Bis[2-(1H-benzimidazol-2-yl)phenolato-κ2N3,O]cobalt(II) dimethyl­formamide disolvate

He, F.; Xi, Y.; Li, J..; Zhang, F.

doi:10.1107/S1600536808029620

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1311

doi:10.1107/S1600536808029620

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Bis[2-(1H-benzimidazol-2-yl)phenolato-κ²N³,O]cobalt(II) dimethylformamide disolvate

Feigang He,^a Yun Xi,^b Jun Li ^b ^* and Fengxing Zhang ^b

^aDepartment of Chemistry, Shannxi Institute of Education, Xi'an, Shaanxi 710061, People's Republic of China, and ^bDepartment of Chemistry, Northwest University, Xi'an, Shaanxi 710069, People's Republic of China
^*Correspondence e-mail: junli@nwu.edu.cn

(Received 14 May 2008; accepted 16 September 2008; online 21 September 2008)

In the crystal structure of the title compound, [Co(C₁₃H₉N₂O)₂]·2C₃H₇NO, the Co^II ion is four-coordinated by two N atoms and two O atoms from two deprotonated 2-(1H-benzimidazol-2-yl)phenol ligands in a distorted tetrahedral geometry. The dimethylformamide solvent molecules are found inside a two-dimensional network structure formed by intermolecular N—H⋯O hydrogen bonds linking the molecules.

Related literature

For related literature, see: Benzekri et al. (1991 ); Crane et al. (1995 ); Lorosch & Haase (1985 ); Maekawa et al. (1989 ); McKee et al. (1981 ); Sundburg & Martin (1974 ); Nalwa et al. (2003 ) and references cited therein; Tong et al. (2005 ).

Experimental

Crystal data

[Co(C₁₃H₉N₂O)₂]·2C₃H₇NO
M_r = 623.57
Orthorhombic, P b c n
a = 15.440 (2) Å
b = 8.7022 (12) Å
c = 22.156 (3) Å
V = 2977.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 298 (2) K
0.34 × 0.28 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.816, T_max = 0.946
12837 measured reflections
3157 independent reflections
2167 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.107
S = 1.03
3157 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	1.94	2.772 (2)	164

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029620/bv2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029620/bv2101Isup2.hkl

checkCIF report

Comment top

Complexes with imidazole-related and imidazole-containing ligands serve as models for metalloproteins and have been extensively studied in recent years (Sundburg et al., 1974; Maekawa et al., 1989; Lorosch & Haase, 1985; Benzekri et al., 1991; Crane et al., 1995; McKee et al., 1981). It has been shown in the previous reports, that the benzimidazole-based derivatives are a novel class of N,O-donor ligands that could form sublimable luminescent complexes as possible electroluminescent materials (Nalwa et al., 2003; Tong et al., 2005). The bidentate ligand 2-(2'-hydroxyphenyl)benzimidazole(hpbm) is an N,O bidentate ligand that comprises two donor groups of relevance to the coordination of metal centers in biological systems, namely phenolate (tyrosine) and imidazole (histidine). In present paper, we report the synthesis and crystal structure of the dimethylformamide solvate of the Co^II complex with two deprotonated ligands, [Co(pbm)₂].2(DMF).

The structure of the complex is shown in Fig. 1. The molecules of the cobalt complex are disposed about a twofold symmetry axis. The Co—O and Co—N bond lengths are 1.9135 (2) Å, and 1.9784 (2)Å respectively (Table 1). The cobalt atoms adopt a distorted four-coordinate environment with a dihedral angle of 75.4 (3)° between the two coordinating ligands (as defined by the Co—N—O planes). The O—Co—O and N—Co—N bond angles are 131.26 (2)° and 123.60 (2)°. In the title complex, the stronger hydrogen bonds are formed through oxygen atom of DMF with uncoordinated nitrogen atom of the ligand. The weaker hydrogen bonds are formed through uncoordinated oxygen atom of the ligand with carbon atom of another ligand.Through above the interaction, a novel two-dimensional network structure was formed where we happened to find the solvent molecules inside.

Related literature top

For related literature, see: Benzekri et al. (1991); Crane et al. (1995); Lorosch & Haase (1985); Maekawa et al. (1989); McKee et al. (1981); Sundburg & Martin (1974); Nalwa et al. (2003) and references cited therein; Tong et al. (2005).

