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The title three-component cocrystal, C6F3I3·2C5H5NO·H2O, has been prepared as a strong candidate for multiple I...O inter­actions. Its crystal structure is compared with its 1:1 close relative, C6F3I3·C5H5NO [Aakeröy et al. (2014a). CrystEngComm, 16, 28-31]. The 1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene and water species both have crystallographic twofold axial symmetry. The main synthon in both structures is the [pi]-[pi] stacking of benzene rings, complemented by a number of O-H...O, C-F...[pi] and, fundamentally, C-I...O inter­actions. As expected, the latter are among the strongest and more directional inter­actions of the sort reported in the literature, confirming that pyridine N-oxide is an eager acceptor. On the other hand, the structure presents only two of these contacts per 1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene mol­ecule instead of the expected three. Possible reasons for this limitation are analyzed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961402796X/sk3575sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961402796X/sk3575Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205322961402796X/sk3575sup3.pdf
Supplementary material

CCDC reference: 1040764

Introduction top

The halogen bond is a noncovalent inter­action known for more than half a century which experiences nowadays an impressive expansion in fields like molecular recognition (Metrangolo et al., 2007; Cavallo et al., 2010), crystal engineering (Metrangolo et al., 2008a) or functional materials (Fourmigué, 2009; Primagi et al., 2013). An inter­esting example of the application of the halogen bond in advanced materials was the design and realization of supra­molecular liquid crystals based on halogen bonds. Both calamitic and banana-shaped supra­molecular mesogens have been prepared and studied (Bruce, 2012). However, discotic supra­molecular mesogens based on halogen bonds have not yet been synthesized. It seems that the main limitation for achieving this goal is the low tendency of aromatic compounds bearing several terminal halogen atoms to coordinate three or more halogen-acceptor moieties. This difficulty has been extensively analyzed and discussed (Aakeröy et al., 2014a; Bruce, 2012; Lucassen et al., 2007; Metrangolo et al., 2008a); its origin apparently lies on the way the electronic distribution on the donor sites is modified by the coordination of an acceptor.

A possible way to overcome this limitation is to use the strongest halogen donors having the appropriate geometry (such as 1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene, denoted hereafter as I3F3Bz) and the strongest halogen acceptors.

In this line of action, Metrangolo and coworkers prepared extended honeycomb structures where all three I atoms of I3F3Bz participate in halogen bonds, through the combined use of halide anions as tridentate binding acceptors and bulky cations as templates (Metrangolo et al., 2008b). Since then, some other structures with a triple coordinated I3F3Bz to anionic acceptors have been reported (Cauliez et al., 2010; Cavallo et al., 2013; Pfrunder et al., 2012; Triguero et al., 2008). Nevertheless, to the best of our knowledge, there are only two successful cases of triple coordination of neutral acceptors to such single donor. In the first case, Bruce and coworkers (Roper et al., 2010) succeeded in coordinating three molecules of 4-(di­methyl­amino)­pyridine (DMAP; a base recognized as a strong electron donor in the field of coordination chemistry) to each I3F3Bz molecule. In the second case, Aakeröy and coworkers (Aakeröy et al., 2014b) recently obtained a 1:1 cocrystal of I3F3Bz and 1,1'-bi­benzyl-2,2'-bi­imidazole, where each I3F3Bz molecule acts as donor in three different halogen-bond (XB) inter­actions.

An alternative to these two acceptors could be the use of pyridine N-oxide (O—Py), whose superior capacity as an XB acceptor relative to pyridine (Py) has been established (Messina et al., 2001) and inter­preted in terms of the high electronic density on the O atom. In a recent report, Aakeröy and coworkers (Aakeröy et al. 2014a) crystallized several cocrystals based on iodo–fluoro aromatics as XB donors and N-oxides of different pyridines and bi­pyridines as XB acceptors, including one containing I3F3Bz and O—Py. They used a 1:1 stoichiometry during the solvent-assisted grinding preparation of their crystals and, indeed, they obtained a cocrystal which showed this same 1:1 stoichiometry. With the aim of enhancing the probabilities of obtaining a higher number of halogen-acceptor units per acceptor centre, we attempted to use in our synthesis a 1:9 I3F3Bz:O—Py molar ratio. Unexpectedly, the compound we obtained, and which we discuss in this report, included water (probably originating from the hydrated O—Py used, see Experimental) with an active structural role in the crystal architecture. The crystals are in fact three-component cocrystals with a 1:2:1 I3F3Bz.2(O—Py).H2O stoichiometry, namely 1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene–pyridine N-oxide–water (1/2/1), (I), and which, albeit obvious differences derived from composition and stoichiometry, present an inter­action scheme which strongly resembles that of Aakeröy's 1:1 cocrystals. We thus present herein the crystal structure of (I) which we shall discuss in comparison with Aakeröy's close relative C6F3I3.C5H5NO, (II) (see Scheme).

