Charge-enhanced pyri­dyl tri­fluoro­borate organocatalysts: crystal structures and reactivity

The crystal structures of eleven 3- and 4-pyri­dyl borate salts with a variety of cations are reported. These are potassium tri­fluoro­(pyridin-3/4-yl)borate, K⁺·C₅H₄BF₃N⁻, 1 and 2 (as the monohydrate), tetra­butyl­ammonium tri­fluoro­(pyridin-3/4-yl)borate, C₁₆H₃₆N⁺·C₅H₄BF₃N⁻, 3 and 4, tetra­phenyl­phospho­nium tri­fluoro­(pyridin-3/4-yl)borate, C₂₄H₂₀P⁺·C₅H₄BF₃N⁻, 5 and 6, tetra­kis­(3,5-di­meth­oxy­phen­yl)phospho­nium tri­fluoro­(pyridin-3/4-yl)borate, C₃₂H₃₆O₈P⁺·C₅H₄BF₃N⁻, 7 and 8, and tetra­kis­[4-(di­methyl­amino)­phen­yl]phospho­nium tri­fluoro­(pyridin-3/4-yl)borate, C₃₂H₄₀N₄P⁺·C₅H₄BF₃N⁻, 9 and 10, and the hemihydrate, C₃₂H₄₀N₄P⁺·C₅H₄BF₃N⁻·0.5H₂O, 10h. The effects of the position of the pyridine N atom and the identity of the cations on the crystal packing of the salts are examined. The N⋯H and F⋯H anion–cation con­tacts and the Hirshfeld surface com­positions of the anions for the salts containing organic cations are com­pared to the reactivity of the salts in a low-polarity solvent to look for trends between solid-state features and solution-state reactivity.

1. Introduction

When referring to a catalyst for a chemical reaction, often the first type of species to come to mind is a transition metal. Substances of this sort play an enormous role in modern chemistry, ranging from applications from polymer synthesis to protein modification to the generation of vital chemical feedstocks such as ammonia (Wang et al., 2025; Ghosh, 2025; Varadwaj et al., 2025). Despite their ubiquity, transition-metal catalysts are not without their drawbacks. First, many of them require the use of scarce late transition metals, such as palladium or ruthenium, in order to function. As a result, they are costly to manufacture and expensive to purchase. Significant work has gone into their replacement with abundant early transition metals, such as nickel or titanium, as more sus­tain­able and `greener' alternatives (Sun et al., 2025; Butler et al., 2024). Unfortunately, many of these species still suffer from a major drawback of transition-metal catalysts: air and moisture sensitivity. The impressive chemical reactions enabled by transition-metal catalysts are often made more difficult, especially at large scale, by the need to operate under strictly inert conditions. Thus, there is a demand for catalysts that are stable under ambient conditions.

In the last few decades, transition-metal-free catalysts that use only organic mol­ecules to catalyze chemical reactions have been developed for a variety of transformations (List, 2007). These catalysts, known as organocatalysts, tend to be more tolerant of air and moisture than transition-metal catalysts. However, they are often less catalytically active and therefore require higher catalyst loadings to achieve reasonable reaction rates. For example, chiral amine organocatalysts, such as (S)-proline, may require loadings of up to 40%, while transition-metal catalysts, such as the ruthenium-based family of Grubb's catalysts, often operate with catalyst loadings of less than 1% (Mukherjee et al., 2007; Kajetanowicz & Grela, 2021).

Our group has demonstrated that the addition of positively charged centers to Brønsted acid organocatalysts can significantly increase their catalytic activity (Fan & Kass, 2016; Samet et al., 2015; Ma & Kass, 2016; Riegel et al., 2022). It follows that the addition of a negatively charged center could increase the activity of Brønsted bases or nucleophilic catalysts. The latter, derived from a pyridine scaffold such as 4-(di­methyl­amino)­pyridine (DMAP), have been used as catalysts for a wide range of reactions, including esterifications (Neises & Steglich, 1978), macrolactonizations (Boden & Keck, 1985), and silylations (Chaudhary & Hernandez, 1979). Given the widespread applications of nucleophilic catalysts, the development of more reactive analogues by incorporation of a negative charge center could potentially increase their effectiveness. Recent work has demonstrated the validity of anion-enhanced nucleophilic catalysts with the development of anionic sulfonamide-based catalysts (Helberg et al., 2020; Burger, Franta, O'Donoghue et al., 2025; Burger, Franta, Ofial et al., 2025) that showed significant improvement in reactivity over DMAP and related neutral pyridine derivatives. Re­cent­ly, our group has developed a similar family of negatively charged organocatalysts based on a pyri­dyl borate scaf­fold (Dempsey, Lovstedt et al., 2023; Dempsey, Cao et al., 2023). These were found to have increased nucleophilicity com­pared to DMAP, and the most reactive of which was com­parable in performance to the anionic sulfonamide catalysts (Dempsey, Lovstedt et al., 2023). Following on from our previous studies, in this article, we report the crystal structures of ten different 3- or 4-pyri­dyl tri­fluoro­borate salts (Fig. 1). Some of the salts had been investigated as anionic catalysts in our previous work, while several novel salts have been synthesized and characterized. Using the crystal structures, we examine the inter­molecular inter­actions between the ion pairs of the various salts and search for trends between selected crystallographic parameters and anion nucleophilicity. Additionally, the effects of counter-ion identity on the nucleophilicity of the catalysts will be examined.

Figure 1 Pyridyl tri­fluoro­borate salts investigated in this work.

2. Experimental

2.1. Synthesis

The 3- and 4-pyri­dyl tri­fluoro­borate salts were synthesized as illustrated in Fig. 2 for the 3-substituted derivatives (Dempsey, Lovstedt et al., 2023). Potassium bifluoride was reacted with one of the two different pyri­dyl boronic acids to give the corresponding pyri­dyl tri­fluoro­borate anion as its potassium salt. Cation exchange via ion metathesis afforded the desired salts. Single crystals of each were grown by evaporation (see the supporting information for specific details). These com­pounds were also characterized by NMR spectroscopy (¹H, ¹³C, ¹¹B, ¹⁹F, and ³¹P) and high-resolution mass spectrometry. The results of these analyses are provided in the supporting information.

Figure 2 The synthetic pathway for the 3-pyri­dyl tri­fluoro­borate salts. The 4-pyri­dyl salts were synthesized in an analogous manner.

2.2. Crystal structure, data collection and refinement

Crystals were placed onto the tip of a 0.15 mm MiTeGen loop and mounted on a Bruker D8 Venture diffractometer equipped with a PHOTON III CPAD detector and IµS 3.0 Mo and IµS 2.0 Cu microfocus X-ray sources for data collection. A preliminary set of unit-cell constants was calculated from reflections harvested from three sets of frames. These initial sets of frames were oriented such that orthogonal wedges of reciprocal space were surveyed. This produced initial orientation matrices which were used to determine a data collection strategy to ensure com­plete data coverage to a desired resolution using the APEX5 software package (Bruker, 2023). The data collection was carried out using Cu Kα radiation for com­pounds 3 and 4, and Mo Kα radiation for com­pounds 1, 2, 5–10, and 10h (the hemihydrate of 10). All major sections of frames were collected with 1.2° steps in ω or φ at different detector positions in 2θ. The intensity data were corrected for absorption and decay using the SADABS or TWINABS software (Krause et al., 2015; Sheldrick, 2012). Final unit-cell constants were calculated from the xyz centroids of strong reflections from the actual data collection after integration in the SAINT software (Bruker, 2016). The structures were solved using SHELXT (Sheldrick, 2015a) and refined using SHELXL2019 (Sheldrick, 2015b) within the ShelXle program (Hübschle et al., 2011). Space groups were determined based on systematic absences and intensity statistics. A dual-space method solution was calculated which provided most non-H atoms from the E-map. Full-matrix least-squares/difference Fourier cycles were performed which located the remaining non-H atoms. All non-H atoms were refined with anisotropic displacement parameters. H atoms on water mol­ecules were located in the difference map. All other H atoms were placed in ideal positions and refined as riding atoms with relative isotropic displacement parameters. Crystal structure images were created using Mercury (Macrae et al., 2020). Crystal information and refinement details for each structure are provided in Table 1.

Table 1
Experimental details

Experiments were carried out using a Bruker D8 Venture diffractometer equipped with a PHOTON III CPAD detector.

	1	2	3	4
Crystal data
Chemical formula	K^+·C5H4BF3N^−	K^+·C5H4BF3N^−·H2O	C16H36N^+·C5H4BF3N^−	C16H36N^+·C5H4BF3N^−
Mr	185.00	203.02	388.36	388.36
Crystal system, space group	Orthorhombic, P212121	Monoclinic, P21/c	Monoclinic, P21/n	Monoclinic, P21/c
Temperature (K)	100	100	100	100
a, b, c (Å)	5.8637 (2), 7.2260 (3), 16.5602 (8)	10.8271 (15), 8.5041 (11), 8.8435 (12)	9.4405 (7), 15.9663 (10), 15.4847 (11)	8.8089 (6), 13.2030 (8), 19.9075 (14)
α, β, γ (°)	90, 90, 90	90, 90.043 (5), 90	90, 100.159 (2), 90	90, 98.652 (2), 90
V (Å^3)	701.67 (5)	814.26 (19)	2297.4 (3)	2289.0 (3)
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm^−1)	0.74	0.65	0.08	0.08
Crystal size (mm)	0.16 × 0.09 × 0.04	0.17 × 0.17 × 0.07	0.32 × 0.06 × 0.06	0.08 × 0.07 × 0.06
Data collection
Absorption correction	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)
Tmin, Tmax	0.665, 0.746	0.579, 0.745	0.662, 0.745	0.705, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	11196, 1733, 1694	19163, 1723, 1514	23792, 4228, 3058	24696, 4206, 2997
Rint	0.034	0.075	0.071	0.059
(sin θ/λ)max (Å^−1)	0.666	0.632	0.605	0.603
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.019, 0.060, 0.99	0.032, 0.085, 1.11	0.043, 0.106, 1.03	0.040, 0.098, 1.03
No. of reflections	1733	1723	4228	4206
No. of parameters	100	158	248	248
No. of restraints	0	176	0	0
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained	H-atom parameters constrained
Δρmax, Δρmin (e Å^−3)	0.27, −0.17	0.47, −0.32	0.20, −0.19	0.19, −0.20
Absolute structure	Flack x determined using 680 quotients [(I^+) − (I^−)]/[(I^+) + (I^−)] (Parsons et al., 2013)	–	–	–
Absolute structure parameter	0.008 (16)	–	–	–

	5	6	7	8
Crystal data
Chemical formula	C24H20P^+·C5H4BF3N^−	C24H20P^+·C5H4BF3N^−	C32H36O8P^+·C5H4BF3N^−	C32H36O8P^+·C5H4BF3N^−
Mr	485.27	485.27	725.48	725.48
Crystal system, space group	Monoclinic, Pc	Triclinic, P1	Monoclinic, P21/n	Triclinic, P
Temperature (K)	126	125	150	150
a, b, c (Å)	10.1711 (2), 9.3254 (2), 13.7076 (3)	9.4898 (3), 10.2000 (3), 14.4239 (5)	21.3755 (8), 7.5380 (3), 23.0617 (8)	14.702 (4), 15.141 (5), 16.017 (5)
α, β, γ (°)	90, 108.701 (1), 90	99.787 (2), 101.625 (2), 113.231 (2)	90, 99.998 (2), 90	84.473 (11), 88.059 (10), 85.136 (10)
V (Å^3)	1231.52 (5)	1207.43 (7)	3659.5 (2)	3534.7 (18)
Z	2	2	4	4
Radiation type	Cu Kα	Cu Kα	Mo Kα	Mo Kα
μ (mm^−1)	1.33	1.36	0.14	0.15
Crystal size (mm)	0.25 × 0.25 × 0.24	0.10 × 0.07 × 0.06	0.31 × 0.07 × 0.05	0.16 × 0.07 × 0.05
Data collection
Absorption correction	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (TWINABS; Sheldrick, 2012)
Tmin, Tmax	0.661, 0.754	0.605, 0.754	0.661, 0.746	0.682, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	24137, 4783, 4708	24637, 9470, 9274	43069, 9058, 6479	12796, 12796, 9875
Rint	0.035	0.034	0.052	–
(sin θ/λ)max (Å^−1)	0.625	0.638	0.667	0.600
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.029, 0.076, 1.02	0.038, 0.106, 1.06	0.046, 0.123, 1.02	0.053, 0.132, 1.06
No. of reflections	4783	9470	9058	12796
No. of parameters	316	631	468	967
No. of restraints	2	3	0	30
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρmax, Δρmin (e Å^−3)	0.25, −0.26	0.35, −0.26	0.45, −0.35	0.44, −0.35
Absolute structure	Flack x determined using 2179 quotients [(I^+) − (I^−)]/[(I^+) + (I^−)] (Parsons et al., 2013)	Flack x determined using 4183 quotients [(I^+) − (I^−)]/[(I^+) + (I^−)] (Parsons et al., 2013)	–	–
Absolute structure parameter	−0.011 (12)	0.000 (15)	–	–

	9	10	10h
Crystal data
Chemical formula	C32H40N4P^+·C5H4BF3N^−	C32H40N4P^+·C5H4BF3N^−	C32H40N4P^+·C5H4BF3N^−·0.5H2O
Mr	657.55	657.55	666.56
Crystal system, space group	Monoclinic, P21/n	Monoclinic, P21/n	Monoclinic, P21/n
Temperature (K)	150	100	150
a, b, c (Å)	15.802 (2), 12.0571 (15), 18.121 (2)	15.9231 (9), 11.5958 (6), 18.7330 (12)	11.9373 (3), 23.4315 (7), 13.0949 (3)
α, β, γ (°)	90, 94.405 (3), 90	90, 96.696 (2), 90	90, 105.938 (1), 90
V (Å^3)	3442.4 (8)	3435.3 (3)	3521.96 (16)
Z	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm^−1)	0.13	0.13	0.13
Crystal size (mm)	0.17 × 0.10 × 0.05	0.34 × 0.25 × 0.04	0.16 × 0.16 × 0.10
Data collection
Absorption correction	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)
Tmin, Tmax	0.629, 0.746	0.629, 0.745	0.644, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	31607, 6295, 4970	52555, 6526, 4822	31433, 7198, 5810
Rint	0.037	0.060	0.032
(sin θ/λ)max (Å^−1)	0.602	0.610	0.625
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.039, 0.106, 1.04	0.051, 0.142, 1.04	0.044, 0.117, 1.04
No. of reflections	6295	6526	7198
No. of parameters	487	525	448
No. of restraints	186	367	4
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å^−3)	0.21, −0.31	0.96, −0.35	0.55, −0.46
Computer programs: APEX5 (Bruker, 2023), SAINT (Bruker, 2016), SHELXT2018 (Sheldrick, 2015a), SHELXL2019 (Sheldrick, 2015b), Mercury (Macrae et al., 2020), and ShelXle (Hübschle et al., 2011).

2.3. Hirshfeld surface analysis

Hirshfeld surfaces and fingerprint plots for the crystal structures of com­pounds 3–10 and 10h were com­puted using the CrystalExplorer program (Spackman et al., 2021).

2.4. S_N2 reaction kinetics

Data were collected using a Bruker Avance 400 MHz spectrometer. In a nitro­gen-atmosphere glovebox, an amount of each salt to make a 25 mM solution and iodo­octane to make a 500 mM solution were dissolved in deuterated di­chloro­methane (DCM) and placed in a screw cap NMR tube. The tube was inverted several times to ensure mixing, placed in the NMR spectrometer, and ¹H spectra were taken at inter­vals ranging from 10 to 20 min. Pseudo-first-order rate constants were obtained using the Reaction Monitoring program within the MNova software package (Mestrelab Research, 2023). Additional experimental details are provided in the sup­por­ting information.

3. Crystal structure analysis

This section will analyze and discuss the crystal packing of the various salts with a particular focus on close con­tacts between the F and N atoms of the anions with H atoms of the cations. Additionally, the effects of the counter-ion and the position of the pyridine N atom in the anion on the packing of the anions will be examined. A close con­tact is defined as a distance between atoms less than the sum of their van der Waals radii. The van der Waals radii used in this work are as follows: H 1.10 Å, C 1.70 Å, N 1.55 Å, O 1.52 Å, and F 1.47 Å (Mantina et al., 2009). Close con­tacts involving H atoms are defined after normalizing the H-atom bond lengths to the distances observed in neutron diffraction: 1.089 Å for C—H bonds and 0.993 Å for O—H bonds. The standard uncertainties of con­tacts involving H atoms constrained as riding atoms are the uncertainties in the distance between the acceptor atom and the donor atom upon which the H atom is riding. The uncertainties for average distances are the average of the uncertainties of the individual measurements. The terms ortho, meta, and para are used to refer to the positions of aromatic H atoms in relation to the P atom for cations and the B atom for anions.

3.1. Potassium salts

Compounds 1 and 2 are the potassium salts of the 3-pyri­dyl and 4-pyri­dyl tri­fluoro­borate anions, respectively. Salt 1 crystallized in the ortho­rhom­bic space group P2₁2₁2₁ with Z′ = 1 (Fig. 3). The F atoms of the anion inter­act with the potassium cation, forming a layered structure in which layers of tri­fluoro­borate and potassium cations inter­act, separated by layers of pyridine moieties. This layered structure can be clearly seen when viewing a packing diagram of the salt along the crystallographic a and b axes (Fig. 4). The pyridine N atom links the two layers via an inter­action with a potassium cation in the next layer. The anions form anion–anion con­tacts via C—H⋯π con­tacts between the pyridine groups.

Figure 3 The asymmetric unit of salt 1. The following applies to all images of crystal structures: non-H atoms are drawn as displacement ellipsoids at the 50% probability level. H atoms are drawn as fixed sized spheres.

Figure 4 A 3×3×3 crystal packing diagram of salt 1, viewed along the crystallographic b axis.

Attempts to obtain a neat form of salt 2 were unsuccessful; however, the monohydrate was obtained in the monoclinic space group P2₁/c (Fig. 5). The crystal was a pseudo-merohedral twin with two twin domains having an approximate ratio of 55:45. Like salt 1, the crystal packing of 2 consists of layers of tri­fluoro­borate moieties and potassium cations alternating with layers of pyridine moieties, which can be clearly seen when viewing a packing diagram of the crystal along the crystallographic c axis (Fig. 6). The pyridine group of the anion is disordered and was modeled in two positions with equal occupancy, with the second position of the pyridine ring rotated by approximately 84° from the first (Fig. 5, top right). The cocrystallized water mol­ecule plays a vital role in the packing of this crystal, linking the pyridine layers with the tri­fluoro­borate–potassium layers via a 1.81 (3) Å O—H⋯N hy­dro­gen bond involving the pyridine N atom, and a K⋯O con­tact with a potassium cation (Fig. 5, bottom).

Figure 5 (Top left) The asymmetric unit of salt 2 showing only one of the disordered parts of the anion. (Top right) A superposition of the two equally occupied disordered parts of the anion. (Bottom) A selection of close con­tacts in 2. O—H bond distances have been normalized to 0.993 Å.

Figure 6 A 3×3×3 crystal packing diagram of 2, viewed along the crystallographic c axis.

The second H atom of the water mol­ecule forms a hy­dro­gen bond with an F atom from an adjacent tri­fluoro­borate moiety. There are no significant con­tacts between the anions in the structure, and the closest anion–anion con­tacts are between H atoms. The importance of the water in the crystal packing offers a potential explanation for why single crystals of the neat salt were difficult to obtain.

3.2. Tetra­butyl­ammonium (TBA) salts

Compounds 3 and 4 are the tetra­butyl­ammonium salts of the 3- and 4-pyri­dyl tri­fluoro­borate anions, respectively. Salt 3 crystallized in the monoclinic space group P2₁/n with Z′ = 1 (Fig. 7). An inspection of the crystal packing shows that 3 packs with a `channel' structure, with channels of anions running along the crystallographic a axis separated by channels of cations (Fig. 8). This packing motif is particularly apparent when viewing the crystal along the crystallographic a axis. The anions in 3 pack as dimers inter­acting across a crystallographic inversion center via two 2.430 (2) Å C—H⋯F con­tacts between ortho atoms H5 and F3 (Fig. 9). There are four con­tacts between the F atoms of the anion and the cations, with distances ranging from 2.312 (2) to 2.576 (2) Å, with an average H⋯F con­tact distance of 2.394 (2) Å. The pyridine N atom of the anion forms con­tacts with two α-H atoms on an adjacent cation, with distances of 2.609 (3) and 2.583 (2) Å.

Figure 7 The asymmetric unit of 3. H atoms have been omitted from the cation for clarity.

Figure 8 A 3×3×3 packing diagram of salt 3, viewed along the crystallographic a axis. The image on the right shows the same view with the cations hidden to highlight the arrangement of the anions.

Figure 9 Anion–anion con­tacts in 3.

Compound 4 crystallized in the monoclinic space group P2₁/c with Z′ = 1 (Fig. 10). The crystal packing of 4 shows that the anions are com­pletely separated by cations and there are no anion–anion con­tacts in the structure (Fig. 11). In com­parison to 3, 4 has twice as many anion–cation con­tacts involving the F atoms of the anion, ranging from 2.279 (2) to 2.494 (2) Å. The average H⋯F distance in 4 is 2.391 (2) Å, similar to 3 [2.394 (2) Å]. The environment of the pyridine N atom is quite different com­pared to 3. Unlike in 3, which had close con­tacts between the pyridine N atom and two α-H atoms of the cation, the pyridine N atom in 4 only forms one close con­tact to a methyl H atom on the cation, with an N⋯H distance of 2.654 (2) Å.

Figure 10 The asymmetric unit of 4. H atoms have been omitted from the cation for clarity.

Figure 11 A 3×3×3 packed unit cell of 4, viewed along the a axis. The image on the right is the same view with the cations hidden.

3.3. Tetra­phenyl­phospho­nium salts

Compounds 5 and 6 contain the tetra­phenyl­phospho­nium (PPh₄⁺) cation. The 3-pyri­dyl tri­fluoro­borate salt 5 crystallized in the monoclinic space group Pc with Z′ = 1 (Fig. 12). The crystal packing of 5 shows a layer-like structure, with the ions arranged such that the cations and anions form alternating rows parallel to the b and c axes, alternating along the a axis of the crystal (Fig. 13). As with com­pound 4, the anions are com­pletely separated by cations in the crystal packing and there are no close con­tacts between the anions in 5. There are eight cation–anion con­tacts involving the F atoms of the anion ranging from 2.122 (2) to 2.480 (3) Å, with an average distance of 2.310 (3) Å, a shorter average distance than for the two TBA salts. The pyridine N atom of the anion has four close con­tacts with H atoms on different cations. Of these, the con­tacts with the ortho-H atom on C29 and the meta-H atom on C20 are in a position such that they are likely inter­acting with the lone electron pair of the pyridine N atom, while the other two con­tacts are on the face of the pyridine ring and are likely C—H⋯π con­tacts. Of the con­tacts likely involving the N-atom lone pair, the con­tact with the ortho-H atom [2.591 (3) Å] is shorter than that of the meta-H atom [2.699 (3) Å], consistent with com­putations that suggest the ortho-H atoms of PPh₄-derived cations are the preferred site for inter­actions with anions (Dempsey & Kass, 2022).

Figure 12 The asymmetric unit of 5. H atoms have been omitted from the cation for clarity.

Figure 13 A 3×3×3 packing diagram of salt 5, viewed along the crystallographic b axis. The image on the right shows the same view with the cations hidden.

The 4-pyri­dyl analogue 6 crystallized in the triclinic space group P1 with Z′ = 2 (Fig. 14). There are two unique ion pairs in the unit cell that are distinguished by the suffixes A and B. The anions are arranged such that one anion has the pyridine N atom oriented in the direction of the positive a axis, while the other has the pyridine N atom oriented in the direction of the negative c axis, forming alternating rows of anions (Fig. 15). There is a single anion–anion con­tact in the packing of 6, with the anions linked by a single 2.657 (6) Å C—H⋯F con­tact between a meta-H atom on anion A with an F atom on anion B (Fig. 16). Anion A has ten cation–anion con­tacts involving the F atoms of the anion ranging from 2.216 (5) to 2.626 (4) Å, with an average con­tact distance of 2.427 (4) Å. Anion B has eight analogous con­tacts ranging from 2.296 (3) to 2.620 (3) Å, with a slightly longer average con­tact distance of 2.459 (4) Å. The pyridine N atoms of the two anions in the structure differ slightly in their crystallographic environments. Anion A has three close con­tacts between the pyridine N atom and three different cations. Only one of these, the 2.566 (5) Å con­tact with the meta-H atom on C26A, is positioned in such a way that the H atom is able to inter­act with the lone pair of the pyridine N atom. The other two C—H⋯N inter­actions occur on the `face' of the N atom and are likely electrostatic in nature rather than a hy­dro­gen bond, but it should be noted that the con­tact with the para-H atom on C9A is the shortest of the three con­tacts at 2.494 (5) Å. Anion B only forms two con­tacts with the pyridine N atom. In this case, both con­tacts are positioned in such a way that the H atom could be inter­acting with the lone pair of the pyridine N atom. The shortest con­tact is with the ortho-H atom of C13A at a distance of 2.463 (7) Å, while the second is much longer at 2.780 (6) Å with the para-H atom of C15B.

Figure 14 The asymmetric unit of 6. H atoms have been omitted from the cations for clarity.

Figure 15 A 3×3×3 packing diagram of salt 6, viewed along the crystallographic c axis. The image on the right shows the same view with the cations hidden.

Figure 16 Close con­tacts between anions in 6.

3.4. Tetra­kis(3,5-di­meth­oxy­phen­yl)phospho­nium salts

Compounds 7 and 8 contain the tetra­kis­(3,5-di­meth­oxy­phen­yl)phospho­nium cation (MeO-Phos). The 3-pyri­dyl bo­rate salt 7 crystallized in the space group P2₁/n with Z′ = 1 (Fig. 17). Similar to salt 3, the crystal packing of 7 shows a channel motif, where anions form channels that are separated by cations (Fig. 18). These channels run roughly parallel to the b axis and layers of cations and anions alternate along the crystallographic a and c axes. Within each channel the anions are linked via a short con­tact of 2.480 (3) Å between the meta-H atom of the anion and an F atom of an adjacent anion. The result of this is a one-dimensional polymeric chain of anions (Fig. 19). This polymeric structure of the anion channels is quite different from the structure of the anion channels in 3, where the channels were formed by repeating units of anion dimers. There is a total of seven cation–anion con­tacts involving the F atoms of the anions. These con­tacts range in length from 2.287 (2) to 2.627 (3) Å, with an average length of 2.429 (3) Å, a similar average length to anion A in 6 [2.427 (4) Å]. The pyridine N atom of the anion in 7 forms three close con­tacts with two different cations. Like in anion A of salt 6, two of the con­tacts formed in 7 occur towards the faces of the pyridine ring. Both of these con­tacts are with methyl H atoms of the cation, and these con­tacts are both long, with lengths of 2.836 (3) and 2.778 (3) Å. The third con­tact is between N1 and the H atom on para atom C26 of the cation. This H atom is directly in line with the N-atom lone pair and forms a short C—H⋯N con­tact of 2.250 (3) Å.

Figure 17 The asymmetric unit of 7. H atoms have been omitted from the cation for clarity.

Figure 18 The left image shows a 3×3×3 packing diagram of salt 7, viewed along the crystallographic b axis. The image on the right shows the same view with the cations hidden.

Figure 19 Anion–anion con­tacts present in salt 7.

The 4-pyri­dyl borate analogue 8 crystallized in the triclinic space group P with Z′ = 2 as a non-merohedral twin with two twin domains of equal volume (Fig. 20). The packing in 8 shows a channel motif, with the anions forming one-dimensional `head-to-tail' chains in the direction of the a axis, with adjacent layers of chains related by inversion symmetry (Fig. 21). The anions in the chains are linked by con­tacts between a meta-H atom of the pyridine ring with an F atom in the next anion. Like in 6, there are two unique cations and anions in the asymmetric unit of the crystal, differentiated by the suffixes A and B. The two unique anions alternate in the anion channel, exhibiting a polymeric structure like that seen in 7 (Fig. 22, bottom). Anion B is disordered and modeled in two parts, with an occupancy ratio of approximately 66:34 (Fig. 22, top). The primary difference between the two disordered anions is a rotation of the BF₃ group. Anion A has eight cation–anion con­tacts involving the F atoms of the anion (Fig. 22, top). The con­tacts range from 2.260 (5) to 2.644 (5) Å, with an average length of 2.440 (5) Å. The two disordered parts of anion B differ in the number of con­tacts involving the F atoms of the anion. The majorly occupied portion of anion B also has eight con­tacts between the cations and the F atoms of the anion ranging from 2.210 (10) to 2.612 (7) Å, with an average length of 2.400 (8) Å, slightly shorter than the average distance for anion A. In the minorly occupied part of anion B, the BF₃ group is rotated in such a way that atom F1B′ has no con­tacts with the cation, and overall, the number of cation con­tacts involving the F atoms of the anion has reduced to five, ranging from 2.299 (10) to 2.610 (10) Å, with an average distance of 2.486 (14) Å. Averaging the cation–fluorine con­tact distances for all three anions in 8 gives a distance of 2.442 (9) Å, slightly longer than the average distance in 7 [2.429 (3) Å]. Anion A shows three C—H⋯N con­tacts between the pyridine N atom and methyl groups on two cations. As seen in several of the other 4-pyri­dyl anions, two of the con­tacts [with methyl H atoms on C21B and C28A of 2.633 (5) and 2.797 (5) Å, respectively] are on the face of the pyridine ring, while the third con­tact, with a methyl H atom on C13B, is in a location such that it could be inter­acting with the pyridine lone pair. However, this con­tact is likely not a C—H⋯N hy­dro­gen bond, as the con­tact is quite long [2.855 (5) Å] and the C—H⋯N angle is 100°, both factors suggesting this is a primarily electrostatic con­tact rather than a hy­dro­gen-bonding inter­action. The majorly and minorly occupied parts of disordered anion B have slightly different environments of the pyridine N atom. The majorly occupied part of anion B shows only two close con­tacts involving the pyridine N atom, one with a H atom on methyl atom C29A [2.74 (2) Å] and the other with the H atom on para atom C9A [2.661 (10) Å]. The con­tact with the para-H atom is in line with the lone pair of the pyridine N atom, while the con­tact with the methyl H atom occurs more on the face of the pyridine ring. The minorly occupied part of anion B has con­tacts with these same H atoms, although the pyridine N atom has shifted further from C29A and closer to C9A, resulting in new con­tact distances of 2.81 (4) Å for the methyl H atom on C29A and 2.411 (10) Å for the para-H atom on C9A. Additionally, the minorly occupied portion of anion B has con­tacts with two of the methyl H atoms of C13A [distances of 2.69 (4) and 2.67 (4) Å] with the pyridine N atom. The new C—H⋯N con­tacts occur on the face of the pyridine ring.

Figure 20 The asymmetric unit of 8. Only the majorly occupied part of anion B is shown. H atoms have been omitted from the cations for clarity.

Figure 21 The image on the left shows a 3×3×3 packing diagram of salt 8, viewed along the crystallographic a axis. Only the majorly occupied part of anion B is shown. The image on the right shows the same view with the cations hidden.

Figure 22 (Top) A superposition of the two parts of the disordered anion in 8. (Bottom) The head-to-tail chain packing of the anions in 8. Only the majorly occupied part of anion B is shown.

3.5. Tetra­kis[4-(di­methyl­amino)­phen­yl]phospho­nium salts

Compounds 9 and 10 contain the tetra­kis­[4-(di­methyl­amino)­phen­yl]phospho­nium cation (NMe₂-Phos). Compound 9 crystallized in the monoclinic space group P2₁/n with Z′ = 1 (Fig. 23). Like com­pound 3, the anions in 9 crystallize as dimers across a crystallographic inversion center. The anion dimers are com­pletely separated from other anion dimers by cations (Fig. 24). A close con­tact is made between the meta-H atom of one anion with an F atom of the inversion-related anion. The anion is disordered and modeled in two parts, each with 50% occupancy (Fig. 25, top). In the crystal structure, the disordered parts are differentiated by the addition of a prime (′) suffix to the second part. Because the anions have equal occupancy, the two anions will be referred to as the `primed' and `unprimed' anions. The anion dimers are related by an inversion center, however it is unlikely that the anions that are related directly by symmetry pack at the same time (i.e. the primed anion forming a dimer with the primed anion), as this results in a very close 1.67 (3) Å H⋯H con­tact between H5′ and it's inversion-related equivalent (Fig. 25, middle). Instead, the packing most likely consists of the unprimed anion and the primed anion packed across the inversion center (Fig. 25, bottom). In this packing arrangement, the con­tact distance between H5 and H5′ is a more reasonable 2.12 (3) Å. The anions form a C—H⋯F con­tact of 2.63 (5) Å between the meta-H atom on C4 of the unprimed anion and F1′ of the primed anion. The major difference between the primed and unprimed anions is a rotation of the BF₃ groups on the anions. The F atoms of the unprimed anion form six cation–anion con­tacts ranging from 2.165 (7) to 2.549 (5) Å, with an average length of 2.361 (5) Å. The F atoms of the primed anion also form six cation–anion con­tacts, ranging from 2.169 (9) to 2.565 (5) Å, with an average of 2.444 (13) Å. The average con­tact distance for both anions is 2.402 (9) Å. The two anions differ only slightly in the chemical environments of their pyridine N atoms. Both anions form C—H⋯N con­tacts with a methyl H atom on C21. The con­tact with the unprimed anion is shorter, with a distance of 2.521 (10) Å, while the con­tact with the primed anion is 2.81 (2) Å.

Figure 23 The asymmetric unit of 9. H atoms have been omitted from the cation for clarity.

Figure 24 A 3×3×3 packing diagram of salt 9, viewed along the crystallographic b axis. The image on the right shows the same view with the cations hidden. Only the unprimed anion is shown.

Figure 25 (Top) A superposition of the two equally occupied disordered parts of the anion in 9. (Middle) The close con­tact between the primed anion and its inversion-related equivalent highlighting the unlikely 1.67 (3) Å H⋯H con­tact. (Bottom) A more realistic anion dimer between the primed and unprimed anions across the inversion center.

Two different crystals of com­pound 10 were obtained by evaporation from two different solvents. When DCM was used as a solvent, crystals of the neat salt were obtained in the monoclinic space group P2₁/n with Z′ = 1 (Fig. 26). The cation in the crystal structure is well resolved; however, the anion is severely disordered. The anion is modeled in three parts with approximate occupancies of 43.3, 33.2, and 23.5%. Because of the highly disordered nature of the anion, there is more uncertainty in the con­tact distances between the mol­ecules in the crystal structure. The packing is very similar to what is seen in 9, with the anions packed in dimers related by inversion symmetry (Fig. 27). Like in 9, the disorder of the anion results in unrealistically close H⋯H con­tacts between anions across a crystallographic inversion center, and it is unlikely that anions directly related by inversion symmetry pack at the same time; however, any detailed analysis of the anion packing is hampered by the disorder. Treating all of the disordered parts of the anion as a whole, it can be seen that there are 25 con­tacts between the F atoms of the anion and H atoms of the cation, ranging in length from 2.097 (8) to 2.662 (8) Å, with an average con­tact distance of 2.421 (9) Å. The average overall anion-to-cation F⋯H con­tact distance is similar to what is seen in 9. There are only two con­tacts between the anion N and cation H atoms, with a length of 2.77 (2) Å for the con­tact between N1′ and methyl atom H28A, and 2.677 (8) Å for the con­tact between N1′′ and H32. The second con­tact occurs on the face of the pyridine ring.

Figure 26 The asymmetric unit of 10. All parts of the disordered anion are shown superimposed. H atoms have been omitted from the cation for clarity.

Figure 27 A 3×3×3 packed unit cell of 10. The image on the right has the cations hidden to highlight the dimer packing arrangement of the anions.

When crystals of 10 are grown by evaporation from acetone, the com­pound is obtained as a hemihydrate (10h) in the monoclinic space P2₁/n with Z′ = 1 (Fig. 28). The structure solution of this crystal form has both the cation and anion well resolved. Fig. 29 shows the packing of the crystal, viewed along the b axis. The anions form dimers linked by 2.02 (3) Å hy­dro­gen bonds between the pyridine N atom and a single water mol­ecule across a crystallographic inversion center, with the water mol­ecule positioned on the inversion center. There are no con­tacts between anions. The F atoms of the anion form ten cation–anion con­tacts in the crystal structure. These con­tacts range in length from 2.308 (2) to 2.638 (3) Å, with an average of 2.482 (2) Å. This is the longest cation–anion H⋯F average distance of all the salts with organic cations; however, it is also the only salt to have cocrystallized water, which impacts the packing of the anion. The pyridine N atom primarily forms a hy­dro­gen bond with the water mol­ecule, but there is also a 2.595 (4) Å N⋯H con­tact with a methyl H atom on atom C37 of the cation.

Figure 28 The asymmetric unit of 10h.

Figure 29 A 3×3×3 packed unit cell of 10h, viewed along the crystallographic b axis. The image on the right has the cations hidden. Each water mol­ecule shown has a 50% occupancy, leading to an overall anion–water stoichiometry of 2:1.

3.6. Trends in cation–anion N⋯H and F⋯H con­tacts for salts 3–10 and 10h

Because the potassium salts 1 and 2 are not soluble in low-polarity solvents such as DCM, they are not well suited for use as charge-enhanced catalysts and the focus of the upcoming analyses will be on the more soluble salts with organic cations (3–10 and 10h). Table 2 shows the number and average lengths of the cation–anion N⋯H and F⋯H con­tacts for each of the salts containing organic cations. For all of the salts, the F⋯H con­tacts were more numerous and shorter in length than the N⋯H con­tacts. Examining the N⋯H con­tacts (excluding 10h, in which the sole N⋯H con­tact of the anion is with the cocrystallized water mol­ecule), it can be seen that 3 has the shortest observed N⋯H con­tact at 2.583 (2) Å. Salt 10 has the longest N⋯H con­tact distance at 2.726 (14) Å (averaged across all parts of the disordered anion). Arranging the salts by average N⋯H con­tact distance gives the following order: 3 < 6 < 7 < 4 < 9 < 5 < 8 < 10; however, it should be noted that the average lengths for salts 4 and 9, 6 and 7, and 8 and 10 have values that overlap when uncertainties are taken into con­sid­er­a­tion. For the F⋯H con­tact distances, salt 5 has the shortest average distance at 2.310 (3) Å. The longest average F⋯H con­tact distances are in 10h; however, the presence of the water mol­ecule precludes this com­pound from direct com­parison to the others. Ordering the salts by average F⋯H con­tact distance gives: 5 < 4 < 3 < 9 < 10 < 7 < 8 < 6 < 10h, noting that salts 3 and 4, 9, 6, and 8, and 7 and 10 have values that overlap when considering uncertainties. Across salts with the same cation, the position of the N atom in the pyridine ring of the anions has only a small effect on the average N⋯H con­tact distance for most of the salts, with the largest difference being seen in the MeO-Phos salts 7 and 8, which differ by 0.092 (9) Å. Examining the F⋯H con­tacts of the 3- and 4-pyri­dyl tri­fluoro­borate anions with the same cation, it is found that the position of the pyridine N atom on the anion has little effect on the average F⋯H con­tact length of the TBA salts (3 and 4), the MeO-Phos salts (7 and 8), and the neat NMe₂-Phos salts (9 and 10). There is a significant difference between the PPh₄ salts 5 and 6, with the average F⋯H con­tact distance being 0.132 (4) Å shorter in the 3-pyri­dyl salt 5 com­pared to the 4-pyri­dyl analogue 6. The average F⋯H con­tact distance difference between 10 and 10h is 0.061 (10) Å. Overall, there are no significant trends between the position of the pyridine N atom or the identity of the cation on the average lengths of the N⋯H and F⋯H con­tacts in the crystal structures containing organic cations.

Table 2
The number and average lengths of cation–anion N⋯H and F⋯H con­tacts for each of the salts containing organic cations

Salt	Number of N⋯H con­tacts	Average N⋯H con­tact distance (Å)	Number of F⋯H con­tacts	Average F⋯H con­tact distance (Å)
3	2	2.596 (3)	4	2.394 (2)
4	1	2.654 (2)	8	2.391 (2)
5	4	2.670 (4)	9	2.310 (3)
6	5^a	2.612 (6)^b	18^a	2.442 (4)^b
7	3	2.621 (3)	8	2.429 (3)
8	9^a,c	2.713 (9)^b,d	21^a,c	2.441 (8)^b,d
9	2^c	2.665 (15)^d	12^c	2.402 (9)^d
10	2^c	2.726 (14)^d	21^c	2.421 (9)^d
10h	1	2.595 (2)	10	2.482 (4)
Notes: (a) the total number of con­tacts across both anions; (b) the average value across both anions; (c) the total number of con­tacts between all parts of the disordered anion; (d) the average values between all parts of the disordered anion.

4. Hirshfeld surface analysis

Hirshfeld surface analysis offers a unique way to visualize the chemical environment of different mol­ecules within a crystal (Spackman & Jayatilaka, 2009; Spackman et al., 2021). Briefly, Hirshfeld surfaces are a means by which the electron density of the crystal is broken down into the contributions from each of the mol­ecules within the crystal. The distances of atoms to the Hirshfeld surface of a mol­ecule can be plotted for atoms both inside (d_i) and outside (d_e) of the surface to provide a unique plot, called a fingerprint plot, for each mol­ecule in a crystal structure. `Spikes' in the direction of the lower left portion of the fingerprint plots (i.e. small d_i/d_e distances) indicate the presence of close con­tacts between atoms inside and outside of the Hirshfeld surface, corresponding to close con­tacts between atoms in different mol­ecules. Fingerprint plots are colored ranging from blue to green to red by the number of contributing points of the Hirshfeld surface to the particular d_i/d_e distance, with blue points having few contributions and red points having many. Fingerprint plots can be divided to show the types of inter­molecular con­tacts contributing to the surface and the percentage that each con­tact type contributes to the overall surface. Fig. 30 shows the fingerprint plots for the anions of salts 3–10 and 10h. In the cases where the anion was disordered, all parts of the disordered anion were treated as one to generate a single Hirshfeld surface. While the fingerprint plots for each anion are unique, there is little difference in the fingerprint plots between the 3- and 4-pyri­dyl tri­fluoro­borate anions when paired with the same cation, particularly in the region of small d_i/d_e values that correspond to close con­tacts between ions. Of these, the anions that appear the most different are 9, 10, and 10h. The fingerprint plots of com­pounds 9 and 10 are similar, with both showing a sharp spike terminating in the 0.8/0.8 Å d_i/d_e region (9) and the 0.6/0.86 Å d_i/d_e region (10) (Fig. 30, bottom row, left and middle). These spikes are a result of unrealistic H⋯H con­tacts across the inversion center resulting from the disordered anions discussed in Section 3.5. Salt 10h shows a spike terminating in the 1.2/0.8 Å d_i/d_e region that corresponds to the hy­dro­gen bond between the anion and the water mol­ecule (Fig. 30, bottom row, right). Because of the presence of the cocrystallized water in 10h, it is not surprising to see a large difference between this fingerprint plot and those of the neat forms 9 and 10. Table 3 shows the breakdown of the major contributions of different types of con­tacts to the Hirshfeld surface of each anion. The Hirshfeld surfaces of the tetra­butyl­ammonium salts 3 and 4 have roughly the same N⋯H and C⋯H contributions, while the 4-pyri­dyl analogue has about 4% fewer F⋯H and 4% more H⋯H con­tacts. For the PPh₄ salts 5 and 6, there is very little difference in the amount that each type of con­tact contributes to the Hirshfeld surface, with the differences in the amount of each type of con­tact not exceeding 2.1%. The MeO-Phos salts 7 and 8 likewise show little difference in their Hirshfeld surface com­position, with similar N⋯H and O⋯H contributions. The 4-pyri­dyl borate anions in 8 have slightly higher F⋯H contributions. Salt 7 and anion A of 8 have similar 14.6 and 13.2% C⋯H contributions, and 33.0 and 34.0% H⋯H contributions, respectively.

Table 3
Contributions (%) of selected con­tacts to the Hirshfeld surfaces for all of the anions

Minor contributors have been omitted, leading to a <100% sum of contributions for some of the anions.

	Contribution to anion Hirshfeld surface
Salt	F⋯H	N⋯H	C⋯H	H⋯H	O⋯H
3	40.3	8.8	13.5	37.4	NA
4	36.2	9.2	13.6	41.0	NA
5	35.8	8.8	23.4	31.6	NA
6, Anion A	35.6	8.4	22.7	32.2	NA
6, Anion B	34.0	9.1	21.3	31.6	NA
7	35.5	8.7	14.6	33.0	4.4
8, Anion A	38.7	8.0	13.2	34.0	4.1
8, Anion B	37.4	8.6	17.6	29.3	4.3
9	39.3	9.0	14.0	37.0	NA
10	38.8	6.8	16.0	37.5	NA
10h	35.4	8.6	17.9	37.9	0.2

Figure 30 The Hirshfeld surface fingerprint plots for the anions in salts 3–10 and 10h.

Anion B of 8 is the most different in this regard with 17.6% C⋯H and 29.3% H⋯H contributions. The environments of the anions in the NMe₂-Phos salts are again quite similar, with the biggest differences being in the N⋯H (9.0% for 9 and 6.8% for 10) and C⋯H (14.0% for 9 and 16.0% for 10) regions. Comparing salt 10 to 10h, there is a fairly large difference in the F⋯H contributions, with 10h having a smaller surface by 3.4%. Salt 10h has an approximately 2% larger contribution of both N⋯H and C⋯H con­tacts com­pared to 10.

Examining how the identity of the cation affects the Hirshfeld surface com­positions, it can be seen that the average contributions of F⋯H and N⋯H con­tacts to the Hirshfeld surfaces are similar, with F⋯H con­tacts accounting for 38.3, 35.1, 37.2, and 37.8%, and N⋯H con­tacts accounting for 9.0, 8.8, 8.4, and 8.1% for the TBA, PPh₄, MeO-Phos, and NMe₂-Phos salts, respectively. On average, the PPh₄ salts have a higher C⋯H contribution of 22.5% com­pared to 13.6, 15.1, and 16.0% for the TBA, MeO-Phos, and NMe₂-Phos salts, respectively. The TBA salts have the largest average contributions of H⋯H con­tacts at 39.2%, followed closely by 37.5% for the NMe₂-Phos salts. In com­parison, the MeO-Phos and PPh₄ salts have lower H⋯H con­tacts at 32.1 and 31.8% for the MeO-Phos and PPh₄ salts, respectively. The MeO-Phos salts contain an average of 4.3% O⋯H contributions to the surface, contributions that are not present in the TBA salts, the PPh₄ salts, and salt 9, and only offer a very minor 0.2% contribution in 10h due to the cocrystallized water. In summary, it can be seen that the position of the pyridine N atom has little effect on the overall environment of the anions across the salts, regardless of the cation, and that changing the cation primarily affects the amount of C⋯H and H⋯H con­tacts for the anions.

5. Comparisons to reactivity

In contrast to polar solvents, where ion pairs exist primarily as solvated `free' ions, ionic com­pounds in non-polar solvents exist primarily as ion pairs or higher-order aggregates, especially as the concentration of the salt increases (Marcus & Hefter, 2006). Inter­actions between the anions and cations in the crystalline state may be present in the solvated ion pairs and have a correlation to the reactivity of the salts. The nucleophilicity for each of the salts was evaluated by com­paring the pseudo-first-order rate constants of the S_N2 reaction between each salt and 1-iodo­octane in di­chloro­methane (Fig. 31). Given the low dielectric constant of the solvent, it is not unreasonable to expect that the salts exist as ion pairs or higher-order aggregates while in solution, with con­tacts between the ions possibly affecting the reactivity of the salts. As such, it is worthwhile to investigate if trends exist between the crystallographic environment of the anions and their nucleophilicity. Salts 3 and 4 were evaluated previously using this reaction (Dempsey, Lovstedt et al., 2023), although the concentrations of reagents are slightly different in this work. The neutral nucleophiles pyridine and DMAP were also evaluated in this manner. Table 4 gives the reaction rate constants and relative rates for pyridine, DMAP, and salts 3–10. Salts 1 and 2 are insoluble in DCM and as a result could not be evaluated.

