Crystal structure of bis­{2-[(E)-(4-fluoro­benz­yl)imino­meth­yl]phenolato-κ2N,O}nickel(II)

Tajuddin, A.M.; Bahron, H.; Hanafiah, R.M.; Ibrahim, N.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S1600536814020546

research communications

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages 252-255

doi:10.1107/S1600536814020546

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Crystal structure of bis{2-[(E)-(4-fluorobenzyl)iminomethyl]phenolato-κ²N,O}nickel(II)

Amalina Mohd Tajuddin,^a Hadariah Bahron,^a,^b Rohazila Mohammad Hanafiah,^c Nazlina Ibrahim,^c Hoong-Kun Fun ^d,^e ^*‡ and Suchada Chantrapromma ^f §

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^bDDH CoRe, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^cSchool of Biosciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan, 43600 Bangi, Selangor, Malaysia, ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^eDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^fDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

Edited by J. Simpson, University of Otago, New Zealand (Received 9 September 2014; accepted 13 September 2014; online 24 September 2014)

The asymmetric unit of the title complex, [Ni(C₁₄H₁₁FNO)₂], contains one-half of the molecule with the Ni^II cation lying on an inversion centre coordinated by a bidentate Schiff base anion. The cationic Ni^II center is in a distorted square-planar coordination environment chelated by the imine N and phenolate O donor atoms of the two Schiff base ligands. The N and O donor atoms of the two ligands are mutually trans with Ni—N and Ni—O bond lengths of 1.9242 (10) and 1.8336 (9) Å, respectively. The fluorophenyl ring is almost orthogonal to the coordination plane and makes a dihedral angle of 82.98 (7)° with the phenolate ring. In the crystal, molecules are linked into screw chains by weak C—H⋯F hydrogen bonds. Additional C—H⋯π contacts arrange the molecules into sheets parallel to the ac plane.

Keywords: Crystal structure; Ni(II) complex; NO donors; Schiff base; antibacterial activity.

CCDC reference: 1024161

1. Chemical context

In our previous studies, we reported the syntheses and crystal structures of two related Schiff base complexes, bis{2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato-κ²N,O¹}nickel(II) (Bahron et al., 2011 ) and bis{2-[(E)-(4-methoxybenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II) (Bahron et al., 2014 ). In this article, we report the successful synthesis of another Schiff base–Ni^II complex, [Ni(C₁₄H₁₁FNO)₂] (1), and its characterization by spectroscopy and elemental analysis. Crystal structure determination confirms the binding mode of the [(4-fluorobenzyl)iminomethyl]phenolate ligand to the Ni^II cation (Fig. 1). The title complex was also tested for antibacterial activity, and found to be only weakly active.

Figure 1
The molecular structure of (1), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The labelled atoms are related to the unlabelled atoms of the Schiff base ligands by the symmetry code: 1 − x, −y, 1 − z.

2. Structural commentary

The asymmetric unit of (1) contains one-half of the molecule with the Ni^II cation lying on an inversion centre and the Schiff base anion acting as an N,O-bidentate chelate ligand (Fig. 1). The cation binds to the N and the O atoms of two symmetry-related Schiff base ligand such that the N and O atoms are mutually trans. The N₂O₂ donor sets of the two chelating Schiff base ligands in the equatorial plane around Ni1 adopt a slightly distorted square planar coordination geometry with the angles O1—Ni1—N1 = 92.56 (4)° and O1—Ni1—N1ⁱ = 87.44 (4)° [symmetry code: (i) 1 − x, −y, 1 − z]. As expected under inversion symmetry, the trans angles (N11—Ni1—N1ⁱ and O1—Ni1—O1ⁱ) are found to be linear. The Ni1—N1 and Ni1—O1 distances in the N₂O₂ coordination plane are 1.9242 (10) Å and 1.8336 (9) Å, respectively. These compare well with those observed in the two other closely related Ni^II complexes with N₂O₂ coordinating Schiff base ligands (Bahron et al., 2011; 2014). The Ni1/O1/C1/C6/C7/N1 ring adopts an envelope conformation with the Ni1 atom displaced by 0.3885 (5) Å from the O1/C1/C6/C7/N1 plane, with the puckering parameters Q = 0.2429 (10) Å, θ = 65.3 (3) and φ = 4.0 (3)°. Other bond lengths and angles observed in the structure are also normal. The fluorophenyl ring (C9–C14) makes a dihedral angle of 82.98 (7)° with the phenolate ring (C1–C6).

