Benzyl­triphenyl­phospho­nium perchlorate

Li, L.; He, X.

doi:10.1107/S1600536811021660

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1635

doi:10.1107/S1600536811021660

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Benzyltriphenylphosphonium perchlorate

Liwei Li ^a ^* and Xiaoqiang He ^a

^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 ); Huynh et al. (2000 ). For related structures, see: Zhang et al. (2010 ); Fischer & Wiebelhaus (1997 ); Hubner et al. (1997 ); Skapski & Stephens (1974 ).

Experimental

Crystal data

C₂₅H₂₂P⁺·ClO₄⁻
M_r = 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 ) T_min = 0.923, T_max = 0.939
11362 measured reflections
7992 independent reflections
5675 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.185
S = 1.02
7992 reflections
559 parameters
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021660/lh5256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021660/lh5256Isup2.hkl

checkCIF report

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%.

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

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⁺·ClO₄⁻	Z = 4
M_r = 452.85	F(000) = 944
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.096 (1) Å	Cell parameters from 2162 reflections
b = 13.8967 (13) Å	θ = 2.4–26.7°
c = 18.2577 (17) Å	µ = 0.26 mm⁻¹
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 tube	5675 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
T_min = 0.923, T_max = 0.939	k = −16→16
11362 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.099P)² + 1.1578P] where P = (F_o² + 2F_c²)/3
7992 reflections	(Δ/σ)_max < 0.001
559 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₅H₂₂P⁺·ClO₄⁻	γ = 73.195 (2)°
M_r = 452.85	V = 2300.7 (4) Å³
Triclinic, P1	Z = 4
a = 10.096 (1) Å	Mo Kα radiation
b = 13.8967 (13) Å	µ = 0.26 mm⁻¹
c = 18.2577 (17) Å	T = 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)
T_min = 0.923, T_max = 0.939	R_int = 0.019
11362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.02	Δρ_max = 0.95 e Å⁻³
7992 reflections	Δρ_min = −0.36 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.28935 (10)	0.87956 (7)	0.37917 (6)	0.0715 (3)
Cl2	0.64016 (9)	0.63901 (7)	0.12239 (5)	0.0618 (3)
P1	0.78887 (9)	0.70653 (7)	0.35120 (5)	0.0504 (2)
P2	0.15337 (8)	0.25542 (6)	0.15262 (5)	0.0455 (2)
O1	0.2871 (6)	0.8624 (3)	0.4591 (2)	0.160 (2)
O2	0.3355 (3)	0.9704 (2)	0.3405 (2)	0.1007 (10)
O3	0.1552 (4)	0.8940 (3)	0.3548 (3)	0.1497 (19)
O4	0.5282 (5)	0.6397 (6)	0.1692 (2)	0.186 (3)
O5	0.6241 (5)	0.6110 (5)	0.0585 (3)	0.1600 (19)
O6	0.6364 (6)	0.7454 (3)	0.0897 (4)	0.190 (2)
O7	0.7664 (4)	0.5984 (5)	0.1599 (3)	0.190 (3)
O8	0.3807 (3)	0.7868 (2)	0.3676 (2)	0.0951 (9)