Table 4
Pseudo-first-order reaction-rate constants and relative rates for each com­pound in the model S_N2 reaction at 298 K

Compound	k (min^−1)	k (relative to pyridine)
Pyridine	0.000259	1.0
DMAP	0.00171	6.6
3	0.00488	18.9
4	0.00254	9.8
5	0.00698	26.9
6	0.00237	9.1
7	0.00661	25.5
8	0.00420	16.2
9	0.00727	28.1
10	0.00502	19.4

Figure 31 The model SN2 reaction for evaluating the nucleophilicity of the 3-pyri­dyl tri­fluoro­borate salts. The 4-pyri­dyl tri­fluoro­borate salts were evaluated in the same manner.

DMAP showed a moderate 6.6-fold rate increase over pyridine. All of the anionic catalysts had a faster rate that DMAP, however, the difference in reaction rates is small, with the fastest reacting salt 9 having a rate about four times greater than DMAP. Consistent with previous work (Demp­sey, Lovstedt et al., 2023), the 3-pyri­dyl tri­fluoro­borate anions were all more reactive than their 4-pyri­dyl analogues. Salt 3 was the slowest reacting 3-pyri­dyl tri­fluoro­borate salt, while the other three 3-pyri­dyl tri­fluoro­borate salts 5, 7, and 9 all had roughly the same rates. Inter­estingly, the trend is quite different for the 4-pyri­dyl tri­fluoro­borate anions. For these anions, the TBA salt 4 and PPh₄ salt 6 had roughly the same rates, while the MeO-Phos salt 8 and NMe₂-Phos salt 10 exhibited faster rates. Salt 10 was about as reactive as 3, while 4 reacted about half as fast as 3. Fig. 32 shows plots of k versus average N⋯H and F⋯H con­tact distances, as well as F⋯H, N⋯H, C⋯H, and H⋯H Hirshfeld surface contributions. It is clear that no trend exists between the reactivity of the salts and the selected crystallographic properties. Thus, at least in the case of the pyri­dyl tri­fluoro­borate salts and model S_N2 reaction examined in this study, no correlations are observed between solid-state crystal packing and solution-state reactivity.

Figure 32 The plots of k versus various crystallographically determined parameters. The Hirshfeld surface contributions for 6 and 8 are the average across both anions.

6. Conclusion

This work examined the trends between the crystal structures and nucleophilicity of several 3- and 4-pyri­dyl tri­fluoro­borate salts with an assortment of cations. For the salts with organic cations, it was found that the identity of the cation and the position of the N atom on the pyridine ring changed the manner in which the anions packed within the crystals, and that the lengths and number of N⋯H and F⋯H con­tacts did not show any trend with the position of the pyridine N atom or the identity of the cation. Hirshfeld surfaces were used to probe the total crystallographic environments of the anions across the salts, and it was determined that the position of the pyridine N atom had little effect on the overall environment of the anions across the salts regardless of the cation, and that changing the cation had primarily affected the amount of C⋯H and H⋯H con­tacts for the anions. The nucleophilicity of the salts with organic cations was determined using a model S_N2 reaction, and all of the anionic salts showed moderate rate increases over pyridine, with the 3-pyri­dyl tri­fluoro­borate anions being more reactive than their 4-pyri­dyl counterparts. The effect of the counter-ion on the reactivity of the salts was different between the 3- and 4-pyri­dyl anions, suggesting that cation coordination behavior is dependent on the identity of the anion. Lastly, it was determined that cation–anion N⋯H and F⋯H con­tact lengths and anion Hirshfeld surface com­positions had no correlation to the reactivity of the salts.

7. Related literature

The following references are cited in the supporting information for this article: Batey & Quach (2001); Li et al. (2009); Petruzziello et al. (2013); Van Geet (1970).

Supporting information

Computing details

Tetraphenylphosphonium 3-(trifluoro-λ⁴-boranyl)pyridine (5)

Crystal data

C24H20P^+·C5H4BF3N^−	F(000) = 504
Mr = 485.27	Dx = 1.309 Mg m^−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54178 Å
a = 10.1711 (2) Å	Cell parameters from 9926 reflections
b = 9.3254 (2) Å	θ = 4.6–74.5°
c = 13.7076 (3) Å	µ = 1.33 mm^−1
β = 108.701 (1)°	T = 126 K
V = 1231.52 (5) Å^3	Block, colorless
Z = 2	0.25 × 0.25 × 0.24 mm

Data collection

Bruker PHOTON III CPAD diffractometer	4708 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.035
φ and ω scans	θmax = 74.6°, θmin = 4.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.661, Tmax = 0.754	k = −11→11
24137 measured reflections	l = −17→16
4783 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 0.2536P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.25 e Å^−3
4783 reflections	Δρmin = −0.26 e Å^−3
316 parameters	Absolute structure: Flack x determined using 2179 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: −0.011 (12)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.65193 (5)	0.58607 (5)	0.75745 (4)	0.01831 (13)
F1	0.17405 (15)	0.36823 (16)	0.72104 (11)	0.0322 (3)
F2	−0.02348 (17)	0.23878 (16)	0.69920 (15)	0.0413 (4)
F3	−0.00297 (15)	0.37849 (16)	0.56846 (12)	0.0337 (3)
C6	0.5146 (2)	0.5781 (2)	0.63693 (17)	0.0209 (4)
C7	0.5394 (2)	0.6163 (2)	0.54585 (18)	0.0252 (5)
H7	0.628241	0.649689	0.547359	0.030*
C8	0.4322 (3)	0.6047 (3)	0.45303 (19)	0.0308 (5)
H8	0.447875	0.631366	0.390787	0.037*
N1	0.3306 (2)	−0.0153 (2)	0.63810 (18)	0.0346 (5)
C1	0.1397 (2)	0.1549 (2)	0.60669 (18)	0.0248 (5)
C2	0.2649 (3)	0.0942 (3)	0.6661 (2)	0.0288 (5)
H2	0.307785	0.134061	0.732544	0.035*
C3	0.2681 (3)	−0.0713 (3)	0.5450 (2)	0.0360 (6)
H3	0.311039	−0.150387	0.523640	0.043*
C4	0.1445 (3)	−0.0205 (3)	0.4782 (2)	0.0366 (6)
H4	0.104147	−0.062852	0.412346	0.044*
C5	0.0808 (3)	0.0939 (3)	0.5095 (2)	0.0312 (5)
H5	−0.003844	0.131059	0.464333	0.037*
C9	0.3031 (3)	0.5547 (3)	0.4501 (2)	0.0326 (5)
H9	0.230843	0.547022	0.386075	0.039*
C10	0.2785 (2)	0.5157 (3)	0.5408 (2)	0.0311 (5)
H10	0.189803	0.480916	0.538608	0.037*
C11	0.3834 (2)	0.5276 (3)	0.63374 (18)	0.0256 (4)
H11	0.366713	0.501521	0.695738	0.031*
C12	0.8000 (2)	0.6752 (2)	0.74092 (17)	0.0206 (4)
C13	0.9122 (2)	0.5992 (2)	0.73040 (18)	0.0252 (5)
H13	0.913593	0.497398	0.733069	0.030*
C14	1.0228 (3)	0.6746 (3)	0.7159 (2)	0.0306 (5)
H14	1.100629	0.624052	0.709363	0.037*
C15	1.0197 (3)	0.8225 (3)	0.71089 (19)	0.0295 (5)
H15	1.095838	0.872913	0.701325	0.035*
C16	0.9065 (3)	0.8985 (2)	0.7197 (2)	0.0299 (5)
H16	0.904754	1.000219	0.715489	0.036*
C17	0.7963 (3)	0.8249 (2)	0.73467 (19)	0.0263 (5)
H17	0.718413	0.875979	0.740671	0.032*
C18	0.6982 (2)	0.4071 (2)	0.80686 (17)	0.0210 (4)
C19	0.6109 (2)	0.2916 (2)	0.76500 (19)	0.0246 (5)
H19	0.531569	0.305198	0.706010	0.030*
C20	0.6407 (3)	0.1561 (3)	0.8102 (2)	0.0309 (5)
H20	0.581046	0.077516	0.782382	0.037*
C21	0.7561 (3)	0.1367 (3)	0.8949 (2)	0.0340 (6)
H21	0.775067	0.044767	0.926143	0.041*
C22	0.8454 (3)	0.2503 (3)	0.9353 (2)	0.0344 (6)
H22	0.926171	0.235123	0.992893	0.041*
C23	0.8170 (3)	0.3859 (3)	0.89164 (18)	0.0280 (5)
H23	0.877928	0.463670	0.919285	0.034*
C24	0.5976 (2)	0.6883 (2)	0.84979 (17)	0.0221 (4)
C25	0.6894 (2)	0.6997 (3)	0.94918 (19)	0.0279 (5)
H25	0.776767	0.652589	0.967155	0.033*
C26	0.6541 (3)	0.7793 (3)	1.0222 (2)	0.0325 (5)
H26	0.717541	0.787507	1.090008	0.039*
C27	0.5268 (3)	0.8469 (3)	0.9966 (2)	0.0369 (6)
H27	0.502148	0.900191	1.047207	0.044*
C28	0.4355 (3)	0.8370 (4)	0.8977 (2)	0.0441 (7)
H28	0.348301	0.884297	0.880265	0.053*
C29	0.4702 (3)	0.7581 (3)	0.8232 (2)	0.0342 (6)
H29	0.407571	0.752057	0.754927	0.041*
B1	0.0703 (3)	0.2860 (3)	0.6495 (2)	0.0273 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0194 (2)	0.0173 (2)	0.0199 (2)	0.0004 (2)	0.00853 (18)	0.00093 (19)
F1	0.0354 (8)	0.0294 (7)	0.0292 (7)	−0.0050 (6)	0.0069 (6)	−0.0043 (6)
F2	0.0441 (9)	0.0313 (8)	0.0611 (11)	−0.0054 (6)	0.0347 (8)	−0.0011 (7)
F3	0.0266 (7)	0.0283 (7)	0.0411 (9)	0.0009 (6)	0.0039 (6)	0.0018 (6)
C6	0.0223 (10)	0.0193 (10)	0.0217 (11)	−0.0002 (8)	0.0079 (8)	0.0012 (8)
C7	0.0282 (11)	0.0254 (11)	0.0261 (12)	0.0015 (9)	0.0145 (9)	0.0006 (9)
C8	0.0381 (13)	0.0353 (13)	0.0203 (12)	0.0016 (10)	0.0111 (10)	0.0004 (9)
N1	0.0307 (10)	0.0293 (11)	0.0463 (13)	0.0024 (9)	0.0159 (9)	0.0076 (9)
C1	0.0232 (10)	0.0227 (11)	0.0296 (12)	−0.0051 (8)	0.0102 (9)	0.0021 (9)
C2	0.0267 (11)	0.0273 (12)	0.0319 (13)	−0.0033 (9)	0.0089 (10)	0.0030 (9)
C3	0.0402 (14)	0.0231 (12)	0.0541 (17)	−0.0014 (10)	0.0280 (13)	0.0007 (11)
C4	0.0422 (14)	0.0328 (14)	0.0380 (14)	−0.0089 (11)	0.0174 (12)	−0.0087 (11)
C5	0.0276 (12)	0.0309 (13)	0.0326 (14)	−0.0020 (9)	0.0061 (10)	−0.0012 (9)
C9	0.0351 (13)	0.0338 (13)	0.0241 (12)	−0.0002 (11)	0.0029 (10)	−0.0006 (10)
C10	0.0243 (11)	0.0334 (13)	0.0329 (13)	−0.0037 (10)	0.0052 (10)	0.0050 (10)
C11	0.0235 (10)	0.0285 (12)	0.0256 (11)	−0.0002 (9)	0.0090 (9)	0.0063 (9)
C12	0.0215 (9)	0.0200 (10)	0.0209 (10)	−0.0021 (8)	0.0076 (8)	0.0005 (8)
C13	0.0252 (11)	0.0220 (11)	0.0296 (12)	0.0006 (9)	0.0107 (9)	0.0013 (9)
C14	0.0247 (11)	0.0335 (13)	0.0364 (13)	−0.0003 (9)	0.0137 (10)	0.0026 (10)
C15	0.0280 (11)	0.0331 (13)	0.0279 (12)	−0.0101 (9)	0.0097 (9)	0.0025 (9)
C16	0.0382 (13)	0.0213 (11)	0.0309 (13)	−0.0078 (10)	0.0119 (10)	0.0008 (9)
C17	0.0307 (11)	0.0199 (11)	0.0298 (12)	0.0008 (9)	0.0117 (9)	−0.0007 (9)
C18	0.0244 (10)	0.0197 (11)	0.0216 (11)	0.0019 (8)	0.0110 (9)	0.0005 (8)
C19	0.0239 (10)	0.0223 (11)	0.0294 (12)	0.0008 (8)	0.0109 (9)	−0.0020 (9)
C20	0.0314 (12)	0.0191 (11)	0.0474 (15)	−0.0001 (9)	0.0201 (11)	−0.0014 (10)
C21	0.0477 (15)	0.0194 (11)	0.0398 (14)	0.0090 (10)	0.0209 (12)	0.0074 (10)
C22	0.0437 (15)	0.0295 (13)	0.0254 (13)	0.0102 (10)	0.0047 (11)	0.0019 (9)
C23	0.0317 (12)	0.0238 (11)	0.0253 (12)	0.0022 (9)	0.0047 (10)	−0.0026 (9)
C24	0.0271 (10)	0.0183 (10)	0.0249 (11)	0.0015 (8)	0.0139 (9)	0.0021 (8)
C25	0.0238 (10)	0.0315 (12)	0.0286 (12)	0.0026 (9)	0.0087 (9)	−0.0042 (9)
C26	0.0360 (13)	0.0375 (13)	0.0250 (12)	0.0029 (11)	0.0112 (10)	−0.0037 (10)
C27	0.0483 (15)	0.0376 (14)	0.0306 (13)	0.0133 (12)	0.0206 (12)	−0.0017 (10)
C28	0.0443 (16)	0.0531 (18)	0.0360 (15)	0.0286 (13)	0.0145 (12)	0.0012 (12)
C29	0.0364 (13)	0.0393 (14)	0.0248 (12)	0.0164 (11)	0.0071 (10)	0.0024 (10)
B1	0.0255 (13)	0.0247 (13)	0.0321 (13)	−0.0036 (10)	0.0099 (10)	−0.0005 (11)

Geometric parameters (Å, º)

P1—C6	1.791 (2)	C13—C14	1.394 (3)
P1—C12	1.796 (2)	C13—H13	0.9500
P1—C18	1.806 (2)	C14—C15	1.381 (4)
P1—C24	1.807 (2)	C14—H14	0.9500
F1—B1	1.414 (3)	C15—C16	1.390 (4)
F2—B1	1.408 (3)	C15—H15	0.9500
F3—B1	1.416 (3)	C16—C17	1.385 (4)
C6—C7	1.397 (3)	C16—H16	0.9500
C6—C11	1.403 (3)	C17—H17	0.9500
C7—C8	1.389 (4)	C18—C23	1.396 (3)
C7—H7	0.9500	C18—C19	1.396 (3)
C8—C9	1.382 (4)	C19—C20	1.397 (3)
C8—H8	0.9500	C19—H19	0.9500
N1—C3	1.336 (4)	C20—C21	1.373 (4)
N1—C2	1.342 (4)	C20—H20	0.9500
C1—C2	1.393 (3)	C21—C22	1.390 (4)
C1—C5	1.395 (4)	C21—H21	0.9500
C1—B1	1.614 (4)	C22—C23	1.389 (3)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.380 (4)	C23—H23	0.9500
C3—H3	0.9500	C24—C25	1.387 (3)
C4—C5	1.385 (4)	C24—C29	1.389 (3)
C4—H4	0.9500	C25—C26	1.383 (3)
C5—H5	0.9500	C25—H25	0.9500
C9—C10	1.392 (4)	C26—C27	1.380 (4)
C9—H9	0.9500	C26—H26	0.9500
C10—C11	1.379 (3)	C27—C28	1.379 (4)
C10—H10	0.9500	C27—H27	0.9500
C11—H11	0.9500	C28—C29	1.393 (4)
C12—C13	1.390 (3)	C28—H28	0.9500
C12—C17	1.399 (3)	C29—H29	0.9500
C6—P1—C12	109.89 (10)	C14—C15—H15	119.6
C6—P1—C18	109.89 (10)	C16—C15—H15	119.6
C12—P1—C18	110.27 (10)	C17—C16—C15	119.5 (2)
C6—P1—C24	110.16 (10)	C17—C16—H16	120.2
C12—P1—C24	107.53 (10)	C15—C16—H16	120.2
C18—P1—C24	109.06 (10)	C16—C17—C12	119.8 (2)
C7—C6—C11	120.0 (2)	C16—C17—H17	120.1
C7—C6—P1	120.21 (17)	C12—C17—H17	120.1
C11—C6—P1	119.71 (17)	C23—C18—C19	120.0 (2)
C8—C7—C6	119.0 (2)	C23—C18—P1	119.64 (17)
C8—C7—H7	120.5	C19—C18—P1	120.22 (17)
C6—C7—H7	120.5	C18—C19—C20	119.7 (2)
C9—C8—C7	120.8 (2)	C18—C19—H19	120.1
C9—C8—H8	119.6	C20—C19—H19	120.1
C7—C8—H8	119.6	C21—C20—C19	120.0 (2)
C3—N1—C2	116.3 (2)	C21—C20—H20	120.0
C2—C1—C5	115.2 (2)	C19—C20—H20	120.0
C2—C1—B1	121.3 (2)	C20—C21—C22	120.6 (2)
C5—C1—B1	123.5 (2)	C20—C21—H21	119.7
N1—C2—C1	126.0 (2)	C22—C21—H21	119.7
N1—C2—H2	117.0	C23—C22—C21	120.2 (2)
C1—C2—H2	117.0	C23—C22—H22	119.9
N1—C3—C4	123.5 (3)	C21—C22—H22	119.9
N1—C3—H3	118.2	C22—C23—C18	119.5 (2)
C4—C3—H3	118.2	C22—C23—H23	120.3
C3—C4—C5	118.4 (3)	C18—C23—H23	120.3
C3—C4—H4	120.8	C25—C24—C29	120.0 (2)
C5—C4—H4	120.8	C25—C24—P1	117.85 (17)
C4—C5—C1	120.6 (2)	C29—C24—P1	122.13 (18)
C4—C5—H5	119.7	C26—C25—C24	120.1 (2)
C1—C5—H5	119.7	C26—C25—H25	119.9
C8—C9—C10	120.2 (2)	C24—C25—H25	119.9
C8—C9—H9	119.9	C27—C26—C25	120.1 (2)
C10—C9—H9	119.9	C27—C26—H26	119.9
C11—C10—C9	119.8 (2)	C25—C26—H26	119.9
C11—C10—H10	120.1	C28—C27—C26	120.0 (2)
C9—C10—H10	120.1	C28—C27—H27	120.0
C10—C11—C6	120.1 (2)	C26—C27—H27	120.0
C10—C11—H11	119.9	C27—C28—C29	120.5 (2)
C6—C11—H11	119.9	C27—C28—H28	119.8
C13—C12—C17	120.6 (2)	C29—C28—H28	119.8
C13—C12—P1	121.81 (17)	C24—C29—C28	119.3 (2)
C17—C12—P1	117.54 (17)	C24—C29—H29	120.4
C12—C13—C14	119.0 (2)	C28—C29—H29	120.4
C12—C13—H13	120.5	F2—B1—F1	107.8 (2)
C14—C13—H13	120.5	F2—B1—F3	107.6 (2)
C15—C14—C13	120.3 (2)	F1—B1—F3	107.57 (19)
C15—C14—H14	119.8	F2—B1—C1	112.5 (2)
C13—C14—H14	119.8	F1—B1—C1	110.3 (2)
C14—C15—C16	120.7 (2)	F3—B1—C1	111.0 (2)
C12—P1—C6—C7	9.9 (2)	P1—C12—C17—C16	−178.61 (19)
C18—P1—C6—C7	−111.61 (18)	C6—P1—C18—C23	170.02 (18)
C24—P1—C6—C7	128.21 (18)	C12—P1—C18—C23	48.7 (2)
C12—P1—C6—C11	−172.82 (18)	C24—P1—C18—C23	−69.1 (2)
C18—P1—C6—C11	65.7 (2)	C6—P1—C18—C19	−14.3 (2)
C24—P1—C6—C11	−54.5 (2)	C12—P1—C18—C19	−135.55 (18)
C11—C6—C7—C8	0.6 (3)	C24—P1—C18—C19	106.59 (19)
P1—C6—C7—C8	177.90 (18)	C23—C18—C19—C20	1.9 (3)
C6—C7—C8—C9	−0.7 (4)	P1—C18—C19—C20	−173.76 (18)
C3—N1—C2—C1	−0.8 (4)	C18—C19—C20—C21	−0.6 (4)
C5—C1—C2—N1	−0.4 (4)	C19—C20—C21—C22	−1.1 (4)
B1—C1—C2—N1	179.5 (2)	C20—C21—C22—C23	1.5 (4)
C2—N1—C3—C4	1.4 (4)	C21—C22—C23—C18	−0.1 (4)
N1—C3—C4—C5	−0.7 (4)	C19—C18—C23—C22	−1.6 (3)
C3—C4—C5—C1	−0.7 (4)	P1—C18—C23—C22	174.1 (2)
C2—C1—C5—C4	1.1 (3)	C6—P1—C24—C25	177.03 (18)
B1—C1—C5—C4	−178.8 (2)	C12—P1—C24—C25	−63.2 (2)
C7—C8—C9—C10	0.2 (4)	C18—P1—C24—C25	56.3 (2)
C8—C9—C10—C11	0.3 (4)	C6—P1—C24—C29	−5.0 (2)
C9—C10—C11—C6	−0.4 (4)	C12—P1—C24—C29	114.8 (2)
C7—C6—C11—C10	−0.1 (3)	C18—P1—C24—C29	−125.6 (2)
P1—C6—C11—C10	−177.40 (19)	C29—C24—C25—C26	0.5 (4)
C6—P1—C12—C13	−99.2 (2)	P1—C24—C25—C26	178.6 (2)
C18—P1—C12—C13	22.1 (2)	C24—C25—C26—C27	0.5 (4)
C24—P1—C12—C13	140.89 (19)	C25—C26—C27—C28	−1.1 (4)
C6—P1—C12—C17	78.2 (2)	C26—C27—C28—C29	0.5 (5)
C18—P1—C12—C17	−160.50 (18)	C25—C24—C29—C28	−1.1 (4)
C24—P1—C12—C17	−41.7 (2)	P1—C24—C29—C28	−179.0 (2)
C17—C12—C13—C14	1.5 (4)	C27—C28—C29—C24	0.5 (5)
P1—C12—C13—C14	178.81 (19)	C2—C1—B1—F2	−91.9 (3)
C12—C13—C14—C15	−0.7 (4)	C5—C1—B1—F2	88.0 (3)
C13—C14—C15—C16	−0.3 (4)	C2—C1—B1—F1	28.4 (3)
C14—C15—C16—C17	0.6 (4)	C5—C1—B1—F1	−151.7 (2)
C15—C16—C17—C12	0.1 (4)	C2—C1—B1—F3	147.5 (2)
C13—C12—C17—C16	−1.2 (4)	C5—C1—B1—F3	−32.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F1^i	0.95	2.29	3.075 (3)	140
C11—H11···F1	0.95	2.44	3.132 (3)	130
C14—H14···F1^ii	0.95	2.49	3.235 (3)	135
C13—H13···F2^ii	0.95	2.58	3.477 (3)	159
C16—H16···F2^iii	0.95	2.37	3.284 (3)	160
C26—H26···F2^iv	0.95	2.59	3.401 (3)	144
C10—H10···F3	0.95	2.33	3.267 (3)	168
C23—H23···F3^iv	0.95	2.50	3.348 (3)	149
C25—H25···F3^iv	0.95	2.24	3.117 (3)	152

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

Tetraphenylphosphonium 4-(trifluoro-λ⁴-boranyl)pyridine (6)

Crystal data

C24H20P^+·C5H4BF3N^−	Z = 2
Mr = 485.27	F(000) = 504
Triclinic, P1	Dx = 1.335 Mg m^−3
a = 9.4898 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.2000 (3) Å	Cell parameters from 9874 reflections
c = 14.4239 (5) Å	θ = 3.3–79.6°
α = 99.787 (2)°	µ = 1.36 mm^−1
β = 101.625 (2)°	T = 125 K
γ = 113.231 (2)°	Block, colorless
V = 1207.43 (7) Å^3	0.10 × 0.07 × 0.06 mm

Data collection

Bruker PHOTON III CPAD diffractometer	9274 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.034
φ and ω scans	θmax = 79.6°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
Tmin = 0.605, Tmax = 0.754	k = −12→13
24637 measured reflections	l = −18→18
9470 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.5319P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.106	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.35 e Å^−3
9470 reflections	Δρmin = −0.26 e Å^−3
631 parameters	Absolute structure: Flack x determined using 4183 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.000 (15)
Primary atom site location: dual

Special details

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.

Refinement. The reflections -1 0 1 and -1 1 3 were omitted due to suspected interference from the beamstop.

During data collection, there were several sets of frames where the background did not remain constant. The reason behind this is unclear. Frames where this occured were removed from the data processing. As a result, several reflections were not collected. See the Supporting Information section of the associated publication for additional details.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1A	−0.0467 (2)	0.3569 (2)	0.35711 (14)	0.0263 (4)
F2A	0.2176 (3)	0.4093 (3)	0.41191 (16)	0.0351 (5)
F3A	0.1459 (3)	0.5974 (2)	0.40648 (15)	0.0319 (5)
N1A	0.0681 (4)	0.4916 (4)	0.7336 (2)	0.0361 (7)
C1A	0.0901 (4)	0.4709 (4)	0.5382 (2)	0.0226 (6)
C2A	0.1119 (4)	0.6026 (4)	0.6014 (3)	0.0266 (7)
H2A	0.134071	0.688899	0.578974	0.032*
C3A	0.1013 (5)	0.6079 (5)	0.6962 (3)	0.0340 (8)
H3A	0.118595	0.699604	0.737083	0.041*
C4A	0.0467 (4)	0.3654 (5)	0.6738 (3)	0.0348 (8)
H4A	0.022918	0.280762	0.698249	0.042*
C5A	0.0569 (4)	0.3505 (4)	0.5783 (3)	0.0274 (7)
H5A	0.041303	0.257684	0.539889	0.033*
B1A	0.1029 (4)	0.4591 (4)	0.4264 (3)	0.0224 (7)
F1B	0.0670 (3)	−0.1098 (2)	−0.12594 (17)	0.0405 (6)
F2B	0.2219 (3)	0.1393 (2)	−0.08779 (16)	0.0332 (5)
F3B	0.0677 (3)	0.0438 (3)	0.00899 (16)	0.0350 (5)
N1B	0.5707 (5)	−0.0203 (6)	0.1426 (3)	0.0519 (11)
C1B	0.3122 (4)	0.0035 (4)	0.0204 (2)	0.0206 (6)
C2B	0.4327 (4)	0.1222 (4)	0.0979 (2)	0.0293 (7)
H2B	0.428903	0.214973	0.111507	0.035*
C3B	0.5572 (5)	0.1058 (6)	0.1549 (3)	0.0450 (11)
H3B	0.637922	0.189822	0.205857	0.054*
C4B	0.4550 (6)	−0.1354 (6)	0.0686 (4)	0.0478 (11)
H4B	0.460560	−0.227564	0.057965	0.057*
C5B	0.3285 (5)	−0.1272 (4)	0.0072 (3)	0.0294 (7)
H5B	0.251765	−0.212028	−0.044763	0.035*
B1B	0.1646 (4)	0.0188 (4)	−0.0467 (3)	0.0214 (7)
P1B	0.47884 (8)	0.13754 (7)	0.63213 (5)	0.01628 (16)
C6B	0.5862 (4)	0.1130 (3)	0.7405 (2)	0.0182 (6)
C7B	0.7017 (4)	0.0624 (3)	0.7353 (2)	0.0224 (6)
H7B	0.718413	0.034095	0.673806	0.027*
C8B	0.7923 (4)	0.0535 (4)	0.8205 (3)	0.0261 (7)
H8B	0.872361	0.020449	0.817410	0.031*
C9B	0.7659 (4)	0.0927 (4)	0.9097 (2)	0.0254 (7)
H9B	0.826951	0.084935	0.967565	0.031*
C10B	0.6516 (4)	0.1430 (4)	0.9153 (2)	0.0250 (7)
H10B	0.633396	0.168458	0.976794	0.030*
C11B	0.5632 (4)	0.1563 (4)	0.8312 (2)	0.0226 (6)
H11B	0.487601	0.194624	0.835410	0.027*
C12B	0.5249 (4)	0.0604 (3)	0.5276 (2)	0.0191 (6)
C13B	0.4496 (4)	−0.0939 (4)	0.4882 (2)	0.0246 (7)
H13B	0.373329	−0.154803	0.515185	0.030*
C14B	0.4867 (4)	−0.1576 (4)	0.4096 (3)	0.0282 (7)
H14B	0.436000	−0.262402	0.382553	0.034*
C15B	0.5982 (4)	−0.0680 (4)	0.3704 (2)	0.0283 (7)
H15B	0.623210	−0.111872	0.316430	0.034*
C16B	0.6733 (4)	0.0848 (4)	0.4092 (2)	0.0269 (7)
H16B	0.749361	0.145215	0.381898	0.032*
C17B	0.6374 (4)	0.1501 (4)	0.4884 (2)	0.0230 (6)
H17B	0.689145	0.254845	0.515463	0.028*
C18B	0.5452 (4)	0.3335 (3)	0.6497 (2)	0.0200 (6)
C19B	0.6946 (4)	0.4338 (4)	0.7160 (2)	0.0240 (6)
H19B	0.758948	0.398637	0.753781	0.029*
C20B	0.7489 (4)	0.5848 (4)	0.7267 (3)	0.0270 (7)
H20B	0.850120	0.653424	0.772170	0.032*
C21B	0.6551 (4)	0.6353 (4)	0.6710 (3)	0.0258 (7)
H21B	0.692790	0.738771	0.678211	0.031*
C22B	0.5066 (4)	0.5362 (4)	0.6047 (2)	0.0240 (6)
H22B	0.443122	0.572082	0.566968	0.029*
C23B	0.4509 (4)	0.3851 (3)	0.5933 (2)	0.0214 (6)
H23B	0.349581	0.316956	0.547698	0.026*
C24B	0.2641 (4)	0.0435 (3)	0.6065 (2)	0.0185 (6)
C25B	0.1696 (4)	0.0113 (4)	0.5097 (2)	0.0228 (6)
H25B	0.219314	0.036820	0.460244	0.027*
C26B	0.0044 (4)	−0.0575 (4)	0.4864 (2)	0.0264 (7)
H26B	−0.059225	−0.078909	0.420837	0.032*
C27B	−0.0695 (4)	−0.0956 (4)	0.5580 (3)	0.0261 (7)
H27B	−0.183328	−0.142825	0.541577	0.031*
C28B	0.0230 (4)	−0.0648 (4)	0.6534 (2)	0.0258 (7)
H28B	−0.027698	−0.091421	0.702303	0.031*
C29B	0.1900 (4)	0.0051 (4)	0.6784 (2)	0.0222 (6)
H29B	0.252922	0.026510	0.744107	0.027*
P1A	0.81566 (8)	0.62972 (7)	0.12454 (5)	0.01610 (16)
C6A	0.6737 (4)	0.6126 (3)	0.0146 (2)	0.0183 (6)
C7A	0.5383 (4)	0.4764 (3)	−0.0303 (2)	0.0213 (6)
H7A	0.523282	0.395557	−0.002618	0.026*
C8A	0.4260 (4)	0.4590 (4)	−0.1152 (2)	0.0234 (6)
H8A	0.332873	0.366973	−0.145205	0.028*
C9A	0.4503 (4)	0.5770 (4)	−0.1564 (2)	0.0251 (7)
H9A	0.373165	0.566002	−0.214255	0.030*
C10A	0.5869 (4)	0.7108 (4)	−0.1129 (2)	0.0265 (7)
H10A	0.603585	0.790288	−0.142150	0.032*
C11A	0.6994 (4)	0.7300 (3)	−0.0276 (2)	0.0216 (6)
H11A	0.792769	0.821987	0.001796	0.026*
C12A	0.9614 (4)	0.8188 (3)	0.1816 (2)	0.0178 (6)
C13A	0.9077 (4)	0.9259 (3)	0.2055 (2)	0.0206 (6)
H13A	0.796162	0.899750	0.187472	0.025*
C14A	1.0195 (4)	1.0712 (3)	0.2561 (2)	0.0247 (7)
H14A	0.984564	1.145147	0.272276	0.030*
C15A	1.1822 (4)	1.1080 (4)	0.2829 (2)	0.0263 (7)
H15A	1.258011	1.207538	0.317286	0.032*
C16A	1.2350 (4)	1.0021 (4)	0.2604 (2)	0.0259 (7)
H16A	1.346656	1.028678	0.279723	0.031*
C17A	1.1252 (4)	0.8564 (3)	0.2093 (2)	0.0213 (6)
H17A	1.161292	0.783140	0.193542	0.026*
C18A	0.7129 (4)	0.5719 (3)	0.2134 (2)	0.0184 (6)
C19A	0.8040 (4)	0.5737 (4)	0.3033 (2)	0.0233 (6)
H19A	0.915427	0.601196	0.315171	0.028*
C20A	0.7302 (4)	0.5350 (4)	0.3753 (2)	0.0279 (7)
H20A	0.790923	0.533802	0.435899	0.034*
C21A	0.5686 (5)	0.4983 (4)	0.3590 (3)	0.0286 (7)
H21A	0.518900	0.472032	0.408392	0.034*
C22A	0.4791 (4)	0.4997 (4)	0.2706 (3)	0.0254 (7)
H22A	0.368483	0.475194	0.260069	0.031*
C23A	0.5500 (4)	0.5367 (3)	0.1977 (2)	0.0219 (6)
H23A	0.488538	0.538155	0.137406	0.026*
C24A	0.9187 (4)	0.5231 (3)	0.0895 (2)	0.0193 (6)
C25A	0.9713 (4)	0.5427 (4)	0.0068 (2)	0.0236 (6)
H25A	0.944892	0.603069	−0.029982	0.028*
C26A	1.0619 (4)	0.4740 (4)	−0.0215 (3)	0.0264 (7)
H26A	1.098417	0.487555	−0.077407	0.032*
C27A	1.0994 (4)	0.3849 (4)	0.0323 (3)	0.0247 (6)
H27A	1.161433	0.337483	0.013075	0.030*
C28A	1.0461 (4)	0.3655 (4)	0.1139 (3)	0.0242 (6)
H28A	1.072112	0.304539	0.150199	0.029*
C29A	0.9557 (4)	0.4335 (3)	0.1433 (2)	0.0215 (6)
H29A	0.919355	0.419434	0.199214	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.0235 (10)	0.0224 (9)	0.0252 (9)	0.0062 (8)	0.0010 (8)	0.0047 (7)
F2A	0.0290 (11)	0.0517 (13)	0.0284 (10)	0.0241 (10)	0.0090 (8)	0.0047 (9)
F3A	0.0318 (11)	0.0249 (9)	0.0299 (10)	0.0032 (8)	0.0083 (8)	0.0096 (8)
N1A	0.0260 (15)	0.060 (2)	0.0299 (15)	0.0227 (15)	0.0123 (12)	0.0174 (15)
C1A	0.0148 (14)	0.0277 (16)	0.0255 (15)	0.0104 (12)	0.0046 (12)	0.0075 (12)
C2A	0.0256 (16)	0.0315 (17)	0.0283 (17)	0.0173 (14)	0.0100 (13)	0.0078 (13)
C3A	0.0327 (19)	0.047 (2)	0.0299 (18)	0.0240 (17)	0.0127 (15)	0.0095 (16)
C4A	0.0177 (15)	0.048 (2)	0.042 (2)	0.0120 (16)	0.0094 (15)	0.0261 (18)
C5A	0.0161 (15)	0.0276 (16)	0.0339 (18)	0.0059 (13)	0.0040 (13)	0.0110 (14)
B1A	0.0186 (16)	0.0223 (16)	0.0233 (17)	0.0077 (14)	0.0032 (13)	0.0055 (13)
F1B	0.0387 (13)	0.0302 (11)	0.0356 (12)	0.0123 (10)	−0.0091 (10)	−0.0010 (9)
F2B	0.0433 (12)	0.0321 (10)	0.0350 (11)	0.0204 (10)	0.0160 (9)	0.0208 (9)
F3B	0.0332 (11)	0.0523 (13)	0.0379 (11)	0.0291 (11)	0.0187 (9)	0.0222 (10)
N1B	0.038 (2)	0.105 (4)	0.040 (2)	0.047 (2)	0.0206 (17)	0.038 (2)
C1B	0.0202 (15)	0.0237 (14)	0.0216 (14)	0.0092 (12)	0.0110 (12)	0.0113 (12)
C2B	0.0273 (17)	0.0344 (18)	0.0196 (15)	0.0060 (15)	0.0083 (13)	0.0090 (13)
C3B	0.0242 (18)	0.078 (3)	0.0236 (18)	0.012 (2)	0.0064 (15)	0.0197 (19)
C4B	0.059 (3)	0.077 (3)	0.048 (2)	0.055 (3)	0.032 (2)	0.037 (2)
C5B	0.0338 (19)	0.0327 (17)	0.0326 (18)	0.0205 (16)	0.0158 (15)	0.0145 (14)
B1B	0.0218 (17)	0.0222 (16)	0.0214 (16)	0.0106 (14)	0.0055 (13)	0.0082 (13)
P1B	0.0148 (3)	0.0168 (3)	0.0160 (3)	0.0061 (3)	0.0050 (3)	0.0036 (3)
C6B	0.0170 (14)	0.0169 (13)	0.0200 (14)	0.0075 (12)	0.0045 (11)	0.0050 (11)
C7B	0.0221 (15)	0.0225 (14)	0.0239 (15)	0.0108 (13)	0.0083 (12)	0.0053 (12)
C8B	0.0236 (16)	0.0245 (16)	0.0313 (17)	0.0138 (14)	0.0048 (13)	0.0067 (13)
C9B	0.0268 (17)	0.0200 (15)	0.0239 (16)	0.0075 (13)	0.0015 (13)	0.0067 (12)
C10B	0.0240 (16)	0.0277 (16)	0.0183 (14)	0.0080 (13)	0.0054 (12)	0.0040 (12)
C11B	0.0191 (15)	0.0253 (15)	0.0203 (15)	0.0095 (13)	0.0042 (12)	0.0019 (12)
C12B	0.0173 (14)	0.0189 (14)	0.0185 (14)	0.0060 (12)	0.0049 (11)	0.0039 (11)
C13B	0.0234 (16)	0.0242 (16)	0.0261 (16)	0.0090 (13)	0.0120 (13)	0.0049 (12)
C14B	0.0268 (17)	0.0286 (17)	0.0271 (16)	0.0125 (14)	0.0099 (13)	−0.0003 (13)
C15B	0.0246 (16)	0.0427 (19)	0.0211 (15)	0.0192 (16)	0.0087 (13)	0.0039 (13)
C16B	0.0191 (15)	0.0395 (18)	0.0233 (15)	0.0106 (14)	0.0110 (12)	0.0121 (13)
C17B	0.0179 (14)	0.0260 (15)	0.0222 (15)	0.0069 (13)	0.0062 (12)	0.0064 (12)
C18B	0.0193 (14)	0.0213 (14)	0.0197 (14)	0.0085 (12)	0.0085 (12)	0.0043 (11)
C19B	0.0182 (15)	0.0236 (15)	0.0274 (16)	0.0092 (13)	0.0032 (12)	0.0047 (12)
C20B	0.0186 (15)	0.0189 (15)	0.0346 (18)	0.0031 (13)	0.0058 (13)	0.0012 (13)
C21B	0.0272 (17)	0.0188 (14)	0.0303 (17)	0.0067 (13)	0.0131 (14)	0.0077 (12)
C22B	0.0267 (17)	0.0249 (15)	0.0246 (15)	0.0131 (14)	0.0100 (13)	0.0104 (12)
C23B	0.0206 (15)	0.0215 (14)	0.0185 (14)	0.0070 (12)	0.0045 (11)	0.0038 (11)
C24B	0.0182 (14)	0.0151 (13)	0.0197 (14)	0.0056 (11)	0.0055 (11)	0.0032 (11)
C25B	0.0225 (15)	0.0239 (15)	0.0190 (14)	0.0064 (13)	0.0070 (12)	0.0070 (11)
C26B	0.0219 (15)	0.0306 (16)	0.0210 (15)	0.0087 (14)	0.0020 (12)	0.0056 (12)
C27B	0.0167 (15)	0.0258 (16)	0.0305 (17)	0.0054 (13)	0.0066 (13)	0.0053 (13)
C28B	0.0204 (15)	0.0303 (16)	0.0257 (16)	0.0091 (13)	0.0112 (13)	0.0058 (13)
C29B	0.0210 (15)	0.0262 (15)	0.0183 (14)	0.0090 (13)	0.0070 (12)	0.0055 (12)
P1A	0.0162 (3)	0.0173 (3)	0.0162 (3)	0.0080 (3)	0.0060 (3)	0.0055 (3)
C6A	0.0176 (14)	0.0221 (14)	0.0167 (13)	0.0100 (12)	0.0056 (11)	0.0053 (11)
C7A	0.0236 (15)	0.0180 (14)	0.0219 (14)	0.0086 (12)	0.0074 (12)	0.0055 (11)
C8A	0.0192 (15)	0.0222 (15)	0.0249 (15)	0.0063 (12)	0.0067 (12)	0.0045 (12)
C9A	0.0214 (15)	0.0333 (17)	0.0210 (15)	0.0127 (14)	0.0047 (12)	0.0091 (13)
C10A	0.0338 (18)	0.0217 (15)	0.0232 (16)	0.0103 (14)	0.0069 (14)	0.0110 (12)
C11A	0.0232 (15)	0.0193 (14)	0.0211 (14)	0.0074 (12)	0.0078 (12)	0.0067 (11)
C12A	0.0189 (14)	0.0195 (13)	0.0165 (13)	0.0083 (12)	0.0078 (11)	0.0059 (10)
C13A	0.0233 (15)	0.0221 (14)	0.0189 (14)	0.0110 (12)	0.0082 (12)	0.0070 (11)
C14A	0.0357 (18)	0.0185 (14)	0.0197 (14)	0.0108 (14)	0.0102 (13)	0.0059 (11)
C15A	0.0294 (17)	0.0203 (15)	0.0197 (15)	0.0014 (13)	0.0072 (13)	0.0061 (12)
C16A	0.0194 (15)	0.0298 (17)	0.0221 (15)	0.0054 (13)	0.0059 (12)	0.0058 (13)
C17A	0.0217 (15)	0.0243 (15)	0.0200 (14)	0.0102 (13)	0.0097 (12)	0.0071 (12)
C18A	0.0195 (14)	0.0189 (13)	0.0189 (14)	0.0093 (12)	0.0091 (11)	0.0048 (11)
C19A	0.0223 (16)	0.0263 (15)	0.0208 (15)	0.0100 (13)	0.0075 (12)	0.0060 (12)
C20A	0.0330 (18)	0.0336 (18)	0.0193 (15)	0.0154 (15)	0.0094 (13)	0.0090 (13)
C21A	0.0341 (19)	0.0263 (16)	0.0265 (16)	0.0101 (14)	0.0179 (14)	0.0076 (13)
C22A	0.0209 (16)	0.0230 (15)	0.0301 (16)	0.0064 (13)	0.0121 (13)	0.0047 (13)
C23A	0.0212 (15)	0.0205 (14)	0.0239 (15)	0.0093 (12)	0.0081 (12)	0.0043 (12)
C24A	0.0181 (14)	0.0185 (13)	0.0186 (14)	0.0064 (12)	0.0045 (11)	0.0041 (11)
C25A	0.0295 (17)	0.0247 (15)	0.0246 (15)	0.0157 (14)	0.0134 (13)	0.0111 (12)
C26A	0.0303 (17)	0.0266 (16)	0.0272 (16)	0.0133 (14)	0.0172 (14)	0.0073 (13)
C27A	0.0196 (15)	0.0219 (15)	0.0331 (17)	0.0110 (12)	0.0083 (13)	0.0036 (12)
C28A	0.0251 (16)	0.0206 (14)	0.0287 (16)	0.0120 (13)	0.0065 (13)	0.0085 (12)
C29A	0.0229 (15)	0.0199 (14)	0.0201 (14)	0.0078 (12)	0.0054 (12)	0.0069 (11)

Geometric parameters (Å, º)

