supplementary materials


aa2067 scheme

Acta Cryst. (2012). E68, o3284-o3285    [ doi:10.1107/S1600536812044984 ]

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

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

Abstract top

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.

Comment top

In the past decade, a great attention has been paid to electrophilic activation of the CN 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 CN 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.

Refinement top

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 > 2σ(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.

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
[Figure 1] Fig. 1. A packing view of the title compound.
[Figure 2] 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+·C10H20B10N3O3F(000) = 1256
Mr = 580.85Dx = 1.138 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6524 reflections
a = 8.7356 (4) Åθ = 2.6–30.8°
b = 15.8691 (6) ŵ = 0.07 mm1
c = 24.7015 (10) ÅT = 100 K
β = 98.206 (1)°Block, colorless
V = 3389.2 (2) Å30.35 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEXII DUO CCD
diffractometer
10868 independent reflections
Radiation source: fine-focus sealed tube6806 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
φ and ω scansθmax = 31.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 126
Tmin = 0.161, Tmax = 0.374k = 2320
35977 measured reflectionsl = 3435
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-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 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.51 e Å3
Crystal data top
C16H36N+·C10H20B10N3O3V = 3389.2 (2) Å3
Mr = 580.85Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7356 (4) ŵ = 0.07 mm1
b = 15.8691 (6) ÅT = 100 K
c = 24.7015 (10) Å0.35 × 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)
Tmin = 0.161, Tmax = 0.374Rint = 0.086
35977 measured reflectionsθmax = 31.2°
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.142Δρmax = 0.55 e Å3
S = 0.94Δρmin = 0.51 e Å3
10868 reflectionsAbsolute structure: ?
388 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
N41.06470 (12)0.31892 (7)0.19722 (4)0.0152 (2)
C1A0.99038 (15)0.30280 (8)0.25556 (5)0.0166 (3)
H1AA1.07160.29480.27810.020*
H1AB0.93230.35250.26890.020*
C2A0.88276 (16)0.22708 (8)0.26301 (6)0.0189 (3)
H2AA0.78300.24200.25280.023*
H2AB0.92570.18140.23950.023*
C3A0.86245 (16)0.19856 (9)0.32259 (6)0.0211 (3)
H3AA0.83260.24650.34610.025*
H3AB0.96050.17760.33120.025*
C4A0.7411 (2)0.13008 (9)0.33407 (6)0.0311 (4)
H4AA0.73110.11430.37190.047*
H4AB0.64370.15070.32590.047*
H4AC0.77180.08190.31170.047*
C1B0.94265 (15)0.32580 (8)0.15940 (5)0.0164 (3)
