(4-Methoxy­benzoyl­meth­yl)triphenyl­phospho­nium trifluoro­methane­sulfonate

Karami, K.; Büyükgüngör, O.

doi:10.1107/S1600536809000919

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o296

doi:10.1107/S1600536809000919

Open

access

(4-Methoxybenzoylmethyl)triphenylphosphonium trifluoromethanesulfonate

Kazem Karami ^a and Orhan Büyükgüngör ^b ^*

^aDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156/83111, Iran, and ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: karami@cc.iut.ac.ir

(Received 30 December 2008; accepted 8 January 2009; online 14 January 2009)

Colourless crystals of the title compound, C₂₇H₂₄O₂P⁺·CF₃SO₃⁻, have been prepared by the addition of a solution of AgCF₃SO₃ in methanol to a solution of (4-methoxybenzoylmethyl)triphenylphosphonium bromide in dry methanol. There are two crystallographically independent molecules in the asymmetric unit. The crystal structure is stabilized by inter- and intramolecular C—H⋯O hydrogen bonds and further stabilized by C—H⋯π interactions.

Related literature

For background to phosphorus ylides, see: Akkurt et al. (2008 );; Kalyanasundari et al. (1995 , 1999 ); Kolodiazhnyi (1996 ); Laavanya et al. (2001 ); Vicente et al. (1985 ). For the synthesis, see: Burmeister et al. (1973 ).

Experimental

Crystal data

C₂₇H₂₄O₂P⁺·CF₃O₃S⁻
M_r = 560.50
Monoclinic, P 2₁ /c
a = 10.6641 (5) Å
b = 20.2760 (12) Å
c = 25.0960 (11) Å
β = 96.539 (3)°
V = 5391.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 (2) K
0.67 × 0.33 × 0.14 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32: Stoe & Cie, 2002 ) T_min = 0.766, T_max = 0.902
75273 measured reflections
11185 independent reflections
6282 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.188
S = 1.07
11185 reflections
685 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O5	0.97	2.34	3.207 (6)	149
C19—H19B⋯O3ⁱ	0.97	2.54	3.487 (5)	166
C33—H33⋯O6ⁱⁱ	0.93	2.34	3.130 (6)	143
C45—H45⋯O3	0.93	2.52	3.071 (6)	118
C46—H46A⋯O1	0.97	2.48	3.417 (5)	162
C46—H46B⋯O10ⁱⁱⁱ	0.97	2.19	3.137 (7)	165
C44—H44⋯Cg4^iv	0.93	2.83	3.640 (6)	147
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x+1, y, z. Cg4 is the centroid of the C21–C26 benzene ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000919/at2703sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000919/at2703Isup2.hkl

checkCIF report

Comment top

Phosphorus ylide have been increasingly studied over the past decade because of their interesting structure. the utilies of metalated phosphorus ylides in synthetic chemistry have been well documented (Kolodiazhnyi et al., 1996). The α-keto-stabilized phosphorus ylides R₃P═CHCOR show interesting properties such as high stability and ambidentate character as ligands (C-versus O-coordination) (Vicente et al., 1985; Kalyanasundari et al., 1995; Laavanya et al., 2001). Phosphorus ylides are known to demonstrate rich coordination chemistry. One of the significance aspects of our work is taking knowledge about preferred coordination modes of FBPPY, CBPPY, BrBPPY, and MOBPPY to the Hg and Pd metals (Akkurt et al., 2008). The phosphonium salt (I) (Fig. 1) was synthesized according to sequence mentioned in Scheme 2 (Burmeister et al., 1973).

In this communication we have reported the preparations and structures of new tri-folourosulfonate phosphonium ylides.

In the asymmetric unit of (I), there are two crystallographically independent molecules (Fig. 1). A comparison of the bond lengths and bond angles in (I) shows that the phosphonium cation as a ligand is electrostatically under the influence of an anionic part of OTf in the unit cells. X-ray structural analysis established that Fig. 1 contains of discrete [CH₃OC₆H₄COCH₂PPh₃]⁺ cations and OTf^- anions in a 1:1 ratio. An ORTEP plot (Fig. 1) and crystal packing view (Fig. 2) show that the double tetrahedral OTf unit is formed by sharing one tetrahedral edge, and possesses approximate C₃V symmetry. These units are held together by electrostatic forces. In the fact, the crystal of the phosphonium (I) shows a close association between the OTf^- and the inner sphere, with O···H distances of 3.07 (16) and 3.487 (5) Å (see Fig. 2, Table 1).

Comparision of the bond lengths and bond angles within the above crystal show that the phosphonium as a ligand is electrostatically under the influence of an anionic part of trifloro solfonate in the unit cells (for instance, the bond lengths C21—C20, O1—C20, C20—C19, C19—P1 and P1—C1 and bond angles C19—P1—C1, O1—C20—C21 are 1.471 (5), 1.226 (5), 1.517 (6), 1.798 (4) and 1.797 (4) Å and 113.17 (19) and 120.4 (4)° for the title compound and 1.493 (9), 1.212 (9), 1.491 (10), 1787 (6) and 1.806 (8) Å and 122.2 (4)° for the phosphorane molecule (Laavanya et al., 2001).

The P—C bond length [1.727 (2) Å] is shorter than the other P—C bonds and longer than the equivalent bond lengths of 1.66 Å, reported for methylenetriphenylphosphorane, which shows partial double-bond character for these two bonds.

The crystal structure is stabilized by C—H···O hydrogen bonds and further by C—H···π interactions.

Related literature top

For background to phosphorus ylides, see: Akkurt et al. (2008);; Kalyanasundari et al. (1995, 1999); Kolodiazhnyi (1996); Laavanya et al. (2001); Vicente et al. (1985). For the synthesis, see: Burmeister et al. (1973). Cg4 is the centroid of the C21–C26 benzene ring.

Experimental top

The title compound was obtained from reaction between (I) and AgOTf in dry methanol in a 1:1 molar ratio and under stirring for 12 h. The product was washed sveral times with dry diethyl ether and dried in a vacuum. Colourless plate crystals of C₂₇H₂₄F₃O₅P appeared by addition of dry diethyl ether to a chlroform solution. The crystal structure consists of discrete [CH₃OC₆H₄COCH₂PPh₃]+, cations and OTf^- anions in a 1:1 ratio. The obtained crystals of (I) are highly air stable and resistant against moisture.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP plotting of one molecule in the asymmetric unit of the title compound (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding interactions of (I), viewed down a axis.
	Fig. 3. The formation of the title compound.

