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Crystal structure of 1,1′-bis­[1,7-dicarba-closo-dodeca­borane(11)]

aInstitute of Chemical Sciences, School of Engineering & Physical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, Scotland
*Correspondence e-mail: a.j.welch@hw.ac.uk

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 24 September 2014; accepted 7 October 2014; online 24 October 2014)

In the title compound, C4H22B20, the two {1,7-closo-C2B10H11} cages are linked across a centre of inversion, with C—C = 1.5401 (16) Å. The position of the second non-linking cage C atom was established unambiguously by geometric and crystallographic methods and there is no evidence of C/B disorder.

1. Chemical context

Whilst the chemistry of single-cage carboranes is well developed (Grimes, 2011[Grimes, R. N. (2011). Carboranes, 2nd ed., Oxford: Academic Press.]) that of bis­(carboranes) (two discrete carborane units connected via a two-centre two-electron bond) is not. There are several isomeric possibilities for bis­(carboranes) composed of two C2B10 icosa­hedra. Bis(ortho-carborane), 1,1′-bis­[1,2-dicarba-closo-dodeca­borane(11)] (Dupont & Hawthorne, 1964[Dupont, J. A. & Hawthorne, M. F. (1964). J. Am. Chem. Soc. 86, 1643.]), is the best known and its chemistry has been modestly developed (Hawthorne & Owen, 1971[Hawthorne, M. F. & Owen, D. A. (1971). J. Am. Chem. Soc. 93, 873-880.]; Harwell et al., 1996[Harwell, D. E., Mortimer, M. D., Knobler, C. B., Anet, F. A. L. & Hawthorne, M. F. (1996). J. Am. Chem. Soc. 118, 2679-2685.], 1997[Harwell, D. E., McMillan, J., Knobler, C. B. & Hawthorne, M. F. (1997). Inorg. Chem. 36, 5951-5955.]; Yanovsky et al., 1979[Yanovsky, A. I., Furmanova, N. G., Struchkov, Yu. T., Shemyakin, N. F. & Zakharkin, L. I. (1979). Izv. Akad. Nauk SSSR Ser. Khim. pp. 1523-1528.]; Herzog et al., 1999[Herzog, A., Maderna, A., Harakas, G. N., Knobler, C. B. & Hawthorne, M. F. (1999). Chem. Eur. J. 5, 1212-1217.]; Ellis et al., 2010a[Ellis, D., McKay, D., Macgregor, S. A., Rosair, G. M. & Welch, A. J. (2010a). Angew. Chem. Int. Ed. 49, 4943-4945.],b[Ellis, D., Rosair, G. M. & Welch, A. J. (2010b). Chem. Commun. 46, 7394-7396.]). Bis(meta-carborane), 1,1′-bis[1,7-dicarba-closo-dodeca­borane(11)], the subject of this study is, however, less well known. It was first prepared by Zakharkin & Kovredov (1973[Zakharkin, L. I. & Kovredov, A. I. (1973). Izv. Akad. Nauk SSSR Ser. Khim. pp. 1428-1429.]) and later by Yang et al. (1995[Yang, X., Jiang, W., Knobler, C. B., Mortimer, M. D. & Hawthorne, M. F. (1995). Inorg. Chim. Acta, 240, 371-378.]) with the latter authors providing 1H, 13C and 11B NMR spectroscopic and mass spectrometric analysis. We now report the structural study of the title compound, 1,1′-bis[1,7-dicarba-closo-dodeca­borane(11)], (I)[link].

[Scheme 1]

2. Structural commentary

Mol­ecules of (I)[link] are composed of two {1,7-closo-C2B10H11} cages (the contents of the asymmetric unit) linked across a crystallographic inversion centre by the C1—C1A bond [1.5401 (15) Å; symmetry code: (A) ½ − x, ½ − y, 1 − z] (Fig. 1[link]). The two cages are essentially co-linear, B12⋯C1—C1A = 178.72 (7)°, and the facing penta­gons B2/B3/B4/B5/B6 and B2A/B3A/B4A/B5A/B6A are staggered. The five C1—B distances span the range 1.7107 (12)–1.7385 (12) Å, whilst C7—B connectivities lie between 1.6967 (13) and 1.7180 (13) Å, with, in both cases, the two shortest distances being to the B atoms (B2 and B3) that lie between the C atoms. The B2—B3 connectivity, 1.7947 (13) Å, is the longest B—B link, with all (19) others lying between 1.7709 (13) and 1.7891 (15) Å. In general terms these C—B and B—B distances are fully consistent with the averages recently calculated, 1.705 (14) and 1.772 (11) Å, respectively (McAnaw et al., 2013[McAnaw, A., Scott, G., Elrick, L., Rosair, G. M. & Welch, A. J. (2013). Dalton Trans. 42, 645-664.]), from structural studies of the three carborane isomers 1,2-closo-C2B10H12, 1,7-closo-C2B10H12 and 1,12-closo-C2B10H12 (Davidson et al., 1996[Davidson, M. G., Hibbert, T. G., Howard, J. A. K., Mackinnon, A. & Wade, K. (1996). Chem. Commun. pp. 2285-2286.]).

[Figure 1]
Figure 1
Perspective view of the title compound with displacement ellipsoids drawn at the 50% probability level. The label suffix A refers to the symmetry operation (−x + [{1\over 2}], −y + [{1\over 2}], −z + 1).

3. Supra­molecular features

The only H⋯H contact less than 2.40 Å is H6⋯H6B at 2.39 Å [symmetry code: (B) −x + 1, −y + 1, −z + 1]. Although CH units and BH units in carboranes are protonic and hydridic, respectively, there is no evidence of di­hydrogen bonding, the shortest such contact being H7⋯H12C at 2.61 Å [symmetry code: (C) −x + [{1\over 2}], y + [{1\over 2}], −z + [{3\over 2}]].

