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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1080.
Published online 2009 April 22. doi:  10.1107/S1600536809013488
PMCID: PMC2977759

Tris[3,5-bis­(trifluoro­meth­yl)phen­yl]phosphine oxide

Abstract

In the title compound, C24H9F18OP, an intra­molecular C—H(...)O short contact generates a five-membered ring, producing an S(5) ring motif. The dihedral angles between the benzene rings are 57.68 (10), 77.80 (11) and 79.48 (10)°. Each of the six trifluoro­methyl substituents shows rotational disorder over two positions with refined site-occupany ratios of 0.64 (3)/0.36 (3), 0.649 (14)/0.351 (14), 0.52 (2)/0.48 (2), 0.545 (16)/0.455 (16), 0.774 (9)/0.226 (9) and 0.63 (5)/0.37 (5). The crystal structure is stabilized by inter­molecular C—H(...)O and C—H(...)F inter­actions.

Related literature

For C—F bond lengths, see: Allen et al. (1987 [triangle]). For the stereochemistry of triphenyl­phosphine oxide complexes and for P—C bond distances, see: Bandoli et al. (1970 [triangle]); Ruban & Zabel (1976 [triangle]); Baures & Silverton (1990 [triangle]); Lynch et al. (1992 [triangle]); Shawkataly et al. (1997 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1080-scheme1.jpg

Experimental

Crystal data

  • C24H9F18OP
  • M r = 686.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1080-efi1.jpg
  • a = 10.7937 (2) Å
  • b = 11.8786 (10) Å
  • c = 12.5066 (10) Å
  • α = 111.065 (10)°
  • β = 103.645 (10)°
  • γ = 106.562 (10)°
  • V = 1327.7 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 294 K
  • 0.48 × 0.38 × 0.22 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.890, T max = 0.947
  • 7134 measured reflections
  • 4535 independent reflections
  • 3611 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.113
  • S = 1.02
  • 4535 reflections
  • 565 parameters
  • 168 restraints
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013488/sj2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013488/sj2588Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for research grant 1001/PJJAUH/811115.

supplementary crystallographic information

Comment

There has been considerable research on the stereochemistry of triphenyl phosphine oxide complexes (Bandoli et al., 1970; Ruban & Zabel, 1976; Spek, 1987; Baures & Silverton, 1990; Shawkataly et al., 1997) involving different space groups. A search of the Cambridge Structural Database (Version 5.29; Allen, 2007) revealed only 9 reported structures of the parent triphenylphosphine complexes as opposed to complexes of triphenylphosphine oxides. Our interest in complexes of triphenylphosphine led us to determine the X-ray crystal structure of the title compound, Fig. 1, in order to elucidate its conformation.

The bond lengths and angles of the title compound, Fig. 1, are within normal ranges (Allen et al., 1987). An intramolecular C—H···O hydrogen bond generates a five-membered ring, producing a S(5) ring motif (Bernstein et al., 1995). The P atom binds to three C atoms and one O atom in a nearly ideal tetrahedral geometry with the average O—P—C bond angle 112.84°. In the title compound, the P═O distance of 1.475 (3)Å, is less than the value reported for triphenylphospine oxide [1.487 (2)Å (Baures & Silverton, 1990)]. The average P—C bond distance is 1.813Å which is slightly longer than the distance observed in triphenylphosphine oxides previously studied; 1.799 (3)Å in OPPh3 (Baures & Silverton, 1990) and 1.76 (1)Å in its adduct with tricarboxylic acid (Lynch et al., 1992). This slight lengthening is probably due to the presence of electron withdrawing -CF3 groups bonded to the phenyl rings. The trifluoromethyl substituents show rotational disorder over two positions with a refined site-occupany ratio of 0.64 (3)/0.36 (3), 0.649 (14)/0.351 (14), 0.52 (2)/0.48 (2), 0.545 (16)/0.455 (16), 0.774 (9)/0.226 (9), and 0.63 (5)/0.37 (5) and average C—F distance of 1.300Å. This value is slightly shorter than that of the normal -CF3 bond distance (Allen et al., 1987).

The mean C—P—C bond angle is 105.90°, while the O—P—C bond angles show a slight variation: 113.01 (10), 114.31 (9) and 111.18 (10)° for O—P—C9, O—P—C1, and O—P—C17 respectively. The dihedral angles between the phenyl rings and the planes containing O, P and the corresponding ipso-C atoms are 79.52 (13), 29.14 (13), 10.70 (13)°, respectively. These are close to the values for the unsubstituted analogue [77.2 (1), 36.3 (1) and 11.9 (1)°]. The crystal structure is stabilized by intermolecular C—H···O and C—H···F interactions (Table 1).

