Bis[2-(1H-benzimidazol-2-yl)phenolato-κN,O]cobalt(II) dimethyl-formamide disolvate.

In the crystal structure of the title compound, [Co(C(13)H(9)N(2)O)(2)]·2C(3)H(7)NO, 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 tetra-hedral geometry. The dimethyl-formamide solvent mol-ecules are found inside a two-dimensional network structure formed by inter-molecular N-H⋯O hydrogen bonds linking the mol-ecules.

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 = 623.57

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.03

3157 reflections

197 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.34 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

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

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

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

[Co(C13H9N2O)2]·2C3H7NO	Dx = 1.391 Mg m−3
Mr = 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

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

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(Fo2) + 0.8613P] where P = (Fo2 + 2Fc2)/3
3157 reflections	(Δ/σ)max = 0.011
197 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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