Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

Sinnwell, M.A.; Blad, J.N.; Thomas, L.R.; MacGillivray, L.R.

doi:10.1107/S2052252518007583

research papers

IUCrJ

Volume 5| Part 4| July 2018| Pages 491-496

ISSN: 2052-2525

https://doi.org/10.1107/S2052252518007583

CHEMISTRY | CRYSTENG

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Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

Michael A. Sinnwell,^a Jared N. Blad,^a Logan R. Thomas ^a and Leonard R. MacGillivray ^a ^*

^aDepartment of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
^*Correspondence e-mail: len-macgillivray@uiowa.edu

Edited by M. Eddaoudi, King Abdullah University, Saudi Arabia (Received 19 December 2017; accepted 21 May 2018; online 22 June 2018)

Halogen bonds have emerged as noncovalent forces that govern the assembly of molecules in organic solids with a degree of reliability akin to hydrogen bonds. Although the structure-directing roles of halogen bonds are often compared to hydrogen bonds, general knowledge concerning the fundamental structural behavior of halogen bonds has had limited opportunity to develop. Following an investigation of solid-state reactions involving organic syntheses and the development of photoresponsive materials, this work demonstrates the ability of the components of intermolecular N⋯I halogen bonding – a `workhorse' interaction for the crystal engineer – to support a single-crystal-to-single-crystal [2+2] photodimerization. A comparison is provided of the geometric changes experienced by the halogen-bonded components in the single-crystal reaction to the current crystal landscape of N⋯I halogen bonds, as derived from the Cambridge Structural Database. Specifically, a linear-to-bent type of deformation of the halogen-bonded components was observed, which is expected to support the development of functional halogen-bonded materials containing molecules that can undergo movements in close-packed crystal environments.

Keywords: solid-state reactivity; halogen bonds; photodimerization; supramolecular chemistry; single-crystal-to-single-crystal reaction; crystal engineering; co-crystals; organic solid-state reactions; framework-structured solids and amorphous materials; molecular crystals.

CCDC references: 1521899; 1521900

1. Introduction

Halogen bonds are employed in supramolecular chemistry to direct the assembly of molecules in solution and the solid state (Gilday et al., 2015 , Resnati et al., 2015 ). The strength and directionality of halogen bonds parallel that of hydrogen bonds such that halogen bonding provides a reliable force to organize molecules in the construction of functional crystalline solids (Cavallo et al., 2016 ) and other condensed materials (e.g. liquid crystals, polymers).

A hallmark feature of noncovalent bonding when controlling self-assembly is the structural flexibility of components engaged in intermolecular forces (Desiraju, 2011 ). Hydrogen bonds generally exploit the flexibility of X—H donor groups (e.g. X = O, N) to accommodate the orientation and assembly of components into supramolecular structures. Flexibility in the solid state can give rise to atomic and molecular movements that support single-crystal-to-single-crystal (SCSC) transformations (Friščić & MacGillivray, 2005 ). Solids that undergo SCSC transitions bear relevance to applications of organic solid-state materials in areas such as data storage, sensors and shape memory (Kole et al., 2014 ).

The pyridine–iodopolyfluorophenyl (N⋯I) halogen bond has been exploited extensively in the field of crystal engineering to sustain discrete and extended supramolecular frameworks (Cavallo et al., 2016). Computational studies have recently demonstrated that the energies of the N⋯I bond exhibit a relatively high dependence on the C—I⋯N angle θ (ca 150° < θ < 180°) (Tsuzuki et al., 2016 ). It is not clear whether the components of N⋯I halogen bonds, however, can tolerate types of bending motions similar to hydrogen-bonded components in the solid state, although rotary movements of halogen-bonded molecular components have been recently recognized as important in the development of artificial molecular machines (Catalano et al., 2015 ). The bending of components engaged in noncovalent forces (e.g. hydrogen bonds, halogen bonds) can be considered fundamentally important in the development of machine-like materials (Khuong et al., 2006 ). Examples of halogen-bonded solids that support single-crystal processes, however, remain rare and to date have involved molecules that provide internal degrees of molecular flexibility and freedom (e.g. –CH₂– groups, –N=N–) (Sun et al., 2006 ; Luo et al., 2008 ; Raatikainen & Rissanen, 2012 ; Marti-Rujas et al., 2012 ; Jin et al., 2013 ; Bushuyev et al., 2013 ; Bushuyev et al., 2014 ). We are unaware of an SCSC [2+2] photodimerization supported by halogen bonds.

In this contribution, we report a halogen-bonded cocrystal with components that support an SCSC [2+2] photodimerization (Scheme 1). We show the components of (I₄F₁₆cb)·2(bpe) [where I₄F₁₆cb = rctt-tetrakis(2,3,5,6-tetrafluoro-4-iodophenyl)cyclobutane and bpe = trans-1,2-bis(4-pyridyl)ethene], which assemble via N⋯I halogen bonds to form a cocrystal that reacts quantitatively to form tpcb (tpcb = rctt-tetrakis(4-pyridyl)cyclobutane). We demonstrate that the components engaged in halogen bonding exhibit structural flexibility, their geometries undergoing a linear-to-bent type of deformation in the SCSC transformation. The movements span the outer geometries of N⋯I bonds that have been reported to date.

2. Experimental

2.1. Materials and general methods

The bipyridine bpe (SIGMA) and all solvents were commercially available and were used without further purification (FISHER). ¹H NMR spectra were recorded using a Bruker AVANCE-300 NMR spectrometer operating at 300 MHz using DMSO-d₆ as solvent. Photoreactions of (I₄F₁₆cb)·2(bpe) were conducted on a glass plate using UV radiation from a 450 W medium-pressure mercury lamp inside an ACE Glass photochemistry cabinet. Powder X-ray diffraction data were collected from samples mounted on glass slides by a Siemens D5000 X-ray diffractometer using Cu Kα₁ radiation (λ = 1.54056 Å).

2.2. Synthesis of cocrystal (I₄F₁₆cb)·2(bpe)

I₄F₁₆cb was synthesized as reported (Sinnwell & MacGillivray, 2016 ). Cocrystals of (I₄F₁₆cb)·2(bpe) were obtained as colorless plates by combining acetonitrile solutions (1.5 ml each) of I₄F₁₆cb (23 mg, 0.02 mmol) and bpe (11 mg, 0.04 mmol) (1:2 molar ratio). Single crystals suitable for single-crystal X-ray diffraction studies were obtained after a period of approximately 1 d.

2.3. X-ray crystallography

Single-crystal data for (I₄F₁₆cb)·2(bpe) were collected with a Bruker APEXII Kappa diffractometer equipped with an Oxford Cryostream low-temperature device using Mo Kα radiation (λ = 0.71073 Å). All calculations dealing with data collection, initial indexing, frame integration, Lorentz polarization corrections and final unit-cell parameters were carried out by APEX2 (Bruker, 2012 ). Single-crystal diffraction data for (I₄F₁₆cb)·2(tpcb) were collected on a Nonius KappaCCD single-crystal X-ray diffractometer at room temperature using Mo Kα radiation (λ = 0.71073 Å). Data collection, cell refinement and data reduction were performed using COLLECT (Hooft, 1998 ) and HKL SCALEPACK/DENZO, respectively (Otwinowski & Minor, 1997 ). All structures were solved via direct methods using SHELXT (Sheldrick, 2015 ) and refined using SHELXL (Sheldrick, 2015) in the OLEX2 (Dolomanov et al., 2009 ) graphical user interface. All non-H atoms were identified from difference Fourier maps within several refinement steps. H atoms associated with C atoms were refined in geometrically constrained positions with U_iso(H) = 1.2U_eq(C).

2.3.1. Crystal data for (I₄F₁₆cb)·2(bpe)

Crystal system: monoclinic, space group: P2₁/c (No. 14), a = 13.0184 (13), b = 9.7153 (10), c = 19.986 (2) Å, β = 104.649 (5)°, V = 2445.6 (4) Å³, Z = 2, T = 298.15 K, μ(Mo Kα) = 2.653 mm⁻¹, D_calc = 2.059 g cm⁻³, 52 897 reflections measured (5.926° ≤ 2θ ≤ 52.87°), 5012 unique (R_int = 0.0305, R_sigma = 0.0162) which were used in all calculations. The final R₁ was 0.0198 [I > 2σ(I)] and wR₂ was 0.0460 (all data).

2.3.2. Crystal data for (I₄F₁₆cb)·2(tpcb)

Crystal system: monoclinic, space group: P2₁/c (No. 14), a = 12.9647 (13), b = 10.2219 (10), c = 19.519 (10) Å, β = 109.387 (5)°, V = 2440.0 (13) Å³, Z = 2, T = 298.15 K, μ(Mo Kα) = 2.659 mm⁻¹, D_calc = 2.064 g cm⁻³, 12 227 reflections measured (5.956° ≤ 2θ ≤ 50.786°), 4464 unique (R_int = 0.0670, R_sigma = 0.0580) which were used in all calculations. The final R₁ was 0.0330 [I > 2σ(I)] and wR₂ was 0.0627 (all data).

3. Results and discussion

Our interests lie in the design of organic solids using molecules that react to form covalent bonds. The ability to direct the formation of covalent bonds in crystals `by design' can provide a means of synthesizing organic molecules that are difficult or impossible to achieve in solution (e.g. ladderanes) and/or of controlling the bulk-physical properties of solids (e.g. optical). In this context, a major focus has been the use of noncovalent forces to direct the formation of carbon–carbon single (C—C) bonds in cocrystals via [2+2] photodimerizations (MacGillivray et al., 2008 ). The formation of covalent bonds in solids is invariably accompanied by atomic and/or molecular movements (Friščić & MacGillivray, 2005) that often result in crystal cracking and can lead to macroscopic motility in the form of popping (Medishetty et al., 2014 ). Cocrystals sustained by hydrogen bonds have been shown in limited cases to support [2+2] photodimerizations that proceed as SCSC transformations (MacGillivray et al., 2008; Santra & Biradha, 2008 ). An SCSC transformation provides the ability to observe subtle, atomic level changes to structures induced by external stimuli (e.g. UV radiation) and thus provide insight into the structural behaviors and dynamics of molecular components engaged in intermolecular bonding. Although there have been two recent reports of intermolecular N⋯I halogen bonds that support photocycloaddition reactions in the solid state (Caronna et al., 2004 ; Sinnwell & MacGillivray, 2016), we are unaware of any examples of halogen-bonded solids with components that can undergo an SCSC photodimerization.

3.1. Halogen bonds in SCSC photodimerization

The halogen-bonded cocrystal that undergoes SCSC photodimerization is (I₄F₁₆cb)·2(bpe). We have reported the synthesis of I₄F₁₆cb in the solid state using 1,8-bis(4-pyridyl)naphthalene (dpn) as a template (Sinnwell & MacGillivray, 2016). Here we identify I₄F₁₆cb as a rare example of a template that operates by reversal of the noncovalent bonding (Bhattacharya et al., 2013 ). Slow evaporation of a solution of I₄F₁₆cb and bpe (1:2 ratio) in acetonitrile afforded colorless plate-shaped crystals after a period of 1 d. The formulation of (I₄F₁₆cb)·2(bpe) was confirmed by single-crystal and powder X-ray diffraction (at 298 K), as well as by ¹H NMR spectroscopy.

Single-crystal X-ray analysis revealed that (I₄F₁₆cb)·2(bpe) crystallizes in the monoclinic space group P2₁/c. Half a molecule of I₄F₁₆cb and one molecule of bpe lie in the asymmetric unit (Fig. 1). The components form one-dimensional chains sustained by two unique N⋯I halogen bonds (XB1 = N1⋯I1; XB2 = N2⋯I2) (see the table in Fig. 2). Cyclobutane I₄F₁₆cb, which is disordered over two sites [highest occupied site: 0.607 (5)], organizes bpe in a face-to-face π-stacked geometry with two C=C bonds of bpe parallel and separated by 3.83 Å. The olefin lies disordered over two sites [highest occupied site: 0.769 (7)]. The stacking satisfies the criteria for a [2+2] photodimerization (Schmidt, 1971 ). The one-dimensional chains lie offset and parallel along the crystallographic b axis via face-to-face interactions of p-C₆F₄-I and pyridyl rings [centroid–centroid (π–π): π_F–π_F = 3.40, π_F–π_pyr = 3.99 and π_pyr–π_pyr = 3.84 Å]. Olefins of neighboring chains are separated by 7.89 Å which is outside the limits for a photoreaction.

Figure 1
X-ray structure of (I₄F₁₆cb)·2(bpe): (a) C=C distances (inset: halogen-bonding metrics) and (b) layers of chains.

Figure 2
Table of halogen-bond metrics and changes in the geometries of components of (I₄F₁₆cb)·2(bpe) and (I₄F₁₆cb)·(tpcb) with comparisons to the CSD.