Experimental top

The ligand, 2-(2'-hydroxyphenyl)benzimidazole, was synthesized as follows: A solution of 2.32 g (19 mmol) of salicylaldehyde in 15 ml of EtOH was added to a solution of 2.05 g (19 mmol) of o-phenylenediamine in 25 ml of EtOH with stirring and heating. The resulting orange solution was refluxed for hour and then cooled to room temperature. After standing in the refridgerator for 12 h, the orange solution was filtered and 15 ml of ether was added to the solution. Standing in the open air for 2 d yielded orange crystalline needles which were filtered and air-dried. Yield: 60%. The elemental analysis results are completely in agreement with the structural composition of the ligand. m.p. 524–525 K.

The title complex was obtained as follows: To a filtered solution of HL(0.420 g, 2 mmol) and KOH (0.112 g, 2 mmol) in methanol(60 ml) at rt was added a filtered solution of Co(OAc)₂^.H₂O (0.250 g, 1 mmol) in methanol(29 ml) with stirring. The product began to crystallize from the solution tardily. After 1 h the pink solid was filtered off, washed with methanol, and air-dried. X-ray quality single crystals were grown by the vapour diffusion of ether into a DMF solution of the solid above to yield pink crystals of the title complex. Analysis. Calcd for C₃₂H₃₂N₆O₄Co (%): C 61.64, H 5.14, N 13.48. Found (%): C 62.06, H 4.95, N 13.86.

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-hydrogen atoms. H atoms are shown as small spheres of arbitrary radii. [symmetry code: (i) -x + 1, y, -z + 1/2]
	Fig. 2. Two-dimensional network structure with the solvent molecules encapsulated.

Bis[2-(1H-benzimidazol-2-yl)phenolato- κ²N³,O]cobalt(II) dimethylformamide disolvate top

Crystal data top

[Co(C₁₃H₉N₂O)₂]·2C₃H₇NO	D_x = 1.391 Mg m⁻³
M_r = 623.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 4622 reflections
a = 15.440 (2) Å	θ = 3.0–22.7°
b = 8.7022 (12) Å	µ = 0.62 mm⁻¹
c = 22.156 (3) Å	T = 298 K
V = 2977.0 (7) Å³	Flake, pink
Z = 4	0.34 × 0.28 × 0.09 mm
F(000) = 1300

Data collection top

Bruker SMART CCD area-detector diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	2167 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 26.9°, θ_min = 2.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→18
T_min = 0.816, T_max = 0.946	k = −11→9
12837 measured reflections	l = −27→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + 0.8613P] where P = (F_o² + 2F_c²)/3
3157 reflections	(Δ/σ)_max = 0.011
197 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Co(C₁₃H₉N₂O)₂]·2C₃H₇NO	V = 2977.0 (7) Å³
M_r = 623.57	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 15.440 (2) Å	µ = 0.62 mm⁻¹
b = 8.7022 (12) Å	T = 298 K
c = 22.156 (3) Å	0.34 × 0.28 × 0.09 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3157 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2167 reflections with I > 2σ(I)
T_min = 0.816, T_max = 0.946	R_int = 0.036
12837 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3157 reflections	Δρ_min = −0.34 e Å⁻³
197 parameters

