supplementary materials


bg2501 scheme

Acta Cryst. (2013). E69, m236-m237    [ doi:10.1107/S1600536813007757 ]

[5,11,17,23-Tetra-tert-butyl-25,27-(3,6-dioxaoctan-1,8-dioxy)-26,28-bis(pyridin-2-ylmethoxy)calix[4]arene]sodium iodide-1,2,4,5-tetrafluoro-3,6-diiodobenzene-methanol (2/3/4)

G. Cavallo, P. Metrangolo, M. F. Parisi, T. Pilati, G. Resnati and G. Terraneo

Abstract top

The title compound, [Na(C62H76N2O6)]I·1.5C6F4I2·2CH3OH, is composed of five components: a calix[4]arene derivative (hereinafter C4), a sodium cation, an iodide anion, a 1,2,4,5-tetrafluoro-3,6-diiodobenzene (tFdIB) molecule and a methanol molecule in a 1:1:1:1.5:2 ratio. The complex shows several interesting features: (i) the polyoxygenated loop of C4 effectively chelates a sodium cation in the form of a distorted octahedron and separates it from the iodide counter-ion, the shortest Na+...I- distance being greater than 6.5 Å; (ii) the cavity of C4 is filled by a methanol molecule; (iii) a second methanol molecule is hydrogen-bonded to the N atom of a pyridinyl substituent pendant of C4 and halogen-bonded to the I atom of a tFdIB molecule; (iv) the two I atoms of another tFdIB molecule are halogen-bonded to two iodide anions, which act as monodentate halogen-bond acceptorss; (v) one of the two tFdIB molecules is located about a centre of inversion.

Comment top

Calix[4]arenes derivatives are very popular compounds in host/guest supramolecular chemistry and find applications in diverse fields spanning from non linear optics to catalysis (Dondoni & Marra, 2010). Calix-crown-arenes, namely calixarenes with a polyoxyethylene chain bridging two positions at the lower rim, are frequently used to chelate metal cations. In several structures, crown loops formed by five or six glycol units effectively coordinate large metal cations. Only nine calix-crown-arenes contain smaller loops formed by four glycol groups. They are CAWYEF, CAZCUB, CAZDUC, which have two free phenolic functions on the lower rim, and GUDMAU, GUDMEY, GUDMIC, XEGSAE, XEGSEI, XEGSIM, which have two propyloxy functions (code from CSD-Version 5.33 Nov 2011; Allen, 2002). We have already reported that when calix-crown-arenes coordinate potassium (Gattuso, et al., 2006) or caesium cations (Gattuso, et al., 2007), the resulting naked iodide anions form XBs with diiodoperfluoroalkanes. Alternatively, the nitrogen atoms of pyridyl pendants at the lower rim of calixarenes form XBs with tetrafluoro-diiodobenzene (tFdIB) (Messina, et al., 2000). This paper presents a calix-crown-arene having, at the lower rim, two 2-pyridylmethoxy groups and a short loop (compounded by four glycol units connecting positions 25 and 27) which cryptates the small Na+ cation from NaI. The resulting supramolecular salt might act as a polydentate XB donor towards tFdIB, as both pyridyl nitrogen atoms and naked iodide anions can function as donors of electron density (XB acceptors) to iodoperfluorocarbons when singly present in structurally similar systems. Usually, iodide anions are more effective XB acceptors than lone pair possessing nitrogen atoms. In the stucture described here, pyridine nitrogen atoms form no XB. One nitrogen atom is engaged in an intramolecular contact with a hydrogen atom of the glycol loop and the other is linked to a methanol molecule (O7···N2 2.809 (3) Å) via a quite short hydrogen bond (HB). Another methanol molecule occupies the calixarene cavity. It shows no disorder and the hydroxyl H atom and a methyl H atom are weakly linked to the inner faces of two adjacent aromatic rings. The two iodine atoms of one tFdIB molecule are halogen bonded to two iodide anions which work as monodentate XB acceptors. The coordination sphere of iodide anions is completed by three H···I- contacts with three supramolecular cations surrounding the anion. One iodine atom of the other independent tFdIB molecule is engaged in a quite short XB with the oxygen of a MeOH molecule and the other iodine atom forms a quite long contact with a fluorine atom of another tFdIB molecule. Figure 1 shows the supramolecular cation with the included methanol molecule. Figure 2 shows the other components of the system with the numbering scheme. Figure 3 is a view of the main HBs and XBs of the structure.

Related literature top

For applications of calix[4]arenes derivative, see Dondoni & Marra (2010). When calix-crown-arenes coordinate potassium (Gattuso et al., 2006) or caesium cations (Gattuso et al., 2007), the resulting naked iodide anions form XBs with diiodoperfluoroalkanes. Alternatively, the N atoms of pyridyl pendants at the lower rim of calixarenes form XBs with tetrafluoro-diiodobenzene (Messina et al., 2000). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Methanol solutions of C4, sodium iodide, and tFdIB were prepared separately and mixed in a single vial which was closed in a wide mouth flask containing vaseline oil. The solvent was allowed to diffuse at room temperature until good quality crystals were formed.

