Tetra­butyl­ammonium 2-[2,5-dimethyl-3-(4-nitro­phen­yl)-2,3-dihydro-1,2,4-oxadiazo­lium-4-yl]nona­hydro-closo-deca­borate

Mindich, A.L.; Pavlishchuk, A.V.; Bokach, N.A.; Starova, G.L.; Zhizhin, K.Y.

doi:10.1107/S1600536812044984

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3284-o3285

doi:10.1107/S1600536812044984

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Tetrabutylammonium 2-[2,5-dimethyl-3-(4-nitrophenyl)-2,3-dihydro-1,2,4-oxadiazolium-4-yl]nonahydro-closo-decaborate

Aleksey L. Mindich,^a Anna V. Pavlishchuk,^b ^* Nadezhda A. Bokach,^a ^* Galina L. Starova ^a and Konstantin Yu. Zhizhin ^c

^aDepartment of Chemistry, Saint-Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, ^bDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska str. 62, Kiev 01601, Ukraine, and ^cN. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Pr., 119991 Moscow, Russian Federation
^*Correspondence e-mail: annpavlis@ukr.net,

(Received 8 June 2012; accepted 30 October 2012; online 3 November 2012)

The title ionic compound, C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃⁻, consists of a tetrabutylammonium cation and a closo-decaborate cluster anion, which is bound to the substituted 2,3-dihydro-1,2,4-oxadiazole ring through a B—N bond [1.540 (2) Å]. The distances between connected B atoms in the decaborate cluster range from 1.689 (2) to 1.844 (2) Å. The 2,3-dihydro-1,2,4-oxadiazole ring adopts an envelope conformation with the N atom as the flap atom.

Related literature

For related structures and background, see: Mindich et al. (2012 ). For examples of substituted 1,2,4-oxadiazoles, their complexes and properties, see: Kritchenkov et al. (2012 ); Bokach et al. (2011a ,b ); Makarycheva-Mikhailova et al. (2007 ); Kukushkin & Pombeiro (2002 ); Kritchenkov et al. (2011 ); Bokach (2010 ); Sivaev et al. (2002 , 2008 ). For propeties and structure examples of boron clusters, see: Dash et al. (2011 ); Dou et al. (1994 ).

Experimental

Crystal data

C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃⁻
M_r = 580.85
Monoclinic, P 2₁ /n
a = 8.7356 (4) Å
b = 15.8691 (6) Å
c = 24.7015 (10) Å
β = 98.206 (1)°
V = 3389.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.161, T_max = 0.374
35977 measured reflections
10868 independent reflections
6806 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.142
S = 0.94
10868 reflections
388 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044984/aa2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044984/aa2067Isup2.hkl

checkCIF report

Comment top

In the past decade, a great attention has been paid to electrophilic activation of the C≡N bond in nitriles (Bokach, 2010; Bokach et al., 2011a; Bokach et al., 2011b; Kritchenkov et al., 2011; Kritchenkov et al., 2012; Kukushkin & Pombeiro, 2002; Makarycheva-Mikhailova et al., 2007). In a addition an interest in compounds which contain borane clusters is caused by their potential application in medicine, homogeneous catalysis, for non-linear optics and luminescent materials creation, as potential metal extractants, agents for anion recognition and building blocks for coordination polymers creation, etc (Dash et al., 2011). Despite boron clusters are known near the century, examples of coordination compounds based thereon are sparse. Therefore the synthesis of new ligand systems based on borane clusters and investigation of their ability of complex formation are of particular interest. In the framework of our project focused on reactivity of the activated C≡N group in nitrilium derivatives of closo-decaborate clusters (Mindich et al., 2012), the substituted borylated 2,3-dihydro-1,2,4-oxadiazole (Scheme 1) was characterized by a single-crystal X-ray diffraction.

Each unit cell (Fig. 1) of the title compound, [n-Bu₄N]⁺[C₁₀H₂₀B₁₀O₃N₃]^-, consists of four anions and four cations. So far as there are no hydrogen bonds in the title compound, it should be mentioned that crystal packing is generally caused by electrostatic interactions between cations and anions. In the cation of the title compound, the alkyl chains of [n-Bu₄N]⁺ are always in anti or gauche conformations and all bond lengths are close to those reported in the literature (Sivaev et al., 2008).

The anionic part consists of a substituted 2,3-dihydro-1,2,4-oxadiazole ring bound to the closo-decaborate cluster via the N1 atom [d(B2—N1) = 1.540 (3) Å] (Fig. 2). This bond is longer as compared to the starting nitrilium closo-decaborate (1.515 (5) Å) (Dou et al., 1994) and is equal, within 3σ, to those in the previously described closo-decaborate clusters functionalized with substituted 2,3-dihydro-1,2,4-oxadiazoles (1.5438 (18)–1.546 (3) Å) (Mindich et al., 2012).

Ten boron atoms in the decaborate cluster are connected between each other in such way, that they form a bicapped square antiprism. Each of two boron atoms (B1 and B10), which are situated in the vertex of observed polyhedron, are surrounded by four boron atoms. Bond distances between B1 or B10 and connected with them boron atoms (B2 – B5 for B1 and B6 – B9 for B10) range from 1.689 (2) Å to 1.708 (2) Å. Each of the boron atoms B2 – B9 are surrounded by five boron atoms. Bond distances between connected boron atoms B2 – B9 vary from 1.806 (2) Å to 1.844 (2) Å, what is on 0.117 – 0.136 Å longer than for B1—B(2–5) and B10—B(6–9) bonds. In the cluster, the B—B bond distances and angles are typical for 2-substituted-nonahydro-closo-decaborates (Dou et al., 1994; Sivaev et al., 2002).

The double bond in 1,2,4-oxadiazole in the title compound is observed between atoms N1 and C1 [d = 1.2886 (16) Å]. The 2,3-dihydro-1,2,4-oxadiazole ring adopts an envelope conformation with N2 being the flap atom. Deviation of N2 from the plane O1C1N1C5 is equal to 0.327 (2) Å. 1,2,4-oxadiazole contains two methyl groups in the 2-nd and 5-th positions and p-nitrophenyl in the 3-rd position. The angle between mean planes of substituted 1,2,4-oxadiazole ring O1C1N1C5 and phenyl ring C6C7C8C9C10C11 is equal to 86.35 (18)°. The geometrical parameters of the 2,3-dihydro-1,2,4-oxadiazole rings are the same, within 3σ, as those in the previously described borylated 2,3-dihydro-1,2,4-oxadiazoles (Mindich et al., 2012). All bonds and angles are of normal values.

