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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o296.
Published online 2009 January 14. doi:  10.1107/S1600536809000919
PMCID: PMC2968230

(4-Methoxy­benzoyl­meth­yl)triphenyl­phospho­nium trifluoro­methane­sulfonate

Abstract

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 [triangle]);; Kalyanasundari et al. (1995 [triangle], 1999 [triangle]); Kolodiazhnyi (1996 [triangle]); Laavanya et al. (2001 [triangle]); Vicente et al. (1985 [triangle]). For the synthesis, see: Burmeister et al. (1973 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o296-scheme1.jpg

Experimental

Crystal data

  • C27H24O2P+·CF3O3S
  • M r = 560.50
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o296-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.188
  • S = 1.07
  • 11185 reflections
  • 685 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were positioned geometrically and were treated as riding, with C—H distances in the range 0.93-0.97 Å, and with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms and 1.5Ueq(C) for methyl H atoms.

Figures

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.

Crystal data

C27H24O2P+·CF3O3SF(000) = 2320
Mr = 560.50Dx = 1.381 Mg m3Dm = 1.381 Mg m3Dm measured by not measured
Monoclinic, P21/cMelting point: 296 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.6641 (5) ÅCell parameters from 685 reflections
b = 20.2760 (12) Åθ = 1–26.5°
c = 25.0960 (11) ŵ = 0.24 mm1
β = 96.539 (3)°T = 293 K
V = 5391.1 (5) Å3Prism, yellow
Z = 80.67 × 0.33 × 0.14 mm

Data collection

Stoe IPDSII diffractometer11185 independent reflections
Radiation source: fine-focfine-focus us sealed tube6282 reflections with I > 2σ(I)
graphiteRint = 0.082
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.3°
rotation scansh = −13→13
Absorption correction: integration (X-RED32: Stoe & Cie, 2002)k = −25→25
Tmin = 0.766, Tmax = 0.902l = −31→31
75273 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0814P)2] where P = (Fo2 + 2Fc2)/3
11185 reflections(Δ/σ)max < 0.001
685 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.29 e Å3
0 constraints

Special details

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)

