N-Butyl­pyridinium undeca­chloro­carba­dodeca­borate and comparison with similar compounds

The title compound, C₉H₁₄N⁺·CHB₁₁Cl₁₁^-, was obtained in the course of our continuing studies of the low-melting salts of closo- and nido-carborane cage anions with alkyl­pyridinium and dialkyl­imidazolium cations. The title compound is the first example of a pyridinium salt of a perchlorinated carborane anion. The structure consists of one N-butyl­pyridinium cation counterbalanced by one perchlorinated carborane cage anion per asymmetric unit. By changing the counter-ion, different packings are observed, and to try to understand this the new structure is compared with five similar compounds.

S1. Comment

In the last decade, the low-melting salts of the family of the title compound, N-butylpyridinium undecachlorocarbadodecaborate, (I), have been studied (Larsen et al., 2000; Dymon et al., 2008; Reed et al., 2010). Recently, the perchlorinated carborane species became available due to the work of Ozerov and co-workers (Gu et al., 2010). Compound (I) is the first example of a pyridinium salt of a perchlorinated carborane anion. The general synthetic route to obtain such compounds involves metathesis of an alkylpyridinium halide with caesium carborane salts in dichloromethane, with concominent precipitation of the caesium halide by-product (for more details, see Experimental).

The structure of carborane (I) consists of one butylpyridinium cation counterbalanced by an undecachlorinated carborane cage anion per asymmetric unit (Fig. 1). Structural analysis of the cation shows no significant differences from a typical substituted pyridine. The larger ellipsoid observed for atom C1 is due to thermal movement of this terminal C atom of the alkyl chain. Thermal motion of atom C1 makes the C1—C2 bond shorter than a typical C—C distance [C1—C2 = 1.408 (15) Å]. In the anion, all B—B and B—Cl distances are ≈ 1.8 Å and the different torsion angles (near 0°) are within the expected parameters for undecachlorocarbadodecaborate.

An intermolecular analysis shows that atom Cl8 in the undecachlorinated carborane interacts through a halogen–π interaction with the N-butylpyridinium cation [B8—Cl8 → Cg1 = 3.768 (4) Å; Cg1 is the centroid of the pyridine ring] (halogen bonding is a highly directional interaction, more directional than hydrogen bonding and comparable in strength; Metrangolo et al., 2008). It is important to point out that there is no evidence of strong π–π interaction between the N-butylpyridinium rings, so we can presume that the driving force for the crystal packing is related to the hydrogen-bond interaction H10···Cl2ⁱ [2.94 (5) Å; symmetry code: (i) -x + 1, -y + 1, -z + 1] between undecachlorinated carboranes (see Fig. 2) (van den Berg & Seddon, 2003; Lu et al., 2007). It is interesting to note the short Cl1···Cl1ⁱⁱ distance of 3.410 (3) Å [symmetry code: (ii) -x + 1, y, -z + 1/2], suggesting an interaction between these atoms, in addition to the short H···Cl cation–anion distances [minimum distance: H1B···Cl2 = 2.8838 (15) Å].

A supramolecular analysis shows that the most relevant and strongest intermolecular interactions in this structure are clearly the already mentioned hydrogen bonds. A dimer-like anionic substructure can be described as a result of the above-mentioned contacts (Fig. 2). An adequate expansion allows the visualization of the infinite columnar arrangement built by the described dimeric units, where the alternating positions of the carborane are evidenced by the torsion angle between subsequent units [C10—Ce—Ceⁱⁱⁱ—C10ⁱⁱⁱ = 32.91°; Ce is the centroid of the undecachlorocarbadodecaborate; symmetry code: (iii) x, -y + 1, z + 1/2; see Table 1 for more details].

A similar columnar arrangement is formed by the counterions. The alkyl chains are located tail-to-tail in x, but shifted by around 4 Å [C1···C1^iv = 4.09 (2) Å; symmetry code: (iv) -x + 1, y, -z + 1/2]. The aromatic rings of contiguous N-butylpyridinium cations in the column are alternating, with an angle of ~38° between phenyl rings [C7—N1—N1ⁱⁱⁱ—C7ⁱⁱⁱ = 38.2 (3)°; see Fig. 2].

The different packing arrangements of the undecachlorocarbadodecaborate were studied by the analysis of a set of five similar compounds (Fig. 3 and Table 1). One major difference observed in the crystal packing (Fig. 3) is related to the intermolecular C—H···Cl interactions between pairs of undecachlorocarbadodecaborate units. It was found that where the counter-ion is large, the carboranes associate in pairs to form column of dimers [Fig. 3; structures A, B (present structure) and C], but there is a variation in the torsion angle defined by the two C···Ce vectors in the dimers, and also in that relating the centroids of the undecachlorocarbadodecaborate into the double chain; the torsion angle changes as a result of the approach between dimers (shortest distance H···Cl). In the case of structure C, the first of these angles has increased to 76° which leads to the separations between chains being controlled by the H···Cl distance (being shorter and equal). In contrast, for the smaller cations (Fig. 3; structures D, E and F), single strands are formed, where there is a bifurcated interaction of the H atom with two Cl atoms of the adjacent undecachlorocarbadodecaborate unit. Adjacent channels can be coplanar or displaced. The overall packing is therefore seen to be a balance between the various interactions available along with the relative sizes and shapes of the components.

Related literature

For related literature, see: Berg & Seddon (2003); Dymon et al. (2008); Gu et al. (2010); Larsen et al. (2000); Lu et al. (2007); Metrangolo et al. (2008); Reed (2010).

S2. Experimental

The title compound was obtained by a metathesis reaction between caesium undecachlorocarbadodecaborate and N-butylpyridine in a dichloromethane–acetone mixture under aerobic conditions. N-Butylpyridine (100 mg) was dissolved in dichloromethane (20 ml). An equimolar quantity of caesium undecachlorocarbadodecaborate was dissolved in a dichloromethane–acetone mixture (1:1 v/v, 10 ml) and the resulting solution was added to the N-butylpyridine solution. The formation of a white precipitate was evident almost immediately. The reaction mixture was stirred at room temperature for 30 min. Subsequently, the solution was filtered through a Celite plug to remove the CsCl precipitate. The mother liquor was pumped off to dryness, the oily residue was redissolved in a small amount of dry dichloromethane and colourless scale-like crystals[white prisms in CIF - please clarify] of (I) were grown by slow vapour diffusion of hexane into a dichloromethane solution at 243 K.

S3. Refinement

Butyl H atoms were idealized at C—H = 0.96 Å and allowed to ride. Aromatic ring H atoms were idealized at C—H = 0.93 Å. In all cases, H-atom displacement parameters were taken as U_iso(H) = 1.5U_iso(C) for methyl groups or 1.2U_iso(C) otherwise. Atom H10 of the undecachlorocarbadodecaborate anion was located in a difference Fourier map and refined freely. [Please check added text]

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Please provide details; software used to prepare material for publication: Please provide details.