(4-Methoxybenzoylmethyl)triphenylphosphonium trifluoromethanesulfonate top

Crystal data top

C₂₇H₂₄O₂P⁺·CF₃O₃S⁻	F(000) = 2320
M_r = 560.50	D_x = 1.381 Mg m⁻³ D_m = 1.381 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Melting point: 296 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.6641 (5) Å	Cell parameters from 685 reflections
b = 20.2760 (12) Å	θ = 1–26.5°
c = 25.0960 (11) Å	µ = 0.24 mm⁻¹
β = 96.539 (3)°	T = 293 K
V = 5391.1 (5) Å³	Prism, yellow
Z = 8	0.67 × 0.33 × 0.14 mm

Data collection top

Stoe IPDSII diffractometer	11185 independent reflections
Radiation source: fine-focfine-focus us sealed tube	6282 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.3°
rotation scans	h = −13→13
Absorption correction: integration (X-RED32: Stoe & Cie, 2002)	k = −25→25
T_min = 0.766, T_max = 0.902	l = −31→31
75273 measured reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0814P)²] where P = (F_o² + 2F_c²)/3
11185 reflections	(Δ/σ)_max < 0.001
685 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³
0 constraints

Crystal data top

C₂₇H₂₄O₂P⁺·CF₃O₃S⁻	V = 5391.1 (5) Å³
M_r = 560.50	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6641 (5) Å	µ = 0.24 mm⁻¹
b = 20.2760 (12) Å	T = 293 K
c = 25.0960 (11) Å	0.67 × 0.33 × 0.14 mm
β = 96.539 (3)°

