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The title compound, 1-CH2OCH3-2-COOH-1,2-closo-C2B10H10 or C5H16B10O3, forms a discrete centrosymmetric tetramer, via hydrogen bonding, involving two inner and two outer carborane mol­ecules. One conventional eight-membered hydrogen-bonded ring [graph set R22(8)] is formed between two car­bo­xy­lic acid groups of the inner carboranes. This interaction is then supplemented by an open finite hydrogen bond (graph set D) between the ether O atom of the inner carborane and the carboxylic acid H atom of the outer carborane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103019048/ln1176sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103019048/ln1176Isup2.hkl
Contains datablock I

CCDC reference: 224668

Comment top

Crystal engineering is a rapidly growing cross-disciplinary field that seeks to develop protocols for predicting and controlling the structures and thus the functional properties of solids. Heteroboranes have only relatively recently begun to be used for crystal engineering but have great potential (Centore et al., 1994; Hosmane et al., 1998; Macías et al., 1999; Lee et al., 2000; Hardie et al., 2000; Hardie & Raston, 2000, 2001; Welch et al., 2001; O'Dowd et al., 2002). In order to explore crystal engineering with heteroboranes, we have begun a systematic study of the crystal and molecular structures of various carborane carboxylic acids. We have sucessfully determined and reported the structures of the monocarboxylic acids 1-COOH-1,2-closo-C2B10H11 (Welch et al., 2001), 1-CH3-2-COOH-1,2-closo-C2B10H10 (Venkatasubramanian, Donohoe et al., 2003) and 1-Ph-2-COOH-1,2-closo-C2B10H10 (Venkatasubramanian, Donohoe et al., 2003), and the dicarboxylic acid 1,2-(COOH)2-1,2-closo-C2B10H10 (Venkatasubramanian, Ellis et al., 2003). All three monocarboxylic acids form discrete hydrogen-bonded dimers with or without solvent molecules, while the 1,2-dicarboxylic acid forms tetramers incorporating an ethanol (solvent) molecule, the –OH group of which is also involved in hydrogen bonding. 1,12-(COOH)2-1,2-closo-C2B10H10 forms infinite hydrogen-bonded chains (Centore et al., 1994). In this paper, we report the crystal and molecular structures of 1-CH2OCH3-2-COOH-1,2-closo-C2B10H10, the title compound, (I). \sch

Compound (I) forms a centrosymmetric tetramer with two crystallographically independent carborane molecules in the asymmetric fraction of the unit cell. The inner molecule (A) is bound to its inversion-related partner via a conventional double-hydrogen-bonded eight-membered ring involving the two carboxylic acid groups, denoted R22(8) in graph-set terminology (Etter, 1990; Etter & McDonald, 1990). The outer molecule (B) is linked to the inner molecule by a discrete hydrogen bond, graph set D, between its carboxy H atom and the ether O atom of molecule A. The dimensions within these two hydrogen bonds are similar to each other, and both hydrogen bonds are considered to be `strong' (Desiraju & Steiner, 1999). The carboxyl C—O and CO bonds in molecule B are clearly distinguished, at 1.320 (2) and 1.197 (2) Å, respectively, and are fully consistent with the results of previous studies (Leiserowitz, 1976), but in molecule A, the distinction between C3A—O2A [1.250 (2) Å] and C3A—O1A [1.2601 (19) Å] is not so clear, possibly reflecting some degree of H-atom disorder in the eight-membered ring (see Experimental).

The conformation of the carboxy group, θCOOH (the modulus of the average Ccage—Ccage—C—O torsion angle; Venkatasubramanian, Donohoe et al., 2003), in molecule A is 73.7 (2)syn°, similar to that [65.0 (2)syn°] in 1-Me-2-COOH-1,2-closo-C2B10H10 (Venkatasubramanian, Donohoe et al., 2003), whilst in molecule B, θCOOH is 38.0 (2)°, close to that that [39.7 (3)°] in one of the crystallographically independent molecules of 1-Ph-2-COOH-1,2-closo-C2B10H10 (Venkatasubramanian, Donohoe et al., 2003). At the same time, the conformation of the methoxymethyl substituent also differs between the two independent molecules of (I). In molecule A, the C1A—C4A—O3A—C5A torsion angle is −90.62 (18)°, whilst the corresponding angle in molecule B is −172.45 (17)°.

Within the carborane polyhedra, the C—C distances in both molecules A and B [1.669 (2) and 1.656 (2) Å, respectively] are longer than in the parent compounds, 1-CH3OCH2-1,2-closo-C2B10H11 [1.636 (9) and 1.649 (8) Å; Shaw & Welch, 1992] and 1-COOH-1,2-closo-C2B10H11 [1.631 (2) Å; Welch et al., 2001], but fully comparable with that in 1-Me-2-COOH-1,2-closo-C2B10H10 [1.6694 (17) Å; Venkatasubramanian, Donohoe et al., 2003], reflecting the 1,2-disubstitution. The B—C and B—B distances span the ranges 1.703 (2)–1.744 (2) and 1.756 (2)–1.795 (3) Å in molecules A and B, respectively.

Experimental top

Compound (I) was prepared following the procedure of Heying et al. (1963) for other mono-substitited carborane carboxylic acids. MeLi was added dropwise as an ether solution to a stirred solution of 1-CH2OCH3-1,2-closo-C2B10H11 in ether at 273 K, in a ratio of 1:1. Gaseous CO2 was passed through the solution at room temperature for 20 min. The solution was then hydrolysed with 2M HCl. On removal of the solvent from the ether solution, an off-white crystalline solid remained. Diffraction quality crystals of (I) were grown from dichloromethane and 40–60 petroleum ether (Ratio?) by solvent diffusion. Analysis calculated for C5H16B10O3: C 25.84, H 6.94%; found: C 25.44, H 7.13%. Spectroscopic analysis: IR (ν, cm−1): 2589 (B—H), 1760, 1728 (CO); 11B-{1H} FT-NMR (128.4 MHz, δ, p.p.m.): 2.12 (1B), −0.69 (1B), −7.51 (8B). The carboxylic acid H atoms were not observed in the 1H NMR spectrum, due to fast intermolecular exchange. Signals due to the CH2 H atoms (4.05) and CH3 H atoms (3.25) were observed. NMR spectra were recorded from a CDCl3 solution at 293 K on a Bruker DPX400 spectrometer. The IR spectrum was recorded using a Perkin-Elmer Spectrum RX FT—IR system spectrophotometer and a KBr pellet.

Refinement top

The carboxylic acid H atoms were located from a difference Fourier map. The position and Uiso of atom H1B were allowed to refine freely in subsequent refinement cycles. The O1A—H1A distance was restrained to 0.90 (5) Å Please clarify − 0.96 (2) Å in Table 2 and Uiso(H1A) was set to 1.5Ueq(O1A). The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å) with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.99 and B—H = 1.12 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(parent atom).

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A perspective view of the tetramer of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small circles of arbitrary radii. Hydrogen bonds are shown as dotted lines. Atoms marked with a hash (#) are at symmetry position (-x, 1 − y, −z).
