Triphenyl[(triphenylphosphoranylidene)amino]phosphonium tetra­kis­(penta­fluoro­phen­yl)borate

Vanýsek, P.; Zheng, C.

doi:10.1107/S1600536812049914

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o87

https://doi.org/10.1107/S1600536812049914

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Triphenyl[(triphenylphosphoranylidene)amino]phosphonium tetrakis(pentafluorophenyl)borate

Petr Vanýsek ^a and Chong Zheng ^a ^*

^aDepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA
^*Correspondence e-mail: czheng@niu.edu

(Received 28 September 2012; accepted 5 December 2012; online 15 December 2012)

In the title molecular salt, C₃₆H₃₀NP₂⁺·C₂₄BF₂₀⁻, the P—N bond lengths in the cation are equal [1.573 (2) and 1.572 (2) Å], indicating a resonance structure and the P—N—P bond angle is 144.79 (12)°. In the crystal, weak C—H⋯F interactions link the cations and the anions.

Related literature

For details of the preparation, see: Fermín et al. (1999 ); Gobry (2001 ). For electrochemical studies of interfaces between polar organic solvents and water, see: Luo et al. (2006 ); Fermín et al. (1999); Su et al. (2008a ,b ); Stephenson et al. (2005 ). For an X-ray reflectivity study of the interface, see: Luo et al. (2006). For a Gibbs free-energy study of the compound, see: Vanýsek & Novák (2009 ).

Experimental

Crystal data

C₃₆H₃₀NP₂⁺·C₂₄BF₂₀⁻
M_r = 1217.60
Monoclinic, P 2₁ /n
a = 13.3081 (15) Å
b = 25.196 (3) Å
c = 16.0355 (18) Å
β = 100.094 (2)°
V = 5293.7 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.60 × 0.50 × 0.30 mm

Data collection

Bruker SMART CCD PLATFORM diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2006 ) T_min = 0.212, T_max = 0.264
39430 measured reflections
9311 independent reflections
7829 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.07
9311 reflections
758 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C118—H118⋯F302ⁱ	0.93	2.55	3.188 (2)	126
C212—H212⋯F303ⁱ	0.93	2.55	3.229 (3)	131
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1999 ); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049914/br2211sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049914/br2211Isup2.hkl

checkCIF report

Comment top

Salts of very hydrophobic cations and anions are very desirable for electrochemical studies of interfaces between polar organic solvent and water, commonly known as ITIES (Interface between Two Immiscible Electrolyte Solutions). These systems require an aqueous phase with very hydrophilic salt and a nonaqueous one with very hydrophobic salt, to be used as supporting electrolytes for their respective phases without leaching into the opposite phases. Thus, compound such as the current bis(triphenylphosphoranylidene)-ammonium tetrakis(pentafluorophenyl)borate are natural choice of materials for this purpose (Luo et al. 2006, Fermín et al. 1999, Su et al. 2008a,b, Stephenson et al. 2005). Its CAS registry number is 227603–93-2.

In the work of Luo and coworkers (Luo et al. 2006) this compound was used to study the fine structure of interface between two liquids using X-ray reflectivity of the interface. Vanýsek & Novák (2009) calculated the Gibbs energies of the transport for the individual ions between water and dichloroethane, the common organic phase for ITIES work. The structural information is important for understanding these Gibbs free energies.

Related literature top

For details of the preparation, see: Fermín et al. (1999); Gobry (2001). For electrochemical studies of interfaces between polar organic solvents and water, see: Luo et al. (2006); Fermín et al. (1999); Su et al. (2008a,b); Stephenson et al. (2005). For an X-ray reflectivity study of the interface, see: Luo et al. (2006). For a Gibbs free-energy study of the compound, see: Vanýsek & Novák (2009).

Experimental top

The preparation method is based on the metathesis of the starting materials with the elimination of water-soluble LiCl. The framework of the procedure is described in (Fermín et al. 1999). The starting materials used were bis(triphenylphosphoranylidene)-ammonium chloride (Aldrich) and either lithium or potassium tetrakis(pentafluorophenyl)borate (Boulder Scientific Company). In later preparations potassium tetrakis(pentafluorophenyl)borate (also from Boulder Scientific Company) was used, with identical electrochemical results. Both starting materials were dissolved in a methanol:water 2:1 mixture, with a minimum of 10 ml per gram of starting materials used. The solutions were combined and the precipitate formed was rinsed in copious amounts of a methanol:water 2:1 mixture, followed by large amount of distilled water. The product was vacuum-filtered and dried. The recrystallization was done from hot acetone (Gobry 2001). The yield was 82%. It is possible to obtain higher yields, however, the intended use of the product is very sensitive to any impurity, and the product would deteriorate with higher recovery. Also, it was noted that the vacuum filtration needs to be done rapidly, as prolonged drying on the filter apparently contaminates the product with contaminants from the air, which are visible in the electrochemical work. The melting point of the carefully prepared product was 234–235°C.

Structure description top

For details of the preparation, see: Fermín et al. (1999); Gobry (2001). For electrochemical studies of interfaces between polar organic solvents and water, see: Luo et al. (2006); Fermín et al. (1999); Su et al. (2008a,b); Stephenson et al. (2005). For an X-ray reflectivity study of the interface, see: Luo et al. (2006). For a Gibbs free-energy study of the compound, see: Vanýsek & Novák (2009).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Thermal ellipsoid drawing of the title compound shown at the 50% probability level.

