Tetrakis(2,3,5,6-tetra­fluoro-4-iodo­phenyloxy­methyl)­methane bis­(pyridine N-oxide) monohydrate

The title compound, C₂₉H₈F₁₆I₄O₄·2C₅H₅NO·H₂O, is com­posed of the tetrakis-p-iodo­tetra­fluoroether of pentaeryth­ritol, pyridine N-oxide and water. It is characterized by the presence of both halogen bonds and hydrogen bonds connecting the three components. The two particularly short I...O halogen bonds (<2.9 Å) involve one pyridine N-oxide mol­ecule and water. Consistent with the n-σ* character of the I...O halogen bond, the shorter the I...O interaction is, the greater the lengthening of the corresponding C—I bond. As is often the case in similar compounds, the C—I...O angles are approximately linear. The structure shows thin hydro­carbon layers alternating with thick per­fluoro­carbon layers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.038
• wR factor = 0.099
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT431_ALERT_2_A Short Inter HL..A Contact  I1     ..  O5      ..       2.85 Ang.

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     -   C16     ..       7.24 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.14 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   N1     -   C34     ..       5.34 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C30    -   C31     ..       5.65 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C33    -   C34     ..       6.01 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C38    -   C39     ..       5.05 su
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  I3     ..  O6      ..       3.26 Ang.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97, PARST (Nardelli, 1983) and GEO (Pilati, 2004).

Tetrakis(2,3,5,6-tetrafluoro-4-iodophenyoxymethyl)methane bis(pyridine N-oxide) monohydrate

Crystal data

C29H8F16I4O4·2C5H5NO·H2O	Z = 2
Mr = 1440.17	F(000) = 1360
Triclinic, P1	Dx = 2.133 Mg m^−3
a = 8.034 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.412 (3) Å	Cell parameters from 2447 reflections
c = 21.624 (5) Å	θ = 2.8–22.6°
α = 76.25 (5)°	µ = 2.90 mm^−1
β = 82.28 (5)°	T = 293 K
γ = 89.73 (5)°	Prism, colourless
V = 2241.9 (9) Å^3	0.19 × 0.06 × 0.03 mm

Data collection

Bruker APEX CCD area-detector diffractometer	7905 independent reflections
Radiation source: fine-focus sealed tube	5029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.744, Tmax = 0.917	k = −15→15
18906 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0638P)^2] where P = (Fo^2 + 2Fc^2)/3
