Tetra­kis[μ-1,3-bis­(4,5-dihydro-1,3-oxazol-2-yl)benzene-κ² N:N′]tris­ilver(I) tris­(hexa­fluoridophosphate)

Abstract

In the title compound, [Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃, one Ag^I ion, lying on a twofold rotation axis, is coordinated by four N atoms from four 1,3-bis­(4,5-dihydro-1,3-oxazol-2-yl)benzene (L) ligands in a distorted tetra­hedral geometry and the other Ag^I ion is coordinated by two N atoms from two L ligands in a bent arrangement [N—Ag—N = 169.03 (17)°]. Two L ligands adopt a syn conformation, while the other two adopt an anti conformation. They bridge adjacent Ag^I ions, forming a trinuclear complex. One of the PF₆ ⁻ anions is half-occupied, with the P atom located on a twofold rotation axis. The PF₆ ⁻ anions link the complex mol­ecules via Ag⋯F inter­actions [2.80 (2) and 2.85 (2) Å] into a polymeric chain along [100].

Related literature  

For related structures incorporating the 1,4-bis­(4,5-dihydro-2-oxazol­yl)benzene ligand, see: Suen et al. (2011 ▶); Wang et al. (2008 ▶, 2011a ▶,b ▶); Yeh et al. (2011 ▶).

Experimental  

Crystal data  

• [Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃

• M _r = 1623.46

• Monoclinic,

• a = 22.7473 (16) Å

• b = 11.4521 (19) Å

• c = 24.1382 (15) Å

• β = 116.014 (7)°

• V = 5651.0 (11) ų

• Z = 4

• Mo Kα radiation

• μ = 1.23 mm⁻¹

• T = 298 K

• 0.60 × 0.40 × 0.30 mm

Data collection  

• Siemens P4 four-circle diffractometer

• Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T _min = 0.634, T _max = 0.964

• 5107 measured reflections

• 4976 independent reflections

• 3885 reflections with I > 2σ(I)

• R _int = 0.020

• 3 standard reflections every 297 reflections intensity decay: 2.0%

Refinement  

• R[F ² > 2σ(F ²)] = 0.050

• wR(F ²) = 0.137

• S = 1.01

• 4976 reflections

• 425 parameters

• H-atom parameters constrained

• Δρ_max = 1.02 e Å⁻³

• Δρ_min = −0.81 e Å⁻³

Data collection: XSCANS (Siemens, 1995 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected bond lengths (Å).

Ag1—N11	2.331 (4)
Ag1—N41	2.418 (5)
Ag2—N31	2.104 (5)
Ag2—N61	2.106 (4)

supplementary crystallographic information

Comment

Several Ag(I), Cd(II) and Cu(II) complexes containing 1,4-bis(4,5-dihydro-2-oxazolyl)benzene ligands have been reported, which show various dimensional structures (Suen et al., 2011; Wang et al., 2008, 2011a,b; Yeh et al., 2011). In the title trinuclear complex, one Ag^I ion, lying on a twofold axis, is coordinated by four N atoms from four 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (L) ligands in a distorted tetrahedral geometry and the other two are each coordinated by two N atoms from two L ligands in a bent linear arrangement (Fig. 1, Table 1). The Ag···Ag separation in the trimer is 7.473 (1) Å. The L ligands show both syn and anti conformations. The PF₆^- anions link the trinuclear cationic complexes via Ag···F interactions [2.80 (2) and 2.85 (2) Å], forming one-dimensional beaded polymeric chains along [100] (Fig. 2).

Experimental

An aqueous solution (5.0 ml) of AgPF₆ (3.0 mmol) was layered carefully over a methanolic solution (5.0 ml) of 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (4.0 mmol) in a tube and kept it in dark. Colourless crystals were obtained after several weeks. These were washed with methanol and collected in 75.8% yield.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (phenyl) and 0.97 (methylene) Å and with U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) 1-x, y, 1/2-z.]

Fig. 2.

The packing diagram of the title compound, showing the one-dimensional beaded chain formed by Ag···F interactions.