Triphenyl[(triphenylphosphoranylidene)amino]phosphonium tetrakis(pentafluorophenyl)borate top

Crystal data top

C₃₆H₃₀NP₂⁺·C₂₄BF₂₀⁻	F(000) = 2448
M_r = 1217.60	D_x = 1.528 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 264 reflections
a = 13.3081 (15) Å	θ = 3–14°
b = 25.196 (3) Å	µ = 0.20 mm⁻¹
c = 16.0355 (18) Å	T = 298 K
β = 100.094 (2)°	Fragment, colorless
V = 5293.7 (10) Å³	0.60 × 0.50 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD PLATFORM diffractometer	9311 independent reflections
Radiation source: fine-focus sealed tube	7829 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	k = −29→29
T_min = 0.212, T_max = 0.264	l = −19→19
39430 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0481P)² + 1.7949P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
9311 reflections	Δρ_max = 0.28 e Å⁻³
758 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (4)

Crystal data top

C₃₆H₃₀NP₂⁺·C₂₄BF₂₀⁻	V = 5293.7 (10) Å³
M_r = 1217.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.3081 (15) Å	µ = 0.20 mm⁻¹
b = 25.196 (3) Å	T = 298 K
c = 16.0355 (18) Å	0.60 × 0.50 × 0.30 mm
β = 100.094 (2)°