When single crystals of (I₄F₁₆cb)·2(bpe) were exposed to UV irradiation (450 W medium-pressure Hg lamp) for a period of 30 h, tpcb formed quantitatively, indicated by the disappearance of the olefinic peaks (7.54 p.p.m.) and the appearance of cyclobutane peaks (4.66 p.p.m.) in the ¹H NMR spectrum (DMSO-d₆). Optical microscopy confirmed that the crystals remained intact during the photodimerization.

An X-ray diffraction analysis (at 298 K) confirmed that (I₄F₁₆cb)·2(bpe) undergoes an SCSC reaction to form (I₄F₁₆cb)·2(tbcb). The bpe olefin reacted to give tpcb and, as a result, maintained the structure of the halogen-bonded chains (XB1 = N1⋯I1; XB2 = N2⋯I2) (Fig. 3). The halogenated cyclobutane of the photoreacted cocrystal adopts two orientations [highest occupied site: 0.764 (7)] with site occupancies that differ from I₄F₁₆cb of the unreacted solid. A comparison of the unit-cell dimensions revealed that the volume and density remained virtually unchanged. A calculated 5% increase in the b axis relates to a change in conformation of I₄F₁₆cb manifested by a splaying of the pendant p-C₆F₄-I groups. The splaying accommodates newly formed tpcb whilst maintaining the halogen bonds.

Figure 3
X-ray structure of (I₄F₁₆cb)·(tpcb) showing cyclobutane formation (inset: halogen-bonding metrics).

3.2. Crystal landscape of halogen bonds

To gain insight into the geometric changes experienced by the halogen-bonded components of (I₄F₁₆cb)·2(bpe), we constructed a novel IsoStar scatterplot (Bruno et al., 1997 ) composed of all the structures in the Cambridge Structural Database (CSD, Version 5.38; Groom et al., 2016 ), with N⋯I halogen bonds involving p-C₆F₄-I and 4-pyridyl groups (Fig. 4). A total of 116 halogen bonds from 83 reported crystal structures were analysed to study the positioning of the 4-pyridyl groups in relation to a best fit p-C₆F₄-I moiety. Each 4-pyridyl group of each halogen bond is populated into symmetrically equivalent quadrants, which reflects the symmetry of the p-C₆F₄-I group and defines a `window' of experimental geometries of halogen bonds. The boundary of the window is defined according to conventional N⋯X distances and C—X⋯N angles (θ) used to describe halogen bonds. The boundary is rectangular in shape (see insets, Fig. 4), which reflects the directionality of the N⋯I force. We also took note of the π_centroid—N⋯I angle (φ). Given that the separation distance of the C atoms of the C=C bonds decreases to form the C—C bonds, we expected a change in the π_centroid—N⋯I angle to describe the `sweep' of the 4-pyridyl group away from ca 180° in the photodimerization.

Figure 4
IsoStar scatterplots: XB1 (left) and XB2 (right) of (I₄F₁₆cb)·2(bpe) (gray) and (I₄F₁₆cb)·(tpcb) (black). Highest occupied XB1 and XB2 in one quadrant (inset: criteria for CSD search).

The IsoStar scatterplot analysis shows that the positions of the 4-pyridyl groups before and after the photodimerization lie within the window of geometries reported in the CSD (Fig. 4, wireframe). The ranges of the N⋯I bond distances and C—I⋯N angles from the CSD are 2.667–3.040 Å and 159.5–180.0°, respectively (see table in Fig. 2). The distances and angles for (I₄F₁₆cb)·2(bpe) and (I₄F₁₆cb)·2(tbcb) fall within these ranges. The π_centroid—N⋯I angles from the CSD range from 132.6 to 180.0°. This range is larger than that of the C—I⋯N angles, whereas the corresponding angles for (I₄F₁₆cb)·2(bpe) and (I₄F₁₆cb)·2(tbcb) fall within the values. Considered together, we believe the IsoStar scatterplot shows that the changes in geometry of the 4-pyridyl groups in the photodimerization correspond to a linear-to-bent type of deformation from the plane of the best-fit p-C₆F₄-I group.

The changes in geometry of the halogen bonds in the SCSC transformation involve changes to the N⋯X distances and C—X⋯N angles. Specifically, XB1 underwent N⋯I lengthening from 2.782 (8) to 2.878 (5) Å (see table in Fig. 2). This change in distance was accompanied by a 2.3° increase in the C—I⋯N angle from 170.7 (3) to 173.0 (3)°. For XB2 (Fig. 4, see table in Fig. 2), the N⋯I distance (2.781 Å) remained largely intact while, in contrast to XB1, the C—I⋯N angle underwent a decrease of 1.7°. To accommodate the generation of the cyclobutane, both pyridyl groups underwent movements corresponding to reductions in the π_centroid—N⋯I angles of XB1 and XB2 from 172.6 (9) to 161.1 (2)° and from 175.8 (3) to 166.4 (2)°, respectively.

3.3. Single-crystal reactivity and movements of halogen-bonded components

Metrangolo and Resnati (Caronna et al., 2004) described the first example of a solid-state [2+2] photodimerization mediated by N⋯I halogen bonds (Scheme 2). A tetratopic molecule based on pentaerythritol (pethr) directed the formation of tpcb in a one-dimensional ribbon-type cocrystal assembly (Scheme 2); the solid-state reaction was studied in powder form. In later work, we showed that I₄F₁₆cb itself can be synthesized as a powdered cocrystal using dpn in a cycloaddition sustained by N⋯I halogen bonds (Sinnwell & MacGillivray, 2016) (Scheme 3). For the case of (I₄F₁₆cb)·2(bpe), the SCSC reveals that the components of the N⋯I halogen bonds undergo linear-to-bent bending in order to accommodate the formation of tpcb in the solid state. We note that movements of components in the form of rotations of molecules engaged in N⋯X halogen bonds have been very recently considered as being relevant in the development of molecular-scale machine assemblies (Catalano et al., 2015). X⋯X interactions (Mukherjee & Desiraju, 2014 ) have also been discussed as determinants in supporting the elasticity of molecular crystals that results in macroscopic changes to morphologies (Ghosh et al., 2015 ; Saha & Desiraju, 2016 ). To the best of our knowledge, the role of N⋯I halogen bonds in supporting an SCSC photodimerization has not been reported. These observations are important as they suggest that halogen bonding may be employed in the pursuit of synthetic and materials applications of organic solids that exhibit SCSC photoreactivity and related single-crystal behavior.

4. Conclusions

We have demonstrated the ability of the components of N⋯I halogen bonds to support an SCSC [2+2] photodimerization. The SCSC transformation involves a linear-to-bent change in geometry of the halogen-bonded components. We believe this SCSC transformation provides insight into the dynamic processes of halogen-bonded components where achieving solids that exhibit fluidity, while maintaining structural integrity, can be important with implications in the design of complex materials and chemical systems (Barbour, 2006 ). Our focus now is to develop organic solids with components that assemble by a combination of noncovalent forces (e.g. hydrogen bonds and halogen bonds) and exhibit SCSC reactivity. We also envisage an ability to construct solids wherein halogen-bonded components exhibit a combination of movements (e.g. bending and rotation). Mechanical properties of the resulting materials will also be studied (Karunatilaka et al., 2011 ).

Supporting information

CCDC references: 1521899; 1521900

Crystal structure: contains datablocks publication_text, mcg164, mcg1611a. DOI: https://doi.org/10.1107/S2052252518007583/ed5014sup1.cif

Supporting information. DOI: https://doi.org/10.1107/S2052252518007583/ed5014sup2.pdf

Computing details top

Data collection: apexII (Bruker AXS, 2010) for mcg164; HKL SCALEPACK (Otwinowski & Minor, 1997) for mcg1611a. Cell refinement: apexII (Bruker AXS, 2010) for mcg164; Collect (Nonius BV, 1997-2000) for mcg1611a. Data reduction: apexII (Bruker AXS, 2010) for mcg164; HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997) for mcg1611a. For both structures, program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

rctt-tetrakis-(4-iodo-2,3,5,6-tetrafluorophenyl)cyclobutane, trans-1,2-bis-(4-pyridyl)-ethene (mcg164) top

Crystal data top

1(C₂₈H₄F₁₆I₄)·2(C₁₂H₁₀N₂)	F(000) = 1440
M_r = 1516.35	D_x = 2.059 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0184 (13) Å	Cell parameters from 9832 reflections
b = 9.7153 (10) Å	θ = 4.6–52.7°
c = 19.986 (2) Å	µ = 2.65 mm⁻¹
β = 104.649 (5)°	T = 298 K
V = 2445.6 (4) Å³	Plate, colourless
Z = 2	0.4 × 0.19 × 0.04 mm