Refinement top

Hydrogen atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups and hydroxyl group) times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP-3 view of C4Na+ supramolecular cation with the methanol molecule filling the cavity. Ellipsoids at 50% level. H atoms and the remaining components of the structure are omitted for clarity.
[Figure 2] Fig. 2. : The ORTEP-3 view of the components not reported in Fig. 1, namely I-···tFdIB···I- and tFdIB···MeOH. The orientation adopted for these components is different from that adopted in Fig. 1.
[Figure 3] Fig. 3. Mercury ball and stick view of two asymmetric units around the symmetry center. Short XBs and HB are reported. Hydrogen atoms not involved in H-bonding are omitted for clarity.
[5,11,17,23-Tetra-tert-butyl-25,27-(3,6-dioxaoctan-1,8-dioxy)-26,28-bis(pyridin-2-ylmethoxy)calix[4]arene]sodium iodide–1,2,4,5-tetrafluoro-3,6-diiodobenzene–methanol (2/3/4) top
Crystal data top
[Na(C62H76N2O6)]I·1.5C6F4I2·2CH4OZ = 2
Mr = 1762.01F(000) = 1754
Triclinic, P1Dx = 1.610 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.4019 (12) ÅCell parameters from 33174 reflections
b = 14.2255 (12) Åθ = 2.5–36.2°
c = 21.022 (2) ŵ = 1.79 mm1
α = 85.90 (2)°T = 90 K
β = 84.61 (2)°Prism, colourless
γ = 65.75 (2)°0.42 × 0.30 × 0.20 mm
V = 3635.6 (8) Å3
Data collection top
Bruker APEXII CCD
diffractometer
29534 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.029
φ and ω scansθmax = 36.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 2122
Tmin = 0.866, Tmax = 1.000k = 2323
88833 measured reflectionsl = 3435
33353 independent reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0333P)2 + 3.1236P],
where P = (Fo2 + 2Fc2)/3
33353 reflections(Δ/σ)max = 0.002
847 parametersΔρmax = 2.33 e Å3
0 restraintsΔρmin = 1.52 e Å3
Crystal data top
[Na(C62H76N2O6)]I·1.5C6F4I2·2CH4Oγ = 65.75 (2)°
Mr = 1762.01V = 3635.6 (8) Å3
Triclinic, P1Z = 2
a = 13.4019 (12) ÅMo Kα radiation
b = 14.2255 (12) ŵ = 1.79 mm1
c = 21.022 (2) ÅT = 90 K
α = 85.90 (2)°0.42 × 0.30 × 0.20 mm
β = 84.61 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
33353 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
29534 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 1.000Rint = 0.029
88833 measured reflectionsθmax = 36.4°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.095Δρmax = 2.33 e Å3
S = 1.13Δρmin = 1.52 e Å3
33353 reflectionsAbsolute structure: ?
847 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. Bruker KRYOFLEX low temperature device.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.35237 (2)0.90822 (2)0.08989 (2)0.01904 (3)
I20.34600 (2)0.94345 (2)0.24227 (2)0.03038 (4)
F10.38098 (13)1.07085 (11)0.01520 (7)0.0281 (3)
F20.37976 (14)1.08362 (12)0.14181 (8)0.0324 (3)
F30.34131 (13)0.76760 (12)0.13909 (7)0.0274 (3)
F40.34360 (12)0.75421 (10)0.01259 (7)0.0225 (3)
C630.36335 (17)0.91197 (16)0.00969 (10)0.0169 (3)
C640.37373 (18)0.99386 (17)0.04493 (11)0.0204 (4)
C650.37311 (18)1.00061 (18)0.11085 (11)0.0228 (4)
C660.36154 (18)0.92572 (19)0.14444 (11)0.0220 (4)
C670.35349 (18)0.84232 (18)0.10952 (11)0.0208 (4)
C680.35475 (17)0.83579 (16)0.04374 (10)0.0175 (4)
I30.66213 (2)0.13414 (2)0.44197 (2)0.01774 (3)
F50.53244 (16)0.12749 (14)0.57729 (8)0.0365 (4)
F60.40813 (15)0.02901 (14)0.62120 (7)0.0352 (4)
C690.56585 (16)0.05310 (15)0.47630 (10)0.0157 (3)
C700.51796 (19)0.06462 (17)0.53805 (10)0.0191 (4)
C710.45316 (18)0.01311 (17)0.56077 (10)0.0189 (4)
I40.81611 (2)0.26919 (2)0.40053 (2)0.01718 (3)
Na10.28660 (6)0.48248 (6)0.33541 (4)0.01198 (14)
C10.35809 (15)0.61807 (14)0.16785 (9)0.0123 (3)
H1A0.39130.65370.13620.015*
H1B0.39850.60220.20700.015*
C20.36498 (15)0.51884 (14)0.14083 (9)0.0122 (3)
C30.37844 (15)0.43217 (15)0.18038 (9)0.0118 (3)
C40.36586 (15)0.34727 (15)0.15885 (9)0.0125 (3)
C50.34566 (16)0.34878 (15)0.09473 (9)0.0138 (3)
H50.33780.29120.07930.017*
C60.33659 (16)0.43189 (15)0.05242 (9)0.0138 (3)
C70.34621 (16)0.51596 (15)0.07682 (9)0.0139 (3)
H70.33980.57350.04900.017*
C80.31192 (17)0.43014 (16)0.01729 (9)0.0170 (4)
C90.3974 (2)0.3326 (2)0.04814 (11)0.0287 (5)
H9A0.47060.33200.04710.043*
H9B0.38140.33180.09260.043*
H9C0.39480.27160.02450.043*
C100.3157 (2)0.5231 (2)0.05771 (11)0.0275 (5)
H10A0.26160.58700.03920.041*
H10B0.29890.51910.10150.041*
H10C0.38920.52250.05810.041*