Experimental

The title compound was supplied by Strem Chemicals. Single crystals of (I) were obtained by slow evaporation of an ethanol solution.

Refinement

All of the hydrogen atoms were positioned geometrically and refined with a riding approximation model with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C). The trifluoromethyl substituents show rotational disorder over two positions with a refined site-occupany ratios of 0.64 (3)/0.36 (3) for F1, F2, F3, 0.649 (14)/0.351 (14) for F4, F5, F6, 0.52 (2)/0.48 (2) for F7, F8, F9, 0.545 (16)/0.455 (16) for F10, F11, F12, 0.774 (9)/0.226 (9) for F13, F14, F15 and 0.63 (5)/0.37 (5) for F16, F17, F18 respectively. Rigid-bond restraints were applied for the fluorine groups in order to improve the high displacement ellipsoids of the groups but this was not particularly succesful, except that the refinement convergence was more stable.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Open bonds link the F atoms of the minor disorder components.

Crystal data

C24H9F18OPZ = 2
Mr = 686.28F(000) = 676
Triclinic, P1Dx = 1.717 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7937 (2) ÅCell parameters from 5230 reflections
b = 11.8786 (10) Åθ = 1.9–28.3°
c = 12.5066 (10) ŵ = 0.25 mm1
α = 111.065 (10)°T = 294 K
β = 103.645 (10)°Block, colourless
γ = 106.562 (10)°0.48 × 0.38 × 0.22 mm
V = 1327.7 (3) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4535 independent reflections
Radiation source: fine-focus sealed tube3611 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→12
Tmin = 0.890, Tmax = 0.947k = −13→14
7134 measured reflectionsl = −14→10