xyzUiso*/Ueq
C10.2371 (3)0.4197 (2)0.62037 (15)0.0498 (9)
C20.3253 (4)0.4694 (2)0.62123 (18)0.0650 (11)
H20.32610.50350.64610.078*
C30.4130 (4)0.4678 (3)0.5844 (2)0.0803 (14)
H30.47320.50100.58450.096*
C40.4111 (4)0.4177 (3)0.54798 (19)0.0798 (15)
H40.46990.41750.52330.096*
C50.3252 (4)0.3682 (3)0.54703 (17)0.0723 (13)
H50.32620.33390.52250.087*
C60.2369 (4)0.3695 (2)0.58279 (16)0.0602 (11)
H60.17630.33640.58180.072*
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)
H80.01510.49680.57690.075*
C9−0.1508 (4)0.4638 (3)0.53982 (18)0.0742 (13)
H9−0.16090.49630.51350.089*
C10−0.2396 (5)0.4153 (3)0.5414 (2)0.0873 (16)
H10−0.30850.41400.51510.105*
C11−0.2280 (5)0.3693 (3)0.5808 (2)0.1002 (19)
H11−0.29120.33800.58230.120*
C12−0.1216 (4)0.3684 (3)0.6196 (2)0.0782 (14)
H12−0.11330.33620.64620.094*
C130.1237 (4)0.3494 (2)0.70769 (15)0.0543 (10)
C140.0411 (5)0.3450 (3)0.74678 (19)0.0782 (14)
H14−0.01950.37740.74950.094*
C150.0505 (5)0.2920 (3)0.7812 (2)0.0906 (16)
H15−0.00460.28870.80730.109*
C160.1381 (5)0.2446 (3)0.7779 (2)0.0836 (15)
H160.14350.20940.80180.100*
C170.2186 (5)0.2481 (2)0.7395 (2)0.0775 (13)
H170.27740.21470.73680.093*
C180.2133 (4)0.3009 (2)0.70465 (17)0.0642 (11)
H180.26990.30380.67920.077*
C190.1036 (4)0.4932 (2)0.70104 (15)0.0539 (10)
H19A0.10280.53070.67700.065*
H19B0.02470.49350.71690.065*
C200.2119 (4)0.5012 (2)0.74527 (15)0.0503 (9)
C210.1997 (3)0.55009 (19)0.78769 (15)0.0495 (9)
C220.1026 (4)0.5967 (2)0.78495 (17)0.0592 (10)
H220.04170.59730.75530.071*
C230.0962 (4)0.6414 (2)0.82528 (17)0.0652 (11)
H230.03160.67250.82280.078*
C240.1854 (4)0.6404 (2)0.86965 (17)0.0637 (11)
C250.2826 (4)0.5952 (2)0.87317 (16)0.0637 (12)
H250.34330.59480.90290.076*
C260.2887 (4)0.5508 (2)0.83254 (16)0.0574 (10)
H260.35420.52020.83500.069*
C270.2565 (6)0.6850 (4)0.9558 (2)0.119 (2)
H27A0.23620.72010.97900.179*
H27B0.34150.69030.94730.179*
H27C0.24890.64340.97350.179*
C280.6457 (3)0.3595 (2)0.76582 (15)0.0513 (9)
C290.5704 (4)0.3669 (2)0.71752 (17)0.0659 (12)
H290.53080.40700.70900.079*
C300.5537 (5)0.3152 (3)0.68215 (19)0.0781 (14)
H300.50150.32010.65010.094*
C310.6134 (5)0.2572 (3)0.6939 (2)0.0835 (15)
H310.60300.22240.66960.100*
C320.6883 (5)0.2494 (3)0.7409 (2)0.0913 (16)
H320.72850.20920.74860.110*
C330.7055 (4)0.3002 (2)0.77731 (18)0.0702 (12)
H330.75710.29460.80940.084*
C340.5360 (4)0.40709 (19)0.85901 (15)0.0517 (9)
