Triphen­yl[(4-phenyl­benzo­yl)meth­yl]phospho­nium trifluoro­methane­sulfonate

Rizzoli, C.; Karami, K.; Salah, M.M.

doi:10.1107/S1600536810038286

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2675-o2676

doi:10.1107/S1600536810038286

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Triphenyl[(4-phenylbenzoyl)methyl]phosphonium trifluoromethanesulfonate

Corrado Rizzoli,^a ^* Kazem Karami ^b and Mina Mohamadi Salah ^b

^aDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43100 Parma, Italy, and ^bDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156/83111, Iran
^*Correspondence e-mail: corrado.rizzoli@unipr.it

(Received 20 September 2010; accepted 24 September 2010; online 30 September 2010)

In the cation of the title compound, C₃₂H₂₆OP⁺·CF₃O₃S⁻, the dihedral angle between the benzene rings of the biphenyl group is 42.37 (8)°. In the crystal, the cations and anions interact through intermolecular C—H⋯O hydrogen bonds, forming chains parallel to the b axis. These chains are further linked by C—H⋯π stacking interactions into layers parallel to the bc plane.

Related literature

For the synthesis and characterization of phosphorus ylide metal complexes, see: Kalyanasundari et al. (1995 , 1999 ); Laavanya et al. (2001 ); Vicente et al. (1985 ); Karami (2007 , 2008 ); Akkurt et al. (2008 ). For related structures, see: Karami & Büyükgüngör (2009 ); Shao et al. (1982 ). For the synthesis of the title compound, see: Burmeister et al. (1973 ).

Experimental

Crystal data

C₃₂H₂₆OP⁺·CF₃O₃S⁻
M_r = 606.58
Monoclinic, P 2₁ /c
a = 9.0559 (10) Å
b = 19.382 (2) Å
c = 16.5396 (19) Å
β = 92.577 (2)°
V = 2900.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 294 K
0.25 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.936, T_max = 0.974
29195 measured reflections
5245 independent reflections
3748 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.06
5245 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C21–C26 and C15–C20 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O4ⁱ	0.97	2.22	3.191 (4)	178
C26—H26⋯O3ⁱⁱ	0.93	2.45	3.373 (3)	174
C32—H32⋯O3ⁱⁱ	0.93	2.46	3.369 (4)	168
C1—H1A⋯Cg1ⁱⁱⁱ	0.97	2.84	3.780 (3)	164
C10—H10⋯Cg2^iv	0.93	3.02	3.767 (4)	138
C23—H23⋯Cg3^v	0.93	2.91	3.788 (4)	159
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and SCHAKAL97 (Keller, 1997 ); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038286/lx2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038286/lx2176Isup2.hkl

checkCIF report

Comment top

The synthesis of α–ketostabilized phosphorus ylides has attracted much interest over the last decades due to their stability and ability to act as bifunctional ligands (C- versus O-coordination; Kalyanasundari et al., 1995; Kalyanasundari et al., 1999; Laavanya et al., 2001; Vicente et al., 1985). In this respect, the preferred coordination modes of 4-flourobenzyloxymethylenetriphenylphosphorane ylide (FBPPY), 4-chlorobenzyl-oxymethylenetriphenylphosphorane ylide (CBPPY), and 4-methoxybenzoylmethylenetriphenylphosphorane ylide (MOBPPY) to transition metals such as mercury (II), silver (I) and palladium (II) have been recently investigated by our group (Karami, 2007, 2008; Akkurt et al., 2008). As a part of our ongoing study on the synthesis and characterization of new trifluoromethanesulfonate phosphonium ylides, the title compound has been prepared according to the sequence shown in Figure 3 (Burmeister et al., 1973), and its crystal structure is reported herein.

In the title compound (Fig. 1), bond lengths and angles within the phosphonium cation are not unusual and comparable to those observed for the related 4-methoxybenzoylmethyl derivative (Karami & Büyükgüngör, 2009). The P1–C1 bond length (1.798 (2) Å) is significantly longer than that reported in the free ylide (1.711 Å) of formula Ph₃PC(H)COPh (Shao et al., 1982). The dihedral angle between the benzene rings of the biphenyl group is 42.37 (8)°. Unlike the 4-methoxybenzoylmethyl derivative, the conformation of the cation is not stabilized by intramolecular hydrogen bonds. In the crystal packing (Fig. 2), cations and anions are linked by intermolecular C—H···O hydrogen bonds into chains running parallel to the b axis (see Fig. 2 & Table 1). The chains further interact through C—H···π stacking interactions to form layers parallel to the bc plane (see Fig. 2 & Table 1).

