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Halogen bonding to phospho­rus atoms remains uncommon, with relatively few examples reported in the literature. Here, the preparation and investigation of the cocrystal bis(di­cyclo­hexyl­phenyl­phosphine)(1,6-di­iodo­perfluoro­hexane) by X-ray crystallography and solid-state multinuclear magnetic resonance spectroscopy is described. The crystal structure features two crystallographically unique C—I...P halogen bonds [dI...P = 3.090 (5) Å, 3.264 (5) Å] and crystallographic disorder of one of the 1,6-di­iodo­perfluoro­hexane molecules. The first of these is the shortest and most linear I...P halogen bond reported to date. 13C, 19F, and 31P magic angle spinning solid-state NMR spectra are reported. A 31P chemical shift change of −7.0 p.p.m. in the cocrystal relative to pure di­cyclo­hexyl­phenyl­phosphine, consistent with halogen bond formation, is noted. This work establishes iodo­perfluoro­alkanes as viable halogen bond donors when paired with phospho­rus acceptors, and also shows that di­cyclo­hexyl­phenyl­phosphine can act as a practical halogen bond acceptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520622004322/rm5059sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520622004322/rm5059Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520622004322/rm5059sup3.pdf
Fig. S1 and Tables S1-S2

CCDC reference: 2128052

Computing details top

Data collection: Bruker APEX3; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018).

(I) top
Crystal data top
2(C18H27P)·(C6F12I2)Z = 2
Mr = 1102.59F(000) = 1100
Triclinic, P1Dx = 1.593 Mg m3
a = 10.321 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.231 (4) ÅCell parameters from 5993 reflections
c = 15.663 (4) Åθ = 2.7–23.3°
α = 82.730 (6)°µ = 1.52 mm1
β = 80.201 (5)°T = 293 K
γ = 71.847 (6)°Plate, colourless
V = 2298.5 (11) Å30.13 × 0.09 × 0.05 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
ω and πhi scansθmax = 23.3°, θmin = 1.3°
Absorption correction: multi-scan
SADABS
h = 118
Tmin = 0.604, Tmax = 0.745k = 1616
19267 measured reflectionsl = 1717
6489 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.123H-atom parameters constrained
wR(F2) = 0.192 w = 1/[σ2(Fo2) + 37.981P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
6489 reflectionsΔρmax = 1.13 e Å3
605 parametersΔρmin = 1.21 e Å3
259 restraints
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. none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.85453 (12)0.07248 (8)0.81871 (7)0.0571 (4)
F10.937 (2)0.0922 (8)0.7217 (7)0.170 (8)
F21.1011 (14)0.0336 (11)0.7164 (7)0.165 (8)
F30.8073 (10)0.0621 (8)0.6231 (6)0.105 (4)
F40.9876 (13)0.1049 (7)0.6140 (6)0.110 (4)