C110.1975 (2)0.4313 (2)0.01892 (12)0.0314 (6)
H11A0.14280.49390.00080.047*
H11B0.19480.37050.00480.047*
H11C0.18150.43040.06340.047*
C120.36723 (15)0.25868 (15)0.20404 (9)0.0126 (3)
H12A0.41200.25350.24010.015*
H12B0.40210.19330.18110.015*
C130.25217 (15)0.27271 (14)0.23036 (9)0.0116 (3)
C140.20958 (15)0.30877 (14)0.29168 (9)0.0108 (3)
C150.10034 (15)0.33158 (14)0.31206 (9)0.0109 (3)
C160.03657 (16)0.30926 (15)0.27155 (9)0.0136 (3)
H160.03730.32240.28550.016*
C170.07715 (16)0.26863 (15)0.21161 (9)0.0143 (3)
C180.18510 (16)0.25254 (15)0.19188 (9)0.0140 (3)
H180.21380.22680.15060.017*
C190.00734 (17)0.24537 (17)0.16685 (10)0.0182 (4)
C200.0057 (3)0.3158 (2)0.10669 (13)0.0333 (6)
H20A0.06690.30520.08650.050*
H20B0.04520.38790.11840.050*
H20C0.04720.29910.07660.050*
C210.0657 (2)0.1323 (2)0.14800 (14)0.0323 (6)
H21A0.13910.11970.12820.048*
H21B0.02320.11790.11750.048*
H21C0.07220.08710.18620.048*
C220.1062 (2)0.2629 (3)0.19732 (15)0.0424 (8)
H22A0.14750.24700.16680.064*
H22B0.14500.33510.20910.064*
H22C0.09900.21790.23570.064*
C230.04498 (15)0.38614 (14)0.37376 (9)0.0110 (3)
H23A0.00050.35220.39620.013*
H23B0.10120.38240.40240.013*
C240.02688 (15)0.49852 (14)0.35701 (8)0.0106 (3)
C250.01333 (14)0.57485 (14)0.35639 (8)0.0104 (3)
C260.04157 (15)0.67315 (14)0.32869 (9)0.0108 (3)
C270.14493 (15)0.69689 (15)0.30689 (9)0.0122 (3)
H270.18400.76360.28840.015*
C280.19249 (15)0.62560 (15)0.31141 (9)0.0120 (3)
C290.13076 (15)0.52614 (14)0.33562 (9)0.0116 (3)
H290.16070.47590.33750.014*
C300.30827 (16)0.65194 (16)0.29161 (10)0.0160 (3)
C310.37864 (17)0.64144 (19)0.35165 (11)0.0211 (4)
H31A0.45330.65780.34020.032*
H31B0.38080.68930.38360.032*
H31C0.34660.57060.36940.032*
C320.30418 (19)0.5761 (2)0.24192 (11)0.0226 (4)
H32A0.37850.59320.22950.034*
H32B0.27390.50570.26040.034*
H32C0.25760.58120.20420.034*
C330.3618 (2)0.7615 (2)0.26342 (15)0.0311 (6)
H33A0.43540.77470.25150.047*
H33B0.31720.76950.22540.047*
H33C0.36700.81070.29520.047*
C340.01059 (15)0.75009 (14)0.32028 (9)0.0117 (3)
H34A0.06260.73600.35380.014*
H34B0.04710.82060.32590.014*
C350.07130 (15)0.74521 (14)0.25480 (9)0.0108 (3)
C360.18597 (15)0.69558 (14)0.24474 (9)0.0107 (3)
C370.23745 (15)0.68700 (14)0.18334 (9)0.0114 (3)
C380.17334 (15)0.73731 (15)0.13246 (9)0.0127 (3)
H380.20840.73530.09080.015*
C390.05995 (15)0.79027 (15)0.14072 (9)0.0123 (3)
C400.01065 (15)0.79118 (15)0.20240 (9)0.0124 (3)
H400.06700.82440.20870.015*
C410.01023 (16)0.84392 (16)0.08496 (9)0.0154 (3)
C420.0597 (2)0.8482 (2)0.02385 (11)0.0257 (5)
H42A0.01170.88300.01070.039*
H42B0.10850.77790.01170.039*
H42C0.10370.88640.03140.039*
C430.0810 (2)0.7861 (2)0.07241 (13)0.0300 (5)
H43A0.12620.82030.03660.045*
H43B0.12860.78620.11080.045*
H43C0.03330.71470.06180.045*
C440.08552 (19)0.95498 (18)0.10161 (11)0.0234 (4)
H44A0.13050.98920.06580.035*
H44B0.04100.99220.10990.035*
H44C0.13330.95460.13980.035*
O10.40231 (11)0.43285 (11)0.24340 (6)0.0120 (2)
C450.51836 (15)0.38562 (16)0.25212 (10)0.0154 (3)
H45A0.55950.40220.21460.018*
H45B0.54380.30970.25650.018*
C460.53821 (16)0.42634 (17)0.31143 (10)0.0158 (3)
H46A0.61640.39070.32060.019*
H46B0.51990.50110.30540.019*
O20.47052 (12)0.40849 (12)0.36326 (7)0.0147 (3)
C470.48480 (16)0.44350 (16)0.42234 (9)0.0152 (3)
H47A0.48250.51400.41630.018*
H47B0.55660.39720.43830.018*
C480.39328 (16)0.44326 (16)0.46926 (9)0.0150 (3)
H48A0.39390.37330.47410.018*
H48B0.40180.46430.51160.018*
O30.29249 (11)0.51493 (11)0.44475 (7)0.0136 (2)
C490.19918 (16)0.51223 (16)0.48210 (9)0.0139 (3)
H49A0.19590.53680.52550.017*
H49B0.20390.44080.48620.017*
C500.09859 (16)0.58125 (15)0.44879 (9)0.0134 (3)
H50A0.03270.57520.47080.016*
H50B0.08880.65400.44970.016*
O40.11237 (11)0.55024 (11)0.38350 (6)0.0114 (2)
O50.27846 (11)0.32323 (10)0.33249 (6)0.0114 (2)
C510.34873 (15)0.22820 (15)0.36477 (9)0.0132 (3)
H51A0.41290.23640.37910.016*
H51B0.37590.17120.33460.016*
C520.28679 (15)0.20185 (14)0.42148 (9)0.0123 (3)
N10.28355 (15)0.24742 (14)0.47572 (8)0.0157 (3)
C530.22346 (19)0.23120 (18)0.52636 (10)0.0195 (4)
H530.22090.26290.56510.023*
C540.16501 (18)0.17105 (17)0.52556 (10)0.0201 (4)
H540.12260.16260.56260.024*
C550.16956 (19)0.12328 (17)0.46959 (11)0.0204 (4)
H550.13090.08070.46760.024*
C560.23156 (18)0.13859 (16)0.41647 (10)0.0174 (4)
H560.23630.10660.37750.021*