Data collection top

Stoe IPDSII diffractometer	11185 independent reflections
Absorption correction: integration (X-RED32: Stoe & Cie, 2002)	6282 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.902	R_int = 0.082
75273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.07	Δρ_max = 0.46 e Å⁻³
11185 reflections	Δρ_min = −0.29 e Å⁻³
685 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
C1	0.2371 (3)	0.4197 (2)	0.62037 (15)	0.0498 (9)
C2	0.3253 (4)	0.4694 (2)	0.62123 (18)	0.0650 (11)
H2	0.3261	0.5035	0.6461	0.078*
C3	0.4130 (4)	0.4678 (3)	0.5844 (2)	0.0803 (14)
H3	0.4732	0.5010	0.5845	0.096*
C4	0.4111 (4)	0.4177 (3)	0.54798 (19)	0.0798 (15)
H4	0.4699	0.4175	0.5233	0.096*
C5	0.3252 (4)	0.3682 (3)	0.54703 (17)	0.0723 (13)
H5	0.3262	0.3339	0.5225	0.087*
C6	0.2369 (4)	0.3695 (2)	0.58279 (16)	0.0602 (11)
H6	0.1763	0.3364	0.5818	0.072*
C7	−0.0308 (4)	0.4156 (2)	0.61744 (15)	0.0528 (9)
C8	−0.0458 (4)	0.4641 (2)	0.57783 (16)	0.0622 (11)
H8	0.0151	0.4968	0.5769	0.075*
C9	−0.1508 (4)	0.4638 (3)	0.53982 (18)	0.0742 (13)
H9	−0.1609	0.4963	0.5135	0.089*
C10	−0.2396 (5)	0.4153 (3)	0.5414 (2)	0.0873 (16)
H10	−0.3085	0.4140	0.5151	0.105*
C11	−0.2280 (5)	0.3693 (3)	0.5808 (2)	0.1002 (19)
H11	−0.2912	0.3380	0.5823	0.120*
C12	−0.1216 (4)	0.3684 (3)	0.6196 (2)	0.0782 (14)
H12	−0.1133	0.3362	0.6462	0.094*
C13	0.1237 (4)	0.3494 (2)	0.70769 (15)	0.0543 (10)
C14	0.0411 (5)	0.3450 (3)	0.74678 (19)	0.0782 (14)
H14	−0.0195	0.3774	0.7495	0.094*
C15	0.0505 (5)	0.2920 (3)	0.7812 (2)	0.0906 (16)
H15	−0.0046	0.2887	0.8073	0.109*
C16	0.1381 (5)	0.2446 (3)	0.7779 (2)	0.0836 (15)
H16	0.1435	0.2094	0.8018	0.100*
C17	0.2186 (5)	0.2481 (2)	0.7395 (2)	0.0775 (13)
H17	0.2774	0.2147	0.7368	0.093*
C18	0.2133 (4)	0.3009 (2)	0.70465 (17)	0.0642 (11)
H18	0.2699	0.3038	0.6792	0.077*
C19	0.1036 (4)	0.4932 (2)	0.70104 (15)	0.0539 (10)
H19A	0.1028	0.5307	0.6770	0.065*
H19B	0.0247	0.4935	0.7169	0.065*
C20	0.2119 (4)	0.5012 (2)	0.74527 (15)	0.0503 (9)
C21	0.1997 (3)	0.55009 (19)	0.78769 (15)	0.0495 (9)
C22	0.1026 (4)	0.5967 (2)	0.78495 (17)	0.0592 (10)
H22	0.0417	0.5973	0.7553	0.071*
C23	0.0962 (4)	0.6414 (2)	0.82528 (17)	0.0652 (11)
H23	0.0316	0.6725	0.8228	0.078*
C24	0.1854 (4)	0.6404 (2)	0.86965 (17)	0.0637 (11)
C25	0.2826 (4)	0.5952 (2)	0.87317 (16)	0.0637 (12)
H25	0.3433	0.5948	0.9029	0.076*
C26	0.2887 (4)	0.5508 (2)	0.83254 (16)	0.0574 (10)
H26	0.3542	0.5202	0.8350	0.069*
C27	0.2565 (6)	0.6850 (4)	0.9558 (2)	0.119 (2)
H27A	0.2362	0.7201	0.9790	0.179*
H27B	0.3415	0.6903	0.9473	0.179*
H27C	0.2489	0.6434	0.9735	0.179*
C28	0.6457 (3)	0.3595 (2)	0.76582 (15)	0.0513 (9)
C29	0.5704 (4)	0.3669 (2)	0.71752 (17)	0.0659 (12)
H29	0.5308	0.4070	0.7090	0.079*
C30	0.5537 (5)	0.3152 (3)	0.68215 (19)	0.0781 (14)
H30	0.5015	0.3201	0.6501	0.094*
C31	0.6134 (5)	0.2572 (3)	0.6939 (2)	0.0835 (15)
H31	0.6030	0.2224	0.6696	0.100*
C32	0.6883 (5)	0.2494 (3)	0.7409 (2)	0.0913 (16)
H32	0.7285	0.2092	0.7486	0.110*
C33	0.7055 (4)	0.3002 (2)	0.77731 (18)	0.0702 (12)
H33	0.7571	0.2946	0.8094	0.084*
C34	0.5360 (4)	0.40709 (19)	0.85901 (15)	0.0517 (9)
C35	0.4350 (4)	0.3661 (2)	0.84246 (18)	0.0716 (13)
H35	0.4278	0.3472	0.8085	0.086*
C36	0.3453 (5)	0.3534 (3)	0.8767 (2)	0.1001 (19)
H36	0.2769	0.3262	0.8658	0.120*
C37	0.3577 (6)	0.3812 (4)	0.9268 (3)	0.104 (2)
H37	0.2983	0.3717	0.9501	0.125*
C38	0.4554 (6)	0.4223 (3)	0.9431 (2)	0.0998 (18)
H38	0.4620	0.4412	0.9770	0.120*
C39	0.5447 (5)	0.4357 (2)	0.90883 (18)	0.0732 (13)
H39	0.6110	0.4643	0.9196	0.088*
C40	0.8025 (4)	0.4269 (2)	0.85787 (16)	0.0548 (10)
C41	0.8310 (4)	0.3769 (2)	0.89511 (18)	0.0698 (12)
H41	0.7763	0.3413	0.8965	0.084*
C42	0.9406 (5)	0.3798 (3)	0.9301 (2)	0.0839 (15)
H42	0.9601	0.3459	0.9546	0.101*
C43	1.0204 (5)	0.4323 (3)	0.9288 (2)	0.0912 (17)
H43	1.0938	0.4343	0.9526	0.109*
C44	0.9928 (5)	0.4816 (3)	0.8928 (2)	0.0897 (16)
H44	1.0476	0.5172	0.8920	0.108*
C45	0.8839 (4)	0.4793 (2)	0.8573 (2)	0.0727 (13)
H45	0.8656	0.5134	0.8329	0.087*
C46	0.6179 (4)	0.50060 (19)	0.78234 (16)	0.0514 (9)
H46A	0.5295	0.5006	0.7679	0.062*
H46B	0.6304	0.5360	0.8084	0.062*
C47	0.6978 (4)	0.5137 (2)	0.73732 (16)	0.0534 (10)
C48	0.6536 (3)	0.56138 (19)	0.69497 (15)	0.0495 (9)
C49	0.5466 (4)	0.6000 (2)	0.69589 (17)	0.0607 (11)
H49	0.5008	0.5974	0.7252	0.073*
C50	0.5068 (4)	0.6422 (2)	0.65444 (19)	0.0709 (12)
H50	0.4345	0.6676	0.6556	0.085*
C51	0.5753 (4)	0.6464 (2)	0.61101 (17)	0.0660 (12)
C52	0.6829 (5)	0.6085 (3)	0.6100 (2)	0.0819 (15)
H52	0.7296	0.6115	0.5810	0.098*
C53	0.7206 (4)	0.5672 (2)	0.65113 (18)	0.0676 (12)
H53	0.7932	0.5421	0.6499	0.081*
C54	0.4351 (6)	0.7247 (3)	0.5649 (2)	0.110 (2)
H54A	0.4263	0.7492	0.5320	0.165*
H54B	0.4419	0.7546	0.5947	0.165*
H54C	0.3625	0.6970	0.5663	0.165*
C55	−0.0022 (5)	0.6781 (3)	0.5545 (2)	0.0789 (14)
C56	0.8050 (6)	0.8346 (3)	0.4279 (3)	0.0893 (16)
F1	−0.0619 (3)	0.6251 (2)	0.53358 (14)	0.1184 (12)
F2	−0.0878 (3)	0.72038 (18)	0.56646 (15)	0.1195 (12)
F3	0.0579 (4)	0.7046 (2)	0.51722 (14)	0.1332 (14)
F4	0.8159 (4)	0.8128 (3)	0.47665 (15)	0.1514 (17)
F5	0.8797 (5)	0.8827 (3)	0.4279 (3)	0.211 (3)
F6	0.8564 (4)	0.7876 (2)	0.40148 (19)	0.1530 (16)
O1	0.3065 (3)	0.46701 (15)	0.74453 (11)	0.0653 (8)
O2	0.1719 (3)	0.68647 (18)	0.90766 (14)	0.0893 (11)
O3	0.7972 (3)	0.48392 (16)	0.73638 (12)	0.0718 (9)
O4	0.5451 (4)	0.68504 (19)	0.56762 (13)	0.0946 (11)
O5	0.0177 (4)	0.6331 (2)	0.64958 (14)	0.1079 (13)
O6	0.1662 (4)	0.71576 (19)	0.6272 (2)	0.1266 (16)
O7	0.1802 (3)	0.60495 (18)	0.59502 (17)	0.0979 (12)
