Bis(1-benzofuro[3,2-c]pyridine-κN)dichloridocobalt(II)

In the title complex, [CoCl₂(C₁₁H₇NO)₂], the Co^II atom lies on a twofold rotation axis four-coordinated by two Cl atoms and two N-donor atoms from two 1-benzofuro[3,2-c]pyridine ligands, giving a slightly distorted tetra­hedral coordination environment. The N/Co/N and Cl/Co/Cl planes are nearly perpendicular, with a dihedral angle of 87.1 (1)°. The dihedral angle between the two benzofuropyridine ligands is 45.8 (1)°. In the crystal structure, mol­ecules are linked into a two-dimensional network parallel to the ab plane by C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.053
• wR factor = 0.196
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.90

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   0 ALERT level B = Potentially serious problem
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   1 ALERT level G = General alerts; check

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S1. Comment

Cobalt complexes are of great interest in coordination chemistry in relation to catalysis and enzymatic reactions, magnetism and molecular architectures (Billson et al., 2000; Fritsky et al., 2003; Kotera et al., 2003). Most of these compounds represent discrete mononuclear complexes (Masaki et al., 2002; Khalaji et al., 2006; Zhao et al., 2006) but in some of them the Co atoms are connected into dinuclear units or polymers (Lumme et al., 1996; Yang et al., 2006; Jensen et al., 2000; Lee & Wang, 2007). The furo[3,2-c]pyridine and its derivatives represent quinoline isosters, in which the benzene ring is replaced by the furan and pyridine ring can be readily coordinated to metal centers through N-donor atom (Miklovič et al., 2004; Baran et al., 2005). We report here the synthesis and crystal structure of the title compound, a mononuclear Co^II compound with a benzofuropyridine (BFP) ligand.

The Co^II atom lying on a twofold rotation axis is in a tetrahedral geometry and is coordinated by two BFP ligands and two chloride anions (Fig. 1). The Co—N [2.033 (4) Å] and Co—Cl [2.2259 (15) Å] bond lengths in the title compound are in good agreement with the correspoding mean distances in the related complexes (Amirnasr et al., 2002; Zhao et al., 2006; Khalaji et al., 2006). The bond angles subtended at the Co1 atom range from 103.65 (12) to 118.59 (10)°, indicating a slightly distorted tetrahedral coordination. The dihedral angle between the nearly planar BFP ligands is 45.8 (1)°.

In the crystal structure of the title compound, C—H···Cl interactions (Table 2) involving atoms H2A and Cl1 connect the molecules into a two-dimensional network parallel to the ab plane. The formation of a four-coordinate complex, rather than a possible six-coordinate one, is attributed to the large volume of the monodentate BFP ligand.

Related literature

For ligand synthesis, see: Bobošík et al. (1995); Bencková & Krutošíková (1995, 1999). For general background, see: Baran et al. (2005); Billson et al. (2000); Fritsky et al. (2003); Jensen et al. (2000); Kotera et al. (2003); Lee & Wang (2007); Lumme et al. (1996); Masaki et al. (2002); Miklovič et al. (2004); Yang et al. (2006). For related structures, see: Amirnasr et al. (2002); Khalaji et al. (2006); Zhao et al. (2006).

S2. Experimental

The organic ligand, [1]benzofuro[3,2-c]pyridine, was prepared according to literature procedures of Bobošík et al. (1995) and Bencková & Krutošíková (1995, 1999). To a CoCl₂.6H₂O (1 mmol) solution in ethanol (4 ml) was added the solution of [1]benzofuro[3,2-c]pyridine (3 mmol) in ethanol (4 ml) at room temperature. Small blue crystals were formed after 3 d. These were filtered off, washed with ethanol and recrystallized from tetrahydrofuran.

S3. Refinement

All H atoms were placed in geometrically calculated positions and allowed to ride on their parent atoms, with C—H distances of 0.93 Å and U_iso set at 1.2U_eq of the parent atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures

Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Unlabelled atoms are related to labelled atoms by the symmetry operation (-x, y, 1/2 - z).