Experimental top

Synthesis and crystallization top

A tetra­hydro­furan (THF) solution of I3F3Bz (54,7 mg, 2,5 ml) was added to a THF solution of O—Py (Hyd) (93.2 mg, 1.5 ml). The resulting mixture was allowed to evaporate slowly, the process being controlled by solvent diffusion in vaseline. After a few days, colourless needles were collected and analyzed. Structure determination proved it to correspond to 1:2:1 I3F3Bz:2(O—Py):H2O cocrystals. Water very likely came from the hydrated commercial O—Py. In order to establish the actual mixing ratio of the three components, we decided to assess the amount of water in the starting O—Py by measuring the mass loss of a sample of hydrated (hyd) O—Py heated in a glass oven at 343 K until it reached a constant mass. The result indicated a 1.3:1 H2O:O—Py molar ratio in the starting O—Py (hyd); the masses employed in the crystallization essay corresponded then to a 9.5:7.3:1 H2O:O—Py:I3F3Bz molar ratio.

I3F3Bz was synthesized from 1,3,5-tri­iodo­benzene (146 mg), following the procedure reported by Sander (Wenk et al., 2002), with minor variations. Since the crystals obtained this way showed a light-yellow tint instead of the white colour expected, and since it did not correspond to unwashed I2, we completed the purification with a column cromatography using hexane as eluent, to obtain 429 mg of needle-like white crystals (76% yield)

Physicochemical measurements top

IR spectra of (I), I3F3Bz and O—Py were recorded as KBr pellets on a Nicolet FT–IR 510P spectrometer, and full spectra are provided as Supporting information in Fig. S1. Diagnostic bands (cm-1) for (I): 3381, 3112, 1562, 1463, 1400, 1213, 1166, 1045, 1016, 832, 770, 676, 655, 549, 466; for I3F3Bz: 1564, 1406, 1326, 1050, 705, 654; for O—Py: 3404, 3110, 1654, 1607, 1466, 1231, 1175, 1017, 916, 836, 771, 676, 549, 512, 468. Differential scanning calorimetry (DSC) experiments on selected single crystals of (I) were conducted on a Shimadzu DSC-50 apparatus, at a heating rate of 2 K min-1 under an N2 atmosphere, using aluminum pans. Thermogravimetric analysis (TGA) was performed under similar conditions using a Shimadzu TGA-51H thermobalance. Mass loss has been measured on a Sartorius AC 210 P balance for samples heated in a Buchi B-585 oven.

Refinement top

Crystal data, data collection and structure refinement details for (I) are summarized in Table 1. All H atoms were originally found in difference maps but were treated differently in the refinement. The water H atoms was refined with restrained O—H distances [0.85 (1) Å], while pyridine H atoms were repositioned in their expected positions and allowed to ride (C—H = 0.93 Å). All H atoms were assigned Uiso(H) values of 1.2Ueq(C,O)

Results and discussion top

The asymmetric unit consists of one I3F3Bz and one water molecule sitting on two different twofold axes and an O—Py molecule in a general position, resulting in four full 1:2:1 groups in the unit cell (Z' = 1/2, Z = 4). As expected, the molecular geometry (Fig. 1) does no depart from expected values and will not be discussed in what follows. The most appealing aspects of the structure are the inter­molecular inter­actions. In order to facilitate the comparison of the current structure, (I), and the Aakeröy et al. structure, (II), we present a joint table of the pyridine N-oxide ππ contacts (Table 2) and one of the hydrogen bonding, C—X···O and C—X···π inter­actions (Table 3) common to both structures of inter­est. Atom labelling for the latter has been taken from the CSD. The most conspicuous synthon is the ππ stacking among I3F3Bz molecules, which appears in both structures exactly in the same fashion [Table 2: #1, #2 for (I); #4 and #5 for (II)]. The columnar arrays they give rise to are absolutely comparable (Fig. 2) and this could be considered the fundamental structural brick out of which the packing of both structures is built up. Differences arise, however, when the inter­columnar inter­actions are considered, where the diversity in formulation and stoichiometry begin to show up.