O60.24875 (11)0.65174 (10)0.29724 (6)0.0115 (2)
C570.30091 (16)0.71421 (15)0.31892 (9)0.0137 (3)
H57A0.34060.73420.28200.016*
H57B0.35500.67320.35000.016*
C580.21752 (16)0.80947 (15)0.34979 (9)0.0132 (3)
N20.17300 (16)0.89317 (14)0.31092 (9)0.0179 (3)
C590.0882 (2)0.97461 (18)0.33517 (12)0.0238 (4)
H590.05641.03420.30810.029*
C600.0444 (2)0.97661 (19)0.39779 (12)0.0254 (5)
H600.01871.03440.41250.031*
C610.09456 (19)0.89269 (18)0.43829 (11)0.0214 (4)
H610.06900.89320.48200.026*
C620.18275 (17)0.80765 (16)0.41415 (10)0.0161 (3)
H620.21890.74910.44110.019*
O70.33656 (17)0.90617 (14)0.22139 (8)0.0283 (4)
H7O70.28000.90270.24030.042*
C720.3633 (2)0.9777 (2)0.25185 (14)0.0315 (5)
H72A0.42500.98660.22750.047*
H72B0.38370.95170.29530.047*
H72C0.29971.04420.25390.047*
O80.0537 (2)0.5639 (2)0.16897 (13)0.0536 (7)
H8O80.07590.58070.20690.080*
C730.0623 (3)0.5265 (2)0.16222 (17)0.0409 (7)
H73A0.08380.58470.16060.061*
H73B0.08970.48880.12260.061*
H73C0.09340.48020.19880.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02211 (6)0.01769 (6)0.01537 (6)0.00697 (5)0.00277 (5)0.00068 (4)
I20.02485 (7)0.03401 (9)0.01512 (6)0.00398 (6)0.00076 (5)0.00473 (6)
F10.0363 (8)0.0219 (7)0.0295 (8)0.0157 (6)0.0029 (6)0.0030 (6)
F20.0371 (9)0.0287 (8)0.0293 (8)0.0140 (7)0.0020 (6)0.0148 (6)
F30.0313 (8)0.0266 (7)0.0217 (7)0.0084 (6)0.0027 (6)0.0052 (6)
F40.0296 (7)0.0183 (6)0.0205 (6)0.0115 (5)0.0003 (5)0.0025 (5)
C630.0153 (8)0.0174 (9)0.0153 (8)0.0048 (7)0.0006 (7)0.0020 (7)
C640.0191 (9)0.0172 (9)0.0222 (10)0.0054 (7)0.0006 (8)0.0025 (7)
C650.0182 (9)0.0212 (10)0.0232 (10)0.0045 (8)0.0017 (8)0.0090 (8)
C660.0159 (9)0.0258 (11)0.0170 (9)0.0021 (8)0.0001 (7)0.0045 (8)
C670.0185 (9)0.0217 (10)0.0182 (9)0.0043 (8)0.0006 (7)0.0016 (8)
C680.0156 (8)0.0161 (8)0.0175 (9)0.0039 (7)0.0004 (7)0.0025 (7)
I30.01577 (6)0.01619 (6)0.02253 (6)0.00874 (5)0.00138 (5)0.00536 (5)
F50.0587 (11)0.0454 (10)0.0245 (7)0.0411 (9)0.0089 (7)0.0126 (7)
F60.0538 (10)0.0465 (10)0.0195 (7)0.0370 (9)0.0149 (7)0.0106 (7)
C690.0139 (8)0.0144 (8)0.0197 (9)0.0074 (7)0.0008 (7)0.0041 (7)
C700.0247 (10)0.0197 (9)0.0176 (9)0.0140 (8)0.0007 (7)0.0013 (7)
C710.0219 (9)0.0201 (9)0.0158 (8)0.0106 (8)0.0022 (7)0.0008 (7)
I40.01597 (6)0.01691 (6)0.02085 (6)0.00969 (5)0.00064 (4)0.00334 (4)
Na10.0119 (3)0.0131 (3)0.0112 (3)0.0053 (3)0.0009 (3)0.0002 (3)
C10.0111 (7)0.0137 (7)0.0124 (7)0.0059 (6)0.0016 (6)0.0006 (6)
C20.0127 (7)0.0129 (7)0.0100 (7)0.0044 (6)0.0013 (6)0.0006 (6)
C30.0105 (7)0.0145 (8)0.0088 (7)0.0038 (6)0.0007 (6)0.0007 (6)
C40.0113 (7)0.0132 (7)0.0118 (7)0.0041 (6)0.0012 (6)0.0010 (6)
C50.0153 (8)0.0148 (8)0.0106 (7)0.0054 (6)0.0004 (6)0.0020 (6)
C60.0137 (8)0.0157 (8)0.0097 (7)0.0037 (6)0.0003 (6)0.0019 (6)
C70.0138 (8)0.0139 (8)0.0118 (7)0.0039 (6)0.0009 (6)0.0001 (6)
C80.0195 (9)0.0182 (9)0.0106 (7)0.0048 (7)0.0014 (7)0.0018 (6)
C90.0375 (13)0.0244 (11)0.0148 (9)0.0027 (10)0.0006 (9)0.0047 (8)
C100.0409 (14)0.0264 (11)0.0145 (9)0.0127 (10)0.0059 (9)0.0038 (8)
C110.0267 (12)0.0479 (16)0.0210 (11)0.0161 (12)0.0075 (9)0.0029 (11)
C120.0110 (7)0.0127 (7)0.0120 (7)0.0028 (6)0.0001 (6)0.0000 (6)
C130.0117 (7)0.0115 (7)0.0103 (7)0.0037 (6)0.0007 (6)0.0001 (6)
C140.0111 (7)0.0111 (7)0.0106 (7)0.0047 (6)0.0023 (6)0.0006 (6)
C150.0110 (7)0.0122 (7)0.0102 (7)0.0055 (6)0.0012 (6)0.0002 (6)
C160.0123 (7)0.0157 (8)0.0141 (8)0.0067 (6)0.0010 (6)0.0016 (6)
C170.0160 (8)0.0142 (8)0.0134 (8)0.0063 (7)0.0030 (6)0.0010 (6)
C180.0150 (8)0.0147 (8)0.0122 (7)0.0057 (6)0.0007 (6)0.0019 (6)
C190.0180 (9)0.0238 (10)0.0156 (8)0.0101 (8)0.0044 (7)0.0054 (7)
C200.0423 (15)0.0349 (14)0.0288 (12)0.0189 (12)0.0202 (11)0.0044 (10)
C210.0397 (14)0.0249 (12)0.0365 (14)0.0139 (11)0.0157 (12)0.0060 (10)
C220.0258 (12)0.078 (2)0.0356 (15)0.0310 (15)0.0007 (11)0.0240 (15)
C230.0102 (7)0.0124 (7)0.0103 (7)0.0047 (6)0.0004 (6)0.0001 (6)
C240.0104 (7)0.0119 (7)0.0096 (7)0.0049 (6)0.0004 (5)0.0007 (6)
C250.0086 (7)0.0140 (7)0.0093 (7)0.0053 (6)0.0003 (5)0.0013 (6)
C260.0104 (7)0.0129 (7)0.0105 (7)0.0064 (6)0.0020 (6)0.0018 (6)
C270.0115 (7)0.0128 (7)0.0117 (7)0.0046 (6)0.0013 (6)0.0017 (6)
C280.0105 (7)0.0150 (8)0.0113 (7)0.0062 (6)0.0008 (6)0.0010 (6)
C290.0121 (7)0.0137 (7)0.0106 (7)0.0068 (6)0.0001 (6)0.0004 (6)
C300.0117 (7)0.0172 (8)0.0204 (9)0.0070 (7)0.0049 (7)0.0031 (7)
C310.0134 (8)0.0279 (11)0.0234 (10)0.0099 (8)0.0022 (7)0.0046 (8)
