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

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Crystal structure of tri­phenyl(vinyl)­phospho­nium tetra­phenyl­borate

aDepartment of Chemistry and Physics, Florida Gulf Coast University, Fort Myers, FL 33965, USA, and bUniversity of South Alabama, Department of Chemistry, Mobile, AL 36688, USA
*Correspondence e-mail: amirjafari@fgcu.edu

Edited by P. C. Healy, Griffith University, Australia (Received 9 September 2014; accepted 25 September 2014; online 30 September 2014)

The title ionic salt, C21H20P+·C24H20B, crystallized with two independent vinyl­tri­phenyl­phospho­nium cations and two independent tetra­phenyl­borate anions per asymmetric unit. These four independent moieties contain nearly perfect tetra­hedral symmetry about their respective central C atoms. In the crystal, there are no π-stacking or other inter­molecular inter­actions present.

1. Related literature

For background to the study of phosphine compounds, see: Bellina et al. (2012[Bellina, F., Chiappe, C. & Lessi, M. (2012). Green Chem. 14, 148-155.]). For information on ionic liquids, see: Chowdhury et al. (2007[Chowdhury, S., Mohan, R. S. & Scott, J. L. (2007). Tetrahedron, 63, 2363-2389.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H20P+·C24H20B

  • Mr = 622.55

  • Monoclinic, P 21

  • a = 9.2752 (4) Å

  • b = 35.7838 (15) Å

  • c = 10.9515 (5) Å

  • β = 100.721 (4)°

  • V = 3571.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 180 K

  • 0.43 × 0.18 × 0.17 mm

2.2. Data collection

  • Agilent Xcalibur, Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.958, Tmax = 1.000

  • 24267 measured reflections

  • 12797 independent reflections

  • 9444 reflections with I > 2σ(I)

  • Rint = 0.038

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.105

  • S = 1.01

  • 12797 reflections

  • 849 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.23 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Absolute structure parameter: 0.02 (7)

Data collection: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Chemical Context top

In recent years, phospho­rus-carbon bond-forming reactions have been the object of inter­est in the modern organo­phospho­rus chemistry due to the importance of these products in a variety of fields ranging from material science to the synthesis of biologically active molecules. Phospho­nium salts have been known since the 1980s; however, they were rarely employed until the 1990s, when phosphines were used as precursors on the large scale, see: Bellina et al. (2012).

Phospho­nium-based ionic liquids emerged as a very promising alternative to imidazolium analogs due to their superior thermal stability and inertness in the basic environment. The presence of an acidic hydrogen at the C2 position of imidazolium rings in many ionic liquids, leads to the thermal instability that limits the applications of these inter­esting organic fluids, see: Chowdhury et al. (2007).

In this study, we found that the vinyl­tri­phenyl­phospho­nium bromide could be synthesized via the nucleophilic attack of tri­phenyl­phosphine to allyl bromide to form the corresponding betaine 1, followed by the intra-hydrogen shift reaction (Figure 2). In the next step, metathesis reaction of vinyl­triphenyphospho­nium bromide 2 with sodium tetra­phenyl­borate led to the formation vinyl­triphenyphospho­nium tetra­phenyl­borane 3 (Tm= 72–74° C) as the final product in high yield (78%).

Related literature top

For background to the study of phosphine compounds, see: Bellina et al. (2012). For information on ionic liquids, see: Chowdhury et al. (2007).

Experimental top

Triphenylphosphine (0.5 mmol) and allyl bromide (0.7 mmol) were dissolved in toluene (2.0 ml) and the mixture refluxed for 48 h. The solvent was removed in a vacuum and the crude product was dissolved in 4.0 ml of H2O. Then, a solution of sodium tetraphenylborate (0.6 mmol) in 2.0 ml of H2O was added to the original solution of crude product and was stirred for 24 h. The final product was separated via filtration and washed with H2O (3 x 5 ml) to yield white crystals of the title complex.