7905 reflections	(Δ/σ)max = 0.001
619 parameters	Δρmax = 0.63 e Å^−3
1 restraint	Δρmin = −0.40 e Å^−3

Special details

Experimental. The crystals are small and very fragile. They quicly fade, when extracted from crystallization solvent. A first data collection was only partial because of the decay; the second one was on a crystal completely covered of glue. We collected a redundant number of frames, with short exposure time. Data collection was stopped when the decay became evident.

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.

H atoms of water molecule were refined with the following restraint: SADI O7 H7A O7 H7B All the other H atoms were calculated.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.00200 (5)	0.62541 (3)	−0.330136 (17)	0.06965 (13)
C1	0.2536 (8)	0.2435 (4)	0.0111 (2)	0.0684 (15)
C2	0.1789 (8)	0.3345 (4)	−0.0328 (3)	0.0689 (15)
H2A	0.0949	0.3662	−0.0076	0.083*
H2B	0.2665	0.3856	−0.0538	0.083*
O1	0.1023 (6)	0.2976 (3)	−0.08093 (18)	0.0765 (11)
C3	0.0807 (8)	0.3704 (5)	−0.1336 (3)	0.0691 (15)
C4	0.1676 (7)	0.3688 (4)	−0.1939 (3)	0.0667 (14)
C5	0.1442 (7)	0.4408 (4)	−0.2476 (3)	0.0630 (13)
C6	0.0313 (7)	0.5171 (4)	−0.2463 (2)	0.0652 (14)
C7	−0.0576 (8)	0.5193 (4)	−0.1866 (3)	0.0683 (15)
C8	−0.0330 (8)	0.4471 (5)	−0.1323 (3)	0.0708 (15)
F1	0.2776 (5)	0.2948 (3)	−0.19711 (17)	0.0847 (10)
F2	0.2352 (4)	0.4346 (3)	−0.30323 (14)	0.0768 (9)
F3	−0.1718 (4)	0.5933 (3)	−0.18286 (15)	0.0781 (9)
F4	−0.1222 (4)	0.4539 (3)	−0.07694 (14)	0.0817 (9)
I2	0.93583 (5)	0.24676 (4)	−0.31661 (2)	0.08305 (15)
C9	0.3904 (8)	0.1935 (5)	−0.0263 (2)	0.0727 (16)
H9A	0.4301	0.1333	0.0019	0.087*
H9B	0.3459	0.1720	−0.0608	0.087*
O2	0.5290 (5)	0.2682 (3)	−0.05287 (17)	0.0774 (11)
C10	0.6165 (8)	0.2605 (5)	−0.1091 (3)	0.0687 (15)
C11	0.6097 (8)	0.3412 (5)	−0.1637 (3)	0.0687 (15)
C12	0.7039 (8)	0.3314 (5)	−0.2219 (3)	0.0712 (15)
C13	0.8035 (8)	0.2492 (5)	−0.2276 (3)	0.0705 (15)
C14	0.8069 (9)	0.1755 (5)	−0.1750 (3)	0.0844 (19)
C15	0.7127 (9)	0.1802 (5)	−0.1168 (3)	0.0775 (17)
F5	0.5197 (5)	0.4213 (3)	−0.15942 (16)	0.0839 (10)
F6	0.6927 (5)	0.4125 (3)	−0.27196 (16)	0.0868 (10)
F7	0.8980 (5)	0.0932 (3)	−0.17676 (18)	0.0920 (11)
F8	0.7228 (5)	0.1016 (3)	−0.06546 (17)	0.0968 (11)
I3	0.47724 (6)	0.25419 (4)	0.376670 (19)	0.08055 (14)
C16	0.3247 (8)	0.2895 (4)	0.0601 (3)	0.0659 (14)
H16A	0.4041	0.3452	0.0386	0.079*
H16B	0.2352	0.3162	0.0859	0.079*
O3	0.4079 (6)	0.2079 (3)	0.10029 (18)	0.0785 (11)
C17	0.4196 (8)	0.2206 (5)	0.1590 (3)	0.0735 (16)