C1	0.6743 (3)	0.7966 (3)	0.27025 (19)	0.0552 (8)
H1A	0.6667	0.7578	0.2365	0.066*
H1B	0.5830	0.8198	0.2906	0.066*
C2	0.7194 (3)	0.8937 (3)	0.2221 (2)	0.0540 (8)
C3	0.7893 (4)	0.8939 (4)	0.1541 (2)	0.0749 (11)
H3	0.8134	0.8331	0.1398	0.090*
C4	0.8242 (6)	0.9860 (6)	0.1063 (3)	0.122 (2)
H4	0.8721	0.9865	0.0603	0.147*
C5	0.7882 (7)	1.0740 (6)	0.1274 (6)	0.152 (4)
H5	0.8101	1.1354	0.0950	0.183*
C6	0.7216 (7)	1.0744 (4)	0.1938 (5)	0.129 (2)
H6	0.6995	1.1357	0.2075	0.155*
C7	0.6850 (5)	0.9851 (3)	0.2426 (3)	0.0867 (13)
H7	0.6379	0.9863	0.2886	0.104*
C8	0.7901 (4)	0.7712 (3)	0.42106 (19)	0.0606 (9)
C9	0.9078 (5)	0.7808 (4)	0.4455 (2)	0.0905 (14)
H9	0.9937	0.7507	0.4277	0.109*
C10	0.8984 (8)	0.8365 (6)	0.4974 (3)	0.130 (2)
H10	0.9781	0.8449	0.5133	0.156*
C11	0.7763 (10)	0.8775 (6)	0.5244 (3)	0.133 (2)
H11	0.7719	0.9134	0.5595	0.160*
C12	0.6574 (8)	0.8679 (6)	0.5014 (3)	0.138 (3)
H12	0.5726	0.8974	0.5205	0.166*
C13	0.6636 (5)	0.8135 (5)	0.4492 (3)	0.1033 (17)
H13	0.5832	0.8060	0.4336	0.124*
C14	0.9621 (3)	0.6633 (3)	0.31777 (19)	0.0557 (8)
C15	1.0440 (4)	0.7335 (3)	0.2902 (2)	0.0623 (9)
H15	1.0087	0.8041	0.2880	0.075*
C16	1.1773 (4)	0.6984 (4)	0.2661 (2)	0.0709 (10)
H16	1.2330	0.7447	0.2495	0.085*
C17	1.2275 (4)	0.5957 (4)	0.2666 (2)	0.0825 (12)
H17	1.3168	0.5727	0.2494	0.099*
C18	1.1472 (5)	0.5264 (4)	0.2923 (3)	0.0894 (13)
H18	1.1823	0.4566	0.2926	0.107*
C19	1.0149 (4)	0.5594 (3)	0.3177 (3)	0.0760 (11)
H19	0.9608	0.5120	0.3349	0.091*
C20	0.7226 (3)	0.5925 (3)	0.39688 (19)	0.0554 (8)
C21	0.7725 (4)	0.5226 (4)	0.4711 (2)	0.0810 (12)
H21	0.8367	0.5360	0.4970	0.097*
C22	0.7246 (5)	0.4330 (4)	0.5054 (3)	0.0917 (15)
H22	0.7571	0.3862	0.5547	0.110*
C23	0.6308 (5)	0.4131 (3)	0.4677 (3)	0.0820 (13)
H23	0.6006	0.3523	0.4908	0.098*
C24	0.5816 (4)	0.4814 (3)	0.3967 (2)	0.0714 (10)
H24	0.5161	0.4679	0.3717	0.086*
C25	0.6269 (4)	0.5711 (3)	0.3606 (2)	0.0590 (8)
H25	0.5925	0.6171	0.3115	0.071*
C26	0.0749 (4)	0.3622 (3)	0.06520 (19)	0.0562 (8)
H26A	0.0360	0.4268	0.0781	0.067*
H26B	0.1468	0.3749	0.0271	0.067*
C27	−0.0372 (3)	0.3416 (2)	0.02821 (18)	0.0512 (8)
C28	−0.1743 (4)	0.3715 (3)	0.0479 (2)	0.0628 (9)
H28	−0.1990	0.4019	0.0870	0.075*
C29	−0.2753 (4)	0.3568 (3)	0.0101 (2)	0.0731 (11)
H29	−0.3677	0.3783	0.0233	0.088*
C30	−0.2404 (4)	0.3103 (3)	−0.0472 (2)	0.0757 (11)
H30	−0.3084	0.2999	−0.0724	0.091*
C31	−0.1051 (5)	0.2801 (4)	−0.0662 (2)	0.0838 (12)
H31	−0.0809	0.2496	−0.1052	0.101*
C32	−0.0035 (4)	0.2938 (3)	−0.0288 (2)	0.0698 (10)
H32	0.0886	0.2709	−0.0417	0.084*
C33	0.2236 (3)	0.1339 (2)	0.13166 (18)	0.0489 (7)
C34	0.1405 (4)	0.0721 (3)	0.1291 (2)	0.0665 (9)
H34	0.0462	0.0928	0.1387	0.080*
C35	0.1983 (5)	−0.0215 (3)	0.1121 (3)	0.0847 (12)
H35	0.1432	−0.0647	0.1120	0.102*
C36	0.3346 (6)	−0.0497 (4)	0.0957 (3)	0.0930 (15)
