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

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COMMUNICATIONS
ISSN: 2056-9890

Benzyl­tri­phenyl­phospho­nium perchlorate

aCollege of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen, Hubei 448000, People's Republic of China
*Correspondence e-mail: jclgllw@126.com

(Received 19 May 2011; accepted 6 June 2011; online 11 June 2011)

The asymmetric unit of the title compound, C25H22P+·ClO4, contains two independent cations and two independent anions. The closest inter­molecular contact is a weak inter­molecular C—H⋯π(arene) inter­action.

Related literature

For the applications of large cations and anions, see: Fox et al. (2004[Fox, D. C., Fiedler, A. T., Halfen, H. L., Brunold, T. C. & Halfen, J. A. (2004). J. Am. Chem. Soc. 126, 7627-7638.]); Huynh et al. (2000[Huynh, M. H. V., El-Samanody, E.-S., Demadis, K. D., White, P. S. & Meyer, T. J. (2000). Inorg. Chem. 39, 3075-3085.]). For related structures, see: Zhang et al. (2010[Zhang, D. P., Zhang, L. F., Chen, Y. T., Wang, H. L., Ni, Z. H., Wernsdorfer, W. & Jiang, J. Z. (2010). Chem. Commun. 46, 3550-3552.]); Fischer & Wiebelhaus (1997[Fischer, A. & Wiebelhaus, D. (1997). Z. Krist. New Cryst. Struct. 212, 335-336.]); Hubner et al. (1997[Hubner, J., Wulff-Molder, D., Vogt, H. & Meisel, M. (1997). Z. Naturforsch. Teil B, 52, 1321-1325.]); Skapski & Stephens (1974[Skapski, A. C. & Stephens, F. A. (1974). J. Cryst. Mol. Struct. 4, 77-85.]).

[Scheme 1]

Experimental

Crystal data
  • C25H22P+·ClO4

  • Mr = 452.85

  • Triclinic, [P \overline 1]

  • a = 10.096 (1) Å

  • b = 13.8967 (13) Å

  • c = 18.2577 (17) Å

  • α = 69.765 (2)°

  • β = 84.826 (2)°

  • γ = 73.195 (2)°

  • V = 2300.7 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.31 × 0.29 × 0.24 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.923, Tmax = 0.939

  • 11362 measured reflections

  • 7992 independent reflections

  • 5675 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.185

  • S = 1.02

  • 7992 reflections

  • 559 parameters

  • H-atom parameters constrained

  • Δρmax = 0.95 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C27–C32 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯Cgi 0.93 2.83 3.757 (9) 176
Symmetry code: (i) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison,Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Large cations and anions are often employed to act as counter ions in coordination chemistry (Fox et al., 2004; Huynh et al., 2000). Here, we report the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. The P atoms are bonded in slightly distorted tetrahedral environments. The P—C bond distances are comparable to those in related componds containing Ph3(PhCH2)P+ cations (Zhang, et al., 2010; Fischer & Wiebelhaus, 1997; Hubner, et al., 1997; Skapski & Stephens, 1974). The closest intermolecular contact is a weak intermolecular C—H···π(arene) interaction. .

Related literature top

For the applications of large cations and anions, see: Fox et al. (2004); Huynh et al. (2000). For related structures, see: Zhang et al. (2010); Fischer & Wiebelhaus (1997); Hubner et al. (1997); Skapski & Stephens (1974).

Experimental top

The title compound was synthesized by reacting [Ph3(PhCH2)]Cl and NaClO4.H2O(1:1, molar ratio) in ethanol. The mixture was stirred for for about 10 min at room temperature, then filtered, and then the filtrate was allowed to slowly evaporate undisturbed for ten days to afford colorless crystals suitable for X-ray diffraction with a yield about 85%.