H1BA0.99440.33200.12220.020*
H1BB0.88470.27350.16120.020*
C2B0.82901 (16)0.39833 (8)0.17181 (6)0.0198 (3)
H2BA0.76410.38820.20640.024*
H2BB0.88540.45040.17490.024*
C3B0.72812 (17)0.40682 (9)0.12650 (6)0.0232 (3)
H3BA0.79460.41440.09190.028*
H3BB0.66490.45700.13320.028*
C4B0.62259 (17)0.33156 (10)0.12169 (7)0.0273 (3)
H4BA0.56350.34100.09230.041*
H4BB0.68410.28160.11440.041*
H4BC0.55370.32470.15530.041*
C1C1.16972 (15)0.24577 (8)0.17577 (5)0.0168 (3)
H1CA1.23020.26290.14150.020*
H1CB1.10510.19890.16790.020*
C2C1.28027 (16)0.21468 (8)0.21379 (6)0.0182 (3)
H2CA1.33610.26200.22630.022*
H2CB1.22230.18770.24550.022*
C3C1.39420 (15)0.15209 (8)0.18342 (6)0.0194 (3)
H3CA1.44610.17820.15030.023*
H3CB1.33800.10340.17290.023*
C4C1.51453 (17)0.12333 (10)0.21844 (7)0.0282 (3)
H4CA1.58310.08350.19830.042*
H4CB1.57270.17110.22790.042*
H4CC1.46360.09730.25120.042*
C1D1.15761 (16)0.40003 (8)0.19808 (6)0.0172 (3)
H1DA1.24400.38940.21780.021*
H1DB1.09250.44200.21850.021*
C2D1.22037 (16)0.43691 (8)0.14269 (6)0.0194 (3)
H2DA1.28820.39640.12200.023*
H2DB1.13550.44870.12250.023*
C3D1.30961 (19)0.51795 (9)0.14965 (6)0.0260 (3)
H3DA1.39310.50590.17050.031*
H3DB1.24100.55830.17020.031*
C4D1.3761 (2)0.55653 (10)0.09510 (6)0.0320 (4)
H4DA1.43140.60710.10130.048*
H4DB1.44550.51710.07480.048*
H4DC1.29360.56970.07470.048*
O10.54528 (11)0.16501 (6)0.01773 (4)0.0202 (2)
N10.74065 (12)0.12499 (6)0.04378 (4)0.0144 (2)
N20.66334 (12)0.13225 (7)0.05053 (5)0.0165 (2)
C10.59955 (15)0.15096 (8)0.03466 (6)0.0168 (3)
C20.49407 (16)0.17008 (9)0.07497 (6)0.0222 (3)
H2A0.39570.18790.05610.033*
H2B0.53770.21430.09890.033*
H2C0.48050.12050.09610.033*
C40.60748 (16)0.04754 (8)0.06730 (6)0.0182 (3)
H4A0.51610.05210.09380.027*
H4B0.58370.01710.03590.027*
H4C0.68620.01800.08310.027*
C50.80327 (15)0.12692 (8)0.00925 (5)0.0148 (3)
H50.85790.07410.01400.018*
C60.91407 (15)0.20041 (8)0.00974 (5)0.0156 (3)
C70.87874 (16)0.28045 (8)0.00783 (6)0.0206 (3)
H70.78200.29080.01800.025*
C80.98651 (17)0.34482 (9)0.01034 (6)0.0222 (3)
H80.96300.39860.02160.027*
C91.13015 (16)0.32699 (8)0.00431 (5)0.0181 (3)
C101.16758 (15)0.24852 (8)0.02307 (5)0.0172 (3)
H101.26410.23860.03360.021*
C111.05790 (15)0.18518 (8)0.02585 (5)0.0163 (3)
H111.08040.13210.03860.020*
N31.24830 (15)0.39366 (8)0.00029 (5)0.0226 (3)
O3A1.21039 (14)0.46527 (6)0.01226 (5)0.0338 (3)
O3B1.37898 (12)0.37441 (7)0.00819 (5)0.0314 (3)
B10.84962 (19)0.16988 (10)0.15185 (7)0.0202 (3)
H120.79880.23240.15570.030*
B20.84165 (17)0.10294 (9)0.09822 (6)0.0152 (3)
B30.78915 (18)0.07008 (10)0.16335 (6)0.0185 (3)
H130.67640.06090.17770.028*
B40.97278 (19)0.11400 (10)0.19715 (7)0.0219 (3)
H141.00380.13990.23750.033*
B51.02284 (18)0.14771 (10)0.13054 (7)0.0190 (3)