C18	0.3428 (8)	0.1551 (4)	0.2133 (3)	0.0714 (15)
C19	0.3592 (8)	0.1654 (5)	0.2751 (3)	0.0736 (16)
C20	0.4583 (8)	0.2446 (5)	0.2837 (3)	0.0730 (15)
C21	0.5378 (8)	0.3072 (5)	0.2295 (3)	0.0747 (16)
C22	0.5198 (9)	0.2975 (5)	0.1700 (3)	0.0782 (17)
F9	0.2433 (5)	0.0776 (3)	0.20766 (17)	0.0866 (10)
F10	0.2728 (4)	0.0974 (3)	0.32449 (15)	0.0801 (9)
F11	0.6360 (5)	0.3842 (3)	0.23644 (19)	0.0969 (11)
F12	0.6067 (5)	0.3650 (3)	0.11880 (18)	0.0970 (11)
I4	−0.42953 (7)	−0.10221 (4)	0.30680 (3)	0.1135 (2)
C23	0.1196 (8)	0.1595 (5)	0.0408 (3)	0.0731 (16)
H23A	0.0818	0.1314	0.0075	0.088*
H23B	0.1658	0.1044	0.0709	0.088*
O4	−0.0207 (6)	0.2038 (3)	0.07404 (18)	0.0818 (12)
C24	−0.1123 (8)	0.1368 (5)	0.1246 (3)	0.0727 (16)
C25	−0.1180 (8)	0.1465 (5)	0.1858 (3)	0.0719 (15)
C26	−0.2103 (9)	0.0803 (5)	0.2360 (3)	0.0792 (17)
C27	−0.2989 (8)	−0.0013 (5)	0.2287 (3)	0.0757 (16)
C28	−0.2956 (8)	−0.0105 (5)	0.1670 (3)	0.0749 (16)
C29	−0.2066 (9)	0.0577 (5)	0.1161 (3)	0.0805 (18)
F13	−0.0333 (5)	0.2278 (3)	0.19620 (18)	0.0952 (11)
F14	−0.2047 (5)	0.0975 (3)	0.29516 (16)	0.0905 (10)
F15	−0.3832 (5)	−0.0894 (3)	0.1570 (2)	0.1023 (12)
F16	−0.2064 (6)	0.0403 (3)	0.05771 (18)	0.1036 (12)
O5	0.0082 (6)	0.7591 (4)	0.5454 (2)	0.0900 (13)
N1	0.0943 (6)	0.8477 (4)	0.5353 (2)	0.0692 (13)
C30	0.0667 (8)	0.9050 (5)	0.5766 (3)	0.0816 (19)
H30	−0.0123	0.8841	0.6131	0.098*
C31	0.1544 (9)	0.9954 (5)	0.5660 (3)	0.0821 (18)
H31	0.1361	1.0369	0.5950	0.098*
C32	0.2702 (9)	1.0246 (6)	0.5117 (4)	0.092 (2)
H32	0.3307	1.0864	0.5034	0.111*
C33	0.2948 (9)	0.9643 (6)	0.4715 (4)	0.092 (2)
H33	0.3746	0.9825	0.4351	0.110*
C34	0.2036 (9)	0.8758 (5)	0.4836 (3)	0.0834 (18)
H34	0.2190	0.8343	0.4546	0.100*
O6	0.4776 (6)	0.2635 (4)	0.5261 (3)	0.1141 (18)
N2	0.5576 (7)	0.3450 (5)	0.5341 (3)	0.0917 (16)
C35	0.6879 (9)	0.3837 (6)	0.4918 (4)	0.091 (2)
H35	0.7218	0.3545	0.4574	0.109*
C36	0.7723 (8)	0.4664 (5)	0.4988 (3)	0.0805 (17)
H36	0.8619	0.4957	0.4680	0.097*
C37	0.7278 (10)	0.5078 (6)	0.5506 (4)	0.100 (2)
H37	0.7853	0.5646	0.5559	0.120*
C38	0.5982 (12)	0.4629 (7)	0.5930 (3)	0.101 (2)
H38	0.5655	0.4887	0.6289	0.121*
C39	0.5144 (10)	0.3828 (6)	0.5855 (4)	0.095 (2)
H39	0.4251	0.3528	0.6162	0.114*
O7	0.1344 (6)	0.2585 (5)	0.5599 (2)	0.1017 (16)
H7A	0.074 (11)	0.241 (7)	0.531 (4)	0.153*
H7B	0.247 (8)	0.259 (7)	0.544 (5)	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0728 (3)	0.0793 (2)	0.0526 (2)	−0.00414 (19)	−0.01167 (17)	−0.00570 (16)
C1	0.085 (4)	0.064 (3)	0.051 (3)	0.007 (3)	0.003 (3)	−0.009 (2)