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0656P)2 + 0.1383P] where P = (Fo2 + 2Fc2)/3
4535 reflections(Δ/σ)max = 0.001
565 parametersΔρmax = 0.20 e Å3
168 restraintsΔρmin = −0.27 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
P10.69584 (5)0.56123 (5)0.16458 (4)0.03853 (15)
O10.66832 (14)0.62576 (14)0.08623 (14)0.0516 (4)
C10.56380 (18)0.52657 (18)0.22911 (18)0.0408 (4)
C20.4957 (2)0.6106 (2)0.24927 (19)0.0473 (5)
H2A0.51910.68090.23050.057*
C30.3928 (2)0.5897 (2)0.2974 (2)0.0532 (5)
C40.3564 (2)0.4856 (2)0.3248 (2)0.0552 (5)
H4A0.28660.47160.35620.066*
C50.4241 (2)0.4021 (2)0.3053 (2)0.0506 (5)
C60.5283 (2)0.42242 (19)0.25787 (19)0.0460 (5)
H6A0.57400.36610.24550.055*
C70.3816 (3)0.2847 (3)0.3293 (3)0.0733 (7)
C80.3197 (4)0.6811 (4)0.3178 (3)0.0804 (8)
C90.70486 (19)0.40435 (18)0.08552 (17)0.0404 (4)
C100.5806 (2)0.29374 (19)0.00606 (18)0.0459 (5)
H10A0.49540.3003−0.00210.055*
C110.5843 (2)0.1740 (2)−0.0606 (2)0.0531 (5)
C120.7100 (2)0.1634 (2)−0.0525 (2)0.0574 (6)
H12A0.71170.0828−0.09820.069*
C130.8329 (2)0.2734 (2)0.02403 (19)0.0537 (5)
C140.8311 (2)0.3936 (2)0.09427 (18)0.0474 (5)
H14A0.91460.46690.14720.057*
C150.4488 (3)0.0560 (3)−0.1458 (3)0.0801 (8)
C160.9705 (3)0.2659 (3)0.0296 (3)0.0809 (9)
C170.85895 (18)0.66656 (17)0.29756 (17)0.0378 (4)
C180.94351 (19)0.78052 (18)0.29999 (18)0.0422 (4)
H18A0.91760.79860.23370.051*
C191.0671 (2)0.86781 (18)0.40158 (19)0.0445 (5)
C201.1054 (2)0.84267 (19)0.50081 (19)0.0475 (5)
H20A1.18790.90150.56880.057*
C211.0203 (2)0.72894 (19)0.49895 (18)0.0436 (4)
C220.89764 (19)0.64089 (18)0.39795 (18)0.0417 (4)
H22A0.84110.56470.39700.050*
C231.1590 (3)0.9907 (2)0.4026 (2)0.0608 (6)
C241.0639 (3)0.7057 (2)0.6091 (2)0.0627 (6)
F1A0.3107 (17)0.2938 (11)0.4026 (13)0.127 (3)0.64 (3)
F2A0.3053 (13)0.1725 (6)0.2330 (7)0.106 (2)0.64 (3)
F3A0.4911 (12)0.2685 (12)0.3845 (8)0.103 (3)0.64 (3)
F1B0.347 (2)0.3116 (17)0.4269 (11)0.101 (4)0.36 (3)
F2B0.265 (3)0.1929 (19)0.2265 (17)0.167 (8)0.36 (3)
F3B0.474 (3)0.238 (3)0.345 (4)0.143 (8)0.36 (3)
F4A0.2145 (11)0.6369 (9)0.3520 (13)0.132 (3)0.649 (14)
F5A0.4017 (7)0.7979 (6)0.3979 (11)0.149 (4)0.649 (14)
F6A0.2564 (13)0.6778 (13)0.2152 (7)0.149 (4)0.649 (14)
F4B0.3833 (18)0.7925 (14)0.307 (2)0.129 (5)0.351 (14)
F5B0.2026 (13)0.6458 (12)0.242 (2)0.153 (9)0.351 (14)
F6B0.319 (2)0.733 (2)0.4278 (10)0.134 (7)0.351 (14)
F7A1.0083 (16)0.289 (3)−0.0448 (13)0.171 (6)0.52 (2)
F8A0.9558 (9)0.1390 (8)0.010 (2)0.166 (6)0.52 (2)
F9A1.0656 (11)0.3334 (14)0.1386 (10)0.123 (5)0.52 (2)
F7B1.0531 (13)0.3664 (12)0.009 (2)0.142 (5)0.48 (2)