2-carboxy-1,2-dicarba-1-methoxymethyl-closo-dodecaborane(12) top
Crystal data top
C5H16B10O3F(000) = 1920
Mr = 232.28Dx = 1.222 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 41 reflections
a = 22.746 (2) Åθ = 3.6–16.7°
b = 9.699 (1) ŵ = 0.07 mm1
c = 23.439 (3) ÅT = 160 K
β = 102.296 (10)°Block, colourless
V = 5052.1 (10) Å30.24 × 0.20 × 0.18 mm
Z = 16
Data collection top
Bruker P4
diffractometer
Rint = 0.027
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = 126
ω scansk = 111
5399 measured reflectionsl = 2727
4418 independent reflections3 standard reflections every 97 reflections
3670 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0657P)2 + 3.9862P]
where P = (Fo2 + 2Fc2)/3
4418 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.30 e Å3
Crystal data top
C5H16B10O3V = 5052.1 (10) Å3
Mr = 232.28Z = 16
Monoclinic, C2/cMo Kα radiation
a = 22.746 (2) ŵ = 0.07 mm1
b = 9.699 (1) ÅT = 160 K
c = 23.439 (3) Å0.24 × 0.20 × 0.18 mm
β = 102.296 (10)°
Data collection top
Bruker P4
diffractometer
Rint = 0.027
5399 measured reflections3 standard reflections every 97 reflections
4418 independent reflections intensity decay: none
3670 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å3
4418 reflectionsΔρmin = 0.30 e Å3
334 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.00055 (5)0.60029 (13)0.06038 (5)0.0311 (3)
H1A0.0274 (10)0.576 (2)0.0250 (10)0.047*
O2A0.07239 (6)0.46186 (13)0.04153 (5)0.0340 (3)
O3A0.13373 (5)0.25680 (12)0.12789 (5)0.0275 (3)
C1A0.15047 (7)0.49657 (16)0.16314 (6)0.0185 (3)
C2A0.08986 (7)0.58734 (16)0.13164 (6)0.0184 (3)
C3A0.05167 (7)0.54434 (16)0.07319 (7)0.0195 (3)
C4A0.17225 (7)0.37224 (17)0.13281 (7)0.0243 (4)
H410.17630.40030.09320.029*
H420.21260.34500.15500.029*
C5A0.14700 (10)0.1606 (2)0.17587 (9)0.0403 (5)
H510.18910.13160.18190.060*
H520.12080.07980.16690.060*
H530.14010.20510.21140.060*
B3A0.08559 (8)0.4863 (2)0.19134 (8)0.0216 (4)
H3A0.05700.39180.18990.026*
B4A0.15891 (8)0.5003 (2)0.23734 (8)0.0233 (4)
H4A0.17870.41420.26710.028*
B5A0.20416 (8)0.6037 (2)0.20129 (8)0.0232 (4)
H5A0.25370.58510.20750.028*
B6A0.16037 (8)0.65600 (19)0.13251 (8)0.0225 (4)
H6A0.18020.67100.09310.027*
B7A0.05432 (8)0.6558 (2)0.18247 (8)0.0248 (4)
H7A0.00460.67280.17570.030*
B8A0.09856 (9)0.6032 (2)0.25079 (8)0.0279 (4)
H8A0.07840.58560.28980.033*
B9A0.17178 (9)0.6767 (2)0.25694 (8)0.0268 (4)
H9A0.19990.70820.30020.032*
B10A0.17283 (9)0.7726 (2)0.19198 (9)0.0273 (4)
H10A0.20150.86660.19230.033*
B11A0.09967 (8)0.75995 (19)0.14596 (8)0.0247 (4)
H11A0.07970.84440.11530.030*
B12A0.10707 (9)0.7725 (2)0.22282 (9)0.0298 (4)
H12A0.09240.86700.24350.036*
O1B0.10315 (6)0.13197 (14)0.02540 (6)0.0366 (3)
H1B0.1170 (12)0.177 (3)0.0619 (13)0.070 (8)*
O2B0.17922 (6)0.01391 (15)0.05931 (6)0.0412 (3)
O3B0.17993 (6)0.21967 (13)0.06254 (7)0.0402 (3)
C1B0.11232 (7)0.03599 (17)0.09825 (7)0.0225 (4)
C2B0.12003 (7)0.05047 (17)0.03617 (7)0.0232 (4)
C3B0.13840 (8)0.02565 (18)0.02187 (7)0.0265 (4)
C4B0.12256 (8)0.19061 (17)0.09643 (8)0.0287 (4)
H43A0.11940.22620.13660.034*
H44A0.09150.23660.07940.034*
C5B0.18878 (11)0.3644 (2)0.05319 (12)0.0533 (6)
H54A0.18440.41120.09090.080*
H55A0.22920.38110.02970.080*
H56A0.15880.40010.03260.080*
B3B0.04804 (8)0.0213 (2)0.07700 (9)0.0277 (4)
H3B0.01370.04720.06360.033*
B4B0.05624 (9)0.0326 (2)0.15040 (9)0.0305 (5)
H4B0.02690.02870.18590.037*
B5B0.13352 (9)0.0643 (2)0.15013 (9)0.0287 (4)
H5B0.15490.02330.18550.034*
B6B0.17443 (9)0.0720 (2)0.07676 (8)0.0253 (4)
H6B0.22220.03600.06310.030*
B7B0.06934 (10)0.1823 (2)0.04241 (9)0.0342 (5)
H7B0.04870.22020.00600.041*
B8B0.02888 (10)0.1750 (2)0.11616 (10)0.0372 (5)
H8B0.01910.20980.12920.045*
B9B0.08116 (10)0.2025 (2)0.16202 (9)0.0362 (5)
H9B0.06770.25510.20540.043*
B10B0.15412 (10)0.2261 (2)0.11671 (9)0.0319 (5)
H10B0.18870.29370.13020.038*
B11B0.14664 (10)0.2141 (2)0.04283 (9)0.0317 (5)
H11B0.17640.27310.00680.038*
B12B0.08923 (11)0.2947 (2)0.09521 (10)0.0395 (5)
H12B0.08100.40850.09430.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0229 (6)0.0420 (7)0.0248 (6)0.0036 (6)0.0034 (5)0.0032 (6)
O2A0.0389 (7)0.0373 (7)0.0224 (6)0.0090 (6)0.0010 (5)0.0100 (5)
O3A0.0346 (7)0.0201 (6)0.0253 (6)0.0010 (5)0.0008 (5)0.0023 (5)
C1A0.0173 (7)0.0207 (8)0.0166 (7)0.0005 (6)0.0016 (6)0.0006 (6)
C2A0.0177 (7)0.0185 (7)0.0189 (7)0.0009 (6)0.0033 (6)0.0012 (6)
C3A0.0213 (8)0.0197 (8)0.0173 (7)0.0012 (6)0.0036 (6)0.0009 (6)
C4A0.0240 (8)0.0237 (8)0.0251 (8)0.0031 (7)0.0047 (6)0.0049 (7)
C5A0.0541 (12)0.0247 (10)0.0377 (11)0.0013 (9)0.0002 (9)0.0060 (8)
B3A0.0201 (9)0.0279 (10)0.0173 (8)0.0011 (7)0.0052 (7)0.0006 (7)
B4A0.0233 (9)0.0303 (10)0.0154 (8)0.0004 (8)0.0021 (7)0.0013 (7)
B5A0.0183 (8)0.0269 (10)0.0231 (9)0.0023 (7)0.0017 (7)0.0042 (8)
B6A0.0208 (9)0.0233 (9)0.0234 (9)0.0027 (7)0.0046 (7)0.0005 (7)
B7A0.0211 (9)0.0299 (10)0.0239 (9)0.0021 (8)0.0054 (7)0.0089 (8)
B8A0.0248 (9)0.0396 (11)0.0200 (9)0.0006 (8)0.0066 (7)0.0082 (8)
B9A0.0242 (9)0.0317 (10)0.0227 (9)0.0004 (8)0.0007 (7)0.0080 (8)
B10A0.0251 (9)0.0243 (10)0.0303 (10)0.0033 (8)0.0009 (8)0.0060 (8)
B11A0.0230 (9)0.0197 (9)0.0297 (10)0.0003 (7)0.0016 (7)0.0042 (8)
B12A0.0277 (10)0.0314 (11)0.0288 (10)0.0022 (8)0.0024 (8)0.0126 (8)
O1B0.0451 (8)0.0340 (7)0.0276 (7)0.0062 (6)0.0008 (6)0.0100 (6)