F50.9439 (10)0.0931 (6)0.5504 (5)0.076 (3)
F61.1400 (10)0.0683 (6)0.5520 (5)0.074 (3)
C10.9616 (19)0.0122 (13)0.7122 (11)0.084 (6)
C20.9428 (15)0.0312 (9)0.6229 (8)0.046 (4)
C31.0090 (16)0.0259 (10)0.5441 (9)0.053 (4)
P10.7051 (4)0.1885 (3)0.9742 (3)0.0499 (11)
P20.2100 (4)0.5613 (3)0.5934 (3)0.0563 (12)
C70.5526 (16)0.2876 (10)0.9505 (11)0.051 (4)
C80.4892 (17)0.2810 (11)0.8825 (11)0.060 (5)
H80.5239050.2298780.8496440.072*
C90.3735 (17)0.3511 (13)0.8632 (11)0.067 (5)
H90.3324590.3486060.8153910.080*
C100.3188 (18)0.4241 (12)0.9141 (13)0.070 (5)
H100.2384550.4696420.9021740.083*
C110.3804 (19)0.4308 (12)0.9814 (12)0.067 (5)
H110.3432290.4812791.0150060.080*
C120.4978 (18)0.3631 (12)1.0005 (11)0.062 (5)
H120.5404480.3678561.0466900.075*
C130.8177 (15)0.2419 (10)1.0136 (9)0.048 (4)
H130.7635010.2818901.0594350.057*
C140.8761 (17)0.3020 (12)0.9394 (10)0.065 (5)
H14A0.9231290.2639950.8916300.079*
H14B0.8003890.3512290.9184120.079*
C150.9762 (19)0.3446 (12)0.9679 (12)0.077 (6)
H15A1.0134790.3788540.9184810.093*
H15B0.9274530.3876441.0115560.093*
C161.0932 (17)0.2694 (13)1.0051 (12)0.076 (6)
H16A1.1468550.2294860.9599590.091*
H16B1.1534350.2976561.0253140.091*
C171.0363 (19)0.2121 (13)1.0801 (12)0.078 (6)
H17A1.1114740.1628341.1015960.094*
H17B0.9890950.2510151.1271330.094*
C180.9367 (17)0.1704 (11)1.0507 (11)0.067 (5)
H18A0.9865410.1276221.0070610.080*
H18B0.9006130.1351981.0999140.080*
C190.6403 (16)0.1243 (10)1.0717 (9)0.050 (4)
H190.6583690.1475091.1226820.060*
C200.7189 (18)0.0201 (11)1.0722 (11)0.071 (5)
H20A0.7050780.0039861.0211550.085*
H20B0.8165860.0120441.0688770.085*
C210.673 (2)0.0357 (12)1.1533 (12)0.086 (6)
H21A0.7211160.1010151.1484150.103*
H21B0.6971060.0171241.2039420.103*
C220.522 (2)0.0218 (13)1.1654 (12)0.077 (6)
H22A0.4956830.0536271.2201110.093*
H22B0.4996460.0489141.1191000.093*
C230.4414 (18)0.0791 (13)1.1651 (12)0.077 (6)
H23A0.4534870.1041911.2161250.093*
H23B0.3442470.0855661.1680000.093*
C240.4881 (16)0.1346 (12)1.0829 (11)0.067 (5)
H24A0.4671140.1134831.0323830.080*
H24B0.4366480.1995691.0861100.080*
C250.2951 (16)0.6179 (11)0.6505 (10)0.054 (4)
C260.2725 (16)0.7138 (11)0.6462 (10)0.057 (5)
H260.2079460.7533620.6130540.069*
C270.3464 (19)0.7501 (14)0.6915 (12)0.077 (6)
H270.3409070.8125930.6810410.092*
C280.4267 (18)0.6965 (15)0.7508 (12)0.074 (6)
H280.4643500.7230160.7869480.089*
C290.4508 (19)0.6005 (14)0.7556 (11)0.073 (5)
H290.5148650.5613960.7893690.087*
C300.3782 (16)0.5639 (11)0.7097 (10)0.058 (5)
H300.3858210.5011220.7190700.070*
C310.0325 (15)0.5913 (11)0.6525 (11)0.055 (4)
H310.0138620.5586760.6235770.066*
C320.0270 (17)0.5470 (12)0.7451 (13)0.078 (6)
H32A0.0681480.4804680.7437450.093*