F8B0.9664 (8)0.1631 (12)−0.0554 (10)0.112 (4)0.48 (2)
F9B1.0478 (16)0.292 (2)0.1352 (11)0.141 (6)0.48 (2)
F10A0.3748 (10)0.0774 (10)−0.2275 (11)0.124 (4)0.545 (16)
F11A0.3666 (10)0.0405 (10)−0.0809 (7)0.124 (3)0.545 (16)
F12A0.4594 (10)−0.0513 (8)−0.1913 (19)0.174 (6)0.545 (16)
F10B0.4473 (14)−0.0498 (9)−0.1405 (11)0.125 (5)0.455 (16)
F11B0.4366 (18)0.0163 (16)−0.2650 (6)0.151 (6)0.455 (16)
F12B0.3425 (7)0.0689 (11)−0.140 (3)0.215 (10)0.455 (16)
F13A1.2266 (7)1.0906 (3)0.5147 (3)0.107 (2)0.774 (9)
F14A1.0835 (3)1.0359 (4)0.3402 (5)0.0925 (13)0.774 (9)
F15A1.2459 (5)0.9734 (4)0.3515 (6)0.102 (2)0.774 (9)
F13B1.2974 (10)1.030 (2)0.481 (2)0.119 (7)0.226 (9)
F14B1.136 (3)1.0800 (13)0.438 (4)0.163 (11)0.226 (9)
F15B1.184 (3)0.9613 (17)0.3041 (18)0.156 (11)0.226 (9)
F16A1.1855 (12)0.6770 (8)0.6200 (8)0.082 (2)0.63 (5)
F17A1.1071 (13)0.8101 (11)0.7152 (10)0.094 (3)0.63 (5)
F18A0.9620 (17)0.6078 (13)0.6047 (10)0.092 (3)0.63 (5)
F16B1.162 (2)0.689 (2)0.625 (2)0.132 (7)0.37 (5)
F17B1.068 (5)0.802 (2)0.7088 (18)0.117 (6)0.37 (5)
F18B0.978 (2)0.5964 (15)0.6035 (17)0.073 (4)0.37 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0314 (2)0.0401 (3)0.0421 (3)0.0116 (2)0.01248 (19)0.0200 (2)
O10.0436 (8)0.0596 (9)0.0578 (9)0.0192 (7)0.0165 (6)0.0363 (7)
C10.0311 (9)0.0424 (10)0.0435 (10)0.0110 (8)0.0108 (8)0.0194 (8)
C20.0456 (11)0.0496 (11)0.0509 (12)0.0213 (9)0.0184 (9)0.0258 (9)
C30.0473 (11)0.0668 (13)0.0562 (13)0.0304 (11)0.0239 (10)0.0309 (11)
C40.0409 (11)0.0706 (14)0.0581 (13)0.0201 (10)0.0243 (10)0.0321 (12)
C50.0439 (11)0.0504 (11)0.0528 (12)0.0113 (9)0.0182 (9)0.0250 (10)
C60.0419 (10)0.0449 (11)0.0531 (12)0.0181 (9)0.0180 (9)0.0240 (9)
C70.0803 (19)0.0633 (16)0.084 (2)0.0198 (15)0.0439 (17)0.0412 (16)
C80.087 (2)0.109 (3)0.098 (2)0.069 (2)0.0594 (19)0.064 (2)
C90.0359 (9)0.0433 (10)0.0375 (10)0.0137 (8)0.0111 (8)0.0175 (8)
C100.0381 (10)0.0464 (11)0.0447 (11)0.0129 (8)0.0076 (8)0.0207 (9)
C110.0488 (12)0.0432 (11)0.0479 (12)0.0105 (9)0.0056 (9)0.0153 (9)
C120.0634 (14)0.0495 (12)0.0467 (12)0.0260 (11)0.0127 (10)0.0120 (10)
C130.0475 (11)0.0623 (13)0.0435 (11)0.0258 (10)0.0140 (9)0.0157 (10)
C140.0365 (10)0.0518 (11)0.0404 (10)0.0141 (9)0.0103 (8)0.0131 (9)
C150.0668 (18)0.0488 (15)0.079 (2)0.0073 (13)−0.0006 (15)0.0127 (14)
C160.0639 (16)0.093 (2)0.0667 (18)0.0435 (17)0.0220 (15)0.0102 (16)
C170.0345 (9)0.0346 (9)0.0435 (10)0.0132 (7)0.0170 (8)0.0164 (8)
C180.0431 (10)0.0394 (10)0.0453 (11)0.0158 (8)0.0205 (8)0.0191 (8)
C190.0430 (10)0.0332 (9)0.0508 (11)0.0101 (8)0.0226 (9)0.0137 (9)