O2B0.0458 (8)0.0455 (8)0.0282 (7)0.0076 (7)0.0011 (6)0.0038 (6)
O3B0.0301 (7)0.0248 (7)0.0613 (9)0.0059 (5)0.0000 (6)0.0020 (6)
C1B0.0211 (8)0.0262 (9)0.0208 (8)0.0005 (7)0.0062 (6)0.0021 (7)
C2B0.0262 (8)0.0232 (8)0.0217 (8)0.0042 (7)0.0084 (7)0.0002 (6)
C3B0.0298 (9)0.0273 (9)0.0232 (8)0.0037 (7)0.0075 (7)0.0004 (7)
C4B0.0285 (9)0.0246 (9)0.0329 (9)0.0027 (7)0.0061 (7)0.0071 (7)
C5B0.0517 (13)0.0287 (11)0.0769 (17)0.0117 (10)0.0079 (12)0.0044 (11)
B3B0.0207 (9)0.0365 (11)0.0271 (10)0.0066 (8)0.0077 (8)0.0066 (8)
B4B0.0254 (10)0.0404 (12)0.0244 (10)0.0001 (9)0.0025 (8)0.0061 (8)
B5B0.0293 (10)0.0353 (11)0.0238 (9)0.0052 (8)0.0109 (8)0.0021 (8)
B6B0.0250 (9)0.0264 (10)0.0262 (9)0.0047 (8)0.0089 (8)0.0036 (8)
B7B0.0436 (12)0.0289 (11)0.0347 (11)0.0141 (9)0.0189 (9)0.0048 (9)
B8B0.0339 (11)0.0408 (12)0.0388 (12)0.0138 (10)0.0117 (9)0.0156 (10)
B9B0.0399 (12)0.0392 (12)0.0302 (11)0.0022 (10)0.0092 (9)0.0111 (9)
B10B0.0401 (12)0.0299 (11)0.0282 (10)0.0071 (9)0.0128 (9)0.0013 (8)
B11B0.0458 (12)0.0226 (10)0.0283 (10)0.0013 (9)0.0118 (9)0.0038 (8)
B12B0.0542 (14)0.0270 (11)0.0411 (12)0.0101 (10)0.0191 (11)0.0089 (9)
Geometric parameters (Å, º) top
O1A—C3A1.2601 (19)O1B—C3B1.320 (2)
O1A—H1A0.96 (2)O1B—H1B0.95 (3)
O2A—C3A1.250 (2)O2B—C3B1.197 (2)
C1A—C4A1.535 (2)C1B—C4B1.517 (2)
C2A—C3A1.516 (2)C1B—C2B1.656 (2)
C4A—O3A1.411 (2)C1B—B4B1.703 (2)
O3A—C5A1.443 (2)C1B—B5B1.705 (2)
C1A—C2A1.669 (2)C1B—B3B1.734 (2)
C1A—B5A1.705 (2)C1B—B6B1.744 (2)
C1A—B4A1.709 (2)C2B—C3B1.526 (2)
C1A—B6A1.740 (2)C4B—O3B1.404 (2)
C1A—B3A1.743 (2)O3B—C5B1.428 (2)
C2A—B7A1.710 (2)C2B—B7B1.707 (2)
C2A—B11A1.713 (2)C2B—B11B1.718 (3)
C2A—B3A1.728 (2)C2B—B6B1.727 (2)
C2A—B6A1.733 (2)C2B—B3B1.735 (3)
C4A—H410.9900C4B—H43A0.9900
C4A—H420.9900C4B—H44A0.9900
C5A—H510.9800C5B—H54A0.9800
C5A—H520.9800C5B—H55A0.9800
C5A—H530.9800C5B—H56A0.9800
B3A—B8A1.772 (3)B3B—B8B1.756 (3)
B3A—B7A1.786 (3)B3B—B4B1.773 (3)
B3A—B4A1.788 (3)B3B—B7B1.778 (3)
B3A—H3A1.1200B3B—H3B1.1200
B4A—B5A1.775 (3)B4B—B8B1.776 (3)
B4A—B8A1.779 (3)B4B—B9B1.783 (3)
B4A—B9A1.779 (3)B4B—B5B1.783 (3)
B4A—H4A1.1200B4B—H4B1.1200
B5A—B9A1.776 (3)B5B—B10B1.772 (3)
B5A—B6A1.779 (3)B5B—B6B1.774 (3)
B5A—B10A1.781 (3)B5B—B9B1.776 (3)
B5A—H5A1.1200B5B—H5B1.1200
B6A—B10A1.771 (3)B6B—B10B1.772 (3)
B6A—B11A1.791 (3)B6B—B11B1.774 (3)
B6A—H6A1.1200B6B—H6B1.1200
B7A—B12A1.770 (3)B7B—B8B1.778 (3)
B7A—B8A1.775 (3)B7B—B12B1.779 (3)
B7A—B11A1.787 (3)B7B—B11B1.787 (3)
B7A—H7A1.1200B7B—H7B1.1200
B8A—B9A1.789 (3)B8B—B9B1.785 (3)
B8A—B12A1.794 (3)B8B—B12B1.785 (3)
B8A—H8A1.1200B8B—H8B1.1200
B9A—B12A1.780 (3)B9B—B12B1.779 (3)
B9A—B10A1.789 (3)B9B—B10B1.784 (3)
B9A—H9A1.1200B9B—H9B1.1200
B10A—B11A1.784 (3)B10B—B11B1.779 (3)
B10A—B12A1.795 (3)B10B—B12B1.787 (3)
B10A—H10A1.1200B10B—H10B1.1200
B11A—B12A1.778 (3)B11B—B12B1.772 (3)
B11A—H11A1.1200B11B—H11B1.1200
B12A—H12A1.1200B12B—H12B1.1200
C3A—O1A—H1A120.6 (13)C3B—O1B—H1B108.8 (16)
C1A—C2A—C3A120.98 (12)C1B—C2B—C3B119.73 (14)
C2A—C1A—C4A121.82 (12)C2B—C1B—C4B119.28 (14)
C1A—C4A—O3A113.90 (13)C1B—C4B—O3B109.44 (14)
C2A—C3A—O1A114.77 (14)C2B—C3B—O1B112.29 (14)
C2A—C3A—O2A119.79 (14)C2B—C3B—O2B121.40 (16)
O1A—C3A—O2A125.42 (15)O1B—C3B—O2B126.26 (16)
C4A—O3A—C5A115.22 (13)C4B—O3B—C5B111.58 (15)
C4A—C1A—B5A117.14 (12)C4B—C1B—B4B119.56 (14)
C2A—C1A—B5A110.02 (12)C2B—C1B—B4B110.84 (13)
C4A—C1A—B4A120.72 (13)C4B—C1B—B5B121.26 (14)
C2A—C1A—B4A109.99 (12)C2B—C1B—B5B110.17 (13)
B5A—C1A—B4A62.65 (10)B4B—C1B—B5B63.11 (11)
C4A—C1A—B6A115.11 (12)C4B—C1B—B3B116.28 (14)
C2A—C1A—B6A61.06 (9)C2B—C1B—B3B61.52 (10)
B5A—C1A—B6A62.18 (10)B4B—C1B—B3B62.10 (11)
B4A—C1A—B6A113.87 (12)B5B—C1B—B3B113.95 (13)
C4A—C1A—B3A120.90 (13)C4B—C1B—B6B118.39 (13)
C2A—C1A—B3A60.78 (9)C2B—C1B—B6B60.97 (10)
B5A—C1A—B3A113.93 (12)B4B—C1B—B6B114.19 (14)
B4A—C1A—B3A62.36 (10)B5B—C1B—B6B61.89 (11)
B6A—C1A—B3A113.68 (12)B3B—C1B—B6B113.91 (13)
C3A—C2A—B7A118.13 (13)C3B—C2B—B7B119.38 (14)
C1A—C2A—B7A111.42 (12)C1B—C2B—B7B111.16 (13)
C3A—C2A—B11A118.14 (13)C3B—C2B—B11B119.55 (14)
C1A—C2A—B11A111.60 (12)C1B—C2B—B11B111.19 (13)
B7A—C2A—B11A62.93 (11)B7B—C2B—B11B62.92 (12)
C3A—C2A—B3A117.10 (13)C3B—C2B—B6B117.21 (13)
C1A—C2A—B3A61.73 (9)C1B—C2B—B6B62.04 (10)
B7A—C2A—B3A62.60 (10)B7B—C2B—B6B114.37 (13)
B11A—C2A—B3A115.04 (12)B11B—C2B—B6B62.00 (11)
C3A—C2A—B6A117.84 (12)C3B—C2B—B3B117.40 (14)
C1A—C2A—B6A61.47 (9)C1B—C2B—B3B61.44 (10)
B7A—C2A—B6A114.60 (12)B7B—C2B—B3B62.22 (12)
B11A—C2A—B6A62.64 (10)B11B—C2B—B3B114.20 (14)
B3A—C2A—B6A114.84 (12)B6B—C2B—B3B114.75 (13)
O3A—C4A—H41108.8O3B—C4B—H43A109.8
C1A—C4A—H41108.8C1B—C4B—H43A109.8
O3A—C4A—H42108.8O3B—C4B—H44A109.8
C1A—C4A—H42108.8C1B—C4B—H44A109.8
H41—C4A—H42107.7H43A—C4B—H44A108.2
O3A—C5A—H51109.5O3B—C5B—H54A109.5
O3A—C5A—H52109.5O3B—C5B—H55A109.5
H51—C5A—H52109.5H54A—C5B—H55A109.5
O3A—C5A—H53109.5O3B—C5B—H56A109.5
H51—C5A—H53109.5H54A—C5B—H56A109.5
H52—C5A—H53109.5H55A—C5B—H56A109.5
C2A—B3A—C1A57.49 (9)C1B—B3B—C2B57.04 (9)
C2A—B3A—B8A104.20 (13)C1B—B3B—B8B104.64 (14)
C1A—B3A—B8A104.42 (12)C2B—B3B—B8B104.48 (15)
C2A—B3A—B7A58.22 (10)C1B—B3B—B4B58.10 (10)
C1A—B3A—B7A104.57 (12)C2B—B3B—B4B104.09 (13)
B8A—B3A—B7A59.86 (11)B8B—B3B—B4B60.42 (12)
C2A—B3A—B4A103.84 (12)C1B—B3B—B7B104.36 (14)
C1A—B3A—B4A57.87 (9)C2B—B3B—B7B58.13 (11)
