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In the title compound, [Co(C13H9N2O)2], the coordination geometry of the CoII atom is distorted tetra­hedral; the Co atom lies on a twofold axis. Adjacent mol­ecules are linked by N—H...O hydrogen bonds into a three-dimensional network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028084/ng6183sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028084/ng6183Isup2.hkl
Contains datablock I

CCDC reference: 287664

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.114
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.030 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.49 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.19 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.31 From the CIF: _reflns_number_total 2669 Count of symmetry unique reflns 1683 Completeness (_total/calc) 158.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 986 Fraction of Friedel pairs measured 0.586 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

2-(Benzimidazol-2-yl)phenol is a bidentate heterocycle that possesses a benzimidazole nitrogen and a phenol oxygen site, and it also has an additional hydrogen-bond donor unit (NH) (Crane et al., 1995).

In the structure of (I), the CoII atom lies on a twofold axis and is coordinated by two N atoms and two O atoms to give a distorted tetrahedral geometry (Fig. 1). The benzimidazole and phenol groups are nearly planar as the dihedral angle between them is 3.6 (2)°. The angle between the two ligand planes is 83.10 (5)°. The complexes are linked by N—H···O hydrogen bonds [N···O = 2.809 (3) Å] into a three-dimensional network structure.

Experimental top

Cobalt nitrate hexahydrate (0.146 g, 0.5 mmol) and 2-(benzimidazol-2-yl)phenol (0.210 g, 1 mmol) were dissolved in ethanol (3 ml) and water (15 ml). The solution was placed in a 23 ml Teflon-lined stainless steel Parr bomb. The bomb was heated at 433 K for 120 h. The cooled mixture yielded red crystals of (I); these were washed with water and then dried in air (yield ca 70%).