C2	0.088 (4)	0.063 (3)	0.054 (3)	0.001 (3)	−0.007 (3)	−0.014 (2)
O1	0.101 (3)	0.074 (2)	0.055 (2)	−0.002 (2)	−0.019 (2)	−0.0119 (19)
C3	0.072 (4)	0.078 (4)	0.053 (3)	−0.006 (3)	0.007 (3)	−0.015 (3)
C4	0.060 (3)	0.068 (3)	0.070 (4)	0.006 (3)	−0.008 (3)	−0.014 (3)
C5	0.057 (3)	0.070 (3)	0.060 (3)	0.010 (3)	0.005 (2)	−0.019 (3)
C6	0.073 (4)	0.068 (3)	0.054 (3)	−0.004 (3)	−0.008 (3)	−0.013 (2)
C7	0.078 (4)	0.064 (3)	0.054 (3)	0.005 (3)	0.005 (3)	−0.004 (3)
C8	0.080 (4)	0.082 (4)	0.049 (3)	0.000 (3)	0.004 (3)	−0.018 (3)
F1	0.091 (3)	0.087 (2)	0.077 (2)	0.014 (2)	−0.0140 (19)	−0.0213 (18)
F2	0.073 (2)	0.093 (2)	0.0593 (18)	0.0017 (17)	0.0113 (15)	−0.0203 (16)
F3	0.089 (2)	0.083 (2)	0.0585 (18)	0.0181 (19)	−0.0039 (16)	−0.0133 (15)
F4	0.085 (2)	0.104 (2)	0.0499 (17)	0.0057 (19)	0.0109 (16)	−0.0186 (16)
I2	0.0653 (3)	0.1173 (3)	0.0682 (2)	−0.0179 (2)	0.00872 (19)	−0.0349 (2)
C9	0.086 (4)	0.079 (4)	0.045 (3)	0.008 (3)	0.003 (3)	−0.006 (3)
O2	0.094 (3)	0.091 (3)	0.048 (2)	−0.009 (2)	−0.003 (2)	−0.0215 (19)
C10	0.072 (4)	0.082 (4)	0.059 (3)	−0.005 (3)	−0.011 (3)	−0.030 (3)
C11	0.070 (4)	0.079 (4)	0.060 (3)	0.008 (3)	−0.009 (3)	−0.020 (3)
C12	0.070 (4)	0.081 (4)	0.059 (3)	−0.002 (3)	−0.007 (3)	−0.009 (3)
C13	0.070 (4)	0.085 (4)	0.062 (3)	−0.003 (3)	−0.009 (3)	−0.029 (3)
C14	0.092 (5)	0.078 (4)	0.071 (4)	0.018 (4)	0.013 (3)	−0.006 (3)
C15	0.091 (5)	0.094 (4)	0.045 (3)	0.002 (4)	−0.010 (3)	−0.010 (3)
F5	0.083 (2)	0.084 (2)	0.078 (2)	0.0126 (19)	0.0072 (18)	−0.0165 (17)
F6	0.097 (3)	0.088 (2)	0.0624 (19)	0.004 (2)	0.0012 (17)	0.0006 (17)
F7	0.093 (3)	0.093 (3)	0.085 (2)	0.016 (2)	0.000 (2)	−0.0182 (19)
F8	0.107 (3)	0.105 (3)	0.069 (2)	0.022 (2)	−0.002 (2)	−0.008 (2)
I3	0.0828 (3)	0.0996 (3)	0.0663 (2)	0.0025 (2)	−0.0155 (2)	−0.0306 (2)
C16	0.082 (4)	0.069 (3)	0.053 (3)	−0.001 (3)	−0.023 (3)	−0.019 (2)
O3	0.100 (3)	0.080 (3)	0.057 (2)	0.018 (2)	−0.014 (2)	−0.0188 (19)
C17	0.083 (4)	0.072 (4)	0.067 (4)	0.008 (3)	−0.014 (3)	−0.016 (3)
C18	0.086 (4)	0.065 (3)	0.061 (3)	0.004 (3)	−0.016 (3)	−0.009 (3)
C19	0.082 (4)	0.071 (4)	0.068 (4)	−0.004 (3)	−0.010 (3)	−0.018 (3)
C20	0.071 (4)	0.077 (4)	0.072 (4)	0.001 (3)	−0.010 (3)	−0.019 (3)
C21	0.066 (4)	0.084 (4)	0.064 (3)	−0.004 (3)	−0.006 (3)	0.001 (3)
C22	0.096 (5)	0.086 (4)	0.046 (3)	0.006 (4)	−0.015 (3)	0.001 (3)
F9	0.104 (3)	0.077 (2)	0.082 (2)	−0.014 (2)	−0.017 (2)	−0.0229 (18)
F10	0.082 (2)	0.088 (2)	0.0654 (19)	−0.0129 (18)	−0.0003 (17)	−0.0139 (17)