Refinement top

H-atoms were placed in calculated positions and allowed to ride during subsequent refinement with Uiso(H) = 1.2Ueq(C) and C—H distances of 0.93 Å, except for the methyl H atoms which had Uiso(H) = 1.5Ueq(C) and C—H distances of 0.96 Å.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OlEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OlEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A ball-and-stick representaion of the structure of I. Only one of the two cation/anion pairs are shown. Hydrogen atoms on the aromatic rings have been removed for clarity.
[Figure 2] Fig. 2. Reaction scheme for the synthesis of I.
Triphenyl(vinyl)phosphonium tetraphenylborate top
Crystal data top
C21H20P+·C24H20BF(000) = 1320
Mr = 622.55Dx = 1.158 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
a = 9.2752 (4) ÅCell parameters from 4486 reflections
b = 35.7838 (15) Åθ = 3.0–25.0°
c = 10.9515 (5) ŵ = 0.11 mm1
β = 100.721 (4)°T = 180 K
V = 3571.4 (3) Å3Prism, colourless
Z = 40.43 × 0.18 × 0.17 mm
Data collection top
Agilent Xcalibur, Eos
diffractometer
12797 independent reflections
Radiation source: Enhance (Mo) X-ray Source9444 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 16.0514 pixels mm-1θmax = 25.2°, θmin = 2.5°
ω scansh = 911
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 4242
Tmin = 0.958, Tmax = 1.000l = 1312
24267 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.038P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
12797 reflectionsΔρmax = 0.35 e Å3
849 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (7)
Crystal data top
C21H20P+·C24H20BV = 3571.4 (3) Å3
Mr = 622.55Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.2752 (4) ŵ = 0.11 mm1
b = 35.7838 (15) ÅT = 180 K
c = 10.9515 (5) Å0.43 × 0.18 × 0.17 mm
β = 100.721 (4)°
Data collection top
Agilent Xcalibur, Eos
diffractometer
12797 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
9444 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 1.000Rint = 0.038
24267 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.105Δρmax = 0.35 e Å3
S = 1.01Δρmin = 0.23 e Å3
12797 reflectionsAbsolute structure: Flack (1983)
849 parametersAbsolute structure parameter: 0.02 (7)
1 restraint
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 > 2σ(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
xyzUiso*/Ueq
P10.34715 (9)0.43752 (2)0.03996 (8)0.0268 (2)
B10.2156 (4)0.36038 (10)0.5307 (3)0.0258 (9)
C720.4956 (3)0.35850 (9)0.6594 (3)0.0304 (8)
H720.46500.34270.71700.037*
C170.4142 (4)0.36574 (9)0.0218 (3)0.0359 (9)
H170.33800.36860.08960.043*
C790.1227 (3)0.39980 (9)0.5080 (3)0.0257 (7)
C20.4719 (4)0.45131 (9)0.1653 (3)0.0315 (8)
H20.50980.42730.15340.038*
C40.3897 (3)0.46572 (9)0.1772 (3)0.0255 (8)
C180.4917 (4)0.33265 (9)0.0053 (3)0.0398 (9)
H180.46850.31350.06280.048*
C730.1727 (3)0.33367 (8)0.4059 (3)0.0252 (8)
C670.3916 (3)0.37116 (8)0.5581 (3)0.0260 (8)
C210.5619 (3)0.38947 (9)0.1647 (3)0.0305 (8)
H210.58610.40860.22230.037*
C160.4499 (3)0.39493 (9)0.0632 (3)0.0256 (8)
C110.0563 (4)0.44317 (10)0.0802 (3)0.0388 (9)
H110.08780.46150.12960.047*
C100.1559 (3)0.42514 (9)0.0120 (3)0.0281 (8)
C50.5204 (4)0.48620 (9)0.1970 (3)0.0334 (8)
H50.58010.48600.13750.040*
C750.2179 (4)0.30267 (10)0.2179 (3)0.0392 (9)
H750.28190.29790.16370.047*
C90.2993 (4)0.46700 (9)0.2647 (3)0.0300 (8)
H90.21040.45430.25090.036*
C680.4482 (4)0.39505 (9)0.4765 (3)0.0340 (8)
H680.38410.40420.40740.041*
C800.0193 (3)0.40884 (9)0.4016 (3)0.0310 (8)
H800.00060.39130.33800.037*
