cyclo-Bis­(par­aquat-m-ter­phenyl­ene) tetrakis­(hexa­fluoro­phosphate) tetrahydrate

In the title compound, C₆₀H₄₈N₄⁴⁺·4PF₆⁻·4H₂O, the tetra­cation as a whole assumes a chair-like conformation, as seen by joining the centroids of the bridging ter­phenyl­ene moieties with the four methyl­ene C atoms. Two inversion-related hexa­fluoro­phophate anions are inserted into the cavity of the centrosymmetric tetracation, whereas the other two anions are situated away from the cavity. The size of the cavity is approximately 13.23 × 12.86 Ų. The four water mol­ecules are partly inserted into the cavity. In the crystal, the cations, anions and water mol­ecules are held together by O—H...O, O—H...F, C—H...F and C—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.062
• wR factor = 0.149
• Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.114


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

4,4'-Bipyridinium-based tetracationic cyclophanes are found to be versatile macrocycles for constructing rotaxanes and catenanes (Amabilino & Stoddart, 1995). They have potential uses in resolving racemic substrates containing π-electron-rich aromatic rings (Asakawa et al., 1996) and function as non-sequence specific DNA photo cleaving agents (Lorente et al., 1999). cyclo-Bis(paraquat-m-terphenylene) is such a tetracationic cyclophane synthesized by refluxing an equimolar mixture of m-terphenyldibromide (Hart & Rajakumar, 1995) and 4,4'-bipyridine in acetonitrile for 48 h followed by column chromatography and counter-ion exchange with NH₄PF₆. We report here the structure of the tetracation as its tetrakis(hexafluorophophate) tetrahydrate, (I).

The asymmetric unit of (I) consists of one-half of the (C₆₀H₄₈N₄)⁴⁺ tetracation, two PF₆⁻anions and two water molecules. The other half of the tetracation is generated by a crystallographic inversion centre, as shown in Fig. 1. The centrosymmetric macrocyclic tetracation as a whole assumes a chair-like conformation, as seen by joining the centroids of the bridging terphenylene moieties with the four methylene C atoms. The mean planes through the terphenylene ring and bipyridinium ring are inclined by angles of 132.85 (3) and 97.45 (4)° with respect to the methylene plane. In the terphenylene system, the two outer rings are twisted from the central ring by 24.7 (1) and 18.9 (1)°. The dihedral angle between the two connected pyridinium rings is 15.2 (1)°. The macrocyclic valance angles at the methylene C atoms, C19 [110.9 (2)°] and C30 [111.8 (2)°], agree with the values reported for the pyridine-bridged phanes of 4,4'-bipyridine (Scheytza et al., 1999), but these values are larger than those reported for cyclo-bis(paraquat-p-phenylene) tetrakis(hexafluorophophate) (Odell et al., 1988). The overall dimensions of the macrocyclic tetracation are 13.23 Å between the centroids of the bonds connecting pyridinium rings and 12.86 Å between C12 and C12ⁱ [symmetry code: (i) −x, 1 − y, −z].

In the solid state, two inversion-related hexafluorophophate anions are inserted into the cavity of the centrosymmetric tetracation. The two P atoms, P1 and its centrosymmetric equivalent at (-x, 1 − y, −z), lie on the opposite sides of the methylene plane, at 0.874 (1) Å, and the distances separating them from the centroids of the bonds connecting pyridinium rings are each 3.975 Å. The other two anions lie on the opposite sides of the methylene plane at 5.133 (1) Å. The water O atoms, O1W and O2W, are located at 2.125 (3) and 1.989 (3) Å from the methylene plane. The four anions and the four water molecules are linked together by O—H···O and O—H···F hydrogen bonds to form discrete centrosymmetric units, as shown in Fig. 2. These units are linked to the macrocyclic tetracations through C—H···F hydrogen bonds (Table 2), to form a network structure. Two short intermolecular C···F contacts, C21···F4 [2.889 (3) Å] and C27···F6(-x, 1/2 + y, 1/2 − z) [2.933 (4) Å], are observed in the structure. But they are not indicative of C—H···F hydrogen bonding as the H21···F4 or H27···F6 distances are longer than the sum of the van der Waals radii.