F11	0.101 (3)	0.093 (3)	0.095 (3)	−0.025 (2)	−0.026 (2)	−0.010 (2)
F12	0.094 (3)	0.104 (3)	0.079 (2)	−0.017 (2)	−0.014 (2)	0.006 (2)
I4	0.1058 (4)	0.0913 (3)	0.1154 (4)	−0.0032 (3)	0.0478 (3)	−0.0045 (3)
C23	0.085 (4)	0.084 (4)	0.050 (3)	−0.006 (3)	0.007 (3)	−0.024 (3)
O4	0.096 (3)	0.081 (3)	0.058 (2)	0.003 (2)	0.014 (2)	−0.012 (2)
C24	0.075 (4)	0.091 (4)	0.057 (3)	0.004 (3)	0.002 (3)	−0.033 (3)
C25	0.074 (4)	0.085 (4)	0.059 (3)	0.000 (3)	−0.008 (3)	−0.022 (3)
C26	0.089 (5)	0.091 (4)	0.059 (3)	−0.005 (4)	−0.002 (3)	−0.024 (3)
C27	0.072 (4)	0.084 (4)	0.065 (4)	0.011 (3)	0.003 (3)	−0.012 (3)
C28	0.079 (4)	0.078 (4)	0.066 (4)	−0.012 (3)	0.005 (3)	−0.024 (3)
C29	0.093 (5)	0.103 (5)	0.048 (3)	−0.003 (4)	−0.001 (3)	−0.027 (3)
F13	0.106 (3)	0.099 (3)	0.083 (2)	−0.023 (2)	0.003 (2)	−0.036 (2)
F14	0.098 (3)	0.115 (3)	0.0593 (19)	−0.012 (2)	−0.0011 (18)	−0.0267 (19)
F15	0.113 (3)	0.092 (3)	0.105 (3)	−0.024 (2)	−0.002 (2)	−0.037 (2)
F16	0.126 (3)	0.115 (3)	0.073 (2)	−0.017 (3)	−0.003 (2)	−0.035 (2)
O5	0.094 (3)	0.097 (3)	0.075 (3)	0.001 (3)	−0.035 (2)	0.000 (2)
N1	0.058 (3)	0.104 (4)	0.044 (2)	0.012 (3)	−0.005 (2)	−0.013 (2)
C30	0.079 (4)	0.100 (5)	0.051 (3)	0.030 (4)	0.011 (3)	−0.001 (3)
C31	0.082 (5)	0.084 (4)	0.079 (4)	0.012 (4)	−0.022 (4)	−0.012 (3)
C32	0.067 (4)	0.098 (5)	0.104 (5)	0.007 (4)	−0.037 (4)	0.005 (4)
C33	0.071 (4)	0.098 (5)	0.091 (5)	0.035 (4)	0.009 (4)	−0.004 (4)
C34	0.099 (5)	0.073 (4)	0.075 (4)	0.008 (4)	−0.004 (4)	−0.016 (3)
O6	0.076 (3)	0.102 (4)	0.174 (5)	−0.001 (3)	0.006 (3)	−0.065 (4)
N2	0.056 (3)	0.099 (4)	0.124 (5)	0.005 (3)	−0.013 (3)	−0.034 (4)
C35	0.074 (4)	0.095 (5)	0.116 (6)	0.003 (4)	−0.014 (4)	−0.051 (4)
C36	0.070 (4)	0.098 (5)	0.066 (4)	0.007 (4)	−0.009 (3)	−0.003 (3)
C37	0.084 (5)	0.115 (6)	0.114 (6)	−0.011 (4)	−0.026 (5)	−0.044 (5)
C38	0.136 (7)	0.123 (6)	0.051 (4)	0.026 (6)	−0.036 (4)	−0.020 (4)
C39	0.111 (6)	0.083 (5)	0.090 (5)	0.004 (4)	0.007 (4)	−0.029 (4)
O7	0.083 (3)	0.145 (4)	0.080 (3)	−0.017 (3)	0.017 (3)	−0.047 (3)

Geometric parameters (Å, º)

I1—C6	2.083 (5)	C20—C21	1.350 (8)
C1—C16	1.519 (7)	C21—F11	1.350 (7)
C1—C23	1.524 (8)	C21—C22	1.351 (8)
C1—C9	1.525 (8)	C22—F12	1.362 (7)
C1—C2	1.532 (8)	I4—C27	2.059 (6)
C2—O1	1.458 (6)	C23—O4	1.455 (7)
C2—H2A	0.9700	C23—H23A	0.9700
C2—H2B	0.9700	C23—H23B	0.9700
O1—C3	1.342 (7)	O4—C24	1.366 (7)
C3—C8	1.376 (8)	C24—C25	1.355 (8)
C3—C4	1.399 (8)	C24—C29	1.368 (9)
C4—F1	1.334 (6)	C25—C26	1.361 (9)
C4—C5	1.356 (8)	C25—F13	1.366 (7)
C5—F2	1.342 (6)	C26—F14	1.359 (7)
C5—C6	1.367 (8)	C26—C27	1.360 (9)