C870.0463 (4)0.32577 (11)0.8201 (3)0.0449 (10)
H870.01760.33470.86950.054*
C140.0395 (4)0.38877 (11)0.0646 (3)0.0414 (10)
H140.07190.37010.11210.050*
C10.3916 (3)0.46345 (9)0.0853 (3)0.0297 (8)
H10.35550.48770.09590.036*
C830.0698 (4)0.46182 (10)0.5853 (3)0.0443 (10)
H830.08690.47940.64890.053*
C700.6933 (4)0.39238 (10)0.5945 (3)0.0386 (9)
H700.79180.39920.60680.046*
C840.1452 (4)0.42801 (9)0.5987 (3)0.0345 (9)
H840.21360.42390.67110.041*
C770.0138 (4)0.29464 (9)0.2771 (3)0.0355 (9)
H770.10740.28430.26330.043*
C740.2627 (4)0.32536 (9)0.3213 (3)0.0322 (8)
H740.35690.33540.33430.039*
C60.5614 (4)0.50689 (9)0.3053 (3)0.0354 (9)
H60.64880.52030.31840.043*
C850.1718 (3)0.33667 (9)0.6475 (3)0.0264 (8)
C30.5066 (4)0.47268 (9)0.2720 (3)0.0374 (9)
H3A0.47270.45910.34740.056*
H3B0.61070.47620.26120.056*
H3C0.45870.49660.27640.056*
C810.0547 (4)0.44277 (10)0.3868 (3)0.0393 (9)
H810.12160.44750.31400.047*
C190.6038 (4)0.32777 (10)0.0965 (3)0.0374 (9)
H190.65550.30540.10730.045*
C130.1381 (4)0.40692 (11)0.0248 (4)0.0450 (10)
H130.23740.40110.03590.054*
C690.5953 (4)0.40575 (10)0.4934 (3)0.0377 (9)
H690.62700.42180.43700.045*
C900.2321 (4)0.30060 (9)0.6724 (3)0.0355 (9)
H900.29480.29140.62230.043*
C820.0297 (4)0.46938 (10)0.4787 (4)0.0412 (10)
H820.07930.49210.46900.049*
C150.1073 (4)0.39795 (10)0.0846 (3)0.0346 (9)
H150.17330.38590.14650.042*
C780.0317 (4)0.31736 (9)0.3794 (3)0.0311 (8)
H780.03330.32210.43280.037*
C80.3430 (4)0.48758 (9)0.3735 (3)0.0367 (9)
H80.28400.48790.43350.044*
C880.1060 (4)0.29117 (11)0.8424 (3)0.0476 (11)
H880.08320.27640.90600.057*
C890.2021 (4)0.27830 (10)0.7679 (3)0.0444 (10)
H890.24580.25490.78220.053*
C200.6382 (4)0.35622 (10)0.1817 (3)0.0375 (9)
H200.71270.35300.25050.045*
C70.4730 (4)0.50756 (9)0.3932 (3)0.0376 (9)
H70.50050.52140.46560.045*
C860.0791 (3)0.34815 (9)0.7245 (3)0.0311 (8)
H860.03660.37170.71240.037*
C760.0797 (4)0.28730 (9)0.1955 (3)0.0389 (9)
H760.04950.27220.12640.047*
C710.6427 (4)0.36872 (10)0.6768 (3)0.0388 (9)
H710.70800.35950.74500.047*
C120.0905 (4)0.43336 (12)0.0969 (3)0.0494 (10)
H120.15770.44510.15870.059*
P20.08786 (9)0.68072 (2)0.54835 (8)0.0300 (2)
C250.1647 (4)0.64615 (9)0.4583 (3)0.0310 (8)
C370.1002 (3)0.68908 (9)0.4796 (3)0.0301 (8)
C310.1892 (3)0.72348 (9)0.5475 (3)0.0286 (8)
C350.3943 (4)0.76235 (10)0.6324 (3)0.0385 (9)
H350.47660.76710.69320.046*
C360.3151 (4)0.72971 (9)0.6382 (3)0.0323 (8)
H360.34490.71230.70090.039*
C260.1572 (4)0.60903 (10)0.4903 (3)0.0380 (9)
H260.11200.60200.55580.046*
C320.1483 (4)0.74896 (10)0.4528 (3)0.0393 (9)
H320.06630.74450.39150.047*
C230.0020 (4)0.65275 (10)0.7555 (3)0.0387 (9)
H230.09640.65420.70870.046*
C420.1630 (4)0.67238 (9)0.3679 (3)0.0358 (9)
H420.10820.65590.32930.043*
C340.3532 (4)0.78776 (10)0.5384 (4)0.0433 (10)
H340.40840.80930.53480.052*
C410.3067 (4)0.68013 (11)0.3140 (4)0.0479 (10)
H410.34890.66900.23910.057*
C380.1820 (4)0.71415 (10)0.5365 (3)0.0416 (10)
H380.13930.72610.60970.050*
C290.2864 (4)0.62943 (12)0.2914 (4)0.0542 (11)
H290.32940.63610.22430.065*
C400.3871 (4)0.70459 (11)0.3721 (4)0.0507 (11)
H400.48350.71000.33560.061*
C220.1060 (4)0.66368 (9)0.7023 (3)0.0365 (9)
H220.20030.66240.74930.044*
C240.0135 (4)0.63812 (11)0.8853 (3)0.0492 (10)
H24A0.01840.65680.93730.074*
H24B0.11450.63210.91660.074*
H24C0.04550.61610.88540.074*
C300.2276 (4)0.65675 (11)0.3583 (3)0.0449 (10)
H300.23040.68180.33620.054*
C330.2303 (4)0.78124 (10)0.4498 (4)0.0465 (10)
H330.20170.79870.38700.056*
C280.2806 (4)0.59237 (12)0.3250 (4)0.0511 (11)
H280.31950.57410.28020.061*
C390.3264 (4)0.72109 (11)0.4838 (4)0.0507 (11)
H390.38270.73690.52340.061*
C270.2180 (4)0.58236 (10)0.4235 (3)0.0430 (10)
H270.21620.55730.44600.052*
C610.4167 (3)0.57468 (8)0.8922 (3)0.0272 (8)
C520.9188 (4)0.54378 (10)1.1853 (3)0.0393 (9)
H520.99120.53261.24410.047*
C540.7219 (4)0.53955 (9)1.0089 (3)0.0342 (9)
H540.66270.52460.95060.041*
C660.3161 (4)0.56711 (9)0.7820 (3)0.0323 (8)
H660.34290.57250.70610.039*
C500.7902 (4)0.59831 (10)1.0974 (3)0.0360 (9)
H500.77880.62411.09980.043*
C430.5464 (4)0.64126 (9)0.9268 (3)0.0330 (9)
C510.8976 (4)0.58191 (10)1.1854 (3)0.0421 (10)
H510.95580.59671.24500.051*
C550.6257 (3)0.59416 (9)0.7602 (3)0.0335 (9)
C490.6979 (3)0.57829 (9)1.0051 (3)0.0257 (8)
C560.7273 (4)0.56889 (10)0.7309 (3)0.0389 (9)
H560.77130.55250.79240.047*
C630.2317 (4)0.54926 (9)1.0030 (3)0.0359 (9)
H630.20480.54321.07830.043*
C620.3697 (4)0.56437 (9)1.0006 (3)0.0322 (8)
H620.43380.56771.07580.039*
C600.5663 (4)0.61744 (11)0.6606 (4)0.0464 (10)
H600.49680.63500.67350.056*
C530.8306 (4)0.52248 (10)1.0962 (3)0.0360 (9)
H530.84370.49671.09440.043*
C480.6406 (4)0.66971 (10)0.8992 (4)0.0547 (12)
H480.71710.66320.85920.066*
C440.4331 (4)0.65409 (10)0.9846 (3)0.0412 (10)
H440.36710.63671.00540.049*
C590.6042 (5)0.61595 (13)0.5444 (4)0.0584 (12)
H590.56020.63220.48210.070*
C570.7675 (4)0.56666 (12)0.6137 (4)0.0511 (11)
H570.83550.54890.59910.061*
C580.7067 (5)0.59057 (13)0.5208 (4)0.0535 (12)
H580.73420.58970.44350.064*
C650.1788 (4)0.55201 (9)0.7824 (4)0.0389 (9)
H650.11520.54770.70750.047*
B20.5727 (4)0.59688 (10)0.8955 (4)0.0293 (9)
C640.1356 (4)0.54337 (9)0.8924 (4)0.0431 (10)
H640.04260.53370.89240.052*
C460.5112 (6)0.71806 (12)0.9865 (4)0.0648 (14)
H460.50070.74301.00730.078*
C450.4144 (5)0.69151 (11)1.0126 (4)0.0557 (12)
H450.33580.69861.04920.067*
C470.6238 (5)0.70708 (11)0.9292 (5)0.0684 (14)
H470.68960.72480.91010.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0277 (5)0.0279 (5)0.0242 (5)0.0009 (4)0.0031 (4)0.0011 (4)
B10.031 (2)0.026 (2)0.020 (2)0.0004 (17)0.0006 (17)0.0013 (16)
C720.034 (2)0.033 (2)0.0247 (19)0.0045 (16)0.0052 (16)0.0060 (15)
C170.035 (2)0.034 (2)0.034 (2)0.0030 (17)0.0053 (17)0.0023 (17)
C790.0202 (17)0.0269 (18)0.031 (2)0.0013 (14)0.0073 (15)0.0021 (15)
C20.032 (2)0.0285 (19)0.032 (2)0.0037 (15)0.0003 (17)0.0031 (15)
C40.0269 (19)0.0253 (17)0.0236 (19)0.0021 (15)0.0026 (15)0.0024 (14)
C180.048 (2)0.027 (2)0.042 (2)0.0048 (18)0.0020 (19)0.0076 (17)
C730.0252 (19)0.0228 (18)0.0269 (19)0.0067 (14)0.0026 (15)0.0020 (14)
C670.0287 (19)0.0239 (18)0.0247 (19)0.0046 (14)0.0031 (15)0.0025 (15)
C210.032 (2)0.033 (2)0.025 (2)0.0005 (16)0.0026 (16)0.0017 (15)
C160.0218 (17)0.0280 (18)0.027 (2)0.0023 (14)0.0056 (15)0.0015 (15)
C110.035 (2)0.042 (2)0.037 (2)0.0031 (17)0.0017 (17)0.0072 (17)
C100.0266 (19)0.032 (2)0.0239 (19)0.0042 (15)0.0007 (15)0.0057 (15)
C50.031 (2)0.038 (2)0.033 (2)0.0032 (17)0.0121 (16)0.0027 (17)
C750.046 (2)0.042 (2)0.031 (2)0.0094 (19)0.0120 (18)0.0022 (17)
C90.032 (2)0.0237 (18)0.035 (2)0.0003 (15)0.0079 (17)0.0025 (16)
C680.031 (2)0.039 (2)0.030 (2)0.0005 (17)0.0008 (16)0.0018 (16)
C800.033 (2)0.030 (2)0.029 (2)0.0030 (16)0.0044 (16)0.0008 (15)
C870.049 (3)0.057 (3)0.031 (2)0.001 (2)0.0119 (19)0.007 (2)
C140.038 (2)0.052 (2)0.036 (2)0.0099 (19)0.0106 (18)0.0074 (19)
C10.030 (2)0.0288 (19)0.030 (2)0.0032 (16)0.0027 (16)0.0011 (16)
C830.061 (3)0.030 (2)0.043 (2)0.0023 (19)0.011 (2)0.0076 (18)
C700.0238 (19)0.044 (2)0.049 (2)0.0023 (17)0.0074 (18)0.0164 (19)
C840.038 (2)0.031 (2)0.033 (2)0.0025 (16)0.0015 (17)0.0002 (16)