Related literature top

For related structures and background, see: Mindich et al. (2012). For examples of substituted 1,2,4-oxadiazoles, their complexes and properties, see: Kritchenkov et al. (2012); Bokach et al. (2011a,b); Makarycheva-Mikhailova et al. (2007); Kukushkin & Pombeiro (2002); Kritchenkov et al. (2011); Bokach (2010); Sivaev et al. (2002, 2008). For propeties and structure examples of boron clusters, see: Dash et al. (2011); Dou et al. (1994).

Experimental top

Title compound was synthesized and isolated as pure solid by the described method (Mindich et al., 2012). The crystal was obtained by a slow evaporation of a methanol solution of the title compound. XRD study was carried out in the X-ray Diffraction Centre of St.Petersburg State University.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A packing view of the title compound.
	Fig. 2. A view of the title compound with the atomic numbering scheme (thermal ellipsoids are drawn at the 50% probability level.

Tetrabutylammonium 2-[2,5-dimethyl-3-(4-nitrophenyl)-2,3-dihydro- 1,2,4-oxadiazolium-4-yl]nonahydro-closo-decaborate top

Crystal data top

C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃⁻	F(000) = 1256
M_r = 580.85	D_x = 1.138 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6524 reflections
a = 8.7356 (4) Å	θ = 2.6–30.8°
b = 15.8691 (6) Å	µ = 0.07 mm⁻¹
c = 24.7015 (10) Å	T = 100 K
β = 98.206 (1)°	Block, colorless
V = 3389.2 (2) Å³	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	10868 independent reflections
Radiation source: fine-focus sealed tube	6806 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 31.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→6
T_min = 0.161, T_max = 0.374	k = −23→20
35977 measured reflections	l = −34→35