C350.4350 (4)0.3661 (2)0.84246 (18)0.0716 (13)
H350.42780.34720.80850.086*
C360.3453 (5)0.3534 (3)0.8767 (2)0.1001 (19)
H360.27690.32620.86580.120*
C370.3577 (6)0.3812 (4)0.9268 (3)0.104 (2)
H370.29830.37170.95010.125*
C380.4554 (6)0.4223 (3)0.9431 (2)0.0998 (18)
H380.46200.44120.97700.120*
C390.5447 (5)0.4357 (2)0.90883 (18)0.0732 (13)
H390.61100.46430.91960.088*
C400.8025 (4)0.4269 (2)0.85787 (16)0.0548 (10)
C410.8310 (4)0.3769 (2)0.89511 (18)0.0698 (12)
H410.77630.34130.89650.084*
C420.9406 (5)0.3798 (3)0.9301 (2)0.0839 (15)
H420.96010.34590.95460.101*
C431.0204 (5)0.4323 (3)0.9288 (2)0.0912 (17)
H431.09380.43430.95260.109*
C440.9928 (5)0.4816 (3)0.8928 (2)0.0897 (16)
H441.04760.51720.89200.108*
C450.8839 (4)0.4793 (2)0.8573 (2)0.0727 (13)
H450.86560.51340.83290.087*
C460.6179 (4)0.50060 (19)0.78234 (16)0.0514 (9)
H46A0.52950.50060.76790.062*
H46B0.63040.53600.80840.062*
C470.6978 (4)0.5137 (2)0.73732 (16)0.0534 (10)
C480.6536 (3)0.56138 (19)0.69497 (15)0.0495 (9)
C490.5466 (4)0.6000 (2)0.69589 (17)0.0607 (11)
H490.50080.59740.72520.073*
C500.5068 (4)0.6422 (2)0.65444 (19)0.0709 (12)
H500.43450.66760.65560.085*
C510.5753 (4)0.6464 (2)0.61101 (17)0.0660 (12)
C520.6829 (5)0.6085 (3)0.6100 (2)0.0819 (15)
H520.72960.61150.58100.098*
C530.7206 (4)0.5672 (2)0.65113 (18)0.0676 (12)
H530.79320.54210.64990.081*
C540.4351 (6)0.7247 (3)0.5649 (2)0.110 (2)
H54A0.42630.74920.53200.165*
H54B0.44190.75460.59470.165*
H54C0.36250.69700.56630.165*
C55−0.0022 (5)0.6781 (3)0.5545 (2)0.0789 (14)
C560.8050 (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)
F30.0579 (4)0.7046 (2)0.51722 (14)0.1332 (14)
F40.8159 (4)0.8128 (3)0.47665 (15)0.1514 (17)
F50.8797 (5)0.8827 (3)0.4279 (3)0.211 (3)
F60.8564 (4)0.7876 (2)0.40148 (19)0.1530 (16)
O10.3065 (3)0.46701 (15)0.74453 (11)0.0653 (8)
O20.1719 (3)0.68647 (18)0.90766 (14)0.0893 (11)
O30.7972 (3)0.48392 (16)0.73638 (12)0.0718 (9)
O40.5451 (4)0.68504 (19)0.56762 (13)0.0946 (11)
O50.0177 (4)0.6331 (2)0.64958 (14)0.1079 (13)
O60.1662 (4)0.71576 (19)0.6272 (2)0.1266 (16)
O70.1802 (3)0.60495 (18)0.59502 (17)0.0979 (12)
O80.5820 (5)0.7954 (3)0.4125 (3)0.183 (3)
O90.6181 (6)0.9064 (3)0.4313 (2)0.157 (2)
O100.6530 (6)0.8681 (3)0.34844 (17)0.154 (2)
P10.11235 (9)0.41867 (5)0.66285 (4)0.0478 (3)
P20.65496 (9)0.42347 (5)0.81549 (4)0.0482 (3)
S10.10381 (12)0.65597 (6)0.61330 (5)0.0681 (3)