C770.038 (2)0.033 (2)0.031 (2)0.0114 (17)0.0046 (18)0.0031 (17)
C740.030 (2)0.033 (2)0.033 (2)0.0004 (16)0.0047 (17)0.0003 (16)
C60.037 (2)0.030 (2)0.038 (2)0.0052 (16)0.0014 (18)0.0045 (17)
C850.0246 (18)0.0309 (19)0.0216 (18)0.0014 (15)0.0014 (15)0.0051 (15)
C30.039 (2)0.037 (2)0.038 (2)0.0008 (17)0.0118 (18)0.0001 (17)
C810.035 (2)0.045 (2)0.037 (2)0.0111 (18)0.0035 (17)0.0107 (19)
C190.039 (2)0.028 (2)0.047 (2)0.0123 (17)0.0117 (19)0.0083 (18)
C130.029 (2)0.061 (3)0.043 (3)0.003 (2)0.0015 (19)0.017 (2)
C690.033 (2)0.042 (2)0.038 (2)0.0047 (17)0.0073 (18)0.0022 (17)
C900.043 (2)0.034 (2)0.030 (2)0.0001 (17)0.0080 (17)0.0016 (16)
C820.044 (2)0.034 (2)0.048 (3)0.0133 (18)0.015 (2)0.0103 (19)
C150.034 (2)0.043 (2)0.026 (2)0.0069 (17)0.0032 (16)0.0048 (17)
C780.029 (2)0.040 (2)0.026 (2)0.0026 (16)0.0080 (16)0.0031 (16)
C80.045 (2)0.037 (2)0.033 (2)0.0038 (18)0.0195 (18)0.0007 (17)
C880.067 (3)0.051 (3)0.025 (2)0.004 (2)0.009 (2)0.0064 (18)
C890.056 (3)0.037 (2)0.036 (2)0.0000 (19)0.002 (2)0.0040 (18)
C200.034 (2)0.039 (2)0.036 (2)0.0033 (17)0.0021 (17)0.0086 (18)
C70.049 (2)0.034 (2)0.028 (2)0.0055 (18)0.0008 (18)0.0053 (16)
C860.0281 (19)0.033 (2)0.031 (2)0.0005 (16)0.0023 (16)0.0054 (16)
C760.057 (3)0.035 (2)0.023 (2)0.0019 (18)0.0044 (19)0.0067 (16)
C710.029 (2)0.049 (2)0.034 (2)0.0108 (18)0.0059 (17)0.0131 (18)
C120.033 (2)0.065 (3)0.044 (2)0.011 (2)0.0089 (19)0.002 (2)
P20.0279 (5)0.0312 (5)0.0305 (5)0.0010 (4)0.0041 (4)0.0007 (4)
C250.0248 (19)0.038 (2)0.028 (2)0.0019 (16)0.0026 (15)0.0018 (16)
C370.0265 (18)0.027 (2)0.036 (2)0.0002 (15)0.0057 (16)0.0015 (16)
C310.0210 (18)0.0307 (19)0.035 (2)0.0038 (15)0.0072 (15)0.0030 (16)
C350.028 (2)0.047 (2)0.041 (2)0.0085 (18)0.0077 (17)0.0137 (19)
C360.030 (2)0.037 (2)0.031 (2)0.0030 (16)0.0076 (16)0.0026 (16)
C260.040 (2)0.041 (2)0.030 (2)0.0040 (18)0.0012 (17)0.0020 (17)
C320.038 (2)0.037 (2)0.041 (2)0.0008 (18)0.0032 (18)0.0007 (18)
C230.036 (2)0.048 (2)0.033 (2)0.0026 (18)0.0068 (18)0.0014 (18)
C420.031 (2)0.033 (2)0.041 (2)0.0024 (16)0.0033 (17)0.0003 (17)
C340.038 (2)0.040 (2)0.054 (3)0.0076 (18)0.015 (2)0.005 (2)
C410.038 (2)0.046 (2)0.054 (3)0.008 (2)0.006 (2)0.008 (2)
C380.042 (2)0.039 (2)0.046 (2)0.0017 (18)0.014 (2)0.0011 (18)
C290.048 (3)0.072 (3)0.046 (3)0.001 (2)0.020 (2)0.011 (2)
C400.021 (2)0.053 (3)0.076 (3)0.0001 (19)0.005 (2)0.022 (2)
C220.030 (2)0.040 (2)0.039 (2)0.0026 (17)0.0044 (17)0.0001 (17)
C240.043 (2)0.058 (3)0.048 (3)0.000 (2)0.013 (2)0.005 (2)
C300.048 (2)0.040 (2)0.050 (3)0.0008 (19)0.018 (2)0.0051 (19)
C330.044 (2)0.043 (2)0.053 (3)0.003 (2)0.013 (2)0.0112 (19)
C280.054 (3)0.049 (3)0.048 (3)0.015 (2)0.003 (2)0.010 (2)
C390.040 (3)0.047 (2)0.072 (3)0.012 (2)0.026 (2)0.007 (2)
C270.052 (3)0.036 (2)0.036 (2)0.0117 (19)0.005 (2)0.0047 (18)
C610.0252 (18)0.0180 (17)0.038 (2)0.0001 (14)0.0045 (16)0.0008 (15)
C520.031 (2)0.051 (2)0.034 (2)0.0045 (18)0.0019 (17)0.0094 (18)
C540.030 (2)0.035 (2)0.035 (2)0.0058 (16)0.0012 (17)0.0032 (17)
C660.033 (2)0.0299 (19)0.033 (2)0.0006 (16)0.0036 (16)0.0003 (16)
C500.034 (2)0.038 (2)0.035 (2)0.0038 (17)0.0039 (17)0.0023 (17)
C430.0250 (19)0.032 (2)0.037 (2)0.0024 (16)0.0074 (16)0.0071 (16)
C510.039 (2)0.050 (2)0.032 (2)0.0047 (18)0.0082 (18)0.0082 (18)
C550.0256 (19)0.038 (2)0.034 (2)0.0118 (16)0.0036 (16)0.0086 (17)
C490.0208 (17)0.0309 (19)0.0266 (19)0.0031 (14)0.0073 (15)0.0010 (15)
C560.038 (2)0.043 (2)0.034 (2)0.0038 (18)0.0028 (18)0.0019 (17)
C630.035 (2)0.028 (2)0.049 (3)0.0037 (16)0.0183 (19)0.0032 (17)
