metal-organic compounds
cis-Bis{(E)-2-[(2-fluorophenyl)iminomethyl]phenolato-κ2N,O}bis(pyridine-κN)nickel(II)†
aInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro, RJ, Brazil, bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil, and cR&D NanoBusiness, e-Diffraction Pharma, 22451-900 Rio de Janeiro, RJ, Brazil
*Correspondence e-mail: lorenzo.visentin@nanobusiness.com.br
The structure of the title compound, [Ni(C13H9FNO)2(C5H5N)2], consists of an NiII atom on a crystallographic center of symmetry, octahedrally bonded through both the N and O atoms to two 2-[(2-fluorophenyl)iminomethyl]phenolate (L) ligands, as well as two pyridine ligands. The F atoms of L are disordered over two positions related by a 180° rotation of the fluorophenyl group around its external C—N bond.
Related literature
For related nickel compounds, see: Dang et al. (2009); Orpen et al. (1989). For related N-salicylidene anilines, see: Lindeman et al. (1981); Temel et al. (2007); Çelik et al. (2009).
Experimental
Crystal data
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Data collection: COLLECT (Hooft, 1998); cell PHICHI (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536812045576/br2213sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045576/br2213Isup2.hkl
For 2-fluorophenyliminomethyl)phenol ligand (LH). To a solution of 2-hydroxybenzaldehyde (2.6 ml, 25.0 mmol) in 50.0 ml of ethanol was added a mixture of NaOH/HCl (3.0 ml, pH 5.0) and 2-fluoroaniline (2.4 ml, 25.0 mmol). The reaction mixture was kept under reflux for 2 h with continuous stirring. The reaction mixture was cooled to 273 K for 24 h, the yellow precipitate was collected and washed with water and ethanol. Yield: 70%. M.P. 328–330 K; Elemental Analysis, CHN, for C13H10F1N1O1 (Found C, 78.63; H, 5.62; N, 6.96. Calculate: C, 79.16; H, 6.37;N, 7.10%).
For C36H26F2N4O2Ni. A solution of LH (0.430 g, 0.2 mmol), 3.0 ml of MeOH / MeONa (10% w/v) and 5.0 ml of pyridine in 20.0 ml of acetone was stirred for five minutes. Then nickel(II) acetate (0.176 g, 0.1 mmol) was added. The reaction mixture was stirred for 24 h at room temperature. The solution was filtered off and red block crystals suitable for X-ray analysis were obtained by slow evaporation of the solution at room temperature. Yield: 55%. M.P. 569–571 K; Elemental Analysis, CHN, for C36H26F2N4O2Ni (Found C, 67.86; H,4.15; N, 7.38. Calculated: C, 68.39; H, 4.45; N, 8.14%).
H atoms of the unsaturated carbon were positioned geometrically (C–H = 0.93 Å for Csp2 atoms) and treated as riding on their respective C atoms, with Uiso(H) values set at 1.2UeqCsp2. The H9 and H13 atoms were omitted for solve of the disorder in the F1 and F1' atoms attached in C9 and C13.