H32B0.0813840.5699040.7766020.093*
C330.1170 (18)0.5663 (12)0.7927 (11)0.074 (5)
H33A0.1623170.5280170.7716290.088*
H33B0.1116760.5476250.8538980.088*
C340.2030 (18)0.6634 (12)0.7845 (12)0.074 (5)
H34A0.2972350.6670260.8089000.088*
H34B0.1710480.7001410.8178020.088*
C350.1995 (18)0.7023 (12)0.6941 (11)0.073 (5)
H35A0.2492030.7678540.6930370.088*
H35B0.2472760.6728650.6636960.088*
C360.0570 (15)0.6905 (10)0.6461 (10)0.052 (4)
H36A0.0145950.7289540.6697080.063*
H36B0.0629350.7114960.5854030.063*
C370.1979 (14)0.6283 (10)0.4867 (9)0.045 (4)
H370.1508250.6936620.4962400.055*
C380.1154 (15)0.5947 (10)0.4330 (9)0.050 (4)
H38A0.0230380.6026770.4636520.060*
H38B0.1581710.5291200.4260020.060*
C390.1073 (15)0.6476 (11)0.3436 (10)0.054 (4)
H39A0.0592640.6218930.3097840.064*
H39B0.0555070.7120770.3501360.064*
C400.2504 (15)0.6413 (11)0.2960 (10)0.057 (5)
H40A0.2965710.5777900.2820600.068*
H40B0.2423150.6797840.2417130.068*
C410.3372 (16)0.6714 (12)0.3480 (10)0.061 (5)
H41A0.4302100.6594570.3173890.074*
H41B0.2998160.7375630.3537740.074*
C420.3406 (15)0.6205 (11)0.4369 (10)0.052 (4)
H42A0.3906970.6450170.4702200.062*
H42B0.3901350.5555450.4308640.062*
I2A0.29643 (13)0.33716 (10)0.58439 (9)0.0791 (5)0.469 (12)
F7A0.2401 (17)0.1627 (18)0.6452 (18)0.123 (8)0.469 (12)
F8A0.4465 (19)0.1626 (16)0.6660 (17)0.152 (11)0.469 (12)
F9A0.3239 (19)0.1617 (17)0.4774 (17)0.145 (10)0.469 (12)
F10A0.5315 (16)0.1600 (16)0.4972 (17)0.109 (7)0.469 (12)
F11A0.3470 (18)0.004 (2)0.5700 (18)0.098 (7)0.469 (12)
F12A0.5472 (18)0.0013 (15)0.6042 (14)0.095 (7)0.469 (12)
C4A0.350 (3)0.1874 (14)0.6088 (16)0.099 (6)0.469 (12)
C5A0.419 (2)0.1344 (14)0.5313 (14)0.088 (5)0.469 (12)
C6A0.467 (3)0.0275 (15)0.5433 (16)0.082 (5)0.469 (12)
I2B0.29643 (13)0.33716 (10)0.58439 (9)0.0791 (5)0.531 (12)
F7B0.1972 (16)0.1863 (12)0.5467 (11)0.097 (7)0.531 (12)
F8B0.307 (2)0.1532 (17)0.6615 (11)0.123 (8)0.531 (12)
F9B0.437 (2)0.1717 (14)0.4467 (9)0.106 (7)0.531 (12)
F10B0.5385 (18)0.1351 (16)0.5651 (13)0.131 (9)0.531 (12)
F11B0.352 (3)0.0342 (19)0.4624 (13)0.173 (12)0.531 (12)
F12B0.399 (3)0.008 (2)0.5966 (12)0.120 (8)0.531 (12)
C4B0.305 (2)0.1936 (14)0.5763 (17)0.093 (6)0.531 (12)
C5B0.432 (2)0.1325 (14)0.5281 (13)0.083 (4)0.531 (12)
C6B0.442 (2)0.0302 (15)0.5217 (16)0.085 (5)0.531 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0591 (8)0.0619 (7)0.0473 (7)0.0132 (6)0.0056 (6)0.0082 (6)
F10.38 (3)0.054 (7)0.057 (8)0.072 (11)0.033 (11)0.007 (6)
F20.123 (12)0.230 (18)0.067 (9)0.082 (12)0.040 (8)0.052 (9)
F30.055 (7)0.159 (11)0.075 (8)0.029 (7)0.021 (6)0.053 (7)
F40.189 (13)0.093 (8)0.074 (8)0.097 (9)0.028 (8)0.029 (6)
F50.126 (9)0.074 (7)0.043 (6)0.056 (7)0.002 (6)0.004 (5)