4. Database survey

A search of the Cambridge Structural Database (Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. Engl. 53, 662-671.]) for the 1,7-closo-C2B10 fragment using Conquest (Version 1.16) returned 132 hits of which only two involve the 1,1′-bis­(1,7-dicarba-closo-dodeca­borane) unit. In DUWJAH (Stadlbauer et al., 2010[Stadlbauer, S., Lonnecke, P., Welzel, P. & Hey-Hawkins, E. (2010). Eur. J. Org. Chem. 3129-3139.]), there are {P(NMe2)2} groups attached to C7 and C7′ whilst in DUWJEL (Stadlbauer et al., 2010[Stadlbauer, S., Lonnecke, P., Welzel, P. & Hey-Hawkins, E. (2010). Eur. J. Org. Chem. 3129-3139.]) these cage atoms are bound to {P(NMe2)(OMe)} units. Of the remaining 130 hits there are five cases of the parent mol­ecule 1,7-closo-C2B10H12 co-crystallized with other mol­ecules, the first of these to be reported being the hexa­methyl­phospho­r­amide adduct TOKGOP (Davidson et al., 1996[Davidson, M. G., Hibbert, T. G., Howard, J. A. K., Mackinnon, A. & Wade, K. (1996). Chem. Commun. pp. 2285-2286.]), whilst all others involve either a single 1,7-closo-C2B10 cage with non-H substituents on one or more C or B atoms or multiple cages linked by other than a direct two-centre two-electron bond.

5. Synthesis and crystallization

The compound was prepared by the CuI-mediated coupling of li­thia­ted meta-carborane, a method first reported by Yang et al. (1992[Yang, X., Jiang, W., Knobler, C. B. & Hawthorne, M. F. (1992). J. Am. Chem. Soc. 114, 9719-9721.]) for para-carborane and later used by Ren & Xie (2008[Ren, S. & Xie, Z. (2008). Organometallics, 27, 5167-5168.]) for the coupling of ortho-carborane. The purity of the product was confirmed by elemental microanalysis and by mass spectrometry and NMR spectroscopy, the last by comparison with data reported by Yang et al. (1995[Yang, X., Jiang, W., Knobler, C. B., Mortimer, M. D. & Hawthorne, M. F. (1995). Inorg. Chim. Acta, 240, 371-378.]). Colourless plates were afforded by the slow evaporation of a di­chloro­methane solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The complete mol­ecule is generated by a crystallographic centre of symmetry at the mid-point of the C1—C1A bond. Initially only the linking atom C1 was identified as a C atom with all other cage atoms described as boron and with H atoms allowed positional refinement. This model (the Prostructure) was refined and then analysed by both the Vertex-to-Centroid Distance (McAnaw et al., 2013[McAnaw, A., Scott, G., Elrick, L., Rosair, G. M. & Welch, A. J. (2013). Dalton Trans. 42, 645-664.]) and the Boron–Hydrogen Distance (McAnaw et al., 2014[McAnaw, A., Lopez, M. E., Ellis, D., Rosair, G. M. & Welch, A. J. (2014). Dalton Trans. 43, 5095-5105.]) methods. Both methods led to the same unambiguous conclusion regarding the location of the second C atom, C7, and there is no evidence of C/B disorder, a frequent problem in crystallographic studies of carboranes and heterocarboranes. Having identified C7, the refinement was completed with H atoms continuing to be freely refined positionally and with Uiso(H) = 1.2Ueq(C,B).

Table 1
Experimental details

Crystal data
Chemical formula C4H22B20
Mr 286.41
Crystal system, space group Monoclinic, C2/c
Temperature (K) 100
a, b, c (Å) 12.1518 (13), 6.8308 (7), 19.9613 (19)
β (°) 93.005 (6)
V3) 1654.6 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.05
Crystal size (mm) 0.56 × 0.38 × 0.16
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.692, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections 19831, 3108, 2261
Rint 0.037
(sin θ/λ)max−1) 0.767
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.130, 1.04
No. of reflections 3108
No. of parameters 142
H-atom treatment Only H-atom coordinates refined
Δρmax, Δρmin (e Å−3) 0.33, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Chemical context top

Whilst the chemistry of single-cage carboranes is well developed (Grimes, 2011) that of bis­(carboranes) (two discrete carborane units connected via a two-centre two-electron bond) is not. There are several isomeric possibilities for bis­(carboranes) composed of two C2B10 icosahedra. Bis(ortho-carborane), 1,1'-bis­[1,2-dicarba-closo-dodecaborane(11)] (Dupont & Hawthorne, 1964), is the best known and its chemistry has been modestly developed (Hawthorne & Owen, 1971; Harwell et al., 1996, 1997; Yanovsky et al., 1979; Herzog et al., 1999; Ellis et al., 2010a,b). Bis(meta-carborane), 1,1'-bis­[1,7-dicarba-closo-dodecaborane(11)], the subject of this study is, however, less well known. It was first prepared by Zakharkin & Kovredov (1973) and later by Yang et al. (1995) with the latter authors providing 1H, 13C and 11B NMR spectroscopic and mass spectrometric analysis. We now report the structural study of the title compound, 1,1'-bis­[1,7-dicarba-closo-dodecaborane(11)], (I).

Structural commentary top

Molecules of (I) are composed of two {1,7-closo-C2B10H11} cages (the contents of the asymmetric unit) linked across a crystallographic inversion centre by the C1—C1A bond [1.5401 (15) Å; symmetry code: (A) 1/2-x, 1/2-y, 1-z] (Fig. 1). The two cages are essentially co-linear, B12···C1—C1A = 178.72 (7)°, and the facing penta­gons B2/B3/B4/B5/B6 and B2A/B3A/B4A/B5A/B6A are staggered. The five C1—B distances span the range 1.7107 (12)–1.7385 (12) Å, whilst C7—B connectivities lie between 1.6967 (13) and 1.7180 (13) Å, with, in both cases, the two shortest distances being to the B atoms (B2 and B3) that lie between the C atoms. The B2—B3 connectivity, 1.7947 (13) Å, is the longest B—B link, with all (19) others lying between 1.7709 (13) and 1.7891 (15) Å. In general terms these C—B and B—B distances are fully consistent with the averages recently calculated, 1.705 (14) and 1.772 (11) Å, respectively (McAnaw et al., 2013), from structural studies of the three carborane isomers 1,2-closo-C2B10H12, 1,7-closo-C2B10H12 and 1,12-closo-C2B10H12 (Davidson et al., 1996).