3. Supramolecular features

In the crystal packing, the molecules are linked into screw chains by weak C2—H2A⋯F1 interactions (Fig. 2, Table 1). C—H⋯π interactions involving both the fluorophenyl and the phenolate rings, C5—H5A⋯Cg1 and C13—H13A⋯Cg2, connect the molecules into chains along the c-axis direction (Fig. 3, Table 1). They also contribute to the formation of sheets parallel to the ac plane, which are further stacked along the b axis as shown in Fig. 4.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.99	2.19	2.7300 (18)	113
C14—H14A⋯O1ⁱ	0.95	2.52	3.212 (2)	130
C2—H2A⋯F1ⁱⁱ	0.95	2.65	3.5312 (19)	155
C5—H5A⋯Cg1ⁱⁱⁱ	0.95	2.69	3.4010 (18)	133
C13—H13A⋯Cg2^iv	0.95	2.69	3.4252 (13)	134
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Screw chains of molecules of (1) linked by C—H⋯F contacts drawn as dashed lines.

Figure 3
C—H⋯π contacts for (1) drawn as dotted lines with ring centroids shown as coloured spheres. Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

Figure 4
The packing of (1) viewed along the b axis showing molecular sheets of the Ni^II complex.

4. Database survey

A search of the Cambridge Database (Version 5.35, November 2013 with 3 updates) revealed a total of 1191 Ni^II complexes with an NiN₂O₂ coordination sphere. No fewer than 333 of these had the Ni atom chelated by two 3-(iminomethyl)phenolate residues. No corresponding structures with a benzyl or substituted benzyl unit bound to the imino N atom were found. However extending the search to allow additional substitution on the phenolate ring resulted in eight discrete structures including the two closely related structures mentioned previously (Bahron et al., 2011, 2014), and several other related complexes (see, for example Guo et al. 2013a,b ; Senol et al. 2011 ; Chen et al. 2010 ).

5. Synthesis and crystallization

An ethanolic solution of 4-fluorobenzylamine (4 mmol, 0.5010 g) was added to salicylaldehyde (4 mmol, 0.4970 g), dissolved in absolute ethanol (2 ml), forming a bright-yellow solution. The mixture was heated under reflux for an hour to produce the ligand, (E)-2-[(4-fluorobenzylimino)methyl]phenol. Nickel(II) acetate tetrahydrate (2 mmol, 0.4983 g) was dissolved separately in absolute ethanol (10 ml) and added to a flask containing the cooled ligand solution. The mixture was stirred and refluxed for 3 h upon which a dark-green solid formed. This was filtered off, washed with ice-cold ethanol and air-dried at room temperature. The solid product was recrystallized from chloroform, yielding green crystals. Yield 68.6%; m.p. 471–473 K. Analytical data for C₂₈H₂₂F₂N₂O₂Ni: C, 65.28; H, 4.30; N, 5.44. Found: C, 65.87; H, 4.39; N, 5.55. IR (KBr, cm⁻¹): ν(C=N) 1612 (s), ν(C—N) 1390 (w), ν(C—O) 1221 (s), ν(Ni—N) 597 (w), ν(Ni—O) 451 (w). The infrared spectra of the title complex revealed a strong band of 1612 cm⁻¹ in the spectrum assignable to C=N stretching frequency upon complexation (Nair et al., 2012 ). The appearance of new bands at 451 and 597 cm⁻¹ in the spectrum of the title complex attributable to Ni—O and Ni—N vibrations, respectively, supports the suggestion above of the participation of the N atom of the imine group and O atom of the phenolic group of the ligand in the complexation with Ni^II cation (Ouf et al., 2010 ). Accordingly, it can be deduced that the ligand binds to the Ni^II cation in an N,O-bidentate fashion in 2:1 ratio.