F60.067 (7)0.080 (7)0.049 (6)0.018 (5)0.011 (5)0.005 (5)
C10.068 (15)0.112 (18)0.059 (14)0.010 (13)0.007 (11)0.010 (13)
C20.057 (12)0.049 (10)0.030 (10)0.010 (9)0.006 (8)0.010 (8)
C30.060 (12)0.046 (10)0.049 (11)0.011 (9)0.014 (10)0.002 (8)
P10.049 (3)0.056 (3)0.041 (3)0.009 (2)0.005 (2)0.013 (2)
P20.046 (3)0.064 (3)0.060 (3)0.020 (2)0.010 (2)0.001 (2)
C70.054 (11)0.035 (9)0.060 (12)0.012 (8)0.002 (10)0.005 (9)
C80.063 (13)0.061 (12)0.056 (12)0.013 (10)0.018 (10)0.009 (9)
C90.046 (12)0.089 (14)0.055 (12)0.010 (11)0.012 (10)0.014 (11)
C100.043 (12)0.060 (13)0.076 (15)0.013 (9)0.002 (11)0.014 (11)
C110.064 (13)0.060 (12)0.073 (14)0.015 (11)0.015 (11)0.004 (10)
C120.062 (13)0.069 (13)0.055 (12)0.020 (10)0.014 (10)0.007 (10)
C130.057 (11)0.048 (9)0.034 (9)0.010 (8)0.009 (8)0.003 (8)
C140.064 (12)0.076 (12)0.048 (11)0.011 (10)0.019 (10)0.016 (9)
C150.091 (15)0.069 (13)0.086 (15)0.048 (12)0.019 (12)0.012 (11)
C160.053 (12)0.087 (14)0.089 (15)0.025 (11)0.019 (11)0.007 (12)
C170.081 (14)0.091 (14)0.081 (14)0.047 (12)0.041 (12)0.022 (12)
C180.070 (13)0.070 (12)0.067 (13)0.027 (10)0.034 (10)0.018 (10)
C190.059 (11)0.057 (10)0.034 (10)0.018 (9)0.001 (8)0.012 (8)
C200.072 (13)0.059 (12)0.069 (13)0.004 (10)0.005 (11)0.001 (10)
C210.113 (19)0.057 (12)0.063 (14)0.009 (12)0.010 (13)0.013 (10)
C220.085 (16)0.093 (16)0.062 (13)0.045 (13)0.011 (12)0.013 (11)
C230.061 (13)0.086 (15)0.078 (15)0.017 (11)0.003 (11)0.007 (12)
C240.048 (12)0.075 (13)0.073 (13)0.012 (10)0.011 (10)0.000 (10)
C250.054 (11)0.049 (10)0.066 (12)0.017 (8)0.030 (9)0.004 (9)
C260.050 (11)0.066 (12)0.052 (11)0.011 (9)0.019 (9)0.008 (9)
C270.074 (14)0.088 (14)0.080 (15)0.033 (12)0.026 (12)0.007 (12)
C280.053 (12)0.117 (18)0.061 (14)0.022 (12)0.014 (10)0.037 (13)
C290.074 (14)0.079 (15)0.055 (13)0.002 (11)0.019 (11)0.011 (11)
C300.062 (12)0.045 (10)0.057 (12)0.004 (9)0.022 (10)0.000 (9)
C310.046 (11)0.055 (11)0.062 (12)0.009 (9)0.011 (9)0.012 (9)
C320.046 (12)0.072 (13)0.105 (17)0.021 (10)0.039 (12)0.029 (12)
C330.060 (13)0.081 (14)0.066 (13)0.006 (11)0.004 (11)0.009 (11)
C340.059 (13)0.080 (14)0.078 (15)0.015 (11)0.006 (11)0.008 (11)
C350.064 (13)0.081 (13)0.057 (13)0.005 (10)0.006 (11)0.027 (11)
C360.039 (10)0.066 (11)0.044 (10)0.008 (8)0.001 (8)0.001 (8)
C370.038 (10)0.049 (10)0.045 (10)0.016 (8)0.010 (8)0.005 (8)
C380.042 (10)0.058 (10)0.050 (11)0.013 (8)0.002 (8)0.012 (9)
C390.044 (10)0.071 (11)0.048 (11)0.015 (9)0.015 (9)0.004 (9)
C400.047 (11)0.073 (12)0.045 (11)0.007 (9)0.008 (9)0.008 (9)
C410.043 (11)0.083 (13)0.053 (12)0.019 (9)0.003 (9)0.008 (10)
C420.038 (10)0.061 (11)0.057 (12)0.017 (8)0.000 (9)0.010 (9)
I2A0.0527 (8)0.1017 (11)0.0855 (10)0.0293 (7)0.0171 (7)0.0103 (8)