S20.64543 (14)0.85241 (7)0.40166 (5)0.0844 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.043 (2)0.057 (2)0.048 (2)0.0017 (19)0.0011 (16)0.0038 (19)
C20.057 (3)0.072 (3)0.066 (3)−0.004 (2)0.007 (2)0.002 (2)
C30.056 (3)0.102 (4)0.084 (3)−0.018 (3)0.015 (2)0.012 (3)
C40.056 (3)0.127 (5)0.059 (3)0.010 (3)0.017 (2)0.010 (3)
C50.066 (3)0.100 (4)0.052 (2)0.010 (3)0.013 (2)−0.003 (2)
C60.064 (3)0.066 (3)0.052 (2)−0.002 (2)0.011 (2)−0.002 (2)
C70.049 (2)0.059 (3)0.051 (2)−0.002 (2)0.0066 (17)−0.0054 (19)
C80.053 (2)0.071 (3)0.061 (3)0.001 (2)−0.0010 (19)0.001 (2)
C90.063 (3)0.099 (4)0.057 (3)0.009 (3)−0.006 (2)−0.002 (2)
C100.052 (3)0.137 (5)0.071 (3)−0.001 (3)−0.005 (2)−0.005 (3)
C110.062 (3)0.137 (5)0.099 (4)−0.040 (3)−0.004 (3)−0.006 (4)
C120.068 (3)0.090 (4)0.074 (3)−0.022 (3)−0.001 (2)0.013 (3)
C130.053 (2)0.060 (3)0.050 (2)−0.004 (2)0.0040 (18)0.0005 (19)
C140.071 (3)0.096 (4)0.071 (3)0.013 (3)0.021 (2)0.020 (3)
C150.083 (4)0.112 (5)0.081 (3)−0.005 (3)0.023 (3)0.031 (3)
C160.096 (4)0.077 (4)0.076 (3)−0.016 (3)−0.001 (3)0.027 (3)
C170.088 (3)0.068 (3)0.075 (3)0.013 (3)0.001 (3)0.011 (3)
C180.066 (3)0.067 (3)0.061 (3)0.005 (2)0.011 (2)0.004 (2)
C190.048 (2)0.059 (2)0.053 (2)0.0056 (19)0.0005 (18)−0.0051 (19)
C200.046 (2)0.055 (2)0.049 (2)−0.0009 (19)0.0031 (17)0.0014 (18)
C210.047 (2)0.053 (2)0.048 (2)−0.0055 (18)0.0044 (16)0.0001 (18)
C220.059 (2)0.059 (3)0.058 (2)0.004 (2)−0.0016 (19)−0.004 (2)
C230.065 (3)0.061 (3)0.069 (3)0.007 (2)0.004 (2)−0.012 (2)
C240.065 (3)0.065 (3)0.063 (3)−0.010 (2)0.013 (2)−0.012 (2)
C250.050 (2)0.087 (3)0.052 (2)−0.006 (2)−0.0022 (18)−0.010 (2)
C260.046 (2)0.071 (3)0.054 (2)0.001 (2)−0.0003 (18)−0.001 (2)
C270.111 (5)0.167 (7)0.077 (4)0.003 (4)−0.001 (3)−0.065 (4)
C280.041 (2)0.057 (2)0.056 (2)0.0049 (18)0.0039 (17)0.0036 (19)
C290.064 (3)0.071 (3)0.059 (3)0.015 (2)−0.006 (2)−0.003 (2)
C300.071 (3)0.098 (4)0.062 (3)0.011 (3)−0.003 (2)−0.013 (3)
C310.082 (3)0.084 (4)0.085 (4)0.005 (3)0.007 (3)−0.031 (3)
C320.104 (4)0.074 (3)0.093 (4)0.032 (3)−0.003 (3)−0.013 (3)
C330.079 (3)0.069 (3)0.059 (3)0.021 (3)−0.005 (2)−0.006 (2)
C340.051 (2)0.051 (2)0.054 (2)0.0043 (18)0.0060 (17)0.0061 (18)
C350.060 (3)0.094 (4)0.060 (3)−0.013 (3)0.006 (2)0.006 (2)
C360.067 (3)0.139 (5)0.098 (4)−0.030 (3)0.024 (3)0.001 (4)
C370.082 (4)0.144 (6)0.095 (4)0.003 (4)0.043 (3)0.019 (4)
