Bis(tetra­ethyl­ammonium) dodeca­cyanododecaborate(2−)

Juhasz, M.A.; Kamin, A.A.

doi:10.1107/S2056989026008480

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ISSN: 2056-9890

Volume 82| Part 9| September 2026| Pages 1087-1090

https://doi.org/10.1107/S2056989026008480

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Bis(tetraethylammonium) dodecacyanododecaborate(2−)

Marcus A. Juhasz ^a ^* and Ashlyn A. Kamin ^a

^aDepartment of Chemistry, Whitman College, 345 Boyer Ave., Walla Walla, WA, USA, 99362
^*Correspondence e-mail: [email protected]

Edited by D. R. Manke, University of Massachusetts Dartmouth, USA (Received 11 June 2026; accepted 17 August 2026; online 28 August 2026)

The title compound, 2C₈H₂₀N⁺·B₁₂C₁₂N₁₂²⁻, was prepared using microwave-promoted cross-coupling and crystallized from an acetonitrile-water solution. The structure was determined at 101 K, indicating the title compound crystallizes in the trigonal space group P3 and features a B₁₂(CN)₁₂²⁻ subunit with nearly icosahedral symmetry. The anionic subunit interacts with the Et₄N⁺ cation in the structure by multiple weak Csp³–H⋯N hydrogen bonds between CN groups on the anion and methyl and methylene H atoms on the cation.

Keywords: crystal structure; boranes; borates; boron clusters; microwave synthesis; cyanation.

CCDC reference: 2051082

1. Chemical context

Clusters based on an icosahedral framework of boron atoms, such as the borane anion closo-B₁₂H₁₂^2– (Pitochelli & Hawthorne, 1960 ), and the related boron and carbon-based carborane clusters closo-CB₁₁H₁₂⁻ (Knoth, 1967 ) and ortho-C₂B₁₀H₁₂ (Heying et al., 1963 ) were first reported over 60 years ago. In contrast to many other boron hydride compounds, which are often reactive under ambient conditions, e.g., the simplest isolable borane, diborane (B₂H₆), is a pyrophoric gas, icosahedral boranes and carboranes are highly stable solids. closo-B₁₂H₁₂^2–, which has the same core skeleton of twelve borons as the title compound, has been described as `the most stable molecule in all of chemistry' (Grimes, 2004 ), with its Cs⁺ salts exhibiting thermal stability under vacuum at temperatures above 800°C (Muetterties et al., 1964 ).

Anionic boron clusters within the icosahedral family (e.g. closo-CB₁₁H₁₂⁻ and closo-B₁₂H₁₂^2–) exhibit delocalization of charge within the core of twelve heavy atoms. This property contributes to their exceptional stability and makes these species useful as weakly-coordinating anions (WCAs) for applications where a tightly-bound counter-anion would attenuate the activity of a key cationic species, for example, a metal center in a catalyst. The closo-CB₁₁H₁₂⁻ and closo-B₁₂H₁₂^2– anions have also been suggested as promising electrolytes for batteries (Carter et al., 2014 ; Giri et al., 2014 ; Fisher et al., 2019 ; Guzik et al., 2019 ; Ceppetelli et al., 2025 ; Akrouchi et al., 2026 ). The replacement of hydrogens on parent boron cluster anions with sterically-hindering and/or electron-withdrawing groups (EWGs) is an established approach for improving their performance as WCAs (Strauss, 1993 ; Reed, 1998 ) and derivatization of boron anions has been investigated as a strategy for tuning their properties for charge storage applications (Bukovsky et al., 2017 ; Ready et al., 2024 ). Halogenation is one of the most common synthetic modifications to closo-CB₁₁H₁₂⁻ and closo-B₁₂H₁₂^2–, and a variety of methods for halogenation of these boron clusters have been reported (Douvris & Michl, 2013 ; Sivaev et al., 2002 ).

Cyano (CN) groups, one of the strongest known electron-withdrawing substituents, have been investigated as well. Initial attempts to cyanate closo-B₁₂H₁₂^2– by UV irradiation of perchlorinated and perbrominated precursors in the presence of KCN yielded a maximum of 9 CN groups per cluster (Trofimenko & Cripps, 1965 ; Trofimenko, 1966 ). Nearly 50 years later, computational studies predicted that the completely cyanated cluster, closo-B₁₂(CN)₁₂^2– would be a promising electrolyte for batteries (Zhao et al., 2016 ). Subsequently, an updated UV-irradiation synthesis was finally achieved many years later, but the target closo-B₁₂(CN)₁₂^2–, present in ca. 10–15% abundance, was not isolated from the mixture of products (Mayer et al., 2020 ). A subsequent preparation of closo-B₁₂(CN)₁₂^2– by microwave-promoted cross-coupling and isolation of this anion as a tetraethylammonium ion salt in 35% yield was reported (Kamin & Juhasz, 2020 ).

2. Structural commentary

The title salt (Fig. 1) crystallizes in the trigonal space group P $[\overline{3}]$ with three 2C₈H₂₀N⁺·B₁₂C₁₂N₁₂^2– formula units in the unit cell. The B₁₂(CN)₁₂^2– subunit has nearly icosahedral symmetry. B—B bonds within the B12 skeleton range from 1.784 (2) to 1.802 (2) Å; all B—C bond lengths are nearly identical, each falling within 0.007 Å of the average B—C distance of 1.547 Å; the C≡N lengths also fall in a narrow range from 1.111 (2) to 1.147 (2) Å. The B—C≡N angles are all nearly linear, ranging from 179.8 (2) to 173.4 (1)°. The tetraethylammonium cation has a tetrahedral geometry about the central nitrogen atom and no unusual bond lengths or angles.

Figure 1
Molecular structure of the title compound with atom labels and ellipsoids at the 50% probability level. Symmetry codes: (i) 1 − y, x − y, z; (ii) 1 + y − x, 1 − x, z (iii) −x, −y, −z; (iv) −y + x, x, −z; (v) −y, x − y, z; (vi) y − x, −x, z; (vii) y, −x + y, −z.

3. Supramolecular features

Neither the Et₄N⁺ cation nor the B₁₂(CN)₁₂^2– anion in the title compound contains functional groups capable of conventional hydrogen-bond donation. However, multiple weak Csp³—H⋯N hydrogen bonds are present, with H⋯N distances shorter than the sum of the van der Waals radii for these atoms (Table 1, Fig. 2). The closest cation–anion contact is between N6 in a cyano group in the anion and the methylene hydrogen H22b in the cation, with an N6⋯H22b distance of 2.496 (1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20b⋯N14ⁱ	0.99	2.72 (1)	3.6826 (17)	165 (1)
C22—H22b⋯N6	0.99	2.50 (1)	3.4716 (17)	169 (1)
C26—H26a⋯N16ⁱⁱ	0.99	2.69 (1)	3.4422 (17)	133 (1)
C24—H24a⋯N1ⁱⁱⁱ	0.99	2.83 (1)	3.6183 (18)	137 (1)
C24—H24b⋯N14^iv	0.99	3.02 (1)	3.6812 (17)	125 (1)
C27—H27a⋯N7^v	0.98	2.75 (1)	3.4681 (18)	131 (1)
C19—H19b⋯N18	0.98	2.66 (1)	3.4792 (18)	142 (1)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 2
Packing diagram along the c crystallographic axis with C—H⋯N hydrogen bonds shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (Update 6.01 February 2026; Groom et al., 2016 ) using ConQuest (version 2025.1 May 2025; Bruno et al., 2002 ) revealed only two related structures that contain the dodecacyanododecaborate(2−) moiety. One of these structures is a Cu^I acetonitrile complex [Cu₂B₁₂(CN)₁₂(CH₃CN)₆] that crystallizes in the P $[\overline{1}]$ space group and features the B₁₂(CN)₁₂^2– dianion coordinated to each of two Cu^I centers via a 1.999 Å Cu—N bond (Kamin & Juhasz, 2020). The other structure (Mayer et al., 2020) is a tetraphenylphosphonium salt [(C₆H₅)₄P]₂[B₁₂(CN)₁₂] that crystallizes in the P2₁/n space group and features a cation–anion contact of 2.725 Å between CN and Ph-H, just within the carbon/hydrogen van der Waals distance of 2.75 Å.

