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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809013488/sj2588sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809013488/sj2588Isup2.hkl
Contains datablock I

CCDC reference: 731306

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.041
  • wR factor = 0.113
  • Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C15
Author Response: this is due to the disorder component of the neighbouring atoms.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C23
Author Response: this is due to the disorder component of the neighbouring atoms.

Alert level B PLAT213_ALERT_2_B Atom F14B has ADP max/min Ratio ............. 4.80 prola PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C7
Author Response: this is due to the disorder component of the neighbouring atoms.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8
Author Response: this is due to the disorder component of the neighbouring atoms.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C16
Author Response: this is due to the disorder component of the neighbouring atoms.

Alert level C Value of measurement temperature given = 294.000 Value of melting point given = 0.000 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.03 PLAT213_ALERT_2_C Atom F12A has ADP max/min Ratio ............. 3.40 prola PLAT213_ALERT_2_C Atom F2B has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom F12B has ADP max/min Ratio ............. 3.80 prola PLAT213_ALERT_2_C Atom F15B has ADP max/min Ratio ............. 3.90 prola PLAT220_ALERT_2_C Large Non-Solvent F Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24
Author Response: this is due to the disorder component of the neighbouring atoms.

Alert level G PLAT301_ALERT_3_G Note Main Residue Disorder .................... 29.00 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 168 PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 1000 Deg. PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... !
2 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

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 PO 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).

Related literature top

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

Experimental top

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

Refinement top

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.

Computing details top

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

Figures top
[Figure 1] 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.
Tris[3,5-bis(trifluoromethyl)phenyl]phosphine oxide top
Crystal data top
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 top
Bruker SMART APEXII CCD area-detector
diffractometer
4535 independent reflections
Radiation source: fine-focus sealed tube3611 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1112
Tmin = 0.890, Tmax = 0.947k = 1314
7134 measured reflectionsl = 1410
Refinement top
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 = 1.02 w = 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
Crystal data top
C24H9F18OPγ = 106.562 (10)°
Mr = 686.28V = 1327.7 (3) Å3
Triclinic, P1Z = 2
a = 10.7937 (2) ÅMo Kα radiation
b = 11.8786 (10) ŵ = 0.25 mm1
c = 12.5066 (10) ÅT = 294 K
α = 111.065 (10)°0.48 × 0.38 × 0.22 mm
β = 103.645 (10)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4535 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3611 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.947Rint = 0.021
7134 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041168 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
4535 reflectionsΔρmin = 0.27 e Å3
565 parameters
Special details top

