Tris(pyridin-2-yl­methanol)nickel(II) hexa­fluoridophosphate trifluoro­acetate

Hamaguchi, T.; Nagata, T.; Kawata, S.; Ando, I.

doi:10.1107/S160053681104431X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1632

doi:10.1107/S160053681104431X

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Tris(pyridin-2-ylmethanol)nickel(II) hexafluoridophosphate trifluoroacetate

Tomohiko Hamaguchi,^a ^* Tomoko Nagata,^a Satoshi Kawata ^a and Isao Ando ^a

^aDepartment of Chemistry, Faculty of Science, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
^*Correspondence e-mail: thama@fukuoka-u.ac.jp

(Received 26 September 2011; accepted 25 October 2011; online 29 October 2011)

In the crystal structure of the title complex, [Ni(C₆H₇NO)₃](PF₆)(C₂F₃O₂), the Ni^II ion is in a slightly distorted octahedral NiO₃N₃ coordination geometry with each of the three N and three O atoms in a meridional coordination. In the crystal, the complex molecules and the trifluoroacetate anions are connected via O—H⋯O hydrogen bonding into layers parallel to the ab plane.

Related literature

For related complexes, see: Ito & Onaka (2004 ); Kermagoret & Braunstein (2008 ).

Experimental

Crystal data

[Ni(C₆H₇NO)₃](PF₆)(C₂F₃O₂)
M_r = 644.08
Triclinic, $[P \overline 1]$
a = 9.6381 (2) Å
b = 11.9668 (4) Å
c = 11.9892 (3) Å
α = 109.950 (1)°
β = 95.348 (1)°
γ = 101.411 (1)°
V = 1254.60 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 200 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.813, T_max = 1.000
12517 measured reflections
5736 independent reflections
5234 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.05
5736 reflections
376 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	2.0461 (12)
Ni1—N2	2.0601 (14)
Ni1—O2	2.0647 (12)
Ni1—N1	2.0662 (14)
Ni1—O3	2.0714 (12)
Ni1—N3	2.0769 (14)

O1—Ni1—N1	78.11 (5)
N2—Ni1—O2	78.53 (5)
O3—Ni1—N3	78.09 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.87	1.76	2.6003 (19)	162.5
O2—H2⋯O5ⁱⁱ	0.92	1.77	2.6965 (18)	175.8
O3—H3⋯O5ⁱⁱⁱ	0.98	1.65	2.6267 (18)	173.8
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 2002 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Yadokari-XG (Wakita, 2001 ; Kabuto et al., 2009 ), ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: Yadokari-XG and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681104431X/nc2249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104431X/nc2249Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound is composed of [Ni^II(C₆H₇ON)₃]²⁺ cations, hexafluorophosphate and trifluoroacetate anions. The Ni^II ion is in a slightly distorted octahedral coordination, comprising three N atoms and three O atoms from three pyridine-2-methanol ligands (Fig. 1 and Table 1). The three N and three O atoms make a meridional NiO₃N₃ coordination and the mean bite angle of the pyridine-2-methanol ligand amount to 78.2 (2) °.

In the crystal structure the complexes are connected via O—H···O hydrogen bonding between the hydroxy H atoms of the pyridine-2-methanol ligand and the O atoms of the trifluoroacetate anion into layers that are parallel to the a/b plane. (Fig. 2 and 3 and Table 2).

Related literature top

For related complexes, see: Ito & Onaka (2004); Kermagoret & Braunstein (2008).