F7A0.087 (13)0.107 (15)0.159 (16)0.036 (12)0.037 (11)0.007 (14)
F8A0.16 (2)0.13 (2)0.173 (18)0.017 (18)0.076 (18)0.008 (16)
F9A0.158 (19)0.099 (18)0.18 (2)0.010 (17)0.095 (19)0.014 (16)
F10A0.075 (11)0.097 (13)0.141 (18)0.036 (11)0.027 (10)0.010 (14)
F11A0.069 (12)0.090 (14)0.131 (17)0.036 (11)0.012 (10)0.003 (13)
F12A0.094 (16)0.091 (16)0.087 (14)0.000 (12)0.025 (12)0.014 (11)
C4A0.075 (10)0.116 (12)0.098 (10)0.035 (7)0.002 (8)0.015 (8)
C5A0.068 (9)0.103 (8)0.090 (10)0.038 (7)0.003 (7)0.023 (7)
C6A0.068 (10)0.104 (8)0.076 (13)0.041 (7)0.008 (8)0.021 (8)
I2B0.0527 (8)0.1017 (11)0.0855 (10)0.0293 (7)0.0171 (7)0.0103 (8)
F7B0.052 (9)0.076 (14)0.159 (18)0.013 (9)0.004 (11)0.026 (13)
F8B0.117 (18)0.114 (14)0.109 (10)0.016 (14)0.010 (9)0.013 (10)
F9B0.088 (15)0.102 (12)0.097 (10)0.006 (12)0.007 (8)0.018 (9)
F10B0.069 (11)0.13 (2)0.20 (2)0.002 (11)0.055 (14)0.060 (19)
F11B0.17 (2)0.15 (2)0.22 (2)0.04 (2)0.12 (2)0.02 (2)
F12B0.114 (17)0.100 (12)0.117 (13)0.025 (15)0.024 (11)0.022 (10)
C4B0.063 (8)0.110 (12)0.107 (10)0.044 (6)0.003 (7)0.010 (8)
C5B0.056 (8)0.107 (8)0.091 (9)0.041 (6)0.011 (7)0.012 (7)
C6B0.063 (12)0.108 (8)0.092 (12)0.044 (8)0.011 (8)0.013 (7)
Geometric parameters (Å, º) top
I1—C12.167 (16)C26—C271.39 (2)
F1—C11.303 (19)C26—H260.9300
F2—C11.385 (19)C27—C281.37 (2)
F3—C21.329 (14)C27—H270.9300
F4—C21.324 (14)C28—C291.40 (2)
F5—C31.373 (15)C28—H280.9300
F6—C31.324 (15)C29—C301.39 (2)
C1—C21.487 (19)C29—H290.9300
C2—C31.536 (17)C30—H300.9300
C3—C3i1.51 (3)C31—C361.506 (19)
P1—C131.832 (15)C31—C321.52 (2)
P1—C191.848 (15)C31—H310.9800
P1—C71.863 (16)C32—C331.50 (2)
P2—C251.802 (15)C32—H32A0.9700
P2—C371.847 (15)C32—H32B0.9700
P2—C311.852 (16)C33—C341.47 (2)
C7—C81.37 (2)C33—H33A0.9700
C7—C121.39 (2)C33—H33B0.9700
C8—C91.38 (2)C34—C351.46 (2)
C8—H80.9300C34—H34A0.9700
C9—C101.37 (2)C34—H34B0.9700
C9—H90.9300C35—C361.50 (2)
C10—C111.35 (2)C35—H35A0.9700
C10—H100.9300C35—H35B0.9700
C11—C121.37 (2)C36—H36A0.9700
C11—H110.9300C36—H36B0.9700
C12—H120.9300C37—C421.521 (18)
C13—C181.510 (19)C37—C381.523 (19)
C13—C141.545 (19)C37—H370.9800
C13—H130.9800C38—C391.526 (19)
C14—C151.53 (2)C38—H38A0.9700
C14—H14A0.9700C38—H38B0.9700
C14—H14B0.9700C39—C401.517 (19)
C15—C161.52 (2)C39—H39A0.9700
C15—H15A0.9700C39—H39B0.9700
C15—H15B0.9700C40—C411.51 (2)
C16—C171.52 (2)C40—H40A0.9700
C16—H16A0.9700C40—H40B0.9700
C16—H16B0.9700C41—C421.507 (19)
C17—C181.52 (2)C41—H41A0.9700
C17—H17A0.9700C41—H41B0.9700
C17—H17B0.9700C42—H42A0.9700
C18—H18A0.9700C42—H42B0.9700
C18—H18B0.9700I2A—C4A2.17 (2)
C19—C241.512 (19)F7A—C4A1.32 (2)
C19—C201.54 (2)F8A—C4A1.39 (2)
C19—H190.9800F9A—C5A1.337 (19)
C20—C211.53 (2)F10A—C5A1.343 (18)
C20—H20A0.9700F11A—C6A1.38 (2)