Bis(1-benzofuro[3,2-c]pyridine-κN)dichloridocobalt(II)

Crystal data

[CoCl2(C11H7NO)2]	F(000) = 948
Mr = 468.21	Dx = 1.629 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8019 reflections
a = 7.7063 (2) Å	θ = 3.1–28.1°
b = 12.1886 (3) Å	µ = 1.20 mm^−1
c = 20.4444 (5) Å	T = 298 K
β = 96.217 (3)°	Plate, blue
V = 1909.03 (8) Å^3	0.38 × 0.28 × 0.03 mm
Z = 4

Data collection

Oxford Diffraction Gemini R CCD diffractometer	1942 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: analytical (Clark & Reid, 1995)	h = −9→9
Tmin = 0.698, Tmax = 0.967	k = −15→15
15916 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 12.9573P] where P = (Fo^2 + 2Fc^2)/3
1942 reflections	(Δ/σ)max = 0.001
132 parameters	Δρmax = 0.97 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.0900 (7)	0.1711 (5)	0.3404 (3)	0.0465 (12)
H2A	0.1235	0.1378	0.3028	0.056*
C3	0.1133 (8)	0.1134 (5)	0.3987 (3)	0.0505 (13)
H3A	0.1587	0.0426	0.4010	0.061*
C5	−0.0026 (9)	0.2030 (6)	0.6201 (3)	0.0629 (18)
H5A	0.0322	0.1409	0.6445	0.076*
C6	−0.0707 (9)	0.2930 (7)	0.6481 (3)	0.067 (2)
H6A	−0.0807	0.2924	0.6930	0.080*
C7	−0.1249 (9)	0.3847 (6)	0.6118 (3)	0.0609 (17)
H7A	−0.1717	0.4439	0.6326	0.073*
C8	−0.1110 (7)	0.3902 (5)	0.5448 (3)	0.0484 (13)
H8A	−0.1472	0.4521	0.5205	0.058*
C9	−0.0246 (7)	0.3226 (4)	0.3884 (2)	0.0390 (11)
H9A	−0.0718	0.3928	0.3847	0.047*
C10	0.0656 (7)	0.1663 (4)	0.4527 (3)	0.0418 (11)
C11	0.0114 (7)	0.2096 (5)	0.5533 (3)	0.0471 (13)
C12	−0.0411 (7)	0.3001 (4)	0.5151 (2)	0.0418 (12)
C13	−0.0044 (6)	0.2728 (4)	0.4488 (2)	0.0359 (10)
N1	0.0219 (6)	0.2728 (3)	0.33452 (19)	0.0388 (9)
O4	0.0769 (6)	0.1264 (3)	0.51576 (19)	0.0527 (10)
Cl1	0.2471 (2)	0.45525 (13)	0.24621 (7)	0.0552 (4)
Co1	0.0000	0.36200 (8)	0.2500	0.0387 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.051 (3)	0.043 (3)	0.047 (3)	0.006 (2)	0.014 (2)	−0.003 (2)
C3	0.057 (3)	0.037 (3)	0.057 (3)	0.011 (2)	0.003 (3)	0.002 (2)
C5	0.070 (4)	0.081 (5)	0.037 (3)	−0.022 (4)	−0.003 (3)	0.018 (3)
C6	0.071 (4)	0.100 (6)	0.029 (3)	−0.031 (4)	0.005 (3)	−0.004 (3)
C7	0.066 (4)	0.074 (4)	0.046 (3)	−0.021 (3)	0.016 (3)	−0.016 (3)
C8	0.050 (3)	0.055 (3)	0.041 (3)	−0.011 (3)	0.010 (2)	−0.008 (2)
C9	0.044 (3)	0.037 (2)	0.037 (2)	0.000 (2)	0.008 (2)	0.001 (2)
C10	0.041 (3)	0.041 (3)	0.042 (3)	0.000 (2)	−0.001 (2)	0.008 (2)
C11	0.052 (3)	0.053 (3)	0.036 (3)	−0.013 (2)	0.000 (2)	0.007 (2)
C12	0.045 (3)	0.050 (3)	0.031 (2)	−0.010 (2)	0.004 (2)	0.003 (2)
C13	0.039 (2)	0.035 (2)	0.034 (2)	−0.005 (2)	0.0050 (19)	0.0010 (19)
N1	0.045 (2)	0.039 (2)	0.034 (2)	0.0006 (18)	0.0096 (17)	0.0008 (17)
O4	0.063 (3)	0.048 (2)	0.044 (2)	0.0023 (19)	−0.0042 (18)	0.0157 (17)
Cl1	0.0641 (9)	0.0577 (9)	0.0452 (7)	−0.0172 (7)	0.0122 (6)	0.0013 (6)
Co1	0.0484 (6)	0.0396 (6)	0.0298 (5)	0.000	0.0116 (4)	0.000

Geometric parameters (Å, º)