Experimental top

A solution of NiSO₄.6H₂O (0.5 mmol) in H₂O (1 ml) was added to the solution of pyridine-2-methanol (1.5 mmol) in H₂O (3 ml). Afterwards NH₄PF₆ (6.0 mmol) and CF₃COONa (2.5 mmol) were added to the resulting blue solution. The resulting pale blue precipitate was collected. The crude product was purified by recrystallization from acetone and water. The blue prism-like crystals were obtained a few days later on slow evaporation of the solvent.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2002); cell refinement: RAPID-AUTO (Rigaku, 2002); data reduction: RAPID-AUTO (Rigaku, 2002); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009), ORTEP-3 for Windows (Farrugia ,1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009)and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP drawing for the title complex with labeling showing 50% probability displacement ellipsoids. Please note: The trifluoroacetate anion is disordered.
	Fig. 2. Crystal structure of the title compound view along the b-axis. The C-H H atoms, the PF₆ anions and the disordered F atoms with lower occupation of the trifluoroacetate anions are omitted for clarity. O—H···O hydrogen bonding is shown as dashed blue lines.
	Fig. 3. Crystal structure of the title compound with view along the c-axis. The C-H H atoms and the disordered F atoms with lower occupation of the trifluoroacetate anions are omitted for clarity.

Tris(pyridin-2-ylmethanol)nickel(II) hexafluoridophosphate trifluoroacetate top

Crystal data top

[Ni(C₆H₇NO)₃](PF₆)(C₂F₃O₂)	V = 1254.60 (6) Å³
M_r = 644.08	Z = 2
Triclinic, P1	F(000) = 652
Hall symbol: -P 1	D_x = 1.705 Mg m⁻³
a = 9.6381 (2) Å	Mo Kα radiation, λ = 0.71075 Å
b = 11.9668 (4) Å	µ = 0.94 mm⁻¹
c = 11.9892 (3) Å	T = 200 K
α = 109.950 (1)°	Block, blue
β = 95.348 (1)°	0.40 × 0.30 × 0.20 mm
γ = 101.411 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −12→11
T_min = 0.813, T_max = 1.000	k = −15→15
12517 measured reflections	l = −15→15
5736 independent 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0486P)² + 0.5841P] where P = (F_o² + 2F_c²)/3
5736 reflections	(Δ/σ)_max = 0.001
376 parameters	Δρ_max = 0.50 e Å⁻³
9 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Ni(C₆H₇NO)₃](PF₆)(C₂F₃O₂)	γ = 101.411 (1)°
M_r = 644.08	V = 1254.60 (6) Å³
Triclinic, P1	Z = 2
a = 9.6381 (2) Å	Mo Kα radiation
b = 11.9668 (4) Å	µ = 0.94 mm⁻¹
c = 11.9892 (3) Å	T = 200 K
α = 109.950 (1)°	0.40 × 0.30 × 0.20 mm
β = 95.348 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5736 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	5234 reflections with I > 2σ(I)
T_min = 0.813, T_max = 1.000	R_int = 0.018
12517 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	9 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.05	Δρ_max = 0.50 e Å⁻³
5736 reflections	Δρ_min = −0.45 e Å⁻³
376 parameters