B8A—B3A—B4A59.95 (10)B8B—B3B—B7B60.41 (13)
B7A—B3A—B4A107.30 (13)B4B—B3B—B7B108.28 (15)
C2A—B3A—H3A124.9C1B—B3B—H3B124.9
C1A—B3A—H3A124.6C2B—B3B—H3B125.0
B8A—B3A—H3A123.1B8B—B3B—H3B122.7
B7A—B3A—H3A122.4B4B—B3B—H3B122.2
B4A—B3A—H3A122.8B7B—B3B—H3B122.1
C1A—B4A—B5A58.56 (10)C1B—B4B—B3B59.80 (10)
C1A—B4A—B8A105.58 (12)C1B—B4B—B8B105.11 (14)
B5A—B4A—B8A108.37 (14)B3B—B4B—B8B59.33 (12)
C1A—B4A—B9A105.07 (13)C1B—B4B—B9B104.88 (14)
B5A—B4A—B9A59.96 (11)B3B—B4B—B9B107.93 (15)
B8A—B4A—B9A60.38 (11)B8B—B4B—B9B60.21 (12)
C1A—B4A—B3A59.76 (9)C1B—B4B—B5B58.50 (10)
B5A—B4A—B3A108.48 (13)B3B—B4B—B5B108.33 (14)
B8A—B4A—B3A59.58 (10)B8B—B4B—B5B107.72 (15)
B9A—B4A—B3A108.06 (13)B9B—B4B—B5B59.73 (12)
C1A—B4A—H4A124.1C1B—B4B—H4B124.2
B5A—B4A—H4A121.4B3B—B4B—H4B121.3
B8A—B4A—H4A122.1B8B—B4B—H4B122.5
B9A—B4A—H4A122.3B9B—B4B—H4B122.4
B3A—B4A—H4A121.2B5B—B4B—H4B121.7
C1A—B5A—B4A58.79 (10)C1B—B5B—B10B106.15 (13)
C1A—B5A—B9A105.39 (12)C1B—B5B—B6B60.15 (10)
B4A—B5A—B9A60.14 (11)B10B—B5B—B6B59.96 (11)
C1A—B5A—B6A59.87 (10)C1B—B5B—B9B105.10 (13)
B4A—B5A—B6A108.84 (13)B10B—B5B—B9B60.39 (12)
B9A—B5A—B6A108.21 (13)B6B—B5B—B9B108.43 (14)
C1A—B5A—B10A105.86 (12)C1B—B5B—B4B58.39 (10)
B4A—B5A—B10A108.70 (13)B10B—B5B—B4B108.77 (15)
B9A—B5A—B10A60.39 (11)B6B—B5B—B4B108.90 (13)
B6A—B5A—B10A59.65 (10)B9B—B5B—B4B60.12 (12)
C1A—B5A—H5A123.9C1B—B5B—H5B124.0
B4A—B5A—H5A121.1B10B—B5B—H5B121.7
B9A—B5A—H5A122.2B6B—B5B—H5B120.8
B6A—B5A—H5A121.1B9B—B5B—H5B122.3
B10A—B5A—H5A122.0B4B—B5B—H5B121.3
C2A—B6A—C1A57.47 (9)C2B—B6B—C1B56.99 (9)
C2A—B6A—B10A104.32 (13)C2B—B6B—B10B104.84 (14)
C1A—B6A—B10A104.84 (13)C1B—B6B—B10B104.46 (13)
C2A—B6A—B5A103.84 (12)C2B—B6B—B11B58.75 (11)
C1A—B6A—B5A57.95 (10)C1B—B6B—B11B104.60 (13)
B10A—B6A—B5A60.25 (11)B10B—B6B—B11B60.24 (11)
C2A—B6A—B11A58.13 (10)C2B—B6B—B5B103.86 (13)
C1A—B6A—B11A104.79 (12)C1B—B6B—B5B57.96 (10)
B10A—B6A—B11A60.12 (11)B10B—B6B—B5B59.96 (11)
B5A—B6A—B11A107.74 (13)B11B—B6B—B5B107.69 (14)
C2A—B6A—H6A125.0C2B—B6B—H6B124.7
C1A—B6A—H6A124.4C1B—B6B—H6B124.9
B10A—B6A—H6A122.8B10B—B6B—H6B122.8
B5A—B6A—H6A122.6B11B—B6B—H6B122.0
B11A—B6A—H6A122.2B5B—B6B—H6B122.7
C2A—B7A—B12A104.69 (13)C2B—B7B—B8B104.70 (14)
C2A—B7A—B8A104.80 (13)C2B—B7B—B3B59.65 (10)
B12A—B7A—B8A60.81 (11)B8B—B7B—B3B59.18 (12)
C2A—B7A—B3A59.19 (10)C2B—B7B—B12B104.57 (14)
B12A—B7A—B3A108.59 (13)B8B—B7B—B12B60.24 (13)
B8A—B7A—B3A59.67 (10)B3B—B7B—B12B107.81 (15)
C2A—B7A—B11A58.61 (10)C2B—B7B—B11B58.83 (11)
B12A—B7A—B11A59.98 (11)B8B—B7B—B11B107.91 (15)
B8A—B7A—B11A108.69 (13)B3B—B7B—B11B108.77 (14)
B3A—B7A—B11A108.66 (13)B12B—B7B—B11B59.60 (12)
C2A—B7A—H7A124.8C2B—B7B—H7B124.5
B12A—B7A—H7A122.1B8B—B7B—H7B122.7
B8A—B7A—H7A122.1B3B—B7B—H7B121.2
B3A—B7A—H7A121.1B12B—B7B—H7B122.6
B11A—B7A—H7A121.2B11B—B7B—H7B121.3
B3A—B8A—B7A60.47 (10)B3B—B8B—B4B60.25 (12)
B3A—B8A—B4A60.47 (10)B3B—B8B—B7B60.41 (12)
B7A—B8A—B4A108.19 (13)B4B—B8B—B7B108.15 (14)
B3A—B8A—B9A108.33 (13)B3B—B8B—B9B108.56 (15)
B7A—B8A—B9A107.30 (14)B4B—B8B—B9B60.09 (12)
B4A—B8A—B9A59.82 (11)B7B—B8B—B9B107.83 (16)
B3A—B8A—B12A108.14 (13)B3B—B8B—B12B108.52 (15)
B7A—B8A—B12A59.45 (11)B4B—B8B—B12B107.90 (15)
B4A—B8A—B12A107.55 (14)B7B—B8B—B12B59.89 (13)
B9A—B8A—B12A59.59 (11)B9B—B8B—B12B59.77 (13)
B3A—B8A—H8A121.1B3B—B8B—H8B121.1
B7A—B8A—H8A121.9B4B—B8B—H8B121.7
B4A—B8A—H8A121.7B7B—B8B—H8B121.7
B9A—B8A—H8A122.0B9B—B8B—H8B121.7
B12A—B8A—H8A122.2B12B—B8B—H8B121.8
B5A—B9A—B4A59.90 (10)B5B—B9B—B12B107.56 (15)
B5A—B9A—B12A108.10 (13)B5B—B9B—B4B60.16 (12)
B4A—B9A—B12A108.13 (13)B12B—B9B—B4B107.88 (14)
B5A—B9A—B8A107.86 (13)B5B—B9B—B10B59.70 (12)
B4A—B9A—B8A59.80 (11)B12B—B9B—B10B60.21 (13)
B12A—B9A—B8A60.35 (11)B4B—B9B—B10B108.25 (15)
B5A—B9A—B10A59.96 (11)B5B—B9B—B8B107.67 (14)
B4A—B9A—B10A108.16 (13)B12B—B9B—B8B60.12 (13)
B12A—B9A—B10A60.37 (11)B4B—B9B—B8B59.71 (12)
B8A—B9A—B10A108.63 (13)B10B—B9B—B8B108.37 (15)
B5A—B9A—H9A121.9B5B—B9B—H9B122.1
B4A—B9A—H9A121.8B12B—B9B—H9B121.8
B12A—B9A—H9A121.4B4B—B9B—H9B121.7
B8A—B9A—H9A121.6B10B—B9B—H9B121.5
B10A—B9A—H9A121.4B8B—B9B—H9B121.7
B6A—B10A—B5A60.11 (10)B5B—B10B—B6B60.08 (11)
B6A—B10A—B11A60.50 (10)B5B—B10B—B11B107.55 (14)
B5A—B10A—B11A107.93 (13)B6B—B10B—B11B59.94 (11)
B6A—B10A—B9A107.98 (13)B5B—B10B—B9B59.91 (12)
B5A—B10A—B9A59.65 (11)B6B—B10B—B9B108.14 (14)
B11A—B10A—B9A107.39 (14)B11B—B10B—B9B107.54 (15)
B6A—B10A—B12A108.02 (13)B5B—B10B—B12B107.36 (15)
B5A—B10A—B12A107.22 (14)B6B—B10B—B12B107.67 (14)
B11A—B10A—B12A59.56 (11)B11B—B10B—B12B59.60 (12)
B9A—B10A—B12A59.57 (11)B9B—B10B—B12B59.75 (13)
B6A—B10A—H10A121.3B5B—B10B—H10B122.0
B5A—B10A—H10A122.0B6B—B10B—H10B121.6
B11A—B10A—H10A121.8B11B—B10B—H10B122.1
B9A—B10A—H10A122.1B9B—B10B—H10B121.8
B12A—B10A—H10A122.2B12B—B10B—H10B122.2
C2A—B11A—B12A104.23 (13)C2B—B11B—B12B104.40 (15)
C2A—B11A—B10A104.58 (13)C2B—B11B—B6B59.25 (10)
B12A—B11A—B10A60.51 (11)B12B—B11B—B6B108.22 (15)
C2A—B11A—B7A58.46 (10)C2B—B11B—B10B104.90 (14)
B12A—B11A—B7A59.54 (11)B12B—B11B—B10B60.41 (12)
B10A—B11A—B7A107.98 (14)B6B—B11B—B10B59.82 (11)
C2A—B11A—B6A59.23 (10)C2B—B11B—B7B58.25 (11)
B12A—B11A—B6A107.87 (13)B12B—B11B—B7B59.96 (12)
B10A—B11A—B6A59.37 (10)B6B—B11B—B7B108.25 (14)
B7A—B11A—B6A108.15 (13)B10B—B11B—B7B108.34 (15)
C2A—B11A—H11A124.8C2B—B11B—H11B124.9
B12A—B11A—H11A122.5B12B—B11B—H11B122.3