Data collection: COLLECT (Hooft, 1998); cell
PHICHI (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. ORTEP projection of the title molecule. Thermal ellipsoids are at the 30% probability level. |
[Ni(C13H9FNO)2(C5H5N)2] | Z = 1 |
Mr = 645.32 | F(000) = 332 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Melting point: 569 K |
a = 8.3160 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.344 (2) Å | Cell parameters from 370 reflections |
c = 11.049 (2) Å | θ = 1–27.5° |
α = 109.94 (3)° | µ = 0.67 mm−1 |
β = 98.53 (3)° | T = 295 K |
γ = 111.93 (3)° | Block, red |
V = 786.2 (3) Å3 | 0.17 × 0.16 × 0.12 mm |
Nonius KappaCCD diffractometer | 2909 independent reflections |
Radiation source: fine-focus sealed tube | 2652 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ϕ scans, and ω scans with κ | θmax = 25.5°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −10→9 |
Tmin = 0.895, Tmax = 0.924 | k = −12→12 |
11574 measured reflections | l = −13→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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.389P] where P = (Fo2 + 2Fc2)/3 |
2909 reflections | (Δ/σ)max < 0.001 |
219 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
[Ni(C13H9FNO)2(C5H5N)2] | γ = 111.93 (3)° |
Mr = 645.32 | V = 786.2 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.3160 (17) Å | Mo Kα radiation |
b = 10.344 (2) Å | µ = 0.67 mm−1 |
c = 11.049 (2) Å | T = 295 K |
α = 109.94 (3)° | 0.17 × 0.16 × 0.12 mm |
β = 98.53 (3)° |
Nonius KappaCCD diffractometer | 2909 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2652 reflections with I > 2σ(I) |
Tmin = 0.895, Tmax = 0.924 | Rint = 0.026 |
11574 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.41 e Å−3 |
2909 reflections | Δρmin = −0.32 e Å−3 |
219 parameters |
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 | Occ. (<1) | |
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.04073 (15) | |
C1 | 0.3568 (3) | 0.1876 (2) | −0.0377 (2) | 0.0434 (5) | |
C2 | 0.4086 (3) | 0.3195 (2) | 0.0890 (2) | 0.0438 (5) | |
C3 | 0.3036 (3) | 0.3221 (2) | 0.1802 (2) | 0.0419 (5) | |
C4 | 0.3826 (4) | 0.4568 (3) | 0.3068 (2) | 0.0563 (6) | |
H4 | 0.3208 | 0.4613 | 0.3706 | 0.068* | |
C5 | 0.5489 (4) | 0.5805 (3) | 0.3367 (3) | 0.0677 (8) | |
H5 | 0.5966 | 0.6664 | 0.4200 | 0.081* | |
C6 | 0.6465 (4) | 0.5792 (3) | 0.2444 (3) | 0.0700 (8) | |
H6 | 0.7565 | 0.6642 | 0.2644 | 0.084* | |
C7 | 0.5771 (3) | 0.4504 (3) | 0.1237 (3) | 0.0598 (6) | |
H7 | 0.6427 | 0.4486 | 0.0624 | 0.072* | |
C8 | 0.1974 (3) | −0.0607 (2) | −0.2117 (2) | 0.0388 (4) | |
C9 | 0.1232 (3) | −0.0664 (3) | −0.3351 (2) | 0.0513 (5) | |
C10 | 0.0995 (4) | −0.1814 (3) | −0.4576 (2) | 0.0645 (7) | |
H10 | 0.0511 | −0.1816 | −0.5392 | 0.077* | |
C11 | 0.1480 (4) | −0.2945 (3) | −0.4574 (3) | 0.0661 (7) | |
H11 | 0.1311 | −0.3727 | −0.5389 | 0.079* | |
C12 | 0.2215 (5) | −0.2914 (3) | −0.3360 (3) | 0.0705 (8) | |
H12 | 0.2560 | −0.3671 | −0.3356 | 0.085* | |