C320.0197 (9)0.0343 (12)0.0183 (9)0.0150 (9)0.0048 (8)0.0005 (8)
C330.0206 (10)0.0239 (11)0.0517 (16)0.0111 (9)0.0197 (11)0.0154 (11)
C340.0127 (7)0.0127 (7)0.0110 (7)0.0066 (6)0.0011 (6)0.0018 (6)
C350.0125 (7)0.0111 (7)0.0109 (7)0.0071 (6)0.0005 (6)0.0012 (6)
C360.0123 (7)0.0097 (7)0.0104 (7)0.0048 (6)0.0005 (6)0.0001 (5)
C370.0113 (7)0.0106 (7)0.0128 (7)0.0052 (6)0.0008 (6)0.0014 (6)
C380.0129 (7)0.0146 (8)0.0097 (7)0.0051 (6)0.0007 (6)0.0012 (6)
C390.0131 (7)0.0131 (7)0.0109 (7)0.0058 (6)0.0006 (6)0.0005 (6)
C400.0115 (7)0.0141 (8)0.0119 (7)0.0057 (6)0.0006 (6)0.0002 (6)
C410.0155 (8)0.0180 (8)0.0125 (8)0.0066 (7)0.0026 (6)0.0020 (6)
C420.0225 (10)0.0323 (12)0.0137 (9)0.0034 (9)0.0014 (8)0.0053 (8)
C430.0349 (13)0.0360 (14)0.0283 (12)0.0219 (11)0.0165 (10)0.0057 (10)
C440.0221 (10)0.0197 (10)0.0205 (10)0.0007 (8)0.0032 (8)0.0034 (8)
O10.0100 (5)0.0155 (6)0.0091 (5)0.0038 (5)0.0007 (4)0.0006 (5)
C450.0106 (7)0.0192 (9)0.0146 (8)0.0040 (7)0.0007 (6)0.0021 (7)
C460.0132 (8)0.0206 (9)0.0152 (8)0.0082 (7)0.0020 (6)0.0004 (7)
O20.0153 (6)0.0197 (7)0.0117 (6)0.0096 (5)0.0017 (5)0.0014 (5)
C470.0142 (8)0.0209 (9)0.0132 (8)0.0088 (7)0.0041 (6)0.0023 (7)
C480.0140 (8)0.0192 (9)0.0122 (7)0.0067 (7)0.0050 (6)0.0011 (6)
O30.0121 (6)0.0170 (6)0.0121 (6)0.0061 (5)0.0018 (5)0.0010 (5)
C490.0139 (8)0.0169 (8)0.0105 (7)0.0062 (7)0.0008 (6)0.0008 (6)
C500.0133 (7)0.0164 (8)0.0100 (7)0.0053 (6)0.0006 (6)0.0040 (6)
O40.0104 (5)0.0150 (6)0.0095 (5)0.0056 (5)0.0006 (4)0.0022 (4)
O50.0123 (6)0.0118 (6)0.0109 (5)0.0054 (5)0.0038 (4)0.0015 (4)
C510.0119 (7)0.0139 (8)0.0125 (7)0.0040 (6)0.0021 (6)0.0026 (6)
C520.0114 (7)0.0121 (7)0.0120 (7)0.0035 (6)0.0018 (6)0.0018 (6)
N10.0190 (8)0.0172 (7)0.0123 (7)0.0088 (6)0.0008 (6)0.0012 (6)
C530.0230 (10)0.0237 (10)0.0125 (8)0.0104 (8)0.0012 (7)0.0022 (7)
C540.0211 (9)0.0209 (9)0.0164 (9)0.0083 (8)0.0038 (7)0.0014 (7)
C550.0220 (10)0.0194 (9)0.0223 (10)0.0118 (8)0.0015 (8)0.0002 (8)
C560.0210 (9)0.0157 (8)0.0166 (8)0.0088 (7)0.0006 (7)0.0018 (7)
O60.0129 (6)0.0123 (6)0.0107 (5)0.0065 (5)0.0026 (4)0.0006 (4)
C570.0124 (7)0.0151 (8)0.0151 (8)0.0067 (6)0.0017 (6)0.0022 (6)
C580.0146 (8)0.0149 (8)0.0126 (7)0.0080 (6)0.0019 (6)0.0014 (6)
N20.0223 (8)0.0154 (7)0.0160 (7)0.0075 (7)0.0037 (6)0.0005 (6)
C590.0291 (11)0.0156 (9)0.0228 (10)0.0039 (8)0.0069 (9)0.0015 (8)
C600.0236 (10)0.0210 (10)0.0276 (11)0.0034 (8)0.0019 (9)0.0107 (9)
C610.0227 (10)0.0255 (10)0.0175 (9)0.0108 (8)0.0014 (8)0.0089 (8)
C620.0200 (9)0.0178 (9)0.0132 (8)0.0103 (7)0.0015 (7)0.0021 (7)
O70.0409 (10)0.0284 (9)0.0201 (8)0.0203 (8)0.0069 (7)0.0034 (7)
C720.0371 (14)0.0260 (12)0.0330 (13)0.0151 (11)0.0021 (11)0.0025 (10)
O80.0406 (13)0.0715 (18)0.0456 (14)0.0197 (13)0.0048 (11)0.0123 (13)
C730.0376 (16)0.0337 (15)0.0500 (19)0.0146 (13)0.0064 (13)0.0053 (13)
Geometric parameters (Å, º) top
I1—C632.083 (2)C30—C311.540 (3)
I2—C662.074 (2)C31—H31A0.9800
F1—C641.340 (3)C31—H31B0.9800
F2—C651.339 (3)C31—H31C0.9800
F3—C671.341 (3)C32—H32A0.9800
F4—C681.347 (2)C32—H32B0.9800
C63—C641.384 (3)C32—H32C0.9800
C63—C681.389 (3)C33—H33A0.9800
C64—C651.383 (3)C33—H33B0.9800
C65—C661.386 (4)C33—H33C0.9800
C66—C671.387 (3)C34—C351.523 (3)
C67—C681.381 (3)C34—H34A0.9900
I3—C692.1078 (19)C34—H34B0.9900
F5—C701.340 (3)C35—C401.389 (3)
F6—C711.347 (3)C35—C361.405 (3)
C69—C71i1.378 (3)C36—C371.394 (3)
C69—C701.382 (3)C36—O61.400 (2)
C70—C711.383 (3)C37—C381.397 (3)
C71—C69i1.378 (3)C38—C391.391 (3)
Na1—O42.2915 (16)C38—H380.9500
Na1—O52.3178 (16)C39—C401.397 (3)
Na1—O12.3188 (16)C39—C411.527 (3)
Na1—O62.3443 (16)C40—H400.9500
Na1—O22.3617 (17)C41—C441.530 (3)
Na1—O32.3913 (16)C41—C421.530 (3)
C1—C21.524 (3)C41—C431.538 (3)
C1—C371.525 (3)C42—H42A0.9800
C1—H1A0.9900C42—H42B0.9800
C1—H1B0.9900C42—H42C0.9800
C2—C31.394 (3)C43—H43A0.9800
C2—C71.398 (3)C43—H43B0.9800
C3—O11.393 (2)C43—H43C0.9800
C3—C41.397 (3)C44—H44A0.9800
C4—C51.396 (3)C44—H44B0.9800
C4—C121.518 (3)C44—H44C0.9800
C5—C61.398 (3)O1—C451.443 (2)
C5—H50.9500C45—C461.501 (3)
C6—C71.392 (3)C45—H45A0.9900
C6—C81.536 (3)C45—H45B0.9900
C7—H70.9500C46—O21.428 (2)
C8—C91.530 (3)C46—H46A0.9900
C8—C111.531 (3)C46—H46B0.9900
C8—C101.536 (3)O2—C471.428 (2)
C9—H9A0.9800C47—C481.501 (3)
C9—H9B0.9800C47—H47A0.9900
C9—H9C0.9800C47—H47B0.9900
C10—H10A0.9800C48—O31.433 (2)