S2. Experimental

The title compound was synthesized by refluxing an equimolar mixture of m-terphenyldibromide (Hart & Rajakumar, 1995) and 4,4'-bipyridine in acetonitrile for 48 h, followed by column chromatography and counter-ion exchange with NH₄PF₆ (Rajakumar & Srinivasan, 2002). Single crystals suitable for X-ray studies were grown by vapour diffusion of diisopropyl ether into a solution of (I) in acetonitrile.

S3. Refinement

The H atoms of the tetracation were fixed geometrically and allowed to ride on the corresponding non-H atoms, with C—H distances of 0.93 or 0.96 Å, and with U_iso(H) = 1.2U_eq(C). The H atoms of the water molecules were located from a difference map and their positional parameters were refined with restraints on the O—H distances; the isotropic displacement parameters were set equal to 1.5U_eq(O). The reflection (132) was removed during refinement, as the observed and calculated structure factors showed a large disagreement. The R_int value is high (0.114), owing to the poor diffraction quality of the crystal.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

	Fig. 1. The structure of the macrocyclic tetracation in the title compound. Displacement ellipsoids are drawn at 50% probability level. Only the contents of the asymmetric unit have been numbered.
	Fig. 2. The structure of the title compound, showing the arrangement of anions and water molecules.

(I)