5. Synthesis and crystallization

The title compound was synthesized from the tetraethylammonium salt of dodecaiodododecaborate (2–) (Juhasz et al., 2016 ) by microwave-promoted cyanation in the presence of copper(I) cyanide and palladium(II) chloride in DMF (Kamin & Juhasz, 2020).

Yield = 35%. ¹¹B NMR (acetone-d₆, ppm) for the title compound: δ = −17.6 (s); ¹H NMR (acetone-d₆, ppm) δ = 1.46 [tt, 12H, N(CH₂CH₃)₄], 3.56 [q, 8H, N(CH₂CH₃)₄]; ¹³C NMR (acetone-d₆, ppm) δ = 117.6 [br, (CN)12], 52.6 [N(CH₂CH₃)₄] 7.2 [N(CH₂CH₃)₄]. FTIR (ATR, cm⁻¹) 2986 (m), 2954 (m), 2924 (m), 2235 (m), 1704 (m), 1616 (s). LC-MS m/z = 220.9. HRMS (for the most abundant mass within each isotopic envelope) m/z = 221.0784 ([B₁₂(CN)₁₂]^2–, theoretical = 221.0777), 572.3154 ([Et₄N][B₁₂(CN)₁₂]⁻, theoretical = 572.3160), 443.1622 (H[B₁₂(CN)₁₂]⁻, theoretical = 443.1638).

Crystals were grown by slow evaporation of a saturated solution of the compound dissolved in 5:1 H₂O–acetonitrile. A suitable crystal for diffraction was selected from the solution and fractured to give an appropriately sized fragment.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed at calculated positions and refined as riding with C—H = 0.98 Å for CH₃ groups and C—H = 0.99 Å for CH₂ groups and U_iso(H) = 1.2U_eq(C) for CH₂ groups and U_iso(H) = 1.5U_eq(C) for CH₃ groups.

Table 2
Experimental details

Crystal data
Chemical formula	2C₈H₂₀N⁺·B₁₂C₁₂N₁₂²⁻
M_r	702.62
Crystal system, space group	Trigonal, P $[\overline{3}]$
Temperature (K)	101
a, c (Å)	20.87937 (17), 7.83528 (8)
V (Å³)	2958.15 (5)
Z	3
Radiation type	Cu Kα
μ (mm⁻¹)	0.55
Crystal size (mm)	0.19 × 0.14 × 0.13

Data collection
Diffractometer	Xcalibur, Onyx, Nova
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 )
T_min, T_max	0.798, 1.000
No. of measured, independent and observed [I ≥ 2u(I)] reflections	36416, 4054, 3537
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 1.05
No. of reflections	4054
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31
Computer programs: CrysAlis PRO (Rigaku OD, 2015), OLEX2 (Dolomanov et al., 2009 ; Bourhis et al., 2015 ), Mercury (Macrae et al., 2020 ), publCIF (Westrip, 2010 ) and CHEMDRAW 23.1 (Revvity Signals, 2026 ).

Supporting information

CCDC reference: 2051082

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008480/yy2024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008480/yy2024Isup2.hkl

checkCIF report

Computing details top

Bis(tetraethylammonium) dodecacyanododecaborate(2-) top

Crystal data top

2C₈H₂₀N⁺·B₁₂C₁₂N₁₂²⁻	D_x = 1.183 Mg m⁻³
M_r = 702.62	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P3	Cell parameters from 15853 reflections
a = 20.87937 (17) Å	θ = 4.2–75.1°
c = 7.83528 (8) Å	µ = 0.55 mm⁻¹
V = 2958.15 (5) Å³	T = 101 K
Z = 3	Prism, clear colourless
F(000) = 1101.327	0.19 × 0.14 × 0.13 mm

Data collection top

Xcalibur, Onyx, Nova diffractometer	3537 reflections with I ≥ 2u(I)
Detector resolution: 8.3552 pixels mm^-1	R_int = 0.042
ω scans	θ_max = 75.2°, θ_min = 2.4°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	h = −25→25
T_min = 0.798, T_max = 1.000	k = −25→25
36416 measured reflections	l = −9→9
4054 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	8 constraints
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0557P)² + 0.7451P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4054 reflections	Δρ_max = 0.24 e Å⁻³
268 parameters	Δρ_min = −0.31 e Å⁻³