Data collection top

Bruker SMART CCD PLATFORM diffractometer	9311 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	7829 reflections with I > 2σ(I)
T_min = 0.212, T_max = 0.264	R_int = 0.030
39430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
9311 reflections	Δρ_min = −0.26 e Å⁻³
758 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
P1	0.22856 (4)	0.088527 (18)	0.29937 (3)	0.04277 (13)
P2	0.08106 (4)	−0.000796 (19)	0.25127 (3)	0.04512 (13)
N1	0.16074 (13)	0.04472 (7)	0.24696 (11)	0.0542 (4)
B1	0.91160 (15)	0.33507 (8)	0.35287 (13)	0.0420 (4)
C101	0.22876 (14)	0.14614 (7)	0.23395 (12)	0.0470 (4)
C102	0.20818 (17)	0.14035 (9)	0.14671 (14)	0.0588 (5)
H102	0.1933	0.1070	0.1230	0.071*
C103	0.2096 (2)	0.18354 (11)	0.09540 (16)	0.0738 (7)
H103	0.1961	0.1795	0.0369	0.089*
C104	0.2308 (2)	0.23262 (10)	0.12998 (18)	0.0800 (7)
H104	0.2305	0.2620	0.0948	0.096*
C105	0.2527 (2)	0.23908 (9)	0.21653 (19)	0.0783 (7)
H105	0.2682	0.2726	0.2395	0.094*
C106	0.25171 (18)	0.19583 (8)	0.26909 (15)	0.0627 (6)
H106	0.2663	0.2000	0.3276	0.075*
C107	0.35801 (14)	0.06606 (8)	0.33088 (13)	0.0492 (4)
C108	0.43941 (17)	0.10045 (10)	0.33679 (18)	0.0742 (7)
H108	0.4286	0.1357	0.3204	0.089*
C109	0.53677 (19)	0.08255 (13)	0.3670 (2)	0.0962 (10)
H109	0.5915	0.1059	0.3709	0.115*
C110	0.5536 (2)	0.03128 (14)	0.3912 (2)	0.0895 (9)
H110	0.6197	0.0197	0.4118	0.107*
C111	0.4741 (2)	−0.00317 (11)	0.38521 (19)	0.0833 (8)
H111	0.4857	−0.0384	0.4016	0.100*
C112	0.37625 (18)	0.01402 (9)	0.35500 (16)	0.0671 (6)
H112	0.3221	−0.0097	0.3509	0.081*
C113	0.18575 (14)	0.10953 (7)	0.39451 (12)	0.0455 (4)
C114	0.23645 (16)	0.09499 (9)	0.47400 (13)	0.0578 (5)
H114	0.2970	0.0758	0.4796	0.069*
C115	0.1971 (2)	0.10899 (11)	0.54487 (15)	0.0724 (6)
H115	0.2309	0.0989	0.5982	0.087*
C116	0.1086 (2)	0.13773 (10)	0.53727 (16)	0.0740 (7)
H116	0.0826	0.1471	0.5854	0.089*
C117	0.05825 (19)	0.15274 (10)	0.45875 (16)	0.0704 (6)
H117	−0.0017	0.1723	0.4538	0.084*
C118	0.09619 (16)	0.13889 (8)	0.38735 (14)	0.0576 (5)
H118	0.0619	0.1492	0.3342	0.069*
C201	0.08078 (16)	−0.04373 (8)	0.16191 (13)	0.0536 (5)
C202	−0.0057 (2)	−0.06931 (14)	0.12396 (19)	0.0982 (10)
H202	−0.0675	−0.0625	0.1413	0.118*
C203	−0.0013 (3)	−0.10510 (17)	0.0602 (2)	0.1279 (15)
H203	−0.0601	−0.1231	0.0356	0.154*
C204	0.0878 (3)	−0.11453 (14)	0.0326 (2)	0.1086 (11)
H204	0.0896	−0.1382	−0.0115	0.130*
C205	0.1749 (3)	−0.08897 (13)	0.0701 (2)	0.0983 (10)
H205	0.2363	−0.0956	0.0519	0.118*
C206	0.1715 (2)	−0.05368 (11)	0.13461 (18)	0.0802 (8)
H206	0.2307	−0.0364	0.1601	0.096*
C207	−0.04614 (15)	0.02379 (8)	0.24891 (12)	0.0494 (4)
C208	−0.12093 (16)	−0.00698 (9)	0.27598 (14)	0.0591 (5)
H208	−0.1053	−0.0410	0.2967	0.071*
C209	−0.21786 (18)	0.01270 (12)	0.27225 (15)	0.0723 (7)
H209	−0.2680	−0.0082	0.2895	0.087*
C210	−0.2409 (2)	0.06321 (13)	0.24306 (18)	0.0826 (8)
H210	−0.3061	0.0768	0.2421	0.099*
C211	−0.1687 (2)	0.09353 (11)	0.2155 (2)	0.0900 (8)
H211	−0.1851	0.1276	0.1951	0.108*
C212	−0.07110 (18)	0.07410 (9)	0.21757 (17)	0.0709 (6)
H212	−0.0224	0.0948	0.1979	0.085*
C213	0.11038 (15)	−0.04065 (8)	0.34557 (13)	0.0500 (4)
C214	0.09871 (16)	−0.01864 (9)	0.42253 (13)	0.0577 (5)
H214	0.0696	0.0148	0.4241	0.069*
C215	0.13004 (19)	−0.04620 (11)	0.49680 (15)	0.0719 (6)
H215	0.1222	−0.0310	0.5482	0.086*
C216	0.1718 (2)	−0.09477 (12)	0.49585 (19)	0.0883 (8)
H216	0.1935	−0.1129	0.5463	0.106*
C217	0.1820 (3)	−0.11706 (12)	0.4210 (2)	0.1101 (11)
H217	0.2103	−0.1508	0.4205	0.132*
C218	0.1510 (2)	−0.09061 (10)	0.34541 (18)	0.0825 (8)
H218	0.1577	−0.1067	0.2945	0.099*
C301	0.93347 (13)	0.31757 (7)	0.25836 (11)	0.0429 (4)
C302	0.94568 (14)	0.26411 (7)	0.24073 (12)	0.0463 (4)
C303	0.96279 (15)	0.24450 (8)	0.16489 (13)	0.0526 (5)
C304	0.96834 (16)	0.27838 (9)	0.09941 (13)	0.0554 (5)
C305	0.95460 (15)	0.33148 (9)	0.11172 (13)	0.0545 (5)
C306	0.93588 (14)	0.34953 (7)	0.18875 (12)	0.0479 (4)
C307	0.91300 (14)	0.39991 (7)	0.36903 (11)	0.0464 (4)
C308	0.99731 (16)	0.42967 (8)	0.35719 (13)	0.0530 (5)
C309	1.00838 (18)	0.48316 (9)	0.37307 (14)	0.0629 (6)
C310	0.9343 (2)	0.50981 (8)	0.40492 (15)	0.0685 (6)