Related literature top

For the synthesis and characterization of phosphorus ylide metal complexes, see: Kalyanasundari et al. (1995, 1999); Laavanya et al. (2001); Vicente et al. (1985); Karami (2007, 2008); Akkurt et al. (2008). For related structures, see: Karami & Büyükgüngör (2009); Shao et al. (1982). For the synthesis of the title compound, see: Burmeister et al. (1973).

Experimental top

The title compound was obtained by reaction of (4–phenylbenzoylmethyl)triphenylphosphonium bromide and AgOTf (OTf : trifluoromethanesulfonate) in dry acetone in a 1:1 molar ratio under stirring for 12 h (Fig. 3). The precipitate obtained was washed several times with dry diethyl ether and dried in a vacuum. Orange crystals of the title compound suitable for X–ray analysis formed by addition of dry diethyl ether to a chloroform solution. The crystals are air stable and resistant against moisture.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and C—H···π interactions (dashed lines) in the crystal structure of the title compound.
	Fig. 3. The procedure adopted for the synthesis of the title compound.

Triphenyl[(4-phenylbenzoyl)methyl]phosphonium trifluoromethanesulfonate top

Crystal data top

C₃₂H₂₆OP⁺·CF₃O₃S⁻	F(000) = 1256
M_r = 606.58	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 744 reflections
a = 9.0559 (10) Å	θ = 6.3–22.4°
b = 19.382 (2) Å	µ = 0.22 mm⁻¹
c = 16.5396 (19) Å	T = 294 K
β = 92.577 (2)°	Block, orange
V = 2900.1 (6) Å³	0.25 × 0.20 × 0.17 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	5245 independent reflections
Radiation source: fine-focus sealed tube	3748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.936, T_max = 0.974	k = −23→23
29195 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.082P)²] where P = (F_o² + 2F_c²)/3
5245 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₂H₂₆OP⁺·CF₃O₃S⁻	V = 2900.1 (6) Å³
M_r = 606.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0559 (10) Å	µ = 0.22 mm⁻¹
b = 19.382 (2) Å	T = 294 K
c = 16.5396 (19) Å	0.25 × 0.20 × 0.17 mm
β = 92.577 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5245 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3748 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.974	R_int = 0.043
29195 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	Δρ_max = 0.56 e Å⁻³
5245 reflections	Δρ_min = −0.29 e Å⁻³
379 parameters