C10—H10B0.9800C48—H48A0.9900
C10—H10C0.9800C48—H48B0.9900
C11—H11A0.9800O3—C491.426 (2)
C11—H11B0.9800C49—C501.504 (3)
C11—H11C0.9800C49—H49A0.9900
C12—C131.525 (3)C49—H49B0.9900
C12—H12A0.9900C50—O41.444 (2)
C12—H12B0.9900C50—H50A0.9900
C13—C181.388 (3)C50—H50B0.9900
C13—C141.402 (3)O5—C511.455 (2)
C14—C151.394 (3)C51—C521.502 (3)
C14—O51.400 (2)C51—H51A0.9900
C15—C161.398 (3)C51—H51B0.9900
C15—C231.525 (3)C52—N11.340 (3)
C16—C171.391 (3)C52—C561.394 (3)
C16—H160.9500N1—C531.338 (3)
C17—C181.395 (3)C53—C541.379 (3)
C17—C191.528 (3)C53—H530.9500
C18—H180.9500C54—C551.385 (3)
C19—C221.521 (3)C54—H540.9500
C19—C201.533 (4)C55—C561.387 (3)
C19—C211.535 (3)C55—H550.9500
C20—H20A0.9800C56—H560.9500
C20—H20B0.9800O6—C571.454 (2)
C20—H20C0.9800C57—C581.501 (3)
C21—H21A0.9800C57—H57A0.9900
C21—H21B0.9800C57—H57B0.9900
C21—H21C0.9800C58—N21.346 (3)
C22—H22A0.9800C58—C621.391 (3)
C22—H22B0.9800N2—C591.337 (3)
C22—H22C0.9800C59—C601.387 (4)
C23—C241.525 (3)C59—H590.9500
C23—H23A0.9900C60—C611.380 (4)
C23—H23B0.9900C60—H600.9500
C24—C291.392 (3)C61—C621.385 (3)
C24—C251.395 (3)C61—H610.9500
C25—O41.393 (2)C62—H620.9500
C25—C261.398 (3)O7—C721.418 (3)
C26—C271.398 (3)O7—H7O70.8400
C26—C341.515 (3)C72—H72A0.9800
C27—C281.396 (3)C72—H72B0.9800
C27—H270.9500C72—H72C0.9800
C28—C291.400 (3)O8—C731.418 (4)
C28—C301.531 (3)O8—H8O80.8400
C29—H290.9500C73—H73A0.9800
C30—C331.525 (3)C73—H73B0.9800
C30—C321.536 (3)C73—H73C0.9800
C64—C63—C68116.9 (2)C32—C30—C31109.31 (17)
C64—C63—I1121.17 (17)C30—C31—H31A109.5
C68—C63—I1121.88 (15)C30—C31—H31B109.5
F1—C64—C65118.3 (2)H31A—C31—H31B109.5
F1—C64—C63120.1 (2)C30—C31—H31C109.5
C65—C64—C63121.5 (2)H31A—C31—H31C109.5
F2—C65—C64118.4 (2)H31B—C31—H31C109.5
F2—C65—C66120.2 (2)C30—C32—H32A109.5
C64—C65—C66121.3 (2)C30—C32—H32B109.5
C65—C66—C67117.4 (2)H32A—C32—H32B109.5
C65—C66—I2120.96 (17)C30—C32—H32C109.5
C67—C66—I2121.48 (18)H32A—C32—H32C109.5
F3—C67—C68118.7 (2)H32B—C32—H32C109.5
F3—C67—C66120.4 (2)C30—C33—H33A109.5
C68—C67—C66120.9 (2)C30—C33—H33B109.5
F4—C68—C67117.9 (2)H33A—C33—H33B109.5
F4—C68—C63120.14 (19)C30—C33—H33C109.5
C67—C68—C63121.9 (2)H33A—C33—H33C109.5
C71i—C69—C70116.57 (18)H33B—C33—H33C109.5
C71i—C69—I3122.59 (15)C26—C34—C35112.19 (15)
C70—C69—I3120.84 (16)C26—C34—H34A109.2
F5—C70—C69120.37 (19)C35—C34—H34A109.2
F5—C70—C71118.28 (19)C26—C34—H34B109.2
C69—C70—C71121.3 (2)C35—C34—H34B109.2
F6—C71—C69i119.86 (19)H34A—C34—H34B107.9
F6—C71—C70118.1 (2)C40—C35—C36118.34 (17)
C69i—C71—C70122.1 (2)C40—C35—C34118.62 (16)
O4—Na1—O590.28 (6)C36—C35—C34123.04 (16)
O4—Na1—O1149.51 (6)C37—C36—O6119.79 (16)
O5—Na1—O185.04 (6)C37—C36—C35121.02 (17)
O4—Na1—O685.40 (6)O6—C36—C35119.17 (16)
O5—Na1—O6153.33 (6)C36—C37—C38118.33 (17)
O1—Na1—O685.47 (6)C36—C37—C1123.48 (17)
O4—Na1—O2139.63 (6)C38—C37—C1117.97 (16)
O5—Na1—O292.91 (6)C39—C38—C37122.22 (17)
O1—Na1—O270.80 (5)C39—C38—H38118.9
O6—Na1—O2107.34 (6)C37—C38—H38118.9
O4—Na1—O370.07 (6)C38—C39—C40117.60 (17)
O5—Na1—O3107.73 (6)C38—C39—C41122.19 (17)
O1—Na1—O3139.84 (6)C40—C39—C41120.19 (17)
O6—Na1—O395.50 (6)C35—C40—C39122.24 (17)
O2—Na1—O370.66 (6)C35—C40—H40118.9
C2—C1—C37108.24 (15)C39—C40—H40118.9
C2—C1—H1A110.1C39—C41—C44109.63 (17)
C37—C1—H1A110.1C39—C41—C42112.03 (17)
C2—C1—H1B110.1C44—C41—C42107.59 (18)
C37—C1—H1B110.1C39—C41—C43109.30 (17)
H1A—C1—H1B108.4C44—C41—C43109.0 (2)
C3—C2—C7118.03 (17)C42—C41—C43109.2 (2)
C3—C2—C1121.10 (16)C41—C42—H42A109.5
C7—C2—C1120.53 (17)C41—C42—H42B109.5
O1—C3—C2118.19 (17)H42A—C42—H42B109.5
O1—C3—C4120.02 (16)C41—C42—H42C109.5
C2—C3—C4121.77 (17)H42A—C42—H42C109.5
C5—C4—C3117.84 (17)H42B—C42—H42C109.5
C5—C4—C12120.50 (17)C41—C43—H43A109.5
C3—C4—C12121.56 (17)C41—C43—H43B109.5
C4—C5—C6122.43 (18)H43A—C43—H43B109.5
C4—C5—H5118.8C41—C43—H43C109.5
C6—C5—H5118.8H43A—C43—H43C109.5
C7—C6—C5117.40 (17)H43B—C43—H43C109.5
C7—C6—C8122.46 (18)C41—C44—H44A109.5
C5—C6—C8120.09 (18)C41—C44—H44B109.5
C6—C7—C2122.37 (18)H44A—C44—H44B109.5
C6—C7—H7118.8C41—C44—H44C109.5
C2—C7—H7118.8H44A—C44—H44C109.5
C9—C8—C11109.5 (2)H44B—C44—H44C109.5
C9—C8—C10107.42 (19)C3—O1—C45113.05 (14)
C11—C8—C10108.4 (2)O1—C45—C46108.41 (16)
C9—C8—C6109.69 (17)O1—C45—H45A110.0
C11—C8—C6109.39 (18)C46—C45—H45A110.0
C10—C8—C6112.36 (18)O1—C45—H45B110.0
C8—C9—H9A109.5C46—C45—H45B110.0
C8—C9—H9B109.5H45A—C45—H45B108.4
H9A—C9—H9B109.5O2—C46—C45108.21 (16)