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) top
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)
H10A0.49540.30030.00210.055*
C110.5843 (2)0.1740 (2)0.0606 (2)0.0531 (5)
C120.7100 (2)0.1634 (2)0.0525 (2)0.0574 (6)
H12A0.71170.08280.09820.069*
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) top
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, º) top
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—F12A171.8 (13)
C9—P1—C1—C625.28 (19)C12—C11—C15—F10B44.2 (9)
C17—P1—C1—C687.79 (17)C10—C11—C15—F10B137.9 (8)
O1—P1—C1—C228.91 (18)C12—C11—C15—F10A120.4 (10)
C9—P1—C1—C2154.40 (15)C10—C11—C15—F10A57.5 (10)
C17—P1—C1—C292.53 (16)C12—C11—C15—F11B63.8 (13)
C6—C1—C2—C30.2 (3)C10—C11—C15—F11B114.2 (13)
P1—C1—C2—C3179.48 (16)C12—C11—C15—F11A128.4 (6)
C1—C2—C3—C40.5 (3)C10—C11—C15—F11A53.6 (7)
C1—C2—C3—C8179.6 (2)C12—C13—C16—F7A88.9 (15)
C2—C3—C4—C50.7 (3)C14—C13—C16—F7A89.2 (15)
C8—C3—C4—C5179.8 (2)C12—C13—C16—F9B119.3 (12)
C3—C4—C5—C60.3 (3)C14—C13—C16—F9B62.5 (12)
C3—C4—C5—C7177.3 (2)C12—C13—C16—F8B13.2 (11)
C2—C1—C6—C50.7 (3)C14—C13—C16—F8B165.0 (10)
P1—C1—C6—C5179.01 (15)C12—C13—C16—F9A142.0 (9)
C4—C5—C6—C10.4 (3)C14—C13—C16—F9A39.9 (9)
C7—C5—C6—C1176.6 (2)C12—C13—C16—F8A32.3 (13)
C4—C5—C7—F3B160 (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—F7B50.9 (10)
C6—C5—C7—F2A75.3 (7)O1—P1—C17—C188.74 (17)
C4—C5—C7—F1B37.0 (9)C9—P1—C17—C18116.84 (15)
C6—C5—C7—F1B145.9 (9)C1—P1—C17—C18131.39 (14)
C4—C5—C7—F1A19.6 (9)O1—P1—C17—C22167.85 (15)
C6—C5—C7—F1A163.3 (9)C9—P1—C17—C2266.56 (17)
C4—C5—C7—F3A138.6 (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—F2B97.6 (15)C17—C18—C19—C200.8 (3)
C4—C3—C8—F5B78.3 (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—C21179.81 (19)
C2—C3—C8—F5A64.0 (9)C19—C20—C21—C220.2 (3)
C4—C3—C8—F6A118.7 (8)C19—C20—C21—C24179.0 (2)
C2—C3—C8—F6A60.5 (8)C20—C21—C22—C170.2 (3)
C4—C3—C8—F6B53.5 (15)C24—C21—C22—C17178.99 (19)
C2—C3—C8—F6B127.4 (15)C18—C17—C22—C210.3 (3)
C4—C3—C8—F4A5.7 (8)P1—C17—C22—C21176.79 (14)
C2—C3—C8—F4A173.4 (7)C20—C19—C23—F14B93 (3)
C4—C3—C8—F4B169.1 (12)C18—C19—C23—F14B87 (3)
C2—C3—C8—F4B11.7 (13)C20—C19—C23—F15B128.5 (17)
O1—P1—C9—C1498.19 (17)C18—C19—C23—F15B51.6 (17)
C17—P1—C9—C1425.50 (19)C20—C19—C23—F15A93.1 (4)
C1—P1—C9—C14137.10 (17)C18—C19—C23—F15A87.0 (4)
O1—P1—C9—C1076.64 (17)C20—C19—C23—F13A31.9 (5)
C17—P1—C9—C10159.67 (16)C18—C19—C23—F13A148.0 (4)
C1—P1—C9—C1048.06 (18)C20—C19—C23—F14A148.1 (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—C122.1 (3)C18—C19—C23—F13B154.8 (14)
C9—C10—C11—C15180.0 (2)C22—C21—C24—F16B115.3 (11)
C10—C11—C12—C130.7 (4)C20—C21—C24—F16B65.5 (12)
C15—C11—C12—C13178.5 (2)C22—C21—C24—F17A134.3 (7)
C11—C12—C13—C141.1 (4)C20—C21—C24—F17A44.9 (7)
C11—C12—C13—C16177.0 (3)C22—C21—C24—F18A10.7 (9)
C10—C9—C14—C130.1 (3)C20—C21—C24—F18A168.5 (8)
P1—C9—C14—C13174.68 (17)C22—C21—C24—F18B0.0 (9)
C12—C13—C14—C91.5 (3)C20—C21—C24—F18B179.2 (9)
C16—C13—C14—C9176.6 (2)C22—C21—C24—F17B117 (2)
C12—C11—C15—F12B173 (2)C20—C21—C24—F17B62 (2)
C10—C11—C15—F12B9 (2)C22—C21—C24—F16A111.6 (3)
C12—C11—C15—F12A10.3 (14)C20—C21—C24—F16A69.2 (4)
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formulaC24H9F18OP
Mr686.28
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)10.7937 (2), 11.8786 (10), 12.5066 (10)
α, β, γ (°)111.065 (10), 103.645 (10), 106.562 (10)
V3)1327.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.48 × 0.38 × 0.22
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.890, 0.947
No. of measured, independent and
observed [I > 2σ(I)] reflections
7134, 4535, 3611
Rint0.021
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.113, 1.02
No. of reflections4535
No. of parameters565
No. of restraints168
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
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.
 

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