Special details top

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	0.05841 (6)	0.19921 (3)	0.17248 (4)	0.03733 (18)
S1	0.78232 (9)	0.42703 (4)	0.27665 (5)	0.0666 (2)
F1	0.5564 (3)	0.35241 (16)	0.3102 (3)	0.1880 (17)
F2	0.5301 (3)	0.45799 (15)	0.3327 (2)	0.1577 (13)
F3	0.6656 (4)	0.39779 (16)	0.41126 (19)	0.1544 (13)
O1	0.29798 (19)	0.28836 (9)	0.13868 (13)	0.0625 (5)
O2	0.7193 (4)	0.4436 (2)	0.19884 (16)	0.1420 (13)
O3	0.8484 (3)	0.48364 (11)	0.31695 (15)	0.0894 (7)
O4	0.8683 (3)	0.36544 (12)	0.28273 (18)	0.1039 (9)
C1	0.0380 (3)	0.28830 (11)	0.14394 (15)	0.0435 (6)
H1A	−0.0207	0.2913	0.0935	0.052*
H1B	−0.0145	0.3126	0.1851	0.052*
C2	0.1864 (3)	0.32291 (12)	0.13352 (15)	0.0449 (6)
C3	0.1899 (2)	0.39764 (12)	0.11621 (14)	0.0433 (6)
C4	0.0651 (3)	0.43896 (12)	0.11089 (15)	0.0459 (6)
H4	−0.0267	0.4202	0.1211	0.055*
C5	0.0757 (3)	0.50804 (12)	0.09048 (15)	0.0453 (6)
H5	−0.0088	0.5354	0.0883	0.054*
C6	0.2109 (3)	0.53701 (12)	0.07326 (14)	0.0433 (6)
C7	0.3360 (3)	0.49527 (13)	0.08168 (17)	0.0535 (7)
H7	0.4282	0.5140	0.0724	0.064*
C8	0.3263 (3)	0.42769 (13)	0.10323 (17)	0.0523 (7)
H8	0.4119	0.4013	0.1093	0.063*
C9	0.2251 (3)	0.60970 (12)	0.04788 (14)	0.0437 (6)
C10	0.1499 (3)	0.66280 (13)	0.08446 (16)	0.0549 (7)
H10	0.0825	0.6526	0.1235	0.066*
C11	0.1740 (3)	0.73053 (14)	0.06349 (18)	0.0651 (8)
H11	0.1235	0.7657	0.0888	0.078*
C12	0.2723 (3)	0.74644 (14)	0.00535 (18)	0.0613 (7)
H12	0.2913	0.7923	−0.0070	0.074*
C13	0.3418 (3)	0.69483 (15)	−0.03417 (18)	0.0601 (7)
H13	0.4048	0.7055	−0.0753	0.072*
C14	0.3188 (3)	0.62676 (13)	−0.01322 (17)	0.0539 (7)
H14	0.3667	0.5919	−0.0404	0.065*
C15	0.1376 (3)	0.14886 (12)	0.09454 (14)	0.0414 (5)
C16	0.0457 (3)	0.12156 (13)	0.03274 (15)	0.0530 (6)
H16	−0.0555	0.1299	0.0320	0.064*
C17	0.1047 (4)	0.08214 (16)	−0.02744 (18)	0.0690 (8)
H17	0.0437	0.0642	−0.0690	0.083*
C18	0.2538 (4)	0.06968 (16)	−0.02533 (19)	0.0763 (9)
H18	0.2933	0.0427	−0.0655	0.092*
C19	0.3454 (3)	0.09620 (16)	0.03476 (19)	0.0677 (8)
H19	0.4463	0.0872	0.0353	0.081*
C20	0.2880 (3)	0.13635 (13)	0.09469 (15)	0.0511 (6)
H20	0.3505	0.1550	0.1352	0.061*
C21	0.1644 (2)	0.19295 (12)	0.26621 (14)	0.0398 (5)
C22	0.1840 (3)	0.24969 (14)	0.31672 (16)	0.0594 (7)
H22	0.1494	0.2929	0.3003	0.071*
C23	0.2550 (4)	0.24155 (19)	0.39123 (19)	0.0771 (9)
H23	0.2690	0.2796	0.4249	0.093*
C24	0.3053 (3)	0.1785 (2)	0.41654 (18)	0.0728 (9)
H24	0.3536	0.1739	0.4670	0.087*
C25	0.2845 (3)	0.12184 (17)	0.36745 (17)	0.0627 (7)
H25	0.3177	0.0788	0.3851	0.075*
C26	0.2145 (3)	0.12866 (13)	0.29199 (15)	0.0476 (6)
H26	0.2011	0.0903	0.2586	0.057*
C27	−0.1209 (2)	0.16470 (12)	0.19059 (13)	0.0389 (5)
C28	−0.2382 (3)	0.20647 (13)	0.20946 (15)	0.0473 (6)
H28	−0.2285	0.2542	0.2078	0.057*
C29	−0.3701 (3)	0.17695 (15)	0.23093 (18)	0.0591 (7)
H29	−0.4494	0.2050	0.2431	0.071*
C30	−0.3841 (3)	0.10673 (15)	0.23429 (17)	0.0576 (7)
H30	−0.4729	0.0872	0.2488	0.069*
C31	−0.2677 (3)	0.06509 (14)	0.21634 (16)	0.0555 (7)
H31	−0.2781	0.0174	0.2188	0.067*
C32	−0.1356 (3)	0.09315 (12)	0.19477 (15)	0.0469 (6)
H32	−0.0567	0.0647	0.1831	0.056*
C33	0.6237 (4)	0.4073 (2)	0.3325 (3)	0.0963 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0344 (3)	0.0359 (3)	0.0418 (3)	−0.0018 (2)	0.0030 (2)	−0.0002 (3)