Fig. 3 presents packing views of (I) and (II), drawn along the column direction, where similarities and differences are apparent. Among the former, both structures present C—F···π and a C—I···O inter­actions [Table 3: #6 and #7 for (I); #9, #10 and #11 for (II)] which, save very minor differences, could be considered identical, and correspond to the `framed' zones in the figure.

However, while these are all the inter­actions present in (II), giving a full account of the whole connectivity between the stacked columns to form (101) planes (Fig. 3b), in the case of (I) these blocks appear `split', with the water molecules acting as `wedges' between them (Fig. 3a), and the duplication of the O—Py molecule in the formulation being now apparent. Note the ππ bond connecting pyridine rings and detailled in Table 2 (entry #3). This new substructure, characteristic of (I) but absent in (II), also provides the packing cohesion of the (010) planes by defining chains parallel to the I3F3Bz columns (viewed in projection in the encircled region in Fig. 3a and in full in Fig. 4a). This should be compared with the equivalent nonconnected region in (II) (encircled region in Fig. 3b and Fig. 4b). Additional evidence for the structural role played by the water molecules comes from the fact that even extremely careful heating experiments aimed to dehydrate individual specimens of these single cocrystals using a DSC-based technique, which proved successful in the recent past (Harvey et al., 2014), in the present case only yielded an opaque (white) material without any single-crystal character. The first process detected by thermogravimetric analysis (TGA; Fig. S2 in the Supporting information), at ca 338 K, corresponds to the mass loss expected for the water content of (I) (experimental: 2.2%; expected: 2.5%).

To assess the real strength of the (almost identical) BzI···O—Py inter­actions in (I) and (II), we carried out searches in the Cambridge Structural database (Version 5.3, updated to March 2014; Groom & Allen, 2014) for C—I···O contacts with I···O < 3.25 Å, under different restrictions, viz. (a) fully unrestricted and (b) restricting the donor and acceptor to the BzI···O—Py special arrangement, similar to what is present in (I) and (II). The histograms for these searches are presented in the Supporting information as Fig. S3, but the main results can be summarized by the number of hits, the distance/angle mean values (Å, °), and the distance/angle span (Å, °), viz. (a) 554, 3.147/151.24, 0.947/115.01; (b) 14, 2.776/172.01, 0.142/12.84.

It is easily inferable from these results that the BzI···O—Py inter­action is stronger and more directional than the average C—I···O inter­actions and that among the former, those in (I) and (II) lean towards the strong/directional side. Additional analysis (shown in Fig. S4 of the Supporting information) shows this feature is due to the acceptor O—Py unit rather than the donor unit.

To a certain extent, the result of this exercise (in terms of what was originally planned) could be considered negative, as the aim of linking more than two eager XB acceptors, like O—Py, to a single XB donor proved fruitless. The structure obtained, (I), did not outnumber the X···O inter­actions found in the previously reported analogue (II), even if it shared with it the double BzI···O—Py linkage. However, the presence of the water molecule, albeit undesirable with respect to our original scope, introduced inter­esting structural differences which ended up being the basis of the present discussion. These results suggest that the low tendency of those aromatic compounds bearing terminal halogens to make more that two halogen-bond contacts requires more careful synthetic procedures (e.g. observing stringent anhydrous conditions) and approaches (e.g. use of alkyl-substituted pyridine N-oxides), leaving this as a future line of investigation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the components of (I), with displacement ellipsoids drawn at the 40% probability level. [Symmetry code: (i) -x+1, y, -z+3/2.]
[Figure 2] Fig. 2. The I3F3Bz columnar arrays in (a) (I) and (b) (II). For #n interaction codes, see Table 2.
[Figure 3] Fig. 3. Packing views drawn along the column direction, showing the whole interaction scheme and (a) (I) and (b) (II). For #n interaction codes, see Tables 2 and 3.
[Figure 4] Fig. 4. (a) The [001] O—py···water colum and (b) a view of the similar region in (II). For #n interaction codes, see Tables 2 and 3.
1,3,5-Triiodo-2,4,6-trifluorobenzene–pyridine N-oxide–water (1/2/1) top
Crystal data top
C6F3I3·2C5H5NO·H2OF(000) = 1328
Mr = 717.98Dx = 2.354 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 2090 reflections
a = 14.2226 (12) Åθ = 4.3–27.6°
b = 19.0094 (18) ŵ = 4.67 mm1
c = 7.5203 (5) ÅT = 295 K
β = 94.727 (7)°Prism, colourless
V = 2026.3 (3) Å30.60 × 0.16 × 0.09 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur CCD (Eos, Gemini)
diffractometer
2358 independent reflections
Radiation source: fine-focus sealed tube1830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 16.1158 pixels mm-1θmax = 28.9°, θmin = 3.6°
ω scansh = 1919
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 2425
Tmin = 0.408, Tmax = 1.000l = 1010
6727 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.044P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2358 reflectionsΔρmax = 0.78 e Å3
128 parametersΔρmin = 0.74 e Å3
Crystal data top
C6F3I3·2C5H5NO·H2OV = 2026.3 (3) Å3
Mr = 717.98Z = 4
Monoclinic, C2/cMo Kα radiation
a = 14.2226 (12) ŵ = 4.67 mm1
b = 19.0094 (18) ÅT = 295 K
c = 7.5203 (5) Å0.60 × 0.16 × 0.09 mm
β = 94.727 (7)°
Data collection top
Oxford Diffraction Xcalibur CCD (Eos, Gemini)
diffractometer
2358 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
1830 reflections with I > 2σ(I)
Tmin = 0.408, Tmax = 1.000Rint = 0.050
6727 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0352 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.78 e Å3
2358 reflectionsΔρmin = 0.74 e Å3
128 parameters
Special details top