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

	x	y	z	U_iso*/U_eq
N21	0.34564 (5)	0.32269 (6)	0.54461 (14)	0.0279 (2)
N7	0.60938 (6)	0.17919 (6)	0.48519 (14)	0.0330 (3)
N18	0.43120 (6)	0.18426 (6)	0.15683 (16)	0.0358 (3)
N14	0.73019 (6)	0.49910 (6)	−0.34953 (14)	0.0341 (3)
C15	0.55536 (6)	0.39676 (6)	−0.01584 (15)	0.0262 (3)
C13	0.71055 (6)	0.44991 (6)	−0.25823 (15)	0.0253 (2)
N16	0.51540 (7)	0.41678 (6)	−0.03207 (15)	0.0362 (3)
C17	0.49234 (6)	0.22346 (6)	0.13233 (15)	0.0252 (2)
C8	0.62552 (6)	0.22195 (6)	0.37884 (15)	0.0243 (2)
B10	0.57565 (7)	0.27594 (7)	0.09724 (16)	0.0218 (2)
C20	0.36457 (7)	0.27048 (7)	0.45107 (17)	0.0309 (3)
H20a	0.39309 (7)	0.29568 (7)	0.34724 (17)	0.035 (4)*
H20b	0.39698 (7)	0.26050 (7)	0.52524 (17)	0.033 (4)*
B11	0.60926 (7)	0.36695 (7)	0.01513 (16)	0.0219 (2)
C22	0.29904 (7)	0.28588 (7)	0.70169 (18)	0.0344 (3)
H22a	0.28774 (7)	0.32145 (7)	0.75844 (18)	0.038 (4)*
H22b	0.25153 (7)	0.24316 (7)	0.66448 (18)	0.036 (4)*
C26	0.41885 (7)	0.38975 (7)	0.59355 (17)	0.0302 (3)
H26a	0.44704 (7)	0.37295 (7)	0.66394 (17)	0.031 (4)*
H26b	0.44767 (7)	0.41193 (7)	0.48813 (17)	0.034 (4)*
C24	0.30016 (7)	0.34448 (8)	0.43163 (19)	0.0360 (3)
H24a	0.25308 (7)	0.29923 (8)	0.40314 (19)	0.038 (4)*
H24b	0.28781 (7)	0.37716 (8)	0.49819 (19)	0.045 (4)*
C27	0.41289 (8)	0.44904 (7)	0.6907 (2)	0.0383 (3)
H27a	0.3870 (5)	0.4678 (4)	0.6205 (6)	0.049 (5)*
H27b	0.3852 (5)	0.42814 (16)	0.7966 (7)	0.053 (5)*
H27c	0.46256 (8)	0.4896 (3)	0.7180 (12)	0.053 (5)*
B9	0.64580 (7)	0.27693 (7)	0.22968 (16)	0.0212 (3)
B12	0.68768 (7)	0.39015 (7)	−0.11843 (16)	0.0219 (3)
C19	0.29855 (8)	0.19728 (8)	0.3992 (2)	0.0407 (3)
H19a	0.2649 (3)	0.20634 (8)	0.3296 (12)	0.058 (5)*
H19b	0.31545 (10)	0.1687 (3)	0.3329 (13)	0.052 (5)*
H19c	0.2726 (4)	0.1694 (3)	0.5016 (2)	0.061 (6)*
C23	0.33424 (8)	0.25910 (8)	0.8313 (2)	0.0429 (3)
H23a	0.3440 (6)	0.2223 (5)	0.7782 (5)	0.055 (5)*
H23b	0.3809 (3)	0.30103 (13)	0.8713 (11)	0.059 (5)*
H23c	0.3006 (3)	0.2366 (6)	0.9283 (7)	0.058 (5)*
C25	0.33684 (9)	0.38333 (9)	0.2675 (2)	0.0471 (4)
H25a	0.3020 (2)	0.3913 (6)	0.1997 (7)	0.066 (6)*
H25b	0.3806 (4)	0.4311 (3)	0.2936 (2)	0.055 (5)*
H25c	0.3517 (6)	0.3528 (3)	0.2025 (7)	0.063 (6)*
C2	−0.03993 (6)	0.12892 (6)	0.92264 (15)	0.0245 (2)
N1	−0.05419 (6)	0.17352 (6)	0.89631 (15)	0.0347 (3)
B3	−0.02056 (7)	0.06750 (7)	0.95897 (16)	0.0212 (2)
B4	0.04206 (7)	0.05478 (7)	0.82630 (16)	0.0217 (2)
N6	0.12165 (6)	0.15241 (6)	0.58135 (13)	0.0291 (2)
C5	0.08551 (6)	0.10920 (6)	0.68130 (15)	0.0233 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N21	0.0195 (5)	0.0248 (5)	0.0403 (6)	0.0117 (4)	−0.0003 (4)	−0.0032 (4)
N7	0.0349 (6)	0.0283 (5)	0.0352 (6)	0.0153 (5)	−0.0008 (4)	0.0043 (5)
N18	0.0243 (6)	0.0325 (6)	0.0472 (7)	0.0116 (5)	0.0018 (5)	−0.0002 (5)
N14	0.0370 (6)	0.0304 (6)	0.0355 (6)	0.0171 (5)	0.0044 (5)	0.0060 (5)
C15	0.0228 (6)	0.0223 (6)	0.0290 (6)	0.0079 (5)	−0.0027 (4)	−0.0023 (4)
C13	0.0229 (5)	0.0237 (6)	0.0295 (6)	0.0117 (5)	0.0006 (4)	−0.0002 (5)
N16	0.0385 (6)	0.0327 (6)	0.0439 (6)	0.0226 (5)	−0.0077 (5)	−0.0074 (5)
C17	0.0244 (6)	0.0223 (5)	0.0303 (6)	0.0128 (5)	−0.0002 (4)	−0.0005 (4)
C8	0.0216 (5)	0.0217 (5)	0.0300 (6)	0.0112 (5)	−0.0012 (4)	−0.0015 (5)
B10	0.0191 (6)	0.0191 (6)	0.0270 (6)	0.0095 (5)	−0.0003 (5)	−0.0004 (5)
C20	0.0258 (6)	0.0298 (6)	0.0419 (7)	0.0175 (5)	0.0017 (5)	−0.0021 (5)
B11	0.0199 (6)	0.0191 (6)	0.0262 (6)	0.0094 (5)	−0.0002 (5)	0.0003 (5)
C22	0.0218 (6)	0.0287 (6)	0.0465 (7)	0.0079 (5)	0.0058 (5)	−0.0041 (5)
C26	0.0194 (6)	0.0253 (6)	0.0418 (7)	0.0081 (5)	−0.0007 (5)	0.0007 (5)
C24	0.0280 (6)	0.0345 (7)	0.0525 (8)	0.0208 (6)	−0.0096 (6)	−0.0088 (6)
C27	0.0318 (7)	0.0248 (6)	0.0554 (8)	0.0119 (6)	−0.0071 (6)	−0.0057 (6)
B9	0.0182 (6)	0.0186 (5)	0.0269 (6)	0.0093 (5)	−0.0001 (4)	−0.0004 (5)
B12	0.0184 (6)	0.0191 (6)	0.0279 (6)	0.0092 (5)	0.0005 (5)	0.0008 (5)
C19	0.0323 (7)	0.0336 (7)	0.0581 (9)	0.0180 (6)	−0.0033 (6)	−0.0134 (6)
C23	0.0374 (8)	0.0364 (7)	0.0457 (8)	0.0116 (6)	0.0070 (6)	0.0062 (6)
C25	0.0515 (9)	0.0491 (9)	0.0512 (9)	0.0329 (8)	−0.0102 (7)	0.0006 (7)
C2	0.0203 (5)	0.0222 (6)	0.0285 (6)	0.0087 (5)	0.0006 (4)	0.0009 (4)
N1	0.0330 (6)	0.0302 (6)	0.0449 (6)	0.0187 (5)	0.0017 (5)	0.0022 (5)
B3	0.0184 (6)	0.0185 (6)	0.0269 (6)	0.0094 (5)	0.0005 (5)	0.0000 (5)
B4	0.0183 (6)	0.0189 (6)	0.0279 (6)	0.0093 (5)	−0.0006 (5)	0.0000 (5)
N6	0.0267 (5)	0.0275 (5)	0.0329 (5)	0.0135 (4)	0.0021 (4)	0.0025 (4)
C5	0.0204 (5)	0.0220 (5)	0.0288 (6)	0.0115 (4)	−0.0015 (4)	−0.0020 (4)

Geometric parameters (Å, º) top

N21—C20	1.5206 (15)	C24—H24b	0.9900
N21—C22	1.5180 (16)	C24—C25	1.509 (2)
N21—C26	1.5178 (15)	C27—H27a	0.9800
N21—C24	1.5245 (16)	C27—H27b	0.9800
N7—C8	1.1421 (16)	C27—H27c	0.9800
N18—C17	1.1364 (16)	B9—B9ⁱ	1.786 (2)
N14—C13	1.1462 (16)	B9—B9ⁱⁱ	1.786 (2)
C15—N16	1.1118 (17)	B12—B12ⁱ	1.800 (2)
C15—B11	1.5534 (17)	B12—B12ⁱⁱ	1.800 (2)
C13—B12	1.5455 (17)	C19—H19a	0.9800
C17—B10	1.5479 (17)	C19—H19b	0.9800
C8—B9	1.5417 (17)	C19—H19c	0.9800
B10—B11	1.7843 (17)	C23—H23a	0.9800
B10—B11ⁱ	1.7846 (17)	C23—H23b	0.9800
B10—B9ⁱⁱ	1.7877 (18)	C23—H23c	0.9800
B10—B9	1.7867 (18)	C25—H25a	0.9800
B10—B12ⁱ	1.8018 (18)	C25—H25b	0.9800
C20—H20a	0.9900	C25—H25c	0.9800
C20—H20b	0.9900	C2—N1	1.1292 (16)
C20—C19	1.5146 (18)	C2—B3	1.5519 (17)
B11—B9ⁱⁱ	1.7964 (18)	B3—B3ⁱⁱⁱ	1.7857 (15)
B11—B12	1.7938 (18)	B3—B3^iv	1.7857 (15)
B11—B12ⁱ	1.7928 (18)	B3—B4^v	1.7888 (18)
C22—H22a	0.9900	B3—B4	1.7910 (18)
C22—H22b	0.9900	B3—B4ⁱⁱⁱ	1.7962 (18)
C22—C23	1.515 (2)	B4—B4^vi	1.796 (2)
C26—H26a	0.9900	B4—B4^v	1.796 (2)
C26—H26b	0.9900	B4—C5	1.5408 (17)
C26—C27	1.5105 (18)	N6—C5	1.1471 (16)
C24—H24a	0.9900