Crystal data

C60H48N4^+·4PF6^−·4H2O	F(000) = 1504
Mr = 1476.97	Dx = 1.569 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8192 reflections
a = 11.7669 (1) Å	θ = 2.5–28.3°
b = 16.0300 (2) Å	µ = 0.24 mm^−1
c = 18.4544 (2) Å	T = 183 K
β = 116.089 (1)°	Slab, yellow
V = 3126.27 (6) Å^3	0.46 × 0.30 × 0.26 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	7566 independent reflections
Radiation source: fine-focus sealed tube	4043 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.114
Detector resolution: 8.33 pixels mm^-1	θmax = 28.4°, θmin = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→9
Tmin = 0.896, Tmax = 0.939	l = −22→24
18437 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0121P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
7565 reflections	Δρmax = 0.47 e Å^−3
446 parameters	Δρmin = −0.58 e Å^−3
5 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (6)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
P1	0.12774 (8)	0.57455 (5)	0.16459 (5)	0.0358 (2)
P2	−0.18831 (7)	0.08421 (5)	0.00478 (4)	0.02685 (19)
F1	0.0405 (2)	0.63028 (14)	0.18874 (15)	0.0830 (8)
F2	0.0280 (2)	0.57778 (13)	0.07263 (12)	0.0661 (6)
F3	0.21883 (19)	0.51821 (13)	0.14097 (13)	0.0648 (6)
F4	0.2319 (2)	0.56876 (14)	0.25554 (11)	0.0717 (7)
F5	0.19416 (19)	0.65642 (11)	0.15146 (12)	0.0583 (6)
F6	0.06272 (16)	0.49212 (11)	0.17671 (11)	0.0491 (5)
F7	−0.19394 (16)	0.18290 (11)	0.01615 (11)	0.0469 (5)
F8	−0.06869 (16)	0.09720 (11)	−0.01288 (11)	0.0443 (5)
F9	−0.18191 (16)	−0.01376 (10)	−0.00559 (10)	0.0439 (5)
F10	−0.30869 (16)	0.07251 (11)	0.02214 (11)	0.0438 (5)
F11	−0.09707 (17)	0.07557 (11)	0.09880 (10)	0.0458 (5)
F12	−0.27959 (16)	0.09389 (11)	−0.08871 (10)	0.0438 (5)
O1W	0.2339 (3)	0.33865 (18)	0.14669 (17)	0.0710 (8)
H1W1	0.183 (4)	0.322 (2)	0.1007 (13)	0.106*
H2W1	0.233 (4)	0.3903 (7)	0.139 (2)	0.106*
O2W	0.0514 (3)	0.26365 (19)	0.0086 (2)	0.0816 (9)
H1W2	0.005 (4)	0.225 (2)	0.009 (3)	0.122*
H2W2	−0.002 (4)	0.301 (2)	−0.012 (3)	0.122*
N1	0.5285 (2)	0.69532 (14)	0.35766 (13)	0.0270 (5)
N2	−0.0789 (2)	0.86641 (14)	0.19719 (14)	0.0266 (5)
C1	0.3027 (2)	0.17855 (17)	−0.11955 (16)	0.0260 (6)
C2	0.4201 (3)	0.17936 (19)	−0.11921 (17)	0.0326 (7)
H2	0.4412	0.1368	−0.1453	0.039*
C3	0.5066 (3)	0.24130 (19)	−0.08136 (17)	0.0328 (7)
H3	0.5851	0.2396	−0.0821	0.039*
C4	0.4789 (2)	0.30699 (17)	−0.04166 (16)	0.0249 (6)
C5	0.3596 (3)	0.30665 (17)	−0.04321 (17)	0.0297 (6)
H5	0.3377	0.3498	−0.0181	0.036*
C6	0.2726 (3)	0.24401 (18)	−0.08107 (17)	0.0313 (7)
H6	0.1937	0.2455	−0.0809	0.038*
C7	0.5751 (2)	0.37157 (17)	0.00191 (16)	0.0251 (6)
C8	0.6744 (3)	0.38919 (19)	−0.01728 (18)	0.0338 (7)
H8	0.6793	0.3614	−0.0601	0.041*
C9	0.7657 (3)	0.4470 (2)	0.02590 (18)	0.0366 (7)
