Bis[N,N-bis­(2-hy­droxy­eth­yl)glycinato]cobalt(II)

Zhao, J.-P.; Liu, F.-C.

doi:10.1107/S1600536810023810

metal-organic compounds

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Volume 66| Part 7| July 2010| Page m848

doi:10.1107/S1600536810023810

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Bis[N,N-bis(2-hydroxyethyl)glycinato]cobalt(II)

Jiong-Peng Zhao ^a and Fu-Chen Liu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300191, People's Republic of China
^*Correspondence e-mail: fuchenliutj@yahoo.com

(Received 19 May 2010; accepted 19 June 2010; online 26 June 2010)

The asymmetric unit of the title compound, [Co(C₆H₁₂NO₄)₂], contains one half-molecule with the Co^II ion situated on an inversion center. Intermolecular O—H⋯O hydrogen bonds generate a three-dimensional hydrogen-bonding network, which consolidates the crystal packing.

Related literature

For related structures, see: Ammar et al. (2001 ); Chuklanova et al. (1981 ); Thakuria & Das (2007 ).

Experimental

Crystal data

[Co(C₆H₁₂NO₄)₂]
M_r = 383.26
Monoclinic, P 2₁ /c
a = 9.932 (2) Å
b = 11.388 (2) Å
c = 7.4477 (15) Å
β = 110.12 (3)°
V = 791.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.736, T_max = 1.000
8129 measured reflections
1819 independent reflections
1357 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.159
S = 1.00
1819 reflections
106 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H12⋯O3ⁱ	0.85	1.79	2.632 (4)	171
O1—H11⋯O3ⁱⁱ	0.85	1.89	2.744 (4)	178
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SCXmini Benchtop Crystallography System Software (Rigaku, 2006 ); cell refinement: PROCESS-AUTO (Rigaku, 1998 ); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023810/cv2723sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023810/cv2723Isup2.hkl

checkCIF report

Comment top

As a contribution to a structural study of ML₂ complexes, where L = N,N-bis(2-hydroxyethyl)glycinato ligand, and M = Cu (Ammar et al., 2001; Thakuria & Das, 2007) and Ni (Chuklanova et al., 1981), herewith we report the crystal structure of the title compound CoL₂ (I).

In (I) (Fig. 1), the Co(II) ions are located on the inversion centers and are coordinated by two L ligands forming an octahedral enviromental geometry with four oxygen and two nitrogen atoms. The bond lengths are: Co1—N1 = 2.172 (3) Å, Co1—O2 = 2.088 (3) Å and Co1—O4 = 2.046 (2) Å. Though ML₂ complexes (M = Co, Ni, Cu) have similar structures, there are some differences. The Co and Ni centers are in a regular octahedron coordinated geometry, while the Cu center has an elongated octahedral coordination with two hydroxy atoms in axial positions.

Intermolecular O—H···O hydrogen bonds (Table 1) generate three-dimensional hydrogen-bonding network, which consolidate the crystal packing (Fig. 2).

Related literature top

For related structures, see: Ammar et al. (2001); Chuklanova et al. (1981); Thakuria & Das (2007).

Experimental top

A mixture of Co(II) nitrate (1.0mmol), Dy(III)nitrate (0.5mmol) and N,N-bis(2-hydroxyethyl)glycine, (1 mmol), in 10 ml solvent wITH DMF:MeOH = 1:1 was sealed in a Teflon-lined stainless-steel Parr bomb that was heated at 413 K for 48 h. Red crystals of the title complex were collected after the bomb was allowed to cool to room temperature.Yield 20% based on metal salt.

Computing details top

Data collection: SCXmini Benchtop Crystallography System Software (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. H atom have been omitted for clarity. Symmetry code: (A) -x+1, -y-1, -z+1.
	Fig. 2. A portion of the crystal packing viewed down the c axis. Dashed lines denote O—H···O hydrogen bonds.