B10A—B11A—H11A122.4B6B—B11B—H11B121.2
B7A—B11A—H11A121.6B10B—B11B—H11B122.1
B6A—B11A—H11A121.4B7B—B11B—H11B121.5
B7A—B12A—B11A60.48 (11)B11B—B12B—B9B108.09 (15)
B7A—B12A—B9A107.91 (14)B11B—B12B—B7B60.44 (12)
B11A—B12A—B9A108.07 (13)B9B—B12B—B7B108.08 (16)
B7A—B12A—B8A59.75 (11)B11B—B12B—B8B108.28 (15)
B11A—B12A—B8A108.25 (13)B9B—B12B—B8B60.11 (13)
B9A—B12A—B8A60.06 (11)B7B—B12B—B8B59.87 (13)
B7A—B12A—B10A108.27 (13)B11B—B12B—B10B59.99 (12)
B11A—B12A—B10A59.93 (11)B9B—B12B—B10B60.04 (12)
B9A—B12A—B10A60.06 (11)B7B—B12B—B10B108.39 (15)
B8A—B12A—B10A108.16 (14)B8B—B12B—B10B108.24 (15)
B7A—B12A—H12A121.6B11B—B12B—H12B121.5
B11A—B12A—H12A121.5B9B—B12B—H12B121.7
B9A—B12A—H12A121.8B7B—B12B—H12B121.5
B8A—B12A—H12A121.7B8B—B12B—H12B121.6
B10A—B12A—H12A121.6B10B—B12B—H12B121.6
C4A—C1A—C2A—C3A3.9 (2)C4B—C1B—C2B—C3B1.1 (2)
B5A—C1A—C2A—C3A146.81 (14)B4B—C1B—C2B—C3B146.10 (15)
B4A—C1A—C2A—C3A146.01 (14)B5B—C1B—C2B—C3B145.97 (15)
B6A—C1A—C2A—C3A107.08 (15)B3B—C1B—C2B—C3B107.01 (16)
B3A—C1A—C2A—C3A106.28 (15)B6B—C1B—C2B—C3B107.04 (16)
C4A—C1A—C2A—B7A149.65 (14)C4B—C1B—C2B—B7B144.63 (15)
B5A—C1A—C2A—B7A67.47 (15)B4B—C1B—C2B—B7B0.32 (18)
B4A—C1A—C2A—B7A0.29 (17)B5B—C1B—C2B—B7B68.26 (17)
B6A—C1A—C2A—B7A107.20 (14)B3B—C1B—C2B—B7B38.77 (14)
B3A—C1A—C2A—B7A39.44 (12)B6B—C1B—C2B—B7B107.19 (15)
C4A—C1A—C2A—B11A142.09 (14)C4B—C1B—C2B—B11B147.31 (15)
B5A—C1A—C2A—B11A0.79 (16)B4B—C1B—C2B—B11B67.74 (17)
B4A—C1A—C2A—B11A67.97 (15)B5B—C1B—C2B—B11B0.19 (18)
B6A—C1A—C2A—B11A38.94 (12)B3B—C1B—C2B—B11B106.83 (15)
B3A—C1A—C2A—B11A107.70 (14)B6B—C1B—C2B—B11B39.12 (13)
C4A—C1A—C2A—B3A110.21 (15)C4B—C1B—C2B—B6B108.19 (16)
B5A—C1A—C2A—B3A106.91 (13)B4B—C1B—C2B—B6B106.86 (15)
B4A—C1A—C2A—B3A39.73 (12)B5B—C1B—C2B—B6B38.93 (13)
B6A—C1A—C2A—B3A146.64 (12)B3B—C1B—C2B—B6B145.95 (14)
C4A—C1A—C2A—B6A103.15 (15)C4B—C1B—C2B—B3B105.86 (16)
B5A—C1A—C2A—B6A39.73 (12)B4B—C1B—C2B—B3B39.09 (13)
B4A—C1A—C2A—B6A106.91 (13)B5B—C1B—C2B—B3B107.02 (15)
B3A—C1A—C2A—B6A146.64 (12)B6B—C1B—C2B—B3B145.95 (14)
C1A—C2A—C3A—O1A164.45 (13)C1B—C2B—C3B—O1B53.25 (19)
C1A—C2A—C3A—O2A17.1 (2)C1B—C2B—C3B—O2B129.22 (18)
B7A—C2A—C3A—O2A160.66 (15)C2B—C1B—C4B—O3B55.16 (19)
B11A—C2A—C3A—O2A126.75 (16)B7B—C2B—C3B—O2B87.8 (2)
B3A—C2A—C3A—O2A88.88 (18)B11B—C2B—C3B—O2B14.1 (2)
B6A—C2A—C3A—O2A54.6 (2)B6B—C2B—C3B—O2B57.5 (2)
B7A—C2A—C3A—O1A20.9 (2)B3B—C2B—C3B—O2B159.69 (16)
B11A—C2A—C3A—O1A51.65 (19)B7B—C2B—C3B—O1B89.74 (19)
B3A—C2A—C3A—O1A92.72 (17)B11B—C2B—C3B—O1B163.39 (14)
B6A—C2A—C3A—O1A123.78 (15)B6B—C2B—C3B—O1B124.99 (15)
C5A—O3A—C4A—C1A90.62 (18)B3B—C2B—C3B—O1B17.8 (2)
C2A—C1A—C4A—O3A69.56 (18)C5B—O3B—C4B—C1B172.45 (17)
B5A—C1A—C4A—O3A150.01 (13)B4B—C1B—C4B—O3B162.94 (14)
B4A—C1A—C4A—O3A77.23 (18)B5B—C1B—C4B—O3B88.24 (19)
B6A—C1A—C4A—O3A139.80 (13)B3B—C1B—C4B—O3B125.71 (15)
B3A—C1A—C4A—O3A3.1 (2)B6B—C1B—C4B—O3B15.6 (2)
C3A—C2A—B3A—C1A112.42 (14)C4B—C1B—B3B—C2B110.65 (16)
B7A—C2A—B3A—C1A138.23 (12)B4B—C1B—B3B—C2B138.18 (14)
B11A—C2A—B3A—C1A102.13 (13)B5B—C1B—B3B—C2B100.85 (15)
B6A—C2A—B3A—C1A32.17 (12)B6B—C1B—B3B—C2B32.38 (13)
C3A—C2A—B3A—B8A149.34 (13)C4B—C1B—B3B—B8B151.38 (16)
C1A—C2A—B3A—B8A98.24 (12)C2B—C1B—B3B—B8B97.97 (15)
B7A—C2A—B3A—B8A39.99 (12)B4B—C1B—B3B—B8B40.22 (14)
B11A—C2A—B3A—B8A3.88 (17)B5B—C1B—B3B—B8B2.88 (19)
B6A—C2A—B3A—B8A66.07 (15)B6B—C1B—B3B—B8B65.59 (17)
C3A—C2A—B3A—B7A109.35 (15)C4B—C1B—B3B—B4B111.17 (16)
C1A—C2A—B3A—B7A138.23 (12)C2B—C1B—B3B—B4B138.18 (14)
B11A—C2A—B3A—B7A36.11 (13)B5B—C1B—B3B—B4B37.33 (14)
B6A—C2A—B3A—B7A106.07 (14)B6B—C1B—B3B—B4B105.81 (15)
C3A—C2A—B3A—B4A148.67 (13)C4B—C1B—B3B—B7B146.00 (14)
C1A—C2A—B3A—B4A36.25 (11)C2B—C1B—B3B—B7B35.35 (12)
B7A—C2A—B3A—B4A101.98 (13)B4B—C1B—B3B—B7B102.83 (15)
B11A—C2A—B3A—B4A65.87 (15)B5B—C1B—B3B—B7B65.50 (17)
B6A—C2A—B3A—B4A4.08 (17)B6B—C1B—B3B—B7B2.98 (18)
C4A—C1A—B3A—C2A111.67 (15)C3B—C2B—B3B—C1B110.72 (16)
B5A—C1A—B3A—C2A100.42 (13)B7B—C2B—B3B—C1B138.70 (14)
B4A—C1A—B3A—C2A137.32 (13)B11B—C2B—B3B—C1B101.92 (14)
B6A—C1A—B3A—C2A31.70 (12)B6B—C2B—B3B—C1B32.99 (13)
C4A—C1A—B3A—B8A150.49 (14)C3B—C2B—B3B—B8B151.01 (14)
C2A—C1A—B3A—B8A97.84 (13)C1B—C2B—B3B—B8B98.26 (14)
B5A—C1A—B3A—B8A2.58 (17)B7B—C2B—B3B—B8B40.43 (13)
B4A—C1A—B3A—B8A39.47 (12)B11B—C2B—B3B—B8B3.66 (18)
B6A—C1A—B3A—B8A66.14 (15)B6B—C2B—B3B—B8B65.27 (17)
C4A—C1A—B3A—B7A147.48 (14)C3B—C2B—B3B—B4B146.43 (15)
C2A—C1A—B3A—B7A35.80 (11)C1B—C2B—B3B—B4B35.70 (12)
B5A—C1A—B3A—B7A64.62 (15)B7B—C2B—B3B—B4B102.99 (15)
B4A—C1A—B3A—B7A101.51 (13)B11B—C2B—B3B—B4B66.22 (17)
B6A—C1A—B3A—B7A4.10 (16)B6B—C2B—B3B—B4B2.71 (19)
C4A—C1A—B3A—B4A111.01 (16)C3B—C2B—B3B—B7B110.58 (16)
C2A—C1A—B3A—B4A137.32 (13)C1B—C2B—B3B—B7B138.70 (14)
B5A—C1A—B3A—B4A36.89 (13)B11B—C2B—B3B—B7B36.78 (13)
B6A—C1A—B3A—B4A105.61 (14)B6B—C2B—B3B—B7B105.70 (15)
C4A—C1A—B4A—B5A106.86 (15)C4B—C1B—B4B—B3B106.01 (17)
C2A—C1A—B4A—B5A102.82 (13)C2B—C1B—B4B—B3B38.84 (13)
B6A—C1A—B4A—B5A36.53 (12)B5B—C1B—B4B—B3B141.58 (15)
B3A—C1A—B4A—B5A141.84 (13)B6B—C1B—B4B—B3B105.37 (15)
C4A—C1A—B4A—B8A150.85 (14)C4B—C1B—B4B—B8B145.79 (16)
C2A—C1A—B4A—B8A0.53 (17)C2B—C1B—B4B—B8B0.95 (18)
B5A—C1A—B4A—B8A102.29 (14)B5B—C1B—B4B—B8B101.79 (15)
B6A—C1A—B4A—B8A65.76 (16)B3B—C1B—B4B—B8B39.79 (13)
B3A—C1A—B4A—B8A39.55 (12)B6B—C1B—B4B—B8B65.58 (17)
C4A—C1A—B4A—B9A146.31 (14)C4B—C1B—B4B—B9B151.64 (15)
C2A—C1A—B4A—B9A63.37 (15)C2B—C1B—B4B—B9B63.51 (16)
B5A—C1A—B4A—B9A39.44 (12)B5B—C1B—B4B—B9B39.23 (13)
B6A—C1A—B4A—B9A2.91 (17)B3B—C1B—B4B—B9B102.35 (16)
B3A—C1A—B4A—B9A102.40 (14)B6B—C1B—B4B—B9B3.02 (18)
C4A—C1A—B4A—B3A111.30 (15)C4B—C1B—B4B—B5B112.41 (17)
C2A—C1A—B4A—B3A39.02 (12)C2B—C1B—B4B—B5B102.75 (14)
B5A—C1A—B4A—B3A141.84 (13)B3B—C1B—B4B—B5B141.58 (15)
B6A—C1A—B4A—B3A105.31 (13)B6B—C1B—B4B—B5B36.22 (14)
C2A—B3A—B4A—C1A36.07 (11)C2B—B3B—B4B—C1B35.23 (12)
B8A—B3A—B4A—C1A134.66 (14)B8B—B3B—B4B—C1B134.09 (15)
B7A—B3A—B4A—C1A96.64 (13)B7B—B3B—B4B—C1B95.86 (14)
C2A—B3A—B4A—B5A2.31 (16)C1B—B3B—B4B—B8B134.09 (15)
C1A—B3A—B4A—B5A33.76 (11)C2B—B3B—B4B—B8B98.86 (15)
B8A—B3A—B4A—B5A100.90 (15)B7B—B3B—B4B—B8B38.23 (14)
B7A—B3A—B4A—B5A62.87 (15)C1B—B3B—B4B—B9B97.12 (15)
C2A—B3A—B4A—B8A98.59 (14)C2B—B3B—B4B—B9B61.89 (17)
C1A—B3A—B4A—B8A134.66 (14)B8B—B3B—B4B—B9B36.97 (14)
B7A—B3A—B4A—B8A38.02 (13)B7B—B3B—B4B—B9B1.26 (18)
C2A—B3A—B4A—B9A61.19 (15)C1B—B3B—B4B—B5B33.93 (13)
C1A—B3A—B4A—B9A97.26 (14)C2B—B3B—B4B—B5B1.30 (19)
B8A—B3A—B4A—B9A37.40 (13)B8B—B3B—B4B—B5B100.16 (17)
B7A—B3A—B4A—B9A0.63 (16)B7B—B3B—B4B—B5B61.93 (18)
C4A—C1A—B5A—B4A112.40 (15)C4B—C1B—B5B—B10B147.75 (15)
C2A—C1A—B5A—B4A102.78 (13)C2B—C1B—B5B—B10B1.39 (18)
B6A—C1A—B5A—B4A142.01 (13)B4B—C1B—B5B—B10B102.42 (16)
B3A—C1A—B5A—B4A36.78 (13)B3B—C1B—B5B—B10B65.49 (17)
C4A—C1A—B5A—B9A152.00 (14)B6B—C1B—B5B—B10B39.91 (13)
C2A—C1A—B5A—B9A63.18 (15)C4B—C1B—B5B—B6B107.83 (16)
B4A—C1A—B5A—B9A39.60 (12)C2B—C1B—B5B—B6B38.53 (13)
B6A—C1A—B5A—B9A102.41 (14)B4B—C1B—B5B—B6B142.34 (15)
B3A—C1A—B5A—B9A2.82 (17)B3B—C1B—B5B—B6B105.40 (15)
C4A—C1A—B5A—B6A105.59 (15)C4B—C1B—B5B—B9B149.30 (15)
C2A—C1A—B5A—B6A39.23 (12)C2B—C1B—B5B—B9B64.34 (16)
B4A—C1A—B5A—B6A142.01 (13)B4B—C1B—B5B—B9B39.47 (14)
B3A—C1A—B5A—B6A105.23 (14)B3B—C1B—B5B—B9B2.53 (19)
C4A—C1A—B5A—B10A145.03 (14)B6B—C1B—B5B—B9B102.87 (15)
C2A—C1A—B5A—B10A0.22 (16)C4B—C1B—B5B—B4B109.83 (17)
B4A—C1A—B5A—B10A102.57 (14)C2B—C1B—B5B—B4B103.81 (14)
B6A—C1A—B5A—B10A39.45 (12)B3B—C1B—B5B—B4B36.94 (14)
B3A—C1A—B5A—B10A65.78 (16)B6B—C1B—B5B—B4B142.34 (15)
B8A—B4A—B5A—C1A97.40 (13)B3B—B4B—B5B—C1B34.45 (13)
B9A—B4A—B5A—C1A134.87 (13)B8B—B4B—B5B—C1B97.18 (15)
B3A—B4A—B5A—C1A34.25 (12)B9B—B4B—B5B—C1B134.94 (15)
C1A—B4A—B5A—B9A134.87 (13)C1B—B4B—B5B—B10B97.81 (15)
B8A—B4A—B5A—B9A37.47 (12)B3B—B4B—B5B—B10B63.35 (18)
B3A—B4A—B5A—B9A100.62 (14)B8B—B4B—B5B—B10B0.63 (19)
C1A—B4A—B5A—B6A34.23 (12)B9B—B4B—B5B—B10B37.14 (14)
B8A—B4A—B5A—B6A63.17 (16)C1B—B4B—B5B—B6B34.07 (13)
B9A—B4A—B5A—B6A100.65 (14)B3B—B4B—B5B—B6B0.4 (2)
B3A—B4A—B5A—B6A0.02 (17)B8B—B4B—B5B—B6B63.12 (18)
C1A—B4A—B5A—B10A97.60 (13)B9B—B4B—B5B—B6B100.88 (16)
B8A—B4A—B5A—B10A0.20 (17)C1B—B4B—B5B—B9B134.94 (15)
B9A—B4A—B5A—B10A37.28 (12)B3B—B4B—B5B—B9B100.49 (17)
B3A—B4A—B5A—B10A63.35 (16)B8B—B4B—B5B—B9B37.76 (14)
C3A—C2A—B6A—C1A112.05 (14)C3B—C2B—B6B—C1B111.00 (16)
B7A—C2A—B6A—C1A102.02 (14)B7B—C2B—B6B—C1B102.01 (15)
B11A—C2A—B6A—C1A138.85 (12)B11B—C2B—B6B—C1B138.22 (14)
B3A—C2A—B6A—C1A32.26 (12)B3B—C2B—B6B—C1B32.78 (13)
C3A—C2A—B6A—B10A149.28 (14)C3B—C2B—B6B—B10B151.19 (15)
C1A—C2A—B6A—B10A98.67 (13)C1B—C2B—B6B—B10B97.81 (14)
B7A—C2A—B6A—B10A3.35 (17)B7B—C2B—B6B—B10B4.20 (18)
B11A—C2A—B6A—B10A40.18 (12)B11B—C2B—B6B—B10B40.41 (13)
B3A—C2A—B6A—B10A66.41 (16)B3B—C2B—B6B—B10B65.02 (17)
C3A—C2A—B6A—B5A148.41 (13)C3B—C2B—B6B—B11B110.78 (16)
C1A—C2A—B6A—B5A36.35 (11)C1B—C2B—B6B—B11B138.22 (14)
B7A—C2A—B6A—B5A65.67 (16)B7B—C2B—B6B—B11B36.21 (15)
B11A—C2A—B6A—B5A102.50 (13)B3B—C2B—B6B—B11B105.44 (16)
B3A—C2A—B6A—B5A4.10 (17)C3B—C2B—B6B—B5B146.72 (15)
C3A—C2A—B6A—B11A109.09 (15)C1B—C2B—B6B—B5B35.72 (12)
C1A—C2A—B6A—B11A138.85 (12)B7B—C2B—B6B—B5B66.30 (17)
B7A—C2A—B6A—B11A36.83 (13)B11B—C2B—B6B—B5B102.50 (15)
B3A—C2A—B6A—B11A106.60 (14)B3B—C2B—B6B—B5B2.93 (18)
C4A—C1A—B6A—C2A113.97 (14)C4B—C1B—B6B—C2B109.63 (16)
B5A—C1A—B6A—C2A137.23 (12)B4B—C1B—B6B—C2B101.35 (15)
B4A—C1A—B6A—C2A100.52 (13)B5B—C1B—B6B—C2B138.04 (14)
B3A—C1A—B6A—C2A31.61 (11)B3B—C1B—B6B—C2B32.57 (13)
C4A—C1A—B6A—B10A148.31 (13)C4B—C1B—B6B—B10B151.86 (15)
C2A—C1A—B6A—B10A97.73 (13)C2B—C1B—B6B—B10B98.51 (14)
B5A—C1A—B6A—B10A39.50 (12)B4B—C1B—B6B—B10B2.84 (18)
B4A—C1A—B6A—B10A2.79 (16)B5B—C1B—B6B—B10B39.53 (13)
B3A—C1A—B6A—B10A66.12 (15)B3B—C1B—B6B—B10B65.94 (16)
C4A—C1A—B6A—B5A108.80 (14)C4B—C1B—B6B—B11B145.69 (15)
C2A—C1A—B6A—B5A137.23 (12)C2B—C1B—B6B—B11B36.06 (12)
B4A—C1A—B6A—B5A36.71 (13)B4B—C1B—B6B—B11B65.29 (17)
B3A—C1A—B6A—B5A105.62 (13)B5B—C1B—B6B—B11B101.98 (15)
C4A—C1A—B6A—B11A149.27 (13)B3B—C1B—B6B—B11B3.49 (18)
C2A—C1A—B6A—B11A35.31 (11)C4B—C1B—B6B—B5B112.34 (17)
B5A—C1A—B6A—B11A101.92 (13)C2B—C1B—B6B—B5B138.04 (14)
B4A—C1A—B6A—B11A65.21 (15)B4B—C1B—B6B—B5B36.68 (14)
B3A—C1A—B6A—B11A3.70 (16)B3B—C1B—B6B—B5B105.47 (15)
C1A—B5A—B6A—C2A36.13 (11)C1B—B5B—B6B—C2B35.28 (12)
B4A—B5A—B6A—C2A2.34 (16)B10B—B5B—B6B—C2B99.33 (14)
B9A—B5A—B6A—C2A61.46 (15)B9B—B5B—B6B—C2B61.92 (16)
B10A—B5A—B6A—C2A98.77 (13)B4B—B5B—B6B—C2B1.91 (18)
B4A—B5A—B6A—C1A33.80 (12)B10B—B5B—B6B—C1B134.61 (14)
B9A—B5A—B6A—C1A97.59 (13)B9B—B5B—B6B—C1B97.20 (14)
B10A—B5A—B6A—C1A134.91 (13)B4B—B5B—B6B—C1B33.37 (13)
C1A—B5A—B6A—B10A134.91 (13)C1B—B5B—B6B—B10B134.61 (14)
B4A—B5A—B6A—B10A101.11 (14)B9B—B5B—B6B—B10B37.41 (14)