O8	0.5820 (5)	0.7954 (3)	0.4125 (3)	0.183 (3)
O9	0.6181 (6)	0.9064 (3)	0.4313 (2)	0.157 (2)
O10	0.6530 (6)	0.8681 (3)	0.34844 (17)	0.154 (2)
P1	0.11235 (9)	0.41867 (5)	0.66285 (4)	0.0478 (3)
P2	0.65496 (9)	0.42347 (5)	0.81549 (4)	0.0482 (3)
S1	0.10381 (12)	0.65597 (6)	0.61330 (5)	0.0681 (3)
S2	0.64543 (14)	0.85241 (7)	0.40166 (5)	0.0844 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (2)	0.057 (2)	0.048 (2)	0.0017 (19)	0.0011 (16)	0.0038 (19)
C2	0.057 (3)	0.072 (3)	0.066 (3)	−0.004 (2)	0.007 (2)	0.002 (2)
C3	0.056 (3)	0.102 (4)	0.084 (3)	−0.018 (3)	0.015 (2)	0.012 (3)
C4	0.056 (3)	0.127 (5)	0.059 (3)	0.010 (3)	0.017 (2)	0.010 (3)
C5	0.066 (3)	0.100 (4)	0.052 (2)	0.010 (3)	0.013 (2)	−0.003 (2)
C6	0.064 (3)	0.066 (3)	0.052 (2)	−0.002 (2)	0.011 (2)	−0.002 (2)
C7	0.049 (2)	0.059 (3)	0.051 (2)	−0.002 (2)	0.0066 (17)	−0.0054 (19)
C8	0.053 (2)	0.071 (3)	0.061 (3)	0.001 (2)	−0.0010 (19)	0.001 (2)
C9	0.063 (3)	0.099 (4)	0.057 (3)	0.009 (3)	−0.006 (2)	−0.002 (2)
C10	0.052 (3)	0.137 (5)	0.071 (3)	−0.001 (3)	−0.005 (2)	−0.005 (3)
C11	0.062 (3)	0.137 (5)	0.099 (4)	−0.040 (3)	−0.004 (3)	−0.006 (4)
C12	0.068 (3)	0.090 (4)	0.074 (3)	−0.022 (3)	−0.001 (2)	0.013 (3)
C13	0.053 (2)	0.060 (3)	0.050 (2)	−0.004 (2)	0.0040 (18)	0.0005 (19)
C14	0.071 (3)	0.096 (4)	0.071 (3)	0.013 (3)	0.021 (2)	0.020 (3)
C15	0.083 (4)	0.112 (5)	0.081 (3)	−0.005 (3)	0.023 (3)	0.031 (3)
C16	0.096 (4)	0.077 (4)	0.076 (3)	−0.016 (3)	−0.001 (3)	0.027 (3)
C17	0.088 (3)	0.068 (3)	0.075 (3)	0.013 (3)	0.001 (3)	0.011 (3)
C18	0.066 (3)	0.067 (3)	0.061 (3)	0.005 (2)	0.011 (2)	0.004 (2)
C19	0.048 (2)	0.059 (2)	0.053 (2)	0.0056 (19)	0.0005 (18)	−0.0051 (19)
C20	0.046 (2)	0.055 (2)	0.049 (2)	−0.0009 (19)	0.0031 (17)	0.0014 (18)
C21	0.047 (2)	0.053 (2)	0.048 (2)	−0.0055 (18)	0.0044 (16)	0.0001 (18)
C22	0.059 (2)	0.059 (3)	0.058 (2)	0.004 (2)	−0.0016 (19)	−0.004 (2)
C23	0.065 (3)	0.061 (3)	0.069 (3)	0.007 (2)	0.004 (2)	−0.012 (2)
C24	0.065 (3)	0.065 (3)	0.063 (3)	−0.010 (2)	0.013 (2)	−0.012 (2)
C25	0.050 (2)	0.087 (3)	0.052 (2)	−0.006 (2)	−0.0022 (18)	−0.010 (2)
C26	0.046 (2)	0.071 (3)	0.054 (2)	0.001 (2)	−0.0003 (18)	−0.001 (2)
C27	0.111 (5)	0.167 (7)	0.077 (4)	0.003 (4)	−0.001 (3)	−0.065 (4)
C28	0.041 (2)	0.057 (2)	0.056 (2)	0.0049 (18)	0.0039 (17)	0.0036 (19)
C29	0.064 (3)	0.071 (3)	0.059 (3)	0.015 (2)	−0.006 (2)	−0.003 (2)
C30	0.071 (3)	0.098 (4)	0.062 (3)	0.011 (3)	−0.003 (2)	−0.013 (3)
C31	0.082 (3)	0.084 (4)	0.085 (4)	0.005 (3)	0.007 (3)	−0.031 (3)
C32	0.104 (4)	0.074 (3)	0.093 (4)	0.032 (3)	−0.003 (3)	−0.013 (3)
C33	0.079 (3)	0.069 (3)	0.059 (3)	0.021 (3)	−0.005 (2)	−0.006 (2)
C34	0.051 (2)	0.051 (2)	0.054 (2)	0.0043 (18)	0.0060 (17)	0.0061 (18)
C35	0.060 (3)	0.094 (4)	0.060 (3)	−0.013 (3)	0.006 (2)	0.006 (2)
C36	0.067 (3)	0.139 (5)	0.098 (4)	−0.030 (3)	0.024 (3)	0.001 (4)
C37	0.082 (4)	0.144 (6)	0.095 (4)	0.003 (4)	0.043 (3)	0.019 (4)
C38	0.109 (5)	0.128 (5)	0.068 (3)	0.003 (4)	0.037 (3)	−0.003 (3)
C39	0.077 (3)	0.080 (3)	0.065 (3)	−0.008 (3)	0.020 (2)	−0.004 (2)
C40	0.050 (2)	0.054 (2)	0.059 (2)	0.002 (2)	0.0004 (18)	0.0033 (19)
C41	0.067 (3)	0.058 (3)	0.080 (3)	−0.003 (2)	−0.014 (2)	0.010 (2)
C42	0.081 (3)	0.076 (3)	0.088 (3)	0.013 (3)	−0.024 (3)	0.018 (3)
C43	0.056 (3)	0.101 (4)	0.109 (4)	−0.008 (3)	−0.025 (3)	0.012 (3)
C44	0.064 (3)	0.094 (4)	0.105 (4)	−0.025 (3)	−0.015 (3)	0.017 (3)
C45	0.063 (3)	0.069 (3)	0.083 (3)	−0.012 (2)	−0.005 (2)	0.012 (2)
C46	0.047 (2)	0.052 (2)	0.055 (2)	0.0065 (18)	0.0074 (17)	0.0061 (18)
C47	0.048 (2)	0.052 (2)	0.061 (2)	0.0030 (19)	0.0104 (18)	0.0085 (19)
C48	0.045 (2)	0.049 (2)	0.055 (2)	0.0013 (17)	0.0077 (17)	0.0053 (17)
C49	0.062 (3)	0.063 (3)	0.059 (2)	0.009 (2)	0.016 (2)	0.013 (2)
C50	0.068 (3)	0.069 (3)	0.076 (3)	0.017 (2)	0.010 (2)	0.014 (2)
C51	0.077 (3)	0.063 (3)	0.057 (3)	0.001 (2)	0.002 (2)	0.018 (2)
C52	0.072 (3)	0.106 (4)	0.071 (3)	0.005 (3)	0.021 (2)	0.026 (3)
C53	0.051 (2)	0.086 (3)	0.067 (3)	0.010 (2)	0.011 (2)	0.020 (2)
C54	0.113 (5)	0.102 (5)	0.107 (4)	0.030 (4)	−0.019 (4)	0.036 (4)
C55	0.080 (3)	0.076 (3)	0.082 (3)	−0.003 (3)	0.013 (3)	0.012 (3)
C56	0.105 (4)	0.071 (4)	0.093 (4)	−0.008 (3)	0.013 (3)	−0.011 (3)
F1	0.107 (2)	0.135 (3)	0.104 (2)	−0.025 (2)	−0.0280 (19)	−0.013 (2)
F2	0.102 (2)	0.116 (3)	0.140 (3)	0.044 (2)	0.009 (2)	0.038 (2)
F3	0.146 (3)	0.164 (4)	0.095 (2)	0.002 (3)	0.037 (2)	0.054 (2)
F4	0.140 (3)	0.216 (5)	0.090 (3)	0.046 (3)	−0.023 (2)	0.014 (3)
F5	0.134 (4)	0.124 (4)	0.361 (9)	−0.039 (3)	−0.029 (5)	0.026 (5)
F6	0.148 (4)	0.148 (4)	0.164 (4)	0.042 (3)	0.024 (3)	−0.029 (3)
O1	0.0527 (16)	0.079 (2)	0.0620 (17)	0.0156 (15)	−0.0035 (13)	−0.0125 (15)
O2	0.084 (2)	0.097 (3)	0.086 (2)	−0.001 (2)	0.0076 (19)	−0.042 (2)
O3	0.0541 (17)	0.087 (2)	0.077 (2)	0.0193 (16)	0.0190 (15)	0.0247 (17)
O4	0.106 (3)	0.105 (3)	0.072 (2)	0.026 (2)	0.0070 (19)	0.039 (2)
O5	0.134 (3)	0.120 (3)	0.074 (2)	0.020 (3)	0.028 (2)	0.029 (2)
O6	0.131 (3)	0.079 (3)	0.157 (4)	−0.016 (2)	−0.040 (3)	−0.034 (3)
O7	0.082 (2)	0.078 (2)	0.129 (3)	0.023 (2)	−0.005 (2)	−0.019 (2)
O8	0.132 (4)	0.163 (5)	0.236 (6)	−0.068 (4)	−0.057 (4)	0.103 (5)
O9	0.175 (5)	0.148 (4)	0.147 (4)	0.073 (4)	0.009 (4)	−0.039 (4)
O10	0.218 (6)	0.161 (5)	0.079 (3)	0.029 (4)	−0.004 (3)	0.048 (3)
P1	0.0438 (5)	0.0532 (6)	0.0460 (5)	0.0001 (5)	0.0034 (4)	−0.0011 (5)
P2	0.0453 (5)	0.0489 (6)	0.0502 (5)	0.0029 (5)	0.0047 (4)	0.0062 (5)
S1	0.0765 (8)	0.0559 (7)	0.0675 (7)	0.0042 (6)	−0.0102 (6)	−0.0071 (6)
S2	0.0943 (10)	0.0832 (10)	0.0727 (8)	0.0104 (8)	−0.0036 (7)	0.0098 (7)