Special details top

Experimental. ABSCOR BY T.Higashi 8 march,1995

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	0.5000	0.02008 (5)	0.2500	0.03984 (15)
O1	0.40147 (10)	−0.07066 (19)	0.28840 (6)	0.0548 (4)
O2	0.48308 (13)	0.3080 (2)	0.53185 (8)	0.0767 (6)
N1	0.53688 (11)	0.12752 (19)	0.32438 (7)	0.0382 (4)
N2	0.53681 (11)	0.2071 (2)	0.41924 (7)	0.0414 (4)
H2A	0.5210	0.2194	0.4561	0.050*
N3	0.51069 (13)	0.3913 (2)	0.62601 (8)	0.0522 (5)
C1	0.60775 (12)	0.2234 (2)	0.33281 (9)	0.0371 (5)
C2	0.67200 (14)	0.2690 (2)	0.29255 (10)	0.0473 (5)
H2	0.6718	0.2360	0.2526	0.057*
C3	0.73595 (15)	0.3649 (3)	0.31418 (11)	0.0548 (6)
H3	0.7797	0.3977	0.2883	0.066*
C4	0.73617 (16)	0.4136 (3)	0.37414 (11)	0.0588 (7)
H4	0.7803	0.4781	0.3873	0.071*
C5	0.67330 (16)	0.3694 (3)	0.41443 (10)	0.0542 (6)
H5	0.6740	0.4019	0.4544	0.065*
C6	0.60842 (13)	0.2734 (2)	0.39230 (9)	0.0396 (5)
C7	0.49560 (13)	0.1191 (2)	0.37745 (8)	0.0343 (4)
C8	0.41866 (13)	0.0275 (2)	0.39038 (9)	0.0374 (5)
C9	0.38635 (14)	0.0222 (2)	0.44962 (10)	0.0449 (5)
H9	0.4138	0.0795	0.4794	0.054*
C10	0.31575 (15)	−0.0646 (3)	0.46486 (11)	0.0534 (6)
H10	0.2960	−0.0666	0.5045	0.064*
C11	0.27404 (15)	−0.1491 (3)	0.42092 (11)	0.0568 (6)
H11	0.2257	−0.2076	0.4310	0.068*
C12	0.30338 (15)	−0.1473 (3)	0.36265 (11)	0.0542 (6)
H12	0.2741	−0.2045	0.3337	0.065*
C13	0.37675 (13)	−0.0612 (3)	0.34506 (9)	0.0424 (5)
C14	0.52757 (18)	0.3784 (3)	0.56829 (12)	0.0634 (7)
H14	0.5772	0.4264	0.5539	0.076*
C15	0.5674 (2)	0.4749 (3)	0.66682 (14)	0.0821 (9)
H15A	0.5929	0.4045	0.6951	0.123*
H15B	0.5344	0.5508	0.6883	0.123*
H15C	0.6123	0.5245	0.6441	0.123*
C16	0.43673 (18)	0.3165 (3)	0.65240 (12)	0.0732 (8)
H16A	0.4056	0.2617	0.6217	0.110*
H16B	0.3995	0.3921	0.6703	0.110*
H16C	0.4557	0.2457	0.6829	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0411 (3)	0.0512 (3)	0.0272 (2)	0.000	−0.00169 (17)	0.000
O1	0.0521 (10)	0.0778 (11)	0.0346 (8)	−0.0211 (8)	−0.0020 (7)	−0.0004 (8)
O2	0.0896 (14)	0.0933 (14)	0.0471 (11)	0.0015 (11)	0.0029 (10)	−0.0212 (10)
N1	0.0390 (10)	0.0456 (10)	0.0300 (9)	−0.0014 (8)	0.0011 (7)	0.0010 (7)
N2	0.0454 (10)	0.0508 (11)	0.0279 (9)	−0.0063 (8)	0.0026 (7)	−0.0028 (8)
N3	0.0615 (13)	0.0562 (12)	0.0388 (11)	0.0040 (10)	0.0039 (9)	−0.0020 (9)
C1	0.0357 (11)	0.0411 (11)	0.0346 (10)	0.0010 (9)	−0.0002 (9)	0.0021 (9)
C2	0.0478 (13)	0.0568 (14)	0.0374 (11)	−0.0011 (11)	0.0071 (10)	0.0027 (10)
C3	0.0463 (14)	0.0619 (15)	0.0561 (15)	−0.0103 (11)	0.0105 (11)	0.0023 (12)
C4	0.0506 (15)	0.0655 (16)	0.0604 (16)	−0.0200 (12)	−0.0003 (12)	−0.0033 (12)
C5	0.0577 (15)	0.0608 (15)	0.0440 (13)	−0.0130 (12)	−0.0006 (11)	−0.0083 (11)
C6	0.0390 (12)	0.0444 (12)	0.0355 (10)	−0.0025 (9)	0.0018 (9)	0.0016 (9)
C7	0.0379 (11)	0.0382 (11)	0.0269 (10)	0.0034 (9)	−0.0016 (9)	0.0019 (8)
C8	0.0351 (11)	0.0424 (12)	0.0348 (11)	0.0023 (9)	0.0000 (9)	0.0058 (9)
C9	0.0490 (14)	0.0492 (13)	0.0366 (12)	0.0030 (10)	0.0051 (10)	−0.0004 (10)
C10	0.0519 (14)	0.0624 (15)	0.0458 (13)	0.0038 (12)	0.0155 (11)	0.0097 (12)
C11	0.0433 (14)	0.0650 (16)	0.0620 (17)	−0.0087 (12)	0.0073 (12)	0.0149 (13)
C12	0.0443 (13)	0.0664 (16)	0.0521 (14)	−0.0113 (11)	−0.0065 (11)	0.0046 (12)
C13	0.0358 (12)	0.0517 (13)	0.0395 (12)	−0.0022 (10)	−0.0032 (9)	0.0091 (10)
C14	0.0687 (17)	0.0705 (18)	0.0510 (16)	0.0073 (14)	0.0124 (13)	0.0001 (14)
C15	0.094 (2)	0.083 (2)	0.0694 (19)	0.0018 (17)	−0.0113 (17)	−0.0150 (16)
C16	0.077 (2)	0.0775 (19)	0.0646 (17)	0.0041 (15)	0.0186 (15)	0.0129 (15)