F1A—B1A	1.416 (4)	C22B—C23B	1.385 (4)
F2A—B1A	1.406 (5)	C22B—H22B	0.9500
F3A—B1A	1.404 (4)	C23B—H23B	0.9500
N1A—C4A	1.337 (6)	C24B—C29B	1.392 (4)
N1A—C3A	1.337 (5)	C24B—C25B	1.403 (4)
C1A—C5A	1.398 (5)	C25B—C26B	1.379 (5)
C1A—C2A	1.402 (5)	C25B—H25B	0.9500
C1A—B1A	1.629 (5)	C26B—C27B	1.387 (5)
C2A—C3A	1.385 (5)	C26B—H26B	0.9500
C2A—H2A	0.9500	C27B—C28B	1.382 (5)
C3A—H3A	0.9500	C27B—H27B	0.9500
C4A—C5A	1.388 (5)	C28B—C29B	1.393 (5)
C4A—H4A	0.9500	C28B—H28B	0.9500
C5A—H5A	0.9500	C29B—H29B	0.9500
F1B—B1B	1.411 (4)	P1A—C12A	1.791 (3)
F2B—B1B	1.417 (4)	P1A—C6A	1.794 (3)
F3B—B1B	1.404 (4)	P1A—C24A	1.801 (3)
N1B—C3B	1.329 (7)	P1A—C18A	1.802 (3)
N1B—C4B	1.345 (7)	C6A—C11A	1.394 (4)
C1B—C5B	1.388 (5)	C6A—C7A	1.396 (4)
C1B—C2B	1.398 (5)	C7A—C8A	1.385 (5)
C1B—B1B	1.612 (5)	C7A—H7A	0.9500
C2B—C3B	1.382 (6)	C8A—C9A	1.390 (5)
C2B—H2B	0.9500	C8A—H8A	0.9500
C3B—H3B	0.9500	C9A—C10A	1.386 (5)
C4B—C5B	1.382 (6)	C9A—H9A	0.9500
C4B—H4B	0.9500	C10A—C11A	1.384 (5)
C5B—H5B	0.9500	C10A—H10A	0.9500
P1B—C12B	1.794 (3)	C11A—H11A	0.9500
P1B—C18B	1.797 (3)	C12A—C17A	1.396 (4)
P1B—C6B	1.798 (3)	C12A—C13A	1.398 (4)
P1B—C24B	1.801 (3)	C13A—C14A	1.391 (5)
C6B—C7B	1.393 (5)	C13A—H13A	0.9500
C6B—C11B	1.396 (4)	C14A—C15A	1.388 (5)
C7B—C8B	1.390 (5)	C14A—H14A	0.9500
C7B—H7B	0.9500	C15A—C16A	1.378 (5)
C8B—C9B	1.383 (5)	C15A—H15A	0.9500
C8B—H8B	0.9500	C16A—C17A	1.391 (5)
C9B—C10B	1.381 (5)	C16A—H16A	0.9500
C9B—H9B	0.9500	C17A—H17A	0.9500
C10B—C11B	1.389 (5)	C18A—C19A	1.399 (4)
C10B—H10B	0.9500	C18A—C23A	1.401 (5)
C11B—H11B	0.9500	C19A—C20A	1.393 (5)
C12B—C17B	1.395 (4)	C19A—H19A	0.9500
C12B—C13B	1.398 (4)	C20A—C21A	1.385 (5)
C13B—C14B	1.387 (5)	C20A—H20A	0.9500
C13B—H13B	0.9500	C21A—C22A	1.388 (5)
C14B—C15B	1.388 (5)	C21A—H21A	0.9500
C14B—H14B	0.9500	C22A—C23A	1.387 (4)
C15B—C16B	1.385 (5)	C22A—H22A	0.9500
C15B—H15B	0.9500	C23A—H23A	0.9500
C16B—C17B	1.393 (5)	C24A—C29A	1.395 (4)
C16B—H16B	0.9500	C24A—C25A	1.398 (4)
C17B—H17B	0.9500	C25A—C26A	1.385 (5)
C18B—C19B	1.396 (4)	C25A—H25A	0.9500
C18B—C23B	1.400 (4)	C26A—C27A	1.391 (5)
C19B—C20B	1.387 (5)	C26A—H26A	0.9500
C19B—H19B	0.9500	C27A—C28A	1.385 (5)
C20B—C21B	1.385 (5)	C27A—H27A	0.9500
C20B—H20B	0.9500	C28A—C29A	1.384 (5)
C21B—C22B	1.388 (5)	C28A—H28A	0.9500
C21B—H21B	0.9500	C29A—H29A	0.9500
C4A—N1A—C3A	115.9 (3)	C21B—C22B—H22B	119.9
C5A—C1A—C2A	115.0 (3)	C22B—C23B—C18B	119.4 (3)
C5A—C1A—B1A	122.4 (3)	C22B—C23B—H23B	120.3
C2A—C1A—B1A	122.6 (3)	C18B—C23B—H23B	120.3
C3A—C2A—C1A	120.6 (3)	C29B—C24B—C25B	119.5 (3)
C3A—C2A—H2A	119.7	C29B—C24B—P1B	122.9 (2)
C1A—C2A—H2A	119.7	C25B—C24B—P1B	117.5 (2)
N1A—C3A—C2A	124.0 (4)	C26B—C25B—C24B	120.0 (3)
N1A—C3A—H3A	118.0	C26B—C25B—H25B	120.0
C2A—C3A—H3A	118.0	C24B—C25B—H25B	120.0
N1A—C4A—C5A	124.1 (3)	C25B—C26B—C27B	120.5 (3)
N1A—C4A—H4A	118.0	C25B—C26B—H26B	119.8
C5A—C4A—H4A	118.0	C27B—C26B—H26B	119.8
C4A—C5A—C1A	120.5 (4)	C28B—C27B—C26B	119.8 (3)
C4A—C5A—H5A	119.8	C28B—C27B—H27B	120.1
C1A—C5A—H5A	119.8	C26B—C27B—H27B	120.1
F3A—B1A—F2A	108.7 (3)	C27B—C28B—C29B	120.6 (3)
F3A—B1A—F1A	108.1 (3)	C27B—C28B—H28B	119.7
F2A—B1A—F1A	107.8 (3)	C29B—C28B—H28B	119.7
F3A—B1A—C1A	110.8 (3)	C24B—C29B—C28B	119.7 (3)
F2A—B1A—C1A	111.0 (3)	C24B—C29B—H29B	120.2
F1A—B1A—C1A	110.4 (3)	C28B—C29B—H29B	120.2
C3B—N1B—C4B	115.9 (4)	C12A—P1A—C6A	111.47 (14)
C5B—C1B—C2B	115.0 (3)	C12A—P1A—C24A	108.31 (14)
C5B—C1B—B1B	123.1 (3)	C6A—P1A—C24A	107.44 (14)
C2B—C1B—B1B	121.8 (3)	C12A—P1A—C18A	106.24 (13)
C3B—C2B—C1B	120.7 (4)	C6A—P1A—C18A	109.49 (14)
C3B—C2B—H2B	119.6	C24A—P1A—C18A	113.94 (14)
C1B—C2B—H2B	119.6	C11A—C6A—C7A	120.2 (3)
N1B—C3B—C2B	123.9 (4)	C11A—C6A—P1A	121.3 (2)
N1B—C3B—H3B	118.1	C7A—C6A—P1A	118.5 (2)
C2B—C3B—H3B	118.1	C8A—C7A—C6A	120.1 (3)
N1B—C4B—C5B	123.6 (4)	C8A—C7A—H7A	119.9
N1B—C4B—H4B	118.2	C6A—C7A—H7A	119.9
C5B—C4B—H4B	118.2	C7A—C8A—C9A	119.6 (3)
C4B—C5B—C1B	120.8 (4)	C7A—C8A—H8A	120.2
C4B—C5B—H5B	119.6	C9A—C8A—H8A	120.2
C1B—C5B—H5B	119.6	C10A—C9A—C8A	120.1 (3)
F3B—B1B—F1B	108.1 (3)	C10A—C9A—H9A	120.0
F3B—B1B—F2B	107.9 (3)	C8A—C9A—H9A	120.0
F1B—B1B—F2B	107.1 (3)	C11A—C10A—C9A	120.9 (3)
F3B—B1B—C1B	111.1 (3)	C11A—C10A—H10A	119.5
F1B—B1B—C1B	111.8 (3)	C9A—C10A—H10A	119.5
F2B—B1B—C1B	110.7 (3)	C10A—C11A—C6A	119.1 (3)
C12B—P1B—C18B	110.22 (14)	C10A—C11A—H11A	120.5
C12B—P1B—C6B	108.78 (15)	C6A—C11A—H11A	120.5
C18B—P1B—C6B	107.55 (14)	C17A—C12A—C13A	120.5 (3)
C12B—P1B—C24B	106.69 (14)	C17A—C12A—P1A	120.6 (2)
C18B—P1B—C24B	110.46 (14)	C13A—C12A—P1A	118.6 (2)
C6B—P1B—C24B	113.13 (14)	C14A—C13A—C12A	119.2 (3)
C7B—C6B—C11B	119.9 (3)	C14A—C13A—H13A	120.4
C7B—C6B—P1B	119.9 (2)	C12A—C13A—H13A	120.4
C11B—C6B—P1B	119.9 (2)	C15A—C14A—C13A	120.0 (3)
C8B—C7B—C6B	119.8 (3)	C15A—C14A—H14A	120.0
C8B—C7B—H7B	120.1	C13A—C14A—H14A	120.0
C6B—C7B—H7B	120.1	C16A—C15A—C14A	120.8 (3)
C9B—C8B—C7B	119.9 (3)	C16A—C15A—H15A	119.6
C9B—C8B—H8B	120.0	C14A—C15A—H15A	119.6
C7B—C8B—H8B	120.0	C15A—C16A—C17A	120.1 (3)
C10B—C9B—C8B	120.6 (3)	C15A—C16A—H16A	119.9
C10B—C9B—H9B	119.7	C17A—C16A—H16A	119.9
C8B—C9B—H9B	119.7	C16A—C17A—C12A	119.3 (3)
C9B—C10B—C11B	120.1 (3)	C16A—C17A—H17A	120.3
C9B—C10B—H10B	120.0	C12A—C17A—H17A	120.3
C11B—C10B—H10B	120.0	C19A—C18A—C23A	120.0 (3)
C10B—C11B—C6B	119.6 (3)	C19A—C18A—P1A	117.7 (2)
C10B—C11B—H11B	120.2	C23A—C18A—P1A	122.1 (2)
C6B—C11B—H11B	120.2	C20A—C19A—C18A	119.5 (3)
C17B—C12B—C13B	120.3 (3)	C20A—C19A—H19A	120.3
C17B—C12B—P1B	121.5 (2)	C18A—C19A—H19A	120.3
C13B—C12B—P1B	118.2 (2)	C21A—C20A—C19A	120.3 (3)
C14B—C13B—C12B	119.7 (3)	C21A—C20A—H20A	119.8
C14B—C13B—H13B	120.1	C19A—C20A—H20A	119.8
C12B—C13B—H13B	120.1	C20A—C21A—C22A	120.2 (3)
C13B—C14B—C15B	119.8 (3)	C20A—C21A—H21A	119.9
C13B—C14B—H14B	120.1	C22A—C21A—H21A	119.9
C15B—C14B—H14B	120.1	C23A—C22A—C21A	120.4 (3)
C16B—C15B—C14B	120.6 (3)	C23A—C22A—H22A	119.8
C16B—C15B—H15B	119.7	C21A—C22A—H22A	119.8
C14B—C15B—H15B	119.7	C22A—C23A—C18A	119.6 (3)
C15B—C16B—C17B	120.0 (3)	C22A—C23A—H23A	120.2
C15B—C16B—H16B	120.0	C18A—C23A—H23A	120.2
C17B—C16B—H16B	120.0	C29A—C24A—C25A	120.4 (3)
C16B—C17B—C12B	119.5 (3)	C29A—C24A—P1A	123.7 (2)
C16B—C17B—H17B	120.3	C25A—C24A—P1A	115.8 (2)
C12B—C17B—H17B	120.3	C26A—C25A—C24A	119.9 (3)
C19B—C18B—C23B	120.2 (3)	C26A—C25A—H25A	120.0
C19B—C18B—P1B	119.7 (2)	C24A—C25A—H25A	120.0
C23B—C18B—P1B	120.0 (2)	C25A—C26A—C27A	119.8 (3)
C20B—C19B—C18B	119.8 (3)	C25A—C26A—H26A	120.1
C20B—C19B—H19B	120.1	C27A—C26A—H26A	120.1
C18B—C19B—H19B	120.1	C28A—C27A—C26A	119.9 (3)
C21B—C20B—C19B	119.8 (3)	C28A—C27A—H27A	120.0
C21B—C20B—H20B	120.1	C26A—C27A—H27A	120.0
C19B—C20B—H20B	120.1	C29A—C28A—C27A	121.1 (3)
C20B—C21B—C22B	120.6 (3)	C29A—C28A—H28A	119.5
C20B—C21B—H21B	119.7	C27A—C28A—H28A	119.5
C22B—C21B—H21B	119.7	C28A—C29A—C24A	118.9 (3)
C23B—C22B—C21B	120.1 (3)	C28A—C29A—H29A	120.6
C23B—C22B—H22B	119.9	C24A—C29A—H29A	120.6
C5A—C1A—C2A—C3A	0.4 (5)	C12B—P1B—C24B—C29B	142.4 (3)
B1A—C1A—C2A—C3A	−179.4 (3)	C18B—P1B—C24B—C29B	−97.8 (3)
C4A—N1A—C3A—C2A	0.8 (6)	C6B—P1B—C24B—C29B	22.8 (3)
C1A—C2A—C3A—N1A	−1.1 (6)	C12B—P1B—C24B—C25B	−38.9 (3)
C3A—N1A—C4A—C5A	0.0 (5)	C18B—P1B—C24B—C25B	80.9 (3)
N1A—C4A—C5A—C1A	−0.6 (6)	C6B—P1B—C24B—C25B	−158.5 (2)
C2A—C1A—C5A—C4A	0.3 (5)	C29B—C24B—C25B—C26B	0.2 (5)
B1A—C1A—C5A—C4A	−179.8 (3)	P1B—C24B—C25B—C26B	−178.5 (3)
C5A—C1A—B1A—F3A	−176.7 (3)	C24B—C25B—C26B—C27B	−0.2 (5)
C2A—C1A—B1A—F3A	3.1 (4)	C25B—C26B—C27B—C28B	−0.1 (5)
C5A—C1A—B1A—F2A	−55.9 (4)	C26B—C27B—C28B—C29B	0.4 (5)
C2A—C1A—B1A—F2A	124.0 (3)	C25B—C24B—C29B—C28B	0.0 (5)
C5A—C1A—B1A—F1A	63.6 (4)	P1B—C24B—C29B—C28B	178.7 (3)
C2A—C1A—B1A—F1A	−116.6 (3)	C27B—C28B—C29B—C24B	−0.3 (5)
C5B—C1B—C2B—C3B	0.4 (5)	C12A—P1A—C6A—C11A	11.9 (3)
B1B—C1B—C2B—C3B	179.5 (3)	C24A—P1A—C6A—C11A	−106.7 (3)
C4B—N1B—C3B—C2B	1.0 (6)	C18A—P1A—C6A—C11A	129.1 (3)
C1B—C2B—C3B—N1B	−1.4 (6)	C12A—P1A—C6A—C7A	−170.4 (2)
C3B—N1B—C4B—C5B	0.4 (6)	C24A—P1A—C6A—C7A	71.1 (3)
N1B—C4B—C5B—C1B	−1.4 (6)	C18A—P1A—C6A—C7A	−53.2 (3)
C2B—C1B—C5B—C4B	0.9 (5)	C11A—C6A—C7A—C8A	−2.3 (5)
B1B—C1B—C5B—C4B	−178.2 (3)	P1A—C6A—C7A—C8A	179.9 (3)
C5B—C1B—B1B—F3B	114.1 (3)	C6A—C7A—C8A—C9A	1.2 (5)
C2B—C1B—B1B—F3B	−64.9 (4)	C7A—C8A—C9A—C10A	0.6 (5)
C5B—C1B—B1B—F1B	−6.8 (4)	C8A—C9A—C10A—C11A	−1.1 (5)
C2B—C1B—B1B—F1B	174.2 (3)	C9A—C10A—C11A—C6A	0.0 (5)
C5B—C1B—B1B—F2B	−126.0 (3)	C7A—C6A—C11A—C10A	1.7 (5)
C2B—C1B—B1B—F2B	55.0 (4)	P1A—C6A—C11A—C10A	179.4 (3)
C12B—P1B—C6B—C7B	9.0 (3)	C6A—P1A—C12A—C17A	−130.3 (2)
C18B—P1B—C6B—C7B	−110.4 (3)	C24A—P1A—C12A—C17A	−12.3 (3)
C24B—P1B—C6B—C7B	127.4 (3)	C18A—P1A—C12A—C17A	110.5 (2)
C12B—P1B—C6B—C11B	−176.3 (2)	C6A—P1A—C12A—C13A	55.2 (3)
C18B—P1B—C6B—C11B	64.3 (3)	C24A—P1A—C12A—C13A	173.2 (2)
C24B—P1B—C6B—C11B	−57.9 (3)	C18A—P1A—C12A—C13A	−64.0 (3)
C11B—C6B—C7B—C8B	0.8 (5)	C17A—C12A—C13A—C14A	1.0 (4)
P1B—C6B—C7B—C8B	175.5 (2)	P1A—C12A—C13A—C14A	175.5 (2)
C6B—C7B—C8B—C9B	1.0 (5)	C12A—C13A—C14A—C15A	−0.6 (4)
C7B—C8B—C9B—C10B	−1.0 (5)	C13A—C14A—C15A—C16A	−0.2 (5)
C8B—C9B—C10B—C11B	−0.8 (5)	C14A—C15A—C16A—C17A	0.6 (5)
C9B—C10B—C11B—C6B	2.5 (5)	C15A—C16A—C17A—C12A	−0.2 (5)
C7B—C6B—C11B—C10B	−2.5 (5)	C13A—C12A—C17A—C16A	−0.6 (4)
P1B—C6B—C11B—C10B	−177.2 (2)	P1A—C12A—C17A—C16A	−175.0 (2)
C18B—P1B—C12B—C17B	17.7 (3)	C12A—P1A—C18A—C19A	−61.2 (3)
C6B—P1B—C12B—C17B	−100.0 (3)	C6A—P1A—C18A—C19A	178.3 (2)
C24B—P1B—C12B—C17B	137.6 (3)	C24A—P1A—C18A—C19A	57.9 (3)
C18B—P1B—C12B—C13B	−164.9 (3)	C12A—P1A—C18A—C23A	114.0 (3)
C6B—P1B—C12B—C13B	77.4 (3)	C6A—P1A—C18A—C23A	−6.5 (3)
C24B—P1B—C12B—C13B	−45.0 (3)	C24A—P1A—C18A—C23A	−126.9 (3)
C17B—C12B—C13B—C14B	−0.3 (5)	C23A—C18A—C19A—C20A	2.4 (5)
P1B—C12B—C13B—C14B	−177.7 (3)	P1A—C18A—C19A—C20A	177.7 (3)
C12B—C13B—C14B—C15B	−0.1 (5)	C18A—C19A—C20A—C21A	−1.5 (5)
C13B—C14B—C15B—C16B	0.2 (5)	C19A—C20A—C21A—C22A	0.0 (5)
C14B—C15B—C16B—C17B	0.0 (5)	C20A—C21A—C22A—C23A	0.5 (5)
C15B—C16B—C17B—C12B	−0.4 (5)	C21A—C22A—C23A—C18A	0.4 (5)
C13B—C12B—C17B—C16B	0.5 (5)	C19A—C18A—C23A—C22A	−1.8 (5)
P1B—C12B—C17B—C16B	177.8 (3)	P1A—C18A—C23A—C22A	−176.9 (2)
C12B—P1B—C18B—C19B	−95.6 (3)	C12A—P1A—C24A—C29A	100.9 (3)
C6B—P1B—C18B—C19B	22.9 (3)	C6A—P1A—C24A—C29A	−138.6 (3)
C24B—P1B—C18B—C19B	146.8 (3)	C18A—P1A—C24A—C29A	−17.1 (3)
C12B—P1B—C18B—C23B	81.2 (3)	C12A—P1A—C24A—C25A	−74.8 (3)
C6B—P1B—C18B—C23B	−160.4 (3)	C6A—P1A—C24A—C25A	45.7 (3)
C24B—P1B—C18B—C23B	−36.5 (3)	C18A—P1A—C24A—C25A	167.2 (2)
C23B—C18B—C19B—C20B	0.6 (5)	C29A—C24A—C25A—C26A	−0.6 (5)
P1B—C18B—C19B—C20B	177.4 (3)	P1A—C24A—C25A—C26A	175.2 (3)
C18B—C19B—C20B—C21B	−0.5 (5)	C24A—C25A—C26A—C27A	0.4 (5)
C19B—C20B—C21B—C22B	0.3 (5)	C25A—C26A—C27A—C28A	−0.1 (5)
C20B—C21B—C22B—C23B	−0.2 (5)	C26A—C27A—C28A—C29A	0.0 (5)
C21B—C22B—C23B—C18B	0.4 (5)	C27A—C28A—C29A—C24A	−0.2 (5)
C19B—C18B—C23B—C22B	−0.6 (5)	C25A—C24A—C29A—C28A	0.5 (5)
P1B—C18B—C23B—C22B	−177.3 (2)	P1A—C24A—C29A—C28A	−175.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13B—H13B···F3A^i	0.95	2.55	3.134 (4)	120
C23B—H23B···F2A	0.95	2.62	3.182 (4)	118
C29B—H29B···F2B^ii	0.95	2.63	3.322 (4)	130
C13A—H13A···N1B^iii	0.95	2.58	3.426 (5)	148
C19A—H19A···F3A^iv	0.95	2.33	3.180 (4)	148
C29A—H29A···F1A^iv	0.95	2.46	3.310 (4)	149

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

Tetrakis[4-(dimethylamino)phenyl]phosphonium 3-(trifluoro-λ⁴-boranyl)pyridine (9)

Crystal data

C32H40N4P^+·C5H4BF3N^−	F(000) = 1392
Mr = 657.55	Dx = 1.269 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.802 (2) Å	Cell parameters from 9901 reflections
b = 12.0571 (15) Å	θ = 2.4–27.5°
c = 18.121 (2) Å	µ = 0.13 mm^−1
β = 94.405 (3)°	T = 150 K
V = 3442.4 (8) Å^3	Block, colorless
Z = 4	0.17 × 0.10 × 0.05 mm

Data collection

Bruker PHOTON III CPAD diffractometer	4970 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.037
φ and ω scans	θmax = 25.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −18→19
Tmin = 0.629, Tmax = 0.746	k = −14→13
31607 measured reflections	l = −21→21
6295 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 1.6024P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
6295 reflections	Δρmax = 0.21 e Å^−3
487 parameters	Δρmin = −0.31 e Å^−3
186 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.45065 (3)	0.12762 (4)	0.63779 (2)	0.02868 (12)
N2	0.41083 (10)	0.38399 (13)	0.91545 (8)	0.0409 (4)
N3	0.80188 (10)	−0.06561 (17)	0.66512 (10)	0.0558 (5)
N4	0.26850 (10)	−0.30265 (12)	0.61483 (9)	0.0421 (4)
N5	0.40689 (10)	0.45220 (14)	0.38870 (9)	0.0474 (4)
N1'	0.5665 (15)	0.791 (2)	0.807 (2)	0.072 (2)	0.389 (6)
C1'	0.4604 (9)	0.8504 (14)	0.8893 (10)	0.0456 (16)	0.389 (6)
C2'	0.4892 (13)	0.7824 (14)	0.8346 (13)	0.0555 (15)	0.389 (6)
H2'	0.452151	0.725722	0.815013	0.067*	0.389 (6)
C3'	0.6126 (13)	0.8787 (16)	0.8309 (17)	0.065 (2)	0.389 (6)
H3'	0.663330	0.893268	0.807603	0.078*	0.389 (6)
C4'	0.5929 (19)	0.948 (3)	0.885 (3)	0.0651 (18)	0.389 (6)
H4'	0.630752	1.005235	0.902963	0.078*	0.389 (6)
C5'	0.5158 (12)	0.9333 (18)	0.9149 (12)	0.0566 (17)	0.389 (6)
H5'	0.500389	0.980797	0.953460	0.068*	0.389 (6)
B1'	0.3673 (7)	0.8374 (8)	0.9213 (5)	0.043 (2)	0.389 (6)
F1'	0.3669 (3)	0.8865 (7)	0.9905 (3)	0.104 (2)	0.389 (6)
F2'	0.3465 (3)	0.7268 (4)	0.9300 (6)	0.117 (5)	0.389 (6)
F3'	0.3055 (5)	0.8869 (8)	0.8758 (4)	0.064 (2)	0.389 (6)
N1	0.5733 (9)	0.7642 (11)	0.8039 (12)	0.072 (2)	0.611 (6)
C1	0.4562 (5)	0.8265 (8)	0.8737 (6)	0.0456 (16)	0.611 (6)
C2	0.4955 (7)	0.7536 (8)	0.8275 (8)	0.0555 (15)	0.611 (6)
H2	0.463891	0.690041	0.810966	0.067*	0.611 (6)
C3	0.6195 (8)	0.8501 (8)	0.8312 (10)	0.065 (2)	0.611 (6)
H3	0.676453	0.857233	0.818485	0.078*	0.611 (6)
C4	0.5882 (11)	0.9279 (18)	0.8767 (15)	0.0651 (18)	0.611 (6)
H4	0.622086	0.989172	0.893580	0.078*	0.611 (6)
C5	0.5062 (7)	0.9162 (11)	0.8978 (7)	0.0566 (17)	0.611 (6)
H5	0.483849	0.970185	0.929147	0.068*	0.611 (6)
B1	0.3610 (5)	0.8099 (5)	0.9002 (4)	0.0472 (16)	0.611 (6)
F1	0.3633 (2)	0.7828 (4)	0.97483 (19)	0.0900 (18)	0.611 (6)
F2	0.31805 (16)	0.7250 (2)	0.8604 (2)	0.0639 (10)	0.611 (6)
F3	0.3122 (5)	0.9031 (5)	0.8889 (4)	0.098 (2)	0.611 (6)
C6	0.41932 (10)	0.32583 (14)	0.85190 (10)	0.0318 (4)
C7	0.38485 (10)	0.36489 (14)	0.78274 (10)	0.0324 (4)
H7	0.354918	0.433282	0.780299	0.039*
C8	0.39357 (10)	0.30616 (14)	0.71860 (10)	0.0317 (4)
H8	0.368675	0.334069	0.672940	0.038*
C9	0.43835 (10)	0.20632 (13)	0.71951 (9)	0.0289 (4)
C10	0.47315 (10)	0.16697 (14)	0.78821 (10)	0.0322 (4)
H10	0.504266	0.099481	0.790122	0.039*
C11	0.46329 (10)	0.22367 (14)	0.85266 (10)	0.0333 (4)
H11	0.486324	0.193859	0.898410	0.040*
C12	0.45202 (15)	0.34536 (19)	0.98479 (11)	0.0555 (6)
H12A	0.443133	0.399397	1.023844	0.083*
H12B	0.512984	0.336801	0.979776	0.083*
H12C	0.427840	0.273730	0.997697	0.083*
C13	0.37515 (12)	0.49512 (15)	0.91178 (11)	0.0440 (5)
H13A	0.369696	0.522825	0.962036	0.066*
H13B	0.319068	0.493151	0.884675	0.066*
H13C	0.412632	0.544314	0.886165	0.066*
C14	0.72162 (11)	−0.01967 (17)	0.65698 (10)	0.0401 (4)
C15	0.70818 (11)	0.09397 (17)	0.66961 (10)	0.0419 (5)
H15	0.755379	0.141102	0.681783	0.050*
C16	0.62702 (11)	0.13778 (16)	0.66450 (10)	0.0384 (4)
H16	0.619403	0.214382	0.674305	0.046*
C17	0.55603 (10)	0.07188 (14)	0.64524 (9)	0.0308 (4)
C18	0.56961 (11)	−0.04046 (15)	0.63240 (10)	0.0343 (4)
H18	0.522379	−0.087186	0.619443	0.041*
C19	0.65014 (11)	−0.08521 (16)	0.63810 (10)	0.0404 (4)
H19	0.657242	−0.162129	0.629032	0.048*
C20	0.81321 (16)	−0.1812 (2)	0.64487 (17)	0.0845 (9)
H20A	0.871674	−0.204013	0.659290	0.127*
H20B	0.801762	−0.189704	0.591254	0.127*
H20C	0.773823	−0.227667	0.670444	0.127*
C21	0.87498 (13)	0.0058 (3)	0.66371 (15)	0.0764 (8)
H21A	0.926851	−0.038708	0.670623	0.115*
H21B	0.874160	0.060613	0.703609	0.115*
H21C	0.873571	0.044165	0.615940	0.115*
C22	0.30198 (10)	−0.19830 (14)	0.61940 (10)	0.0319 (4)
C23	0.31328 (10)	−0.13416 (15)	0.55556 (10)	0.0336 (4)
H23	0.293618	−0.161705	0.508191	0.040*
C24	0.35260 (10)	−0.03193 (14)	0.56136 (10)	0.0321 (4)
H24	0.361362	0.008630	0.517653	0.039*
C25	0.37974 (10)	0.01304 (13)	0.63008 (9)	0.0292 (4)
C26	0.36428 (10)	−0.04745 (14)	0.69363 (10)	0.0310 (4)
H26	0.380387	−0.017077	0.741014	0.037*
C27	0.32615 (10)	−0.15020 (14)	0.68869 (10)	0.0324 (4)
H27	0.315998	−0.189233	0.732687	0.039*
C28	0.26586 (13)	−0.37029 (15)	0.68122 (12)	0.0470 (5)
H28A	0.243168	−0.443792	0.667717	0.070*
H28B	0.229299	−0.334579	0.715505	0.070*
H28C	0.323339	−0.378000	0.705089	0.070*
C29	0.24620 (15)	−0.35370 (18)	0.54409 (13)	0.0562 (6)
H29A	0.220112	−0.426155	0.551637	0.084*
H29B	0.297425	−0.363491	0.517542	0.084*
H29C	0.205899	−0.306182	0.514987	0.084*
C30	0.41572 (11)	0.37373 (14)	0.44354 (10)	0.0348 (4)
C31	0.49484 (11)	0.32469 (16)	0.46366 (10)	0.0393 (4)
H31	0.542640	0.344602	0.437785	0.047*
C32	0.50431 (11)	0.24853 (15)	0.52004 (10)	0.0351 (4)
H32	0.558754	0.217610	0.532876	0.042*
C33	0.43571 (10)	0.21564 (14)	0.55882 (9)	0.0306 (4)
C34	0.35608 (10)	0.26127 (15)	0.53780 (10)	0.0329 (4)
H34	0.308116	0.238394	0.562471	0.039*
C35	0.34600 (11)	0.33887 (15)	0.48190 (10)	0.0350 (4)
H35	0.291387	0.369259	0.469052	0.042*
C36	0.32507 (14)	0.49755 (19)	0.36488 (12)	0.0549 (6)
H36A	0.331302	0.551351	0.325121	0.082*
H36B	0.301062	0.534560	0.406659	0.082*
H36C	0.287127	0.437628	0.346626	0.082*
C37	0.48108 (14)	0.4918 (2)	0.35428 (12)	0.0581 (6)
H37A	0.464889	0.553687	0.321060	0.087*
H37B	0.504602	0.431565	0.325871	0.087*
H37C	0.523873	0.517000	0.392637	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0273 (2)	0.0271 (2)	0.0324 (2)	0.00000 (17)	0.00743 (17)	0.00259 (18)
N2	0.0473 (9)	0.0380 (9)	0.0371 (9)	0.0043 (7)	0.0019 (7)	−0.0066 (7)
N3	0.0332 (9)	0.0789 (13)	0.0548 (11)	0.0146 (9)	−0.0004 (8)	−0.0140 (10)
N4	0.0477 (9)	0.0306 (8)	0.0491 (10)	−0.0077 (7)	0.0110 (7)	−0.0044 (7)
N5	0.0486 (9)	0.0477 (10)	0.0466 (10)	−0.0002 (8)	0.0074 (8)	0.0182 (8)
N1'	0.066 (3)	0.076 (7)	0.077 (2)	0.000 (4)	0.0270 (18)	0.009 (5)
C1'	0.0510 (14)	0.039 (4)	0.047 (5)	0.0078 (18)	0.001 (2)	0.016 (3)
C2'	0.057 (2)	0.046 (5)	0.065 (3)	0.004 (3)	0.0133 (15)	0.012 (3)
C3'	0.050 (2)	0.064 (6)	0.083 (2)	0.000 (3)	0.0095 (19)	0.033 (5)
C4'	0.061 (2)	0.056 (8)	0.076 (6)	−0.011 (3)	−0.009 (3)	0.020 (4)
C5'	0.067 (3)	0.048 (4)	0.054 (6)	0.003 (2)	−0.005 (3)	0.012 (3)
B1'	0.039 (4)	0.035 (4)	0.055 (5)	0.006 (3)	0.009 (4)	0.010 (4)
F1'	0.079 (3)	0.162 (7)	0.076 (3)	−0.020 (3)	0.023 (2)	−0.014 (3)
F2'	0.060 (3)	0.049 (3)	0.249 (14)	0.022 (2)	0.062 (6)	0.059 (4)
F3'	0.039 (3)	0.102 (6)	0.050 (3)	0.020 (3)	0.0003 (19)	0.022 (3)
N1	0.066 (3)	0.076 (7)	0.077 (2)	0.000 (4)	0.0270 (18)	0.009 (5)
C1	0.0510 (14)	0.039 (4)	0.047 (5)	0.0078 (18)	0.001 (2)	0.016 (3)
C2	0.057 (2)	0.046 (5)	0.065 (3)	0.004 (3)	0.0133 (15)	0.012 (3)
C3	0.050 (2)	0.064 (6)	0.083 (2)	0.000 (3)	0.0095 (19)	0.033 (5)
C4	0.061 (2)	0.056 (8)	0.076 (6)	−0.011 (3)	−0.009 (3)	0.020 (4)
C5	0.067 (3)	0.048 (4)	0.054 (6)	0.003 (2)	−0.005 (3)	0.012 (3)
B1	0.054 (3)	0.039 (3)	0.051 (3)	0.013 (2)	0.014 (3)	0.015 (3)
F1	0.0665 (18)	0.154 (6)	0.0512 (17)	0.011 (3)	0.0186 (14)	0.026 (2)
F2	0.0537 (14)	0.0555 (14)	0.085 (2)	−0.0002 (10)	0.0205 (14)	0.0090 (13)
F3	0.089 (4)	0.0416 (18)	0.167 (6)	0.032 (2)	0.030 (3)	0.016 (3)
C6	0.0285 (8)	0.0311 (9)	0.0362 (10)	−0.0047 (7)	0.0044 (7)	−0.0012 (8)
C7	0.0308 (9)	0.0273 (9)	0.0396 (10)	0.0021 (7)	0.0063 (7)	0.0017 (8)
C8	0.0314 (9)	0.0298 (9)	0.0345 (9)	−0.0007 (7)	0.0061 (7)	0.0058 (7)
C9	0.0265 (8)	0.0279 (9)	0.0326 (9)	−0.0011 (7)	0.0051 (7)	0.0029 (7)
C10	0.0291 (8)	0.0291 (9)	0.0384 (10)	0.0013 (7)	0.0034 (7)	0.0014 (8)
C11	0.0335 (9)	0.0327 (9)	0.0334 (10)	−0.0007 (7)	0.0003 (7)	0.0042 (8)
C12	0.0713 (15)	0.0560 (14)	0.0380 (12)	0.0042 (11)	−0.0030 (10)	−0.0089 (10)
C13	0.0459 (11)	0.0347 (10)	0.0519 (12)	−0.0015 (8)	0.0060 (9)	−0.0108 (9)
C14	0.0353 (10)	0.0559 (12)	0.0294 (10)	0.0102 (9)	0.0058 (8)	0.0000 (9)
C15	0.0292 (9)	0.0574 (13)	0.0392 (11)	−0.0055 (8)	0.0033 (8)	0.0034 (9)
C16	0.0352 (9)	0.0365 (10)	0.0440 (11)	−0.0024 (8)	0.0055 (8)	0.0018 (8)
C17	0.0286 (8)	0.0331 (9)	0.0317 (9)	0.0013 (7)	0.0077 (7)	0.0024 (7)
C18	0.0349 (9)	0.0361 (10)	0.0323 (9)	0.0020 (8)	0.0049 (7)	−0.0015 (8)
C19	0.0395 (10)	0.0423 (11)	0.0393 (11)	0.0099 (8)	0.0023 (8)	−0.0048 (9)
C20	0.0500 (14)	0.095 (2)	0.106 (2)	0.0396 (14)	−0.0098 (14)	−0.0302 (18)
C21	0.0332 (11)	0.131 (3)	0.0657 (16)	0.0050 (14)	0.0091 (11)	0.0215 (16)
C22	0.0265 (8)	0.0280 (9)	0.0420 (10)	0.0001 (7)	0.0091 (7)	−0.0015 (8)
C23	0.0307 (9)	0.0369 (10)	0.0336 (9)	−0.0011 (7)	0.0059 (7)	−0.0051 (8)
C24	0.0311 (9)	0.0350 (9)	0.0311 (9)	0.0005 (7)	0.0083 (7)	0.0034 (7)
C25	0.0278 (8)	0.0275 (9)	0.0332 (9)	0.0012 (7)	0.0085 (7)	0.0016 (7)
C26	0.0312 (9)	0.0310 (9)	0.0317 (9)	0.0011 (7)	0.0074 (7)	−0.0003 (7)
C27	0.0336 (9)	0.0304 (9)	0.0342 (9)	0.0000 (7)	0.0088 (7)	0.0040 (7)
C28	0.0520 (12)	0.0286 (10)	0.0618 (13)	−0.0047 (9)	0.0133 (10)	0.0037 (9)
C29	0.0624 (14)	0.0449 (12)	0.0606 (14)	−0.0149 (10)	0.0003 (11)	−0.0108 (11)
C30	0.0417 (10)	0.0316 (9)	0.0315 (9)	−0.0022 (8)	0.0059 (8)	0.0022 (8)
C31	0.0363 (10)	0.0433 (11)	0.0399 (10)	−0.0050 (8)	0.0135 (8)	0.0075 (9)
C32	0.0310 (9)	0.0377 (10)	0.0376 (10)	0.0017 (7)	0.0099 (8)	0.0032 (8)
C33	0.0317 (9)	0.0291 (9)	0.0319 (9)	−0.0014 (7)	0.0079 (7)	0.0000 (7)
C34	0.0286 (9)	0.0370 (10)	0.0340 (9)	−0.0025 (7)	0.0081 (7)	0.0010 (8)
C35	0.0320 (9)	0.0381 (10)	0.0349 (10)	0.0029 (7)	0.0033 (7)	0.0015 (8)
C36	0.0651 (14)	0.0582 (14)	0.0421 (12)	0.0157 (11)	0.0095 (10)	0.0160 (10)
C37	0.0634 (14)	0.0618 (14)	0.0499 (13)	−0.0120 (11)	0.0097 (11)	0.0242 (11)

Geometric parameters (Å, º)

P1—C25	1.7775 (17)	C12—H12A	0.9800
P1—C9	1.7820 (17)	C12—H12B	0.9800
P1—C33	1.7829 (18)	C12—H12C	0.9800
P1—C17	1.7912 (16)	C13—H13A	0.9800
N2—C6	1.364 (2)	C13—H13B	0.9800
N2—C12	1.447 (3)	C13—H13C	0.9800
N2—C13	1.453 (2)	C14—C19	1.399 (3)
N3—C14	1.381 (2)	C14—C15	1.408 (3)
N3—C21	1.443 (3)	C15—C16	1.383 (3)
N3—C20	1.456 (3)	C15—H15	0.9500
N4—C22	1.365 (2)	C16—C17	1.397 (2)
N4—C29	1.441 (3)	C16—H16	0.9500
N4—C28	1.457 (2)	C17—C18	1.394 (2)
N5—C30	1.371 (2)	C18—C19	1.379 (2)
N5—C36	1.439 (3)	C18—H18	0.9500
N5—C37	1.451 (2)	C19—H19	0.9500
N1'—C3'	1.336 (12)	C20—H20A	0.9800
N1'—C2'	1.358 (12)	C20—H20B	0.9800
C1'—C5'	1.385 (10)	C20—H20C	0.9800
C1'—C2'	1.390 (11)	C21—H21A	0.9800
C1'—B1'	1.630 (10)	C21—H21B	0.9800
C2'—H2'	0.9500	C21—H21C	0.9800
C3'—C4'	1.351 (13)	C22—C27	1.409 (2)
C3'—H3'	0.9500	C22—C23	1.414 (2)
C4'—C5'	1.378 (12)	C23—C24	1.381 (2)
C4'—H4'	0.9500	C23—H23	0.9500
C5'—H5'	0.9500	C24—C25	1.395 (2)
B1'—F3'	1.367 (10)	C24—H24	0.9500
B1'—F2'	1.385 (9)	C25—C26	1.400 (2)
B1'—F1'	1.387 (9)	C26—C27	1.377 (2)
N1—C2	1.339 (7)	C26—H26	0.9500
N1—C3	1.339 (8)	C27—H27	0.9500
C1—C5	1.390 (7)	C28—H28A	0.9800
C1—C2	1.393 (6)	C28—H28B	0.9800
C1—B1	1.625 (7)	C28—H28C	0.9800
C2—H2	0.9500	C29—H29A	0.9800
C3—C4	1.365 (8)	C29—H29B	0.9800
C3—H3	0.9500	C29—H29C	0.9800
C4—C5	1.386 (8)	C30—C31	1.406 (3)
C4—H4	0.9500	C30—C35	1.411 (2)
C5—H5	0.9500	C31—C32	1.373 (3)
B1—F3	1.370 (7)	C31—H31	0.9500
B1—F1	1.389 (7)	C32—C33	1.394 (2)
B1—F2	1.398 (7)	C32—H32	0.9500
C6—C7	1.409 (2)	C33—C34	1.399 (2)
C6—C11	1.414 (2)	C34—C35	1.379 (2)
C7—C8	1.377 (2)	C34—H34	0.9500
C7—H7	0.9500	C35—H35	0.9500
C8—C9	1.396 (2)	C36—H36A	0.9800
C8—H8	0.9500	C36—H36B	0.9800
C9—C10	1.404 (2)	C36—H36C	0.9800
C10—C11	1.372 (2)	C37—H37A	0.9800
C10—H10	0.9500	C37—H37B	0.9800
C11—H11	0.9500	C37—H37C	0.9800
C25—P1—C9	111.77 (7)	H13B—C13—H13C	109.5
C25—P1—C33	110.84 (8)	N3—C14—C19	121.13 (19)
C9—P1—C33	109.51 (8)	N3—C14—C15	121.44 (18)
C25—P1—C17	106.93 (8)	C19—C14—C15	117.41 (16)
C9—P1—C17	107.30 (8)	C16—C15—C14	120.75 (18)
C33—P1—C17	110.41 (8)	C16—C15—H15	119.6
C6—N2—C12	120.06 (16)	C14—C15—H15	119.6
C6—N2—C13	119.90 (16)	C15—C16—C17	121.47 (18)
C12—N2—C13	118.92 (16)	C15—C16—H16	119.3
C14—N3—C21	119.2 (2)	C17—C16—H16	119.3
C14—N3—C20	119.12 (18)	C18—C17—C16	117.62 (16)
C21—N3—C20	116.9 (2)	C18—C17—P1	120.41 (13)
C22—N4—C29	120.98 (16)	C16—C17—P1	121.97 (14)
C22—N4—C28	120.11 (16)	C19—C18—C17	121.38 (17)
C29—N4—C28	118.35 (16)	C19—C18—H18	119.3
C30—N5—C36	121.23 (16)	C17—C18—H18	119.3
C30—N5—C37	119.89 (17)	C18—C19—C14	121.36 (18)
C36—N5—C37	118.87 (17)	C18—C19—H19	119.3
C3'—N1'—C2'	115.3 (13)	C14—C19—H19	119.3
C5'—C1'—C2'	115.6 (10)	N3—C20—H20A	109.5
C5'—C1'—B1'	121.0 (11)	N3—C20—H20B	109.5
C2'—C1'—B1'	123.4 (11)	H20A—C20—H20B	109.5
N1'—C2'—C1'	124.6 (13)	N3—C20—H20C	109.5
N1'—C2'—H2'	117.7	H20A—C20—H20C	109.5
C1'—C2'—H2'	117.7	H20B—C20—H20C	109.5
N1'—C3'—C4'	125.1 (15)	N3—C21—H21A	109.5
N1'—C3'—H3'	117.4	N3—C21—H21B	109.5
C4'—C3'—H3'	117.4	H21A—C21—H21B	109.5
C3'—C4'—C5'	117.6 (14)	N3—C21—H21C	109.5
C3'—C4'—H4'	121.2	H21A—C21—H21C	109.5
C5'—C4'—H4'	121.2	H21B—C21—H21C	109.5
C4'—C5'—C1'	121.3 (13)	N4—C22—C27	120.71 (16)
C4'—C5'—H5'	119.4	N4—C22—C23	121.81 (16)
C1'—C5'—H5'	119.4	C27—C22—C23	117.47 (15)
F3'—B1'—F2'	108.9 (8)	C24—C23—C22	120.68 (16)
F3'—B1'—F1'	107.8 (7)	C24—C23—H23	119.7
F2'—B1'—F1'	106.9 (8)	C22—C23—H23	119.7
F3'—B1'—C1'	111.5 (10)	C23—C24—C25	121.37 (16)
F2'—B1'—C1'	111.3 (9)	C23—C24—H24	119.3
F1'—B1'—C1'	110.3 (8)	C25—C24—H24	119.3
C2—N1—C3	116.4 (8)	C24—C25—C26	118.07 (15)
C5—C1—C2	114.2 (6)	C24—C25—P1	121.39 (12)
C5—C1—B1	121.3 (6)	C26—C25—P1	119.26 (13)
C2—C1—B1	124.4 (6)	C27—C26—C25	121.20 (16)
N1—C2—C1	126.5 (7)	C27—C26—H26	119.4
N1—C2—H2	116.8	C25—C26—H26	119.4
C1—C2—H2	116.8	C26—C27—C22	121.02 (16)
N1—C3—C4	122.8 (8)	C26—C27—H27	119.5
N1—C3—H3	118.6	C22—C27—H27	119.5
C4—C3—H3	118.6	N4—C28—H28A	109.5
C3—C4—C5	119.1 (8)	N4—C28—H28B	109.5
C3—C4—H4	120.4	H28A—C28—H28B	109.5
C5—C4—H4	120.4	N4—C28—H28C	109.5
C4—C5—C1	120.9 (8)	H28A—C28—H28C	109.5
C4—C5—H5	119.5	H28B—C28—H28C	109.5
C1—C5—H5	119.5	N4—C29—H29A	109.5
F3—B1—F1	108.1 (6)	N4—C29—H29B	109.5
F3—B1—F2	106.1 (6)	H29A—C29—H29B	109.5
F1—B1—F2	107.8 (5)	N4—C29—H29C	109.5
F3—B1—C1	112.2 (7)	H29A—C29—H29C	109.5
F1—B1—C1	111.1 (6)	H29B—C29—H29C	109.5
F2—B1—C1	111.2 (5)	N5—C30—C31	121.14 (16)
N2—C6—C7	121.53 (16)	N5—C30—C35	121.51 (16)
N2—C6—C11	121.33 (16)	C31—C30—C35	117.35 (16)
C7—C6—C11	117.14 (16)	C32—C31—C30	121.21 (15)
C8—C7—C6	121.48 (16)	C32—C31—H31	119.4
C8—C7—H7	119.3	C30—C31—H31	119.4
C6—C7—H7	119.3	C31—C32—C33	121.38 (16)
C7—C8—C9	121.13 (16)	C31—C32—H32	119.3
C7—C8—H8	119.4	C33—C32—H32	119.3
C9—C8—H8	119.4	C32—C33—C34	117.96 (16)
C8—C9—C10	117.74 (15)	C32—C33—P1	120.93 (13)
C8—C9—P1	122.48 (13)	C34—C33—P1	120.89 (12)
C10—C9—P1	119.77 (12)	C35—C34—C33	121.16 (15)
C11—C10—C9	121.59 (16)	C35—C34—H34	119.4
C11—C10—H10	119.2	C33—C34—H34	119.4
C9—C10—H10	119.2	C34—C35—C30	120.89 (16)
C10—C11—C6	120.90 (16)	C34—C35—H35	119.6
C10—C11—H11	119.6	C30—C35—H35	119.6
C6—C11—H11	119.6	N5—C36—H36A	109.5
N2—C12—H12A	109.5	N5—C36—H36B	109.5
N2—C12—H12B	109.5	H36A—C36—H36B	109.5
H12A—C12—H12B	109.5	N5—C36—H36C	109.5
N2—C12—H12C	109.5	H36A—C36—H36C	109.5
H12A—C12—H12C	109.5	H36B—C36—H36C	109.5
H12B—C12—H12C	109.5	N5—C37—H37A	109.5
N2—C13—H13A	109.5	N5—C37—H37B	109.5
N2—C13—H13B	109.5	H37A—C37—H37B	109.5
H13A—C13—H13B	109.5	N5—C37—H37C	109.5
N2—C13—H13C	109.5	H37A—C37—H37C	109.5
H13A—C13—H13C	109.5	H37B—C37—H37C	109.5
C3'—N1'—C2'—C1'	−6 (5)	C14—C15—C16—C17	−1.4 (3)
C5'—C1'—C2'—N1'	1 (4)	C15—C16—C17—C18	1.0 (3)
B1'—C1'—C2'—N1'	−180 (3)	C15—C16—C17—P1	−179.57 (14)
C2'—N1'—C3'—C4'	9 (5)	C25—P1—C17—C18	10.36 (16)
N1'—C3'—C4'—C5'	−6 (7)	C9—P1—C17—C18	130.41 (14)
C3'—C4'—C5'—C1'	0 (6)	C33—P1—C17—C18	−110.31 (15)
C2'—C1'—C5'—C4'	2 (4)	C25—P1—C17—C16	−169.07 (14)
B1'—C1'—C5'—C4'	−177 (3)	C9—P1—C17—C16	−49.01 (16)
C5'—C1'—B1'—F3'	97 (2)	C33—P1—C17—C16	70.27 (16)
C2'—C1'—B1'—F3'	−81 (2)	C16—C17—C18—C19	−0.3 (3)
C5'—C1'—B1'—F2'	−140.8 (19)	P1—C17—C18—C19	−179.74 (14)
C2'—C1'—B1'—F2'	40 (2)	C17—C18—C19—C14	0.0 (3)
C5'—C1'—B1'—F1'	−22 (2)	N3—C14—C19—C18	177.74 (17)
C2'—C1'—B1'—F1'	158.8 (19)	C15—C14—C19—C18	−0.3 (3)
C3—N1—C2—C1	4 (3)	C29—N4—C22—C27	−177.97 (17)
C5—C1—C2—N1	−2 (2)	C28—N4—C22—C27	−6.7 (2)
B1—C1—C2—N1	179.6 (16)	C29—N4—C22—C23	2.4 (3)
C2—N1—C3—C4	−4 (3)	C28—N4—C22—C23	173.74 (16)
N1—C3—C4—C5	2 (4)	N4—C22—C23—C24	−175.53 (15)
C3—C4—C5—C1	0 (4)	C27—C22—C23—C24	4.9 (2)
C2—C1—C5—C4	−1 (3)	C22—C23—C24—C25	−2.2 (2)
B1—C1—C5—C4	178.1 (19)	C23—C24—C25—C26	−1.4 (2)
C5—C1—B1—F3	51.9 (14)	C23—C24—C25—P1	165.59 (13)
C2—C1—B1—F3	−129.5 (13)	C9—P1—C25—C24	153.56 (13)
C5—C1—B1—F1	−69.3 (13)	C33—P1—C25—C24	31.10 (16)
C2—C1—B1—F1	109.3 (12)	C17—P1—C25—C24	−89.29 (15)
C5—C1—B1—F2	170.6 (11)	C9—P1—C25—C26	−39.59 (15)
C2—C1—B1—F2	−10.8 (15)	C33—P1—C25—C26	−162.05 (12)
C12—N2—C6—C7	−175.70 (17)	C17—P1—C25—C26	77.56 (14)
C13—N2—C6—C7	−7.9 (2)	C24—C25—C26—C27	2.3 (2)
C12—N2—C6—C11	4.2 (3)	P1—C25—C26—C27	−165.00 (13)
C13—N2—C6—C11	171.96 (16)	C25—C26—C27—C22	0.5 (2)
N2—C6—C7—C8	179.91 (15)	N4—C22—C27—C26	176.38 (15)
C11—C6—C7—C8	0.0 (2)	C23—C22—C27—C26	−4.0 (2)
C6—C7—C8—C9	−1.2 (2)	C36—N5—C30—C31	176.14 (19)
C7—C8—C9—C10	0.9 (2)	C37—N5—C30—C31	−4.6 (3)
C7—C8—C9—P1	179.72 (13)	C36—N5—C30—C35	−3.8 (3)
C25—P1—C9—C8	−101.35 (14)	C37—N5—C30—C35	175.48 (19)
C33—P1—C9—C8	21.87 (16)	N5—C30—C31—C32	178.04 (18)
C17—P1—C9—C8	141.73 (13)	C35—C30—C31—C32	−2.0 (3)
C25—P1—C9—C10	77.43 (15)	C30—C31—C32—C33	0.9 (3)
C33—P1—C9—C10	−159.35 (13)	C31—C32—C33—C34	1.0 (3)
C17—P1—C9—C10	−39.49 (15)	C31—C32—C33—P1	−173.60 (15)
C8—C9—C10—C11	0.5 (2)	C25—P1—C33—C32	−129.37 (14)
P1—C9—C10—C11	−178.35 (13)	C9—P1—C33—C32	106.86 (15)
C9—C10—C11—C6	−1.7 (3)	C17—P1—C33—C32	−11.07 (17)
N2—C6—C11—C10	−178.52 (16)	C25—P1—C33—C34	56.14 (16)
C7—C6—C11—C10	1.4 (2)	C9—P1—C33—C34	−67.63 (16)
C21—N3—C14—C19	162.58 (19)	C17—P1—C33—C34	174.44 (14)
C20—N3—C14—C19	7.6 (3)	C32—C33—C34—C35	−1.9 (3)
C21—N3—C14—C15	−19.5 (3)	P1—C33—C34—C35	172.78 (14)
C20—N3—C14—C15	−174.4 (2)	C33—C34—C35—C30	0.7 (3)
N3—C14—C15—C16	−177.05 (18)	N5—C30—C35—C34	−178.87 (17)
C19—C14—C15—C16	1.0 (3)	C31—C30—C35—C34	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4′a—H4′a···F1′a^i	0.95	2.33	3.04 (3)	131
C12—H12B···F1b^ii	0.98	2.52	3.333 (4)	141
C21—H21B···N1b^iii	0.98	2.60	3.263 (17)	125
C27—H27···F2b^iv	0.95	2.53	3.468 (4)	168
C28—H28A···F3′a^v	0.98	2.30	3.275 (8)	174
C28—H28A···F3b^v	0.98	2.26	3.218 (6)	167
C29—H29A···F3b^v	0.98	2.40	3.331 (6)	159
C34—H34···F2′a^vi	0.95	2.46	3.323 (5)	151
C34—H34···F2b^vi	0.95	2.53	3.456 (3)	166

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, y−1, z; (v) −x+1/2, y−3/2, −z+3/2; (vi) −x+1/2, y−1/2, −z+3/2.

