Imidazolium trans-bis-(imino-diacetato-κO,N,O')cobaltate(III).

In the title compound, (C(3)H(5)N(2))[Co(C(4)H(5)NO(4))(2)], the cation and anion are located on a twofold rotation axis and inversion center, respectively. Inter-molecular N-H⋯O hydrogen bonds link the cations and anions into layers parallel to the ab plane. The crystal packing also exhibits weak C-H⋯O hydrogen bonds, including bifurcated hydrogen bonds, and C=O⋯π inter-actions.

Related literature

For hydrogen bonds in related compounds containing imidazolium, see: Allen (2002 ▶); Chattopadhyay et al. (1995 ▶); Gao et al. (2009 ▶); Hsu & Schlemper (1980 ▶); Rissanen & Pursiainen (2000 ▶). Bifurcated hydrogen bonds were discussed by Jeffrey et al. (1985 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

(C3H5N2)[Co(C4H5NO4)2]

M = 390.20

Orthorhombic,

a = 16.889 (3) Å

b = 5.2906 (10) Å

c = 16.901 (3) Å

V = 1510.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.19 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.783, T max = 0.797

6218 measured reflections

1495 independent reflections

1299 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.08

1495 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014342/cv2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014342/cv2551Isup2.hkl

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

(C3H5N2)[Co(C4H5NO4)2]	F(000) = 800
Mr = 390.20	Dx = 1.716 Mg m−3
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 2958 reflections
a = 16.889 (3) Å	θ = 2.4–27.0°
b = 5.2906 (10) Å	µ = 1.19 mm−1
c = 16.901 (3) Å	T = 298 K
V = 1510.2 (5) Å3	Block, red
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	1495 independent reflections
Radiation source: fine-focus sealed tube	1299 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −19→20
Tmin = 0.783, Tmax = 0.797	k = −6→4
6218 measured reflections	l = −18→20

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.6086P] where P = (Fo2 + 2Fc2)/3
1495 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.27 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	0.0000	0.02108 (14)
O1	−0.06498 (8)	1.0888 (2)	0.08656 (8)	0.0305 (3)
O2	−0.10143 (10)	0.9556 (3)	0.20572 (10)	0.0502 (5)
O3	0.07296 (7)	1.2495 (2)	0.03073 (9)	0.0306 (3)
O4	0.17666 (11)	1.3151 (3)	0.10704 (14)	0.0775 (7)
N1	0.05329 (8)	0.7739 (3)	0.07205 (9)	0.0240 (3)
H1	0.0644	0.6440	0.0521	0.029*
C1	−0.06105 (12)	0.9354 (4)	0.14545 (12)	0.0319 (4)
C2	−0.00355 (11)	0.7182 (4)	0.13637 (12)	0.0315 (5)
H2A	0.0249	0.6926	0.1856	0.038*
H2B	−0.0324	0.5644	0.1242	0.038*
C3	0.12727 (11)	0.8972 (4)	0.09931 (13)	0.0327 (4)
H3A	0.1724	0.8161	0.0744	0.039*
H3B	0.1324	0.8764	0.1561	0.039*
C4	0.12754 (12)	1.1751 (4)	0.07933 (13)	0.0369 (5)
N2	0.20741 (11)	0.3528 (4)	0.31139 (13)	0.0526 (5)
H2	0.1749	0.2389	0.2952	0.063*
C5	0.2500	0.5000	0.2661 (2)	0.0461 (9)
H5	0.2500	0.5000	0.2110	0.055*
C6	0.22287 (19)	0.4090 (8)	0.38741 (18)	0.0811 (11)
H6	0.1999	0.3346	0.4317	0.097*

	U11	U22	U33	U12	U13	U23
Co1	0.0249 (2)	0.0181 (2)	0.0202 (2)	0.00274 (13)	−0.00159 (13)	−0.00175 (12)
O1	0.0359 (7)	0.0297 (7)	0.0259 (7)	0.0101 (6)	0.0047 (6)	−0.0001 (6)
O2	0.0550 (10)	0.0629 (11)	0.0325 (9)	0.0263 (8)	0.0165 (8)	0.0112 (8)
O3	0.0323 (7)	0.0210 (6)	0.0385 (8)	−0.0005 (5)	−0.0086 (6)	−0.0013 (6)
O4	0.0655 (12)	0.0340 (9)	0.1330 (19)	−0.0079 (9)	−0.0602 (12)	−0.0013 (10)
N1	0.0288 (8)	0.0187 (7)	0.0246 (8)	0.0051 (6)	−0.0019 (6)	−0.0030 (6)
C1	0.0334 (10)	0.0351 (10)	0.0271 (11)	0.0056 (9)	0.0021 (9)	0.0002 (8)
C2	0.0376 (11)	0.0297 (10)	0.0273 (11)	0.0068 (8)	0.0025 (8)	0.0064 (8)
C3	0.0301 (10)	0.0306 (10)	0.0374 (11)	0.0032 (8)	−0.0084 (9)	−0.0001 (9)
C4	0.0345 (10)	0.0269 (10)	0.0492 (13)	0.0013 (8)	−0.0115 (9)	−0.0061 (9)
N2	0.0418 (11)	0.0547 (13)	0.0613 (14)	−0.0206 (10)	−0.0043 (10)	−0.0035 (10)
C5	0.0403 (19)	0.057 (2)	0.041 (2)	−0.0004 (15)	0.000	0.000
C6	0.074 (2)	0.122 (3)	0.0467 (18)	−0.048 (2)	0.0007 (15)	0.0132 (18)

