Bis{2-[(E)-(4-fluoro-benz-yl)imino-meth-yl]-6-meth-oxy-phenolato-κN,O}nickel(II).

In the title compound, [Ni(C(15)H(13)FNO(2))(2)], the Ni(II) atom is tetra-coordinated by two N atoms and two O atoms from two 2-[(4-fluoro-benz-yl)imino-meth-yl]-6-meth-oxy-phenolate ligands in a square-planar geometry. The two N atoms and two O atoms around the Ni(II) atom are trans to each other, as the Ni(II) atom lies on an inversion centre. In the fluoro-phenyl group, five C atoms and an F atom are disordered over two sets of positions of equal occupancy. In the crystal, the complex mol-ecules are linked via inter-molecular C-H⋯F hydrogen bonds, forming chains along [001].

Related literature

For applications of Schiff base complexes, see: Arun et al. (2009 ▶); Bagihalli et al. (2008 ▶); Yamada (1999 ▶). For a related structure, see: Mohd Tajuddin et al. (2010 ▶). For the synthesis of the ligand, see: Bahron et al. (2007 ▶).

Experimental

Crystal data

[Ni(C15H13FNO2)2]

M = 575.24

Triclinic,

a = 5.0110 (2) Å

b = 10.9309 (4) Å

c = 12.2435 (5) Å

α = 109.631 (2)°

β = 99.083 (3)°

γ = 91.020 (3)°

V = 621.92 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.84 mm−1

T = 100 K

0.49 × 0.09 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.685, T max = 0.977

14720 measured reflections

3948 independent reflections

3148 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 1.08

3948 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −1.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025189/hy2443sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025189/hy2443Isup2.hkl

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

[Ni(C15H13FNO2)2]	Z = 1
Mr = 575.24	F(000) = 298
Triclinic, P1	Dx = 1.536 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0110 (2) Å	Cell parameters from 3312 reflections
b = 10.9309 (4) Å	θ = 3.1–29.9°
c = 12.2435 (5) Å	µ = 0.84 mm−1
α = 109.631 (2)°	T = 100 K
β = 99.083 (3)°	Needle, green
γ = 91.020 (3)°	0.49 × 0.09 × 0.03 mm
V = 621.92 (4) Å3