H9	0.8314	0.4576	0.0121	0.044*
C10	0.7603 (3)	0.48925 (18)	0.08945 (18)	0.0330 (7)
H10	0.8222	0.5285	0.1178	0.040*
C11	0.6632 (2)	0.47384 (16)	0.11185 (16)	0.0262 (6)
C12	0.5718 (2)	0.41520 (16)	0.06669 (16)	0.0247 (6)
H12	0.5057	0.4046	0.0802	0.030*
C13	0.6593 (2)	0.51759 (16)	0.18131 (16)	0.0248 (6)
C14	0.7663 (3)	0.55611 (19)	0.24060 (18)	0.0353 (7)
H14	0.8424	0.5529	0.2368	0.042*
C15	0.7629 (3)	0.59849 (19)	0.30430 (18)	0.0354 (7)
H15	0.8357	0.6242	0.3421	0.042*
C16	0.6523 (2)	0.60307 (17)	0.31243 (16)	0.0270 (6)
C17	0.5454 (3)	0.56397 (19)	0.25548 (17)	0.0328 (7)
H17	0.4702	0.5660	0.2606	0.039*
C18	0.5491 (3)	0.52196 (18)	0.19122 (17)	0.0302 (7)
H18	0.4762	0.4960	0.1538	0.036*
C19	0.6496 (3)	0.64937 (19)	0.38273 (17)	0.0331 (7)
H19A	0.6597	0.6101	0.4251	0.040*
H19B	0.7196	0.6884	0.4042	0.040*
C20	0.4477 (3)	0.67449 (18)	0.38806 (16)	0.0296 (6)
H20	0.4709	0.6345	0.4285	0.036*
C21	0.3316 (3)	0.71164 (17)	0.35996 (16)	0.0289 (6)
H21	0.2764	0.6963	0.3814	0.035*
C22	0.2951 (2)	0.77166 (16)	0.30027 (15)	0.0224 (6)
C23	0.3830 (2)	0.79395 (17)	0.27179 (17)	0.0286 (6)
H23	0.3630	0.8351	0.2325	0.034*
C24	0.4979 (3)	0.75561 (18)	0.30133 (17)	0.0315 (7)
H24	0.5561	0.7713	0.2824	0.038*
C25	0.1658 (2)	0.80767 (16)	0.26569 (16)	0.0230 (6)
C26	0.0868 (3)	0.79645 (19)	0.30271 (18)	0.0348 (7)
H26	0.1168	0.7689	0.3520	0.042*
C27	−0.0347 (3)	0.82553 (19)	0.26744 (18)	0.0356 (7)
H27	−0.0871	0.8168	0.2925	0.043*
C28	−0.0043 (3)	0.88032 (18)	0.16074 (18)	0.0322 (7)
H28	−0.0355	0.9097	0.1124	0.039*
C29	0.1177 (3)	0.85160 (18)	0.19426 (17)	0.0325 (7)
H29	0.1687	0.8619	0.1685	0.039*
C30	−0.2132 (2)	0.89381 (18)	0.15814 (18)	0.0333 (7)
H30A	−0.2243	0.9352	0.1172	0.040*
H30B	−0.2342	0.9198	0.1982	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0435 (5)	0.0268 (4)	0.0408 (5)	−0.0115 (4)	0.0219 (4)	−0.0076 (4)
P2	0.0279 (4)	0.0255 (4)	0.0308 (4)	0.0018 (3)	0.0163 (3)	0.0003 (3)
F1	0.1095 (19)	0.0482 (14)	0.140 (2)	0.0025 (13)	0.0996 (19)	−0.0119 (14)
F2	0.0721 (15)	0.0508 (14)	0.0476 (12)	−0.0161 (11)	0.0010 (11)	0.0073 (10)
F3	0.0706 (14)	0.0515 (14)	0.0927 (17)	−0.0008 (11)	0.0545 (14)	−0.0094 (12)
F4	0.0766 (16)	0.0773 (17)	0.0426 (12)	−0.0392 (12)	0.0091 (11)	−0.0043 (11)
F5	0.0832 (15)	0.0348 (11)	0.0697 (14)	−0.0282 (10)	0.0454 (12)	−0.0112 (10)
F6	0.0453 (11)	0.0342 (11)	0.0627 (13)	−0.0151 (8)	0.0190 (10)	0.0054 (9)
F7	0.0549 (12)	0.0269 (10)	0.0679 (13)	0.0031 (8)	0.0352 (10)	−0.0015 (9)
F8	0.0382 (10)	0.0509 (12)	0.0576 (12)	0.0016 (8)	0.0337 (9)	0.0006 (9)
F9	0.0486 (11)	0.0281 (10)	0.0505 (11)	0.0016 (8)	0.0178 (9)	−0.0057 (8)
F10	0.0400 (10)	0.0509 (12)	0.0557 (12)	−0.0025 (8)	0.0349 (9)	−0.0013 (9)
F11	0.0473 (11)	0.0515 (12)	0.0317 (10)	−0.0064 (9)	0.0110 (8)	−0.0017 (9)