B9A—B5A—B6A—B10A37.32 (13)B4B—B5B—B6B—B10B101.24 (16)
C1A—B5A—B6A—B11A96.66 (13)C1B—B5B—B6B—B11B96.46 (14)
B4A—B5A—B6A—B11A62.86 (16)B10B—B5B—B6B—B11B38.16 (14)
B9A—B5A—B6A—B11A0.93 (17)B9B—B5B—B6B—B11B0.75 (18)
B10A—B5A—B6A—B11A38.25 (12)B4B—B5B—B6B—B11B63.09 (18)
C3A—C2A—B7A—B12A149.12 (14)C3B—C2B—B7B—B8B147.36 (15)
C1A—C2A—B7A—B12A64.08 (16)C1B—C2B—B7B—B8B1.44 (19)
B11A—C2A—B7A—B12A40.02 (13)B11B—C2B—B7B—B8B102.29 (16)
B3A—C2A—B7A—B12A103.14 (14)B6B—C2B—B7B—B8B66.43 (18)
B6A—C2A—B7A—B12A3.30 (18)B3B—C2B—B7B—B8B39.88 (13)
C3A—C2A—B7A—B8A147.77 (14)C3B—C2B—B7B—B3B107.48 (17)
C1A—C2A—B7A—B8A0.97 (17)C1B—C2B—B7B—B3B38.44 (13)
B11A—C2A—B7A—B8A103.13 (14)B11B—C2B—B7B—B3B142.17 (14)
B3A—C2A—B7A—B8A40.03 (12)B6B—C2B—B7B—B3B106.31 (15)
B6A—C2A—B7A—B8A66.41 (17)C3B—C2B—B7B—B12B150.16 (16)
C3A—C2A—B7A—B3A107.74 (15)C1B—C2B—B7B—B12B63.93 (18)
C1A—C2A—B7A—B3A39.06 (12)B11B—C2B—B7B—B12B39.81 (14)
B11A—C2A—B7A—B3A143.16 (13)B6B—C2B—B7B—B12B3.9 (2)
B6A—C2A—B7A—B3A106.44 (14)B3B—C2B—B7B—B12B102.36 (16)
C3A—C2A—B7A—B11A109.10 (15)C3B—C2B—B7B—B11B110.35 (17)
C1A—C2A—B7A—B11A104.10 (13)C1B—C2B—B7B—B11B103.73 (14)
B3A—C2A—B7A—B11A143.16 (13)B6B—C2B—B7B—B11B35.86 (14)
B6A—C2A—B7A—B11A36.72 (13)B3B—C2B—B7B—B11B142.17 (14)
C1A—B3A—B7A—C2A35.48 (10)C1B—B3B—B7B—C2B34.87 (11)
B8A—B3A—B7A—C2A133.91 (13)B8B—B3B—B7B—C2B133.77 (14)
B4A—B3A—B7A—C2A95.84 (13)B4B—B3B—B7B—C2B95.53 (14)
C2A—B3A—B7A—B12A96.37 (14)C1B—B3B—B7B—B8B98.90 (14)
C1A—B3A—B7A—B12A60.89 (15)C2B—B3B—B7B—B8B133.77 (14)
B8A—B3A—B7A—B12A37.54 (13)B4B—B3B—B7B—B8B38.23 (14)
B4A—B3A—B7A—B12A0.53 (17)C1B—B3B—B7B—B12B61.91 (17)
C2A—B3A—B7A—B8A133.91 (13)C2B—B3B—B7B—B12B96.78 (15)
C1A—B3A—B7A—B8A98.43 (13)B8B—B3B—B7B—B12B36.99 (14)
B4A—B3A—B7A—B8A38.07 (12)B4B—B3B—B7B—B12B1.25 (19)
C2A—B3A—B7A—B11A32.70 (11)C1B—B3B—B7B—B11B1.21 (18)
C1A—B3A—B7A—B11A2.78 (16)C2B—B3B—B7B—B11B33.66 (13)
B8A—B3A—B7A—B11A101.21 (14)B8B—B3B—B7B—B11B100.11 (16)
B4A—B3A—B7A—B11A63.14 (15)B4B—B3B—B7B—B11B61.87 (17)
C2A—B3A—B8A—B7A39.18 (12)C1B—B3B—B8B—B4B39.07 (13)
C1A—B3A—B8A—B7A98.69 (13)C2B—B3B—B8B—B4B98.19 (14)
B4A—B3A—B8A—B7A137.15 (14)B7B—B3B—B8B—B4B137.49 (15)
C2A—B3A—B8A—B4A97.97 (13)C1B—B3B—B8B—B7B98.42 (15)
C1A—B3A—B8A—B4A38.46 (12)C2B—B3B—B8B—B7B39.30 (13)
B7A—B3A—B8A—B4A137.15 (14)B4B—B3B—B8B—B7B137.49 (15)
C2A—B3A—B8A—B9A60.75 (16)C1B—B3B—B8B—B9B2.0 (2)
C1A—B3A—B8A—B9A1.24 (17)C2B—B3B—B8B—B9B61.12 (18)
B7A—B3A—B8A—B9A99.93 (15)B4B—B3B—B8B—B9B37.07 (15)
B4A—B3A—B8A—B9A37.22 (13)B7B—B3B—B8B—B9B100.42 (17)
C2A—B3A—B8A—B12A2.34 (16)C1B—B3B—B8B—B12B61.41 (18)
C1A—B3A—B8A—B12A61.86 (15)C2B—B3B—B8B—B12B2.29 (18)
B7A—B3A—B8A—B12A36.83 (12)B4B—B3B—B8B—B12B100.48 (16)
B4A—B3A—B8A—B12A100.32 (14)B7B—B3B—B8B—B12B37.01 (14)
C2A—B7A—B8A—B3A39.79 (12)C1B—B4B—B8B—B3B40.02 (13)
B12A—B7A—B8A—B3A138.58 (13)B9B—B4B—B8B—B3B138.75 (16)
B11A—B7A—B8A—B3A101.15 (14)B5B—B4B—B8B—B3B101.21 (15)
C2A—B7A—B8A—B4A1.27 (18)C1B—B4B—B8B—B7B1.82 (19)
B12A—B7A—B8A—B4A100.06 (15)B3B—B4B—B8B—B7B38.20 (14)
B3A—B7A—B8A—B4A38.53 (13)B9B—B4B—B8B—B7B100.56 (17)
B11A—B7A—B8A—B4A62.62 (17)B5B—B4B—B8B—B7B63.01 (18)
C2A—B7A—B8A—B9A61.87 (16)C1B—B4B—B8B—B9B98.74 (15)
B12A—B7A—B8A—B9A36.92 (12)B3B—B4B—B8B—B9B138.75 (16)
B3A—B7A—B8A—B9A101.66 (14)B5B—B4B—B8B—B9B37.55 (14)
B11A—B7A—B8A—B9A0.52 (17)C1B—B4B—B8B—B12B61.51 (17)
C2A—B7A—B8A—B12A98.79 (14)B3B—B4B—B8B—B12B101.53 (16)
B3A—B7A—B8A—B12A138.58 (13)B9B—B4B—B8B—B12B37.23 (14)
B11A—B7A—B8A—B12A37.44 (13)B5B—B4B—B8B—B12B0.32 (19)
C1A—B4A—B8A—B3A39.64 (12)C2B—B7B—B8B—B3B40.11 (13)
B5A—B4A—B8A—B3A101.09 (14)B12B—B7B—B8B—B3B138.72 (15)
B9A—B4A—B8A—B3A138.38 (14)B11B—B7B—B8B—B3B101.59 (15)
C1A—B4A—B8A—B7A1.12 (18)C2B—B7B—B8B—B4B2.0 (2)
B5A—B4A—B8A—B7A62.56 (16)B3B—B7B—B8B—B4B38.12 (14)
B9A—B4A—B8A—B7A99.85 (15)B12B—B7B—B8B—B4B100.59 (16)
B3A—B4A—B8A—B7A38.52 (13)B11B—B7B—B8B—B4B63.47 (18)
C1A—B4A—B8A—B9A98.74 (14)C2B—B7B—B8B—B9B61.53 (19)
B5A—B4A—B8A—B9A37.29 (12)B3B—B7B—B8B—B9B101.65 (16)
B3A—B4A—B8A—B9A138.38 (14)B12B—B7B—B8B—B9B37.07 (15)
C1A—B4A—B8A—B12A61.67 (16)B11B—B7B—B8B—B9B0.1 (2)
B5A—B4A—B8A—B12A0.23 (16)C2B—B7B—B8B—B12B98.60 (15)
B9A—B4A—B8A—B12A37.06 (12)B3B—B7B—B8B—B12B138.72 (15)
B3A—B4A—B8A—B12A101.31 (14)B11B—B7B—B8B—B12B37.12 (14)
C1A—B5A—B9A—B4A38.95 (11)C1B—B5B—B9B—B12B62.30 (18)
B6A—B5A—B9A—B4A101.72 (14)B10B—B5B—B9B—B12B37.96 (14)
B10A—B5A—B9A—B4A138.71 (13)B6B—B5B—B9B—B12B0.73 (19)
C1A—B5A—B9A—B12A61.94 (16)B4B—B5B—B9B—B12B100.93 (16)
B4A—B5A—B9A—B12A100.89 (14)C1B—B5B—B9B—B4B38.63 (13)
B6A—B5A—B9A—B12A0.83 (18)B10B—B5B—B9B—B4B138.89 (15)
B10A—B5A—B9A—B12A37.82 (13)B6B—B5B—B9B—B4B101.67 (15)
C1A—B5A—B9A—B8A1.86 (17)C1B—B5B—B9B—B10B100.26 (14)
B4A—B5A—B9A—B8A37.09 (13)B6B—B5B—B9B—B10B37.22 (13)
B6A—B5A—B9A—B8A64.63 (17)B4B—B5B—B9B—B10B138.89 (15)
B10A—B5A—B9A—B8A101.62 (15)C1B—B5B—B9B—B8B1.11 (19)
C1A—B5A—B9A—B10A99.76 (13)B10B—B5B—B9B—B8B101.36 (17)
B4A—B5A—B9A—B10A138.71 (13)B6B—B5B—B9B—B8B64.14 (19)
B6A—B5A—B9A—B10A36.99 (12)B4B—B5B—B9B—B8B37.53 (15)
C1A—B4A—B9A—B5A38.77 (11)C1B—B4B—B9B—B5B38.64 (12)
B8A—B4A—B9A—B5A138.38 (13)B3B—B4B—B9B—B5B101.18 (14)
B3A—B4A—B9A—B5A101.33 (13)B8B—B4B—B9B—B5B137.76 (15)
C1A—B4A—B9A—B12A62.07 (16)C1B—B4B—B9B—B12B61.75 (18)
B5A—B4A—B9A—B12A100.84 (15)B3B—B4B—B9B—B12B0.79 (19)
B8A—B4A—B9A—B12A37.54 (13)B8B—B4B—B9B—B12B37.37 (15)