Figures

	Fig. 1. The molecular conformation and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The supramolecular interactions (dotted lines) in the crystal packing of (I).
	Fig. 3. The packing arrangements for undecachlorocarbadodecaborate with different counterions. A, B and C are larger counterions, and D, E and F are smaller counterions, where A is Me3—Si—H—Si—Me3, B is (I), C is (C3H7)3-Si-(ODCB), D is Me—Cl—Me, E is Et—Cl—Et and F is MeOH. [Stray/leftover labelling marked with arrows; please revise]

N-Butylpyridinium undecachlorocarbadodecaborate

Crystal data

C9H14N^+·CHB11Cl11^−	F(000) = 2592
Mr = 657.22	Dx = 1.575 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3175 reflections
a = 32.929 (3) Å	θ = 2.7–73.8°
b = 10.2492 (6) Å	µ = 1.11 mm^−1
c = 17.6340 (19) Å	T = 298 K
β = 111.100 (12)°	Prism, colourless
V = 5552.4 (9) Å^3	0.1 × 0.1 × 0.05 mm
Z = 8

Data collection

Oxford Gemini E CCD area-detector diffractometer	3411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
ω scans, thick slices	θmax = 26.3°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −39→40
Tmin = 0.203, Tmax = 1.000	k = −12→11
14744 measured reflections	l = −21→20
5577 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1378P)^2] where P = (Fo^2 + 2Fc^2)/3
5577 reflections	(Δ/σ)max < 0.001
302 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Special details

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

	x	y	z	Uiso*/Ueq
C1	0.5010 (3)	−0.0328 (12)	0.1347 (9)	0.181 (6)
H1A	0.5274	0.0163	0.1584	0.272*
H1B	0.4979	−0.0587	0.0806	0.272*
H1C	0.5022	−0.1089	0.1671	0.272*
C2	0.4653 (2)	0.0449 (11)	0.1320 (6)	0.134 (4)
H2A	0.4656	0.1226	0.1008	0.16*
H2B	0.4699	0.0727	0.187	0.16*
C3	0.4202 (2)	−0.0153 (8)	0.0965 (6)	0.100 (3)
H3A	0.4162	−0.0543	0.0442	0.12*
H3B	0.4172	−0.0835	0.1323	0.12*
C4	0.3865 (2)	0.0862 (7)	0.0865 (5)	0.086 (2)
H4A	0.3903	0.1548	0.0517	0.103*
H4B	0.3909	0.1244	0.1392	0.103*
C5	0.3231 (2)	0.0145 (7)	−0.0272 (4)	0.0754 (17)
H5	0.3392	0.0292	−0.0602	0.091*
C6	0.2812 (2)	−0.0283 (9)	−0.0617 (5)	0.096 (2)
H6	0.2687	−0.0422	−0.1174	0.115*
C7	0.2586 (2)	−0.0501 (9)	−0.0125 (6)	0.101 (3)
H7	0.2298	−0.0776	−0.0348	0.121*
C8	0.2771 (3)	−0.0327 (10)	0.0677 (6)	0.109 (3)
H8	0.2617	−0.0516	0.1015	0.13*
C9	0.3196 (3)	0.0140 (9)	0.1002 (5)	0.098 (3)
H9	0.3326	0.0297	0.1557	0.118*
Cl3	0.43277 (5)	0.58675 (17)	0.54893 (9)	0.0716 (4)
N1	0.34133 (15)	0.0358 (5)	0.0512 (3)	0.0644 (12)
H10	0.4638 (17)	0.569 (5)	0.404 (3)	0.052 (14)*
C10	0.43280 (16)	0.5290 (5)	0.3798 (3)	0.0534 (12)
B1	0.41794 (17)	0.4012 (6)	0.3124 (3)	0.0502 (12)
B2	0.42074 (18)	0.3834 (6)	0.4156 (4)	0.0517 (13)
B3	0.40600 (19)	0.5351 (6)	0.4474 (4)	0.0531 (13)
B4	0.39416 (19)	0.6480 (6)	0.3647 (4)	0.0542 (13)
B5	0.40189 (19)	0.5645 (6)	0.2810 (4)	0.0535 (13)
B6	0.36338 (18)	0.4362 (6)	0.2501 (4)	0.0498 (12)
B7	0.37492 (19)	0.3216 (6)	0.3323 (3)	0.0502 (12)
B8	0.36706 (18)	0.4063 (6)	0.4161 (3)	0.0496 (12)
B9	0.35124 (19)	0.5692 (6)	0.3854 (4)	0.0546 (13)
B10	0.34912 (19)	0.5900 (6)	0.2824 (4)	0.0561 (14)
B11	0.33177 (18)	0.4405 (6)	0.3139 (4)	0.0523 (13)
Cl1	0.45606 (5)	0.32163 (17)	0.27953 (10)	0.0723 (4)
Cl2	0.46167 (5)	0.28691 (17)	0.48432 (9)	0.0740 (4)
Cl4	0.40854 (6)	0.81386 (15)	0.38382 (11)	0.0779 (5)
Cl5	0.42476 (6)	0.64856 (18)	0.21881 (10)	0.0784 (5)
Cl6	0.34122 (5)	0.38479 (17)	0.14697 (8)	0.0684 (4)
Cl7	0.36624 (6)	0.15153 (13)	0.31846 (10)	0.0701 (4)
Cl8	0.34953 (6)	0.32532 (16)	0.48795 (9)	0.0704 (4)
Cl9	0.31609 (5)	0.65982 (16)	0.42309 (11)	0.0743 (5)
Cl10	0.31215 (5)	0.69968 (17)	0.21428 (10)	0.0790 (5)
Cl11	0.27670 (4)	0.38934 (18)	0.27786 (10)	0.0750 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.088 (6)	0.172 (12)	0.271 (15)	−0.001 (7)	0.048 (9)	−0.124 (11)
C2	0.060 (4)	0.159 (10)	0.151 (9)	0.001 (5)	0.001 (5)	−0.065 (8)
C3	0.060 (4)	0.092 (5)	0.136 (7)	0.003 (4)	0.020 (4)	−0.029 (5)
C4	0.069 (4)	0.069 (4)	0.116 (6)	−0.011 (3)	0.026 (4)	−0.014 (4)
C5	0.072 (4)	0.078 (4)	0.078 (4)	0.005 (3)	0.029 (3)	0.005 (4)
C6	0.065 (4)	0.116 (6)	0.089 (5)	−0.001 (4)	0.006 (4)	0.012 (5)
C7	0.054 (4)	0.121 (7)	0.125 (6)	0.012 (4)	0.029 (4)	0.046 (6)
C8	0.076 (5)	0.153 (9)	0.120 (7)	0.013 (5)	0.063 (5)	0.036 (6)
C9	0.089 (5)	0.130 (8)	0.087 (5)	0.009 (5)	0.045 (4)	0.008 (5)
Cl3	0.0741 (9)	0.0783 (10)	0.0587 (7)	−0.0131 (8)	0.0194 (7)	−0.0158 (7)
N1	0.054 (2)	0.059 (3)	0.080 (3)	0.001 (2)	0.025 (2)	−0.003 (2)
C10	0.041 (2)	0.058 (3)	0.061 (3)	−0.003 (2)	0.017 (2)	0.001 (2)
B1	0.043 (3)	0.057 (3)	0.056 (3)	0.007 (2)	0.025 (2)	0.005 (3)
B2	0.049 (3)	0.057 (3)	0.055 (3)	0.002 (2)	0.025 (3)	0.000 (3)
B3	0.048 (3)	0.052 (3)	0.067 (3)	−0.006 (2)	0.029 (3)	0.000 (3)
B4	0.049 (3)	0.051 (3)	0.064 (3)	0.004 (2)	0.024 (3)	0.001 (3)
B5	0.047 (3)	0.057 (3)	0.060 (3)	0.005 (2)	0.024 (3)	0.011 (3)
B6	0.044 (3)	0.051 (3)	0.056 (3)	0.004 (2)	0.020 (2)	0.004 (3)
B7	0.049 (3)	0.054 (3)	0.051 (3)	0.001 (2)	0.021 (2)	0.002 (2)
B8	0.044 (3)	0.053 (3)	0.051 (3)	−0.004 (2)	0.017 (2)	−0.003 (2)
B9	0.047 (3)	0.055 (3)	0.069 (4)	−0.002 (2)	0.031 (3)	−0.007 (3)
B10	0.050 (3)	0.054 (3)	0.068 (4)	0.005 (3)	0.025 (3)	0.004 (3)
B11	0.046 (3)	0.052 (3)	0.060 (3)	0.000 (2)	0.020 (3)	−0.007 (3)
Cl1	0.0621 (8)	0.0850 (10)	0.0819 (9)	0.0234 (7)	0.0404 (8)	0.0018 (8)
Cl2	0.0667 (8)	0.0750 (10)	0.0712 (9)	0.0158 (7)	0.0140 (7)	0.0199 (8)
Cl4	0.0908 (11)	0.0476 (7)	0.1025 (12)	−0.0145 (7)	0.0435 (10)	−0.0073 (8)
Cl5	0.0870 (11)	0.0811 (10)	0.0811 (10)	−0.0066 (8)	0.0472 (9)	0.0212 (8)
Cl6	0.0724 (9)	0.0780 (10)	0.0517 (7)	0.0070 (7)	0.0187 (6)	−0.0059 (7)
Cl7	0.0954 (11)	0.0433 (6)	0.0771 (9)	−0.0041 (7)	0.0377 (9)	−0.0062 (6)
Cl8	0.0846 (10)	0.0706 (9)	0.0716 (9)	−0.0153 (7)	0.0468 (8)	0.0013 (7)
Cl9	0.0665 (8)	0.0718 (9)	0.0992 (11)	0.0036 (7)	0.0476 (9)	−0.0206 (8)
Cl10	0.0681 (9)	0.0713 (9)	0.0871 (11)	0.0252 (8)	0.0152 (8)	0.0167 (8)
Cl11	0.0448 (6)	0.0940 (11)	0.0870 (10)	−0.0164 (7)	0.0247 (7)	−0.0150 (9)

