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

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.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         C19
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          P1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          6

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Deg.
PLAT194_ALERT_1_G Missing _cell_measurement_reflns_used datum ....          ?
PLAT195_ALERT_1_G Missing _cell_measurement_theta_max   datum ....          ?
PLAT196_ALERT_1_G Missing _cell_measurement_theta_min   datum ....          ?
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................         21 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

The O–H H atoms were located in a difference Fourier map and the coordinates were fixed. Their U_iso(H) values were set to 1.5U_eq(O). Other H atoms were placed at calculated positions and were treated as riding on the parent C atoms, with C–H = 0.93 (CH) and 0.97 (CH₂) Å and with U_iso(H) = 1.2U_eq(C). Three F atoms in CF₃COO anions are rotationally disordered between three positions. The two parts of lower occupation were refined only isotropic (sof. 0.6:0.24:0.16).

Computing details

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

	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

Crystal data

[Ni(C6H7NO)3](PF6)(C2F3O2)	V = 1254.60 (6) Å^3
Mr = 644.08	Z = 2
Triclinic, P1	F(000) = 652
Hall symbol: -P 1	Dx = 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

Rigaku R-AXIS RAPID diffractometer	5234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −12→11
Tmin = 0.813, Tmax = 1.000	k = −15→15
12517 measured reflections	l = −15→15
5736 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.5841P] where P = (Fo^2 + 2Fc^2)/3
5736 reflections	(Δ/σ)max = 0.001
376 parameters	Δρmax = 0.50 e Å^−3
9 restraints	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^i	0.87	1.76	2.6003 (19)	162.5
O2—H2···O5^ii	0.92	1.77	2.6965 (18)	175.8
O3—H3···O5^iii	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.