Supra­molecular features top

The only H···H contact less than 2.40 Å is H6···H6B at 2.39 Å [symmetry code: (B) -x+1, -y+1, -z+1]. Although CH units and BH units in carboranes are protonic and hydridic, respectively, there is no evidence of di­hydrogen bonding, the shortest such contact being H7···H12C at 2.61 Å [symmetry code: (C) -x+1/2, y+1/2, -z+1/2].

Database survey top

A search of the Cambridge Structural Database (Groom & Allen, 2014) for the 1,7-closo-C2B10 fragment using Conquest (Version 1.16) returned 132 hits of which only two involve the 1,1'-bis­(1,7-dicarba-closo-dodecaborane) unit. In DUWJAH (Stadlbauer et al., 2010), there are {P(NMe2)2} groups attached to C7 and C7' whilst in DUWJEL (Stadlbauer et al., 2010) these cage atoms are bound to {P(NMe2)(OMe)} units. Of the remaining 130 hits there are five cases of the parent molecule 1,7-closo-C2B10H12 co-crystallised with other molecules, the first of these to be reported being the hexa­methyl­phospho­ramide adduct TOKGOP (Davidson et al., 1996), whilst all others involve either a single 1,7-closo-C2B10 cage with non-H substituents on one or more C or B atoms or multiple cages linked by other than a direct two-centre two-electron bond.

Synthesis and crystallization top

The compound was prepared by the CuI-mediated coupling of li­thia­ted meta-carborane, a method first reported by Yang et al. (1992) for para-carborane and later used by Ren & Xie (2008) for the coupling of ortho-carborane. The purity of the product was confirmed by elemental microanalysis and by mass spectrometry and NMR spectroscopy, the last by comparison with data reported by Yang et al. (1995). Colourless plates were afforded by the slow evaporation of a di­chloro­methane solution.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The complete molecule is generated by a crystallographic centre of symmetry at the mid-point of the C1—C1A bond. Initially only the linking atom C1 was identified as a C atom with all other cage atoms described as boron and with H atoms allowed positional refinement. This model (the Prostructure) was refined and then analysed by both the Vertex-to-Centroid Distance (McAnaw et al., 2013) and the Boron–Hydrogen Distance (McAnaw et al., 2014) methods. Both methods led to the same unambiguous conclusion regarding the location of the second C atom, C7, and there is no evidence of C/B disorder, a frequent problem in crystallographic studies of carboranes and heterocarboranes. Having identified C7, the refinement was completed with H atoms continuing to be freely refined positionally and with Uiso(H) = 1.2Ueq(C,B).