Crystal data

[Ag3(C12H12N2O2)4](PF6)3	F(000) = 3216
Mr = 1623.46	Dx = 1.908 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 36 reflections
a = 22.7473 (16) Å	θ = 4.8–12.5°
b = 11.4521 (19) Å	µ = 1.23 mm−1
c = 24.1382 (15) Å	T = 298 K
β = 116.014 (7)°	Plate, colourless
V = 5651.0 (11) Å3	0.60 × 0.40 × 0.30 mm
Z = 4

Data collection

Siemens P4 four-circle diffractometer	3885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = 0→26
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = 0→13
Tmin = 0.634, Tmax = 0.964	l = −28→25
5107 measured reflections	3 standard reflections every 297 reflections
4976 independent reflections	intensity decay: 2.0%

Refinement

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0628P)2 + 34.3783P] where P = (Fo2 + 2Fc2)/3
4976 reflections	(Δ/σ)max < 0.001
425 parameters	Δρmax = 1.02 e Å−3
0 restraints	Δρmin = −0.81 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.5000	0.06276 (6)	0.2500	0.0564 (2)
Ag2	0.18074 (2)	0.04964 (5)	0.26872 (2)	0.05790 (18)
O11	0.31412 (19)	−0.1417 (4)	0.19947 (19)	0.0637 (11)
O31	0.3068 (2)	−0.0441 (4)	0.45572 (19)	0.0675 (12)
O41	0.3592 (2)	0.2537 (5)	0.08323 (18)	0.0694 (13)
O61	0.14979 (18)	0.1693 (4)	0.09064 (16)	0.0532 (9)
N11	0.4086 (2)	−0.0591 (4)	0.2133 (2)	0.0488 (11)
N31	0.2312 (2)	0.0070 (4)	0.3628 (2)	0.0507 (11)
N41	0.4514 (2)	0.1949 (5)	0.1635 (2)	0.0558 (12)
N61	0.1478 (2)	0.1039 (4)	0.1765 (2)	0.0491 (11)
C11	0.3711 (2)	−0.0898 (5)	0.2366 (3)	0.0458 (12)
C12	0.3785 (3)	−0.0977 (6)	0.1487 (3)	0.0580 (15)
H12A	0.4034	−0.1606	0.1423	0.070*
H12B	0.3753	−0.0337	0.1212	0.070*
C13	0.3111 (3)	−0.1394 (7)	0.1382 (3)	0.0712 (19)
H13A	0.2774	−0.0860	0.1116	0.085*
H13B	0.3021	−0.2166	0.1198	0.085*
C21	0.3827 (3)	−0.0752 (5)	0.3012 (3)	0.0465 (12)
C22	0.3315 (3)	−0.0577 (5)	0.3166 (2)	0.0457 (12)
H22A	0.2888	−0.0556	0.2856	0.055*
C23	0.3426 (3)	−0.0434 (5)	0.3773 (2)	0.0469 (12)
C24	0.4070 (3)	−0.0470 (6)	0.4234 (3)	0.0657 (17)
H24A	0.4155	−0.0356	0.4644	0.079*
C25	0.4578 (3)	−0.0674 (6)	0.4080 (3)	0.0710 (19)
H25A	0.5003	−0.0719	0.4390	0.085*
C26	0.4465 (3)	−0.0810 (6)	0.3481 (3)	0.0639 (17)
H26A	0.4813	−0.0942	0.3384	0.077*
C31	0.2900 (3)	−0.0254 (5)	0.3960 (2)	0.0506 (13)
C32	0.1977 (3)	0.0162 (6)	0.4034 (3)	0.0629 (16)
H32A	0.1619	−0.0390	0.3911	0.075*
H32B	0.1809	0.0944	0.4023	0.075*
C33	0.2505 (4)	−0.0123 (8)	0.4664 (3)	0.080 (2)
H33A	0.2603	0.0549	0.4936	0.096*
H33B	0.2374	−0.0768	0.4846	0.096*