H151.09970.20060.12110.028*
B60.85624 (17)0.00739 (9)0.11691 (6)0.0151 (3)
H160.77070.05060.09290.023*
B70.94918 (18)0.00066 (10)0.18820 (6)0.0185 (3)
H170.94110.03800.22460.028*
B81.11443 (18)0.05523 (10)0.16491 (7)0.0192 (3)
H181.24260.06010.18340.029*
B91.02020 (17)0.04734 (9)0.09450 (6)0.0153 (3)
H191.06440.04700.05340.023*
B101.04235 (17)0.03695 (9)0.13722 (6)0.0163 (3)
H201.09710.09920.13440.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N40.0155 (5)0.0132 (5)0.0167 (6)0.0006 (4)0.0018 (5)0.0020 (4)
C1A0.0177 (6)0.0160 (6)0.0154 (6)0.0003 (5)0.0001 (5)0.0019 (5)
C2A0.0218 (7)0.0156 (6)0.0190 (7)0.0022 (6)0.0023 (6)0.0006 (5)
C3A0.0226 (7)0.0204 (7)0.0204 (7)0.0004 (6)0.0031 (6)0.0005 (6)
C4A0.0443 (10)0.0247 (8)0.0240 (8)0.0107 (7)0.0033 (8)0.0059 (6)
C1B0.0174 (6)0.0148 (6)0.0172 (6)0.0002 (5)0.0036 (5)0.0017 (5)
C2B0.0182 (6)0.0153 (6)0.0259 (8)0.0010 (5)0.0036 (6)0.0030 (6)
C3B0.0204 (7)0.0210 (7)0.0285 (8)0.0039 (6)0.0043 (6)0.0015 (6)
C4B0.0222 (7)0.0287 (8)0.0319 (9)0.0020 (6)0.0066 (7)0.0055 (7)
C1C0.0170 (6)0.0151 (6)0.0179 (7)0.0027 (5)0.0012 (5)0.0046 (5)
C2C0.0197 (6)0.0171 (6)0.0182 (7)0.0007 (6)0.0037 (6)0.0026 (5)
C3C0.0166 (6)0.0169 (6)0.0246 (7)0.0005 (5)0.0033 (6)0.0035 (5)
C4C0.0217 (7)0.0273 (8)0.0367 (9)0.0038 (6)0.0073 (7)0.0018 (7)
C1D0.0183 (6)0.0134 (6)0.0196 (7)0.0020 (5)0.0019 (6)0.0032 (5)
C2D0.0203 (7)0.0185 (7)0.0194 (7)0.0023 (6)0.0027 (6)0.0001 (5)
C3D0.0312 (8)0.0235 (7)0.0225 (8)0.0100 (7)0.0008 (7)0.0012 (6)
C4D0.0419 (10)0.0286 (8)0.0258 (8)0.0187 (8)0.0067 (8)0.0048 (7)
O10.0172 (5)0.0238 (5)0.0190 (5)0.0083 (4)0.0009 (4)0.0019 (4)
N10.0149 (5)0.0131 (5)0.0152 (5)0.0010 (4)0.0022 (4)0.0014 (4)
N20.0140 (5)0.0173 (6)0.0181 (6)0.0036 (5)0.0019 (5)0.0028 (4)
C10.0178 (6)0.0140 (6)0.0182 (7)0.0022 (5)0.0014 (5)0.0010 (5)
C20.0179 (6)0.0272 (8)0.0218 (7)0.0063 (6)0.0035 (6)0.0033 (6)
C40.0161 (6)0.0186 (7)0.0190 (7)0.0002 (5)0.0001 (5)0.0032 (5)
C50.0148 (6)0.0139 (6)0.0155 (6)0.0022 (5)0.0015 (5)0.0004 (5)
C60.0170 (6)0.0145 (6)0.0144 (6)0.0018 (5)0.0002 (5)0.0003 (5)
C70.0199 (7)0.0166 (6)0.0261 (8)0.0025 (6)0.0060 (6)0.0010 (6)
C80.0274 (7)0.0151 (6)0.0246 (8)0.0013 (6)0.0059 (6)0.0019 (6)
C90.0213 (7)0.0166 (6)0.0155 (6)0.0045 (6)0.0005 (6)0.0000 (5)
C100.0163 (6)0.0201 (7)0.0146 (6)0.0009 (5)0.0006 (5)0.0021 (5)
C110.0176 (6)0.0153 (6)0.0154 (6)0.0030 (5)0.0004 (5)0.0001 (5)
N30.0275 (6)0.0213 (6)0.0184 (6)0.0065 (5)0.0014 (5)0.0000 (5)
O3A0.0450 (7)0.0185 (5)0.0398 (7)0.0090 (5)0.0124 (6)0.0067 (5)
O3B0.0245 (6)0.0327 (6)0.0367 (7)0.0082 (5)0.0033 (5)0.0027 (5)
B10.0221 (8)0.0176 (7)0.0194 (8)0.0033 (6)0.0020 (7)0.0053 (6)
B20.0143 (7)0.0152 (7)0.0159 (7)0.0005 (6)0.0012 (6)0.0001 (6)
B30.0192 (7)0.0227 (8)0.0138 (7)0.0045 (6)0.0025 (6)0.0015 (6)
B40.0229 (8)0.0223 (8)0.0190 (8)0.0051 (7)0.0020 (7)0.0069 (6)
B50.0171 (7)0.0145 (7)0.0236 (8)0.0001 (6)0.0028 (6)0.0043 (6)
B60.0151 (7)0.0151 (7)0.0151 (7)0.0008 (6)0.0020 (6)0.0015 (6)
B70.0190 (7)0.0197 (8)0.0163 (7)0.0034 (6)0.0007 (6)0.0012 (6)
B80.0165 (7)0.0188 (7)0.0206 (8)0.0019 (6)0.0030 (6)0.0031 (6)
B90.0142 (7)0.0136 (7)0.0179 (7)0.0003 (6)0.0015 (6)0.0015 (6)
B100.0158 (7)0.0154 (7)0.0176 (7)0.0020 (6)0.0015 (6)0.0001 (6)
Geometric parameters (Å, º) top
N4—C1A1.5154 (17)B2—B61.810 (2)
N4—C1B1.5184 (15)B2—B31.811 (2)
N4—C1D1.5234 (16)B2—B51.813 (2)
N4—C1C1.5268 (16)B3—B71.816 (2)
C1A—C2A1.5206 (18)B3—B61.834 (2)
C2A—C3A1.5255 (19)B3—B41.837 (2)
C3A—C4A1.516 (2)B4—B71.820 (2)
C1B—C2B1.5222 (18)B4—B81.821 (2)
C2B—C3B1.5261 (18)B4—B51.841 (2)
C3B—C4B1.524 (2)B5—B81.822 (2)
C1C—C2C1.5221 (17)B5—B91.823 (2)
C2C—C3C1.5254 (19)B6—B101.698 (2)
C3C—C4C1.5235 (18)B6—B91.827 (2)
C1D—C2D1.5168 (19)B6—B71.835 (2)
C2D—C3D1.5263 (18)B7—B101.702 (2)
C3D—C4D1.518 (2)B7—B81.844 (2)
O1—C11.3319 (16)B8—B101.697 (2)
O1—N21.4929 (13)B8—B91.819 (2)
N1—C11.2886 (16)B9—B101.698 (2)
N1—C51.4903 (15)C2—H2A0.9600
N1—B21.5397 (19)C2—H2B0.9600
N2—C41.4694 (16)C2—H2C0.9600
N2—C51.4781 (17)C4—H4A0.9600
C1—C21.4815 (17)C4—H4B0.9600
C5—C61.5167 (18)C4—H4C0.9600
C6—C71.3910 (18)C5—H50.9800
C6—C111.3923 (17)C7—H70.9300
C7—C81.3846 (19)C8—H80.9300
C8—C91.3839 (18)C10—H100.9300
C9—C101.3841 (18)C11—H110.9300
C9—N31.4710 (17)B1—H121.0971
C10—C111.3836 (18)B3—H131.1035
N3—O3B1.2283 (15)B4—H141.0770
N3—O3A1.2315 (15)B5—H151.1202
B1—B41.689 (2)B6—H161.1197
B1—B21.692 (2)B7—H171.0992
B1—B31.706 (2)B8—H181.1497
B1—B51.708 (2)B9—H191.1365
B2—B91.806 (2)B10—H201.1034
C1A—N4—C1B110.74 (10)B8—B4—B3102.17 (10)
C1A—N4—C1D106.63 (9)B1—B4—B557.68 (9)
C1B—N4—C1D111.72 (9)B7—B4—B5102.46 (10)
C1A—N4—C1C110.87 (10)B8—B4—B559.68 (8)
C1B—N4—C1C106.32 (9)B3—B4—B590.43 (10)
C1D—N4—C1C110.63 (10)B1—B5—B257.33 (9)
N4—C1A—C2A114.97 (10)B1—B5—B8111.81 (11)
C1A—C2A—C3A109.64 (10)B2—B5—B8100.79 (10)
C4A—C3A—C2A112.03 (11)B1—B5—B9112.36 (11)
N4—C1B—C2B115.18 (10)B2—B5—B959.55 (8)
C1B—C2B—C3B110.33 (11)B8—B5—B959.87 (8)
C4B—C3B—C2B114.02 (12)B1—B5—B456.68 (9)
C2C—C1C—N4115.79 (10)B2—B5—B488.61 (10)
C1C—C2C—C3C109.55 (11)B8—B5—B459.61 (9)
C4C—C3C—C2C111.75 (11)B9—B5—B4101.21 (10)
C2D—C1D—N4115.98 (10)B10—B6—B2111.85 (11)
C1D—C2D—C3D110.38 (11)B10—B6—B957.44 (8)
C4D—C3D—C2D112.14 (12)B2—B6—B959.52 (8)
C1—O1—N2106.93 (9)B10—B6—B3112.24 (11)
C1—N1—C5107.55 (11)B2—B6—B359.61 (8)
C1—N1—B2129.79 (11)B9—B6—B3101.84 (10)
C5—N1—B2122.41 (10)B10—B6—B757.44 (9)
C4—N2—C5110.54 (10)B2—B6—B7100.53 (10)
C4—N2—O1104.14 (9)B9—B6—B789.95 (10)
C5—N2—O1102.30 (9)B3—B6—B759.35 (8)
N1—C1—O1114.99 (11)B10—B7—B3112.88 (11)
N1—C1—C2128.25 (13)B10—B7—B4112.24 (11)
O1—C1—C2116.72 (12)B3—B7—B460.67 (9)
N2—C5—N1103.67 (9)B10—B7—B657.21 (8)
N2—C5—C6114.61 (10)B3—B7—B660.28 (8)
N1—C5—C6109.72 (10)B4—B7—B6102.25 (10)
C7—C6—C11119.81 (12)B10—B7—B857.02 (8)
C7—C6—C5121.97 (11)B3—B7—B8102.05 (10)
C11—C6—C5118.14 (11)B4—B7—B859.59 (8)
C8—C7—C6120.53 (12)B6—B7—B889.55 (9)
C9—C8—C7118.26 (12)B10—B8—B957.60 (9)
C8—C9—C10122.54 (13)B10—B8—B4112.42 (11)
C8—C9—N3119.02 (12)B9—B8—B4102.14 (11)
C10—C9—N3118.45 (12)B10—B8—B5113.16 (12)
C11—C10—C9118.38 (12)B9—B8—B560.09 (8)
C10—C11—C6120.43 (12)B4—B8—B560.71 (9)
O3B—N3—O3A123.98 (12)B10—B8—B757.27 (8)
O3B—N3—C9117.83 (12)B9—B8—B789.91 (10)
O3A—N3—C9118.20 (12)B4—B8—B759.54 (9)
B4—B1—B298.06 (11)B5—B8—B7102.26 (10)
B4—B1—B365.50 (10)B10—B9—B2112.08 (10)
B2—B1—B364.43 (9)B10—B9—B857.59 (9)
B4—B1—B565.64 (10)B2—B9—B8101.18 (10)
B2—B1—B564.45 (9)B10—B9—B5113.11 (11)
B3—B1—B599.74 (11)B2—B9—B559.94 (8)
N1—B2—B1119.71 (11)B8—B9—B560.04 (9)
N1—B2—B9117.26 (10)B10—B9—B657.44 (8)
B1—B2—B9114.04 (11)B2—B9—B659.78 (8)
N1—B2—B6116.95 (11)B8—B9—B690.59 (9)
B1—B2—B6114.46 (11)B5—B9—B6102.89 (10)
B9—B2—B660.70 (8)B8—B10—B964.80 (9)
N1—B2—B3130.92 (11)B8—B10—B699.52 (11)
B1—B2—B358.18 (9)B9—B10—B665.12 (9)
B9—B2—B3103.57 (10)B8—B10—B765.71 (9)
B6—B2—B360.84 (8)B9—B10—B799.18 (11)
N1—B2—B5130.61 (11)B6—B10—B765.35 (9)
B1—B2—B558.22 (9)C1—C2—H2A109.5
B9—B2—B560.51 (8)C1—C2—H2B109.5
B6—B2—B5103.97 (10)H2A—C2—H2B109.5
B3—B2—B592.16 (10)C1—C2—H2C109.5
B1—B3—B257.39 (9)H2A—C2—H2C109.5
B1—B3—B7112.18 (11)H2B—C2—H2C109.5
B2—B3—B7101.22 (10)N2—C4—H4A109.5
B1—B3—B6112.57 (10)N2—C4—H4B109.5
B2—B3—B659.56 (8)H4A—C4—H4B109.5
B7—B3—B660.37 (8)N2—C4—H4C109.5
B1—B3—B456.80 (9)H4A—C4—H4C109.5
B2—B3—B488.80 (10)H4B—C4—H4C109.5
B7—B3—B459.76 (9)N2—C5—H5109.5
B6—B3—B4101.67 (10)N1—C5—H5109.5
B1—B4—B7112.83 (12)C6—C5—H5109.5
B1—B4—B8112.80 (12)C8—C7—H7119.7
B7—B4—B860.86 (8)C6—C7—H7119.7
B1—B4—B357.70 (9)C9—C8—H8120.9
B7—B4—B359.57 (9)C7—C8—H8120.9
C1B—N4—C1A—C2A54.33 (14)B7—B3—B6—B2126.43 (11)
C1D—N4—C1A—C2A176.07 (11)B4—B3—B6—B281.59 (10)
C1C—N4—C1A—C2A63.44 (13)B1—B3—B6—B920.73 (15)
N4—C1A—C2A—C3A159.65 (11)B2—B3—B6—B943.63 (9)
C1A—C2A—C3A—C4A172.99 (12)B7—B3—B6—B982.80 (10)
C1A—N4—C1B—C2B62.33 (14)B4—B3—B6—B937.96 (12)
C1D—N4—C1B—C2B56.37 (15)B1—B3—B6—B7103.53 (13)
C1C—N4—C1B—C2B177.15 (11)B2—B3—B6—B7126.43 (11)
N4—C1B—C2B—C3B171.56 (11)B4—B3—B6—B744.84 (10)
C1B—C2B—C3B—C4B64.75 (16)B1—B3—B7—B1080.78 (14)
C1A—N4—C1C—C2C47.08 (14)B2—B3—B7—B1021.61 (14)
C1B—N4—C1C—C2C167.50 (11)B6—B3—B7—B1023.40 (11)
C1D—N4—C1C—C2C71.01 (14)B4—B3—B7—B10103.54 (12)
N4—C1C—C2C—C3C170.86 (11)B1—B3—B7—B422.76 (11)