Bruker APEXII CCD diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3148 reflections with I > 2σ(I)
graphite	Rint = 0.071
φ and ω scans	θmax = 31.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.685, Tmax = 0.977	k = −15→15
14720 measured reflections	l = −17→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.2521P] where P = (Fo2 + 2Fc2)/3
3948 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −1.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107) operating at 100.0 (1) K.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.5000	0.5000	0.0000	0.01452 (11)
O1	0.7199 (3)	0.64851 (13)	0.03573 (12)	0.0179 (3)
O2	1.0870 (3)	0.82320 (14)	0.03948 (13)	0.0216 (3)
N1	0.3601 (3)	0.56402 (15)	0.14468 (14)	0.0152 (3)
C1	0.7786 (4)	0.74804 (18)	0.13306 (17)	0.0156 (4)
C2	0.9789 (4)	0.84687 (19)	0.13974 (18)	0.0169 (4)
C3	1.0462 (5)	0.95465 (19)	0.24012 (19)	0.0200 (4)
H3A	1.1799	1.0191	0.2433	0.024*
C4	0.9191 (5)	0.9703 (2)	0.33805 (19)	0.0221 (4)
H4A	0.9681	1.0448	0.4071	0.027*
C5	0.7253 (5)	0.87862 (19)	0.33413 (18)	0.0204 (4)
H5A	0.6385	0.8902	0.4001	0.024*
C6	0.6530 (4)	0.76618 (18)	0.23190 (18)	0.0170 (4)
C7	0.4439 (4)	0.67372 (19)	0.22852 (17)	0.0162 (4)
H7A	0.3562	0.6949	0.2952	0.019*
C8	0.1401 (4)	0.48995 (19)	0.17120 (17)	0.0168 (4)
H8A	0.0373	0.4283	0.0966	0.020*
H8B	0.0131	0.5514	0.2102	0.020*
C9	0.2526 (4)	0.41510 (19)	0.25017 (18)	0.0177 (4)
C15	1.2842 (5)	0.9193 (2)	0.0404 (2)	0.0233 (4)
H15A	1.3408	0.8945	−0.0367	0.035*
H15B	1.4419	0.9256	0.1012	0.035*
H15C	1.2057	1.0037	0.0574	0.035*
F1	0.549 (4)	0.2029 (11)	0.4639 (17)	0.031 (2)	0.50
C10	0.1167 (9)	0.4015 (4)	0.3345 (4)	0.0197 (8)	0.50
H10A	−0.0475	0.4425	0.3450	0.024*	0.50
C11	0.2113 (10)	0.3290 (4)	0.4062 (4)	0.0228 (8)	0.50
H11A	0.1147	0.3206	0.4644	0.027*	0.50
C12	0.449 (2)	0.2710 (7)	0.3888 (8)	0.0228 (8)	0.50
C13	0.5903 (14)	0.2752 (6)	0.3032 (6)	0.0216 (12)	0.50
H13A	0.7511	0.2312	0.2925	0.026*	0.50
C14	0.4904 (12)	0.3462 (5)	0.2325 (5)	0.0197 (10)	0.50
H14A	0.5823	0.3489	0.1710	0.024*	0.50
F1X	0.583 (4)	0.2322 (11)	0.4752 (17)	0.0270 (16)	0.50
C10X	0.2322 (10)	0.4664 (4)	0.3718 (4)	0.0200 (8)	0.50
H10B	0.1442	0.5442	0.4006	0.024*	0.50
C11X	0.3399 (9)	0.4039 (4)	0.4485 (4)	0.0214 (7)	0.50
H11B	0.3243	0.4367	0.5294	0.026*	0.50
C12X	0.471 (2)	0.2918 (7)	0.4034 (8)	0.0214 (7)	0.50
C13X	0.4963 (13)	0.2427 (6)	0.2862 (6)	0.0201 (12)	0.50
H13B	0.5866	0.1657	0.2571	0.024*	0.50
C14X	0.3865 (11)	0.3080 (5)	0.2107 (5)	0.0164 (9)	0.50
H14B	0.4071	0.2760	0.1303	0.020*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.0169 (2)	0.01101 (16)	0.01719 (18)	−0.00043 (13)	0.00410 (14)	0.00644 (13)
O1	0.0213 (8)	0.0145 (6)	0.0180 (7)	−0.0027 (6)	0.0053 (6)	0.0050 (5)
O2	0.0236 (8)	0.0186 (7)	0.0237 (7)	−0.0048 (6)	0.0078 (6)	0.0073 (6)
N1	0.0152 (8)	0.0143 (7)	0.0171 (8)	−0.0003 (6)	0.0027 (6)	0.0069 (6)
C1	0.0165 (10)	0.0120 (8)	0.0189 (9)	0.0018 (7)	0.0009 (7)	0.0070 (7)
C2	0.0159 (10)	0.0160 (8)	0.0209 (9)	0.0020 (7)	0.0030 (8)	0.0092 (7)
C3	0.0200 (10)	0.0163 (8)	0.0247 (10)	−0.0018 (8)	0.0024 (8)	0.0091 (8)
C4	0.0268 (12)	0.0152 (9)	0.0208 (10)	−0.0034 (8)	0.0020 (9)	0.0027 (8)
C5	0.0238 (11)	0.0174 (9)	0.0191 (9)	0.0010 (8)	0.0049 (8)	0.0046 (8)
C6	0.0189 (10)	0.0141 (8)	0.0192 (9)	0.0007 (7)	0.0030 (8)	0.0073 (7)
C7	0.0179 (10)	0.0164 (8)	0.0168 (9)	0.0034 (7)	0.0044 (7)	0.0079 (7)
C8	0.0147 (9)	0.0171 (8)	0.0208 (9)	0.0007 (7)	0.0043 (8)	0.0090 (7)
C9	0.0169 (10)	0.0171 (8)	0.0203 (9)	−0.0024 (7)	0.0036 (8)	0.0083 (7)
C15	0.0204 (11)	0.0216 (9)	0.0333 (12)	−0.0020 (8)	0.0070 (9)	0.0155 (9)
F1	0.050 (6)	0.024 (4)	0.030 (4)	0.009 (4)	0.008 (3)	0.021 (4)
C10	0.020 (2)	0.0161 (18)	0.025 (2)	−0.0036 (17)	0.0072 (17)	0.0072 (16)
C11	0.032 (2)	0.0187 (16)	0.0222 (19)	0.0007 (15)	0.0068 (16)	0.0117 (14)
C12	0.032 (2)	0.0187 (16)	0.0222 (19)	0.0007 (15)	0.0068 (16)	0.0117 (14)
C13	0.024 (3)	0.018 (3)	0.023 (3)	0.006 (2)	0.005 (3)	0.008 (2)
C14	0.024 (3)	0.017 (2)	0.019 (2)	0.0003 (19)	0.006 (2)	0.0069 (18)
F1X	0.037 (4)	0.026 (5)	0.028 (3)	0.006 (4)	0.009 (3)	0.020 (4)
C10X	0.023 (2)	0.0192 (19)	0.0190 (19)	0.0064 (18)	0.0054 (17)	0.0076 (16)
C11X	0.0254 (19)	0.0235 (18)	0.0163 (17)	0.0022 (15)	0.0007 (14)	0.0096 (14)
C12X	0.0254 (19)	0.0235 (18)	0.0163 (17)	0.0022 (15)	0.0007 (14)	0.0096 (14)
C13X	0.026 (3)	0.016 (3)	0.020 (3)	0.003 (2)	0.006 (3)	0.007 (2)
C14X	0.020 (2)	0.013 (2)	0.018 (2)	0.0003 (17)	0.0049 (19)	0.0067 (17)