C620.032 (2)0.0278 (19)0.037 (2)0.0014 (15)0.0070 (17)0.0012 (16)
C600.037 (2)0.059 (3)0.041 (3)0.0031 (19)0.0003 (19)0.015 (2)
C530.034 (2)0.033 (2)0.043 (2)0.0011 (17)0.0120 (18)0.0086 (17)
C480.040 (2)0.038 (2)0.084 (3)0.0065 (18)0.008 (2)0.015 (2)
C440.047 (2)0.034 (2)0.038 (2)0.0004 (18)0.0060 (19)0.0025 (17)
C590.059 (3)0.074 (3)0.038 (3)0.016 (3)0.001 (2)0.024 (2)
C570.045 (2)0.067 (3)0.042 (3)0.015 (2)0.009 (2)0.014 (2)
C580.061 (3)0.072 (3)0.027 (2)0.031 (2)0.007 (2)0.001 (2)
C650.029 (2)0.030 (2)0.052 (3)0.0008 (16)0.0078 (19)0.0001 (18)
B20.027 (2)0.026 (2)0.034 (2)0.0027 (17)0.0029 (18)0.0035 (18)
C640.025 (2)0.031 (2)0.074 (3)0.0004 (16)0.012 (2)0.004 (2)
C460.076 (4)0.033 (3)0.070 (3)0.006 (3)0.024 (3)0.005 (2)
C450.061 (3)0.040 (3)0.060 (3)0.009 (2)0.004 (2)0.010 (2)
C470.066 (3)0.030 (3)0.099 (4)0.013 (2)0.010 (3)0.018 (2)
Geometric parameters (Å, º) top
P1—C41.792 (3)P2—C251.809 (3)
P1—C161.791 (3)P2—C371.792 (3)
P1—C101.798 (3)P2—C311.797 (3)
P1—C11.767 (3)P2—C221.771 (4)
B1—C791.648 (5)C25—C261.379 (5)
B1—C731.655 (5)C25—C301.386 (5)
B1—C671.650 (5)C37—C421.389 (4)
B1—C851.647 (5)C37—C381.394 (4)
C72—H720.9300C31—C361.403 (4)
C72—C671.403 (4)C31—C321.380 (4)
C72—C711.391 (4)C35—H350.9300
C17—H170.9300C35—C361.387 (5)
C17—C181.380 (4)C35—C341.374 (5)
C17—C161.397 (4)C36—H360.9300
C79—C801.403 (4)C26—H260.9300
C79—C841.404 (4)C26—C271.385 (5)
C2—H20.9300C32—H320.9300
C2—C11.324 (5)C32—C331.387 (5)
C2—C31.481 (4)C23—H230.9300
C4—C51.398 (4)C23—C221.309 (5)
C4—C91.386 (4)C23—C241.497 (5)
C18—H180.9300C42—H420.9300
C18—C191.387 (5)C42—C411.382 (4)
C73—C741.390 (4)C34—H340.9300
C73—C781.413 (4)C34—C331.372 (5)
C67—C681.407 (4)C41—H410.9300
C21—H210.9300C41—C401.380 (5)
C21—C161.386 (4)C38—H380.9300
C21—C201.379 (4)C38—C391.379 (5)
C11—H110.9300C29—H290.9300
C11—C101.394 (4)C29—C301.393 (5)
C11—C121.385 (5)C29—C281.380 (5)
C10—C151.384 (4)C40—H400.9300
C5—H50.9300C40—C391.381 (5)
C5—C61.390 (4)C22—H220.9300
C75—H750.9300C24—H24A0.9600
C75—C741.393 (4)C24—H24B0.9600
C75—C761.375 (5)C24—H24C0.9600
C9—H90.9300C30—H300.9300
C9—C81.396 (4)C33—H330.9300
C68—H680.9300C28—H280.9300
C68—C691.395 (4)C28—C271.364 (5)
C80—H800.9300C39—H390.9300
C80—C811.389 (4)C27—H270.9300
C87—H870.9300C61—C661.408 (4)
C87—C881.360 (5)C61—C621.389 (4)
C87—C861.396 (5)C61—B21.644 (5)
C14—H140.9300C52—H520.9300
C14—C131.373 (5)C52—C511.378 (5)
C14—C151.377 (4)C52—C531.380 (5)
C1—H10.9300C54—H540.9300
C83—H830.9300C54—C491.403 (4)
C83—C841.392 (5)C54—C531.394 (4)
C83—C821.374 (5)C66—H660.9300
C70—H700.9300C66—C651.384 (4)
C70—C691.381 (5)C50—H500.9300
C70—C711.382 (5)C50—C511.381 (4)
C84—H840.9300C50—C491.395 (4)
C77—H770.9300C43—C481.410 (5)
C77—C781.385 (4)C43—C441.401 (5)
C77—C761.381 (5)C43—B21.652 (5)
C74—H740.9300C51—H510.9300
C6—H60.9300C55—C561.386 (5)
C6—C71.375 (5)C55—C601.401 (4)
C85—C901.413 (4)C55—B21.649 (5)
C85—C861.374 (4)C49—B21.648 (5)
C3—H3A0.9600C56—H560.9300
C3—H3B0.9600C56—C571.404 (5)
C3—H3C0.9600C63—H630.9300
C81—H810.9300C63—C621.394 (4)
C81—C821.374 (5)C63—C641.380 (5)
C19—H190.9300C62—H620.9300
C19—C201.377 (5)C60—H600.9300
C13—H130.9300C60—C591.383 (5)
C13—C121.358 (5)C53—H530.9300
C69—H690.9300C48—H480.9300
C90—H900.9300C48—C471.392 (5)
C90—C891.384 (5)C44—H440.9300
C82—H820.9300C44—C451.392 (5)
C15—H150.9300C59—H590.9300
C78—H780.9300C59—C581.374 (6)
C8—H80.9300C57—H570.9300
C8—C71.384 (5)C57—C581.367 (5)
C88—H880.9300C58—H580.9300
C88—C891.394 (5)C65—H650.9300
C89—H890.9300C65—C641.374 (5)
C20—H200.9300C64—H640.9300
C7—H70.9300C46—H460.9300