Refinement top

H atoms were placed using the HFIX commands in SHELXL-97 (Sheldrick, 2008) with C—H distances of 0.93 and 0.97 Å and were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Benzyltriphenylphosphonium perchlorate top
Crystal data top
C25H22P+·ClO4Z = 4
Mr = 452.85F(000) = 944
Triclinic, P1Dx = 1.307 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.096 (1) ÅCell parameters from 2162 reflections
b = 13.8967 (13) Åθ = 2.4–26.7°
c = 18.2577 (17) ŵ = 0.26 mm1
α = 69.765 (2)°T = 293 K
β = 84.826 (2)°Block, colourless
γ = 73.195 (2)°0.31 × 0.29 × 0.24 mm
V = 2300.7 (4) Å3
Data collection top
Bruker APEXII
diffractometer
7992 independent reflections
Radiation source: fine-focus sealed tube5675 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ϕ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1210
Tmin = 0.923, Tmax = 0.939k = 1616
11362 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.099P)2 + 1.1578P]
where P = (Fo2 + 2Fc2)/3
7992 reflections(Δ/σ)max < 0.001
559 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C25H22P+·ClO4γ = 73.195 (2)°
Mr = 452.85V = 2300.7 (4) Å3
Triclinic, P1Z = 4
a = 10.096 (1) ÅMo Kα radiation
b = 13.8967 (13) ŵ = 0.26 mm1
c = 18.2577 (17) ÅT = 293 K
α = 69.765 (2)°0.31 × 0.29 × 0.24 mm
β = 84.826 (2)°
Data collection top
Bruker APEXII
diffractometer
7992 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5675 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.939Rint = 0.019
11362 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.185H-atom parameters constrained
S = 1.02Δρmax = 0.95 e Å3
7992 reflectionsΔρmin = 0.36 e Å3
559 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
xyzUiso*/Ueq
Cl10.28935 (10)0.87956 (7)0.37917 (6)0.0715 (3)
Cl20.64016 (9)0.63901 (7)0.12239 (5)0.0618 (3)
P10.78887 (9)0.70653 (7)0.35120 (5)0.0504 (2)
P20.15337 (8)0.25542 (6)0.15262 (5)0.0455 (2)
O10.2871 (6)0.8624 (3)0.4591 (2)0.160 (2)
O20.3355 (3)0.9704 (2)0.3405 (2)0.1007 (10)
O30.1552 (4)0.8940 (3)0.3548 (3)0.1497 (19)
O40.5282 (5)0.6397 (6)0.1692 (2)0.186 (3)
O50.6241 (5)0.6110 (5)0.0585 (3)0.1600 (19)
O60.6364 (6)0.7454 (3)0.0897 (4)0.190 (2)
O70.7664 (4)0.5984 (5)0.1599 (3)0.190 (3)
O80.3807 (3)0.7868 (2)0.3676 (2)0.0951 (9)
C10.6743 (3)0.7966 (3)0.27025 (19)0.0552 (8)
H1A0.66670.75780.23650.066*
H1B0.58300.81980.29060.066*
C20.7194 (3)0.8937 (3)0.2221 (2)0.0540 (8)
C30.7893 (4)0.8939 (4)0.1541 (2)0.0749 (11)
H30.81340.83310.13980.090*
C40.8242 (6)0.9860 (6)0.1063 (3)0.122 (2)
H40.87210.98650.06030.147*
C50.7882 (7)1.0740 (6)0.1274 (6)0.152 (4)
H50.81011.13540.09500.183*
C60.7216 (7)1.0744 (4)0.1938 (5)0.129 (2)
H60.69951.13570.20750.155*
C70.6850 (5)0.9851 (3)0.2426 (3)0.0867 (13)
H70.63790.98630.28860.104*
C80.7901 (4)0.7712 (3)0.42106 (19)0.0606 (9)
C90.9078 (5)0.7808 (4)0.4455 (2)0.0905 (14)
H90.99370.75070.42770.109*
C100.8984 (8)0.8365 (6)0.4974 (3)0.130 (2)
H100.97810.84490.51330.156*
C110.7763 (10)0.8775 (6)0.5244 (3)0.133 (2)
H110.77190.91340.55950.160*
C120.6574 (8)0.8679 (6)0.5014 (3)0.138 (3)
H120.57260.89740.52050.166*
