Bis{4-[(Z)-(4-fluoro­benzyl­amino)(phenyl)­methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onato-κ2N4,O}nickel(II)

Zhang, X.; Zhang, G.-Y.; Chen, D.; Song, Y.-J.

doi:10.1107/S1600536808009197

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m642

doi:10.1107/S1600536808009197

Open

access

Bis{4-[(Z)-(4-fluorobenzylamino)(phenyl)methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onato-κ²N⁴,O}nickel(II)

Xin Zhang,^a ^* Guo-Ying Zhang,^a Dan Chen ^a and Yu-Jing Song ^a

^aCollege of Chemistry and Life Sciences, Tianjin Normal University, Tianjin 300074, People's Republic of China
^*Correspondence e-mail: zxin_tj@126.com

(Received 10 January 2008; accepted 4 April 2008; online 10 April 2008)

The molecule of the title compound, [Ni(C₂₄H₁₉FN₃O)₂], has twofold rotation symmetry. The Ni^II ion is in a square-planar coordination geometry which is distorted towards tetrahedral and is coordinated by two N atoms of imine and two O atoms of pyrazolone from two Schiff base 4-[(Z)-(4-fluorobenzylamino)phenylmethylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onate ligands.

Related literature

For related literature, see: Sesser et al. (1993 ); Smith et al. (1989 ); Padhy et al. (1985 ); Yu et al. (1993 ); Wu et al. (1993 ); Zhao (2007 ); Peng et al. (2006 ); Xu et al. (2006 ); Bao et al. (2005 ); Ma et al. (2006 ); Wang (2006 ); Li & Wang (2007 ).

Experimental

Crystal data

[Ni(C₂₄H₁₉FN₃O)₂]
M_r = 827.55
Orthorhombic, P b c n
a = 25.475 (2) Å
b = 10.1620 (8) Å
c = 15.700 (1) Å
V = 4064.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 293 (2) K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.866, T_max = 0.910
26008 measured reflections
4867 independent reflections
2916 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.076
S = 1.42
4867 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009197/lx2051sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009197/lx2051Isup2.hkl

checkCIF report

Comment top

Complexes of Schiff bases with paramagnetic metal ions have received the much attention as a new class of potential magnetic resonance imaging (MRI) contrast agent [Sesser et al., 1993; Smith et al., 1989]. In addition, a great many Schiff base complexes with metals have also provoked wide interest because they possess a diverse spectrum of biological and pharmaceutical activities and catalytic properties, such as antitumor and antioxidative activities, as well as the inhibition of lipid peroxidation and so on [Padhy et al., 1985; Yu et al., 1993; Wu et al., 1993]. In this paper, we report the synthesis and crystal structure of the title compound, (I), containing β-ketoamine ligand with organic fluorine based on pyrazolone derivatives.

The molecular structure of (I) is shown in Fig. 1. The molecule has approximate twofold rotation symmetry. The Ni^II ion is in a distorted square-planar coordination geometry which is different from other square-planar geometry (Wang, 2006; Li & Wang, 2007) and is coordinated by two N atoms of imine and two O atoms of pyrazoylone from two Schiff base ligands L. The geometry is distorted towards tetrahedral. The bond angles around Ni^II center range from 96.63 (5) to 146.30 (8)° and the Ni—N [1.951 (1) Å] and Ni—O [1.924 (1) Å] bond lengths in (I) are in the expected range for such complexes (Zhao, 2007; Peng et al., 2006).

In the crystal structure of (I), the exocyclic C═O bond [1.284 (2) Å for C9═O1] is lengthened relative to that in the free ligand [1.252 (3) Å; Xu et al., 2006], indicating the ligands in the complex have partially changed into enol form from keto form. Mean devation of 0.049 Å from the least-square plane defined by the nine constituent atoms (Ni O1 C9 N1 N2 C7 C8 C11 N3). The pyrazolone ring is nearly coplanar with the C1—C6 benzene ring and nearly perpendicular to the other two benzene rings (C12—C17 and C19–C24); the dihedral angles are 40.54 (5), 87.78 (5) and 80.99 (5)°, respectively. There are no significant intermolecular interactions in the crystal structure.

The structures of metal complexes with ligands in which the 4-fluorophenyl group of L is replaced by Ph in Cu(L¹)₂ (distorted square-planar coordination geometry; Bao et al., 2005) and Co(L²)₂ (distorted tetrahedral coordination geometry; Ma et al., 2006) have been reported.