Special details top

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 > 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	Occ. (<1)
Ni1	0.18393 (2)	0.369025 (18)	0.808996 (17)	0.02212 (7)
O1	0.00845 (13)	0.39356 (12)	0.88953 (12)	0.0304 (3)
H1	−0.0596	0.4198	0.8609	0.046*
O2	0.35252 (13)	0.32008 (12)	0.72559 (12)	0.0337 (3)
H2	0.4425	0.3733	0.7547	0.051*
O3	0.33165 (14)	0.49798 (11)	0.95482 (11)	0.0316 (3)
H3	0.3431	0.5104	1.0408	0.047*
N1	0.16982 (15)	0.24566 (12)	0.89561 (13)	0.0257 (3)
N2	0.07694 (15)	0.24685 (13)	0.64160 (13)	0.0264 (3)
N3	0.20297 (15)	0.52595 (13)	0.76794 (12)	0.0255 (3)
C1	0.26677 (19)	0.17914 (16)	0.90061 (18)	0.0338 (4)
H4	0.3381	0.1775	0.8509	0.041*
C2	0.2656 (2)	0.11372 (19)	0.9755 (2)	0.0447 (5)
H5	0.3343	0.0670	0.9765	0.054*
C3	0.1636 (3)	0.1169 (2)	1.0488 (2)	0.0530 (6)
H6	0.1624	0.0740	1.1025	0.064*
C4	0.0627 (2)	0.1836 (2)	1.0432 (2)	0.0458 (5)
H7	−0.0093	0.1864	1.0924	0.055*
C5	0.06813 (18)	0.24611 (15)	0.96467 (16)	0.0286 (3)
C6	−0.04137 (18)	0.31692 (16)	0.95294 (17)	0.0297 (4)
H8	−0.1347	0.2596	0.9086	0.036*
H9	−0.0553	0.3674	1.0338	0.036*
C7	−0.06644 (19)	0.20268 (16)	0.60926 (16)	0.0306 (4)
H10	−0.1254	0.2263	0.6681	0.037*
C8	−0.1309 (2)	0.12438 (17)	0.49383 (18)	0.0377 (4)
H11	−0.2324	0.0945	0.4734	0.045*
C9	−0.0448 (2)	0.09037 (18)	0.40852 (18)	0.0418 (5)
H12	−0.0866	0.0372	0.3282	0.050*
C10	0.1021 (2)	0.13424 (19)	0.44087 (17)	0.0400 (4)
H13	0.1628	0.1117	0.3833	0.048*
C11	0.1602 (2)	0.21193 (17)	0.55887 (16)	0.0317 (4)
C12	0.3203 (2)	0.2616 (2)	0.59846 (19)	0.0488 (6)
H14	0.3690	0.1939	0.5724	0.059*
H15	0.3558	0.3211	0.5607	0.059*
C13	0.1246 (2)	0.53539 (18)	0.67400 (16)	0.0345 (4)
H16	0.0528	0.4656	0.6217	0.041*
C14	0.1440 (2)	0.6415 (2)	0.6504 (2)	0.0446 (5)
H17	0.0860	0.6451	0.5838	0.054*
C15	0.2493 (2)	0.7428 (2)	0.7254 (2)	0.0459 (5)
H18	0.2664	0.8168	0.7102	0.055*
C16	0.3291 (2)	0.73469 (18)	0.82255 (19)	0.0375 (4)
H19	0.4015	0.8034	0.8757	0.045*
C17	0.30264 (17)	0.62549 (15)	0.84201 (15)	0.0255 (3)
C18	0.38677 (18)	0.61428 (15)	0.94787 (16)	0.0282 (3)
H20	0.4892	0.6238	0.9393	0.034*
H21	0.3805	0.6801	1.0230	0.034*
P1	0.59552 (5)	0.02974 (4)	0.74358 (4)	0.03228 (11)
F4	0.5841 (2)	0.0626 (2)	0.88218 (15)	0.0891 (6)
F5	0.61092 (18)	0.00030 (18)	0.60798 (13)	0.0725 (5)
F6	0.76632 (13)	0.04945 (12)	0.77770 (13)	0.0494 (3)
F7	0.61897 (16)	0.17125 (12)	0.76545 (17)	0.0680 (5)
F8	0.42616 (14)	0.01136 (14)	0.71068 (15)	0.0597 (4)
F9	0.57607 (18)	−0.10966 (14)	0.7258 (2)	0.0789 (5)
F1A	0.2162 (3)	0.4114 (5)	0.3777 (4)	0.0633 (9)	0.60
F2A	0.4293 (6)	0.4201 (7)	0.3364 (5)	0.0959 (18)	0.60
F3A	0.3715 (5)	0.5861 (4)	0.4479 (2)	0.0956 (15)	0.60
F1B	0.2326 (11)	0.3584 (9)	0.3289 (9)	0.075 (3)*	0.24
F2B	0.4556 (11)	0.4729 (9)	0.3644 (10)	0.048 (2)*	0.24
F3B	0.3095 (15)	0.5496 (11)	0.4460 (11)	0.097 (4)*	0.24
F1C	0.3378 (19)	0.3456 (13)	0.2889 (13)	0.091 (4)*	0.16
F2C	0.4376 (13)	0.5252 (12)	0.4082 (13)	0.063 (3)*	0.16
F3C	0.2240 (13)	0.4706 (12)	0.4110 (11)	0.054 (3)*	0.16
O4	0.15453 (15)	0.51056 (17)	0.21720 (16)	0.0494 (4)