C380.109 (5)0.128 (5)0.068 (3)0.003 (4)0.037 (3)−0.003 (3)
C390.077 (3)0.080 (3)0.065 (3)−0.008 (3)0.020 (2)−0.004 (2)
C400.050 (2)0.054 (2)0.059 (2)0.002 (2)0.0004 (18)0.0033 (19)
C410.067 (3)0.058 (3)0.080 (3)−0.003 (2)−0.014 (2)0.010 (2)
C420.081 (3)0.076 (3)0.088 (3)0.013 (3)−0.024 (3)0.018 (3)
C430.056 (3)0.101 (4)0.109 (4)−0.008 (3)−0.025 (3)0.012 (3)
C440.064 (3)0.094 (4)0.105 (4)−0.025 (3)−0.015 (3)0.017 (3)
C450.063 (3)0.069 (3)0.083 (3)−0.012 (2)−0.005 (2)0.012 (2)
C460.047 (2)0.052 (2)0.055 (2)0.0065 (18)0.0074 (17)0.0061 (18)
C470.048 (2)0.052 (2)0.061 (2)0.0030 (19)0.0104 (18)0.0085 (19)
C480.045 (2)0.049 (2)0.055 (2)0.0013 (17)0.0077 (17)0.0053 (17)
C490.062 (3)0.063 (3)0.059 (2)0.009 (2)0.016 (2)0.013 (2)
C500.068 (3)0.069 (3)0.076 (3)0.017 (2)0.010 (2)0.014 (2)
C510.077 (3)0.063 (3)0.057 (3)0.001 (2)0.002 (2)0.018 (2)
C520.072 (3)0.106 (4)0.071 (3)0.005 (3)0.021 (2)0.026 (3)
C530.051 (2)0.086 (3)0.067 (3)0.010 (2)0.011 (2)0.020 (2)
C540.113 (5)0.102 (5)0.107 (4)0.030 (4)−0.019 (4)0.036 (4)
C550.080 (3)0.076 (3)0.082 (3)−0.003 (3)0.013 (3)0.012 (3)
C560.105 (4)0.071 (4)0.093 (4)−0.008 (3)0.013 (3)−0.011 (3)
F10.107 (2)0.135 (3)0.104 (2)−0.025 (2)−0.0280 (19)−0.013 (2)
F20.102 (2)0.116 (3)0.140 (3)0.044 (2)0.009 (2)0.038 (2)
F30.146 (3)0.164 (4)0.095 (2)0.002 (3)0.037 (2)0.054 (2)
F40.140 (3)0.216 (5)0.090 (3)0.046 (3)−0.023 (2)0.014 (3)
F50.134 (4)0.124 (4)0.361 (9)−0.039 (3)−0.029 (5)0.026 (5)
F60.148 (4)0.148 (4)0.164 (4)0.042 (3)0.024 (3)−0.029 (3)
O10.0527 (16)0.079 (2)0.0620 (17)0.0156 (15)−0.0035 (13)−0.0125 (15)
O20.084 (2)0.097 (3)0.086 (2)−0.001 (2)0.0076 (19)−0.042 (2)
O30.0541 (17)0.087 (2)0.077 (2)0.0193 (16)0.0190 (15)0.0247 (17)
O40.106 (3)0.105 (3)0.072 (2)0.026 (2)0.0070 (19)0.039 (2)
O50.134 (3)0.120 (3)0.074 (2)0.020 (3)0.028 (2)0.029 (2)
O60.131 (3)0.079 (3)0.157 (4)−0.016 (2)−0.040 (3)−0.034 (3)
O70.082 (2)0.078 (2)0.129 (3)0.023 (2)−0.005 (2)−0.019 (2)
O80.132 (4)0.163 (5)0.236 (6)−0.068 (4)−0.057 (4)0.103 (5)
O90.175 (5)0.148 (4)0.147 (4)0.073 (4)0.009 (4)−0.039 (4)
O100.218 (6)0.161 (5)0.079 (3)0.029 (4)−0.004 (3)0.048 (3)
P10.0438 (5)0.0532 (6)0.0460 (5)0.0001 (5)0.0034 (4)−0.0011 (5)
P20.0453 (5)0.0489 (6)0.0502 (5)0.0029 (5)0.0047 (4)0.0062 (5)
S10.0765 (8)0.0559 (7)0.0675 (7)0.0042 (6)−0.0102 (6)−0.0071 (6)
S20.0943 (10)0.0832 (10)0.0727 (8)0.0104 (8)−0.0036 (7)0.0098 (7)