Related literature top

For related literature, see: Sesser et al. (1993); Smith et al. (1989); Padhy et al. (1985); Yu et al. (1993); Wu et al. (1993); Zhao (2007); Peng et al. (2006); Xu et al. (2006); Bao et al. (2005); Ma et al. (2006); Wang (2006); Li & Wang(2007).

Experimental top

(4Z)-4-[(4-Fluorobenzylamino)(phenyl)-methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1.0 mmol) and Ni(Ac)₂ (1.0 mmol) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for about 1 h, then heated to reflux for 3 h. After allowing the solution to stand in air for 7 d, green lock-shaped crystals were formed with a yield of 40%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with anisotropic displacement ellipsoids drawn at the 30% probability level [Symmetry code: (i) -x + 1,y,-z + 1/2.]

Bis{4-[(Z)-(4-fluorobenzylamino)phenylmethylene]-3-methyl-1-phenyl- 1H-pyrazol-5(4H)-onato-κ²N⁴,O}nickel(II) top

Crystal data top

[Ni(C₂₄H₁₉FN₃O)₂]	F(000) = 1720
M_r = 827.55	D_x = 1.352 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3309 reflections
a = 25.475 (2) Å	θ = 2.5–22.0°
b = 10.1620 (8) Å	µ = 0.54 mm⁻¹
c = 15.700 (1) Å	T = 293 K
V = 4064.4 (5) Å³	BLOCK, red
Z = 4	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	4867 independent reflections
Radiation source: fine-focus sealed tube	2916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ϕ and ω scans	h = −21→33
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −13→12
T_min = 0.866, T_max = 0.910	l = −20→18
26008 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.42	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
4867 reflections	(Δ/σ)_max = 0.001
268 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ni(C₂₄H₁₉FN₃O)₂]	V = 4064.4 (5) Å³
M_r = 827.55	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 25.475 (2) Å	µ = 0.54 mm⁻¹
b = 10.1620 (8) Å	T = 293 K
c = 15.700 (1) Å	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	4867 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2916 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.910	R_int = 0.043
26008 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.42	Δρ_max = 0.20 e Å⁻³
4867 reflections	Δρ_min = −0.25 e Å⁻³
268 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
Ni	0.5000	0.74902 (3)	0.2500	0.03705 (9)
F	0.60501 (7)	1.27896 (15)	0.15762 (10)	0.1420 (6)
O	0.45522 (4)	0.67156 (10)	0.33499 (7)	0.0455 (3)
N1	0.37188 (5)	0.64453 (14)	0.39135 (9)	0.0521 (4)
N2	0.31974 (6)	0.66922 (18)	0.36965 (10)	0.0710 (5)
N3	0.44445 (5)	0.80468 (13)	0.17239 (8)	0.0445 (3)
C1	0.42626 (7)	0.53082 (17)	0.49505 (12)	0.0615 (5)
H1	0.4466	0.4956	0.4514	0.074*
C2	0.43833 (8)	0.50343 (19)	0.57895 (14)	0.0728 (6)
H2	0.4672	0.4508	0.5915	0.087*
C3	0.40835 (9)	0.5529 (2)	0.64395 (13)	0.0712 (6)
H3	0.4169	0.5348	0.7003	0.085*
C4	0.36580 (8)	0.6288 (2)	0.62491 (12)	0.0736 (6)
H4	0.3448	0.6611	0.6686	0.088*
C5	0.35365 (7)	0.65816 (18)	0.54168 (11)	0.0612 (5)
H5	0.3247	0.7106	0.5296	0.073*
C6	0.38418 (6)	0.61033 (16)	0.47621 (11)	0.0473 (4)
C7	0.32123 (7)	0.7208 (2)	0.29336 (13)	0.0677 (6)
C8	0.37393 (6)	0.73431 (16)	0.26211 (10)	0.0466 (4)
C9	0.40520 (6)	0.68240 (16)	0.32787 (10)	0.0428 (4)
C10	0.26929 (8)	0.7559 (2)	0.25261 (14)	0.1213 (12)
H10A	0.2666	0.7134	0.1982	0.182*
H10B	0.2672	0.8496	0.2451	0.182*
H10C	0.2411	0.7272	0.2886	0.182*
C11	0.39386 (6)	0.79288 (16)	0.18624 (10)	0.0446 (4)