C13 | 0.2449 (4) | −0.1764 (3) | −0.2140 (3) | 0.0574 (6) | |
C14 | 0.0620 (5) | −0.2436 (3) | 0.0879 (3) | 0.0752 (8) | |
H14 | −0.0445 | −0.3115 | 0.0149 | 0.090* | |
C15 | 0.1386 (6) | −0.3036 (4) | 0.1603 (4) | 0.0860 (10) | |
H15 | 0.0836 | −0.4091 | 0.1363 | 0.103* | |
C16 | 0.2949 (4) | −0.2069 (4) | 0.2667 (3) | 0.0716 (8) | |
H16 | 0.3489 | −0.2448 | 0.3167 | 0.086* | |
C17 | 0.3709 (4) | −0.0527 (4) | 0.2986 (3) | 0.0793 (9) | |
H17 | 0.4783 | 0.0167 | 0.3704 | 0.095* | |
C18 | 0.2847 (4) | −0.0020 (3) | 0.2217 (3) | 0.0674 (7) | |
H18 | 0.3368 | 0.1034 | 0.2450 | 0.081* | |
N1 | 0.2146 (2) | 0.05438 (19) | −0.08618 (16) | 0.0381 (4) | |
N2 | 0.1329 (2) | −0.0937 (2) | 0.11714 (19) | 0.0463 (4) | |
O1 | 0.1449 (2) | 0.21035 (17) | 0.15535 (15) | 0.0486 (4) | |
H1 | 0.438 (4) | 0.204 (3) | −0.085 (3) | 0.060 (7)* | |
F1 | 0.0721 (4) | 0.0386 (3) | −0.3371 (2) | 0.0771 (9) | 0.700 (4) |
F1' | 0.2941 (10) | −0.1824 (8) | −0.1059 (5) | 0.086 (2) | 0.300 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0372 (2) | 0.0367 (2) | 0.0399 (2) | 0.01420 (16) | 0.00849 (15) | 0.01184 (16) |
C1 | 0.0392 (11) | 0.0459 (11) | 0.0413 (11) | 0.0147 (9) | 0.0096 (9) | 0.0210 (9) |
C2 | 0.0423 (11) | 0.0365 (10) | 0.0426 (11) | 0.0118 (9) | 0.0013 (9) | 0.0181 (9) |
C3 | 0.0453 (11) | 0.0330 (9) | 0.0389 (10) | 0.0185 (9) | −0.0003 (8) | 0.0113 (8) |
C4 | 0.0629 (15) | 0.0420 (12) | 0.0468 (12) | 0.0257 (11) | 0.0013 (11) | 0.0051 (10) |
C5 | 0.0727 (17) | 0.0331 (11) | 0.0590 (15) | 0.0178 (12) | −0.0163 (13) | 0.0004 (11) |
C6 | 0.0599 (15) | 0.0407 (13) | 0.0728 (17) | 0.0015 (11) | −0.0091 (14) | 0.0206 (12) |
C7 | 0.0515 (14) | 0.0476 (13) | 0.0606 (15) | 0.0063 (11) | 0.0030 (11) | 0.0258 (11) |
C8 | 0.0333 (9) | 0.0387 (10) | 0.0382 (10) | 0.0125 (8) | 0.0109 (8) | 0.0144 (8) |
C9 | 0.0509 (13) | 0.0586 (13) | 0.0438 (12) | 0.0271 (11) | 0.0104 (10) | 0.0208 (10) |
C10 | 0.0603 (15) | 0.0769 (18) | 0.0370 (12) | 0.0270 (14) | 0.0055 (11) | 0.0124 (11) |
C11 | 0.0730 (17) | 0.0494 (13) | 0.0513 (14) | 0.0183 (13) | 0.0222 (13) | 0.0045 (11) |
C12 | 0.101 (2) | 0.0541 (15) | 0.0755 (18) | 0.0470 (16) | 0.0434 (17) | 0.0295 (13) |
C13 | 0.0748 (17) | 0.0597 (14) | 0.0545 (14) | 0.0419 (13) | 0.0264 (12) | 0.0282 (12) |
C14 | 0.090 (2) | 0.0529 (15) | 0.0689 (17) | 0.0363 (15) | −0.0046 (15) | 0.0190 (13) |
C15 | 0.117 (3) | 0.0642 (18) | 0.083 (2) | 0.0542 (19) | 0.012 (2) | 0.0334 (16) |
C16 | 0.0747 (18) | 0.103 (2) | 0.0810 (19) | 0.0589 (18) | 0.0324 (16) | 0.0635 (18) |
C17 | 0.0539 (15) | 0.097 (2) | 0.086 (2) | 0.0232 (15) | 0.0016 (14) | 0.0591 (19) |
C18 | 0.0504 (14) | 0.0648 (16) | 0.0787 (18) | 0.0138 (12) | 0.0018 (13) | 0.0435 (14) |
N1 | 0.0367 (8) | 0.0374 (8) | 0.0353 (8) | 0.0162 (7) | 0.0070 (7) | 0.0130 (7) |
N2 | 0.0430 (10) | 0.0518 (10) | 0.0495 (10) | 0.0241 (8) | 0.0144 (8) | 0.0252 (8) |
O1 | 0.0457 (8) | 0.0416 (8) | 0.0439 (8) | 0.0158 (7) | 0.0116 (6) | 0.0081 (6) |