Related literature top

For related literature, see: Groom & Allen (2014); Davidson et al. (1996); Dupont & Hawthorne (1964); Ellis et al. (2010a, 2010b); Grimes (2011); Harwell et al. (1996, 1997); Herzog et al. (1999); McAnaw et al. (2013, 2014); Owen & Hawthorne (1971); Ren & Xie (2008); Yang et al. (1992, 1995); Yanovsky et al. (1979); Zakharkin & Kovredov (1973).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
Perspective view of the title compound with displacement ellipsoids drawn at the 50% probability level. The label suffix A refers to the symmetry operation (-x+1/2, -y+1/2, -z+1).
1,1'-Bis[1,7-dicarba-closo-dodecaborane(11)] top
Crystal data top
C4H22B20F(000) = 584
Mr = 286.41Dx = 1.150 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 12.1518 (13) ÅCell parameters from 4828 reflections
b = 6.8308 (7) Åθ = 3.4–32.2°
c = 19.9613 (19) ŵ = 0.05 mm1
β = 93.005 (6)°T = 100 K
V = 1654.6 (3) Å3Plate, colourless
Z = 40.56 × 0.38 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
2261 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 33.0°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1818
Tmin = 0.692, Tmax = 0.747k = 1010
19831 measured reflectionsl = 3030
3108 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Only H-atom coordinates refined
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0689P)2 + 0.3243P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
3108 reflectionsΔρmax = 0.33 e Å3
142 parametersΔρmin = 0.24 e Å3
Crystal data top
C4H22B20V = 1654.6 (3) Å3
Mr = 286.41Z = 4
Monoclinic, C2/cMo Kα radiation
a = 12.1518 (13) ŵ = 0.05 mm1
b = 6.8308 (7) ÅT = 100 K
c = 19.9613 (19) Å0.56 × 0.38 × 0.16 mm
β = 93.005 (6)°
Data collection top
Bruker APEXII CCD
diffractometer
3108 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
2261 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.747Rint = 0.037
19831 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.130Only H-atom coordinates refined
S = 1.04Δρmax = 0.33 e Å3
3108 reflectionsΔρmin = 0.24 e Å3
142 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.26856 (6)0.25524 (11)0.53744 (4)0.01245 (16)
B20.29131 (8)0.48296 (14)0.57171 (5)0.01579 (19)
H20.2736 (8)0.6130 (16)0.5456 (5)0.019*
B30.17518 (8)0.33659 (14)0.59232 (5)0.01583 (19)
H30.0950 (8)0.3915 (16)0.5773 (5)0.019*
B40.21591 (8)0.08725 (14)0.59283 (5)0.01628 (19)
H40.1605 (8)0.0227 (15)0.5742 (5)0.020*
B50.35699 (8)0.07852 (13)0.57241 (5)0.01582 (19)
H50.3839 (8)0.0388 (15)0.5406 (5)0.019*
B60.40335 (7)0.32253 (14)0.55914 (5)0.01591 (19)
H60.4600 (8)0.3529 (15)0.5201 (5)0.019*
C70.25880 (7)0.44568 (13)0.65235 (4)0.01717 (18)
H70.2280 (9)0.5573 (16)0.6744 (5)0.021*
B80.20858 (8)0.21700 (15)0.66948 (5)0.0191 (2)
H80.1434 (9)0.2019 (15)0.7044 (6)0.023*
B90.32124 (9)0.05629 (15)0.65735 (5)0.0194 (2)
H90.3297 (9)0.0839 (16)0.6842 (5)0.023*
B100.43699 (8)0.20190 (15)0.63657 (5)0.0185 (2)
H100.5214 (9)0.1591 (17)0.6502 (5)0.022*
B110.39611 (8)0.45205 (14)0.63588 (5)0.0178 (2)
H110.4447 (8)0.5781 (16)0.6513 (5)0.021*
B120.34531 (8)0.28755 (15)0.69637 (5)0.0187 (2)
H120.3626 (8)0.3182 (15)0.7501 (5)0.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0119 (3)0.0128 (3)0.0124 (4)0.0003 (3)0.0010 (3)0.0007 (3)
B20.0178 (4)0.0138 (4)0.0154 (4)0.0005 (3)0.0024 (3)0.0020 (3)
B30.0145 (4)0.0191 (4)0.0138 (4)0.0009 (3)0.0001 (3)0.0030 (3)
B40.0177 (4)0.0170 (4)0.0140 (4)0.0025 (3)0.0001 (3)0.0010 (3)
B50.0165 (4)0.0154 (4)0.0151 (4)0.0026 (3)0.0031 (3)0.0006 (3)
B60.0124 (4)0.0190 (4)0.0160 (4)0.0012 (3)0.0016 (3)0.0020 (3)
C70.0167 (4)0.0201 (4)0.0144 (4)0.0023 (3)0.0020 (3)0.0044 (3)
B80.0207 (5)0.0229 (5)0.0137 (4)0.0019 (4)0.0002 (4)0.0009 (3)