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
I10.50000.70155 (3)0.25000.0697 (2)
I20.70350 (2)0.42760 (2)0.15588 (4)0.04207 (14)
F10.50000.3763 (2)0.25000.0550 (11)
F20.6537 (2)0.59032 (16)0.1621 (4)0.0510 (7)
O10.8668 (3)0.6459 (2)0.5808 (5)0.0560 (10)
N10.8666 (3)0.6535 (2)0.4053 (5)0.0413 (9)
C10.50000.4472 (3)0.25000.0319 (13)
C20.5813 (3)0.4823 (3)0.2083 (6)0.0352 (10)
C30.5777 (3)0.5545 (3)0.2059 (6)0.0376 (11)
C40.50000.5925 (4)0.25000.0372 (14)
C50.8508 (4)0.7170 (3)0.3336 (8)0.0574 (14)
H50.83920.75480.40690.069*
C60.8514 (5)0.7272 (3)0.1536 (8)0.0667 (17)
H60.84150.77190.10530.080*
C70.8670 (4)0.6707 (4)0.0442 (7)0.0594 (15)
H70.86750.67670.07850.071*
C80.8815 (4)0.6060 (4)0.1197 (8)0.0597 (15)
H80.89160.56710.04890.072*
C90.8813 (4)0.5989 (3)0.3003 (8)0.0540 (13)
H90.89160.55470.35140.065*
O1W1.00000.5512 (3)0.75000.0665 (16)
H1W0.9542 (18)0.5777 (11)0.713 (9)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.1090 (5)0.0333 (3)0.0712 (4)0.0000.0347 (4)0.000
I20.0413 (2)0.0472 (2)0.0380 (2)0.00513 (14)0.00465 (14)0.00077 (13)
F10.056 (2)0.034 (2)0.076 (3)0.0000.016 (2)0.000
F20.0498 (17)0.0462 (17)0.0590 (18)0.0109 (14)0.0165 (14)0.0014 (14)
O10.060 (2)0.068 (3)0.0399 (18)0.010 (2)0.0047 (17)0.0011 (18)
N10.041 (2)0.040 (2)0.043 (2)0.0044 (19)0.0049 (18)0.0011 (18)
C10.039 (3)0.028 (3)0.028 (3)0.0000.002 (3)0.000
C20.036 (2)0.039 (3)0.031 (2)0.004 (2)0.0018 (18)0.0010 (19)
C30.040 (3)0.043 (3)0.029 (2)0.003 (2)0.0006 (19)0.0029 (19)
C40.045 (4)0.037 (3)0.029 (3)0.0000.001 (3)0.000
C50.070 (4)0.046 (3)0.057 (3)0.004 (3)0.006 (3)0.003 (3)
C60.097 (5)0.047 (3)0.056 (3)0.004 (3)0.001 (3)0.006 (3)
C70.064 (4)0.074 (4)0.041 (3)0.009 (3)0.009 (3)0.002 (3)
C80.065 (4)0.061 (4)0.056 (3)0.007 (3)0.018 (3)0.012 (3)
C90.066 (3)0.040 (3)0.057 (3)0.001 (3)0.014 (3)0.003 (3)
O1W0.080 (4)0.058 (4)0.060 (4)0.0000.000 (3)0.000
Geometric parameters (Å, º) top
I1—C42.072 (7)C4—C3i1.383 (6)
I2—C22.091 (4)C5—C61.368 (8)
F1—C11.349 (7)C5—H50.9300
F2—C31.341 (5)C6—C71.382 (9)
O1—N11.328 (5)C6—H60.9300
N1—C91.331 (7)C7—C81.364 (9)
N1—C51.332 (7)C7—H70.9300
C1—C2i1.393 (5)C8—C91.365 (8)
C1—C21.393 (5)C8—H80.9300
C2—C31.374 (7)C9—H90.9300
C3—C41.383 (6)O1W—H1W0.851 (10)
O1—N1—C9121.1 (4)N1—C5—C6121.0 (6)
O1—N1—C5119.2 (4)N1—C5—H5119.5
C9—N1—C5119.7 (5)C6—C5—H5119.5
F1—C1—C2i118.6 (3)C5—C6—C7119.5 (6)
F1—C1—C2118.6 (3)C5—C6—H6120.3
C2i—C1—C2122.7 (6)C7—C6—H6120.3
C3—C2—C1116.8 (4)C8—C7—C6118.6 (5)
C3—C2—I2121.7 (4)C8—C7—H7120.7
C1—C2—I2121.5 (4)C6—C7—H7120.7
F2—C3—C2118.7 (4)C7—C8—C9119.4 (6)
F2—C3—C4118.0 (5)C7—C8—H8120.3
C2—C3—C4123.3 (5)C9—C8—H8120.3
C3—C4—C3i117.0 (6)N1—C9—C8121.7 (5)
C3—C4—I1121.5 (3)N1—C9—H9119.1
C3i—C4—I1121.5 (3)C8—C9—H9119.1
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC6F3I3·2C5H5NO·H2O
Mr717.98
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)14.2226 (12), 19.0094 (18), 7.5203 (5)
β (°) 94.727 (7)
V3)2026.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)4.67
Crystal size (mm)0.60 × 0.16 × 0.09
Data collection
DiffractometerOxford Diffraction Xcalibur CCD (Eos, Gemini)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.408, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6727, 2358, 1830
Rint0.050
(sin θ/λ)max1)0.680
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.096, 1.06
No. of reflections2358
No. of parameters128
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.78, 0.74