C41	0.3914 (3)	0.2206 (5)	0.1427 (2)	0.0464 (12)
C42	0.4700 (3)	0.2166 (8)	0.1130 (3)	0.081 (2)
H42A	0.4845	0.1450	0.1013	0.098*
H42B	0.5049	0.2738	0.1252	0.098*
C43	0.4086 (3)	0.2623 (8)	0.0603 (3)	0.080 (2)
H43A	0.4142	0.3426	0.0508	0.096*
H43B	0.3968	0.2150	0.0237	0.096*
C51	0.3518 (2)	0.2183 (5)	0.1772 (2)	0.0429 (12)
C52	0.2861 (2)	0.1886 (5)	0.1481 (2)	0.0430 (12)
H52A	0.2663	0.1709	0.1062	0.052*
C53	0.2499 (2)	0.1855 (4)	0.1822 (2)	0.0407 (11)
C54	0.2793 (3)	0.2170 (5)	0.2441 (2)	0.0469 (13)
H54A	0.2550	0.2162	0.2667	0.056*
C55	0.3442 (3)	0.2492 (5)	0.2721 (3)	0.0516 (14)
H55A	0.3635	0.2712	0.3134	0.062*
C56	0.3809 (3)	0.2492 (5)	0.2392 (3)	0.0495 (13)
H56A	0.4249	0.2697	0.2584	0.059*
C61	0.1804 (2)	0.1498 (5)	0.1510 (2)	0.0427 (12)
C62	0.0795 (3)	0.0839 (7)	0.1278 (3)	0.0641 (18)
H62A	0.0479	0.1267	0.1368	0.077*
H62B	0.0684	0.0015	0.1238	0.077*
C63	0.0821 (3)	0.1300 (6)	0.0701 (3)	0.0555 (14)
H63A	0.0713	0.0690	0.0393	0.067*
H63B	0.0518	0.1943	0.0527	0.067*
P1	0.5000	0.4236 (2)	0.7500	0.0619 (6)
F1	0.5316 (14)	0.3242 (15)	0.7277 (12)	0.136 (9)	0.50
F2	0.4658 (10)	0.5162 (10)	0.7741 (9)	0.102 (4)	0.50
F3	0.5624 (8)	0.503 (2)	0.7726 (12)	0.172 (9)	0.50
F4	0.4740 (10)	0.490 (2)	0.6891 (7)	0.151 (6)	0.50
F5	0.5275 (10)	0.3615 (19)	0.8141 (7)	0.135 (5)	0.50
F6	0.4354 (9)	0.3566 (19)	0.7311 (13)	0.156 (8)	0.50
P2	0.12182 (9)	0.19994 (18)	0.52246 (10)	0.0733 (5)
F7	0.0734 (4)	0.1210 (9)	0.4738 (4)	0.231 (5)
F8	0.0936 (4)	0.2993 (9)	0.4800 (5)	0.241 (6)
F9	0.1540 (4)	0.1000 (7)	0.5635 (6)	0.266 (7)
F10	0.0687 (4)	0.2167 (15)	0.5419 (5)	0.290 (8)
F11	0.1701 (3)	0.2775 (6)	0.5752 (3)	0.156 (3)
F12	0.1760 (4)	0.1934 (12)	0.5037 (4)	0.248 (6)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Ag1	0.0330 (3)	0.0662 (4)	0.0635 (4)	0.000	0.0150 (3)	0.000
Ag2	0.0457 (3)	0.0879 (4)	0.0438 (3)	0.0038 (2)	0.0231 (2)	0.0128 (2)
O11	0.045 (2)	0.090 (3)	0.059 (2)	−0.027 (2)	0.0255 (19)	−0.016 (2)
O31	0.082 (3)	0.080 (3)	0.041 (2)	0.009 (2)	0.028 (2)	0.010 (2)
O41	0.056 (2)	0.114 (4)	0.048 (2)	0.017 (3)	0.031 (2)	0.018 (2)
O61	0.042 (2)	0.075 (3)	0.042 (2)	0.0003 (19)	0.0179 (16)	0.0088 (19)
N11	0.035 (2)	0.057 (3)	0.057 (3)	−0.008 (2)	0.023 (2)	−0.003 (2)
N31	0.054 (3)	0.059 (3)	0.042 (2)	−0.003 (2)	0.024 (2)	0.004 (2)
N41	0.039 (3)	0.080 (4)	0.056 (3)	0.005 (2)	0.029 (2)	0.011 (2)
N61	0.035 (2)	0.074 (3)	0.043 (2)	0.004 (2)	0.0216 (19)	0.007 (2)
C11	0.036 (3)	0.043 (3)	0.056 (3)	0.000 (2)	0.017 (2)	0.000 (2)