Tetrakis(3,5-dimethoxyphenyl)phosphonium 3-(trifluoro-λ⁴-boranyl)pyridine (7)

Crystal data

C32H36O8P^+·C5H4BF3N^−	F(000) = 1520
Mr = 725.48	Dx = 1.317 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 21.3755 (8) Å	Cell parameters from 9939 reflections
b = 7.5380 (3) Å	θ = 2.9–30.2°
c = 23.0617 (8) Å	µ = 0.14 mm^−1
β = 99.998 (2)°	T = 150 K
V = 3659.5 (2) Å^3	Needle, colorless
Z = 4	0.31 × 0.07 × 0.05 mm

Data collection

Bruker PHOTON III CPAD diffractometer	6479 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.052
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −28→27
Tmin = 0.661, Tmax = 0.746	k = −9→10
43069 measured reflections	l = −29→30
9058 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 1.7829P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
9058 reflections	Δρmax = 0.45 e Å^−3
468 parameters	Δρmin = −0.35 e Å^−3
0 restraints

Special details

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.

Refinement. The reflection 2 0 0 was omitted due to suspected interference from the beam stop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.74832 (2)	0.43494 (5)	0.49757 (2)	0.01564 (9)
O1	0.67099 (6)	0.98709 (16)	0.38141 (5)	0.0286 (3)
N1	0.41185 (9)	0.1082 (2)	0.27786 (8)	0.0406 (4)
F1	0.53816 (8)	0.5462 (2)	0.28402 (6)	0.0695 (5)
B1	0.54294 (10)	0.4264 (3)	0.23920 (9)	0.0308 (5)
C1	0.50060 (8)	0.2506 (2)	0.24319 (7)	0.0251 (4)
O2	0.51516 (5)	0.55684 (17)	0.42136 (6)	0.0337 (3)
F2	0.60706 (5)	0.38069 (18)	0.24095 (6)	0.0523 (4)
C2	0.51184 (9)	0.0920 (3)	0.21601 (8)	0.0321 (4)
H2	0.545552	0.084974	0.194148	0.039*
O3	0.98153 (6)	0.57829 (17)	0.56268 (6)	0.0330 (3)
O4	0.82488 (6)	0.98500 (17)	0.61559 (6)	0.0344 (3)
O5	0.62670 (6)	−0.10705 (16)	0.54358 (5)	0.0293 (3)
O6	0.70289 (6)	0.27058 (17)	0.70543 (5)	0.0284 (3)
O7	0.86328 (7)	−0.10963 (16)	0.43999 (6)	0.0341 (3)
O8	0.78613 (7)	0.32865 (18)	0.29005 (5)	0.0362 (3)
F3	0.52340 (5)	0.51555 (15)	0.18508 (5)	0.0361 (3)
C3	0.47449 (10)	−0.0562 (3)	0.22041 (8)	0.0355 (4)
H3	0.482700	−0.165445	0.202586	0.043*
C4	0.42522 (10)	−0.0405 (3)	0.25132 (9)	0.0370 (5)
H4	0.399254	−0.141534	0.253880	0.044*
C6	0.45026 (9)	0.2472 (3)	0.27389 (8)	0.0334 (4)
H6	0.442198	0.352617	0.293928	0.040*
C7	0.68552 (7)	0.5733 (2)	0.46077 (7)	0.0176 (3)
C8	0.62297 (7)	0.5162 (2)	0.45556 (7)	0.0205 (3)
H8	0.613065	0.408582	0.473378	0.025*
C9	0.57517 (8)	0.6200 (2)	0.42374 (7)	0.0222 (3)
C10	0.58923 (8)	0.7778 (2)	0.39732 (7)	0.0236 (4)
H10	0.556282	0.846917	0.375221	0.028*
C11	0.65219 (8)	0.8329 (2)	0.40375 (7)	0.0206 (3)
C16	0.79495 (8)	0.7286 (2)	0.56214 (7)	0.0199 (3)
H16	0.751799	0.760325	0.561333	0.024*
C15	0.81061 (7)	0.5739 (2)	0.53493 (6)	0.0176 (3)
C14	0.46412 (9)	0.6660 (3)	0.39394 (12)	0.0463 (6)
H14A	0.423614	0.611185	0.398270	0.069*
H14B	0.466149	0.678837	0.352021	0.069*
H14C	0.467467	0.783147	0.412661	0.069*
C13	0.62344 (10)	1.0932 (3)	0.34577 (10)	0.0451 (6)
H13A	0.643615	1.195811	0.330539	0.068*
H13B	0.592570	1.134229	0.369645	0.068*
H13C	0.601655	1.022005	0.312788	0.068*
C12	0.70093 (8)	0.7312 (2)	0.43524 (7)	0.0190 (3)
H12	0.743883	0.768735	0.439228	0.023*
C18	0.90736 (8)	0.7913 (2)	0.59148 (7)	0.0216 (3)
H18	0.940385	0.866419	0.610439	0.026*
C17	0.84382 (8)	0.8356 (2)	0.59053 (7)	0.0218 (3)
C19	0.92158 (8)	0.6352 (2)	0.56414 (7)	0.0221 (3)
C20	0.87347 (7)	0.5247 (2)	0.53606 (7)	0.0201 (3)
H20	0.883453	0.417524	0.517984	0.024*
C21	1.03224 (8)	0.7009 (3)	0.57952 (9)	0.0355 (5)
H21A	1.072374	0.646319	0.573946	0.053*
H21B	1.034613	0.732857	0.621042	0.053*
H21C	1.024565	0.807855	0.555156	0.053*
C22	0.87307 (10)	1.0935 (3)	0.64872 (11)	0.0508 (7)
H22A	0.853203	1.191030	0.666991	0.076*
H22B	0.900263	1.142065	0.622468	0.076*
H22C	0.898814	1.021900	0.679427	0.076*
C23	0.71876 (7)	0.2940 (2)	0.54944 (7)	0.0173 (3)
C24	0.72610 (7)	0.3454 (2)	0.60870 (7)	0.0190 (3)
H24	0.748467	0.450486	0.622346	0.023*
C25	0.69950 (8)	0.2372 (2)	0.64674 (7)	0.0202 (3)
C26	0.66628 (7)	0.0831 (2)	0.62688 (7)	0.0200 (3)
H26	0.648755	0.010146	0.653586	0.024*
C27	0.65911 (7)	0.0378 (2)	0.56809 (7)	0.0196 (3)
C28	0.68572 (7)	0.1429 (2)	0.52849 (7)	0.0189 (3)
H28	0.681156	0.110873	0.488132	0.023*
C29	0.59409 (11)	−0.2118 (3)	0.58029 (9)	0.0388 (5)
H29A	0.569573	−0.304410	0.556626	0.058*
H29B	0.565275	−0.136108	0.598051	0.058*
H29C	0.625000	−0.266952	0.611434	0.058*
C30	0.73309 (10)	0.4310 (3)	0.72883 (8)	0.0333 (4)
H30A	0.730265	0.440680	0.770671	0.050*
H30B	0.711846	0.532853	0.707498	0.050*
H30C	0.777843	0.429207	0.724334	0.050*
C31	0.77782 (7)	0.3000 (2)	0.44405 (7)	0.0173 (3)
C32	0.77038 (8)	0.3606 (2)	0.38626 (7)	0.0210 (3)
H32	0.748649	0.468463	0.374992	0.025*
C33	0.79558 (8)	0.2591 (2)	0.34526 (7)	0.0225 (3)
C34	0.82735 (8)	0.1007 (2)	0.36117 (7)	0.0229 (3)
H34	0.844266	0.032560	0.332865	0.027*
C35	0.83390 (8)	0.0438 (2)	0.41942 (7)	0.0218 (3)
C36	0.80963 (7)	0.1430 (2)	0.46152 (7)	0.0196 (3)
H36	0.814738	0.104106	0.501244	0.024*
C37	0.89146 (12)	−0.2156 (3)	0.40014 (10)	0.0465 (6)
H37A	0.913651	−0.316322	0.421391	0.070*
H37B	0.921809	−0.143744	0.382980	0.070*
H37C	0.858263	−0.259617	0.368708	0.070*
C38	0.80772 (12)	0.2293 (3)	0.24432 (9)	0.0458 (6)
H38A	0.795592	0.291167	0.206677	0.069*
H38B	0.788279	0.111146	0.241673	0.069*
H38C	0.854054	0.217547	0.253349	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01424 (19)	0.01484 (19)	0.01799 (19)	−0.00018 (16)	0.00322 (14)	0.00059 (15)
O1	0.0270 (7)	0.0229 (6)	0.0322 (7)	−0.0034 (5)	−0.0055 (5)	0.0114 (5)
N1	0.0447 (11)	0.0395 (10)	0.0427 (10)	−0.0095 (8)	0.0215 (8)	0.0031 (8)
F1	0.1052 (13)	0.0589 (9)	0.0519 (8)	−0.0445 (9)	0.0348 (8)	−0.0224 (7)
B1	0.0301 (11)	0.0331 (12)	0.0290 (10)	−0.0068 (9)	0.0049 (8)	0.0069 (9)
C1	0.0217 (8)	0.0308 (9)	0.0214 (8)	−0.0010 (7)	0.0004 (6)	0.0078 (7)
O2	0.0133 (6)	0.0305 (7)	0.0555 (8)	0.0003 (5)	0.0006 (5)	0.0112 (6)
F2	0.0247 (6)	0.0603 (9)	0.0684 (9)	−0.0074 (6)	−0.0020 (6)	0.0358 (7)
C2	0.0264 (9)	0.0407 (11)	0.0305 (9)	−0.0014 (8)	0.0085 (7)	0.0002 (8)
O3	0.0146 (6)	0.0345 (7)	0.0504 (8)	−0.0024 (5)	0.0065 (5)	−0.0183 (6)
O4	0.0224 (6)	0.0284 (7)	0.0476 (8)	0.0070 (5)	−0.0072 (6)	−0.0199 (6)
O5	0.0376 (7)	0.0237 (6)	0.0294 (6)	−0.0138 (5)	0.0137 (5)	−0.0046 (5)
O6	0.0364 (7)	0.0315 (7)	0.0178 (6)	−0.0101 (6)	0.0066 (5)	−0.0026 (5)
O7	0.0485 (8)	0.0222 (7)	0.0365 (7)	0.0149 (6)	0.0213 (6)	0.0064 (5)
O8	0.0503 (9)	0.0398 (8)	0.0208 (6)	0.0143 (7)	0.0125 (6)	0.0037 (6)
F3	0.0316 (6)	0.0336 (6)	0.0424 (6)	0.0012 (5)	0.0041 (5)	0.0163 (5)
C3	0.0395 (11)	0.0339 (11)	0.0324 (10)	−0.0037 (9)	0.0041 (8)	−0.0033 (8)
C4	0.0431 (12)	0.0342 (11)	0.0340 (10)	−0.0137 (9)	0.0076 (9)	0.0043 (8)
C6	0.0370 (11)	0.0312 (10)	0.0349 (10)	−0.0015 (8)	0.0143 (8)	0.0037 (8)
C7	0.0169 (7)	0.0175 (8)	0.0183 (7)	0.0014 (6)	0.0031 (6)	−0.0017 (6)
C8	0.0174 (8)	0.0186 (8)	0.0254 (8)	−0.0011 (6)	0.0041 (6)	0.0010 (6)
C9	0.0162 (8)	0.0218 (8)	0.0281 (8)	0.0003 (6)	0.0027 (6)	0.0002 (7)
C10	0.0200 (8)	0.0223 (9)	0.0263 (8)	0.0022 (7)	−0.0024 (6)	0.0010 (7)
C11	0.0240 (8)	0.0170 (8)	0.0195 (8)	−0.0010 (6)	0.0001 (6)	0.0014 (6)
C16	0.0158 (7)	0.0204 (8)	0.0228 (8)	0.0026 (6)	0.0010 (6)	−0.0002 (6)
C15	0.0167 (7)	0.0177 (8)	0.0184 (7)	−0.0013 (6)	0.0027 (6)	0.0031 (6)
C14	0.0153 (9)	0.0352 (12)	0.0845 (17)	0.0026 (8)	−0.0023 (10)	0.0150 (11)
C13	0.0389 (12)	0.0340 (11)	0.0544 (13)	−0.0036 (9)	−0.0148 (10)	0.0248 (10)
C12	0.0174 (8)	0.0198 (8)	0.0191 (7)	−0.0019 (6)	0.0010 (6)	0.0001 (6)
C18	0.0176 (8)	0.0212 (8)	0.0249 (8)	−0.0016 (6)	0.0005 (6)	−0.0027 (6)
C17	0.0225 (8)	0.0185 (8)	0.0231 (8)	0.0039 (6)	0.0008 (6)	−0.0036 (6)
C19	0.0169 (8)	0.0250 (9)	0.0248 (8)	−0.0006 (7)	0.0044 (6)	−0.0024 (7)
C20	0.0190 (8)	0.0190 (8)	0.0228 (8)	−0.0007 (6)	0.0047 (6)	−0.0033 (6)
C21	0.0168 (9)	0.0415 (12)	0.0496 (12)	−0.0068 (8)	0.0098 (8)	−0.0168 (9)
C22	0.0311 (11)	0.0394 (12)	0.0739 (16)	0.0086 (9)	−0.0132 (10)	−0.0363 (12)
C23	0.0151 (7)	0.0173 (8)	0.0199 (7)	0.0013 (6)	0.0045 (6)	0.0021 (6)
C24	0.0175 (8)	0.0182 (8)	0.0213 (8)	0.0003 (6)	0.0033 (6)	0.0000 (6)
C25	0.0181 (8)	0.0224 (8)	0.0204 (8)	0.0014 (6)	0.0044 (6)	0.0008 (6)
C26	0.0177 (8)	0.0196 (8)	0.0237 (8)	−0.0004 (6)	0.0066 (6)	0.0032 (6)
C27	0.0164 (8)	0.0159 (8)	0.0269 (8)	−0.0012 (6)	0.0044 (6)	0.0000 (6)
C28	0.0183 (8)	0.0190 (8)	0.0198 (7)	0.0000 (6)	0.0042 (6)	−0.0006 (6)
C29	0.0505 (13)	0.0299 (10)	0.0397 (11)	−0.0198 (9)	0.0187 (9)	−0.0030 (8)
C30	0.0414 (11)	0.0341 (11)	0.0247 (9)	−0.0113 (9)	0.0066 (8)	−0.0073 (8)
C31	0.0141 (7)	0.0172 (8)	0.0213 (8)	−0.0017 (6)	0.0051 (6)	−0.0015 (6)
C32	0.0215 (8)	0.0194 (8)	0.0222 (8)	0.0013 (7)	0.0037 (6)	0.0008 (6)
C33	0.0238 (8)	0.0259 (9)	0.0183 (8)	−0.0018 (7)	0.0049 (6)	0.0004 (6)
C34	0.0231 (8)	0.0230 (9)	0.0245 (8)	−0.0029 (7)	0.0097 (6)	−0.0041 (7)
C35	0.0206 (8)	0.0170 (8)	0.0293 (9)	−0.0006 (6)	0.0082 (6)	0.0012 (6)
C36	0.0180 (8)	0.0194 (8)	0.0222 (8)	−0.0008 (6)	0.0058 (6)	0.0013 (6)
C37	0.0694 (16)	0.0277 (11)	0.0512 (13)	0.0207 (10)	0.0352 (12)	0.0067 (9)
C38	0.0711 (16)	0.0447 (13)	0.0251 (10)	0.0119 (11)	0.0178 (10)	−0.0026 (9)

Geometric parameters (Å, º)

P1—C15	1.7927 (16)	C14—H14B	0.9800
P1—C7	1.7927 (16)	C14—H14C	0.9800
P1—C23	1.7946 (16)	C13—H13A	0.9800
P1—C31	1.7959 (16)	C13—H13B	0.9800
O1—C11	1.3602 (19)	C13—H13C	0.9800
O1—C13	1.435 (2)	C12—H12	0.9500
N1—C4	1.332 (3)	C18—C19	1.394 (2)
N1—C6	1.344 (2)	C18—C17	1.395 (2)
F1—B1	1.390 (3)	C18—H18	0.9500
B1—F2	1.407 (2)	C19—C20	1.393 (2)
B1—F3	1.415 (2)	C20—H20	0.9500
B1—C1	1.616 (3)	C21—H21A	0.9800
C1—C6	1.387 (2)	C21—H21B	0.9800
C1—C2	1.390 (3)	C21—H21C	0.9800
O2—C9	1.360 (2)	C22—H22A	0.9800
O2—C14	1.424 (2)	C22—H22B	0.9800
C2—C3	1.387 (3)	C22—H22C	0.9800
C2—H2	0.9500	C23—C28	1.383 (2)
O3—C19	1.357 (2)	C23—C24	1.403 (2)
O3—C21	1.426 (2)	C24—C25	1.390 (2)
O4—C17	1.3594 (19)	C24—H24	0.9500
O4—C22	1.429 (2)	C25—C26	1.397 (2)
O5—C27	1.3622 (19)	C26—C27	1.381 (2)
O5—C29	1.425 (2)	C26—H26	0.9500
O6—C25	1.3661 (19)	C27—C28	1.402 (2)
O6—C30	1.431 (2)	C28—H28	0.9500
O7—C35	1.362 (2)	C29—H29A	0.9800
O7—C37	1.428 (2)	C29—H29B	0.9800
O8—C33	1.359 (2)	C29—H29C	0.9800
O8—C38	1.434 (2)	C30—H30A	0.9800
C3—C4	1.375 (3)	C30—H30B	0.9800
C3—H3	0.9500	C30—H30C	0.9800
C4—H4	0.9500	C31—C36	1.389 (2)
C6—H6	0.9500	C31—C32	1.392 (2)
C7—C8	1.390 (2)	C32—C33	1.395 (2)
C7—C12	1.392 (2)	C32—H32	0.9500
C8—C9	1.391 (2)	C33—C34	1.391 (2)
C8—H8	0.9500	C34—C35	1.394 (2)
C9—C10	1.393 (2)	C34—H34	0.9500
C10—C11	1.391 (2)	C35—C36	1.395 (2)
C10—H10	0.9500	C36—H36	0.9500
C11—C12	1.392 (2)	C37—H37A	0.9800
C16—C17	1.390 (2)	C37—H37B	0.9800
C16—C15	1.392 (2)	C37—H37C	0.9800
C16—H16	0.9500	C38—H38A	0.9800
C15—C20	1.390 (2)	C38—H38B	0.9800
C14—H14A	0.9800	C38—H38C	0.9800
C15—P1—C7	108.68 (7)	O3—C19—C20	115.06 (14)
C15—P1—C23	110.08 (7)	O3—C19—C18	123.99 (15)
C7—P1—C23	109.79 (7)	C20—C19—C18	120.95 (15)
C15—P1—C31	109.94 (7)	C15—C20—C19	118.84 (15)
C7—P1—C31	109.11 (7)	C15—C20—H20	120.6
C23—P1—C31	109.23 (7)	C19—C20—H20	120.6
C11—O1—C13	117.84 (14)	O3—C21—H21A	109.5
C4—N1—C6	116.27 (17)	O3—C21—H21B	109.5
F1—B1—F2	109.56 (17)	H21A—C21—H21B	109.5
F1—B1—F3	107.37 (17)	O3—C21—H21C	109.5
F2—B1—F3	106.15 (15)	H21A—C21—H21C	109.5
F1—B1—C1	112.11 (16)	H21B—C21—H21C	109.5
F2—B1—C1	110.51 (17)	O4—C22—H22A	109.5
F3—B1—C1	110.92 (15)	O4—C22—H22B	109.5
C6—C1—C2	115.08 (17)	H22A—C22—H22B	109.5
C6—C1—B1	122.43 (17)	O4—C22—H22C	109.5
C2—C1—B1	122.50 (16)	H22A—C22—H22C	109.5
C9—O2—C14	117.38 (14)	H22B—C22—H22C	109.5
C3—C2—C1	120.88 (17)	C28—C23—C24	122.13 (14)
C3—C2—H2	119.6	C28—C23—P1	118.19 (12)
C1—C2—H2	119.6	C24—C23—P1	119.55 (12)
C19—O3—C21	117.69 (14)	C25—C24—C23	117.65 (15)
C17—O4—C22	117.48 (14)	C25—C24—H24	121.2
C27—O5—C29	117.62 (13)	C23—C24—H24	121.2
C25—O6—C30	118.15 (13)	O6—C25—C24	124.08 (15)
C35—O7—C37	118.15 (14)	O6—C25—C26	114.49 (14)
C33—O8—C38	118.24 (15)	C24—C25—C26	121.43 (15)
C4—C3—C2	118.09 (19)	C27—C26—C25	119.43 (15)
C4—C3—H3	121.0	C27—C26—H26	120.3
C2—C3—H3	121.0	C25—C26—H26	120.3
N1—C4—C3	123.73 (19)	O5—C27—C26	124.58 (14)
N1—C4—H4	118.1	O5—C27—C28	114.66 (14)
C3—C4—H4	118.1	C26—C27—C28	120.76 (15)
N1—C6—C1	125.91 (19)	C23—C28—C27	118.58 (14)
N1—C6—H6	117.0	C23—C28—H28	120.7
C1—C6—H6	117.0	C27—C28—H28	120.7
C8—C7—C12	121.50 (14)	O5—C29—H29A	109.5
C8—C7—P1	119.40 (12)	O5—C29—H29B	109.5
C12—C7—P1	119.00 (12)	H29A—C29—H29B	109.5
C7—C8—C9	118.63 (15)	O5—C29—H29C	109.5
C7—C8—H8	120.7	H29A—C29—H29C	109.5
C9—C8—H8	120.7	H29B—C29—H29C	109.5
O2—C9—C8	115.18 (15)	O6—C30—H30A	109.5
O2—C9—C10	123.71 (15)	O6—C30—H30B	109.5
C8—C9—C10	121.10 (15)	H30A—C30—H30B	109.5
C11—C10—C9	119.10 (15)	O6—C30—H30C	109.5
C11—C10—H10	120.4	H30A—C30—H30C	109.5
C9—C10—H10	120.4	H30B—C30—H30C	109.5
O1—C11—C10	123.95 (15)	C36—C31—C32	121.73 (14)
O1—C11—C12	115.14 (14)	C36—C31—P1	119.71 (12)
C10—C11—C12	120.90 (15)	C32—C31—P1	118.50 (12)
C17—C16—C15	118.58 (15)	C31—C32—C33	118.43 (15)
C17—C16—H16	120.7	C31—C32—H32	120.8
C15—C16—H16	120.7	C33—C32—H32	120.8
C20—C15—C16	121.49 (14)	O8—C33—C34	124.36 (15)
C20—C15—P1	119.21 (12)	O8—C33—C32	114.30 (15)
C16—C15—P1	119.30 (12)	C34—C33—C32	121.34 (15)
O2—C14—H14A	109.5	C33—C34—C35	118.75 (15)
O2—C14—H14B	109.5	C33—C34—H34	120.6
H14A—C14—H14B	109.5	C35—C34—H34	120.6
O2—C14—H14C	109.5	O7—C35—C34	124.07 (15)
H14A—C14—H14C	109.5	O7—C35—C36	114.68 (14)
H14B—C14—H14C	109.5	C34—C35—C36	121.25 (15)
O1—C13—H13A	109.5	C31—C36—C35	118.50 (15)
O1—C13—H13B	109.5	C31—C36—H36	120.7
H13A—C13—H13B	109.5	C35—C36—H36	120.7
O1—C13—H13C	109.5	O7—C37—H37A	109.5
H13A—C13—H13C	109.5	O7—C37—H37B	109.5
H13B—C13—H13C	109.5	H37A—C37—H37B	109.5
C11—C12—C7	118.74 (15)	O7—C37—H37C	109.5
C11—C12—H12	120.6	H37A—C37—H37C	109.5
C7—C12—H12	120.6	H37B—C37—H37C	109.5
C19—C18—C17	118.87 (15)	O8—C38—H38A	109.5
C19—C18—H18	120.6	O8—C38—H38B	109.5
C17—C18—H18	120.6	H38A—C38—H38B	109.5
O4—C17—C16	115.21 (15)	O8—C38—H38C	109.5
O4—C17—C18	123.53 (15)	H38A—C38—H38C	109.5
C16—C17—C18	121.25 (15)	H38B—C38—H38C	109.5
F1—B1—C1—C6	20.4 (3)	C21—O3—C19—C18	−13.0 (3)
F2—B1—C1—C6	142.96 (17)	C17—C18—C19—O3	−179.49 (16)
F3—B1—C1—C6	−99.6 (2)	C17—C18—C19—C20	0.2 (2)
F1—B1—C1—C2	−159.71 (18)	C16—C15—C20—C19	−1.3 (2)
F2—B1—C1—C2	−37.2 (2)	P1—C15—C20—C19	178.70 (12)
F3—B1—C1—C2	80.3 (2)	O3—C19—C20—C15	−179.34 (14)
C6—C1—C2—C3	−0.1 (3)	C18—C19—C20—C15	0.9 (2)
B1—C1—C2—C3	179.99 (17)	C15—P1—C23—C28	−160.18 (12)
C1—C2—C3—C4	1.4 (3)	C7—P1—C23—C28	80.23 (14)
C6—N1—C4—C3	−0.9 (3)	C31—P1—C23—C28	−39.38 (14)
C2—C3—C4—N1	−0.9 (3)	C15—P1—C23—C24	23.88 (15)
C4—N1—C6—C1	2.4 (3)	C7—P1—C23—C24	−95.72 (13)
C2—C1—C6—N1	−1.8 (3)	C31—P1—C23—C24	144.68 (12)
B1—C1—C6—N1	178.03 (19)	C28—C23—C24—C25	0.8 (2)
C15—P1—C7—C8	−146.50 (13)	P1—C23—C24—C25	176.59 (12)
C23—P1—C7—C8	−26.04 (15)	C30—O6—C25—C24	3.0 (2)
C31—P1—C7—C8	93.63 (13)	C30—O6—C25—C26	−176.64 (15)
C15—P1—C7—C12	37.00 (14)	C23—C24—C25—O6	180.00 (15)
C23—P1—C7—C12	157.45 (12)	C23—C24—C25—C26	−0.3 (2)
C31—P1—C7—C12	−82.88 (13)	O6—C25—C26—C27	179.08 (14)
C12—C7—C8—C9	0.3 (2)	C24—C25—C26—C27	−0.6 (2)
P1—C7—C8—C9	−176.07 (12)	C29—O5—C27—C26	4.8 (2)
C14—O2—C9—C8	174.40 (18)	C29—O5—C27—C28	−175.04 (16)
C14—O2—C9—C10	−4.8 (3)	C25—C26—C27—O5	−178.67 (15)
C7—C8—C9—O2	−179.06 (14)	C25—C26—C27—C28	1.1 (2)
C7—C8—C9—C10	0.2 (2)	C24—C23—C28—C27	−0.3 (2)
O2—C9—C10—C11	178.30 (16)	P1—C23—C28—C27	−176.14 (12)
C8—C9—C10—C11	−0.9 (3)	O5—C27—C28—C23	179.14 (14)
C13—O1—C11—C10	−4.4 (3)	C26—C27—C28—C23	−0.7 (2)
C13—O1—C11—C12	176.64 (16)	C15—P1—C31—C36	83.25 (14)
C9—C10—C11—O1	−177.88 (15)	C7—P1—C31—C36	−157.66 (12)
C9—C10—C11—C12	1.1 (2)	C23—P1—C31—C36	−37.64 (14)
C17—C16—C15—C20	0.5 (2)	C15—P1—C31—C32	−94.02 (14)
C17—C16—C15—P1	−179.50 (12)	C7—P1—C31—C32	25.07 (15)
C7—P1—C15—C20	−141.79 (13)	C23—P1—C31—C32	145.09 (13)
C23—P1—C15—C20	97.94 (13)	C36—C31—C32—C33	0.2 (2)
C31—P1—C15—C20	−22.44 (15)	P1—C31—C32—C33	177.46 (12)
C7—P1—C15—C16	38.19 (14)	C38—O8—C33—C34	2.9 (3)
C23—P1—C15—C16	−82.08 (14)	C38—O8—C33—C32	−177.06 (17)
C31—P1—C15—C16	157.55 (12)	C31—C32—C33—O8	−179.90 (15)
O1—C11—C12—C7	178.48 (14)	C31—C32—C33—C34	0.2 (2)
C10—C11—C12—C7	−0.5 (2)	O8—C33—C34—C35	179.97 (16)
C8—C7—C12—C11	−0.2 (2)	C32—C33—C34—C35	−0.1 (3)
P1—C7—C12—C11	176.26 (12)	C37—O7—C35—C34	2.7 (3)
C22—O4—C17—C16	175.87 (18)	C37—O7—C35—C36	−177.76 (17)
C22—O4—C17—C18	−5.4 (3)	C33—C34—C35—O7	179.16 (16)
C15—C16—C17—O4	179.42 (14)	C33—C34—C35—C36	−0.4 (3)
C15—C16—C17—C18	0.7 (2)	C32—C31—C36—C35	−0.7 (2)
C19—C18—C17—O4	−179.67 (16)	P1—C31—C36—C35	−177.89 (12)
C19—C18—C17—C16	−1.1 (2)	O7—C35—C36—C31	−178.81 (14)
C21—O3—C19—C20	167.27 (16)	C34—C35—C36—C31	0.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···F1	0.98	2.58	3.338 (3)	134
C3—H3···F3^i	0.95	2.61	3.532 (2)	163
C18—H18···F3^ii	0.95	2.42	3.3274 (19)	160
C21—H21B···F3^ii	0.98	2.44	3.269 (2)	142
C37—H37B···F3^iii	0.98	2.43	3.384 (2)	164
C34—H34···F2^iii	0.95	2.43	3.378 (2)	175
C13—H13A···F2^iv	0.98	2.50	3.220 (2)	130
C26—H26···N1^v	0.95	2.38	3.312 (2)	165

Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x, y+1, z; (v) −x+1, −y, −z+1.

Tetrakis[4-(dimethylamino)phenyl]phosphonium 3-(trifluoro-λ⁴-boranyl)pyridine hemihydrate (10h)

Crystal data

C32H40N4P^+·C5H4BF3N^−·0.5H2O	F(000) = 1412
Mr = 666.56	Dx = 1.257 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.9373 (3) Å	Cell parameters from 9885 reflections
b = 23.4315 (7) Å	θ = 2.2–26.4°
c = 13.0949 (3) Å	µ = 0.13 mm^−1
β = 105.938 (1)°	T = 150 K
V = 3521.96 (16) Å^3	Block, colorless
Z = 4	0.16 × 0.16 × 0.10 mm

Data collection

Bruker PHOTON III CPAD diffractometer	5810 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.032
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→12
Tmin = 0.644, Tmax = 0.745	k = −29→24
31433 measured reflections	l = −16→16
7198 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 1.994P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
7198 reflections	Δρmax = 0.55 e Å^−3
448 parameters	Δρmin = −0.46 e Å^−3
4 restraints

Special details

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.

Refinement. The reflection -1 0 1 was omitted due to suspected interference from the beam stop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0092 (3)	0.4864 (2)	0.0516 (3)	0.0768 (12)	0.5
H1O	−0.058 (4)	0.509 (2)	0.017 (4)	0.115*	0.5
H2O	0.036 (5)	0.471 (3)	−0.006 (3)	0.115*	0.5
P1	0.35366 (4)	0.57954 (2)	0.30747 (3)	0.02337 (11)
N2	0.62231 (15)	0.70480 (8)	0.69354 (13)	0.0427 (4)
N3	0.05675 (16)	0.41949 (8)	0.47601 (14)	0.0465 (4)
N4	0.15366 (13)	0.72342 (7)	−0.07423 (12)	0.0339 (4)
N5	0.69183 (15)	0.42104 (7)	0.19069 (14)	0.0414 (4)
C6	0.43819 (14)	0.62084 (7)	0.41528 (13)	0.0243 (3)
C7	0.38621 (15)	0.66467 (7)	0.45910 (13)	0.0278 (4)
H7	0.307599	0.674863	0.425949	0.033*
C8	0.44670 (16)	0.69320 (8)	0.54910 (13)	0.0307 (4)
H8	0.409532	0.722905	0.576890	0.037*
C9	0.56386 (16)	0.67883 (8)	0.60090 (13)	0.0311 (4)
C10	0.61639 (15)	0.63597 (8)	0.55462 (14)	0.0314 (4)
H10	0.695751	0.626435	0.586006	0.038*
C11	0.55480 (14)	0.60757 (8)	0.46458 (13)	0.0282 (4)
H11	0.592151	0.578467	0.435460	0.034*
C12	0.5674 (2)	0.74926 (10)	0.74012 (16)	0.0504 (6)
H12A	0.622482	0.763133	0.805443	0.076*
H12B	0.498195	0.733795	0.756711	0.076*
H12C	0.544606	0.780864	0.689674	0.076*
C13	0.74098 (19)	0.68813 (11)	0.74708 (17)	0.0546 (6)
H13A	0.768075	0.709374	0.813785	0.082*
H13B	0.791525	0.696630	0.701364	0.082*
H13C	0.743497	0.647117	0.762235	0.082*
C14	0.25350 (14)	0.53684 (7)	0.35398 (13)	0.0251 (3)
C15	0.17760 (15)	0.49825 (8)	0.28736 (14)	0.0308 (4)
H15	0.171941	0.498002	0.213568	0.037*
C16	0.11104 (16)	0.46068 (8)	0.32684 (15)	0.0346 (4)
H16	0.058818	0.435773	0.279386	0.042*
C17	0.11879 (15)	0.45841 (8)	0.43611 (15)	0.0330 (4)
C18	0.19445 (15)	0.49760 (8)	0.50254 (14)	0.0317 (4)
H18	0.200901	0.497853	0.576481	0.038*
C19	0.25930 (14)	0.53561 (7)	0.46194 (13)	0.0282 (4)
H19	0.309282	0.561657	0.508661	0.034*
C20	−0.0224 (2)	0.38044 (11)	0.4066 (2)	0.0660 (7)
H20A	−0.065923	0.359067	0.447471	0.099*
H20B	0.021953	0.353795	0.375059	0.099*
H20C	−0.076908	0.401954	0.350098	0.099*
C21	0.0756 (2)	0.41331 (10)	0.58964 (18)	0.0520 (6)
H21A	0.030200	0.380867	0.603767	0.078*
H21B	0.050691	0.448213	0.618416	0.078*
H21C	0.158514	0.406674	0.623548	0.078*
C22	0.28387 (14)	0.62600 (7)	0.20185 (12)	0.0249 (3)
C23	0.35070 (15)	0.66922 (7)	0.17287 (13)	0.0281 (4)
H23	0.427530	0.676024	0.216171	0.034*
C24	0.30799 (15)	0.70188 (7)	0.08371 (13)	0.0288 (4)
H24	0.355738	0.730572	0.066068	0.035*
C25	0.19401 (15)	0.69336 (8)	0.01794 (13)	0.0280 (4)
C26	0.12519 (15)	0.65174 (8)	0.04962 (13)	0.0304 (4)
H26	0.046533	0.646580	0.009322	0.036*
C27	0.17012 (14)	0.61835 (8)	0.13818 (13)	0.0288 (4)
H27	0.122755	0.589601	0.156198	0.035*
C28	0.22431 (17)	0.76784 (8)	−0.10373 (15)	0.0368 (4)
H28A	0.183019	0.783469	−0.173297	0.055*
H28B	0.298815	0.751581	−0.107203	0.055*
H28C	0.238630	0.798352	−0.050519	0.055*
C29	0.03639 (16)	0.71444 (9)	−0.14094 (14)	0.0385 (5)
H29A	0.026077	0.734854	−0.208204	0.058*
H29B	−0.019640	0.728823	−0.104700	0.058*
H29C	0.023332	0.673552	−0.155062	0.058*
C30	0.44818 (14)	0.53186 (7)	0.26407 (13)	0.0257 (3)
C31	0.46440 (15)	0.47655 (7)	0.30415 (13)	0.0289 (4)
H31	0.420628	0.463914	0.350461	0.035*
C32	0.54210 (15)	0.43975 (8)	0.27848 (14)	0.0297 (4)
H32	0.549597	0.402000	0.305997	0.036*
C33	0.61053 (15)	0.45691 (8)	0.21239 (14)	0.0307 (4)
C34	0.59329 (18)	0.51272 (9)	0.17110 (16)	0.0404 (5)
H34	0.637302	0.525635	0.125187	0.048*
C35	0.51396 (17)	0.54884 (8)	0.19599 (15)	0.0372 (4)
H35	0.503620	0.586117	0.166335	0.045*
C36	0.69501 (18)	0.36144 (8)	0.2216 (2)	0.0466 (5)
H36A	0.760606	0.342461	0.204213	0.070*
H36B	0.622063	0.342844	0.183213	0.070*
H36C	0.704522	0.358780	0.298183	0.070*
C37	0.7521 (2)	0.43706 (11)	0.1126 (2)	0.0661 (8)
H37A	0.812315	0.408683	0.112261	0.099*
H37B	0.788444	0.474575	0.130700	0.099*
H37C	0.696255	0.438748	0.042081	0.099*
F1	0.17889 (12)	0.72596 (6)	0.52427 (13)	0.0667 (4)
F2	0.01083 (10)	0.77434 (6)	0.46398 (9)	0.0521 (3)
F3	0.08873 (11)	0.76497 (7)	0.64070 (9)	0.0596 (4)
B1	0.11693 (18)	0.77193 (10)	0.54633 (18)	0.0361 (5)
N1	0.3327 (3)	0.92772 (11)	0.5427 (3)	0.0858 (9)
C1	0.19072 (17)	0.83090 (9)	0.54591 (15)	0.0380 (4)
C2	0.1621 (2)	0.87156 (10)	0.46593 (18)	0.0533 (6)
H2	0.092420	0.867663	0.409959	0.064*
C3	0.2348 (3)	0.91781 (11)	0.4674 (3)	0.0782 (10)
H3	0.213007	0.944312	0.410496	0.094*
C4	0.3577 (2)	0.88971 (14)	0.6217 (3)	0.0722 (9)
H4	0.425685	0.895915	0.678613	0.087*
C5	0.29187 (18)	0.84239 (11)	0.6263 (2)	0.0529 (6)
H5	0.315496	0.817088	0.684963	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.059 (2)	0.102 (3)	0.062 (2)	0.029 (2)	0.0050 (19)	−0.025 (2)
P1	0.0240 (2)	0.0240 (2)	0.0220 (2)	0.00180 (17)	0.00607 (16)	0.00026 (17)
N2	0.0461 (10)	0.0444 (10)	0.0298 (8)	−0.0142 (8)	−0.0027 (7)	−0.0016 (7)
N3	0.0490 (10)	0.0465 (10)	0.0484 (10)	−0.0166 (8)	0.0208 (8)	0.0007 (8)
N4	0.0311 (8)	0.0427 (9)	0.0261 (8)	0.0082 (7)	0.0049 (6)	0.0071 (7)
N5	0.0464 (9)	0.0295 (8)	0.0565 (11)	0.0051 (7)	0.0281 (8)	−0.0042 (8)
C6	0.0250 (8)	0.0235 (8)	0.0232 (8)	0.0000 (6)	0.0044 (6)	0.0031 (6)
C7	0.0287 (9)	0.0274 (9)	0.0249 (8)	0.0025 (7)	0.0036 (7)	0.0022 (7)
C8	0.0390 (10)	0.0271 (9)	0.0256 (9)	−0.0018 (8)	0.0083 (7)	0.0001 (7)
C9	0.0353 (9)	0.0304 (9)	0.0240 (8)	−0.0115 (8)	0.0019 (7)	0.0073 (7)
C10	0.0244 (8)	0.0346 (10)	0.0316 (9)	−0.0057 (7)	0.0018 (7)	0.0102 (8)
C11	0.0259 (8)	0.0288 (9)	0.0303 (9)	−0.0002 (7)	0.0083 (7)	0.0068 (7)
C12	0.0719 (15)	0.0460 (13)	0.0302 (10)	−0.0204 (11)	0.0091 (10)	−0.0069 (9)
C13	0.0488 (13)	0.0667 (16)	0.0354 (11)	−0.0218 (11)	−0.0100 (9)	0.0069 (11)
C14	0.0236 (8)	0.0257 (9)	0.0259 (8)	0.0013 (7)	0.0069 (7)	−0.0008 (7)
C15	0.0320 (9)	0.0339 (10)	0.0265 (9)	−0.0002 (7)	0.0080 (7)	−0.0038 (7)
C16	0.0326 (9)	0.0334 (10)	0.0369 (10)	−0.0050 (8)	0.0079 (8)	−0.0069 (8)
C17	0.0294 (9)	0.0317 (10)	0.0407 (10)	−0.0001 (8)	0.0142 (8)	0.0002 (8)
C18	0.0334 (9)	0.0358 (10)	0.0272 (9)	0.0005 (8)	0.0106 (7)	0.0003 (8)
C19	0.0274 (8)	0.0296 (9)	0.0273 (9)	−0.0010 (7)	0.0071 (7)	−0.0026 (7)
C20	0.0748 (17)	0.0562 (15)	0.0733 (17)	−0.0363 (14)	0.0309 (14)	−0.0083 (13)
C21	0.0572 (13)	0.0511 (14)	0.0546 (13)	−0.0061 (11)	0.0268 (11)	0.0129 (11)
C22	0.0266 (8)	0.0263 (9)	0.0209 (8)	0.0049 (7)	0.0050 (6)	−0.0007 (6)
C23	0.0285 (9)	0.0257 (9)	0.0268 (8)	0.0013 (7)	0.0019 (7)	−0.0021 (7)
C24	0.0316 (9)	0.0253 (9)	0.0286 (9)	0.0027 (7)	0.0067 (7)	0.0009 (7)
C25	0.0300 (9)	0.0325 (9)	0.0215 (8)	0.0107 (7)	0.0072 (7)	−0.0006 (7)
C26	0.0225 (8)	0.0424 (10)	0.0256 (8)	0.0050 (7)	0.0052 (7)	0.0011 (8)
C27	0.0255 (8)	0.0355 (10)	0.0266 (8)	0.0015 (7)	0.0093 (7)	−0.0002 (7)
C28	0.0450 (11)	0.0370 (11)	0.0283 (9)	0.0097 (9)	0.0098 (8)	0.0056 (8)
C29	0.0357 (10)	0.0504 (12)	0.0258 (9)	0.0135 (9)	0.0026 (8)	0.0029 (8)
C30	0.0286 (8)	0.0255 (9)	0.0237 (8)	0.0022 (7)	0.0083 (7)	0.0000 (7)
C31	0.0326 (9)	0.0285 (9)	0.0272 (9)	0.0009 (7)	0.0109 (7)	0.0028 (7)
C32	0.0331 (9)	0.0238 (9)	0.0323 (9)	0.0017 (7)	0.0092 (7)	0.0016 (7)
C33	0.0334 (9)	0.0277 (9)	0.0327 (9)	0.0010 (7)	0.0117 (8)	−0.0056 (7)
C34	0.0504 (12)	0.0361 (11)	0.0456 (11)	0.0047 (9)	0.0315 (10)	0.0060 (9)
C35	0.0485 (11)	0.0285 (10)	0.0413 (11)	0.0069 (8)	0.0239 (9)	0.0093 (8)
C36	0.0389 (11)	0.0275 (10)	0.0760 (15)	0.0039 (8)	0.0203 (11)	−0.0102 (10)
C37	0.0771 (17)	0.0567 (15)	0.0865 (19)	0.0168 (13)	0.0596 (16)	−0.0018 (13)
F1	0.0526 (8)	0.0458 (8)	0.1091 (12)	0.0009 (6)	0.0346 (8)	0.0010 (8)
F2	0.0416 (7)	0.0757 (9)	0.0383 (6)	−0.0097 (6)	0.0095 (5)	0.0000 (6)
F3	0.0531 (8)	0.0906 (11)	0.0356 (7)	−0.0201 (7)	0.0132 (6)	0.0102 (7)
B1	0.0288 (10)	0.0466 (13)	0.0372 (11)	−0.0043 (9)	0.0163 (9)	−0.0026 (10)
N1	0.101 (2)	0.0645 (16)	0.125 (2)	−0.0404 (15)	0.087 (2)	−0.0418 (17)
C1	0.0383 (10)	0.0438 (11)	0.0384 (10)	0.0017 (9)	0.0214 (9)	−0.0035 (9)
C2	0.0762 (16)	0.0457 (13)	0.0433 (12)	−0.0057 (12)	0.0254 (12)	−0.0008 (10)
C3	0.136 (3)	0.0435 (14)	0.078 (2)	−0.0203 (17)	0.069 (2)	−0.0067 (14)
C4	0.0449 (14)	0.083 (2)	0.100 (2)	−0.0202 (14)	0.0382 (15)	−0.0409 (19)
C5	0.0342 (11)	0.0660 (16)	0.0610 (14)	−0.0031 (10)	0.0171 (10)	−0.0110 (12)

Geometric parameters (Å, º)