S1	0.0717 (5)	0.0581 (5)	0.0714 (5)	−0.0069 (4)	0.0203 (4)	−0.0080 (4)
F1	0.116 (2)	0.126 (2)	0.327 (5)	−0.0639 (19)	0.070 (3)	−0.014 (3)
F2	0.0997 (18)	0.150 (2)	0.229 (3)	0.0702 (17)	0.0710 (19)	0.072 (2)
F3	0.179 (3)	0.161 (3)	0.130 (2)	0.054 (2)	0.077 (2)	0.072 (2)
O1	0.0444 (10)	0.0477 (11)	0.0966 (15)	0.0018 (8)	0.0148 (10)	0.0106 (10)
O2	0.148 (3)	0.214 (4)	0.0626 (17)	−0.034 (2)	−0.0075 (17)	0.0103 (19)
O3	0.1034 (17)	0.0534 (12)	0.1110 (19)	−0.0142 (12)	0.0002 (14)	−0.0081 (12)
O4	0.1033 (18)	0.0602 (14)	0.153 (3)	0.0123 (13)	0.0578 (17)	−0.0148 (14)
C1	0.0414 (13)	0.0375 (13)	0.0520 (14)	−0.0040 (10)	0.0054 (11)	0.0025 (10)
C2	0.0416 (14)	0.0432 (13)	0.0507 (14)	−0.0023 (11)	0.0098 (11)	0.0003 (11)
C3	0.0420 (13)	0.0422 (13)	0.0462 (14)	−0.0041 (10)	0.0084 (10)	−0.0010 (10)
C4	0.0384 (13)	0.0478 (14)	0.0517 (14)	−0.0064 (11)	0.0058 (11)	0.0020 (11)
C5	0.0424 (13)	0.0436 (14)	0.0503 (14)	0.0012 (11)	0.0061 (11)	0.0007 (11)
C6	0.0464 (14)	0.0426 (13)	0.0414 (13)	−0.0025 (11)	0.0066 (10)	−0.0041 (10)
C7	0.0417 (14)	0.0457 (15)	0.0742 (18)	−0.0067 (11)	0.0147 (13)	0.0010 (13)
C8	0.0387 (13)	0.0423 (14)	0.0769 (19)	0.0013 (11)	0.0137 (12)	−0.0007 (12)
C9	0.0452 (13)	0.0424 (13)	0.0435 (13)	−0.0021 (11)	0.0018 (11)	−0.0002 (10)
C10	0.0666 (17)	0.0495 (16)	0.0497 (15)	0.0016 (13)	0.0129 (13)	−0.0033 (12)
C11	0.091 (2)	0.0433 (15)	0.0612 (18)	0.0113 (15)	0.0022 (16)	−0.0048 (13)
C12	0.0691 (18)	0.0428 (15)	0.0709 (19)	−0.0043 (13)	−0.0090 (15)	0.0096 (13)
C13	0.0476 (15)	0.0601 (18)	0.0730 (19)	−0.0016 (13)	0.0078 (13)	0.0194 (15)
C14	0.0504 (15)	0.0471 (15)	0.0652 (17)	0.0008 (12)	0.0148 (13)	0.0026 (12)
C15	0.0467 (14)	0.0397 (13)	0.0382 (13)	0.0008 (10)	0.0056 (10)	0.0023 (10)
C16	0.0560 (15)	0.0547 (16)	0.0481 (15)	−0.0007 (12)	0.0000 (12)	−0.0033 (12)
C17	0.088 (2)	0.068 (2)	0.0516 (17)	−0.0058 (17)	0.0021 (15)	−0.0153 (14)
C18	0.102 (3)	0.071 (2)	0.0576 (19)	0.0077 (19)	0.0256 (18)	−0.0164 (15)
C19	0.0650 (18)	0.0716 (19)	0.068 (2)	0.0138 (15)	0.0215 (15)	−0.0001 (16)
C20	0.0474 (15)	0.0577 (16)	0.0488 (15)	0.0050 (12)	0.0083 (12)	−0.0014 (12)
C21	0.0345 (12)	0.0438 (13)	0.0413 (13)	−0.0028 (10)	0.0044 (9)	−0.0023 (10)
C22	0.0720 (19)	0.0517 (16)	0.0539 (17)	−0.0014 (14)	−0.0032 (14)	−0.0094 (13)
C23	0.087 (2)	0.085 (2)	0.0588 (19)	−0.0074 (19)	−0.0087 (16)	−0.0219 (17)
C24	0.0621 (19)	0.107 (3)	0.0481 (17)	0.0019 (18)	−0.0105 (14)	−0.0032 (17)
C25	0.0531 (16)	0.078 (2)	0.0571 (18)	0.0112 (14)	−0.0008 (13)	0.0138 (15)
C26	0.0446 (14)	0.0495 (15)	0.0485 (14)	0.0015 (11)	0.0005 (11)	0.0010 (11)
C27	0.0351 (12)	0.0427 (13)	0.0387 (12)	−0.0022 (10)	−0.0001 (10)	0.0016 (10)
C28	0.0417 (13)	0.0434 (14)	0.0567 (15)	−0.0007 (11)	0.0018 (11)	−0.0025 (11)
C29	0.0372 (14)	0.0685 (19)	0.0719 (19)	0.0000 (13)	0.0076 (13)	−0.0009 (14)
C30	0.0399 (14)	0.0691 (19)	0.0642 (18)	−0.0146 (13)	0.0041 (12)	0.0028 (14)
C31	0.0545 (16)	0.0468 (15)	0.0649 (18)	−0.0150 (12)	0.0011 (13)	0.0038 (12)
C32	0.0434 (13)	0.0422 (14)	0.0554 (15)	−0.0022 (11)	0.0039 (11)	0.0027 (11)
C33	0.078 (2)	0.077 (3)	0.137 (4)	0.019 (2)	0.036 (2)	0.028 (2)