Data collection top

Bruker Nonius APEX II Kappa diffractometer	4016 reflections with I > 2σ(I)
CCD phi and ω scans	R_int = 0.031
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014) was used for absorption correction. wR2(int) was 0.0875 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.8065. The λ/2 correction factor is 0.00150.	θ_max = 26.4°, θ_min = 3.0°
T_min = 0.601, T_max = 0.745	h = −16→16
52897 measured reflections	k = −12→11
5012 independent reflections	l = −25→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.020	H-atom parameters constrained
wR(F²) = 0.046	w = 1/[σ²(F_o²) + (0.015P)² + 2.190P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.002
5012 reflections	Δρ_max = 0.45 e Å⁻³
639 parameters	Δρ_min = −0.41 e Å⁻³
704 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1A	0.2919 (2)	0.6429 (3)	0.35741 (17)	0.0312 (3)	0.607 (5)
I2A	0.7779 (3)	−0.3592 (4)	0.8045 (2)	0.0334 (3)	0.607 (5)
F1A	0.5211 (8)	0.4995 (7)	0.3638 (5)	0.0555 (17)	0.607 (5)
F2A	0.6152 (3)	0.2793 (4)	0.4288 (2)	0.0555 (11)	0.607 (5)
F3A	0.3424 (4)	0.2371 (5)	0.5447 (3)	0.0595 (12)	0.607 (5)
F4A	0.2517 (7)	0.4575 (10)	0.4809 (6)	0.0626 (19)	0.607 (5)
F5A	0.7232 (3)	−0.0517 (4)	0.57418 (19)	0.0501 (10)	0.607 (5)
F6A	0.8322 (6)	−0.2068 (11)	0.6747 (5)	0.0554 (16)	0.607 (5)
F7A	0.5405 (7)	−0.2192 (7)	0.7743 (4)	0.0568 (15)	0.607 (5)
F8A	0.4315 (3)	−0.0608 (5)	0.6754 (2)	0.0621 (12)	0.607 (5)
C1A	0.3811 (6)	0.4839 (6)	0.4177 (3)	0.0305 (10)	0.607 (5)
C2A	0.4758 (6)	0.4381 (7)	0.4096 (5)	0.0326 (18)	0.607 (5)
C3A	0.5239 (5)	0.3219 (6)	0.4419 (4)	0.0331 (15)	0.607 (5)
C4A	0.4821 (5)	0.2448 (5)	0.4873 (3)	0.0286 (13)	0.607 (5)
C5A	0.3907 (6)	0.2958 (7)	0.4997 (4)	0.0361 (16)	0.607 (5)
C6A	0.3427 (8)	0.4150 (11)	0.4672 (6)	0.039 (2)	0.607 (5)
C7A	0.5335 (4)	0.1052 (4)	0.5069 (2)	0.0345 (12)	0.607 (5)
H7A	0.6107	0.1159	0.5226	0.041*	0.607 (5)
C8A	0.4949 (4)	0.0049 (4)	0.5547 (2)	0.0347 (12)	0.607 (5)
H8A	0.4302	0.0395	0.5654	0.042*	0.607 (5)
C9A	0.5739 (5)	−0.0465 (5)	0.6206 (3)	0.0279 (12)	0.607 (5)
C10A	0.6746 (6)	−0.0888 (6)	0.6241 (3)	0.0350 (15)	0.607 (5)
C11A	0.7341 (6)	−0.1690 (9)	0.6779 (4)	0.035 (2)	0.607 (5)
C12A	0.6919 (7)	−0.2189 (10)	0.7301 (4)	0.033 (2)	0.607 (5)
C13A	0.5904 (6)	−0.1750 (8)	0.7274 (4)	0.0355 (18)	0.607 (5)
C14A	0.5327 (5)	−0.0918 (6)	0.6751 (3)	0.0367 (15)	0.607 (5)
I1B	0.3107 (3)	0.6472 (5)	0.3555 (3)	0.0312 (3)	0.393 (5)
I2B	0.7664 (5)	−0.3457 (7)	0.8050 (4)	0.0334 (3)	0.393 (5)
F1B	0.5133 (12)	0.4602 (11)	0.3717 (7)	0.049 (2)	0.393 (5)
F2B	0.5807 (4)	0.2351 (6)	0.4396 (3)	0.0391 (13)	0.393 (5)
F3B	0.2945 (5)	0.2550 (7)	0.5455 (4)	0.0468 (15)	0.393 (5)
F4B	0.2270 (11)	0.4834 (16)	0.4770 (8)	0.050 (2)	0.393 (5)
F5B	0.7765 (4)	−0.0620 (7)	0.5782 (3)	0.0480 (15)	0.393 (5)
F6B	0.8606 (9)	−0.2221 (18)	0.6847 (8)	0.055 (3)	0.393 (5)
F7B	0.5544 (10)	−0.1726 (11)	0.7662 (7)	0.059 (2)	0.393 (5)
F8B	0.4671 (5)	−0.0155 (7)	0.6593 (3)	0.0557 (17)	0.393 (5)
C1B	0.3651 (9)	0.4773 (10)	0.4200 (5)	0.0305 (10)	0.393 (5)
C2B	0.4570 (9)	0.4118 (10)	0.4139 (6)	0.029 (2)	0.393 (5)
C3B	0.4941 (7)	0.2939 (9)	0.4522 (5)	0.0231 (19)	0.393 (5)
C4B	0.4393 (7)	0.2331 (8)	0.4946 (4)	0.0207 (17)	0.393 (5)
C5B	0.3528 (7)	0.3072 (10)	0.5039 (5)	0.025 (2)	0.393 (5)
C6B	0.3156 (12)	0.4240 (14)	0.4673 (8)	0.027 (3)	0.393 (5)
C7B	0.4571 (5)	0.0852 (5)	0.5191 (3)	0.0204 (15)	0.393 (5)
H7B	0.4184	0.0658	0.5542	0.024*	0.393 (5)
C8B	0.5722 (5)	0.0265 (6)	0.5420 (3)	0.0221 (15)	0.393 (5)
H8B	0.6213	0.0940	0.5309	0.027*	0.393 (5)
C9B	0.6203 (7)	−0.0309 (8)	0.6134 (4)	0.0272 (18)	0.393 (5)
C10B	0.7171 (7)	−0.0883 (9)	0.6237 (4)	0.029 (2)	0.393 (5)
C11B	0.7626 (11)	−0.1727 (14)	0.6787 (6)	0.032 (3)	0.393 (5)
C12B	0.7069 (10)	−0.2048 (13)	0.7259 (6)	0.026 (3)	0.393 (5)
C13B	0.6083 (9)	−0.1469 (12)	0.7186 (6)	0.037 (3)	0.393 (5)
C14B	0.5645 (7)	−0.0641 (9)	0.6616 (5)	0.0290 (19)	0.393 (5)
N1A	0.8132 (8)	0.3344 (13)	0.2394 (6)	0.052 (2)	0.769 (7)
N2A	1.1305 (5)	0.9429 (10)	0.5981 (5)	0.0437 (12)	0.769 (7)
C15A	0.9114 (8)	0.3747 (14)	0.2407 (5)	0.058 (2)	0.769 (7)
H15A	0.9407	0.3445	0.2054	0.070*	0.769 (7)
C16A	0.9726 (5)	0.4586 (6)	0.2911 (3)	0.0506 (14)	0.769 (7)
H16A	1.0400	0.4858	0.2886	0.061*	0.769 (7)
C17A	0.9323 (5)	0.5018 (5)	0.3454 (3)	0.0391 (13)	0.769 (7)
C18A	0.8324 (5)	0.4550 (6)	0.3458 (3)	0.0469 (14)	0.769 (7)
H18A	0.8025	0.4803	0.3816	0.056*	0.769 (7)
C19A	0.7765 (8)	0.3712 (15)	0.2936 (6)	0.058 (2)	0.769 (7)
H19A	0.7104	0.3388	0.2961	0.070*	0.769 (7)
C20A	0.9949 (3)	0.5949 (4)	0.3980 (2)	0.0426 (12)	0.769 (7)
H20A	1.0635	0.6150	0.3951	0.051*	0.769 (7)
C21A	0.9632 (4)	0.6525 (4)	0.4487 (2)	0.0420 (11)	0.769 (7)
H21A	0.8958	0.6285	0.4526	0.050*	0.769 (7)
C22A	1.0230 (4)	0.7513 (6)	0.5001 (3)	0.0360 (12)	0.769 (7)
C23A	1.1225 (5)	0.7988 (8)	0.5002 (4)	0.0531 (18)	0.769 (7)
H23A	1.1558	0.7671	0.4671	0.064*	0.769 (7)
C24A	1.1731 (6)	0.8935 (9)	0.5491 (4)	0.0509 (18)	0.769 (7)
H24A	1.2402	0.9242	0.5477	0.061*	0.769 (7)
C25A	1.0349 (5)	0.8954 (9)	0.5981 (4)	0.0559 (13)	0.769 (7)
H25A	1.0037	0.9275	0.6321	0.067*	0.769 (7)
C26A	0.9789 (5)	0.8019 (8)	0.5510 (3)	0.0539 (13)	0.769 (7)
H26A	0.9118	0.7732	0.5534	0.065*	0.769 (7)
N1B	0.821 (3)	0.317 (5)	0.247 (2)	0.052 (2)	0.231 (7)
N2B	1.108 (2)	0.949 (4)	0.6002 (17)	0.0437 (12)	0.231 (7)
C15B	0.912 (3)	0.387 (5)	0.2552 (18)	0.056 (7)	0.231 (7)
H15B	0.9493	0.3799	0.2213	0.067*	0.231 (7)
C16B	0.9526 (14)	0.468 (2)	0.3126 (10)	0.045 (5)	0.231 (7)
H16B	1.0208	0.5041	0.3206	0.054*	0.231 (7)
C17B	0.8912 (14)	0.4952 (17)	0.3576 (8)	0.032 (4)	0.231 (7)
C18B	0.7920 (14)	0.439 (2)	0.3454 (11)	0.045 (4)	0.231 (7)
H18B	0.7486	0.4553	0.3750	0.054*	0.231 (7)
C19B	0.758 (3)	0.356 (5)	0.287 (2)	0.055 (6)	0.231 (7)
H19B	0.6878	0.3252	0.2759	0.066*	0.231 (7)
C20B	0.9305 (10)	0.5860 (13)	0.4177 (6)	0.041 (4)	0.231 (7)
H20B	0.8871	0.5934	0.4480	0.049*	0.231 (7)
C21B	1.0177 (10)	0.6569 (12)	0.4338 (7)	0.035 (3)	0.231 (7)
H21B	1.0634	0.6461	0.4052	0.042*	0.231 (7)
C22B	1.0528 (16)	0.754 (2)	0.4929 (10)	0.0360 (12)	0.231 (7)
C23B	1.1490 (16)	0.817 (3)	0.5087 (14)	0.046 (5)	0.231 (7)
H23B	1.1998	0.7947	0.4851	0.055*	0.231 (7)
C24B	1.171 (2)	0.916 (4)	0.5602 (18)	0.067 (9)	0.231 (7)
H24B	1.2347	0.9631	0.5670	0.081*	0.231 (7)
C25B	1.017 (2)	0.883 (3)	0.5859 (13)	0.0559 (13)	0.231 (7)
H25B	0.9687	0.9020	0.6122	0.067*	0.231 (7)
C26B	0.9890 (18)	0.787 (3)	0.5343 (12)	0.0539 (13)	0.231 (7)
H26B	0.9237	0.7430	0.5275	0.065*	0.231 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.0326 (8)	0.0234 (2)	0.03566 (19)	0.0052 (5)	0.0047 (5)	0.00708 (13)
I2A	0.0369 (8)	0.0318 (7)	0.02747 (10)	0.0087 (4)	0.0007 (4)	0.0084 (4)
F1A	0.058 (3)	0.045 (4)	0.072 (3)	0.013 (3)	0.031 (2)	0.033 (3)
F2A	0.040 (2)	0.050 (2)	0.080 (3)	0.0150 (17)	0.0234 (18)	0.0266 (19)
F3A	0.079 (3)	0.047 (2)	0.068 (2)	0.021 (2)	0.047 (3)	0.0261 (17)
F4A	0.063 (5)	0.053 (4)	0.084 (3)	0.029 (3)	0.042 (4)	0.029 (3)
F5A	0.045 (2)	0.061 (2)	0.0489 (19)	0.011 (2)	0.020 (2)	0.0282 (15)
F6A	0.033 (4)	0.077 (4)	0.056 (3)	0.008 (3)	0.011 (3)	0.031 (2)
F7A	0.062 (3)	0.061 (4)	0.056 (3)	0.019 (3)	0.0318 (19)	0.022 (3)
F8A	0.051 (2)	0.082 (3)	0.061 (2)	0.037 (2)	0.0272 (17)	0.025 (2)
C1A	0.036 (2)	0.0203 (13)	0.0324 (14)	0.0025 (13)	0.0041 (14)	0.0060 (11)
C2A	0.035 (3)	0.020 (3)	0.041 (4)	−0.002 (2)	0.007 (2)	0.010 (2)
C3A	0.034 (3)	0.027 (3)	0.038 (3)	−0.001 (2)	0.008 (2)	0.009 (2)
C4A	0.034 (3)	0.022 (2)	0.029 (3)	0.001 (2)	0.005 (2)	0.0042 (19)
C5A	0.049 (4)	0.026 (3)	0.037 (3)	0.005 (3)	0.018 (3)	0.009 (2)
C6A	0.039 (5)	0.033 (3)	0.047 (4)	0.010 (3)	0.014 (3)	0.006 (3)
C7A	0.037 (3)	0.025 (2)	0.036 (2)	−0.0002 (18)	−0.0015 (19)	0.0062 (18)
C8A	0.036 (3)	0.030 (2)	0.035 (2)	0.0054 (19)	0.0025 (19)	0.0061 (19)
C9A	0.033 (3)	0.022 (2)	0.028 (3)	0.005 (2)	0.005 (2)	0.0069 (19)
C10A	0.041 (3)	0.035 (3)	0.031 (3)	0.001 (3)	0.014 (2)	0.010 (2)
C11A	0.030 (4)	0.038 (4)	0.037 (3)	0.004 (3)	0.003 (2)	0.006 (2)
C12A	0.044 (4)	0.029 (4)	0.026 (3)	0.002 (3)	0.006 (3)	0.009 (3)
C13A	0.045 (3)	0.037 (4)	0.027 (3)	0.007 (3)	0.013 (2)	0.008 (3)
C14A	0.045 (3)	0.037 (3)	0.030 (3)	0.010 (3)	0.013 (2)	0.006 (2)
I1B	0.0326 (8)	0.0234 (2)	0.03566 (19)	0.0052 (5)	0.0047 (5)	0.00708 (13)
I2B	0.0369 (8)	0.0318 (7)	0.02747 (10)	0.0087 (4)	0.0007 (4)	0.0084 (4)
F1B	0.056 (4)	0.038 (5)	0.060 (4)	0.008 (4)	0.027 (3)	0.027 (4)
F2B	0.032 (3)	0.040 (3)	0.052 (3)	0.014 (2)	0.022 (2)	0.018 (2)
F3B	0.046 (4)	0.052 (3)	0.055 (3)	0.020 (3)	0.035 (3)	0.025 (2)
F4B	0.046 (5)	0.050 (5)	0.061 (4)	0.031 (3)	0.028 (3)	0.021 (4)
F5B	0.025 (3)	0.066 (3)	0.056 (3)	0.010 (3)	0.016 (3)	0.032 (2)
F6B	0.028 (5)	0.077 (5)	0.058 (5)	0.016 (4)	0.005 (4)	0.028 (4)
F7B	0.066 (5)	0.065 (6)	0.054 (4)	0.024 (4)	0.030 (3)	0.022 (4)
F8B	0.049 (3)	0.083 (5)	0.042 (3)	0.040 (3)	0.025 (2)	0.022 (3)
C1B	0.036 (2)	0.0203 (13)	0.0324 (14)	0.0025 (13)	0.0041 (14)	0.0060 (11)
C2B	0.034 (4)	0.020 (4)	0.031 (4)	−0.008 (3)	0.008 (3)	0.007 (3)
C3B	0.023 (4)	0.019 (4)	0.031 (4)	0.005 (3)	0.014 (3)	0.008 (3)
C4B	0.022 (4)	0.021 (3)	0.022 (3)	0.004 (3)	0.009 (3)	0.006 (2)
C5B	0.026 (4)	0.031 (4)	0.022 (3)	0.014 (3)	0.014 (3)	0.008 (3)
C6B	0.028 (6)	0.023 (4)	0.031 (4)	0.009 (4)	0.006 (4)	0.006 (3)
C7B	0.021 (3)	0.015 (3)	0.024 (3)	0.003 (2)	0.004 (2)	0.006 (2)
C8B	0.021 (3)	0.017 (3)	0.027 (3)	0.002 (2)	0.003 (2)	0.007 (2)
C9B	0.027 (4)	0.026 (4)	0.030 (3)	0.003 (3)	0.010 (3)	0.003 (3)
C10B	0.023 (4)	0.026 (4)	0.037 (4)	−0.004 (3)	0.002 (3)	0.010 (3)
C11B	0.029 (6)	0.034 (5)	0.032 (4)	−0.001 (4)	0.003 (3)	0.010 (3)
C12B	0.030 (4)	0.018 (5)	0.025 (5)	0.002 (3)	−0.003 (3)	0.005 (3)
C13B	0.046 (5)	0.035 (5)	0.029 (4)	0.007 (4)	0.010 (3)	0.007 (3)
C14B	0.028 (4)	0.028 (4)	0.034 (4)	0.014 (3)	0.014 (3)	0.011 (3)
N1A	0.065 (2)	0.038 (4)	0.043 (3)	−0.008 (3)	−0.006 (2)	−0.009 (3)
N2A	0.038 (3)	0.0477 (18)	0.0438 (15)	−0.003 (3)	0.008 (2)	−0.0190 (13)
C15A	0.072 (3)	0.052 (5)	0.045 (4)	−0.010 (3)	0.005 (3)	−0.021 (3)
C16A	0.055 (3)	0.049 (3)	0.046 (3)	−0.006 (2)	0.010 (2)	−0.018 (2)
C17A	0.041 (3)	0.034 (2)	0.037 (3)	0.001 (2)	−0.001 (2)	−0.0071 (19)
C18A	0.043 (4)	0.050 (3)	0.042 (2)	−0.007 (3)	0.001 (3)	−0.014 (2)
C19A	0.060 (4)	0.053 (5)	0.053 (4)	−0.014 (3)	−0.001 (3)	−0.011 (3)
C20A	0.038 (2)	0.044 (2)	0.042 (2)	−0.0054 (18)	0.0019 (18)	−0.0096 (18)
C21A	0.040 (3)	0.044 (2)	0.038 (2)	−0.007 (2)	0.0029 (18)	−0.0075 (18)
C22A	0.034 (3)	0.0355 (15)	0.0334 (19)	0.001 (2)	−0.0011 (19)	−0.0060 (14)
C23A	0.050 (4)	0.063 (4)	0.044 (3)	−0.013 (3)	0.007 (3)	−0.032 (3)
C24A	0.046 (3)	0.055 (4)	0.055 (4)	−0.010 (2)	0.018 (3)	−0.026 (3)
C25A	0.047 (3)	0.069 (3)	0.051 (3)	−0.016 (2)	0.012 (2)	−0.032 (2)
C26A	0.048 (2)	0.064 (3)	0.050 (3)	−0.0146 (19)	0.0134 (19)	−0.026 (2)
N1B	0.065 (2)	0.038 (4)	0.043 (3)	−0.008 (3)	−0.006 (2)	−0.009 (3)
N2B	0.038 (3)	0.0477 (18)	0.0438 (15)	−0.003 (3)	0.008 (2)	−0.0190 (13)
C15B	0.071 (8)	0.050 (12)	0.045 (11)	−0.013 (8)	0.009 (7)	−0.024 (9)
C16B	0.035 (7)	0.052 (9)	0.046 (9)	−0.017 (6)	0.010 (6)	−0.029 (7)
C17B	0.027 (8)	0.035 (7)	0.031 (6)	0.001 (6)	−0.001 (5)	−0.009 (5)
C18B	0.031 (8)	0.050 (9)	0.049 (7)	−0.010 (6)	−0.002 (6)	−0.012 (6)
C19B	0.063 (8)	0.047 (12)	0.046 (8)	−0.010 (7)	−0.005 (7)	−0.010 (8)
C20B	0.040 (7)	0.044 (6)	0.036 (6)	−0.008 (5)	0.005 (5)	−0.011 (5)
C21B	0.035 (6)	0.031 (6)	0.036 (6)	0.000 (5)	0.002 (5)	−0.007 (4)
C22B	0.034 (3)	0.0355 (15)	0.0334 (19)	0.001 (2)	−0.0011 (19)	−0.0060 (14)
C23B	0.030 (6)	0.052 (9)	0.052 (9)	−0.010 (5)	0.006 (6)	−0.022 (7)
C24B	0.053 (8)	0.083 (15)	0.067 (12)	−0.027 (9)	0.016 (8)	−0.052 (12)
C25B	0.047 (3)	0.069 (3)	0.051 (3)	−0.016 (2)	0.012 (2)	−0.032 (2)
C26B	0.048 (2)	0.064 (3)	0.050 (3)	−0.0146 (19)	0.0134 (19)	−0.026 (2)