Geometric parameters (Å, °)

C1—C21.378 (6)C31—C321.357 (7)
C1—C61.387 (6)C31—H310.9300
C1—P11.797 (4)C32—C331.376 (7)
C2—C31.389 (6)C32—H320.9300
C2—H20.9300C33—H330.9300
C3—C41.365 (7)C34—C391.372 (6)
C3—H30.9300C34—C351.387 (6)
C4—C51.357 (7)C34—P21.796 (4)
C4—H40.9300C35—C361.381 (7)
C5—C61.373 (6)C35—H350.9300
C5—H50.9300C36—C371.370 (8)
C6—H60.9300C36—H360.9300
C7—C121.368 (6)C37—C381.360 (9)
C7—C81.394 (6)C37—H370.9300
C7—P11.799 (4)C38—C391.380 (7)
C8—C91.386 (6)C38—H380.9300
C8—H80.9300C39—H390.9300
C9—C101.369 (7)C40—C451.373 (6)
C9—H90.9300C40—C411.390 (6)
C10—C111.355 (8)C40—P21.797 (4)
C10—H100.9300C41—C421.380 (6)
C11—C121.409 (7)C41—H410.9300
C11—H110.9300C42—C431.366 (7)
C12—H120.9300C42—H420.9300
C13—C181.379 (6)C43—C441.356 (7)
C13—C141.394 (6)C43—H430.9300
C13—P11.795 (4)C44—C451.382 (6)
C14—C151.376 (7)C44—H440.9300
C14—H140.9300C45—H450.9300
C15—C161.349 (7)C46—C471.514 (5)
C15—H150.9300C46—P21.794 (4)
C16—C171.364 (7)C46—H46A0.9700
C16—H160.9300C46—H46B0.9700
C17—C181.379 (6)C47—O31.223 (5)
C17—H170.9300C47—C481.473 (5)
C18—H180.9300C48—C531.384 (6)
C19—C201.517 (5)C48—C491.386 (5)
C19—P11.798 (4)C49—C501.376 (6)
C19—H19A0.9700C49—H490.9300
C19—H19B0.9700C50—C511.382 (6)
C20—O11.226 (4)C50—H500.9300
C20—C211.471 (5)C51—O41.350 (5)
C21—C261.387 (5)C51—C521.384 (7)
C21—C221.398 (6)C52—C531.354 (6)
C22—C231.366 (6)C52—H520.9300
C22—H220.9300C53—H530.9300
C23—C241.380 (6)C54—O41.417 (6)
C23—H230.9300C54—H54A0.9600
C24—O21.355 (5)C54—H54B0.9600
C24—C251.379 (6)C54—H54C0.9600
C25—C261.367 (6)C55—F31.308 (6)
C25—H250.9300C55—F21.312 (6)
C26—H260.9300C55—F11.326 (6)
C27—O21.423 (6)C55—S11.811 (5)
C27—H27A0.9600C56—F51.260 (7)
C27—H27B0.9600C56—F41.293 (7)
C27—H27C0.9600C56—F61.317 (6)
C28—C331.376 (6)C56—S21.791 (7)
C28—C291.384 (5)O5—S11.441 (4)
C28—P21.794 (4)O6—S11.408 (4)
C29—C301.371 (6)O7—S11.424 (4)
C29—H290.9300O8—S21.381 (5)
C30—C311.355 (7)O9—S21.374 (5)
C30—H300.9300O10—S21.384 (4)
C2—C1—C6119.7 (4)C39—C34—P2119.8 (3)
C2—C1—P1123.3 (3)C35—C34—P2120.5 (3)
C6—C1—P1116.8 (3)C36—C35—C34119.7 (5)
C1—C2—C3118.9 (5)C36—C35—H35120.2
C1—C2—H2120.6C34—C35—H35120.2
C3—C2—H2120.6C37—C36—C35119.5 (5)
C4—C3—C2120.2 (5)C37—C36—H36120.2
C4—C3—H3119.9C35—C36—H36120.2
C2—C3—H3119.9C38—C37—C36121.2 (5)
C5—C4—C3121.4 (4)C38—C37—H37119.4
C5—C4—H4119.3C36—C37—H37119.4
C3—C4—H4119.3C37—C38—C39119.5 (5)
C4—C5—C6119.1 (5)C37—C38—H38120.2
C4—C5—H5120.5C39—C38—H38120.2
C6—C5—H5120.5C34—C39—C38120.3 (5)
C5—C6—C1120.7 (4)C34—C39—H39119.9
C5—C6—H6119.6C38—C39—H39119.9
C1—C6—H6119.6C45—C40—C41118.8 (4)
C12—C7—C8119.9 (4)C45—C40—P2122.4 (3)
C12—C7—P1123.5 (3)C41—C40—P2118.7 (3)
C8—C7—P1116.6 (3)C42—C41—C40120.1 (4)
C9—C8—C7120.4 (4)C42—C41—H41120.0
C9—C8—H8119.8C40—C41—H41120.0
C7—C8—H8119.8C43—C42—C41120.2 (5)
C10—C9—C8119.4 (5)C43—C42—H42119.9
C10—C9—H9120.3C41—C42—H42119.9
C8—C9—H9120.3C44—C43—C42120.1 (4)
C11—C10—C9120.6 (5)C44—C43—H43119.9
C11—C10—H10119.7C42—C43—H43119.9
C9—C10—H10119.7C43—C44—C45120.5 (5)
C10—C11—C12120.9 (5)C43—C44—H44119.7