C311	0.85109 (19)	0.48278 (9)	0.42072 (14)	0.0654 (6)
C312	0.84172 (16)	0.42897 (8)	0.40271 (13)	0.0530 (5)
C313	1.00187 (14)	0.31447 (7)	0.43143 (12)	0.0461 (4)
C314	1.09755 (15)	0.29544 (8)	0.42482 (14)	0.0536 (5)
C315	1.17082 (16)	0.28180 (9)	0.49416 (17)	0.0669 (6)
C316	1.15124 (18)	0.28808 (10)	0.57383 (16)	0.0713 (7)
C317	1.05887 (19)	0.30817 (10)	0.58441 (14)	0.0669 (6)
C318	0.98807 (15)	0.32090 (8)	0.51411 (13)	0.0529 (5)
C319	0.79839 (13)	0.30774 (7)	0.35379 (11)	0.0430 (4)
C320	0.77678 (14)	0.26317 (7)	0.39764 (12)	0.0467 (4)
C321	0.68163 (16)	0.24029 (8)	0.38989 (13)	0.0532 (5)
C322	0.60085 (16)	0.26158 (9)	0.33584 (14)	0.0587 (5)
C323	0.61746 (15)	0.30516 (9)	0.28948 (13)	0.0576 (5)
C324	0.71371 (14)	0.32658 (8)	0.29868 (12)	0.0479 (4)
F302	0.94100 (10)	0.22779 (4)	0.30197 (7)	0.0595 (3)
F303	0.97370 (11)	0.19200 (5)	0.15422 (9)	0.0742 (4)
F304	0.98522 (11)	0.26021 (6)	0.02472 (8)	0.0785 (4)
F305	0.95914 (12)	0.36579 (5)	0.04829 (8)	0.0769 (4)
F306	0.91801 (10)	0.40232 (4)	0.19218 (7)	0.0616 (3)
F308	1.07512 (9)	0.40554 (5)	0.32848 (9)	0.0659 (3)
F309	1.09217 (12)	0.50916 (6)	0.35857 (11)	0.0893 (5)
F310	0.94318 (14)	0.56211 (5)	0.42144 (11)	0.1008 (5)
F311	0.77742 (13)	0.50779 (6)	0.45293 (10)	0.0935 (5)
F312	0.75641 (9)	0.40614 (5)	0.42110 (8)	0.0664 (3)
F314	1.12606 (9)	0.28882 (6)	0.34921 (8)	0.0721 (4)
F315	1.26140 (10)	0.26230 (7)	0.48210 (11)	0.0992 (5)
F316	1.22159 (13)	0.27484 (8)	0.64166 (11)	0.1081 (6)
F317	1.03870 (13)	0.31549 (8)	0.66281 (9)	0.1008 (5)
F318	0.89929 (9)	0.34100 (6)	0.52933 (8)	0.0679 (3)
F320	0.85042 (9)	0.23824 (4)	0.45267 (8)	0.0590 (3)
F321	0.66743 (10)	0.19687 (5)	0.43540 (9)	0.0748 (4)
F322	0.50761 (10)	0.23982 (7)	0.32793 (10)	0.0859 (4)
F323	0.53981 (9)	0.32680 (7)	0.23466 (9)	0.0838 (4)
F324	0.72415 (9)	0.36956 (5)	0.25024 (7)	0.0612 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0420 (3)	0.0386 (2)	0.0477 (3)	−0.00422 (19)	0.0077 (2)	−0.00334 (19)
P2	0.0464 (3)	0.0417 (3)	0.0464 (3)	−0.0080 (2)	0.0059 (2)	−0.0044 (2)
N1	0.0582 (10)	0.0510 (9)	0.0530 (10)	−0.0141 (8)	0.0086 (8)	−0.0045 (7)
B1	0.0403 (11)	0.0400 (10)	0.0454 (11)	0.0034 (8)	0.0066 (9)	0.0007 (9)
C101	0.0431 (10)	0.0453 (10)	0.0545 (11)	−0.0031 (8)	0.0138 (8)	0.0000 (8)
C102	0.0622 (13)	0.0597 (13)	0.0559 (12)	−0.0098 (10)	0.0139 (10)	−0.0008 (10)
C103	0.0812 (17)	0.0812 (17)	0.0610 (14)	−0.0122 (13)	0.0184 (12)	0.0128 (12)
C104	0.0964 (19)	0.0672 (16)	0.0828 (18)	−0.0039 (14)	0.0331 (15)	0.0241 (14)
C105	0.103 (2)	0.0440 (12)	0.095 (2)	−0.0081 (12)	0.0368 (16)	0.0011 (12)
C106	0.0812 (15)	0.0469 (11)	0.0631 (13)	−0.0071 (10)	0.0213 (11)	−0.0029 (10)
C107	0.0462 (10)	0.0480 (11)	0.0541 (11)	0.0013 (8)	0.0106 (8)	−0.0097 (9)
C108	0.0492 (12)	0.0613 (14)	0.111 (2)	−0.0041 (10)	0.0112 (12)	−0.0058 (13)
C109	0.0464 (14)	0.097 (2)	0.143 (3)	−0.0048 (14)	0.0106 (15)	−0.0153 (19)
C110	0.0524 (15)	0.112 (2)	0.104 (2)	0.0246 (15)	0.0116 (14)	−0.0087 (18)
C111	0.0806 (18)	0.0742 (17)	0.095 (2)	0.0304 (15)	0.0159 (15)	0.0037 (14)
C112	0.0615 (13)	0.0541 (13)	0.0853 (16)	0.0069 (10)	0.0119 (12)	−0.0011 (11)
C113	0.0474 (10)	0.0404 (9)	0.0490 (10)	−0.0040 (8)	0.0096 (8)	−0.0015 (8)
C114	0.0520 (11)	0.0656 (13)	0.0533 (12)	0.0031 (10)	0.0023 (9)	−0.0056 (10)
C115	0.0772 (16)	0.0892 (17)	0.0493 (12)	0.0032 (13)	0.0070 (11)	−0.0033 (12)
C116	0.0854 (17)	0.0832 (17)	0.0589 (14)	0.0027 (14)	0.0280 (13)	−0.0085 (12)
C117	0.0711 (15)	0.0704 (15)	0.0755 (16)	0.0178 (12)	0.0290 (12)	0.0033 (12)
C118	0.0581 (12)	0.0584 (12)	0.0577 (12)	0.0119 (10)	0.0136 (10)	0.0076 (10)
C201	0.0562 (12)	0.0546 (12)	0.0504 (11)	−0.0132 (9)	0.0103 (9)	−0.0098 (9)
C202	0.0683 (16)	0.135 (3)	0.092 (2)	−0.0332 (17)	0.0164 (14)	−0.0606 (19)
C203	0.102 (2)	0.165 (4)	0.116 (3)	−0.048 (2)	0.017 (2)	−0.085 (3)
C204	0.131 (3)	0.116 (3)	0.083 (2)	−0.031 (2)	0.0339 (19)	−0.0561 (19)
C205	0.099 (2)	0.104 (2)	0.101 (2)	−0.0166 (18)	0.0425 (18)	−0.0427 (18)
C206	0.0694 (15)	0.0855 (17)	0.0899 (18)	−0.0198 (13)	0.0258 (13)	−0.0352 (15)
C207	0.0503 (11)	0.0502 (11)	0.0463 (10)	−0.0041 (9)	0.0042 (8)	−0.0026 (8)
C208	0.0541 (12)	0.0654 (13)	0.0574 (12)	−0.0054 (10)	0.0089 (10)	0.0011 (10)