Geometric parameters (Å, º) top

P1—C21	1.790 (2)	C13—H13	0.9300
P1—C15	1.792 (2)	C14—H14	0.9300
P1—C27	1.794 (2)	C15—C20	1.383 (3)
P1—C1	1.798 (2)	C15—C16	1.393 (3)
S1—O3	1.404 (2)	C16—C17	1.381 (4)
S1—O2	1.421 (3)	C16—H16	0.9300
S1—O4	1.427 (2)	C17—C18	1.371 (4)
S1—C33	1.783 (4)	C17—H17	0.9300
F1—C33	1.273 (5)	C18—C19	1.366 (4)
F2—C33	1.298 (4)	C18—H18	0.9300
F3—C33	1.354 (5)	C19—C20	1.380 (4)
O1—C2	1.212 (3)	C19—H19	0.9300
C1—C2	1.519 (3)	C20—H20	0.9300
C1—H1A	0.9700	C21—C26	1.387 (3)
C1—H1B	0.9700	C21—C22	1.388 (3)
C2—C3	1.477 (3)	C22—C23	1.373 (4)
C3—C4	1.385 (3)	C22—H22	0.9300
C3—C8	1.391 (3)	C23—C24	1.363 (5)
C4—C5	1.385 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.374 (4)
C5—C6	1.387 (3)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.380 (4)
C6—C7	1.394 (3)	C25—H25	0.9300
C6—C9	1.477 (3)	C26—H26	0.9300
C7—C8	1.361 (3)	C27—C28	1.382 (3)
C7—H7	0.9300	C27—C32	1.395 (3)
C8—H8	0.9300	C28—C29	1.385 (3)
C9—C10	1.388 (3)	C28—H28	0.9300
C9—C14	1.389 (3)	C29—C30	1.368 (4)
C10—C11	1.378 (4)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.371 (4)
C11—C12	1.374 (4)	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.376 (3)
C12—C13	1.365 (4)	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.382 (4)