Geometric parameters (Å, º) top

C1—C2	1.378 (6)	C31—C32	1.357 (7)
C1—C6	1.387 (6)	C31—H31	0.9300
C1—P1	1.797 (4)	C32—C33	1.376 (7)
C2—C3	1.389 (6)	C32—H32	0.9300
C2—H2	0.9300	C33—H33	0.9300
C3—C4	1.365 (7)	C34—C39	1.372 (6)
C3—H3	0.9300	C34—C35	1.387 (6)
C4—C5	1.357 (7)	C34—P2	1.796 (4)
C4—H4	0.9300	C35—C36	1.381 (7)
C5—C6	1.373 (6)	C35—H35	0.9300
C5—H5	0.9300	C36—C37	1.370 (8)
C6—H6	0.9300	C36—H36	0.9300
C7—C12	1.368 (6)	C37—C38	1.360 (9)
C7—C8	1.394 (6)	C37—H37	0.9300
C7—P1	1.799 (4)	C38—C39	1.380 (7)
C8—C9	1.386 (6)	C38—H38	0.9300
C8—H8	0.9300	C39—H39	0.9300
C9—C10	1.369 (7)	C40—C45	1.373 (6)
C9—H9	0.9300	C40—C41	1.390 (6)
C10—C11	1.355 (8)	C40—P2	1.797 (4)
C10—H10	0.9300	C41—C42	1.380 (6)
C11—C12	1.409 (7)	C41—H41	0.9300
C11—H11	0.9300	C42—C43	1.366 (7)
C12—H12	0.9300	C42—H42	0.9300
C13—C18	1.379 (6)	C43—C44	1.356 (7)
C13—C14	1.394 (6)	C43—H43	0.9300
C13—P1	1.795 (4)	C44—C45	1.382 (6)
C14—C15	1.376 (7)	C44—H44	0.9300
C14—H14	0.9300	C45—H45	0.9300
C15—C16	1.349 (7)	C46—C47	1.514 (5)
C15—H15	0.9300	C46—P2	1.794 (4)
C16—C17	1.364 (7)	C46—H46A	0.9700
C16—H16	0.9300	C46—H46B	0.9700
C17—C18	1.379 (6)	C47—O3	1.223 (5)
C17—H17	0.9300	C47—C48	1.473 (5)
C18—H18	0.9300	C48—C53	1.384 (6)
C19—C20	1.517 (5)	C48—C49	1.386 (5)
C19—P1	1.798 (4)	C49—C50	1.376 (6)
C19—H19A	0.9700	C49—H49	0.9300
C19—H19B	0.9700	C50—C51	1.382 (6)
C20—O1	1.226 (4)	C50—H50	0.9300
C20—C21	1.471 (5)	C51—O4	1.350 (5)
C21—C26	1.387 (5)	C51—C52	1.384 (7)
C21—C22	1.398 (6)	C52—C53	1.354 (6)
C22—C23	1.366 (6)	C52—H52	0.9300
C22—H22	0.9300	C53—H53	0.9300
C23—C24	1.380 (6)	C54—O4	1.417 (6)
C23—H23	0.9300	C54—H54A	0.9600
C24—O2	1.355 (5)	C54—H54B	0.9600
C24—C25	1.379 (6)	C54—H54C	0.9600
C25—C26	1.367 (6)	C55—F3	1.308 (6)
C25—H25	0.9300	C55—F2	1.312 (6)
C26—H26	0.9300	C55—F1	1.326 (6)
C27—O2	1.423 (6)	C55—S1	1.811 (5)
C27—H27A	0.9600	C56—F5	1.260 (7)
C27—H27B	0.9600	C56—F4	1.293 (7)
C27—H27C	0.9600	C56—F6	1.317 (6)
C28—C33	1.376 (6)	C56—S2	1.791 (7)
C28—C29	1.384 (5)	O5—S1	1.441 (4)
C28—P2	1.794 (4)	O6—S1	1.408 (4)
C29—C30	1.371 (6)	O7—S1	1.424 (4)
C29—H29	0.9300	O8—S2	1.381 (5)
C30—C31	1.355 (7)	O9—S2	1.374 (5)
C30—H30	0.9300	O10—S2	1.384 (4)