Geometric parameters (Å, º)

C1—C2	1.406 (12)	B1—B7	1.776 (8)
C1—H1A	0.96	B1—B5	1.783 (8)
C1—H1B	0.96	B1—B2	1.797 (8)
C1—H1C	0.96	B2—Cl2	1.758 (6)
C2—C3	1.521 (10)	B2—B3	1.779 (9)
C2—H2A	0.97	B2—B8	1.787 (8)
C2—H2B	0.97	B2—B7	1.799 (8)
C3—C4	1.484 (10)	B3—B9	1.775 (8)
C3—H3A	0.97	B3—B8	1.784 (8)
C3—H3B	0.97	B3—B4	1.790 (9)
C4—N1	1.484 (7)	B4—B10	1.764 (9)
C4—H4A	0.97	B4—Cl4	1.764 (6)
C4—H4B	0.97	B4—B9	1.776 (8)
C5—N1	1.312 (8)	B4—B5	1.802 (9)
C5—C6	1.363 (10)	B5—Cl5	1.762 (6)
C5—H5	0.93	B5—B10	1.766 (8)
C6—C7	1.349 (11)	B5—B6	1.771 (9)
C6—H6	0.93	B6—Cl6	1.779 (6)
C7—C8	1.335 (12)	B6—B11	1.787 (8)
C7—H7	0.93	B6—B10	1.795 (9)
C8—C9	1.394 (12)	B6—B7	1.797 (8)
C8—H8	0.93	B7—Cl7	1.769 (6)
C9—N1	1.323 (8)	B7—B11	1.810 (8)
C9—H9	0.93	B7—B8	1.811 (8)
Cl3—B3	1.768 (7)	B8—B9	1.775 (9)
C10—B5	1.712 (8)	B8—Cl8	1.776 (6)
C10—B4	1.713 (8)	B8—B11	1.793 (8)
C10—B1	1.717 (8)	B9—B11	1.778 (8)
C10—B3	1.720 (7)	B9—Cl9	1.788 (6)
C10—B2	1.721 (8)	B9—B10	1.806 (9)
C10—H10	1.04 (5)	B10—Cl10	1.771 (6)
B1—Cl1	1.761 (5)	B10—B11	1.793 (9)
B1—B6	1.773 (8)	B11—Cl11	1.771 (6)
C2—C1—H1A	109.5	B9—B4—B3	59.7 (3)
C2—C1—H1B	109.5	C10—B4—B5	58.2 (3)
H1A—C1—H1B	109.5	B10—B4—B5	59.4 (3)
C2—C1—H1C	109.5	Cl4—B4—B5	120.4 (4)
H1A—C1—H1C	109.5	B9—B4—B5	108.1 (4)
H1B—C1—H1C	109.5	B3—B4—B5	107.9 (4)
C1—C2—C3	117.8 (9)	C10—B5—Cl5	120.5 (4)
C1—C2—H2A	107.9	C10—B5—B10	104.2 (4)
C3—C2—H2A	107.9	Cl5—B5—B10	125.4 (4)
C1—C2—H2B	107.9	C10—B5—B6	104.6 (4)
C3—C2—H2B	107.9	Cl5—B5—B6	126.2 (4)
H2A—C2—H2B	107.2	B10—B5—B6	61.0 (3)
C4—C3—C2	110.0 (7)	C10—B5—B1	58.8 (3)
C4—C3—H3A	109.7	Cl5—B5—B1	120.5 (4)
C2—C3—H3A	109.7	B10—B5—B1	108.5 (4)
C4—C3—H3B	109.7	B6—B5—B1	59.8 (3)
C2—C3—H3B	109.7	C10—B5—B4	58.3 (3)
H3A—C3—H3B	108.2	Cl5—B5—B4	119.7 (4)
C3—C4—N1	113.5 (6)	B10—B5—B4	59.2 (3)
C3—C4—H4A	108.9	B6—B5—B4	107.9 (4)
N1—C4—H4A	108.9	B1—B5—B4	107.7 (4)
C3—C4—H4B	108.9	B5—B6—B1	60.4 (3)
N1—C4—H4B	108.9	B5—B6—Cl6	121.2 (4)
H4A—C4—H4B	107.7	B1—B6—Cl6	121.7 (4)
N1—C5—C6	122.0 (7)	B5—B6—B11	107.7 (4)
N1—C5—H5	119	B1—B6—B11	107.8 (4)
C6—C5—H5	119	Cl6—B6—B11	122.3 (4)
C7—C6—C5	118.0 (8)	B5—B6—B10	59.4 (3)
C7—C6—H6	121	B1—B6—B10	107.7 (4)
C5—C6—H6	121	Cl6—B6—B10	121.7 (4)
C8—C7—C6	120.8 (7)	B11—B6—B10	60.1 (3)
C8—C7—H7	119.6	B5—B6—B7	108.5 (4)
C6—C7—H7	119.6	B1—B6—B7	59.7 (3)
C7—C8—C9	119.3 (7)	Cl6—B6—B7	121.4 (4)
C7—C8—H8	120.4	B11—B6—B7	60.7 (3)
C9—C8—H8	120.4	B10—B6—B7	108.8 (4)
N1—C9—C8	119.2 (8)	Cl7—B7—B1	121.7 (4)
N1—C9—H9	120.4	Cl7—B7—B6	123.8 (4)
C8—C9—H9	120.4	B1—B7—B6	59.5 (3)
C5—N1—C9	120.6 (6)	Cl7—B7—B2	120.4 (4)
C5—N1—C4	120.7 (6)	B1—B7—B2	60.3 (3)
C9—N1—C4	118.7 (6)	B6—B7—B2	107.4 (4)
B5—C10—B4	63.5 (3)	Cl7—B7—B11	124.1 (4)
B5—C10—B1	62.7 (3)	B1—B7—B11	106.6 (4)
B4—C10—B1	115.1 (4)	B6—B7—B11	59.4 (3)
B5—C10—B3	115.6 (4)	B2—B7—B11	106.4 (4)
B4—C10—B3	62.9 (3)	Cl7—B7—B8	121.5 (4)
B1—C10—B3	114.7 (4)	B1—B7—B8	107.4 (4)
B5—C10—B2	115.2 (4)	B6—B7—B8	107.1 (4)
B4—C10—B2	114.7 (4)	B2—B7—B8	59.3 (3)
B1—C10—B2	63.0 (3)	B11—B7—B8	59.3 (3)
B3—C10—B2	62.3 (3)	B9—B8—Cl8	121.5 (4)
B5—C10—H10	118 (3)	B9—B8—B3	59.8 (3)
B4—C10—H10	111 (3)	Cl8—B8—B3	120.5 (4)
B1—C10—H10	125 (3)	B9—B8—B2	107.7 (4)
B3—C10—H10	112 (3)	Cl8—B8—B2	121.3 (4)
B2—C10—H10	121 (3)	B3—B8—B2	59.8 (3)
C10—B1—Cl1	121.5 (4)	B9—B8—B11	59.8 (3)
C10—B1—B6	104.3 (4)	Cl8—B8—B11	123.3 (4)
Cl1—B1—B6	125.0 (4)	B3—B8—B11	107.4 (4)
C10—B1—B7	105.2 (4)	B2—B8—B11	107.7 (4)
Cl1—B1—B7	124.5 (4)	B9—B8—B7	108.3 (4)
B6—B1—B7	60.8 (3)	Cl8—B8—B7	122.4 (4)
C10—B1—B5	58.5 (3)	B3—B8—B7	108.0 (4)
Cl1—B1—B5	119.9 (4)	B2—B8—B7	60.0 (3)
B6—B1—B5	59.8 (3)	B11—B8—B7	60.3 (3)