F1 | 0.120 (2) | 0.0914 (17) | 0.0525 (13) | 0.0771 (17) | 0.0231 (13) | 0.0362 (12) |
F1' | 0.143 (6) | 0.110 (5) | 0.060 (3) | 0.104 (5) | 0.038 (3) | 0.045 (3) |
N1—Ni1 | 2.128 (2) | C8—N1 | 1.431 (3) |
N2—Ni1 | 2.251 (2) | C9—C10 | 1.390 (3) |
Ni1—O1i | 2.003 (2) | C10—C11 | 1.373 (4) |
Ni1—O1 | 2.003 (2) | C10—H10 | 0.9300 |
Ni1—N1i | 2.128 (2) | C11—C12 | 1.374 (4) |
Ni1—N2i | 2.251 (2) | C11—H11 | 0.9300 |
C1—N1 | 1.294 (3) | C12—C13 | 1.388 (4) |
C1—C2 | 1.444 (3) | C12—H12 | 0.9300 |
C1—H1 | 0.92 (3) | C14—N2 | 1.333 (3) |
C2—C7 | 1.419 (3) | C14—C15 | 1.383 (4) |
C2—C3 | 1.428 (3) | C14—H14 | 0.9300 |
C3—O1 | 1.300 (3) | C15—C16 | 1.359 (5) |
C3—C4 | 1.430 (3) | C15—H15 | 0.9300 |
C4—C5 | 1.384 (4) | C16—C17 | 1.366 (4) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.394 (5) | C17—C18 | 1.384 (4) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.368 (4) | C18—N2 | 1.324 (3) |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | F1—C9 | 1.311 (3) |
C8—C9 | 1.382 (3) | F1'—C13 | 1.234 (5) |
C8—C13 | 1.387 (3) | ||
O1—Ni1—N1 | 88.26 (7) | C4—C5—C6 | 121.4 (2) |
O1i—Ni1—N1 | 91.74 (7) | C4—C5—H5 | 119.3 |
O1—Ni1—N1i | 91.74 (7) | C6—C5—H5 | 119.3 |
O1i—Ni1—N1i | 88.26 (7) | C5—C4—C3 | 121.5 (3) |
O1—Ni1—N2 | 89.03 (7) | C5—C4—H4 | 119.3 |
O1i—Ni1—N2 | 90.97 (7) | C3—C4—H4 | 119.3 |
N1—Ni1—N2 | 91.69 (7) | C11—C12—C13 | 120.6 (3) |
N1i—Ni1—N2 | 88.31 (7) | C11—C12—H12 | 119.7 |
O1—Ni1—N2i | 90.97 (7) | C13—C12—H12 | 119.7 |
O1i—Ni1—N2i | 89.03 (7) | C11—C10—C9 | 119.6 (2) |
N1—Ni1—N2i | 88.31 (7) | C11—C10—H10 | 120.2 |
N1i—Ni1—N2i | 91.69 (7) | C9—C10—H10 | 120.2 |
C3—O1—Ni1 | 131.3 (1) | N2—C18—C17 | 124.2 (3) |
C1—N1—C8 | 116.6 (2) | N2—C18—H18 | 117.9 |
C1—N1—Ni1 | 125.0 (2) | C17—C18—H18 | 117.9 |
C8—N1—Ni1 | 118.3 (1) | C10—C11—C12 | 119.5 (2) |
C18—N2—C14 | 115.9 (2) | C10—C11—H11 | 120.2 |
C18—N2—Ni1 | 121.7 (2) | C12—C11—H11 | 120.2 |
C14—N2—Ni1 | 122.3 (2) | C6—C7—C2 | 122.2 (3) |
C9—C8—C13 | 117.5 (2) | C6—C7—H7 | 118.9 |
C9—C8—N1 | 121.6 (2) | C2—C7—H7 | 118.9 |
C13—C8—N1 | 120.9 (2) | C7—C6—C5 | 118.7 (2) |
N1—C1—C2 | 127.1 (2) | C7—C6—H6 | 120.7 |
N1—C1—H1 | 120 (2) | C5—C6—H6 | 120.7 |
C2—C1—H1 | 113 (2) | N2—C14—C15 | 123.4 (3) |
O1—C3—C2 | 124.2 (2) | N2—C14—H14 | 118.3 |
O1—C3—C4 | 119.2 (2) | C15—C14—H14 | 118.3 |
C2—C3—C4 | 116.6 (2) | C15—C16—C17 | 118.4 (3) |
C7—C2—C3 | 119.6 (2) | C15—C16—H16 | 120.8 |
C7—C2—C1 | 116.6 (2) | C17—C16—H16 | 120.8 |
C3—C2—C1 | 123.8 (2) | C16—C17—C18 | 118.6 (3) |
F1—C9—C8 | 119.2 (2) | C16—C17—H17 | 120.7 |
F1—C9—C10 | 118.9 (2) | C18—C17—H17 | 120.7 |
C8—C9—C10 | 121.9 (2) | C16—C15—C14 | 119.4 (3) |
F1'—C13—C8 | 118.5 (3) | C16—C15—H15 | 120.3 |
F1'—C13—C12 | 120.4 (3) | C14—C15—H15 | 120.3 |
C8—C13—C12 | 120.9 (2) | ||
C8—N1—C1—C2 | −177.3 (2) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C13H9FNO)2(C5H5N)2] |
Mr | 645.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.3160 (17), 10.344 (2), 11.049 (2) |
α, β, γ (°) | 109.94 (3), 98.53 (3), 111.93 (3) |