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0609P)²] where P = (F_o² + 2F_c²)/3
10868 reflections	(Δ/σ)_max < 0.001
388 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃⁻	V = 3389.2 (2) Å³
M_r = 580.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7356 (4) Å	µ = 0.07 mm⁻¹
b = 15.8691 (6) Å	T = 100 K
c = 24.7015 (10) Å	0.35 × 0.25 × 0.20 mm
β = 98.206 (1)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	10868 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6806 reflections with I > 2σ(I)
T_min = 0.161, T_max = 0.374	R_int = 0.086
35977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 0.94	Δρ_max = 0.55 e Å⁻³
10868 reflections	Δρ_min = −0.51 e Å⁻³
388 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
N4	1.06470 (12)	0.31892 (7)	−0.19722 (4)	0.0152 (2)
C1A	0.99038 (15)	0.30280 (8)	−0.25556 (5)	0.0166 (3)
H1AA	1.0716	0.2948	−0.2781	0.020*
H1AB	0.9323	0.3525	−0.2689	0.020*
C2A	0.88276 (16)	0.22708 (8)	−0.26301 (6)	0.0189 (3)
H2AA	0.7830	0.2420	−0.2528	0.023*
H2AB	0.9257	0.1814	−0.2395	0.023*
C3A	0.86245 (16)	0.19856 (9)	−0.32259 (6)	0.0211 (3)
H3AA	0.8326	0.2465	−0.3461	0.025*
H3AB	0.9605	0.1776	−0.3312	0.025*
C4A	0.7411 (2)	0.13008 (9)	−0.33407 (6)	0.0311 (4)
H4AA	0.7311	0.1143	−0.3719	0.047*
H4AB	0.6437	0.1507	−0.3259	0.047*
H4AC	0.7718	0.0819	−0.3117	0.047*
C1B	0.94265 (15)	0.32580 (8)	−0.15940 (5)	0.0164 (3)
H1BA	0.9944	0.3320	−0.1222	0.020*
H1BB	0.8847	0.2735	−0.1612	0.020*
C2B	0.82901 (16)	0.39833 (8)	−0.17181 (6)	0.0198 (3)
H2BA	0.7641	0.3882	−0.2064	0.024*
H2BB	0.8854	0.4504	−0.1749	0.024*
C3B	0.72812 (17)	0.40682 (9)	−0.12650 (6)	0.0232 (3)
H3BA	0.7946	0.4144	−0.0919	0.028*
H3BB	0.6649	0.4570	−0.1332	0.028*
C4B	0.62259 (17)	0.33156 (10)	−0.12169 (7)	0.0273 (3)
H4BA	0.5635	0.3410	−0.0923	0.041*
H4BB	0.6841	0.2816	−0.1144	0.041*
H4BC	0.5537	0.3247	−0.1553	0.041*
C1C	1.16972 (15)	0.24577 (8)	−0.17577 (5)	0.0168 (3)
H1CA	1.2302	0.2629	−0.1415	0.020*
H1CB	1.1051	0.1989	−0.1679	0.020*
C2C	1.28027 (16)	0.21468 (8)	−0.21379 (6)	0.0182 (3)
H2CA	1.3361	0.2620	−0.2263	0.022*
H2CB	1.2223	0.1877	−0.2455	0.022*
C3C	1.39420 (15)	0.15209 (8)	−0.18342 (6)	0.0194 (3)
H3CA	1.4461	0.1782	−0.1503	0.023*
H3CB	1.3380	0.1034	−0.1729	0.023*
C4C	1.51453 (17)	0.12333 (10)	−0.21844 (7)	0.0282 (3)
H4CA	1.5831	0.0835	−0.1983	0.042*
H4CB	1.5727	0.1711	−0.2279	0.042*
H4CC	1.4636	0.0973	−0.2512	0.042*
C1D	1.15761 (16)	0.40003 (8)	−0.19808 (6)	0.0172 (3)
H1DA	1.2440	0.3894	−0.2178	0.021*
H1DB	1.0925	0.4420	−0.2185	0.021*
C2D	1.22037 (16)	0.43691 (8)	−0.14269 (6)	0.0194 (3)
H2DA	1.2882	0.3964	−0.1220	0.023*
H2DB	1.1355	0.4487	−0.1225	0.023*
C3D	1.30961 (19)	0.51795 (9)	−0.14965 (6)	0.0260 (3)
H3DA	1.3931	0.5059	−0.1705	0.031*
H3DB	1.2410	0.5583	−0.1702	0.031*
C4D	1.3761 (2)	0.55653 (10)	−0.09510 (6)	0.0320 (4)
H4DA	1.4314	0.6071	−0.1013	0.048*
H4DB	1.4455	0.5171	−0.0748	0.048*
H4DC	1.2936	0.5697	−0.0747	0.048*
O1	0.54528 (11)	0.16501 (6)	−0.01773 (4)	0.0202 (2)
N1	0.74065 (12)	0.12499 (6)	0.04378 (4)	0.0144 (2)
N2	0.66334 (12)	0.13225 (7)	−0.05053 (5)	0.0165 (2)
C1	0.59955 (15)	0.15096 (8)	0.03466 (6)	0.0168 (3)
C2	0.49407 (16)	0.17008 (9)	0.07497 (6)	0.0222 (3)
H2A	0.3957	0.1879	0.0561	0.033*
H2B	0.5377	0.2143	0.0989	0.033*
H2C	0.4805	0.1205	0.0961	0.033*
C4	0.60748 (16)	0.04754 (8)	−0.06730 (6)	0.0182 (3)
H4A	0.5161	0.0521	−0.0938	0.027*
H4B	0.5837	0.0171	−0.0359	0.027*
H4C	0.6862	0.0180	−0.0831	0.027*
C5	0.80327 (15)	0.12692 (8)	−0.00925 (5)	0.0148 (3)
H5	0.8579	0.0741	−0.0140	0.018*
C6	0.91407 (15)	0.20041 (8)	−0.00974 (5)	0.0156 (3)
C7	0.87874 (16)	0.28045 (8)	0.00783 (6)	0.0206 (3)
H7	0.7820	0.2908	0.0180	0.025*
C8	0.98651 (17)	0.34482 (9)	0.01034 (6)	0.0222 (3)
H8	0.9630	0.3986	0.0216	0.027*
C9	1.13015 (16)	0.32699 (8)	−0.00431 (5)	0.0181 (3)
C10	1.16758 (15)	0.24852 (8)	−0.02307 (5)	0.0172 (3)
H10	1.2641	0.2386	−0.0336	0.021*
C11	1.05790 (15)	0.18518 (8)	−0.02585 (5)	0.0163 (3)
H11	1.0804	0.1321	−0.0386	0.020*
N3	1.24830 (15)	0.39366 (8)	0.00029 (5)	0.0226 (3)