Bis[N,N-bis(2-hydroxyethyl)glycinato]cobalt(II) top

Crystal data top

[Co(C₆H₁₂NO₄)₂]	F(000) = 402
M_r = 383.26	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.932 (2) Å	Cell parameters from 7077 reflections
b = 11.388 (2) Å	θ = 3.4–27.6°
c = 7.4477 (15) Å	µ = 1.13 mm⁻¹
β = 110.12 (3)°	T = 293 K
V = 791.0 (3) Å³	Block, red
Z = 2	0.2 × 0.18 × 0.18 mm

Data collection top

Rigaku SCXmini diffractometer	1819 independent reflections
Radiation source: fine-focus sealed tube	1357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.736, T_max = 1.000	k = −14→14
8129 measured reflections	l = −9→9

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
1819 reflections	(Δ/σ)_max < 0.001
106 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Co(C₆H₁₂NO₄)₂]	V = 791.0 (3) Å³
M_r = 383.26	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.932 (2) Å	µ = 1.13 mm⁻¹
b = 11.388 (2) Å	T = 293 K
c = 7.4477 (15) Å	0.2 × 0.18 × 0.18 mm
β = 110.12 (3)°

Data collection top

Rigaku SCXmini diffractometer	1819 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1357 reflections with I > 2σ(I)
T_min = 0.736, T_max = 1.000	R_int = 0.072
8129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.00	Δρ_max = 0.48 e Å⁻³
1819 reflections	Δρ_min = −0.36 e Å⁻³
106 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.5000	0.5000	0.5000	0.0244 (3)
O1	0.0043 (3)	0.3365 (3)	0.0259 (4)	0.0552 (9)
H11	−0.0846	0.3211	−0.0073	0.066*
O2	0.5173 (3)	0.4447 (3)	0.7743 (4)	0.0347 (7)
H12	0.5746	0.3883	0.8218	0.042*
O3	0.2823 (3)	0.7874 (2)	0.5700 (4)	0.0449 (8)
O4	0.4555 (3)	0.6656 (2)	0.5703 (4)	0.0333 (6)
N1	0.2727 (3)	0.4762 (2)	0.4479 (5)	0.0270 (7)
C1	0.0483 (4)	0.3862 (4)	0.2103 (6)	0.0431 (10)
H1A	0.0377	0.3299	0.3022	0.052*
H1B	−0.0090	0.4550	0.2118	0.052*
C2	0.2040 (4)	0.4198 (3)	0.2589 (5)	0.0329 (9)
H2A	0.2579	0.3496	0.2538	0.040*
H2B	0.2115	0.4730	0.1610	0.040*
C3	0.2708 (4)	0.3967 (4)	0.6042 (6)	0.0363 (9)
H3A	0.2918	0.3173	0.5750	0.044*
H3B	0.1758	0.3970	0.6137	0.044*
C4	0.3792 (4)	0.4339 (4)	0.7929 (6)	0.0401 (10)
H4A	0.3510	0.5086	0.8317	0.048*
H4B	0.3830	0.3762	0.8902	0.048*
C5	0.2141 (4)	0.5937 (3)	0.4614 (6)	0.0309 (8)
H5A	0.1554	0.5882	0.5416	0.037*
H5B	0.1521	0.6172	0.3347	0.037*
C6	0.3256 (4)	0.6887 (3)	0.5411 (5)	0.0310 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0203 (4)	0.0227 (4)	0.0279 (4)	0.0026 (3)	0.0055 (3)	−0.0003 (3)
O1	0.0397 (18)	0.066 (2)	0.053 (2)	−0.0136 (15)	0.0076 (15)	−0.0177 (16)
O2	0.0302 (14)	0.0401 (16)	0.0306 (15)	0.0078 (13)	0.0065 (11)	0.0075 (12)
O3	0.0249 (15)	0.0323 (15)	0.068 (2)	0.0053 (12)	0.0029 (14)	−0.0206 (14)
O4	0.0227 (13)	0.0269 (13)	0.0468 (17)	0.0006 (11)	0.0076 (12)	−0.0064 (11)
N1	0.0241 (16)	0.0217 (15)	0.0329 (17)	−0.0002 (12)	0.0067 (13)	−0.0023 (11)
C1	0.037 (2)	0.047 (2)	0.039 (2)	−0.013 (2)	0.0060 (18)	−0.0058 (19)
C2	0.0244 (19)	0.037 (2)	0.036 (2)	−0.0001 (16)	0.0081 (16)	−0.0030 (17)
C3	0.034 (2)	0.035 (2)	0.041 (2)	−0.0042 (18)	0.0142 (18)	0.0034 (17)
C4	0.034 (2)	0.050 (3)	0.036 (2)	0.003 (2)	0.0119 (18)	0.0074 (19)
C5	0.0216 (18)	0.034 (2)	0.035 (2)	0.0020 (16)	0.0072 (15)	−0.0028 (16)
C6	0.0258 (19)	0.032 (2)	0.031 (2)	0.0047 (16)	0.0048 (15)	−0.0049 (15)