C209	0.0535 (13)	0.100 (2)	0.0646 (14)	−0.0073 (13)	0.0125 (11)	−0.0033 (13)
C210	0.0543 (14)	0.103 (2)	0.0866 (18)	0.0136 (14)	0.0031 (13)	−0.0163 (16)
C211	0.0741 (18)	0.0708 (17)	0.117 (2)	0.0143 (14)	−0.0046 (16)	0.0090 (16)
C212	0.0595 (14)	0.0594 (14)	0.0907 (17)	0.0003 (11)	0.0042 (12)	0.0106 (12)
C213	0.0479 (10)	0.0448 (10)	0.0557 (12)	−0.0067 (8)	0.0050 (9)	0.0008 (9)
C214	0.0595 (12)	0.0587 (12)	0.0546 (12)	−0.0034 (10)	0.0089 (10)	0.0011 (10)
C215	0.0724 (15)	0.0866 (18)	0.0551 (13)	−0.0064 (13)	0.0069 (11)	0.0059 (12)
C216	0.098 (2)	0.087 (2)	0.0738 (18)	0.0075 (16)	0.0001 (15)	0.0252 (15)
C217	0.159 (3)	0.0665 (17)	0.101 (2)	0.0421 (19)	0.013 (2)	0.0207 (17)
C218	0.116 (2)	0.0552 (14)	0.0746 (17)	0.0185 (14)	0.0122 (15)	0.0001 (12)
C301	0.0374 (9)	0.0428 (10)	0.0478 (10)	0.0004 (7)	0.0055 (8)	−0.0002 (8)
C302	0.0449 (10)	0.0439 (10)	0.0498 (11)	0.0006 (8)	0.0073 (8)	0.0016 (8)
C303	0.0513 (11)	0.0456 (11)	0.0611 (12)	−0.0009 (8)	0.0103 (9)	−0.0108 (9)
C304	0.0545 (12)	0.0646 (13)	0.0482 (11)	−0.0031 (10)	0.0121 (9)	−0.0122 (10)
C305	0.0552 (12)	0.0616 (13)	0.0473 (11)	−0.0041 (10)	0.0113 (9)	0.0062 (9)
C306	0.0487 (10)	0.0419 (10)	0.0531 (11)	−0.0010 (8)	0.0085 (8)	0.0009 (8)
C307	0.0486 (10)	0.0446 (10)	0.0435 (10)	0.0048 (8)	0.0012 (8)	−0.0018 (8)
C308	0.0547 (12)	0.0484 (11)	0.0528 (11)	−0.0012 (9)	0.0008 (9)	−0.0032 (9)
C309	0.0701 (14)	0.0510 (12)	0.0612 (13)	−0.0111 (11)	−0.0061 (11)	−0.0009 (10)
C310	0.0911 (18)	0.0402 (11)	0.0653 (14)	0.0018 (11)	−0.0111 (12)	−0.0093 (10)
C311	0.0793 (16)	0.0544 (13)	0.0573 (13)	0.0225 (12)	−0.0022 (11)	−0.0126 (10)
C312	0.0551 (12)	0.0521 (11)	0.0494 (11)	0.0085 (9)	0.0025 (9)	−0.0031 (9)
C313	0.0424 (10)	0.0415 (10)	0.0522 (11)	0.0000 (8)	0.0025 (8)	0.0016 (8)
C314	0.0456 (11)	0.0520 (11)	0.0609 (12)	0.0030 (9)	0.0033 (9)	−0.0023 (9)
C315	0.0439 (12)	0.0655 (14)	0.0854 (17)	0.0069 (10)	−0.0053 (11)	0.0032 (12)
C316	0.0595 (14)	0.0737 (15)	0.0698 (16)	0.0021 (11)	−0.0189 (12)	0.0110 (12)
C317	0.0733 (15)	0.0719 (15)	0.0501 (13)	−0.0051 (12)	−0.0042 (11)	0.0057 (11)
C318	0.0486 (11)	0.0543 (12)	0.0541 (12)	0.0004 (9)	0.0040 (9)	0.0018 (9)
C319	0.0417 (10)	0.0455 (10)	0.0417 (10)	0.0038 (8)	0.0073 (8)	−0.0026 (8)
C320	0.0472 (10)	0.0464 (10)	0.0458 (10)	0.0043 (8)	0.0063 (8)	0.0003 (8)
C321	0.0573 (12)	0.0499 (11)	0.0534 (11)	−0.0073 (9)	0.0126 (9)	−0.0006 (9)
C322	0.0455 (11)	0.0729 (14)	0.0571 (12)	−0.0124 (10)	0.0075 (9)	−0.0053 (11)
C323	0.0427 (11)	0.0766 (14)	0.0501 (11)	0.0060 (10)	−0.0016 (9)	0.0001 (10)
C324	0.0473 (11)	0.0510 (11)	0.0450 (10)	0.0036 (8)	0.0072 (8)	0.0034 (8)
F302	0.0773 (8)	0.0417 (6)	0.0612 (7)	0.0070 (5)	0.0170 (6)	0.0067 (5)
F303	0.0954 (10)	0.0495 (7)	0.0810 (9)	0.0035 (6)	0.0244 (7)	−0.0173 (6)
F304	0.0904 (10)	0.0924 (10)	0.0574 (8)	−0.0034 (8)	0.0261 (7)	−0.0191 (7)
F305	0.1014 (10)	0.0772 (9)	0.0558 (7)	−0.0018 (7)	0.0238 (7)	0.0140 (6)
F306	0.0833 (8)	0.0429 (6)	0.0588 (7)	0.0033 (5)	0.0135 (6)	0.0070 (5)
F308	0.0517 (7)	0.0638 (7)	0.0835 (9)	−0.0074 (6)	0.0159 (6)	−0.0063 (6)
F309	0.0929 (11)	0.0649 (8)	0.1046 (11)	−0.0309 (8)	0.0017 (8)	0.0006 (8)
F310	0.1391 (15)	0.0436 (7)	0.1065 (12)	0.0027 (8)	−0.0149 (10)	−0.0187 (7)
F311	0.1077 (12)	0.0761 (9)	0.0955 (11)	0.0365 (8)	0.0145 (9)	−0.0252 (8)
F312	0.0588 (7)	0.0692 (8)	0.0741 (8)	0.0123 (6)	0.0193 (6)	−0.0087 (6)
F314	0.0485 (7)	0.0950 (10)	0.0732 (8)	0.0164 (6)	0.0115 (6)	−0.0094 (7)
F315	0.0496 (8)	0.1182 (13)	0.1218 (13)	0.0288 (8)	−0.0072 (8)	0.0010 (10)
F316	0.0850 (11)	0.1322 (14)	0.0890 (11)	0.0130 (10)	−0.0353 (9)	0.0211 (10)
F317	0.1074 (12)	0.1400 (15)	0.0498 (8)	0.0071 (11)	−0.0006 (8)	0.0090 (8)
F318	0.0613 (7)	0.0901 (9)	0.0535 (7)	0.0097 (6)	0.0135 (6)	−0.0017 (6)
F320	0.0547 (7)	0.0544 (7)	0.0653 (7)	0.0043 (5)	0.0033 (5)	0.0157 (5)
F321	0.0767 (9)	0.0646 (8)	0.0830 (9)	−0.0181 (6)	0.0140 (7)	0.0145 (7)
F322	0.0519 (7)	0.1139 (12)	0.0890 (10)	−0.0278 (7)	0.0045 (7)	0.0040 (9)
F323	0.0474 (7)	0.1192 (12)	0.0777 (9)	0.0048 (7)	−0.0092 (6)	0.0232 (8)
F324	0.0561 (7)	0.0659 (7)	0.0585 (7)	0.0054 (6)	0.0018 (5)	0.0185 (6)