O3A	1.21039 (14)	0.46527 (6)	0.01226 (5)	0.0338 (3)
O3B	1.37898 (12)	0.37441 (7)	−0.00819 (5)	0.0314 (3)
B1	0.84962 (19)	0.16988 (10)	0.15185 (7)	0.0202 (3)
H12	0.7988	0.2324	0.1557	0.030*
B2	0.84165 (17)	0.10294 (9)	0.09822 (6)	0.0152 (3)
B3	0.78915 (18)	0.07008 (10)	0.16335 (6)	0.0185 (3)
H13	0.6764	0.0609	0.1777	0.028*
B4	0.97278 (19)	0.11400 (10)	0.19715 (7)	0.0219 (3)
H14	1.0038	0.1399	0.2375	0.033*
B5	1.02284 (18)	0.14771 (10)	0.13054 (7)	0.0190 (3)
H15	1.0997	0.2006	0.1211	0.028*
B6	0.85624 (17)	−0.00739 (9)	0.11691 (6)	0.0151 (3)
H16	0.7707	−0.0506	0.0929	0.023*
B7	0.94918 (18)	0.00066 (10)	0.18820 (6)	0.0185 (3)
H17	0.9411	−0.0380	0.2246	0.028*
B8	1.11443 (18)	0.05523 (10)	0.16491 (7)	0.0192 (3)
H18	1.2426	0.0601	0.1834	0.029*
B9	1.02020 (17)	0.04734 (9)	0.09450 (6)	0.0153 (3)
H19	1.0644	0.0470	0.0534	0.023*
B10	1.04235 (17)	−0.03695 (9)	0.13722 (6)	0.0163 (3)
H20	1.0971	−0.0992	0.1344	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0155 (5)	0.0132 (5)	0.0167 (6)	0.0006 (4)	0.0018 (5)	0.0020 (4)
C1A	0.0177 (6)	0.0160 (6)	0.0154 (6)	0.0003 (5)	−0.0001 (5)	0.0019 (5)
C2A	0.0218 (7)	0.0156 (6)	0.0190 (7)	−0.0022 (6)	0.0023 (6)	0.0006 (5)
C3A	0.0226 (7)	0.0204 (7)	0.0204 (7)	−0.0004 (6)	0.0031 (6)	−0.0005 (6)
C4A	0.0443 (10)	0.0247 (8)	0.0240 (8)	−0.0107 (7)	0.0033 (8)	−0.0059 (6)
C1B	0.0174 (6)	0.0148 (6)	0.0172 (6)	0.0002 (5)	0.0036 (5)	0.0017 (5)
C2B	0.0182 (6)	0.0153 (6)	0.0259 (8)	0.0010 (5)	0.0036 (6)	0.0030 (6)
C3B	0.0204 (7)	0.0210 (7)	0.0285 (8)	0.0039 (6)	0.0043 (6)	−0.0015 (6)
C4B	0.0222 (7)	0.0287 (8)	0.0319 (9)	0.0020 (6)	0.0066 (7)	0.0055 (7)
C1C	0.0170 (6)	0.0151 (6)	0.0179 (7)	0.0027 (5)	0.0012 (5)	0.0046 (5)
C2C	0.0197 (6)	0.0171 (6)	0.0182 (7)	0.0007 (6)	0.0037 (6)	0.0026 (5)
C3C	0.0166 (6)	0.0169 (6)	0.0246 (7)	0.0005 (5)	0.0033 (6)	0.0035 (5)
C4C	0.0217 (7)	0.0273 (8)	0.0367 (9)	0.0038 (6)	0.0073 (7)	0.0018 (7)
C1D	0.0183 (6)	0.0134 (6)	0.0196 (7)	−0.0020 (5)	0.0019 (6)	0.0032 (5)
C2D	0.0203 (7)	0.0185 (7)	0.0194 (7)	−0.0023 (6)	0.0027 (6)	−0.0001 (5)
C3D	0.0312 (8)	0.0235 (7)	0.0225 (8)	−0.0100 (7)	0.0008 (7)	0.0012 (6)
C4D	0.0419 (10)	0.0286 (8)	0.0258 (8)	−0.0187 (8)	0.0067 (8)	−0.0048 (7)
O1	0.0172 (5)	0.0238 (5)	0.0190 (5)	0.0083 (4)	0.0009 (4)	−0.0019 (4)
N1	0.0149 (5)	0.0131 (5)	0.0152 (5)	0.0010 (4)	0.0022 (4)	−0.0014 (4)
N2	0.0140 (5)	0.0173 (6)	0.0181 (6)	0.0036 (5)	0.0019 (5)	−0.0028 (4)
C1	0.0178 (6)	0.0140 (6)	0.0182 (7)	0.0022 (5)	0.0014 (5)	−0.0010 (5)
C2	0.0179 (6)	0.0272 (8)	0.0218 (7)	0.0063 (6)	0.0035 (6)	−0.0033 (6)
C4	0.0161 (6)	0.0186 (7)	0.0190 (7)	−0.0002 (5)	0.0001 (5)	−0.0032 (5)
C5	0.0148 (6)	0.0139 (6)	0.0155 (6)	0.0022 (5)	0.0015 (5)	−0.0004 (5)
C6	0.0170 (6)	0.0145 (6)	0.0144 (6)	0.0018 (5)	−0.0002 (5)	0.0003 (5)
C7	0.0199 (7)	0.0166 (6)	0.0261 (8)	0.0025 (6)	0.0060 (6)	−0.0010 (6)
C8	0.0274 (7)	0.0151 (6)	0.0246 (8)	0.0013 (6)	0.0059 (6)	−0.0019 (6)
C9	0.0213 (7)	0.0166 (6)	0.0155 (6)	−0.0045 (6)	−0.0005 (6)	0.0000 (5)
C10	0.0163 (6)	0.0201 (7)	0.0146 (6)	0.0009 (5)	0.0006 (5)	0.0021 (5)
C11	0.0176 (6)	0.0153 (6)	0.0154 (6)	0.0030 (5)	0.0004 (5)	0.0001 (5)
N3	0.0275 (6)	0.0213 (6)	0.0184 (6)	−0.0065 (5)	0.0014 (5)	0.0000 (5)
O3A	0.0450 (7)	0.0185 (5)	0.0398 (7)	−0.0090 (5)	0.0124 (6)	−0.0067 (5)
O3B	0.0245 (6)	0.0327 (6)	0.0367 (7)	−0.0082 (5)	0.0033 (5)	−0.0027 (5)
B1	0.0221 (8)	0.0176 (7)	0.0194 (8)	0.0033 (6)	−0.0020 (7)	−0.0053 (6)
B2	0.0143 (7)	0.0152 (7)	0.0159 (7)	0.0005 (6)	0.0012 (6)	−0.0001 (6)
B3	0.0192 (7)	0.0227 (8)	0.0138 (7)	0.0045 (6)	0.0025 (6)	−0.0015 (6)
B4	0.0229 (8)	0.0223 (8)	0.0190 (8)	0.0051 (7)	−0.0020 (7)	−0.0069 (6)
B5	0.0171 (7)	0.0145 (7)	0.0236 (8)	0.0001 (6)	−0.0028 (6)	−0.0043 (6)
B6	0.0151 (7)	0.0151 (7)	0.0151 (7)	−0.0008 (6)	0.0020 (6)	−0.0015 (6)
B7	0.0190 (7)	0.0197 (8)	0.0163 (7)	0.0034 (6)	0.0007 (6)	0.0012 (6)
B8	0.0165 (7)	0.0188 (7)	0.0206 (8)	0.0019 (6)	−0.0030 (6)	−0.0031 (6)
B9	0.0142 (7)	0.0136 (7)	0.0179 (7)	0.0003 (6)	0.0015 (6)	−0.0015 (6)
B10	0.0158 (7)	0.0154 (7)	0.0176 (7)	0.0020 (6)	0.0015 (6)	−0.0001 (6)