Geometric parameters (Å, º) top

Co1—O4	2.046 (2)	N1—C2	1.483 (5)
Co1—O4ⁱ	2.046 (2)	C1—C2	1.512 (5)
Co1—O2	2.088 (3)	C1—H1A	0.9700
Co1—O2ⁱ	2.088 (3)	C1—H1B	0.9700
Co1—N1ⁱ	2.172 (3)	C2—H2A	0.9700
Co1—N1	2.172 (3)	C2—H2B	0.9700
O1—C1	1.409 (5)	C3—C4	1.507 (5)
O1—H11	0.8499	C3—H3A	0.9700
O2—C4	1.430 (5)	C3—H3B	0.9700
O2—H12	0.8500	C4—H4A	0.9700
O3—C6	1.249 (4)	C4—H4B	0.9700
O4—C6	1.260 (4)	C5—C6	1.515 (5)
N1—C5	1.476 (4)	C5—H5A	0.9700
N1—C3	1.480 (5)	C5—H5B	0.9700

O4—Co1—O4ⁱ	180.0	C2—C1—H1B	110.4
O4—Co1—O2	88.86 (11)	H1A—C1—H1B	108.6
O4ⁱ—Co1—O2	91.14 (11)	N1—C2—C1	115.8 (3)
O4—Co1—O2ⁱ	91.14 (11)	N1—C2—H2A	108.3
O4ⁱ—Co1—O2ⁱ	88.86 (11)	C1—C2—H2A	108.3
O2—Co1—O2ⁱ	180.0	N1—C2—H2B	108.3
O4—Co1—N1ⁱ	98.17 (10)	C1—C2—H2B	108.3
O4ⁱ—Co1—N1ⁱ	81.83 (10)	H2A—C2—H2B	107.4
O2—Co1—N1ⁱ	97.61 (11)	N1—C3—C4	111.3 (3)
O2ⁱ—Co1—N1ⁱ	82.39 (11)	N1—C3—H3A	109.4
O4—Co1—N1	81.83 (10)	C4—C3—H3A	109.4
O4ⁱ—Co1—N1	98.17 (10)	N1—C3—H3B	109.4
O2—Co1—N1	82.39 (11)	C4—C3—H3B	109.4
O2ⁱ—Co1—N1	97.61 (11)	H3A—C3—H3B	108.0
N1ⁱ—Co1—N1	180.0	O2—C4—C3	109.6 (3)
C1—O1—H11	108.0	O2—C4—H4A	109.8
C4—O2—Co1	111.2 (2)	C3—C4—H4A	109.8
C4—O2—H12	115.0	O2—C4—H4B	109.8
Co1—O2—H12	116.9	C3—C4—H4B	109.8
C6—O4—Co1	116.5 (2)	H4A—C4—H4B	108.2
C5—N1—C3	112.9 (3)	N1—C5—C6	114.9 (3)
C5—N1—C2	113.2 (3)	N1—C5—H5A	108.5
C3—N1—C2	110.9 (3)	C6—C5—H5A	108.5
C5—N1—Co1	106.5 (2)	N1—C5—H5B	108.5
C3—N1—Co1	103.3 (2)	C6—C5—H5B	108.5
C2—N1—Co1	109.5 (2)	H5A—C5—H5B	107.5
O1—C1—C2	106.5 (3)	O3—C6—O4	123.4 (3)
O1—C1—H1A	110.4	O3—C6—C5	117.5 (3)
C2—C1—H1A	110.4	O4—C6—C5	119.1 (3)
O1—C1—H1B	110.4