C1C—C2C—C3C—C4C176.20 (12)B2—B3—B7—B481.93 (10)
C1A—N4—C1D—C2D169.95 (11)B6—B3—B7—B4126.94 (10)
C1B—N4—C1D—C2D48.84 (15)B1—B3—B7—B6104.18 (12)
C1C—N4—C1D—C2D69.41 (13)B2—B3—B7—B645.01 (9)
N4—C1D—C2D—C3D179.60 (11)B4—B3—B7—B6126.94 (10)
C1D—C2D—C3D—C4D179.35 (13)B1—B3—B7—B821.72 (14)
C1—O1—N2—C496.65 (11)B2—B3—B7—B837.46 (12)
C1—O1—N2—C518.51 (12)B6—B3—B7—B882.46 (10)
C5—N1—C1—O15.28 (15)B4—B3—B7—B844.48 (10)
B2—N1—C1—O1179.62 (11)B1—B4—B7—B1081.48 (14)
C5—N1—C1—C2172.03 (13)B8—B4—B7—B1022.80 (11)
B2—N1—C1—C22.3 (2)B3—B4—B7—B10104.60 (12)
N2—O1—C1—N18.72 (15)B5—B4—B7—B1021.55 (15)
N2—O1—C1—C2173.65 (11)B1—B4—B7—B323.12 (11)
C4—N2—C5—N189.84 (11)B8—B4—B7—B3127.40 (11)
O1—N2—C5—N120.57 (11)B5—B4—B7—B383.05 (11)
C4—N2—C5—C6150.60 (10)B1—B4—B7—B622.14 (14)
O1—N2—C5—C698.99 (11)B8—B4—B7—B682.14 (10)
C1—N1—C5—N216.91 (13)B3—B4—B7—B645.26 (9)
B2—N1—C5—N2168.24 (10)B5—B4—B7—B637.79 (12)
C1—N1—C5—C6105.94 (12)B1—B4—B7—B8104.28 (13)
B2—N1—C5—C668.91 (14)B3—B4—B7—B8127.40 (11)
N2—C5—C6—C770.62 (16)B5—B4—B7—B844.35 (10)
N1—C5—C6—C745.51 (17)B2—B6—B7—B10109.30 (11)
N2—C5—C6—C11112.55 (13)B9—B6—B7—B1050.36 (9)
N1—C5—C6—C11131.33 (12)B3—B6—B7—B10154.20 (11)
C11—C6—C7—C81.1 (2)B10—B6—B7—B3154.20 (11)
C5—C6—C7—C8175.64 (13)B2—B6—B7—B344.90 (9)
C6—C7—C8—C90.9 (2)B9—B6—B7—B3103.84 (10)
C7—C8—C9—C102.3 (2)B10—B6—B7—B4108.71 (11)
C7—C8—C9—N3177.48 (13)B2—B6—B7—B40.58 (11)
C8—C9—C10—C111.7 (2)B9—B6—B7—B458.35 (10)
N3—C9—C10—C11178.13 (12)B3—B6—B7—B445.48 (9)
C9—C10—C11—C60.43 (19)B10—B6—B7—B850.02 (9)
C7—C6—C11—C101.8 (2)B2—B6—B7—B859.27 (10)
C5—C6—C11—C10175.09 (12)B9—B6—B7—B80.34 (9)
C8—C9—N3—O3B173.56 (13)B3—B6—B7—B8104.18 (10)
C10—C9—N3—O3B6.26 (19)B1—B4—B8—B1081.44 (15)
C8—C9—N3—O3A6.58 (19)B7—B4—B8—B1022.89 (11)
C10—C9—N3—O3A173.61 (13)B3—B4—B8—B1021.59 (15)
C1—N1—B2—B147.65 (19)B5—B4—B8—B10104.86 (13)
C5—N1—B2—B1125.96 (13)B1—B4—B8—B921.70 (15)
C1—N1—B2—B9167.10 (13)B7—B4—B8—B982.63 (10)
C5—N1—B2—B919.29 (16)B3—B4—B8—B938.14 (12)
C1—N1—B2—B697.94 (15)B5—B4—B8—B945.12 (9)
C5—N1—B2—B688.46 (13)B1—B4—B8—B523.42 (11)
C1—N1—B2—B324.4 (2)B7—B4—B8—B5127.75 (11)
C5—N1—B2—B3162.03 (12)B3—B4—B8—B583.27 (11)
C1—N1—B2—B5119.62 (16)B1—B4—B8—B7104.33 (13)
C5—N1—B2—B553.98 (18)B3—B4—B8—B744.49 (10)
B4—B1—B2—N1179.91 (11)B5—B4—B8—B7127.75 (11)
B3—B1—B2—N1122.24 (13)B1—B5—B8—B1080.67 (14)
B5—B1—B2—N1121.88 (13)B2—B5—B8—B1021.70 (14)
B4—B1—B2—B933.61 (14)B9—B5—B8—B1023.30 (10)
B3—B1—B2—B991.46 (12)B4—B5—B8—B10103.64 (12)
B5—B1—B2—B924.42 (11)B1—B5—B8—B9103.97 (12)
B4—B1—B2—B633.70 (14)B2—B5—B8—B945.01 (9)
B3—B1—B2—B624.16 (11)B4—B5—B8—B9126.94 (11)
B5—B1—B2—B691.73 (12)B1—B5—B8—B422.97 (11)
B4—B1—B2—B357.86 (10)B2—B5—B8—B481.93 (10)