O5	0.38100 (14)	0.53211 (14)	0.18470 (12)	0.0372 (3)
C19	0.28069 (19)	0.50937 (18)	0.23870 (16)	0.0320 (4)
C20	0.3227 (3)	0.4746 (3)	0.3470 (2)	0.0605 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01984 (11)	0.02370 (12)	0.02007 (11)	0.00408 (8)	0.00167 (7)	0.00581 (8)
O1	0.0279 (6)	0.0369 (7)	0.0343 (7)	0.0153 (5)	0.0108 (5)	0.0175 (6)
O2	0.0225 (6)	0.0426 (7)	0.0292 (6)	0.0059 (5)	0.0058 (5)	0.0058 (5)
O3	0.0354 (7)	0.0307 (6)	0.0223 (6)	−0.0020 (5)	−0.0054 (5)	0.0102 (5)
N1	0.0229 (6)	0.0228 (6)	0.0273 (7)	0.0037 (5)	−0.0003 (5)	0.0064 (5)
N2	0.0275 (7)	0.0248 (7)	0.0227 (7)	0.0042 (5)	0.0015 (5)	0.0055 (5)
N3	0.0244 (7)	0.0279 (7)	0.0217 (7)	0.0032 (5)	0.0020 (5)	0.0085 (5)
C1	0.0264 (8)	0.0289 (9)	0.0426 (10)	0.0080 (7)	0.0000 (7)	0.0099 (8)
C2	0.0370 (10)	0.0365 (10)	0.0634 (14)	0.0103 (8)	−0.0038 (9)	0.0243 (10)
C3	0.0543 (13)	0.0514 (13)	0.0652 (15)	0.0095 (10)	0.0025 (11)	0.0402 (12)
C4	0.0453 (12)	0.0497 (12)	0.0522 (13)	0.0087 (9)	0.0137 (10)	0.0313 (11)
C5	0.0263 (8)	0.0252 (8)	0.0304 (8)	0.0019 (6)	0.0023 (6)	0.0085 (7)
C6	0.0247 (8)	0.0284 (8)	0.0344 (9)	0.0035 (6)	0.0079 (7)	0.0105 (7)
C7	0.0280 (8)	0.0312 (9)	0.0293 (9)	0.0016 (7)	−0.0013 (7)	0.0117 (7)
C8	0.0383 (10)	0.0316 (9)	0.0357 (10)	−0.0020 (7)	−0.0101 (8)	0.0131 (8)
C9	0.0574 (13)	0.0314 (9)	0.0267 (9)	0.0082 (9)	−0.0084 (8)	0.0040 (8)
C10	0.0544 (12)	0.0372 (10)	0.0248 (9)	0.0169 (9)	0.0052 (8)	0.0044 (8)
C11	0.0346 (9)	0.0300 (9)	0.0269 (8)	0.0094 (7)	0.0046 (7)	0.0051 (7)
C12	0.0325 (10)	0.0682 (15)	0.0309 (10)	0.0091 (9)	0.0099 (8)	0.0007 (10)
C13	0.0352 (9)	0.0379 (10)	0.0258 (8)	0.0003 (7)	−0.0039 (7)	0.0132 (7)
C14	0.0460 (11)	0.0492 (12)	0.0394 (11)	0.0012 (9)	−0.0067 (9)	0.0269 (10)
C15	0.0483 (12)	0.0403 (11)	0.0511 (13)	0.0000 (9)	−0.0021 (10)	0.0282 (10)
C16	0.0339 (9)	0.0326 (9)	0.0414 (10)	−0.0022 (7)	−0.0023 (8)	0.0159 (8)
C17	0.0210 (7)	0.0298 (8)	0.0247 (8)	0.0049 (6)	0.0050 (6)	0.0092 (7)
C18	0.0257 (8)	0.0256 (8)	0.0283 (8)	0.0018 (6)	−0.0021 (6)	0.0080 (7)
P1	0.0319 (2)	0.0294 (2)	0.0314 (2)	0.00634 (18)	0.00592 (18)	0.00648 (19)
F4	0.0957 (13)	0.1473 (19)	0.0426 (9)	0.0587 (13)	0.0304 (9)	0.0368 (11)
F5	0.0719 (10)	0.1113 (14)	0.0344 (7)	0.0355 (10)	0.0129 (7)	0.0187 (8)
F6	0.0357 (6)	0.0454 (7)	0.0592 (8)	0.0106 (5)	0.0001 (5)	0.0114 (6)
F7	0.0577 (9)	0.0331 (7)	0.1023 (13)	0.0123 (6)	−0.0049 (8)	0.0157 (8)
F8	0.0328 (7)	0.0575 (8)	0.0740 (10)	0.0086 (6)	0.0046 (6)	0.0086 (7)
F9	0.0600 (9)	0.0381 (7)	0.1392 (17)	0.0055 (7)	0.0159 (10)	0.0374 (9)
F1A	0.0651 (18)	0.089 (3)	0.061 (2)	0.0150 (19)	0.0181 (15)	0.059 (2)
F2A	0.082 (3)	0.167 (5)	0.110 (4)	0.085 (4)	0.032 (3)	0.105 (4)
F3A	0.075 (2)	0.159 (4)	0.0224 (12)	−0.018 (3)	−0.0068 (13)	0.0261 (17)
O4	0.0281 (7)	0.0754 (11)	0.0610 (10)	0.0183 (7)	0.0077 (6)	0.0425 (9)
O5	0.0281 (6)	0.0558 (8)	0.0263 (6)	0.0041 (6)	0.0028 (5)	0.0171 (6)
C19	0.0276 (8)	0.0416 (10)	0.0291 (9)	0.0093 (7)	0.0032 (7)	0.0158 (8)
C20	0.0362 (11)	0.114 (2)	0.0521 (14)	0.0214 (13)	0.0112 (10)	0.0533 (16)