C20—H20B0.9700F12A—C6A1.31 (2)
C21—C221.49 (2)C4A—C5A1.49 (2)
C21—H21A0.9700C5A—C6A1.54 (2)
C21—H21B0.9700C6A—C6Aii1.62 (5)
C22—C231.50 (2)I2B—C4B2.180 (19)
C22—H22A0.9700F7B—C4B1.31 (2)
C22—H22B0.9700F8B—C4B1.40 (2)
C23—C241.54 (2)F9B—C5B1.338 (19)
C23—H23A0.9700F10B—C5B1.342 (18)
C23—H23B0.9700F11B—C6B1.40 (2)
C24—H24A0.9700F12B—C6B1.31 (2)
C24—H24B0.9700C4B—C5B1.49 (2)
C25—C301.38 (2)C5B—C6B1.54 (2)
C25—C261.40 (2)C6B—C6Bii1.39 (5)
F1—C1—F2104.7 (15)C28—C27—C26121.7 (18)
F1—C1—C2110.0 (15)C28—C27—H27119.1
F2—C1—C2105.5 (14)C26—C27—H27119.1
F1—C1—I1112.0 (12)C27—C28—C29118.1 (17)
F2—C1—I1106.9 (11)C27—C28—H28121.0
C2—C1—I1116.8 (11)C29—C28—H28121.0
F4—C2—F3107.0 (12)C30—C29—C28119.5 (17)
F4—C2—C1106.5 (13)C30—C29—H29120.2
F3—C2—C1104.9 (13)C28—C29—H29120.2
F4—C2—C3108.6 (11)C25—C30—C29122.2 (16)
F3—C2—C3109.1 (11)C25—C30—H30118.9
C1—C2—C3119.9 (12)C29—C30—H30118.9
F6—C3—F5107.5 (11)C36—C31—C32112.8 (13)
F6—C3—C3i112.2 (16)C36—C31—P2119.0 (11)
F5—C3—C3i106.2 (15)C32—C31—P2112.1 (11)
F6—C3—C2108.5 (12)C36—C31—H31103.6
F5—C3—C2105.9 (11)C32—C31—H31103.6
C3i—C3—C2115.9 (15)P2—C31—H31103.6
C13—P1—C19104.4 (7)C33—C32—C31113.0 (14)
C13—P1—C7104.3 (7)C33—C32—H32A109.0
C19—P1—C7104.4 (7)C31—C32—H32A109.0
C25—P2—C37104.2 (7)C33—C32—H32B109.0
C25—P2—C31102.9 (8)C31—C32—H32B109.0
C37—P2—C31105.7 (7)H32A—C32—H32B107.8
C8—C7—C12119.8 (15)C34—C33—C32115.4 (16)
C8—C7—P1116.6 (13)C34—C33—H33A108.4
C12—C7—P1123.5 (14)C32—C33—H33A108.4
C7—C8—C9119.4 (16)C34—C33—H33B108.4
C7—C8—H8120.3C32—C33—H33B108.4
C9—C8—H8120.3H33A—C33—H33B107.5
C10—C9—C8120.2 (17)C35—C34—C33112.3 (16)
C10—C9—H9119.9C35—C34—H34A109.1
C8—C9—H9119.9C33—C34—H34A109.1
C11—C10—C9120.7 (17)C35—C34—H34B109.1
C11—C10—H10119.7C33—C34—H34B109.1
C9—C10—H10119.7H34A—C34—H34B107.9
C10—C11—C12120.1 (18)C34—C35—C36114.1 (15)
C10—C11—H11119.9C34—C35—H35A108.7
C12—C11—H11119.9C36—C35—H35A108.7
C11—C12—C7119.8 (17)C34—C35—H35B108.7
C11—C12—H12120.1C36—C35—H35B108.7
C7—C12—H12120.1H35A—C35—H35B107.6
C18—C13—C14108.6 (13)C35—C36—C31112.3 (13)
C18—C13—P1112.0 (10)C35—C36—H36A109.1
C14—C13—P1110.6 (10)C31—C36—H36A109.1
C18—C13—H13108.5C35—C36—H36B109.1
C14—C13—H13108.5C31—C36—H36B109.1
P1—C13—H13108.5H36A—C36—H36B107.9
C15—C14—C13112.7 (13)C42—C37—C38109.5 (12)
C15—C14—H14A109.1C42—C37—P2110.7 (10)
C13—C14—H14A109.1C38—C37—P2110.8 (10)
C15—C14—H14B109.1C42—C37—H37108.6
C13—C14—H14B109.1C38—C37—H37108.6
H14A—C14—H14B107.8P2—C37—H37108.6
C16—C15—C14110.5 (14)C37—C38—C39111.6 (12)
C16—C15—H15A109.5C37—C38—H38A109.3
C14—C15—H15A109.5C39—C38—H38A109.3
C16—C15—H15B109.5C37—C38—H38B109.3
C14—C15—H15B109.5C39—C38—H38B109.3
H15A—C15—H15B108.1H38A—C38—H38B108.0
C17—C16—C15110.3 (14)C40—C39—C38110.6 (12)