Geometric parameters (Å, º) top

N4—C1A	1.5154 (17)	B2—B6	1.810 (2)
N4—C1B	1.5184 (15)	B2—B3	1.811 (2)
N4—C1D	1.5234 (16)	B2—B5	1.813 (2)
N4—C1C	1.5268 (16)	B3—B7	1.816 (2)
C1A—C2A	1.5206 (18)	B3—B6	1.834 (2)
C2A—C3A	1.5255 (19)	B3—B4	1.837 (2)
C3A—C4A	1.516 (2)	B4—B7	1.820 (2)
C1B—C2B	1.5222 (18)	B4—B8	1.821 (2)
C2B—C3B	1.5261 (18)	B4—B5	1.841 (2)
C3B—C4B	1.524 (2)	B5—B8	1.822 (2)
C1C—C2C	1.5221 (17)	B5—B9	1.823 (2)
C2C—C3C	1.5254 (19)	B6—B10	1.698 (2)
C3C—C4C	1.5235 (18)	B6—B9	1.827 (2)
C1D—C2D	1.5168 (19)	B6—B7	1.835 (2)
C2D—C3D	1.5263 (18)	B7—B10	1.702 (2)
C3D—C4D	1.518 (2)	B7—B8	1.844 (2)
O1—C1	1.3319 (16)	B8—B10	1.697 (2)
O1—N2	1.4929 (13)	B8—B9	1.819 (2)
N1—C1	1.2886 (16)	B9—B10	1.698 (2)
N1—C5	1.4903 (15)	C2—H2A	0.9600
N1—B2	1.5397 (19)	C2—H2B	0.9600
N2—C4	1.4694 (16)	C2—H2C	0.9600
N2—C5	1.4781 (17)	C4—H4A	0.9600
C1—C2	1.4815 (17)	C4—H4B	0.9600
C5—C6	1.5167 (18)	C4—H4C	0.9600
C6—C7	1.3910 (18)	C5—H5	0.9800
C6—C11	1.3923 (17)	C7—H7	0.9300
C7—C8	1.3846 (19)	C8—H8	0.9300
C8—C9	1.3839 (18)	C10—H10	0.9300
C9—C10	1.3841 (18)	C11—H11	0.9300
C9—N3	1.4710 (17)	B1—H12	1.0971
C10—C11	1.3836 (18)	B3—H13	1.1035
N3—O3B	1.2283 (15)	B4—H14	1.0770
N3—O3A	1.2315 (15)	B5—H15	1.1202
B1—B4	1.689 (2)	B6—H16	1.1197
B1—B2	1.692 (2)	B7—H17	1.0992
B1—B3	1.706 (2)	B8—H18	1.1497
B1—B5	1.708 (2)	B9—H19	1.1365
B2—B9	1.806 (2)	B10—H20	1.1034