C200.0388 (10)0.0391 (10)0.0475 (11)0.0075 (8)0.0123 (9)0.0115 (9)
C210.0408 (10)0.0410 (10)0.0428 (11)0.0144 (8)0.0122 (8)0.0168 (8)
C220.0382 (10)0.0351 (9)0.0477 (11)0.0101 (8)0.0158 (8)0.0187 (8)
C230.0576 (14)0.0456 (13)0.0674 (15)0.0077 (11)0.0273 (12)0.0216 (12)
C240.0612 (16)0.0544 (14)0.0514 (14)0.0100 (12)0.0050 (11)0.0234 (12)
F1A0.156 (6)0.100 (4)0.199 (9)0.056 (5)0.140 (7)0.095 (5)
F2A0.147 (6)0.0449 (19)0.087 (3)0.008 (3)0.025 (3)0.028 (2)
F3A0.122 (5)0.106 (4)0.112 (4)0.048 (4)0.041 (4)0.082 (3)
F1B0.126 (8)0.108 (6)0.062 (6)0.012 (5)0.039 (5)0.059 (4)
F2B0.131 (9)0.079 (7)0.196 (14)−0.035 (6)−0.045 (8)0.094 (9)
F3B0.172 (17)0.151 (14)0.28 (2)0.125 (13)0.168 (16)0.178 (16)
F4A0.153 (6)0.162 (5)0.219 (9)0.124 (5)0.154 (6)0.131 (6)
F5A0.138 (4)0.082 (3)0.185 (8)0.075 (3)0.027 (5)0.016 (4)
F6A0.191 (8)0.279 (10)0.141 (4)0.204 (8)0.107 (6)0.152 (6)
F4B0.152 (11)0.130 (8)0.209 (14)0.112 (8)0.119 (11)0.109 (9)
F5B0.077 (6)0.133 (7)0.193 (15)0.075 (6)−0.001 (6)0.025 (8)
F6B0.189 (15)0.206 (15)0.096 (6)0.162 (14)0.088 (8)0.075 (8)
F7A0.129 (8)0.337 (18)0.133 (7)0.135 (11)0.106 (7)0.128 (10)
F8A0.103 (4)0.117 (5)0.245 (14)0.081 (4)0.045 (7)0.035 (7)
F9A0.044 (3)0.141 (5)0.100 (7)0.043 (3)0.000 (3)−0.015 (5)
F7B0.089 (5)0.136 (7)0.263 (15)0.059 (4)0.118 (8)0.111 (7)
F8B0.087 (3)0.101 (5)0.108 (6)0.054 (4)0.041 (3)−0.008 (4)
F9B0.094 (8)0.283 (17)0.092 (8)0.119 (10)0.042 (6)0.098 (10)
F10A0.097 (5)0.083 (4)0.093 (5)−0.011 (3)−0.048 (4)0.029 (4)
F11A0.076 (5)0.111 (5)0.111 (4)−0.028 (3)0.020 (3)0.037 (3)
F12A0.093 (4)0.052 (4)0.230 (12)0.018 (3)0.008 (7)−0.044 (5)
F10B0.131 (8)0.055 (5)0.108 (5)−0.022 (5)−0.014 (5)0.037 (5)
F11B0.157 (9)0.101 (6)0.063 (3)−0.033 (6)−0.031 (4)0.014 (4)
F12B0.042 (3)0.084 (7)0.32 (2)0.004 (3)0.003 (9)−0.052 (10)
F13A0.117 (4)0.0482 (17)0.0828 (18)−0.024 (2)0.0195 (18)0.0112 (12)
F14A0.0812 (16)0.061 (2)0.141 (3)0.0181 (15)0.033 (2)0.065 (2)
F15A0.096 (3)0.075 (2)0.185 (6)0.042 (2)0.105 (4)0.071 (3)
F13B0.050 (5)0.114 (11)0.152 (12)−0.021 (6)0.003 (6)0.084 (10)
F14B0.181 (19)0.039 (7)0.34 (3)0.065 (11)0.207 (19)0.072 (13)
F15B0.189 (18)0.103 (10)0.097 (9)−0.053 (12)0.077 (12)0.036 (6)
F16A0.054 (3)0.098 (5)0.101 (4)0.036 (3)0.010 (2)0.063 (4)
F17A0.111 (5)0.066 (4)0.045 (3)0.003 (5)−0.007 (3)0.013 (2)
F18A0.078 (4)0.111 (6)0.065 (4)−0.003 (4)0.012 (2)0.059 (4)
F16B0.093 (7)0.223 (18)0.171 (12)0.108 (10)0.048 (7)0.149 (13)
F17B0.205 (18)0.109 (11)0.039 (6)0.080 (10)0.038 (8)0.028 (6)
F18B0.082 (7)0.052 (5)0.070 (6)0.018 (5)0.005 (4)0.035 (4)