O1—H1O	0.961 (9)	C21—H21B	0.9800
O1—H2O	0.962 (9)	C21—H21C	0.9800
P1—C22	1.7775 (17)	C22—C27	1.396 (2)
P1—C6	1.7791 (17)	C22—C23	1.404 (2)
P1—C30	1.7878 (16)	C23—C24	1.372 (2)
P1—C14	1.7893 (17)	C23—H23	0.9500
N2—C9	1.365 (2)	C24—C25	1.410 (2)
N2—C13	1.451 (3)	C24—H24	0.9500
N2—C12	1.451 (3)	C25—C26	1.409 (2)
N3—C17	1.366 (2)	C26—C27	1.379 (2)
N3—C20	1.444 (3)	C26—H26	0.9500
N3—C21	1.450 (3)	C27—H27	0.9500
N4—C25	1.366 (2)	C28—H28A	0.9800
N4—C29	1.448 (2)	C28—H28B	0.9800
N4—C28	1.457 (2)	C28—H28C	0.9800
N5—C33	1.371 (2)	C29—H29A	0.9800
N5—C36	1.451 (3)	C29—H29B	0.9800
N5—C37	1.452 (3)	C29—H29C	0.9800
C6—C11	1.399 (2)	C30—C31	1.392 (2)
C6—C7	1.402 (2)	C30—C35	1.398 (2)
C7—C8	1.375 (2)	C31—C32	1.374 (2)
C7—H7	0.9500	C31—H31	0.9500
C8—C9	1.417 (3)	C32—C33	1.402 (2)
C8—H8	0.9500	C32—H32	0.9500
C9—C10	1.406 (3)	C33—C34	1.408 (3)
C10—C11	1.377 (2)	C34—C35	1.374 (3)
C10—H10	0.9500	C34—H34	0.9500
C11—H11	0.9500	C35—H35	0.9500
C12—H12A	0.9800	C36—H36A	0.9800
C12—H12B	0.9800	C36—H36B	0.9800
C12—H12C	0.9800	C36—H36C	0.9800
C13—H13A	0.9800	C37—H37A	0.9800
C13—H13B	0.9800	C37—H37B	0.9800
C13—H13C	0.9800	C37—H37C	0.9800
C14—C19	1.397 (2)	F1—B1	1.381 (3)
C14—C15	1.402 (2)	F2—B1	1.421 (3)
C15—C16	1.378 (3)	F3—B1	1.377 (2)
C15—H15	0.9500	B1—C1	1.640 (3)
C16—C17	1.409 (3)	N1—C3	1.326 (4)
C16—H16	0.9500	N1—C4	1.336 (4)
C17—C18	1.409 (3)	C1—C2	1.387 (3)
C18—C19	1.379 (2)	C1—C5	1.393 (3)
C18—H18	0.9500	C2—C3	1.385 (4)
C19—H19	0.9500	C2—H2	0.9500
C20—H20A	0.9800	C3—H3	0.9500
C20—H20B	0.9800	C4—C5	1.370 (4)
C20—H20C	0.9800	C4—H4	0.9500
C21—H21A	0.9800	C5—H5	0.9500
H1O—O1—H2O	104.3 (12)	C23—C22—P1	118.18 (12)
C22—P1—C6	109.08 (8)	C24—C23—C22	121.76 (16)
C22—P1—C30	109.71 (7)	C24—C23—H23	119.1
C6—P1—C30	108.80 (8)	C22—C23—H23	119.1
C22—P1—C14	113.15 (8)	C23—C24—C25	120.77 (16)
C6—P1—C14	108.69 (8)	C23—C24—H24	119.6
C30—P1—C14	107.33 (8)	C25—C24—H24	119.6
C9—N2—C13	120.15 (19)	N4—C25—C26	121.63 (16)
C9—N2—C12	120.93 (17)	N4—C25—C24	120.91 (16)
C13—N2—C12	118.92 (17)	C26—C25—C24	117.44 (15)
C17—N3—C20	120.80 (18)	C27—C26—C25	121.09 (16)
C17—N3—C21	120.78 (18)	C27—C26—H26	119.5
C20—N3—C21	118.23 (18)	C25—C26—H26	119.5
C25—N4—C29	120.41 (16)	C26—C27—C22	121.28 (16)
C25—N4—C28	120.88 (15)	C26—C27—H27	119.4
C29—N4—C28	118.57 (15)	C22—C27—H27	119.4
C33—N5—C36	119.85 (16)	N4—C28—H28A	109.5
C33—N5—C37	120.21 (17)	N4—C28—H28B	109.5
C36—N5—C37	117.71 (17)	H28A—C28—H28B	109.5
C11—C6—C7	118.04 (15)	N4—C28—H28C	109.5
C11—C6—P1	121.39 (13)	H28A—C28—H28C	109.5
C7—C6—P1	120.34 (12)	H28B—C28—H28C	109.5
C8—C7—C6	121.33 (16)	N4—C29—H29A	109.5
C8—C7—H7	119.3	N4—C29—H29B	109.5
C6—C7—H7	119.3	H29A—C29—H29B	109.5
C7—C8—C9	120.78 (17)	N4—C29—H29C	109.5
C7—C8—H8	119.6	H29A—C29—H29C	109.5
C9—C8—H8	119.6	H29B—C29—H29C	109.5
N2—C9—C10	121.44 (17)	C31—C30—C35	117.47 (15)
N2—C9—C8	121.05 (18)	C31—C30—P1	119.78 (12)
C10—C9—C8	117.49 (16)	C35—C30—P1	122.60 (13)
C11—C10—C9	121.17 (16)	C32—C31—C30	121.70 (16)
C11—C10—H10	119.4	C32—C31—H31	119.1
C9—C10—H10	119.4	C30—C31—H31	119.1
C10—C11—C6	121.14 (17)	C31—C32—C33	121.18 (16)
C10—C11—H11	119.4	C31—C32—H32	119.4
C6—C11—H11	119.4	C33—C32—H32	119.4
N2—C12—H12A	109.5	N5—C33—C32	121.16 (17)
N2—C12—H12B	109.5	N5—C33—C34	121.78 (16)
H12A—C12—H12B	109.5	C32—C33—C34	117.05 (16)
N2—C12—H12C	109.5	C35—C34—C33	121.22 (16)
H12A—C12—H12C	109.5	C35—C34—H34	119.4
H12B—C12—H12C	109.5	C33—C34—H34	119.4
N2—C13—H13A	109.5	C34—C35—C30	121.34 (17)
N2—C13—H13B	109.5	C34—C35—H35	119.3
H13A—C13—H13B	109.5	C30—C35—H35	119.3
N2—C13—H13C	109.5	N5—C36—H36A	109.5
H13A—C13—H13C	109.5	N5—C36—H36B	109.5
H13B—C13—H13C	109.5	H36A—C36—H36B	109.5
C19—C14—C15	117.42 (15)	N5—C36—H36C	109.5
C19—C14—P1	120.27 (13)	H36A—C36—H36C	109.5
C15—C14—P1	121.80 (12)	H36B—C36—H36C	109.5
C16—C15—C14	121.28 (16)	N5—C37—H37A	109.5
C16—C15—H15	119.4	N5—C37—H37B	109.5
C14—C15—H15	119.4	H37A—C37—H37B	109.5
C15—C16—C17	121.40 (17)	N5—C37—H37C	109.5
C15—C16—H16	119.3	H37A—C37—H37C	109.5
C17—C16—H16	119.3	H37B—C37—H37C	109.5
N3—C17—C18	121.48 (17)	F3—B1—F1	111.86 (19)
N3—C17—C16	121.48 (17)	F3—B1—F2	107.40 (15)
C18—C17—C16	117.04 (16)	F1—B1—F2	106.81 (17)
C19—C18—C17	121.04 (16)	F3—B1—C1	111.52 (17)
C19—C18—H18	119.5	F1—B1—C1	109.73 (15)
C17—C18—H18	119.5	F2—B1—C1	109.37 (17)
C18—C19—C14	121.79 (16)	C3—N1—C4	115.0 (2)
C18—C19—H19	119.1	C2—C1—C5	114.9 (2)
C14—C19—H19	119.1	C2—C1—B1	124.06 (19)
N3—C20—H20A	109.5	C5—C1—B1	121.02 (19)
N3—C20—H20B	109.5	C3—C2—C1	120.2 (3)
H20A—C20—H20B	109.5	C3—C2—H2	119.9
N3—C20—H20C	109.5	C1—C2—H2	119.9
H20A—C20—H20C	109.5	N1—C3—C2	124.6 (3)
H20B—C20—H20C	109.5	N1—C3—H3	117.7
N3—C21—H21A	109.5	C2—C3—H3	117.7
N3—C21—H21B	109.5	N1—C4—C5	124.4 (3)
H21A—C21—H21B	109.5	N1—C4—H4	117.8
N3—C21—H21C	109.5	C5—C4—H4	117.8
H21A—C21—H21C	109.5	C4—C5—C1	120.8 (3)
H21B—C21—H21C	109.5	C4—C5—H5	119.6
C27—C22—C23	117.56 (15)	C1—C5—H5	119.6
C27—C22—P1	123.87 (13)
C22—P1—C6—C11	−130.06 (14)	P1—C22—C23—C24	171.18 (13)
C30—P1—C6—C11	−10.41 (16)	C22—C23—C24—C25	0.5 (3)
C14—P1—C6—C11	106.16 (14)	C29—N4—C25—C26	1.9 (3)
C22—P1—C6—C7	55.59 (15)	C28—N4—C25—C26	177.61 (16)
C30—P1—C6—C7	175.25 (13)	C29—N4—C25—C24	−179.81 (16)
C14—P1—C6—C7	−68.19 (15)	C28—N4—C25—C24	−4.1 (2)
C11—C6—C7—C8	−1.3 (2)	C23—C24—C25—N4	−176.03 (16)
P1—C6—C7—C8	173.23 (13)	C23—C24—C25—C26	2.3 (2)
C6—C7—C8—C9	−0.4 (3)	N4—C25—C26—C27	174.56 (16)
C13—N2—C9—C10	−0.5 (3)	C24—C25—C26—C27	−3.7 (2)
C12—N2—C9—C10	179.56 (17)	C25—C26—C27—C22	2.4 (3)
C13—N2—C9—C8	178.00 (17)	C23—C22—C27—C26	0.4 (2)
C12—N2—C9—C8	−2.0 (3)	P1—C22—C27—C26	−172.22 (13)
C7—C8—C9—N2	−176.30 (16)	C22—P1—C30—C31	−146.75 (14)
C7—C8—C9—C10	2.2 (2)	C6—P1—C30—C31	94.00 (15)
N2—C9—C10—C11	176.10 (16)	C14—P1—C30—C31	−23.44 (16)
C8—C9—C10—C11	−2.4 (2)	C22—P1—C30—C35	37.76 (18)
C9—C10—C11—C6	0.8 (3)	C6—P1—C30—C35	−81.50 (17)
C7—C6—C11—C10	1.1 (2)	C14—P1—C30—C35	161.07 (16)
P1—C6—C11—C10	−173.35 (13)	C35—C30—C31—C32	0.1 (3)
C22—P1—C14—C19	−127.60 (14)	P1—C30—C31—C32	−175.57 (14)
C6—P1—C14—C19	−6.28 (16)	C30—C31—C32—C33	1.5 (3)
C30—P1—C14—C19	111.22 (14)	C36—N5—C33—C32	10.2 (3)
C22—P1—C14—C15	60.82 (16)	C37—N5—C33—C32	172.8 (2)
C6—P1—C14—C15	−177.86 (14)	C36—N5—C33—C34	−170.91 (19)
C30—P1—C14—C15	−60.35 (16)	C37—N5—C33—C34	−8.3 (3)
C19—C14—C15—C16	0.2 (3)	C31—C32—C33—N5	177.00 (17)
P1—C14—C15—C16	172.00 (14)	C31—C32—C33—C34	−2.0 (3)
C14—C15—C16—C17	−1.7 (3)	N5—C33—C34—C35	−178.04 (19)
C20—N3—C17—C18	178.6 (2)	C32—C33—C34—C35	0.9 (3)
C21—N3—C17—C18	−6.3 (3)	C33—C34—C35—C30	0.7 (3)
C20—N3—C17—C16	−2.2 (3)	C31—C30—C35—C34	−1.2 (3)
C21—N3—C17—C16	172.89 (19)	P1—C30—C35—C34	174.39 (16)
C15—C16—C17—N3	−177.06 (18)	F3—B1—C1—C2	−128.8 (2)
C15—C16—C17—C18	2.2 (3)	F1—B1—C1—C2	106.7 (2)
N3—C17—C18—C19	178.08 (18)	F2—B1—C1—C2	−10.2 (3)
C16—C17—C18—C19	−1.2 (3)	F3—B1—C1—C5	53.9 (2)
C17—C18—C19—C14	−0.3 (3)	F1—B1—C1—C5	−70.6 (2)
C15—C14—C19—C18	0.8 (3)	F2—B1—C1—C5	172.57 (17)
P1—C14—C19—C18	−171.11 (14)	C5—C1—C2—C3	2.9 (3)
C6—P1—C22—C27	−140.81 (14)	B1—C1—C2—C3	−174.5 (2)
C30—P1—C22—C27	100.11 (15)	C4—N1—C3—C2	−1.3 (4)
C14—P1—C22—C27	−19.71 (17)	C1—C2—C3—N1	−1.3 (4)
C6—P1—C22—C23	46.58 (15)	C3—N1—C4—C5	2.1 (4)
C30—P1—C22—C23	−72.51 (14)	N1—C4—C5—C1	−0.4 (4)
C14—P1—C22—C23	167.67 (12)	C2—C1—C5—C4	−2.1 (3)
C27—C22—C23—C24	−1.9 (2)	B1—C1—C5—C4	175.35 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1a—H1Oa···N1^i	0.96 (1)	2.07 (3)	2.893 (4)	143 (4)
O1a—H2Oa···N1^ii	0.96 (1)	2.04 (3)	2.873 (4)	144 (4)
C7—H7···F1	0.95	2.56	3.174 (2)	123
C15—H15···O1a	0.95	2.47	3.200 (4)	134
C20—H20A···F1^iii	0.98	2.49	3.384 (3)	152
C24—H24···F2^iv	0.95	2.57	3.274 (2)	131
C28—H28A···F3^v	0.98	2.43	3.294 (2)	148
C28—H28B···F2^iv	0.98	2.52	3.434 (2)	155
C29—H29A···F3^v	0.98	2.41	3.309 (2)	153
C36—H36A···N4^vi	0.98	2.70	3.585 (3)	151
C37—H37B···N1^iv	0.98	2.68	3.505 (4)	142

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x, −y+1, −z+1; (iv) x+1/2, −y+3/2, z−1/2; (v) x, y, z−1; (vi) −x+1, −y+1, −z.

Tetrakis(3,5-dimethoxyphenyl)phosphonium 4-(trifluoro-λ⁴-boranyl)pyridine (8)

Crystal data

C32H36O8P^+·C5H4BF3N^−	Z = 4
Mr = 725.48	F(000) = 1520
Triclinic, P1	Dx = 1.363 Mg m^−3
a = 14.702 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.141 (5) Å	Cell parameters from 9534 reflections
c = 16.017 (5) Å	θ = 2.6–25.3°
α = 84.473 (11)°	µ = 0.15 mm^−1
β = 88.059 (10)°	T = 150 K
γ = 85.136 (10)°	Needle, colorless
V = 3534.7 (18) Å^3	0.16 × 0.07 × 0.05 mm

Data collection

Bruker PHOTON III CPAD diffractometer	12796 independent reflections
Radiation source: micro-focus	9875 reflections with I > 2σ(I)
φ and ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −17→17
Tmin = 0.682, Tmax = 0.745	k = −17→18
12796 measured reflections	l = 0→19

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 3.4901P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
12796 reflections	Δρmax = 0.44 e Å^−3
967 parameters	Δρmin = −0.34 e Å^−3
30 restraints

Special details

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.

Refinement. Refined as a 2-component non-merohedral twin. The domain ratio is approximately 50:50. Relevent information about the twin domains is included below.

Cell for domain 2: 14.709 15.217 16.047 84.53 88.04 85.04

Figure of merit: 0.828 %(0.1): 88.4 %(0.2): 94.9 %(0.3): 96.3

Orientation matrix: 0.00541931 0.05824635 -0.03354565 0.01041879 0.02796004 0.05240631 0.06724761 -0.01464892 -0.00707880

Rotated from first domain by 179.8 degrees about reciprocal axis -0.002 0.999 1.000 and real axis -0.125 1.000 0.884

Twin law to convert hkl from first to -1.000 0.000 -0.004 this domain (SHELXL TWIN matrix): -0.134 0.061 0.938 -0.130 1.062 -0.061

Statistics for singles of twin component 1 ——————————————-

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 9.0 0.0539 0.856 - 1.007 0.978 - 1.051 0.738 19959 12626 2 9.0 0.0510 0.615 - 0.888 0.977 - 1.024 0.733 5595 3644 3 9.0 0.0525 0.823 - 0.926 0.977 - 1.053 0.796 6303 3880 4 9.0 0.0444 0.645 - 0.815 0.977 - 1.051 0.702 5891 4003 5 0.0 0.0835 0.965 - 1.359 0.985 - 1.040 0.854 5286 3704

All scans 0.0600 0.615 - 1.359 0.977 - 1.053 0.764 43034 27857

Statistics for singles of twin component 2 ——————————————-

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 9.0 0.0550 0.826 - 0.971 0.966 - 1.044 0.738 19915 12655 2 9.0 0.0576 0.585 - 0.793 0.965 - 1.034 0.733 5549 3613 3 9.0 0.0612 0.851 - 1.065 0.982 - 1.044 0.796 6321 3801 4 9.0 0.0545 0.682 - 0.895 0.965 - 1.043 0.702 5859 3824 5 0.0 0.0769 0.904 - 0.998 0.981 - 1.038 0.854 5264 3752

All scans 0.0618 0.585 - 1.065 0.965 - 1.044 0.764 42908 27645

Statistics for all composite reflections —————————————-

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 9.0 0.0679 0.835 - 0.997 0.977 - 1.046 0.738 15762 11647 2 9.0 0.0641 0.590 - 0.873 0.970 - 1.028 0.733 5558 4178 3 9.0 0.0705 0.840 - 0.995 0.982 - 1.050 0.796 4676 3353 4 9.0 0.0534 0.648 - 0.856 0.972 - 1.045 0.702 5215 3969 5 0.0 0.0759 0.932 - 1.258 0.984 - 1.038 0.854 2819 2441

All scans 0.0677 0.590 - 1.258 0.970 - 1.050 0.764 34030 25588

Statistics for all single and composite reflections —————————————————

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 9.0 0.0591 0.826 - 1.007 0.966 - 1.051 0.738 55636 36928 2 9.0 0.0581 0.585 - 0.888 0.965 - 1.034 0.733 16702 11435 3 9.0 0.0615 0.823 - 1.065 0.977 - 1.053 0.796 17300 11034 4 9.0 0.0508 0.645 - 0.895 0.965 - 1.051 0.702 16965 11796 5 0.0 0.0789 0.904 - 1.359 0.981 - 1.040 0.854 13369 9897

All scans 0.0632 0.585 - 1.359 0.965 - 1.053 0.764 119972 81090

su = K * Sqrt[ sigma^{2(I) + (g<I>)}2 ] where sigma(I) is estimated by SAINT

The above statistics are based on all non-rejected data, ignoring reflections without equivalents when estimating R(int) and K.

==============================================================================

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1B	−0.2104 (6)	0.8340 (6)	0.2840 (5)	0.112 (3)	0.663 (4)
F2B	−0.2143 (3)	0.7385 (3)	0.1892 (4)	0.0869 (14)	0.663 (4)
F3B	−0.1727 (4)	0.8723 (5)	0.1488 (4)	0.105 (3)	0.663 (4)
B1B	−0.1667 (5)	0.8067 (6)	0.2138 (5)	0.055 (2)	0.663 (4)
C1B	−0.0618 (4)	0.7711 (5)	0.2354 (6)	0.0431 (17)	0.663 (4)
C2B	−0.0441 (7)	0.7022 (9)	0.2994 (11)	0.0531 (13)	0.663 (4)
H2B	−0.093767	0.675878	0.328765	0.064*	0.663 (4)
C3B	0.0446 (8)	0.6718 (8)	0.3206 (12)	0.051 (3)	0.663 (4)
H3B	0.053412	0.625763	0.364970	0.062*	0.663 (4)
N1B	0.1188 (7)	0.7043 (9)	0.2814 (13)	0.053 (3)	0.663 (4)
C4B	0.1019 (5)	0.7707 (16)	0.2195 (18)	0.0497 (17)	0.663 (4)
H4B	0.152769	0.795175	0.190541	0.060*	0.663 (4)
C5B	0.0160 (4)	0.8049 (10)	0.1960 (11)	0.044 (3)	0.663 (4)
H5B	0.009400	0.852153	0.152556	0.053*	0.663 (4)
F1B'	−0.1454 (6)	0.9257 (5)	0.2229 (7)	0.0869 (14)	0.337 (4)
F2B'	−0.2149 (11)	0.8064 (11)	0.2748 (9)	0.105 (3)	0.337 (4)
F3B'	−0.1768 (9)	0.8195 (10)	0.1414 (8)	0.112 (3)	0.337 (4)
B1B'	−0.1483 (9)	0.8370 (7)	0.2182 (9)	0.055 (2)	0.337 (4)
C1B'	−0.0487 (8)	0.7864 (10)	0.2408 (12)	0.0431 (17)	0.337 (4)
C2B'	−0.0431 (14)	0.7062 (17)	0.293 (2)	0.0531 (13)	0.337 (4)
H2B'	−0.097357	0.684296	0.317893	0.064*	0.337 (4)
C3B'	0.0402 (17)	0.6584 (19)	0.309 (3)	0.051 (3)	0.337 (4)
H3B'	0.040778	0.604003	0.343954	0.062*	0.337 (4)
N1B'	0.1203 (14)	0.685 (2)	0.277 (3)	0.053 (3)	0.337 (4)
C4B'	0.1150 (9)	0.762 (3)	0.226 (4)	0.0497 (17)	0.337 (4)
H4B'	0.170408	0.783572	0.203388	0.060*	0.337 (4)
C5B'	0.0346 (9)	0.811 (2)	0.205 (2)	0.044 (3)	0.337 (4)
H5B'	0.035607	0.861453	0.164884	0.053*	0.337 (4)
F1A	0.68568 (18)	0.30814 (16)	0.89801 (16)	0.0574 (7)
F2A	0.57907 (17)	0.22720 (16)	0.96888 (14)	0.0524 (6)
F3A	0.69490 (15)	0.15717 (16)	0.89666 (15)	0.0493 (6)
N1A	0.4657 (2)	0.2726 (2)	0.6663 (2)	0.0501 (9)
C1A	0.5736 (2)	0.2466 (2)	0.8127 (2)	0.0323 (8)
C2A	0.6012 (3)	0.2938 (3)	0.7393 (2)	0.0380 (9)
H2A	0.658474	0.318732	0.736745	0.046*
C3A	0.5472 (3)	0.3052 (3)	0.6698 (3)	0.0459 (10)
H3A	0.569229	0.338534	0.621099	0.055*
C4A	0.4383 (3)	0.2262 (3)	0.7361 (3)	0.0455 (11)
H4A	0.381009	0.201576	0.736168	0.055*
C5A	0.4889 (3)	0.2114 (2)	0.8093 (3)	0.0386 (9)
H5A	0.465646	0.177378	0.857024	0.046*
B1A	0.6344 (3)	0.2344 (3)	0.8957 (3)	0.0384 (10)
P1A	0.50167 (6)	0.72490 (6)	0.73998 (5)	0.02328 (19)
O1A	0.78277 (17)	0.53973 (16)	0.84740 (17)	0.0407 (7)
O2A	0.68112 (19)	0.47828 (18)	0.58277 (17)	0.0448 (7)
O3A	0.39095 (18)	0.47200 (16)	0.94836 (17)	0.0405 (6)
O4A	0.20021 (16)	0.74181 (17)	0.90311 (16)	0.0338 (6)
O5A	0.25360 (17)	0.69964 (18)	0.53194 (16)	0.0389 (6)
O6A	0.47866 (17)	0.91268 (16)	0.46093 (15)	0.0360 (6)
O7A	0.47610 (19)	1.00364 (16)	0.90581 (17)	0.0433 (7)
O8A	0.74042 (16)	0.94804 (16)	0.73365 (16)	0.0320 (6)
C6A	0.5955 (2)	0.6434 (2)	0.7250 (2)	0.0267 (8)
C7A	0.5990 (2)	0.5965 (2)	0.6539 (2)	0.0295 (8)
H7A	0.556159	0.610557	0.610527	0.035*
C8A	0.6680 (2)	0.5283 (2)	0.6494 (2)	0.0333 (8)
C9A	0.7302 (2)	0.5066 (2)	0.7135 (2)	0.0350 (9)
H9A	0.776026	0.458901	0.709531	0.042*
C10A	0.7250 (2)	0.5540 (2)	0.7815 (2)	0.0311 (8)
C11A	0.6575 (2)	0.6242 (2)	0.7880 (2)	0.0270 (8)
H11A	0.654547	0.658053	0.835069	0.032*
C12A	0.6165 (3)	0.4942 (3)	0.5188 (3)	0.0496 (11)
H12A	0.631840	0.453496	0.475467	0.074*
H12B	0.617188	0.555849	0.493813	0.074*
H12C	0.555484	0.484355	0.542612	0.074*
C13A	0.8455 (3)	0.4621 (3)	0.8494 (3)	0.0458 (10)
H13A	0.881092	0.457417	0.900465	0.069*
H13B	0.886734	0.466404	0.800084	0.069*
H13C	0.811521	0.409126	0.848972	0.069*
C14A	0.4198 (2)	0.6765 (2)	0.8120 (2)	0.0245 (7)
C15A	0.4401 (2)	0.5906 (2)	0.8499 (2)	0.0273 (8)
H15A	0.495219	0.557126	0.836127	0.033*
C16A	0.3782 (2)	0.5555 (2)	0.9079 (2)	0.0293 (8)
C17A	0.2978 (2)	0.6042 (2)	0.9287 (2)	0.0297 (8)
H17A	0.256778	0.579796	0.970075	0.036*
C18A	0.2776 (2)	0.6884 (2)	0.8892 (2)	0.0275 (8)
C19A	0.3385 (2)	0.7249 (2)	0.8291 (2)	0.0264 (7)
H19A	0.324207	0.782042	0.800527	0.032*
C20A	0.4747 (3)	0.4198 (3)	0.9294 (3)	0.0433 (10)
H20A	0.480164	0.365465	0.968000	0.065*
H20B	0.526802	0.454702	0.935749	0.065*
H20C	0.473901	0.403921	0.871553	0.065*
C21A	0.1424 (2)	0.7160 (3)	0.9736 (2)	0.0371 (9)
H21A	0.089449	0.759606	0.976312	0.056*
H21B	0.176679	0.713431	1.025364	0.056*
H21C	0.121585	0.657195	0.967461	0.056*
C22A	0.4466 (2)	0.7581 (2)	0.6426 (2)	0.0252 (7)
C23A	0.4826 (2)	0.8231 (2)	0.5867 (2)	0.0281 (8)
H23A	0.535648	0.850028	0.600047	0.034*
C24A	0.4396 (2)	0.8481 (2)	0.5108 (2)	0.0287 (8)
C25A	0.3629 (2)	0.8078 (2)	0.4905 (2)	0.0304 (8)
H25A	0.333955	0.824878	0.438618	0.037*
C26A	0.3290 (2)	0.7424 (2)	0.5466 (2)	0.0289 (8)
C27A	0.3702 (2)	0.7168 (2)	0.6228 (2)	0.0287 (8)
H27A	0.346542	0.671731	0.660857	0.034*
C28A	0.4344 (3)	0.9447 (3)	0.3840 (2)	0.0387 (9)
H28A	0.469285	0.990710	0.353759	0.058*
H28B	0.372500	0.970100	0.396614	0.058*
H28C	0.431356	0.895330	0.349233	0.058*
C29A	0.2125 (3)	0.7183 (3)	0.4516 (2)	0.0399 (10)
H29A	0.159618	0.683279	0.449608	0.060*
H29B	0.257127	0.702416	0.407507	0.060*
H29C	0.192635	0.781820	0.442604	0.060*
C30A	0.5460 (2)	0.8198 (2)	0.7783 (2)	0.0241 (7)
C31A	0.4921 (2)	0.8701 (2)	0.8337 (2)	0.0280 (8)
H31A	0.435913	0.850506	0.856435	0.034*
C32A	0.5230 (2)	0.9487 (2)	0.8543 (2)	0.0291 (8)
C33A	0.6067 (2)	0.9771 (2)	0.8233 (2)	0.0276 (8)
H33A	0.627400	1.030832	0.838809	0.033*
C34A	0.6591 (2)	0.9258 (2)	0.7695 (2)	0.0247 (7)
C35A	0.6287 (2)	0.8470 (2)	0.7463 (2)	0.0237 (7)
H35A	0.664454	0.812411	0.708868	0.028*
C36A	0.3881 (3)	0.9793 (3)	0.9367 (3)	0.0539 (12)
H36A	0.361545	1.023371	0.973546	0.081*
H36B	0.394552	0.920527	0.968354	0.081*
H36C	0.347942	0.977494	0.889399	0.081*
C37A	0.7718 (3)	1.0318 (2)	0.7501 (3)	0.0379 (9)
H37A	0.828116	1.041793	0.717335	0.057*
H37B	0.783829	1.030880	0.810032	0.057*
H37C	0.724927	1.079853	0.734272	0.057*
P1B	−0.00412 (6)	0.74139 (6)	0.72783 (6)	0.0244 (2)
O1B	−0.09796 (18)	0.51854 (17)	0.53723 (17)	0.0406 (6)
O2B	−0.27341 (17)	0.80466 (17)	0.53465 (16)	0.0387 (6)
O3B	0.0537 (2)	0.45871 (19)	0.92246 (18)	0.0514 (8)
O4B	0.27103 (16)	0.52142 (16)	0.69547 (16)	0.0355 (6)
O5B	0.0935 (2)	0.93724 (19)	0.46129 (17)	0.0477 (7)
O6B	0.26922 (17)	0.92423 (17)	0.70832 (19)	0.0439 (7)
O7B	−0.07268 (17)	0.98389 (16)	0.92770 (17)	0.0378 (6)
O8B	−0.26768 (16)	0.74029 (16)	0.93708 (16)	0.0323 (6)
C6B	−0.0832 (2)	0.7063 (2)	0.6568 (2)	0.0266 (8)
C7B	−0.0665 (2)	0.6230 (2)	0.6270 (2)	0.0303 (8)
H7B	−0.019838	0.581540	0.650253	0.036*
C8B	−0.1192 (2)	0.6012 (2)	0.5626 (2)	0.0319 (8)
C9B	−0.1879 (2)	0.6616 (2)	0.5289 (2)	0.0329 (8)
H9B	−0.222621	0.647248	0.483824	0.039*
C10B	−0.2054 (2)	0.7432 (2)	0.5620 (2)	0.0301 (8)
C11B	−0.1540 (2)	0.7663 (2)	0.6263 (2)	0.0287 (8)
H11B	−0.166766	0.821808	0.648996	0.034*
C12B	−0.1353 (3)	0.4987 (3)	0.4606 (2)	0.0431 (10)
H12D	−0.110659	0.439331	0.447340	0.065*
H12E	−0.118823	0.543025	0.415177	0.065*
H12F	−0.201904	0.500101	0.466822	0.065*
C13B	−0.3241 (3)	0.7857 (3)	0.4635 (2)	0.0430 (10)
H13D	−0.368823	0.835897	0.448242	0.064*
H13E	−0.355874	0.731772	0.478164	0.064*
H13F	−0.281876	0.776548	0.415828	0.064*
C14B	0.0666 (2)	0.6447 (2)	0.7661 (2)	0.0246 (7)
C15B	0.0369 (2)	0.5893 (2)	0.8331 (2)	0.0281 (8)
H15B	−0.017131	0.606020	0.863903	0.034*
C16B	0.0869 (2)	0.5087 (2)	0.8553 (2)	0.0338 (8)
C17B	0.1657 (2)	0.4831 (2)	0.8097 (2)	0.0300 (8)
H17B	0.198916	0.427458	0.824163	0.036*
C18B	0.1945 (2)	0.5398 (2)	0.7435 (2)	0.0271 (8)
C19B	0.1459 (2)	0.6210 (2)	0.7204 (2)	0.0257 (7)
H19B	0.166349	0.659377	0.674413	0.031*
C20B	0.1043 (3)	0.3763 (3)	0.9497 (3)	0.0649 (15)
H20D	0.071825	0.346234	0.997294	0.097*
H20E	0.164995	0.388329	0.967021	0.097*
H20F	0.110578	0.338049	0.903534	0.097*
C21B	0.3221 (3)	0.4372 (3)	0.7151 (3)	0.0445 (10)
H21D	0.376728	0.433207	0.678471	0.067*
H21E	0.284103	0.388910	0.706491	0.067*
H21F	0.340244	0.432182	0.773809	0.067*
C22B	0.0670 (2)	0.8174 (2)	0.6703 (2)	0.0281 (8)
C23B	0.0482 (2)	0.8462 (2)	0.5859 (2)	0.0319 (8)
H23B	−0.002064	0.826355	0.559186	0.038*
C24B	0.1050 (3)	0.9040 (3)	0.5432 (2)	0.0370 (9)
C25B	0.1783 (3)	0.9336 (2)	0.5822 (3)	0.0384 (9)
H25B	0.215793	0.974586	0.552037	0.046*
C26B	0.1970 (2)	0.9034 (2)	0.6654 (3)	0.0353 (9)
C27B	0.1409 (2)	0.8443 (2)	0.7097 (2)	0.0315 (8)
H27B	0.153307	0.822706	0.766164	0.038*
C28B	0.0196 (3)	0.9054 (3)	0.4157 (3)	0.0519 (11)
H28D	0.016437	0.936852	0.359323	0.078*
H28E	−0.038627	0.916646	0.446018	0.078*
H28F	0.031588	0.841288	0.411257	0.078*
C29B	0.3214 (3)	0.9942 (3)	0.6702 (3)	0.0510 (12)
H29D	0.365451	1.008921	0.710262	0.076*
H29E	0.280298	1.046997	0.654158	0.076*
H29F	0.354214	0.974311	0.620160	0.076*
C30B	−0.0691 (2)	0.7919 (2)	0.8102 (2)	0.0240 (7)
C31B	−0.0451 (2)	0.8703 (2)	0.8395 (2)	0.0274 (8)
H31B	0.006517	0.898689	0.816384	0.033*
C32B	−0.0985 (2)	0.9061 (2)	0.9036 (2)	0.0293 (8)
C33B	−0.1729 (2)	0.8636 (2)	0.9388 (2)	0.0286 (8)
H33B	−0.207765	0.887570	0.983532	0.034*
C34B	−0.1959 (2)	0.7856 (2)	0.9079 (2)	0.0254 (7)
C35B	−0.1442 (2)	0.7497 (2)	0.8428 (2)	0.0272 (8)
H35B	−0.160296	0.697003	0.821145	0.033*
C36B	−0.1269 (3)	1.0250 (3)	0.9918 (3)	0.0405 (9)
H36D	−0.099902	1.078986	1.004561	0.061*
H36E	−0.128767	0.983414	1.042541	0.061*
H36F	−0.189105	1.040652	0.972068	0.061*
C37B	−0.3262 (3)	0.7769 (3)	1.0007 (3)	0.0442 (10)
H37D	−0.376192	0.738583	1.014542	0.066*
H37E	−0.351506	0.836644	0.980048	0.066*
H37F	−0.291095	0.780340	1.051022	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1B	0.090 (5)	0.169 (8)	0.070 (4)	0.053 (5)	0.013 (3)	−0.038 (4)
F2B	0.054 (2)	0.063 (3)	0.143 (4)	0.002 (2)	−0.006 (3)	−0.013 (3)
F3B	0.072 (3)	0.123 (5)	0.106 (5)	−0.017 (3)	−0.030 (3)	0.074 (4)
B1B	0.061 (5)	0.056 (6)	0.044 (4)	0.008 (5)	0.021 (4)	0.000 (4)
C1B	0.046 (3)	0.046 (4)	0.038 (3)	−0.008 (3)	0.002 (2)	−0.007 (3)
C2B	0.055 (3)	0.055 (3)	0.049 (4)	−0.015 (2)	−0.003 (2)	0.008 (2)
C3B	0.063 (3)	0.041 (5)	0.052 (6)	−0.008 (3)	−0.021 (3)	−0.008 (5)
N1B	0.053 (2)	0.046 (7)	0.063 (3)	−0.003 (3)	−0.013 (2)	−0.024 (5)
C4B	0.042 (3)	0.054 (5)	0.055 (5)	−0.009 (4)	0.002 (5)	−0.012 (3)
C5B	0.050 (4)	0.043 (3)	0.039 (5)	−0.007 (4)	0.006 (5)	−0.002 (3)
F1B'	0.054 (2)	0.063 (3)	0.143 (4)	0.002 (2)	−0.006 (3)	−0.013 (3)
F2B'	0.072 (3)	0.123 (5)	0.106 (5)	−0.017 (3)	−0.030 (3)	0.074 (4)
F3B'	0.090 (5)	0.169 (8)	0.070 (4)	0.053 (5)	0.013 (3)	−0.038 (4)
B1B'	0.061 (5)	0.056 (6)	0.044 (4)	0.008 (5)	0.021 (4)	0.000 (4)
C1B'	0.046 (3)	0.046 (4)	0.038 (3)	−0.008 (3)	0.002 (2)	−0.007 (3)
C2B'	0.055 (3)	0.055 (3)	0.049 (4)	−0.015 (2)	−0.003 (2)	0.008 (2)
C3B'	0.063 (3)	0.041 (5)	0.052 (6)	−0.008 (3)	−0.021 (3)	−0.008 (5)
N1B'	0.053 (2)	0.046 (7)	0.063 (3)	−0.003 (3)	−0.013 (2)	−0.024 (5)
C4B'	0.042 (3)	0.054 (5)	0.055 (5)	−0.009 (4)	0.002 (5)	−0.012 (3)
C5B'	0.050 (4)	0.043 (3)	0.039 (5)	−0.007 (4)	0.006 (5)	−0.002 (3)
F1A	0.0645 (16)	0.0558 (16)	0.0563 (16)	−0.0209 (13)	−0.0189 (13)	−0.0074 (12)
F2A	0.0595 (15)	0.0575 (15)	0.0376 (13)	0.0088 (12)	−0.0001 (11)	−0.0045 (11)
F3A	0.0417 (13)	0.0548 (15)	0.0501 (14)	0.0124 (11)	−0.0084 (11)	−0.0103 (12)
N1A	0.046 (2)	0.055 (2)	0.050 (2)	0.0126 (18)	−0.0142 (18)	−0.0190 (19)
C1A	0.033 (2)	0.0251 (19)	0.040 (2)	0.0037 (15)	0.0000 (16)	−0.0130 (16)
C2A	0.038 (2)	0.036 (2)	0.042 (2)	−0.0036 (17)	−0.0033 (18)	−0.0110 (18)
C3A	0.052 (3)	0.045 (2)	0.040 (2)	0.005 (2)	0.002 (2)	−0.0064 (19)
C4A	0.031 (2)	0.044 (2)	0.065 (3)	−0.0001 (18)	−0.007 (2)	−0.021 (2)
C5A	0.035 (2)	0.032 (2)	0.050 (2)	−0.0027 (16)	0.0014 (18)	−0.0127 (18)
B1A	0.040 (3)	0.035 (2)	0.042 (3)	−0.005 (2)	−0.001 (2)	−0.012 (2)
P1A	0.0227 (4)	0.0238 (5)	0.0236 (5)	−0.0020 (4)	−0.0011 (4)	−0.0036 (4)
O1A	0.0345 (14)	0.0321 (14)	0.0554 (18)	0.0029 (11)	−0.0158 (13)	−0.0031 (13)
O2A	0.0470 (16)	0.0451 (16)	0.0440 (17)	0.0057 (13)	−0.0038 (13)	−0.0207 (13)
O3A	0.0434 (15)	0.0283 (14)	0.0480 (17)	−0.0050 (12)	0.0014 (13)	0.0071 (12)
O4A	0.0270 (13)	0.0391 (15)	0.0340 (14)	−0.0001 (11)	0.0062 (11)	−0.0019 (11)
O5A	0.0345 (14)	0.0529 (17)	0.0313 (14)	−0.0162 (12)	−0.0097 (11)	−0.0002 (12)
O6A	0.0385 (14)	0.0349 (14)	0.0335 (14)	−0.0084 (11)	−0.0098 (11)	0.0103 (11)
O7A	0.0513 (17)	0.0321 (14)	0.0487 (17)	−0.0096 (12)	0.0224 (13)	−0.0175 (12)
O8A	0.0267 (12)	0.0310 (14)	0.0397 (15)	−0.0085 (10)	0.0021 (11)	−0.0063 (11)
C6A	0.0247 (17)	0.0246 (18)	0.0311 (19)	−0.0035 (14)	−0.0007 (15)	−0.0023 (15)
C7A	0.0272 (19)	0.0323 (19)	0.031 (2)	−0.0042 (15)	−0.0016 (15)	−0.0095 (16)
C8A	0.033 (2)	0.029 (2)	0.040 (2)	−0.0050 (15)	0.0067 (17)	−0.0127 (17)
C9A	0.0278 (19)	0.030 (2)	0.047 (2)	0.0004 (15)	−0.0029 (17)	−0.0045 (18)
C10A	0.0272 (18)	0.0245 (18)	0.043 (2)	−0.0081 (15)	−0.0045 (16)	−0.0039 (16)
C11A	0.0246 (17)	0.0235 (18)	0.033 (2)	−0.0015 (14)	−0.0028 (15)	−0.0038 (15)
C12A	0.057 (3)	0.049 (3)	0.044 (3)	0.004 (2)	−0.004 (2)	−0.018 (2)
C13A	0.041 (2)	0.034 (2)	0.060 (3)	0.0034 (18)	−0.012 (2)	0.0030 (19)
C14A	0.0242 (17)	0.0266 (18)	0.0244 (18)	−0.0062 (14)	−0.0042 (14)	−0.0052 (14)
C15A	0.0297 (18)	0.0239 (18)	0.0289 (19)	−0.0024 (14)	−0.0023 (15)	−0.0049 (14)
C16A	0.0337 (19)	0.0243 (18)	0.031 (2)	−0.0083 (15)	−0.0035 (16)	−0.0017 (15)
C17A	0.0281 (18)	0.035 (2)	0.0263 (19)	−0.0090 (15)	0.0001 (15)	−0.0019 (15)
C18A	0.0243 (17)	0.0300 (19)	0.0294 (19)	−0.0025 (14)	−0.0046 (15)	−0.0072 (15)
C19A	0.0284 (18)	0.0275 (18)	0.0232 (18)	−0.0023 (14)	−0.0027 (14)	−0.0014 (14)
C20A	0.048 (2)	0.027 (2)	0.053 (3)	−0.0021 (18)	−0.004 (2)	0.0009 (18)
C21A	0.0292 (19)	0.047 (2)	0.035 (2)	−0.0044 (17)	0.0067 (16)	−0.0043 (18)
C22A	0.0277 (18)	0.0232 (18)	0.0252 (18)	0.0004 (14)	−0.0020 (14)	−0.0072 (14)
C23A	0.0266 (18)	0.0300 (19)	0.0284 (19)	−0.0044 (15)	−0.0011 (15)	−0.0038 (15)
C24A	0.0303 (18)	0.0263 (19)	0.0292 (19)	−0.0031 (15)	0.0016 (15)	−0.0010 (15)
C25A	0.0297 (19)	0.035 (2)	0.0265 (19)	−0.0011 (16)	−0.0031 (15)	−0.0023 (15)
C26A	0.0234 (17)	0.035 (2)	0.029 (2)	−0.0041 (15)	−0.0004 (15)	−0.0089 (16)
C27A	0.0265 (18)	0.034 (2)	0.0259 (19)	−0.0030 (15)	0.0003 (15)	−0.0041 (15)
C28A	0.041 (2)	0.039 (2)	0.034 (2)	−0.0029 (17)	−0.0079 (17)	0.0106 (17)
C29A	0.034 (2)	0.054 (3)	0.033 (2)	−0.0124 (18)	−0.0102 (17)	−0.0009 (19)
C30A	0.0257 (17)	0.0244 (18)	0.0224 (17)	−0.0004 (14)	−0.0059 (14)	−0.0027 (14)
C31A	0.0275 (18)	0.0269 (18)	0.0294 (19)	−0.0029 (14)	0.0020 (15)	−0.0023 (15)
C32A	0.0360 (19)	0.0244 (18)	0.0265 (19)	0.0015 (15)	0.0021 (15)	−0.0054 (14)
C33A	0.0322 (19)	0.0241 (18)	0.0275 (19)	−0.0053 (14)	−0.0032 (15)	−0.0036 (14)
C34A	0.0253 (17)	0.0253 (18)	0.0228 (18)	−0.0016 (14)	−0.0031 (14)	0.0011 (14)
C35A	0.0244 (17)	0.0239 (18)	0.0228 (18)	0.0021 (14)	−0.0038 (14)	−0.0045 (14)
C36A	0.052 (3)	0.043 (2)	0.069 (3)	−0.005 (2)	0.028 (2)	−0.026 (2)
C37A	0.035 (2)	0.031 (2)	0.050 (2)	−0.0131 (16)	0.0011 (18)	−0.0062 (18)
P1B	0.0207 (4)	0.0252 (5)	0.0276 (5)	−0.0002 (3)	−0.0016 (4)	−0.0049 (4)
O1B	0.0467 (16)	0.0340 (15)	0.0431 (16)	0.0017 (12)	−0.0084 (13)	−0.0151 (12)
O2B	0.0308 (13)	0.0436 (16)	0.0418 (16)	0.0061 (12)	−0.0130 (12)	−0.0077 (12)
O3B	0.0545 (18)	0.0496 (18)	0.0406 (17)	0.0210 (14)	0.0116 (14)	0.0166 (14)
O4B	0.0271 (13)	0.0328 (14)	0.0441 (16)	0.0085 (11)	0.0074 (11)	−0.0029 (12)
O5B	0.0501 (17)	0.0519 (18)	0.0381 (16)	−0.0011 (14)	0.0032 (13)	0.0067 (13)
O6B	0.0300 (14)	0.0334 (15)	0.068 (2)	−0.0089 (11)	−0.0032 (13)	0.0010 (14)
O7B	0.0342 (14)	0.0335 (14)	0.0490 (16)	−0.0060 (11)	0.0042 (12)	−0.0190 (12)
O8B	0.0307 (13)	0.0304 (13)	0.0368 (15)	−0.0077 (11)	0.0086 (11)	−0.0065 (11)
C6B	0.0242 (17)	0.0299 (19)	0.0264 (19)	−0.0022 (14)	−0.0016 (14)	−0.0063 (15)
C7B	0.0288 (19)	0.0297 (19)	0.033 (2)	0.0009 (15)	−0.0044 (15)	−0.0053 (16)
C8B	0.0312 (19)	0.030 (2)	0.036 (2)	−0.0024 (15)	0.0006 (16)	−0.0090 (16)
C9B	0.0302 (19)	0.038 (2)	0.031 (2)	−0.0025 (16)	−0.0036 (16)	−0.0070 (17)
C10B	0.0221 (17)	0.035 (2)	0.032 (2)	0.0008 (15)	−0.0051 (15)	0.0024 (16)
C11B	0.0275 (18)	0.0280 (19)	0.031 (2)	−0.0012 (15)	−0.0009 (15)	−0.0078 (15)
C12B	0.048 (2)	0.046 (2)	0.038 (2)	−0.0093 (19)	−0.0004 (19)	−0.0168 (19)
C13B	0.035 (2)	0.057 (3)	0.036 (2)	0.0020 (19)	−0.0145 (18)	0.0001 (19)
C14B	0.0223 (17)	0.0239 (18)	0.0286 (19)	−0.0004 (14)	−0.0037 (14)	−0.0076 (14)
C15B	0.0259 (18)	0.0315 (19)	0.0259 (19)	0.0062 (15)	−0.0015 (14)	−0.0039 (15)
C16B	0.035 (2)	0.036 (2)	0.028 (2)	0.0022 (16)	−0.0010 (16)	0.0017 (16)
C17B	0.0307 (19)	0.0282 (19)	0.030 (2)	0.0063 (15)	−0.0061 (15)	−0.0059 (15)
C18B	0.0227 (17)	0.0281 (19)	0.032 (2)	0.0001 (14)	−0.0017 (15)	−0.0097 (15)
C19B	0.0231 (17)	0.0270 (18)	0.0272 (19)	−0.0020 (14)	−0.0023 (14)	−0.0033 (14)
C20B	0.074 (3)	0.057 (3)	0.049 (3)	0.032 (3)	0.014 (2)	0.029 (2)
C21B	0.034 (2)	0.040 (2)	0.056 (3)	0.0181 (18)	0.0048 (19)	−0.007 (2)
C22B	0.0231 (17)	0.0261 (18)	0.034 (2)	0.0015 (14)	0.0027 (15)	−0.0017 (15)
C23B	0.0295 (19)	0.032 (2)	0.034 (2)	0.0010 (15)	−0.0003 (16)	−0.0026 (16)
C24B	0.039 (2)	0.035 (2)	0.035 (2)	0.0029 (17)	0.0068 (17)	−0.0007 (17)
C25B	0.035 (2)	0.028 (2)	0.049 (3)	−0.0006 (16)	0.0137 (18)	0.0037 (18)
C26B	0.0254 (19)	0.0277 (19)	0.052 (3)	0.0006 (15)	0.0025 (17)	−0.0021 (17)
C27B	0.0272 (19)	0.0253 (19)	0.042 (2)	0.0015 (14)	0.0013 (16)	−0.0039 (16)
C28B	0.054 (3)	0.063 (3)	0.037 (2)	−0.001 (2)	0.000 (2)	−0.002 (2)
C29B	0.036 (2)	0.035 (2)	0.082 (3)	−0.0141 (18)	0.010 (2)	−0.005 (2)
C30B	0.0189 (16)	0.0253 (18)	0.0273 (18)	0.0035 (13)	−0.0036 (14)	−0.0030 (14)
C31B	0.0224 (17)	0.0257 (18)	0.034 (2)	−0.0023 (14)	0.0003 (15)	−0.0043 (15)
C32B	0.0267 (18)	0.0259 (19)	0.036 (2)	−0.0016 (14)	−0.0055 (15)	−0.0063 (15)
C33B	0.0274 (18)	0.0300 (19)	0.0282 (19)	0.0039 (14)	−0.0014 (15)	−0.0063 (15)
C34B	0.0244 (17)	0.0237 (18)	0.0274 (19)	−0.0005 (14)	−0.0020 (14)	0.0001 (14)
C35B	0.0278 (18)	0.0214 (18)	0.033 (2)	−0.0005 (14)	−0.0043 (15)	−0.0039 (15)
C36B	0.043 (2)	0.033 (2)	0.048 (2)	−0.0016 (17)	−0.0021 (19)	−0.0201 (18)
C37B	0.039 (2)	0.049 (3)	0.047 (3)	−0.0091 (19)	0.0155 (19)	−0.013 (2)

Geometric parameters (Å, º)

F1B—B1B	1.357 (9)	C28A—H28A	0.9800
F2B—B1B	1.389 (11)	C28A—H28B	0.9800
F3B—B1B	1.368 (8)	C28A—H28C	0.9800
B1B—C1B	1.627 (8)	C29A—H29A	0.9800
C1B—C5B	1.399 (6)	C29A—H29B	0.9800
C1B—C2B	1.405 (7)	C29A—H29C	0.9800
C2B—C3B	1.388 (7)	C30A—C35A	1.382 (5)
C2B—H2B	0.9500	C30A—C31A	1.406 (5)
C3B—N1B	1.346 (6)	C31A—C32A	1.382 (5)
C3B—H3B	0.9500	C31A—H31A	0.9500
N1B—C4B	1.355 (8)	C32A—C33A	1.398 (5)
C4B—C5B	1.374 (7)	C33A—C34A	1.385 (5)
C4B—H4B	0.9500	C33A—H33A	0.9500
C5B—H5B	0.9500	C34A—C35A	1.396 (5)
F1B'—B1B'	1.357 (10)	C35A—H35A	0.9500
F2B'—B1B'	1.389 (11)	C36A—H36A	0.9800
F3B'—B1B'	1.370 (8)	C36A—H36B	0.9800
B1B'—C1B'	1.628 (8)	C36A—H36C	0.9800
C1B'—C5B'	1.399 (7)	C37A—H37A	0.9800
C1B'—C2B'	1.405 (7)	C37A—H37B	0.9800
C2B'—C3B'	1.388 (7)	C37A—H37C	0.9800
C2B'—H2B'	0.9500	P1B—C22B	1.790 (4)
C3B'—N1B'	1.346 (7)	P1B—C14B	1.793 (3)
C3B'—H3B'	0.9500	P1B—C30B	1.795 (3)
N1B'—C4B'	1.355 (9)	P1B—C6B	1.800 (3)
C4B'—C5B'	1.375 (8)	O1B—C8B	1.361 (4)
C4B'—H4B'	0.9500	O1B—C12B	1.429 (4)
C5B'—H5B'	0.9500	O2B—C10B	1.360 (4)
F1A—B1A	1.404 (5)	O2B—C13B	1.447 (4)
F2A—B1A	1.405 (5)	O3B—C16B	1.356 (4)
F3A—B1A	1.406 (5)	O3B—C20B	1.436 (5)
N1A—C4A	1.331 (6)	O4B—C18B	1.366 (4)
N1A—C3A	1.338 (6)	O4B—C21B	1.436 (4)
C1A—C2A	1.382 (5)	O5B—C24B	1.371 (5)
C1A—C5A	1.399 (5)	O5B—C28B	1.469 (5)
C1A—B1A	1.615 (6)	O6B—C26B	1.359 (4)
C2A—C3A	1.378 (6)	O6B—C29B	1.437 (5)
C2A—H2A	0.9500	O7B—C32B	1.361 (4)
C3A—H3A	0.9500	O7B—C36B	1.436 (4)
C4A—C5A	1.400 (6)	O8B—C34B	1.353 (4)
C4A—H4A	0.9500	O8B—C37B	1.433 (4)
C5A—H5A	0.9500	C6B—C7B	1.391 (5)
P1A—C22A	1.790 (3)	C6B—C11B	1.391 (5)
P1A—C14A	1.792 (4)	C7B—C8B	1.391 (5)
P1A—C30A	1.795 (3)	C7B—H7B	0.9500
P1A—C6A	1.796 (3)	C8B—C9B	1.390 (5)
O1A—C10A	1.367 (4)	C9B—C10B	1.392 (5)
O1A—C13A	1.430 (4)	C9B—H9B	0.9500
O2A—C8A	1.367 (4)	C10B—C11B	1.386 (5)
O2A—C12A	1.411 (5)	C11B—H11B	0.9500
O3A—C16A	1.364 (4)	C12B—H12D	0.9800
O3A—C20A	1.445 (5)	C12B—H12E	0.9800
O4A—C18A	1.364 (4)	C12B—H12F	0.9800
O4A—C21A	1.435 (4)	C13B—H13D	0.9800
O5A—C26A	1.368 (4)	C13B—H13E	0.9800
O5A—C29A	1.434 (4)	C13B—H13F	0.9800
O6A—C24A	1.356 (4)	C14B—C15B	1.379 (5)
O6A—C28A	1.436 (4)	C14B—C19B	1.395 (5)
O7A—C32A	1.358 (4)	C15B—C16B	1.391 (5)
O7A—C36A	1.435 (5)	C15B—H15B	0.9500
O8A—C34A	1.363 (4)	C16B—C17B	1.394 (5)
O8A—C37A	1.436 (4)	C17B—C18B	1.378 (5)
C6A—C11A	1.375 (5)	C17B—H17B	0.9500
C6A—C7A	1.397 (5)	C18B—C19B	1.392 (5)
C7A—C8A	1.390 (5)	C19B—H19B	0.9500
C7A—H7A	0.9500	C20B—H20D	0.9800
C8A—C9A	1.394 (5)	C20B—H20E	0.9800
C9A—C10A	1.358 (5)	C20B—H20F	0.9800
C9A—H9A	0.9500	C21B—H21D	0.9800
C10A—C11A	1.400 (5)	C21B—H21E	0.9800
C11A—H11A	0.9500	C21B—H21F	0.9800
C12A—H12A	0.9800	C22B—C27B	1.384 (5)
C12A—H12B	0.9800	C22B—C23B	1.409 (5)
C12A—H12C	0.9800	C23B—C24B	1.379 (5)
C13A—H13A	0.9800	C23B—H23B	0.9500
C13A—H13B	0.9800	C24B—C25B	1.391 (6)
C13A—H13C	0.9800	C25B—C26B	1.395 (6)
C14A—C19A	1.381 (5)	C25B—H25B	0.9500
C14A—C15A	1.394 (5)	C26B—C27B	1.396 (5)
C15A—C16A	1.380 (5)	C27B—H27B	0.9500
C15A—H15A	0.9500	C28B—H28D	0.9800
C16A—C17A	1.388 (5)	C28B—H28E	0.9800
C17A—C18A	1.381 (5)	C28B—H28F	0.9800
C17A—H17A	0.9500	C29B—H29D	0.9800
C18A—C19A	1.398 (5)	C29B—H29E	0.9800
C19A—H19A	0.9500	C29B—H29F	0.9800
C20A—H20A	0.9800	C30B—C35B	1.384 (5)
C20A—H20B	0.9800	C30B—C31B	1.395 (5)
C20A—H20C	0.9800	C31B—C32B	1.395 (5)
C21A—H21A	0.9800	C31B—H31B	0.9500
C21A—H21B	0.9800	C32B—C33B	1.391 (5)
C21A—H21C	0.9800	C33B—C34B	1.394 (5)
C22A—C27A	1.391 (5)	C33B—H33B	0.9500
C22A—C23A	1.392 (5)	C34B—C35B	1.396 (5)
C23A—C24A	1.393 (5)	C35B—H35B	0.9500
C23A—H23A	0.9500	C36B—H36D	0.9800
C24A—C25A	1.390 (5)	C36B—H36E	0.9800
C25A—C26A	1.384 (5)	C36B—H36F	0.9800
C25A—H25A	0.9500	C37B—H37D	0.9800
C26A—C27A	1.388 (5)	C37B—H37E	0.9800
C27A—H27A	0.9500	C37B—H37F	0.9800
F1B—B1B—F3B	111.3 (8)	O5A—C29A—H29C	109.5
F1B—B1B—F2B	106.5 (7)	H29A—C29A—H29C	109.5
F3B—B1B—F2B	105.7 (7)	H29B—C29A—H29C	109.5
F1B—B1B—C1B	109.4 (7)	C35A—C30A—C31A	121.2 (3)
F3B—B1B—C1B	112.9 (5)	C35A—C30A—P1A	119.1 (3)
F2B—B1B—C1B	110.9 (6)	C31A—C30A—P1A	119.4 (3)
C5B—C1B—C2B	114.8 (5)	C32A—C31A—C30A	118.2 (3)
C5B—C1B—B1B	125.3 (5)	C32A—C31A—H31A	120.9
C2B—C1B—B1B	119.9 (5)	C30A—C31A—H31A	120.9
C3B—C2B—C1B	121.2 (5)	O7A—C32A—C31A	123.6 (3)
C3B—C2B—H2B	119.4	O7A—C32A—C33A	114.9 (3)
C1B—C2B—H2B	119.4	C31A—C32A—C33A	121.6 (3)
N1B—C3B—C2B	123.2 (5)	C34A—C33A—C32A	119.1 (3)
N1B—C3B—H3B	118.4	C34A—C33A—H33A	120.5
C2B—C3B—H3B	118.4	C32A—C33A—H33A	120.5
C3B—N1B—C4B	115.7 (5)	O8A—C34A—C33A	124.2 (3)
N1B—C4B—C5B	124.3 (5)	O8A—C34A—C35A	115.1 (3)
N1B—C4B—H4B	117.9	C33A—C34A—C35A	120.6 (3)
C5B—C4B—H4B	117.9	C30A—C35A—C34A	119.3 (3)
C4B—C5B—C1B	120.8 (5)	C30A—C35A—H35A	120.3
C4B—C5B—H5B	119.6	C34A—C35A—H35A	120.3
C1B—C5B—H5B	119.6	O7A—C36A—H36A	109.5
F1B'—B1B'—F3B'	111.4 (10)	O7A—C36A—H36B	109.5
F1B'—B1B'—F2B'	108.4 (9)	H36A—C36A—H36B	109.5
F3B'—B1B'—F2B'	104.8 (9)	O7A—C36A—H36C	109.5
F1B'—B1B'—C1B'	109.3 (8)	H36A—C36A—H36C	109.5
F3B'—B1B'—C1B'	112.3 (8)	H36B—C36A—H36C	109.5
F2B'—B1B'—C1B'	110.6 (8)	O8A—C37A—H37A	109.5
C5B'—C1B'—C2B'	114.8 (6)	O8A—C37A—H37B	109.5
C5B'—C1B'—B1B'	125.1 (6)	H37A—C37A—H37B	109.5
C2B'—C1B'—B1B'	119.7 (6)	O8A—C37A—H37C	109.5
C3B'—C2B'—C1B'	121.2 (6)	H37A—C37A—H37C	109.5
C3B'—C2B'—H2B'	119.4	H37B—C37A—H37C	109.5
C1B'—C2B'—H2B'	119.4	C22B—P1B—C14B	108.26 (16)
N1B'—C3B'—C2B'	123.3 (7)	C22B—P1B—C30B	112.03 (16)
N1B'—C3B'—H3B'	118.4	C14B—P1B—C30B	112.53 (16)
C2B'—C3B'—H3B'	118.4	C22B—P1B—C6B	108.47 (17)
C3B'—N1B'—C4B'	115.7 (6)	C14B—P1B—C6B	107.42 (16)
N1B'—C4B'—C5B'	124.2 (7)	C30B—P1B—C6B	107.96 (16)
N1B'—C4B'—H4B'	117.9	C8B—O1B—C12B	117.8 (3)
C5B'—C4B'—H4B'	117.9	C10B—O2B—C13B	117.3 (3)
C4B'—C5B'—C1B'	120.8 (6)	C16B—O3B—C20B	118.0 (3)
C4B'—C5B'—H5B'	119.6	C18B—O4B—C21B	117.2 (3)
C1B'—C5B'—H5B'	119.6	C24B—O5B—C28B	117.8 (3)
C4A—N1A—C3A	115.3 (4)	C26B—O6B—C29B	117.2 (3)
C2A—C1A—C5A	114.8 (4)	C32B—O7B—C36B	117.7 (3)
C2A—C1A—B1A	122.2 (3)	C34B—O8B—C37B	118.1 (3)
C5A—C1A—B1A	123.0 (4)	C7B—C6B—C11B	121.4 (3)
C3A—C2A—C1A	121.2 (4)	C7B—C6B—P1B	119.0 (3)
C3A—C2A—H2A	119.4	C11B—C6B—P1B	119.3 (3)
C1A—C2A—H2A	119.4	C6B—C7B—C8B	119.0 (3)
N1A—C3A—C2A	124.4 (4)	C6B—C7B—H7B	120.5
N1A—C3A—H3A	117.8	C8B—C7B—H7B	120.5
C2A—C3A—H3A	117.8	O1B—C8B—C9B	124.5 (3)
N1A—C4A—C5A	124.0 (4)	O1B—C8B—C7B	115.0 (3)
N1A—C4A—H4A	118.0	C9B—C8B—C7B	120.5 (3)
C5A—C4A—H4A	118.0	C8B—C9B—C10B	119.3 (3)
C1A—C5A—C4A	120.3 (4)	C8B—C9B—H9B	120.4
C1A—C5A—H5A	119.8	C10B—C9B—H9B	120.4
C4A—C5A—H5A	119.8	O2B—C10B—C11B	115.8 (3)
F1A—B1A—F2A	108.4 (3)	O2B—C10B—C9B	123.0 (3)
F1A—B1A—F3A	108.5 (3)	C11B—C10B—C9B	121.2 (3)
F2A—B1A—F3A	107.8 (3)	C10B—C11B—C6B	118.5 (3)
F1A—B1A—C1A	109.7 (3)	C10B—C11B—H11B	120.7
F2A—B1A—C1A	111.2 (3)	C6B—C11B—H11B	120.7
F3A—B1A—C1A	111.2 (3)	O1B—C12B—H12D	109.5
C22A—P1A—C14A	108.05 (16)	O1B—C12B—H12E	109.5
C22A—P1A—C30A	109.46 (15)	H12D—C12B—H12E	109.5
C14A—P1A—C30A	111.94 (16)	O1B—C12B—H12F	109.5
C22A—P1A—C6A	110.24 (16)	H12D—C12B—H12F	109.5
C14A—P1A—C6A	109.02 (16)	H12E—C12B—H12F	109.5
C30A—P1A—C6A	108.12 (16)	O2B—C13B—H13D	109.5
C10A—O1A—C13A	116.9 (3)	O2B—C13B—H13E	109.5
C8A—O2A—C12A	116.9 (3)	H13D—C13B—H13E	109.5
C16A—O3A—C20A	117.2 (3)	O2B—C13B—H13F	109.5
C18A—O4A—C21A	117.8 (3)	H13D—C13B—H13F	109.5
C26A—O5A—C29A	118.1 (3)	H13E—C13B—H13F	109.5
C24A—O6A—C28A	117.4 (3)	C15B—C14B—C19B	120.9 (3)
C32A—O7A—C36A	117.1 (3)	C15B—C14B—P1B	120.1 (3)
C34A—O8A—C37A	117.7 (3)	C19B—C14B—P1B	118.5 (3)
C11A—C6A—C7A	122.1 (3)	C14B—C15B—C16B	119.4 (3)
C11A—C6A—P1A	118.3 (3)	C14B—C15B—H15B	120.3
C7A—C6A—P1A	119.3 (3)	C16B—C15B—H15B	120.3
C8A—C7A—C6A	117.0 (3)	O3B—C16B—C15B	115.7 (3)
C8A—C7A—H7A	121.5	O3B—C16B—C17B	123.6 (3)
C6A—C7A—H7A	121.5	C15B—C16B—C17B	120.7 (3)
O2A—C8A—C7A	123.4 (3)	C18B—C17B—C16B	118.9 (3)
O2A—C8A—C9A	114.9 (3)	C18B—C17B—H17B	120.6
C7A—C8A—C9A	121.7 (3)	C16B—C17B—H17B	120.6
C10A—C9A—C8A	119.7 (3)	O4B—C18B—C17B	123.5 (3)
C10A—C9A—H9A	120.2	O4B—C18B—C19B	115.0 (3)
C8A—C9A—H9A	120.2	C17B—C18B—C19B	121.5 (3)
C9A—C10A—O1A	124.9 (3)	C18B—C19B—C14B	118.6 (3)
C9A—C10A—C11A	120.6 (3)	C18B—C19B—H19B	120.7
O1A—C10A—C11A	114.6 (3)	C14B—C19B—H19B	120.7
C6A—C11A—C10A	119.0 (3)	O3B—C20B—H20D	109.5
C6A—C11A—H11A	120.5	O3B—C20B—H20E	109.5
C10A—C11A—H11A	120.5	H20D—C20B—H20E	109.5
O2A—C12A—H12A	109.5	O3B—C20B—H20F	109.5
O2A—C12A—H12B	109.5	H20D—C20B—H20F	109.5
H12A—C12A—H12B	109.5	H20E—C20B—H20F	109.5
O2A—C12A—H12C	109.5	O4B—C21B—H21D	109.5
H12A—C12A—H12C	109.5	O4B—C21B—H21E	109.5
H12B—C12A—H12C	109.5	H21D—C21B—H21E	109.5
O1A—C13A—H13A	109.5	O4B—C21B—H21F	109.5
O1A—C13A—H13B	109.5	H21D—C21B—H21F	109.5
H13A—C13A—H13B	109.5	H21E—C21B—H21F	109.5
O1A—C13A—H13C	109.5	C27B—C22B—C23B	121.8 (3)
H13A—C13A—H13C	109.5	C27B—C22B—P1B	118.6 (3)
H13B—C13A—H13C	109.5	C23B—C22B—P1B	119.5 (3)
C19A—C14A—C15A	121.5 (3)	C24B—C23B—C22B	117.9 (3)
C19A—C14A—P1A	119.6 (3)	C24B—C23B—H23B	121.0
C15A—C14A—P1A	118.9 (3)	C22B—C23B—H23B	121.0
C16A—C15A—C14A	118.4 (3)	O5B—C24B—C23B	123.4 (4)
C16A—C15A—H15A	120.8	O5B—C24B—C25B	115.3 (3)
C14A—C15A—H15A	120.8	C23B—C24B—C25B	121.3 (4)
O3A—C16A—C15A	123.3 (3)	C24B—C25B—C26B	120.1 (3)
O3A—C16A—C17A	115.6 (3)	C24B—C25B—H25B	119.9
C15A—C16A—C17A	121.1 (3)	C26B—C25B—H25B	119.9
C18A—C17A—C16A	119.8 (3)	O6B—C26B—C25B	125.2 (3)
C18A—C17A—H17A	120.1	O6B—C26B—C27B	115.1 (3)
C16A—C17A—H17A	120.1	C25B—C26B—C27B	119.7 (4)
O4A—C18A—C17A	125.1 (3)	C22B—C27B—C26B	119.2 (4)
O4A—C18A—C19A	114.7 (3)	C22B—C27B—H27B	120.4
C17A—C18A—C19A	120.1 (3)	C26B—C27B—H27B	120.4
C14A—C19A—C18A	119.0 (3)	O5B—C28B—H28D	109.5
C14A—C19A—H19A	120.5	O5B—C28B—H28E	109.5
C18A—C19A—H19A	120.5	H28D—C28B—H28E	109.5
O3A—C20A—H20A	109.5	O5B—C28B—H28F	109.5
O3A—C20A—H20B	109.5	H28D—C28B—H28F	109.5
H20A—C20A—H20B	109.5	H28E—C28B—H28F	109.5
O3A—C20A—H20C	109.5	O6B—C29B—H29D	109.5
H20A—C20A—H20C	109.5	O6B—C29B—H29E	109.5
H20B—C20A—H20C	109.5	H29D—C29B—H29E	109.5
O4A—C21A—H21A	109.5	O6B—C29B—H29F	109.5
O4A—C21A—H21B	109.5	H29D—C29B—H29F	109.5
H21A—C21A—H21B	109.5	H29E—C29B—H29F	109.5
O4A—C21A—H21C	109.5	C35B—C30B—C31B	121.7 (3)
H21A—C21A—H21C	109.5	C35B—C30B—P1B	116.9 (3)
H21B—C21A—H21C	109.5	C31B—C30B—P1B	121.4 (3)
C27A—C22A—C23A	120.9 (3)	C32B—C31B—C30B	118.5 (3)
C27A—C22A—P1A	119.7 (3)	C32B—C31B—H31B	120.8
C23A—C22A—P1A	119.4 (3)	C30B—C31B—H31B	120.8
C22A—C23A—C24A	119.0 (3)	O7B—C32B—C33B	123.8 (3)
C22A—C23A—H23A	120.5	O7B—C32B—C31B	115.4 (3)
C24A—C23A—H23A	120.5	C33B—C32B—C31B	120.8 (3)
O6A—C24A—C25A	124.5 (3)	C32B—C33B—C34B	119.6 (3)
O6A—C24A—C23A	114.9 (3)	C32B—C33B—H33B	120.2
C25A—C24A—C23A	120.6 (3)	C34B—C33B—H33B	120.2
C26A—C25A—C24A	119.4 (3)	O8B—C34B—C33B	124.0 (3)
C26A—C25A—H25A	120.3	O8B—C34B—C35B	115.6 (3)
C24A—C25A—H25A	120.3	C33B—C34B—C35B	120.4 (3)
O5A—C26A—C25A	123.3 (3)	C30B—C35B—C34B	119.0 (3)
O5A—C26A—C27A	115.6 (3)	C30B—C35B—H35B	120.5
C25A—C26A—C27A	121.1 (3)	C34B—C35B—H35B	120.5
C26A—C27A—C22A	118.9 (3)	O7B—C36B—H36D	109.5
C26A—C27A—H27A	120.5	O7B—C36B—H36E	109.5
C22A—C27A—H27A	120.5	H36D—C36B—H36E	109.5
O6A—C28A—H28A	109.5	O7B—C36B—H36F	109.5
O6A—C28A—H28B	109.5	H36D—C36B—H36F	109.5
H28A—C28A—H28B	109.5	H36E—C36B—H36F	109.5
O6A—C28A—H28C	109.5	O8B—C37B—H37D	109.5
H28A—C28A—H28C	109.5	O8B—C37B—H37E	109.5
H28B—C28A—H28C	109.5	H37D—C37B—H37E	109.5
O5A—C29A—H29A	109.5	O8B—C37B—H37F	109.5
O5A—C29A—H29B	109.5	H37D—C37B—H37F	109.5
H29A—C29A—H29B	109.5	H37E—C37B—H37F	109.5
F1B—B1B—C1B—C5B	−121.6 (13)	C14A—P1A—C30A—C35A	158.9 (2)
F3B—B1B—C1B—C5B	2.9 (16)	C6A—P1A—C30A—C35A	38.8 (3)
F2B—B1B—C1B—C5B	121.3 (13)	C22A—P1A—C30A—C31A	92.5 (3)
F1B—B1B—C1B—C2B	56.9 (13)	C14A—P1A—C30A—C31A	−27.3 (3)
F3B—B1B—C1B—C2B	−178.6 (12)	C6A—P1A—C30A—C31A	−147.4 (3)
F2B—B1B—C1B—C2B	−60.2 (12)	C35A—C30A—C31A—C32A	1.3 (5)
C5B—C1B—C2B—C3B	0.2 (13)	P1A—C30A—C31A—C32A	−172.3 (3)
B1B—C1B—C2B—C3B	−178.5 (10)	C36A—O7A—C32A—C31A	−3.0 (5)
C1B—C2B—C3B—N1B	−1.1 (13)	C36A—O7A—C32A—C33A	177.6 (3)
C2B—C3B—N1B—C4B	1 (2)	C30A—C31A—C32A—O7A	178.7 (3)
C3B—N1B—C4B—C5B	0 (3)	C30A—C31A—C32A—C33A	−1.9 (5)
N1B—C4B—C5B—C1B	−1 (3)	O7A—C32A—C33A—C34A	−179.4 (3)
C2B—C1B—C5B—C4B	1 (2)	C31A—C32A—C33A—C34A	1.1 (5)
B1B—C1B—C5B—C4B	179.3 (18)	C37A—O8A—C34A—C33A	−2.6 (5)
F1B'—B1B'—C1B'—C5B'	−50 (3)	C37A—O8A—C34A—C35A	175.4 (3)
F3B'—B1B'—C1B'—C5B'	74 (3)	C32A—C33A—C34A—O8A	178.1 (3)
F2B'—B1B'—C1B'—C5B'	−170 (3)	C32A—C33A—C34A—C35A	0.3 (5)
F1B'—B1B'—C1B'—C2B'	137 (2)	C31A—C30A—C35A—C34A	0.0 (5)
F3B'—B1B'—C1B'—C2B'	−99 (2)	P1A—C30A—C35A—C34A	173.6 (2)
F2B'—B1B'—C1B'—C2B'	18 (2)	O8A—C34A—C35A—C30A	−178.8 (3)
C5B'—C1B'—C2B'—C3B'	3 (2)	C33A—C34A—C35A—C30A	−0.8 (5)
B1B'—C1B'—C2B'—C3B'	175.6 (18)	C22B—P1B—C6B—C7B	101.9 (3)
C1B'—C2B'—C3B'—N1B'	1 (3)	C14B—P1B—C6B—C7B	−14.9 (3)
C2B'—C3B'—N1B'—C4B'	−2 (5)	C30B—P1B—C6B—C7B	−136.5 (3)
C3B'—N1B'—C4B'—C5B'	−1 (7)	C22B—P1B—C6B—C11B	−71.5 (3)
N1B'—C4B'—C5B'—C1B'	5 (7)	C14B—P1B—C6B—C11B	171.7 (3)
C2B'—C1B'—C5B'—C4B'	−5 (5)	C30B—P1B—C6B—C11B	50.1 (3)
B1B'—C1B'—C5B'—C4B'	−178 (4)	C11B—C6B—C7B—C8B	3.1 (5)
C5A—C1A—C2A—C3A	1.0 (5)	P1B—C6B—C7B—C8B	−170.2 (3)
B1A—C1A—C2A—C3A	−178.4 (3)	C12B—O1B—C8B—C9B	13.2 (5)
C4A—N1A—C3A—C2A	−0.3 (6)	C12B—O1B—C8B—C7B	−167.1 (3)
C1A—C2A—C3A—N1A	−0.4 (6)	C6B—C7B—C8B—O1B	179.8 (3)
C3A—N1A—C4A—C5A	0.3 (6)	C6B—C7B—C8B—C9B	−0.5 (6)
C2A—C1A—C5A—C4A	−1.0 (5)	O1B—C8B—C9B—C10B	177.8 (3)
B1A—C1A—C5A—C4A	178.4 (3)	C7B—C8B—C9B—C10B	−1.9 (6)
N1A—C4A—C5A—C1A	0.3 (6)	C13B—O2B—C10B—C11B	175.5 (3)
C2A—C1A—B1A—F1A	29.9 (5)	C13B—O2B—C10B—C9B	−5.1 (5)
C5A—C1A—B1A—F1A	−149.5 (3)	C8B—C9B—C10B—O2B	−177.7 (3)
C2A—C1A—B1A—F2A	149.7 (3)	C8B—C9B—C10B—C11B	1.7 (6)
C5A—C1A—B1A—F2A	−29.7 (5)	O2B—C10B—C11B—C6B	−179.8 (3)
C2A—C1A—B1A—F3A	−90.2 (4)	C9B—C10B—C11B—C6B	0.8 (5)
C5A—C1A—B1A—F3A	90.4 (4)	C7B—C6B—C11B—C10B	−3.2 (5)
C22A—P1A—C6A—C11A	166.3 (3)	P1B—C6B—C11B—C10B	170.1 (3)
C14A—P1A—C6A—C11A	−75.2 (3)	C22B—P1B—C14B—C15B	159.1 (3)
C30A—P1A—C6A—C11A	46.7 (3)	C30B—P1B—C14B—C15B	34.8 (3)
C22A—P1A—C6A—C7A	−19.1 (3)	C6B—P1B—C14B—C15B	−83.9 (3)
C14A—P1A—C6A—C7A	99.4 (3)	C22B—P1B—C14B—C19B	−28.9 (3)
C30A—P1A—C6A—C7A	−138.7 (3)	C30B—P1B—C14B—C19B	−153.3 (3)
C11A—C6A—C7A—C8A	0.5 (5)	C6B—P1B—C14B—C19B	88.0 (3)
P1A—C6A—C7A—C8A	−173.9 (3)	C19B—C14B—C15B—C16B	0.0 (5)
C12A—O2A—C8A—C7A	−4.4 (5)	P1B—C14B—C15B—C16B	171.7 (3)
C12A—O2A—C8A—C9A	176.3 (4)	C20B—O3B—C16B—C15B	−177.9 (4)
C6A—C7A—C8A—O2A	−178.3 (3)	C20B—O3B—C16B—C17B	2.1 (6)
C6A—C7A—C8A—C9A	0.9 (5)	C14B—C15B—C16B—O3B	179.2 (3)
O2A—C8A—C9A—C10A	178.1 (3)	C14B—C15B—C16B—C17B	−0.9 (5)
C7A—C8A—C9A—C10A	−1.3 (6)	O3B—C16B—C17B—C18B	−178.7 (3)
C8A—C9A—C10A—O1A	−179.0 (3)	C15B—C16B—C17B—C18B	1.4 (5)
C8A—C9A—C10A—C11A	0.2 (6)	C21B—O4B—C18B—C17B	1.3 (5)
C13A—O1A—C10A—C9A	−8.5 (5)	C21B—O4B—C18B—C19B	−178.1 (3)
C13A—O1A—C10A—C11A	172.3 (3)	C16B—C17B—C18B—O4B	179.4 (3)
C7A—C6A—C11A—C10A	−1.6 (5)	C16B—C17B—C18B—C19B	−1.1 (5)
P1A—C6A—C11A—C10A	172.9 (3)	O4B—C18B—C19B—C14B	179.8 (3)
C9A—C10A—C11A—C6A	1.2 (5)	C17B—C18B—C19B—C14B	0.3 (5)
O1A—C10A—C11A—C6A	−179.5 (3)	C15B—C14B—C19B—C18B	0.3 (5)
C22A—P1A—C14A—C19A	−56.0 (3)	P1B—C14B—C19B—C18B	−171.6 (2)
C30A—P1A—C14A—C19A	64.6 (3)	C14B—P1B—C22B—C27B	−55.4 (3)
C6A—P1A—C14A—C19A	−175.8 (3)	C30B—P1B—C22B—C27B	69.3 (3)
C22A—P1A—C14A—C15A	124.4 (3)	C6B—P1B—C22B—C27B	−171.6 (3)
C30A—P1A—C14A—C15A	−115.0 (3)	C14B—P1B—C22B—C23B	122.7 (3)
C6A—P1A—C14A—C15A	4.6 (3)	C30B—P1B—C22B—C23B	−112.6 (3)
C19A—C14A—C15A—C16A	−2.3 (5)	C6B—P1B—C22B—C23B	6.4 (3)
P1A—C14A—C15A—C16A	177.3 (3)	C27B—C22B—C23B—C24B	−1.3 (5)
C20A—O3A—C16A—C15A	1.0 (5)	P1B—C22B—C23B—C24B	−179.3 (3)
C20A—O3A—C16A—C17A	−178.9 (3)	C28B—O5B—C24B—C23B	−3.5 (5)
C14A—C15A—C16A—O3A	179.6 (3)	C28B—O5B—C24B—C25B	177.4 (3)
C14A—C15A—C16A—C17A	−0.4 (5)	C22B—C23B—C24B—O5B	−179.4 (3)
O3A—C16A—C17A—C18A	−178.1 (3)	C22B—C23B—C24B—C25B	−0.4 (5)
C15A—C16A—C17A—C18A	2.0 (5)	O5B—C24B—C25B—C26B	−179.4 (3)
C21A—O4A—C18A—C17A	11.2 (5)	C23B—C24B—C25B—C26B	1.5 (6)
C21A—O4A—C18A—C19A	−169.3 (3)	C29B—O6B—C26B—C25B	11.1 (5)
C16A—C17A—C18A—O4A	178.7 (3)	C29B—O6B—C26B—C27B	−171.4 (3)
C16A—C17A—C18A—C19A	−0.8 (5)	C24B—C25B—C26B—O6B	176.5 (3)
C15A—C14A—C19A—C18A	3.4 (5)	C24B—C25B—C26B—C27B	−1.0 (5)
P1A—C14A—C19A—C18A	−176.2 (2)	C23B—C22B—C27B—C26B	1.8 (5)
O4A—C18A—C19A—C14A	178.7 (3)	P1B—C22B—C27B—C26B	179.8 (3)
C17A—C18A—C19A—C14A	−1.8 (5)	O6B—C26B—C27B—C22B	−178.4 (3)
C14A—P1A—C22A—C27A	−23.9 (3)	C25B—C26B—C27B—C22B	−0.7 (5)
C30A—P1A—C22A—C27A	−146.0 (3)	C22B—P1B—C30B—C35B	162.0 (2)
C6A—P1A—C22A—C27A	95.2 (3)	C14B—P1B—C30B—C35B	−75.7 (3)
C14A—P1A—C22A—C23A	158.0 (3)	C6B—P1B—C30B—C35B	42.7 (3)
C30A—P1A—C22A—C23A	35.9 (3)	C22B—P1B—C30B—C31B	−17.7 (3)
C6A—P1A—C22A—C23A	−82.9 (3)	C14B—P1B—C30B—C31B	104.5 (3)
C27A—C22A—C23A—C24A	1.5 (5)	C6B—P1B—C30B—C31B	−137.1 (3)
P1A—C22A—C23A—C24A	179.6 (3)	C35B—C30B—C31B—C32B	0.3 (5)
C28A—O6A—C24A—C25A	3.6 (5)	P1B—C30B—C31B—C32B	180.0 (3)
C28A—O6A—C24A—C23A	−176.6 (3)	C36B—O7B—C32B—C33B	−1.4 (5)
C22A—C23A—C24A—O6A	179.1 (3)	C36B—O7B—C32B—C31B	178.2 (3)
C22A—C23A—C24A—C25A	−1.1 (5)	C30B—C31B—C32B—O7B	−178.3 (3)
O6A—C24A—C25A—C26A	−180.0 (3)	C30B—C31B—C32B—C33B	1.4 (5)
C23A—C24A—C25A—C26A	0.2 (5)	O7B—C32B—C33B—C34B	177.8 (3)
C29A—O5A—C26A—C25A	5.4 (5)	C31B—C32B—C33B—C34B	−1.8 (5)
C29A—O5A—C26A—C27A	−175.2 (3)	C37B—O8B—C34B—C33B	3.2 (5)
C24A—C25A—C26A—O5A	179.6 (3)	C37B—O8B—C34B—C35B	−176.5 (3)
C24A—C25A—C26A—C27A	0.2 (5)	C32B—C33B—C34B—O8B	−179.0 (3)
O5A—C26A—C27A—C22A	−179.3 (3)	C32B—C33B—C34B—C35B	0.7 (5)
C25A—C26A—C27A—C22A	0.2 (5)	C31B—C30B—C35B—C34B	−1.4 (5)
C23A—C22A—C27A—C26A	−1.1 (5)	P1B—C30B—C35B—C34B	178.9 (2)
P1A—C22A—C27A—C26A	−179.1 (3)	O8B—C34B—C35B—C30B	−179.4 (3)
C22A—P1A—C30A—C35A	−81.3 (3)	C33B—C34B—C35B—C30B	0.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3Ba—H3Ba···O1B^i	0.95	2.61	3.546 (11)	168
C4A—H4A···F2B′b^i	0.95	2.47	3.376 (16)	160
C9A—H9A···N1B′b^ii	0.95	2.55	3.48 (2)	168
C11A—H11A···O8B^iii	0.95	2.51	3.365 (4)	150
C13A—H13A···O3B^iii	0.98	2.58	3.309 (5)	132
C13A—H13C···F1A	0.98	2.55	3.466 (5)	155
C19A—H19A···O6B	0.95	2.58	3.518 (4)	171
C20A—H20A···F2A	0.98	2.44	3.196 (4)	133
C20A—H20B···O3A^iv	0.98	2.63	3.442 (5)	140
C21A—H21B···F1A^iv	0.98	2.38	3.286 (4)	153
C27A—H27A···O4B	0.95	2.62	3.490 (5)	153
C33A—H33A···F3A^v	0.95	2.50	3.437 (4)	171
C36A—H36B···F2A^iv	0.98	2.37	3.344 (5)	173
C12B—H12F···O2A^vi	0.98	2.51	3.298 (5)	138
C13B—H13D···O6A^vi	0.98	2.45	3.340 (5)	151
C13B—H13F···F1Ba	0.98	2.44	3.328 (8)	150
C13B—H13F···F2B′b	0.98	2.45	3.374 (14)	157
C17B—H17B···F2Ba^i	0.95	2.53	3.369 (6)	147
C19B—H19B···O5A	0.95	2.62	3.512 (4)	156
C20B—H20F···F2Ba^i	0.98	2.40	3.258 (7)	146
C21B—H21D···N1A	0.98	2.68	3.264 (5)	118
C27B—H27B···O4A	0.95	2.50	3.434 (5)	170
C29B—H29E···F1Ba^vii	0.98	2.29	3.089 (8)	138
C29B—H29E···F2B′b^vii	0.98	2.68	3.459 (19)	136
C35B—H35B···O1A^vi	0.95	2.58	3.434 (4)	149
C36B—H36E···F3Ba^viii	0.98	2.39	3.339 (6)	164
C36B—H36F···F3A^ix	0.98	2.59	3.462 (5)	149
C37B—H37F···F2Ba^viii	0.98	2.52	3.463 (7)	162
C37B—H37F···F3B′b^viii	0.98	2.40	3.343 (13)	161

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+2; (v) x, y+1, z; (vi) x−1, y, z; (vii) −x, −y+2, −z+1; (viii) x, y, z+1; (ix) x−1, y+1, z.

Tetrabutylammonium 4-(trifluoro-λ⁴-boranyl)pyridine (4)

Crystal data

C16H36N^+·C5H4BF3N^−	F(000) = 848
Mr = 388.36	Dx = 1.127 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.8089 (6) Å	Cell parameters from 4787 reflections
b = 13.2030 (8) Å	θ = 2.8–24.2°
c = 19.9075 (14) Å	µ = 0.08 mm^−1
β = 98.652 (2)°	T = 100 K
V = 2289.0 (3) Å^3	Block, colorless
Z = 4	0.08 × 0.07 × 0.06 mm

Data collection

Bruker PHOTON III CPAD diffractometer	2997 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.059
φ and ω scans	θmax = 25.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.705, Tmax = 0.745	k = −15→15
24696 measured reflections	l = −24→24
4206 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.5478P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4206 reflections	Δρmax = 0.19 e Å^−3
248 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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.

Refinement. The reflection 0 3 3 was omitted due to suspected interference from the beam stop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.87060 (12)	0.49765 (8)	0.67911 (5)	0.0453 (3)
F2	0.65154 (11)	0.47930 (7)	0.72698 (6)	0.0442 (3)
F3	0.82431 (10)	0.60208 (7)	0.76526 (5)	0.0337 (2)
B1	0.7554 (2)	0.55092 (14)	0.70641 (10)	0.0292 (4)
N1	0.49052 (18)	0.76296 (12)	0.55814 (8)	0.0422 (4)
C1	0.66453 (17)	0.62910 (12)	0.65199 (8)	0.0251 (4)
C2	0.6301 (2)	0.60776 (14)	0.58298 (9)	0.0357 (4)
H2	0.665192	0.546334	0.565779	0.043*
C3	0.5455 (2)	0.67478 (16)	0.53925 (10)	0.0460 (5)
H3	0.524931	0.657088	0.492507	0.055*
C4	0.52407 (19)	0.78411 (13)	0.62389 (10)	0.0345 (4)
H4	0.487413	0.846205	0.639452	0.041*
C5	0.60904 (18)	0.72161 (11)	0.67133 (9)	0.0279 (4)
H5	0.629611	0.742146	0.717545	0.033*
N2	0.74082 (14)	0.15814 (9)	0.69976 (6)	0.0209 (3)
C6	0.76162 (18)	0.24535 (11)	0.75001 (8)	0.0229 (3)
H6A	0.689105	0.235614	0.782936	0.027*
H6B	0.732103	0.308770	0.724870	0.027*
C7	0.92162 (18)	0.25941 (11)	0.78970 (8)	0.0243 (4)
H7A	0.992356	0.284487	0.759207	0.029*
H7B	0.961282	0.193905	0.809206	0.029*
C8	0.91231 (19)	0.33566 (13)	0.84636 (8)	0.0302 (4)
H8A	0.872531	0.400645	0.826029	0.036*
H8B	0.838493	0.310606	0.875421	0.036*
C9	1.06596 (19)	0.35429 (13)	0.89024 (8)	0.0326 (4)
H9A	1.053447	0.404484	0.925260	0.049*
H9B	1.139467	0.379669	0.861882	0.049*
H9C	1.104250	0.290750	0.911951	0.049*
C10	0.84169 (18)	0.17047 (11)	0.64480 (8)	0.0234 (3)
H10A	0.950325	0.170159	0.666687	0.028*
H10B	0.826395	0.110799	0.614426	0.028*
C11	0.81427 (18)	0.26513 (11)	0.60160 (8)	0.0266 (4)
H11A	0.835245	0.325918	0.630630	0.032*
H11B	0.705651	0.267628	0.579788	0.032*
C12	0.9189 (2)	0.26477 (12)	0.54732 (9)	0.0323 (4)
H12A	1.026689	0.257161	0.569467	0.039*
H12B	0.893299	0.205688	0.517113	0.039*
C13	0.9045 (2)	0.36077 (13)	0.50480 (9)	0.0401 (5)
H13A	0.976764	0.358011	0.471909	0.060*
H13B	0.928045	0.419653	0.534520	0.060*
H13C	0.799516	0.366588	0.480550	0.060*
C14	0.57123 (17)	0.15722 (12)	0.67020 (8)	0.0237 (3)
H14A	0.512396	0.136794	0.706616	0.028*
H14B	0.540311	0.227358	0.656899	0.028*
C15	0.52366 (17)	0.08887 (11)	0.60931 (8)	0.0244 (4)
H15A	0.570451	0.021081	0.618167	0.029*
H15B	0.560651	0.117607	0.568783	0.029*
C16	0.34948 (18)	0.07931 (13)	0.59609 (8)	0.0304 (4)
H16A	0.313904	0.049740	0.636688	0.036*
H16B	0.303844	0.147700	0.588920	0.036*
C17	0.29292 (19)	0.01396 (12)	0.53485 (8)	0.0315 (4)
H17A	0.180805	0.008450	0.529523	0.047*
H17B	0.338556	−0.053685	0.541389	0.047*
H17C	0.322818	0.044843	0.494029	0.047*
C18	0.78669 (18)	0.05778 (11)	0.73517 (8)	0.0224 (3)
H18A	0.753390	0.002086	0.703017	0.027*
H18B	0.900135	0.055184	0.745415	0.027*
C19	0.72230 (18)	0.03815 (11)	0.80036 (8)	0.0249 (4)
H19A	0.610095	0.050193	0.792758	0.030*
H19B	0.769620	0.085471	0.836058	0.030*
C20	0.7547 (2)	−0.07010 (12)	0.82368 (8)	0.0307 (4)
H20A	0.867028	−0.081429	0.831589	0.037*
H20B	0.709146	−0.116969	0.787328	0.037*
C21	0.6899 (2)	−0.09388 (12)	0.88836 (8)	0.0333 (4)
H21A	0.710302	−0.164963	0.900737	0.050*
H21B	0.578837	−0.081920	0.880960	0.050*
H21C	0.738729	−0.050127	0.925148	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0359 (6)	0.0465 (6)	0.0497 (7)	0.0148 (5)	−0.0059 (5)	−0.0126 (5)
F2	0.0324 (6)	0.0310 (5)	0.0643 (7)	−0.0073 (4)	−0.0084 (5)	0.0158 (5)
F3	0.0326 (5)	0.0384 (6)	0.0290 (5)	−0.0045 (4)	0.0006 (4)	−0.0002 (4)
B1	0.0238 (10)	0.0256 (10)	0.0364 (11)	−0.0014 (8)	−0.0015 (8)	−0.0038 (8)
N1	0.0381 (9)	0.0520 (10)	0.0380 (10)	0.0104 (8)	0.0109 (7)	0.0148 (8)
C1	0.0191 (8)	0.0266 (8)	0.0302 (9)	−0.0032 (7)	0.0056 (7)	−0.0016 (7)
C2	0.0330 (10)	0.0424 (10)	0.0317 (10)	0.0089 (8)	0.0052 (8)	−0.0057 (8)
C3	0.0429 (11)	0.0671 (14)	0.0279 (10)	0.0151 (10)	0.0050 (9)	0.0015 (10)
C4	0.0312 (9)	0.0262 (9)	0.0485 (12)	0.0009 (7)	0.0137 (8)	0.0073 (8)
C5	0.0287 (9)	0.0252 (8)	0.0305 (9)	−0.0048 (7)	0.0069 (7)	0.0005 (7)
N2	0.0225 (7)	0.0206 (6)	0.0189 (7)	0.0016 (5)	0.0011 (5)	−0.0013 (5)
C6	0.0285 (8)	0.0188 (8)	0.0208 (8)	0.0009 (6)	0.0017 (7)	−0.0042 (6)
C7	0.0249 (8)	0.0247 (8)	0.0227 (8)	−0.0003 (7)	0.0013 (7)	−0.0024 (7)
C8	0.0291 (9)	0.0325 (9)	0.0273 (9)	0.0014 (7)	−0.0010 (7)	−0.0077 (7)
C9	0.0313 (9)	0.0379 (10)	0.0277 (9)	−0.0052 (8)	0.0017 (7)	−0.0079 (8)
C10	0.0253 (8)	0.0252 (8)	0.0201 (8)	0.0001 (7)	0.0046 (7)	−0.0015 (7)
C11	0.0287 (9)	0.0247 (8)	0.0255 (9)	−0.0009 (7)	0.0008 (7)	0.0005 (7)
C12	0.0391 (10)	0.0293 (9)	0.0292 (9)	−0.0040 (8)	0.0069 (8)	0.0017 (7)
C13	0.0484 (11)	0.0384 (10)	0.0344 (10)	−0.0055 (9)	0.0090 (9)	0.0090 (8)
C14	0.0206 (8)	0.0262 (8)	0.0235 (8)	0.0015 (6)	0.0006 (7)	0.0001 (7)
C15	0.0253 (8)	0.0244 (8)	0.0219 (8)	0.0006 (7)	−0.0013 (7)	−0.0011 (7)
C16	0.0258 (9)	0.0352 (9)	0.0289 (9)	−0.0015 (7)	−0.0002 (7)	−0.0038 (7)
C17	0.0300 (9)	0.0330 (9)	0.0284 (9)	−0.0011 (7)	−0.0051 (7)	0.0021 (7)
C18	0.0239 (8)	0.0199 (8)	0.0226 (8)	0.0021 (6)	0.0005 (6)	−0.0001 (6)
C19	0.0279 (9)	0.0230 (8)	0.0237 (9)	0.0001 (7)	0.0033 (7)	−0.0012 (7)
C20	0.0363 (10)	0.0245 (8)	0.0316 (9)	0.0008 (7)	0.0063 (8)	0.0016 (7)
C21	0.0356 (10)	0.0295 (9)	0.0349 (10)	−0.0012 (8)	0.0055 (8)	0.0074 (8)