C22—N21—C20	111.00 (10)	H27c—C27—H27b	109.5
C26—N21—C20	106.27 (9)	B10—B9—C8	120.88 (9)
C26—N21—C22	110.92 (10)	B10ⁱ—B9—C8	120.82 (9)
C24—N21—C20	110.98 (10)	B11ⁱ—B9—C8	118.65 (9)
C24—N21—C22	106.54 (10)	B11ⁱ—B9—B10	59.74 (7)
C24—N21—C26	111.20 (10)	B11ⁱ—B9—B10ⁱ	59.72 (7)
B11—C15—N16	177.20 (13)	B9ⁱ—B9—C8	124.36 (8)
B12—C13—N14	173.43 (13)	B9ⁱⁱ—B9—C8	124.42 (8)
B10—C17—N18	179.13 (13)	B9ⁱⁱ—B9—B10ⁱ	107.84 (7)
B9—C8—N7	177.53 (12)	B9ⁱ—B9—B10ⁱ	59.99 (8)
B11—B10—C17	121.49 (10)	B9ⁱⁱ—B9—B10	60.05 (8)
B11ⁱ—B10—C17	121.57 (10)	B9ⁱ—B9—B10	107.89 (7)
B9—B10—C17	121.98 (10)	B9ⁱ—B9—B11ⁱ	107.76 (6)
B9ⁱⁱ—B10—C17	121.95 (10)	B9ⁱⁱ—B9—B11ⁱ	107.80 (6)
B9—B10—B11ⁱ	60.40 (7)	B10ⁱⁱ—B12—C13	114.83 (9)
B9ⁱⁱ—B10—B11ⁱ	108.25 (9)	B11ⁱⁱ—B12—C13	119.11 (9)
B9—B10—B11	108.27 (9)	B11—B12—C13	120.22 (9)
B9ⁱⁱ—B10—B11	60.38 (7)	B11ⁱⁱ—B12—B10ⁱⁱ	59.52 (7)
B12ⁱ—B10—C17	120.54 (10)	B11—B12—B10ⁱⁱ	59.52 (7)
B12ⁱ—B10—B11ⁱ	60.02 (7)	B12ⁱⁱ—B12—C13	127.28 (8)
B12ⁱ—B10—B11	59.99 (7)	B12ⁱ—B12—C13	128.02 (8)
B12ⁱ—B10—B9	108.77 (9)	B12ⁱ—B12—B10ⁱⁱ	107.48 (6)
B12ⁱ—B10—B9ⁱⁱ	108.73 (9)	B12ⁱⁱ—B12—B10ⁱⁱ	107.51 (6)
H20a—C20—N21	108.54 (6)	B12ⁱ—B12—B11	59.86 (8)
H20b—C20—N21	108.54 (6)	B12ⁱⁱ—B12—B11ⁱⁱ	59.91 (8)
H20b—C20—H20a	107.5	B12ⁱ—B12—B11ⁱⁱ	107.61 (7)
C19—C20—N21	114.90 (10)	B12ⁱⁱ—B12—B11	107.56 (7)
C19—C20—H20a	108.54 (8)	H19a—C19—C20	109.5
C19—C20—H20b	108.54 (8)	H19b—C19—C20	109.5
B10—B11—C15	120.33 (10)	H19b—C19—H19a	109.5
B10ⁱⁱ—B11—C15	121.93 (10)	H19c—C19—C20	109.5
B9ⁱⁱ—B11—C15	119.63 (10)	H19c—C19—H19a	109.5
B9ⁱⁱ—B11—B10	59.90 (7)	H19c—C19—H19b	109.5
B9ⁱⁱ—B11—B10ⁱⁱ	59.86 (7)	H23a—C23—C22	109.5
B12ⁱ—B11—C15	122.13 (10)	H23b—C23—C22	109.5
B12—B11—C15	123.16 (10)	H23b—C23—H23a	109.5
B12—B11—B10ⁱⁱ	60.47 (7)	H23c—C23—C22	109.5
B12ⁱ—B11—B10ⁱⁱ	108.53 (9)	H23c—C23—H23a	109.5
B12—B11—B10	108.53 (9)	H23c—C23—H23b	109.5
B12ⁱ—B11—B10	60.49 (7)	H25a—C25—C24	109.5
B12—B11—B9ⁱⁱ	108.70 (9)	H25b—C25—C24	109.5
B12ⁱ—B11—B9ⁱⁱ	108.75 (9)	H25b—C25—H25a	109.5
H22a—C22—N21	108.50 (6)	H25c—C25—C24	109.5
H22b—C22—N21	108.50 (6)	H25c—C25—H25a	109.5
H22b—C22—H22a	107.5	H25c—C25—H25b	109.5
C23—C22—N21	115.09 (11)	B3—C2—N1	179.85 (12)
C23—C22—H22a	108.50 (8)	B3ⁱⁱⁱ—B3—C2	121.29 (9)
C23—C22—H22b	108.50 (8)	B3^iv—B3—C2	122.00 (9)
H26a—C26—N21	108.47 (6)	B4—B3—C2	121.82 (9)
H26b—C26—N21	108.47 (7)	B4^v—B3—C2	121.34 (10)
H26b—C26—H26a	107.5	B4ⁱⁱⁱ—B3—C2	121.07 (9)
C27—C26—N21	115.19 (10)	B4^v—B3—B3^iv	108.39 (6)
C27—C26—H26a	108.47 (7)	B4—B3—B3^iv	60.29 (6)
C27—C26—H26b	108.47 (8)	B4ⁱⁱⁱ—B3—B3^iv	59.92 (8)
H24a—C24—N21	108.40 (7)	B4^v—B4—B3^vi	107.77 (7)
H24b—C24—N21	108.40 (6)	B4^vi—B4—B3^iv	107.69 (6)
H24b—C24—H24a	107.5	B4^vi—B4—B3^vi	59.95 (8)
C25—C24—N21	115.53 (11)	B4^v—B4—B3^iv	107.62 (6)
C25—C24—H24a	108.40 (8)	B4^vi—B4—B3	107.67 (7)
C25—C24—H24b	108.40 (8)	B4^v—B4—B3	59.83 (8)
H27a—C27—C26	109.5	C5—B4—B3	121.53 (9)
H27b—C27—C26	109.5	C5—B4—B3^vi	119.17 (9)
H27b—C27—H27a	109.5	C5—B4—B3^iv	117.01 (9)
H27c—C27—C26	109.5	C5—B4—B4^v	126.55 (8)
H27c—C27—H27a	109.5	N6—C5—B4	175.28 (12)