C2—C1—C6	119.7 (4)	C39—C34—P2	119.8 (3)
C2—C1—P1	123.3 (3)	C35—C34—P2	120.5 (3)
C6—C1—P1	116.8 (3)	C36—C35—C34	119.7 (5)
C1—C2—C3	118.9 (5)	C36—C35—H35	120.2
C1—C2—H2	120.6	C34—C35—H35	120.2
C3—C2—H2	120.6	C37—C36—C35	119.5 (5)
C4—C3—C2	120.2 (5)	C37—C36—H36	120.2
C4—C3—H3	119.9	C35—C36—H36	120.2
C2—C3—H3	119.9	C38—C37—C36	121.2 (5)
C5—C4—C3	121.4 (4)	C38—C37—H37	119.4
C5—C4—H4	119.3	C36—C37—H37	119.4
C3—C4—H4	119.3	C37—C38—C39	119.5 (5)
C4—C5—C6	119.1 (5)	C37—C38—H38	120.2
C4—C5—H5	120.5	C39—C38—H38	120.2
C6—C5—H5	120.5	C34—C39—C38	120.3 (5)
C5—C6—C1	120.7 (4)	C34—C39—H39	119.9
C5—C6—H6	119.6	C38—C39—H39	119.9
C1—C6—H6	119.6	C45—C40—C41	118.8 (4)
C12—C7—C8	119.9 (4)	C45—C40—P2	122.4 (3)
C12—C7—P1	123.5 (3)	C41—C40—P2	118.7 (3)
C8—C7—P1	116.6 (3)	C42—C41—C40	120.1 (4)
C9—C8—C7	120.4 (4)	C42—C41—H41	120.0
C9—C8—H8	119.8	C40—C41—H41	120.0
C7—C8—H8	119.8	C43—C42—C41	120.2 (5)
C10—C9—C8	119.4 (5)	C43—C42—H42	119.9
C10—C9—H9	120.3	C41—C42—H42	119.9
C8—C9—H9	120.3	C44—C43—C42	120.1 (4)
C11—C10—C9	120.6 (5)	C44—C43—H43	119.9
C11—C10—H10	119.7	C42—C43—H43	119.9
C9—C10—H10	119.7	C43—C44—C45	120.5 (5)
C10—C11—C12	120.9 (5)	C43—C44—H44	119.7
C10—C11—H11	119.5	C45—C44—H44	119.7
C12—C11—H11	119.5	C40—C45—C44	120.3 (4)
C7—C12—C11	118.7 (5)	C40—C45—H45	119.8
C7—C12—H12	120.6	C44—C45—H45	119.8
C11—C12—H12	120.6	C47—C46—P2	112.7 (3)
C18—C13—C14	119.4 (4)	C47—C46—H46A	109.0
C18—C13—P1	121.4 (3)	P2—C46—H46A	109.0
C14—C13—P1	119.2 (3)	C47—C46—H46B	109.0
C15—C14—C13	119.0 (5)	P2—C46—H46B	109.0
C15—C14—H14	120.5	H46A—C46—H46B	107.8
C13—C14—H14	120.5	O3—C47—C48	121.1 (4)
C16—C15—C14	121.2 (5)	O3—C47—C46	119.3 (3)
C16—C15—H15	119.4	C48—C47—C46	119.5 (3)
C14—C15—H15	119.4	C53—C48—C49	117.8 (4)
C15—C16—C17	120.2 (5)	C53—C48—C47	118.5 (4)
C15—C16—H16	119.9	C49—C48—C47	123.7 (4)
C17—C16—H16	119.9	C50—C49—C48	121.5 (4)
C16—C17—C18	120.3 (5)	C50—C49—H49	119.2
C16—C17—H17	119.9	C48—C49—H49	119.2
C18—C17—H17	119.9	C49—C50—C51	119.3 (4)
C17—C18—C13	119.9 (4)	C49—C50—H50	120.4
C17—C18—H18	120.1	C51—C50—H50	120.4
C13—C18—H18	120.1	O4—C51—C50	124.9 (4)
C20—C19—P1	113.4 (3)	O4—C51—C52	115.5 (4)
C20—C19—H19A	108.9	C50—C51—C52	119.6 (4)
P1—C19—H19A	108.9	C53—C52—C51	120.3 (4)
C20—C19—H19B	108.9	C53—C52—H52	119.8
P1—C19—H19B	108.9	C51—C52—H52	119.8
H19A—C19—H19B	107.7	C52—C53—C48	121.5 (4)
O1—C20—C21	122.2 (3)	C52—C53—H53	119.2
O1—C20—C19	119.2 (3)	C48—C53—H53	119.2
C21—C20—C19	118.6 (3)	O4—C54—H54A	109.5
C26—C21—C22	117.9 (4)	O4—C54—H54B	109.5
C26—C21—C20	119.0 (4)	H54A—C54—H54B	109.5
C22—C21—C20	123.1 (3)	O4—C54—H54C	109.5
C23—C22—C21	120.8 (4)	H54A—C54—H54C	109.5
C23—C22—H22	119.6	H54B—C54—H54C	109.5
C21—C22—H22	119.6	F3—C55—F2	107.8 (5)
C22—C23—C24	120.0 (4)	F3—C55—F1	107.7 (5)
C22—C23—H23	120.0	F2—C55—F1	107.8 (5)
C24—C23—H23	120.0	F3—C55—S1	111.9 (4)
O2—C24—C25	123.6 (4)	F2—C55—S1	111.1 (4)
O2—C24—C23	116.0 (4)	F1—C55—S1	110.4 (4)
C25—C24—C23	120.4 (4)	F5—C56—F4	106.1 (6)
C26—C25—C24	119.3 (4)	F5—C56—F6	105.2 (6)
C26—C25—H25	120.3	F4—C56—F6	103.4 (5)
C24—C25—H25	120.3	F5—C56—S2	114.7 (5)
C25—C26—C21	121.7 (4)	F4—C56—S2	113.3 (5)
C25—C26—H26	119.2	F6—C56—S2	113.2 (4)
C21—C26—H26	119.2	C24—O2—C27	118.3 (4)
O2—C27—H27A	109.5	C51—O4—C54	119.2 (4)
O2—C27—H27B	109.5	C13—P1—C1	112.27 (19)
H27A—C27—H27B	109.5	C13—P1—C19	109.13 (19)
O2—C27—H27C	109.5	C1—P1—C19	113.18 (19)
H27A—C27—H27C	109.5	C13—P1—C7	111.24 (19)
H27B—C27—H27C	109.5	C1—P1—C7	104.86 (17)
C33—C28—C29	119.1 (4)	C19—P1—C7	105.94 (18)
C33—C28—P2	119.9 (3)	C28—P2—C46	108.42 (18)
C29—C28—P2	120.8 (3)	C28—P2—C34	107.57 (19)
C30—C29—C28	120.3 (4)	C46—P2—C34	108.02 (17)
C30—C29—H29	119.8	C28—P2—C40	114.50 (18)
C28—C29—H29	119.8	C46—P2—C40	111.87 (19)
C31—C30—C29	120.0 (4)	C34—P2—C40	106.16 (18)
C31—C30—H30	120.0	O6—S1—O7	115.7 (3)
C29—C30—H30	120.0	O6—S1—O5	115.9 (3)
C30—C31—C32	120.4 (5)	O7—S1—O5	113.5 (3)
C30—C31—H31	119.8	O6—S1—C55	102.9 (3)
C32—C31—H31	119.8	O7—S1—C55	104.1 (3)
C31—C32—C33	120.7 (5)	O5—S1—C55	102.2 (2)
C31—C32—H32	119.6	O9—S2—O8	114.9 (4)
C33—C32—H32	119.6	O9—S2—O10	112.2 (4)
C28—C33—C32	119.5 (4)	O8—S2—O10	117.8 (4)
C28—C33—H33	120.3	O9—S2—C56	102.3 (3)
C32—C33—H33	120.3	O8—S2—C56	103.0 (3)
C39—C34—C35	119.7 (4)	O10—S2—C56	104.2 (3)

