Acta Cryst. (2008). E64, m1394 [ doi:10.1107/S1600536808032303 ]
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2N,O}cobalt(II)In the title compound, [Co(C14H10Br2NO)2], the CoII ion is coordinated by an O and an N atom from two equivalent 2-[(E)-benzyliminomethyl]-4,6-dibromophenolate ligands, displaying a distorted tetrahedral geometry. The CoII ion occupies a special position on a twofold rotation axis and thus the molecular symmetry of the complex is C2. The two phenolate rings are perpendicular [89.8 (3)°].
To a solution containing 2 mmol (0.738 g) 2-((E)-(benzylimino)methyl)-4,6-dibromophenol dissolved in 20 mL ethanol, 1 mmol of CoCl2.6H2O (0.238 g) were added, and the resulting mixture was stirred for about 1 h. The slow evaporisation of the solvent after about 3 d yielded dark brown single crystals. Yield: 51.4%. Calcd. for C28H20Br4CoN2O2: C, 42.30; H, 2.54; N, 3.52; Found: C, 42.24; H, 3.41; N,3.46%.
All H atoms were located from difference Fourier syntheses, H atoms from the C—H groups were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93 Å, 0.96 Å, 0.97 Å) and Uiso(H) values equal to 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).
![[Figure 1]](./kp2194fig1thm.gif)
| Fig. 1. The structure of (I), showing displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x, y, -z+0.5] |
| [Co(C14H10Br2NO)2] | F(000) = 1540 |
| Mr = 795.03 | Dx = 1.971 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 2269 reflections |
| a = 23.875 (3) Å | θ = 1.0–27.7° |
| b = 4.8190 (6) Å | µ = 6.64 mm−1 |
| c = 24.209 (3) Å | T = 296 K |
| β = 105.873 (1)° | Block, brown |
| V = 2679.1 (6) Å3 | 0.30 × 0.26 × 0.22 mm |
| Z = 4 |
| Bruker SMART APEXII CCD diffractometer | 3094 independent reflections |
| Radiation source: fine-focus sealed tube | 2627 reflections with I > 2σ(I) |
| graphite | Rint = 0.027 |
| φ and ω scans | θmax = 27.7°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −30→30 |
| Tmin = 0.165, Tmax = 0.232 | k = −6→6 |
| 11046 measured reflections | l = −30→31 |
| 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.172 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.1045P)2 + 20.5054P] where P = (Fo2 + 2Fc2)/3 |
| 3094 reflections | (Δ/σ)max < 0.001 |
| 168 parameters | Δρmax = 0.98 e Å−3 |
| 0 restraints | Δρmin = −1.45 e Å−3 |
| [Co(C14H10Br2NO)2] | V = 2679.1 (6) Å3 |
| Mr = 795.03 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 23.875 (3) Å | µ = 6.64 mm−1 |
| b = 4.8190 (6) Å | T = 296 K |
| c = 24.209 (3) Å | 0.30 × 0.26 × 0.22 mm |
| β = 105.873 (1)° |
| Bruker SMART APEXII CCD diffractometer | 3094 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 2627 reflections with I > 2σ(I) |
| Tmin = 0.165, Tmax = 0.232 | Rint = 0.027 |
| 11046 measured reflections | θmax = 27.7° |
| R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.1045P)2 + 20.5054P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.172 | Δρmax = 0.98 e Å−3 |
| S = 1.07 | Δρmin = −1.45 e Å−3 |
| 3094 reflections | Absolute structure: ? |
| 168 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| H-atom parameters constrained |
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 > 2sigma(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 | 0.0000 | 0.9824 (2) | 0.2500 | 0.0481 (3) | |