C21—P1—C15	111.69 (11)	C16—C15—P1	119.27 (19)
C21—P1—C27	106.52 (10)	C17—C16—C15	120.0 (3)
C15—P1—C27	108.17 (11)	C17—C16—H16	120.0
C21—P1—C1	109.71 (11)	C15—C16—H16	120.0
C15—P1—C1	111.96 (11)	C18—C17—C16	119.5 (3)
C27—P1—C1	108.60 (11)	C18—C17—H17	120.3
O3—S1—O2	113.5 (2)	C16—C17—H17	120.3
O3—S1—O4	113.63 (16)	C19—C18—C17	121.2 (3)
O2—S1—O4	116.7 (2)	C19—C18—H18	119.4
O3—S1—C33	104.93 (19)	C17—C18—H18	119.4
O2—S1—C33	102.5 (2)	C18—C19—C20	119.9 (3)
O4—S1—C33	103.55 (16)	C18—C19—H19	120.0
C2—C1—P1	111.90 (16)	C20—C19—H19	120.0
C2—C1—H1A	109.2	C19—C20—C15	120.0 (3)
P1—C1—H1A	109.2	C19—C20—H20	120.0
C2—C1—H1B	109.2	C15—C20—H20	120.0
P1—C1—H1B	109.2	C26—C21—C22	119.7 (2)
H1A—C1—H1B	107.9	C26—C21—P1	118.85 (18)
O1—C2—C3	122.0 (2)	C22—C21—P1	121.1 (2)
O1—C2—C1	119.1 (2)	C23—C22—C21	119.4 (3)
C3—C2—C1	118.8 (2)	C23—C22—H22	120.3
C4—C3—C8	118.4 (2)	C21—C22—H22	120.3
C4—C3—C2	123.7 (2)	C24—C23—C22	121.0 (3)
C8—C3—C2	117.9 (2)	C24—C23—H23	119.5
C5—C4—C3	120.6 (2)	C22—C23—H23	119.5
C5—C4—H4	119.7	C23—C24—C25	120.0 (3)
C3—C4—H4	119.7	C23—C24—H24	120.0
C4—C5—C6	120.9 (2)	C25—C24—H24	120.0
C4—C5—H5	119.6	C24—C25—C26	120.2 (3)
C6—C5—H5	119.6	C24—C25—H25	119.9
C5—C6—C7	117.7 (2)	C26—C25—H25	119.9
C5—C6—C9	122.2 (2)	C25—C26—C21	119.7 (2)
C7—C6—C9	120.1 (2)	C25—C26—H26	120.2
C8—C7—C6	121.5 (2)	C21—C26—H26	120.2
C8—C7—H7	119.2	C28—C27—C32	119.7 (2)
C6—C7—H7	119.2	C28—C27—P1	121.99 (18)
C7—C8—C3	120.8 (2)	C32—C27—P1	117.89 (17)
C7—C8—H8	119.6	C27—C28—C29	119.7 (2)
C3—C8—H8	119.6	C27—C28—H28	120.1
C10—C9—C14	117.9 (2)	C29—C28—H28	120.1
C10—C9—C6	122.2 (2)	C30—C29—C28	120.3 (2)
C14—C9—C6	119.9 (2)	C30—C29—H29	119.9
C11—C10—C9	120.7 (3)	C28—C29—H29	119.9
C11—C10—H10	119.7	C29—C30—C31	120.2 (2)
C9—C10—H10	119.7	C29—C30—H30	119.9
C12—C11—C10	120.3 (3)	C31—C30—H30	119.9
C12—C11—H11	119.8	C30—C31—C32	120.6 (2)
C10—C11—H11	119.8	C30—C31—H31	119.7
C13—C12—C11	119.9 (3)	C32—C31—H31	119.7
C13—C12—H12	120.1	C31—C32—C27	119.5 (2)
C11—C12—H12	120.1	C31—C32—H32	120.3
C12—C13—C14	120.1 (3)	C27—C32—H32	120.3
C12—C13—H13	119.9	F1—C33—F2	109.2 (4)
C14—C13—H13	119.9	F1—C33—F3	105.9 (4)
C13—C14—C9	120.9 (2)	F2—C33—F3	104.8 (4)
C13—C14—H14	119.5	F1—C33—S1	114.5 (3)
C9—C14—H14	119.5	F2—C33—S1	112.4 (3)
C20—C15—C16	119.4 (2)	F3—C33—S1	109.3 (3)
C20—C15—P1	121.34 (19)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C21–C26 and C15–C20 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱ	0.97	2.22	3.191 (4)	178
C26—H26···O3ⁱⁱ	0.93	2.45	3.373 (3)	174
C32—H32···O3ⁱⁱ	0.93	2.46	3.369 (4)	168
C1—H1A···Cg1ⁱⁱⁱ	0.97	2.84	3.780 (3)	164
C10—H10···Cg2^iv	0.93	3.02	3.767 (4)	138
C23—H23···Cg3^v	0.93	2.91	3.788 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₃₂H₂₆OP⁺·CF₃O₃S⁻
M_r	606.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.0559 (10), 19.382 (2), 16.5396 (19)
β (°)	92.577 (2)
V (Å³)	2900.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.936, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	29195, 5245, 3748
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.06
No. of reflections	5245
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.29

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997), SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C21–C26 and C15–C20 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱ	0.97	2.22	3.191 (4)	177.9
C26—H26···O3ⁱⁱ	0.93	2.45	3.373 (3)	173.7
C32—H32···O3ⁱⁱ	0.93	2.46	3.369 (4)	167.8
C1—H1A···Cg1ⁱⁱⁱ	0.97	2.84	3.780 (3)	163.6
C10—H10···Cg2^iv	0.93	3.02	3.767 (4)	138.3
C23—H23···Cg3^v	0.93	2.91	3.788 (4)	158.7

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

Acknowledgements

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

References

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Volume 66| Part 10| October 2010| Pages o2675-o2676

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