C1A—N4—C1B	110.74 (10)	B8—B4—B3	102.17 (10)
C1A—N4—C1D	106.63 (9)	B1—B4—B5	57.68 (9)
C1B—N4—C1D	111.72 (9)	B7—B4—B5	102.46 (10)
C1A—N4—C1C	110.87 (10)	B8—B4—B5	59.68 (8)
C1B—N4—C1C	106.32 (9)	B3—B4—B5	90.43 (10)
C1D—N4—C1C	110.63 (10)	B1—B5—B2	57.33 (9)
N4—C1A—C2A	114.97 (10)	B1—B5—B8	111.81 (11)
C1A—C2A—C3A	109.64 (10)	B2—B5—B8	100.79 (10)
C4A—C3A—C2A	112.03 (11)	B1—B5—B9	112.36 (11)
N4—C1B—C2B	115.18 (10)	B2—B5—B9	59.55 (8)
C1B—C2B—C3B	110.33 (11)	B8—B5—B9	59.87 (8)
C4B—C3B—C2B	114.02 (12)	B1—B5—B4	56.68 (9)
C2C—C1C—N4	115.79 (10)	B2—B5—B4	88.61 (10)
C1C—C2C—C3C	109.55 (11)	B8—B5—B4	59.61 (9)
C4C—C3C—C2C	111.75 (11)	B9—B5—B4	101.21 (10)
C2D—C1D—N4	115.98 (10)	B10—B6—B2	111.85 (11)
C1D—C2D—C3D	110.38 (11)	B10—B6—B9	57.44 (8)
C4D—C3D—C2D	112.14 (12)	B2—B6—B9	59.52 (8)
C1—O1—N2	106.93 (9)	B10—B6—B3	112.24 (11)
C1—N1—C5	107.55 (11)	B2—B6—B3	59.61 (8)
C1—N1—B2	129.79 (11)	B9—B6—B3	101.84 (10)
C5—N1—B2	122.41 (10)	B10—B6—B7	57.44 (9)
C4—N2—C5	110.54 (10)	B2—B6—B7	100.53 (10)
C4—N2—O1	104.14 (9)	B9—B6—B7	89.95 (10)
C5—N2—O1	102.30 (9)	B3—B6—B7	59.35 (8)
N1—C1—O1	114.99 (11)	B10—B7—B3	112.88 (11)
N1—C1—C2	128.25 (13)	B10—B7—B4	112.24 (11)
O1—C1—C2	116.72 (12)	B3—B7—B4	60.67 (9)
N2—C5—N1	103.67 (9)	B10—B7—B6	57.21 (8)
N2—C5—C6	114.61 (10)	B3—B7—B6	60.28 (8)
N1—C5—C6	109.72 (10)	B4—B7—B6	102.25 (10)
C7—C6—C11	119.81 (12)	B10—B7—B8	57.02 (8)
C7—C6—C5	121.97 (11)	B3—B7—B8	102.05 (10)
C11—C6—C5	118.14 (11)	B4—B7—B8	59.59 (8)
C8—C7—C6	120.53 (12)	B6—B7—B8	89.55 (9)
C9—C8—C7	118.26 (12)	B10—B8—B9	57.60 (9)
C8—C9—C10	122.54 (13)	B10—B8—B4	112.42 (11)
C8—C9—N3	119.02 (12)	B9—B8—B4	102.14 (11)
C10—C9—N3	118.45 (12)	B10—B8—B5	113.16 (12)
C11—C10—C9	118.38 (12)	B9—B8—B5	60.09 (8)
C10—C11—C6	120.43 (12)	B4—B8—B5	60.71 (9)
O3B—N3—O3A	123.98 (12)	B10—B8—B7	57.27 (8)
O3B—N3—C9	117.83 (12)	B9—B8—B7	89.91 (10)
O3A—N3—C9	118.20 (12)	B4—B8—B7	59.54 (9)
B4—B1—B2	98.06 (11)	B5—B8—B7	102.26 (10)
B4—B1—B3	65.50 (10)	B10—B9—B2	112.08 (10)
B2—B1—B3	64.43 (9)	B10—B9—B8	57.59 (9)
B4—B1—B5	65.64 (10)	B2—B9—B8	101.18 (10)
B2—B1—B5	64.45 (9)	B10—B9—B5	113.11 (11)
B3—B1—B5	99.74 (11)	B2—B9—B5	59.94 (8)
N1—B2—B1	119.71 (11)	B8—B9—B5	60.04 (9)
N1—B2—B9	117.26 (10)	B10—B9—B6	57.44 (8)
B1—B2—B9	114.04 (11)	B2—B9—B6	59.78 (8)
N1—B2—B6	116.95 (11)	B8—B9—B6	90.59 (9)
B1—B2—B6	114.46 (11)	B5—B9—B6	102.89 (10)
B9—B2—B6	60.70 (8)	B8—B10—B9	64.80 (9)
N1—B2—B3	130.92 (11)	B8—B10—B6	99.52 (11)
B1—B2—B3	58.18 (9)	B9—B10—B6	65.12 (9)
B9—B2—B3	103.57 (10)	B8—B10—B7	65.71 (9)
B6—B2—B3	60.84 (8)	B9—B10—B7	99.18 (11)
N1—B2—B5	130.61 (11)	B6—B10—B7	65.35 (9)
B1—B2—B5	58.22 (9)	C1—C2—H2A	109.5
B9—B2—B5	60.51 (8)	C1—C2—H2B	109.5
B6—B2—B5	103.97 (10)	H2A—C2—H2B	109.5
B3—B2—B5	92.16 (10)	C1—C2—H2C	109.5
B1—B3—B2	57.39 (9)	H2A—C2—H2C	109.5
B1—B3—B7	112.18 (11)	H2B—C2—H2C	109.5
B2—B3—B7	101.22 (10)	N2—C4—H4A	109.5
B1—B3—B6	112.57 (10)	N2—C4—H4B	109.5
B2—B3—B6	59.56 (8)	H4A—C4—H4B	109.5
B7—B3—B6	60.37 (8)	N2—C4—H4C	109.5
B1—B3—B4	56.80 (9)	H4A—C4—H4C	109.5
B2—B3—B4	88.80 (10)	H4B—C4—H4C	109.5
B7—B3—B4	59.76 (9)	N2—C5—H5	109.5
B6—B3—B4	101.67 (10)	N1—C5—H5	109.5
B1—B4—B7	112.83 (12)	C6—C5—H5	109.5
B1—B4—B8	112.80 (12)	C8—C7—H7	119.7
B7—B4—B8	60.86 (8)	C6—C7—H7	119.7
B1—B4—B3	57.70 (9)	C9—C8—H8	120.9
B7—B4—B3	59.57 (9)	C7—C8—H8	120.9

