Tetra-butyl-ammonium 2-[2,5-dimethyl-3-(4-nitro-phen-yl)-2,3-dihydro-1,2,4-oxadiazo-lium-4-yl]nona-hydro-closo-deca-borate.

The title ionic compound, C16H36N(+)·C10H20B10N3O3(-), consists of a tetra-butyl-ammonium cation and a closo-deca-borate 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 deca-borate 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 = 580.85

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.142

S = 0.94

10868 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044984/aa2067sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H36N+·C10H20B10N3O3−	F(000) = 1256
Mr = 580.85	Dx = 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

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

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(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3
10868 reflections	(Δ/σ)max < 0.001
388 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)