Bis{2-[(E)-(4-fluoro­benz­yl)imino­meth­yl]-6-meth­oxy­phenolato-κ2N,O1}nickel(II)

Bahron, H.; Tajuddin, A.M.; Ibrahim, W.N.W.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811025189

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1010-m1011

doi:10.1107/S1600536811025189

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Bis{2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato-κ²N,O¹}nickel(II)

Hadariah Bahron,^a Amalina Mohd Tajuddin,^a Wan Nazihah Wan Ibrahim,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 14 June 2011; accepted 27 June 2011; online 2 July 2011)

In the title compound, [Ni(C₁₅H₁₃FNO₂)₂], the Ni^II atom is tetracoordinated by two N atoms and two O atoms from two 2-[(4-fluorobenzyl)iminomethyl]-6-methoxyphenolate 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 fluorophenyl group, five C atoms and an F atom are disordered over two sets of positions of equal occupancy. In the crystal, the complex molecules are linked via intermolecular 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_r = 575.24
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.114
S = 1.08
3948 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −1.20 e Å⁻³

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025189/hy2443sup1.cif

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

checkCIF report

Comment top

Schiff base complexes are attractive due to their simple synthesis, versatility and diverse range of applications (Yamada, 1999). Nickel(II) Schiff base complexes have been reported to possess various properties such as anti-bacterial, anti-fungal (Bagihalli et al., 2008) and catalytic activities (Arun et al., 2009). The title compound is bis-bidentate and related to the previously reported bis[2-(1-benzyliminoethyl)phenolato]palladium(II) (Mohd Tajuddin et al., 2010), but with different metal centres and substituents on the iminoalkylphenolato and benzyl moieties.

The asymmetric unit has one half of the molecule, in which the Ni^II atom lies on an inversion centre (Fig. 1). The geometry around the Ni^II atom is square-planar, in which two N atoms and two O atoms are coplanar and trans to each other. The fluorophenyl group is disordered with five C atoms and an F atom over two sets of positions in an occupancy ratio of 0.50:0.50. The distances between the Ni atom and O and N atoms are 1.8298 (14) and 1.9223 (16) Å, respectively. In the crystal structure, the complex molecules are linked via C—H···F hydrogen bonds (Table 1, Fig. 2), forming a one-dimensional chain along [0 0 1].

Related literature top

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 top

The ligand 2-[(E)-(4-fluorobenzylimino)methyl]-6-methoxyphenol (0.519 g, 2 mmol), which was prepared according to the previously published method (Bahron et al., 2007), was dissolved in ethanol (5 ml) in a round-bottomed flask. Nickel(II) acetate ( 0.251 g, 1 mmol) was dissolved separately in ethanol (5 ml ) and added into the flask containing the ligand solution. The mixture was stirred and refluxed for 5 h, upon which a green precipitate was formed. It was isolated by gravity filtration, washed with cold ethanol and air dried at room temperature. The solid product was recrystallized from chloroform, yielding green crystals (yield: 83.9%). Melting point: 493–498 K. Analysis, calculated for C₃₀H₂₆F₂N₂NiO₄: C 62.64, H 4.56, N 4.87%; found: C 62.83, H 4.61, N 4.62%. IR (cm^-1): ν(C═N) 1612 (s), ν(C–O) 1249 (s), ν(C–H) 2837 (w), ν(C–N) 1340 (m), ν(C–OCH₃) 1082 (m), ν(Ni–O) 648 (w), ν(Ni–N) 462 (w). ¹H NMR (CDCl₃, 300 MHz, p.p.m.): δ = 6.238 (1H, s, HC═N), 6.741–7.559 (7H, m, H–aromatic), 5.695 (2H, s, CH₂), 3.703 (3H, s, OCH₃).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. [Symmetry code: (i) -x+1, -y+1, -z.]
	Fig. 2. The crystal packing of the title compound. Only major components of the disordered atoms are shown. Dashed lines denote hydrogen bonds.

Bis{2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato- κ²N,O¹}nickel(II) top

Crystal data top

[Ni(C₁₅H₁₃FNO₂)₂]	Z = 1
M_r = 575.24	F(000) = 298
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0469P)² + 0.2521P] where P = (F_o² + 2F_c²)/3
3948 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −1.20 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₃FNO₂)₂]	γ = 91.020 (3)°
M_r = 575.24	V = 621.92 (4) Å³
Triclinic, P1	Z = 1
a = 5.0110 (2) Å	Mo Kα radiation
b = 10.9309 (4) Å	µ = 0.84 mm⁻¹
c = 12.2435 (5) Å	T = 100 K
α = 109.631 (2)°	0.49 × 0.09 × 0.03 mm
β = 99.083 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3948 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3148 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.977	R_int = 0.071
14720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.08	Δρ_max = 0.55 e Å⁻³
3948 reflections	Δρ_min = −1.20 e Å⁻³
222 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₃FNO₂)₂]
M_r	575.24
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.0110 (2), 10.9309 (4), 12.2435 (5)
α, β, γ (°)	109.631 (2), 99.083 (3), 91.020 (3)
V (Å³)	621.92 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.49 × 0.09 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.685, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	14720, 3948, 3148
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 1.08
No. of reflections	3948
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −1.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HB, AMT and WNWI acknowledge the Ministry of Higher Education of Malaysia for research grant No. 600-RMI/ST/FRGS5/3/Fst(7/2009) and Universiti Teknologi MARA and Universiti Sains Malaysia for the facilities. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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