Triphen-yl[(4-phenyl-benzo-yl)meth-yl]phospho-nium trifluoro-methane-sulfonate.

In the cation of the title compound, C(32)H(26)OP(+)·CF(3)O(3)S(-), the dihedral angle between the benzene rings of the biphenyl group is 42.37 (8)°. In the crystal, the cations and anions inter-act through inter-molecular C-H⋯O hydrogen bonds, forming chains parallel to the b axis. These chains are further linked by C-H⋯π stacking inter-actions 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 = 606.58

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.06

5245 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C32H26OP+·CF3O3S−	F(000) = 1256
Mr = 606.58	Dx = 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

Bruker SMART 1000 CCD diffractometer	5245 independent reflections
Radiation source: fine-focus sealed tube	3748 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 25.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.936, Tmax = 0.974	k = −23→23
29195 measured reflections	l = −19→19

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(Fo2) + (0.082P)2] where P = (Fo2 + 2Fc2)/3
5245 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···Cg2iv	0.93	3.02	3.767 (4)	138
C23—H23···Cg3v	0.93	2.91	3.788 (4)	159

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⋯Cg2iv	0.93	3.02	3.767 (4)	138
C23—H23⋯Cg3v	0.93	2.91	3.788 (4)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .