4-Pyrrolidino­pyridine as halogen-bond acceptor in cocrystals

Bosch, E.

doi:10.1107/S2056989026006092

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Volume 82| Part 7| July 2026|

https://doi.org/10.1107/S2056989026006092

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4-Pyrrolidinopyridine as halogen-bond acceptor in cocrystals

Eric Bosch ^a ^*

^aDepartment of Chemistry and Biochemistry, Missouri State University, 901 South National Avenue, Springfield MO 65897, USA
^*Correspondence e-mail: [email protected]

Edited by J. Reibenspies, Texas A & M University, USA (Received 15 May 2026; accepted 9 June 2026; online 16 June 2026)

The potential of 4-pyrrolidinopyridine as halogen-bond acceptor is further explored and the structures of 1:1 cocrystals 1-iodo-3,5-dinitrobenzene–4-pyrrolidinopyridine, C₆H₃IN₂O₄·C₉H₁₂N₂, and 1-iodo-3,5-bis(trifluoromethyl)benzene–4-pyrrolidinopyridine C₈H₃F₆I·C₉H₁₂N₂, are reported. This is the first reported halogen-bonded cocrystal with 1-iodo-3,5-bis(trifluoromethyl)benzene. The halogen bonds in these structures have similar I⋯N separations of 2.871 (2) and 2.858 (4) Å, respectively, with C—I⋯N angles of 172.91 (9) and 171.38 (14)°, respectively. The components within the cocrystal 1-iodo-3,5-bisdinitrobenzene–4-pyrrolidinopyridine are coplanar and form sheets that π-stack with donor–acceptor, donor–donor and acceptor–acceptor interactions within the layers. In contrast, the components in the cocrystal 1-iodo-3,5-bis(trifluoromethyl)benzene–4-pyrrolidinopyridine are twisted with a dihedral angle of 44.052 (2)° between the pyridine and benzene rings and the donor and acceptor molecules are individually π-stacked with no donor–acceptor stacking interactions. Analysis of the intermolecular interaction energy between molecules within the crystal structures reveals that in cocrystal 1-iodo-3,5-dinitrobenzene–4-pyrrolidinopyridine the donor-acceptor π-stacking is the strongest interaction whereas in cocrystal 1-iodo-3,5-bis(trifluoromethyl)benzene–4-pyrrolidinopyridine, the head-to-tail π-stacking of the pyrrolidinopyridine molecules is the strongest interaction.

Keywords: crystal structure; halogen bond; cocrystal; 4-pyrrolidinopyridine; halogen bond acceptor; π-stacking.

CCDC references: 2560994; 2560993

1. Chemical context

Halogen bonding is now an accepted intermolecular force with a multitude of applications in the general field of supramolecular chemistry (Metrangolo & Resnati, 2008 ; Cavallo et al., 2016 ; Liu & Yang (2025 ). Electron-poor iodoarenes, for example polyfluoroiodobenzenes, are common halogen-bond donors often coupled with pyridines as halogen-bond acceptor. 4-(N,N-Dimethylamino)pyridine (4DMAP) is a strong base and in general forms stronger halogen bonds than other pyridines with lower I⋯N separations (Präsang et al., 2009 ). Thus, the I⋯N separation in the cocrystals formed between 1,2,4,5-tetrafluoro-3,6-diiodobenzene and 4DMAP and 4,4-bipyridine are 2.664 and 2.854 Å, respectively (Roper et al., 2010 ; Walsh et al., 2001 ). 4-Pyrrolidinopyridine, 4PYPY, is reported to be a slightly stronger base than 4DMAP (Kaljurand et al., 2005 ); however, few halogen-bonded cocrystals featuring 4PYPY as halogen-bond acceptor have been reported. These include the 1:1 cocrystal of 4PYPY with 4-bromo-2,2′,3,3′,5,5′,6,6′-octafluoro-4′-iodobiphenyl (Aakeroy et al., 2013 ) and the 1:1 and 1:2 halogen-bonded cocrystals of 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione (Nicolas et al., 2016 ). Recently, Rissanen and coworkers reported the complex of 4PYPY with N-iodosaccharin (Schumacher et al., 2024 ) and the complex 1-{[(diphenylphosphoryl)oxy]iodanyl}-4-(pyrrolidin-1-yl)-1-pyridine (Mohan et al., 2024 ) with exceptionally short I⋯N (4PYPY) distances. Here we report two cocrystals formed between halogen-bond donors 1-iodo-3,5-dinitrobenzene (DNIB) and 1-iodo-3,5-bis(trifluoromethyl)benzene (BTFIB) with 4PYPY as halogen-bond acceptor.

2. Molecular electrostatic potentials

The molecular electrostatic potentials (MEP) of the molecules in this study were calculated using the program Spartan '20 version 1.1.4 (Wavefunction, 2020 ) with density functional theory at the B3LYP-D3/6-311+G** level with an isovalue of 0.2 electrons bohr⁻³. The molecular electrostatic potentials for DNIB and BTFIB revealed that the σ-hole on the iodine atom in DNIB at 173.2 kJ mol⁻¹ is similar to that calculated for iodopentafluorobenzene using the same experimental conditions (174.6 kJ mol⁻¹). In contrast, the calculated σ-hole on the iodine atom in BTFIB at 146.6 kJ mol⁻¹ is similar to the weaker halogen-bond donors iodopentachlorobenezne (154.9 kJ mol⁻¹) and bromopentafluorobenzene (144.5 kJ mol⁻¹). The minimum negative electrostatic potential on the pyridine N atom in 4PYPY at −228 kJ mol⁻¹ is slightly more negative than that on 4DMAP, −217.4 kJ mol⁻¹ (Fig. 1).

Figure 1
Molecular electrostatic potential plots drawn over the 0.002 isodensity surface for (a) DNIB, (b) BTFIB, (c) 4PYPY, and (d) DMAP. Maxima are annotated for (a) and (b) and minima annotated for (c) and (d) in kJ mol⁻¹.

3. Structural commentary

The 1:1 cocrystal DNIB·4PYPY crystallizes in the triclinic space group P $[\overline{1}]$ with one molecule of each component in the asymmetric unit as shown in Fig. 2. The halogen-bond donor and acceptor moieties are essentially coplanar with a dihedral angle of 7.38 (14)° between the pyridyl and benzene rings. The I⋯N separation is 2.871 (2) Å, 77.6% of the sum of the van der Waals radii (Alvarez, 2013 ) and the C—I⋯N angle is essentially linear at 172.91 (8)°.

Figure 2
Asymmetric unit of the cocrystal DNIB·4PYPY with displacement ellipsoids drawn at the 50% level and the halogen bond shown as a grey dashed line.

The 1:1 cocrystal BTFIB·4PYPY crystallizes in the triclinic space group P $[\overline{1}]$ with one molecule of each component in the asymmetric unit as shown in Fig. 3. The two moieties are not coplanar with a dihedral angle of 44.052 (2)° between the pyridyl and benzene rings. The I⋯N separation is 2.858 (4) Å, 77.2% of the sum of the van der Waals radii and the C—I⋯N angle is 171.38 (14)°.

Figure 3
Asymmetric unit of the cocrystal TFMIB·4PYPY with displacement ellipsoids drawn at the 50% level and the halogen bond shown as a dashed line.

These cocrystals confirm the viability of 4PYPY as a good halogen-bond acceptor. It is interesting, however, to note that the halogen-bond distance, or I⋯N separation, in the two complexes is similar for the halogen bond donors, at 2.871 (2) and 2.858 (4) Å, despite the large variation in the σ-hole on these halogen-bond donors of 173.2 and 146.6 kJ mol⁻¹, respectively. This reasonably highlights the role that other crystal packing interactions have in modulating the I⋯N separation. Also, comparison of the cocrystal DNIB·4PYPY with the previously reported cocrystal DNIB·DMAP (Nwachukwu et al., 2018 ) reveals that the I⋯N separation in DNIB·DMAP is slightly longer at 2.8936 (16) Å than those reported here for DNIB·4PYPY, in line with the more negative electrostatic potential of 4PYPY.

4. Supramolecular features

The halogen-bonded pairs of molecules in cocrystal DNIB·4PYPY pack side-by-side to form planar sheets as shown in Fig. 4. The weak bifurcated C—H⋯O(nitro) interaction between adjacent molecules within each plane that is parallel to the b-axis (Bosch et al., 2022 ).

Figure 4
Partial view of one of the planar sheets within the cocrystal DNIB·4PYPY. The halogen bond is shown as a grey dashed line.

The halogen-bonded complexes are head-to-tail π-stacked where the closest interaction is between a halogen-bonded donor–acceptor (DA) pair with a centroid–centroid distance and closest perpendicular distances between the pyridyl and phenyl groups of 3.9166 (16) and 3.3735 (10) Å, respectively. Each halogen-bonded 4PYPY molecule is also offset π-stacked in a head-to-tail orientation with another 4PYPY with closest perpendicular distance and centroid-to-centroid distances of 3.8823 (10) and 4.9846 (17) Å, respectively. Accordingly, each DNIB molecule is also offset π-stacked in a head-to-tail orientation with another DNIB molecule with a centroid-to-centroid distance of 4.4801 (16) Å (Fig. 5). Thus, while all halogen-bonded pairs of molecules within each plane have the same orientation, the orientation of the molecules in the π-stacked sheets alternates. Details of hydrogen-bonding interactions are given in Table 1.

Table 1
Hydrogen-bond geometry (Å, °) for DNIB·4PYPY

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.61	3.499 (3)	156
C7—H7B⋯I1ⁱⁱ	0.99	3.22	4.104 (3)	150
C8—H8A⋯O2ⁱⁱⁱ	0.99	2.55	3.301 (4)	133
C8—H8A⋯O4^iv	0.99	2.61	3.420 (4)	140
C9—H9A⋯O4^v	0.99	2.61	3.186 (3)	117
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 5
(A) Oblique partial view of the π-stacking within cocrystal DNIB·4PYPY. The halogen bond and the DNIB⋯4PYPY centroid-to-centroid π-stacking interaction are shown as grey dashed lines and labelled a and b, respectively. Centroid-to-centroid connections are also shown as blue dashed lines for π-stacking interactions between two 4PYPY molecules and maroon dashed line between two DNIB molecules. (B) Side view of the molecules in (A) with the molecules rotated into the horizontal plane.

The crystal packing within cocrystal BTFIB·4PYPY is significantly different to that within DNIB·4PYPY with the two components separately π-stacking while forming corrugated sheets. The individual molecules in each stack are offset π-stacked, with a head-to-tail arrangement as shown with the view along the b-axis direction (Fig. 6). There are two unique π-stacking interactions within the stacks of each component of cocrystal BTFIB·4PYPY. With respect to the 4PYPY molecules the separations are similar, with pyridine centroid-to-centroid distances of 4.512 (3) and 4.796 (3) Å, and interplanar distances of 3.5831 (18) and 3.5377 (18) Å. The BTFIB molecules are also π-stacked with two distinct stacking arrangements with interplanar distances of 3.6688 (17) and 3.9066 (17) Å. The first of these π-stacked molecules is rotated through 180° with a benzene centroid-to-centroid distance of 3.670 (2) Å indicating no shift with maximal surface–surface interaction. The second π-stacked BTFIB molecule while also rotated through 180° is shifted with a higher benzene centroid-to-centroid distance of 4.684 (2) Å. There are two close C—H⋯F interactions with H⋯F separations marginally less than the sum of the van der Waals radii. Details of hydrogen-bonding interactions are given in Table 2.

Table 2
Hydrogen-bond geometry (Å, °) for BTFIB·4PYPY

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯F6ⁱ	0.99	2.54	3.465 (5)	156
C1—H1⋯F5ⁱⁱ	0.95	2.59	3.265 (5)	128
Symmetry codes: (i) ; (ii) .

Figure 6
Partial view of the packing within cocrystal BTFIB·4PYPY viewed along the b-axis direction.

5. Hirshfeld surface analysis

The program CrystalExplorer21 (Spackman et al., 2021 ) was used to calculate the Hirshfeld surface using density functional theory at the B3LYP/DGDZVP level. The fingerprint plots derived from the Hirshfeld surface provide a breakdown of the intermolecular contacts in terms of the atoms within the Hirshfeld surface and atoms outside the surface.

The Hirshfeld surface analysis of a 4PYPY molecule within the DNIB·4PYPY cocrystal is shown in Fig. 7. The red colour indicates an interaction in which the atom-to-atom separation is less than the sum of the van der Waals radii. The N⋯I halogen bond represents the closest interaction, while the pale-red areas correspond to C—H⋯O interactions. Based on fingerprint analysis wherein the atom-to-atom surface contacts are analysed by element, the N⋯I contact corresponds to 3.3% of the surface area of the 4PYPY molecule. The most common atom-to-atom interaction is H⋯H, accounting for 46.2% of surface-to-surface interactions with the H⋯O and H⋯C interactions accounting for 20.9 and 14.3% of the surface area, respectively.

Figure 7
Plot of the Hirshfeld surface of 4PYPY molecule within the DNIB·4PYPY cocrystal with d_norm mapped over the surface. Included are three molecules with strong interactions with the central 4PYPY molecule with the N⋯I halogen bond and the H⋯O interaction shown as purple and grey dashed lines, respectively.

6. Intermolecular energy of interaction

The program CrystalExplorer21 was also used to calculate the intermolecular energies of interaction within each crystal structure (Mackenzie et al., 2017 ). The strongest intermolecular interaction in the cocrystal DNIB·4PYPY is the π-stacking between the two components. In Fig. 8(a) this is shown as the interaction between the central 4PYPY molecule and the green molecule labelled PSCT. This interaction exhibits the highest dispersion component and moderate electrostatic component to the overall intermolecular interaction energy of −45.5 kJ mol⁻¹. The head-to-tail π-stacking between two 4PYPY molecules, shown in Fig. 8(a) as the interaction between the central molecule and the molecule labelled PSPY, turquoise, has lower dispersion and electrostatic components with a total intermolecular interaction energy of −42.5 kJ mol⁻¹. In contrast, the intermolecular interaction between the halogen bonded molecules has the lowest surface area contact resulting in the lowest dispersion component. This interaction does have the highest electrostatic component with an overall intermolecular interaction energy of −29.9 kJ mol⁻¹. The π-stacking between two DNIB molecules has interaction energy of −26.1 kJ mol⁻¹ shown as PSDN in Fig. 8(b).

Figure 8
(a) Plot showing the three molecules with the strongest intermolecular interaction energy to the central 4PYPY molecule, shown with the Hirshfeld surface, in cocrystal DNIB·4PYPY. The halogen bonded molecule is shown in red and labelled XB, π-stacked DNIB shown green and labelled PSCT, and the head-to-tail π-stacked 4PYPY shown in blue labelled PSPY. (b) Plot showing the three molecules with the strongest intermolecular interaction energy to the central DNIB molecule in cocrystal DNIB·4PYPY. Note that colours in (b) are not related to colours in (a). The turquoise molecule labelled PSDN corresponds to an offset π-stacked DNIB molecule.

The intermolecular interaction energies within the BTFIB·4PYPY cocrystal were similarly calculated individually for each component. In this cocrystal, the two unique 4PYPY π-stacking interactions, labelled PSPY1 and PSPY2 in Fig. 9(a), are the strongest with interaction energies of −43.4 and −40.5 kJ mol⁻¹, respectively. The π-stacked BTFIB molecules with maximum overlap have interaction energy of −38.4 kJ mol⁻¹ illustrated as PSTF1 in Fig. 9(b). The offset π-stacked BTFIB⋯BTFIB interaction, PSTF2 in Fig. 9(b), has lower electrostatic and dispersion components to the overall energy of interaction of −26.7 kJ mol⁻¹. The halogen-bond interaction, XB in Fig. 9(b), has the highest electrostatic component of the intermolecular interactions with an overall energy of interaction of −24.3 kJ mol⁻¹.

Figure 9
(a) Plot showing the two unique 4PYPY π-stacking interactions to the central 4PYPY molecule within cocrystal BTFIB·4PYPY. PSPY1 corresponds to the molecule with the higher degree of overlap. (b) Plot showing the three molecules with the strongest intermolecular interaction energy to the central BTFIB molecule in cocrystal BTFIB·4PYPY. Note that colours in (b) are not related to colours in (a). The dark-blue molecule labelled PSTF1 corresponds to the molecule with higher overlap, and the molecule XB is the 4PYPY molecule halogen bonded to the central BTFIB.

7. Database survey

While 1-iodo-3,5-dinitrobenzene is not a common halogen-bond donor, a search of the Cambridge Crystallographic Database (CSD, Version 6.0.1, Nov 2025; Groom et al., 2016 ) using Conquest Version 2025.3.0, Build 466532 (Bruno et al., 2002 ) for structures containing the DNIB halogen bonded to an amine yielded eight structures. Thus in 2009, Rissanen reported polymorphism in the 2:1 halogen-bonded cocrystals of DNIB with 1,4-diazabicyclo[2.2.2]octane (Raatikainen & Rissanen, 2009 ). This study also reported the 1:1 cocrystal DNIB with 4,4-bipyridine that featured both a halogen bond and a C—H⋯N hydrogen bond to the more acidic H atom between the two nitro substituents. In 2018, 1:1 halogen-bonded cocrystals of DNIB with the thiophene-substituted pyridines 4-([2,2′-bithiophen]-5-yl)pyridine and 4-[5-(furan-2-yl)thiophen-2-yl]pyridine were reported as part of a computational study of substituent and hybridization effects on halogen bonding (Nguyen et al., 2018 ). In the same year, we reported the structure of the cocrystal of DNIB with 4-(N,N-dimethylamino)pyridine (Nwachukwu et al., 2018). Desiraju and coworkers also incorporated halogen bonding to DNIB in their elegant study of cocrystallization and the formation of ternary cocrystals (Jain et al., 2021 ). In contrast, there are no halogen-bonding studies with 1-iodo-3,5-bis(trifluoromethyl)benzene, BTFIB, prior to this report.

8. Synthesis and crystallization

The compounds and solvents used in this study are commercially available and were used without purification. Equimolar amounts, 0.1 mmol, of each component were weighed and placed in a small screw-cap vial and dichloromethane added to effect complete solution of both compounds. The lid was loosely attached to permit slow evaporation of the solvent. Once crystals formed, the remaining solvent was removed and the crystals removed for X-ray studies. The mixture of 1-iodo-3,5-dinitrobenzene and 4-pyrrolidinopyridine, formed a mass of orange-coloured crystals, DNIB·4PYPY, the mixture 1-iodo-3,5-bis(trifluoromethyl)benzene and 4-pyrrolidinopyridine formed colourless crystals, BTFIB·4PYPY.

9. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The structure of BTFIB·4PYPY was solved with SHELXT in space group P $[\overline{1}]$ with two molecules of each component in the asymmetric unit. PLATON ADDSYM (Spek, 2003 ) was used to transform this to the structure containing only one molecule of each component in the same space group. H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and refined as riding with U_iso(H) = 1.2–1.5U_eq(C).

Table 3
Experimental details

	DNIB·4PYPY	BTFIB·4PYPY
Crystal data
Chemical formula	C₆H₃IN₂O₄·C₉H₁₂N₂	C₈H₃F₆I·C₉H₁₂N₂
M_r	442.21	488.21
Crystal system, space group	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$
Temperature (K)	100	100
a, b, c (Å)	7.9441 (14), 8.4866 (15), 12.139 (2)	7.9777 (4), 8.5138 (4), 14.1679 (7)
α, β, γ (°)	82.209 (2), 87.800 (2), 83.219 (2)	101.579 (1), 103.264 (1), 100.370 (1)
V (Å³)	805.0 (2)	891.40 (8)
Z	2	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	2.02	1.86
Crystal size (mm)	0.18 × 0.05 × 0.04	0.41 × 0.20 × 0.11

Data collection
Diffractometer	Bruker APEXI CCD	Bruker APEXI CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.565, 0.746	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8115, 3527, 3181	11576, 3979, 3517
R_int	0.025	0.021
(sin θ/λ)_max (Å⁻¹)	0.641	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.057, 1.04	0.042, 0.110, 1.03
No. of reflections	3527	3979
No. of parameters	217	235
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.53	2.23, −1.21
Computer programs: SMART and SAINT (Bruker, 2014 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and X-SEED-4 (Barbour, 2020 ).

Supporting information

CCDC references: 2560994; 2560993

Crystal structure: contains datablocks DNIB4PYPY, BTFIB4PYPY. DOI: https://doi.org/10.1107/S2056989026006092/jy2073sup1.cif

Structure factors: contains datablock DNIB4PYPY. DOI: https://doi.org/10.1107/S2056989026006092/jy2073DNIB4PYPYsup2.hkl

Structure factors: contains datablock BTFIB4PYPY. DOI: https://doi.org/10.1107/S2056989026006092/jy2073BTFIB4PYPYsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026006092/jy2073DNIB4PYPYsup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989026006092/jy2073BTFIB4PYPYsup5.cdx

checkCIF report

Computing details top

4-(Pyrrolidin-1-yl)pyridine–1-iodo-3,5-dinitrobenzene (1/1) (DNIB4PYPY) top

Crystal data top

C₆H₃IN₂O₄·C₉H₁₂N₂	Z = 2
M_r = 442.21	F(000) = 436
Triclinic, P1	D_x = 1.824 Mg m⁻³
a = 7.9441 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4866 (15) Å	Cell parameters from 4152 reflections
c = 12.139 (2) Å	θ = 2.4–27.1°
α = 82.209 (2)°	µ = 2.02 mm⁻¹
β = 87.800 (2)°	T = 100 K
γ = 83.219 (2)°	Block, red
V = 805.0 (2) Å³	0.18 × 0.05 × 0.04 mm

Data collection top

Bruker APEXI CCD diffractometer	3181 reflections with I > 2σ(I)
Detector resolution: 8.3660 pixels mm^-1	R_int = 0.025
φ and ω scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.565, T_max = 0.746	k = −10→10
8115 measured reflections	l = −15→15
3527 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0285P)² + 0.2789P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
3527 reflections	Δρ_max = 0.91 e Å⁻³
217 parameters	Δρ_min = −0.53 e Å⁻³
0 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
I1	0.39367 (2)	0.48998 (2)	0.65240 (2)	0.01837 (6)
O2	0.6369 (3)	1.0467 (2)	0.92236 (17)	0.0283 (5)
O3	0.8608 (3)	0.5175 (2)	1.08618 (16)	0.0275 (4)
O4	0.7828 (3)	0.3099 (2)	1.02383 (17)	0.0296 (5)
O1	0.4709 (3)	1.0748 (2)	0.78321 (19)	0.0346 (5)
N1	0.2416 (3)	0.3150 (3)	0.50366 (19)	0.0227 (5)
N2	0.0925 (3)	0.0008 (3)	0.29720 (19)	0.0192 (5)
N3	0.5626 (3)	0.9924 (3)	0.85229 (19)	0.0225 (5)
N4	0.7850 (3)	0.4544 (3)	1.02106 (19)	0.0209 (5)
C5	0.1385 (3)	0.1016 (3)	0.3650 (2)	0.0159 (5)
C10	0.5159 (3)	0.5906 (3)	0.7724 (2)	0.0163 (5)
C15	0.6085 (3)	0.4906 (3)	0.8549 (2)	0.0161 (5)
H15	0.617536	0.377528	0.857578	0.019*
C3	0.2955 (4)	0.1573 (3)	0.5187 (2)	0.0223 (6)
H3	0.370755	0.118433	0.577767	0.027*
C1	0.0823 (3)	0.2664 (3)	0.3493 (2)	0.0189 (5)
H1	0.007726	0.310176	0.290738	0.023*
C4	0.2489 (3)	0.0479 (3)	0.4543 (2)	0.0207 (5)
H4	0.290598	−0.062168	0.469952	0.025*
C6	0.1261 (4)	−0.1737 (3)	0.3195 (2)	0.0227 (6)
H6A	0.103579	−0.212086	0.398760	0.027*
H6B	0.245087	−0.210446	0.299989	0.027*
C11	0.5032 (3)	0.7561 (3)	0.7701 (2)	0.0174 (5)
H11	0.441806	0.825365	0.713548	0.021*
C12	0.5819 (3)	0.8174 (3)	0.8518 (2)	0.0174 (5)
C14	0.6874 (3)	0.5607 (3)	0.9333 (2)	0.0173 (5)
C2	0.1363 (3)	0.3640 (3)	0.4197 (2)	0.0213 (6)
H2	0.095426	0.474592	0.407427	0.026*
C13	0.6760 (3)	0.7230 (3)	0.9350 (2)	0.0191 (5)
H13	0.729706	0.768028	0.989943	0.023*
C7	0.0035 (4)	−0.2332 (4)	0.2450 (2)	0.0283 (6)
H7A	0.056018	−0.330624	0.214921	0.034*
H7B	−0.101840	−0.257661	0.286700	0.034*
C8	−0.0334 (4)	−0.0957 (4)	0.1520 (2)	0.0285 (6)
H8A	0.053908	−0.100886	0.091809	0.034*
H8B	−0.146104	−0.097701	0.120528	0.034*
C9	−0.0290 (4)	0.0531 (4)	0.2081 (2)	0.0256 (6)
H9A	0.010003	0.141619	0.155250	0.031*
H9B	−0.142273	0.088875	0.238628	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02050 (9)	0.02056 (9)	0.01580 (9)	−0.00533 (6)	−0.00338 (6)	−0.00528 (6)
O2	0.0354 (12)	0.0230 (10)	0.0305 (11)	−0.0106 (9)	−0.0011 (9)	−0.0109 (9)
O3	0.0299 (11)	0.0341 (11)	0.0204 (10)	−0.0045 (9)	−0.0075 (8)	−0.0076 (9)
O4	0.0407 (12)	0.0213 (10)	0.0257 (11)	0.0004 (9)	−0.0106 (9)	−0.0003 (8)
O1	0.0449 (14)	0.0203 (10)	0.0383 (13)	−0.0011 (10)	−0.0136 (11)	−0.0015 (9)
N1	0.0267 (13)	0.0237 (12)	0.0204 (12)	−0.0061 (10)	−0.0014 (9)	−0.0089 (10)
N2	0.0217 (11)	0.0183 (11)	0.0183 (11)	−0.0015 (9)	−0.0070 (9)	−0.0044 (9)
N3	0.0264 (12)	0.0165 (11)	0.0258 (13)	−0.0042 (9)	0.0002 (10)	−0.0056 (10)
N4	0.0203 (11)	0.0249 (12)	0.0175 (11)	−0.0008 (9)	−0.0019 (9)	−0.0038 (9)
C5	0.0156 (12)	0.0175 (12)	0.0156 (12)	−0.0027 (10)	0.0004 (10)	−0.0045 (10)
C10	0.0152 (12)	0.0207 (12)	0.0146 (12)	−0.0046 (10)	0.0006 (9)	−0.0066 (10)
C15	0.0170 (12)	0.0165 (12)	0.0157 (12)	−0.0038 (10)	0.0018 (9)	−0.0045 (10)
C3	0.0222 (14)	0.0278 (14)	0.0182 (13)	−0.0031 (11)	−0.0057 (11)	−0.0055 (11)
C1	0.0199 (13)	0.0190 (13)	0.0175 (13)	−0.0004 (10)	−0.0020 (10)	−0.0030 (10)
C4	0.0199 (13)	0.0221 (13)	0.0195 (13)	0.0008 (11)	−0.0052 (10)	−0.0022 (11)
C6	0.0305 (15)	0.0175 (13)	0.0216 (14)	−0.0053 (11)	−0.0051 (11)	−0.0046 (11)
C11	0.0174 (13)	0.0219 (13)	0.0130 (12)	−0.0039 (10)	0.0006 (10)	−0.0012 (10)
C12	0.0197 (13)	0.0133 (12)	0.0204 (13)	−0.0040 (10)	0.0035 (10)	−0.0061 (10)
C14	0.0170 (12)	0.0208 (13)	0.0145 (12)	−0.0014 (10)	−0.0007 (10)	−0.0039 (10)
C2	0.0244 (14)	0.0169 (13)	0.0227 (14)	−0.0027 (11)	0.0027 (11)	−0.0035 (11)
C13	0.0193 (13)	0.0219 (13)	0.0181 (13)	−0.0061 (10)	−0.0009 (10)	−0.0066 (10)
C7	0.0324 (16)	0.0304 (15)	0.0265 (15)	−0.0126 (13)	0.0002 (12)	−0.0123 (13)
C8	0.0247 (15)	0.0373 (17)	0.0263 (16)	−0.0060 (13)	−0.0058 (12)	−0.0104 (13)
C9	0.0252 (15)	0.0287 (15)	0.0241 (15)	−0.0002 (12)	−0.0098 (12)	−0.0076 (12)

Geometric parameters (Å, º) top

I1—C10	2.106 (2)	C1—C2	1.380 (4)
O2—N3	1.222 (3)	C1—H1	0.9500
O3—N4	1.225 (3)	C4—H4	0.9500
O4—N4	1.225 (3)	C6—C7	1.525 (4)
O1—N3	1.221 (3)	C6—H6A	0.9900
N1—C2	1.334 (4)	C6—H6B	0.9900
N1—C3	1.346 (4)	C11—C12	1.382 (3)
N2—C5	1.353 (3)	C11—H11	0.9500
N2—C6	1.464 (3)	C12—C13	1.384 (4)
N2—C9	1.465 (3)	C14—C13	1.373 (4)
N3—C12	1.476 (3)	C2—H2	0.9500
N4—C14	1.479 (3)	C13—H13	0.9500
C5—C1	1.407 (4)	C7—C8	1.519 (4)
C5—C4	1.414 (4)	C7—H7A	0.9900
C10—C11	1.393 (4)	C7—H7B	0.9900
C10—C15	1.394 (3)	C8—C9	1.518 (4)
C15—C14	1.393 (3)	C8—H8A	0.9900
C15—H15	0.9500	C8—H8B	0.9900
C3—C4	1.382 (4)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900