H36	0.3720	−0.1120	0.0838	0.112*
C37	0.4177 (5)	0.0113 (4)	0.0964 (3)	0.0917 (15)
H37	0.5112	−0.0094	0.0850	0.110*
C38	0.3631 (4)	0.1051 (3)	0.1140 (2)	0.0705 (10)
H38	0.4193	0.1477	0.1140	0.085*
C39	0.2891 (3)	0.2915 (3)	0.18479 (19)	0.0527 (8)
C40	0.3374 (4)	0.3763 (3)	0.1383 (2)	0.0707 (10)
H40	0.3000	0.4159	0.0886	0.085*
C41	0.4405 (4)	0.4020 (4)	0.1654 (3)	0.0766 (11)
H41	0.4723	0.4593	0.1340	0.092*
C42	0.4957 (4)	0.3453 (4)	0.2366 (3)	0.0829 (12)
H42	0.5657	0.3633	0.2542	0.099*
C43	0.4493 (5)	0.2603 (4)	0.2841 (3)	0.1044 (16)
H43	0.4878	0.2213	0.3336	0.125*
C44	0.3452 (5)	0.2332 (4)	0.2579 (2)	0.0835 (12)
H44	0.3137	0.1759	0.2896	0.100*
C45	0.0268 (3)	0.2423 (2)	0.22866 (18)	0.0488 (7)
C46	−0.0568 (4)	0.3353 (3)	0.2398 (2)	0.0644 (9)
H46	−0.0501	0.4017	0.2065	0.077*
C47	−0.1488 (4)	0.3286 (4)	0.3002 (3)	0.0777 (12)
H47	−0.2051	0.3905	0.3075	0.093*
C48	−0.1582 (4)	0.2316 (4)	0.3495 (2)	0.0825 (13)
H48	−0.2206	0.2277	0.3905	0.099*
C49	−0.0760 (4)	0.1392 (4)	0.3391 (2)	0.0806 (12)
H49	−0.0838	0.0733	0.3726	0.097*
C50	0.0186 (4)	0.1442 (3)	0.2786 (2)	0.0649 (9)
H50	0.0756	0.0820	0.2720	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0651 (6)	0.0486 (5)	0.0899 (7)	−0.0150 (4)	0.0148 (5)	−0.0140 (5)
Cl2	0.0601 (5)	0.0640 (5)	0.0710 (6)	−0.0234 (4)	0.0099 (4)	−0.0318 (4)
P1	0.0498 (5)	0.0578 (5)	0.0429 (4)	−0.0128 (4)	−0.0004 (3)	−0.0176 (4)
P2	0.0456 (4)	0.0445 (4)	0.0463 (4)	−0.0120 (3)	−0.0011 (3)	−0.0151 (3)
O1	0.264 (6)	0.110 (3)	0.104 (3)	−0.054 (3)	0.062 (3)	−0.046 (2)
O2	0.096 (2)	0.0658 (18)	0.127 (3)	−0.0368 (16)	0.0062 (19)	−0.0054 (17)
O3	0.071 (2)	0.083 (2)	0.282 (6)	−0.0226 (18)	−0.009 (3)	−0.042 (3)
O4	0.129 (3)	0.391 (8)	0.104 (3)	−0.143 (5)	0.050 (3)	−0.118 (4)
O5	0.181 (4)	0.223 (5)	0.132 (3)	−0.067 (4)	0.037 (3)	−0.127 (4)
O6	0.203 (5)	0.078 (3)	0.278 (7)	−0.031 (3)	−0.013 (5)	−0.047 (4)
O7	0.087 (3)	0.207 (5)	0.190 (5)	0.000 (3)	−0.034 (3)	0.015 (4)
O8	0.091 (2)	0.0691 (18)	0.115 (2)	−0.0128 (15)	0.0239 (18)	−0.0320 (17)
C1	0.057 (2)	0.059 (2)	0.0480 (18)	−0.0189 (16)	−0.0023 (15)	−0.0130 (15)
C2	0.0462 (18)	0.0493 (18)	0.0586 (19)	−0.0103 (14)	−0.0053 (15)	−0.0094 (15)
C3	0.060 (2)	0.094 (3)	0.053 (2)	−0.022 (2)	0.0016 (17)	−0.002 (2)
C4	0.079 (3)	0.145 (6)	0.090 (4)	−0.041 (4)	−0.006 (3)	0.035 (4)
C5	0.086 (4)	0.096 (5)	0.205 (9)	−0.046 (4)	−0.047 (5)	0.064 (5)
C6	0.102 (4)	0.056 (3)	0.213 (8)	−0.024 (3)	−0.040 (5)	−0.015 (4)
C7	0.076 (3)	0.063 (3)	0.117 (4)	−0.010 (2)	−0.011 (2)	−0.031 (3)
C8	0.063 (2)	0.076 (2)	0.0439 (17)	−0.0122 (18)	−0.0019 (15)	−0.0258 (17)
C9	0.082 (3)	0.140 (4)	0.073 (3)	−0.036 (3)	0.001 (2)	−0.059 (3)
C10	0.153 (6)	0.200 (7)	0.095 (4)	−0.084 (5)	0.016 (4)	−0.096 (5)
C11	0.210 (8)	0.136 (5)	0.085 (4)	−0.052 (5)	0.008 (5)	−0.073 (4)
