Imidazolium trans-bis­(imino­diacetato-κ3O,N,O′)cobaltate(III)

Gao, X.-L.; Lu, L.-P.; Zhu, M.-L.

doi:10.1107/S1600536809014342

metal-organic compounds

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Volume 65| Part 5| May 2009| Page m561

doi:10.1107/S1600536809014342

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Imidazolium trans-bis(iminodiacetato-κ³O,N,O′)cobaltate(III)

Xiao-Li Gao,^a Li-Ping Lu ^a and Miao-Li Zhu ^a ^*

^aInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: miaoli@sxu.edu.cn

(Received 14 April 2009; accepted 17 April 2009; online 25 April 2009)

In the title compound, (C₃H₅N₂)[Co(C₄H₅NO₄)₂], the cation and anion are located on a twofold rotation axis and inversion center, respectively. Intermolecular 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 interactions.

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_r = 390.20
Orthorhombic, P c c a
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 1.08
1495 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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⋯O4^iv	0.93	2.36	3.117 (4)	138
C1—O2⋯Cg1^v	1.23 (1)	3.54 (1)	3.953 (2)	0 ?
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+2, z]$ ; (v) $[-x-1, y+1, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

In continuation of our study of weak C—H···O and C═O···π interactions in the building of three-dimensional structures (Gao et al., 2009), we present here the crystal structure of the title 1:1 adduct, (I).

In (I) (Fig. 1), the cation and anion are located on a two-fold rotation axis and inversion center, respectively. Strong N2—H···O2ⁱⁱ hydrogen bonds (Table 1) link imidazolium and trans-bis(iminodiacetato-N,O,O')cobalt(III) with the direction of (120) to form one-dimensional chains (Fig. 2) with graph-set notation C₂²(13). These chains further assemble to other trans-bis(iminodiacetato-N,O,O')cobalt(III) anions in two-dimensional structures on (001) plane via C5—H···O4^vi, C5—H···O4^viii and C3^viii—H···O2^iv (Table 1) hydrogen bonds, as shown in Fig. 2. Further, the layers assemble to a three-dimensional structure by strong N1—H···Oⁱ hydrogen bond and weak C1═O2···π(centroid of imidazolium ring) interaction (Table 1). Imidazolium has three donors, two N—H and one C—H, the latter forming a non-conventional bifurcated hydrogen bond between imidazolium C5—H and carboxylate groups O4H and O4F from trans-bis(iminodiacetato-N,O,O')cobalt(III). Interestingly, this type of hydrogen bond in imidazolium compounds was found in a search of the Cambridge Structural Database (CSD version 5.30; Allen, 2002). Among the 200 hits for imidazolium compounds, there are only seven compounds having the similar bifurcated hydrogen bonds (C—H from imidazolium), namely, imidazolium hydrogen maleate (Hsu & Schlemper, 1980), benzo-18-crown-6 imidazolium clathrate perchlorate (Rissanen & Pursiainen, 2000), bis(imidazolium) bis(oxalato-O,O')copper(II) (Chattopadhyay et al., 1995). Their distances of H···O are in the range of 2.10 to 2.49 Å. However, analysis in sum of three angles about H atom are all less than 360° in the seven compounds, which indicated that these weak hydrogen bonds are not of characters of bifurcated hydrogen bonds from H-bond classification (Jeffrey et al., 1985).

Related literature top

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 top

Chemicals were readily available from commercial sources and were used as received without further purification. To a 10 ml of solution containing imidazole (0.14 g, 2 mmol) in a flask with constant stirring, added dropwise Co(CH₃COO)₂.3H₂O (0.23 g, 1 mmol) in 5 ml of aqueous solution and 5 ml aqueous solution containing iminodiacetic acid (0.27 g, 2 mmol) was added dropwise. The mixture was stirred for 3 h, and then filtered. The dark-red filtrate was left to stand at room temperature, and after three weeks, dark-red crystals of the title compound were formed.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level and atomic numbering [symmetry codes: (i) -x, -y, -z; (ii) 1/2 - x, -1 - y, z].

Fig. 2. A portion of the crystal packing showing hydrogen-bonding patterns with graph-set notations R₃²(9), R₃²(9) and R₂²(12), respectively. Dotted lines denote hydrogen bonds. H atoms non-involved in hydrogen-bonding omitted for clarity. [Symmetry codes: (i) 1/2 - x, 1 - y, z; (ii) -x, -1 + y, 1/2 - z; (iii) x, 1 - y, 1/2 + z; (iv) 1/2 + x, 2 - y, 1/2 - z; (v) 1/2 - x, y, 1/2 + z; (vi) x, -1 + y, z; (vii) -x, 1 - y, -z; (viii) 1/2 - x, 2 - y, z; (ix) 1/2 + x, y, -z.]

Imidazolium trans-bis(iminodiacetato-κ³O,N,O')cobaltate(III) top

Crystal data top

(C₃H₅N₂)[Co(C₄H₅NO₄)₂]	F(000) = 800
M_r = 390.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0405P)² + 0.6086P] where P = (F_o² + 2F_c²)/3
1495 reflections	(Δ/σ)_max < 0.001
111 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

(C₃H₅N₂)[Co(C₄H₅NO₄)₂]	V = 1510.2 (5) Å³
M_r = 390.20	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 16.889 (3) Å	µ = 1.19 mm⁻¹
b = 5.2906 (10) Å	T = 298 K
c = 16.901 (3) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1495 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1299 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.797	R_int = 0.025
6218 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
1495 reflections	Δρ_min = −0.27 e Å⁻³
111 parameters

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	0.0000	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.86	1.95	2.775 (3)	162
C3—H3B···O2^v	0.97	2.43	3.338 (3)	156
C5—H5···O4ⁱⁱⁱ	0.93	2.36	3.117 (4)	138
C5—H5···O4^vi	0.93	2.36	3.117 (4)	138
C1—O2···Cg1^vii	1.23 (1)	3.54 (1)	3.953 (2)

Symmetry codes: (iii) x, y−1, z; (iv) −x, y−1, −z+1/2; (v) −x, y, −z+1/2; (vi) −x+1/2, −y+2, z; (vii) −x−1, y+1, −z+1/2.

Experimental details

Crystal data
Chemical formula	(C₃H₅N₂)[Co(C₄H₅NO₄)₂]
M_r	390.20
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	298
a, b, c (Å)	16.889 (3), 5.2906 (10), 16.901 (3)
V (Å³)	1510.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.783, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	6218, 1495, 1299
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.079, 1.08
No. of reflections	1495
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.79	2.12	2.880 (2)	161.1
N2—H2···O2ⁱⁱ	0.86	1.95	2.775 (3)	161.8
C3—H3B···O2ⁱⁱⁱ	0.97	2.43	3.338 (3)	155.9
C5—H5···O4ⁱ	0.93	2.36	3.117 (4)	138.1
C5—H5···O4^iv	0.93	2.36	3.117 (4)	138.1
C1—O2···Cg1^v	1.230 (2)	3.54 (1)	3.953 (2)	.

Symmetry codes: (i) x, y−1, z; (ii) −x, y−1, −z+1/2; (iii) −x, y, −z+1/2; (iv) −x+1/2, −y+2, z; (v) −x−1, y+1, −z+1/2.

Acknowledgements

The authors acknowledge the National Natural Science Foundation of China (grant No. 20471033), the Natural Science Foundation of Shanxi Province (grant No. 20051013) and the Overseas Returned Scholar Foundation of Shanxi Province for financial support in 2008.

References

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