C15—B11—B10—C17	2.61 (12)	B11—B12—B11ⁱⁱ—B12ⁱⁱ	100.81 (12)
C15—B11—B10ⁱⁱ—C17ⁱⁱ	−3.30 (13)	B11—B12—B12ⁱ—C13ⁱ	105.40 (10)
C15—B11—B10—B11ⁱ	149.86 (12)	B11—B12—B12ⁱⁱ—C13ⁱⁱ	153.60 (8)
C15—B11—B10ⁱⁱ—B11ⁱⁱ	−150.51 (12)	B11—B12—B12ⁱⁱ—B11ⁱⁱ	−99.85 (4)
C15—B11—B10—B9	−146.28 (11)	B11ⁱⁱ—B12—B12ⁱ—B11	99.81 (4)
C15—B11—B10ⁱⁱ—B9ⁱⁱ	108.16 (14)	B11—B12—B12ⁱⁱ—B11ⁱ	−0.04 (11)
C15—B11—B10ⁱⁱ—B9ⁱ	145.64 (11)	B11—B12—B12ⁱ—B11ⁱ	−99.85 (4)
C15—B11—B10—B9ⁱⁱ	−108.84 (14)	B11—B12ⁱ—B12—B12ⁱⁱ	137.58 (6)
C15—B11—B10ⁱⁱ—B12	−112.81 (14)	B11—B12—B12ⁱ—B12ⁱⁱ	−137.58 (6)
C15—B11—B10—B12ⁱ	112.15 (14)	B11—B12ⁱ—B12ⁱⁱ—B12	−37.76 (7)
C15—B11—B9ⁱⁱ—C8ⁱⁱ	−0.92 (12)	B11—B12—B12ⁱⁱ—B12ⁱ	37.73 (7)
C15—B11—B9ⁱⁱ—B10ⁱⁱ	−111.93 (13)	C22—N21—C20—C19	55.98 (12)
C15—B11—B9ⁱⁱ—B10	109.99 (13)	C22—N21—C26—C27	−58.61 (11)
C15—B11—B9ⁱⁱ—B9	147.32 (12)	C22—N21—C24—C25	179.24 (11)
C15—B11—B9ⁱⁱ—B9ⁱ	−149.33 (12)	C26—N21—C20—C19	176.67 (11)
C15—B11—B12—C13	8.09 (13)	C26—N21—C22—C23	−59.37 (11)
C15—B11—B12ⁱ—C13ⁱ	−5.96 (12)	C26—N21—C24—C25	58.26 (12)
C15—B11—B12—B10ⁱⁱ	110.86 (14)	C24—N21—C20—C19	−62.30 (12)
C15—B11—B12ⁱ—B10	−109.25 (14)	C24—N21—C22—C23	179.46 (10)
C15—B11—B12—B11ⁱⁱ	148.16 (10)	C24—N21—C26—C27	59.76 (11)
C15—B11—B12ⁱ—B11ⁱ	−146.55 (9)	B9—B10—B11ⁱ—C15ⁱ	108.16 (8)
C15—B11—B12ⁱ—B12	112.64 (13)	B9—B10—B11ⁱ—B10ⁱ	−37.36 (8)
C15—B11—B12—B12ⁱ	−110.99 (13)	B9ⁱⁱ—B10—B11ⁱ—B9	37.48 (9)
C15—B11—B12ⁱ—B12ⁱⁱ	150.44 (10)	B9—B10—B11—B9ⁱⁱ	−37.44 (9)
C15—B11—B12—B12ⁱⁱ	−148.78 (10)	B9ⁱⁱ—B10—B11—B12	101.33 (7)
C13—B12—B10ⁱⁱ—C17ⁱⁱ	0.61 (11)	B9—B10ⁱ—B11ⁱⁱ—B12	−63.89 (9)
C13—B12—B10ⁱⁱ—B11	111.79 (13)	B9ⁱ—B10ⁱⁱ—B11—B12	−101.54 (12)
C13—B12—B10ⁱⁱ—B11ⁱⁱ	−110.46 (13)	B9—B10—B11ⁱ—B12ⁱ	−139.03 (9)
C13—B12—B10ⁱⁱ—B9ⁱⁱ	148.82 (10)	B9—B10—B11—B12	63.89 (9)
C13—B12—B10ⁱⁱ—B9ⁱ	−147.48 (10)	B9—B10—B11—B12ⁱ	101.57 (11)
C13—B12—B11ⁱⁱ—C15ⁱⁱ	−5.96 (12)	B9ⁱⁱ—B10—B11—B12ⁱ	139.02 (9)
C13—B12—B11—B10ⁱⁱ	−102.77 (13)	B9—B10—B11ⁱ—B12ⁱⁱ	−101.38 (7)
C13—B12—B11—B10	156.88 (11)	B9—B10—B9ⁱⁱ—C8ⁱⁱ	−114.48 (7)
C13—B12—B11ⁱⁱ—B10ⁱⁱ	103.30 (13)	B9—B10—B9ⁱⁱ—B10ⁱⁱ	100.93 (8)
C13—B12—B11ⁱⁱ—B10ⁱ	−156.35 (10)	B9—B10—B9ⁱⁱ—B9ⁱ	37.58 (9)
C13—B12—B11—B9ⁱⁱ	−139.54 (11)	B9ⁱⁱ—B10—B9—B9ⁱ	−37.59 (9)
C13—B12—B11ⁱⁱ—B9ⁱ	140.11 (10)	B9—B10—B12ⁱ—C13ⁱ	148.82 (9)
C13—B12—B11ⁱⁱ—B12ⁱⁱ	−118.60 (14)	B9—B10—B12ⁱ—B11ⁱ	37.02 (9)
C13—B12—B11—B12ⁱ	119.08 (15)	B9—B10ⁱ—B12ⁱⁱ—B12	63.51 (9)
C13—B12—B12ⁱ—C13ⁱ	−1.15 (14)	B9ⁱⁱ—B10—B12ⁱ—B12	0.27 (9)
C13—B12—B12ⁱⁱ—C13ⁱⁱ	−1.15 (14)	B9—B10—B12ⁱ—B12	−63.43 (9)
C13—B12—B12ⁱ—B10	−143.66 (13)	B9—B10—B12ⁱ—B12ⁱⁱ	−0.20 (9)
C13—B12—B12ⁱⁱ—B10ⁱ	142.46 (13)	B9—B11ⁱ—B10—B12ⁱ	139.03 (9)
C13—B12—B12ⁱ—B11ⁱ	153.60 (12)	B9ⁱⁱ—B11—B10—B12ⁱ	−139.02 (9)
C13—B12—B12ⁱ—B11	−106.55 (17)	B9—B11ⁱ—B12ⁱⁱ—B12	−63.50 (8)
C13—B12—B12ⁱⁱ—B11ⁱ	−154.79 (12)	B9ⁱⁱ—B11—B12—B12ⁱ	101.38 (10)
C13—B12—B12ⁱⁱ—B11ⁱⁱ	105.40 (17)	B9—B11ⁱ—B12ⁱ—B12	63.59 (9)
C13—B12—B12ⁱⁱ—B12ⁱ	−117.03 (11)	B9ⁱⁱ—B11—B12ⁱ—B12	−101.30 (10)
C13—B12—B12ⁱ—B12ⁱⁱ	115.87 (11)	B9—B9ⁱ—B10ⁱⁱ—B12	−63.75 (7)
C17—B10—B11ⁱ—C15ⁱ	−3.30 (13)	B9ⁱⁱ—B9—B10—B12ⁱ	101.26 (7)
C17—B10—B11ⁱ—B10ⁱ	−148.82 (12)	B9—B9ⁱⁱ—B10ⁱⁱ—B12	63.67 (7)
C17—B10—B11—B10ⁱⁱ	148.80 (12)	B9—B9ⁱⁱ—B10—B12ⁱ	−101.33 (7)
C17—B10—B11—B9ⁱⁱ	111.45 (14)	B9—B9ⁱⁱ—B11—B10ⁱⁱ	−100.75 (12)
C17—B10—B11ⁱ—B9	−111.46 (14)	B9—B9ⁱⁱ—B11—B12	−63.72 (10)
C17—B10—B11—B12ⁱ	−109.53 (14)	B9ⁱ—B9ⁱⁱ—B11—B12	−0.37 (10)
C17—B10—B11ⁱ—B12ⁱⁱ	147.16 (11)	B9—B9ⁱ—B11ⁱⁱ—B12	63.61 (10)
C17—B10—B11—B12	−147.22 (11)	B9—B9ⁱⁱ—B11—B12ⁱ	0.26 (10)
C17—B10—B11ⁱ—B12ⁱ	109.52 (14)	B12—B10ⁱⁱ—B11—B9ⁱⁱ	139.03 (9)