B7—B1—B5	108.9 (4)	B8—B9—B3	60.3 (3)
C10—B1—B2	58.6 (3)	B8—B9—B4	108.8 (4)
Cl1—B1—B2	120.2 (4)	B3—B9—B4	60.6 (3)
B6—B1—B2	108.6 (4)	B8—B9—B11	60.6 (3)
B7—B1—B2	60.5 (3)	B3—B9—B11	108.5 (4)
B5—B1—B2	108.1 (4)	B4—B9—B11	107.6 (4)
C10—B2—Cl2	121.3 (4)	B8—B9—Cl9	122.2 (4)
C10—B2—B3	58.9 (3)	B3—B9—Cl9	121.6 (4)
Cl2—B2—B3	120.2 (4)	B4—B9—Cl9	120.7 (4)
C10—B2—B8	104.3 (4)	B11—B9—Cl9	122.2 (4)
Cl2—B2—B8	125.8 (4)	B8—B9—B10	108.6 (4)
B3—B2—B8	60.0 (3)	B3—B9—B10	107.8 (4)
C10—B2—B1	58.4 (3)	B4—B9—B10	59.0 (3)
Cl2—B2—B1	120.2 (4)	B11—B9—B10	60.0 (4)
B3—B2—B1	108.1 (4)	Cl9—B9—B10	121.1 (4)
B8—B2—B1	107.6 (4)	B4—B10—B5	61.4 (3)
C10—B2—B7	104.1 (4)	B4—B10—Cl10	120.9 (4)
Cl2—B2—B7	125.0 (4)	B5—B10—Cl10	121.6 (4)
B3—B2—B7	108.8 (4)	B4—B10—B11	107.5 (4)
B8—B2—B7	60.7 (3)	B5—B10—B11	107.6 (4)
B1—B2—B7	59.2 (3)	Cl10—B10—B11	122.3 (4)
C10—B3—Cl3	121.3 (4)	B4—B10—B6	108.6 (4)
C10—B3—B9	104.0 (4)	B5—B10—B6	59.7 (3)
Cl3—B3—B9	126.2 (4)	Cl10—B10—B6	122.5 (4)
C10—B3—B2	58.9 (3)	B11—B10—B6	59.7 (3)
Cl3—B3—B2	119.2 (4)	B4—B10—B9	59.7 (3)
B9—B3—B2	108.1 (4)	B5—B10—B9	108.4 (4)
C10—B3—B8	104.5 (4)	Cl10—B10—B9	121.7 (4)
Cl3—B3—B8	125.1 (4)	B11—B10—B9	59.2 (3)
B9—B3—B8	59.8 (3)	B6—B10—B9	107.2 (4)
B2—B3—B8	60.2 (3)	Cl11—B11—B9	122.4 (4)
C10—B3—B4	58.4 (3)	Cl11—B11—B6	121.3 (4)
Cl3—B3—B4	121.0 (4)	B9—B11—B6	108.8 (4)
B9—B3—B4	59.7 (3)	Cl11—B11—B8	120.8 (4)
B2—B3—B4	108.2 (4)	B9—B11—B8	59.6 (3)
B8—B3—B4	107.8 (4)	B6—B11—B8	108.3 (4)
C10—B4—B10	104.2 (4)	Cl11—B11—B10	122.8 (4)
C10—B4—Cl4	121.5 (4)	B9—B11—B10	60.8 (4)
B10—B4—Cl4	124.8 (4)	B6—B11—B10	60.2 (3)
C10—B4—B9	104.2 (4)	B8—B11—B10	108.4 (4)
B10—B4—B9	61.4 (4)	Cl11—B11—B7	120.1 (4)
Cl4—B4—B9	125.3 (4)	B9—B11—B7	108.2 (4)
C10—B4—B3	58.8 (3)	B6—B11—B7	59.9 (3)
B10—B4—B3	109.0 (4)	B8—B11—B7	60.4 (3)
Cl4—B4—B3	120.1 (4)	B10—B11—B7	108.3 (4)
C1—C2—C3—C4	−171.0 (12)	B2—B3—B8—Cl8	110.7 (5)
C2—C3—C4—N1	179.3 (8)	B4—B3—B8—Cl8	−148.1 (4)
N1—C5—C6—C7	−0.6 (12)	C10—B3—B8—B2	40.3 (4)
C5—C6—C7—C8	−1.4 (14)	Cl3—B3—B8—B2	−106.5 (5)
C6—C7—C8—C9	2.8 (15)	B9—B3—B8—B2	138.3 (4)
C7—C8—C9—N1	−2.3 (14)	B4—B3—B8—B2	101.2 (4)
C6—C5—N1—C9	1.1 (11)	C10—B3—B8—B11	−60.4 (5)
C6—C5—N1—C4	−178.2 (7)	Cl3—B3—B8—B11	152.7 (4)
C8—C9—N1—C5	0.4 (12)	B9—B3—B8—B11	37.5 (4)
C8—C9—N1—C4	179.7 (8)	B2—B3—B8—B11	−100.7 (4)
C3—C4—N1—C5	−78.6 (9)	B4—B3—B8—B11	0.5 (5)
C3—C4—N1—C9	102.1 (9)	C10—B3—B8—B7	3.2 (5)
B5—C10—B1—Cl1	108.1 (5)	Cl3—B3—B8—B7	−143.6 (4)
B4—C10—B1—Cl1	145.2 (4)	B9—B3—B8—B7	101.2 (4)
B3—C10—B1—Cl1	−144.5 (4)	B2—B3—B8—B7	−37.1 (4)
B2—C10—B1—Cl1	−108.5 (5)	B4—B3—B8—B7	64.1 (5)
B5—C10—B1—B6	−40.0 (4)	C10—B2—B8—B9	−3.1 (5)
B4—C10—B1—B6	−2.9 (5)	Cl2—B2—B8—B9	144.6 (4)
B3—C10—B1—B6	67.3 (5)	B3—B2—B8—B9	37.2 (4)
B2—C10—B1—B6	103.3 (4)	B1—B2—B8—B9	−64.0 (5)
B5—C10—B1—B7	−103.2 (4)	B7—B2—B8—B9	−101.4 (4)
B4—C10—B1—B7	−66.1 (5)	C10—B2—B8—Cl8	−149.8 (4)
B3—C10—B1—B7	4.1 (5)	Cl2—B2—B8—Cl8	−2.0 (7)
B2—C10—B1—B7	40.1 (4)	B3—B2—B8—Cl8	−109.5 (5)
B4—C10—B1—B5	37.1 (4)	B1—B2—B8—Cl8	149.3 (4)
B3—C10—B1—B5	107.3 (5)	B7—B2—B8—Cl8	111.9 (5)
B2—C10—B1—B5	143.3 (4)	C10—B2—B8—B3	−40.2 (4)
B5—C10—B1—B2	−143.3 (4)	Cl2—B2—B8—B3	107.5 (5)
B4—C10—B1—B2	−106.2 (5)	B1—B2—B8—B3	−101.1 (5)
B3—C10—B1—B2	−36.0 (4)	B7—B2—B8—B3	−138.5 (4)
B5—C10—B2—Cl2	144.3 (4)	C10—B2—B8—B11	60.0 (5)
B4—C10—B2—Cl2	−144.7 (4)	Cl2—B2—B8—B11	−152.3 (4)
B1—C10—B2—Cl2	108.4 (4)	B3—B2—B8—B11	100.3 (5)
B3—C10—B2—Cl2	−108.7 (5)	B1—B2—B8—B11	−0.9 (6)
B5—C10—B2—B3	−107.0 (5)	B7—B2—B8—B11	−38.3 (4)
B4—C10—B2—B3	−36.0 (4)	C10—B2—B8—B7	98.3 (4)
B1—C10—B2—B3	−142.9 (4)	Cl2—B2—B8—B7	−114.0 (5)
B5—C10—B2—B8	−66.2 (5)	B3—B2—B8—B7	138.5 (4)