Geometric parameters (Å, º) top

P1—N1	1.5727 (16)	C209—H209	0.9300
P1—C101	1.7913 (19)	C210—C211	1.361 (4)
P1—C113	1.7992 (19)	C210—H210	0.9300
P1—C107	1.800 (2)	C211—C212	1.383 (4)
P2—N1	1.5717 (16)	C211—H211	0.9300
P2—C201	1.795 (2)	C212—H212	0.9300
P2—C207	1.797 (2)	C213—C218	1.370 (3)
P2—C213	1.800 (2)	C213—C214	1.386 (3)
B1—C301	1.653 (3)	C214—C215	1.378 (3)
B1—C307	1.654 (3)	C214—H214	0.9300
B1—C319	1.659 (3)	C215—C216	1.346 (4)
B1—C313	1.664 (3)	C215—H215	0.9300
C101—C106	1.385 (3)	C216—C217	1.352 (4)
C101—C102	1.385 (3)	C216—H216	0.9300
C102—C103	1.367 (3)	C217—C218	1.382 (4)
C102—H102	0.9300	C217—H217	0.9300
C103—C104	1.364 (4)	C218—H218	0.9300
C103—H103	0.9300	C301—C306	1.381 (3)
C104—C105	1.377 (4)	C301—C302	1.392 (3)
C104—H104	0.9300	C302—F302	1.352 (2)
C105—C106	1.379 (3)	C302—C303	1.368 (3)
C105—H105	0.9300	C303—F303	1.345 (2)
C106—H106	0.9300	C303—C304	1.365 (3)
C107—C112	1.376 (3)	C304—F304	1.338 (2)
C107—C108	1.377 (3)	C304—C305	1.369 (3)
C108—C109	1.377 (4)	C305—F305	1.344 (2)
C108—H108	0.9300	C305—C306	1.379 (3)
C109—C110	1.356 (4)	C306—F306	1.354 (2)
C109—H109	0.9300	C307—C312	1.381 (3)
C110—C111	1.360 (4)	C307—C308	1.390 (3)
C110—H110	0.9300	C308—F308	1.349 (2)
C111—C112	1.377 (3)	C308—C309	1.375 (3)
C111—H111	0.9300	C309—F309	1.348 (3)
C112—H112	0.9300	C309—C310	1.363 (3)
C113—C114	1.383 (3)	C310—F310	1.345 (2)
C113—C118	1.390 (3)	C310—C311	1.362 (4)
C114—C115	1.378 (3)	C311—F311	1.343 (3)
C114—H114	0.9300	C311—C312	1.387 (3)
C115—C116	1.369 (4)	C312—F312	1.351 (2)
C115—H115	0.9300	C313—C318	1.380 (3)
C116—C117	1.372 (4)	C313—C314	1.382 (3)
C116—H116	0.9300	C314—F314	1.343 (2)
C117—C118	1.375 (3)	C314—C315	1.387 (3)
C117—H117	0.9300	C315—F315	1.347 (3)
C118—H118	0.9300	C315—C316	1.357 (4)
C201—C202	1.365 (3)	C316—F316	1.347 (3)
C201—C206	1.378 (3)	C316—C317	1.367 (3)
C202—C203	1.372 (4)	C317—F317	1.343 (3)
C202—H202	0.9300	C317—C318	1.374 (3)
C203—C204	1.357 (5)	C318—F318	1.346 (2)
C203—H203	0.9300	C319—C320	1.382 (3)
C204—C205	1.370 (4)	C319—C324	1.388 (3)
C204—H204	0.9300	C320—F320	1.353 (2)
C205—C206	1.371 (4)	C320—C321	1.377 (3)
C205—H205	0.9300	C321—F321	1.347 (2)
C206—H206	0.9300	C321—C322	1.367 (3)
C207—C212	1.383 (3)	C322—F322	1.342 (2)
C207—C208	1.390 (3)	C322—C323	1.366 (3)
C208—C209	1.374 (3)	C323—F323	1.349 (2)
C208—H208	0.9300	C323—C324	1.374 (3)
C209—C210	1.372 (4)	C324—F324	1.354 (2)