An antibacterial activity investigation of the title complex against B. subtilis, S. aureus and E. coli showed very mild or no inhibition with clear inhibition diameters of 7–8 mm at the highest concentration of 50 μM. The negative control of a 9:1 mixture of DMSO:acetone and the positive control of 30 U of chloramphenicol showed inhibition diameters of 6 mm and 20 mm, respectively.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.95 Å for aromatic and 0.99 Å for CH₂ hydrogen atoms. The U_iso values were constrained to be 1.2U_eq of the carrier atoms.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₁FNO)₂]
M_r	515.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.8611 (3), 5.83340 (1), 16.9942 (3)
β (°)	125.998 (1)
V (Å³)	1111.70 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.92
Crystal size (mm)	0.47 × 0.19 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.674, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	13419, 3235, 2896
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.072, 1.05
No. of reflections	3235
No. of parameters	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.49
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008 ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1024161

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814020546/sj5425sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020546/sj5425Isup2.hkl

checkCIF report

Chemical context top

Schiff base ligands are well-known and important compounds because of their wide range of biological activities and uses in industrial systems (Feng et al., 2013; Kumar et al., 2010; Liu et al., 2005) as well as being versatile ligands for transition metals. Transition metal complexes with Schiff base ligands, especially those of Pd^II and Ni^II, have been shown to display a variety of structural features and, in some cases, exhibit interesting reactivity. In particular they can be photoluminescent (Guo et al., 2013a) and are used as catalysts for many organic reactions such as Heck and Suzuki cross-coupling reactions (Kumari et al., 2012; Teo et al., 2011). In our previous studies, we reported the syntheses and crystal structures of two related Schiff base complexes, bis{2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato-κ²N,O¹}nickel(II) (Bahron et al., 2011) and bis{2-[(E)-(4-methoxybenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II) (Bahron et al., 2014). In this article, we report the successful synthesis of another Schiff base–Ni^II complex, [Ni(C₁₄H₁₁FNO)₂] (1), and its characterization by spectroscopy and elemental analysis. The X-ray structure (Fig. 1) confirms the binding mode of the 4-fluorobenzyl)iminomethyl]phenolate ligand to the Ni^II cation. The title complex was also tested for antibacterial activity, and found to be only weakly active.

Structural commentary top

The asymmetric unit of (1) contains one-half of the molecule with the Ni^II cation lying on an inversion centre and the Schiff base anion acting as an N,O-bidentate chelate ligand (Fig. 1). The Ni1 cation binds to the N and the O atoms of two symmetry-related Schiff base ligand such that the N and O atoms are mutually trans. The N₂O₂ donor sets of the two chelating Schiff base ligands in the equatorial plane around Ni1 adopt a slightly distorted square planar coordination geometry with the angles O1—Ni1—N1 = 92.56 (4)° and O1—Ni1—N1ⁱ = 87.44 (4)° [symmetry code: (i) 1 - x, -y, 1 - z]. As expected under inversion symmetry, the trans angles are found to be N11—Ni1—N1ⁱ = 180.00 (6)° and O1—Ni1—O1ⁱ = 180.0°. The Ni1—N1 and Ni1—O1 distances in the N₂O₂ coordination plane are 1.9242 (10) Å and 1.8336 (9) Å, respectively. These compare well with those observed in the two other closely related Ni^II complexes with N₂O₂ coordinating Schiff base ligands (Bahron et al., 2011; 2014). The Ni1/O1/C1/C6/C7/N1 ring adopts an envelope conformation with the Ni1 atom displaced by 0.3885 (5) Å from the plane of the phenolate ring atoms, with the puckering parameters Q = 0.2429 (10) Å, θ = 65.3 (3) and ϕ = 4.0 (3)°. Other bond lengths and angles observed in the structure are also normal. The fluorophenyl ring (C9–C14) makes a dihedral angle of 82.98 (7)° with the phenolate ring (C1–C6).

Supramolecular features top

In the crystal packing, the molecules are linked into screw chains by weak C2–H2A···F1 interactions (Fig. 2, Table 1). C—H···π interactions involving both the fluorophenyl and the phenolate rings, C5—H5A···Cg1 and C13—H13A···Cg2, connect the molecules into chains along the c-axis direction (Fig. 3, Table 1). They also contribute to the formation of sheets parallel to the ac plane, which are further stacked along the b axis as shown in Fig. 4.