B90.0250 (5)0.0186 (4)0.0142 (4)0.0019 (3)0.0020 (4)0.0008 (3)
B100.0165 (4)0.0219 (5)0.0167 (5)0.0037 (3)0.0042 (3)0.0034 (3)
B110.0156 (4)0.0203 (4)0.0169 (5)0.0009 (3)0.0033 (3)0.0034 (3)
B120.0197 (4)0.0212 (4)0.0147 (4)0.0030 (3)0.0028 (3)0.0019 (3)
Geometric parameters (Å, º) top
C1—C1i1.5401 (15)B5—B91.7786 (14)
C1—B21.7158 (12)B5—B101.7790 (13)
C1—B31.7107 (12)B6—H61.086 (11)
C1—B41.7385 (12)B6—B101.7802 (14)
C1—B51.7380 (12)B6—B111.7751 (14)
C1—B61.7342 (12)C7—H70.966 (11)
B2—H21.046 (11)C7—B81.7179 (13)
B2—B31.7947 (13)C7—B111.7180 (13)
B2—B61.7758 (13)C7—B121.7167 (13)
B2—C71.6967 (13)B8—H81.087 (11)
B2—B111.7709 (13)B8—B91.7812 (14)
B3—H31.072 (10)B8—B121.7854 (14)
B3—B41.7735 (13)B9—H91.099 (11)
B3—C71.7017 (13)B9—B101.7891 (15)
B3—B81.7717 (14)B9—B121.7787 (14)
B4—H41.063 (10)B10—H101.087 (10)
B4—B51.7839 (13)B10—B111.7794 (14)
B4—B81.7745 (14)B10—B121.7742 (14)
B4—B91.7802 (14)B11—H111.079 (11)
B5—H51.084 (10)B11—B121.7832 (14)
B5—B61.7836 (13)B12—H121.103 (11)
C1i—C1—B2117.51 (8)B2—C7—B363.76 (5)
C1i—C1—B3117.79 (8)B2—C7—H7115.4 (6)
C1i—C1—B4119.19 (8)B2—C7—B8115.35 (7)
C1i—C1—B5120.07 (8)B2—C7—B1162.48 (5)
C1i—C1—B6118.65 (8)B2—C7—B12114.41 (7)
B2—C1—B4113.69 (6)B3—C7—H7115.8 (6)
B2—C1—B5112.72 (6)B3—C7—B862.41 (6)
B2—C1—B661.95 (5)B3—C7—B11115.24 (6)
B3—C1—B263.17 (5)B3—C7—B12114.33 (7)
B3—C1—B461.88 (5)B8—C7—H7118.5 (6)
B3—C1—B5112.66 (6)B8—C7—B11114.82 (7)
B3—C1—B6113.79 (6)B11—C7—H7118.1 (6)
B5—C1—B461.74 (5)B12—C7—H7120.3 (7)
B6—C1—B4112.98 (6)B12—C7—B862.64 (6)
B6—C1—B561.82 (5)B12—C7—B1162.55 (6)
C1—B2—H2123.1 (6)B3—B8—B460.01 (5)
C1—B2—B358.28 (5)B3—B8—H8117.4 (6)
C1—B2—B659.53 (5)B3—B8—B9107.98 (7)
C1—B2—B11105.96 (6)B3—B8—B12107.70 (7)
B3—B2—H2116.3 (5)B4—B8—H8125.3 (6)
B6—B2—H2126.3 (5)B4—B8—B960.09 (6)
B6—B2—B3107.85 (7)B4—B8—B12107.82 (7)
C7—B2—C1101.62 (6)C7—B8—B358.35 (5)
C7—B2—H2123.3 (6)C7—B8—B4104.36 (7)
C7—B2—B358.26 (5)C7—B8—H8119.5 (6)
C7—B2—B6105.06 (7)C7—B8—B9104.46 (7)
C7—B2—B1159.35 (5)C7—B8—B1258.65 (5)
B11—B2—H2125.6 (6)B9—B8—H8128.3 (6)
B11—B2—B3108.18 (7)B9—B8—B1259.83 (6)
B11—B2—B660.06 (5)B12—B8—H8122.0 (6)
C1—B3—B258.55 (5)B4—B9—B859.77 (5)
C1—B3—H3124.0 (5)B4—B9—H9120.1 (6)
C1—B3—B459.83 (5)B4—B9—B10108.09 (7)
C1—B3—B8106.11 (7)B5—B9—B460.17 (5)
B2—B3—H3117.1 (6)B5—B9—B8107.75 (7)
B4—B3—B2108.29 (6)B5—B9—H9121.1 (6)
B4—B3—H3126.0 (6)B5—B9—B1059.82 (6)
C7—B3—C1101.63 (6)B5—B9—B12107.39 (7)
C7—B3—B257.99 (5)B8—B9—H9121.6 (6)
C7—B3—H3122.9 (6)B8—B9—B10107.95 (7)
C7—B3—B4105.09 (7)B10—B9—H9122.8 (6)
C7—B3—B859.24 (5)B12—B9—B4107.87 (7)
B8—B3—B2108.01 (7)B12—B9—B860.20 (6)
B8—B3—H3124.6 (6)B12—B9—H9123.5 (6)
B8—B3—B460.07 (5)B12—B9—B1059.64 (6)
C1—B4—B358.29 (5)B5—B10—B660.15 (5)
C1—B4—H4119.4 (6)B5—B10—B959.80 (5)
C1—B4—B559.11 (5)B5—B10—H10121.7 (6)
C1—B4—B8104.80 (6)B5—B10—B11107.91 (7)
C1—B4—B9105.30 (6)B6—B10—B9108.12 (7)
B3—B4—H4120.4 (6)B6—B10—H10120.9 (6)
B3—B4—B5107.58 (6)B9—B10—H10122.4 (6)
B3—B4—B859.91 (5)B11—B10—B659.83 (5)
B3—B4—B9107.94 (7)B11—B10—B9108.24 (7)
B5—B4—H4119.6 (6)B11—B10—H10121.3 (6)
B8—B4—H4126.6 (6)B12—B10—B5107.57 (7)
B8—B4—B5107.81 (7)B12—B10—B6107.92 (7)
B8—B4—B960.14 (6)B12—B10—B959.89 (6)
B9—B4—H4126.0 (6)B12—B10—H10122.5 (6)
B9—B4—B559.87 (5)B12—B10—B1160.24 (6)
C1—B5—B459.14 (5)B2—B11—B660.10 (5)
C1—B5—H5118.5 (5)B2—B11—B10108.06 (7)
C1—B5—B658.98 (5)B2—B11—H11118.2 (6)
C1—B5—B9105.39 (6)B2—B11—B12107.67 (7)
C1—B5—B10105.26 (6)B6—B11—B1060.11 (5)
B4—B5—H5118.8 (5)B6—B11—H11126.3 (6)
B6—B5—B4108.51 (6)B6—B11—B12107.75 (7)
B6—B5—H5119.8 (5)C7—B11—B258.17 (5)
B9—B5—B459.96 (5)C7—B11—B6104.18 (6)
B9—B5—H5126.3 (5)C7—B11—B10104.34 (7)
B9—B5—B6108.43 (7)C7—B11—H11119.2 (6)
B9—B5—B1060.38 (6)C7—B11—B1258.69 (5)
B10—B5—B4108.37 (7)B10—B11—H11128.0 (6)