Geometric parameters (Å, º) top

Co1—O1	1.9135 (15)	C4—H4	0.9300
Co1—O1ⁱ	1.9135 (15)	C5—C6	1.394 (3)
Co1—N1	1.9784 (16)	C5—H5	0.9300
Co1—N1ⁱ	1.9784 (16)	C7—C8	1.459 (3)
O1—C13	1.315 (2)	C8—C9	1.405 (3)
O2—C14	1.224 (3)	C8—C13	1.423 (3)
N1—C7	1.339 (2)	C9—C10	1.369 (3)
N1—C1	1.389 (2)	C9—H9	0.9300
N2—C7	1.360 (2)	C10—C11	1.379 (3)
N2—C6	1.383 (2)	C10—H10	0.9300
N2—H2A	0.8600	C11—C12	1.368 (3)
N3—C14	1.310 (3)	C11—H11	0.9300
N3—C16	1.439 (3)	C12—C13	1.413 (3)
N3—C15	1.454 (3)	C12—H12	0.9300
C1—C6	1.388 (3)	C14—H14	0.9300
C1—C2	1.392 (3)	C15—H15A	0.9600
C2—C3	1.379 (3)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.394 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.374 (3)	C16—H16C	0.9600

O1—Co1—O1ⁱ	131.26 (11)	N1—C7—C8	126.16 (18)
O1—Co1—N1	93.07 (6)	N2—C7—C8	123.70 (17)
O1ⁱ—Co1—N1	109.66 (7)	C9—C8—C13	118.69 (19)
O1—Co1—N1ⁱ	109.66 (7)	C9—C8—C7	119.39 (19)
O1ⁱ—Co1—N1ⁱ	93.07 (6)	C13—C8—C7	121.88 (18)
N1—Co1—N1ⁱ	123.60 (10)	C10—C9—C8	122.1 (2)
C13—O1—Co1	129.02 (13)	C10—C9—H9	118.9
C7—N1—C1	106.85 (16)	C8—C9—H9	118.9
C7—N1—Co1	124.63 (14)	C9—C10—C11	119.5 (2)
C1—N1—Co1	128.51 (13)	C9—C10—H10	120.3
C7—N2—C6	108.38 (16)	C11—C10—H10	120.3
C7—N2—H2A	125.8	C12—C11—C10	120.3 (2)
C6—N2—H2A	125.8	C12—C11—H11	119.8
C14—N3—C16	121.1 (2)	C10—C11—H11	119.8
C14—N3—C15	122.0 (2)	C11—C12—C13	122.1 (2)
C16—N3—C15	116.8 (2)	C11—C12—H12	118.9
C6—C1—N1	108.77 (17)	C13—C12—H12	118.9
C6—C1—C2	120.93 (19)	O1—C13—C12	117.6 (2)
N1—C1—C2	130.30 (19)	O1—C13—C8	125.17 (19)
C3—C2—C1	117.4 (2)	C12—C13—C8	117.24 (19)
C3—C2—H2	121.3	O2—C14—N3	125.1 (3)
C1—C2—H2	121.3	O2—C14—H14	117.5
C2—C3—C4	121.1 (2)	N3—C14—H14	117.5
C2—C3—H3	119.4	N3—C15—H15A	109.5
C4—C3—H3	119.4	N3—C15—H15B	109.5
C5—C4—C3	122.2 (2)	H15A—C15—H15B	109.5
C5—C4—H4	118.9	N3—C15—H15C	109.5
C3—C4—H4	118.9	H15A—C15—H15C	109.5
C4—C5—C6	116.6 (2)	H15B—C15—H15C	109.5
C4—C5—H5	121.7	N3—C16—H16A	109.5
C6—C5—H5	121.7	N3—C16—H16B	109.5
N2—C6—C1	105.86 (17)	H16A—C16—H16B	109.5
N2—C6—C5	132.3 (2)	N3—C16—H16C	109.5
C1—C6—C5	121.82 (19)	H16A—C16—H16C	109.5
N1—C7—N2	110.13 (17)	H16B—C16—H16C	109.5