C17—B10—B9—C8	3.47 (12)	B12—B10ⁱⁱ—B11—B12ⁱ	37.65 (8)
C17—B10—B9ⁱⁱ—C8ⁱⁱ	−3.36 (13)	B12ⁱ—B10—B11—B12	−37.69 (8)
C17—B10—B9—B10ⁱ	148.02 (9)	B12—B11—B10ⁱⁱ—C17ⁱⁱ	109.52 (8)
C17—B10—B9ⁱⁱ—B10ⁱⁱ	−147.94 (9)	B12—B11—B10ⁱⁱ—B11ⁱⁱ	−37.70 (8)
C17—B10—B9—B11ⁱ	110.80 (14)	B12—B11—B10ⁱⁱ—B9ⁱⁱ	−139.03 (9)
C17—B10—B9ⁱⁱ—B11	−110.71 (14)	B12—B11—B9ⁱⁱ—C8ⁱⁱ	148.04 (9)
C17—B10—B9—B9ⁱ	−148.67 (10)	B12—B11—B9ⁱⁱ—B10ⁱⁱ	37.03 (9)
C17—B10—B9—B9ⁱⁱ	−111.08 (13)	B12—B11—B12ⁱ—C13ⁱ	−118.60 (7)
C17—B10—B9ⁱⁱ—B9ⁱ	148.70 (10)	B12—B11—B12ⁱ—B11ⁱ	100.81 (8)
C17—B10—B9ⁱⁱ—B9	111.12 (13)	B12ⁱ—B11—B12—B12ⁱⁱ	−37.79 (9)
C17—B10—B12ⁱ—C13ⁱ	0.61 (12)	B12—B11—B12ⁱ—B12ⁱⁱ	37.80 (9)
C17—B10—B12ⁱ—B11ⁱ	−111.18 (14)	B12—B12ⁱ—B10—B11ⁱ	−100.45 (11)
C17—B10—B12ⁱ—B11	111.08 (14)	C2—B3—B3ⁱⁱⁱ—C2ⁱⁱⁱ	0.79 (10)
C17—B10—B12ⁱ—B12	148.36 (12)	C2—B3—B3^iv—C2^iv	−0.79 (10)
C17—B10—B12ⁱ—B12ⁱⁱ	−148.40 (12)	C2—B3—B3^iv—B3^vi	−148.58 (15)
C8—B9—B10ⁱ—C17ⁱ	−3.36 (12)	C2—B3—B3ⁱⁱⁱ—B3^v	148.31 (15)
C8—B9—B10—B11ⁱ	−107.33 (14)	C2—B3—B3ⁱⁱⁱ—B4^vii	−147.87 (13)
C8—B9—B10ⁱ—B11ⁱⁱ	−152.16 (11)	C2—B3—B3ⁱⁱⁱ—B4ⁱⁱⁱ	−110.27 (15)
C8—B9—B10ⁱ—B11ⁱ	107.35 (13)	C2—B3—B3^iv—B4	−111.06 (16)
C8—B9—B10—B11	152.18 (11)	C2—B3—B3ⁱⁱⁱ—B4^v	110.75 (17)
C8—B9—B10ⁱ—B9ⁱ	−114.48 (14)	C2—B3—B3^iv—B4ⁱⁱⁱ	109.96 (15)
C8—B9—B10—B9ⁱⁱ	114.55 (14)	C2—B3—B3^iv—B4^iv	147.64 (13)
C8—B9—B10ⁱ—B12ⁱⁱ	144.19 (10)	C2—B3—B4—B3^iv	111.34 (14)
C8—B9—B10—B12ⁱ	−144.19 (11)	C2—B3—B4ⁱⁱⁱ—B3^iv	−111.46 (12)
C8—B9—B11ⁱ—C15ⁱ	−0.92 (12)	C2—B3—B4^v—B3ⁱⁱⁱ	−110.66 (14)
C8—B9—B11ⁱ—B10ⁱ	−110.91 (13)	C2—B3—B4^v—B3^v	−148.00 (9)
C8—B9—B11ⁱ—B10	111.00 (13)	C2—B3—B4ⁱⁱⁱ—B3ⁱⁱⁱ	110.62 (12)
C8—B9—B11ⁱ—B12ⁱⁱ	−147.98 (10)	C2—B3—B4—B3^vi	148.70 (9)
C8—B9—B11ⁱ—B12ⁱ	148.04 (10)	C2—B3—B4^v—B4^vi	148.91 (9)
C8—B9—B9ⁱⁱ—C8ⁱⁱ	−0.09 (12)	C2—B3—B4—B4^v	−110.49 (13)
C8—B9—B9ⁱ—C8ⁱ	−0.09 (13)	C2—B3—B4ⁱⁱⁱ—B4^iv	−148.85 (12)
C8—B9—B9ⁱ—B10ⁱ	108.77 (16)	C2—B3—B4ⁱⁱⁱ—B4^vii	147.85 (12)
C8—B9—B9ⁱⁱ—B10	−108.86 (17)	C2—B3—B4^v—B4	111.28 (13)
C8—B9—B9ⁱⁱ—B10ⁱⁱ	150.84 (12)	C2—B3—B4—B4^vi	−148.10 (10)
C8—B9—B9ⁱ—B10ⁱⁱ	−150.90 (12)	C2—B3—B4^v—C5^v	−4.60 (12)
C8—B9—B9ⁱ—B11ⁱⁱ	146.04 (12)	C2—B3—B4ⁱⁱⁱ—C5ⁱⁱⁱ	−1.83 (12)
C8—B9—B9ⁱⁱ—B11	−146.07 (12)	C2—B3—B4—C5	6.34 (13)
C8—B9—B9ⁱⁱ—B9ⁱ	113.23 (11)	B3—B3ⁱⁱⁱ—B3^v—B3^vii	63.90 (6)
C8—B9—B9ⁱ—B9ⁱⁱ	−113.32 (11)	B3—B3^iv—B3^vi—B3^vii	−63.90 (6)
B10—B11—B10ⁱⁱ—C17ⁱⁱ	−148.82 (10)	B3—B3^iv—B3^vi—B4	37.56 (11)
B10—B11—B10ⁱⁱ—B11ⁱⁱ	63.97 (7)	B3^vi—B3^iv—B3—B4	−37.52 (11)
B10ⁱⁱ—B11—B10—B11ⁱ	−63.96 (7)	B3ⁱⁱⁱ—B3—B3^iv—B4	101.42 (8)
B10—B11ⁱ—B10ⁱ—B9	37.35 (9)	B3^v—B3ⁱⁱⁱ—B3—B4	−0.12 (10)
B10—B11—B10ⁱⁱ—B9ⁱ	0.12 (9)	B3—B3ⁱⁱⁱ—B3^v—B4^vi	0.07 (10)
B10ⁱⁱ—B11—B10—B9	−0.10 (9)	B3—B3ⁱⁱⁱ—B3^v—B4^vii	101.46 (8)
B10—B11—B10ⁱⁱ—B9ⁱⁱ	−37.36 (9)	B3^vii—B3^vi—B4—B3	63.10 (11)
B10ⁱⁱ—B11—B10—B12ⁱ	−101.67 (11)	B3—B3ⁱⁱⁱ—B4^vii—B3^v	−100.44 (12)
B10—B11—B10ⁱⁱ—B12	101.66 (11)	B3^iv—B3^vi—B4—B3	−37.34 (10)
B10—B11—B9ⁱⁱ—C8ⁱⁱ	−110.91 (8)	B3^iv—B3—B4—B3^vi	37.36 (10)
B10—B11—B9ⁱⁱ—B10ⁱⁱ	138.08 (9)	B3ⁱⁱⁱ—B3—B4—B3^iv	−100.44 (12)
B10—B11ⁱ—B9—B10ⁱ	−138.08 (9)	B3^vi—B3^iv—B4—B3	137.92 (9)
B10—B11ⁱ—B9—B9ⁱ	−100.75 (9)	B3ⁱⁱⁱ—B3—B4—B3^vi	−63.08 (11)
B10—B11—B9ⁱⁱ—B9ⁱ	100.67 (9)	B3—B3^iv—B4—B3^vi	−137.92 (9)
B10—B11—B9ⁱⁱ—B9	37.33 (9)	B3^iv—B3—B4—B4^v	138.17 (8)
B10—B11ⁱ—B9—B9ⁱⁱ	−37.41 (9)	B3—B3ⁱⁱⁱ—B4^vii—B4^iv	−0.01 (10)
B10—B11—B12ⁱ—C13ⁱ	103.30 (8)	B3ⁱⁱⁱ—B3—B4—B4^vi	0.12 (10)
B10ⁱⁱ—B11—B12ⁱ—B10	100.36 (10)	B3^iv—B3—B4—B4^vi	100.56 (6)
B10—B11—B12—B10ⁱⁱ	−100.35 (10)	B3ⁱⁱⁱ—B3—B4—B4^v	37.73 (9)