C6—C1—C2—C3	−0.4 (6)	C48—C49—C50—C51	−0.4 (7)
P1—C1—C2—C3	−175.8 (3)	C49—C50—C51—O4	179.0 (4)
C1—C2—C3—C4	0.1 (7)	C49—C50—C51—C52	−0.3 (7)
C2—C3—C4—C5	−0.6 (8)	O4—C51—C52—C53	−178.9 (5)
C3—C4—C5—C6	1.4 (7)	C50—C51—C52—C53	0.5 (8)
C4—C5—C6—C1	−1.7 (7)	C51—C52—C53—C48	0.1 (8)
C2—C1—C6—C5	1.2 (6)	C49—C48—C53—C52	−0.7 (7)
P1—C1—C6—C5	176.9 (3)	C47—C48—C53—C52	178.0 (4)
C12—C7—C8—C9	−1.5 (7)	C25—C24—O2—C27	−5.1 (7)
P1—C7—C8—C9	177.4 (3)	C23—C24—O2—C27	176.0 (5)
C7—C8—C9—C10	−0.3 (7)	C50—C51—O4—C54	−0.3 (8)
C8—C9—C10—C11	2.5 (8)	C52—C51—O4—C54	179.0 (5)
C9—C10—C11—C12	−3.0 (9)	C18—C13—P1—C1	−5.4 (4)
C8—C7—C12—C11	1.1 (7)	C14—C13—P1—C1	173.9 (3)
P1—C7—C12—C11	−177.8 (4)	C18—C13—P1—C19	−131.8 (3)
C10—C11—C12—C7	1.2 (9)	C14—C13—P1—C19	47.5 (4)
C18—C13—C14—C15	−0.4 (7)	C18—C13—P1—C7	111.7 (4)
P1—C13—C14—C15	−179.7 (4)	C14—C13—P1—C7	−69.0 (4)
C13—C14—C15—C16	0.2 (8)	C2—C1—P1—C13	−117.5 (3)
C14—C15—C16—C17	−0.8 (9)	C6—C1—P1—C13	66.9 (3)
C15—C16—C17—C18	1.6 (8)	C2—C1—P1—C19	6.6 (4)
C16—C17—C18—C13	−1.8 (7)	C6—C1—P1—C19	−169.0 (3)
C14—C13—C18—C17	1.2 (7)	C2—C1—P1—C7	121.6 (3)
P1—C13—C18—C17	−179.5 (3)	C6—C1—P1—C7	−54.0 (3)
P1—C19—C20—O1	15.7 (5)	C20—C19—P1—C13	55.0 (3)
P1—C19—C20—C21	−164.4 (3)	C20—C19—P1—C1	−70.8 (3)
O1—C20—C21—C26	−10.1 (6)	C20—C19—P1—C7	174.8 (3)
C19—C20—C21—C26	170.1 (4)	C12—C7—P1—C13	3.7 (5)
O1—C20—C21—C22	169.4 (4)	C8—C7—P1—C13	−175.2 (3)
C19—C20—C21—C22	−10.5 (6)	C12—C7—P1—C1	125.3 (4)
C26—C21—C22—C23	0.0 (6)	C8—C7—P1—C1	−53.6 (4)
C20—C21—C22—C23	−179.5 (4)	C12—C7—P1—C19	−114.8 (4)
C21—C22—C23—C24	−0.7 (7)	C8—C7—P1—C19	66.4 (4)
C22—C23—C24—O2	180.0 (4)	C33—C28—P2—C46	160.1 (3)
C22—C23—C24—C25	1.1 (7)	C29—C28—P2—C46	−25.3 (4)
O2—C24—C25—C26	−179.6 (4)	C33—C28—P2—C34	−83.3 (4)
C23—C24—C25—C26	−0.8 (7)	C29—C28—P2—C34	91.3 (4)
C24—C25—C26—C21	0.1 (7)	C33—C28—P2—C40	34.5 (4)
C22—C21—C26—C25	0.3 (6)	C29—C28—P2—C40	−151.0 (3)
C20—C21—C26—C25	179.8 (4)	C47—C46—P2—C28	−53.4 (3)
C33—C28—C29—C30	1.3 (7)	C47—C46—P2—C34	−169.7 (3)
P2—C28—C29—C30	−173.3 (4)	C47—C46—P2—C40	73.8 (3)
C28—C29—C30—C31	−1.5 (8)	C39—C34—P2—C28	160.9 (3)
C29—C30—C31—C32	1.0 (8)	C35—C34—P2—C28	−19.6 (4)
C30—C31—C32—C33	−0.3 (9)	C39—C34—P2—C46	−82.2 (4)
C29—C28—C33—C32	−0.6 (7)	C35—C34—P2—C46	97.3 (4)
P2—C28—C33—C32	174.0 (4)	C39—C34—P2—C40	37.9 (4)
C31—C32—C33—C28	0.2 (8)	C35—C34—P2—C40	−142.6 (3)
C39—C34—C35—C36	−1.2 (7)	C45—C40—P2—C28	114.2 (4)
P2—C34—C35—C36	179.2 (4)	C41—C40—P2—C28	−70.3 (4)
C34—C35—C36—C37	−0.5 (9)	C45—C40—P2—C46	−9.7 (5)
C35—C36—C37—C38	1.6 (10)	C41—C40—P2—C46	165.8 (3)
C36—C37—C38—C39	−0.8 (10)	C45—C40—P2—C34	−127.3 (4)
C35—C34—C39—C38	1.9 (7)	C41—C40—P2—C34	48.2 (4)
P2—C34—C39—C38	−178.5 (4)	F3—C55—S1—O6	55.2 (5)
C37—C38—C39—C34	−0.9 (9)	F2—C55—S1—O6	−65.4 (4)
C45—C40—C41—C42	−1.0 (7)	F1—C55—S1—O6	175.1 (4)
P2—C40—C41—C42	−176.7 (4)	F3—C55—S1—O7	−65.9 (5)
C40—C41—C42—C43	0.9 (8)	F2—C55—S1—O7	173.5 (4)
C41—C42—C43—C44	−0.5 (9)	F1—C55—S1—O7	54.0 (4)
C42—C43—C44—C45	0.2 (9)	F3—C55—S1—O5	175.7 (4)
C41—C40—C45—C44	0.7 (7)	F2—C55—S1—O5	55.1 (4)
P2—C40—C45—C44	176.2 (4)	F1—C55—S1—O5	−64.4 (4)
C43—C44—C45—C40	−0.3 (9)	F5—C56—S2—O9	−53.1 (7)
P2—C46—C47—O3	−19.7 (5)	F4—C56—S2—O9	68.9 (5)
P2—C46—C47—C48	159.4 (3)	F6—C56—S2—O9	−173.7 (5)
O3—C47—C48—C53	6.2 (6)	F5—C56—S2—O8	−172.5 (6)
C46—C47—C48—C53	−172.8 (4)	F4—C56—S2—O8	−50.5 (6)
O3—C47—C48—C49	−175.2 (4)	F6—C56—S2—O8	66.8 (6)
C46—C47—C48—C49	5.8 (6)	F5—C56—S2—O10	64.0 (6)
C53—C48—C49—C50	0.9 (7)	F4—C56—S2—O10	−174.0 (5)
C47—C48—C49—C50	−177.7 (4)	F6—C56—S2—O10	−56.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O5	0.97	2.34	3.207 (6)	149
C19—H19B···O3ⁱ	0.97	2.54	3.487 (5)	166
C33—H33···O6ⁱⁱ	0.93	2.34	3.130 (6)	143
C45—H45···O3	0.93	2.52	3.071 (6)	118
C46—H46A···O1	0.97	2.48	3.417 (5)	162
C46—H46B···O10ⁱⁱⁱ	0.97	2.19	3.137 (7)	165
C44—H44···Cg4^iv	0.93	2.83	3.640 (6)	147