Geometric parameters (Å, º) top

Ni1—O1	2.0461 (12)	C10—C11	1.389 (3)
Ni1—N2	2.0601 (14)	C10—H13	0.9500
Ni1—O2	2.0647 (12)	C11—C12	1.506 (3)
Ni1—N1	2.0662 (14)	C12—H14	0.9900
Ni1—O3	2.0714 (12)	C12—H15	0.9900
Ni1—N3	2.0769 (14)	C13—C14	1.374 (3)
O1—C6	1.421 (2)	C13—H16	0.9500
O1—H1	0.8716	C14—C15	1.381 (3)
O2—C12	1.417 (2)	C14—H17	0.9500
O2—H2	0.9235	C15—C16	1.377 (3)
O3—C18	1.422 (2)	C15—H18	0.9500
O3—H3	0.9822	C16—C17	1.384 (3)
N1—C5	1.340 (2)	C16—H19	0.9500
N1—C1	1.352 (2)	C17—C18	1.501 (2)
N2—C11	1.342 (2)	C18—H20	0.9900
N2—C7	1.346 (2)	C18—H21	0.9900
N3—C17	1.340 (2)	P1—F5	1.5697 (15)
N3—C13	1.347 (2)	P1—F9	1.5777 (15)
C1—C2	1.377 (3)	P1—F7	1.5881 (14)
C1—H4	0.9500	P1—F4	1.5915 (16)
C2—C3	1.376 (4)	P1—F8	1.5960 (14)
C2—H5	0.9500	P1—F6	1.6087 (13)
C3—C4	1.385 (3)	F1A—C20	1.308 (4)
C3—H6	0.9500	F2A—C20	1.316 (4)
C4—C5	1.387 (3)	F3A—C20	1.417 (5)
C4—H7	0.9500	F1B—C20	1.420 (10)
C5—C6	1.503 (2)	F2B—C20	1.284 (11)
C6—H8	0.9900	F3B—C20	1.255 (12)
C6—H9	0.9900	F1C—C20	1.505 (14)
C7—C8	1.380 (3)	F2C—C20	1.188 (11)
C7—H10	0.9500	F3C—C20	1.279 (12)
C8—C9	1.381 (3)	O4—C19	1.223 (2)
C8—H11	0.9500	O5—C19	1.249 (2)
C9—C10	1.376 (3)	C19—C20	1.536 (3)
C9—H12	0.9500