Geometric parameters (Å, º) top

I1A—C1A	2.116 (7)	C10B—C11B	1.378 (11)
I2A—C12A	2.117 (7)	C11B—C12B	1.365 (12)
F1A—C2A	1.347 (7)	C12B—C13B	1.375 (11)
F2A—C3A	1.345 (7)	C13B—C14B	1.394 (11)
F3A—C5A	1.347 (7)	N1A—C15A	1.331 (7)
F4A—C6A	1.346 (7)	N1A—C19A	1.337 (7)
F5A—C10A	1.357 (6)	N2A—C24A	1.332 (6)
F6A—C11A	1.345 (7)	N2A—C25A	1.326 (6)
F7A—C13A	1.339 (7)	C15A—H15A	0.9300
F8A—C14A	1.354 (7)	C15A—C16A	1.381 (7)
C1A—C2A	1.358 (8)	C16A—H16A	0.9300
C1A—C6A	1.388 (8)	C16A—C17A	1.386 (7)
C2A—C3A	1.370 (7)	C17A—C18A	1.380 (7)
C3A—C4A	1.389 (7)	C17A—C20A	1.468 (5)
C4A—C5A	1.368 (8)	C18A—H18A	0.9300
C4A—C7A	1.520 (6)	C18A—C19A	1.377 (6)
C5A—C6A	1.396 (8)	C19A—H19A	0.9300
C7A—H7A	0.9800	C20A—H20A	0.9300
C7A—C8Aⁱ	1.602 (6)	C20A—C21A	1.311 (6)
C7A—C8A	1.536 (6)	C21A—H21A	0.9300
C8A—C7Aⁱ	1.602 (6)	C21A—C22A	1.476 (5)
C8A—H8A	0.9800	C22A—C23A	1.375 (6)
C8A—C9A	1.534 (6)	C22A—C26A	1.378 (5)
C9A—C10A	1.359 (7)	C23A—H23A	0.9300
C9A—C14A	1.400 (7)	C23A—C24A	1.383 (7)
C10A—C11A	1.394 (8)	C24A—H24A	0.9300
C11A—C12A	1.384 (8)	C25A—H25A	0.9300
C12A—C13A	1.376 (8)	C25A—C26A	1.377 (6)
C13A—C14A	1.383 (7)	C26A—H26A	0.9300
I1B—C1B	2.105 (10)	N1B—C15B	1.339 (17)
I2B—C12B	2.085 (10)	N1B—C19B	1.340 (17)
F1B—C2B	1.336 (10)	N2B—C24B	1.314 (16)
F2B—C3B	1.343 (8)	N2B—C25B	1.326 (16)
F3B—C5B	1.358 (9)	C15B—H15B	0.9300
F4B—C6B	1.347 (11)	C15B—C16B	1.383 (16)
F5B—C10B	1.360 (9)	C16B—H16B	0.9300
F6B—C11B	1.340 (11)	C16B—C17B	1.371 (15)
F7B—C13B	1.340 (10)	C17B—C18B	1.368 (15)
F8B—C14B	1.344 (9)	C17B—C20B	1.473 (13)
C1B—C2B	1.389 (11)	C18B—H18B	0.9300
C1B—C6B	1.372 (11)	C18B—C19B	1.391 (16)
C2B—C3B	1.394 (11)	C19B—H19B	0.9300
C3B—C4B	1.372 (9)	C20B—H20B	0.9300
C4B—C5B	1.388 (9)	C20B—C21B	1.297 (15)
C4B—C7B	1.516 (8)	C21B—H21B	0.9300
C5B—C6B	1.370 (10)	C21B—C22B	1.487 (14)
C7B—H7B	0.9800	C22B—C23B	1.361 (15)
C7B—C8Bⁱ	1.607 (8)	C22B—C26B	1.353 (15)
C7B—C8B	1.560 (7)	C23B—H23B	0.9300
C8B—C7Bⁱ	1.606 (8)	C23B—C24B	1.382 (16)
C8B—H8B	0.9800	C24B—H24B	0.9300
C8B—C9B	1.512 (8)	C25B—H25B	0.9300
C9B—C10B	1.346 (10)	C25B—C26B	1.367 (16)
C9B—C14B	1.383 (10)	C26B—H26B	0.9300