C130.6636 (5)0.8135 (5)0.4492 (3)0.1033 (17)
H130.58320.80600.43360.124*
C140.9621 (3)0.6633 (3)0.31777 (19)0.0557 (8)
C151.0440 (4)0.7335 (3)0.2902 (2)0.0623 (9)
H151.00870.80410.28800.075*
C161.1773 (4)0.6984 (4)0.2661 (2)0.0709 (10)
H161.23300.74470.24950.085*
C171.2275 (4)0.5957 (4)0.2666 (2)0.0825 (12)
H171.31680.57270.24940.099*
C181.1472 (5)0.5264 (4)0.2923 (3)0.0894 (13)
H181.18230.45660.29260.107*
C191.0149 (4)0.5594 (3)0.3177 (3)0.0760 (11)
H190.96080.51200.33490.091*
C200.7226 (3)0.5925 (3)0.39688 (19)0.0554 (8)
C210.7725 (4)0.5226 (4)0.4711 (2)0.0810 (12)
H210.83670.53600.49700.097*
C220.7246 (5)0.4330 (4)0.5054 (3)0.0917 (15)
H220.75710.38620.55470.110*
C230.6308 (5)0.4131 (3)0.4677 (3)0.0820 (13)
H230.60060.35230.49080.098*
C240.5816 (4)0.4814 (3)0.3967 (2)0.0714 (10)
H240.51610.46790.37170.086*
C250.6269 (4)0.5711 (3)0.3606 (2)0.0590 (8)
H250.59250.61710.31150.071*
C260.0749 (4)0.3622 (3)0.06520 (19)0.0562 (8)
H26A0.03600.42680.07810.067*
H26B0.14680.37490.02710.067*
C270.0372 (3)0.3416 (2)0.02821 (18)0.0512 (8)
C280.1743 (4)0.3715 (3)0.0479 (2)0.0628 (9)
H280.19900.40190.08700.075*
C290.2753 (4)0.3568 (3)0.0101 (2)0.0731 (11)
H290.36770.37830.02330.088*
C300.2404 (4)0.3103 (3)0.0472 (2)0.0757 (11)
H300.30840.29990.07240.091*
C310.1051 (5)0.2801 (4)0.0662 (2)0.0838 (12)
H310.08090.24960.10520.101*
C320.0035 (4)0.2938 (3)0.0288 (2)0.0698 (10)
H320.08860.27090.04170.084*
C330.2236 (3)0.1339 (2)0.13166 (18)0.0489 (7)
C340.1405 (4)0.0721 (3)0.1291 (2)0.0665 (9)
H340.04620.09280.13870.080*
C350.1983 (5)0.0215 (3)0.1121 (3)0.0847 (12)
H350.14320.06470.11200.102*
C360.3346 (6)0.0497 (4)0.0957 (3)0.0930 (15)
H360.37200.11200.08380.112*
C370.4177 (5)0.0113 (4)0.0964 (3)0.0917 (15)
H370.51120.00940.08500.110*
C380.3631 (4)0.1051 (3)0.1140 (2)0.0705 (10)
H380.41930.14770.11400.085*
C390.2891 (3)0.2915 (3)0.18479 (19)0.0527 (8)
C400.3374 (4)0.3763 (3)0.1383 (2)0.0707 (10)
H400.30000.41590.08860.085*
C410.4405 (4)0.4020 (4)0.1654 (3)0.0766 (11)
H410.47230.45930.13400.092*
C420.4957 (4)0.3453 (4)0.2366 (3)0.0829 (12)
H420.56570.36330.25420.099*
C430.4493 (5)0.2603 (4)0.2841 (3)0.1044 (16)
H430.48780.22130.33360.125*
C440.3452 (5)0.2332 (4)0.2579 (2)0.0835 (12)
H440.31370.17590.28960.100*
C450.0268 (3)0.2423 (2)0.22866 (18)0.0488 (7)
C460.0568 (4)0.3353 (3)0.2398 (2)0.0644 (9)
H460.05010.40170.20650.077*
C470.1488 (4)0.3286 (4)0.3002 (3)0.0777 (12)
H470.20510.39050.30750.093*
C480.1582 (4)0.2316 (4)0.3495 (2)0.0825 (13)
H480.22060.22770.39050.099*
C490.0760 (4)0.1392 (4)0.3391 (2)0.0806 (12)
H490.08380.07330.37260.097*
C500.0186 (4)0.1442 (3)0.2786 (2)0.0649 (9)
H500.07560.08200.27200.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0651 (6)0.0486 (5)0.0899 (7)0.0150 (4)0.0148 (5)0.0140 (5)
Cl20.0601 (5)0.0640 (5)0.0710 (6)0.0234 (4)0.0099 (4)0.0318 (4)
P10.0498 (5)0.0578 (5)0.0429 (4)0.0128 (4)0.0004 (3)0.0176 (4)
P20.0456 (4)0.0445 (4)0.0463 (4)0.0120 (3)0.0011 (3)0.0151 (3)
O10.264 (6)0.110 (3)0.104 (3)0.054 (3)0.062 (3)0.046 (2)
O20.096 (2)0.0658 (18)0.127 (3)0.0368 (16)0.0062 (19)0.0054 (17)