Co1—O3i	1.8790 (12)	C1—C2	1.512 (3)
Co1—O3	1.8790 (12)	C2—H2A	0.9700
Co1—O1	1.8882 (13)	C2—H2B	0.9700
Co1—O1i	1.8882 (13)	C3—C4	1.508 (3)
Co1—N1i	1.9299 (14)	C3—H3A	0.9700
Co1—N1	1.9299 (14)	C3—H3B	0.9700
O1—C1	1.286 (2)	N2—C5	1.308 (3)
O2—C1	1.230 (2)	N2—C6	1.344 (4)
O3—C4	1.296 (2)	N2—H2	0.8599
O4—C4	1.207 (3)	C5—N2ii	1.308 (3)
N1—C2	1.480 (2)	C5—H5	0.9300
N1—C3	1.483 (2)	C6—C6ii	1.329 (6)
N1—H1	0.7879	C6—H6	0.9300
O3i—Co1—O3	180.00 (9)	O1—C1—C2	115.72 (17)
O3i—Co1—O1	90.44 (6)	N1—C2—C1	109.88 (16)
O3—Co1—O1	89.56 (6)	N1—C2—H2A	109.7
O3i—Co1—O1i	89.56 (6)	C1—C2—H2A	109.7
O3—Co1—O1i	90.44 (6)	N1—C2—H2B	109.7
O1—Co1—O1i	180.0	C1—C2—H2B	109.7
O3i—Co1—N1i	87.43 (6)	H2A—C2—H2B	108.2
O3—Co1—N1i	92.57 (6)	N1—C3—C4	111.22 (15)
O1—Co1—N1i	93.65 (6)	N1—C3—H3A	109.4
O1i—Co1—N1i	86.35 (6)	C4—C3—H3A	109.4
O3i—Co1—N1	92.57 (6)	N1—C3—H3B	109.4
O3—Co1—N1	87.43 (6)	C4—C3—H3B	109.4
O1—Co1—N1	86.35 (6)	H3A—C3—H3B	108.0
O1i—Co1—N1	93.65 (6)	O4—C4—O3	123.3 (2)
N1i—Co1—N1	180.00 (7)	O4—C4—C3	120.91 (19)
C1—O1—Co1	114.38 (12)	O3—C4—C3	115.83 (16)
C4—O3—Co1	115.36 (12)	C5—N2—C6	108.8 (2)
C2—N1—C3	113.95 (15)	C5—N2—H2	125.6
C2—N1—Co1	106.52 (11)	C6—N2—H2	125.6
C3—N1—Co1	108.42 (11)	N2ii—C5—N2	108.3 (3)
C2—N1—H1	107.2	N2ii—C5—H5	125.9
C3—N1—H1	108.4	N2—C5—H5	125.9
Co1—N1—H1	112.5	C6ii—C6—N2	107.09 (15)
O2—C1—O1	123.87 (19)	C6ii—C6—H6	126.5
O2—C1—C2	120.40 (18)	N2—C6—H6	126.5
O3i—Co1—O1—C1	77.41 (15)	O1i—Co1—N1—C3	80.29 (12)
O3—Co1—O1—C1	−102.59 (15)	Co1—O1—C1—O2	−176.80 (17)
N1i—Co1—O1—C1	164.87 (14)	Co1—O1—C1—C2	2.0 (2)
N1—Co1—O1—C1	−15.13 (14)	C3—N1—C2—C1	92.47 (19)
O1—Co1—O3—C4	90.08 (15)	Co1—N1—C2—C1	−27.03 (19)
O1i—Co1—O3—C4	−89.92 (15)	O2—C1—C2—N1	−163.64 (19)
N1i—Co1—O3—C4	−176.29 (15)	O1—C1—C2—N1	17.5 (3)
N1—Co1—O3—C4	3.71 (15)	C2—N1—C3—C4	−104.50 (19)
O3i—Co1—N1—C2	−66.96 (12)	Co1—N1—C3—C4	13.92 (19)
O3—Co1—N1—C2	113.04 (12)	Co1—O3—C4—O4	−176.8 (2)
O1—Co1—N1—C2	23.32 (12)	Co1—O3—C4—C3	3.9 (2)
O1i—Co1—N1—C2	−156.68 (12)	N1—C3—C4—O4	168.6 (2)
O3i—Co1—N1—C3	170.01 (12)	N1—C3—C4—O3	−12.2 (3)
O3—Co1—N1—C3	−9.99 (12)	C6—N2—C5—N2ii	0.4 (2)
O1—Co1—N1—C3	−99.71 (12)	C5—N2—C6—C6ii	−1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3iii	0.79	2.12	2.880 (2)	161
N2—H2···O2iv	0.86	1.95	2.775 (3)	162
C3—H3B···O2v	0.97	2.43	3.338 (3)	156
C5—H5···O4iii	0.93	2.36	3.117 (4)	138
C5—H5···O4vi	0.93	2.36	3.117 (4)	138
C1—O2···Cg1vii	1.230 (2)	3.54 (1)	3.953 (2)	.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the imidazolium ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.79	2.12	2.880 (2)	161
N2—H2⋯O2ii	0.86	1.95	2.775 (3)	162
C3—H3B⋯O2iii	0.97	2.43	3.338 (3)	156
C5—H5⋯O4i	0.93	2.36	3.117 (4)	138
C5—H5⋯O4iv	0.93	2.36	3.117 (4)	138
C1—O2⋯Cg1v	1.23 (1)	3.54 (1)	3.953 (2)	0 ?

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