C12	0.155 (6)	0.154 (6)	0.094 (4)	0.019 (5)	0.005 (4)	−0.079 (4)
C13	0.082 (3)	0.151 (5)	0.082 (3)	0.000 (3)	0.002 (2)	−0.071 (3)
C14	0.0532 (19)	0.067 (2)	0.0485 (18)	−0.0123 (16)	−0.0010 (14)	−0.0246 (16)
C15	0.060 (2)	0.072 (2)	0.055 (2)	−0.0162 (18)	−0.0025 (16)	−0.0214 (18)
C16	0.060 (2)	0.096 (3)	0.062 (2)	−0.030 (2)	0.0039 (18)	−0.025 (2)
C17	0.056 (2)	0.114 (4)	0.076 (3)	−0.011 (2)	0.008 (2)	−0.042 (3)
C18	0.075 (3)	0.086 (3)	0.114 (4)	−0.012 (2)	0.022 (3)	−0.055 (3)
C19	0.069 (2)	0.082 (3)	0.093 (3)	−0.027 (2)	0.019 (2)	−0.049 (2)
C20	0.0523 (19)	0.0539 (19)	0.0472 (17)	−0.0061 (15)	0.0060 (14)	−0.0095 (15)
C21	0.070 (3)	0.087 (3)	0.062 (2)	−0.011 (2)	−0.0063 (19)	−0.002 (2)
C22	0.083 (3)	0.074 (3)	0.069 (3)	−0.002 (2)	0.010 (2)	0.018 (2)
C23	0.083 (3)	0.052 (2)	0.091 (3)	−0.013 (2)	0.031 (3)	−0.011 (2)
C24	0.080 (3)	0.055 (2)	0.079 (3)	−0.0220 (19)	0.020 (2)	−0.025 (2)
C25	0.069 (2)	0.0526 (19)	0.0527 (19)	−0.0155 (17)	0.0056 (16)	−0.0166 (16)
C26	0.065 (2)	0.0484 (18)	0.0510 (18)	−0.0173 (16)	−0.0062 (15)	−0.0091 (15)
C27	0.0562 (19)	0.0437 (17)	0.0445 (17)	−0.0099 (14)	−0.0061 (14)	−0.0050 (13)
C28	0.062 (2)	0.059 (2)	0.057 (2)	−0.0007 (17)	−0.0044 (17)	−0.0189 (17)
C29	0.052 (2)	0.081 (3)	0.070 (2)	−0.0072 (19)	−0.0079 (18)	−0.014 (2)
C30	0.072 (3)	0.079 (3)	0.074 (3)	−0.020 (2)	−0.025 (2)	−0.017 (2)
C31	0.086 (3)	0.110 (3)	0.068 (3)	−0.021 (3)	−0.010 (2)	−0.047 (2)
C32	0.059 (2)	0.097 (3)	0.054 (2)	−0.013 (2)	0.0014 (17)	−0.034 (2)
C33	0.0496 (18)	0.0500 (17)	0.0473 (17)	−0.0107 (14)	−0.0012 (13)	−0.0186 (14)
C34	0.063 (2)	0.060 (2)	0.084 (3)	−0.0208 (18)	0.0059 (19)	−0.0319 (19)
C35	0.098 (3)	0.067 (3)	0.105 (3)	−0.028 (2)	0.002 (3)	−0.044 (2)
C36	0.099 (4)	0.072 (3)	0.105 (3)	0.015 (3)	−0.026 (3)	−0.052 (3)
C37	0.060 (2)	0.114 (4)	0.106 (3)	0.015 (2)	−0.013 (2)	−0.071 (3)
C38	0.0455 (19)	0.090 (3)	0.086 (3)	−0.0079 (18)	−0.0018 (18)	−0.049 (2)
C39	0.0507 (18)	0.0539 (19)	0.0576 (19)	−0.0124 (15)	−0.0020 (15)	−0.0248 (16)
C40	0.077 (3)	0.079 (3)	0.063 (2)	−0.040 (2)	−0.0002 (19)	−0.017 (2)
C41	0.076 (3)	0.085 (3)	0.085 (3)	−0.041 (2)	0.001 (2)	−0.033 (2)
C42	0.064 (2)	0.094 (3)	0.110 (4)	−0.026 (2)	−0.011 (2)	−0.051 (3)
C43	0.103 (4)	0.111 (4)	0.094 (3)	−0.038 (3)	−0.047 (3)	−0.009 (3)
C44	0.090 (3)	0.082 (3)	0.077 (3)	−0.040 (2)	−0.026 (2)	−0.004 (2)
C45	0.0440 (17)	0.0532 (18)	0.0451 (16)	−0.0082 (14)	−0.0045 (13)	−0.0147 (14)
C46	0.060 (2)	0.067 (2)	0.066 (2)	−0.0085 (17)	0.0042 (17)	−0.0300 (18)
C47	0.060 (2)	0.099 (3)	0.076 (3)	−0.005 (2)	0.007 (2)	−0.046 (3)
C48	0.061 (2)	0.128 (4)	0.059 (2)	−0.023 (3)	0.0150 (19)	−0.038 (3)
C49	0.080 (3)	0.093 (3)	0.058 (2)	−0.029 (2)	0.008 (2)	−0.009 (2)
C50	0.064 (2)	0.061 (2)	0.055 (2)	−0.0069 (17)	0.0026 (17)	−0.0105 (17)