Ni1—O1	1.8297 (14)	C9—C10X	1.425 (5)
Ni1—N1	1.9223 (16)	C9—C14	1.428 (6)
O1—C1	1.303 (2)	C15—H15A	0.9800
O2—C2	1.367 (2)	C15—H15B	0.9800
O2—C15	1.425 (2)	C15—H15C	0.9800
N1—C7	1.299 (2)	F1—C12	1.41 (2)
N1—C8	1.495 (2)	C10—C11	1.404 (6)
C1—C6	1.409 (3)	C10—H10A	0.9500
C1—C2	1.434 (3)	C11—C12	1.371 (12)
C2—C3	1.376 (3)	C11—H11A	0.9500
C3—C4	1.407 (3)	C12—C13	1.367 (13)
C3—H3A	0.9500	C13—C14	1.390 (9)
C4—C5	1.367 (3)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.420 (3)	F1X—C12X	1.32 (2)
C5—H5A	0.9500	C10X—C11X	1.388 (6)
C6—C7	1.429 (3)	C10X—H10B	0.9500
C7—H7A	0.9500	C11X—C12X	1.389 (10)
C8—C9	1.516 (3)	C11X—H11B	0.9500
C8—H8A	0.9900	C12X—C13X	1.380 (12)
C8—H8B	0.9900	C13X—C14X	1.402 (9)
C9—C14X	1.344 (5)	C13X—H13B	0.9500
C9—C10	1.369 (5)	C14X—H14B	0.9500
O1—Ni1—O1i	180.00 (9)	C10X—C9—C14	111.5 (3)
O1—Ni1—N1	93.00 (7)	C14X—C9—C8	122.0 (3)
O1i—Ni1—N1	87.00 (7)	C10—C9—C8	121.1 (3)
O1—Ni1—N1i	87.00 (7)	C10X—C9—C8	118.4 (2)
O1i—Ni1—N1i	93.00 (6)	C14—C9—C8	121.3 (3)
N1—Ni1—N1i	180.0	O2—C15—H15A	109.5
C1—O1—Ni1	130.38 (13)	O2—C15—H15B	109.5
C2—O2—C15	116.49 (16)	H15A—C15—H15B	109.5
C7—N1—C8	113.22 (16)	O2—C15—H15C	109.5
C7—N1—Ni1	124.50 (14)	H15A—C15—H15C	109.5
C8—N1—Ni1	122.29 (12)	H15B—C15—H15C	109.5
O1—C1—C6	123.93 (18)	C9—C10—C11	122.4 (4)
O1—C1—C2	118.37 (18)	C9—C10—H10A	118.8
C6—C1—C2	117.68 (17)	C11—C10—H10A	118.8
O2—C2—C3	125.29 (19)	C12—C11—C10	117.3 (6)
O2—C2—C1	114.03 (17)	C12—C11—H11A	121.3
C3—C2—C1	120.68 (19)	C10—C11—H11A	121.3
C2—C3—C4	120.63 (19)	C13—C12—C11	123.9 (9)
C2—C3—H3A	119.7	C13—C12—F1	118.8 (12)
C4—C3—H3A	119.7	C11—C12—F1	117.3 (12)
C5—C4—C3	120.18 (19)	C12—C13—C14	117.6 (7)
C5—C4—H4A	119.9	C12—C13—H13A	121.2
C3—C4—H4A	119.9	C14—C13—H13A	121.2
C4—C5—C6	120.33 (19)	C13—C14—C9	121.4 (5)
C4—C5—H5A	119.8	C13—C14—H14A	119.3
C6—C5—H5A	119.8	C9—C14—H14A	119.3
C1—C6—C5	120.49 (19)	C11X—C10X—C9	120.6 (3)
C1—C6—C7	120.17 (18)	C11X—C10X—H10B	119.7
C5—C6—C7	119.30 (18)	C9—C10X—H10B	119.7
N1—C7—C6	127.39 (18)	C10X—C11X—C12X	118.0 (5)
N1—C7—H7A	116.3	C10X—C11X—H11B	121.0
C6—C7—H7A	116.3	C12X—C11X—H11B	121.0