C12	0.35452 (6)	0.84084 (18)	0.12212 (11)	0.0498 (4)
C13	0.33603 (7)	0.75812 (19)	0.05954 (11)	0.0587 (5)
H13	0.3490	0.6728	0.0555	0.070*
C14	0.29816 (7)	0.8014 (2)	0.00249 (13)	0.0735 (6)
H14	0.2860	0.7452	−0.0399	0.088*
C15	0.27871 (8)	0.9262 (3)	0.00842 (16)	0.0874 (8)
H15	0.2533	0.9549	−0.0298	0.105*
C16	0.29663 (8)	1.0086 (2)	0.07052 (18)	0.0909 (8)
H16	0.2833	1.0936	0.0744	0.109*
C17	0.33442 (7)	0.9671 (2)	0.12765 (14)	0.0735 (6)
H17	0.3464	1.0240	0.1698	0.088*
C18	0.46406 (6)	0.86510 (17)	0.09264 (10)	0.0527 (5)
H18A	0.4346	0.8985	0.0601	0.063*
H18B	0.4814	0.7984	0.0586	0.063*
C19	0.50202 (7)	0.97610 (18)	0.11001 (10)	0.0507 (4)
C20	0.48434 (9)	1.0994 (2)	0.13394 (13)	0.0776 (6)
H20	0.4485	1.1140	0.1399	0.093*
C21	0.51909 (13)	1.2011 (3)	0.14913 (16)	0.0981 (8)
H21	0.5070	1.2840	0.1647	0.118*
C22	0.57081 (12)	1.1778 (3)	0.14100 (14)	0.0883 (8)
C23	0.59040 (9)	1.0606 (3)	0.11648 (14)	0.0788 (7)
H23	0.6264	1.0477	0.1113	0.095*
C24	0.55516 (7)	0.95964 (19)	0.09921 (12)	0.0612 (5)
H24	0.5678	0.8791	0.0799	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.02468 (14)	0.06300 (18)	0.02347 (13)	0.000	0.00016 (12)	0.000
F	0.1785 (15)	0.1505 (13)	0.0970 (12)	−0.1026 (12)	−0.0011 (10)	−0.0095 (10)
O	0.0322 (6)	0.0664 (7)	0.0379 (7)	0.0036 (6)	0.0040 (5)	0.0071 (6)
N1	0.0325 (8)	0.0818 (10)	0.0421 (9)	−0.0017 (7)	0.0053 (6)	0.0073 (8)
N2	0.0316 (9)	0.1299 (15)	0.0514 (11)	−0.0065 (9)	0.0032 (7)	0.0108 (10)
N3	0.0349 (8)	0.0695 (9)	0.0291 (7)	−0.0051 (7)	−0.0005 (6)	0.0011 (7)
C1	0.0614 (13)	0.0680 (13)	0.0551 (13)	0.0088 (10)	0.0174 (9)	0.0123 (11)
C2	0.0678 (14)	0.0820 (15)	0.0686 (15)	0.0128 (11)	0.0094 (12)	0.0304 (12)
C3	0.0771 (16)	0.0885 (15)	0.0480 (13)	−0.0108 (12)	0.0019 (11)	0.0194 (11)
C4	0.0771 (16)	0.0996 (16)	0.0442 (13)	0.0030 (13)	0.0142 (10)	−0.0034 (12)
C5	0.0516 (12)	0.0838 (14)	0.0482 (12)	0.0107 (10)	0.0091 (9)	0.0030 (10)
C6	0.0410 (10)	0.0609 (11)	0.0400 (11)	−0.0061 (9)	0.0066 (8)	0.0055 (8)
C7	0.0327 (10)	0.1215 (18)	0.0488 (12)	−0.0031 (10)	−0.0004 (9)	0.0073 (12)
C8	0.0312 (8)	0.0730 (12)	0.0357 (11)	−0.0037 (8)	−0.0012 (7)	0.0015 (9)
C9	0.0341 (9)	0.0583 (10)	0.0359 (10)	−0.0038 (8)	0.0052 (8)	−0.0020 (8)
C10	0.0306 (11)	0.260 (4)	0.0731 (16)	−0.0052 (15)	−0.0036 (10)	0.0410 (19)
C11	0.0332 (9)	0.0644 (11)	0.0360 (10)	0.0005 (8)	−0.0043 (7)	−0.0042 (8)
C12	0.0321 (10)	0.0721 (13)	0.0452 (11)	−0.0058 (9)	−0.0051 (8)	0.0063 (10)
C13	0.0461 (11)	0.0822 (13)	0.0479 (11)	−0.0086 (10)	−0.0115 (8)	0.0055 (11)
C14	0.0585 (14)	0.1094 (17)	0.0527 (13)	−0.0275 (12)	−0.0213 (10)	0.0174 (12)
C15	0.0522 (14)	0.113 (2)	0.097 (2)	−0.0190 (14)	−0.0315 (12)	0.0466 (16)
C16	0.0561 (14)	0.0820 (16)	0.134 (2)	0.0067 (11)	−0.0280 (14)	0.0224 (16)
C17	0.0502 (13)	0.0788 (14)	0.0915 (17)	0.0026 (11)	−0.0198 (11)	−0.0045 (12)
C18	0.0408 (10)	0.0854 (13)	0.0319 (10)	−0.0046 (9)	−0.0045 (8)	0.0085 (9)
C19	0.0462 (11)	0.0744 (12)	0.0316 (9)	−0.0046 (10)	−0.0041 (8)	0.0125 (8)
C20	0.0710 (15)	0.0945 (17)	0.0675 (16)	−0.0001 (13)	0.0161 (11)	−0.0024 (13)
C21	0.130 (2)	0.0836 (16)	0.0808 (19)	−0.0205 (17)	0.0294 (17)	−0.0168 (14)
C22	0.108 (2)	0.104 (2)	0.0527 (14)	−0.0481 (19)	−0.0053 (14)	0.0039 (14)
C23	0.0555 (14)	0.1039 (18)	0.0770 (17)	−0.0236 (13)	−0.0132 (11)	0.0407 (15)
C24	0.0466 (12)	0.0723 (13)	0.0646 (13)	−0.0031 (10)	−0.0003 (9)	0.0268 (11)