O30.071 (2)0.083 (2)0.282 (6)0.0226 (18)0.009 (3)0.042 (3)
O40.129 (3)0.391 (8)0.104 (3)0.143 (5)0.050 (3)0.118 (4)
O50.181 (4)0.223 (5)0.132 (3)0.067 (4)0.037 (3)0.127 (4)
O60.203 (5)0.078 (3)0.278 (7)0.031 (3)0.013 (5)0.047 (4)
O70.087 (3)0.207 (5)0.190 (5)0.000 (3)0.034 (3)0.015 (4)
O80.091 (2)0.0691 (18)0.115 (2)0.0128 (15)0.0239 (18)0.0320 (17)
C10.057 (2)0.059 (2)0.0480 (18)0.0189 (16)0.0023 (15)0.0130 (15)
C20.0462 (18)0.0493 (18)0.0586 (19)0.0103 (14)0.0053 (15)0.0094 (15)
C30.060 (2)0.094 (3)0.053 (2)0.022 (2)0.0016 (17)0.002 (2)
C40.079 (3)0.145 (6)0.090 (4)0.041 (4)0.006 (3)0.035 (4)
C50.086 (4)0.096 (5)0.205 (9)0.046 (4)0.047 (5)0.064 (5)
C60.102 (4)0.056 (3)0.213 (8)0.024 (3)0.040 (5)0.015 (4)
C70.076 (3)0.063 (3)0.117 (4)0.010 (2)0.011 (2)0.031 (3)
C80.063 (2)0.076 (2)0.0439 (17)0.0122 (18)0.0019 (15)0.0258 (17)
C90.082 (3)0.140 (4)0.073 (3)0.036 (3)0.001 (2)0.059 (3)
C100.153 (6)0.200 (7)0.095 (4)0.084 (5)0.016 (4)0.096 (5)
C110.210 (8)0.136 (5)0.085 (4)0.052 (5)0.008 (5)0.073 (4)
C120.155 (6)0.154 (6)0.094 (4)0.019 (5)0.005 (4)0.079 (4)
C130.082 (3)0.151 (5)0.082 (3)0.000 (3)0.002 (2)0.071 (3)
C140.0532 (19)0.067 (2)0.0485 (18)0.0123 (16)0.0010 (14)0.0246 (16)
C150.060 (2)0.072 (2)0.055 (2)0.0162 (18)0.0025 (16)0.0214 (18)
C160.060 (2)0.096 (3)0.062 (2)0.030 (2)0.0039 (18)0.025 (2)
C170.056 (2)0.114 (4)0.076 (3)0.011 (2)0.008 (2)0.042 (3)
C180.075 (3)0.086 (3)0.114 (4)0.012 (2)0.022 (3)0.055 (3)
C190.069 (2)0.082 (3)0.093 (3)0.027 (2)0.019 (2)0.049 (2)
C200.0523 (19)0.0539 (19)0.0472 (17)0.0061 (15)0.0060 (14)0.0095 (15)
C210.070 (3)0.087 (3)0.062 (2)0.011 (2)0.0063 (19)0.002 (2)
C220.083 (3)0.074 (3)0.069 (3)0.002 (2)0.010 (2)0.018 (2)
C230.083 (3)0.052 (2)0.091 (3)0.013 (2)0.031 (3)0.011 (2)
C240.080 (3)0.055 (2)0.079 (3)0.0220 (19)0.020 (2)0.025 (2)
C250.069 (2)0.0526 (19)0.0527 (19)0.0155 (17)0.0056 (16)0.0166 (16)
C260.065 (2)0.0484 (18)0.0510 (18)0.0173 (16)0.0062 (15)0.0091 (15)
C270.0562 (19)0.0437 (17)0.0445 (17)0.0099 (14)0.0061 (14)0.0050 (13)
C280.062 (2)0.059 (2)0.057 (2)0.0007 (17)0.0044 (17)0.0189 (17)
C290.052 (2)0.081 (3)0.070 (2)0.0072 (19)0.0079 (18)0.014 (2)
C300.072 (3)0.079 (3)0.074 (3)0.020 (2)0.025 (2)0.017 (2)
C310.086 (3)0.110 (3)0.068 (3)0.021 (3)0.010 (2)0.047 (2)
C320.059 (2)0.097 (3)0.054 (2)0.013 (2)0.0014 (17)0.034 (2)
C330.0496 (18)0.0500 (17)0.0473 (17)0.0107 (14)0.0012 (13)0.0186 (14)
C340.063 (2)0.060 (2)0.084 (3)0.0208 (18)0.0059 (19)0.0319 (19)
C350.098 (3)0.067 (3)0.105 (3)0.028 (2)0.002 (3)0.044 (2)
C360.099 (4)0.072 (3)0.105 (3)0.015 (3)0.026 (3)0.052 (3)
C370.060 (2)0.114 (4)0.106 (3)0.015 (2)0.013 (2)0.071 (3)
C380.0455 (19)0.090 (3)0.086 (3)0.0079 (18)0.0018 (18)0.049 (2)
C390.0507 (18)0.0539 (19)0.0576 (19)0.0124 (15)0.0020 (15)0.0248 (16)
C400.077 (3)0.079 (3)0.063 (2)0.040 (2)0.0002 (19)0.017 (2)
C410.076 (3)0.085 (3)0.085 (3)0.041 (2)0.001 (2)0.033 (2)
C420.064 (2)0.094 (3)0.110 (4)0.026 (2)0.011 (2)0.051 (3)
C430.103 (4)0.111 (4)0.094 (3)0.038 (3)0.047 (3)0.009 (3)
