Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111035165/sf3157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111035165/sf3157Isup2.hkl |
CCDC reference: 851750
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).
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.
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 Uiso(H) = 1.5Uiso(C) for methyl groups or 1.2Uiso(C) otherwise. Atom H10 of the undecachlorocarbadodecaborate anion was located in a difference Fourier map and refined freely. [Please check added text]
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.
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) Å3 | 0.1 × 0.1 × 0.05 mm |
Z = 8 |
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 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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.233 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1378P)2] where P = (Fo2 + 2Fc2)/3 |
5577 reflections | (Δ/σ)max < 0.001 |
302 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C9H14N+·CHB11Cl11− | V = 5552.4 (9) Å3 |
Mr = 657.22 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.929 (3) Å | µ = 1.11 mm−1 |
b = 10.2492 (6) Å | T = 298 K |
c = 17.6340 (19) Å | 0.1 × 0.1 × 0.05 mm |
β = 111.100 (12)° |
Oxford Gemini E CCD area-detector diffractometer | 5577 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 3411 reflections with I > 2σ(I) |
Tmin = 0.203, Tmax = 1.000 | Rint = 0.066 |
14744 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.233 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.89 e Å−3 |
5577 reflections | Δρmin = −0.46 e Å−3 |
302 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
Crystal data | |
Chemical formula | C9H14N+·CHB11Cl11− |
Mr | 657.22 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 32.929 (3), 10.2492 (6), 17.6340 (19) |
β (°) | 111.100 (12) |
V (Å3) | 5552.4 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.11 |
Crystal size (mm) | 0.1 × 0.1 × 0.05 |
Data collection | |
Diffractometer | Oxford Gemini E CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.203, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14744, 5577, 3411 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.233, 1.05 |
No. of reflections | 5577 |
No. of parameters | 302 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.89, −0.46 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Please provide details.
Counterion | Cx—Ce—Cev—Cxv (°) | Cei—Ceii—Ceiii—Ceiv (°) | Cl···H (Å)a | Distance between chains (Å)b | Distance between chains (Å)c |
A Me3Si–H–SiMe3 | 0.00 | 180.00 | 3.040 | 3.732 | 3.786–3.832 |
B C4H9-C5H5N) | 32.91 | 176.25 | 2.936 | 3.557–4.431 | 3.759–3.940 |
C (C3H7)3-Si-(ODCB) | 76.25 | 167.49 | 2.923 | 2.923 | 3.776–4.076 |
D Me-Cl-Me | 0.00 | 115.96 | 2.966 | 3.520–4.058 | 3.454 |
E Et-Cl-Et | 89.04 | 152.10 | 2.846–3.213 | 3.577–3.672 | 3.577–3.672 |
F MeOH | 107.29 | 147.14 | 2.961–3.101 | 3.359 | 3.462–3.578 |
Note: superscripts i, ii, iii, iv and v refer to different symmetry operations according to each structure, x refers to the corresponding C number and Ce denotes the centroid of the undecachlorocarbadodecaborate. (a) The closest H···Cl distance forming dimers or not depending on the compound. (b) The distance between units forming the chain. (c) The distance between units of contiguous chains. References: entries A and C: Hoffmann et al. (2006); B this work; D, E and F: Stoyanov et al. (2008). |
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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···C1iv = 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.