Geometric parameters (Å, º)

F1—B1	1.409 (2)	C11—C12	1.522 (2)
F2—B1	1.419 (2)	C11—H11A	0.9900
F3—B1	1.408 (2)	C11—H11B	0.9900
B1—C1	1.618 (2)	C12—C13	1.519 (2)
N1—C4	1.327 (2)	C12—H12A	0.9900
N1—C3	1.337 (2)	C12—H12B	0.9900
C1—C2	1.390 (2)	C13—H13A	0.9800
C1—C5	1.391 (2)	C13—H13B	0.9800
C2—C3	1.379 (2)	C13—H13C	0.9800
C2—H2	0.9500	C14—C15	1.519 (2)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.386 (2)	C14—H14B	0.9900
C4—H4	0.9500	C15—C16	1.522 (2)
C5—H5	0.9500	C15—H15A	0.9900
N2—C6	1.5181 (18)	C15—H15B	0.9900
N2—C10	1.5184 (19)	C16—C17	1.515 (2)
N2—C14	1.5211 (18)	C16—H16A	0.9900
N2—C18	1.5265 (18)	C16—H16B	0.9900
C6—C7	1.520 (2)	C17—H17A	0.9800
C6—H6A	0.9900	C17—H17B	0.9800
C6—H6B	0.9900	C17—H17C	0.9800
C7—C8	1.523 (2)	C18—C19	1.515 (2)
C7—H7A	0.9900	C18—H18A	0.9900
C7—H7B	0.9900	C18—H18B	0.9900
C8—C9	1.517 (2)	C19—C20	1.517 (2)
C8—H8A	0.9900	C19—H19A	0.9900
C8—H8B	0.9900	C19—H19B	0.9900
C9—H9A	0.9800	C20—C21	1.517 (2)
C9—H9B	0.9800	C20—H20A	0.9900
C9—H9C	0.9800	C20—H20B	0.9900
C10—C11	1.516 (2)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800
F3—B1—F1	108.37 (13)	C12—C11—H11B	109.7
F3—B1—F2	107.19 (15)	H11A—C11—H11B	108.2
F1—B1—F2	108.17 (14)	C13—C12—C11	112.60 (14)
F3—B1—C1	111.03 (13)	C13—C12—H12A	109.1
F1—B1—C1	111.88 (15)	C11—C12—H12A	109.1
F2—B1—C1	110.04 (13)	C13—C12—H12B	109.1
C4—N1—C3	115.11 (15)	C11—C12—H12B	109.1
C2—C1—C5	114.70 (15)	H12A—C12—H12B	107.8
C2—C1—B1	123.00 (14)	C12—C13—H13A	109.5
C5—C1—B1	122.25 (14)	C12—C13—H13B	109.5
C3—C2—C1	120.71 (16)	H13A—C13—H13B	109.5
C3—C2—H2	119.6	C12—C13—H13C	109.5
C1—C2—H2	119.6	H13A—C13—H13C	109.5
N1—C3—C2	124.45 (17)	H13B—C13—H13C	109.5
N1—C3—H3	117.8	C15—C14—N2	116.78 (12)
C2—C3—H3	117.8	C15—C14—H14A	108.1
N1—C4—C5	124.34 (16)	N2—C14—H14A	108.1
N1—C4—H4	117.8	C15—C14—H14B	108.1
C5—C4—H4	117.8	N2—C14—H14B	108.1
C4—C5—C1	120.68 (16)	H14A—C14—H14B	107.3
C4—C5—H5	119.7	C14—C15—C16	109.70 (13)
C1—C5—H5	119.7	C14—C15—H15A	109.7
C6—N2—C10	111.58 (11)	C16—C15—H15A	109.7
C6—N2—C14	105.97 (11)	C14—C15—H15B	109.7
C10—N2—C14	111.66 (11)	C16—C15—H15B	109.7
C6—N2—C18	110.90 (11)	H15A—C15—H15B	108.2
C10—N2—C18	106.43 (11)	C17—C16—C15	112.78 (14)
C14—N2—C18	110.37 (11)	C17—C16—H16A	109.0
N2—C6—C7	116.47 (12)	C15—C16—H16A	109.0
N2—C6—H6A	108.2	C17—C16—H16B	109.0
C7—C6—H6A	108.2	C15—C16—H16B	109.0
N2—C6—H6B	108.2	H16A—C16—H16B	107.8
C7—C6—H6B	108.2	C16—C17—H17A	109.5
H6A—C6—H6B	107.3	C16—C17—H17B	109.5
C6—C7—C8	108.46 (12)	H17A—C17—H17B	109.5
C6—C7—H7A	110.0	C16—C17—H17C	109.5
C8—C7—H7A	110.0	H17A—C17—H17C	109.5
C6—C7—H7B	110.0	H17B—C17—H17C	109.5
C8—C7—H7B	110.0	C19—C18—N2	115.91 (12)
H7A—C7—H7B	108.4	C19—C18—H18A	108.3
C9—C8—C7	113.01 (13)	N2—C18—H18A	108.3
C9—C8—H8A	109.0	C19—C18—H18B	108.3
C7—C8—H8A	109.0	N2—C18—H18B	108.3
C9—C8—H8B	109.0	H18A—C18—H18B	107.4
C7—C8—H8B	109.0	C18—C19—C20	110.26 (13)
H8A—C8—H8B	107.8	C18—C19—H19A	109.6
C8—C9—H9A	109.5	C20—C19—H19A	109.6
C8—C9—H9B	109.5	C18—C19—H19B	109.6
H9A—C9—H9B	109.5	C20—C19—H19B	109.6
C8—C9—H9C	109.5	H19A—C19—H19B	108.1
H9A—C9—H9C	109.5	C19—C20—C21	112.18 (14)
H9B—C9—H9C	109.5	C19—C20—H20A	109.2
C11—C10—N2	115.89 (12)	C21—C20—H20A	109.2
C11—C10—H10A	108.3	C19—C20—H20B	109.2
N2—C10—H10A	108.3	C21—C20—H20B	109.2
C11—C10—H10B	108.3	H20A—C20—H20B	107.9
N2—C10—H10B	108.3	C20—C21—H21A	109.5
H10A—C10—H10B	107.4	C20—C21—H21B	109.5
C10—C11—C12	109.78 (13)	H21A—C21—H21B	109.5
C10—C11—H11A	109.7	C20—C21—H21C	109.5
C12—C11—H11A	109.7	H21A—C21—H21C	109.5
C10—C11—H11B	109.7	H21B—C21—H21C	109.5
F3—B1—C1—C2	158.12 (15)	N2—C6—C7—C8	−168.96 (13)
F1—B1—C1—C2	36.9 (2)	C6—C7—C8—C9	179.02 (14)
F2—B1—C1—C2	−83.4 (2)	C6—N2—C10—C11	−59.95 (16)
F3—B1—C1—C5	−24.6 (2)	C14—N2—C10—C11	58.44 (16)
F1—B1—C1—C5	−145.85 (15)	C18—N2—C10—C11	178.95 (12)
F2—B1—C1—C5	93.88 (18)	N2—C10—C11—C12	−177.78 (12)
C5—C1—C2—C3	−0.8 (3)	C10—C11—C12—C13	−176.46 (14)
B1—C1—C2—C3	176.65 (17)	C6—N2—C14—C15	169.56 (13)
C4—N1—C3—C2	0.6 (3)	C10—N2—C14—C15	47.87 (17)
C1—C2—C3—N1	−0.1 (3)	C18—N2—C14—C15	−70.31 (16)
C3—N1—C4—C5	−0.2 (3)	N2—C14—C15—C16	167.71 (13)
N1—C4—C5—C1	−0.8 (3)	C14—C15—C16—C17	178.66 (13)
C2—C1—C5—C4	1.2 (2)	C6—N2—C18—C19	47.57 (16)
B1—C1—C5—C4	−176.27 (15)	C10—N2—C18—C19	169.11 (12)
C10—N2—C6—C7	−61.29 (16)	C14—N2—C18—C19	−69.56 (15)
C14—N2—C6—C7	176.97 (13)	N2—C18—C19—C20	170.67 (13)
C18—N2—C6—C7	57.18 (17)	C18—C19—C20—C21	−179.08 (13)

Potassium 3-(trifluoro-λ⁴-boranyl)pyridine (1)

Crystal data

K^+·C5H4BF3N^−	Dx = 1.751 Mg m^−3
Mr = 185.00	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7864 reflections
a = 5.8637 (2) Å	θ = 3.1–28.2°
b = 7.2260 (3) Å	µ = 0.74 mm^−1
c = 16.5602 (8) Å	T = 100 K
V = 701.67 (5) Å^3	Block, colorless
Z = 4	0.16 × 0.09 × 0.04 mm
F(000) = 368

Data collection

Bruker PHOTON III CPAD diffractometer	1694 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.034
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→7
Tmin = 0.665, Tmax = 0.746	k = −9→8
11196 measured reflections	l = −21→22
1733 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.033P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.060	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.27 e Å^−3
1733 reflections	Δρmin = −0.17 e Å^−3
100 parameters	Absolute structure: Flack x determined using 680 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.008 (16)
Primary atom site location: dual

Special details

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.

Refinement. The reflection -1 1 2 was omitted due to suspected interference from the beam stop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.09981 (6)	0.49413 (4)	0.45110 (2)	0.01714 (12)
F1	0.40856 (19)	0.47057 (16)	0.56403 (6)	0.0249 (2)
F2	0.69714 (18)	0.64992 (13)	0.51333 (6)	0.0201 (2)
F3	0.76718 (19)	0.35200 (13)	0.54936 (6)	0.0202 (2)
N1	0.6230 (2)	0.5750 (2)	0.80556 (8)	0.0175 (3)
C1	0.7073 (3)	0.5777 (2)	0.66153 (9)	0.0139 (3)
C2	0.5683 (3)	0.5408 (2)	0.72818 (9)	0.0149 (3)
H2	0.423318	0.487067	0.717930	0.018*
C3	0.8274 (3)	0.6516 (2)	0.81927 (10)	0.0181 (3)
H3	0.870417	0.675902	0.873549	0.022*
C4	0.9797 (3)	0.6972 (2)	0.75821 (11)	0.0185 (3)
H4	1.122580	0.752645	0.770347	0.022*
C5	0.9177 (3)	0.6597 (2)	0.67894 (9)	0.0170 (3)
H5	1.019008	0.689953	0.636174	0.020*
B1	0.6408 (3)	0.5132 (3)	0.57211 (10)	0.0156 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01961 (19)	0.01560 (17)	0.01620 (18)	0.00227 (15)	−0.00401 (11)	−0.00193 (13)
F1	0.0196 (5)	0.0353 (6)	0.0197 (5)	−0.0068 (5)	−0.0058 (4)	0.0009 (4)
F2	0.0287 (5)	0.0152 (5)	0.0164 (5)	0.0017 (4)	0.0025 (4)	0.0031 (4)
F3	0.0305 (5)	0.0125 (4)	0.0176 (5)	0.0015 (4)	−0.0008 (4)	−0.0026 (4)
N1	0.0177 (7)	0.0178 (6)	0.0169 (7)	0.0007 (6)	0.0022 (5)	−0.0024 (5)
C1	0.0148 (7)	0.0099 (6)	0.0170 (7)	0.0015 (6)	−0.0004 (6)	0.0002 (5)
C2	0.0140 (7)	0.0124 (7)	0.0184 (7)	0.0004 (5)	0.0007 (6)	−0.0012 (5)
C3	0.0214 (8)	0.0177 (7)	0.0153 (7)	0.0015 (7)	−0.0028 (6)	−0.0042 (6)
C4	0.0149 (7)	0.0161 (7)	0.0245 (8)	−0.0021 (6)	−0.0019 (6)	−0.0054 (6)
C5	0.0179 (8)	0.0142 (7)	0.0189 (7)	−0.0020 (7)	0.0023 (6)	−0.0015 (6)
B1	0.0186 (8)	0.0135 (8)	0.0147 (8)	−0.0002 (7)	−0.0012 (6)	0.0006 (6)

Geometric parameters (Å, º)

K1—F1	2.6084 (11)	F2—B1	1.426 (2)
K1—F3^i	2.6868 (10)	F3—B1	1.431 (2)
K1—F2^ii	2.6997 (10)	N1—C3	1.340 (2)
K1—F3^iii	2.7399 (11)	N1—C2	1.344 (2)
K1—N1^iv	2.7865 (14)	C1—C2	1.398 (2)
K1—F2^iii	2.8114 (11)	C1—C5	1.398 (2)
K1—B1^iii	3.3583 (18)	C1—B1	1.601 (2)
K1—C3^iv	3.4857 (18)	C2—H2	0.9500
K1—B1^ii	3.5886 (19)	C3—C4	1.389 (2)
K1—K1^v	4.8649 (5)	C3—H3	0.9500
K1—K1^i	4.8649 (5)	C4—C5	1.389 (2)
K1—K1^vi	4.9892 (5)	C4—H4	0.9500
F1—B1	1.403 (2)	C5—H5	0.9500
F1—K1—F3^i	71.81 (3)	F1—K1—K1^vi	53.69 (2)
F1—K1—F2^ii	76.06 (3)	F3^i—K1—K1^vi	118.44 (2)
F3^i—K1—F2^ii	144.13 (3)	F2^ii—K1—K1^vi	25.69 (2)
F1—K1—F3^iii	92.51 (3)	F3^iii—K1—K1^vi	120.22 (2)
F3^i—K1—F3^iii	85.00 (2)	N1^iv—K1—K1^vi	133.56 (3)
F2^ii—K1—F3^iii	112.21 (3)	F2^iii—K1—K1^vi	94.46 (2)
F1—K1—N1^iv	159.03 (4)	B1^iii—K1—K1^vi	104.29 (3)
F3^i—K1—N1^iv	90.11 (4)	C3^iv—K1—K1^vi	148.16 (3)
F2^ii—K1—N1^iv	117.30 (4)	B1^ii—K1—K1^vi	42.28 (3)
F3^iii—K1—N1^iv	96.47 (4)	K1^v—K1—K1^vi	94.319 (6)
F1—K1—F2^iii	110.26 (3)	K1^i—K1—K1^vi	141.591 (14)
F3^i—K1—F2^iii	132.89 (3)	B1—F1—K1	136.72 (10)
F2^ii—K1—F2^iii	73.51 (2)	B1—F2—K1^vi	117.53 (9)
F3^iii—K1—F2^iii	48.28 (3)	B1—F2—K1^vii	99.63 (9)
N1^iv—K1—F2^iii	89.72 (4)	K1^vi—F2—K1^vii	129.72 (4)
F1—K1—B1^iii	97.53 (4)	B1—F3—K1^v	124.71 (10)
F3^i—K1—B1^iii	109.43 (4)	B1—F3—K1^vii	102.69 (9)
F2^ii—K1—B1^iii	90.00 (4)	K1^v—F3—K1^vii	127.39 (4)
F3^iii—K1—B1^iii	24.57 (4)	C3—N1—C2	116.80 (14)
N1^iv—K1—B1^iii	98.50 (4)	C3—N1—K1^viii	110.30 (10)
F2^iii—K1—B1^iii	24.74 (4)	C2—N1—K1^viii	132.84 (11)
F1—K1—C3^iv	158.15 (4)	C2—C1—C5	115.62 (14)
F3^i—K1—C3^iv	88.83 (4)	C2—C1—B1	122.21 (15)
F2^ii—K1—C3^iv	125.19 (4)	C5—C1—B1	121.93 (14)
F3^iii—K1—C3^iv	75.35 (4)	N1—C2—C1	125.37 (15)
N1^iv—K1—C3^iv	21.13 (4)	N1—C2—H2	117.3
F2^iii—K1—C3^iv	75.34 (4)	C1—C2—H2	117.3
B1^iii—K1—C3^iv	79.06 (4)	N1—C3—C4	123.38 (15)
F1—K1—B1^ii	95.45 (4)	N1—C3—K1^viii	48.57 (8)
F3^i—K1—B1^ii	153.98 (4)	C4—C3—K1^viii	171.84 (12)
F2^ii—K1—B1^ii	20.63 (3)	N1—C3—H3	118.3
F3^iii—K1—B1^ii	118.89 (4)	C4—C3—H3	118.3
N1^iv—K1—B1^ii	96.70 (4)	K1^viii—C3—H3	69.8
F2^iii—K1—B1^ii	72.44 (4)	C3—C4—C5	118.24 (15)
B1^iii—K1—B1^ii	94.41 (4)	C3—C4—H4	120.9
C3^iv—K1—B1^ii	106.30 (4)	C5—C4—H4	120.9
F1—K1—K1^v	45.23 (3)	C4—C5—C1	120.57 (15)
F3^i—K1—K1^v	26.58 (2)	C4—C5—H5	119.7
F2^ii—K1—K1^v	119.40 (2)	C1—C5—H5	119.7
F3^iii—K1—K1^v	87.68 (2)	F1—B1—F2	108.17 (13)
N1^iv—K1—K1^v	116.13 (3)	F1—B1—F3	107.37 (14)
F2^iii—K1—K1^v	132.42 (2)	F2—B1—F3	105.33 (12)
B1^iii—K1—K1^v	108.31 (3)	F1—B1—C1	112.87 (13)
C3^iv—K1—K1^v	115.00 (3)	F2—B1—C1	111.94 (14)
B1^ii—K1—K1^v	135.62 (3)	F3—B1—C1	110.77 (13)
F1—K1—K1^i	97.60 (3)	F1—B1—K1^vii	135.40 (10)
F3^i—K1—K1^i	63.00 (2)	F2—B1—K1^vii	55.62 (7)
F2^ii—K1—K1^i	138.22 (3)	F3—B1—K1^vii	52.74 (7)
F3^iii—K1—K1^i	26.03 (2)	C1—B1—K1^vii	111.65 (10)
N1^iv—K1—K1^i	82.84 (3)	F1—B1—K1^vi	98.20 (10)
F2^iii—K1—K1^i	70.26 (2)	F2—B1—K1^vi	41.85 (7)
B1^iii—K1—K1^i	49.32 (3)	F3—B1—K1^vi	144.49 (11)
C3^iv—K1—K1^i	63.66 (3)	C1—B1—K1^vi	80.01 (9)
B1^ii—K1—K1^i	142.70 (3)	K1^vii—B1—K1^vi	91.75 (4)
K1^v—K1—K1^i	74.121 (10)
C3—N1—C2—C1	0.3 (2)	K1^vi—F2—B1—K1^vii	−145.02 (9)
K1^viii—N1—C2—C1	−176.81 (11)	K1^vii—F2—B1—K1^vi	145.02 (9)
C5—C1—C2—N1	−1.1 (2)	K1^v—F3—B1—F1	−21.59 (16)
B1—C1—C2—N1	173.35 (15)	K1^vii—F3—B1—F1	134.38 (10)
C2—N1—C3—C4	0.6 (2)	K1^v—F3—B1—F2	−136.71 (9)
K1^viii—N1—C3—C4	178.36 (14)	K1^vii—F3—B1—F2	19.25 (13)
C2—N1—C3—K1^viii	−177.75 (18)	K1^v—F3—B1—C1	102.07 (13)
N1—C3—C4—C5	−0.7 (3)	K1^vii—F3—B1—C1	−101.96 (12)
C3—C4—C5—C1	−0.1 (3)	K1^v—F3—B1—K1^vii	−155.97 (10)
C2—C1—C5—C4	0.9 (2)	K1^v—F3—B1—K1^vi	−155.68 (11)
B1—C1—C5—C4	−173.50 (16)	K1^vii—F3—B1—K1^vi	0.29 (19)
K1—F1—B1—F2	22.7 (2)	C2—C1—B1—F1	18.4 (2)
K1—F1—B1—F3	−90.55 (17)	C5—C1—B1—F1	−167.55 (15)
K1—F1—B1—C1	147.09 (11)	C2—C1—B1—F2	140.72 (15)
K1—F1—B1—K1^vii	−36.4 (2)	C5—C1—B1—F2	−45.2 (2)
K1—F1—B1—K1^vi	64.52 (14)	C2—C1—B1—F3	−102.06 (17)
K1^vi—F2—B1—F1	81.86 (14)	C5—C1—B1—F3	72.0 (2)
K1^vii—F2—B1—F1	−133.12 (11)	C2—C1—B1—K1^vii	−158.96 (12)
K1^vi—F2—B1—F3	−163.56 (8)	C5—C1—B1—K1^vii	15.11 (18)
K1^vii—F2—B1—F3	−18.54 (12)	C2—C1—B1—K1^vi	113.14 (14)
K1^vi—F2—B1—C1	−43.11 (16)	C5—C1—B1—K1^vi	−72.80 (14)
K1^vii—F2—B1—C1	101.91 (12)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) x−1, y, z; (iv) −x+1/2, −y+1, z−1/2; (v) x+1/2, −y+1/2, −z+1; (vi) x+1/2, −y+3/2, −z+1; (vii) x+1, y, z; (viii) −x+1/2, −y+1, z+1/2.

Potassium 4-(trifluoro-λ⁴-boranyl)pyridine monohydrate (2)

Crystal data

K^+·C5H4BF3N^−·H2O	F(000) = 408
Mr = 203.02	Dx = 1.656 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8271 (15) Å	Cell parameters from 8760 reflections
b = 8.5041 (11) Å	θ = 3.1–26.6°
c = 8.8435 (12) Å	µ = 0.65 mm^−1
β = 90.043 (5)°	T = 100 K
V = 814.26 (19) Å^3	Plate, colorless
Z = 4	0.17 × 0.17 × 0.07 mm

Data collection

Bruker PHOTON III CPAD diffractometer	1514 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.075
φ and ω scans	θmax = 26.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −13→13
Tmin = 0.579, Tmax = 0.745	k = −10→10
19163 measured reflections	l = −11→11
1723 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.6967P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
1723 reflections	Δρmax = 0.47 e Å^−3
158 parameters	Δρmin = −0.32 e Å^−3
176 restraints

Special details

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.

Refinement. Refined as a 2-component pseudo-merohedral twin. The ratio of twin components is approximately 45:55. The twin law relating the two domains is -1 0 0 0 1 0 0 0 1.

The reflection 1 0 0 was omitted due to suspected interference from the beam stop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
K1	0.05832 (4)	0.25194 (9)	0.50200 (10)	0.01522 (14)
O1	0.17804 (14)	0.11458 (19)	0.2496 (4)	0.0201 (4)
H1O	0.160 (3)	0.023 (3)	0.280 (5)	0.030*
H2O	0.255 (2)	0.115 (4)	0.239 (6)	0.030*
B1	0.1549 (6)	0.6075 (6)	0.2442 (7)	0.0163 (6)	0.5
F1	0.1103 (6)	0.7656 (6)	0.2363 (6)	0.0163 (3)	0.5
F2	0.1082 (7)	0.5429 (6)	0.3822 (5)	0.0163 (3)	0.5
F3	0.1017 (6)	0.5257 (6)	0.1236 (5)	0.0163 (3)	0.5
C1	0.3039 (5)	0.6000 (7)	0.2376 (9)	0.0133 (6)	0.5
C2	0.3705 (4)	0.6666 (7)	0.3549 (5)	0.0182 (12)	0.5
H2	0.328417	0.710340	0.439243	0.022*	0.5
C3	0.4990 (5)	0.6697 (7)	0.3498 (6)	0.0195 (12)	0.5
H3	0.542111	0.718389	0.430847	0.023*	0.5
N1	0.5647 (3)	0.6078 (8)	0.2369 (6)	0.0189 (7)	0.5
C4	0.5017 (4)	0.5409 (6)	0.1241 (6)	0.0158 (11)	0.5
H4	0.546378	0.496042	0.042391	0.019*	0.5
C5	0.3732 (4)	0.5341 (6)	0.1213 (6)	0.0173 (12)	0.5
H5	0.332463	0.483904	0.039246	0.021*	0.5
B1'	0.1540 (6)	0.6129 (6)	0.2386 (8)	0.0163 (6)	0.5
F1'	0.1008 (5)	0.7661 (6)	0.2512 (7)	0.0163 (3)	0.5
F2'	0.1050 (6)	0.5249 (6)	0.3628 (5)	0.0163 (3)	0.5
F3'	0.1117 (6)	0.5439 (6)	0.1045 (5)	0.0163 (3)	0.5
C1'	0.3029 (5)	0.6245 (6)	0.2360 (8)	0.0133 (6)	0.5
C2'	0.3763 (4)	0.5140 (6)	0.3088 (7)	0.0208 (12)	0.5
H2'	0.338910	0.431080	0.364296	0.025*	0.5
C3'	0.5043 (4)	0.5242 (6)	0.3006 (7)	0.0207 (12)	0.5
H3'	0.552046	0.446093	0.350492	0.025*	0.5
N1'	0.5637 (3)	0.6380 (7)	0.2264 (8)	0.0189 (7)	0.5
C4'	0.4943 (4)	0.7444 (6)	0.1548 (6)	0.0185 (12)	0.5
H4'	0.534361	0.825625	0.099805	0.022*	0.5
C5'	0.3657 (4)	0.7413 (6)	0.1575 (6)	0.0171 (11)	0.5
H5'	0.320416	0.819899	0.104961	0.020*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0153 (2)	0.0117 (2)	0.0186 (2)	0.0003 (4)	−0.0028 (6)	0.00063 (18)
O1	0.0143 (7)	0.0169 (8)	0.0292 (10)	−0.0001 (6)	−0.0043 (15)	0.0017 (13)
B1	0.0140 (10)	0.0118 (11)	0.0232 (15)	0.0007 (9)	0.0000 (17)	−0.0008 (16)
F1	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
F2	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
F3	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
C1	0.0158 (10)	0.0098 (17)	0.0142 (14)	0.0008 (10)	−0.0015 (15)	−0.0037 (16)
C2	0.022 (3)	0.019 (3)	0.013 (3)	0.004 (2)	−0.001 (2)	−0.002 (2)
C3	0.022 (3)	0.014 (3)	0.021 (3)	0.000 (2)	−0.008 (2)	−0.004 (2)
N1	0.0150 (9)	0.013 (2)	0.0288 (18)	0.0005 (10)	−0.0004 (15)	0.0014 (15)
C4	0.017 (2)	0.016 (3)	0.015 (3)	0.001 (2)	0.005 (2)	0.000 (2)
C5	0.017 (2)	0.013 (3)	0.022 (3)	0.002 (2)	−0.003 (2)	−0.003 (2)
B1'	0.0140 (10)	0.0118 (11)	0.0232 (15)	0.0007 (9)	0.0000 (17)	−0.0008 (16)
F1'	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
F2'	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
F3'	0.0163 (5)	0.0114 (5)	0.0211 (6)	−0.0009 (3)	−0.0019 (8)	−0.0001 (6)
C1'	0.0158 (10)	0.0098 (17)	0.0142 (14)	0.0008 (10)	−0.0015 (15)	−0.0037 (16)
C2'	0.019 (2)	0.017 (3)	0.025 (3)	0.000 (2)	0.004 (2)	0.002 (2)
C3'	0.020 (2)	0.020 (3)	0.022 (3)	0.002 (2)	0.001 (2)	0.000 (2)
N1'	0.0150 (9)	0.013 (2)	0.0288 (18)	0.0005 (10)	−0.0004 (15)	0.0014 (15)
C4'	0.017 (2)	0.016 (3)	0.022 (3)	0.000 (2)	0.003 (2)	−0.001 (2)
C5'	0.016 (2)	0.016 (3)	0.019 (3)	0.002 (2)	−0.001 (2)	−0.001 (2)

Geometric parameters (Å, º)

K1—F3^i	2.636 (5)	C2—H2	0.9500
K1—F2'	2.675 (5)	C3—N1	1.335 (3)
K1—F2^ii	2.710 (6)	C3—H3	0.9500
K1—F3'^iii	2.721 (6)	N1—C4	1.335 (3)
K1—F3'^i	2.736 (5)	C4—C5	1.393 (4)
K1—F2	2.745 (5)	C4—H4	0.9500
K1—O1^i	2.786 (3)	C5—H5	0.9500
K1—F1'^ii	2.786 (6)	B1'—F3'	1.399 (5)
K1—F1^iii	2.790 (6)	B1'—F1'	1.428 (4)
K1—F3^iii	2.816 (6)	B1'—F2'	1.432 (5)
K1—F1'^iii	2.827 (7)	B1'—C1'	1.616 (4)
K1—O1	2.834 (3)	C1'—C2'	1.388 (4)
K1—H1O	2.98 (4)	C1'—C5'	1.390 (5)
O1—H1O	0.84 (3)	C2'—C3'	1.391 (4)
O1—H2O	0.84 (2)	C2'—H2'	0.9500
B1—F3	1.398 (5)	C3'—N1'	1.334 (3)
B1—F1	1.430 (4)	C3'—H3'	0.9500
B1—F2	1.431 (5)	N1'—C4'	1.335 (3)
B1—C1	1.616 (4)	C4'—C5'	1.393 (4)
C1—C2	1.385 (8)	C4'—H4'	0.9500
C1—C5	1.391 (8)	C5'—H5'	0.9500
C2—C3	1.392 (4)
F3^i—K1—F2^ii	122.73 (15)	F1—B1—C1	111.9 (4)
F3^i—K1—F3'^iii	71.29 (16)	F2—B1—C1	111.7 (4)
F2^ii—K1—F3'^iii	95.70 (12)	F3—B1—K1^v	54.0 (3)
F3^i—K1—F3'^i	4.97 (16)	F1—B1—K1^v	53.1 (3)
F2'—K1—F3'^i	155.6 (2)	F2—B1—K1^v	116.4 (3)
F2^ii—K1—F3'^i	127.39 (15)	C1—B1—K1^v	131.9 (4)
F3'^iii—K1—F3'^i	70.10 (19)	F3—B1—K1^ii	113.3 (3)
F3^i—K1—F2	158.4 (2)	F1—B1—K1^ii	58.5 (3)
F2^ii—K1—F2	72.34 (19)	F2—B1—K1^ii	48.6 (3)
F3^i—K1—O1^i	87.81 (13)	C1—B1—K1^ii	135.2 (4)
F2^ii—K1—O1^i	75.51 (12)	K1^v—B1—K1^ii	80.59 (13)
F2—K1—O1^i	81.06 (12)	B1—F1—K1^v	102.6 (4)
F3^i—K1—F1'^ii	75.01 (14)	B1—F1—K1^ii	97.1 (4)
F2^ii—K1—F1'^ii	47.73 (16)	K1^v—F1—K1^ii	100.70 (19)
F2—K1—F1'^ii	118.28 (17)	B1—F2—K1^ii	108.1 (3)
O1^i—K1—F1'^ii	72.19 (15)	B1—F2—K1	138.2 (3)
F3^i—K1—F1^iii	117.49 (14)	K1^ii—F2—K1	107.66 (19)
F2^ii—K1—F1^iii	79.85 (16)	B1—F3—K1^iv	146.1 (4)
F2—K1—F1^iii	78.44 (17)	B1—F3—K1^v	102.4 (3)
O1^i—K1—F1^iii	151.74 (12)	K1^iv—F3—K1^v	109.98 (19)
F3^i—K1—F3^iii	70.02 (19)	C2—C1—C5	116.0 (5)
F2^ii—K1—F3^iii	100.35 (17)	C2—C1—B1	118.4 (6)
F2—K1—F3^iii	125.77 (13)	C5—C1—B1	125.6 (6)
O1^i—K1—F3^iii	150.93 (12)	C1—C2—C3	120.2 (4)
F1^iii—K1—F3^iii	47.82 (12)	C1—C2—H2	119.9
F3^i—K1—F1'^iii	117.99 (19)	C3—C2—H2	119.9
F2^ii—K1—F1'^iii	82.35 (17)	N1—C3—C2	123.4 (3)
F2—K1—F1'^iii	77.05 (14)	N1—C3—H3	118.3
O1^i—K1—F1'^iii	152.67 (12)	C2—C3—H3	118.3
F1^iii—K1—F1'^iii	3.3 (2)	C3—N1—C4	117.0 (3)
F3^iii—K1—F1'^iii	48.88 (15)	N1—C4—C5	122.7 (3)
F3^i—K1—O1	82.57 (11)	N1—C4—H4	118.6
F2'—K1—O1	84.76 (12)	C5—C4—H4	118.6
F2^ii—K1—O1	150.20 (12)	C1—C5—C4	120.6 (4)
F3'^iii—K1—O1	76.65 (11)	C1—C5—H5	119.7
F3'^i—K1—O1	77.61 (11)	C4—C5—H5	119.7
F2—K1—O1	88.70 (12)	F3'—B1'—F1'	108.5 (4)
O1^i—K1—O1	125.05 (6)	F3'—B1'—F2'	108.0 (4)
F1'^ii—K1—O1	151.39 (12)	F1'—B1'—F2'	105.5 (4)
F1^iii—K1—O1	73.82 (13)	F3'—B1'—C1'	109.8 (4)
F3^iii—K1—O1	71.91 (12)	F1'—B1'—C1'	110.4 (4)
F1'^iii—K1—O1	70.88 (13)	F2'—B1'—C1'	114.4 (4)
F3^i—K1—H1O	67.5 (6)	K1^v—B1'—K1^ii	81.21 (13)
F2'—K1—H1O	101.2 (6)	K1^ii—F1'—K1^v	103.97 (19)
F2^ii—K1—H1O	156.5 (7)	B1'—F2'—K1	151.3 (3)
F3'^iii—K1—H1O	66.3 (6)	K1—F2'—K1^ii	105.48 (18)
F3'^i—K1—H1O	62.6 (6)	K1^v—F3'—K1^iv	109.90 (19)
F2—K1—H1O	105.2 (6)	C2'—C1'—C5'	115.8 (5)
O1^i—K1—H1O	127.7 (7)	C2'—C1'—B1'	121.5 (4)
F1'^ii—K1—H1O	135.3 (5)	C5'—C1'—B1'	122.6 (4)
F1^iii—K1—H1O	76.8 (7)	C1'—C2'—C3'	120.2 (4)
F3^iii—K1—H1O	61.4 (6)	C1'—C2'—H2'	119.9
F1'^iii—K1—H1O	74.4 (7)	C3'—C2'—H2'	119.9
O1—K1—H1O	16.5 (5)	N1'—C3'—C2'	123.5 (3)
K1^iv—O1—K1	103.79 (5)	N1'—C3'—H3'	118.3
K1^iv—O1—H1O	121 (3)	C2'—C3'—H3'	118.3
K1—O1—H1O	91 (3)	C3'—N1'—C4'	117.0 (3)
K1^iv—O1—H2O	112 (4)	N1'—C4'—C5'	122.8 (4)
K1—O1—H2O	123 (4)	N1'—C4'—H4'	118.6
H1O—O1—H2O	105 (3)	C5'—C4'—H4'	118.6
F3—B1—F1	106.9 (4)	C1'—C5'—C4'	120.7 (4)
F3—B1—F2	108.3 (4)	C1'—C5'—H5'	119.6
F1—B1—F2	106.4 (4)	C4'—C5'—H5'	119.6
F3—B1—C1	111.3 (5)
F3—B1—F1—K1^v	4.6 (4)	F3'—B1'—F1'—K1^ii	112.9 (4)
F2—B1—F1—K1^v	−111.0 (4)	F2'—B1'—F1'—K1^ii	−2.7 (5)
C1—B1—F1—K1^v	126.8 (4)	C1'—B1'—F1'—K1^ii	−126.7 (4)
K1^ii—B1—F1—K1^v	−102.7 (3)	K1^v—B1'—F1'—K1^ii	107.0 (3)
F3—B1—F1—K1^ii	107.3 (4)	F3'—B1'—F1'—K1^v	5.9 (4)
F2—B1—F1—K1^ii	−8.3 (4)	F2'—B1'—F1'—K1^v	−109.7 (4)
C1—B1—F1—K1^ii	−130.5 (5)	C1'—B1'—F1'—K1^v	126.3 (4)
K1^v—B1—F1—K1^ii	102.7 (3)	K1^ii—B1'—F1'—K1^v	−107.0 (3)
F3—B1—F2—K1^ii	−105.3 (4)	F3'—B1'—F2'—K1	47.8 (9)
F1—B1—F2—K1^ii	9.4 (5)	F1'—B1'—F2'—K1	163.6 (7)
C1—B1—F2—K1^ii	131.8 (4)	C1'—B1'—F2'—K1	−74.9 (8)
K1^v—B1—F2—K1^ii	−47.1 (3)	K1^v—B1'—F2'—K1	103.6 (7)
F3—B1—F2—K1	42.3 (7)	K1^ii—B1'—F2'—K1	161.1 (8)
F1—B1—F2—K1	156.9 (5)	F3'—B1'—F2'—K1^ii	−113.3 (4)
C1—B1—F2—K1	−80.7 (6)	F1'—B1'—F2'—K1^ii	2.6 (4)
K1^v—B1—F2—K1	100.4 (5)	C1'—B1'—F2'—K1^ii	124.0 (3)
K1^ii—B1—F2—K1	147.5 (6)	K1^v—B1'—F2'—K1^ii	−57.4 (3)
F1—B1—F3—K1^iv	−167.2 (6)	F1'—B1'—F3'—K1^v	−6.2 (4)
F2—B1—F3—K1^iv	−52.8 (8)	F2'—B1'—F3'—K1^v	107.7 (3)
C1—B1—F3—K1^iv	70.3 (8)	C1'—B1'—F3'—K1^v	−126.9 (3)
K1^v—B1—F3—K1^iv	−162.6 (8)	K1^ii—B1'—F3'—K1^v	49.1 (3)
K1^ii—B1—F3—K1^iv	−104.8 (6)	F1'—B1'—F3'—K1^iv	−148.2 (6)
F1—B1—F3—K1^v	−4.6 (4)	F2'—B1'—F3'—K1^iv	−34.3 (7)
F2—B1—F3—K1^v	109.8 (3)	C1'—B1'—F3'—K1^iv	91.1 (6)
C1—B1—F3—K1^v	−127.1 (3)	K1^v—B1'—F3'—K1^iv	−141.9 (6)
K1^ii—B1—F3—K1^v	57.8 (3)	K1^ii—B1'—F3'—K1^iv	−92.8 (5)
F3—B1—C1—C2	−175.8 (6)	F3'—B1'—C1'—C2'	−98.4 (7)
F1—B1—C1—C2	64.6 (7)	F1'—B1'—C1'—C2'	142.0 (7)
F2—B1—C1—C2	−54.6 (6)	F2'—B1'—C1'—C2'	23.2 (7)
K1^v—B1—C1—C2	124.1 (6)	K1^v—B1'—C1'—C2'	−155.0 (5)
K1^ii—B1—C1—C2	−2.1 (7)	K1^ii—B1'—C1'—C2'	86.1 (7)
F3—B1—C1—C5	5.5 (7)	F3'—B1'—C1'—C5'	79.3 (7)
F1—B1—C1—C5	−114.1 (6)	F1'—B1'—C1'—C5'	−40.3 (8)
F2—B1—C1—C5	126.7 (6)	F2'—B1'—C1'—C5'	−159.0 (6)
K1^v—B1—C1—C5	−54.6 (7)	K1^v—B1'—C1'—C5'	22.8 (8)
K1^ii—B1—C1—C5	179.1 (5)	K1^ii—B1'—C1'—C5'	−96.1 (7)
C5—C1—C2—C3	2.1 (9)	C5'—C1'—C2'—C3'	0.1 (10)
B1—C1—C2—C3	−176.7 (5)	B1'—C1'—C2'—C3'	178.0 (6)
C1—C2—C3—N1	−1.5 (11)	C1'—C2'—C3'—N1'	0.8 (10)
C2—C3—N1—C4	0.4 (10)	C2'—C3'—N1'—C4'	−1.3 (11)
C3—N1—C4—C5	−0.1 (10)	C3'—N1'—C4'—C5'	1.0 (11)
C2—C1—C5—C4	−1.9 (9)	C2'—C1'—C5'—C4'	−0.3 (10)
B1—C1—C5—C4	176.9 (5)	B1'—C1'—C5'—C4'	−178.2 (5)
N1—C4—C5—C1	0.9 (10)	N1'—C4'—C5'—C1'	−0.2 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2O···N1a^vi	0.84 (2)	1.97 (3)	2.789 (4)	167 (5)
O1—H2O···N1′b^vi	0.84 (2)	2.00 (3)	2.811 (4)	164 (5)

Symmetry code: (vi) −x+1, y−1/2, −z+1/2.

Tetrabutylammonium 3-(trifluoro-λ⁴-boranyl)pyridine (3)

Crystal data

C16H36N^+·C5H4BF3N^−	F(000) = 848
Mr = 388.36	Dx = 1.123 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.4405 (7) Å	Cell parameters from 3752 reflections
b = 15.9663 (10) Å	θ = 2.5–23.7°
c = 15.4847 (11) Å	µ = 0.08 mm^−1
β = 100.159 (2)°	T = 100 K
V = 2297.4 (3) Å^3	Needle, colorless
Z = 4	0.32 × 0.06 × 0.06 mm

Data collection

Bruker PHOTON III CPAD diffractometer	3058 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.071
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
Tmin = 0.662, Tmax = 0.745	k = −19→19
23792 measured reflections	l = −18→18
4228 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0346P)^2 + 0.6405P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4228 reflections	Δρmax = 0.20 e Å^−3
248 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.88416 (12)	0.78406 (6)	0.89273 (7)	0.0376 (3)
F2	0.85524 (12)	0.86741 (9)	0.77248 (7)	0.0548 (4)
F3	0.85042 (11)	0.92405 (7)	0.90785 (8)	0.0431 (3)
N1	1.31027 (17)	0.84681 (10)	0.81989 (10)	0.0351 (4)
C1	1.08801 (18)	0.87906 (10)	0.87342 (10)	0.0228 (4)
C2	1.1697 (2)	0.83722 (11)	0.82018 (12)	0.0306 (4)
H2	1.120207	0.797726	0.779878	0.037*
C3	1.3785 (2)	0.90266 (12)	0.87700 (12)	0.0331 (5)
H3	1.478360	0.911692	0.878312	0.040*
C4	1.3111 (2)	0.94767 (11)	0.93398 (12)	0.0297 (4)
H4	1.363945	0.986189	0.974048	0.036*
C5	1.16515 (19)	0.93592 (10)	0.93196 (11)	0.0253 (4)
H5	1.117347	0.966800	0.970723	0.030*
B1	0.9169 (2)	0.86348 (13)	0.86199 (13)	0.0285 (5)
N2	0.51952 (14)	0.68985 (8)	0.67735 (9)	0.0206 (3)
C6	0.55876 (18)	0.78225 (10)	0.68569 (11)	0.0220 (4)
H6A	0.474443	0.813581	0.698623	0.026*
H6B	0.637523	0.789267	0.736596	0.026*
C7	0.60565 (19)	0.82169 (10)	0.60587 (11)	0.0255 (4)
H7A	0.539154	0.804631	0.551967	0.031*
H7B	0.703576	0.802241	0.601186	0.031*
C8	0.6048 (2)	0.91665 (11)	0.61495 (12)	0.0295 (4)
H8A	0.504107	0.936350	0.608656	0.035*
H8B	0.655184	0.932296	0.674348	0.035*
C9	0.6772 (2)	0.96014 (12)	0.54691 (13)	0.0378 (5)
H9A	0.668518	1.020958	0.552770	0.057*
H9B	0.630497	0.942896	0.488002	0.057*
H9C	0.779171	0.944601	0.556122	0.057*
C10	0.64301 (17)	0.63822 (10)	0.65451 (11)	0.0229 (4)
H10A	0.610801	0.579304	0.646126	0.027*
H10B	0.664522	0.658442	0.597781	0.027*
C11	0.78118 (18)	0.64010 (11)	0.72169 (11)	0.0254 (4)
H11A	0.761661	0.620686	0.779170	0.031*
H11B	0.817924	0.698225	0.728742	0.031*
C12	0.89374 (18)	0.58393 (11)	0.69219 (12)	0.0268 (4)
H12A	0.859015	0.525315	0.689066	0.032*
H12B	0.907044	0.600834	0.632627	0.032*
C13	1.03727 (19)	0.58868 (11)	0.75411 (13)	0.0325 (4)
H13A	1.104665	0.548847	0.735217	0.049*
H13B	1.023696	0.574717	0.813737	0.049*
H13C	1.076154	0.645532	0.753359	0.049*
C14	0.48417 (18)	0.66370 (10)	0.76532 (10)	0.0219 (4)
H14A	0.567004	0.678209	0.811552	0.026*
H14B	0.400865	0.697128	0.776374	0.026*
C15	0.44949 (19)	0.57175 (10)	0.77462 (11)	0.0238 (4)
H15A	0.532599	0.537181	0.765408	0.029*
H15B	0.365803	0.556096	0.729500	0.029*
C16	0.41552 (19)	0.55487 (10)	0.86562 (11)	0.0266 (4)
H16A	0.500845	0.568673	0.910331	0.032*
H16B	0.335559	0.591685	0.875558	0.032*
C17	0.3737 (2)	0.46395 (11)	0.87654 (12)	0.0322 (4)
H17A	0.356264	0.455080	0.936402	0.048*
H17B	0.451970	0.427263	0.865701	0.048*
H17C	0.286106	0.450956	0.834569	0.048*
C18	0.39153 (17)	0.67565 (10)	0.60365 (10)	0.0222 (4)
H18A	0.423999	0.684250	0.546899	0.027*
H18B	0.360832	0.616502	0.605745	0.027*
C19	0.26154 (18)	0.73134 (10)	0.60573 (11)	0.0252 (4)
H19A	0.283380	0.789286	0.589490	0.030*
H19B	0.239229	0.732379	0.665842	0.030*
C20	0.13183 (18)	0.69847 (11)	0.54184 (12)	0.0268 (4)
H20A	0.155765	0.696487	0.482144	0.032*
H20B	0.110519	0.640621	0.558674	0.032*
C21	−0.00164 (19)	0.75262 (11)	0.54028 (13)	0.0316 (4)
H21A	−0.083728	0.726695	0.502052	0.047*
H21B	0.015554	0.808440	0.517916	0.047*
H21C	−0.022531	0.757523	0.599858	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0421 (7)	0.0299 (6)	0.0443 (7)	−0.0100 (5)	0.0170 (5)	−0.0041 (5)
F2	0.0357 (7)	0.0923 (10)	0.0309 (6)	−0.0241 (7)	−0.0092 (5)	0.0119 (6)
F3	0.0295 (6)	0.0334 (6)	0.0674 (8)	0.0033 (5)	0.0113 (6)	−0.0060 (5)
N1	0.0321 (9)	0.0376 (9)	0.0363 (9)	0.0086 (7)	0.0082 (7)	0.0018 (7)
C1	0.0282 (10)	0.0190 (8)	0.0195 (9)	0.0005 (7)	0.0000 (7)	0.0029 (7)
C2	0.0337 (11)	0.0285 (10)	0.0282 (10)	0.0007 (8)	0.0019 (8)	−0.0043 (8)
C3	0.0236 (10)	0.0359 (11)	0.0382 (11)	0.0019 (8)	0.0010 (9)	0.0136 (9)
C4	0.0302 (11)	0.0248 (9)	0.0300 (10)	−0.0036 (8)	−0.0060 (8)	0.0046 (8)
C5	0.0301 (10)	0.0210 (9)	0.0234 (9)	0.0020 (8)	0.0010 (8)	0.0013 (7)
B1	0.0272 (11)	0.0305 (11)	0.0268 (11)	−0.0042 (9)	0.0019 (9)	−0.0004 (9)
N2	0.0174 (7)	0.0218 (7)	0.0218 (7)	0.0013 (6)	0.0014 (6)	−0.0020 (6)
C6	0.0201 (9)	0.0184 (8)	0.0262 (9)	0.0006 (7)	0.0003 (7)	−0.0028 (7)
C7	0.0216 (9)	0.0265 (9)	0.0281 (9)	0.0006 (7)	0.0037 (8)	0.0006 (7)
C8	0.0261 (10)	0.0272 (10)	0.0336 (10)	0.0014 (8)	0.0011 (8)	0.0029 (8)
C9	0.0320 (11)	0.0338 (11)	0.0476 (12)	−0.0006 (9)	0.0068 (9)	0.0100 (9)
C10	0.0201 (9)	0.0237 (9)	0.0250 (9)	0.0037 (7)	0.0044 (7)	−0.0026 (7)
C11	0.0196 (9)	0.0276 (9)	0.0279 (10)	0.0031 (7)	0.0009 (7)	−0.0024 (7)
C12	0.0209 (9)	0.0254 (9)	0.0334 (10)	0.0033 (8)	0.0027 (8)	−0.0013 (7)
C13	0.0214 (10)	0.0295 (10)	0.0449 (12)	0.0026 (8)	0.0015 (8)	0.0012 (8)
C14	0.0192 (9)	0.0269 (9)	0.0194 (9)	0.0009 (7)	0.0026 (7)	−0.0012 (7)
C15	0.0233 (9)	0.0232 (9)	0.0245 (9)	0.0008 (7)	0.0030 (7)	−0.0018 (7)
C16	0.0286 (10)	0.0261 (9)	0.0241 (9)	0.0040 (8)	0.0019 (8)	0.0004 (7)
C17	0.0366 (11)	0.0299 (10)	0.0302 (10)	0.0026 (8)	0.0062 (9)	0.0039 (8)
C18	0.0204 (9)	0.0239 (9)	0.0207 (9)	−0.0017 (7)	−0.0004 (7)	−0.0024 (7)
C19	0.0223 (9)	0.0245 (9)	0.0275 (10)	0.0001 (7)	0.0009 (8)	−0.0023 (7)
C20	0.0206 (9)	0.0271 (9)	0.0310 (10)	−0.0012 (7)	0.0000 (8)	−0.0026 (7)
C21	0.0243 (10)	0.0272 (10)	0.0397 (11)	0.0005 (8)	−0.0040 (8)	−0.0042 (8)