C10—C11—H11119.5C45—C44—H44119.7
C12—C11—H11119.5C40—C45—C44120.3 (4)
C7—C12—C11118.7 (5)C40—C45—H45119.8
C7—C12—H12120.6C44—C45—H45119.8
C11—C12—H12120.6C47—C46—P2112.7 (3)
C18—C13—C14119.4 (4)C47—C46—H46A109.0
C18—C13—P1121.4 (3)P2—C46—H46A109.0
C14—C13—P1119.2 (3)C47—C46—H46B109.0
C15—C14—C13119.0 (5)P2—C46—H46B109.0
C15—C14—H14120.5H46A—C46—H46B107.8
C13—C14—H14120.5O3—C47—C48121.1 (4)
C16—C15—C14121.2 (5)O3—C47—C46119.3 (3)
C16—C15—H15119.4C48—C47—C46119.5 (3)
C14—C15—H15119.4C53—C48—C49117.8 (4)
C15—C16—C17120.2 (5)C53—C48—C47118.5 (4)
C15—C16—H16119.9C49—C48—C47123.7 (4)
C17—C16—H16119.9C50—C49—C48121.5 (4)
C16—C17—C18120.3 (5)C50—C49—H49119.2
C16—C17—H17119.9C48—C49—H49119.2
C18—C17—H17119.9C49—C50—C51119.3 (4)
C17—C18—C13119.9 (4)C49—C50—H50120.4
C17—C18—H18120.1C51—C50—H50120.4
C13—C18—H18120.1O4—C51—C50124.9 (4)
C20—C19—P1113.4 (3)O4—C51—C52115.5 (4)
C20—C19—H19A108.9C50—C51—C52119.6 (4)
P1—C19—H19A108.9C53—C52—C51120.3 (4)
C20—C19—H19B108.9C53—C52—H52119.8
P1—C19—H19B108.9C51—C52—H52119.8
H19A—C19—H19B107.7C52—C53—C48121.5 (4)
O1—C20—C21122.2 (3)C52—C53—H53119.2
O1—C20—C19119.2 (3)C48—C53—H53119.2
C21—C20—C19118.6 (3)O4—C54—H54A109.5
C26—C21—C22117.9 (4)O4—C54—H54B109.5
C26—C21—C20119.0 (4)H54A—C54—H54B109.5
C22—C21—C20123.1 (3)O4—C54—H54C109.5
C23—C22—C21120.8 (4)H54A—C54—H54C109.5
C23—C22—H22119.6H54B—C54—H54C109.5
C21—C22—H22119.6F3—C55—F2107.8 (5)
C22—C23—C24120.0 (4)F3—C55—F1107.7 (5)
C22—C23—H23120.0F2—C55—F1107.8 (5)
C24—C23—H23120.0F3—C55—S1111.9 (4)
O2—C24—C25123.6 (4)F2—C55—S1111.1 (4)
O2—C24—C23116.0 (4)F1—C55—S1110.4 (4)
C25—C24—C23120.4 (4)F5—C56—F4106.1 (6)
C26—C25—C24119.3 (4)F5—C56—F6105.2 (6)
C26—C25—H25120.3F4—C56—F6103.4 (5)
C24—C25—H25120.3F5—C56—S2114.7 (5)
C25—C26—C21121.7 (4)F4—C56—S2113.3 (5)
C25—C26—H26119.2F6—C56—S2113.2 (4)
C21—C26—H26119.2C24—O2—C27118.3 (4)
O2—C27—H27A109.5C51—O4—C54119.2 (4)
O2—C27—H27B109.5C13—P1—C1112.27 (19)
H27A—C27—H27B109.5C13—P1—C19109.13 (19)
O2—C27—H27C109.5C1—P1—C19113.18 (19)
H27A—C27—H27C109.5C13—P1—C7111.24 (19)
H27B—C27—H27C109.5C1—P1—C7104.86 (17)
C33—C28—C29119.1 (4)C19—P1—C7105.94 (18)
C33—C28—P2119.9 (3)C28—P2—C46108.42 (18)
C29—C28—P2120.8 (3)C28—P2—C34107.57 (19)
C30—C29—C28120.3 (4)C46—P2—C34108.02 (17)
C30—C29—H29119.8C28—P2—C40114.50 (18)
C28—C29—H29119.8C46—P2—C40111.87 (19)
C31—C30—C29120.0 (4)C34—P2—C40106.16 (18)
C31—C30—H30120.0O6—S1—O7115.7 (3)
C29—C30—H30120.0O6—S1—O5115.9 (3)
C30—C31—C32120.4 (5)O7—S1—O5113.5 (3)
C30—C31—H31119.8O6—S1—C55102.9 (3)
C32—C31—H31119.8O7—S1—C55104.1 (3)
C31—C32—C33120.7 (5)O5—S1—C55102.2 (2)
C31—C32—H32119.6O9—S2—O8114.9 (4)
C33—C32—H32119.6O9—S2—O10112.2 (4)
C28—C33—C32119.5 (4)O8—S2—O10117.8 (4)
C28—C33—H33120.3O9—S2—C56102.3 (3)
C32—C33—H33120.3O8—S2—C56103.0 (3)
C39—C34—C35119.7 (4)O10—S2—C56104.2 (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—O4179.0 (4)
C1—C2—C3—C40.1 (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—C61.4 (7)C50—C51—C52—C530.5 (8)
C4—C5—C6—C1−1.7 (7)C51—C52—C53—C480.1 (8)
C2—C1—C6—C51.2 (6)C49—C48—C53—C52−0.7 (7)