C2A—C1A—I1A	123.7 (5)	C12B—C11B—C10B	119.5 (11)
C2A—C1A—C6A	115.3 (6)	C11B—C12B—I2B	120.9 (8)
C6A—C1A—I1A	120.9 (5)	C11B—C12B—C13B	118.5 (10)
F1A—C2A—C1A	120.2 (7)	C13B—C12B—I2B	120.5 (8)
F1A—C2A—C3A	117.2 (6)	F7B—C13B—C12B	119.3 (9)
C1A—C2A—C3A	122.3 (7)	F7B—C13B—C14B	120.6 (9)
F2A—C3A—C2A	118.9 (6)	C12B—C13B—C14B	120.1 (9)
F2A—C3A—C4A	118.2 (5)	F8B—C14B—C9B	123.5 (8)
C2A—C3A—C4A	122.9 (6)	F8B—C14B—C13B	114.7 (9)
C3A—C4A—C7A	115.4 (5)	C9B—C14B—C13B	121.7 (8)
C5A—C4A—C3A	115.2 (5)	C15A—N1A—C19A	116.3 (6)
C5A—C4A—C7A	128.5 (6)	C25A—N2A—C24A	116.1 (6)
F3A—C5A—C4A	122.9 (6)	N1A—C15A—H15A	117.9
F3A—C5A—C6A	115.6 (6)	N1A—C15A—C16A	124.2 (6)
C4A—C5A—C6A	121.5 (6)	C16A—C15A—H15A	117.9
F4A—C6A—C1A	119.4 (7)	C15A—C16A—H16A	120.4
F4A—C6A—C5A	118.3 (7)	C15A—C16A—C17A	119.2 (5)
C1A—C6A—C5A	122.2 (7)	C17A—C16A—H16A	120.4
C4A—C7A—H7A	109.7	C16A—C17A—C20A	119.7 (5)
C4A—C7A—C8A	122.3 (5)	C18A—C17A—C16A	116.7 (4)
C4A—C7A—C8Aⁱ	113.3 (4)	C18A—C17A—C20A	123.6 (5)
C8A—C7A—H7A	109.7	C17A—C18A—H18A	119.7
C8Aⁱ—C7A—H7A	109.7	C19A—C18A—C17A	120.5 (5)
C8A—C7A—C8Aⁱ	90.4 (3)	C19A—C18A—H18A	119.7
C7A—C8A—C7Aⁱ	89.6 (3)	N1A—C19A—C18A	122.9 (6)
C7A—C8A—H8A	110.6	N1A—C19A—H19A	118.5
C7Aⁱ—C8A—H8A	110.6	C18A—C19A—H19A	118.5
C9A—C8A—C7A	119.2 (4)	C17A—C20A—H20A	116.9
C9A—C8A—C7Aⁱ	114.7 (3)	C21A—C20A—C17A	126.1 (5)
C9A—C8A—H8A	110.6	C21A—C20A—H20A	116.9
C10A—C9A—C8A	124.7 (5)	C20A—C21A—H21A	116.5
C10A—C9A—C14A	114.8 (4)	C20A—C21A—C22A	127.0 (5)
C14A—C9A—C8A	117.7 (5)	C22A—C21A—H21A	116.5
F5A—C10A—C9A	120.4 (6)	C23A—C22A—C21A	123.3 (4)
F5A—C10A—C11A	116.4 (6)	C23A—C22A—C26A	116.6 (4)
C9A—C10A—C11A	123.3 (5)	C26A—C22A—C21A	120.1 (4)
F6A—C11A—C10A	117.8 (7)	C22A—C23A—H23A	119.8
F6A—C11A—C12A	120.1 (7)	C22A—C23A—C24A	120.3 (5)
C12A—C11A—C10A	121.9 (6)	C24A—C23A—H23A	119.8
C11A—C12A—I2A	121.0 (6)	N2A—C24A—C23A	123.2 (6)
C13A—C12A—I2A	124.0 (5)	N2A—C24A—H24A	118.4
C13A—C12A—C11A	115.0 (6)	C23A—C24A—H24A	118.4
F7A—C13A—C12A	120.3 (6)	N2A—C25A—H25A	117.8
F7A—C13A—C14A	116.7 (6)	N2A—C25A—C26A	124.3 (6)
C12A—C13A—C14A	122.9 (7)	C26A—C25A—H25A	117.8
F8A—C14A—C9A	119.9 (5)	C22A—C26A—H26A	120.3
F8A—C14A—C13A	118.0 (6)	C25A—C26A—C22A	119.5 (5)
C13A—C14A—C9A	122.0 (6)	C25A—C26A—H26A	120.3
C2B—C1B—I1B	118.0 (8)	C15B—N1B—C19B	117 (2)
C6B—C1B—I1B	125.1 (8)	C24B—N2B—C25B	114.2 (19)
C6B—C1B—C2B	116.9 (9)	N1B—C15B—H15B	119.0
F1B—C2B—C1B	121.2 (10)	N1B—C15B—C16B	121.9 (19)
F1B—C2B—C3B	117.8 (9)	C16B—C15B—H15B	119.0
C1B—C2B—C3B	121.0 (9)	C15B—C16B—H16B	120.3
F2B—C3B—C2B	115.9 (8)	C17B—C16B—C15B	119.4 (15)
F2B—C3B—C4B	121.6 (7)	C17B—C16B—H16B	120.3
C4B—C3B—C2B	122.1 (8)	C16B—C17B—C20B	120.7 (14)
C3B—C4B—C5B	115.1 (6)	C18B—C17B—C16B	119.1 (12)
C3B—C4B—C7B	123.1 (7)	C18B—C17B—C20B	120.2 (15)
C5B—C4B—C7B	120.8 (7)	C17B—C18B—H18B	120.9
F3B—C5B—C4B	119.1 (7)	C17B—C18B—C19B	118.1 (16)
F3B—C5B—C6B	117.3 (8)	C19B—C18B—H18B	120.9
C6B—C5B—C4B	123.2 (8)	N1B—C19B—C18B	123 (2)
F4B—C6B—C1B	120.3 (10)	N1B—C19B—H19B	118.4
F4B—C6B—C5B	118.6 (9)	C18B—C19B—H19B	118.4
C5B—C6B—C1B	121.1 (10)	C17B—C20B—H20B	115.8
C4B—C7B—H7B	110.4	C21B—C20B—C17B	128.4 (14)
C4B—C7B—C8Bⁱ	114.0 (5)	C21B—C20B—H20B	115.8
C4B—C7B—C8B	119.9 (6)	C20B—C21B—H21B	116.3
C8B—C7B—H7B	110.4	C20B—C21B—C22B	127.3 (15)
C8Bⁱ—C7B—H7B	110.4	C22B—C21B—H21B	116.3
C8B—C7B—C8Bⁱ	90.1 (4)	C23B—C22B—C21B	123.5 (16)
C7B—C8B—C7Bⁱ	89.9 (4)	C26B—C22B—C21B	121.6 (16)
C7B—C8B—H8B	108.8	C26B—C22B—C23B	114.8 (15)
C7Bⁱ—C8B—H8B	108.8	C22B—C23B—H23B	120.3
C9B—C8B—C7Bⁱ	115.5 (5)	C22B—C23B—C24B	119.4 (18)
C9B—C8B—C7B	123.4 (6)	C24B—C23B—H23B	120.3
C9B—C8B—H8B	108.8	N2B—C24B—C23B	126 (2)
C10B—C9B—C8B	116.5 (7)	N2B—C24B—H24B	117.2
C10B—C9B—C14B	115.7 (7)	C23B—C24B—H24B	117.2
C14B—C9B—C8B	125.3 (8)	N2B—C25B—H25B	118.5
F5B—C10B—C11B	116.3 (8)	N2B—C25B—C26B	123 (2)
C9B—C10B—F5B	119.2 (7)	C26B—C25B—H25B	118.5
C9B—C10B—C11B	124.4 (9)	C22B—C26B—C25B	122.6 (17)
F6B—C11B—C10B	119.4 (10)	C22B—C26B—H26B	118.7
F6B—C11B—C12B	121.1 (11)	C25B—C26B—H26B	118.7

I1A—C1A—C2A—F1A	3.9 (8)	C2B—C1B—C6B—C5B	−3.3 (17)
I1A—C1A—C2A—C3A	−169.9 (6)	C2B—C3B—C4B—C5B	−8.4 (14)
I1A—C1A—C6A—F4A	−5.5 (13)	C2B—C3B—C4B—C7B	160.5 (8)
I1A—C1A—C6A—C5A	169.4 (8)	C3B—C4B—C5B—F3B	−179.6 (9)
I2A—C12A—C13A—F7A	1.2 (13)	C3B—C4B—C5B—C6B	7.8 (16)
I2A—C12A—C13A—C14A	−174.7 (6)	C3B—C4B—C7B—C8B	41.5 (10)
F1A—C2A—C3A—F2A	3.0 (10)	C3B—C4B—C7B—C8Bⁱ	−63.5 (10)
F1A—C2A—C3A—C4A	−176.4 (7)	C4B—C5B—C6B—F4B	175.7 (12)
F2A—C3A—C4A—C5A	178.3 (6)	C4B—C5B—C6B—C1B	−2 (2)
F2A—C3A—C4A—C7A	−11.1 (8)	C4B—C7B—C8B—C7Bⁱ	−118.1 (7)
F3A—C5A—C6A—F4A	−2.6 (14)	C4B—C7B—C8B—C9B	121.0 (7)
F3A—C5A—C6A—C1A	−177.5 (9)	C5B—C4B—C7B—C8B	−150.2 (8)
F5A—C10A—C11A—F6A	−2.3 (10)	C5B—C4B—C7B—C8Bⁱ	104.8 (9)
F5A—C10A—C11A—C12A	−176.8 (8)	C6B—C1B—C2B—F1B	−176.8 (12)
F6A—C11A—C12A—I2A	−1.6 (13)	C6B—C1B—C2B—C3B	2.6 (12)
F6A—C11A—C12A—C13A	−179.0 (9)	C7B—C4B—C5B—F3B	11.3 (14)
F7A—C13A—C14A—F8A	0.5 (10)	C7B—C4B—C5B—C6B	−161.3 (11)
F7A—C13A—C14A—C9A	−175.8 (6)	C7Bⁱ—C8B—C9B—C10B	66.5 (7)
C1A—C2A—C3A—F2A	176.9 (5)	C7B—C8B—C9B—C10B	174.6 (5)
C1A—C2A—C3A—C4A	−2.5 (10)	C7Bⁱ—C8B—C9B—C14B	−94.5 (8)
C2A—C1A—C6A—F4A	177.0 (8)	C7B—C8B—C9B—C14B	13.6 (10)
C2A—C1A—C6A—C5A	−8.1 (13)	C8Bⁱ—C7B—C8B—C7Bⁱ	−0.002 (2)
C2A—C3A—C4A—C5A	−2.3 (10)	C8Bⁱ—C7B—C8B—C9B	−120.9 (6)
C2A—C3A—C4A—C7A	168.3 (6)	C8B—C9B—C10B—F5B	16.4 (7)
C3A—C4A—C5A—F3A	−177.0 (6)	C8B—C9B—C10B—C11B	−164.3 (9)
C3A—C4A—C5A—C6A	1.7 (11)	C8B—C9B—C14B—F8B	−19.2 (12)
C3A—C4A—C7A—C8Aⁱ	−71.7 (6)	C8B—C9B—C14B—C13B	163.8 (9)
C3A—C4A—C7A—C8A	−178.1 (5)	C9B—C10B—C11B—F6B	−178.7 (11)
C4A—C5A—C6A—F4A	178.6 (9)	C9B—C10B—C11B—C12B	1.5 (15)
C4A—C5A—C6A—C1A	3.7 (15)	C10B—C9B—C14B—F8B	179.7 (7)
C4A—C7A—C8A—C7Aⁱ	118.2 (5)	C10B—C9B—C14B—C13B	2.6 (11)
C4A—C7A—C8A—C9A	−123.5 (5)	C10B—C11B—C12B—I2B	174.5 (8)
C5A—C4A—C7A—C8A	−9.0 (8)	C10B—C11B—C12B—C13B	−2.6 (19)
C5A—C4A—C7A—C8Aⁱ	97.4 (7)	C11B—C12B—C13B—F7B	−177.1 (13)
C6A—C1A—C2A—F1A	−178.8 (9)	C11B—C12B—C13B—C14B	3.8 (19)
C6A—C1A—C2A—C3A	7.4 (9)	C12B—C13B—C14B—F8B	178.8 (11)
C7A—C4A—C5A—F3A	13.8 (11)	C12B—C13B—C14B—C9B	−3.9 (17)
C7A—C4A—C5A—C6A	−167.5 (8)	C14B—C9B—C10B—F5B	179.3 (8)
C7Aⁱ—C8A—C9A—C10A	60.5 (6)	C14B—C9B—C10B—C11B	−1.5 (9)
C7A—C8A—C9A—C10A	−43.8 (5)	N1A—C15A—C16A—C17A	2.0 (19)
C7Aⁱ—C8A—C9A—C14A	−99.6 (5)	N2A—C25A—C26A—C22A	0.5 (9)
C7A—C8A—C9A—C14A	156.1 (4)	C15A—N1A—C19A—C18A	5 (2)
C8Aⁱ—C7A—C8A—C7Aⁱ	−0.001 (1)	C15A—C16A—C17A—C18A	1.0 (10)
C8Aⁱ—C7A—C8A—C9A	118.3 (5)	C15A—C16A—C17A—C20A	−177.9 (8)
C8A—C9A—C10A—F5A	19.3 (5)	C16A—C17A—C18A—C19A	−0.9 (11)
C8A—C9A—C10A—C11A	−161.7 (6)	C16A—C17A—C20A—C21A	174.1 (5)
C8A—C9A—C14A—F8A	−15.2 (7)	C17A—C18A—C19A—N1A	−2 (2)
C8A—C9A—C14A—C13A	161.1 (6)	C17A—C20A—C21A—C22A	−177.0 (5)
C9A—C10A—C11A—F6A	178.6 (6)	C18A—C17A—C20A—C21A	−4.7 (7)
C9A—C10A—C11A—C12A	4.1 (11)	C19A—N1A—C15A—C16A	−5 (2)
C10A—C9A—C14A—F8A	−177.2 (4)	C20A—C17A—C18A—C19A	177.9 (9)
C10A—C9A—C14A—C13A	−1.0 (8)	C20A—C21A—C22A—C23A	1.4 (9)
C10A—C11A—C12A—I2A	172.8 (6)	C20A—C21A—C22A—C26A	−179.4 (6)
C10A—C11A—C12A—C13A	−4.6 (13)	C21A—C22A—C23A—C24A	178.7 (7)
C11A—C12A—C13A—F7A	178.4 (8)	C21A—C22A—C26A—C25A	−179.1 (6)
C11A—C12A—C13A—C14A	2.5 (13)	C22A—C23A—C24A—N2A	0.3 (13)
C12A—C13A—C14A—F8A	176.5 (8)	C23A—C22A—C26A—C25A	0.1 (10)
C12A—C13A—C14A—C9A	0.2 (12)	C24A—N2A—C25A—C26A	−0.7 (9)
C14A—C9A—C10A—F5A	179.9 (5)	C25A—N2A—C24A—C23A	0.3 (12)
C14A—C9A—C10A—C11A	−1.1 (6)	C26A—C22A—C23A—C24A	−0.5 (11)
I1B—C1B—C2B—F1B	4.3 (10)	N1B—C15B—C16B—C17B	−10 (7)
I1B—C1B—C2B—C3B	−176.2 (8)	N2B—C25B—C26B—C22B	−1 (2)
I1B—C1B—C6B—F4B	−2.3 (19)	C15B—N1B—C19B—C18B	−15 (9)
I1B—C1B—C6B—C5B	175.5 (10)	C15B—C16B—C17B—C18B	1 (4)
I2B—C12B—C13B—F7B	5.7 (17)	C15B—C16B—C17B—C20B	−178 (3)
I2B—C12B—C13B—C14B	−173.4 (9)	C16B—C17B—C18B—C19B	0 (4)
F1B—C2B—C3B—F2B	−3.8 (14)	C16B—C17B—C20B—C21B	5 (3)
F1B—C2B—C3B—C4B	−177.1 (10)	C17B—C18B—C19B—N1B	7 (7)
F2B—C3B—C4B—C5B	178.7 (9)	C17B—C20B—C21B—C22B	176.5 (18)
F2B—C3B—C4B—C7B	−12.4 (13)	C18B—C17B—C20B—C21B	−173.7 (18)
F3B—C5B—C6B—F4B	3 (2)	C19B—N1B—C15B—C16B	16 (9)
F3B—C5B—C6B—C1B	−174.8 (11)	C20B—C17B—C18B—C19B	179 (3)
F5B—C10B—C11B—F6B	0.6 (16)	C20B—C21B—C22B—C23B	176 (2)
F5B—C10B—C11B—C12B	−179.2 (11)	C20B—C21B—C22B—C26B	−6 (3)
F6B—C11B—C12B—I2B	−5.3 (19)	C21B—C22B—C23B—C24B	173 (3)
F6B—C11B—C12B—C13B	177.6 (14)	C21B—C22B—C26B—C25B	−175 (2)
F7B—C13B—C14B—F8B	−0.3 (15)	C22B—C23B—C24B—N2B	5 (5)
F7B—C13B—C14B—C9B	177.0 (10)	C23B—C22B—C26B—C25B	3 (3)
C1B—C2B—C3B—F2B	176.8 (7)	C24B—N2B—C25B—C26B	0 (2)
C1B—C2B—C3B—C4B	3.5 (13)	C25B—N2B—C24B—C23B	−3 (5)
C2B—C1B—C6B—F4B	178.9 (12)	C26B—C22B—C23B—C24B	−5 (4)