C1B—N4—C1A—C2A	−54.33 (14)	B7—B3—B6—B2	−126.43 (11)
C1D—N4—C1A—C2A	−176.07 (11)	B4—B3—B6—B2	−81.59 (10)
C1C—N4—C1A—C2A	63.44 (13)	B1—B3—B6—B9	20.73 (15)
N4—C1A—C2A—C3A	−159.65 (11)	B2—B3—B6—B9	43.63 (9)
C1A—C2A—C3A—C4A	−172.99 (12)	B7—B3—B6—B9	−82.80 (10)
C1A—N4—C1B—C2B	−62.33 (14)	B4—B3—B6—B9	−37.96 (12)
C1D—N4—C1B—C2B	56.37 (15)	B1—B3—B6—B7	103.53 (13)
C1C—N4—C1B—C2B	177.15 (11)	B2—B3—B6—B7	126.43 (11)
N4—C1B—C2B—C3B	−171.56 (11)	B4—B3—B6—B7	44.84 (10)
C1B—C2B—C3B—C4B	−64.75 (16)	B1—B3—B7—B10	−80.78 (14)
C1A—N4—C1C—C2C	47.08 (14)	B2—B3—B7—B10	−21.61 (14)
C1B—N4—C1C—C2C	167.50 (11)	B6—B3—B7—B10	23.40 (11)
C1D—N4—C1C—C2C	−71.01 (14)	B4—B3—B7—B10	−103.54 (12)
N4—C1C—C2C—C3C	170.86 (11)	B1—B3—B7—B4	22.76 (11)
C1C—C2C—C3C—C4C	−176.20 (12)	B2—B3—B7—B4	81.93 (10)
C1A—N4—C1D—C2D	169.95 (11)	B6—B3—B7—B4	126.94 (10)
C1B—N4—C1D—C2D	48.84 (15)	B1—B3—B7—B6	−104.18 (12)
C1C—N4—C1D—C2D	−69.41 (13)	B2—B3—B7—B6	−45.01 (9)
N4—C1D—C2D—C3D	−179.60 (11)	B4—B3—B7—B6	−126.94 (10)
C1D—C2D—C3D—C4D	−179.35 (13)	B1—B3—B7—B8	−21.72 (14)
C1—O1—N2—C4	96.65 (11)	B2—B3—B7—B8	37.46 (12)
C1—O1—N2—C5	−18.51 (12)	B6—B3—B7—B8	82.46 (10)
C5—N1—C1—O1	5.28 (15)	B4—B3—B7—B8	−44.48 (10)
B2—N1—C1—O1	179.62 (11)	B1—B4—B7—B10	81.48 (14)
C5—N1—C1—C2	−172.03 (13)	B8—B4—B7—B10	−22.80 (11)
B2—N1—C1—C2	2.3 (2)	B3—B4—B7—B10	104.60 (12)
N2—O1—C1—N1	8.72 (15)	B5—B4—B7—B10	21.55 (15)
N2—O1—C1—C2	−173.65 (11)	B1—B4—B7—B3	−23.12 (11)
C4—N2—C5—N1	−89.84 (11)	B8—B4—B7—B3	−127.40 (11)
O1—N2—C5—N1	20.57 (11)	B5—B4—B7—B3	−83.05 (11)
C4—N2—C5—C6	150.60 (10)	B1—B4—B7—B6	22.14 (14)
O1—N2—C5—C6	−98.99 (11)	B8—B4—B7—B6	−82.14 (10)
C1—N1—C5—N2	−16.91 (13)	B3—B4—B7—B6	45.26 (9)
B2—N1—C5—N2	168.24 (10)	B5—B4—B7—B6	−37.79 (12)
C1—N1—C5—C6	105.94 (12)	B1—B4—B7—B8	104.28 (13)
B2—N1—C5—C6	−68.91 (14)	B3—B4—B7—B8	127.40 (11)
N2—C5—C6—C7	70.62 (16)	B5—B4—B7—B8	44.35 (10)
N1—C5—C6—C7	−45.51 (17)	B2—B6—B7—B10	−109.30 (11)
N2—C5—C6—C11	−112.55 (13)	B9—B6—B7—B10	−50.36 (9)
N1—C5—C6—C11	131.33 (12)	B3—B6—B7—B10	−154.20 (11)
C11—C6—C7—C8	−1.1 (2)	B10—B6—B7—B3	154.20 (11)
C5—C6—C7—C8	175.64 (13)	B2—B6—B7—B3	44.90 (9)
C6—C7—C8—C9	−0.9 (2)	B9—B6—B7—B3	103.84 (10)
C7—C8—C9—C10	2.3 (2)	B10—B6—B7—B4	108.71 (11)
C7—C8—C9—N3	−177.48 (13)	B2—B6—B7—B4	−0.58 (11)
C8—C9—C10—C11	−1.7 (2)	B9—B6—B7—B4	58.35 (10)
N3—C9—C10—C11	178.13 (12)	B3—B6—B7—B4	−45.48 (9)
C9—C10—C11—C6	−0.43 (19)	B10—B6—B7—B8	50.02 (9)
C7—C6—C11—C10	1.8 (2)	B2—B6—B7—B8	−59.27 (10)
C5—C6—C11—C10	−175.09 (12)	B9—B6—B7—B8	−0.34 (9)
C8—C9—N3—O3B	173.56 (13)	B3—B6—B7—B8	−104.18 (10)
C10—C9—N3—O3B	−6.26 (19)	B1—B4—B8—B10	−81.44 (15)
C8—C9—N3—O3A	−6.58 (19)	B7—B4—B8—B10	22.89 (11)
C10—C9—N3—O3A	173.61 (13)	B3—B4—B8—B10	−21.59 (15)
C1—N1—B2—B1	−47.65 (19)	B5—B4—B8—B10	−104.86 (13)
C5—N1—B2—B1	125.96 (13)	B1—B4—B8—B9	−21.70 (15)
C1—N1—B2—B9	167.10 (13)	B7—B4—B8—B9	82.63 (10)
C5—N1—B2—B9	−19.29 (16)	B3—B4—B8—B9	38.14 (12)
C1—N1—B2—B6	97.94 (15)	B5—B4—B8—B9	−45.12 (9)
C5—N1—B2—B6	−88.46 (13)	B1—B4—B8—B5	23.42 (11)
C1—N1—B2—B3	24.4 (2)	B7—B4—B8—B5	127.75 (11)
C5—N1—B2—B3	−162.03 (12)	B3—B4—B8—B5	83.27 (11)
C1—N1—B2—B5	−119.62 (16)	B1—B4—B8—B7	−104.33 (13)
C5—N1—B2—B5	53.98 (18)	B3—B4—B8—B7	−44.49 (10)
B4—B1—B2—N1	−179.91 (11)	B5—B4—B8—B7	−127.75 (11)
B3—B1—B2—N1	122.24 (13)	B1—B5—B8—B10	80.67 (14)
B5—B1—B2—N1	−121.88 (13)	B2—B5—B8—B10	21.70 (14)
B4—B1—B2—B9	−33.61 (14)	B9—B5—B8—B10	−23.30 (10)
B3—B1—B2—B9	−91.46 (12)	B4—B5—B8—B10	103.64 (12)
B5—B1—B2—B9	24.42 (11)	B1—B5—B8—B9	103.97 (12)
B4—B1—B2—B6	33.70 (14)	B2—B5—B8—B9	45.01 (9)
B3—B1—B2—B6	−24.16 (11)	B4—B5—B8—B9	126.94 (11)
B5—B1—B2—B6	91.73 (12)	B1—B5—B8—B4	−22.97 (11)
B4—B1—B2—B3	57.86 (10)	B2—B5—B8—B4	−81.93 (10)
B5—B1—B2—B3	115.89 (11)	B9—B5—B8—B4	−126.94 (11)
B4—B1—B2—B5	−58.03 (11)	B1—B5—B8—B7	21.25 (14)
B3—B1—B2—B5	−115.89 (11)	B2—B5—B8—B7	−37.71 (12)
B4—B1—B3—B2	−112.89 (11)	B9—B5—B8—B7	−82.72 (10)
B5—B1—B3—B2	−55.44 (10)	B4—B5—B8—B7	44.23 (10)
B4—B1—B3—B7	−23.54 (11)	B3—B7—B8—B10	−109.60 (12)
B2—B1—B3—B7	89.35 (11)	B4—B7—B8—B10	−154.69 (12)
B5—B1—B3—B7	33.91 (14)	B6—B7—B8—B10	−50.17 (9)
B4—B1—B3—B6	−89.42 (12)	B10—B7—B8—B9	50.51 (9)
B2—B1—B3—B6	23.47 (11)	B3—B7—B8—B9	−59.09 (10)
B5—B1—B3—B6	−31.97 (15)	B4—B7—B8—B9	−104.18 (10)
B2—B1—B3—B4	112.89 (11)	B6—B7—B8—B9	0.34 (9)
B5—B1—B3—B4	57.45 (10)	B10—B7—B8—B4	154.69 (12)
N1—B2—B3—B1	−103.53 (16)	B3—B7—B8—B4	45.09 (10)
B9—B2—B3—B1	110.09 (12)	B6—B7—B8—B4	104.52 (10)
B6—B2—B3—B1	154.75 (12)	B10—B7—B8—B5	109.80 (12)
B5—B2—B3—B1	49.94 (10)	B3—B7—B8—B5	0.21 (12)
N1—B2—B3—B7	147.20 (13)	B4—B7—B8—B5	−44.89 (10)
B1—B2—B3—B7	−109.27 (12)	B6—B7—B8—B5	59.63 (10)
B9—B2—B3—B7	0.82 (12)	N1—B2—B9—B10	−131.89 (12)
B6—B2—B3—B7	45.48 (10)	B1—B2—B9—B10	80.93 (14)
B5—B2—B3—B7	−59.33 (11)	B6—B2—B9—B10	−24.71 (11)
N1—B2—B3—B6	101.72 (15)	B3—B2—B9—B10	20.03 (14)
B1—B2—B3—B6	−154.75 (12)	B5—B2—B9—B10	104.75 (13)
B9—B2—B3—B6	−44.66 (10)	N1—B2—B9—B8	168.73 (11)
B5—B2—B3—B6	−104.81 (10)	B1—B2—B9—B8	21.55 (14)
N1—B2—B3—B4	−153.98 (14)	B6—B2—B9—B8	−84.09 (10)
B1—B2—B3—B4	−50.45 (10)	B3—B2—B9—B8	−39.35 (12)
B9—B2—B3—B4	59.64 (11)	B5—B2—B9—B8	45.37 (10)
B6—B2—B3—B4	104.30 (10)	N1—B2—B9—B5	123.36 (13)
B5—B2—B3—B4	−0.51 (10)	B1—B2—B9—B5	−23.82 (11)
B2—B1—B4—B7	−33.46 (14)	B6—B2—B9—B5	−129.46 (11)
B3—B1—B4—B7	23.61 (11)	B3—B2—B9—B5	−84.72 (11)
B5—B1—B4—B7	−90.62 (12)	N1—B2—B9—B6	−107.18 (12)
B2—B1—B4—B8	33.20 (14)	B1—B2—B9—B6	105.64 (12)
