Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961402796X/sk3575sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961402796X/sk3575Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205322961402796X/sk3575sup3.pdf |
CCDC reference: 1040764
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).
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)
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.
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)
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 π–π 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 π–π 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 π–π 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.
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).
C6F3I3·2C5H5NO·H2O | F(000) = 1328 |
Mr = 717.98 | Dx = 2.354 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 2090 reflections |
a = 14.2226 (12) Å | θ = 4.3–27.6° |
b = 19.0094 (18) Å | µ = 4.67 mm−1 |
c = 7.5203 (5) Å | T = 295 K |
β = 94.727 (7)° | Prism, colourless |
V = 2026.3 (3) Å3 | 0.60 × 0.16 × 0.09 mm |
Z = 4 |
Oxford Diffraction Xcalibur CCD (Eos, Gemini) diffractometer | 2358 independent reflections |
Radiation source: fine-focus sealed tube | 1830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 16.1158 pixels mm-1 | θmax = 28.9°, θmin = 3.6° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −24→25 |
Tmin = 0.408, Tmax = 1.000 | l = −10→10 |
6727 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H 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 reflections | Δρmax = 0.78 e Å−3 |
128 parameters | Δρmin = −0.74 e Å−3 |
C6F3I3·2C5H5NO·H2O | V = 2026.3 (3) Å3 |
Mr = 717.98 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.2226 (12) Å | µ = 4.67 mm−1 |
b = 19.0094 (18) Å | T = 295 K |
c = 7.5203 (5) Å | 0.60 × 0.16 × 0.09 mm |
β = 94.727 (7)° |
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 = 1.000 | Rint = 0.050 |
6727 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 2 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.78 e Å−3 |
2358 reflections | Δρmin = −0.74 e Å−3 |
128 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.5000 | 0.70155 (3) | 0.2500 | 0.0697 (2) | |
I2 | 0.70350 (2) | 0.42760 (2) | 0.15588 (4) | 0.04207 (14) | |
F1 | 0.5000 | 0.3763 (2) | 0.2500 | 0.0550 (11) | |
F2 | 0.6537 (2) | 0.59032 (16) | 0.1621 (4) | 0.0510 (7) | |
O1 | 0.8668 (3) | 0.6459 (2) | 0.5808 (5) | 0.0560 (10) | |
N1 | 0.8666 (3) | 0.6535 (2) | 0.4053 (5) | 0.0413 (9) | |
C1 | 0.5000 | 0.4472 (3) | 0.2500 | 0.0319 (13) | |
C2 | 0.5813 (3) | 0.4823 (3) | 0.2083 (6) | 0.0352 (10) | |
C3 | 0.5777 (3) | 0.5545 (3) | 0.2059 (6) | 0.0376 (11) | |
C4 | 0.5000 | 0.5925 (4) | 0.2500 | 0.0372 (14) | |
C5 | 0.8508 (4) | 0.7170 (3) | 0.3336 (8) | 0.0574 (14) | |
H5 | 0.8392 | 0.7548 | 0.4069 | 0.069* | |
C6 | 0.8514 (5) | 0.7272 (3) | 0.1536 (8) | 0.0667 (17) | |
H6 | 0.8415 | 0.7719 | 0.1053 | 0.080* | |
C7 | 0.8670 (4) | 0.6707 (4) | 0.0442 (7) | 0.0594 (15) | |
H7 | 0.8675 | 0.6767 | −0.0785 | 0.071* | |
C8 | 0.8815 (4) | 0.6060 (4) | 0.1197 (8) | 0.0597 (15) | |
H8 | 0.8916 | 0.5671 | 0.0489 | 0.072* | |
C9 | 0.8813 (4) | 0.5989 (3) | 0.3003 (8) | 0.0540 (13) | |
H9 | 0.8916 | 0.5547 | 0.3514 | 0.065* | |
O1W | 1.0000 | 0.5512 (3) | 0.7500 | 0.0665 (16) | |
H1W | 0.9542 (18) | 0.5777 (11) | 0.713 (9) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.1090 (5) | 0.0333 (3) | 0.0712 (4) | 0.000 | 0.0347 (4) | 0.000 |
I2 | 0.0413 (2) | 0.0472 (2) | 0.0380 (2) | 0.00513 (14) | 0.00465 (14) | −0.00077 (13) |
F1 | 0.056 (2) | 0.034 (2) | 0.076 (3) | 0.000 | 0.016 (2) | 0.000 |
F2 | 0.0498 (17) | 0.0462 (17) | 0.0590 (18) | −0.0109 (14) | 0.0165 (14) | 0.0014 (14) |