| Br1 | 0.25733 (3) | 0.73207 (15) | 0.14570 (3) | 0.0446 (2) | |
| Br2 | 0.06423 (3) | 1.45190 (13) | 0.09822 (2) | 0.0389 (2) | |
| O1 | 0.04168 (16) | 1.1622 (8) | 0.20173 (16) | 0.0316 (8) | |
| N1 | −0.06936 (19) | 0.7651 (9) | 0.20554 (18) | 0.0269 (9) | |
| C1 | 0.0898 (2) | 1.0738 (10) | 0.1927 (2) | 0.0260 (10) | |
| C2 | 0.1095 (2) | 1.1793 (11) | 0.1464 (2) | 0.0285 (10) | |
| C3 | 0.1595 (2) | 1.0865 (12) | 0.1339 (2) | 0.0313 (11) | |
| H3A | 0.1707 | 1.1621 | 0.1032 | 0.038* | |
| C4 | 0.1925 (2) | 0.8813 (13) | 0.1672 (2) | 0.0321 (11) | |
| C5 | 0.1772 (2) | 0.7738 (12) | 0.2136 (2) | 0.0336 (11) | |
| H5A | 0.2005 | 0.6395 | 0.2364 | 0.040* | |
| C6 | 0.1268 (2) | 0.8649 (12) | 0.2269 (2) | 0.0281 (10) | |
| C7 | −0.1144 (2) | 0.7334 (12) | 0.2242 (2) | 0.0309 (11) | |
| H7A | −0.1425 | 0.6106 | 0.2037 | 0.037* | |
| C8 | −0.0702 (3) | 0.6166 (12) | 0.1512 (2) | 0.0327 (11) | |
| H8A | −0.0934 | 0.4492 | 0.1482 | 0.039* | |
| H8B | −0.0309 | 0.5631 | 0.1517 | 0.039* | |
| C9 | −0.0954 (3) | 0.7997 (11) | 0.1000 (2) | 0.0320 (11) | |
| C10 | −0.1555 (3) | 0.8139 (16) | 0.0759 (3) | 0.0483 (16) | |
| H10A | −0.1807 | 0.7055 | 0.0901 | 0.058* | |
| C11 | −0.1773 (4) | 0.9955 (19) | 0.0296 (3) | 0.059 (2) | |
| H11A | −0.2174 | 1.0061 | 0.0137 | 0.071* | |
| C12 | −0.1433 (4) | 1.1523 (16) | 0.0075 (3) | 0.0555 (19) | |
| H12A | −0.1593 | 1.2715 | −0.0229 | 0.067* | |
| C13 | −0.0827 (4) | 1.1356 (17) | 0.0309 (3) | 0.0533 (17) | |
| H13A | −0.0581 | 1.2426 | 0.0157 | 0.064* | |
| C14 | −0.0597 (3) | 0.9608 (14) | 0.0764 (3) | 0.0420 (14) | |
| H14A | −0.0195 | 0.9504 | 0.0915 | 0.050* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Co1 | 0.0443 (5) | 0.0596 (6) | 0.0428 (5) | 0.000 | 0.0163 (4) | 0.000 |
| Br1 | 0.0289 (3) | 0.0637 (4) | 0.0467 (4) | 0.0012 (2) | 0.0197 (3) | −0.0043 (3) |
| Br2 | 0.0460 (4) | 0.0389 (3) | 0.0348 (3) | 0.0015 (2) | 0.0160 (3) | 0.0099 (2) |
| O1 | 0.0320 (19) | 0.039 (2) | 0.0299 (19) | 0.0049 (16) | 0.0186 (16) | 0.0067 (16) |
| N1 | 0.027 (2) | 0.033 (2) | 0.021 (2) | 0.0010 (16) | 0.0071 (17) | 0.0003 (16) |
| C1 | 0.028 (2) | 0.030 (2) | 0.022 (2) | −0.0039 (19) | 0.0092 (19) | −0.0012 (18) |
| C2 | 0.033 (3) | 0.031 (3) | 0.024 (2) | −0.006 (2) | 0.011 (2) | −0.0022 (19) |
| C3 | 0.032 (3) | 0.038 (3) | 0.028 (3) | −0.010 (2) | 0.014 (2) | −0.005 (2) |
| C4 | 0.026 (2) | 0.042 (3) | 0.032 (3) | −0.004 (2) | 0.012 (2) | −0.006 (2) |
| C5 | 0.027 (3) | 0.044 (3) | 0.029 (3) | 0.001 (2) | 0.006 (2) | 0.000 (2) |
| C6 | 0.026 (2) | 0.038 (3) | 0.022 (2) | −0.002 (2) | 0.0078 (19) | −0.001 (2) |
| C7 | 0.027 (3) | 0.042 (3) | 0.023 (2) | −0.004 (2) | 0.006 (2) | −0.003 (2) |
| C8 | 0.041 (3) | 0.034 (3) | 0.025 (2) | 0.006 (2) | 0.013 (2) | −0.002 (2) |
| C9 | 0.045 (3) | 0.031 (3) | 0.023 (2) | 0.001 (2) | 0.013 (2) | −0.0074 (19) |
| C10 | 0.043 (4) | 0.061 (4) | 0.042 (4) | 0.007 (3) | 0.014 (3) | 0.004 (3) |
| C11 | 0.048 (4) | 0.076 (5) | 0.046 (4) | 0.016 (4) | 0.000 (3) | 0.003 (4) |
| C12 | 0.084 (6) | 0.051 (4) | 0.025 (3) | 0.005 (4) | 0.005 (3) | 0.001 (3) |
| C13 | 0.065 (5) | 0.056 (4) | 0.036 (3) | −0.011 (4) | 0.010 (3) | 0.006 (3) |
| C14 | 0.044 (3) | 0.052 (4) | 0.029 (3) | −0.007 (3) | 0.008 (3) | 0.000 (2) |
| Co1—O1i | 1.935 (4) | C6—C7i | 1.441 (7) |
| Co1—O1 | 1.935 (4) | C7—C6i | 1.441 (7) |