C12	0.048 (3)	0.067 (4)	0.063 (4)	−0.009 (3)	0.029 (3)	−0.009 (3)
C13	0.063 (4)	0.096 (5)	0.057 (4)	−0.026 (4)	0.029 (3)	−0.019 (4)
C21	0.039 (3)	0.046 (3)	0.053 (3)	−0.006 (2)	0.018 (2)	0.001 (2)
C22	0.040 (3)	0.045 (3)	0.044 (3)	−0.003 (2)	0.011 (2)	0.003 (2)
C23	0.043 (3)	0.046 (3)	0.045 (3)	−0.003 (2)	0.013 (2)	0.005 (2)
C24	0.066 (4)	0.074 (4)	0.041 (3)	−0.009 (3)	0.008 (3)	0.005 (3)
C25	0.045 (3)	0.087 (5)	0.059 (4)	−0.003 (3)	0.001 (3)	0.011 (3)
C26	0.037 (3)	0.075 (4)	0.069 (4)	−0.003 (3)	0.014 (3)	0.008 (3)
C31	0.065 (4)	0.047 (3)	0.038 (3)	−0.005 (3)	0.021 (3)	0.002 (2)
C32	0.076 (4)	0.064 (4)	0.064 (4)	0.001 (3)	0.045 (3)	0.005 (3)
C33	0.087 (5)	0.112 (6)	0.050 (4)	−0.007 (5)	0.039 (4)	−0.001 (4)
C41	0.047 (3)	0.051 (3)	0.046 (3)	0.000 (2)	0.024 (2)	0.001 (2)
C42	0.065 (4)	0.126 (7)	0.074 (4)	0.016 (4)	0.050 (4)	0.027 (4)
C43	0.069 (4)	0.128 (7)	0.061 (4)	0.005 (4)	0.046 (4)	0.011 (4)
C51	0.039 (3)	0.048 (3)	0.045 (3)	0.007 (2)	0.021 (2)	0.005 (2)
C52	0.042 (3)	0.050 (3)	0.041 (3)	0.006 (2)	0.021 (2)	0.004 (2)
C53	0.035 (3)	0.045 (3)	0.044 (3)	0.007 (2)	0.019 (2)	0.004 (2)
C54	0.045 (3)	0.059 (3)	0.045 (3)	0.010 (3)	0.027 (2)	0.005 (2)
C55	0.049 (3)	0.065 (4)	0.044 (3)	−0.001 (3)	0.023 (3)	−0.006 (3)
C56	0.039 (3)	0.060 (4)	0.050 (3)	0.003 (3)	0.020 (2)	0.000 (3)
C61	0.040 (3)	0.047 (3)	0.043 (3)	0.008 (2)	0.021 (2)	0.004 (2)
C62	0.035 (3)	0.109 (5)	0.047 (3)	−0.011 (3)	0.017 (2)	0.005 (3)
C63	0.041 (3)	0.071 (4)	0.049 (3)	0.004 (3)	0.015 (2)	0.006 (3)
P1	0.0493 (12)	0.0745 (16)	0.0784 (16)	0.000	0.0431 (12)	0.000
F1	0.21 (3)	0.091 (9)	0.20 (2)	0.038 (14)	0.18 (2)	0.011 (13)
F2	0.124 (13)	0.075 (6)	0.157 (12)	0.029 (8)	0.108 (11)	0.014 (8)
F3	0.071 (9)	0.21 (2)	0.23 (2)	−0.047 (10)	0.064 (13)	−0.034 (19)
F4	0.142 (13)	0.225 (18)	0.118 (11)	0.074 (14)	0.086 (11)	0.076 (12)
F5	0.157 (13)	0.161 (15)	0.105 (9)	0.074 (12)	0.074 (9)	0.066 (10)
F6	0.101 (11)	0.142 (19)	0.25 (3)	−0.054 (11)	0.101 (15)	−0.039 (16)
P2	0.0472 (9)	0.0794 (13)	0.0804 (12)	0.0067 (9)	0.0161 (9)	−0.0022 (10)
F7	0.147 (7)	0.200 (9)	0.208 (9)	−0.008 (6)	−0.048 (6)	−0.083 (7)
F8	0.140 (6)	0.246 (11)	0.283 (12)	0.054 (7)	0.043 (7)	0.168 (10)
F9	0.118 (6)	0.153 (7)	0.368 (14)	−0.043 (5)	−0.041 (7)	0.137 (8)
F10	0.091 (5)	0.61 (2)	0.194 (8)	0.005 (9)	0.086 (6)	−0.080 (12)
F11	0.110 (5)	0.137 (5)	0.166 (6)	−0.005 (4)	0.010 (4)	−0.052 (5)
F12	0.139 (6)	0.457 (18)	0.165 (7)	0.096 (9)	0.082 (6)	−0.042 (9)