N1—P1—C101	108.38 (9)	C211—C210—C209	120.2 (2)
N1—P1—C113	114.97 (9)	C211—C210—H210	119.9
C101—P1—C113	106.94 (9)	C209—C210—H210	119.9
N1—P1—C107	111.15 (9)	C210—C211—C212	120.5 (3)
C101—P1—C107	108.65 (9)	C210—C211—H211	119.8
C113—P1—C107	106.52 (9)	C212—C211—H211	119.8
N1—P2—C201	108.16 (9)	C207—C212—C211	119.9 (2)
N1—P2—C207	112.82 (9)	C207—C212—H212	120.1
C201—P2—C207	108.72 (9)	C211—C212—H212	120.1
N1—P2—C213	113.29 (9)	C218—C213—C214	118.4 (2)
C201—P2—C213	107.71 (10)	C218—C213—P2	122.58 (18)
C207—P2—C213	105.94 (9)	C214—C213—P2	118.88 (16)
P2—N1—P1	144.79 (12)	C215—C214—C213	120.2 (2)
C301—B1—C307	114.10 (15)	C215—C214—H214	119.9
C301—B1—C319	101.75 (14)	C213—C214—H214	119.9
C307—B1—C319	113.19 (15)	C216—C215—C214	120.8 (2)
C301—B1—C313	113.04 (15)	C216—C215—H215	119.6
C307—B1—C313	101.69 (14)	C214—C215—H215	119.6
C319—B1—C313	113.59 (15)	C215—C216—C217	119.6 (3)
C106—C101—C102	119.78 (19)	C215—C216—H216	120.2
C106—C101—P1	121.14 (16)	C217—C216—H216	120.2
C102—C101—P1	119.06 (15)	C216—C217—C218	121.2 (3)
C103—C102—C101	120.2 (2)	C216—C217—H217	119.4
C103—C102—H102	119.9	C218—C217—H217	119.4
C101—C102—H102	119.9	C213—C218—C217	119.9 (3)
C104—C103—C102	120.1 (2)	C213—C218—H218	120.1
C104—C103—H103	120.0	C217—C218—H218	120.1
C102—C103—H103	120.0	C306—C301—C302	112.34 (17)
C103—C104—C105	120.6 (2)	C306—C301—B1	128.20 (16)
C103—C104—H104	119.7	C302—C301—B1	119.35 (16)
C105—C104—H104	119.7	F302—C302—C303	115.92 (16)
C104—C105—C106	120.0 (2)	F302—C302—C301	119.07 (16)
C104—C105—H105	120.0	C303—C302—C301	125.00 (18)
C106—C105—H105	120.0	F303—C303—C304	119.71 (18)
C105—C106—C101	119.4 (2)	F303—C303—C302	120.45 (19)
C105—C106—H106	120.3	C304—C303—C302	119.84 (18)
C101—C106—H106	120.3	F304—C304—C303	120.99 (19)
C112—C107—C108	118.8 (2)	F304—C304—C305	120.7 (2)
C112—C107—P1	119.44 (16)	C303—C304—C305	118.27 (18)
C108—C107—P1	121.60 (17)	F305—C305—C304	119.63 (19)
C109—C108—C107	119.9 (2)	F305—C305—C306	120.30 (19)
C109—C108—H108	120.1	C304—C305—C306	120.06 (18)
C107—C108—H108	120.1	F306—C306—C305	114.89 (17)
C110—C109—C108	120.7 (3)	F306—C306—C301	120.71 (17)
C110—C109—H109	119.6	C305—C306—C301	124.39 (18)
C108—C109—H109	119.6	C312—C307—C308	113.18 (18)
C109—C110—C111	120.0 (2)	C312—C307—B1	126.54 (18)
C109—C110—H110	120.0	C308—C307—B1	119.91 (16)
C111—C110—H110	120.0	F308—C308—C309	116.18 (19)
C110—C111—C112	120.0 (3)	F308—C308—C307	119.32 (17)
C110—C111—H111	120.0	C309—C308—C307	124.5 (2)
C112—C111—H111	120.0	F309—C309—C310	120.0 (2)
C107—C112—C111	120.5 (2)	F309—C309—C308	120.6 (2)
C107—C112—H112	119.7	C310—C309—C308	119.4 (2)
C111—C112—H112	119.7	F310—C310—C311	119.9 (2)
C114—C113—C118	119.32 (18)	F310—C310—C309	120.8 (2)
C114—C113—P1	121.85 (15)	C311—C310—C309	119.2 (2)
C118—C113—P1	118.74 (15)	F311—C311—C310	120.6 (2)
C115—C114—C113	119.9 (2)	F311—C311—C312	119.6 (2)
C115—C114—H114	120.1	C310—C311—C312	119.8 (2)
C113—C114—H114	120.1	F312—C312—C307	121.39 (18)
C116—C115—C114	120.5 (2)	F312—C312—C311	114.77 (19)
C116—C115—H115	119.8	C307—C312—C311	123.8 (2)
C114—C115—H115	119.8	C318—C313—C314	113.21 (17)
C115—C116—C117	120.1 (2)	C318—C313—B1	119.40 (16)
C115—C116—H116	119.9	C314—C313—B1	127.07 (17)
C117—C116—H116	119.9	F314—C314—C313	121.49 (18)
C116—C117—C118	120.2 (2)	F314—C314—C315	115.01 (19)
C116—C117—H117	119.9	C313—C314—C315	123.5 (2)
C118—C117—H117	119.9	F315—C315—C316	120.1 (2)
C117—C118—C113	120.1 (2)	F315—C315—C314	119.7 (2)
C117—C118—H118	120.0	C316—C315—C314	120.1 (2)
C113—C118—H118	120.0	F316—C316—C315	120.7 (2)
C202—C201—C206	119.3 (2)	F316—C316—C317	120.3 (2)
C202—C201—P2	121.60 (18)	C315—C316—C317	119.0 (2)
C206—C201—P2	118.94 (16)	F317—C317—C316	119.9 (2)
C201—C202—C203	120.0 (3)	F317—C317—C318	121.0 (2)
C201—C202—H202	120.0	C316—C317—C318	119.1 (2)
C203—C202—H202	120.0	F318—C318—C317	115.86 (19)
C204—C203—C202	120.8 (3)	F318—C318—C313	119.16 (17)
C204—C203—H203	119.6	C317—C318—C313	125.0 (2)
C202—C203—H203	119.6	C320—C319—C324	112.57 (17)
C203—C204—C205	119.7 (3)	C320—C319—B1	127.74 (16)
C203—C204—H204	120.1	C324—C319—B1	119.32 (16)
C205—C204—H204	120.1	F320—C320—C321	114.46 (17)
C206—C205—C204	119.9 (3)	F320—C320—C319	121.18 (16)
C206—C205—H205	120.1	C321—C320—C319	124.36 (18)
C204—C205—H205	120.1	F321—C321—C322	119.54 (18)
C205—C206—C201	120.3 (2)	F321—C321—C320	120.35 (18)
C205—C206—H206	119.8	C322—C321—C320	120.11 (19)
C201—C206—H206	119.8	F322—C322—C323	120.8 (2)
C212—C207—C208	119.0 (2)	F322—C322—C321	120.7 (2)
C212—C207—P2	119.29 (16)	C323—C322—C321	118.45 (19)
C208—C207—P2	121.65 (16)	F323—C323—C322	120.07 (19)
C209—C208—C207	120.2 (2)	F323—C323—C324	120.3 (2)
C209—C208—H208	119.9	C322—C323—C324	119.63 (18)
C207—C208—H208	119.9	F324—C324—C323	116.12 (17)
C210—C209—C208	120.1 (2)	F324—C324—C319	119.03 (16)
C210—C209—H209	119.9	C323—C324—C319	124.86 (18)
C208—C209—H209	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C118—H118···F302ⁱ	0.93	2.55	3.188 (2)	126
C212—H212···F303ⁱ	0.93	2.55	3.229 (3)	131