C440.090 (3)0.082 (3)0.077 (3)0.040 (2)0.026 (2)0.004 (2)
C450.0440 (17)0.0532 (18)0.0451 (16)0.0082 (14)0.0045 (13)0.0147 (14)
C460.060 (2)0.067 (2)0.066 (2)0.0085 (17)0.0042 (17)0.0300 (18)
C470.060 (2)0.099 (3)0.076 (3)0.005 (2)0.007 (2)0.046 (3)
C480.061 (2)0.128 (4)0.059 (2)0.023 (3)0.0150 (19)0.038 (3)
C490.080 (3)0.093 (3)0.058 (2)0.029 (2)0.008 (2)0.009 (2)
C500.064 (2)0.061 (2)0.055 (2)0.0069 (17)0.0026 (17)0.0105 (17)
Geometric parameters (Å, º) top
Cl1—O11.394 (4)C21—H210.9300
Cl1—O31.401 (4)C22—C231.361 (7)
Cl1—O21.405 (3)C22—H220.9300
Cl1—O81.422 (3)C23—C241.349 (6)
Cl2—O41.354 (4)C23—H230.9300
Cl2—O71.373 (4)C24—C251.380 (5)
Cl2—O61.380 (4)C24—H240.9300
Cl2—O51.386 (4)C25—H250.9300
P1—C81.799 (3)C26—C271.510 (5)
P1—C141.802 (3)C26—H26A0.9700
P1—C201.803 (4)C26—H26B0.9700
P1—C11.811 (3)C27—C281.378 (5)
P2—C331.791 (3)C27—C321.386 (5)
P2—C391.794 (3)C28—C291.380 (5)
P2—C451.798 (3)C28—H280.9300
P2—C261.813 (3)C29—C301.379 (6)
C1—C21.503 (5)C29—H290.9300
C1—H1A0.9700C30—C311.359 (6)
C1—H1B0.9700C30—H300.9300
C2—C31.371 (5)C31—C321.373 (5)
C2—C71.388 (5)C31—H310.9300
C3—C41.399 (7)C32—H320.9300
C3—H30.9300C33—C341.377 (5)
C4—C51.348 (11)C33—C381.389 (5)
C4—H40.9300C34—C351.391 (5)
C5—C61.333 (11)C34—H340.9300
C5—H50.9300C35—C361.354 (6)
C6—C71.382 (8)C35—H350.9300
C6—H60.9300C36—C371.358 (7)
C7—H70.9300C36—H360.9300
C8—C91.364 (5)C37—C381.396 (5)
C8—C131.377 (5)C37—H370.9300
C9—C101.399 (7)C38—H380.9300
C9—H90.9300C39—C441.371 (5)
C10—C111.327 (9)C39—C401.383 (5)
C10—H100.9300C40—C411.375 (5)
C11—C121.362 (9)C40—H400.9300
C11—H110.9300C41—C421.337 (6)
C12—C131.394 (7)C41—H410.9300
C12—H120.9300C42—C431.381 (6)
C13—H130.9300C42—H420.9300
C14—C191.387 (5)C43—C441.385 (6)
C14—C151.392 (5)C43—H430.9300
C15—C161.381 (5)C44—H440.9300
C15—H150.9300C45—C501.374 (5)
C16—C171.366 (6)C45—C461.395 (4)
C16—H160.9300C46—C471.372 (5)
C17—C181.370 (6)C46—H460.9300
C17—H170.9300C47—C481.362 (6)
C18—C191.375 (5)C47—H470.9300
C18—H180.9300C48—C491.378 (6)
C19—H190.9300C48—H480.9300
C20—C251.371 (5)C49—C501.389 (5)
C20—C211.401 (5)C49—H490.9300
C21—C221.390 (6)C50—H500.9300
O1—Cl1—O3108.3 (3)C23—C22—C21120.6 (4)
O1—Cl1—O2108.6 (3)C23—C22—H22119.7
O3—Cl1—O2111.0 (2)C21—C22—H22119.7
O1—Cl1—O8107.3 (3)C24—C23—C22120.1 (4)
O3—Cl1—O8110.1 (2)C24—C23—H23120.0
O2—Cl1—O8111.4 (2)C22—C23—H23120.0
O4—Cl2—O7115.8 (3)C23—C24—C25121.0 (4)
O4—Cl2—O6103.7 (4)C23—C24—H24119.5
O7—Cl2—O6100.5 (4)C25—C24—H24119.5
O4—Cl2—O5112.0 (3)C20—C25—C24120.2 (3)
O7—Cl2—O5118.6 (4)C20—C25—H25119.9
O6—Cl2—O5103.3 (4)C24—C25—H25119.9
C8—P1—C14109.83 (16)C27—C26—P2114.9 (2)
C8—P1—C20109.12 (16)C27—C26—H26A108.5
C14—P1—C20109.48 (16)P2—C26—H26A108.5
C8—P1—C1109.95 (17)C27—C26—H26B108.5
C14—P1—C1110.92 (15)P2—C26—H26B108.5
C20—P1—C1107.50 (16)H26A—C26—H26B107.5
C33—P2—C39109.73 (15)C28—C27—C32118.3 (3)
C33—P2—C45111.81 (15)C28—C27—C26121.8 (3)
C39—P2—C45107.62 (15)C32—C27—C26119.8 (3)
C33—P2—C26109.90 (15)C27—C28—C29120.5 (3)
C39—P2—C26108.29 (16)C27—C28—H28119.8
C45—P2—C26109.41 (15)C29—C28—H28119.8
C2—C1—P1114.7 (2)C30—C29—C28120.5 (4)