C86—H860.9300C46—C451.373 (6)
C76—H760.9300C46—C471.372 (6)
C71—H710.9300C45—H450.9300
C12—H120.9300C47—H470.9300
C4—P1—C10109.76 (15)C37—P2—C25109.67 (15)
C16—P1—C4109.36 (14)C37—P2—C31108.98 (14)
C16—P1—C10107.26 (14)C31—P2—C25108.67 (16)
C1—P1—C4107.97 (15)C22—P2—C25107.82 (16)
C1—P1—C16111.24 (16)C22—P2—C37111.71 (17)
C1—P1—C10111.25 (15)C22—P2—C31109.93 (16)
C79—B1—C73109.3 (2)C26—C25—P2118.5 (3)
C79—B1—C67107.4 (2)C26—C25—C30120.9 (3)
C67—B1—C73111.3 (3)C30—C25—P2120.7 (3)
C85—B1—C79111.1 (3)C42—C37—P2120.9 (3)
C85—B1—C73106.7 (3)C42—C37—C38119.8 (3)
C85—B1—C67111.0 (2)C38—C37—P2119.2 (3)
C67—C72—H72118.8C36—C31—P2120.0 (3)
C71—C72—H72118.8C32—C31—P2119.7 (3)
C71—C72—C67122.4 (3)C32—C31—C36120.2 (3)
C18—C17—H17120.0C36—C35—H35119.5
C18—C17—C16120.0 (3)C34—C35—H35119.5
C16—C17—H17120.0C34—C35—C36121.0 (3)
C80—C79—B1125.5 (3)C31—C36—H36120.7
C80—C79—C84114.3 (3)C35—C36—C31118.7 (3)
C84—C79—B1120.3 (3)C35—C36—H36120.7
C1—C2—H2117.1C25—C26—H26120.5
C1—C2—C3125.7 (3)C25—C26—C27119.0 (4)
C3—C2—H2117.1C27—C26—H26120.5
C5—C4—P1118.3 (3)C31—C32—H32120.2
C9—C4—P1122.1 (3)C31—C32—C33119.5 (3)
C9—C4—C5119.6 (3)C33—C32—H32120.2
C17—C18—H18119.7C22—C23—H23117.2
C17—C18—C19120.5 (3)C22—C23—C24125.5 (3)
C19—C18—H18119.7C24—C23—H23117.2
C74—C73—B1126.3 (3)C37—C42—H42119.9
C74—C73—C78115.0 (3)C41—C42—C37120.2 (3)
C78—C73—B1118.6 (3)C41—C42—H42119.9
C72—C67—B1125.4 (3)C35—C34—H34120.1
C72—C67—C68114.6 (3)C33—C34—C35119.7 (3)
C68—C67—B1120.0 (3)C33—C34—H34120.1
C16—C21—H21119.4C42—C41—H41120.3
C20—C21—H21119.4C40—C41—C42119.4 (4)
C20—C21—C16121.3 (3)C40—C41—H41120.3
C17—C16—P1119.2 (2)C37—C38—H38120.2
C21—C16—P1122.2 (2)C39—C38—C37119.7 (4)
C21—C16—C17118.6 (3)C39—C38—H38120.2
C10—C11—H11120.6C30—C29—H29120.1
C12—C11—H11120.6C28—C29—H29120.1
C12—C11—C10118.8 (3)C28—C29—C30119.7 (4)
C11—C10—P1120.6 (3)C41—C40—H40119.5
C15—C10—P1119.5 (2)C41—C40—C39120.9 (4)
C15—C10—C11119.9 (3)C39—C40—H40119.5
C4—C5—H5119.9P2—C22—H22117.2
C6—C5—C4120.2 (3)C23—C22—P2125.6 (3)
C6—C5—H5119.9C23—C22—H22117.2
C74—C75—H75119.8C23—C24—H24A109.5
C76—C75—H75119.8C23—C24—H24B109.5
C76—C75—C74120.4 (3)C23—C24—H24C109.5
C4—C9—H9120.3H24A—C24—H24B109.5
C4—C9—C8119.4 (3)H24A—C24—H24C109.5
C8—C9—H9120.3H24B—C24—H24C109.5
C67—C68—H68118.2C25—C30—C29119.2 (4)
C69—C68—C67123.6 (3)C25—C30—H30120.4
C69—C68—H68118.2C29—C30—H30120.4
C79—C80—H80118.5C32—C33—H33119.6
C81—C80—C79123.0 (3)C34—C33—C32120.8 (4)
C81—C80—H80118.5C34—C33—H33119.6
C88—C87—H87119.4C29—C28—H28119.8
C88—C87—C86121.2 (4)C27—C28—C29120.4 (4)
C86—C87—H87119.4C27—C28—H28119.8
C13—C14—H14119.7C38—C39—C40119.9 (4)
C13—C14—C15120.5 (4)C38—C39—H39120.0
C15—C14—H14119.7C40—C39—H39120.0
P1—C1—H1117.2C26—C27—H27119.6
C2—C1—P1125.6 (3)C28—C27—C26120.8 (4)
C2—C1—H1117.2C28—C27—H27119.6
C84—C83—H83119.8C66—C61—B2123.5 (3)
C82—C83—H83119.8C62—C61—C66114.7 (3)
C82—C83—C84120.4 (3)C62—C61—B2121.6 (3)
C69—C70—H70120.6C51—C52—H52120.6
C69—C70—C71118.8 (3)C51—C52—C53118.8 (3)
C71—C70—H70120.6C53—C52—H52120.6
C79—C84—H84118.5C49—C54—H54118.5
C83—C84—C79123.0 (3)C53—C54—H54118.5
C83—C84—H84118.5C53—C54—C49122.9 (3)
C78—C77—H77119.9C61—C66—H66118.8
C76—C77—H77119.9C65—C66—C61122.4 (3)
C76—C77—C78120.1 (3)C65—C66—H66118.8
C73—C74—C75122.8 (3)C51—C50—H50118.2
C73—C74—H74118.6C51—C50—C49123.6 (3)
C75—C74—H74118.6C49—C50—H50118.2
C5—C6—H6119.9C48—C43—B2121.9 (3)
C7—C6—C5120.1 (3)C44—C43—C48114.0 (3)
C7—C6—H6119.9C44—C43—B2124.1 (3)
C90—C85—B1118.3 (3)C52—C51—C50120.3 (3)
C86—C85—B1126.5 (3)C52—C51—H51119.9
C86—C85—C90115.2 (3)C50—C51—H51119.9