C17—C16—H16A109.6C40—C39—H39A109.5
C15—C16—H16A109.6C38—C39—H39A109.5
C17—C16—H16B109.6C40—C39—H39B109.5
C15—C16—H16B109.6C38—C39—H39B109.5
H16A—C16—H16B108.1H39A—C39—H39B108.1
C18—C17—C16110.5 (14)C41—C40—C39113.0 (13)
C18—C17—H17A109.5C41—C40—H40A109.0
C16—C17—H17A109.5C39—C40—H40A109.0
C18—C17—H17B109.5C41—C40—H40B109.0
C16—C17—H17B109.5C39—C40—H40B109.0
H17A—C17—H17B108.1H40A—C40—H40B107.8
C13—C18—C17113.4 (14)C42—C41—C40111.0 (13)
C13—C18—H18A108.9C42—C41—H41A109.4
C17—C18—H18A108.9C40—C41—H41A109.4
C13—C18—H18B108.9C42—C41—H41B109.4
C17—C18—H18B108.9C40—C41—H41B109.4
H18A—C18—H18B107.7H41A—C41—H41B108.0
C24—C19—C20107.9 (13)C41—C42—C37113.1 (13)
C24—C19—P1115.3 (11)C41—C42—H42A109.0
C20—C19—P1110.7 (10)C37—C42—H42A109.0
C24—C19—H19107.5C41—C42—H42B109.0
C20—C19—H19107.5C37—C42—H42B109.0
P1—C19—H19107.5H42A—C42—H42B107.8
C21—C20—C19112.8 (14)F7A—C4A—F8A109.3 (16)
C21—C20—H20A109.0F7A—C4A—C5A110 (2)
C19—C20—H20A109.0F8A—C4A—C5A105 (2)
C21—C20—H20B109.0F7A—C4A—I2A110.1 (18)
C19—C20—H20B109.0F8A—C4A—I2A106.5 (17)
H20A—C20—H20B107.8C5A—C4A—I2A115.0 (14)
C22—C21—C20111.8 (16)F9A—C5A—F10A111.0 (15)
C22—C21—H21A109.3F9A—C5A—C4A103.1 (18)
C20—C21—H21A109.3F10A—C5A—C4A108.8 (19)
C22—C21—H21B109.3F9A—C5A—C6A109.3 (18)
C20—C21—H21B109.3F10A—C5A—C6A106.0 (17)
H21A—C21—H21B107.9C4A—C5A—C6A118.7 (17)
C21—C22—C23111.8 (15)F12A—C6A—F11A110.2 (16)
C21—C22—H22A109.2F12A—C6A—C5A109.2 (19)
C23—C22—H22A109.2F11A—C6A—C5A104.0 (19)
C21—C22—H22B109.2F12A—C6A—C6Aii113 (3)
C23—C22—H22B109.2F11A—C6A—C6Aii103 (2)
H22A—C22—H22B107.9C5A—C6A—C6Aii117 (2)
C22—C23—C24111.4 (15)F7B—C4B—F8B109.0 (15)
C22—C23—H23A109.3F7B—C4B—C5B108.4 (18)
C24—C23—H23A109.3F8B—C4B—C5B102.9 (18)
C22—C23—H23B109.3F7B—C4B—I2B112.7 (15)
C24—C23—H23B109.3F8B—C4B—I2B105.4 (17)
H23A—C23—H23B108.0C5B—C4B—I2B117.7 (14)
C19—C24—C23112.4 (14)F9B—C5B—F10B111.0 (15)
C19—C24—H24A109.1F9B—C5B—C4B104.7 (18)
C23—C24—H24A109.1F10B—C5B—C4B106.9 (17)
C19—C24—H24B109.1F9B—C5B—C6B106.4 (17)
C23—C24—H24B109.1F10B—C5B—C6B108.7 (17)
H24A—C24—H24B107.8C4B—C5B—C6B119.1 (16)
C30—C25—C26117.1 (14)F12B—C6B—C6Bii112 (3)
C30—C25—P2117.7 (12)F12B—C6B—F11B108.9 (15)
C26—C25—P2124.9 (12)C6Bii—C6B—F11B97 (3)
C27—C26—C25120.2 (16)F12B—C6B—C5B112 (2)
C27—C26—H26119.9C6Bii—C6B—C5B122 (2)
C25—C26—H26119.9F11B—C6B—C5B104.3 (18)
F1—C1—C2—F4171.4 (15)C26—C25—C30—C298 (3)
F2—C1—C2—F459.0 (17)P2—C25—C30—C29178.5 (13)
I1—C1—C2—F459.5 (16)C28—C29—C30—C258 (3)
F1—C1—C2—F375.4 (17)C25—P2—C31—C3668.1 (14)
F2—C1—C2—F3172.2 (13)C37—P2—C31—C3640.9 (14)
I1—C1—C2—F353.7 (16)C25—P2—C31—C3266.6 (13)
F1—C1—C2—C348 (2)C37—P2—C31—C32175.6 (11)
F2—C1—C2—C364.7 (19)C36—C31—C32—C3345 (2)
I1—C1—C2—C3176.7 (11)P2—C31—C32—C33177.0 (12)