Database survey top

A search of the Cambridge Database (Version 5.35, November 2013 with 3 updates) revealed a total of 1191 Ni^II complexes with an NiN₂O₂ coordination sphere. No fewer than 333 of these had the Ni atom chelated by two 3-(iminomethyl)phenolate residues. No corresponding structures with a benzyl or substituted benzyl unit bound to the imino N atom were found. However extending the search to allow additional substitution on the phenolate ring resulted in eight discrete structures including the two closely related structures mentioned previously (Bahron et al., 2011, 2014), and several other related complexes (see for example Guo et al. 2013a,b; Senol et al. 2011; Chen et al. 2010).

Synthesis and crystallization top

An ethanolic solution of 4-fluorobenzylamine (4 mmol, 0.5010 g) was added to salicylaldehyde (4 mmol, 0.4970 g), dissolved in absolute ethanol (2 ml), forming a bright-yellow solution. The mixture was heated under reflux for an hour to produce the ligand, (E)-2-[(4-fluorobenzylimino)methyl]phenol. Nickel(II) acetate tetrahydrate (2 mmol, 0.4983 g) was dissolved separately in absolute ethanol (10 ml) and added to a flask containing the cooled ligand solution. The mixture was stirred and refluxed for 3 hours upon which a dark-green solid formed. This was filtered off, washed with ice-cold ethanol and air dried at room temperature. The solid product was recrystallized from chloroform, yielding green crystals. Yield 68.6%. Melting point 471–473 K. Analytical data for C₂₈H₂₂F₂N₂O₂Ni: C, 65.28; H, 4.30; N, 5.44. Found: C, 65.87; H, 4.39; N, 5.55. IR (KBr, cm^-1): ν(C=N) 1612 (s), ν(C—N) 1390 (w), ν(C—O) 1221 (s), ν(Ni—N) 597 (w), ν(Ni—O) 451 (w). The infrared spectra of the title complex revealed a strong band of 1612 cm^-1 in the spectrum assignable to C=N stretching frequency upon complexation (Nair et al., 2012). The appearance of new bands at 451 and 597 cm^-1 in the spectrum of the title complex attributable to Ni—O and Ni—N vibrations, respectively, supports the suggestion above of the participation of the N atom of the imine group and O atom of the phenolic group of the ligand in the complexation with Ni^II cation (Ouf et al., 2010). Accordingly, it can be deduced that the ligand binds to the Ni^II cation in an N,O-bidentate fashion in 2:1 ratio.

An antibacterial activity investigation of the title complex against B. subtilis, S. aureus and E. coli showed very mild or no inhibition with clear inhibition diameters of 7–8 mm at the highest concentration of 50 υM. The negative control of a 9:1 mixture of DMSO:acetone and the positive control of 30 U of chloramphenicol showed inhibition diameters of 6 mm and 20 mm, respectively.

Refinement top

Related literature top

For related literature, see: Bahron et al. (2011, 2014); Chen et al. (2010); Feng et al. (2013); Guo et al. (2013a, 2013b); Kumar et al. (2010); Kumari et al. (2012); Liu et al. (2005); Nair et al. (2012); Ouf et al. (2010); Senol et al. (2011); Teo et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (1), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The labelled atoms are related to the unlabelled atoms of the Schiff base ligands by the symmetry code: 1 - x, -y, 1 - z.
	Fig. 2. Screw chains of molecules of (1) linked by C—H···F contacts drawn as dashed lines.
	Fig. 3. C—H···π contacts for (1) drawn as dotted lines with ring centroids shown as coloured spheres. Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.
	Fig. 4. The packing of (1) viewed along the b axis showing molecular sheets of the Ni^II complex.

Bis{2-[(E)-(4-fluorobenzyl)iminomethyl]phenolato- K²N,O¹}nickel(II) top

Crystal data top

[Ni(C₁₄H₁₁FNO)₂]	F(000) = 532
M_r = 515.17	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 471–476 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.8611 (3) Å	Cell parameters from 3235 reflections
b = 5.83340 (1) Å	θ = 1.8–30.0°
c = 16.9942 (3) Å	µ = 0.92 mm⁻¹
β = 125.998 (1)°	T = 100 K
V = 1111.70 (4) Å³	Plate, green
Z = 2	0.47 × 0.19 × 0.11 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3235 independent reflections
Radiation source: sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.674, T_max = 0.906	k = −8→8
13419 measured reflections	l = −23→23