F12	0.0378 (10)	0.0584 (13)	0.0329 (10)	0.0086 (9)	0.0134 (8)	0.0054 (9)
O1W	0.076 (2)	0.0548 (18)	0.085 (2)	0.0184 (16)	0.0375 (17)	−0.0041 (16)
O2W	0.069 (2)	0.051 (2)	0.107 (2)	−0.0071 (14)	0.0215 (19)	0.0237 (18)
N1	0.0273 (12)	0.0243 (13)	0.0276 (12)	0.0025 (10)	0.0105 (10)	−0.0050 (10)
N2	0.0257 (12)	0.0195 (12)	0.0357 (14)	0.0022 (10)	0.0144 (11)	−0.0009 (11)
C1	0.0272 (15)	0.0225 (14)	0.0273 (14)	0.0044 (11)	0.0110 (12)	0.0016 (12)
C2	0.0291 (16)	0.0335 (17)	0.0384 (17)	0.0049 (13)	0.0179 (13)	−0.0056 (14)
C3	0.0272 (15)	0.0380 (18)	0.0372 (16)	0.0014 (13)	0.0179 (13)	−0.0026 (14)
C4	0.0251 (14)	0.0241 (15)	0.0271 (14)	0.0066 (11)	0.0127 (12)	0.0074 (12)
C5	0.0329 (16)	0.0240 (15)	0.0362 (16)	0.0085 (12)	0.0190 (13)	0.0009 (13)
C6	0.0258 (15)	0.0284 (16)	0.0446 (18)	0.0047 (12)	0.0198 (14)	0.0010 (14)
C7	0.0288 (15)	0.0221 (14)	0.0273 (14)	0.0064 (12)	0.0152 (12)	0.0071 (12)
C8	0.0372 (17)	0.0344 (17)	0.0370 (17)	0.0012 (14)	0.0231 (14)	−0.0006 (14)
C9	0.0320 (17)	0.0428 (19)	0.0433 (18)	−0.0047 (14)	0.0241 (15)	−0.0014 (15)
C10	0.0336 (16)	0.0294 (16)	0.0400 (18)	0.0004 (13)	0.0199 (14)	0.0016 (14)
C11	0.0246 (14)	0.0211 (14)	0.0320 (15)	0.0063 (11)	0.0116 (12)	0.0090 (12)
C12	0.0257 (14)	0.0212 (14)	0.0297 (14)	0.0062 (11)	0.0145 (12)	0.0086 (12)
C13	0.0264 (15)	0.0164 (13)	0.0311 (15)	0.0052 (11)	0.0123 (12)	0.0044 (12)
C14	0.0244 (16)	0.0373 (18)	0.0459 (19)	0.0007 (13)	0.0172 (14)	−0.0042 (15)
C15	0.0257 (16)	0.0379 (18)	0.0390 (17)	−0.0013 (13)	0.0110 (13)	−0.0058 (15)
C16	0.0250 (15)	0.0239 (15)	0.0292 (15)	0.0042 (12)	0.0093 (12)	0.0015 (12)
C17	0.0255 (15)	0.0382 (18)	0.0385 (17)	0.0011 (13)	0.0177 (13)	−0.0036 (14)
C18	0.0244 (15)	0.0282 (16)	0.0349 (16)	−0.0002 (12)	0.0102 (12)	−0.0044 (13)
C19	0.0281 (16)	0.0357 (17)	0.0331 (16)	0.0092 (13)	0.0114 (13)	0.0013 (14)
C20	0.0350 (16)	0.0272 (16)	0.0285 (15)	0.0018 (13)	0.0158 (13)	0.0027 (13)
C21	0.0302 (15)	0.0269 (15)	0.0344 (16)	0.0002 (13)	0.0186 (13)	0.0024 (13)
C22	0.0288 (14)	0.0151 (13)	0.0244 (14)	−0.0024 (11)	0.0127 (11)	−0.0048 (11)
C23	0.0301 (16)	0.0232 (15)	0.0360 (16)	0.0044 (12)	0.0179 (13)	0.0056 (13)
C24	0.0353 (17)	0.0262 (16)	0.0395 (17)	−0.0003 (13)	0.0223 (14)	0.0052 (13)
C25	0.0270 (14)	0.0166 (13)	0.0282 (14)	−0.0008 (11)	0.0146 (12)	−0.0047 (11)
C26	0.0374 (17)	0.0360 (18)	0.0366 (17)	0.0100 (14)	0.0214 (14)	0.0108 (14)
C27	0.0358 (17)	0.0365 (18)	0.0436 (18)	0.0062 (14)	0.0258 (15)	0.0087 (15)
C28	0.0358 (17)	0.0286 (16)	0.0342 (16)	0.0013 (13)	0.0172 (14)	0.0057 (13)
C29	0.0326 (16)	0.0328 (17)	0.0363 (17)	0.0008 (13)	0.0190 (14)	0.0053 (14)
C30	0.0255 (15)	0.0266 (16)	0.0451 (18)	0.0053 (12)	0.0131 (14)	0.0014 (14)