Geometric parameters (Å, º) top

Cl1—O1	1.394 (4)	C21—H21	0.9300
Cl1—O3	1.401 (4)	C22—C23	1.361 (7)
Cl1—O2	1.405 (3)	C22—H22	0.9300
Cl1—O8	1.422 (3)	C23—C24	1.349 (6)
Cl2—O4	1.354 (4)	C23—H23	0.9300
Cl2—O7	1.373 (4)	C24—C25	1.380 (5)
Cl2—O6	1.380 (4)	C24—H24	0.9300
Cl2—O5	1.386 (4)	C25—H25	0.9300
P1—C8	1.799 (3)	C26—C27	1.510 (5)
P1—C14	1.802 (3)	C26—H26A	0.9700
P1—C20	1.803 (4)	C26—H26B	0.9700
P1—C1	1.811 (3)	C27—C28	1.378 (5)
P2—C33	1.791 (3)	C27—C32	1.386 (5)
P2—C39	1.794 (3)	C28—C29	1.380 (5)
P2—C45	1.798 (3)	C28—H28	0.9300
P2—C26	1.813 (3)	C29—C30	1.379 (6)
C1—C2	1.503 (5)	C29—H29	0.9300
C1—H1A	0.9700	C30—C31	1.359 (6)
C1—H1B	0.9700	C30—H30	0.9300
C2—C3	1.371 (5)	C31—C32	1.373 (5)
C2—C7	1.388 (5)	C31—H31	0.9300
C3—C4	1.399 (7)	C32—H32	0.9300
C3—H3	0.9300	C33—C34	1.377 (5)
C4—C5	1.348 (11)	C33—C38	1.389 (5)
C4—H4	0.9300	C34—C35	1.391 (5)
C5—C6	1.333 (11)	C34—H34	0.9300
C5—H5	0.9300	C35—C36	1.354 (6)
C6—C7	1.382 (8)	C35—H35	0.9300
C6—H6	0.9300	C36—C37	1.358 (7)
C7—H7	0.9300	C36—H36	0.9300
C8—C9	1.364 (5)	C37—C38	1.396 (5)
C8—C13	1.377 (5)	C37—H37	0.9300
C9—C10	1.399 (7)	C38—H38	0.9300
C9—H9	0.9300	C39—C44	1.371 (5)
C10—C11	1.327 (9)	C39—C40	1.383 (5)
C10—H10	0.9300	C40—C41	1.375 (5)
C11—C12	1.362 (9)	C40—H40	0.9300
C11—H11	0.9300	C41—C42	1.337 (6)
C12—C13	1.394 (7)	C41—H41	0.9300
C12—H12	0.9300	C42—C43	1.381 (6)
C13—H13	0.9300	C42—H42	0.9300
C14—C19	1.387 (5)	C43—C44	1.385 (6)
C14—C15	1.392 (5)	C43—H43	0.9300
C15—C16	1.381 (5)	C44—H44	0.9300
C15—H15	0.9300	C45—C50	1.374 (5)
C16—C17	1.366 (6)	C45—C46	1.395 (4)
C16—H16	0.9300	C46—C47	1.372 (5)
C17—C18	1.370 (6)	C46—H46	0.9300
C17—H17	0.9300	C47—C48	1.362 (6)
C18—C19	1.375 (5)	C47—H47	0.9300
C18—H18	0.9300	C48—C49	1.378 (6)
C19—H19	0.9300	C48—H48	0.9300
C20—C25	1.371 (5)	C49—C50	1.389 (5)
C20—C21	1.401 (5)	C49—H49	0.9300
C21—C22	1.390 (6)	C50—H50	0.9300