C2—N1—C3	115.5 (2)	C12—C11—C10	118.5 (2)
C5—N2—C6	123.9 (2)	C12—C11—H11	120.7
C5—N2—C9	122.4 (2)	C10—C11—H11	120.7
C6—N2—C9	112.3 (2)	C11—C12—C13	123.5 (2)
O1—N3—O2	123.7 (2)	C11—C12—N3	118.6 (2)
O1—N3—C12	117.8 (2)	C13—C12—N3	117.9 (2)
O2—N3—C12	118.5 (2)	C13—C14—C15	123.4 (2)
O4—N4—O3	124.9 (2)	C13—C14—N4	118.3 (2)
O4—N4—C14	117.5 (2)	C15—C14—N4	118.2 (2)
O3—N4—C14	117.6 (2)	N1—C2—C1	125.1 (2)
N2—C5—C1	122.0 (2)	N1—C2—H2	117.5
N2—C5—C4	121.9 (2)	C1—C2—H2	117.5
C1—C5—C4	116.1 (2)	C14—C13—C12	116.1 (2)
C11—C10—C15	120.1 (2)	C14—C13—H13	121.9
C11—C10—I1	120.25 (19)	C12—C13—H13	121.9
C15—C10—I1	119.66 (18)	C8—C7—C6	104.7 (2)
C14—C15—C10	118.3 (2)	C8—C7—H7A	110.8
C14—C15—H15	120.8	C6—C7—H7A	110.8
C10—C15—H15	120.8	C8—C7—H7B	110.8
N1—C3—C4	124.6 (2)	C6—C7—H7B	110.8
N1—C3—H3	117.7	H7A—C7—H7B	108.9
C4—C3—H3	117.7	C9—C8—C7	104.1 (2)
C2—C1—C5	119.4 (2)	C9—C8—H8A	110.9
C2—C1—H1	120.3	C7—C8—H8A	110.9
C5—C1—H1	120.3	C9—C8—H8B	110.9
C3—C4—C5	119.3 (2)	C7—C8—H8B	110.9
C3—C4—H4	120.3	H8A—C8—H8B	109.0
C5—C4—H4	120.3	N2—C9—C8	103.6 (2)
N2—C6—C7	104.0 (2)	N2—C9—H9A	111.0
N2—C6—H6A	111.0	C8—C9—H9A	111.0
C7—C6—H6A	111.0	N2—C9—H9B	111.0
N2—C6—H6B	111.0	C8—C9—H9B	111.0
C7—C6—H6B	111.0	H9A—C9—H9B	109.0
H6A—C6—H6B	109.0

C6—N2—C5—C1	−170.4 (3)	O1—N3—C12—C13	−175.5 (3)
C9—N2—C5—C1	−4.8 (4)	O2—N3—C12—C13	3.5 (4)
C6—N2—C5—C4	11.0 (4)	C10—C15—C14—C13	1.3 (4)
C9—N2—C5—C4	176.6 (2)	C10—C15—C14—N4	179.8 (2)
C11—C10—C15—C14	−0.4 (4)	O4—N4—C14—C13	174.3 (2)
I1—C10—C15—C14	−179.76 (18)	O3—N4—C14—C13	−5.0 (4)
C2—N1—C3—C4	−0.1 (4)	O4—N4—C14—C15	−4.2 (4)
N2—C5—C1—C2	−178.6 (2)	O3—N4—C14—C15	176.4 (2)
C4—C5—C1—C2	0.1 (4)	C3—N1—C2—C1	−0.5 (4)
N1—C3—C4—C5	0.7 (4)	C5—C1—C2—N1	0.5 (4)
N2—C5—C4—C3	178.1 (3)	C15—C14—C13—C12	−0.9 (4)
C1—C5—C4—C3	−0.6 (4)	N4—C14—C13—C12	−179.3 (2)
C5—N2—C6—C7	161.7 (3)	C11—C12—C13—C14	−0.5 (4)
C9—N2—C6—C7	−5.2 (3)	N3—C12—C13—C14	178.4 (2)
C15—C10—C11—C12	−0.9 (4)	N2—C6—C7—C8	24.1 (3)
I1—C10—C11—C12	178.47 (19)	C6—C7—C8—C9	−33.9 (3)
C10—C11—C12—C13	1.4 (4)	C5—N2—C9—C8	177.2 (2)
C10—C11—C12—N3	−177.5 (2)	C6—N2—C9—C8	−15.7 (3)
O1—N3—C12—C11	3.4 (4)	C7—C8—C9—N2	30.1 (3)
O2—N3—C12—C11	−177.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.61	3.499 (3)	156
C7—H7B···I1ⁱⁱ	0.99	3.22	4.104 (3)	150
C8—H8A···O2ⁱⁱⁱ	0.99	2.55	3.301 (4)	133
C8—H8A···O4^iv	0.99	2.61	3.420 (4)	140
C9—H9A···O4^v	0.99	2.61	3.186 (3)	117

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

4-(Pyrrolidin-1-yl)pyridine–1-iodo-3,5-bis(trifluoromethyl)benzene (1/1) (BTFIB4PYPY) top

Crystal data top

C₈H₃F₆I·C₉H₁₂N₂	Z = 2
M_r = 488.21	F(000) = 476
Triclinic, P1	D_x = 1.819 Mg m⁻³
a = 7.9777 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5138 (4) Å	Cell parameters from 7472 reflections
c = 14.1679 (7) Å	θ = 2.5–27.2°
α = 101.579 (1)°	µ = 1.86 mm⁻¹
β = 103.264 (1)°	T = 100 K
γ = 100.370 (1)°	Cut, colourless
V = 891.40 (8) Å³	0.41 × 0.20 × 0.11 mm