B4—C10—B2—B8	4.8 (6)	B1—B2—B8—B7	37.4 (4)
B1—C10—B2—B8	−102.1 (4)	Cl7—B7—B8—B9	−150.6 (4)
B3—C10—B2—B8	40.8 (4)	B1—B7—B8—B9	62.4 (5)
B5—C10—B2—B1	35.9 (4)	B6—B7—B8—B9	−0.2 (5)
B4—C10—B2—B1	106.9 (5)	B2—B7—B8—B9	100.3 (4)
B3—C10—B2—B1	142.9 (4)	B11—B7—B8—B9	−36.9 (4)
B5—C10—B2—B7	−3.4 (5)	Cl7—B7—B8—Cl8	−1.0 (6)
B4—C10—B2—B7	67.6 (5)	B1—B7—B8—Cl8	−147.9 (4)
B1—C10—B2—B7	−39.3 (3)	B6—B7—B8—Cl8	149.5 (4)
B3—C10—B2—B7	103.6 (4)	B2—B7—B8—Cl8	−110.1 (5)
Cl1—B1—B2—C10	110.6 (5)	B11—B7—B8—Cl8	112.7 (5)
B6—B1—B2—C10	−95.7 (4)	Cl7—B7—B8—B3	146.1 (4)
B7—B1—B2—C10	−134.4 (4)	B1—B7—B8—B3	−0.9 (5)
B5—B1—B2—C10	−32.4 (4)	B6—B7—B8—B3	−63.5 (5)
C10—B1—B2—Cl2	−110.4 (5)	B2—B7—B8—B3	37.0 (4)
Cl1—B1—B2—Cl2	0.2 (7)	B11—B7—B8—B3	−100.2 (5)
B6—B1—B2—Cl2	153.9 (4)	Cl7—B7—B8—B2	109.1 (5)
B7—B1—B2—Cl2	115.2 (5)	B1—B7—B8—B2	−37.9 (4)
B5—B1—B2—Cl2	−142.8 (4)	B6—B7—B8—B2	−100.5 (4)
C10—B1—B2—B3	32.9 (4)	B11—B7—B8—B2	−137.2 (4)
Cl1—B1—B2—B3	143.5 (4)	Cl7—B7—B8—B11	−113.7 (5)
B6—B1—B2—B3	−62.9 (5)	B1—B7—B8—B11	99.3 (4)
B7—B1—B2—B3	−101.5 (4)	B6—B7—B8—B11	36.7 (4)
B5—B1—B2—B3	0.5 (5)	B2—B7—B8—B11	137.2 (4)
C10—B1—B2—B8	96.3 (4)	Cl8—B8—B9—B3	109.4 (4)
Cl1—B1—B2—B8	−153.1 (4)	B2—B8—B9—B3	−37.1 (4)
B6—B1—B2—B8	0.6 (6)	B11—B8—B9—B3	−137.7 (4)
B7—B1—B2—B8	−38.1 (4)	B7—B8—B9—B3	−100.6 (4)
B5—B1—B2—B8	63.9 (5)	Cl8—B8—B9—B4	147.1 (4)
C10—B1—B2—B7	134.4 (4)	B3—B8—B9—B4	37.7 (4)
Cl1—B1—B2—B7	−115.0 (5)	B2—B8—B9—B4	0.5 (6)
B6—B1—B2—B7	38.6 (4)	B11—B8—B9—B4	−100.0 (5)
B5—B1—B2—B7	101.9 (4)	B7—B8—B9—B4	−62.9 (5)
B5—C10—B3—Cl3	−146.2 (4)	Cl8—B8—B9—B11	−112.8 (5)
B4—C10—B3—Cl3	−109.4 (5)	B3—B8—B9—B11	137.7 (4)
B1—C10—B3—Cl3	143.7 (4)	B2—B8—B9—B11	100.6 (4)
B2—C10—B3—Cl3	107.5 (5)	B7—B8—B9—B11	37.1 (4)
B5—C10—B3—B9	3.5 (6)	Cl8—B8—B9—Cl9	−1.3 (7)
B4—C10—B3—B9	40.2 (4)	B3—B8—B9—Cl9	−110.7 (5)
B1—C10—B3—B9	−66.6 (5)	B2—B8—B9—Cl9	−147.8 (4)
B2—C10—B3—B9	−102.9 (4)	B11—B8—B9—Cl9	111.6 (5)
B5—C10—B3—B2	106.4 (5)	B7—B8—B9—Cl9	148.7 (4)
B4—C10—B3—B2	143.1 (4)	Cl8—B8—B9—B10	−150.2 (4)
B1—C10—B3—B2	36.3 (4)	B3—B8—B9—B10	100.3 (4)
B5—C10—B3—B8	65.4 (6)	B2—B8—B9—B10	63.2 (5)
B4—C10—B3—B8	102.2 (5)	B11—B8—B9—B10	−37.4 (4)
B1—C10—B3—B8	−4.7 (6)	B7—B8—B9—B10	−0.3 (5)
B2—C10—B3—B8	−41.0 (4)	C10—B3—B9—B8	98.8 (4)
B5—C10—B3—B4	−36.7 (4)	Cl3—B3—B9—B8	−113.5 (5)
B1—C10—B3—B4	−106.8 (5)	B2—B3—B9—B8	37.4 (4)
B2—C10—B3—B4	−143.1 (4)	B4—B3—B9—B8	138.4 (4)
Cl2—B2—B3—C10	110.6 (4)	C10—B3—B9—B4	−39.6 (4)
B8—B2—B3—C10	−133.0 (4)	Cl3—B3—B9—B4	108.1 (5)
B1—B2—B3—C10	−32.7 (4)	B2—B3—B9—B4	−100.9 (4)
B7—B2—B3—C10	−95.5 (4)	B8—B3—B9—B4	−138.4 (4)
C10—B2—B3—Cl3	−111.0 (4)	C10—B3—B9—B11	60.6 (5)
Cl2—B2—B3—Cl3	−0.4 (6)	Cl3—B3—B9—B11	−151.7 (4)
B8—B2—B3—Cl3	116.0 (4)	B2—B3—B9—B11	−0.8 (5)
B1—B2—B3—Cl3	−143.7 (4)	B8—B3—B9—B11	−38.2 (4)
B7—B2—B3—Cl3	153.6 (4)	B4—B3—B9—B11	100.2 (5)
C10—B2—B3—B9	95.8 (4)	C10—B3—B9—Cl9	−149.5 (4)
Cl2—B2—B3—B9	−153.7 (4)	Cl3—B3—B9—Cl9	−1.8 (7)
B8—B2—B3—B9	−37.3 (4)	B2—B3—B9—Cl9	149.2 (4)
B1—B2—B3—B9	63.0 (5)	B8—B3—B9—Cl9	111.7 (5)
B7—B2—B3—B9	0.3 (5)	B4—B3—B9—Cl9	−109.9 (5)
C10—B2—B3—B8	133.0 (4)	C10—B3—B9—B10	−2.9 (6)
Cl2—B2—B3—B8	−116.4 (5)	Cl3—B3—B9—B10	144.8 (4)
B1—B2—B3—B8	100.3 (4)	B2—B3—B9—B10	−64.3 (5)
B7—B2—B3—B8	37.6 (4)	B8—B3—B9—B10	−101.7 (5)
C10—B2—B3—B4	32.5 (4)	B4—B3—B9—B10	36.7 (4)
Cl2—B2—B3—B4	143.1 (4)	C10—B4—B9—B8	2.2 (6)
B8—B2—B3—B4	−100.5 (4)	B10—B4—B9—B8	100.8 (5)
B1—B2—B3—B4	−0.2 (5)	Cl4—B4—B9—B8	−145.0 (4)
B7—B2—B3—B4	−62.9 (5)	B3—B4—B9—B8	−37.6 (4)
B5—C10—B4—B10	39.2 (4)	B5—B4—B9—B8	63.0 (5)
B1—C10—B4—B10	2.4 (6)	C10—B4—B9—B3	39.8 (4)