C2—C3—H3A109.5C56—C55—C60113.2 (3)
C2—C3—H3B109.5C56—C55—B2125.2 (3)
C2—C3—H3C109.5C60—C55—B2121.6 (3)
H3A—C3—H3B109.5C54—C49—B2120.4 (3)
H3A—C3—H3C109.5C50—C49—C54114.4 (3)
H3B—C3—H3C109.5C50—C49—B2125.1 (3)
C80—C81—H81119.7C55—C56—H56118.1
C82—C81—C80120.5 (3)C55—C56—C57123.8 (4)
C82—C81—H81119.7C57—C56—H56118.1
C18—C19—H19120.1C62—C63—H63120.4
C20—C19—C18119.7 (3)C64—C63—H63120.4
C20—C19—H19120.1C64—C63—C62119.2 (3)
C14—C13—H13120.0C61—C62—C63123.7 (3)
C12—C13—C14119.9 (4)C61—C62—H62118.1
C12—C13—H13120.0C63—C62—H62118.1
C68—C69—H69120.2C55—C60—H60117.9
C70—C69—C68119.6 (3)C59—C60—C55124.2 (4)
C70—C69—H69120.2C59—C60—H60117.9
C85—C90—H90118.5C52—C53—C54120.0 (3)
C89—C90—C85123.0 (3)C52—C53—H53120.0
C89—C90—H90118.5C54—C53—H53120.0
C83—C82—C81118.8 (3)C43—C48—H48118.6
C83—C82—H82120.6C47—C48—C43122.8 (4)
C81—C82—H82120.6C47—C48—H48118.6
C10—C15—H15120.2C43—C44—H44118.3
C14—C15—C10119.7 (3)C45—C44—C43123.3 (4)
C14—C15—H15120.2C45—C44—H44118.3
C73—C78—H78118.7C60—C59—H59119.9
C77—C78—C73122.6 (3)C58—C59—C60120.1 (4)
C77—C78—H78118.7C58—C59—H59119.9
C9—C8—H8119.6C56—C57—H57120.0
C7—C8—C9120.7 (3)C58—C57—C56120.1 (4)
C7—C8—H8119.6C58—C57—H57120.0
C87—C88—H88120.7C59—C58—H58120.7
C87—C88—C89118.7 (4)C57—C58—C59118.5 (4)
C89—C88—H88120.7C57—C58—H58120.7
C90—C89—C88119.5 (3)C66—C65—H65119.7
C90—C89—H89120.3C64—C65—C66120.6 (3)
C88—C89—H89120.3C64—C65—H65119.7
C21—C20—H20120.1C61—B2—C43107.8 (3)
C19—C20—C21119.9 (3)C61—B2—C55111.1 (3)
C19—C20—H20120.1C61—B2—C49108.6 (3)
C6—C7—C8119.9 (3)C55—B2—C43108.9 (3)
C6—C7—H7120.1C49—B2—C43110.4 (3)
C8—C7—H7120.1C49—B2—C55110.1 (3)
C87—C86—H86118.8C63—C64—H64120.3
C85—C86—C87122.5 (3)C65—C64—C63119.3 (3)
C85—C86—H86118.8C65—C64—H64120.3
C75—C76—C77119.0 (3)C45—C46—H46120.7
C75—C76—H76120.5C47—C46—H46120.7
C77—C76—H76120.5C47—C46—C45118.7 (4)
C72—C71—H71119.5C44—C45—H45119.8
C70—C71—C72121.0 (3)C46—C45—C44120.4 (4)
C70—C71—H71119.5C46—C45—H45119.8
C11—C12—H12119.4C48—C47—H47119.6
C13—C12—C11121.2 (4)C46—C47—C48120.7 (4)
C13—C12—H12119.4C46—C47—H47119.6

Experimental details

Crystal data
Chemical formulaC21H20P+·C24H20B
Mr622.55
Crystal system, space groupMonoclinic, P21
Temperature (K)180
a, b, c (Å)9.2752 (4), 35.7838 (15), 10.9515 (5)
β (°) 100.721 (4)
V3)3571.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.43 × 0.18 × 0.17
Data collection
DiffractometerAgilent Xcalibur, Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2014)
Tmin, Tmax0.958, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
24267, 12797, 9444
Rint0.038
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.105, 1.01
No. of reflections12797
No. of parameters849
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.23
Absolute structureFlack (1983)
Absolute structure parameter0.02 (7)

Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OlEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

 

Acknowledgements

The authors are grateful to the Department of Chemistry and Physics of FGCU for the financial support of this work. They also acknowledge the National Science Foundation for their generous support (NSF-CAREER grant to RES, CHE-0846680).

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationBellina, F., Chiappe, C. & Lessi, M. (2012). Green Chem. 14, 148–155.  Web of Science CrossRef CAS Google Scholar
First citationChowdhury, S., Mohan, R. S. & Scott, J. L. (2007). Tetrahedron, 63, 2363–2389.  Web of Science CrossRef CAS Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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