Refinement top

The crystal is a racemic twin, can be refined in P41212 with a Flack (1983) parameter of 0.49 (3) and in P43212 with a Flack parameter of 0.52 (2). As the Flack parameter of the former is slightly lower, the space group P41212 was chosen. All H atoms were positioned geometrically and refined with a riding model, with distances C—H = 0.93 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids are drawn at the 50% probability level and H atoms as spheres of arbitrary radii. [symmetry code: (i) y, x, −z].
Bis[2-(benzimidazol-2-yl)phenolato-κ2N,O] cobalt(II) top
Crystal data top
[Co(C13H9N2O)2]Dx = 1.420 Mg m3
Mr = 477.37Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 1671 reflections
Hall symbol: P 4abw 2nwθ = 3.0–25.4°
a = 9.9452 (3) ŵ = 0.80 mm1
c = 22.581 (2) ÅT = 293 K
V = 2233.4 (2) Å3Block, red
Z = 40.17 × 0.15 × 0.14 mm
F(000) = 980
Data collection top
Bruker CCD area-detector
diffractometer
2669 independent reflections
Radiation source: fine-focus sealed tube2346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.876, Tmax = 0.896k = 1210
15456 measured reflectionsl = 2929
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0615P)2 + 0.7603P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2669 reflectionsΔρmax = 0.49 e Å3
150 parametersΔρmin = 0.22 e Å3
0 restraintsAbsolute structure: Flack (1983), 986 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.49 (3)
Crystal data top
[Co(C13H9N2O)2]Z = 4
Mr = 477.37Mo Kα radiation
Tetragonal, P41212µ = 0.80 mm1
a = 9.9452 (3) ÅT = 293 K
c = 22.581 (2) Å0.17 × 0.15 × 0.14 mm
V = 2233.4 (2) Å3
Data collection top
Bruker CCD area-detector
diffractometer
2669 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2346 reflections with I > 2σ(I)
Tmin = 0.876, Tmax = 0.896Rint = 0.033
15456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.49 e Å3
S = 1.09Δρmin = 0.22 e Å3
2669 reflectionsAbsolute structure: Flack (1983), 986 Friedel pairs
150 parametersAbsolute structure parameter: 0.49 (3)
0 restraints
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
xyzUiso*/Ueq
Co10.37726 (4)0.37726 (4)0.00000.03744 (16)
O10.2037 (2)0.4154 (2)0.03236 (9)0.0456 (5)
N10.2675 (3)0.6494 (3)0.12591 (13)0.0510 (7)
H10.20640.69590.14340.061*
N20.3659 (2)0.5170 (2)0.06036 (10)0.0396 (5)
C10.1079 (3)0.4912 (3)0.00874 (12)0.0409 (6)
C20.1249 (3)0.5715 (3)0.04303 (12)0.0416 (6)
C30.0171 (3)0.6494 (4)0.06224 (16)0.0591 (9)
H30.02870.70450.09510.071*
C40.1050 (4)0.6481 (5)0.0347 (2)0.0726 (11)
H40.17520.70090.04880.087*
C50.1229 (4)0.5677 (4)0.01408 (18)0.0693 (11)
H50.20640.56490.03260.083*
C60.0187 (4)0.4914 (4)0.03585 (16)0.0559 (8)
H60.03270.43870.06930.067*
C70.2512 (3)0.5771 (3)0.07535 (12)0.0373 (6)
C80.4003 (3)0.6350 (4)0.14439 (14)0.0511 (8)
C90.4700 (4)0.6868 (5)0.19162 (19)0.0786 (13)
H90.42870.74270.21920.094*
C100.6028 (4)0.6528 (6)0.1964 (2)0.0936 (16)
H100.65310.68690.22770.112*
C110.6642 (4)0.5686 (5)0.1556 (2)0.0853 (14)
H110.75470.54740.16030.102*
C120.5946 (3)0.5155 (4)0.10820 (17)0.0635 (10)
H120.63550.45800.08120.076*
C130.4605 (3)0.5521 (3)0.10286 (12)0.0434 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.03945 (19)0.03945 (19)0.0334 (2)0.0056 (2)0.00447 (15)0.00447 (15)
O10.0435 (12)0.0504 (12)0.0428 (10)0.0063 (9)0.0075 (9)0.0115 (9)
N10.0430 (14)0.0604 (19)0.0496 (13)0.0091 (12)0.0040 (11)0.0198 (13)
N20.0363 (12)0.0446 (13)0.0378 (11)0.0047 (10)0.0029 (10)0.0059 (9)
C10.0385 (15)0.0407 (14)0.0436 (14)0.0007 (11)0.0009 (12)0.0066 (12)
C20.0370 (13)0.0460 (14)0.0419 (13)0.0032 (13)0.0045 (12)0.0022 (11)
C30.0457 (18)0.072 (2)0.0595 (18)0.0157 (16)0.0040 (15)0.0063 (17)
C40.041 (2)0.096 (3)0.080 (2)0.0243 (19)0.0017 (17)0.003 (2)
C50.0386 (17)0.086 (3)0.083 (3)0.0074 (18)0.0125 (18)0.009 (2)
C60.0483 (19)0.064 (2)0.0552 (18)0.0013 (16)0.0123 (15)0.0017 (16)
C70.0382 (14)0.0387 (14)0.0350 (12)0.0021 (11)0.0055 (11)0.0029 (11)
C80.0436 (17)0.060 (2)0.0500 (15)0.0008 (15)0.0017 (12)0.0136 (14)