Data collection top

Bruker APEXI CCD diffractometer	3517 reflections with I > 2σ(I)
Detector resolution: 8.3660 pixels mm^-1	R_int = 0.021
φ and ω scans	θ_max = 27.2°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.669, T_max = 0.746	k = −10→10
11576 measured reflections	l = −18→18
3979 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0623P)² + 1.7968P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3979 reflections	Δρ_max = 2.23 e Å⁻³
235 parameters	Δρ_min = −1.21 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
I1	0.25075 (3)	0.40397 (3)	0.25028 (2)	0.04031 (12)
F3	0.1815 (5)	0.9266 (4)	−0.0400 (2)	0.0699 (10)
F2	0.4058 (5)	0.9949 (4)	0.0867 (4)	0.0981 (16)
F6	0.3083 (8)	0.2154 (6)	−0.1345 (3)	0.1099 (19)
F5	0.0807 (4)	0.2808 (6)	−0.2053 (3)	0.1068 (19)
F1	0.1466 (8)	0.9537 (6)	0.1061 (3)	0.1139 (19)
F4	0.3331 (6)	0.4094 (4)	−0.1980 (3)	0.0930 (15)
C14	0.2424 (5)	0.7210 (5)	0.0425 (3)	0.0371 (9)
C11	0.2431 (5)	0.3922 (5)	0.0328 (3)	0.0348 (8)
H11	0.242389	0.279409	0.029139	0.042*
C12	0.2414 (5)	0.4538 (5)	−0.0508 (3)	0.0311 (8)
C15	0.2465 (5)	0.6632 (5)	0.1279 (3)	0.0348 (9)
H15	0.249785	0.735595	0.189071	0.042*
C10	0.2459 (5)	0.4985 (5)	0.1227 (3)	0.0347 (8)
C16	0.2362 (5)	0.3388 (5)	−0.1481 (3)	0.0318 (8)
C13	0.2399 (5)	0.6171 (5)	−0.0480 (3)	0.0343 (8)
H13	0.237243	0.657398	−0.106043	0.041*
C17	0.2452 (7)	0.8988 (6)	0.0480 (4)	0.0541 (13)
N2	0.2661 (4)	−0.1161 (4)	0.5764 (3)	0.0356 (7)
N1	0.2667 (5)	0.2330 (5)	0.4051 (3)	0.0431 (9)
C4	0.3814 (5)	0.1550 (5)	0.5581 (3)	0.0351 (8)
H4	0.461763	0.186897	0.623266	0.042*
C5	0.2673 (5)	−0.0044 (5)	0.5219 (3)	0.0326 (8)
C9	0.1582 (5)	−0.2865 (5)	0.5391 (3)	0.0414 (10)
H9A	0.177820	−0.341771	0.475465	0.050*
H9B	0.030462	−0.289137	0.528127	0.050*
C6	0.3750 (5)	−0.0824 (5)	0.6811 (3)	0.0335 (8)
H6A	0.368445	0.024343	0.721668	0.040*
H6B	0.500531	−0.080878	0.684121	0.040*
C2	0.1594 (6)	0.0792 (6)	0.3706 (3)	0.0412 (10)
H2	0.081913	0.051437	0.304785	0.049*
C7	0.2906 (6)	−0.2267 (5)	0.7170 (3)	0.0408 (9)
H7A	0.191991	−0.201739	0.744282	0.049*
H7B	0.379140	−0.252966	0.769246	0.049*
C1	0.1534 (5)	−0.0393 (6)	0.4230 (3)	0.0390 (9)
H1	0.073671	−0.144412	0.393517	0.047*
C3	0.3751 (5)	0.2644 (6)	0.4979 (3)	0.0384 (9)
H3	0.453833	0.370463	0.524397	0.046*
C8	0.2226 (6)	−0.3690 (6)	0.6224 (4)	0.0461 (10)
H8A	0.318785	−0.422350	0.610027	0.055*
H8B	0.124415	−0.453024	0.627894	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.03090 (16)	0.05218 (19)	0.02766 (16)	−0.00391 (11)	0.00906 (11)	−0.00150 (11)
F3	0.095 (3)	0.0434 (16)	0.0525 (18)	0.0249 (16)	−0.0135 (17)	0.0018 (13)
F2	0.079 (2)	0.0322 (15)	0.132 (4)	0.0066 (15)	−0.045 (2)	−0.0038 (18)
F6	0.204 (5)	0.118 (3)	0.0405 (18)	0.122 (4)	0.039 (2)	0.0124 (19)
F5	0.0302 (15)	0.164 (4)	0.067 (2)	−0.0023 (19)	0.0075 (15)	−0.075 (3)
F1	0.192 (5)	0.102 (3)	0.087 (3)	0.112 (4)	0.059 (3)	0.019 (2)
F4	0.126 (3)	0.068 (2)	0.081 (3)	−0.018 (2)	0.081 (3)	−0.0143 (18)
C14	0.0242 (18)	0.040 (2)	0.037 (2)	0.0097 (16)	−0.0009 (15)	−0.0041 (17)
C11	0.0293 (19)	0.0337 (19)	0.034 (2)	−0.0036 (15)	0.0115 (16)	−0.0022 (16)
C12	0.0241 (17)	0.0339 (19)	0.0293 (18)	0.0017 (14)	0.0082 (14)	−0.0017 (15)
C15	0.0208 (17)	0.042 (2)	0.0309 (19)	0.0047 (15)	0.0046 (14)	−0.0097 (16)
C10	0.0225 (17)	0.046 (2)	0.0267 (18)	−0.0022 (15)	0.0087 (14)	−0.0025 (16)
C16	0.0313 (19)	0.0316 (19)	0.0319 (19)	0.0047 (15)	0.0129 (15)	0.0045 (15)
C13	0.0252 (18)	0.039 (2)	0.0322 (19)	0.0077 (15)	0.0016 (15)	0.0008 (16)
C17	0.052 (3)	0.049 (3)	0.045 (3)	0.025 (2)	−0.011 (2)	−0.010 (2)
N2	0.0256 (15)	0.0365 (17)	0.0321 (17)	−0.0010 (13)	0.0048 (13)	−0.0084 (14)
N1	0.0373 (19)	0.057 (2)	0.0322 (18)	0.0114 (17)	0.0122 (15)	0.0012 (16)
C4	0.0291 (18)	0.044 (2)	0.0239 (18)	0.0019 (16)	0.0063 (15)	−0.0040 (16)
C5	0.0246 (17)	0.041 (2)	0.0257 (18)	0.0056 (15)	0.0079 (14)	−0.0058 (15)
C9	0.029 (2)	0.038 (2)	0.043 (2)	−0.0012 (16)	0.0085 (17)	−0.0123 (18)
C6	0.0290 (18)	0.036 (2)	0.0283 (19)	0.0026 (15)	0.0090 (15)	−0.0044 (15)
C2	0.031 (2)	0.056 (3)	0.0280 (19)	0.0111 (19)	0.0056 (16)	−0.0055 (18)
C7	0.037 (2)	0.040 (2)	0.038 (2)	0.0008 (17)	0.0137 (18)	−0.0025 (18)
C1	0.0275 (19)	0.047 (2)	0.031 (2)	0.0051 (17)	0.0041 (16)	−0.0080 (17)
C3	0.033 (2)	0.046 (2)	0.030 (2)	0.0012 (17)	0.0130 (16)	−0.0024 (17)
C8	0.037 (2)	0.039 (2)	0.048 (3)	−0.0032 (18)	0.0093 (19)	−0.0060 (19)