N1—C8—C9	111.72 (16)	F1X—C12X—C13X	118.8 (11)
N1—C8—H8A	109.3	F1X—C12X—C11X	119.3 (10)
C9—C8—H8A	109.3	C13X—C12X—C11X	121.9 (8)
N1—C8—H8B	109.3	C12X—C13X—C14X	119.0 (7)
C9—C8—H8B	109.3	C12X—C13X—H13B	120.5
H8A—C8—H8B	107.9	C14X—C13X—H13B	120.5
C14X—C9—C10	108.2 (3)	C9—C14X—C13X	121.0 (5)
C14X—C9—C10X	119.5 (3)	C9—C14X—H14B	119.5
C10—C9—C14	117.3 (3)	C13X—C14X—H14B	119.5
N1—Ni1—O1—C1	8.77 (19)	N1—C8—C9—C10	143.9 (3)
N1i—Ni1—O1—C1	−171.23 (19)	N1—C8—C9—C10X	102.8 (3)
O1—Ni1—N1—C7	−4.67 (18)	N1—C8—C9—C14	−42.0 (3)
O1i—Ni1—N1—C7	175.33 (18)	C14X—C9—C10—C11	29.7 (5)
O1—Ni1—N1—C8	175.40 (15)	C10X—C9—C10—C11	−85.9 (6)
O1i—Ni1—N1—C8	−4.60 (15)	C14—C9—C10—C11	3.4 (6)
Ni1—O1—C1—C6	−7.0 (3)	C8—C9—C10—C11	177.8 (3)
Ni1—O1—C1—C2	174.36 (14)	C9—C10—C11—C12	0.0 (7)
C15—O2—C2—C3	−0.3 (3)	C10—C11—C12—C13	−2.9 (9)
C15—O2—C2—C1	179.05 (18)	C10—C11—C12—F1	177.4 (7)
O1—C1—C2—O2	−0.1 (3)	C11—C12—C13—C14	2.1 (10)
C6—C1—C2—O2	−178.77 (18)	F1—C12—C13—C14	−178.2 (7)
O1—C1—C2—C3	179.33 (19)	C12—C13—C14—C9	1.6 (8)
C6—C1—C2—C3	0.6 (3)	C14X—C9—C14—C13	−79.1 (9)
O2—C2—C3—C4	179.04 (19)	C10—C9—C14—C13	−4.2 (6)
C1—C2—C3—C4	−0.3 (3)	C10X—C9—C14—C13	34.5 (6)
C2—C3—C4—C5	−0.4 (3)	C8—C9—C14—C13	−178.6 (4)
C3—C4—C5—C6	0.8 (3)	C14X—C9—C10X—C11X	−2.6 (6)
O1—C1—C6—C5	−178.92 (19)	C10—C9—C10X—C11X	77.3 (5)
C2—C1—C6—C5	−0.3 (3)	C14—C9—C10X—C11X	−29.9 (5)
O1—C1—C6—C7	−1.2 (3)	C8—C9—C10X—C11X	−177.9 (3)
C2—C1—C6—C7	177.37 (18)	C9—C10X—C11X—C12X	1.1 (8)
C4—C5—C6—C1	−0.4 (3)	C10X—C11X—C12X—F1X	178.0 (9)
C4—C5—C6—C7	−178.1 (2)	C10X—C11X—C12X—C13X	0.1 (10)
C8—N1—C7—C6	179.02 (19)	F1X—C12X—C13X—C14X	−177.8 (9)
Ni1—N1—C7—C6	−0.9 (3)	C11X—C12X—C13X—C14X	0.1 (11)
C1—C6—C7—N1	5.2 (3)	C10—C9—C14X—C13X	−34.3 (6)
C5—C6—C7—N1	−177.1 (2)	C10X—C9—C14X—C13X	2.8 (7)
C7—N1—C8—C9	−80.9 (2)	C14—C9—C14X—C13X	81.2 (9)
Ni1—N1—C8—C9	99.07 (17)	C8—C9—C14X—C13X	177.9 (4)
N1—C8—C9—C14X	−72.4 (3)	C12X—C13X—C14X—C9	−1.6 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···F1ii	0.95	2.51	3.363 (18)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯F1i	0.95	2.51	3.363 (18)	150

Symmetry code: (i) .