O1 | 0.060 (2) | 0.068 (3) | 0.0399 (18) | −0.010 (2) | 0.0047 (17) | 0.0011 (18) |
N1 | 0.041 (2) | 0.040 (2) | 0.043 (2) | −0.0044 (19) | 0.0049 (18) | −0.0011 (18) |
C1 | 0.039 (3) | 0.028 (3) | 0.028 (3) | 0.000 | 0.002 (3) | 0.000 |
C2 | 0.036 (2) | 0.039 (3) | 0.031 (2) | 0.004 (2) | 0.0018 (18) | −0.0010 (19) |
C3 | 0.040 (3) | 0.043 (3) | 0.029 (2) | −0.003 (2) | 0.0006 (19) | 0.0029 (19) |
C4 | 0.045 (4) | 0.037 (3) | 0.029 (3) | 0.000 | −0.001 (3) | 0.000 |
C5 | 0.070 (4) | 0.046 (3) | 0.057 (3) | 0.004 (3) | 0.006 (3) | −0.003 (3) |
C6 | 0.097 (5) | 0.047 (3) | 0.056 (3) | −0.004 (3) | 0.001 (3) | 0.006 (3) |
C7 | 0.064 (4) | 0.074 (4) | 0.041 (3) | −0.009 (3) | 0.009 (3) | 0.002 (3) |
C8 | 0.065 (4) | 0.061 (4) | 0.056 (3) | −0.007 (3) | 0.018 (3) | −0.012 (3) |
C9 | 0.066 (3) | 0.040 (3) | 0.057 (3) | −0.001 (3) | 0.014 (3) | 0.003 (3) |
O1W | 0.080 (4) | 0.058 (4) | 0.060 (4) | 0.000 | 0.000 (3) | 0.000 |
I1—C4 | 2.072 (7) | C4—C3i | 1.383 (6) |
I2—C2 | 2.091 (4) | C5—C6 | 1.368 (8) |
F1—C1 | 1.349 (7) | C5—H5 | 0.9300 |
F2—C3 | 1.341 (5) | C6—C7 | 1.382 (9) |
O1—N1 | 1.328 (5) | C6—H6 | 0.9300 |
N1—C9 | 1.331 (7) | C7—C8 | 1.364 (9) |
N1—C5 | 1.332 (7) | C7—H7 | 0.9300 |
C1—C2i | 1.393 (5) | C8—C9 | 1.365 (8) |
C1—C2 | 1.393 (5) | C8—H8 | 0.9300 |
C2—C3 | 1.374 (7) | C9—H9 | 0.9300 |
C3—C4 | 1.383 (6) | O1W—H1W | 0.851 (10) |
O1—N1—C9 | 121.1 (4) | N1—C5—C6 | 121.0 (6) |
O1—N1—C5 | 119.2 (4) | N1—C5—H5 | 119.5 |
C9—N1—C5 | 119.7 (5) | C6—C5—H5 | 119.5 |
F1—C1—C2i | 118.6 (3) | C5—C6—C7 | 119.5 (6) |
F1—C1—C2 | 118.6 (3) | C5—C6—H6 | 120.3 |
C2i—C1—C2 | 122.7 (6) | C7—C6—H6 | 120.3 |
C3—C2—C1 | 116.8 (4) | C8—C7—C6 | 118.6 (5) |
C3—C2—I2 | 121.7 (4) | C8—C7—H7 | 120.7 |
C1—C2—I2 | 121.5 (4) | C6—C7—H7 | 120.7 |
F2—C3—C2 | 118.7 (4) | C7—C8—C9 | 119.4 (6) |
F2—C3—C4 | 118.0 (5) | C7—C8—H8 | 120.3 |
C2—C3—C4 | 123.3 (5) | C9—C8—H8 | 120.3 |
C3—C4—C3i | 117.0 (6) | N1—C9—C8 | 121.7 (5) |
C3—C4—I1 | 121.5 (3) | N1—C9—H9 | 119.1 |
C3i—C4—I1 | 121.5 (3) | C8—C9—H9 | 119.1 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C6F3I3·2C5H5NO·H2O |
Mr | 717.98 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 14.2226 (12), 19.0094 (18), 7.5203 (5) |
β (°) | 94.727 (7) |
V (Å3) | 2026.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.67 |
Crystal size (mm) | 0.60 × 0.16 × 0.09 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur CCD (Eos, Gemini) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.408, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6727, 2358, 1830 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.680 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.096, 1.06 |
No. of reflections | 2358 |
No. of parameters | 128 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.78, −0.74 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
Group1···Group2 | CCD (Å) | DA (°) | SA (°) | IPD (Å) | |
(I) | |||||
#1 | Cg1···Cg1ii | 3.828 (2) | 0 | 22.8 | 3.528 (2) |
#2 | Cg1···Cg1iii | 3.828 (2) | 0 | 22.8 | 3.528 (2) |
#3 | Cg2···Cg2iv | 3.787 (3) | 21 | 10.5 | 3.723 (2) |
(II) | |||||
#4 | Cg1···Cg1v | 3.7015 (14) | 0 | 20.7 | 3.4619 (10) |
#5 | Cg1···Cg1vi | 3.8182 (14) | 0 | 24.9 | 3.4620 (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). |
D—X···A' | D—X | X···A | D···A | D—X···A | |
(I) | |||||
#6 | O1W—H1W···O1 | 0.85 (3) | 2.00 (4) | 2.838 (5) | 166 (5) |
#7 | C2—I2···O1vii | 2.091 (5) | 2.807 (4) | 4.898 (6) | 179.26 (15) |
#8 | C3—F2···Cg2 | 1.341 (6) | 3.319 (4) | 4.580 (5) | 156.5 (3) |
(II) | |||||
#9 | C21—I21···O11 | 2.093 | 2.741 | 4.832 | 176.89 (8) |
#10 | C23—I23···O11viii | 2.087 | 2.808 | 4.895 | 179.53 (8) |
#11 | C24—F24···Cg2vi | 1.34 | 3.063 (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. |