cis-Bis{(E)-2-[(2-fluoro-phen-yl)imino-meth-yl]phenolato-κ(2) N,O}bis-(pyridine-κN)nickel(II).

The structure of the title compound, [Ni(C13H9FNO)2(C5H5N)2], consists of an Ni(II) atom on a crystallographic center of symmetry, octa-hedrally bonded through both the N and O atoms to two 2-[(2-fluoro-phen-yl)imino-meth-yl]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 fluoro-phenyl 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 = 645.32

Triclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.05

2909 reflections

219 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045576/br2213sup1.cif

Click here for additional data file.

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

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

[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

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)