O4—Co1—O2—C4	75.2 (3)	O4ⁱ—Co1—N1—C2	−48.4 (2)
O4ⁱ—Co1—O2—C4	−104.8 (3)	O2—Co1—N1—C2	−138.4 (2)
O2ⁱ—Co1—O2—C4	−9 (84)	O2ⁱ—Co1—N1—C2	41.6 (2)
N1ⁱ—Co1—O2—C4	173.3 (3)	N1ⁱ—Co1—N1—C2	35 (100)
N1—Co1—O2—C4	−6.7 (3)	C5—N1—C2—C1	−67.2 (4)
O4ⁱ—Co1—O4—C6	37 (100)	C3—N1—C2—C1	60.8 (4)
O2—Co1—O4—C6	−88.4 (3)	Co1—N1—C2—C1	174.1 (3)
O2ⁱ—Co1—O4—C6	91.6 (3)	O1—C1—C2—N1	179.1 (3)
N1ⁱ—Co1—O4—C6	174.1 (3)	C5—N1—C3—C4	−70.5 (4)
N1—Co1—O4—C6	−5.9 (3)	C2—N1—C3—C4	161.4 (3)
O4—Co1—N1—C5	8.9 (2)	Co1—N1—C3—C4	44.2 (3)
O4ⁱ—Co1—N1—C5	−171.1 (2)	Co1—O2—C4—C3	32.5 (4)
O2—Co1—N1—C5	98.9 (2)	N1—C3—C4—O2	−53.5 (4)
O2ⁱ—Co1—N1—C5	−81.1 (2)	C3—N1—C5—C6	101.7 (4)
N1ⁱ—Co1—N1—C5	−88 (100)	C2—N1—C5—C6	−131.4 (3)
O4—Co1—N1—C3	−110.2 (2)	Co1—N1—C5—C6	−11.0 (4)
O4ⁱ—Co1—N1—C3	69.8 (2)	Co1—O4—C6—O3	−177.0 (3)
O2—Co1—N1—C3	−20.3 (2)	Co1—O4—C6—C5	1.1 (5)
O2ⁱ—Co1—N1—C3	159.7 (2)	N1—C5—C6—O3	−174.3 (3)
N1ⁱ—Co1—N1—C3	153 (100)	N1—C5—C6—O4	7.4 (5)
O4—Co1—N1—C2	131.6 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H12···O3ⁱⁱ	0.85	1.79	2.632 (4)	171
O1—H11···O3ⁱⁱⁱ	0.85	1.89	2.744 (4)	178

Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₆H₁₂NO₄)₂]
M_r	383.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.932 (2), 11.388 (2), 7.4477 (15)
β (°)	110.12 (3)
V (Å³)	791.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.2 × 0.18 × 0.18

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.736, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8129, 1819, 1357
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.159, 1.00
No. of reflections	1819
No. of parameters	106
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.36

Computer programs: SCXmini Benchtop Crystallography System Software (Rigaku, 2006), PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H12···O3ⁱ	0.85	1.79	2.632 (4)	170.6
O1—H11···O3ⁱⁱ	0.85	1.89	2.744 (4)	177.5

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge financial support from Tianjin Municipal Education Commission (grant No. 20060503).

References

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