F4—C2—C3—F673.5 (14)C31—C32—C33—C3446 (2)
F3—C2—C3—F6170.2 (12)C32—C33—C34—C3549 (2)
C1—C2—C3—F649.3 (19)C33—C34—C35—C3652 (2)
F4—C2—C3—F5171.3 (12)C34—C35—C36—C3152 (2)
F3—C2—C3—F555.0 (14)C32—C31—C36—C3548.4 (19)
C1—C2—C3—F566.0 (18)P2—C31—C36—C35177.2 (12)
F4—C2—C3—C3i54 (2)C25—P2—C37—C4263.7 (12)
F3—C2—C3—C3i62 (2)C31—P2—C37—C42171.7 (10)
C1—C2—C3—C3i176.6 (17)C25—P2—C37—C38174.6 (11)
C13—P1—C7—C8146.8 (12)C31—P2—C37—C3866.5 (12)
C19—P1—C7—C8103.9 (13)C42—C37—C38—C3956.2 (16)
C13—P1—C7—C1236.7 (15)P2—C37—C38—C39178.6 (10)
C19—P1—C7—C1272.5 (14)C37—C38—C39—C4055.6 (17)
C12—C7—C8—C92 (2)C38—C39—C40—C4153.7 (18)
P1—C7—C8—C9178.3 (12)C39—C40—C41—C4252.7 (18)
C7—C8—C9—C103 (3)C40—C41—C42—C3754.0 (18)
C8—C9—C10—C113 (3)C38—C37—C42—C4155.7 (17)
C9—C10—C11—C121 (3)P2—C37—C42—C41178.2 (11)
C10—C11—C12—C70 (3)F7A—C4A—C5A—F9A63 (2)
C8—C7—C12—C110 (2)F8A—C4A—C5A—F9A178.8 (19)
P1—C7—C12—C11176.3 (12)I2A—C4A—C5A—F9A62 (2)
C19—P1—C13—C1861.0 (13)F7A—C4A—C5A—F10A179 (2)
C7—P1—C13—C18170.3 (11)F8A—C4A—C5A—F10A61 (2)
C19—P1—C13—C14177.7 (11)I2A—C4A—C5A—F10A56 (2)
C7—P1—C13—C1468.5 (12)F7A—C4A—C5A—C6A58 (3)
C18—C13—C14—C1554.1 (19)F8A—C4A—C5A—C6A60 (3)
P1—C13—C14—C15177.3 (12)I2A—C4A—C5A—C6A177.0 (16)
C13—C14—C15—C1656 (2)F9A—C5A—C6A—F12A172 (2)
C14—C15—C16—C1757 (2)F10A—C5A—C6A—F12A68 (2)
C15—C16—C17—C1857 (2)C4A—C5A—C6A—F12A54 (3)
C14—C13—C18—C1754.8 (19)F9A—C5A—C6A—F11A54 (2)
P1—C13—C18—C17177.2 (12)F10A—C5A—C6A—F11A174 (2)
C16—C17—C18—C1358 (2)C4A—C5A—C6A—F11A63 (3)
C13—P1—C19—C24135.8 (12)F9A—C5A—C6A—C6Aii58 (3)
C7—P1—C19—C2426.7 (14)F10A—C5A—C6A—C6Aii61 (3)
C13—P1—C19—C20101.3 (12)C4A—C5A—C6A—C6Aii176 (2)
C7—P1—C19—C20149.5 (12)F7B—C4B—C5B—F9B68 (2)
C24—C19—C20—C2155.1 (19)F8B—C4B—C5B—F9B177.0 (17)
P1—C19—C20—C21177.9 (13)I2B—C4B—C5B—F9B62 (2)
C19—C20—C21—C2255 (2)F7B—C4B—C5B—F10B174.6 (18)
C20—C21—C22—C2354 (2)F8B—C4B—C5B—F10B59 (2)
C21—C22—C23—C2454 (2)I2B—C4B—C5B—F10B56 (2)
C20—C19—C24—C2355.5 (18)F7B—C4B—C5B—C6B51 (3)
P1—C19—C24—C23179.8 (12)F8B—C4B—C5B—C6B64 (2)
C22—C23—C24—C1956 (2)I2B—C4B—C5B—C6B179.5 (15)
C37—P2—C25—C30148.6 (13)F9B—C5B—C6B—F12B162 (2)
C31—P2—C25—C30101.2 (14)F10B—C5B—C6B—F12B78 (2)
C37—P2—C25—C2638.4 (16)C4B—C5B—C6B—F12B44 (3)
C31—P2—C25—C2671.8 (16)F9B—C5B—C6B—C6Bii63 (3)
C30—C25—C26—C278 (2)F10B—C5B—C6B—C6Bii57 (3)
P2—C25—C26—C27178.5 (13)C4B—C5B—C6B—C6Bii179 (3)
C25—C26—C27—C2810 (3)F9B—C5B—C6B—F11B44 (2)
C26—C27—C28—C2910 (3)F10B—C5B—C6B—F11B164 (2)
C27—C28—C29—C309 (3)C4B—C5B—C6B—F11B73 (3)
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C38—H38A···I2Aiii0.973.334.098 (15)138
C42—H42A···I2Aiv0.973.283.948 (14)127
Symmetry codes: (iii) x, y+1, z+1; (iv) x+1, y+1, z+1.
 

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