Geometric parameters (Å, º) top

Ni—Oⁱ	1.924 (1)	C10—H10B	0.9600
Ni—O	1.924 (1)	C10—H10C	0.9600
Ni—N3ⁱ	1.951 (1)	C11—C12	1.502 (2)
Ni—N3	1.951 (1)	C12—C13	1.376 (2)
F—C22	1.373 (2)	C12—C17	1.384 (2)
O—C9	1.284 (2)	C13—C14	1.388 (2)
N1—C9	1.365 (2)	C13—H13	0.9300
N1—N2	1.394 (2)	C14—C15	1.365 (3)
N1—C6	1.412 (2)	C14—H14	0.9300
N2—C7	1.308 (2)	C15—C16	1.364 (3)
N3—C11	1.313 (2)	C15—H15	0.9300
N3—C18	1.481 (2)	C16—C17	1.382 (3)
C1—C6	1.375 (2)	C16—H16	0.9300
C1—C2	1.381 (2)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.511 (2)
C2—C3	1.370 (3)	C18—H18A	0.9700
C2—H2	0.9300	C18—H18B	0.9700
C3—C4	1.364 (3)	C19—C24	1.374 (2)
C3—H3	0.9300	C19—C20	1.383 (3)
C4—C5	1.376 (2)	C20—C21	1.381 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.378 (2)	C21—C22	1.345 (3)
C5—H5	0.9300	C21—H21	0.9300
C7—C8	1.436 (2)	C22—C23	1.347 (3)
C7—C10	1.513 (3)	C23—C24	1.390 (3)
C8—C9	1.407 (2)	C23—H23	0.9300
C8—C11	1.425 (2)	C24—H24	0.9300
C10—H10A	0.9600