O1—Cl1—O3	108.3 (3)	C23—C22—C21	120.6 (4)
O1—Cl1—O2	108.6 (3)	C23—C22—H22	119.7
O3—Cl1—O2	111.0 (2)	C21—C22—H22	119.7
O1—Cl1—O8	107.3 (3)	C24—C23—C22	120.1 (4)
O3—Cl1—O8	110.1 (2)	C24—C23—H23	120.0
O2—Cl1—O8	111.4 (2)	C22—C23—H23	120.0
O4—Cl2—O7	115.8 (3)	C23—C24—C25	121.0 (4)
O4—Cl2—O6	103.7 (4)	C23—C24—H24	119.5
O7—Cl2—O6	100.5 (4)	C25—C24—H24	119.5
O4—Cl2—O5	112.0 (3)	C20—C25—C24	120.2 (3)
O7—Cl2—O5	118.6 (4)	C20—C25—H25	119.9
O6—Cl2—O5	103.3 (4)	C24—C25—H25	119.9
C8—P1—C14	109.83 (16)	C27—C26—P2	114.9 (2)
C8—P1—C20	109.12 (16)	C27—C26—H26A	108.5
C14—P1—C20	109.48 (16)	P2—C26—H26A	108.5
C8—P1—C1	109.95 (17)	C27—C26—H26B	108.5
C14—P1—C1	110.92 (15)	P2—C26—H26B	108.5
C20—P1—C1	107.50 (16)	H26A—C26—H26B	107.5
C33—P2—C39	109.73 (15)	C28—C27—C32	118.3 (3)
C33—P2—C45	111.81 (15)	C28—C27—C26	121.8 (3)
C39—P2—C45	107.62 (15)	C32—C27—C26	119.8 (3)
C33—P2—C26	109.90 (15)	C27—C28—C29	120.5 (3)
C39—P2—C26	108.29 (16)	C27—C28—H28	119.8
C45—P2—C26	109.41 (15)	C29—C28—H28	119.8
C2—C1—P1	114.7 (2)	C30—C29—C28	120.5 (4)
C2—C1—H1A	108.6	C30—C29—H29	119.8
P1—C1—H1A	108.6	C28—C29—H29	119.8
C2—C1—H1B	108.6	C31—C30—C29	119.0 (4)
P1—C1—H1B	108.6	C31—C30—H30	120.5
H1A—C1—H1B	107.6	C29—C30—H30	120.5
C3—C2—C7	119.2 (4)	C30—C31—C32	121.1 (4)
C3—C2—C1	119.2 (3)	C30—C31—H31	119.5
C7—C2—C1	121.5 (3)	C32—C31—H31	119.5
C2—C3—C4	119.8 (5)	C31—C32—C27	120.6 (4)
C2—C3—H3	120.1	C31—C32—H32	119.7
C4—C3—H3	120.1	C27—C32—H32	119.7
C5—C4—C3	119.6 (6)	C34—C33—C38	120.0 (3)
C5—C4—H4	120.2	C34—C33—P2	121.1 (3)
C3—C4—H4	120.2	C38—C33—P2	118.8 (3)
C6—C5—C4	121.1 (6)	C33—C34—C35	119.6 (4)
C6—C5—H5	119.4	C33—C34—H34	120.2
C4—C5—H5	119.4	C35—C34—H34	120.2
C5—C6—C7	121.0 (7)	C36—C35—C34	120.1 (4)
C5—C6—H6	119.5	C36—C35—H35	119.9
C7—C6—H6	119.5	C34—C35—H35	119.9
C6—C7—C2	119.2 (5)	C35—C36—C37	121.1 (4)
C6—C7—H7	120.4	C35—C36—H36	119.4
C2—C7—H7	120.4	C37—C36—H36	119.4
C9—C8—C13	120.0 (4)	C36—C37—C38	120.1 (4)
C9—C8—P1	123.3 (3)	C36—C37—H37	119.9
C13—C8—P1	116.7 (3)	C38—C37—H37	119.9
C8—C9—C10	119.4 (5)	C33—C38—C37	119.0 (4)
C8—C9—H9	120.3	C33—C38—H38	120.5
C10—C9—H9	120.3	C37—C38—H38	120.5
C11—C10—C9	120.5 (6)	C44—C39—C40	119.5 (3)
C11—C10—H10	119.8	C44—C39—P2	118.6 (3)
C9—C10—H10	119.8	C40—C39—P2	121.9 (3)
C10—C11—C12	121.2 (5)	C41—C40—C39	120.1 (4)
C10—C11—H11	119.4	C41—C40—H40	120.0
C12—C11—H11	119.4	C39—C40—H40	120.0