Geometric parameters (Å, °)

P1—O11.4726 (15)C14—H14A0.9300
P1—C91.8122 (19)C15—F12B1.215 (9)
P1—C171.8160 (19)C15—F12A1.246 (7)
P1—C11.8163 (19)C15—F10B1.277 (9)
C1—C61.386 (3)C15—F10A1.290 (7)
C1—C21.387 (3)C15—F11B1.352 (10)
C2—C31.386 (3)C15—F11A1.354 (8)
C2—H2A0.9300C16—F7A1.187 (11)
C3—C41.376 (3)C16—F9B1.256 (11)
C3—C81.500 (3)C16—F8B1.279 (7)
C4—C51.379 (3)C16—F9A1.280 (10)
C4—H4A0.9300C16—F8A1.392 (11)
C5—C61.392 (3)C16—F7B1.417 (9)
C5—C71.498 (3)C17—C181.385 (3)
C6—H6A0.9300C17—C221.394 (3)
C7—F3B1.286 (19)C18—C191.391 (3)
C7—F2A1.287 (7)C18—H18A0.9300
C7—F1B1.320 (13)C19—C201.377 (3)
C7—F1A1.321 (8)C19—C231.506 (3)
C7—F3A1.323 (11)C20—C211.389 (3)
C7—F2B1.368 (15)C20—H20A0.9300
C8—F5B1.232 (10)C21—C221.383 (3)
C8—F5A1.263 (6)C21—C241.496 (3)
C8—F6A1.285 (7)C22—H22A0.9300
C8—F6B1.293 (8)C23—F14B1.117 (9)
C8—F4A1.341 (5)C23—F15B1.268 (16)
C8—F4B1.374 (10)C23—F15A1.277 (4)
C9—C141.387 (3)C23—F13A1.317 (4)
C9—C101.393 (3)C23—F14A1.346 (4)
C10—C111.384 (3)C23—F13B1.412 (10)
C10—H10A0.9300C24—F16B1.11 (3)
C11—C121.382 (3)C24—F17A1.308 (11)
C11—C151.504 (3)C24—F18A1.327 (11)
C12—C131.377 (3)C24—F18B1.330 (17)
C12—H12A0.9300C24—F17B1.33 (2)
C13—C141.390 (3)C24—F16A1.436 (15)
C13—C161.500 (3)
O1—P1—C9114.30 (9)F10B—C15—F11B97.3 (8)
O1—P1—C17111.18 (8)F10A—C15—F11B52.6 (6)
C9—P1—C17107.20 (8)F12A—C15—F11A105.5 (8)
O1—P1—C1113.04 (8)F10B—C15—F11A77.7 (7)
C9—P1—C1105.36 (9)F10A—C15—F11A101.5 (6)
C17—P1—C1105.12 (8)F11B—C15—F11A139.0 (6)
C6—C1—C2119.39 (18)F12B—C15—C11116.7 (4)
C6—C1—P1123.91 (14)F12A—C15—C11115.2 (5)
C2—C1—P1116.70 (15)F10B—C15—C11113.1 (6)
C3—C2—C1120.0 (2)F10A—C15—C11111.6 (4)
C3—C2—H2A120.0F11B—C15—C11110.5 (4)
C1—C2—H2A120.0F11A—C15—C11108.7 (4)
C4—C3—C2120.7 (2)F7A—C16—F9B126.0 (9)
C4—C3—C8120.1 (2)F7A—C16—F8B67.9 (8)
C2—C3—C8119.2 (2)F9B—C16—F8B112.0 (8)
C3—C4—C5119.53 (19)F7A—C16—F9A112.2 (10)
C3—C4—H4A120.2F8B—C16—F9A124.6 (7)
C5—C4—H4A120.2F7A—C16—F8A109.7 (7)
C4—C5—C6120.4 (2)F9B—C16—F8A80.4 (9)
C4—C5—C7120.3 (2)F9A—C16—F8A100.0 (9)
C6—C5—C7119.3 (2)F9B—C16—F7B101.4 (8)
C1—C6—C5120.01 (18)F8B—C16—F7B100.6 (6)
C1—C6—H6A120.0F9A—C16—F7B82.5 (9)
C5—C6—H6A120.0F8A—C16—F7B136.6 (8)
F3B—C7—F2A86.2 (14)F7A—C16—C13112.9 (6)
F3B—C7—F1B108.0 (14)F9B—C16—C13113.6 (7)
F2A—C7—F1B118.1 (8)F8B—C16—C13116.5 (4)
F3B—C7—F1A118.5 (11)F9A—C16—C13113.4 (6)
F2A—C7—F1A104.9 (7)F8A—C16—C13107.7 (6)
F2A—C7—F3A104.5 (7)F7B—C16—C13110.8 (5)
F1B—C7—F3A92.2 (9)C18—C17—C22119.66 (17)
F1A—C7—F3A105.4 (8)C18—C17—P1117.27 (15)
F3B—C7—F2B110.3 (12)C22—C17—P1122.98 (14)
F1B—C7—F2B108.4 (11)C17—C18—C19119.98 (19)
F1A—C7—F2B92.6 (10)C17—C18—H18A120.0
F3A—C7—F2B128.3 (13)C19—C18—H18A120.0
F3B—C7—C5114.7 (9)C20—C19—C18120.43 (18)
F2A—C7—C5115.9 (5)C20—C19—C23120.03 (18)
F1B—C7—C5111.4 (7)C18—C19—C23119.5 (2)
F1A—C7—C5113.4 (4)C19—C20—C21119.68 (18)