C6—C7	1.396 (7)	C27—C28	1.365 (8)
C7—F3	1.359 (6)	C28—F15	1.349 (7)
C7—C8	1.369 (8)	C28—C29	1.370 (8)
C8—F4	1.332 (6)	C29—F16	1.337 (6)
I2—C13	2.078 (6)	O5—N1	1.335 (7)
C9—O2	1.462 (7)	N1—C34	1.304 (8)
C9—H9A	0.9700	N1—C30	1.309 (8)
C9—H9B	0.9700	C30—C31	1.360 (10)
O2—C10	1.346 (7)	C30—H30	0.9300
C10—C15	1.352 (9)	C31—C32	1.375 (10)
C10—C11	1.406 (8)	C31—H31	0.9300
C11—F5	1.307 (7)	C32—C33	1.316 (10)
C11—C12	1.412 (8)	C32—H32	0.9300
C12—F6	1.352 (7)	C33—C34	1.350 (10)
C12—C13	1.379 (8)	C33—H33	0.9300
C13—C14	1.321 (8)	C34—H34	0.9300
C14—F7	1.327 (7)	O6—N2	1.328 (7)
C14—C15	1.394 (8)	N2—C35	1.313 (9)
C15—F8	1.347 (7)	N2—C39	1.333 (9)
I3—C20	2.070 (6)	C35—C36	1.353 (10)
C16—O3	1.448 (7)	C35—H35	0.9300
C16—H16A	0.9700	C36—C37	1.370 (10)
C16—H16B	0.9700	C36—H36	0.9300
O3—C17	1.336 (7)	C37—C38	1.332 (11)
C17—C18	1.360 (8)	C37—H37	0.9300
C17—C22	1.394 (9)	C38—C39	1.324 (10)
C18—F9	1.352 (7)	C38—H38	0.9300
C18—C19	1.399 (8)	C39—H39	0.9300
C19—F10	1.342 (7)	O7—H7A	0.92 (6)
C19—C20	1.392 (8)	O7—H7B	0.92 (6)
C16—C1—C23	113.6 (5)	C21—C20—C19	115.9 (6)
C16—C1—C9	111.1 (5)	C21—C20—I3	125.8 (5)
C23—C1—C9	105.6 (4)	C19—C20—I3	118.3 (4)
C16—C1—C2	104.6 (4)	F11—C21—C20	117.2 (6)
C23—C1—C2	110.5 (5)	F11—C21—C22	119.7 (5)
C9—C1—C2	111.6 (4)	C20—C21—C22	123.1 (6)
O1—C2—C1	108.9 (4)	C21—C22—F12	118.0 (6)
O1—C2—H2A	109.9	C21—C22—C17	123.0 (6)
C1—C2—H2A	109.9	F12—C22—C17	119.0 (5)
O1—C2—H2B	109.9	O4—C23—C1	108.6 (5)
C1—C2—H2B	109.9	O4—C23—H23A	110.0
H2A—C2—H2B	108.3	C1—C23—H23A	110.0
C3—O1—C2	114.6 (4)	O4—C23—H23B	110.0
O1—C3—C8	122.6 (5)	C1—C23—H23B	110.0
O1—C3—C4	121.2 (5)	H23A—C23—H23B	108.4
C8—C3—C4	116.1 (5)	C24—O4—C23	115.3 (5)
F1—C4—C5	120.5 (5)	C25—C24—O4	121.8 (6)
F1—C4—C3	117.8 (5)	C25—C24—C29	116.3 (6)
C5—C4—C3	121.7 (5)	O4—C24—C29	121.9 (5)
F2—C5—C4	117.7 (5)	C24—C25—C26	121.8 (6)
F2—C5—C6	120.1 (5)	C24—C25—F13	118.3 (6)
C4—C5—C6	122.2 (5)	C26—C25—F13	119.8 (5)
C5—C6—C7	116.8 (5)	F14—C26—C27	121.1 (6)
C5—C6—I1	120.9 (4)	F14—C26—C25	116.3 (6)
C7—C6—I1	122.3 (4)	C27—C26—C25	122.6 (6)
F3—C7—C8	119.9 (5)	C26—C27—C28	115.8 (6)
F3—C7—C6	119.1 (5)	C26—C27—I4	121.0 (5)
C8—C7—C6	121.0 (5)	C28—C27—I4	123.2 (5)
F4—C8—C7	117.7 (5)	F15—C28—C27	118.1 (5)
F4—C8—C3	120.2 (5)	F15—C28—C29	120.1 (5)
C7—C8—C3	122.1 (5)	C27—C28—C29	121.8 (6)
O2—C9—C1	108.6 (5)	F16—C29—C24	120.8 (5)
O2—C9—H9A	110.0	F16—C29—C28	117.4 (6)
C1—C9—H9A	110.0	C24—C29—C28	121.7 (5)
O2—C9—H9B	110.0	C34—N1—C30	121.3 (6)
C1—C9—H9B	110.0	C34—N1—O5	118.9 (5)
H9A—C9—H9B	108.4	C30—N1—O5	119.8 (5)
