cis-Bis{(E)-2-[(2-fluoro­phen­yl)imino­meth­yl]phenolato-κ2N,O}bis­(pyridine-κN)nickel(II)

Souza, M.C.G.; Ferreira, L. da C.; Comerlato, N.M.; Ferreira, G.B.; Visentin, L. do C.

doi:10.1107/S1600536812045576

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1470

doi:10.1107/S1600536812045576

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cis-Bis{(E)-2-[(2-fluorophenyl)iminomethyl]phenolato-κ²N,O}bis(pyridine-κN)nickel(II)†

Marcela C. G. Souza,^a Leonardo da C. Ferreira,^a Nadia M. Comerlato,^a Glaucio B. Ferreira ^b and Lorenzo do Canto Visentin ^c ^*

^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

(Received 29 October 2012; accepted 4 November 2012; online 10 November 2012)

The structure of the title compound, [Ni(C₁₃H₉FNO)₂(C₅H₅N)₂], consists of an Ni^II 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

[Ni(C₁₃H₉FNO)₂(C₅H₅N)₂]
M_r = 645.32
Triclinic, $[P \overline 1]$
a = 8.3160 (17) Å
b = 10.344 (2) Å
c = 11.049 (2) Å
α = 109.94 (3)°
β = 98.53 (3)°
γ = 111.93 (3)°
V = 786.2 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.67 mm⁻¹
T = 295 K
0.17 × 0.16 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.895, T_max = 0.924
11574 measured reflections
2909 independent reflections
2652 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.05
2909 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045576/br2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045576/br2213Isup2.hkl

checkCIF report

Comment top

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 Ni^II 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.

Related literature top

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 top

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%).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: 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).

Figures top

Fig. 1. ORTEP projection of the title molecule. Thermal ellipsoids are at the 30% probability level.

cis-Bis{(E)-2-[(2-fluorophenyl)iminomethyl]phenolato- κ²N,O}bis(pyridine-κN)nickel(II) top

Crystal data top

[Ni(C₁₃H₉FNO)₂(C₅H₅N)₂]	Z = 1
M_r = 645.32	F(000) = 332
Triclinic, P1	D_x = 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

Data collection top

Nonius KappaCCD diffractometer	2909 independent reflections
Radiation source: fine-focus sealed tube	2652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ scans, and ω scans with κ	θ_max = 25.5°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→9
T_min = 0.895, T_max = 0.924	k = −12→12
11574 measured reflections	l = −13→13

Refinement top

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(F_o²) + (0.0566P)² + 0.389P] where P = (F_o² + 2F_c²)/3
2909 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ni(C₁₃H₉FNO)₂(C₅H₅N)₂]	γ = 111.93 (3)°
M_r = 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)°

Data collection top

Nonius KappaCCD diffractometer	2909 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2652 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.924	R_int = 0.026
11574 measured reflections

Refinement top

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	Δρ_max = 0.41 e Å⁻³
2909 reflections	Δρ_min = −0.32 e Å⁻³
219 parameters

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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]
M_r	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)
T_min, T_max	0.895, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	11574, 2909, 2652
R_int	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
Δρ_max, Δρ_min (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.

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