B3—C10—B4—B10	−103.8 (4)	B10—B4—B9—B3	138.4 (5)
B2—C10—B4—B10	−68.0 (5)	Cl4—B4—B9—B3	−107.4 (5)
B5—C10—B4—Cl4	−108.6 (5)	B5—B4—B9—B3	100.5 (4)
B1—C10—B4—Cl4	−145.4 (4)	C10—B4—B9—B11	−62.0 (5)
B3—C10—B4—Cl4	108.5 (5)	B10—B4—B9—B11	36.7 (4)
B2—C10—B4—Cl4	144.2 (4)	Cl4—B4—B9—B11	150.9 (4)
B5—C10—B4—B9	102.7 (5)	B3—B4—B9—B11	−101.8 (5)
B1—C10—B4—B9	65.9 (5)	B5—B4—B9—B11	−1.2 (6)
B3—C10—B4—B9	−40.3 (4)	C10—B4—B9—Cl9	151.2 (4)
B2—C10—B4—B9	−4.5 (6)	B10—B4—B9—Cl9	−110.2 (5)
B5—C10—B4—B3	142.9 (4)	Cl4—B4—B9—Cl9	4.0 (7)
B1—C10—B4—B3	106.2 (5)	B3—B4—B9—Cl9	111.4 (5)
B2—C10—B4—B3	35.8 (4)	B5—B4—B9—Cl9	−148.1 (4)
B1—C10—B4—B5	−36.8 (4)	C10—B4—B9—B10	−98.6 (4)
B3—C10—B4—B5	−142.9 (4)	Cl4—B4—B9—B10	114.2 (5)
B2—C10—B4—B5	−107.2 (5)	B3—B4—B9—B10	−138.4 (5)
Cl3—B3—B4—C10	110.0 (4)	B5—B4—B9—B10	−37.9 (4)
B9—B3—B4—C10	−133.5 (4)	C10—B4—B10—B5	−38.6 (4)
B2—B3—B4—C10	−32.7 (4)	Cl4—B4—B10—B5	107.8 (5)
B8—B3—B4—C10	−96.4 (4)	B9—B4—B10—B5	−137.3 (4)
C10—B3—B4—B10	95.5 (5)	B3—B4—B10—B5	−100.0 (4)
Cl3—B3—B4—B10	−154.5 (4)	C10—B4—B10—Cl10	−150.3 (4)
B9—B3—B4—B10	−38.0 (4)	Cl4—B4—B10—Cl10	−3.9 (7)
B2—B3—B4—B10	62.7 (5)	B9—B4—B10—Cl10	111.0 (5)
B8—B3—B4—B10	−0.9 (5)	B3—B4—B10—Cl10	148.3 (4)
C10—B3—B4—Cl4	−110.8 (5)	B5—B4—B10—Cl10	−111.7 (5)
Cl3—B3—B4—Cl4	−0.8 (6)	C10—B4—B10—B11	62.4 (5)
B9—B3—B4—Cl4	115.7 (5)	Cl4—B4—B10—B11	−151.2 (4)
B2—B3—B4—Cl4	−143.6 (4)	B9—B4—B10—B11	−36.3 (4)
B8—B3—B4—Cl4	152.8 (4)	B3—B4—B10—B11	1.0 (6)
C10—B3—B4—B9	133.5 (4)	B5—B4—B10—B11	101.0 (5)
Cl3—B3—B4—B9	−116.5 (5)	C10—B4—B10—B6	−0.8 (5)
B2—B3—B4—B9	100.7 (4)	Cl4—B4—B10—B6	145.6 (4)
B8—B3—B4—B9	37.1 (4)	B9—B4—B10—B6	−99.5 (5)
C10—B3—B4—B5	32.6 (4)	B3—B4—B10—B6	−62.2 (5)
Cl3—B3—B4—B5	142.6 (4)	B5—B4—B10—B6	37.8 (4)
B9—B3—B4—B5	−100.9 (5)	C10—B4—B10—B9	98.7 (4)
B2—B3—B4—B5	−0.2 (5)	Cl4—B4—B10—B9	−114.9 (5)
B8—B3—B4—B5	−63.8 (5)	B3—B4—B10—B9	37.3 (4)
B4—C10—B5—Cl5	108.2 (5)	B5—B4—B10—B9	137.3 (4)
B1—C10—B5—Cl5	−109.4 (5)	C10—B5—B10—B4	38.6 (4)
B3—C10—B5—Cl5	144.7 (4)	Cl5—B5—B10—B4	−106.5 (6)
B2—C10—B5—Cl5	−145.5 (4)	B6—B5—B10—B4	137.7 (4)
B4—C10—B5—B10	−39.1 (4)	B1—B5—B10—B4	100.0 (5)
B1—C10—B5—B10	103.3 (4)	C10—B5—B10—Cl10	149.2 (4)
B3—C10—B5—B10	−2.6 (6)	Cl5—B5—B10—Cl10	4.0 (8)
B2—C10—B5—B10	67.2 (5)	B6—B5—B10—Cl10	−111.8 (5)
B4—C10—B5—B6	−102.3 (4)	B1—B5—B10—Cl10	−149.4 (4)
B1—C10—B5—B6	40.1 (4)	B4—B5—B10—Cl10	110.6 (5)
B3—C10—B5—B6	−65.8 (5)	C10—B5—B10—B11	−62.1 (5)
B2—C10—B5—B6	4.1 (5)	Cl5—B5—B10—B11	152.8 (5)
B4—C10—B5—B1	−142.4 (4)	B6—B5—B10—B11	37.0 (4)
B3—C10—B5—B1	−105.9 (5)	B1—B5—B10—B11	−0.7 (6)
B2—C10—B5—B1	−36.1 (4)	B4—B5—B10—B11	−100.7 (5)
B1—C10—B5—B4	142.4 (4)	C10—B5—B10—B6	−99.0 (4)
B3—C10—B5—B4	36.5 (4)	Cl5—B5—B10—B6	115.8 (6)
B2—C10—B5—B4	106.3 (5)	B1—B5—B10—B6	−37.6 (4)
Cl1—B1—B5—C10	−110.7 (4)	B4—B5—B10—B6	−137.7 (4)
B6—B1—B5—C10	133.8 (4)	C10—B5—B10—B9	0.5 (6)
B7—B1—B5—C10	96.6 (4)	Cl5—B5—B10—B9	−144.6 (5)
B2—B1—B5—C10	32.4 (4)	B6—B5—B10—B9	99.6 (5)
C10—B1—B5—Cl5	109.3 (5)	B1—B5—B10—B9	61.9 (6)
Cl1—B1—B5—Cl5	−1.4 (7)	B4—B5—B10—B9	−38.1 (4)
B6—B1—B5—Cl5	−116.8 (5)	B5—B6—B10—B4	−38.6 (4)
B7—B1—B5—Cl5	−154.1 (4)	B1—B6—B10—B4	−0.9 (5)
B2—B1—B5—Cl5	141.8 (4)	Cl6—B6—B10—B4	−148.6 (4)
C10—B1—B5—B10	−95.7 (4)	B11—B6—B10—B4	99.8 (5)
Cl1—B1—B5—B10	153.6 (4)	B7—B6—B10—B4	62.3 (5)
B6—B1—B5—B10	38.2 (4)	B1—B6—B10—B5	37.7 (4)
B7—B1—B5—B10	0.9 (6)	Cl6—B6—B10—B5	−110.0 (5)
B2—B1—B5—B10	−63.2 (5)	B11—B6—B10—B5	138.4 (4)
C10—B1—B5—B6	−133.8 (4)	B7—B6—B10—B5	100.9 (4)
Cl1—B1—B5—B6	115.5 (5)	B5—B6—B10—Cl10	110.3 (5)
B7—B1—B5—B6	−37.2 (4)	B1—B6—B10—Cl10	148.0 (4)
B2—B1—B5—B6	−101.4 (4)	Cl6—B6—B10—Cl10	0.3 (7)