C11—C12—C13	119.6 (6)	C42—C41—C40	120.6 (4)
C11—C12—H12	120.2	C42—C41—H41	119.7
C13—C12—H12	120.2	C40—C41—H41	119.7
C8—C13—C12	119.4 (5)	C41—C42—C43	120.4 (4)
C8—C13—H13	120.3	C41—C42—H42	119.8
C12—C13—H13	120.3	C43—C42—H42	119.8
C19—C14—C15	118.9 (3)	C42—C43—C44	119.9 (4)
C19—C14—P1	120.1 (3)	C42—C43—H43	120.1
C15—C14—P1	121.0 (3)	C44—C43—H43	120.1
C16—C15—C14	120.1 (4)	C39—C44—C43	119.5 (4)
C16—C15—H15	119.9	C39—C44—H44	120.2
C14—C15—H15	119.9	C43—C44—H44	120.2
C17—C16—C15	120.0 (4)	C50—C45—C46	120.2 (3)
C17—C16—H16	120.0	C50—C45—P2	121.8 (2)
C15—C16—H16	120.0	C46—C45—P2	117.8 (3)
C16—C17—C18	120.4 (4)	C47—C46—C45	119.7 (4)
C16—C17—H17	119.8	C47—C46—H46	120.1
C18—C17—H17	119.8	C45—C46—H46	120.1
C17—C18—C19	120.4 (4)	C48—C47—C46	120.4 (4)
C17—C18—H18	119.8	C48—C47—H47	119.8
C19—C18—H18	119.8	C46—C47—H47	119.8
C18—C19—C14	120.1 (4)	C47—C48—C49	120.4 (4)
C18—C19—H19	120.0	C47—C48—H48	119.8
C14—C19—H19	120.0	C49—C48—H48	119.8
C25—C20—C21	119.0 (3)	C48—C49—C50	120.2 (4)
C25—C20—P1	122.0 (3)	C48—C49—H49	119.9
C21—C20—P1	118.9 (3)	C50—C49—H49	119.9
C22—C21—C20	119.0 (4)	C45—C50—C49	119.2 (4)
C22—C21—H21	120.5	C45—C50—H50	120.4
C20—C21—H21	120.5	C49—C50—H50	120.4

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C27–C32 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.93	2.83	3.757 (9)	176

Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂P⁺·ClO₄⁻
M_r	452.85
Crystal system, space group	Triclinic, 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)
V (Å³)	2300.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.31 × 0.29 × 0.24

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	11362, 7992, 5675
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.185, 1.02
No. of reflections	7992
No. of parameters	559
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.93	2.83	3.757 (9)	176

Symmetry code: (i) x+1, y+1, z.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
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Skapski, A. C. & Stephens, F. A. (1974). J. Cryst. Mol. Struct. 4, 77–85. CSD CrossRef CAS Google Scholar
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. CrossRef CAS Google Scholar

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Volume 67| Part 7| July 2011| Page o1635

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