Oⁱ—Ni—O	131.70 (6)	H10B—C10—H10C	109.5
Oⁱ—Ni—N3ⁱ	96.99 (5)	N3—C11—C8	121.8 (1)
O—Ni—N3ⁱ	96.63 (5)	N3—C11—C12	121.0 (1)
Oⁱ—Ni—N3	96.63 (5)	C8—C11—C12	117.27 (14)
O—Ni—N3	96.99 (5)	C13—C12—C17	119.0 (2)
N3ⁱ—Ni—N3	146.30 (8)	C13—C12—C11	120.6 (2)
C9—O—Ni	119.5 (1)	C17—C12—C11	120.4 (2)
C9—N1—N2	111.3 (1)	C12—C13—C14	120.4 (2)
C9—N1—C6	128.4 (1)	C12—C13—H13	119.8
N2—N1—C6	119.1 (1)	C14—C13—H13	119.8
C7—N2—N1	105.6 (1)	C15—C14—C13	120.2 (2)
C11—N3—C18	120.6 (1)	C15—C14—H14	119.9
C11—N3—Ni	125.6 (1)	C13—C14—H14	119.9
C18—N3—Ni	113.79 (9)	C14—C15—C16	119.9 (2)
C6—C1—C2	119.8 (2)	C14—C15—H15	120.1
C6—C1—H1	120.1	C16—C15—H15	120.1
C2—C1—H1	120.1	C15—C16—C17	120.6 (2)
C3—C2—C1	120.8 (2)	C15—C16—H16	119.7
C3—C2—H2	119.6	C17—C16—H16	119.7
C1—C2—H2	119.6	C12—C17—C16	120.0 (2)
C4—C3—C2	119.2 (2)	C12—C17—H17	120.0
C4—C3—H3	120.4	C16—C17—H17	120.0
C2—C3—H3	120.4	N3—C18—C19	111.9 (1)
C3—C4—C5	120.6 (2)	N3—C18—H18A	109.2
C3—C4—H4	119.7	C19—C18—H18A	109.2
C5—C4—H4	119.7	N3—C18—H18B	109.2
C6—C5—C4	120.3 (2)	C19—C18—H18B	109.2
C6—C5—H5	119.8	H18A—C18—H18B	107.9
C4—C5—H5	119.8	C24—C19—C20	117.7 (2)
C1—C6—C5	119.2 (2)	C24—C19—C18	121.2 (2)
C1—C6—N1	121.4 (2)	C20—C19—C18	121.1 (2)
C5—C6—N1	119.5 (2)	C21—C20—C19	121.0 (2)
N2—C7—C8	112.2 (2)	C21—C20—H20	119.5
N2—C7—C10	117.2 (2)	C19—C20—H20	119.5
C8—C7—C10	130.6 (2)	C22—C21—C20	118.7 (2)
C9—C8—C11	124.6 (2)	C22—C21—H21	120.7
C9—C8—C7	104.1 (2)	C20—C21—H21	120.7
C11—C8—C7	131.2 (2)	C21—C22—C23	123.1 (2)
O—C9—N1	122.0 (2)	C21—C22—F	118.2 (3)
O—C9—C8	131.2 (2)	C23—C22—F	118.8 (3)
N1—C9—C8	106.8 (1)	C22—C23—C24	118.0 (2)
C7—C10—H10A	109.5	C22—C23—H23	121.0
C7—C10—H10B	109.5	C24—C23—H23	121.0
H10A—C10—H10B	109.5	C19—C24—C23	121.5 (2)
C7—C10—H10C	109.5	C19—C24—H24	119.3
H10A—C10—H10C	109.5	C23—C24—H24	119.3