Geometric parameters (Å, º)

Ag1—N11	2.331 (4)	C32—H32A	0.9700
Ag1—N41	2.418 (5)	C32—H32B	0.9700
Ag2—N31	2.104 (5)	C33—H33A	0.9700
Ag2—N61	2.106 (4)	C33—H33B	0.9700
O11—C11	1.348 (6)	C41—C51	1.472 (7)
O11—C13	1.450 (7)	C42—C43	1.511 (10)
O31—C31	1.335 (7)	C42—H42A	0.9700
O31—C33	1.460 (8)	C42—H42B	0.9700
O41—C41	1.348 (7)	C43—H43A	0.9700
O41—C43	1.457 (7)	C43—H43B	0.9700
O61—C61	1.329 (6)	C51—C52	1.387 (7)
O61—C63	1.467 (7)	C51—C56	1.391 (7)
N11—C11	1.260 (7)	C52—C53	1.396 (7)
N11—C12	1.469 (7)	C52—H52A	0.9300
N31—C31	1.276 (8)	C53—C54	1.391 (7)
N31—C32	1.485 (7)	C53—C61	1.479 (7)
N41—C41	1.264 (7)	C54—C55	1.378 (8)
N41—C42	1.478 (7)	C54—H54A	0.9300
N61—C61	1.269 (7)	C55—C56	1.382 (7)
N61—C62	1.498 (7)	C55—H55A	0.9300
C11—C21	1.474 (8)	C56—H56A	0.9300
C12—C13	1.517 (8)	C62—C63	1.515 (8)
C12—H12A	0.9700	C62—H62A	0.9700
C12—H12B	0.9700	C62—H62B	0.9700
C13—H13A	0.9700	C63—H63A	0.9700
C13—H13B	0.9700	C63—H63B	0.9700
C21—C22	1.384 (8)	P1—F4	1.527 (12)
C21—C26	1.396 (8)	P1—F6	1.539 (16)
C22—C23	1.383 (8)	P1—F1	1.562 (13)
C22—H22A	0.9300	P1—F5	1.564 (11)
C23—C24	1.398 (8)	P1—F3	1.566 (16)
C23—C31	1.469 (8)	P1—F2	1.570 (11)
C24—C25	1.380 (10)	P2—F8	1.476 (8)
C24—H24A	0.9300	P2—F9	1.481 (7)
C25—C26	1.363 (10)	P2—F12	1.488 (8)
C25—H25A	0.9300	P2—F10	1.490 (7)
C26—H26A	0.9300	P2—F7	1.509 (7)
C32—C33	1.504 (10)	P2—F11	1.546 (6)
N11—Ag1—N11i	106.5 (2)	O61—C63—C62	104.7 (4)
N11—Ag1—N41i	134.17 (16)	O61—C63—H63A	110.8
N11i—Ag1—N41i	93.01 (17)	C62—C63—H63A	110.8
N11—Ag1—N41	93.01 (17)	O61—C63—H63B	110.8
N11i—Ag1—N41	134.17 (16)	C62—C63—H63B	110.8
N41i—Ag1—N41	102.5 (3)	H63A—C63—H63B	108.9
N31—Ag2—N61	169.03 (17)	F4ii—P1—F4	120 (2)
C11—O11—C13	105.7 (4)	F4ii—P1—F6	116.9 (11)
C31—O31—C33	107.0 (5)	F4—P1—F6	92.7 (16)
C41—O41—C43	105.9 (5)	F4ii—P1—F6ii	92.7 (16)
C61—O61—C63	106.7 (4)	F4—P1—F6ii	116.9 (11)
C11—N11—C12	107.2 (4)	F6—P1—F6ii	120.2 (18)
C11—N11—Ag1	131.5 (4)	F4ii—P1—F1ii	94.4 (10)
C12—N11—Ag1	120.5 (3)	F6ii—P1—F1ii	93.3 (12)
C31—N31—C32	107.7 (5)	F4ii—P1—F1	130.8 (17)
C31—N31—Ag2	132.2 (4)	F4—P1—F1	94.4 (10)
