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

In the title complex, [Co(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Co(II) cation (site symmetry ) is six-coordinated by two 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate ligands and two water mol-ecules in a distorted octa-hedral environment. In the crystal structure, the complex mol-ecules and dimethyl-formamide solvent mol-ecules are linked by extensive O-H⋯O and N-H⋯O hydrogen bonding into sheets lying parallel to (21).

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 = 635.50

Triclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.120

S = 1.06

2393 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.52 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042054/jh2216Isup2.hkl

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

[Co(C8H9N2O4)2(H2O)2]·2C3H7NO	Z = 1
Mr = 635.50	F(000) = 333
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0593P)2 + 0.0702P] where P = (Fo2 + 2Fc2)/3
2393 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.52 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	0.5000	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*

	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)

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)

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···O6iv	0.86	1.84	2.685 (4)	166

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) ; (ii) ; (iii) .