B10—B5—H5127.0 (5)B10—B11—B1259.73 (6)
B10—B5—B659.96 (5)B12—B11—H11120.9 (6)
C1—B6—B258.52 (5)C7—B12—B858.71 (5)
C1—B6—B559.20 (5)C7—B12—B9104.62 (7)
C1—B6—H6119.8 (5)C7—B12—B10104.62 (7)
C1—B6—B10105.37 (7)C7—B12—B1158.76 (5)
C1—B6—B11105.00 (6)C7—B12—H12117.3 (6)
B2—B6—B5107.77 (6)B8—B12—H12118.1 (5)
B2—B6—H6120.2 (6)B9—B12—B859.97 (6)
B2—B6—B10107.81 (7)B9—B12—B11108.54 (7)
B5—B6—H6120.1 (6)B9—B12—H12127.8 (6)
B10—B6—B559.89 (5)B10—B12—B8108.42 (7)
B10—B6—H6125.9 (5)B10—B12—B960.47 (6)
B11—B6—B259.83 (5)B10—B12—B1160.02 (6)
B11—B6—B5107.90 (7)B10—B12—H12128.5 (5)
B11—B6—H6125.9 (6)B11—B12—B8108.44 (7)
B11—B6—B1060.07 (5)B11—B12—H12119.0 (6)
C1i—C1—B2—B3109.00 (9)B4—B9—B12—C72.16 (9)
C1i—C1—B2—B6109.58 (9)B4—B9—B12—B837.42 (7)
C1i—C1—B2—C7149.66 (8)B4—B9—B12—B10100.91 (7)
C1i—C1—B2—B11149.18 (8)B4—B9—B12—B1163.62 (8)
C1i—C1—B3—B2108.57 (9)B5—C1—B2—B3104.85 (7)
C1i—C1—B3—B4110.08 (9)B5—C1—B2—B636.57 (6)
C1i—C1—B3—C7149.09 (8)B5—C1—B2—C764.19 (8)
C1i—C1—B3—B8149.86 (8)B5—C1—B2—B113.04 (8)
C1i—C1—B4—B3107.87 (9)B5—C1—B3—B2104.94 (7)
C1i—C1—B4—B5110.57 (10)B5—C1—B3—B436.40 (6)
C1i—C1—B4—B8147.27 (9)B5—C1—B3—C764.43 (8)
C1i—C1—B4—B9150.21 (8)B5—C1—B3—B83.37 (8)
C1i—C1—B5—B4109.18 (9)B5—C1—B4—B3141.56 (7)
C1i—C1—B5—B6108.56 (10)B5—C1—B4—B8102.16 (7)
C1i—C1—B5—B9148.89 (9)B5—C1—B4—B939.65 (6)
C1i—C1—B5—B10148.25 (8)B5—C1—B6—B2141.43 (7)
C1i—C1—B6—B2107.77 (9)B5—C1—B6—B1039.68 (6)
C1i—C1—B6—B5110.79 (10)B5—C1—B6—B11102.16 (7)
C1i—C1—B6—B10150.48 (8)B5—B4—B8—B3100.40 (7)
C1i—C1—B6—B11147.05 (9)B5—B4—B8—C761.04 (8)
C1—B2—B3—B434.67 (6)B5—B4—B8—B937.60 (7)
C1—B2—B3—C7131.37 (7)B5—B4—B8—B120.16 (9)
C1—B2—B3—B898.24 (7)B5—B4—B9—B8137.81 (7)
C1—B2—B6—B534.22 (6)B5—B4—B9—B1037.16 (6)
C1—B2—B6—B1097.46 (7)B5—B4—B9—B12100.20 (8)
C1—B2—B6—B11134.99 (7)B5—B6—B10—B937.05 (6)
C1—B2—C7—B340.67 (6)B5—B6—B10—B11138.05 (7)
C1—B2—C7—B84.28 (8)B5—B6—B10—B12100.38 (7)
C1—B2—C7—B11101.80 (7)B5—B6—B11—B2100.57 (7)
C1—B2—C7—B1265.63 (8)B5—B6—B11—C761.17 (8)
C1—B2—B11—B639.35 (6)B5—B6—B11—B1037.42 (6)
C1—B2—B11—C794.25 (7)B5—B6—B11—B120.02 (9)
C1—B2—B11—B101.73 (8)B5—B9—B10—B637.21 (6)
C1—B2—B11—B1261.36 (8)B5—B9—B10—B11100.53 (7)
C1—B3—B4—B534.03 (6)B5—B9—B10—B12137.84 (7)
C1—B3—B4—B8134.83 (7)B5—B9—B12—C761.30 (8)
C1—B3—B4—B997.24 (7)B5—B9—B12—B8100.89 (7)
C1—B3—C7—B240.82 (6)B5—B9—B12—B1037.44 (6)
C1—B3—C7—B8101.96 (7)B5—B9—B12—B110.15 (9)
C1—B3—C7—B114.14 (9)B5—B10—B11—B20.07 (9)
C1—B3—C7—B1265.61 (8)B5—B10—B11—B637.54 (6)
C1—B3—B8—B439.66 (6)B5—B10—B11—C760.79 (8)
C1—B3—B8—C794.14 (7)B5—B10—B11—B12100.41 (7)
C1—B3—B8—B92.08 (9)B5—B10—B12—C761.27 (8)
C1—B3—B8—B1261.11 (8)B5—B10—B12—B80.13 (9)
C1—B4—B5—B633.59 (6)B5—B10—B12—B937.48 (6)
C1—B4—B5—B9134.64 (7)B5—B10—B12—B11100.98 (7)
C1—B4—B5—B1097.16 (7)B6—C1—B2—B3141.42 (7)
C1—B4—B8—B338.61 (6)B6—C1—B2—C7100.76 (7)
C1—B4—B8—C70.75 (8)B6—C1—B2—B1139.60 (6)
C1—B4—B8—B999.38 (7)B6—C1—B3—B236.98 (7)
C1—B4—B8—B1261.94 (8)B6—C1—B3—B4104.36 (7)
C1—B4—B9—B539.28 (6)B6—C1—B3—C73.54 (9)
C1—B4—B9—B898.53 (7)B6—C1—B3—B864.59 (8)
C1—B4—B9—B102.12 (8)B6—C1—B4—B3105.68 (7)
C1—B4—B9—B1260.92 (8)B6—C1—B4—B535.88 (6)
C1—B5—B6—B233.94 (6)B6—C1—B4—B866.28 (8)
C1—B5—B6—B10134.63 (7)B6—C1—B4—B93.77 (9)
C1—B5—B6—B1197.13 (7)B6—C1—B5—B4142.25 (7)
C1—B5—B9—B439.31 (6)B6—C1—B5—B9102.54 (7)
C1—B5—B9—B81.78 (9)B6—C1—B5—B1039.69 (6)
C1—B5—B9—B1099.06 (7)B6—B2—B3—C134.38 (6)
C1—B5—B9—B1261.70 (8)B6—B2—B3—B40.29 (9)
C1—B5—B10—B639.22 (6)B6—B2—B3—C796.99 (7)
C1—B5—B10—B999.28 (7)B6—B2—B3—B863.86 (8)
C1—B5—B10—B111.82 (9)B6—B2—C7—B3101.93 (7)
C1—B5—B10—B1261.77 (8)B6—B2—C7—B865.55 (8)
C1—B6—B10—B539.35 (6)B6—B2—C7—B1140.53 (6)
C1—B6—B10—B92.29 (9)B6—B2—C7—B124.36 (9)
C1—B6—B10—B1198.71 (7)B6—B2—B11—C7133.60 (7)