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0322P)² + 0.7123P] where P = (F_o² + 2F_c²)/3
3235 reflections	(Δ/σ)_max = 0.001
160 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Ni(C₁₄H₁₁FNO)₂]	V = 1111.70 (4) Å³
M_r = 515.17	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8611 (3) Å	µ = 0.92 mm⁻¹
b = 5.83340 (1) Å	T = 100 K
c = 16.9942 (3) Å	0.47 × 0.19 × 0.11 mm
β = 125.998 (1)°

Data collection top

Bruker APEXII CCD area detector diffractometer	3235 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2896 reflections with I > 2σ(I)
T_min = 0.674, T_max = 0.906	R_int = 0.024
13419 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.05	Δρ_max = 0.45 e Å⁻³
3235 reflections	Δρ_min = −0.49 e Å⁻³
160 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ni1	0.5000	0.0000	0.5000	0.01062 (7)
F1	1.07321 (8)	−0.19874 (17)	0.63754 (7)	0.0297 (2)
N1	0.58764 (8)	0.26207 (18)	0.50481 (7)	0.01200 (19)
O1	0.41017 (8)	−0.01507 (15)	0.36693 (7)	0.01520 (18)
C1	0.38843 (10)	0.1456 (2)	0.30461 (9)	0.0133 (2)
C2	0.29659 (11)	0.1091 (2)	0.20455 (9)	0.0160 (2)
H2A	0.2528	−0.0303	0.1840	0.019*
C3	0.27066 (11)	0.2756 (2)	0.13703 (9)	0.0174 (2)
H3A	0.2085	0.2490	0.0704	0.021*
C4	0.33373 (12)	0.4832 (2)	0.16425 (10)	0.0175 (2)
H4A	0.3147	0.5959	0.1168	0.021*
C5	0.42385 (11)	0.5206 (2)	0.26118 (9)	0.0151 (2)
H5A	0.4676	0.6600	0.2804	0.018*
C6	0.45190 (10)	0.3546 (2)	0.33205 (8)	0.0125 (2)
C7	0.55207 (10)	0.3936 (2)	0.43090 (9)	0.0125 (2)
H7A	0.5968	0.5294	0.4434	0.015*
C8	0.70465 (10)	0.3283 (2)	0.59589 (9)	0.0134 (2)
H8A	0.7024	0.3042	0.6524	0.016*
H8B	0.7198	0.4930	0.5933	0.016*
C9	0.80423 (10)	0.1869 (2)	0.60823 (8)	0.0133 (2)
C10	0.86635 (11)	0.2669 (2)	0.57233 (9)	0.0166 (2)
H10A	0.8456	0.4110	0.5402	0.020*
C11	0.95823 (11)	0.1396 (3)	0.58258 (10)	0.0202 (3)
H11A	1.0010	0.1957	0.5588	0.024*
C12	0.98511 (11)	−0.0701 (3)	0.62825 (10)	0.0196 (3)
C13	0.92625 (11)	−0.1569 (2)	0.66508 (9)	0.0174 (2)
H13A	0.9471	−0.3019	0.6965	0.021*
C14	0.83553 (11)	−0.0255 (2)	0.65471 (9)	0.0152 (2)
H14A	0.7942	−0.0816	0.6798	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01005 (10)	0.01029 (11)	0.01063 (11)	−0.00089 (7)	0.00557 (8)	0.00019 (7)
F1	0.0240 (4)	0.0360 (5)	0.0340 (5)	0.0125 (4)	0.0197 (4)	0.0035 (4)
N1	0.0105 (4)	0.0115 (5)	0.0129 (4)	−0.0003 (3)	0.0063 (4)	−0.0010 (4)
O1	0.0168 (4)	0.0142 (4)	0.0122 (4)	−0.0036 (3)	0.0072 (3)	0.0005 (3)
C1	0.0123 (5)	0.0149 (5)	0.0138 (5)	0.0010 (4)	0.0084 (4)	0.0009 (4)
C2	0.0141 (5)	0.0177 (6)	0.0148 (5)	−0.0015 (4)	0.0077 (5)	−0.0003 (4)
C3	0.0141 (5)	0.0218 (6)	0.0136 (5)	0.0016 (4)	0.0066 (4)	0.0010 (5)
C4	0.0176 (6)	0.0188 (6)	0.0157 (6)	0.0029 (4)	0.0096 (5)	0.0049 (5)
C5	0.0153 (5)	0.0144 (6)	0.0167 (6)	0.0012 (4)	0.0100 (5)	0.0022 (4)
C6	0.0115 (5)	0.0133 (5)	0.0135 (5)	0.0014 (4)	0.0077 (4)	0.0010 (4)
C7	0.0122 (5)	0.0115 (5)	0.0158 (5)	−0.0002 (4)	0.0093 (4)	−0.0005 (4)
C8	0.0119 (5)	0.0116 (5)	0.0140 (5)	−0.0017 (4)	0.0062 (4)	−0.0020 (4)
C9	0.0103 (5)	0.0149 (5)	0.0114 (5)	−0.0012 (4)	0.0045 (4)	−0.0015 (4)
C10	0.0154 (5)	0.0179 (6)	0.0156 (5)	−0.0010 (4)	0.0086 (5)	0.0007 (4)
C11	0.0174 (6)	0.0271 (7)	0.0192 (6)	−0.0004 (5)	0.0126 (5)	−0.0003 (5)
C12	0.0139 (5)	0.0249 (7)	0.0182 (6)	0.0039 (5)	0.0085 (5)	−0.0020 (5)
C13	0.0139 (5)	0.0162 (6)	0.0161 (6)	0.0013 (4)	0.0054 (5)	−0.0002 (4)
C14	0.0123 (5)	0.0152 (6)	0.0155 (5)	−0.0018 (4)	0.0068 (4)	−0.0008 (4)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8336 (9)	C5—H5A	0.9500
Ni1—O1	1.8336 (9)	C6—C7	1.4351 (16)
Ni1—N1ⁱ	1.9242 (10)	C7—H7A	0.9500
Ni1—N1	1.9242 (10)	C8—C9	1.5133 (16)
F1—C12	1.3613 (15)	C8—H8A	0.9900
N1—C7	1.2967 (16)	C8—H8B	0.9900
N1—C8	1.4915 (15)	C9—C14	1.3943 (17)
O1—C1	1.3097 (15)	C9—C10	1.3960 (17)
C1—C6	1.4130 (17)	C10—C11	1.3937 (18)
C1—C2	1.4187 (17)	C10—H10A	0.9500
C2—C3	1.3801 (18)	C11—C12	1.378 (2)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.4031 (19)	C12—C13	1.3834 (19)
C3—H3A	0.9500	C13—C14	1.3926 (17)
C4—C5	1.3794 (18)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.4100 (17)