C10—O2—C9	116.2 (4)	N1—C30—C31	119.5 (6)
O2—C10—C15	124.3 (5)	N1—C30—H30	120.2
O2—C10—C11	118.5 (5)	C31—C30—H30	120.2
C15—C10—C11	117.2 (5)	C30—C31—C32	119.0 (7)
F5—C11—C10	120.2 (5)	C30—C31—H31	120.5
F5—C11—C12	122.5 (5)	C32—C31—H31	120.5
C10—C11—C12	117.3 (5)	C33—C32—C31	119.4 (7)
F6—C12—C13	122.3 (5)	C33—C32—H32	120.3
F6—C12—C11	113.8 (5)	C31—C32—H32	120.3
C13—C12—C11	123.9 (5)	C32—C33—C34	119.6 (7)
C14—C13—C12	116.8 (5)	C32—C33—H33	120.2
C14—C13—I2	124.0 (5)	C34—C33—H33	120.2
C12—C13—I2	119.2 (4)	N1—C34—C33	121.1 (6)
C13—C14—F7	120.4 (6)	N1—C34—H34	119.4
C13—C14—C15	121.5 (6)	C33—C34—H34	119.4
F7—C14—C15	118.1 (5)	C35—N2—O6	118.0 (6)
F8—C15—C10	118.9 (5)	C35—N2—C39	120.6 (7)
F8—C15—C14	117.8 (6)	O6—N2—C39	121.4 (7)
C10—C15—C14	123.3 (6)	N2—C35—C36	119.3 (7)
O3—C16—C1	106.9 (4)	N2—C35—H35	120.3
O3—C16—H16A	110.3	C36—C35—H35	120.3
C1—C16—H16A	110.3	C35—C36—C37	121.0 (7)
O3—C16—H16B	110.3	C35—C36—H36	119.5
C1—C16—H16B	110.3	C37—C36—H36	119.5
H16A—C16—H16B	108.6	C38—C37—C36	116.8 (7)
C17—O3—C16	114.8 (4)	C38—C37—H37	121.6
O3—C17—C18	122.4 (6)	C36—C37—H37	121.6
O3—C17—C22	123.0 (5)	C39—C38—C37	122.1 (7)
C18—C17—C22	114.4 (5)	C39—C38—H38	119.0
F9—C18—C17	119.0 (5)	C37—C38—H38	119.0
F9—C18—C19	118.1 (5)	C38—C39—N2	120.2 (7)
C17—C18—C19	122.9 (6)	C38—C39—H39	119.9
F10—C19—C20	122.5 (5)	N2—C39—H39	119.9
F10—C19—C18	116.9 (5)	H7A—O7—H7B	108 (8)
C20—C19—C18	120.6 (6)
C16—C1—C2—O1	−178.4 (5)	O3—C17—C18—C19	177.6 (6)
C23—C1—C2—O1	−55.8 (6)	C22—C17—C18—C19	1.6 (9)
C9—C1—C2—O1	61.4 (6)	F9—C18—C19—F10	−0.6 (9)
C1—C2—O1—C3	−159.7 (5)	C17—C18—C19—F10	178.1 (6)
C2—O1—C3—C8	−68.6 (8)	F9—C18—C19—C20	−179.2 (5)
C2—O1—C3—C4	114.8 (6)	C17—C18—C19—C20	−0.5 (10)
O1—C3—C4—F1	−2.5 (9)	F10—C19—C20—C21	−179.9 (6)
C8—C3—C4—F1	−179.3 (5)	C18—C19—C20—C21	−1.4 (9)
O1—C3—C4—C5	178.7 (5)	F10—C19—C20—I3	1.8 (8)
C8—C3—C4—C5	1.8 (9)	C18—C19—C20—I3	−179.7 (5)
F1—C4—C5—F2	−0.1 (8)	C19—C20—C21—F11	−179.4 (5)
C3—C4—C5—F2	178.8 (5)	I3—C20—C21—F11	−1.3 (9)
F1—C4—C5—C6	179.2 (5)	C19—C20—C21—C22	2.2 (10)
C3—C4—C5—C6	−1.9 (9)	I3—C20—C21—C22	−179.7 (5)
F2—C5—C6—C7	−179.4 (5)	F11—C21—C22—F12	1.9 (9)
C4—C5—C6—C7	1.3 (9)	C20—C21—C22—F12	−179.8 (6)
F2—C5—C6—I1	−0.2 (8)	F11—C21—C22—C17	−179.5 (6)
C4—C5—C6—I1	−179.5 (5)	C20—C21—C22—C17	−1.1 (11)
C5—C6—C7—F3	−179.7 (5)	O3—C17—C22—C21	−176.8 (6)
I1—C6—C7—F3	1.1 (8)	C18—C17—C22—C21	−0.8 (10)
C5—C6—C7—C8	−0.7 (9)	O3—C17—C22—F12	1.9 (9)
I1—C6—C7—C8	−179.9 (5)	C18—C17—C22—F12	177.8 (6)
F3—C7—C8—F4	−1.0 (9)	C16—C1—C23—O4	61.6 (6)