C32—N31—Ag2	120.1 (4)	F6—P1—F1	93.3 (12)
C41—N41—C42	106.4 (5)	F1ii—P1—F1	86.4 (13)
C41—N41—Ag1	119.6 (4)	F4ii—P1—F5ii	177.0 (16)
C42—N41—Ag1	129.0 (4)	F4—P1—F5ii	57.1 (9)
C61—N61—C62	107.9 (4)	F6—P1—F5ii	64.2 (9)
C61—N61—Ag2	128.5 (4)	F6ii—P1—F5ii	89.0 (10)
C62—N61—Ag2	123.4 (3)	F1ii—P1—F5ii	88.0 (11)
N11—C11—O11	118.0 (5)	F1—P1—F5ii	51.1 (9)
N11—C11—C21	126.8 (5)	F4ii—P1—F5	57.1 (9)
O11—C11—C21	115.2 (5)	F4—P1—F5	177.0 (17)
N11—C12—C13	103.9 (5)	F6—P1—F5	89.0 (10)
N11—C12—H12A	111.0	F6ii—P1—F5	64.2 (9)
C13—C12—H12A	111.0	F1ii—P1—F5	51.1 (9)
N11—C12—H12B	111.0	F1—P1—F5	88.0 (11)
C13—C12—H12B	111.0	F5ii—P1—F5	125.9 (18)
H12A—C12—H12B	109.0	F4ii—P1—F3	57.7 (9)
O11—C13—C12	104.0 (5)	F4—P1—F3	87.4 (11)
O11—C13—H13A	111.0	F6—P1—F3	173.3 (12)
C12—C13—H13A	111.0	F6ii—P1—F3	65.4 (11)
O11—C13—H13B	111.0	F1ii—P1—F3	141.7 (17)
C12—C13—H13B	111.0	F1—P1—F3	93.3 (12)
H13A—C13—H13B	109.0	F5ii—P1—F3	121.0 (10)
C22—C21—C26	119.2 (6)	F5—P1—F3	90.6 (16)
C22—C21—C11	121.3 (5)	F4ii—P1—F3ii	87.4 (11)
C26—C21—C11	119.5 (5)	F4—P1—F3ii	57.7 (9)
C23—C22—C21	121.1 (5)	F6—P1—F3ii	65.4 (11)
C23—C22—H22A	119.4	F6ii—P1—F3ii	173.3 (12)
C21—C22—H22A	119.4	F1ii—P1—F3ii	93.3 (12)
C22—C23—C24	118.8 (6)	F1—P1—F3ii	141.7 (17)
C22—C23—C31	123.2 (5)	F5ii—P1—F3ii	90.6 (16)
C24—C23—C31	118.0 (5)	F5—P1—F3ii	121.0 (10)
C25—C24—C23	119.9 (6)	F3—P1—F3ii	109.4 (18)
C25—C24—H24A	120.0	F4ii—P1—F2	49.6 (8)
C23—C24—H24A	120.0	F4—P1—F2	88.4 (9)
C26—C25—C24	121.0 (6)	F6—P1—F2	83.2 (11)
C26—C25—H25A	119.5	F6ii—P1—F2	142.3 (15)
C24—C25—H25A	119.5	F1ii—P1—F2	89.3 (8)
C25—C26—C21	119.9 (6)	F1—P1—F2	175.7 (8)
C25—C26—H26A	120.0	F5ii—P1—F2	128.7 (14)
C21—C26—H26A	120.0	F5—P1—F2	89.3 (8)
N31—C31—O31	116.8 (5)	F3—P1—F2	90.1 (9)
N31—C31—C23	128.2 (5)	F4ii—P1—F2ii	88.4 (9)
O31—C31—C23	115.0 (5)	F4—P1—F2ii	49.6 (8)
N31—C32—C33	103.9 (5)	F6—P1—F2ii	142.3 (15)
N31—C32—H32A	111.0	F6ii—P1—F2ii	83.2 (11)
C33—C32—H32A	111.0	F1ii—P1—F2ii	175.7 (8)
N31—C32—H32B	111.0	F1—P1—F2ii	89.3 (8)
C33—C32—H32B	111.0	F5ii—P1—F2ii	89.3 (8)