C2—C1—H1A108.6C30—C29—H29119.8
P1—C1—H1A108.6C28—C29—H29119.8
C2—C1—H1B108.6C31—C30—C29119.0 (4)
P1—C1—H1B108.6C31—C30—H30120.5
H1A—C1—H1B107.6C29—C30—H30120.5
C3—C2—C7119.2 (4)C30—C31—C32121.1 (4)
C3—C2—C1119.2 (3)C30—C31—H31119.5
C7—C2—C1121.5 (3)C32—C31—H31119.5
C2—C3—C4119.8 (5)C31—C32—C27120.6 (4)
C2—C3—H3120.1C31—C32—H32119.7
C4—C3—H3120.1C27—C32—H32119.7
C5—C4—C3119.6 (6)C34—C33—C38120.0 (3)
C5—C4—H4120.2C34—C33—P2121.1 (3)
C3—C4—H4120.2C38—C33—P2118.8 (3)
C6—C5—C4121.1 (6)C33—C34—C35119.6 (4)
C6—C5—H5119.4C33—C34—H34120.2
C4—C5—H5119.4C35—C34—H34120.2
C5—C6—C7121.0 (7)C36—C35—C34120.1 (4)
C5—C6—H6119.5C36—C35—H35119.9
C7—C6—H6119.5C34—C35—H35119.9
C6—C7—C2119.2 (5)C35—C36—C37121.1 (4)
C6—C7—H7120.4C35—C36—H36119.4
C2—C7—H7120.4C37—C36—H36119.4
C9—C8—C13120.0 (4)C36—C37—C38120.1 (4)
C9—C8—P1123.3 (3)C36—C37—H37119.9
C13—C8—P1116.7 (3)C38—C37—H37119.9
C8—C9—C10119.4 (5)C33—C38—C37119.0 (4)
C8—C9—H9120.3C33—C38—H38120.5
C10—C9—H9120.3C37—C38—H38120.5
C11—C10—C9120.5 (6)C44—C39—C40119.5 (3)
C11—C10—H10119.8C44—C39—P2118.6 (3)
C9—C10—H10119.8C40—C39—P2121.9 (3)
C10—C11—C12121.2 (5)C41—C40—C39120.1 (4)
C10—C11—H11119.4C41—C40—H40120.0
C12—C11—H11119.4C39—C40—H40120.0
C11—C12—C13119.6 (6)C42—C41—C40120.6 (4)
C11—C12—H12120.2C42—C41—H41119.7
C13—C12—H12120.2C40—C41—H41119.7
C8—C13—C12119.4 (5)C41—C42—C43120.4 (4)
C8—C13—H13120.3C41—C42—H42119.8
C12—C13—H13120.3C43—C42—H42119.8
C19—C14—C15118.9 (3)C42—C43—C44119.9 (4)
C19—C14—P1120.1 (3)C42—C43—H43120.1
C15—C14—P1121.0 (3)C44—C43—H43120.1
C16—C15—C14120.1 (4)C39—C44—C43119.5 (4)
C16—C15—H15119.9C39—C44—H44120.2
C14—C15—H15119.9C43—C44—H44120.2
C17—C16—C15120.0 (4)C50—C45—C46120.2 (3)
C17—C16—H16120.0C50—C45—P2121.8 (2)
C15—C16—H16120.0C46—C45—P2117.8 (3)
C16—C17—C18120.4 (4)C47—C46—C45119.7 (4)
C16—C17—H17119.8C47—C46—H46120.1
C18—C17—H17119.8C45—C46—H46120.1
C17—C18—C19120.4 (4)C48—C47—C46120.4 (4)
C17—C18—H18119.8C48—C47—H47119.8
C19—C18—H18119.8C46—C47—H47119.8
C18—C19—C14120.1 (4)C47—C48—C49120.4 (4)
C18—C19—H19120.0C47—C48—H48119.8
C14—C19—H19120.0C49—C48—H48119.8
C25—C20—C21119.0 (3)C48—C49—C50120.2 (4)
C25—C20—P1122.0 (3)C48—C49—H49119.9
C21—C20—P1118.9 (3)C50—C49—H49119.9
C22—C21—C20119.0 (4)C45—C50—C49119.2 (4)
C22—C21—H21120.5C45—C50—H50120.4
C20—C21—H21120.5C49—C50—H50120.4
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C27–C32 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cgi0.932.833.757 (9)176
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC25H22P+·ClO4
Mr452.85
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.096 (1), 13.8967 (13), 18.2577 (17)
α, β, γ (°)69.765 (2), 84.826 (2), 73.195 (2)
V3)2300.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.31 × 0.29 × 0.24
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.923, 0.939
No. of measured, independent and
observed [I > 2σ(I)] reflections
11362, 7992, 5675
Rint0.019
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.185, 1.02
No. of reflections7992
No. of parameters559
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.95, 0.36

