0.0366 (13)	0.0268 (12)	0.0336 (12)	−0.0164 (11)	0.0115 (10)	−0.0143 (10)

Co1—O1Wi	2.0895 (14)	N2—H2	0.8600
Co1—O1W	2.0895 (14)	N3—C9	1.319 (3)
Co1—N1i	2.0982 (16)	N3—C8	1.440 (3)
Co1—N1	2.0982 (16)	N3—C7	1.453 (3)
Co1—O4	2.1543 (14)	C6—C5	1.476 (3)
Co1—O4i	2.1543 (14)	C5—C4	1.374 (3)
O4—C6	1.240 (2)	C4—C3	1.486 (3)
O1W—H1W2	0.8500	C2—C1	1.482 (3)
O1W—H1W1	0.8500	C1—H1A	0.9600
O3—C6	1.287 (2)	C1—H1B	0.9600
O2—C3	1.282 (3)	C1—H1C	0.9600
O2—H2A	0.863 (10)	C7—H7A	0.9600
O1—C3	1.237 (2)	C7—H7B	0.9600
O5—C9	1.237 (3)	C7—H7C	0.9600
N1—C2	1.327 (3)	C8—H8A	0.9600
N1—C5	1.371 (2)	C8—H8B	0.9600
N2—C2	1.353 (3)	C8—H8C	0.9600
N2—C4	1.368 (3)	C9—H9	0.9300
O1Wi—Co1—O1W	180.00 (8)	N1—C5—C6	117.57 (17)
O1Wi—Co1—N1i	90.58 (6)	C4—C5—C6	132.78 (18)
O1W—Co1—N1i	89.42 (6)	N2—C4—C5	105.63 (17)
O1Wi—Co1—N1	89.42 (6)	N2—C4—C3	123.03 (18)
O1W—Co1—N1	90.58 (6)	C5—C4—C3	131.33 (19)
N1i—Co1—N1	180.0	O1—C3—O2	124.18 (18)
O1Wi—Co1—O4	90.84 (5)	O1—C3—C4	119.29 (19)
O1W—Co1—O4	89.16 (5)	O2—C3—C4	116.53 (17)
N1i—Co1—O4	101.17 (6)	N1—C2—N2	110.61 (17)
N1—Co1—O4	78.83 (6)	N1—C2—C1	125.33 (18)
O1Wi—Co1—O4i	89.16 (5)	N2—C2—C1	124.06 (18)
O1W—Co1—O4i	90.84 (5)	C2—C1—H1A	109.5
N1i—Co1—O4i	78.83 (6)	C2—C1—H1B	109.5
N1—Co1—O4i	101.17 (6)	H1A—C1—H1B	109.5
O4—Co1—O4i	180.0	C2—C1—H1C	109.5
C6—O4—Co1	113.98 (12)	H1A—C1—H1C	109.5
Co1—O1W—H1W2	114.5	H1B—C1—H1C	109.5
Co1—O1W—H1W1	114.9	N3—C7—H7A	109.5
H1W2—O1W—H1W1	106.7	N3—C7—H7B	109.5
C3—O2—H2A	108.9 (18)	H7A—C7—H7B	109.5
C2—N1—C5	106.13 (15)	N3—C7—H7C	109.5
C2—N1—Co1	142.57 (14)	H7A—C7—H7C	109.5
C5—N1—Co1	111.29 (12)	H7B—C7—H7C	109.5
C2—N2—C4	107.99 (16)	N3—C8—H8A	109.5
C2—N2—H2	126.0	N3—C8—H8B	109.5
C4—N2—H2	126.0	H8A—C8—H8B	109.5
C9—N3—C8	121.9 (2)	N3—C8—H8C	109.5
C9—N3—C7	120.7 (2)	H8A—C8—H8C	109.5
C8—N3—C7	117.2 (2)	H8B—C8—H8C	109.5
O4—C6—O3	123.66 (18)	O5—C9—N3	124.9 (2)
O4—C6—C5	118.29 (17)	O5—C9—H9	117.5
O3—C6—C5	118.04 (17)	N3—C9—H9	117.5
N1—C5—C4	109.64 (17)
O1Wi—Co1—O4—C6	−87.79 (14)	O4—C6—C5—C4	−179.21 (19)
O1W—Co1—O4—C6	92.21 (14)	O3—C6—C5—C4	−0.4 (3)
N1i—Co1—O4—C6	−178.54 (13)	C2—N2—C4—C5	0.0 (2)
N1—Co1—O4—C6	1.46 (13)	C2—N2—C4—C3	178.91 (17)
O1Wi—Co1—N1—C2	−89.6 (2)	N1—C5—C4—N2	0.0 (2)
O1W—Co1—N1—C2	90.4 (2)	C6—C5—C4—N2	178.5 (2)
O4—Co1—N1—C2	179.4 (2)	N1—C5—C4—C3	−178.80 (19)
O4i—Co1—N1—C2	−0.6 (2)	C6—C5—C4—C3	−0.3 (4)
O1Wi—Co1—N1—C5	89.19 (13)	N2—C4—C3—O1	−0.1 (3)
O1W—Co1—N1—C5	−90.81 (13)	C5—C4—C3—O1	178.5 (2)
O4—Co1—N1—C5	−1.78 (12)	N2—C4—C3—O2	−179.72 (17)
O4i—Co1—N1—C5	178.22 (12)	C5—C4—C3—O2	−1.1 (3)
Co1—O4—C6—O3	−179.57 (15)	C5—N1—C2—N2	0.0 (2)
Co1—O4—C6—C5	−0.8 (2)	Co1—N1—C2—N2	178.85 (15)
C2—N1—C5—C4	0.0 (2)	C5—N1—C2—C1	−179.54 (18)
Co1—N1—C5—C4	−179.25 (13)	Co1—N1—C2—C1	−0.7 (4)
C2—N1—C5—C6	−178.74 (17)	C4—N2—C2—N1	0.0 (2)
Co1—N1—C5—C6	2.0 (2)	C4—N2—C2—C1	179.55 (18)
O4—C6—C5—N1	−0.8 (3)	C8—N3—C9—O5	−2.9 (4)
O3—C6—C5—N1	178.00 (16)	C7—N3—C9—O5	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ii	0.86	1.83	2.670 (2)	166
O2—H2A···O3	0.86 (1)	1.59 (1)	2.452 (2)	173 (3)
O1W—H1W2···O1iii	0.85	1.91	2.7579 (19)	178
O1W—H1W1···O1iv	0.85	2.03	2.847 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5i	0.86	1.83	2.670 (2)	166
O2—H2A⋯O3	0.863 (10)	1.593 (11)	2.452 (2)	173 (3)
O1W—H1W2⋯O1ii	0.85	1.91	2.7579 (19)	178
O1W—H1W1⋯O1iii	0.85	2.03	2.847 (2)	160

Symmetry codes: (i) ; (ii) ; (iii) .