C6—C7—C8—F4	−180.0 (5)	C9—C1—C23—O4	−176.4 (4)
F3—C7—C8—C3	179.7 (6)	C2—C1—C23—O4	−55.5 (6)
C6—C7—C8—C3	0.7 (10)	C1—C23—O4—C24	−152.3 (5)
O1—C3—C8—F4	2.7 (9)	C23—O4—C24—C25	115.0 (6)
C4—C3—C8—F4	179.5 (5)	C23—O4—C24—C29	−66.7 (8)
O1—C3—C8—C7	−178.0 (6)	O4—C24—C25—C26	179.5 (6)
C4—C3—C8—C7	−1.2 (9)	C29—C24—C25—C26	1.0 (10)
C16—C1—C9—O2	−52.7 (6)	O4—C24—C25—F13	2.0 (9)
C23—C1—C9—O2	−176.3 (5)	C29—C24—C25—F13	−176.4 (6)
C2—C1—C9—O2	63.6 (6)	C24—C25—C26—F14	179.4 (6)
C1—C9—O2—C10	−148.7 (5)	F13—C25—C26—F14	−3.1 (9)
C9—O2—C10—C15	−66.1 (8)	C24—C25—C26—C27	1.8 (11)
C9—O2—C10—C11	114.5 (6)	F13—C25—C26—C27	179.3 (6)
O2—C10—C11—F5	−0.1 (9)	F14—C26—C27—C28	179.8 (6)
C15—C10—C11—F5	−179.6 (6)	C25—C26—C27—C28	−2.7 (10)
O2—C10—C11—C12	179.5 (5)	F14—C26—C27—I4	0.2 (9)
C15—C10—C11—C12	0.0 (9)	C25—C26—C27—I4	177.7 (5)
F5—C11—C12—F6	0.4 (9)	C26—C27—C28—F15	−179.2 (6)
C10—C11—C12—F6	−179.2 (5)	I4—C27—C28—F15	0.4 (9)
F5—C11—C12—C13	178.2 (6)	C26—C27—C28—C29	0.8 (10)
C10—C11—C12—C13	−1.4 (9)	I4—C27—C28—C29	−179.6 (5)
F6—C12—C13—C14	178.7 (6)	C25—C24—C29—F16	−178.5 (6)
C11—C12—C13—C14	1.1 (10)	O4—C24—C29—F16	3.1 (10)
F6—C12—C13—I2	−2.0 (8)	C25—C24—C29—C28	−2.9 (10)
C11—C12—C13—I2	−179.6 (5)	O4—C24—C29—C28	178.7 (6)
C12—C13—C14—F7	179.1 (6)	F15—C28—C29—F16	−2.2 (10)
I2—C13—C14—F7	−0.2 (10)	C27—C28—C29—F16	177.8 (6)
C12—C13—C14—C15	0.7 (11)	F15—C28—C29—C24	−178.0 (6)
I2—C13—C14—C15	−178.7 (5)	C27—C28—C29—C24	2.0 (11)
O2—C10—C15—F8	0.3 (10)	C34—N1—C30—C31	−0.5 (9)
C11—C10—C15—F8	179.8 (5)	O5—N1—C30—C31	−179.7 (5)
O2—C10—C15—C14	−177.8 (6)	N1—C30—C31—C32	0.1 (9)
C11—C10—C15—C14	1.7 (10)	C30—C31—C32—C33	−0.5 (10)
C13—C14—C15—F8	179.8 (6)	C31—C32—C33—C34	1.3 (10)
F7—C14—C15—F8	1.3 (10)	C30—N1—C34—C33	1.3 (10)
C13—C14—C15—C10	−2.1 (12)	O5—N1—C34—C33	−179.4 (6)
F7—C14—C15—C10	179.4 (6)	C32—C33—C34—N1	−1.8 (11)
C23—C1—C16—O3	63.5 (6)	O6—N2—C35—C36	−179.8 (6)
C9—C1—C16—O3	−55.4 (6)	C39—N2—C35—C36	−3.9 (11)
C2—C1—C16—O3	−176.0 (5)	N2—C35—C36—C37	2.5 (11)
C1—C16—O3—C17	−155.0 (5)	C35—C36—C37—C38	−0.2 (11)
C16—O3—C17—C18	116.5 (6)	C36—C37—C38—C39	−0.7 (12)
C16—O3—C17—C22	−67.9 (8)	C37—C38—C39—N2	−0.6 (12)
O3—C17—C18—F9	−3.7 (9)	C35—N2—C39—C38	3.0 (11)
C22—C17—C18—F9	−179.7 (5)	O6—N2—C39—C38	178.7 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O6	0.92 (7)	1.84 (6)	2.753 (7)	170 (6)
O7—H7A···O5^i	0.91 (10)	1.86 (10)	2.741 (7)	161 (8)
C30—H30···F10^i	0.93	2.38	3.227 (7)	152
C38—H38···F6^ii	0.93	2.49	3.036 (8)	117

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