F3A—C7—C5111.8 (6)C19—C20—H20A120.2
F2B—C7—C5103.9 (8)C21—C20—H20A120.2
F5B—C8—F5A126.4 (6)C22—C21—C20120.38 (19)
F5A—C8—F6A110.9 (6)C22—C21—C24121.32 (18)
F5B—C8—F6B108.5 (8)C20—C21—C24118.29 (18)
F5A—C8—F6B57.5 (8)C21—C22—C17119.86 (17)
F6A—C8—F6B133.5 (5)C21—C22—H22A120.1
F5B—C8—F4A65.5 (10)C17—C22—H22A120.1
F5A—C8—F4A109.6 (5)F14B—C23—F15B117.7 (15)
F6A—C8—F4A102.7 (5)F14B—C23—F15A128.5 (7)
F6B—C8—F4A54.4 (8)F14B—C23—F13A55 (2)
F5B—C8—F4B96.6 (8)F15B—C23—F13A133.0 (8)
F5A—C8—F4B48.0 (6)F15A—C23—F13A109.2 (3)
F6A—C8—F4B66.4 (7)F14B—C23—F14A50 (2)
F6B—C8—F4B101.1 (9)F15B—C23—F14A76.9 (14)
F4A—C8—F4B136.2 (4)F15A—C23—F14A105.2 (3)
F5B—C8—C3119.3 (6)F13A—C23—F14A103.7 (3)
F5A—C8—C3112.2 (3)F14B—C23—F13B104.7 (14)
F6A—C8—C3110.6 (4)F15B—C23—F13B95.3 (11)
F6B—C8—C3115.2 (4)F15A—C23—F13B62.9 (10)
F4A—C8—C3110.3 (3)F13A—C23—F13B53.5 (10)
F4B—C8—C3113.1 (4)F14A—C23—F13B139.5 (5)
C14—C9—C10119.36 (18)F14B—C23—C19117.4 (6)
C14—C9—P1122.02 (14)F15B—C23—C19110.3 (7)
C10—C9—P1118.42 (14)F15A—C23—C19113.7 (3)
C11—C10—C9119.79 (18)F13A—C23—C19112.7 (2)
C11—C10—H10A120.1F14A—C23—C19111.5 (2)
C9—C10—H10A120.1F13B—C23—C19108.5 (5)
C12—C11—C10120.84 (18)F16B—C24—F17A97.2 (13)
C12—C11—C15120.3 (2)F16B—C24—F18A110.4 (12)
C10—C11—C15118.9 (2)F17A—C24—F18A108.7 (7)
C13—C12—C11119.3 (2)F16B—C24—F18B99.9 (13)
C13—C12—H12A120.3F17A—C24—F18B113.2 (9)
C11—C12—H12A120.3F16B—C24—F17B112.9 (19)
C12—C13—C14120.58 (19)F18A—C24—F17B96.7 (14)
C12—C13—C16120.3 (2)F18B—C24—F17B103.4 (16)
C14—C13—C16119.1 (2)F17A—C24—F16A101.4 (7)
C9—C14—C13120.04 (18)F18A—C24—F16A109.1 (9)
C9—C14—H14A120.0F18B—C24—F16A98.5 (9)
C13—C14—H14A120.0F17B—C24—F16A117 (2)
F12B—C15—F12A125.6 (6)F16B—C24—C21114.0 (12)
F12B—C15—F10B110.1 (12)F17A—C24—C21114.0 (7)
F12B—C15—F10A59.9 (12)F18A—C24—C21111.6 (6)
F12A—C15—F10A113.0 (7)F18B—C24—C21116.0 (8)
F10B—C15—F10A132.8 (6)F17B—C24—C21109.9 (12)
F12B—C15—F11B107.1 (10)F16A—C24—C21111.6 (4)
F12A—C15—F11B67.5 (6)
O1—P1—C1—C6150.78 (16)C10—C11—C15—F12A−171.8 (13)
C9—P1—C1—C625.28 (19)C12—C11—C15—F10B44.2 (9)
C17—P1—C1—C6−87.79 (17)C10—C11—C15—F10B−137.9 (8)
O1—P1—C1—C2−28.91 (18)C12—C11—C15—F10A−120.4 (10)
C9—P1—C1—C2−154.40 (15)C10—C11—C15—F10A57.5 (10)
C17—P1—C1—C292.53 (16)C12—C11—C15—F11B−63.8 (13)
C6—C1—C2—C3−0.2 (3)C10—C11—C15—F11B114.2 (13)
P1—C1—C2—C3179.48 (16)C12—C11—C15—F11A128.4 (6)
C1—C2—C3—C4−0.5 (3)C10—C11—C15—F11A−53.6 (7)
C1—C2—C3—C8−179.6 (2)C12—C13—C16—F7A88.9 (15)
C2—C3—C4—C50.7 (3)C14—C13—C16—F7A−89.2 (15)
C8—C3—C4—C5179.8 (2)C12—C13—C16—F9B−119.3 (12)
C3—C4—C5—C6−0.3 (3)C14—C13—C16—F9B62.5 (12)
C3—C4—C5—C7−177.3 (2)C12—C13—C16—F8B13.2 (11)
C2—C1—C6—C50.7 (3)C14—C13—C16—F8B−165.0 (10)
P1—C1—C6—C5−179.01 (15)C12—C13—C16—F9A−142.0 (9)
C4—C5—C6—C1−0.4 (3)C14—C13—C16—F9A39.9 (9)
C7—C5—C6—C1176.6 (2)C12—C13—C16—F8A−32.3 (13)