Geometric parameters (Å, º)

P1—F1	1.566 (2)	C9—H9	0.93
P1—F2	1.584 (2)	C10—C11	1.397 (3)
P1—F4	1.587 (2)	C10—H10	0.93
P1—F6	1.5912 (18)	C11—C12	1.396 (4)
P1—F5	1.5995 (18)	C11—C13	1.480 (4)
P1—F3	1.602 (2)	C12—H12	0.93
P2—F9	1.5880 (18)	C13—C18	1.389 (3)
P2—F12	1.5889 (17)	C13—C14	1.397 (4)
P2—F8	1.5920 (16)	C14—C15	1.374 (4)
P2—F10	1.5948 (16)	C14—H14	0.93
P2—F11	1.5950 (17)	C15—C16	1.375 (4)
P2—F7	1.6010 (18)	C15—H15	0.93
O1W—H1W1	0.84 (2)	C16—C17	1.385 (4)
O1W—H2W1	0.84 (1)	C16—C19	1.507 (4)
O2W—H1W2	0.83 (4)	C17—C18	1.381 (4)
O2W—H2W2	0.83 (4)	C17—H17	0.93
N1—C20	1.341 (3)	C18—H18	0.93
N1—C24	1.347 (3)	C19—H19A	0.97
N1—C19	1.486 (3)	C19—H19B	0.97
N2—C27	1.337 (3)	C20—C21	1.366 (4)
N2—C28	1.339 (3)	C20—H20	0.93
N2—C30	1.486 (3)	C21—C22	1.381 (4)
C1—C2	1.379 (4)	C21—H21	0.93
C1—C6	1.397 (4)	C22—C23	1.397 (3)
C1—C30^i	1.517 (4)	C22—C25	1.484 (4)
C2—C3	1.373 (4)	C23—C24	1.362 (4)
C2—H2	0.93	C23—H23	0.93
C3—C4	1.400 (4)	C24—H24	0.93
C3—H3	0.93	C25—C29	1.378 (4)
C4—C5	1.392 (3)	C25—C26	1.386 (3)
C4—C7	1.483 (4)	C26—C27	1.366 (4)
C5—C6	1.384 (4)	C26—H26	0.93
C5—H5	0.93	C27—H27	0.93
C6—H6	0.93	C28—C29	1.369 (4)
C7—C8	1.392 (3)	C28—H28	0.93
C7—C12	1.400 (4)	C29—H29	0.93
C8—C9	1.376 (4)	C30—C1^i	1.517 (4)
C8—H8	0.93	C30—H30A	0.97
C9—C10	1.379 (4)	C30—H30B	0.97
F1—P1—F2	90.94 (13)	C11—C10—H10	119.6
F1—P1—F4	91.76 (14)	C12—C11—C10	117.3 (3)
F2—P1—F4	177.30 (14)	C12—C11—C13	121.8 (2)
F1—P1—F6	91.03 (11)	C10—C11—C13	120.9 (3)
F2—P1—F6	90.11 (10)	C11—C12—C7	122.9 (2)
F4—P1—F6	89.91 (11)	C11—C12—H12	118.6
F1—P1—F5	90.01 (12)	C7—C12—H12	118.6
F2—P1—F5	89.56 (11)	C18—C13—C14	116.5 (2)
F4—P1—F5	90.37 (11)	C18—C13—C11	121.7 (2)
F6—P1—F5	178.92 (12)	C14—C13—C11	121.8 (2)
F1—P1—F3	179.12 (14)	C15—C14—C13	122.2 (3)
F2—P1—F3	89.78 (12)	C15—C14—H14	118.9
F4—P1—F3	87.52 (13)	C13—C14—H14	118.9
F6—P1—F3	89.46 (11)	C14—C15—C16	120.3 (3)
F5—P1—F3	89.50 (11)	C14—C15—H15	119.8
F9—P2—F12	90.63 (10)	C16—C15—H15	119.8
F9—P2—F8	90.67 (10)	C15—C16—C17	118.7 (3)
F12—P2—F8	90.07 (9)	C15—C16—C19	120.0 (2)
F9—P2—F10	90.07 (10)	C17—C16—C19	121.3 (2)