Symmetry code: (i) −x+1, −y, −z+1.

rctt-tetrakis-(4-iodo-2,3,5,6-tetrafluorophenyl)cyclobutane, rctt-tetrakis(4-pyridyl)-cyclobutane (mcg1611a) top

Crystal data top

C₂₈H₄F₁₆I₄·C₂₄H₂₀N₄	F(000) = 1440
M_r = 1516.35	D_x = 2.064 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9647 (13) Å	Cell parameters from 8250 reflections
b = 10.2219 (10) Å	θ = 1–25.4°
c = 19.519 (10) Å	µ = 2.66 mm⁻¹
β = 109.387 (5)°	T = 298 K
V = 2440.0 (13) Å³	Plate, colourless
Z = 2	0.14 × 0.12 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	3198 reflections with I > 2σ(I)
CCD phi and ω scans	R_int = 0.067
Absorption correction: multi-scan HKL Scalepack (Otwinowski & Minor, 1997)	θ_max = 25.4°, θ_min = 3.0°
T_min = 0.751, T_max = 0.955	h = −11→15
12227 measured reflections	k = −12→12
4464 independent reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
4464 reflections	Δρ_max = 0.50 e Å⁻³
548 parameters	Δρ_min = −0.52 e Å⁻³
473 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1A	−0.1907 (4)	1.6322 (4)	−0.1469 (3)	0.0526 (10)	0.764 (7)
I2A	0.2939 (5)	0.6677 (5)	0.3260 (3)	0.0494 (9)	0.764 (7)
F1A	0.0241 (9)	1.4716 (9)	−0.1434 (6)	0.071 (2)	0.764 (7)
F2A	0.1175 (5)	1.2574 (5)	−0.0745 (3)	0.0595 (14)	0.764 (7)
F3A	−0.1480 (6)	1.2366 (6)	0.0417 (4)	0.0649 (16)	0.764 (7)
F4A	−0.2349 (7)	1.4538 (8)	−0.0225 (6)	0.069 (2)	0.764 (7)
F5A	0.2264 (4)	0.9452 (5)	0.0830 (2)	0.0551 (13)	0.764 (7)
F6A	0.3461 (5)	0.8058 (8)	0.1941 (4)	0.0588 (16)	0.764 (7)
F7A	0.0545 (6)	0.8029 (8)	0.2883 (3)	0.0628 (16)	0.764 (7)
F8A	−0.0620 (4)	0.9523 (5)	0.1799 (3)	0.0629 (15)	0.764 (7)
C1A	−0.1106 (7)	1.4689 (7)	−0.0869 (4)	0.037 (3)	0.764 (7)
C2A	−0.0195 (7)	1.4143 (7)	−0.0971 (4)	0.041 (2)	0.764 (7)
C3A	0.0279 (6)	1.3042 (6)	−0.0622 (4)	0.0367 (14)	0.764 (7)
C4A	−0.0131 (6)	1.2337 (6)	−0.0159 (4)	0.0337 (16)	0.764 (7)
C5A	−0.1026 (7)	1.2912 (7)	−0.0034 (4)	0.0389 (18)	0.764 (7)
C6A	−0.1485 (10)	1.4052 (10)	−0.0381 (7)	0.044 (3)	0.764 (7)
C7A	0.0367 (5)	1.0996 (4)	0.0074 (3)	0.0349 (15)	0.764 (7)
H7A	0.1165	1.1072	0.0276	0.042*	0.764 (7)
C8A	−0.0046 (5)	1.0064 (5)	0.0556 (2)	0.0354 (16)	0.764 (7)
H8A	−0.0699	1.0421	0.0634	0.042*	0.764 (7)
C9A	0.0767 (6)	0.9560 (6)	0.1265 (3)	0.0351 (15)	0.764 (7)
C10A	0.1819 (6)	0.9175 (6)	0.1351 (3)	0.0394 (17)	0.764 (7)
C11A	0.2457 (6)	0.8422 (7)	0.1926 (4)	0.040 (2)	0.764 (7)
C12A	0.2047 (8)	0.7998 (13)	0.2456 (6)	0.0402 (13)	0.764 (7)
C13A	0.1017 (6)	0.8405 (9)	0.2396 (4)	0.0388 (18)	0.764 (7)
C14A	0.0410 (6)	0.9186 (7)	0.1831 (3)	0.0420 (17)	0.764 (7)
I1B	−0.1957 (11)	1.6278 (10)	−0.1526 (8)	0.0378 (17)	0.236 (7)
I2B	0.2834 (17)	0.6676 (14)	0.3282 (8)	0.0420 (15)	0.236 (7)
F1B	0.020 (3)	1.439 (3)	−0.1344 (19)	0.067 (7)	0.236 (7)
F2B	0.0865 (15)	1.2183 (18)	−0.0608 (10)	0.060 (5)	0.236 (7)
F3B	−0.1926 (16)	1.2608 (19)	0.0419 (11)	0.055 (5)	0.236 (7)
F4B	−0.251 (3)	1.488 (3)	−0.0273 (19)	0.068 (7)	0.236 (7)
F5B	0.2848 (13)	0.9379 (18)	0.0909 (8)	0.061 (4)	0.236 (7)
F6B	0.373 (2)	0.780 (3)	0.2021 (18)	0.075 (7)	0.236 (7)
F7B	0.066 (2)	0.839 (3)	0.2755 (15)	0.085 (8)	0.236 (7)
F8B	−0.0255 (13)	0.9934 (18)	0.1660 (10)	0.063 (5)	0.236 (7)
C1B	−0.1228 (19)	1.466 (2)	−0.0872 (13)	0.041 (11)	0.236 (7)
C2B	−0.0345 (18)	1.3947 (19)	−0.0915 (14)	0.040 (8)	0.236 (7)
C3B	0.0014 (17)	1.2834 (19)	−0.0518 (13)	0.0367 (14)	0.236 (7)
C4B	−0.0533 (18)	1.2290 (16)	−0.0085 (12)	0.030 (5)	0.236 (7)
C5B	−0.137 (2)	1.306 (2)	0.0003 (16)	0.049 (8)	0.236 (7)
C6B	−0.169 (3)	1.419 (3)	−0.038 (2)	0.034 (7)	0.236 (7)
C7B	−0.0382 (13)	1.0867 (13)	0.0171 (8)	0.031 (4)	0.236 (7)
H7B	−0.0741	1.0730	0.0535	0.037*	0.236 (7)
C8B	0.0761 (13)	1.0252 (15)	0.0438 (7)	0.032 (4)	0.236 (7)
H8B	0.1289	1.0836	0.0332	0.039*	0.236 (7)
C9B	0.1249 (15)	0.9701 (18)	0.1210 (8)	0.031 (4)	0.236 (7)
C10B	0.2263 (15)	0.9117 (18)	0.1355 (9)	0.039 (5)	0.236 (7)
C11B	0.2747 (19)	0.831 (2)	0.1938 (10)	0.041 (7)	0.236 (7)
C12B	0.221 (3)	0.803 (4)	0.2426 (19)	0.0402 (13)	0.236 (7)
C13B	0.124 (2)	0.869 (3)	0.2314 (14)	0.046 (7)	0.236 (7)
C14B	0.0729 (16)	0.943 (2)	0.1698 (12)	0.039 (5)	0.236 (7)
N1	0.6965 (4)	−0.1635 (3)	0.7554 (2)	0.0575 (11)
N2	0.3935 (3)	0.4660 (3)	0.42034 (19)	0.0532 (10)
C15	0.5952 (5)	−0.1261 (4)	0.7446 (2)	0.0603 (14)
H15	0.5652	−0.1435	0.7808	0.072*
C16	0.5307 (4)	−0.0626 (4)	0.6829 (2)	0.0563 (13)
H16	0.4600	−0.0371	0.6786	0.068*
C17	0.5717 (4)	−0.0373 (4)	0.6279 (2)	0.0451 (12)
C18	0.6795 (4)	−0.0707 (4)	0.6398 (2)	0.0518 (13)
H18	0.7123	−0.0504	0.6054	0.062*
C19	0.7387 (4)	−0.1347 (4)	0.7035 (3)	0.0584 (13)
H19	0.8107	−0.1585	0.7102	0.070*
C20	0.4943 (4)	0.0110 (4)	0.5551 (2)	0.0503 (12)
H20	0.4289	0.0505	0.5610	0.060*
C21	0.5389 (4)	0.0970 (4)	0.5075 (2)	0.0455 (12)
H21	0.6186	0.1036	0.5285	0.055*
C22	0.4893 (4)	0.2312 (4)	0.4838 (2)	0.0433 (12)
C23	0.3978 (4)	0.2813 (4)	0.4957 (2)	0.0524 (13)
H23	0.3662	0.2371	0.5254	0.063*
C24	0.3535 (4)	0.3987 (4)	0.4627 (3)	0.0574 (13)
H24	0.2919	0.4311	0.4713	0.069*
C25	0.4812 (4)	0.4166 (4)	0.4106 (2)	0.0580 (14)
H25	0.5108	0.4626	0.3804	0.070*
C26	0.5329 (4)	0.3033 (4)	0.4409 (2)	0.0564 (13)
H26	0.5961	0.2760	0.4326	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.0633 (13)	0.0362 (10)	0.0451 (12)	0.0059 (7)	0.0004 (6)	0.0057 (5)
I2A	0.0658 (18)	0.0398 (9)	0.0336 (8)	0.0117 (9)	0.0044 (9)	0.0090 (6)
F1A	0.088 (4)	0.059 (4)	0.085 (4)	0.017 (3)	0.053 (3)	0.038 (3)
F2A	0.059 (3)	0.054 (3)	0.079 (3)	0.021 (2)	0.042 (2)	0.023 (2)
F3A	0.085 (5)	0.051 (3)	0.078 (3)	0.023 (3)	0.054 (3)	0.028 (2)
F4A	0.071 (4)	0.055 (4)	0.094 (4)	0.030 (3)	0.045 (3)	0.032 (3)
F5A	0.051 (3)	0.067 (2)	0.050 (2)	0.015 (3)	0.021 (2)	0.0258 (18)
F6A	0.053 (4)	0.065 (4)	0.060 (3)	0.021 (3)	0.020 (3)	0.023 (3)
F7A	0.077 (3)	0.070 (4)	0.053 (3)	0.028 (3)	0.038 (2)	0.024 (2)
F8A	0.061 (3)	0.073 (3)	0.060 (3)	0.027 (3)	0.027 (2)	0.024 (2)
C1A	0.040 (4)	0.025 (4)	0.038 (5)	0.000 (3)	0.003 (3)	−0.001 (3)
C2A	0.046 (4)	0.033 (3)	0.045 (5)	−0.001 (3)	0.015 (3)	0.009 (3)
C3A	0.043 (4)	0.033 (3)	0.040 (3)	0.004 (2)	0.021 (2)	0.008 (2)
C4A	0.039 (4)	0.032 (3)	0.029 (3)	0.000 (2)	0.010 (3)	0.003 (2)
C5A	0.048 (4)	0.033 (3)	0.039 (4)	0.002 (3)	0.019 (3)	0.004 (3)
C6A	0.045 (5)	0.042 (4)	0.047 (5)	0.010 (3)	0.016 (4)	0.004 (4)
C7A	0.037 (4)	0.029 (3)	0.035 (3)	0.002 (2)	0.007 (3)	0.009 (2)
C8A	0.038 (4)	0.033 (3)	0.034 (3)	0.006 (2)	0.010 (2)	0.010 (2)
C9A	0.044 (3)	0.027 (3)	0.031 (3)	0.003 (3)	0.009 (3)	0.006 (2)
C10A	0.047 (4)	0.039 (4)	0.032 (3)	0.006 (3)	0.013 (3)	0.005 (3)
C11A	0.049 (4)	0.030 (4)	0.038 (3)	0.012 (3)	0.012 (3)	0.003 (3)
C12A	0.054 (4)	0.032 (2)	0.031 (2)	0.008 (3)	0.010 (2)	0.0020 (17)
C13A	0.055 (4)	0.030 (4)	0.034 (4)	0.005 (3)	0.017 (3)	0.005 (3)
C14A	0.054 (4)	0.036 (4)	0.039 (3)	0.011 (3)	0.018 (3)	0.010 (3)
I1B	0.049 (3)	0.023 (2)	0.0350 (19)	0.010 (2)	0.004 (2)	0.0101 (17)
I2B	0.053 (2)	0.034 (3)	0.036 (2)	0.0027 (19)	0.0104 (17)	0.0051 (18)
F1B	0.075 (11)	0.059 (13)	0.091 (12)	0.032 (9)	0.058 (10)	0.045 (9)
F2B	0.060 (9)	0.071 (10)	0.065 (9)	0.030 (8)	0.043 (7)	0.019 (8)
F3B	0.074 (12)	0.057 (9)	0.055 (7)	0.022 (7)	0.049 (9)	0.019 (6)
F4B	0.085 (11)	0.053 (12)	0.091 (13)	0.043 (8)	0.062 (10)	0.029 (9)
F5B	0.046 (9)	0.086 (9)	0.055 (7)	0.024 (8)	0.023 (7)	0.027 (6)
F6B	0.062 (9)	0.075 (13)	0.090 (13)	0.035 (7)	0.027 (8)	0.031 (9)
F7B	0.107 (12)	0.086 (16)	0.085 (12)	0.040 (10)	0.064 (10)	0.044 (10)
F8B	0.059 (8)	0.077 (11)	0.062 (9)	0.031 (8)	0.033 (6)	0.020 (7)
C1B	0.048 (14)	0.035 (13)	0.048 (17)	0.016 (12)	0.025 (15)	0.015 (14)
C2B	0.046 (11)	0.036 (9)	0.048 (13)	0.008 (8)	0.027 (10)	0.013 (9)
C3B	0.043 (4)	0.033 (3)	0.040 (3)	0.004 (2)	0.021 (2)	0.008 (2)
C4B	0.040 (9)	0.026 (6)	0.028 (9)	0.007 (6)	0.020 (8)	0.002 (5)
C5B	0.068 (13)	0.037 (8)	0.061 (13)	0.028 (8)	0.048 (12)	0.018 (8)
C6B	0.043 (13)	0.025 (8)	0.039 (12)	0.011 (8)	0.020 (11)	0.005 (8)
C7B	0.042 (9)	0.024 (6)	0.028 (8)	0.003 (5)	0.014 (6)	−0.001 (5)
C8B	0.036 (8)	0.024 (7)	0.038 (7)	−0.001 (6)	0.012 (6)	0.006 (6)
C9B	0.037 (8)	0.022 (9)	0.036 (6)	0.004 (7)	0.013 (5)	0.005 (6)
C10B	0.040 (8)	0.035 (10)	0.040 (7)	0.010 (7)	0.013 (6)	0.006 (7)
C11B	0.053 (9)	0.032 (13)	0.036 (8)	0.014 (8)	0.012 (7)	0.007 (9)
C12B	0.054 (4)	0.032 (2)	0.031 (2)	0.008 (3)	0.010 (2)	0.0020 (17)
C13B	0.062 (8)	0.042 (14)	0.038 (8)	0.014 (9)	0.021 (7)	0.006 (8)
C14B	0.043 (8)	0.034 (11)	0.045 (8)	0.011 (7)	0.022 (6)	0.010 (7)
N1	0.073 (3)	0.045 (2)	0.040 (2)	0.004 (2)	−0.001 (2)	0.0052 (18)
N2	0.067 (3)	0.036 (2)	0.048 (2)	0.006 (2)	0.008 (2)	0.0035 (18)
C15	0.085 (4)	0.054 (3)	0.037 (3)	0.004 (3)	0.013 (3)	0.009 (2)
C16	0.068 (3)	0.052 (3)	0.044 (3)	0.007 (2)	0.011 (3)	−0.001 (2)
C17	0.058 (3)	0.026 (2)	0.040 (2)	0.007 (2)	0.002 (2)	0.0005 (19)
C18	0.071 (4)	0.035 (2)	0.046 (3)	−0.007 (2)	0.016 (3)	0.006 (2)
C19	0.057 (3)	0.048 (3)	0.058 (3)	0.006 (2)	0.002 (3)	0.003 (3)
C20	0.065 (3)	0.036 (2)	0.041 (2)	0.008 (2)	0.006 (2)	0.001 (2)
C21	0.053 (3)	0.032 (2)	0.043 (2)	0.002 (2)	0.005 (2)	0.002 (2)
C22	0.058 (3)	0.029 (2)	0.031 (2)	0.003 (2)	−0.001 (2)	−0.0002 (18)
C23	0.068 (4)	0.042 (3)	0.046 (3)	−0.007 (3)	0.018 (2)	0.007 (2)
C24	0.062 (3)	0.041 (3)	0.065 (3)	0.005 (2)	0.014 (3)	0.002 (3)
C25	0.085 (4)	0.039 (3)	0.050 (3)	−0.003 (3)	0.022 (3)	0.011 (2)
C26	0.074 (4)	0.037 (2)	0.053 (3)	0.003 (2)	0.015 (3)	0.005 (2)