V (Å3) | 786.2 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.67 |
Crystal size (mm) | 0.17 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.895, 0.924 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11574, 2909, 2652 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.105, 1.05 |
No. of reflections | 2909 |
No. of parameters | 219 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.32 |
Computer programs: COLLECT (Hooft, 1998), PHICHI (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
Footnotes
†In memoriam Professor Jairo Bordinhão.
Acknowledgements
The authors are grateful to their sponsors, CNPq, CAPES and FAPERJ for financial support and also to the Laboratório de Difração de Raios X, (LDRX), Universidade Federal Fluminense, Brazil, for the diffractometer facility. Thanks are due to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a license for the use of the Cambridge Structural Database. We thank Professor James Lewis Wardell for scientific support of this work.
References
Çelik, Ö., Kasumov, V. T. & Şahin, E. (2009). Acta Cryst. E65, o2786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dang, Y.-Q., Yang, H.-J. & Tian, L.-J. (2009). Acta Cryst. E65, m231. Web of Science CSD CrossRef IUCr Journals Google Scholar
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893–898. Web of Science CrossRef CAS IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Lindeman, S. V., Andrianov, V. G., Kravcheni, S. G., Potapov, V. M., Potekhin, K. A. & Struchkov, Yu. T. (1981). Zh. Strukt. Khim. 22, 123–131. CAS Google Scholar
Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G. & Taylor, R. (1989). J. Chem. Soc. Dalton Trans. pp. S1–83. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Temel, E., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o2642. Web of Science CSD CrossRef IUCr Journals Google Scholar
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N-Salicylidene anilines (Lindeman et al., 1981; Temel et al., 2007; Çelik et al., 2009;) are Schiff bases easily prepared by condensation of salicylaldehyde and an aniline. These molecules act as ligands with transition metals. The NiII cation is octahedrally coordinated by four N and two O atoms with only slight distortion from the ideal coordination geometry. The two independent 2-(E)-(2-fluorophenyliminomethyl)phenolato ligands are bidentate and provide each one N atom from the imine moiety and one phenolato O atom. The coordination is completed by the two pyridine N atoms in trans arrangement. The Ni—N and Ni—O distances (Table 1) are in the typical ranges and like all other interatomic distances are in good agreement with literature data (Dang, et al., 2009; Orpen et al., 1989). The dihedral angle between C8-C13 and C2-C7 phenyl rings is 82.9 (1)°, This compound exhibits a statistical disorder, showing two partial fluorine atoms in unequal proportions (0.700 (4):0.300 (4)), F1 and F1', respectively.