F12—P2—F10	89.63 (9)	C18—C17—C16	120.7 (3)
F8—P2—F10	179.21 (11)	C18—C17—H17	119.6
F9—P2—F11	90.02 (10)	C16—C17—H17	119.6
F12—P2—F11	179.34 (11)	C17—C18—C13	121.4 (3)
F8—P2—F11	90.08 (10)	C17—C18—H18	119.3
F10—P2—F11	90.21 (9)	C13—C18—H18	119.3
F9—P2—F7	179.45 (12)	N1—C19—C16	110.9 (2)
F12—P2—F7	89.92 (10)	N1—C19—H19A	109.5
F8—P2—F7	89.36 (9)	C16—C19—H19A	109.5
F10—P2—F7	89.90 (9)	N1—C19—H19B	109.5
F11—P2—F7	89.43 (10)	C16—C19—H19B	109.5
H1W1—O1W—H2W1	100.8 (15)	H19A—C19—H19B	108.0
H1W2—O2W—H2W2	100 (5)	N1—C20—C21	120.5 (3)
C20—N1—C24	120.2 (2)	N1—C20—H20	119.8
C20—N1—C19	120.4 (2)	C21—C20—H20	119.8
C24—N1—C19	119.3 (2)	C20—C21—C22	121.0 (3)
C27—N2—C28	120.5 (2)	C20—C21—H21	119.5
C27—N2—C30	119.5 (2)	C22—C21—H21	119.5
C28—N2—C30	120.0 (2)	C21—C22—C23	117.1 (2)
C2—C1—C6	117.9 (3)	C21—C22—C25	121.0 (2)
C2—C1—C30^i	119.8 (2)	C23—C22—C25	121.8 (2)
C6—C1—C30^i	122.3 (2)	C24—C23—C22	120.2 (3)
C3—C2—C1	121.8 (3)	C24—C23—H23	119.9
C3—C2—H2	119.1	C22—C23—H23	119.9
C1—C2—H2	119.1	N1—C24—C23	120.9 (3)
C2—C3—C4	121.3 (3)	N1—C24—H24	119.5
C2—C3—H3	119.4	C23—C24—H24	119.5
C4—C3—H3	119.4	C29—C25—C26	117.1 (2)
C5—C4—C3	116.8 (3)	C29—C25—C22	121.5 (2)
C5—C4—C7	122.4 (2)	C26—C25—C22	121.4 (2)
C3—C4—C7	120.7 (2)	C27—C26—C25	120.6 (3)
C6—C5—C4	121.9 (3)	C27—C26—H26	119.7
C6—C5—H5	119.0	C25—C26—H26	119.7
C4—C5—H5	119.0	N2—C27—C26	120.6 (3)
C5—C6—C1	120.3 (2)	N2—C27—H27	119.7
C5—C6—H6	119.8	C26—C27—H27	119.7
C1—C6—H6	119.8	N2—C28—C29	120.4 (3)
C8—C7—C12	117.2 (3)	N2—C28—H28	119.8
C8—C7—C4	122.0 (2)	C29—C28—H28	119.8
C12—C7—C4	120.7 (2)	C28—C29—C25	120.9 (3)
C9—C8—C7	121.2 (3)	C28—C29—H29	119.6
C9—C8—H8	119.4	C25—C29—H29	119.6
C7—C8—H8	119.4	N2—C30—C1^i	111.8 (2)
C8—C9—C10	120.5 (3)	N2—C30—H30A	109.2
C8—C9—H9	119.8	C1^i—C30—H30A	109.2
C10—C9—H9	119.8	N2—C30—H30B	109.2
C9—C10—C11	120.9 (3)	C1^i—C30—H30B	109.2
C9—C10—H10	119.6	H30A—C30—H30B	107.9
C6—C1—C2—C3	1.1 (4)	C19—C16—C17—C18	179.8 (3)
C30^i—C1—C2—C3	−176.6 (3)	C16—C17—C18—C13	−0.2 (4)
C1—C2—C3—C4	−0.4 (5)	C14—C13—C18—C17	1.5 (4)
C2—C3—C4—C5	−0.6 (4)	C11—C13—C18—C17	−179.0 (3)
C2—C3—C4—C7	177.4 (3)	C20—N1—C19—C16	115.3 (3)