H32A—C32—H32B	109.0	F5—P1—F2ii	128.7 (14)
O31—C33—C32	104.3 (5)	F3ii—P1—F2ii	90.1 (9)
O31—C33—H33A	110.9	F2—P1—F2ii	95.1 (9)
C32—C33—H33A	110.9	F6ii—F1—F5ii	133 (2)
O31—C33—H33B	110.9	F6ii—F1—P1	69.6 (14)
C32—C33—H33B	110.9	F5ii—F1—P1	64.5 (9)
H33A—C33—H33B	108.9	F3ii—F2—F4ii	132.4 (16)
N41—C41—O41	118.5 (5)	F3ii—F2—P1	70.6 (13)
N41—C41—C51	126.3 (5)	F4ii—F2—P1	63.5 (8)
O41—C41—C51	115.2 (5)	F2ii—F3—F4ii	116.2 (18)
N41—C42—C43	105.0 (5)	F2ii—F3—P1	70.9 (11)
N41—C42—H42A	110.8	F4ii—F3—P1	59.8 (8)
C43—C42—H42A	110.8	F2ii—F3—F6ii	96 (2)
N41—C42—H42B	110.8	F4ii—F3—F6ii	89 (2)
C43—C42—H42B	110.8	P1—F3—F6ii	56.5 (9)
H42A—C42—H42B	108.8	F2ii—F4—F5ii	104.8 (12)
O41—C43—C42	103.9 (5)	F2ii—F4—F3ii	105.1 (17)
O41—C43—H43A	111.0	F5ii—F4—F3ii	97.0 (18)
C42—C43—H43A	111.0	F2ii—F4—P1	66.9 (8)
O41—C43—H43B	111.0	F5ii—F4—P1	62.7 (7)
C42—C43—H43B	111.0	F3ii—F4—P1	62.5 (8)
H43A—C43—H43B	109.0	F1ii—F5—F4ii	106.5 (13)
C52—C51—C56	120.5 (5)	F1ii—F5—P1	64.4 (8)
C52—C51—C41	120.6 (5)	F4ii—F5—P1	60.2 (7)
C56—C51—C41	118.9 (5)	F1ii—F5—F6ii	97.1 (15)
C51—C52—C53	119.3 (5)	F4ii—F5—F6ii	90.2 (15)
C51—C52—H52A	120.3	P1—F5—F6ii	57.2 (7)
C53—C52—H52A	120.3	F1ii—F6—P1	72.1 (15)
C54—C53—C52	119.8 (5)	F1ii—F6—F5ii	107 (2)
C54—C53—C61	121.4 (4)	P1—F6—F5ii	58.6 (7)
C52—C53—C61	118.8 (5)	F1ii—F6—F3ii	113 (3)
C55—C54—C53	120.3 (5)	P1—F6—F3ii	58.1 (8)
C55—C54—H54A	119.9	F5ii—F6—F3ii	84.0 (17)
C53—C54—H54A	119.9	F8—P2—F9	175.8 (7)
C54—C55—C56	120.3 (5)	F8—P2—F12	89.7 (6)
C54—C55—H55A	119.8	F9—P2—F12	86.1 (7)
C56—C55—H55A	119.8	F8—P2—F10	87.3 (7)
C55—C56—C51	119.7 (5)	F9—P2—F10	96.8 (8)
C55—C56—H56A	120.1	F12—P2—F10	175.4 (9)
C51—C56—H56A	120.1	F8—P2—F7	88.6 (6)
N61—C61—O61	117.7 (5)	F9—P2—F7	92.0 (6)
N61—C61—C53	126.2 (5)	F12—P2—F7	98.8 (6)
O61—C61—C53	116.1 (4)	F10—P2—F7	84.6 (6)
N61—C62—C63	103.0 (4)	F8—P2—F11	93.7 (6)
N61—C62—H62A	111.2	F9—P2—F11	85.9 (5)
C63—C62—H62A	111.2	F12—P2—F11	84.0 (5)
N61—C62—H62B	111.2	F10—P2—F11	92.8 (6)
C63—C62—H62B	111.2	F7—P2—F11	176.4 (6)
H62A—C62—H62B	109.1

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