B5—B1—B2—B3115.89 (11)B9—B5—B8—B4126.94 (11)
B4—B1—B2—B558.03 (11)B1—B5—B8—B721.25 (14)
B3—B1—B2—B5115.89 (11)B2—B5—B8—B737.71 (12)
B4—B1—B3—B2112.89 (11)B9—B5—B8—B782.72 (10)
B5—B1—B3—B255.44 (10)B4—B5—B8—B744.23 (10)
B4—B1—B3—B723.54 (11)B3—B7—B8—B10109.60 (12)
B2—B1—B3—B789.35 (11)B4—B7—B8—B10154.69 (12)
B5—B1—B3—B733.91 (14)B6—B7—B8—B1050.17 (9)
B4—B1—B3—B689.42 (12)B10—B7—B8—B950.51 (9)
B2—B1—B3—B623.47 (11)B3—B7—B8—B959.09 (10)
B5—B1—B3—B631.97 (15)B4—B7—B8—B9104.18 (10)
B2—B1—B3—B4112.89 (11)B6—B7—B8—B90.34 (9)
B5—B1—B3—B457.45 (10)B10—B7—B8—B4154.69 (12)
N1—B2—B3—B1103.53 (16)B3—B7—B8—B445.09 (10)
B9—B2—B3—B1110.09 (12)B6—B7—B8—B4104.52 (10)
B6—B2—B3—B1154.75 (12)B10—B7—B8—B5109.80 (12)
B5—B2—B3—B149.94 (10)B3—B7—B8—B50.21 (12)
N1—B2—B3—B7147.20 (13)B4—B7—B8—B544.89 (10)
B1—B2—B3—B7109.27 (12)B6—B7—B8—B559.63 (10)
B9—B2—B3—B70.82 (12)N1—B2—B9—B10131.89 (12)
B6—B2—B3—B745.48 (10)B1—B2—B9—B1080.93 (14)
B5—B2—B3—B759.33 (11)B6—B2—B9—B1024.71 (11)
N1—B2—B3—B6101.72 (15)B3—B2—B9—B1020.03 (14)
B1—B2—B3—B6154.75 (12)B5—B2—B9—B10104.75 (13)
B9—B2—B3—B644.66 (10)N1—B2—B9—B8168.73 (11)
B5—B2—B3—B6104.81 (10)B1—B2—B9—B821.55 (14)
N1—B2—B3—B4153.98 (14)B6—B2—B9—B884.09 (10)
B1—B2—B3—B450.45 (10)B3—B2—B9—B839.35 (12)
B9—B2—B3—B459.64 (11)B5—B2—B9—B845.37 (10)
B6—B2—B3—B4104.30 (10)N1—B2—B9—B5123.36 (13)
B5—B2—B3—B40.51 (10)B1—B2—B9—B523.82 (11)
B2—B1—B4—B733.46 (14)B6—B2—B9—B5129.46 (11)
B3—B1—B4—B723.61 (11)B3—B2—B9—B584.72 (11)
B5—B1—B4—B790.62 (12)N1—B2—B9—B6107.18 (12)
B2—B1—B4—B833.20 (14)B1—B2—B9—B6105.64 (12)
B3—B1—B4—B890.27 (12)B3—B2—B9—B644.74 (10)
B5—B1—B4—B823.95 (11)B5—B2—B9—B6129.46 (11)
B2—B1—B4—B357.07 (9)B4—B8—B9—B10109.00 (11)
B5—B1—B4—B3114.23 (10)B5—B8—B9—B10154.48 (11)
B2—B1—B4—B557.16 (10)B7—B8—B9—B1050.25 (9)
B3—B1—B4—B5114.23 (10)B10—B8—B9—B2109.17 (11)
B2—B3—B4—B150.92 (9)B4—B8—B9—B20.17 (12)
B7—B3—B4—B1154.65 (11)B5—B8—B9—B245.31 (9)
B6—B3—B4—B1109.46 (11)B7—B8—B9—B258.92 (10)
B1—B3—B4—B7154.65 (11)B10—B8—B9—B5154.48 (11)
B2—B3—B4—B7103.73 (10)B4—B8—B9—B545.48 (10)
B6—B3—B4—B745.19 (9)B7—B8—B9—B5104.23 (10)
B1—B3—B4—B8109.43 (12)B10—B8—B9—B649.91 (9)
B2—B3—B4—B858.51 (11)B4—B8—B9—B659.09 (11)
B7—B3—B4—B845.22 (10)B5—B8—B9—B6104.57 (10)
B6—B3—B4—B80.04 (13)B7—B8—B9—B60.34 (9)
B1—B3—B4—B550.42 (9)B1—B5—B9—B1079.76 (14)
B2—B3—B4—B50.50 (9)B2—B5—B9—B10103.02 (12)
B7—B3—B4—B5104.24 (10)B8—B5—B9—B1023.29 (11)
B6—B3—B4—B559.05 (11)B4—B5—B9—B1021.36 (14)
B4—B1—B5—B2112.78 (11)B1—B5—B9—B223.26 (11)
B3—B1—B5—B255.43 (10)B8—B5—B9—B2126.31 (10)
B4—B1—B5—B823.76 (11)B4—B5—B9—B281.66 (10)
B2—B1—B5—B889.02 (12)B1—B5—B9—B8103.05 (13)
B3—B1—B5—B833.59 (14)B2—B5—B9—B8126.31 (10)
B4—B1—B5—B988.92 (12)B4—B5—B9—B844.66 (10)
B2—B1—B5—B923.85 (11)B1—B5—B9—B619.93 (15)