C1—B6—B10—B1261.03 (8)B6—B2—B11—B1037.61 (6)
C1—B6—B11—B238.64 (6)B6—B2—B11—B12100.71 (7)
C1—B6—B11—C70.75 (8)B6—B5—B9—B4101.17 (7)
C1—B6—B11—B1099.35 (7)B6—B5—B9—B863.64 (8)
C1—B6—B11—B1261.94 (8)B6—B5—B9—B1037.20 (6)
B2—C1—B3—B4141.34 (7)B6—B5—B9—B120.16 (9)
B2—C1—B3—C740.52 (6)B6—B5—B10—B9138.50 (7)
B2—C1—B3—B8101.57 (7)B6—B5—B10—B1137.39 (6)
B2—C1—B4—B337.50 (6)B6—B5—B10—B12100.98 (7)
B2—C1—B4—B5104.06 (7)B6—B10—B11—B237.61 (6)
B2—C1—B4—B81.90 (9)B6—B10—B11—C798.32 (7)
B2—C1—B4—B964.42 (8)B6—B10—B11—B12137.94 (7)
B2—C1—B5—B4105.64 (7)B6—B10—B12—C72.23 (9)
B2—C1—B5—B636.62 (6)B6—B10—B12—B863.62 (9)
B2—C1—B5—B965.92 (8)B6—B10—B12—B9100.97 (7)
B2—C1—B5—B103.07 (9)B6—B10—B12—B1137.49 (6)
B2—C1—B6—B5141.43 (7)B6—B11—B12—C796.11 (7)
B2—C1—B6—B10101.75 (7)B6—B11—B12—B863.51 (8)
B2—C1—B6—B1139.27 (6)B6—B11—B12—B90.08 (9)
B2—B3—B4—C134.14 (6)B6—B11—B12—B1037.57 (6)
B2—B3—B4—B50.11 (9)C7—B2—B3—C1131.37 (7)
B2—B3—B4—B8100.68 (7)C7—B2—B3—B496.70 (7)
B2—B3—B4—B963.09 (8)C7—B2—B3—B833.13 (6)
B2—B3—C7—B8142.78 (7)C7—B2—B6—C194.81 (7)
B2—B3—C7—B1136.68 (7)C7—B2—B6—B560.59 (8)
B2—B3—C7—B12106.43 (7)C7—B2—B6—B102.65 (8)
B2—B3—B8—B4101.16 (7)C7—B2—B6—B1140.18 (6)
B2—B3—B8—C732.64 (6)C7—B2—B11—B6133.60 (7)
B2—B3—B8—B963.59 (8)C7—B2—B11—B1095.98 (7)
B2—B3—B8—B120.40 (9)C7—B2—B11—B1232.89 (6)
B2—B6—B10—B5100.62 (7)C7—B3—B4—C194.86 (7)
B2—B6—B10—B963.57 (8)C7—B3—B4—B560.82 (8)
B2—B6—B10—B1137.43 (6)C7—B3—B4—B839.97 (6)
B2—B6—B10—B120.24 (9)C7—B3—B4—B92.38 (8)
B2—B6—B11—C739.39 (6)C7—B3—B8—B4133.80 (7)
B2—B6—B11—B10137.99 (7)C7—B3—B8—B996.23 (7)
B2—B6—B11—B12100.58 (7)C7—B3—B8—B1233.04 (6)
B2—C7—B8—B336.90 (7)C7—B8—B9—B498.46 (7)
B2—C7—B8—B43.29 (9)C7—B8—B9—B560.75 (8)
B2—C7—B8—B965.54 (8)C7—B8—B9—B102.43 (9)
B2—C7—B8—B12105.65 (7)C7—B8—B9—B1239.52 (6)
B2—C7—B11—B640.36 (6)C7—B8—B12—B9133.82 (7)
B2—C7—B11—B10102.59 (7)C7—B8—B12—B1096.25 (7)
B2—C7—B11—B12142.73 (7)C7—B8—B12—B1132.62 (6)
B2—C7—B12—B8107.13 (7)C7—B11—B12—B832.60 (6)
B2—C7—B12—B966.93 (9)C7—B11—B12—B996.20 (7)
B2—C7—B12—B104.21 (9)C7—B11—B12—B10133.68 (7)
B2—C7—B12—B1136.14 (7)B8—B3—B4—C1134.83 (7)
B2—B11—B12—C732.68 (6)B8—B3—B4—B5100.79 (7)
B2—B11—B12—B80.09 (9)B8—B3—B4—B937.59 (6)
B2—B11—B12—B963.51 (8)B8—B3—C7—B2142.78 (7)
B2—B11—B12—B10101.00 (7)B8—B3—C7—B11106.10 (8)
B3—C1—B2—B6141.42 (7)B8—B3—C7—B1236.35 (7)
B3—C1—B2—C740.66 (6)B8—B4—B5—C196.92 (7)
B3—C1—B2—B11101.82 (7)B8—B4—B5—B663.33 (8)
B3—C1—B4—B5141.56 (7)B8—B4—B5—B937.72 (6)
B3—C1—B4—B839.40 (6)B8—B4—B5—B100.24 (9)
B3—C1—B4—B9101.91 (7)B8—B4—B9—B5137.81 (7)
B3—C1—B5—B436.45 (6)B8—B4—B9—B10100.65 (7)
B3—C1—B5—B6105.80 (7)B8—B4—B9—B1237.61 (7)
B3—C1—B5—B93.26 (8)B8—C7—B11—B2106.91 (7)
B3—C1—B5—B1066.11 (8)B8—C7—B11—B666.55 (9)
B3—C1—B6—B237.46 (7)B8—C7—B11—B104.32 (9)
B3—C1—B6—B5103.98 (7)B8—C7—B11—B1235.82 (7)
B3—C1—B6—B1064.29 (8)B8—C7—B12—B940.20 (6)
B3—C1—B6—B111.82 (9)B8—C7—B12—B10102.92 (7)
B3—B2—B6—C133.87 (6)B8—C7—B12—B11143.27 (7)
B3—B2—B6—B50.35 (9)B8—B9—B10—B5100.51 (7)
B3—B2—B6—B1063.59 (8)B8—B9—B10—B663.30 (8)
B3—B2—B6—B11101.12 (7)B8—B9—B10—B110.02 (9)
B3—B2—C7—B836.39 (7)B8—B9—B10—B1237.33 (6)
B3—B2—C7—B11142.47 (7)B8—B9—B12—C739.58 (6)
B3—B2—C7—B12106.30 (8)B8—B9—B12—B10138.33 (7)
B3—B2—B11—B6100.55 (7)B8—B9—B12—B11101.04 (7)
B3—B2—B11—C733.05 (6)B9—B4—B5—C1134.64 (7)
B3—B2—B11—B1062.94 (8)B9—B4—B5—B6101.05 (7)
B3—B2—B11—B120.16 (9)B9—B4—B5—B1037.48 (6)
B3—B4—B5—C133.70 (6)B9—B4—B8—B3138.00 (7)
B3—B4—B5—B60.11 (9)B9—B4—B8—C798.63 (7)
B3—B4—B5—B9100.94 (7)B9—B4—B8—B1237.44 (7)
B3—B4—B5—B1063.46 (8)B9—B5—B6—C197.24 (7)
B3—B4—B8—C739.36 (6)B9—B5—B6—B263.30 (8)
B3—B4—B8—B9138.00 (7)B9—B5—B6—B1037.39 (6)
B3—B4—B8—B12100.56 (7)B9—B5—B6—B110.11 (8)
B3—B4—B9—B5100.32 (7)B9—B5—B10—B6138.50 (7)