C10—B1—B5—B4	−33.0 (4)	B11—B6—B10—Cl10	−111.3 (5)
Cl1—B1—B5—B4	−143.7 (4)	B7—B6—B10—Cl10	−148.8 (4)
B6—B1—B5—B4	100.8 (4)	B5—B6—B10—B11	−138.4 (4)
B7—B1—B5—B4	63.6 (5)	B1—B6—B10—B11	−100.7 (4)
B2—B1—B5—B4	−0.6 (5)	Cl6—B6—B10—B11	111.6 (5)
B10—B4—B5—C10	−134.6 (5)	B7—B6—B10—B11	−37.5 (4)
Cl4—B4—B5—C10	110.5 (5)	B5—B6—B10—B9	−101.6 (5)
B9—B4—B5—C10	−95.9 (5)	B1—B6—B10—B9	−63.9 (5)
B3—B4—B5—C10	−32.8 (4)	Cl6—B6—B10—B9	148.4 (4)
C10—B4—B5—Cl5	−109.5 (5)	B11—B6—B10—B9	36.8 (4)
B10—B4—B5—Cl5	115.9 (5)	B7—B6—B10—B9	−0.7 (5)
Cl4—B4—B5—Cl5	1.0 (6)	B8—B9—B10—B4	−101.2 (4)
B9—B4—B5—Cl5	154.7 (4)	B3—B9—B10—B4	−37.4 (4)
B3—B4—B5—Cl5	−142.2 (4)	B11—B9—B10—B4	−138.9 (4)
C10—B4—B5—B10	134.6 (5)	Cl9—B9—B10—B4	109.4 (5)
Cl4—B4—B5—B10	−114.9 (5)	B8—B9—B10—B5	−62.4 (5)
B9—B4—B5—B10	38.8 (4)	B3—B9—B10—B5	1.5 (6)
B3—B4—B5—B10	101.9 (5)	B4—B9—B10—B5	38.9 (4)
C10—B4—B5—B6	96.4 (4)	B11—B9—B10—B5	−100.0 (5)
B10—B4—B5—B6	−38.2 (4)	Cl9—B9—B10—B5	148.3 (4)
Cl4—B4—B5—B6	−153.1 (4)	B8—B9—B10—Cl10	149.0 (4)
B9—B4—B5—B6	0.6 (6)	B3—B9—B10—Cl10	−147.1 (4)
B3—B4—B5—B6	63.6 (5)	B4—B9—B10—Cl10	−109.7 (5)
C10—B4—B5—B1	33.2 (4)	B11—B9—B10—Cl10	111.4 (5)
B10—B4—B5—B1	−101.4 (5)	Cl9—B9—B10—Cl10	−0.4 (7)
Cl4—B4—B5—B1	143.7 (4)	B8—B9—B10—B11	37.7 (4)
B9—B4—B5—B1	−62.6 (5)	B3—B9—B10—B11	101.5 (5)
B3—B4—B5—B1	0.5 (5)	B4—B9—B10—B11	138.9 (4)
C10—B5—B6—B1	−39.6 (4)	Cl9—B9—B10—B11	−111.7 (5)
Cl5—B5—B6—B1	107.5 (5)	B8—B9—B10—B6	0.6 (5)
B10—B5—B6—B1	−137.9 (4)	B3—B9—B10—B6	64.5 (5)
B4—B5—B6—B1	−100.5 (4)	B4—B9—B10—B6	101.8 (4)
C10—B5—B6—Cl6	−150.8 (4)	B11—B9—B10—B6	−37.1 (4)
Cl5—B5—B6—Cl6	−3.7 (7)	Cl9—B9—B10—B6	−148.8 (4)
B10—B5—B6—Cl6	110.9 (5)	B8—B9—B11—Cl11	109.4 (5)
B1—B5—B6—Cl6	−111.2 (4)	B3—B9—B11—Cl11	147.4 (4)
B4—B5—B6—Cl6	148.3 (4)	B4—B9—B11—Cl11	−148.5 (4)
C10—B5—B6—B11	61.2 (5)	Cl9—B9—B11—Cl11	−2.3 (7)
Cl5—B5—B6—B11	−151.6 (4)	B10—B9—B11—Cl11	−112.3 (5)
B10—B5—B6—B11	−37.1 (4)	B8—B9—B11—B6	−100.7 (4)
B1—B5—B6—B11	100.8 (4)	B3—B9—B11—B6	−62.6 (5)
B4—B5—B6—B11	0.3 (5)	B4—B9—B11—B6	1.4 (6)
C10—B5—B6—B10	98.3 (4)	Cl9—B9—B11—B6	147.7 (4)
Cl5—B5—B6—B10	−114.5 (5)	B10—B9—B11—B6	37.6 (4)
B1—B5—B6—B10	137.9 (4)	B3—B9—B11—B8	38.1 (4)
B4—B5—B6—B10	37.5 (4)	B4—B9—B11—B8	102.1 (4)
C10—B5—B6—B7	−3.0 (5)	Cl9—B9—B11—B8	−111.6 (5)
Cl5—B5—B6—B7	144.2 (4)	B10—B9—B11—B8	138.4 (4)
B10—B5—B6—B7	−101.3 (4)	B8—B9—B11—B10	−138.4 (4)
B1—B5—B6—B7	36.6 (4)	B3—B9—B11—B10	−100.3 (4)
B4—B5—B6—B7	−63.9 (5)	B4—B9—B11—B10	−36.2 (4)
C10—B1—B6—B5	39.4 (4)	Cl9—B9—B11—B10	110.0 (5)
Cl1—B1—B6—B5	−107.3 (5)	B8—B9—B11—B7	−37.1 (4)
B7—B1—B6—B5	139.1 (4)	B3—B9—B11—B7	0.9 (6)
B2—B1—B6—B5	100.6 (5)	B4—B9—B11—B7	65.0 (5)
C10—B1—B6—Cl6	149.9 (4)	Cl9—B9—B11—B7	−148.8 (4)
Cl1—B1—B6—Cl6	3.2 (7)	B10—B9—B11—B7	101.2 (4)
B7—B1—B6—Cl6	−110.4 (5)	B5—B6—B11—Cl11	149.2 (4)
B5—B1—B6—Cl6	110.5 (5)	B1—B6—B11—Cl11	−147.0 (4)
B2—B1—B6—Cl6	−148.9 (4)	Cl6—B6—B11—Cl11	1.6 (7)
C10—B1—B6—B11	−61.2 (5)	B10—B6—B11—Cl11	112.4 (5)
Cl1—B1—B6—B11	152.1 (4)	B7—B6—B11—Cl11	−109.0 (5)
B7—B1—B6—B11	38.4 (4)	B5—B6—B11—B9	−1.1 (5)
B5—B1—B6—B11	−100.6 (4)	B1—B6—B11—B9	62.7 (5)
B2—B1—B6—B11	0.0 (6)	Cl6—B6—B11—B9	−148.7 (4)
C10—B1—B6—B10	2.2 (5)	B10—B6—B11—B9	−37.9 (4)
Cl1—B1—B6—B10	−144.5 (4)	B7—B6—B11—B9	100.7 (5)
B7—B1—B6—B10	101.8 (4)	B5—B6—B11—B8	−64.3 (5)
B5—B1—B6—B10	−37.2 (4)	B1—B6—B11—B8	−0.5 (6)
B2—B1—B6—B10	63.4 (5)	Cl6—B6—B11—B8	148.1 (4)
C10—B1—B6—B7	−99.6 (4)	B10—B6—B11—B8	−101.1 (4)
Cl1—B1—B6—B7	113.6 (5)	B7—B6—B11—B8	37.4 (4)
B5—B1—B6—B7	−139.1 (4)	B5—B6—B11—B10	36.8 (4)
B2—B1—B6—B7	−38.5 (4)	B1—B6—B11—B10	100.6 (5)
C10—B1—B7—Cl7	−148.7 (4)	Cl6—B6—B11—B10	−110.8 (5)