O1ⁱ—Ni1—O1	180.0	N1—C7—C6	126.56 (11)
O1ⁱ—Ni1—N1ⁱ	92.56 (4)	N1—C7—H7A	116.7
O1—Ni1—N1ⁱ	87.44 (4)	C6—C7—H7A	116.7
O1ⁱ—Ni1—N1	87.44 (4)	N1—C8—C9	110.45 (9)
O1—Ni1—N1	92.56 (4)	N1—C8—H8A	109.6
N1ⁱ—Ni1—N1	180.00 (6)	C9—C8—H8A	109.6
C7—N1—C8	114.48 (10)	N1—C8—H8B	109.6
C7—N1—Ni1	123.90 (8)	C9—C8—H8B	109.6
C8—N1—Ni1	121.62 (8)	H8A—C8—H8B	108.1
C1—O1—Ni1	129.03 (8)	C14—C9—C10	118.57 (11)
O1—C1—C6	123.23 (11)	C14—C9—C8	121.18 (11)
O1—C1—C2	118.67 (11)	C10—C9—C8	120.25 (11)
C6—C1—C2	118.10 (11)	C11—C10—C9	121.36 (12)
C3—C2—C1	120.18 (12)	C11—C10—H10A	119.3
C3—C2—H2A	119.9	C9—C10—H10A	119.3
C1—C2—H2A	119.9	C12—C11—C10	117.89 (12)
C2—C3—C4	121.73 (12)	C12—C11—H11A	121.1
C2—C3—H3A	119.1	C10—C11—H11A	121.1
C4—C3—H3A	119.1	F1—C12—C11	118.81 (12)
C5—C4—C3	118.79 (12)	F1—C12—C13	118.24 (13)
C5—C4—H4A	120.6	C11—C12—C13	122.95 (12)
C3—C4—H4A	120.6	C12—C13—C14	118.04 (12)
C4—C5—C6	120.87 (12)	C12—C13—H13A	121.0
C4—C5—H5A	119.6	C14—C13—H13A	121.0
C6—C5—H5A	119.6	C13—C14—C9	121.18 (12)
C5—C6—C1	120.33 (11)	C13—C14—H14A	119.4
C5—C6—C7	118.85 (11)	C9—C14—H14A	119.4
C1—C6—C7	120.62 (11)