Geometric parameters (Å, º) top

I1A—C1A	2.105 (6)	C4B—C5B	1.398 (16)
I2A—C12A	2.102 (6)	C4B—C7B	1.529 (15)
F1A—C2A	1.348 (8)	C5B—C6B	1.365 (15)
F2A—C3A	1.348 (6)	C7B—H7B	0.9800
F3A—C5A	1.333 (7)	C7B—C8B	1.534 (16)
F4A—C6A	1.350 (8)	C7B—C8Bⁱ	1.60 (2)
F5A—C10A	1.355 (7)	C8B—C7Bⁱ	1.60 (2)
F6A—C11A	1.344 (7)	C8B—H8B	0.9800
F7A—C13A	1.346 (8)	C8B—C9B	1.535 (15)
F8A—C14A	1.360 (7)	C9B—C10B	1.385 (16)
C1A—C2A	1.380 (8)	C9B—C14B	1.366 (17)
C1A—C6A	1.371 (8)	C10B—C11B	1.380 (15)
C2A—C3A	1.354 (7)	C11B—C12B	1.381 (16)
C3A—C4A	1.391 (8)	C12B—C13B	1.377 (16)
C4A—C5A	1.394 (9)	C13B—C14B	1.388 (16)
C4A—C7A	1.520 (6)	N1—C15	1.316 (6)
C5A—C6A	1.379 (8)	N1—C19	1.336 (6)
C7A—H7A	0.9800	N2—C24	1.308 (6)
C7A—C8Aⁱ	1.588 (7)	N2—C25	1.316 (6)
C7A—C8A	1.552 (7)	C15—H15	0.9300
C8A—C7Aⁱ	1.588 (7)	C15—C16	1.379 (6)
C8A—H8A	0.9800	C16—H16	0.9300
C8A—C9A	1.525 (7)	C16—C17	1.371 (6)
C9A—C10A	1.375 (8)	C17—C18	1.381 (6)
C9A—C14A	1.385 (9)	C17—C20	1.525 (6)
C10A—C11A	1.386 (7)	C18—H18	0.9300
C11A—C12A	1.381 (8)	C18—C19	1.389 (6)
C12A—C13A	1.366 (8)	C19—H19	0.9300
C13A—C14A	1.377 (7)	C20—H20	0.9800
I1B—C1B	2.114 (14)	C20—C21ⁱⁱ	1.596 (5)
I2B—C12B	2.116 (14)	C20—C21	1.525 (6)
F1B—C2B	1.345 (16)	C21—C20ⁱⁱ	1.596 (5)
F2B—C3B	1.350 (15)	C21—H21	0.9800
F3B—C5B	1.334 (16)	C21—C22	1.520 (5)
F4B—C6B	1.352 (16)	C22—C23	1.381 (6)
F5B—C10B	1.357 (16)	C22—C26	1.369 (7)
F6B—C11B	1.341 (16)	C23—H23	0.9300
F7B—C13B	1.346 (16)	C23—C24	1.392 (6)
F8B—C14B	1.355 (16)	C24—H24	0.9300
C1B—C2B	1.381 (15)	C25—H25	0.9300
C1B—C6B	1.373 (15)	C25—C26	1.370 (6)
C2B—C3B	1.369 (15)	C26—H26	0.9300
C3B—C4B	1.387 (16)

C2A—C1A—I1A	121.8 (5)	C8Bⁱ—C7B—H7B	109.4
C6A—C1A—I1A	122.6 (6)	C8B—C7B—C8Bⁱ	89.1 (11)
C6A—C1A—C2A	115.4 (6)	C7B—C8B—C7Bⁱ	90.9 (11)
F1A—C2A—C1A	119.4 (6)	C7B—C8B—H8B	110.0
F1A—C2A—C3A	118.5 (6)	C7Bⁱ—C8B—H8B	110.0
C3A—C2A—C1A	122.1 (7)	C7B—C8B—C9B	121.4 (14)
F2A—C3A—C2A	118.7 (6)	C9B—C8B—C7Bⁱ	113.0 (12)
F2A—C3A—C4A	118.0 (5)	C9B—C8B—H8B	110.0
C2A—C3A—C4A	123.3 (6)	C10B—C9B—C8B	114.3 (14)
C3A—C4A—C5A	114.6 (5)	C14B—C9B—C8B	128.5 (15)
C3A—C4A—C7A	116.5 (6)	C14B—C9B—C10B	115.2 (13)
C5A—C4A—C7A	128.5 (6)	F5B—C10B—C9B	118.6 (13)
F3A—C5A—C4A	121.1 (6)	F5B—C10B—C11B	116.8 (15)
F3A—C5A—C6A	117.8 (7)	C11B—C10B—C9B	124.6 (15)
C6A—C5A—C4A	121.2 (6)	F6B—C11B—C10B	119.0 (17)
F4A—C6A—C1A	119.8 (6)	F6B—C11B—C12B	121.3 (17)
F4A—C6A—C5A	117.0 (6)	C10B—C11B—C12B	119.6 (16)
C1A—C6A—C5A	123.2 (7)	C11B—C12B—I2B	121.8 (13)
C4A—C7A—H7A	109.6	C13B—C12B—I2B	122.3 (13)
C4A—C7A—C8Aⁱ	114.0 (4)	C13B—C12B—C11B	115.9 (14)
C4A—C7A—C8A	122.5 (5)	F7B—C13B—C12B	117.4 (16)
C8A—C7A—H7A	109.6	F7B—C13B—C14B	118.1 (17)
C8Aⁱ—C7A—H7A	109.6	C12B—C13B—C14B	123.3 (16)
C8A—C7A—C8Aⁱ	89.8 (4)	F8B—C14B—C9B	123.9 (14)
C7A—C8A—C7Aⁱ	90.2 (4)	F8B—C14B—C13B	115.1 (15)
C7Aⁱ—C8A—H8A	110.9	C9B—C14B—C13B	120.8 (15)
C7A—C8A—H8A	110.9	C15—N1—C19	116.9 (4)
C9A—C8A—C7Aⁱ	113.4 (4)	C24—N2—C25	115.7 (4)
C9A—C8A—C7A	119.0 (5)	N1—C15—H15	117.9
C9A—C8A—H8A	110.9	N1—C15—C16	124.1 (5)
C10A—C9A—C8A	124.4 (6)	C16—C15—H15	117.9
C10A—C9A—C14A	113.9 (5)	C15—C16—H16	120.3
C14A—C9A—C8A	120.3 (6)	C17—C16—C15	119.5 (5)
F5A—C10A—C9A	120.1 (5)	C17—C16—H16	120.3
F5A—C10A—C11A	115.8 (6)	C16—C17—C18	117.1 (4)
C9A—C10A—C11A	123.9 (6)	C16—C17—C20	119.0 (5)
F6A—C11A—C10A	119.0 (6)	C18—C17—C20	123.6 (4)
F6A—C11A—C12A	120.5 (5)	C17—C18—H18	120.2
C12A—C11A—C10A	120.4 (6)	C17—C18—C19	119.7 (5)
C11A—C12A—I2A	120.5 (5)	C19—C18—H18	120.2
C13A—C12A—I2A	122.6 (5)	N1—C19—C18	122.6 (5)
C13A—C12A—C11A	116.7 (6)	N1—C19—H19	118.7
F7A—C13A—C12A	120.9 (5)	C18—C19—H19	118.7
F7A—C13A—C14A	117.3 (6)	C17—C20—H20	110.6
C12A—C13A—C14A	121.8 (7)	C17—C20—C21ⁱⁱ	114.6 (3)
F8A—C14A—C9A	118.4 (5)	C17—C20—C21	119.3 (4)
F8A—C14A—C13A	118.3 (6)	C21—C20—H20	110.6
C13A—C14A—C9A	123.0 (6)	C21ⁱⁱ—C20—H20	110.6
C2B—C1B—I1B	126.1 (13)	C21—C20—C21ⁱⁱ	89.6 (3)
C6B—C1B—I1B	118.7 (12)	C20—C21—C20ⁱⁱ	90.4 (3)
C6B—C1B—C2B	115.1 (14)	C20ⁱⁱ—C21—H21	110.2
F1B—C2B—C1B	118.7 (16)	C20—C21—H21	110.2
F1B—C2B—C3B	118.9 (16)	C22—C21—C20	119.9 (4)
C3B—C2B—C1B	122.3 (16)	C22—C21—C20ⁱⁱ	114.3 (3)
F2B—C3B—C2B	118.3 (15)	C22—C21—H21	110.2
F2B—C3B—C4B	119.2 (14)	C23—C22—C21	125.6 (4)
C2B—C3B—C4B	122.2 (15)	C26—C22—C21	117.0 (5)
C3B—C4B—C5B	115.1 (12)	C26—C22—C23	117.1 (4)
C3B—C4B—C7B	123.0 (15)	C22—C23—H23	120.4
C5B—C4B—C7B	121.1 (15)	C22—C23—C24	119.1 (5)
F3B—C5B—C4B	118.5 (14)	C24—C23—H23	120.4
F3B—C5B—C6B	120.1 (16)	N2—C24—C23	123.8 (5)
C6B—C5B—C4B	121.1 (15)	N2—C24—H24	118.1
F4B—C6B—C1B	118.6 (16)	C23—C24—H24	118.1
F4B—C6B—C5B	117.8 (16)	N2—C25—H25	117.1
C5B—C6B—C1B	123.6 (16)	N2—C25—C26	125.7 (5)
C4B—C7B—H7B	109.4	C26—C25—H25	117.1
C4B—C7B—C8Bⁱ	117.5 (14)	C22—C26—C25	118.6 (5)
C4B—C7B—C8B	120.4 (14)	C22—C26—H26	120.7
C8B—C7B—H7B	109.4	C25—C26—H26	120.7