Oⁱ—Ni—O—C9	−111.23 (12)	C11—C8—C9—N1	175.72 (15)
N3ⁱ—Ni—O—C9	143.24 (12)	C7—C8—C9—N1	−0.71 (18)
N3—Ni—O—C9	−5.86 (12)	C18—N3—C11—C8	179.54 (14)
C9—N1—N2—C7	0.5 (2)	Ni—N3—C11—C8	−0.8 (2)
C6—N1—N2—C7	168.80 (16)	C18—N3—C11—C12	−0.4 (2)
Oⁱ—Ni—N3—C11	137.19 (14)	Ni—N3—C11—C12	179.28 (12)
O—Ni—N3—C11	3.64 (14)	C9—C8—C11—N3	−1.0 (3)
N3ⁱ—Ni—N3—C11	−109.53 (14)	C7—C8—C11—N3	174.36 (17)
Oⁱ—Ni—N3—C18	−43.14 (11)	C9—C8—C11—C12	178.89 (16)
O—Ni—N3—C18	−176.69 (11)	C7—C8—C11—C12	−5.7 (3)
N3ⁱ—Ni—N3—C18	70.14 (10)	N3—C11—C12—C13	90.9 (2)
C6—C1—C2—C3	1.0 (3)	C8—C11—C12—C13	−89.0 (2)
C1—C2—C3—C4	0.7 (3)	N3—C11—C12—C17	−92.2 (2)
C2—C3—C4—C5	−1.4 (3)	C8—C11—C12—C17	87.9 (2)
C3—C4—C5—C6	0.4 (3)	C17—C12—C13—C14	0.6 (3)
C2—C1—C6—C5	−2.0 (3)	C11—C12—C13—C14	177.48 (16)
C2—C1—C6—N1	177.55 (16)	C12—C13—C14—C15	−0.4 (3)
C4—C5—C6—C1	1.3 (3)	C13—C14—C15—C16	0.1 (3)
C4—C5—C6—N1	−178.28 (17)	C14—C15—C16—C17	0.1 (4)
C9—N1—C6—C1	−43.5 (3)	C13—C12—C17—C16	−0.4 (3)
N2—N1—C6—C1	150.35 (16)	C11—C12—C17—C16	−177.32 (19)
C9—N1—C6—C5	136.03 (18)	C15—C16—C17—C12	0.1 (4)
N2—N1—C6—C5	−30.1 (2)	C11—N3—C18—C19	126.69 (16)
N1—N2—C7—C8	−0.9 (2)	Ni—N3—C18—C19	−53.00 (16)
N1—N2—C7—C10	179.03 (17)	N3—C18—C19—C24	104.07 (18)
N2—C7—C8—C9	1.1 (2)	N3—C18—C19—C20	−78.6 (2)
C10—C7—C8—C9	−178.9 (2)	C24—C19—C20—C21	−2.1 (3)
N2—C7—C8—C11	−175.04 (18)	C18—C19—C20—C21	−179.47 (19)
C10—C7—C8—C11	5.0 (4)	C19—C20—C21—C22	−0.6 (4)
Ni—O—C9—N1	−171.42 (12)	C20—C21—C22—C23	1.8 (4)
Ni—O—C9—C8	6.3 (2)	C20—C21—C22—F	−178.94 (19)
N2—N1—C9—O	178.37 (15)	C21—C22—C23—C24	−0.2 (4)
C6—N1—C9—O	11.4 (3)	F—C22—C23—C24	−179.45 (17)
N2—N1—C9—C8	0.20 (19)	C20—C19—C24—C23	3.7 (3)
C6—N1—C9—C8	−166.79 (16)	C18—C19—C24—C23	−178.87 (16)
C11—C8—C9—O	−2.2 (3)	C22—C23—C24—C19	−2.7 (3)
C7—C8—C9—O	−178.65 (18)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₄H₁₉FN₃O)₂]
M_r	827.55
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	25.475 (2), 10.1620 (8), 15.700 (1)
V (Å³)	4064.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.866, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	26008, 4867, 2916
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.076, 1.42
No. of reflections	4867
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bao, F., Feng, J. & Ng, S. W. (2005). Acta Cryst. E61, m2393–m2394. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1998). SAINT, SADABS and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, L.-Z. & Wang, L.-H. (2007). Acta Cryst. E63, m1791. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, R.-M., Sun, S.-F. & Ng, S. W. (2006). Acta Cryst. E62, m2711–m2712. Web of Science CSD CrossRef IUCr Journals Google Scholar
Padhy, S. & Kauffman, G. B. (1985). Coord. Chem. Rev. 63, 127–160. Google Scholar
Peng, S., Zhou, C. & Yang, T. (2006). Acta Cryst. E62, m1066–m1068. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sesser, J. L., Mody, T. D., Hemmi, G. W. & Lynch, V. (1993). Inorg. Chem. 32, 3175–3187. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, P. S., Brainard, J. R., Morris, D. E., Jarvinen, G. D. & Ryan, R. R. (1989). J. Am. Chem. Soc. 111, 7437–7443. CSD CrossRef CAS Web of Science Google Scholar
Wang, C. (2006). Acta Cryst. E62, m1754–m1755. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, J. G., Deng, R. W. & Chen, Z. N. (1993). Transition Met. Chem. 18, 23–26. CrossRef CAS Web of Science Google Scholar
Xu, H.-Z., Si, X.-K., Zhu, Y.-Q. & Song, H.-B. (2006). Acta Cryst. E62, o3266–o3268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, S. Y., Wang, S. X., Luo, Q. H., Wang, L. F., Peng, Z. R. & Gao, X. (1993). Polyhedron, 12, 1093–1096. CrossRef CAS Web of Science Google Scholar
Zhao, X.-F. (2007). Acta Cryst. E63, m704–m705. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.