O1ⁱ—Ni1—N1—C7	−161.69 (10)	C8—N1—C7—C6	171.36 (11)
O1—Ni1—N1—C7	18.31 (10)	Ni1—N1—C7—C6	−8.09 (17)
O1ⁱ—Ni1—N1—C8	18.90 (9)	C5—C6—C7—N1	177.97 (11)
O1—Ni1—N1—C8	−161.10 (9)	C1—C6—C7—N1	−7.20 (18)
N1ⁱ—Ni1—O1—C1	158.63 (10)	C7—N1—C8—C9	−97.31 (12)
N1—Ni1—O1—C1	−21.37 (10)	Ni1—N1—C8—C9	82.15 (11)
Ni1—O1—C1—C6	12.98 (17)	N1—C8—C9—C14	−87.37 (13)
Ni1—O1—C1—C2	−166.89 (9)	N1—C8—C9—C10	92.19 (13)
O1—C1—C2—C3	179.45 (11)	C14—C9—C10—C11	−0.29 (18)
C6—C1—C2—C3	−0.42 (17)	C8—C9—C10—C11	−179.86 (12)
C1—C2—C3—C4	0.48 (19)	C9—C10—C11—C12	0.9 (2)
C2—C3—C4—C5	−0.03 (19)	C10—C11—C12—F1	178.90 (12)
C3—C4—C5—C6	−0.47 (19)	C10—C11—C12—C13	−0.9 (2)
C4—C5—C6—C1	0.52 (18)	F1—C12—C13—C14	−179.49 (11)
C4—C5—C6—C7	175.37 (11)	C11—C12—C13—C14	0.3 (2)
O1—C1—C6—C5	−179.94 (11)	C12—C13—C14—C9	0.31 (19)
C2—C1—C6—C5	−0.07 (17)	C10—C9—C14—C13	−0.32 (18)
O1—C1—C6—C7	5.30 (18)	C8—C9—C14—C13	179.25 (11)
C2—C1—C6—C7	−174.83 (11)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.99	2.19	2.7300 (18)	113
C14—H14A···O1ⁱ	0.95	2.52	3.212 (2)	130
C2—H2A···F1ⁱⁱ	0.95	2.65	3.5312 (19)	155
C5—H5A···Cg1ⁱⁱⁱ	0.95	2.69	3.4010 (18)	133
C13—H13A···Cg2^iv	0.95	2.69	3.4252 (13)	134

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −y−1/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.99	2.19	2.7300 (18)	113
C14—H14A···O1ⁱ	0.95	2.52	3.212 (2)	130
C2—H2A···F1ⁱⁱ	0.95	2.65	3.5312 (19)	155
C5—H5A···Cg1ⁱⁱⁱ	0.95	2.685	3.4010 (18)	133
C13—H13A···Cg2^iv	0.95	2.693	3.4252 (13)	134

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −y−1/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₁FNO)₂]
M_r	515.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.8611 (3), 5.83340 (1), 16.9942 (3)
β (°)	125.998 (1)
V (Å³)	1111.70 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.47 × 0.19 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.674, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	13419, 3235, 2896
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.072, 1.05
No. of reflections	3235
No. of parameters	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.49

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors would like to acknowledge the Ministry of Education of Malaysia for research grants No. 600-RMI/FRGS 5/3 (51/2013) and (52/2013), Universiti Teknologi MARA for research grant No. 600-RMI/DANA 5/3/CG (15/2012) and Universiti Sains Malaysia for the use of the X-ray diffraction facilities. The authors would also like to acknowledge Universiti Kebangsaan Malaysia for the usage of its research facility for biological activity investigation.

References

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Volume 70| Part 10| October 2014| Pages 252-255

doi:10.1107/S1600536814020546

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