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄O₂P⁺·CF₃O₃S⁻
M_r	560.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.6641 (5), 20.2760 (12), 25.0960 (11)
β (°)	96.539 (3)
V (Å³)	5391.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.67 × 0.33 × 0.14

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32: Stoe & Cie, 2002)
T_min, T_max	0.766, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	75273, 11185, 6282
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.188, 1.07
No. of reflections	11185
No. of parameters	685
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.29

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O5	0.97	2.34	3.207 (6)	149
C19—H19B···O3ⁱ	0.97	2.54	3.487 (5)	166
C33—H33···O6ⁱⁱ	0.93	2.34	3.130 (6)	143
C45—H45···O3	0.93	2.52	3.071 (6)	118
C46—H46A···O1	0.97	2.48	3.417 (5)	162
C46—H46B···O10ⁱⁱⁱ	0.97	2.19	3.137 (7)	165
C44—H44···Cg4^iv	0.93	2.83	3.640 (6)	147

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) x+1, y, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

Akkurt, M., Karami, K., Yalçın, Ş. P. & Büyükgüngör, O. (2008). Acta Cryst. E64, m612–m613. Web of Science CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burmeister, J. L., Silver, J. L., Weleski, E. T., Schweizer, E. E. & Kopay, C. M. (1973). Synth. Inorg. Met. Org. Chem. 3, 339–358. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kalyanasundari, M., Panchanatheswaran, K., Parthasarathi, V. & Robinson, W. T. (1999). Bull. Chem. Soc. Jpn, 72, 33–36. CSD CrossRef CAS Google Scholar
Kalyanasundari, M., Panchanatheswaran, K., Robinson, W. T. & Wen, H. (1995). J. Organomet. Chem. 491, 103–109. CSD CrossRef CAS Web of Science Google Scholar
Kolodiazhnyi, O. I. (1996). Tetrahedron, 52, 1855–1929. CrossRef CAS Web of Science Google Scholar
Laavanya, P., Venkatasubramanian, U., Panchanatheswaran, K. & Bauer, J. A. K. (2001). Chem. Commun. pp. 1660–1661. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Vicente, J., Chicote, M. T., Cayuelas, J. A., Fernandez-Baeza, J., Jones, P. G., Sheldrick, G. M. & Espinet, P. (1985). J. Chem. Soc. Dalton Trans. pp. 1163–1168. CSD CrossRef Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o296

doi:10.1107/S1600536809000919

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(4-Meth­oxy­benzoyl­meth­yl)tri­phenyl­phospho­nium tri­fluoro­methane­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4-Methoxybenzoylmethyl)triphenylphosphonium trifluoromethanesulfonate