C90.072 (3)0.091 (3)0.073 (2)0.004 (2)0.013 (2)0.037 (2)
C100.068 (3)0.126 (4)0.087 (3)0.003 (3)0.029 (2)0.037 (3)
C110.049 (2)0.110 (4)0.097 (3)0.010 (2)0.026 (2)0.014 (3)
C120.044 (2)0.081 (3)0.066 (2)0.0119 (17)0.0029 (15)0.0134 (19)
C130.0398 (17)0.0484 (18)0.0421 (13)0.0019 (12)0.0010 (12)0.0037 (13)
Geometric parameters (Å, º) top
Co1—O1i1.912 (2)C4—C51.372 (6)
Co1—O11.912 (2)C4—H40.9300
Co1—N21.950 (2)C5—C61.375 (6)
Co1—N2i1.950 (2)C5—H50.9300
O1—C11.327 (3)C6—H60.9300
N1—C71.359 (4)C8—C91.373 (5)
N1—C81.392 (4)C8—C131.385 (4)
N1—H10.8600C9—C101.368 (6)
N2—C71.331 (3)C9—H90.9300
N2—C131.388 (4)C10—C111.387 (7)
C1—C61.400 (4)C10—H100.9300
C1—C21.426 (4)C11—C121.380 (6)
C2—C31.392 (4)C11—H110.9300
C2—C71.454 (4)C12—C131.388 (4)
C3—C41.364 (5)C12—H120.9300
C3—H30.9300
O1i—Co1—O1120.25 (13)C4—C5—H5119.7
O1—Co1—N294.22 (9)C6—C5—H5119.7
O1i—Co1—N2112.81 (9)C5—C6—C1121.5 (3)
O1i—Co1—N2i94.22 (9)C5—C6—H6119.3
O1—Co1—N2i112.81 (9)C1—C6—H6119.3
N2—Co1—N2i124.83 (15)N2—C7—N1110.4 (3)
C1—O1—Co1127.38 (18)N2—C7—C2126.6 (2)
C7—N1—C8108.1 (2)N1—C7—C2123.0 (3)
C7—N1—H1126.0C9—C8—C13122.1 (3)
C8—N1—H1126.0C9—C8—N1132.3 (3)
C7—N2—C13107.0 (2)C13—C8—N1105.6 (3)
C7—N2—Co1123.2 (2)C10—C9—C8117.1 (4)
C13—N2—Co1128.55 (19)C10—C9—H9121.4
O1—C1—C6118.1 (3)C8—C9—H9121.4
O1—C1—C2124.2 (3)C9—C10—C11121.5 (4)
C6—C1—C2117.7 (3)C9—C10—H10119.2
C3—C2—C1118.4 (3)C11—C10—H10119.2
C3—C2—C7119.2 (3)C12—C11—C10121.7 (4)
C1—C2—C7122.4 (3)C12—C11—H11119.2
C4—C3—C2122.6 (4)C10—C11—H11119.2
C4—C3—H3118.7C11—C12—C13116.7 (4)
C2—C3—H3118.7C11—C12—H12121.6
C3—C4—C5119.2 (4)C13—C12—H12121.6
C3—C4—H4120.4C8—C13—C12120.9 (3)
C5—C4—H4120.4C8—C13—N2109.0 (3)
C4—C5—C6120.7 (3)C12—C13—N2130.2 (3)
O1i—Co1—O1—C1106.6 (2)Co1—N2—C7—C213.5 (4)
N2—Co1—O1—C113.0 (2)C8—N1—C7—N20.0 (4)
N2i—Co1—O1—C1143.7 (2)C8—N1—C7—C2178.7 (3)
O1i—Co1—N2—C7110.1 (2)C3—C2—C7—N2174.7 (3)
O1—Co1—N2—C715.3 (2)C1—C2—C7—N23.8 (5)
N2i—Co1—N2—C7136.9 (2)C3—C2—C7—N13.9 (5)
O1i—Co1—N2—C1355.1 (3)C1—C2—C7—N1177.6 (3)
O1—Co1—N2—C13179.6 (3)C7—N1—C8—C9179.2 (4)
N2i—Co1—N2—C1357.9 (2)C7—N1—C8—C130.1 (4)
Co1—O1—C1—C6171.5 (2)C13—C8—C9—C100.3 (7)
Co1—O1—C1—C27.7 (4)N1—C8—C9—C10179.2 (4)
O1—C1—C2—C3178.2 (3)C8—C9—C10—C110.6 (8)
C6—C1—C2—C32.6 (4)C9—C10—C11—C120.2 (9)
O1—C1—C2—C70.3 (4)C10—C11—C12—C130.9 (8)
C6—C1—C2—C7178.9 (3)C9—C8—C13—C121.5 (6)
C1—C2—C3—C42.3 (5)N1—C8—C13—C12179.3 (3)
C7—C2—C3—C4179.1 (4)C9—C8—C13—N2179.4 (4)
C2—C3—C4—C50.4 (7)N1—C8—C13—N20.2 (4)
C3—C4—C5—C61.3 (7)C11—C12—C13—C81.7 (6)
C4—C5—C6—C11.0 (6)C11—C12—C13—N2179.3 (4)
O1—C1—C6—C5179.8 (3)C7—N2—C13—C80.2 (4)
C2—C1—C6—C51.0 (5)Co1—N2—C13—C8166.9 (2)
C13—N2—C7—N10.2 (3)C7—N2—C13—C12179.3 (4)
Co1—N2—C7—N1167.8 (2)Co1—N2—C13—C1212.2 (5)
C13—N2—C7—C2178.6 (3)
Symmetry code: (i) y, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.862.072.809 (3)144
Symmetry code: (ii) y+1/2, x+1/2, z+1/4.

Experimental details

Crystal data
Chemical formula[Co(C13H9N2O)2]
Mr477.37
Crystal system, space groupTetragonal, P41212
Temperature (K)293
a, c (Å)9.9452 (3), 22.581 (2)
V3)2233.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.80
Crystal size (mm)0.17 × 0.15 × 0.14
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.876, 0.896
No. of measured, independent and
observed [I > 2σ(I)] reflections
15456, 2669, 2346
Rint0.033
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.09
No. of reflections2669
No. of parameters150
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.22
Absolute structureFlack (1983), 986 Friedel pairs
Absolute structure parameter0.49 (3)

Computer programs: SMART (Bruker, 2005), SAINT-Plus (Bruker, 2005), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005), SHELXTL.

Selected geometric parameters (Å, º) top
Co1—O11.912 (2)Co1—N21.950 (2)
O1i—Co1—O1120.25 (13)O1i—Co1—N2112.81 (9)
O1—Co1—N294.22 (9)N2—Co1—N2i124.83 (15)
Symmetry code: (i) y, x, z.
 

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