O1ⁱ—Co1—O1—C13	117.1 (2)	C1—N1—C7—N2	0.6 (2)
N1—Co1—O1—C13	−2.6 (2)	Co1—N1—C7—N2	−179.44 (13)
N1ⁱ—Co1—O1—C13	−130.02 (19)	C1—N1—C7—C8	−178.17 (18)
O1—Co1—N1—C7	0.38 (17)	Co1—N1—C7—C8	1.8 (3)
O1ⁱ—Co1—N1—C7	−135.71 (16)	C6—N2—C7—N1	−0.9 (2)
N1ⁱ—Co1—N1—C7	116.49 (17)	C6—N2—C7—C8	177.94 (18)
O1—Co1—N1—C1	−179.71 (17)	N1—C7—C8—C9	175.51 (19)
O1ⁱ—Co1—N1—C1	44.19 (18)	N2—C7—C8—C9	−3.1 (3)
N1ⁱ—Co1—N1—C1	−63.60 (15)	N1—C7—C8—C13	−2.3 (3)
C7—N1—C1—C6	−0.1 (2)	N2—C7—C8—C13	179.04 (19)
Co1—N1—C1—C6	179.93 (14)	C13—C8—C9—C10	−0.4 (3)
C7—N1—C1—C2	179.2 (2)	C7—C8—C9—C10	−178.3 (2)
Co1—N1—C1—C2	−0.7 (3)	C8—C9—C10—C11	−0.5 (3)
C6—C1—C2—C3	0.1 (3)	C9—C10—C11—C12	0.5 (4)
N1—C1—C2—C3	−179.1 (2)	C10—C11—C12—C13	0.4 (4)
C1—C2—C3—C4	0.2 (4)	Co1—O1—C13—C12	−176.47 (16)
C2—C3—C4—C5	−0.2 (4)	Co1—O1—C13—C8	2.8 (3)
C3—C4—C5—C6	−0.3 (4)	C11—C12—C13—O1	177.9 (2)
C7—N2—C6—C1	0.8 (2)	C11—C12—C13—C8	−1.4 (3)
C7—N2—C6—C5	−178.3 (2)	C9—C8—C13—O1	−177.9 (2)
N1—C1—C6—N2	−0.4 (2)	C7—C8—C13—O1	−0.1 (3)
C2—C1—C6—N2	−179.79 (19)	C9—C8—C13—C12	1.3 (3)
N1—C1—C6—C5	178.78 (19)	C7—C8—C13—C12	179.18 (19)
C2—C1—C6—C5	−0.6 (3)	C16—N3—C14—O2	2.0 (4)
C4—C5—C6—N2	179.6 (2)	C15—N3—C14—O2	179.0 (3)
C4—C5—C6—C1	0.7 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	1.94	2.772 (2)	164

Experimental details

Crystal data
Chemical formula	[Co(C₁₃H₉N₂O)₂]·2C₃H₇NO
M_r	623.57
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	15.440 (2), 8.7022 (12), 22.156 (3)
V (Å³)	2977.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.34 × 0.28 × 0.09

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.816, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	12837, 3157, 2167
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.636

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 1.03
No. of reflections	3157
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.34

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	1.94	2.772 (2)	163.5

Acknowledgements

This work was supported by the State Key Laboratory of Fine Chemicals, Dalian University of Technology, China.

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