C3—C4—C5—C6	0.9 (4)	C24—N1—C19—C16	−61.7 (3)
C7—C4—C5—C6	−177.1 (3)	C15—C16—C19—N1	142.0 (3)
C4—C5—C6—C1	−0.2 (4)	C17—C16—C19—N1	−38.5 (4)
C2—C1—C6—C5	−0.8 (4)	C24—N1—C20—C21	2.7 (4)
C30^i—C1—C6—C5	176.8 (3)	C19—N1—C20—C21	−174.3 (2)
C5—C4—C7—C8	−158.1 (3)	N1—C20—C21—C22	−0.4 (4)
C3—C4—C7—C8	24.0 (4)	C20—C21—C22—C23	−1.7 (4)
C5—C4—C7—C12	24.4 (4)	C20—C21—C22—C25	175.6 (2)
C3—C4—C7—C12	−153.5 (3)	C21—C22—C23—C24	1.6 (4)
C12—C7—C8—C9	0.2 (4)	C25—C22—C23—C24	−175.7 (3)
C4—C7—C8—C9	−177.4 (3)	C20—N1—C24—C23	−2.8 (4)
C7—C8—C9—C10	−0.2 (5)	C19—N1—C24—C23	174.2 (3)
C8—C9—C10—C11	0.6 (5)	C22—C23—C24—N1	0.6 (4)
C9—C10—C11—C12	−0.9 (4)	C21—C22—C25—C29	−164.1 (3)
C9—C10—C11—C13	178.4 (3)	C23—C22—C25—C29	13.0 (4)
C10—C11—C12—C7	0.9 (4)	C21—C22—C25—C26	13.9 (4)
C13—C11—C12—C7	−178.5 (2)	C23—C22—C25—C26	−168.9 (3)
C8—C7—C12—C11	−0.5 (4)	C29—C25—C26—C27	2.3 (4)
C4—C7—C12—C11	177.1 (2)	C22—C25—C26—C27	−175.9 (3)
C12—C11—C13—C18	−19.1 (4)	C28—N2—C27—C26	−0.8 (4)
C10—C11—C13—C18	161.5 (3)	C30—N2—C27—C26	177.1 (3)
C12—C11—C13—C14	160.4 (3)	C25—C26—C27—N2	−1.0 (5)
C10—C11—C13—C14	−18.9 (4)	C27—N2—C28—C29	1.1 (4)
C18—C13—C14—C15	−2.0 (4)	C30—N2—C28—C29	−176.7 (3)
C11—C13—C14—C15	178.5 (3)	N2—C28—C29—C25	0.3 (4)
C13—C14—C15—C16	1.2 (5)	C26—C25—C29—C28	−1.9 (4)
C14—C15—C16—C17	0.2 (4)	C22—C25—C29—C28	176.2 (3)
C14—C15—C16—C19	179.7 (3)	C27—N2—C30—C1^i	−75.0 (3)
C15—C16—C17—C18	−0.7 (4)	C28—N2—C30—C1^i	102.8 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2W	0.84 (2)	1.96 (3)	2.782 (4)	166 (4)
O1W—H2W1···F3	0.84 (1)	2.06 (1)	2.883 (4)	167 (4)
O2W—H1W2···F7	0.83 (4)	2.49 (5)	3.222 (4)	147 (4)
O2W—H1W2···F8	0.83 (4)	2.19 (4)	2.963 (4)	155 (5)
O2W—H2W2···F2^i	0.83 (4)	2.20 (4)	2.890 (4)	141 (5)
C19—H19A···F9^ii	0.97	2.32	3.051 (4)	131
C21—H21···F7^iii	0.93	2.49	3.365 (4)	158
C24—H24···O1W^iv	0.93	2.48	3.161 (5)	130
C27—H27···O1W^iii	0.93	2.46	3.364 (5)	163
C28—H28···F9^v	0.93	2.43	3.321 (3)	160
C29—H29···F12^i	0.93	2.46	3.384 (4)	171
C30—H30B···F4^iii	0.97	2.53	3.280 (4)	134

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