C2—N1	1.346 (7)	C8—H8A	0.93
C2—C3	1.379 (8)	C9—N1	1.340 (6)
C2—H2A	0.93	C9—C13	1.369 (7)
C3—C10	1.362 (8)	C9—H9A	0.93
C3—H3A	0.93	C10—O4	1.373 (6)
C5—C6	1.368 (11)	C10—C13	1.405 (7)
C5—C11	1.384 (8)	C11—C12	1.385 (7)
C5—H5A	0.93	C11—O4	1.397 (7)
C6—C7	1.382 (11)	C12—C13	1.454 (7)
C6—H6A	0.93	N1—Co1	2.033 (4)
C7—C8	1.386 (8)	Cl1—Co1	2.2259 (15)
C7—H7A	0.93	Co1—N1^i	2.033 (4)
C8—C12	1.391 (8)	Co1—Cl1^i	2.2259 (15)
N1—C2—C3	124.0 (5)	C3—C10—C13	121.8 (5)
N1—C2—H2A	118.0	O4—C10—C13	111.4 (5)
C3—C2—H2A	118.0	C5—C11—C12	123.5 (6)
C10—C3—C2	115.9 (5)	C5—C11—O4	124.8 (6)
C10—C3—H3A	122.0	C12—C11—O4	111.7 (4)
C2—C3—H3A	122.0	C11—C12—C8	119.1 (5)
C6—C5—C11	116.2 (6)	C11—C12—C13	105.6 (5)
C6—C5—H5A	121.9	C8—C12—C13	135.3 (5)
C11—C5—H5A	121.9	C9—C13—C10	117.7 (5)
C5—C6—C7	122.0 (6)	C9—C13—C12	136.5 (5)
C5—C6—H6A	119.0	C10—C13—C12	105.7 (4)
C7—C6—H6A	119.0	C9—N1—C2	118.7 (4)
C6—C7—C8	121.3 (6)	C9—N1—Co1	116.8 (3)
C6—C7—H7A	119.4	C2—N1—Co1	124.3 (3)
C8—C7—H7A	119.4	C10—O4—C11	105.6 (4)
C7—C8—C12	117.9 (6)	N1^i—Co1—N1	115.3 (2)
C7—C8—H8A	121.0	N1^i—Co1—Cl1	103.65 (12)
C12—C8—H8A	121.0	N1—Co1—Cl1	108.07 (13)
N1—C9—C13	121.8 (5)	N1^i—Co1—Cl1^i	108.07 (13)
N1—C9—H9A	119.1	N1—Co1—Cl1^i	103.65 (12)
C13—C9—H9A	119.1	Cl1—Co1—Cl1^i	118.59 (10)
C3—C10—O4	126.8 (5)
N1—C2—C3—C10	−1.3 (9)	O4—C10—C13—C12	−0.7 (6)
C11—C5—C6—C7	1.0 (10)	C11—C12—C13—C9	179.2 (6)
C5—C6—C7—C8	−0.7 (10)	C8—C12—C13—C9	−1.0 (11)
C6—C7—C8—C12	0.3 (9)	C11—C12—C13—C10	0.8 (6)
C2—C3—C10—O4	−179.7 (5)	C8—C12—C13—C10	−179.4 (6)
C2—C3—C10—C13	0.6 (8)	C13—C9—N1—C2	0.0 (8)
C6—C5—C11—C12	−0.8 (9)	C13—C9—N1—Co1	−175.6 (4)
C6—C5—C11—O4	−179.8 (6)	C3—C2—N1—C9	1.0 (8)
C5—C11—C12—C8	0.4 (8)	C3—C2—N1—Co1	176.3 (4)
O4—C11—C12—C8	179.5 (5)	C3—C10—O4—C11	−179.5 (6)
C5—C11—C12—C13	−179.8 (5)	C13—C10—O4—C11	0.3 (6)
O4—C11—C12—C13	−0.7 (6)	C5—C11—O4—C10	179.3 (5)
C7—C8—C12—C11	−0.1 (8)	C12—C11—O4—C10	0.3 (6)
C7—C8—C12—C13	−179.8 (6)	C9—N1—Co1—N1^i	−157.1 (4)
N1—C9—C13—C10	−0.6 (7)	C2—N1—Co1—N1^i	27.5 (4)
N1—C9—C13—C12	−178.9 (5)	C9—N1—Co1—Cl1	87.5 (4)
C3—C10—C13—C9	0.3 (8)	C2—N1—Co1—Cl1	−87.9 (4)
O4—C10—C13—C9	−179.4 (4)	C9—N1—Co1—Cl1^i	−39.2 (4)
C3—C10—C13—C12	179.1 (5)	C2—N1—Co1—Cl1^i	145.4 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cl1^ii	0.93	2.68	3.481 (6)	145

Symmetry code: (ii) −x+1/2, y−1/2, −z+1/2.