B3—B4—B9—B837.49 (6)B9—B5—B10—B11101.10 (7)
B3—B4—B9—B1063.16 (8)B9—B5—B10—B1237.52 (7)
B3—B4—B9—B120.12 (9)B9—B8—B12—C7133.82 (7)
B3—C7—B8—B440.19 (6)B9—B8—B12—B1037.57 (7)
B3—C7—B8—B9102.44 (7)B9—B8—B12—B11101.21 (7)
B3—C7—B8—B12142.55 (7)B9—B10—B11—B263.17 (8)
B3—C7—B11—B237.16 (7)B9—B10—B11—B6100.78 (7)
B3—C7—B11—B63.20 (9)B9—B10—B11—C72.46 (8)
B3—C7—B11—B1065.42 (9)B9—B10—B11—B1237.16 (6)
B3—C7—B11—B12105.57 (8)B9—B10—B12—C798.74 (7)
B3—C7—B12—B836.26 (7)B9—B10—B12—B837.35 (7)
B3—C7—B12—B93.94 (9)B9—B10—B12—B11138.46 (7)
B3—C7—B12—B1066.66 (9)B10—B5—B6—C1134.63 (7)
B3—C7—B12—B11107.01 (7)B10—B5—B6—B2100.69 (7)
B3—B8—B9—B437.54 (6)B10—B5—B6—B1137.50 (6)
B3—B8—B9—B50.17 (9)B10—B5—B9—B4138.38 (7)
B3—B8—B9—B1063.35 (8)B10—B5—B9—B8100.84 (7)
B3—B8—B9—B12100.44 (7)B10—B5—B9—B1237.36 (6)
B3—B8—B12—C732.92 (6)B10—B6—B11—B2137.99 (7)
B3—B8—B12—B9100.91 (7)B10—B6—B11—C798.59 (7)
B3—B8—B12—B1063.34 (9)B10—B6—B11—B1237.41 (6)
B3—B8—B12—B110.30 (9)B10—B9—B12—C798.75 (7)
B4—C1—B2—B336.99 (6)B10—B9—B12—B8138.33 (7)
B4—C1—B2—B6104.43 (7)B10—B9—B12—B1137.29 (6)
B4—C1—B2—C73.67 (8)B10—B11—B12—C7133.68 (7)
B4—C1—B2—B1164.83 (8)B10—B11—B12—B8101.09 (7)
B4—C1—B3—B2141.34 (7)B10—B11—B12—B937.49 (6)
B4—C1—B3—C7100.83 (7)B11—B2—B3—C197.89 (7)
B4—C1—B3—B839.78 (6)B11—B2—B3—B463.22 (8)
B4—C1—B5—B6142.25 (7)B11—B2—B3—C733.48 (6)
B4—C1—B5—B939.71 (6)B11—B2—B3—B80.35 (9)
B4—C1—B5—B10102.57 (7)B11—B2—B6—C1134.99 (7)
B4—C1—B6—B2105.58 (7)B11—B2—B6—B5100.77 (7)
B4—C1—B6—B535.85 (6)B11—B2—B6—B1037.53 (6)
B4—C1—B6—B103.83 (9)B11—B2—C7—B3142.47 (7)
B4—C1—B6—B1166.31 (8)B11—B2—C7—B8106.08 (7)
B4—B3—C7—B2102.40 (7)B11—B2—C7—B1236.17 (7)
B4—B3—C7—B840.38 (6)B11—B6—B10—B5138.05 (7)
B4—B3—C7—B1165.72 (8)B11—B6—B10—B9101.00 (7)
B4—B3—C7—B124.03 (9)B11—B6—B10—B1237.67 (6)
B4—B3—B8—C7133.80 (7)B11—C7—B8—B3106.76 (7)
B4—B3—B8—B937.58 (6)B11—C7—B8—B466.57 (9)
B4—B3—B8—B12100.77 (7)B11—C7—B8—B94.32 (9)
B4—B5—B6—C133.65 (6)B11—C7—B8—B1235.79 (7)
B4—B5—B6—B20.28 (9)B11—C7—B12—B8143.27 (7)
B4—B5—B6—B10100.97 (7)B11—C7—B12—B9103.06 (7)
B4—B5—B6—B1163.47 (8)B11—C7—B12—B1040.35 (6)
B4—B5—B9—B837.54 (6)B11—B10—B12—C739.72 (6)
B4—B5—B9—B10138.38 (7)B11—B10—B12—B8101.11 (7)
B4—B5—B9—B12101.01 (7)B11—B10—B12—B9138.46 (7)
B4—B5—B10—B6101.21 (7)B12—C7—B8—B3142.55 (7)
B4—B5—B10—B937.29 (6)B12—C7—B8—B4102.36 (7)
B4—B5—B10—B1163.81 (8)B12—C7—B8—B940.10 (6)
B4—B5—B10—B120.22 (9)B12—C7—B11—B2142.73 (7)
B4—B8—B9—B537.71 (6)B12—C7—B11—B6102.37 (7)
B4—B8—B9—B10100.90 (7)B12—C7—B11—B1040.14 (6)
B4—B8—B9—B12137.98 (7)B12—B8—B9—B4137.98 (7)
B4—B8—B12—C796.27 (7)B12—B8—B9—B5100.27 (8)
B4—B8—B12—B937.55 (6)B12—B8—B9—B1037.08 (6)
B4—B8—B12—B100.02 (9)B12—B9—B10—B5137.84 (7)
B4—B8—B12—B1163.66 (9)B12—B9—B10—B6100.64 (7)
B4—B9—B10—B537.31 (6)B12—B9—B10—B1137.31 (6)
B4—B9—B10—B60.11 (9)B12—B10—B11—B2100.33 (7)
B4—B9—B10—B1163.22 (8)B12—B10—B11—B6137.94 (7)
B4—B9—B10—B12100.53 (7)B12—B10—B11—C739.62 (6)
Symmetry code: (i) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC4H22B20
Mr286.41
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)12.1518 (13), 6.8308 (7), 19.9613 (19)
β (°) 93.005 (6)
V3)1654.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.05
Crystal size (mm)0.56 × 0.38 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.692, 0.747
No. of measured, independent and
observed [I > 2σ(I)] reflections
19831, 3108, 2261
Rint0.037
(sin θ/λ)max1)0.767
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.130, 1.04
No. of reflections3108
No. of parameters142
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.33, 0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

The authors thank the EPSRC for a DTA studentship awarded to LE.

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