O1—Ni1—N2	98.09 (6)	N2—C11—C10	121.78 (18)
O1—Ni1—O2	172.33 (5)	N2—C11—C12	117.35 (16)
O1—Ni1—N1	78.11 (5)	C10—C11—C12	120.87 (18)
N2—Ni1—O2	78.53 (5)	O2—C12—C11	109.50 (16)
N2—Ni1—N1	97.35 (6)	O2—C12—H14	109.8
O2—Ni1—N1	95.41 (6)	C11—C12—H14	109.8
O1—Ni1—O3	95.00 (5)	O2—C12—H15	109.8
N2—Ni1—O3	166.15 (6)	C11—C12—H15	109.8
O2—Ni1—O3	89.01 (5)	H14—C12—H15	108.2
N1—Ni1—O3	89.74 (5)	N3—C13—C14	122.91 (17)
O1—Ni1—N3	93.77 (5)	N3—C13—H16	118.5
N2—Ni1—N3	96.49 (6)	C14—C13—H16	118.5
O2—Ni1—N3	93.45 (6)	C13—C14—C15	118.77 (18)
N1—Ni1—N3	164.81 (6)	C13—C14—H17	120.6
O3—Ni1—N3	78.09 (5)	C15—C14—H17	120.6
C6—O1—Ni1	118.49 (10)	C16—C15—C14	118.86 (18)
C6—O1—H1	112.8	C16—C15—H18	120.6
Ni1—O1—H1	122.2	C14—C15—H18	120.6
C12—O2—Ni1	115.90 (11)	C15—C16—C17	119.37 (18)
C12—O2—H2	114.4	C15—C16—H19	120.3
Ni1—O2—H2	118.1	C17—C16—H19	120.3
C18—O3—Ni1	117.12 (10)	N3—C17—C16	122.05 (16)
C18—O3—H3	106.7	N3—C17—C18	117.36 (15)
Ni1—O3—H3	130.7	C16—C17—C18	120.58 (15)
C5—N1—C1	118.61 (16)	O3—C18—C17	110.11 (13)
C5—N1—Ni1	116.13 (11)	O3—C18—H20	109.6
C1—N1—Ni1	124.57 (13)	C17—C18—H20	109.6
C11—N2—C7	118.69 (15)	O3—C18—H21	109.6
C11—N2—Ni1	115.61 (12)	C17—C18—H21	109.6
C7—N2—Ni1	125.69 (12)	H20—C18—H21	108.2
C17—N3—C13	118.01 (15)	F5—P1—F9	90.77 (11)
C17—N3—Ni1	116.35 (11)	F5—P1—F7	90.50 (11)
C13—N3—Ni1	125.64 (12)	F9—P1—F7	178.09 (10)
N1—C1—C2	122.16 (19)	F5—P1—F4	178.33 (12)
N1—C1—H4	118.9	F9—P1—F4	90.26 (12)
C2—C1—H4	118.9	F7—P1—F4	88.43 (12)
C3—C2—C1	119.20 (19)	F5—P1—F8	90.97 (9)
C3—C2—H5	120.4	F9—P1—F8	91.58 (9)
C1—C2—H5	120.4	F7—P1—F8	89.83 (8)
C2—C3—C4	119.1 (2)	F4—P1—F8	90.31 (10)
C2—C3—H6	120.5	F5—P1—F6	89.37 (8)
C4—C3—H6	120.5	F9—P1—F6	88.81 (8)
C3—C4—C5	119.1 (2)	F7—P1—F6	89.77 (7)
C3—C4—H7	120.5	F4—P1—F6	89.35 (9)
C5—C4—H7	120.5	F8—P1—F6	179.48 (9)
N1—C5—C4	121.87 (17)	O4—C19—O5	129.17 (18)
N1—C5—C6	117.09 (15)	O4—C19—C20	115.85 (17)
C4—C5—C6	121.03 (17)	O5—C19—C20	114.97 (16)
O1—C6—C5	108.67 (14)	F2C—C20—F3C	111.5 (9)
O1—C6—H8	110.0	F3B—C20—F2B	102.8 (7)
C5—C6—H8	110.0	F1A—C20—F2A	109.8 (4)
O1—C6—H9	110.0	F1A—C20—F3A	104.4 (3)
C5—C6—H9	110.0	F2A—C20—F3A	106.6 (4)
H8—C6—H9	108.3	F3B—C20—F1B	108.1 (7)
N2—C7—C8	122.40 (18)	F2B—C20—F1B	110.5 (6)
N2—C7—H10	118.8	F2C—C20—F1C	102.0 (9)
C8—C7—H10	118.8	F3C—C20—F1C	107.2 (8)
C7—C8—C9	118.65 (18)	F2C—C20—C19	118.3 (6)
C7—C8—H11	120.7	F3B—C20—C19	113.8 (6)
C9—C8—H11	120.7	F3C—C20—C19	113.1 (6)
C10—C9—C8	119.43 (18)	F2B—C20—C19	113.3 (5)
C10—C9—H12	120.3	F1A—C20—C19	115.0 (2)
C8—C9—H12	120.3	F2A—C20—C19	113.6 (3)
C9—C10—C11	119.03 (19)	F3A—C20—C19	106.5 (3)
C9—C10—H13	120.5	F1B—C20—C19	108.2 (4)
C11—C10—H13	120.5	F1C—C20—C19	103.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.87	1.76	2.6003 (19)	162.5
O2—H2···O5ⁱⁱ	0.92	1.77	2.6965 (18)	175.8
O3—H3···O5ⁱⁱⁱ	0.98	1.65	2.6267 (18)	173.8