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

ππ contacts for I, II. top
Group1···Group2CCD (Å)DA (°)SA (°)IPD (Å)
(I)
#1Cg1···Cg1ii3.828 (2)022.83.528 (2)
#2Cg1···Cg1iii3.828 (2)022.83.528 (2)
#3Cg2···Cg2iv3.787 (3)2110.53.723 (2)
(II)
#4Cg1···Cg1v3.7015 (14)020.73.4619 (10)
#5Cg1···Cg1vi3.8182 (14)024.93.4620 (10)
Symmetry codes: for (I), (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1; (iv) -x+2, y, -z+1/2; for (II), (v) -x+1, -y, -z; (vi) -x+1, -y+1, -z

For ring codes, see Fig. 1. CCD is the centre-to-centre distance (distance between ring centroids); DA is the dihedral angle; SA is the (mean) slippage angle (angle subtended by the intercentroid vector to the plane normal); IPD is the (mean) interplanar distance (distance from one plane to the neighbouring centroid). For details, see Janiak (2000).
Hydrogen-bond or halogen-bond geometry for (I) and (II) (Å, °) (X = H, I or F) top
DX···A'DXX···AD···ADX···A
(I)
#6O1W—H1W···O10.85 (3)2.00 (4)2.838 (5)166 (5)
#7C2—I2···O1vii2.091 (5)2.807 (4)4.898 (6)179.26 (15)
#8C3—F2···Cg21.341 (6)3.319 (4)4.580 (5)156.5 (3)
(II)
#9C21—I21···O112.0932.7414.832176.89 (8)
#10C23—I23···O11viii2.0872.8084.895179.53 (8)
#11C24—F24···Cg2vi1.343.063 (2)4.313 (3)154.82 (15)
Symmetry codes, for (I): (vii) x, -y+1, z-1/2; for (II): (vi) -x+1, -y+1, -z; (viii) x+1/2, y+1/2, z-1/2. For ring codes, see Fig 1.
 

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