Geometric parameters (Å, º)

F1—B1	1.408 (2)	C11—C12	1.521 (2)
F2—B1	1.407 (2)	C11—H11A	0.9900
F3—B1	1.411 (2)	C11—H11B	0.9900
N1—C2	1.337 (2)	C12—C13	1.517 (2)
N1—C3	1.338 (2)	C12—H12A	0.9900
C1—C5	1.394 (2)	C12—H12B	0.9900
C1—C2	1.395 (2)	C13—H13A	0.9800
C1—B1	1.613 (3)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C3—C4	1.378 (3)	C14—C15	1.517 (2)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.386 (3)	C14—H14B	0.9900
C4—H4	0.9500	C15—C16	1.523 (2)
C5—H5	0.9500	C15—H15A	0.9900
N2—C14	1.517 (2)	C15—H15B	0.9900
N2—C10	1.520 (2)	C16—C17	1.521 (2)
N2—C6	1.521 (2)	C16—H16A	0.9900
N2—C18	1.526 (2)	C16—H16B	0.9900
C6—C7	1.521 (2)	C17—H17A	0.9800
C6—H6A	0.9900	C17—H17B	0.9800
C6—H6B	0.9900	C17—H17C	0.9800
C7—C8	1.523 (2)	C18—C19	1.520 (2)
C7—H7A	0.9900	C18—H18A	0.9900
C7—H7B	0.9900	C18—H18B	0.9900
C8—C9	1.521 (3)	C19—C20	1.525 (2)
C8—H8A	0.9900	C19—H19A	0.9900
C8—H8B	0.9900	C19—H19B	0.9900
C9—H9A	0.9800	C20—C21	1.525 (2)
C9—H9B	0.9800	C20—H20A	0.9900
C9—H9C	0.9800	C20—H20B	0.9900
C10—C11	1.519 (2)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800
C2—N1—C3	115.89 (16)	C12—C11—H11B	109.6
C5—C1—C2	114.61 (16)	H11A—C11—H11B	108.2
C5—C1—B1	124.75 (16)	C13—C12—C11	111.97 (14)
C2—C1—B1	120.58 (15)	C13—C12—H12A	109.2
N1—C2—C1	126.87 (17)	C11—C12—H12A	109.2
N1—C2—H2	116.6	C13—C12—H12B	109.2
C1—C2—H2	116.6	C11—C12—H12B	109.2
N1—C3—C4	123.21 (17)	H12A—C12—H12B	107.9
N1—C3—H3	118.4	C12—C13—H13A	109.5
C4—C3—H3	118.4	C12—C13—H13B	109.5
C3—C4—C5	119.00 (17)	H13A—C13—H13B	109.5
C3—C4—H4	120.5	C12—C13—H13C	109.5
C5—C4—H4	120.5	H13A—C13—H13C	109.5
C4—C5—C1	120.41 (17)	H13B—C13—H13C	109.5
C4—C5—H5	119.8	C15—C14—N2	115.91 (13)
C1—C5—H5	119.8	C15—C14—H14A	108.3
F2—B1—F1	107.22 (15)	N2—C14—H14A	108.3
F2—B1—F3	108.79 (16)	C15—C14—H14B	108.3
F1—B1—F3	107.69 (15)	N2—C14—H14B	108.3
F2—B1—C1	109.46 (15)	H14A—C14—H14B	107.4
F1—B1—C1	112.15 (15)	C14—C15—C16	110.08 (13)
F3—B1—C1	111.39 (15)	C14—C15—H15A	109.6
C14—N2—C10	111.04 (12)	C16—C15—H15A	109.6
C14—N2—C6	106.23 (12)	C14—C15—H15B	109.6
C10—N2—C6	111.14 (12)	C16—C15—H15B	109.6
C14—N2—C18	111.11 (12)	H15A—C15—H15B	108.2
C10—N2—C18	106.51 (12)	C17—C16—C15	111.88 (14)
C6—N2—C18	110.89 (12)	C17—C16—H16A	109.2
C7—C6—N2	115.73 (13)	C15—C16—H16A	109.2
C7—C6—H6A	108.3	C17—C16—H16B	109.2
N2—C6—H6A	108.3	C15—C16—H16B	109.2
C7—C6—H6B	108.3	H16A—C16—H16B	107.9
N2—C6—H6B	108.3	C16—C17—H17A	109.5
H6A—C6—H6B	107.4	C16—C17—H17B	109.5
C6—C7—C8	109.29 (14)	H17A—C17—H17B	109.5
C6—C7—H7A	109.8	C16—C17—H17C	109.5
C8—C7—H7A	109.8	H17A—C17—H17C	109.5
C6—C7—H7B	109.8	H17B—C17—H17C	109.5
C8—C7—H7B	109.8	C19—C18—N2	115.65 (13)
H7A—C7—H7B	108.3	C19—C18—H18A	108.4
C9—C8—C7	112.37 (15)	N2—C18—H18A	108.4
C9—C8—H8A	109.1	C19—C18—H18B	108.4
C7—C8—H8A	109.1	N2—C18—H18B	108.4
C9—C8—H8B	109.1	H18A—C18—H18B	107.4
C7—C8—H8B	109.1	C18—C19—C20	110.10 (13)
H8A—C8—H8B	107.9	C18—C19—H19A	109.6
C8—C9—H9A	109.5	C20—C19—H19A	109.6
C8—C9—H9B	109.5	C18—C19—H19B	109.6
H9A—C9—H9B	109.5	C20—C19—H19B	109.6
C8—C9—H9C	109.5	H19A—C19—H19B	108.2
H9A—C9—H9C	109.5	C21—C20—C19	112.45 (14)
H9B—C9—H9C	109.5	C21—C20—H20A	109.1
C11—C10—N2	115.55 (13)	C19—C20—H20A	109.1
C11—C10—H10A	108.4	C21—C20—H20B	109.1
N2—C10—H10A	108.4	C19—C20—H20B	109.1
C11—C10—H10B	108.4	H20A—C20—H20B	107.8
N2—C10—H10B	108.4	C20—C21—H21A	109.5
H10A—C10—H10B	107.5	C20—C21—H21B	109.5
C10—C11—C12	110.11 (14)	H21A—C21—H21B	109.5
C10—C11—H11A	109.6	C20—C21—H21C	109.5
C12—C11—H11A	109.6	H21A—C21—H21C	109.5
C10—C11—H11B	109.6	H21B—C21—H21C	109.5
C3—N1—C2—C1	0.0 (3)	N2—C6—C7—C8	166.00 (14)
C5—C1—C2—N1	−0.5 (3)	C6—C7—C8—C9	169.08 (14)
B1—C1—C2—N1	176.85 (17)	C14—N2—C10—C11	−56.39 (18)
C2—N1—C3—C4	0.7 (3)	C6—N2—C10—C11	61.63 (18)
N1—C3—C4—C5	−0.8 (3)	C18—N2—C10—C11	−177.49 (14)
C3—C4—C5—C1	0.3 (2)	N2—C10—C11—C12	178.21 (13)
C2—C1—C5—C4	0.3 (2)	C10—C11—C12—C13	175.89 (15)
B1—C1—C5—C4	−176.91 (16)	C10—N2—C14—C15	−55.74 (18)
C5—C1—B1—F2	130.15 (17)	C6—N2—C14—C15	−176.69 (13)
C2—C1—B1—F2	−46.9 (2)	C18—N2—C14—C15	62.61 (17)
C5—C1—B1—F1	−110.97 (18)	N2—C14—C15—C16	−179.67 (14)
C2—C1—B1—F1	72.0 (2)	C14—C15—C16—C17	177.55 (14)
C5—C1—B1—F3	9.8 (2)	C14—N2—C18—C19	67.62 (17)
C2—C1—B1—F3	−167.22 (15)	C10—N2—C18—C19	−171.33 (14)
C14—N2—C6—C7	177.19 (13)	C6—N2—C18—C19	−50.30 (18)
C10—N2—C6—C7	56.30 (17)	N2—C18—C19—C20	−167.65 (14)
C18—N2—C6—C7	−61.97 (17)	C18—C19—C20—C21	−179.29 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N1^i	0.99	2.69	3.550 (2)	146
C6—H6B···F2	0.99	2.38	3.188 (2)	138
C14—H14B···N1^i	0.99	2.66	3.528 (2)	146
C18—H18A···F1^ii	0.99	2.40	3.317 (2)	153

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, z−1/2.

Tetrakis[4-(dimethylamino)phenyl]phosphonium 4-(trifluoro-λ⁴-boranyl)pyridine (10)

Crystal data

C32H40N4P^+·C5H4BF3N^−	F(000) = 1392
Mr = 657.55	Dx = 1.271 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.9231 (9) Å	Cell parameters from 9959 reflections
b = 11.5958 (6) Å	θ = 2.2–25.4°
c = 18.7330 (12) Å	µ = 0.13 mm^−1
β = 96.696 (2)°	T = 100 K
V = 3435.3 (3) Å^3	Plate, colorless
Z = 4	0.34 × 0.25 × 0.04 mm

Data collection

Bruker PHOTON III CPAD diffractometer	4822 reflections with I > 2σ(I)
Radiation source: micro-focus	Rint = 0.060
φ and ω scans	θmax = 25.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −19→19
Tmin = 0.629, Tmax = 0.745	k = −13→14
52555 measured reflections	l = −21→22
6526 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 3.1705P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6526 reflections	Δρmax = 0.96 e Å^−3
525 parameters	Δρmin = −0.35 e Å^−3
367 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.54259 (3)	0.86531 (5)	0.65187 (3)	0.02679 (16)
N2	0.59659 (14)	0.61950 (18)	0.93419 (12)	0.0402 (5)
N3	0.71812 (13)	1.31256 (17)	0.62542 (12)	0.0383 (5)
N4	0.59700 (12)	0.54629 (19)	0.41080 (11)	0.0369 (5)
N5	0.19016 (13)	1.0540 (2)	0.63350 (12)	0.0438 (6)
C6	0.55979 (13)	0.79132 (19)	0.73548 (13)	0.0269 (5)
C7	0.60011 (13)	0.68346 (19)	0.74258 (13)	0.0294 (5)
H7	0.620071	0.649210	0.701679	0.035*
C8	0.61138 (14)	0.62622 (19)	0.80736 (13)	0.0314 (5)
H8	0.637616	0.552520	0.810064	0.038*
C9	0.58463 (14)	0.6752 (2)	0.86971 (13)	0.0303 (5)
C10	0.54519 (14)	0.7842 (2)	0.86282 (14)	0.0309 (5)
H10	0.527162	0.820116	0.904009	0.037*
C11	0.53241 (14)	0.8396 (2)	0.79745 (13)	0.0304 (5)
H11	0.504413	0.912038	0.794213	0.036*
C12	0.62369 (17)	0.4996 (2)	0.93774 (16)	0.0437 (7)
H12A	0.627795	0.472789	0.987631	0.066*
H12B	0.679085	0.492990	0.920141	0.066*
H12C	0.582441	0.452309	0.907827	0.066*
C13	0.56544 (19)	0.6698 (3)	0.99730 (16)	0.0504 (7)
H13A	0.581682	0.620649	1.039176	0.076*
H13B	0.503681	0.675992	0.989155	0.076*
H13C	0.589992	0.746772	1.006031	0.076*
C14	0.60959 (13)	0.98723 (19)	0.64734 (13)	0.0271 (5)
C15	0.62483 (13)	1.06193 (19)	0.70642 (13)	0.0286 (5)
H15	0.609248	1.039033	0.751761	0.034*
C16	0.66199 (14)	1.16775 (19)	0.69956 (14)	0.0304 (5)
H16	0.672001	1.216715	0.740326	0.036*
C17	0.68550 (13)	1.20480 (19)	0.63297 (14)	0.0307 (5)
C18	0.67379 (14)	1.1272 (2)	0.57471 (14)	0.0323 (5)
H18	0.692248	1.147834	0.530000	0.039*
C19	0.63570 (14)	1.0215 (2)	0.58206 (13)	0.0301 (5)
H19	0.627129	0.971160	0.541858	0.036*
C20	0.72313 (16)	1.3939 (2)	0.68497 (16)	0.0424 (7)
H20A	0.743695	1.468343	0.669416	0.064*
H20B	0.762164	1.364181	0.725077	0.064*
H20C	0.666896	1.403779	0.700501	0.064*
C21	0.74206 (16)	1.3507 (2)	0.55692 (16)	0.0424 (7)
H21A	0.772125	1.424433	0.563310	0.064*
H21B	0.691202	1.360551	0.522620	0.064*
H21C	0.779045	1.293033	0.538536	0.064*
C22	0.55920 (13)	0.77061 (19)	0.58036 (13)	0.0275 (5)
C23	0.64071 (14)	0.73373 (19)	0.56963 (13)	0.0295 (5)
H23	0.687839	0.759584	0.601370	0.035*
C24	0.65363 (14)	0.66091 (19)	0.51407 (13)	0.0293 (5)
H24	0.709470	0.637042	0.508142	0.035*
C25	0.58500 (14)	0.62094 (19)	0.46555 (13)	0.0289 (5)
C26	0.50377 (14)	0.6600 (2)	0.47598 (13)	0.0322 (5)
H26	0.456464	0.636028	0.443796	0.039*
C27	0.49162 (14)	0.7325 (2)	0.53200 (13)	0.0307 (5)
H27	0.435954	0.757135	0.537898	0.037*
C28	0.68053 (16)	0.5234 (2)	0.39124 (15)	0.0401 (6)
H28A	0.679101	0.453520	0.361731	0.060*
H28B	0.720072	0.512449	0.434865	0.060*
H28C	0.699084	0.588812	0.363866	0.060*
C29	0.52574 (17)	0.5162 (3)	0.35836 (15)	0.0440 (7)
H29A	0.543423	0.457950	0.325294	0.066*
H29B	0.505976	0.585219	0.331191	0.066*
H29C	0.479805	0.485304	0.383230	0.066*
C30	0.43606 (14)	0.9172 (2)	0.64250 (13)	0.0285 (5)
C31	0.37014 (14)	0.8531 (2)	0.66544 (14)	0.0346 (6)
H31	0.381482	0.777946	0.684405	0.042*
C32	0.28892 (15)	0.8959 (2)	0.66131 (14)	0.0380 (6)
H32	0.245241	0.849496	0.676687	0.046*
C33	0.26989 (15)	1.0080 (2)	0.63444 (13)	0.0349 (6)
C34	0.33579 (15)	1.0707 (2)	0.60904 (14)	0.0348 (6)
H34	0.324418	1.144720	0.588453	0.042*
C35	0.41692 (15)	1.0266 (2)	0.61344 (13)	0.0317 (5)
H35	0.460438	1.071319	0.596426	0.038*
C36	0.13085 (17)	1.0003 (3)	0.67635 (17)	0.0616 (9)
H36A	0.077550	1.043417	0.670705	0.092*
H36B	0.154527	1.000604	0.727044	0.092*
H36C	0.120370	0.920636	0.660285	0.092*
C37	0.17988 (19)	1.1785 (3)	0.62189 (19)	0.0597 (9)
H37A	0.121110	1.200271	0.625764	0.090*
H37B	0.194170	1.198370	0.573908	0.090*
H37C	0.217494	1.220158	0.658247	0.090*
B1	0.6218 (4)	0.1975 (7)	0.8905 (4)	0.0374 (10)	0.332 (3)
F1	0.6397 (6)	0.2910 (7)	0.8485 (6)	0.056 (3)	0.332 (3)
F2	0.6755 (7)	0.1072 (9)	0.8794 (7)	0.0489 (12)	0.332 (3)
F3	0.6337 (7)	0.2281 (10)	0.9626 (5)	0.038 (2)	0.332 (3)
C1	0.5233 (5)	0.1546 (13)	0.8705 (7)	0.0382 (12)	0.332 (3)
C2	0.4864 (6)	0.0732 (11)	0.9130 (6)	0.0555 (15)	0.332 (3)
H2	0.518486	0.042875	0.954704	0.067*	0.332 (3)
C3	0.4047 (7)	0.0369 (17)	0.8949 (9)	0.0767 (18)	0.332 (3)
H3	0.381921	−0.016927	0.925698	0.092*	0.332 (3)
N1	0.3542 (6)	0.0732 (15)	0.8356 (8)	0.0851 (19)	0.332 (3)
C4	0.3871 (5)	0.1599 (11)	0.7990 (7)	0.0711 (17)	0.332 (3)
H4	0.350777	0.198584	0.762860	0.085*	0.332 (3)
C5	0.4701 (5)	0.1951 (11)	0.8111 (6)	0.0542 (16)	0.332 (3)
H5	0.491597	0.247531	0.778755	0.065*	0.332 (3)
B1'	0.6182 (5)	0.1440 (6)	0.9235 (4)	0.0374 (10)	0.235 (2)
F1'	0.6364 (5)	0.0858 (9)	0.9882 (4)	0.092 (3)	0.235 (2)
F2'	0.6685 (8)	0.1036 (12)	0.8738 (6)	0.0489 (12)	0.235 (2)
F3'	0.6339 (9)	0.2604 (7)	0.9357 (8)	0.099 (6)	0.235 (2)
C1'	0.5179 (5)	0.1247 (10)	0.8931 (5)	0.0382 (12)	0.235 (2)
C2'	0.4662 (6)	0.0480 (13)	0.9263 (7)	0.0555 (15)	0.235 (2)
H2'	0.487838	0.010872	0.969767	0.067*	0.235 (2)
C3'	0.3848 (9)	0.026 (2)	0.8966 (13)	0.0767 (18)	0.235 (2)
H3'	0.354294	−0.033517	0.916792	0.092*	0.235 (2)
N1'	0.3457 (7)	0.086 (2)	0.8396 (12)	0.0851 (19)	0.235 (2)
C4'	0.4002 (7)	0.1401 (16)	0.8000 (8)	0.0711 (17)	0.235 (2)
H4'	0.382378	0.155921	0.750782	0.085*	0.235 (2)
C5'	0.4804 (7)	0.1726 (16)	0.8284 (7)	0.0542 (16)	0.235 (2)
H5'	0.510536	0.227890	0.803972	0.065*	0.235 (2)
B1''	0.6152 (3)	0.1767 (5)	0.8979 (4)	0.0374 (10)	0.433 (2)
F1''	0.6547 (6)	0.0728 (6)	0.8901 (6)	0.107 (4)	0.433 (2)
F2''	0.6176 (7)	0.2022 (10)	0.9704 (4)	0.080 (4)	0.433 (2)
F3''	0.6564 (5)	0.2636 (7)	0.8642 (6)	0.074 (2)	0.433 (2)
C1''	0.5163 (4)	0.1717 (10)	0.8603 (6)	0.0382 (12)	0.433 (2)
C2''	0.4580 (4)	0.0929 (7)	0.8828 (5)	0.0555 (15)	0.433 (2)
H2''	0.474887	0.043463	0.922309	0.067*	0.433 (2)
C3''	0.3770 (4)	0.0859 (10)	0.8488 (6)	0.0767 (18)	0.433 (2)
H3''	0.339932	0.030923	0.866026	0.092*	0.433 (2)
N1''	0.3466 (4)	0.1527 (7)	0.7923 (4)	0.0851 (19)	0.433 (2)
C4''	0.4036 (4)	0.2273 (7)	0.7691 (4)	0.0711 (17)	0.433 (2)
H4''	0.385490	0.275011	0.729014	0.085*	0.433 (2)
C5''	0.4858 (4)	0.2379 (9)	0.8003 (5)	0.0542 (16)	0.433 (2)
H5''	0.522451	0.290946	0.780783	0.065*	0.433 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0211 (3)	0.0214 (3)	0.0372 (4)	0.0012 (2)	0.0006 (2)	−0.0018 (2)
N2	0.0442 (12)	0.0344 (12)	0.0418 (13)	0.0027 (10)	0.0038 (10)	0.0068 (10)
N3	0.0353 (11)	0.0249 (11)	0.0539 (15)	−0.0035 (9)	0.0018 (10)	0.0057 (10)
N4	0.0311 (11)	0.0413 (12)	0.0382 (13)	−0.0041 (9)	0.0036 (9)	−0.0112 (10)
N5	0.0283 (11)	0.0612 (15)	0.0415 (14)	0.0179 (10)	0.0029 (10)	−0.0003 (11)
C6	0.0198 (10)	0.0224 (11)	0.0380 (14)	−0.0017 (8)	0.0019 (9)	−0.0030 (9)
C7	0.0222 (11)	0.0247 (12)	0.0399 (15)	−0.0001 (9)	−0.0026 (10)	−0.0052 (10)
C8	0.0273 (11)	0.0205 (11)	0.0443 (15)	0.0011 (9)	−0.0051 (10)	−0.0014 (10)
C9	0.0228 (11)	0.0279 (12)	0.0393 (15)	−0.0048 (9)	−0.0001 (10)	0.0014 (10)
C10	0.0264 (11)	0.0271 (12)	0.0396 (15)	−0.0031 (9)	0.0050 (10)	−0.0025 (10)
C11	0.0242 (11)	0.0242 (12)	0.0425 (15)	−0.0006 (9)	0.0032 (10)	−0.0010 (10)
C12	0.0385 (14)	0.0347 (15)	0.0572 (19)	−0.0020 (11)	0.0022 (13)	0.0136 (13)
C13	0.0501 (17)	0.0575 (18)	0.0453 (18)	0.0068 (14)	0.0124 (14)	0.0118 (14)
C14	0.0213 (10)	0.0228 (11)	0.0365 (14)	0.0038 (8)	0.0010 (9)	0.0000 (9)
C15	0.0235 (11)	0.0259 (12)	0.0359 (14)	0.0014 (9)	0.0015 (10)	−0.0002 (10)
C16	0.0255 (11)	0.0233 (12)	0.0416 (15)	−0.0005 (9)	0.0011 (10)	−0.0029 (10)
C17	0.0189 (10)	0.0234 (12)	0.0487 (16)	0.0018 (8)	−0.0009 (10)	0.0029 (10)
C18	0.0255 (11)	0.0314 (13)	0.0399 (15)	0.0030 (10)	0.0034 (10)	0.0061 (11)
C19	0.0259 (11)	0.0268 (12)	0.0370 (14)	0.0024 (9)	0.0012 (10)	−0.0008 (10)
C20	0.0343 (13)	0.0250 (13)	0.066 (2)	−0.0035 (10)	−0.0029 (13)	−0.0006 (12)
C21	0.0309 (13)	0.0323 (14)	0.0623 (19)	−0.0040 (10)	−0.0015 (12)	0.0137 (12)
C22	0.0230 (11)	0.0230 (11)	0.0357 (14)	0.0011 (9)	0.0004 (9)	−0.0010 (9)
C23	0.0232 (11)	0.0261 (12)	0.0375 (14)	−0.0002 (9)	−0.0032 (10)	−0.0021 (10)
C24	0.0228 (11)	0.0280 (12)	0.0366 (14)	0.0021 (9)	0.0010 (10)	−0.0016 (10)
C25	0.0299 (12)	0.0266 (12)	0.0294 (13)	−0.0014 (9)	0.0004 (10)	−0.0003 (10)
C26	0.0257 (11)	0.0327 (13)	0.0364 (14)	−0.0038 (9)	−0.0042 (10)	−0.0042 (10)
C27	0.0215 (11)	0.0309 (13)	0.0389 (14)	0.0016 (9)	−0.0004 (10)	0.0002 (10)
C28	0.0410 (14)	0.0420 (15)	0.0377 (15)	0.0043 (11)	0.0059 (12)	−0.0057 (12)
C29	0.0431 (15)	0.0499 (16)	0.0383 (16)	−0.0107 (12)	0.0014 (12)	−0.0111 (13)
C30	0.0233 (11)	0.0266 (12)	0.0352 (14)	0.0031 (9)	0.0020 (10)	−0.0030 (10)
C31	0.0268 (12)	0.0334 (13)	0.0432 (15)	0.0017 (10)	0.0023 (11)	0.0028 (11)
C32	0.0243 (12)	0.0476 (16)	0.0417 (16)	0.0011 (10)	0.0024 (11)	0.0027 (12)
C33	0.0262 (12)	0.0477 (15)	0.0297 (14)	0.0094 (11)	−0.0014 (10)	−0.0044 (11)
C34	0.0338 (13)	0.0321 (13)	0.0376 (15)	0.0100 (10)	0.0008 (11)	−0.0004 (11)
C35	0.0287 (12)	0.0314 (13)	0.0348 (14)	0.0029 (10)	0.0031 (10)	−0.0004 (10)
C36	0.0303 (14)	0.104 (3)	0.0516 (19)	0.0202 (16)	0.0073 (13)	0.0041 (18)
C37	0.0433 (16)	0.065 (2)	0.070 (2)	0.0302 (15)	−0.0004 (15)	−0.0025 (17)
B1	0.0224 (15)	0.043 (2)	0.045 (2)	0.0019 (15)	−0.0035 (16)	−0.0317 (18)
F1	0.085 (7)	0.030 (3)	0.056 (5)	−0.006 (3)	0.018 (4)	−0.020 (3)
F2	0.032 (2)	0.056 (2)	0.055 (3)	0.0152 (19)	−0.0091 (19)	−0.022 (2)
F3	0.038 (4)	0.032 (4)	0.039 (3)	0.009 (4)	−0.011 (3)	−0.016 (3)
C1	0.0357 (17)	0.034 (4)	0.045 (4)	0.008 (2)	0.0041 (18)	−0.013 (2)
C2	0.056 (3)	0.051 (4)	0.064 (5)	−0.004 (3)	0.023 (3)	−0.011 (3)
C3	0.044 (4)	0.083 (5)	0.107 (6)	−0.016 (4)	0.027 (4)	−0.041 (3)
N1	0.040 (2)	0.124 (5)	0.091 (4)	−0.009 (3)	0.005 (3)	−0.055 (3)
C4	0.046 (3)	0.087 (5)	0.077 (4)	0.028 (3)	−0.009 (3)	−0.036 (3)
C5	0.041 (2)	0.068 (6)	0.054 (4)	0.017 (3)	0.004 (2)	−0.003 (3)
B1'	0.0224 (15)	0.043 (2)	0.045 (2)	0.0019 (15)	−0.0035 (16)	−0.0317 (18)
F1'	0.072 (6)	0.122 (8)	0.082 (5)	−0.009 (6)	0.003 (4)	0.021 (5)
F2'	0.032 (2)	0.056 (2)	0.055 (3)	0.0152 (19)	−0.0091 (19)	−0.022 (2)
F3'	0.069 (8)	0.055 (4)	0.167 (16)	0.006 (5)	−0.016 (11)	−0.036 (7)
C1'	0.0357 (17)	0.034 (4)	0.045 (4)	0.008 (2)	0.0041 (18)	−0.013 (2)
C2'	0.056 (3)	0.051 (4)	0.064 (5)	−0.004 (3)	0.023 (3)	−0.011 (3)
C3'	0.044 (4)	0.083 (5)	0.107 (6)	−0.016 (4)	0.027 (4)	−0.041 (3)
N1'	0.040 (2)	0.124 (5)	0.091 (4)	−0.009 (3)	0.005 (3)	−0.055 (3)
C4'	0.046 (3)	0.087 (5)	0.077 (4)	0.028 (3)	−0.009 (3)	−0.036 (3)
C5'	0.041 (2)	0.068 (6)	0.054 (4)	0.017 (3)	0.004 (2)	−0.003 (3)
B1''	0.0224 (15)	0.043 (2)	0.045 (2)	0.0019 (15)	−0.0035 (16)	−0.0317 (18)
F1''	0.114 (8)	0.080 (5)	0.113 (8)	0.057 (5)	−0.052 (6)	−0.038 (5)
F2''	0.094 (7)	0.092 (8)	0.051 (3)	0.015 (5)	−0.010 (3)	−0.017 (4)
F3''	0.039 (3)	0.092 (6)	0.092 (6)	−0.018 (3)	0.011 (3)	−0.027 (4)
C1''	0.0357 (17)	0.034 (4)	0.045 (4)	0.008 (2)	0.0041 (18)	−0.013 (2)
C2''	0.056 (3)	0.051 (4)	0.064 (5)	−0.004 (3)	0.023 (3)	−0.011 (3)
C3''	0.044 (4)	0.083 (5)	0.107 (6)	−0.016 (4)	0.027 (4)	−0.041 (3)
N1''	0.040 (2)	0.124 (5)	0.091 (4)	−0.009 (3)	0.005 (3)	−0.055 (3)
C4''	0.046 (3)	0.087 (5)	0.077 (4)	0.028 (3)	−0.009 (3)	−0.036 (3)
C5''	0.041 (2)	0.068 (6)	0.054 (4)	0.017 (3)	0.004 (2)	−0.003 (3)

Geometric parameters (Å, º)

P1—C22	1.776 (2)	C29—H29A	0.9800
P1—C6	1.779 (2)	C29—H29B	0.9800
P1—C14	1.779 (2)	C29—H29C	0.9800
P1—C30	1.789 (2)	C30—C31	1.395 (3)
N2—C9	1.363 (3)	C30—C35	1.399 (3)
N2—C12	1.455 (3)	C31—C32	1.379 (3)
N2—C13	1.457 (4)	C31—H31	0.9500
N3—C17	1.367 (3)	C32—C33	1.414 (4)
N3—C21	1.450 (3)	C32—H32	0.9500
N3—C20	1.456 (3)	C33—C34	1.404 (4)
N4—C25	1.372 (3)	C34—C35	1.383 (3)
N4—C28	1.445 (3)	C34—H34	0.9500
N4—C29	1.454 (3)	C35—H35	0.9500
N5—C33	1.375 (3)	C36—H36A	0.9800
N5—C36	1.449 (4)	C36—H36B	0.9800
N5—C37	1.467 (4)	C36—H36C	0.9800
C6—C11	1.403 (3)	C37—H37A	0.9800
C6—C7	1.405 (3)	C37—H37B	0.9800
C7—C8	1.377 (3)	C37—H37C	0.9800
C7—H7	0.9500	B1—F2	1.382 (4)
C8—C9	1.408 (3)	B1—F3	1.387 (4)
C8—H8	0.9500	B1—F1	1.389 (4)
C9—C10	1.411 (3)	B1—C1	1.647 (5)
C10—C11	1.376 (3)	C1—C5	1.398 (5)
C10—H10	0.9500	C1—C2	1.406 (5)
C11—H11	0.9500	C2—C3	1.372 (6)
C12—H12A	0.9800	C2—H2	0.9500
C12—H12B	0.9800	C3—N1	1.359 (7)
C12—H12C	0.9800	C3—H3	0.9500
C13—H13A	0.9800	N1—C4	1.356 (6)
C13—H13B	0.9800	C4—C5	1.377 (6)
C13—H13C	0.9800	C4—H4	0.9500
C14—C19	1.395 (3)	C5—H5	0.9500
C14—C15	1.404 (3)	B1'—F2'	1.380 (4)
C15—C16	1.375 (3)	B1'—F3'	1.386 (4)
C15—H15	0.9500	B1'—F1'	1.388 (4)
C16—C17	1.411 (4)	B1'—C1'	1.648 (5)
C16—H16	0.9500	C1'—C5'	1.401 (5)
C17—C18	1.410 (3)	C1'—C2'	1.405 (5)
C18—C19	1.382 (3)	C2'—C3'	1.373 (6)
C18—H18	0.9500	C2'—H2'	0.9500
C19—H19	0.9500	C3'—N1'	1.362 (7)
C20—H20A	0.9800	C3'—H3'	0.9500
C20—H20B	0.9800	N1'—C4'	1.359 (7)
C20—H20C	0.9800	C4'—C5'	1.377 (6)
C21—H21A	0.9800	C4'—H4'	0.9500
C21—H21B	0.9800	C5'—H5'	0.9500
C21—H21C	0.9800	B1''—F1''	1.375 (4)
C22—C27	1.395 (3)	B1''—F2''	1.385 (4)
C22—C23	1.403 (3)	B1''—F3''	1.394 (4)
C23—C24	1.374 (3)	B1''—C1''	1.649 (5)
C23—H23	0.9500	C1''—C5''	1.401 (5)
C24—C25	1.416 (3)	C1''—C2''	1.402 (5)
C24—H24	0.9500	C2''—C3''	1.373 (6)
C25—C26	1.406 (3)	C2''—H2''	0.9500
C26—C27	1.375 (3)	C3''—N1''	1.355 (6)
C26—H26	0.9500	C3''—H3''	0.9500
C27—H27	0.9500	N1''—C4''	1.361 (6)
C28—H28A	0.9800	C4''—C5''	1.375 (5)
C28—H28B	0.9800	C4''—H4''	0.9500
C28—H28C	0.9800	C5''—H5''	0.9500
C22—P1—C6	110.17 (11)	N4—C29—H29A	109.5
C22—P1—C14	108.22 (11)	N4—C29—H29B	109.5
C6—P1—C14	113.17 (11)	H29A—C29—H29B	109.5
C22—P1—C30	110.91 (11)	N4—C29—H29C	109.5
C6—P1—C30	107.19 (11)	H29A—C29—H29C	109.5
C14—P1—C30	107.16 (10)	H29B—C29—H29C	109.5
C9—N2—C12	120.2 (2)	C31—C30—C35	117.7 (2)
C9—N2—C13	120.2 (2)	C31—C30—P1	121.96 (18)
C12—N2—C13	118.2 (2)	C35—C30—P1	120.27 (18)
C17—N3—C21	120.9 (2)	C32—C31—C30	121.7 (2)
C17—N3—C20	120.0 (2)	C32—C31—H31	119.2
C21—N3—C20	118.9 (2)	C30—C31—H31	119.2
C25—N4—C28	121.2 (2)	C31—C32—C33	120.8 (2)
C25—N4—C29	119.4 (2)	C31—C32—H32	119.6
C28—N4—C29	117.0 (2)	C33—C32—H32	119.6
C33—N5—C36	119.1 (2)	N5—C33—C34	121.3 (2)
C33—N5—C37	118.1 (2)	N5—C33—C32	121.3 (2)
C36—N5—C37	115.9 (2)	C34—C33—C32	117.3 (2)
C11—C6—C7	117.3 (2)	C35—C34—C33	121.2 (2)
C11—C6—P1	120.36 (17)	C35—C34—H34	119.4
C7—C6—P1	122.30 (18)	C33—C34—H34	119.4
C8—C7—C6	121.6 (2)	C34—C35—C30	121.2 (2)
C8—C7—H7	119.2	C34—C35—H35	119.4
C6—C7—H7	119.2	C30—C35—H35	119.4
C7—C8—C9	121.1 (2)	N5—C36—H36A	109.5
C7—C8—H8	119.5	N5—C36—H36B	109.5
C9—C8—H8	119.5	H36A—C36—H36B	109.5
N2—C9—C8	121.3 (2)	N5—C36—H36C	109.5
N2—C9—C10	121.3 (2)	H36A—C36—H36C	109.5
C8—C9—C10	117.4 (2)	H36B—C36—H36C	109.5
C11—C10—C9	121.1 (2)	N5—C37—H37A	109.5
C11—C10—H10	119.4	N5—C37—H37B	109.5
C9—C10—H10	119.4	H37A—C37—H37B	109.5
C10—C11—C6	121.5 (2)	N5—C37—H37C	109.5
C10—C11—H11	119.3	H37A—C37—H37C	109.5
C6—C11—H11	119.3	H37B—C37—H37C	109.5
N2—C12—H12A	109.5	F2—B1—F3	108.9 (4)
N2—C12—H12B	109.5	F2—B1—F1	109.6 (5)
H12A—C12—H12B	109.5	F3—B1—F1	109.8 (4)
N2—C12—H12C	109.5	F2—B1—C1	109.0 (6)
H12A—C12—H12C	109.5	F3—B1—C1	108.4 (5)
H12B—C12—H12C	109.5	F1—B1—C1	111.1 (5)
N2—C13—H13A	109.5	C5—C1—C2	115.0 (5)
N2—C13—H13B	109.5	C5—C1—B1	123.4 (4)
H13A—C13—H13B	109.5	C2—C1—B1	121.6 (3)
N2—C13—H13C	109.5	C3—C2—C1	120.8 (6)
H13A—C13—H13C	109.5	C3—C2—H2	119.6
H13B—C13—H13C	109.5	C1—C2—H2	119.6
C19—C14—C15	118.3 (2)	N1—C3—C2	124.1 (6)
C19—C14—P1	120.66 (18)	N1—C3—H3	118.0
C15—C14—P1	120.14 (18)	C2—C3—H3	118.0
C16—C15—C14	120.9 (2)	C4—N1—C3	114.6 (6)
C16—C15—H15	119.5	N1—C4—C5	123.8 (6)
C14—C15—H15	119.5	N1—C4—H4	118.1
C15—C16—C17	121.1 (2)	C5—C4—H4	118.1
C15—C16—H16	119.5	C4—C5—C1	120.8 (6)
C17—C16—H16	119.5	C4—C5—H5	119.6
N3—C17—C18	121.4 (2)	C1—C5—H5	119.6
N3—C17—C16	120.9 (2)	F2'—B1'—F3'	109.5 (5)
C18—C17—C16	117.7 (2)	F2'—B1'—F1'	110.2 (5)
C19—C18—C17	120.6 (2)	F3'—B1'—F1'	108.3 (5)
C19—C18—H18	119.7	F2'—B1'—C1'	109.6 (6)
C17—C18—H18	119.7	F3'—B1'—C1'	109.7 (6)
C18—C19—C14	121.3 (2)	F1'—B1'—C1'	109.4 (5)
C18—C19—H19	119.4	C5'—C1'—C2'	114.9 (5)
C14—C19—H19	119.4	C5'—C1'—B1'	122.9 (4)
N3—C20—H20A	109.5	C2'—C1'—B1'	121.8 (4)
N3—C20—H20B	109.5	C3'—C2'—C1'	120.7 (6)
H20A—C20—H20B	109.5	C3'—C2'—H2'	119.6
N3—C20—H20C	109.5	C1'—C2'—H2'	119.6
H20A—C20—H20C	109.5	N1'—C3'—C2'	123.2 (7)
H20B—C20—H20C	109.5	N1'—C3'—H3'	118.4
N3—C21—H21A	109.5	C2'—C3'—H3'	118.4
N3—C21—H21B	109.5	C4'—N1'—C3'	113.5 (7)
H21A—C21—H21B	109.5	N1'—C4'—C5'	122.5 (7)
N3—C21—H21C	109.5	N1'—C4'—H4'	118.8
H21A—C21—H21C	109.5	C5'—C4'—H4'	118.8
H21B—C21—H21C	109.5	C4'—C5'—C1'	120.5 (6)
C27—C22—C23	117.8 (2)	C4'—C5'—H5'	119.7
C27—C22—P1	120.95 (17)	C1'—C5'—H5'	119.7
C23—C22—P1	121.21 (17)	F1''—B1''—F2''	109.3 (4)
C24—C23—C22	121.2 (2)	F1''—B1''—F3''	109.8 (4)
C24—C23—H23	119.4	F2''—B1''—F3''	109.2 (4)
C22—C23—H23	119.4	F1''—B1''—C1''	110.4 (6)
C23—C24—C25	121.0 (2)	F2''—B1''—C1''	110.1 (6)
C23—C24—H24	119.5	F3''—B1''—C1''	107.9 (4)
C25—C24—H24	119.5	C5''—C1''—C2''	114.7 (5)
N4—C25—C26	121.2 (2)	C5''—C1''—B1''	123.3 (3)
N4—C25—C24	121.5 (2)	C2''—C1''—B1''	121.8 (3)
C26—C25—C24	117.3 (2)	C3''—C2''—C1''	121.3 (6)
C27—C26—C25	121.1 (2)	C3''—C2''—H2''	119.4
C27—C26—H26	119.4	C1''—C2''—H2''	119.4
C25—C26—H26	119.4	N1''—C3''—C2''	124.0 (6)
C26—C27—C22	121.5 (2)	N1''—C3''—H3''	118.0
C26—C27—H27	119.2	C2''—C3''—H3''	118.0
C22—C27—H27	119.2	C3''—N1''—C4''	115.0 (5)
N4—C28—H28A	109.5	N1''—C4''—C5''	123.9 (6)
N4—C28—H28B	109.5	N1''—C4''—H4''	118.0
H28A—C28—H28B	109.5	C5''—C4''—H4''	118.0
N4—C28—H28C	109.5	C4''—C5''—C1''	121.1 (6)
H28A—C28—H28C	109.5	C4''—C5''—H5''	119.5
H28B—C28—H28C	109.5	C1''—C5''—H5''	119.5
C22—P1—C6—C11	−165.58 (17)	C6—P1—C30—C31	−37.8 (2)
C14—P1—C6—C11	73.1 (2)	C14—P1—C30—C31	−159.5 (2)
C30—P1—C6—C11	−44.8 (2)	C22—P1—C30—C35	−99.4 (2)
C22—P1—C6—C7	14.0 (2)	C6—P1—C30—C35	140.3 (2)
C14—P1—C6—C7	−107.34 (19)	C14—P1—C30—C35	18.5 (2)
C30—P1—C6—C7	134.73 (18)	C35—C30—C31—C32	−1.3 (4)
C11—C6—C7—C8	0.9 (3)	P1—C30—C31—C32	176.8 (2)
P1—C6—C7—C8	−178.63 (17)	C30—C31—C32—C33	−1.0 (4)
C6—C7—C8—C9	−1.6 (3)	C36—N5—C33—C34	−164.1 (3)
C12—N2—C9—C8	−10.9 (3)	C37—N5—C33—C34	−14.5 (4)
C13—N2—C9—C8	−177.6 (2)	C36—N5—C33—C32	15.6 (4)
C12—N2—C9—C10	169.3 (2)	C37—N5—C33—C32	165.2 (3)
C13—N2—C9—C10	2.6 (3)	C31—C32—C33—N5	−176.6 (2)
C7—C8—C9—N2	−179.2 (2)	C31—C32—C33—C34	3.2 (4)
C7—C8—C9—C10	0.6 (3)	N5—C33—C34—C35	176.6 (2)
N2—C9—C10—C11	−179.3 (2)	C32—C33—C34—C35	−3.1 (4)
C8—C9—C10—C11	0.9 (3)	C33—C34—C35—C30	0.9 (4)
C9—C10—C11—C6	−1.6 (3)	C31—C30—C35—C34	1.4 (4)
C7—C6—C11—C10	0.7 (3)	P1—C30—C35—C34	−176.73 (19)
P1—C6—C11—C10	−179.79 (17)	F2—B1—C1—C5	−111.0 (17)
C22—P1—C14—C19	26.6 (2)	F3—B1—C1—C5	130.6 (16)
C6—P1—C14—C19	149.00 (18)	F1—B1—C1—C5	9.9 (18)
C30—P1—C14—C19	−93.1 (2)	F2—B1—C1—C2	69.0 (15)
C22—P1—C14—C15	−164.60 (17)	F3—B1—C1—C2	−49.4 (16)
C6—P1—C14—C15	−42.2 (2)	F1—B1—C1—C2	−170.1 (14)
C30—P1—C14—C15	75.7 (2)	C5—C1—C2—C3	1 (3)
C19—C14—C15—C16	2.1 (3)	B1—C1—C2—C3	−178.9 (16)
P1—C14—C15—C16	−166.94 (17)	C1—C2—C3—N1	1 (3)
C14—C15—C16—C17	0.4 (3)	C2—C3—N1—C4	−8 (3)
C21—N3—C17—C18	−0.1 (3)	C3—N1—C4—C5	12 (3)
C20—N3—C17—C18	175.1 (2)	N1—C4—C5—C1	−10 (3)
C21—N3—C17—C16	−179.8 (2)	C2—C1—C5—C4	3 (2)
C20—N3—C17—C16	−4.6 (3)	B1—C1—C5—C4	−177.0 (13)
C15—C16—C17—N3	176.4 (2)	F2'—B1'—C1'—C5'	−58.8 (16)
C15—C16—C17—C18	−3.3 (3)	F3'—B1'—C1'—C5'	61.5 (16)
N3—C17—C18—C19	−175.8 (2)	F1'—B1'—C1'—C5'	−179.7 (15)
C16—C17—C18—C19	3.9 (3)	F2'—B1'—C1'—C2'	113.8 (15)
C17—C18—C19—C14	−1.5 (3)	F3'—B1'—C1'—C2'	−125.9 (15)
C15—C14—C19—C18	−1.5 (3)	F1'—B1'—C1'—C2'	−7.2 (15)
P1—C14—C19—C18	167.46 (17)	C5'—C1'—C2'—C3'	−1 (3)
C6—P1—C22—C27	109.6 (2)	B1'—C1'—C2'—C3'	−175 (2)
C14—P1—C22—C27	−126.2 (2)	C1'—C2'—C3'—N1'	−8 (4)
C30—P1—C22—C27	−9.0 (2)	C2'—C3'—N1'—C4'	21 (4)
C6—P1—C22—C23	−71.9 (2)	C3'—N1'—C4'—C5'	−26 (3)
C14—P1—C22—C23	52.3 (2)	N1'—C4'—C5'—C1'	18 (3)
C30—P1—C22—C23	169.60 (19)	C2'—C1'—C5'—C4'	−3 (3)
C27—C22—C23—C24	−1.1 (4)	B1'—C1'—C5'—C4'	170.2 (14)
P1—C22—C23—C24	−179.66 (18)	F1''—B1''—C1''—C5''	−114.4 (13)
C22—C23—C24—C25	0.2 (4)	F2''—B1''—C1''—C5''	124.8 (13)
C28—N4—C25—C26	167.9 (2)	F3''—B1''—C1''—C5''	5.7 (15)
C29—N4—C25—C26	6.3 (4)	F1''—B1''—C1''—C2''	60.3 (13)
C28—N4—C25—C24	−12.6 (4)	F2''—B1''—C1''—C2''	−60.5 (13)
C29—N4—C25—C24	−174.2 (2)	F3''—B1''—C1''—C2''	−179.7 (12)
C23—C24—C25—N4	−178.6 (2)	C5''—C1''—C2''—C3''	−1.9 (19)
C23—C24—C25—C26	0.9 (3)	B1''—C1''—C2''—C3''	−176.9 (11)
N4—C25—C26—C27	178.3 (2)	C1''—C2''—C3''—N1''	0 (2)
C24—C25—C26—C27	−1.2 (4)	C2''—C3''—N1''—C4''	1.7 (18)
C25—C26—C27—C22	0.4 (4)	C3''—N1''—C4''—C5''	−1.1 (15)
C23—C22—C27—C26	0.7 (4)	N1''—C4''—C5''—C1''	−1.1 (17)
P1—C22—C27—C26	179.35 (19)	C2''—C1''—C5''—C4''	2.5 (19)
C22—P1—C30—C31	82.6 (2)	B1''—C1''—C5''—C4''	177.5 (10)