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

Experimental details

Crystal data
Chemical formula	[Ni(C₆H₇NO)₃](PF₆)(C₂F₃O₂)
M_r	644.08
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	9.6381 (2), 11.9668 (4), 11.9892 (3)
α, β, γ (°)	109.950 (1), 95.348 (1), 101.411 (1)
V (Å³)	1254.60 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.813, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12517, 5736, 5234
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.05
No. of reflections	5736
No. of parameters	376
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.45

Computer programs: RAPID-AUTO (Rigaku, 2002), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009), ORTEP-3 for Windows (Farrugia ,1997) and Mercury (Macrae et al., 2008), Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009)and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Ni1—O1	2.0461 (12)	Ni1—N1	2.0662 (14)
Ni1—N2	2.0601 (14)	Ni1—O3	2.0714 (12)
Ni1—O2	2.0647 (12)	Ni1—N3	2.0769 (14)

O1—Ni1—N1	78.11 (5)	O3—Ni1—N3	78.09 (5)
N2—Ni1—O2	78.53 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.87	1.76	2.6003 (19)	162.5
O2—H2···O5ⁱⁱ	0.92	1.77	2.6965 (18)	175.8
O3—H3···O5ⁱⁱⁱ	0.98	1.65	2.6267 (18)	173.8

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

Acknowledgements

This work was supported in part by funds (No. 115001) from the Central Research Institute of Fukuoka University.

References

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