P1—C1—C6—C5176.9 (3)C47—C48—C53—C52178.0 (4)
C12—C7—C8—C9−1.5 (7)C25—C24—O2—C27−5.1 (7)
P1—C7—C8—C9177.4 (3)C23—C24—O2—C27176.0 (5)
C7—C8—C9—C10−0.3 (7)C50—C51—O4—C54−0.3 (8)
C8—C9—C10—C112.5 (8)C52—C51—O4—C54179.0 (5)
C9—C10—C11—C12−3.0 (9)C18—C13—P1—C1−5.4 (4)
C8—C7—C12—C111.1 (7)C14—C13—P1—C1173.9 (3)
P1—C7—C12—C11−177.8 (4)C18—C13—P1—C19−131.8 (3)
C10—C11—C12—C71.2 (9)C14—C13—P1—C1947.5 (4)
C18—C13—C14—C15−0.4 (7)C18—C13—P1—C7111.7 (4)
P1—C13—C14—C15−179.7 (4)C14—C13—P1—C7−69.0 (4)
C13—C14—C15—C160.2 (8)C2—C1—P1—C13−117.5 (3)
C14—C15—C16—C17−0.8 (9)C6—C1—P1—C1366.9 (3)
C15—C16—C17—C181.6 (8)C2—C1—P1—C196.6 (4)
C16—C17—C18—C13−1.8 (7)C6—C1—P1—C19−169.0 (3)
C14—C13—C18—C171.2 (7)C2—C1—P1—C7121.6 (3)
P1—C13—C18—C17−179.5 (3)C6—C1—P1—C7−54.0 (3)
P1—C19—C20—O115.7 (5)C20—C19—P1—C1355.0 (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—C7174.8 (3)
C19—C20—C21—C26170.1 (4)C12—C7—P1—C133.7 (5)
O1—C20—C21—C22169.4 (4)C8—C7—P1—C13−175.2 (3)
C19—C20—C21—C22−10.5 (6)C12—C7—P1—C1125.3 (4)
C26—C21—C22—C230.0 (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—C1966.4 (4)
C22—C23—C24—O2180.0 (4)C33—C28—P2—C46160.1 (3)
C22—C23—C24—C251.1 (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—C3491.3 (4)
C24—C25—C26—C210.1 (7)C33—C28—P2—C4034.5 (4)
C22—C21—C26—C250.3 (6)C29—C28—P2—C40−151.0 (3)
C20—C21—C26—C25179.8 (4)C47—C46—P2—C28−53.4 (3)
C33—C28—C29—C301.3 (7)C47—C46—P2—C34−169.7 (3)
P2—C28—C29—C30−173.3 (4)C47—C46—P2—C4073.8 (3)
C28—C29—C30—C31−1.5 (8)C39—C34—P2—C28160.9 (3)
C29—C30—C31—C321.0 (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—C4697.3 (4)
P2—C28—C33—C32174.0 (4)C39—C34—P2—C4037.9 (4)
C31—C32—C33—C280.2 (8)C35—C34—P2—C40−142.6 (3)
C39—C34—C35—C36−1.2 (7)C45—C40—P2—C28114.2 (4)
P2—C34—C35—C36179.2 (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—C381.6 (10)C41—C40—P2—C46165.8 (3)
C36—C37—C38—C39−0.8 (10)C45—C40—P2—C34−127.3 (4)
C35—C34—C39—C381.9 (7)C41—C40—P2—C3448.2 (4)
P2—C34—C39—C38−178.5 (4)F3—C55—S1—O655.2 (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—O6175.1 (4)
P2—C40—C41—C42−176.7 (4)F3—C55—S1—O7−65.9 (5)
C40—C41—C42—C430.9 (8)F2—C55—S1—O7173.5 (4)
C41—C42—C43—C44−0.5 (9)F1—C55—S1—O754.0 (4)
C42—C43—C44—C450.2 (9)F3—C55—S1—O5175.7 (4)
C41—C40—C45—C440.7 (7)F2—C55—S1—O555.1 (4)
P2—C40—C45—C44176.2 (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—O968.9 (5)
P2—C46—C47—C48159.4 (3)F6—C56—S2—O9−173.7 (5)
O3—C47—C48—C536.2 (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—O866.8 (6)
C46—C47—C48—C495.8 (6)F5—C56—S2—O1064.0 (6)
C53—C48—C49—C500.9 (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, °)

D—H···AD—HH···AD···AD—H···A
C19—H19A···O50.972.343.207 (6)149
C19—H19B···O3i0.972.543.487 (5)166
C33—H33···O6ii0.932.343.130 (6)143
C45—H45···O30.932.523.071 (6)118
C46—H46A···O10.972.483.417 (5)162
C46—H46B···O10iii0.972.193.137 (7)165
C44—H44···Cg4iv0.932.833.640 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2703).

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