Cl1—B1—B7—Cl7	−1.2 (7)	B7—B6—B11—B10	138.6 (4)
B6—B1—B7—Cl7	113.2 (5)	B5—B6—B11—B7	−101.8 (4)
B5—B1—B7—Cl7	150.0 (4)	B1—B6—B11—B7	−38.0 (4)
B2—B1—B7—Cl7	−109.5 (5)	Cl6—B6—B11—B7	110.7 (5)
C10—B1—B7—B6	98.1 (4)	B10—B6—B11—B7	−138.6 (4)
Cl1—B1—B7—B6	−114.4 (5)	B9—B8—B11—Cl11	−111.9 (5)
B5—B1—B7—B6	36.8 (4)	Cl8—B8—B11—Cl11	−1.9 (7)
B2—B1—B7—B6	137.4 (4)	B3—B8—B11—Cl11	−149.5 (4)
C10—B1—B7—B2	−39.2 (4)	B2—B8—B11—Cl11	147.5 (4)
Cl1—B1—B7—B2	108.2 (5)	B7—B8—B11—Cl11	109.4 (5)
B6—B1—B7—B2	−137.4 (4)	Cl8—B8—B11—B9	110.0 (5)
B5—B1—B7—B2	−100.6 (5)	B3—B8—B11—B9	−37.6 (4)
C10—B1—B7—B11	60.6 (5)	B2—B8—B11—B9	−100.6 (4)
Cl1—B1—B7—B11	−152.0 (4)	B7—B8—B11—B9	−138.7 (4)
B6—B1—B7—B11	−37.6 (4)	B9—B8—B11—B6	101.5 (4)
B5—B1—B7—B11	−0.8 (5)	Cl8—B8—B11—B6	−148.6 (4)
B2—B1—B7—B11	99.8 (4)	B3—B8—B11—B6	63.9 (5)
C10—B1—B7—B8	−1.8 (5)	B2—B8—B11—B6	0.9 (5)
Cl1—B1—B7—B8	145.7 (4)	B7—B8—B11—B6	−37.3 (4)
B6—B1—B7—B8	−99.9 (4)	B9—B8—B11—B10	37.7 (4)
B5—B1—B7—B8	−63.2 (5)	Cl8—B8—B11—B10	147.6 (4)
B2—B1—B7—B8	37.4 (4)	B3—B8—B11—B10	0.1 (5)
B5—B6—B7—Cl7	−146.8 (4)	B2—B8—B11—B10	−62.9 (5)
B1—B6—B7—Cl7	−109.9 (5)	B7—B8—B11—B10	−101.0 (4)
Cl6—B6—B7—Cl7	0.9 (6)	B9—B8—B11—B7	138.7 (4)
B11—B6—B7—Cl7	112.9 (5)	Cl8—B8—B11—B7	−111.3 (5)
B10—B6—B7—Cl7	150.2 (4)	B3—B8—B11—B7	101.2 (4)
B5—B6—B7—B1	−36.9 (4)	B2—B8—B11—B7	38.2 (4)
Cl6—B6—B7—B1	110.8 (4)	B4—B10—B11—Cl11	148.2 (4)
B11—B6—B7—B1	−137.2 (4)	B5—B10—B11—Cl11	−147.1 (4)
B10—B6—B7—B1	−99.9 (4)	Cl10—B10—B11—Cl11	1.4 (7)
B5—B6—B7—B2	1.2 (5)	B6—B10—B11—Cl11	−110.1 (5)
B1—B6—B7—B2	38.1 (4)	B9—B10—B11—Cl11	111.7 (5)
Cl6—B6—B7—B2	148.9 (4)	B4—B10—B11—B9	36.5 (4)
B11—B6—B7—B2	−99.1 (4)	B5—B10—B11—B9	101.3 (5)
B10—B6—B7—B2	−61.9 (5)	Cl10—B10—B11—B9	−110.3 (5)
B5—B6—B7—B11	100.3 (4)	B6—B10—B11—B9	138.2 (4)
B1—B6—B7—B11	137.2 (4)	B4—B10—B11—B6	−101.7 (4)
Cl6—B6—B7—B11	−112.0 (4)	B5—B10—B11—B6	−37.0 (4)
B10—B6—B7—B11	37.3 (4)	Cl10—B10—B11—B6	111.5 (5)
B5—B6—B7—B8	63.6 (5)	B9—B10—B11—B6	−138.2 (4)
B1—B6—B7—B8	100.5 (4)	B4—B10—B11—B8	−0.7 (5)
Cl6—B6—B7—B8	−148.7 (4)	B5—B10—B11—B8	64.1 (5)
B11—B6—B7—B8	−36.7 (4)	Cl10—B10—B11—B8	−147.4 (4)
B10—B6—B7—B8	0.6 (5)	B6—B10—B11—B8	101.0 (4)
C10—B2—B7—Cl7	150.4 (4)	B9—B10—B11—B8	−37.2 (4)
Cl2—B2—B7—Cl7	4.3 (6)	B4—B10—B11—B7	−64.6 (5)
B3—B2—B7—Cl7	−148.1 (4)	B5—B10—B11—B7	0.1 (6)
B8—B2—B7—Cl7	−110.8 (4)	Cl10—B10—B11—B7	148.6 (4)
B1—B2—B7—Cl7	111.5 (5)	B6—B10—B11—B7	37.1 (4)
C10—B2—B7—B1	38.9 (4)	B9—B10—B11—B7	−101.1 (4)
Cl2—B2—B7—B1	−107.2 (5)	Cl7—B7—B11—Cl11	−1.2 (7)
B3—B2—B7—B1	100.3 (4)	B1—B7—B11—Cl11	148.7 (4)
B8—B2—B7—B1	137.6 (4)	B6—B7—B11—Cl11	111.0 (5)
C10—B2—B7—B6	1.2 (5)	B2—B7—B11—Cl11	−148.1 (4)
Cl2—B2—B7—B6	−144.9 (4)	B8—B7—B11—Cl11	−110.6 (5)
B3—B2—B7—B6	62.6 (5)	Cl7—B7—B11—B9	146.2 (4)
B8—B2—B7—B6	99.9 (4)	B1—B7—B11—B9	−63.9 (5)
B1—B2—B7—B6	−37.7 (4)	B6—B7—B11—B9	−101.6 (5)
C10—B2—B7—B11	−61.2 (5)	B2—B7—B11—B9	−0.7 (5)
Cl2—B2—B7—B11	152.7 (4)	B8—B7—B11—B9	36.8 (4)
B3—B2—B7—B11	0.3 (5)	Cl7—B7—B11—B6	−112.3 (5)
B8—B2—B7—B11	37.5 (4)	B1—B7—B11—B6	37.6 (4)
B1—B2—B7—B11	−100.1 (4)	B2—B7—B11—B6	100.8 (4)
C10—B2—B7—B8	−98.7 (4)	B8—B7—B11—B6	138.4 (4)
Cl2—B2—B7—B8	115.1 (5)	Cl7—B7—B11—B8	109.4 (5)
B3—B2—B7—B8	−37.3 (4)	B1—B7—B11—B8	−100.8 (4)
B1—B2—B7—B8	−137.6 (4)	B6—B7—B11—B8	−138.4 (4)
C10—B3—B8—B9	−98.0 (4)	B2—B7—B11—B8	−37.5 (4)
Cl3—B3—B8—B9	115.2 (5)	Cl7—B7—B11—B10	−149.5 (4)
B2—B3—B8—B9	−138.3 (4)	B1—B7—B11—B10	0.4 (5)
B4—B3—B8—B9	−37.1 (4)	B6—B7—B11—B10	−37.2 (4)
C10—B3—B8—Cl8	151.0 (4)	B2—B7—B11—B10	63.6 (5)
Cl3—B3—B8—Cl8	4.2 (7)	B8—B7—B11—B10	101.2 (4)
B9—B3—B8—Cl8	−111.0 (5)