C4—C5—C7—F3B−160 (2)C14—C13—C16—F8A149.6 (13)
C6—C5—C7—F3B23 (2)C12—C13—C16—F7B127.3 (10)
C4—C5—C7—F2A101.8 (7)C14—C13—C16—F7B−50.9 (10)
C6—C5—C7—F2A−75.3 (7)O1—P1—C17—C18−8.74 (17)
C4—C5—C7—F1B−37.0 (9)C9—P1—C17—C18116.84 (15)
C6—C5—C7—F1B145.9 (9)C1—P1—C17—C18−131.39 (14)
C4—C5—C7—F1A−19.6 (9)O1—P1—C17—C22167.85 (15)
C6—C5—C7—F1A163.3 (9)C9—P1—C17—C22−66.56 (17)
C4—C5—C7—F3A−138.6 (5)C1—P1—C17—C2245.21 (17)
C6—C5—C7—F3A44.3 (6)C22—C17—C18—C190.8 (3)
C4—C5—C7—F2B79.5 (15)P1—C17—C18—C19177.48 (14)
C6—C5—C7—F2B−97.6 (15)C17—C18—C19—C20−0.8 (3)
C4—C3—C8—F5B−78.3 (16)C17—C18—C19—C23179.34 (18)
C2—C3—C8—F5B100.9 (16)C18—C19—C20—C210.3 (3)
C4—C3—C8—F5A116.9 (9)C23—C19—C20—C21−179.81 (19)
C2—C3—C8—F5A−64.0 (9)C19—C20—C21—C220.2 (3)
C4—C3—C8—F6A−118.7 (8)C19—C20—C21—C24−179.0 (2)
C2—C3—C8—F6A60.5 (8)C20—C21—C22—C17−0.2 (3)
C4—C3—C8—F6B53.5 (15)C24—C21—C22—C17178.99 (19)
C2—C3—C8—F6B−127.4 (15)C18—C17—C22—C21−0.3 (3)
C4—C3—C8—F4A−5.7 (8)P1—C17—C22—C21−176.79 (14)
C2—C3—C8—F4A173.4 (7)C20—C19—C23—F14B−93 (3)
C4—C3—C8—F4B169.1 (12)C18—C19—C23—F14B87 (3)
C2—C3—C8—F4B−11.7 (13)C20—C19—C23—F15B128.5 (17)
O1—P1—C9—C1498.19 (17)C18—C19—C23—F15B−51.6 (17)
C17—P1—C9—C14−25.50 (19)C20—C19—C23—F15A93.1 (4)
C1—P1—C9—C14−137.10 (17)C18—C19—C23—F15A−87.0 (4)
O1—P1—C9—C10−76.64 (17)C20—C19—C23—F13A−31.9 (5)
C17—P1—C9—C10159.67 (16)C18—C19—C23—F13A148.0 (4)
C1—P1—C9—C1048.06 (18)C20—C19—C23—F14A−148.1 (3)
C14—C9—C10—C111.7 (3)C18—C19—C23—F14A31.8 (4)
P1—C9—C10—C11176.64 (16)C20—C19—C23—F13B25.4 (14)
C9—C10—C11—C12−2.1 (3)C18—C19—C23—F13B−154.8 (14)
C9—C10—C11—C15−180.0 (2)C22—C21—C24—F16B115.3 (11)
C10—C11—C12—C130.7 (4)C20—C21—C24—F16B−65.5 (12)
C15—C11—C12—C13178.5 (2)C22—C21—C24—F17A−134.3 (7)
C11—C12—C13—C141.1 (4)C20—C21—C24—F17A44.9 (7)
C11—C12—C13—C16−177.0 (3)C22—C21—C24—F18A−10.7 (9)
C10—C9—C14—C130.1 (3)C20—C21—C24—F18A168.5 (8)
P1—C9—C14—C13−174.68 (17)C22—C21—C24—F18B0.0 (9)
C12—C13—C14—C9−1.5 (3)C20—C21—C24—F18B179.2 (9)
C16—C13—C14—C9176.6 (2)C22—C21—C24—F17B−117 (2)
C12—C11—C15—F12B173 (2)C20—C21—C24—F17B62 (2)
C10—C11—C15—F12B−9(2)C22—C21—C24—F16A111.6 (3)
C12—C11—C15—F12A10.3 (14)C20—C21—C24—F16A−69.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C18—H18A···O10.932.582.992 (3)108
C10—H10A···O1i0.932.383.203 (3)147
C20—H20A···F10Aii0.932.503.418 (12)167

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y+1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2588).

References

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  • Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1992). Aust. J. Chem., 45, 835–844.
  • Ruban, G. & Zabel, V. (1976). Cryst. Struct. Commun.5, 671–677.
  • Shawkataly, O. B., Ramalingam, K., Selvakumar, S., Fun, H.-K. & Razak, I. A. (1997). Acta Cryst. C53, 1451–1452.
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