B10—B11—B12ⁱ—B11ⁱ	−37.30 (9)	B3—B3^iv—B4ⁱⁱⁱ—B4^vii	100.43 (6)
B10ⁱ—B11ⁱⁱ—B12—B11	63.06 (10)	B3—B3ⁱⁱⁱ—B4^v—B4^vi	100.69 (9)
B10—B11ⁱ—B12ⁱ—B11	37.30 (9)	B3—B3^iv—B4—B4^vi	−100.52 (9)
B10—B11—B12—B11ⁱⁱ	−63.05 (10)	B3^iv—B3—B4^v—B4	−37.62 (9)
B10ⁱⁱ—B11—B12ⁱ—B12	−37.75 (8)	B3—B3ⁱⁱⁱ—B4^v—B4	37.39 (9)
B10ⁱⁱ—B11—B12—B12ⁱ	138.15 (9)	B3ⁱⁱⁱ—B3—B4^v—B4	−138.06 (8)
B10—B11—B12ⁱ—B12	−138.11 (9)	B3—B3^iv—B4—B4^v	−37.23 (9)
B10—B11ⁱ—B12ⁱ—B12	100.36 (6)	B3^vii—B3^vi—B4—C5	−153.50 (9)
B10—B11ⁱ—B12ⁱⁱ—B12	0.05 (9)	B3^iv—B3^vi—B4—C5	106.06 (7)
B10—B11—B12ⁱ—B12ⁱⁱ	−100.31 (6)	B3ⁱⁱⁱ—B3—B4—C5	154.56 (9)
B10—B11—B12—B12ⁱ	37.80 (8)	B3^iv—B3—B4—C5	−105.00 (7)
B10—B11—B12—B12ⁱⁱ	0.01 (9)	B3^vi—B3^iv—B4—C5	−109.63 (6)
B10—B9—B10ⁱ—C17ⁱ	−147.94 (7)	B3—B3^iv—B4—C5	112.45 (6)
B10—B9—B10ⁱ—B11ⁱ	−37.24 (10)	B3—B4—B3^vi—C2^vi	−148.00 (7)
B10ⁱ—B9—B10—B11	−63.27 (9)	B3—B4—B3^iv—C2^iv	−110.62 (6)
B10—B9ⁱⁱ—B10ⁱⁱ—B11	37.22 (10)	B3—B4ⁱⁱⁱ—B3^iv—B3^vi	−100.44 (6)
B10—B9—B10ⁱ—B11ⁱⁱ	63.26 (9)	B3^iv—B4ⁱⁱⁱ—B3—B4	36.97 (7)
B10ⁱ—B9—B10—B9ⁱⁱ	−100.90 (12)	B3^iv—B4—B3—B4ⁱⁱⁱ	−36.81 (7)
B10—B9—B10ⁱ—B9ⁱ	100.93 (12)	B3ⁱⁱⁱ—B4^v—B3—B4	138.06 (11)
B10—B9ⁱⁱ—B10ⁱⁱ—B12	0.36 (9)	B3^iv—B4—B3—B4^v	−138.17 (11)
B10—B9—B10ⁱ—B12ⁱⁱ	−0.39 (9)	B3—B4—B3^iv—B4^iv	100.94 (9)
B10—B9—B11ⁱ—C15ⁱ	−111.93 (8)	B3—B4ⁱⁱⁱ—B3^iv—B4	−36.87 (7)
B10—B9—B11ⁱ—B10ⁱ	138.08 (9)	B3^vi—B4—B3—B4^v	−100.81 (12)
B10—B9ⁱⁱ—B11—B10ⁱⁱ	−138.08 (9)	B3^vi—B4—B3—B4ⁱⁱⁱ	0.55 (8)
B10—B9ⁱⁱ—B11—B12	−101.05 (7)	B3—B4—B3^vi—B4^iv	−0.47 (8)
B10—B9—B11ⁱ—B12ⁱ	37.03 (9)	B3—B4—B3^vi—B4^vi	100.72 (12)
B10—B9—B11ⁱ—B12ⁱⁱ	101.02 (7)	B3—B4—B3^iv—B4ⁱⁱⁱ	37.01 (7)
B10—B9ⁱⁱ—B11—B12ⁱ	−37.06 (9)	B3—B4^v—B3ⁱⁱⁱ—B4^vii	−100.90 (9)
B10—B9—B9ⁱⁱ—C8ⁱⁱ	108.77 (9)	B3—B4—B4^vi—B3^v	−0.08 (11)
B10—B9—B9ⁱ—C8ⁱ	150.84 (8)	B3—B4^v—B4^vi—B3^vii	62.92 (6)
B10—B9—B9ⁱ—B10ⁱⁱ	0.03 (10)	B3—B4^v—B4—B3^iv	37.17 (9)
B10—B9ⁱⁱ—B9—B10ⁱ	100.33 (4)	B3—B4ⁱⁱⁱ—B4^vii—B3^v	0.13 (7)
B10—B9—B9ⁱ—B10ⁱ	−100.30 (4)	B3—B4—B4^v—B3ⁱⁱⁱ	−37.30 (9)
B10—B9—B9ⁱⁱ—B10ⁱⁱ	−100.30 (4)	B3—B4ⁱⁱⁱ—B4^iv—B3^vii	−62.92 (8)
B10—B9—B9ⁱⁱ—B11	−37.21 (8)	B3—B4—B4^vi—B3^vii	−63.12 (6)
B10—B9ⁱⁱ—B9—B11ⁱ	37.27 (8)	B3—B4ⁱⁱⁱ—B4^iv—B3^vi	0.13 (7)
B10—B9—B9ⁱ—B11ⁱⁱ	−63.02 (8)	B3—B4—B4^vi—B3^vi	−100.30 (4)
B10ⁱ—B9—B9ⁱⁱ—B11	63.12 (8)	B3—B4^v—B4—B3^vi	100.22 (4)
B10—B9—B9ⁱ—B9ⁱⁱ	37.61 (7)	B3—B4—B4^v—B3^v	−100.30 (4)
B10—B9ⁱⁱ—B9—B9ⁱ	137.91 (6)	B3—B4—B4^vi—B4^v	37.53 (7)
B10—B9ⁱⁱ—B9ⁱ—B9	−37.58 (7)	B3—B4^v—B4—B4^vi	137.83 (6)
B10—B9—B9ⁱⁱ—B9ⁱ	−137.91 (6)	B3—B4ⁱⁱⁱ—B4^vii—B4^iv	100.65 (7)
B10—B12ⁱ—B11ⁱ—B9	−36.77 (9)	B3—B4^v—B4^vi—B4	−37.61 (7)
B10—B12ⁱ—B11—B9ⁱⁱ	36.81 (9)	B3—B4—B4^v—B4^vi	−137.83 (6)
B10—B12ⁱ—B11—B12	138.11 (10)	B3—B4ⁱⁱⁱ—B4^iv—B4^vii	−100.53 (7)
B10ⁱⁱ—B12—B11—B12ⁱ	−138.15 (10)	B3ⁱⁱⁱ—B4^v—B4—C5	−146.08 (9)
B10ⁱⁱ—B12—B12ⁱ—B10	−0.05 (7)	B3^vii—B4^vi—B4—C5	143.56 (9)
B10ⁱ—B12ⁱⁱ—B12—B11	−62.78 (9)	B3—B4—B4^vi—C5^vi	150.92 (8)
B10—B12ⁱ—B12—B11	−37.12 (8)	B3—B4^v—B4—C5	−108.78 (9)
B10ⁱⁱ—B12—B12ⁱ—B11	37.07 (8)	B3—B4—B4^v—C5^v	106.39 (9)
B10—B12ⁱ—B12—B11ⁱⁱ	62.70 (9)	B3^v—B4^vi—B4—C5	−153.40 (8)
B10—B12ⁱ—B12ⁱⁱ—B12	−100.51 (7)	B4—B3—B3^iv—C2^iv	110.27 (8)
B10—B12ⁱ—B12—B12ⁱⁱ	100.46 (7)	B4—B3—B3ⁱⁱⁱ—C2ⁱⁱⁱ	−147.64 (9)
C20—N21—C22—C23	58.53 (11)	B4—B3^vi—B3^vii—B3^v	0.07 (7)
C20—N21—C26—C27	−179.36 (10)	B4—B3^iv—B3^vi—B3^vii	−101.46 (8)
C20—N21—C24—C25	−59.82 (11)	B4—B3^iv—B3—B4ⁱⁱⁱ	138.98 (6)
B11—B10—B11ⁱ—C15ⁱ	−150.51 (10)	B4—B3—B3^iv—B4^iv	−101.30 (6)
B11—B10—B11ⁱ—B10ⁱ	63.97 (7)	B4—B3^vi—B3^iv—B4ⁱⁱⁱ	101.39 (6)
B11—B10—B11ⁱ—B9	101.33 (11)	B4—B3—B3^iv—B4ⁱⁱⁱ	−138.98 (7)