I1A—C1A—C2A—F1A	4.3 (9)	F6B—C11B—C12B—I2B	−5 (5)
I1A—C1A—C2A—C3A	−175.5 (6)	F6B—C11B—C12B—C13B	175 (3)
I1A—C1A—C6A—F4A	−5.8 (15)	F7B—C13B—C14B—F8B	9 (4)
I1A—C1A—C6A—C5A	173.9 (9)	F7B—C13B—C14B—C9B	−177 (3)
I2A—C12A—C13A—F7A	3.9 (16)	C1B—C2B—C3B—F2B	178.3 (18)
I2A—C12A—C13A—C14A	−174.6 (8)	C1B—C2B—C3B—C4B	4.8 (16)
F1A—C2A—C3A—F2A	0.8 (9)	C2B—C1B—C6B—F4B	175 (3)
F1A—C2A—C3A—C4A	−176.9 (8)	C2B—C1B—C6B—C5B	−4 (4)
F2A—C3A—C4A—C5A	177.2 (6)	C2B—C3B—C4B—C5B	−9 (3)
F2A—C3A—C4A—C7A	−9.0 (9)	C2B—C3B—C4B—C7B	160.3 (17)
F3A—C5A—C6A—F4A	1.2 (15)	C3B—C4B—C5B—F3B	−179 (2)
F3A—C5A—C6A—C1A	−178.5 (10)	C3B—C4B—C5B—C6B	7 (4)
F5A—C10A—C11A—F6A	1.8 (7)	C3B—C4B—C7B—C8B	42 (3)
F5A—C10A—C11A—C12A	−174.9 (9)	C3B—C4B—C7B—C8Bⁱ	−64 (3)
F6A—C11A—C12A—I2A	−4.0 (14)	C4B—C5B—C6B—F4B	180 (3)
F6A—C11A—C12A—C13A	−179.4 (10)	C4B—C5B—C6B—C1B	−1 (5)
F7A—C13A—C14A—F8A	−0.2 (11)	C4B—C7B—C8B—C7Bⁱ	−121.7 (18)
F7A—C13A—C14A—C9A	−175.0 (7)	C4B—C7B—C8B—C9B	120.4 (19)
C1A—C2A—C3A—F2A	−179.3 (6)	C5B—C4B—C7B—C8B	−149 (2)
C1A—C2A—C3A—C4A	2.9 (8)	C5B—C4B—C7B—C8Bⁱ	105 (3)
C2A—C1A—C6A—F4A	177.7 (9)	C6B—C1B—C2B—F1B	−175 (3)
C2A—C1A—C6A—C5A	−2.6 (15)	C6B—C1B—C2B—C3B	2 (2)
C2A—C3A—C4A—C5A	−5.0 (9)	C7B—C4B—C5B—F3B	11 (4)
C2A—C3A—C4A—C7A	168.7 (5)	C7B—C4B—C5B—C6B	−163 (3)
C3A—C4A—C5A—F3A	−177.8 (6)	C7B—C8B—C9B—C10B	176.7 (13)
C3A—C4A—C5A—C6A	3.4 (11)	C7Bⁱ—C8B—C9B—C10B	70.4 (18)
C3A—C4A—C7A—C8A	−176.7 (5)	C7Bⁱ—C8B—C9B—C14B	−92 (2)
C3A—C4A—C7A—C8Aⁱ	−70.5 (7)	C7B—C8B—C9B—C14B	14 (3)
C4A—C5A—C6A—F4A	−180.0 (9)	C8Bⁱ—C7B—C8B—C7Bⁱ	−0.003 (1)
C4A—C5A—C6A—C1A	0.3 (16)	C8Bⁱ—C7B—C8B—C9B	−117.9 (18)
C4A—C7A—C8A—C7Aⁱ	118.7 (6)	C8B—C9B—C10B—F5B	17.3 (18)
C4A—C7A—C8A—C9A	−124.1 (6)	C8B—C9B—C10B—C11B	−164.6 (15)
C5A—C4A—C7A—C8A	−4.0 (9)	C8B—C9B—C14B—F8B	−19 (3)
C5A—C4A—C7A—C8Aⁱ	102.2 (8)	C8B—C9B—C14B—C13B	167 (2)
C6A—C1A—C2A—F1A	−179.2 (10)	C9B—C10B—C11B—F6B	−180 (2)
C6A—C1A—C2A—C3A	1.0 (9)	C9B—C10B—C11B—C12B	0 (2)
C7A—C4A—C5A—F3A	9.4 (11)	C10B—C9B—C14B—F8B	178.3 (19)
C7A—C4A—C5A—C6A	−169.4 (9)	C10B—C9B—C14B—C13B	4 (3)
C7A—C8A—C9A—C10A	−40.1 (7)	C10B—C11B—C12B—I2B	175 (2)
C7Aⁱ—C8A—C9A—C10A	64.0 (7)	C10B—C11B—C12B—C13B	−4 (5)
C7Aⁱ—C8A—C9A—C14A	−101.5 (7)	C11B—C12B—C13B—F7B	176 (3)
C7A—C8A—C9A—C14A	154.3 (6)	C11B—C12B—C13B—C14B	9 (6)
C8Aⁱ—C7A—C8A—C7Aⁱ	0.000 (1)	C12B—C13B—C14B—F8B	176 (3)
C8Aⁱ—C7A—C8A—C9A	117.1 (6)	C12B—C13B—C14B—C9B	−9 (5)
C8A—C9A—C10A—F5A	12.3 (8)	C14B—C9B—C10B—F5B	−177.6 (19)
C8A—C9A—C10A—C11A	−163.1 (6)	C14B—C9B—C10B—C11B	0.4 (15)
C8A—C9A—C14A—F8A	−13.2 (9)	N1—C15—C16—C17	1.1 (7)
C8A—C9A—C14A—C13A	161.7 (7)	N2—C25—C26—C22	2.0 (7)
C9A—C10A—C11A—F6A	177.4 (6)	C15—N1—C19—C18	−1.3 (7)
C9A—C10A—C11A—C12A	0.7 (9)	C15—C16—C17—C18	−3.9 (6)
C10A—C9A—C14A—F8A	179.9 (6)	C15—C16—C17—C20	169.4 (4)
C10A—C9A—C14A—C13A	−5.3 (9)	C16—C17—C18—C19	4.1 (6)
C10A—C11A—C12A—I2A	172.7 (7)	C16—C17—C20—C21ⁱⁱ	−103.9 (5)
C10A—C11A—C12A—C13A	−2.7 (15)	C16—C17—C20—C21	151.7 (4)
C11A—C12A—C13A—F7A	179.2 (9)	C17—C18—C19—N1	−1.6 (7)
C11A—C12A—C13A—C14A	0.8 (17)	C17—C20—C21—C20ⁱⁱ	118.3 (4)
C12A—C13A—C14A—F8A	178.3 (10)	C17—C20—C21—C22	−123.1 (4)
C12A—C13A—C14A—C9A	3.5 (14)	C18—C17—C20—C21ⁱⁱ	69.0 (6)
C14A—C9A—C10A—F5A	178.6 (6)	C18—C17—C20—C21	−35.4 (6)
C14A—C9A—C10A—C11A	3.3 (7)	C19—N1—C15—C16	1.6 (7)
I1B—C1B—C2B—F1B	9 (2)	C20—C17—C18—C19	−168.9 (4)
I1B—C1B—C2B—C3B	−173.8 (18)	C20—C21—C22—C23	−6.4 (6)
I1B—C1B—C6B—F4B	−8 (4)	C20ⁱⁱ—C21—C22—C23	99.1 (5)
I1B—C1B—C6B—C5B	172 (3)	C20ⁱⁱ—C21—C22—C26	−74.2 (5)
I2B—C12B—C13B—F7B	−3 (5)	C20—C21—C22—C26	−179.8 (4)
I2B—C12B—C13B—C14B	−170 (3)	C21ⁱⁱ—C20—C21—C20ⁱⁱ	0.001 (1)
F1B—C2B—C3B—F2B	−4 (3)	C21ⁱⁱ—C20—C21—C22	118.6 (4)
F1B—C2B—C3B—C4B	−178 (3)	C21—C22—C23—C24	−171.7 (4)
F2B—C3B—C4B—C5B	177 (2)	C21—C22—C26—C25	171.4 (4)
F2B—C3B—C4B—C7B	−13 (3)	C22—C23—C24—N2	0.0 (7)
F3B—C5B—C6B—F4B	6 (5)	C23—C22—C26—C25	−2.6 (6)
F3B—C5B—C6B—C1B	−174 (3)	C24—N2—C25—C26	−0.3 (7)
F5B—C10B—C11B—F6B	−2 (2)	C25—N2—C24—C23	−0.7 (6)
F5B—C10B—C11B—C12B	178 (3)	C26—C22—C23—C24	1.6 (6)

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y, −z+1.

Acknowledgements

We thank Drs A. E. Brummett and N. J. Schnicker for assistance with PyMOL.

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. DMR-1708673 to LRM).

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IUCrJ

Volume 5| Part 4| July 2018| Pages 491-496

ISSN: 2052-2525

https://doi.org/10.1107/S2052252518007583

CHEMISTRY | CRYSTENG

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research papers\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization

1. Introduction

2. Experimental

2.1. Materials and general methods

2.2. Synthesis of cocrystal (I4F16cb)·2(bpe)

2.3. X-ray crystallography

2.3.1. Crystal data for (I4F16cb)·2(bpe)

2.3.2. Crystal data for (I4F16cb)·2(tpcb)

3. Results and discussion

3.1. Halogen bonds in SCSC photo­dimerization

3.2. Crystal landscape of halogen bonds

3.3. Single-crystal reactivity and movements of halogen-bonded components

4. Conclusions

Supporting information

Acknowledgements

Funding information

References

research papers

2.2. Synthesis of cocrystal (I₄F₁₆cb)·2(bpe)

2.3.1. Crystal data for (I₄F₁₆cb)·2(bpe)

2.3.2. Crystal data for (I₄F₁₆cb)·2(tpcb)

3.1. Halogen bonds in SCSC photodimerization