C8—C9—H9C109.5O2—C46—H46A110.1
H9A—C9—H9C109.5C45—C46—H46A110.1
H9B—C9—H9C109.5O2—C46—H46B110.1
C8—C10—H10A109.5C45—C46—H46B110.1
C8—C10—H10B109.5H46A—C46—H46B108.4
H10A—C10—H10B109.5C46—O2—C47112.42 (15)
C8—C10—H10C109.5O2—C47—C48107.57 (15)
H10A—C10—H10C109.5O2—C47—H47A110.2
H10B—C10—H10C109.5C48—C47—H47A110.2
C8—C11—H11A109.5O2—C47—H47B110.2
C8—C11—H11B109.5C48—C47—H47B110.2
H11A—C11—H11B109.5H47A—C47—H47B108.5
C8—C11—H11C109.5O3—C48—C47107.30 (16)
H11A—C11—H11C109.5O3—C48—H48A110.3
H11B—C11—H11C109.5C47—C48—H48A110.3
C4—C12—C13112.14 (15)O3—C48—H48B110.3
C4—C12—H12A109.2C47—C48—H48B110.3
C13—C12—H12A109.2H48A—C48—H48B108.5
C4—C12—H12B109.2C49—O3—C48111.92 (15)
C13—C12—H12B109.2O3—C49—C50107.78 (15)
H12A—C12—H12B107.9O3—C49—H49A110.2
C18—C13—C14118.23 (17)C50—C49—H49A110.2
C18—C13—C12119.32 (16)O3—C49—H49B110.2
C14—C13—C12122.42 (16)C50—C49—H49B110.2
C15—C14—O5119.88 (16)H49A—C49—H49B108.5
C15—C14—C13121.28 (17)O4—C50—C49108.38 (15)
O5—C14—C13118.83 (16)O4—C50—H50A110.0
C14—C15—C16117.95 (17)C49—C50—H50A110.0
C14—C15—C23123.50 (16)O4—C50—H50B110.0
C16—C15—C23118.40 (16)C49—C50—H50B110.0
C17—C16—C15122.51 (18)H50A—C50—H50B108.4
C17—C16—H16118.7C25—O4—C50113.27 (14)
C15—C16—H16118.7C14—O5—C51113.19 (14)
C16—C17—C18117.38 (18)O5—C51—C52110.60 (15)
C16—C17—C19122.69 (18)O5—C51—H51A109.5
C18—C17—C19119.90 (18)C52—C51—H51A109.5
C13—C18—C17122.43 (18)O5—C51—H51B109.5
C13—C18—H18118.8C52—C51—H51B109.5
C17—C18—H18118.8H51A—C51—H51B108.1
C22—C19—C17112.65 (18)N1—C52—C56122.70 (18)
C22—C19—C20108.6 (2)N1—C52—C51115.58 (17)
C17—C19—C20108.70 (18)C56—C52—C51121.62 (18)
C22—C19—C21108.4 (2)C53—N1—C52117.53 (18)
C17—C19—C21109.11 (18)N1—C53—C54123.8 (2)
C20—C19—C21109.3 (2)N1—C53—H53118.1
C19—C20—H20A109.5C54—C53—H53118.1
C19—C20—H20B109.5C53—C54—C55118.5 (2)
H20A—C20—H20B109.5C53—C54—H54120.8
C19—C20—H20C109.5C55—C54—H54120.8
H20A—C20—H20C109.5C54—C55—C56118.9 (2)
H20B—C20—H20C109.5C54—C55—H55120.6
C19—C21—H21A109.5C56—C55—H55120.6
C19—C21—H21B109.5C55—C56—C52118.64 (19)
H21A—C21—H21B109.5C55—C56—H56120.7
C19—C21—H21C109.5C52—C56—H56120.7
H21A—C21—H21C109.5C36—O6—C57113.85 (14)
H21B—C21—H21C109.5O6—C57—C58110.95 (15)
C19—C22—H22A109.5O6—C57—H57A109.4
C19—C22—H22B109.5C58—C57—H57A109.5
H22A—C22—H22B109.5O6—C57—H57B109.5
C19—C22—H22C109.5C58—C57—H57B109.4
H22A—C22—H22C109.5H57A—C57—H57B108.0
H22B—C22—H22C109.5N2—C58—C62122.41 (19)
C24—C23—C15108.56 (15)N2—C58—C57116.37 (17)
C24—C23—H23A110.0C62—C58—C57121.02 (18)
C15—C23—H23A110.0C59—N2—C58117.68 (19)
C24—C23—H23B110.0N2—C59—C60123.4 (2)
C15—C23—H23B110.0N2—C59—H59118.3
H23A—C23—H23B108.4C60—C59—H59118.3
C29—C24—C25117.87 (17)C61—C60—C59118.5 (2)
C29—C24—C23120.68 (16)C61—C60—H60120.8
C25—C24—C23121.14 (16)C59—C60—H60120.8
O4—C25—C24118.04 (16)C60—C61—C62119.0 (2)
O4—C25—C26119.89 (16)C60—C61—H61120.5
C24—C25—C26122.06 (16)C62—C61—H61120.5
C25—C26—C27117.68 (16)C61—C62—C58118.9 (2)
C25—C26—C34121.30 (16)C61—C62—H62120.6
C27—C26—C34120.99 (17)C58—C62—H62120.6
C28—C27—C26122.05 (17)C72—O7—H7O7109.5
C28—C27—H27119.0O7—C72—H72A109.5
C26—C27—H27119.0O7—C72—H72B109.5
C27—C28—C29117.82 (17)H72A—C72—H72B109.5
C27—C28—C30122.92 (17)O7—C72—H72C109.5
C29—C28—C30119.25 (17)H72A—C72—H72C109.5
C24—C29—C28122.10 (17)H72B—C72—H72C109.5
C24—C29—H29118.9C73—O8—H8O8109.5
C28—C29—H29118.9O8—C73—H73A109.5
C33—C30—C28112.45 (17)O8—C73—H73B109.5
C33—C30—C32108.7 (2)H73A—C73—H73B109.5
C28—C30—C32109.79 (17)O8—C73—H73C109.5
C33—C30—C31108.6 (2)H73A—C73—H73C109.5
C28—C30—C31107.87 (17)H73B—C73—H73C109.5
C68—C63—C64—F1179.13 (19)C29—C24—C25—C267.3 (3)
I1—C63—C64—F12.5 (3)C23—C24—C25—C26166.34 (17)
C68—C63—C64—C651.4 (3)O4—C25—C26—C27174.81 (16)
I1—C63—C64—C65175.26 (17)C24—C25—C26—C276.3 (3)
F1—C64—C65—F20.0 (3)O4—C25—C26—C347.4 (3)
C63—C64—C65—F2177.8 (2)C24—C25—C26—C34171.47 (17)
F1—C64—C65—C66177.5 (2)C25—C26—C27—C280.8 (3)
C63—C64—C65—C660.3 (3)C34—C26—C27—C28176.97 (17)
F2—C65—C66—C67179.1 (2)C26—C27—C28—C293.4 (3)
C64—C65—C66—C671.6 (3)C26—C27—C28—C30176.19 (18)
F2—C65—C66—I23.3 (3)C25—C24—C29—C282.8 (3)
C64—C65—C66—I2174.18 (17)C23—C24—C29—C28170.86 (17)
C65—C66—C67—F3179.5 (2)C27—C28—C29—C242.4 (3)
I2—C66—C67—F33.7 (3)C30—C28—C29—C24177.21 (17)
C65—C66—C67—C681.3 (3)C27—C28—C30—C333.2 (3)
I2—C66—C67—C68174.51 (16)C29—C28—C30—C33177.3 (2)
F3—C67—C68—F40.0 (3)C27—C28—C30—C32124.4 (2)