Geometric parameters (Å, º) top

I1—C10	2.116 (4)	N1—C3	1.343 (6)
F3—C17	1.319 (6)	N1—C2	1.354 (6)
F2—C17	1.316 (6)	C4—C3	1.383 (6)
F6—C16	1.311 (5)	C4—C5	1.413 (6)
F5—C16	1.264 (5)	C4—H4	0.9500
F1—C17	1.338 (7)	C5—C1	1.424 (5)
F4—C16	1.309 (5)	C9—C8	1.528 (7)
C14—C15	1.391 (6)	C9—H9A	0.9900
C14—C13	1.397 (6)	C9—H9B	0.9900
C14—C17	1.496 (6)	C6—C7	1.527 (6)
C11—C12	1.388 (6)	C6—H6A	0.9900
C11—C10	1.400 (5)	C6—H6B	0.9900
C11—H11	0.9500	C2—C1	1.367 (7)
C12—C13	1.385 (6)	C2—H2	0.9500
C12—C16	1.508 (5)	C7—C8	1.529 (6)
C15—C10	1.388 (6)	C7—H7A	0.9900
C15—H15	0.9500	C7—H7B	0.9900
C13—H13	0.9500	C1—H1	0.9500
N2—C5	1.340 (6)	C3—H3	0.9500
N2—C9	1.470 (5)	C8—H8A	0.9900
N2—C6	1.478 (5)	C8—H8B	0.9900

C15—C14—C13	121.3 (4)	N2—C5—C4	122.5 (4)
C15—C14—C17	119.5 (4)	N2—C5—C1	122.0 (4)
C13—C14—C17	119.2 (4)	C4—C5—C1	115.5 (4)
C12—C11—C10	119.1 (4)	N2—C9—C8	104.0 (3)
C12—C11—H11	120.5	N2—C9—H9A	111.0
C10—C11—H11	120.5	C8—C9—H9A	111.0
C13—C12—C11	121.7 (4)	N2—C9—H9B	111.0
C13—C12—C16	119.2 (4)	C8—C9—H9B	111.0
C11—C12—C16	119.1 (3)	H9A—C9—H9B	109.0
C10—C15—C14	119.3 (3)	N2—C6—C7	103.0 (3)
C10—C15—H15	120.3	N2—C6—H6A	111.2
C14—C15—H15	120.3	C7—C6—H6A	111.2
C15—C10—C11	120.3 (4)	N2—C6—H6B	111.2
C15—C10—I1	120.8 (3)	C7—C6—H6B	111.2
C11—C10—I1	118.8 (3)	H6A—C6—H6B	109.1
F5—C16—F4	107.9 (4)	N1—C2—C1	125.3 (4)
F5—C16—F6	108.4 (5)	N1—C2—H2	117.3
F4—C16—F6	101.9 (4)	C1—C2—H2	117.3
F5—C16—C12	112.6 (3)	C6—C7—C8	103.7 (4)
F4—C16—C12	112.6 (3)	C6—C7—H7A	111.0
F6—C16—C12	112.7 (3)	C8—C7—H7A	111.0
C12—C13—C14	118.3 (4)	C6—C7—H7B	111.0
C12—C13—H13	120.9	C8—C7—H7B	111.0
C14—C13—H13	120.9	H7A—C7—H7B	109.0
F2—C17—F3	107.1 (5)	C2—C1—C5	119.6 (4)
F2—C17—F1	106.4 (5)	C2—C1—H1	120.2
F3—C17—F1	106.1 (4)	C5—C1—H1	120.2
F2—C17—C14	112.5 (4)	N1—C3—C4	125.3 (4)
F3—C17—C14	113.2 (4)	N1—C3—H3	117.3
F1—C17—C14	111.1 (5)	C4—C3—H3	117.3
C5—N2—C9	124.1 (3)	C9—C8—C7	103.9 (4)
C5—N2—C6	123.8 (3)	C9—C8—H8A	111.0
C9—N2—C6	112.1 (3)	C7—C8—H8A	111.0
C3—N1—C2	114.7 (4)	C9—C8—H8B	111.0
C3—C4—C5	119.4 (4)	C7—C8—H8B	111.0
C3—C4—H4	120.3	H8A—C8—H8B	109.0
C5—C4—H4	120.3

C10—C11—C12—C13	−0.9 (6)	C15—C14—C17—F1	−38.9 (6)
C10—C11—C12—C16	−179.3 (3)	C13—C14—C17—F1	142.6 (4)
C13—C14—C15—C10	−0.9 (6)	C9—N2—C5—C4	−175.8 (4)
C17—C14—C15—C10	−179.3 (4)	C6—N2—C5—C4	3.6 (6)
C14—C15—C10—C11	0.7 (6)	C9—N2—C5—C1	4.0 (6)
C14—C15—C10—I1	−179.7 (3)	C6—N2—C5—C1	−176.6 (3)
C12—C11—C10—C15	0.1 (6)	C3—C4—C5—N2	−179.7 (4)
C12—C11—C10—I1	−179.5 (3)	C3—C4—C5—C1	0.5 (5)
C13—C12—C16—F5	−83.0 (5)	C5—N2—C9—C8	172.2 (4)
C11—C12—C16—F5	95.5 (5)	C6—N2—C9—C8	−7.3 (4)
C13—C12—C16—F4	39.3 (5)	C5—N2—C6—C7	165.2 (4)
C11—C12—C16—F4	−142.2 (4)	C9—N2—C6—C7	−15.4 (4)
C13—C12—C16—F6	153.9 (4)	C3—N1—C2—C1	1.0 (6)
C11—C12—C16—F6	−27.6 (6)	N2—C6—C7—C8	31.7 (4)
C11—C12—C13—C14	0.8 (6)	N1—C2—C1—C5	−0.3 (6)
C16—C12—C13—C14	179.2 (3)	N2—C5—C1—C2	179.7 (4)
C15—C14—C13—C12	0.1 (6)	C4—C5—C1—C2	−0.5 (5)
C17—C14—C13—C12	178.6 (4)	C2—N1—C3—C4	−0.9 (6)
C15—C14—C17—F2	80.2 (6)	C5—C4—C3—N1	0.2 (6)
C13—C14—C17—F2	−98.3 (5)	N2—C9—C8—C7	27.0 (4)
C15—C14—C17—F3	−158.2 (4)	C6—C7—C8—C9	−36.7 (4)
C13—C14—C17—F3	23.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···F6ⁱ	0.99	2.54	3.465 (5)	156
C1—H1···F5ⁱⁱ	0.95	2.59	3.265 (5)	128

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

Acknowledgements

EB acknowledges the Missouri State University Provost Incentive Fund for the purchase of the X-ray diffractometer used in this contribution.

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