B3—B1—B4—B8	90.27 (12)	B3—B2—B9—B6	44.74 (10)
B5—B1—B4—B8	−23.95 (11)	B5—B2—B9—B6	129.46 (11)
B2—B1—B4—B3	−57.07 (9)	B4—B8—B9—B10	−109.00 (11)
B5—B1—B4—B3	−114.23 (10)	B5—B8—B9—B10	−154.48 (11)
B2—B1—B4—B5	57.16 (10)	B7—B8—B9—B10	−50.25 (9)
B3—B1—B4—B5	114.23 (10)	B10—B8—B9—B2	109.17 (11)
B2—B3—B4—B1	50.92 (9)	B4—B8—B9—B2	0.17 (12)
B7—B3—B4—B1	154.65 (11)	B5—B8—B9—B2	−45.31 (9)
B6—B3—B4—B1	109.46 (11)	B7—B8—B9—B2	58.92 (10)
B1—B3—B4—B7	−154.65 (11)	B10—B8—B9—B5	154.48 (11)
B2—B3—B4—B7	−103.73 (10)	B4—B8—B9—B5	45.48 (10)
B6—B3—B4—B7	−45.19 (9)	B7—B8—B9—B5	104.23 (10)
B1—B3—B4—B8	−109.43 (12)	B10—B8—B9—B6	49.91 (9)
B2—B3—B4—B8	−58.51 (11)	B4—B8—B9—B6	−59.09 (11)
B7—B3—B4—B8	45.22 (10)	B5—B8—B9—B6	−104.57 (10)
B6—B3—B4—B8	0.04 (13)	B7—B8—B9—B6	−0.34 (9)
B1—B3—B4—B5	−50.42 (9)	B1—B5—B9—B10	−79.76 (14)
B2—B3—B4—B5	0.50 (9)	B2—B5—B9—B10	−103.02 (12)
B7—B3—B4—B5	104.24 (10)	B8—B5—B9—B10	23.29 (11)
B6—B3—B4—B5	59.05 (11)	B4—B5—B9—B10	−21.36 (14)
B4—B1—B5—B2	112.78 (11)	B1—B5—B9—B2	23.26 (11)
B3—B1—B5—B2	55.43 (10)	B8—B5—B9—B2	126.31 (10)
B4—B1—B5—B8	23.76 (11)	B4—B5—B9—B2	81.66 (10)
B2—B1—B5—B8	−89.02 (12)	B1—B5—B9—B8	−103.05 (13)
B3—B1—B5—B8	−33.59 (14)	B2—B5—B9—B8	−126.31 (10)
B4—B1—B5—B9	88.92 (12)	B4—B5—B9—B8	−44.66 (10)
B2—B1—B5—B9	−23.85 (11)	B1—B5—B9—B6	−19.93 (15)
B3—B1—B5—B9	31.57 (14)	B2—B5—B9—B6	−43.19 (10)
B2—B1—B5—B4	−112.78 (11)	B8—B5—B9—B6	83.12 (10)
B3—B1—B5—B4	−57.35 (10)	B4—B5—B9—B6	38.47 (12)
N1—B2—B5—B1	103.70 (15)	B2—B6—B9—B10	152.64 (12)
B9—B2—B5—B1	−154.29 (12)	B3—B6—B9—B10	108.96 (12)
B6—B2—B5—B1	−110.36 (11)	B7—B6—B9—B10	50.37 (9)
B3—B2—B5—B1	−49.90 (9)	B10—B6—B9—B2	−152.64 (12)
N1—B2—B5—B8	−147.21 (13)	B3—B6—B9—B2	−43.68 (10)
B1—B2—B5—B8	109.10 (12)	B7—B6—B9—B2	−102.27 (10)
B9—B2—B5—B8	−45.19 (9)	B10—B6—B9—B8	−50.02 (9)
B6—B2—B5—B8	−1.26 (12)	B2—B6—B9—B8	102.62 (10)
B3—B2—B5—B8	59.19 (10)	B3—B6—B9—B8	58.94 (11)
N1—B2—B5—B9	−102.01 (15)	B7—B6—B9—B8	0.34 (9)
B1—B2—B5—B9	154.29 (12)	B10—B6—B9—B5	−109.36 (12)
B6—B2—B5—B9	43.93 (9)	B2—B6—B9—B5	43.28 (10)
B3—B2—B5—B9	104.38 (10)	B3—B6—B9—B5	−0.40 (13)
N1—B2—B5—B4	154.11 (13)	B7—B6—B9—B5	−59.00 (11)
B1—B2—B5—B4	50.41 (9)	B4—B8—B10—B9	90.44 (12)
B9—B2—B5—B4	−103.88 (10)	B5—B8—B10—B9	23.96 (11)
B6—B2—B5—B4	−59.94 (10)	B7—B8—B10—B9	113.94 (10)
B3—B2—B5—B4	0.51 (9)	B9—B8—B10—B6	−56.60 (9)
B7—B4—B5—B1	109.29 (12)	B4—B8—B10—B6	33.84 (14)
B8—B4—B5—B1	154.30 (12)	B5—B8—B10—B6	−32.64 (13)
B3—B4—B5—B1	50.43 (9)	B7—B8—B10—B6	57.33 (10)
B1—B4—B5—B2	−50.93 (9)	B9—B8—B10—B7	−113.94 (10)
B7—B4—B5—B2	58.36 (11)	B4—B8—B10—B7	−23.49 (11)
B8—B4—B5—B2	103.37 (10)	B5—B8—B10—B7	−89.98 (12)
B3—B4—B5—B2	−0.50 (9)	B2—B9—B10—B8	−89.45 (11)
B1—B4—B5—B8	−154.30 (12)	B5—B9—B10—B8	−23.94 (11)
B7—B4—B5—B8	−45.02 (10)	B6—B9—B10—B8	−114.82 (10)
B3—B4—B5—B8	−103.87 (10)	B2—B9—B10—B6	25.38 (11)
B1—B4—B5—B9	−109.50 (12)	B8—B9—B10—B6	114.82 (10)
B7—B4—B5—B9	−0.21 (13)	B5—B9—B10—B6	90.88 (11)
B8—B4—B5—B9	44.81 (10)	B2—B9—B10—B7	−31.89 (14)
B3—B4—B5—B9	−59.07 (11)	B8—B9—B10—B7	57.55 (10)
N1—B2—B6—B10	132.36 (12)	B5—B9—B10—B7	33.62 (14)
B1—B2—B6—B10	−80.28 (14)	B6—B9—B10—B7	−57.27 (10)
B9—B2—B6—B10	24.67 (10)	B2—B6—B10—B8	31.12 (13)
B3—B2—B6—B10	−103.74 (12)	B9—B6—B10—B8	56.38 (9)
B5—B2—B6—B10	−19.16 (13)	B3—B6—B10—B8	−33.73 (13)
N1—B2—B6—B9	107.69 (12)	B7—B6—B10—B8	−57.59 (10)
B1—B2—B6—B9	−104.95 (13)	B2—B6—B10—B9	−25.26 (10)
B3—B2—B6—B9	−128.41 (11)	B3—B6—B10—B9	−90.11 (11)
B5—B2—B6—B9	−43.83 (9)	B7—B6—B10—B9	−113.97 (11)
N1—B2—B6—B3	−123.90 (13)	B2—B6—B10—B7	88.71 (11)
B1—B2—B6—B3	23.46 (11)	B9—B6—B10—B7	113.97 (11)
B9—B2—B6—B3	128.41 (11)	B3—B6—B10—B7	23.86 (11)
B5—B2—B6—B3	84.58 (11)	B3—B7—B10—B8	89.79 (12)
N1—B2—B6—B7	−168.65 (10)	B4—B7—B10—B8	23.47 (11)
B1—B2—B6—B7	−21.29 (13)	B6—B7—B10—B8	114.01 (11)
B9—B2—B6—B7	83.66 (10)	B3—B7—B10—B9	32.88 (14)
B3—B2—B6—B7	−44.75 (9)	B4—B7—B10—B9	−33.43 (14)
B5—B2—B6—B7	39.83 (11)	B6—B7—B10—B9	57.10 (10)
B1—B3—B6—B10	80.18 (14)	B8—B7—B10—B9	−56.90 (10)
B2—B3—B6—B10	103.08 (12)	B3—B7—B10—B6	−24.22 (11)
B7—B3—B6—B10	−23.35 (10)	B4—B7—B10—B6	−90.53 (12)
B4—B3—B6—B10	21.49 (14)	B8—B7—B10—B6	−114.01 (11)
B1—B3—B6—B2	−22.90 (11)

Experimental details

Crystal data
Chemical formula	C₁₆H₃₆N⁺·C₁₀H₂₀B₁₀N₃O₃⁻
M_r	580.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.7356 (4), 15.8691 (6), 24.7015 (10)
β (°)	98.206 (1)
V (Å³)	3389.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.161, 0.374
No. of measured, independent and observed [I > 2σ(I)] reflections	35977, 10868, 6806
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.728

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.142, 0.94
No. of reflections	10868
No. of parameters	388
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.51

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Russian Fund for Basic Research (grants11–03–00262 and 11–03–90417), the Federal Targeted Program Scientific and Scientific-Pedagogical Personnel of Innovative Russia in 2009–2013 (contract P1294 from 09/06/2010) and the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041). ALM expresses his gratitude to the Government of Saint-Petersburg for a grant for graduate and undergraduate students (2011). Financial support from the Visby Program through the Swedish Institute is gratefully acknowledged.

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