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₆H₃₀NP₂⁺·C₂₄BF₂₀⁻
M_r	1217.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.3081 (15), 25.196 (3), 16.0355 (18)
β (°)	100.094 (2)
V (Å³)	5293.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.60 × 0.50 × 0.30

Data collection
Diffractometer	Bruker SMART CCD PLATFORM
Absorption correction	Multi-scan (SADABS; Sheldrick, 2006)
T_min, T_max	0.212, 0.264
No. of measured, independent and observed [I > 2σ(I)] reflections	39430, 9311, 7829
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.07
No. of reflections	9311
No. of parameters	758
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: SMART (Bruker, 1999), SMART and SAINT (Bruker, 1999), SAINT (Bruker, 1999), SIR97 (Altomare et al., 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C118—H118···F302ⁱ	0.93	2.55	3.188 (2)	126
C212—H212···F303ⁱ	0.93	2.55	3.229 (3)	131

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge support from the NSF-CHE0615129.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1999). SMART and SAINT. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Fermín, D. J., Duong, H. D., Ding, Z., Brevet, P. F. & Girault, H. H. (1999). Phys. Chem. Chem. Phys. 1, 1461–1467. Google Scholar
Gobry, V. (2001). Thesis, École Polytechnique Fédérale de Lausanne, Switzerland. Google Scholar
Luo, G., Málková, S., Yoon, J., Schultz, D. G., Lin, B., Meron, M., Benjamin, I., Vanýsek, P. & Schlossman, M. L. (2006). J. Electroanal. Chem. 593, 142–158. CrossRef CAS Google Scholar
Sheldrick, G. M. (2006). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stephenson, M. J., Holmes, S. M. & Dryfe, R. A. W. (2005). Angew. Chem. Int. Ed. 44, 3075–3078. Web of Science CrossRef CAS Google Scholar
Su, B., Li, F., Partovi-Nia, R., Gros, C., Barbe, J.-M., Samec, Z. & Girault, H. H. (2008a). Chem. Commun. 40, 5037–5038. Web of Science CrossRef Google Scholar
Su, B., Partovi-Nia, R., Li, F., Hojeij, M., Prudent, M., Corminboeuf, C., Samec, Z. & Girault, H. H. (2008b). Angew. Chem. Int. Ed. 47, 4675–4678. Web of Science CrossRef CAS Google Scholar
Vanýsek, P. & Novák, V. (2009). ECS Trans. 19, 55–63. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tri­phenyl[(tri­phenylphosphoranyl­idene)amino]phosphonium tetra­kis­(penta­fluoro­phen­yl)borate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Triphenyl[(triphenylphosphoranylidene)amino]phosphonium tetrakis(pentafluorophenyl)borate