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C27–C32 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cgi0.932.833.757 (9)176
Symmetry code: (i) x+1, y+1, z.
 

References

First citationBruker (2001). SAINT-Plus. Bruker AXS Inc., Madison,Wisconsin, USA.  Google Scholar
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFischer, A. & Wiebelhaus, D. (1997). Z. Krist. New Cryst. Struct. 212, 335–336.  CAS Google Scholar
First citationFox, D. C., Fiedler, A. T., Halfen, H. L., Brunold, T. C. & Halfen, J. A. (2004). J. Am. Chem. Soc. 126, 7627–7638.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHubner, J., Wulff-Molder, D., Vogt, H. & Meisel, M. (1997). Z. Naturforsch. Teil B, 52, 1321–1325.  Google Scholar
First citationHuynh, M. H. V., El-Samanody, E.-S., Demadis, K. D., White, P. S. & Meyer, T. J. (2000). Inorg. Chem. 39, 3075–3085.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSkapski, A. C. & Stephens, F. A. (1974). J. Cryst. Mol. Struct. 4, 77–85.  CSD CrossRef CAS Google Scholar
First citationZhang, D. P., Zhang, L. F., Chen, Y. T., Wang, H. L., Ni, Z. H., Wernsdorfer, W. & Jiang, J. Z. (2010). Chem. Commun. 46, 3550–3552.  CrossRef CAS Google Scholar

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