B3—B1—B5—B931.57 (14)B2—B5—B9—B643.19 (10)
B2—B1—B5—B4112.78 (11)B8—B5—B9—B683.12 (10)
B3—B1—B5—B457.35 (10)B4—B5—B9—B638.47 (12)
N1—B2—B5—B1103.70 (15)B2—B6—B9—B10152.64 (12)
B9—B2—B5—B1154.29 (12)B3—B6—B9—B10108.96 (12)
B6—B2—B5—B1110.36 (11)B7—B6—B9—B1050.37 (9)
B3—B2—B5—B149.90 (9)B10—B6—B9—B2152.64 (12)
N1—B2—B5—B8147.21 (13)B3—B6—B9—B243.68 (10)
B1—B2—B5—B8109.10 (12)B7—B6—B9—B2102.27 (10)
B9—B2—B5—B845.19 (9)B10—B6—B9—B850.02 (9)
B6—B2—B5—B81.26 (12)B2—B6—B9—B8102.62 (10)
B3—B2—B5—B859.19 (10)B3—B6—B9—B858.94 (11)
N1—B2—B5—B9102.01 (15)B7—B6—B9—B80.34 (9)
B1—B2—B5—B9154.29 (12)B10—B6—B9—B5109.36 (12)
B6—B2—B5—B943.93 (9)B2—B6—B9—B543.28 (10)
B3—B2—B5—B9104.38 (10)B3—B6—B9—B50.40 (13)
N1—B2—B5—B4154.11 (13)B7—B6—B9—B559.00 (11)
B1—B2—B5—B450.41 (9)B4—B8—B10—B990.44 (12)
B9—B2—B5—B4103.88 (10)B5—B8—B10—B923.96 (11)
B6—B2—B5—B459.94 (10)B7—B8—B10—B9113.94 (10)
B3—B2—B5—B40.51 (9)B9—B8—B10—B656.60 (9)
B7—B4—B5—B1109.29 (12)B4—B8—B10—B633.84 (14)
B8—B4—B5—B1154.30 (12)B5—B8—B10—B632.64 (13)
B3—B4—B5—B150.43 (9)B7—B8—B10—B657.33 (10)
B1—B4—B5—B250.93 (9)B9—B8—B10—B7113.94 (10)
B7—B4—B5—B258.36 (11)B4—B8—B10—B723.49 (11)
B8—B4—B5—B2103.37 (10)B5—B8—B10—B789.98 (12)
B3—B4—B5—B20.50 (9)B2—B9—B10—B889.45 (11)
B1—B4—B5—B8154.30 (12)B5—B9—B10—B823.94 (11)
B7—B4—B5—B845.02 (10)B6—B9—B10—B8114.82 (10)
B3—B4—B5—B8103.87 (10)B2—B9—B10—B625.38 (11)
B1—B4—B5—B9109.50 (12)B8—B9—B10—B6114.82 (10)
B7—B4—B5—B90.21 (13)B5—B9—B10—B690.88 (11)
B8—B4—B5—B944.81 (10)B2—B9—B10—B731.89 (14)
B3—B4—B5—B959.07 (11)B8—B9—B10—B757.55 (10)
N1—B2—B6—B10132.36 (12)B5—B9—B10—B733.62 (14)
B1—B2—B6—B1080.28 (14)B6—B9—B10—B757.27 (10)
B9—B2—B6—B1024.67 (10)B2—B6—B10—B831.12 (13)
B3—B2—B6—B10103.74 (12)B9—B6—B10—B856.38 (9)
B5—B2—B6—B1019.16 (13)B3—B6—B10—B833.73 (13)
N1—B2—B6—B9107.69 (12)B7—B6—B10—B857.59 (10)
B1—B2—B6—B9104.95 (13)B2—B6—B10—B925.26 (10)
B3—B2—B6—B9128.41 (11)B3—B6—B10—B990.11 (11)
B5—B2—B6—B943.83 (9)B7—B6—B10—B9113.97 (11)
N1—B2—B6—B3123.90 (13)B2—B6—B10—B788.71 (11)
B1—B2—B6—B323.46 (11)B9—B6—B10—B7113.97 (11)
B9—B2—B6—B3128.41 (11)B3—B6—B10—B723.86 (11)
B5—B2—B6—B384.58 (11)B3—B7—B10—B889.79 (12)
N1—B2—B6—B7168.65 (10)B4—B7—B10—B823.47 (11)
B1—B2—B6—B721.29 (13)B6—B7—B10—B8114.01 (11)
B9—B2—B6—B783.66 (10)B3—B7—B10—B932.88 (14)
B3—B2—B6—B744.75 (9)B4—B7—B10—B933.43 (14)
B5—B2—B6—B739.83 (11)B6—B7—B10—B957.10 (10)
B1—B3—B6—B1080.18 (14)B8—B7—B10—B956.90 (10)
B2—B3—B6—B10103.08 (12)B3—B7—B10—B624.22 (11)
B7—B3—B6—B1023.35 (10)B4—B7—B10—B690.53 (12)
B4—B3—B6—B1021.49 (14)B8—B7—B10—B6114.01 (11)
B1—B3—B6—B222.90 (11)
Acknowledgements top

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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