C66—C67—C68—F4178.21 (19)C29—C28—C30—C3256.1 (2)
F3—C67—C68—C63177.80 (19)C27—C28—C30—C31116.6 (2)
C66—C67—C68—C630.4 (3)C29—C28—C30—C3162.9 (2)
C64—C63—C68—F4179.50 (19)C25—C26—C34—C3593.1 (2)
I1—C63—C68—F42.9 (3)C27—C26—C34—C3584.6 (2)
C64—C63—C68—C671.8 (3)C26—C34—C35—C4077.5 (2)
I1—C63—C68—C67174.88 (16)C26—C34—C35—C36101.9 (2)
C71i—C69—C70—F5179.9 (2)C40—C35—C36—C373.9 (3)
I3—C69—C70—F50.3 (3)C34—C35—C36—C37175.61 (17)
C71i—C69—C70—C710.9 (4)C40—C35—C36—O6177.93 (16)
I3—C69—C70—C71178.94 (17)C34—C35—C36—O62.6 (3)
F5—C70—C71—F60.0 (3)O6—C36—C37—C38175.90 (16)
C69—C70—C71—F6179.2 (2)C35—C36—C37—C385.9 (3)
F5—C70—C71—C69i179.9 (2)O6—C36—C37—C19.7 (3)
C69—C70—C71—C69i0.9 (4)C35—C36—C37—C1168.53 (17)
C37—C1—C2—C392.9 (2)C2—C1—C37—C3699.8 (2)
C37—C1—C2—C780.3 (2)C2—C1—C37—C3874.7 (2)
C7—C2—C3—O1177.01 (16)C36—C37—C38—C393.7 (3)
C1—C2—C3—O19.7 (3)C1—C37—C38—C39171.06 (17)
C7—C2—C3—C44.6 (3)C37—C38—C39—C400.5 (3)
C1—C2—C3—C4168.65 (17)C37—C38—C39—C41179.11 (18)
O1—C3—C4—C5177.88 (16)C36—C35—C40—C390.6 (3)
C2—C3—C4—C53.8 (3)C34—C35—C40—C39179.94 (17)
O1—C3—C4—C125.7 (3)C38—C39—C40—C352.7 (3)
C2—C3—C4—C12172.64 (17)C41—C39—C40—C35178.69 (18)
C3—C4—C5—C60.7 (3)C38—C39—C41—C44129.4 (2)
C12—C4—C5—C6175.76 (17)C40—C39—C41—C4452.0 (2)
C4—C5—C6—C71.3 (3)C38—C39—C41—C4210.1 (3)
C4—C5—C6—C8178.73 (18)C40—C39—C41—C42171.41 (19)
C5—C6—C7—C20.4 (3)C38—C39—C41—C43111.1 (2)
C8—C6—C7—C2177.78 (18)C40—C39—C41—C4367.4 (2)
C3—C2—C7—C62.5 (3)C2—C3—O1—C4594.2 (2)
C1—C2—C7—C6170.87 (17)C4—C3—O1—C4587.4 (2)
C7—C6—C8—C9127.5 (2)C3—O1—C45—C46157.52 (16)
C5—C6—C8—C955.3 (3)O1—C45—C46—O254.9 (2)
C7—C6—C8—C11112.4 (2)C45—C46—O2—C47179.18 (16)
C5—C6—C8—C1164.9 (3)C46—O2—C47—C48167.37 (16)
C7—C6—C8—C108.1 (3)O2—C47—C48—O362.3 (2)
C5—C6—C8—C10174.66 (19)C47—C48—O3—C49173.38 (16)
C5—C4—C12—C1382.9 (2)C48—O3—C49—C50174.10 (15)
C3—C4—C12—C1393.5 (2)O3—C49—C50—O453.3 (2)
C4—C12—C13—C1877.2 (2)C24—C25—O4—C5096.29 (19)
C4—C12—C13—C14100.6 (2)C26—C25—O4—C5084.8 (2)
C18—C13—C14—C154.9 (3)C49—C50—O4—C25154.11 (15)
C12—C13—C14—C15172.94 (17)C15—C14—O5—C5199.66 (19)
C18—C13—C14—O5176.02 (16)C13—C14—O5—C5181.2 (2)
C12—C13—C14—O56.2 (3)C14—O5—C51—C5280.68 (19)
O5—C14—C15—C16175.64 (16)O5—C51—C52—N184.9 (2)
C13—C14—C15—C165.3 (3)O5—C51—C52—C5691.6 (2)
O5—C14—C15—C238.8 (3)C56—C52—N1—C530.6 (3)
C13—C14—C15—C23170.32 (17)C51—C52—N1—C53175.90 (18)
C14—C15—C16—C172.0 (3)C52—N1—C53—C540.3 (3)
C23—C15—C16—C17173.79 (18)N1—C53—C54—C550.9 (4)
C15—C16—C17—C181.5 (3)C53—C54—C55—C560.7 (3)
C15—C16—C17—C19179.23 (19)C54—C55—C56—C520.2 (3)
C14—C13—C18—C171.2 (3)N1—C52—C56—C550.9 (3)
C12—C13—C18—C17176.70 (18)C51—C52—C56—C55175.48 (19)
C16—C17—C18—C131.9 (3)C37—C36—O6—C5780.4 (2)
C19—C17—C18—C13179.72 (19)C35—C36—O6—C57101.37 (19)
C16—C17—C19—C224.8 (3)C36—O6—C57—C5870.3 (2)
C18—C17—C19—C22177.5 (2)O6—C57—C58—N289.6 (2)
C16—C17—C19—C20115.6 (2)O6—C57—C58—C6285.5 (2)
C18—C17—C19—C2062.1 (3)C62—C58—N2—C593.9 (3)
C16—C17—C19—C21125.3 (2)C57—C58—N2—C59171.15 (19)
C18—C17—C19—C2157.0 (3)C58—N2—C59—C600.2 (3)
C14—C15—C23—C24102.5 (2)N2—C59—C60—C613.8 (4)
C16—C15—C23—C2473.0 (2)C59—C60—C61—C623.5 (3)
C15—C23—C24—C2980.7 (2)C60—C61—C62—C580.3 (3)
C15—C23—C24—C2592.8 (2)N2—C58—C62—C614.1 (3)
C29—C24—C25—O4173.84 (16)C57—C58—C62—C61170.66 (18)
C23—C24—C25—O412.5 (2)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C63—I1···O72.75 (1)179 (1)
C69—I3···I43.38 (1)175 (1)
C66—I2···F6ii3.21 (1)149 (1)
O7—H7O7···N20.842.002.809 (3)161
Symmetry code: (ii) x, y+1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C63—I1···O7.2.7515 (18).179.21 (7)
C69—I3···I4.3.3746 (5).174.93 (6)
C66—I2···F6i.3.2088 (17).148.66 (8)
O7—H7O7···N20.842.002.809 (3)161
Symmetry code: (i) x, y+1, z1.
Acknowledgements top

GC, PM, GR and GT acknowledge the Fondazione Cariplo (projects 2009–2550 and 2010–1351) for financial support.

references
References top

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Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.

Dondoni, A. & Marra, A. (2010). Chem. Rev. 110, 4949–4977.

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

Gattuso, G., Liantonio, R., Metrangolo, P., Meyer, F., Pappalardo, A., Parisi, M. F., Pilati, T., Pisagatti, I. & Resnati, G. (2006). Supramol. Chem. 18, 235–243.

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.