B11ⁱ—B10—B11—B9ⁱⁱ	−101.31 (11)	B4—B3—B3ⁱⁱⁱ—B4^v	−37.68 (8)
B11—B10ⁱⁱ—B11ⁱⁱ—B12	37.71 (9)	B4^v—B3—B3^iv—B4	37.59 (8)
B11—B10—B11ⁱ—B12ⁱ	−37.70 (9)	B4—B3^vi—B3^vii—B4^iv	−101.39 (10)
B11ⁱ—B10—B11—B12	0.02 (9)	B4—B3—B3ⁱⁱⁱ—B4ⁱⁱⁱ	101.30 (10)
B11—B10—B11ⁱ—B12ⁱⁱ	−0.05 (9)	B4—B3—B3ⁱⁱⁱ—B4^vii	63.71 (8)
B11—B10—B9ⁱⁱ—C8ⁱⁱ	107.35 (8)	B4—B3—B4^v—B3^v	100.72 (8)
B11—B10—B9ⁱⁱ—B10ⁱⁱ	−37.24 (9)	B4—B3^vi—B4^iv—B3^vii	100.90 (15)
B11—B10—B9—B11ⁱ	−100.49 (10)	B4—B3—B4ⁱⁱⁱ—B3ⁱⁱⁱ	−100.94 (15)
B11ⁱ—B10—B9ⁱⁱ—B11	100.50 (10)	B4^v—B3—B4—B4^vi	−37.61 (9)
B11—B10—B9—B9ⁱⁱ	37.63 (8)	B4—B3^vi—B4^iv—B4ⁱⁱⁱ	0.21 (10)
B11ⁱ—B10—B9—B9ⁱⁱ	138.12 (9)	B4—B3^vi—B4^iv—B4^vii	63.51 (9)
B11—B10—B9ⁱⁱ—B9	−138.17 (9)	B4—B3—B4^v—B4^vi	37.63 (9)
B11—B10—B9ⁱⁱ—B9ⁱ	−100.59 (6)	B4—B3—B4ⁱⁱⁱ—B4^iv	−0.42 (10)
B11—B10—B9—B9ⁱ	0.04 (9)	B4ⁱⁱⁱ—B3—B4^v—B4	−101.19 (8)
B11ⁱ—B10—B9ⁱⁱ—B9	−37.68 (8)	B4—B3^iv—B4ⁱⁱⁱ—B4^vii	63.56 (7)
B11—B10ⁱⁱ—B9ⁱ—B9	−0.10 (9)	B4—B3—B4ⁱⁱⁱ—B4^vii	−63.72 (9)
B11—B10ⁱⁱ—B9ⁱⁱ—B9	100.53 (6)	B4ⁱⁱⁱ—B3—B4—B4^v	101.36 (8)
B11—B10—B12ⁱ—C13ⁱ	−110.46 (8)	B4ⁱⁱⁱ—B3—B4—B4^vi	63.75 (7)
B11—B10—B12ⁱ—B11ⁱ	137.74 (9)	B4ⁱⁱⁱ—B3^iv—B4—C5	149.47 (9)
B11—B10ⁱⁱ—B12—B11ⁱⁱ	−137.74 (9)	B4—B3—B4ⁱⁱⁱ—C5ⁱⁱⁱ	146.60 (9)
B11—B10—B12ⁱ—B12	37.29 (9)	B4^v—B3—B4—C5	116.84 (7)
B11—B10—B12ⁱ—B12ⁱⁱ	100.52 (9)	B4—B3—B4^v—C5^v	−115.88 (7)
B11—B10ⁱⁱ—B12—B12ⁱ	−37.22 (9)	B4ⁱⁱⁱ—B3—B4—C5	−141.81 (10)
B11—B10ⁱⁱ—B12—B12ⁱⁱ	−100.45 (9)	B4^iv—B3^vi—B4—C5	142.93 (9)
B11—B9ⁱⁱ—B10—B9	138.17 (10)	B4—B4^vi—B3^v—B3^vii	−100.43 (9)
B11ⁱ—B9—B10—B9ⁱⁱ	−138.12 (10)	B4—B4^vi—B3^v—B3ⁱⁱⁱ	0.01 (8)
B11—B9ⁱⁱ—B10ⁱⁱ—B12	−36.86 (9)	B4—B4^vi—B3^vii—B3^v	100.69 (10)
B11—B9ⁱⁱ—B10—B12ⁱ	36.84 (9)	B4—B4^v—B3ⁱⁱⁱ—B4^vii	−63.51 (10)
B11—B9ⁱⁱ—B9—B11ⁱ	0.07 (8)	B4—B4^vi—B3^v—B4^vii	−63.56 (4)
B11—B9ⁱⁱ—B9—B9ⁱ	100.70 (7)	B4—B4^vi—B3^vii—B4^iv	−0.21 (10)
B11—B9ⁱⁱ—B9ⁱ—B9	−100.63 (7)	B4—B4^vi—B4^v—B3ⁱⁱⁱ	−100.65 (5)
B11—B12—B10ⁱⁱ—C17ⁱⁱ	−111.18 (8)	B4—B4^v—B4^vi—B3^vii	100.53 (5)
B11—B12ⁱ—B10—B11ⁱ	−137.74 (9)	B4^v—B4^vi—B4—C5	−115.79 (6)
B11—B12—B10ⁱⁱ—B11ⁱⁱ	137.74 (9)	B4^vi—B4^v—B4—C5	113.39 (6)
B11—B12—B10ⁱⁱ—B9ⁱ	100.73 (7)	C5—B4—B3^vi—C2^vi	−4.60 (12)
B11—B12—B10ⁱⁱ—B9ⁱⁱ	37.02 (9)	C5—B4—B3^iv—C2^iv	1.83 (12)
B11—B12ⁱ—B10—B9	−100.72 (7)	C5—B4—B3^iv—B4^iv	−146.60 (9)
B11—B12ⁱ—B10—B9ⁱⁱ	−37.01 (9)	C5—B4—B3^vi—B4^vi	−115.88 (14)
B11—B12—B11ⁱⁱ—C15ⁱⁱ	−146.55 (7)	C5—B4—B4^v—B3^v	150.92 (12)
B11—B12—B11ⁱⁱ—B10ⁱⁱ	−37.30 (10)	C5—B4—B4^vi—B3^vi	106.39 (17)
B11—B12—B11ⁱⁱ—B9ⁱ	−0.49 (9)	C5—B4—B4^v—C5^v	−2.40 (13)
B11—B12ⁱ—B11ⁱ—B9	0.53 (9)	C5—B4—B4^vi—C5^vi	−2.40 (13)
B11ⁱⁱ—B12—B11—B12ⁱ	−100.85 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20b···N14^viii	0.99	2.72 (1)	3.6826 (17)	165 (1)
C22—H22b···N6	0.99	2.50 (1)	3.4716 (17)	169 (1)
C26—H26a···N16^ix	0.99	2.69 (1)	3.4422 (17)	133 (1)
C24—H24a···N1^x	0.99	2.83 (1)	3.6183 (18)	137 (1)
C24—H24b···N14^xi	0.99	3.02 (1)	3.6812 (17)	125 (1)
C27—H27a···N7^xii	0.98	2.75 (1)	3.4681 (18)	131 (1)
C19—H19b···N18	0.98	2.66 (1)	3.4792 (18)	142 (1)

Symmetry codes: (viii) −y+1, x−y, z+1; (ix) x, y, z+1; (x) y, −x+y, −z+1; (xi) −x+1, −y+1, −z; (xii) x−y, x, −z+1.

Acknowledgements

The authors acknowledge Professor Doug Juers for assistance with crystallography and Whitman College and the National Science Foundation for funding.

Funding information

Funding for this research was provided by: National Science Foundation (grant No. CHE-1764344 to Marcus A. Juhasz).

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