| Co1—N1 | 2.005 (4) | C7—H7A | 0.9300 |
| Co1—N1i | 2.005 (4) | C8—C9 | 1.505 (8) |
| Br1—C4 | 1.902 (5) | C8—H8A | 0.9700 |
| Br2—C2 | 1.888 (6) | C8—H8B | 0.9700 |
| O1—C1 | 1.298 (6) | C9—C14 | 1.388 (8) |
| N1—C7 | 1.285 (7) | C9—C10 | 1.396 (9) |
| N1—C8 | 1.493 (7) | C10—C11 | 1.404 (11) |
| C1—C2 | 1.424 (7) | C10—H10A | 0.9300 |
| C1—C6 | 1.442 (7) | C11—C12 | 1.323 (12) |
| C2—C3 | 1.383 (7) | C11—H11A | 0.9300 |
| C3—C4 | 1.379 (8) | C12—C13 | 1.405 (11) |
| C3—H3A | 0.9300 | C12—H12A | 0.9300 |
| C4—C5 | 1.376 (8) | C13—C14 | 1.375 (10) |
| C5—C6 | 1.399 (8) | C13—H13A | 0.9300 |
| C5—H5A | 0.9300 | C14—H14A | 0.9300 |
| O1i—Co1—O1 | 126.8 (2) | N1—C7—C6i | 127.9 (5) |
| O1i—Co1—N1 | 94.16 (17) | N1—C7—H7A | 116.0 |
| O1—Co1—N1 | 113.29 (17) | C6i—C7—H7A | 116.0 |
| O1i—Co1—N1i | 113.29 (17) | N1—C8—C9 | 110.5 (4) |
| O1—Co1—N1i | 94.16 (17) | N1—C8—H8A | 109.6 |
| N1—Co1—N1i | 117.1 (3) | C9—C8—H8A | 109.6 |
| C1—O1—Co1 | 125.4 (3) | N1—C8—H8B | 109.6 |
| C7—N1—C8 | 116.2 (5) | C9—C8—H8B | 109.6 |
| C7—N1—Co1 | 121.4 (4) | H8A—C8—H8B | 108.1 |
| C8—N1—Co1 | 122.3 (4) | C14—C9—C10 | 118.5 (6) |
| O1—C1—C2 | 120.9 (5) | C14—C9—C8 | 121.1 (6) |
| O1—C1—C6 | 124.4 (4) | C10—C9—C8 | 120.5 (6) |
| C2—C1—C6 | 114.7 (4) | C9—C10—C11 | 118.6 (7) |
| C3—C2—C1 | 123.3 (5) | C9—C10—H10A | 120.7 |
| C3—C2—Br2 | 118.2 (4) | C11—C10—H10A | 120.7 |
| C1—C2—Br2 | 118.6 (4) | C12—C11—C10 | 123.0 (7) |
| C4—C3—C2 | 119.6 (5) | C12—C11—H11A | 118.5 |
| C4—C3—H3A | 120.2 | C10—C11—H11A | 118.5 |
| C2—C3—H3A | 120.2 | C11—C12—C13 | 118.8 (7) |
| C5—C4—C3 | 120.6 (5) | C11—C12—H12A | 120.6 |
| C5—C4—Br1 | 120.0 (5) | C13—C12—H12A | 120.6 |
| C3—C4—Br1 | 119.3 (4) | C14—C13—C12 | 120.0 (7) |
| C4—C5—C6 | 120.6 (5) | C14—C13—H13A | 120.0 |
| C4—C5—H5A | 119.7 | C12—C13—H13A | 120.0 |
| C6—C5—H5A | 119.7 | C13—C14—C9 | 121.2 (7) |
| C5—C6—C7i | 115.6 (5) | C13—C14—H14A | 119.4 |
| C5—C6—C1 | 121.2 (5) | C9—C14—H14A | 119.4 |
| C7i—C6—C1 | 123.2 (5) |
| Symmetry codes: (i) −x, y, −z+1/2. |
| Co1—O1 | 1.935 (4) | Co1—N1 | 2.005 (4) |
| O1i—Co1—O1 | 126.8 (2) | O1—Co1—N1 | 113.29 (17) |
| O1i—Co1—N1 | 94.16 (17) | N1—Co1—N1i | 117.1 (3) |
| Symmetry codes: (i) −x, y, −z+1/2. |
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, K. Y. & Jeon, Y. M. (2003). Inorg. Chem. Commun. 6, 1294–296.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. [2000 here, but originally cited as 1997 - which is correct?]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The Schiff bases are widely employed as ligands in coordination chemistry. The advantages of Schiff bases enable their use in the synthesis of metal complexes of interest in bioinorganic chemistry, catalysis, encapsulation, transport and separation processes, and magnetochemistry (Choi & Jeon, 2003). Salicylaldehyde and its derivatives are useful carbonyl precursors for the synthesis of a large variety of Schiff bases. In this paper we report on a new cobalt(II) complex (I).
In the title complex CoII atom is tetrahedrally coordinated by two O atoms and two N atoms from two 2-((E)-(benzylimino)methyl)-4,6-dibromophenol bidentate chelating ligand. The Co1—O1 distance of 1.935 (4) Å is shorter than the distance of Co1—N1 (2.005 (4) Å) (Table 1). The dihedral angle between two phenol rings is 89.8 (3)°.