B3A—B4A—B9A—B12A0.49 (17)B5B—B4B—B9B—B12B100.39 (16)
C1A—B4A—B9A—B8A99.61 (13)C1B—B4B—B9B—B10B1.93 (18)
B5A—B4A—B9A—B8A138.38 (13)B3B—B4B—B9B—B10B64.47 (17)
B3A—B4A—B9A—B8A37.05 (12)B8B—B4B—B9B—B10B101.05 (16)
C1A—B4A—B9A—B10A1.81 (16)B5B—B4B—B9B—B10B36.71 (14)
B5A—B4A—B9A—B10A36.95 (12)C1B—B4B—B9B—B8B99.13 (15)
B8A—B4A—B9A—B10A101.42 (14)B3B—B4B—B9B—B8B36.59 (14)
B3A—B4A—B9A—B10A64.38 (16)B5B—B4B—B9B—B8B137.76 (15)
B3A—B8A—B9A—B5A0.37 (18)B3B—B8B—B9B—B5B0.6 (2)
B7A—B8A—B9A—B5A64.22 (17)B4B—B8B—B9B—B5B37.73 (14)
B4A—B8A—B9A—B5A37.14 (12)B7B—B8B—B9B—B5B63.37 (19)
B12A—B8A—B9A—B5A101.08 (14)B12B—B8B—B9B—B5B100.49 (16)
B3A—B8A—B9A—B4A37.51 (13)B3B—B8B—B9B—B12B101.08 (17)
B7A—B8A—B9A—B4A101.36 (14)B4B—B8B—B9B—B12B138.22 (15)
B12A—B8A—B9A—B4A138.22 (13)B7B—B8B—B9B—B12B37.12 (14)
B3A—B8A—B9A—B12A100.71 (14)B3B—B8B—B9B—B4B37.14 (15)
B7A—B8A—B9A—B12A36.86 (12)B7B—B8B—B9B—B4B101.10 (16)
B4A—B8A—B9A—B12A138.22 (13)B12B—B8B—B9B—B4B138.22 (15)
B3A—B8A—B9A—B10A63.12 (17)B3B—B8B—B9B—B10B63.7 (2)
B7A—B8A—B9A—B10A0.74 (17)B4B—B8B—B9B—B10B100.85 (16)
B4A—B8A—B9A—B10A100.63 (14)B7B—B8B—B9B—B10B0.3 (2)
B12A—B8A—B9A—B10A37.59 (13)B12B—B8B—B9B—B10B37.37 (15)
C2A—B6A—B10A—B5A97.96 (13)C1B—B5B—B10B—B6B40.00 (13)
C1A—B6A—B10A—B5A38.39 (11)B9B—B5B—B10B—B6B138.48 (14)
B11A—B6A—B10A—B5A137.16 (14)B4B—B5B—B10B—B6B101.46 (15)
C2A—B6A—B10A—B11A39.19 (12)C1B—B5B—B10B—B11B2.02 (19)
C1A—B6A—B10A—B11A98.77 (13)B6B—B5B—B10B—B11B37.98 (14)
B5A—B6A—B10A—B11A137.16 (14)B9B—B5B—B10B—B11B100.50 (16)
C2A—B6A—B10A—B9A61.03 (15)B4B—B5B—B10B—B11B63.47 (18)
C1A—B6A—B10A—B9A1.46 (16)C1B—B5B—B10B—B9B98.47 (14)
B5A—B6A—B10A—B9A36.93 (12)B6B—B5B—B10B—B9B138.48 (14)
B11A—B6A—B10A—B9A100.22 (14)B4B—B5B—B10B—B9B37.02 (13)
C2A—B6A—B10A—B12A1.95 (17)C1B—B5B—B10B—B12B60.77 (17)
C1A—B6A—B10A—B12A61.52 (16)B6B—B5B—B10B—B12B100.77 (15)
B5A—B6A—B10A—B12A99.91 (15)B9B—B5B—B10B—B12B37.70 (14)
B11A—B6A—B10A—B12A37.25 (13)B4B—B5B—B10B—B12B0.68 (19)
C1A—B5A—B10A—B6A39.55 (12)C2B—B6B—B10B—B5B97.64 (14)
B4A—B5A—B10A—B6A101.36 (14)C1B—B6B—B10B—B5B38.55 (12)
B9A—B5A—B10A—B6A138.52 (13)B11B—B6B—B10B—B5B137.31 (15)
C1A—B5A—B10A—B11A1.09 (17)C2B—B6B—B10B—B11B39.67 (13)
B4A—B5A—B10A—B11A62.89 (16)C1B—B6B—B10B—B11B98.77 (14)
B9A—B5A—B10A—B11A100.05 (15)B5B—B6B—B10B—B11B137.31 (15)
B6A—B5A—B10A—B11A38.47 (13)C2B—B6B—B10B—B9B60.52 (17)
C1A—B5A—B10A—B9A98.97 (13)C1B—B6B—B10B—B9B1.42 (18)
B4A—B5A—B10A—B9A37.16 (12)B11B—B6B—B10B—B9B100.19 (16)
B6A—B5A—B10A—B9A138.52 (13)B5B—B6B—B10B—B9B37.13 (13)
C1A—B5A—B10A—B12A61.71 (15)C2B—B6B—B10B—B12B2.61 (18)
B4A—B5A—B10A—B12A0.09 (17)C1B—B6B—B10B—B12B61.70 (17)
B9A—B5A—B10A—B12A37.25 (12)B11B—B6B—B10B—B12B37.06 (14)
B6A—B5A—B10A—B12A101.27 (14)B5B—B6B—B10B—B12B100.25 (16)
B5A—B9A—B10A—B6A37.13 (12)B12B—B9B—B10B—B5B137.49 (15)
B4A—B9A—B10A—B6A0.21 (17)B4B—B9B—B10B—B5B36.91 (14)
B12A—B9A—B10A—B6A100.76 (14)B8B—B9B—B10B—B5B100.15 (16)
B8A—B9A—B10A—B6A63.18 (16)B5B—B9B—B10B—B6B37.20 (13)
B4A—B9A—B10A—B5A36.93 (12)B12B—B9B—B10B—B6B100.29 (16)
B12A—B9A—B10A—B5A137.89 (13)B4B—B9B—B10B—B6B0.29 (19)
B8A—B9A—B10A—B5A100.31 (14)B8B—B9B—B10B—B6B62.95 (19)
B5A—B9A—B10A—B11A100.98 (14)B5B—B9B—B10B—B11B100.50 (15)
B4A—B9A—B10A—B11A64.05 (16)B12B—B9B—B10B—B11B36.99 (14)
B12A—B9A—B10A—B11A36.91 (12)B4B—B9B—B10B—B11B63.60 (19)
B8A—B9A—B10A—B11A0.67 (17)B8B—B9B—B10B—B11B0.4 (2)
B5A—B9A—B10A—B12A137.89 (13)B5B—B9B—B10B—B12B137.49 (15)
B4A—B9A—B10A—B12A100.96 (14)B4B—B9B—B10B—B12B100.58 (16)
B8A—B9A—B10A—B12A37.58 (13)B8B—B9B—B10B—B12B37.34 (15)
C3A—C2A—B11A—B12A148.80 (13)C3B—C2B—B11B—B12B150.03 (15)
C1A—C2A—B11A—B12A64.12 (15)C1B—C2B—B11B—B12B63.74 (16)
B7A—C2A—B11A—B12A39.70 (12)B7B—C2B—B11B—B12B39.94 (13)
B3A—C2A—B11A—B12A3.72 (17)B6B—C2B—B11B—B12B102.88 (15)
B6A—C2A—B11A—B12A102.56 (13)B3B—C2B—B11B—B12B3.43 (18)
C3A—C2A—B11A—B10A148.51 (14)C3B—C2B—B11B—B6B107.09 (16)
C1A—C2A—B11A—B10A1.43 (17)C1B—C2B—B11B—B6B39.14 (13)
B7A—C2A—B11A—B10A102.39 (14)B7B—C2B—B11B—B6B142.82 (14)
B3A—C2A—B11A—B10A66.41 (16)B3B—C2B—B11B—B6B106.31 (15)
B6A—C2A—B11A—B10A39.87 (12)C3B—C2B—B11B—B10B147.31 (15)
C3A—C2A—B11A—B7A109.10 (15)C1B—C2B—B11B—B10B1.08 (18)
C1A—C2A—B11A—B7A103.82 (13)B7B—C2B—B11B—B10B102.60 (16)
B3A—C2A—B11A—B7A35.98 (12)B6B—C2B—B11B—B10B40.22 (13)
B6A—C2A—B11A—B7A142.26 (13)B3B—C2B—B11B—B10B66.10 (17)
C3A—C2A—B11A—B6A108.64 (15)C3B—C2B—B11B—B7B110.09 (16)
C1A—C2A—B11A—B6A38.44 (12)C1B—C2B—B11B—B7B103.68 (14)
B7A—C2A—B11A—B6A142.26 (13)B6B—C2B—B11B—B7B142.82 (14)
B3A—C2A—B11A—B6A106.28 (13)B3B—C2B—B11B—B7B36.51 (14)
B6A—B10A—B11A—C2A39.80 (12)C1B—B6B—B11B—C2B35.27 (11)
B5A—B10A—B11A—C2A1.51 (17)B10B—B6B—B11B—C2B133.80 (15)
B9A—B10A—B11A—C2A61.41 (16)B5B—B6B—B11B—C2B95.77 (14)
B12A—B10A—B11A—C2A98.33 (14)C2B—B6B—B11B—B12B96.24 (16)
B6A—B10A—B11A—B12A138.12 (14)C1B—B6B—B11B—B12B60.98 (17)
B5A—B10A—B11A—B12A99.84 (15)B10B—B6B—B11B—B12B37.55 (14)
B9A—B10A—B11A—B12A36.92 (13)B5B—B6B—B11B—B12B0.47 (19)
B6A—B10A—B11A—B7A100.86 (14)C2B—B6B—B11B—B10B133.80 (15)
B5A—B10A—B11A—B7A62.57 (16)C1B—B6B—B11B—B10B98.53 (14)
B9A—B10A—B11A—B7A0.35 (17)B5B—B6B—B11B—B10B38.03 (14)
B12A—B10A—B11A—B7A37.26 (13)C2B—B6B—B11B—B7B32.76 (13)
B5A—B10A—B11A—B6A38.29 (13)C1B—B6B—B11B—B7B2.51 (18)
B9A—B10A—B11A—B6A101.21 (14)B10B—B6B—B11B—B7B101.04 (16)
B12A—B10A—B11A—B6A138.12 (14)B5B—B6B—B11B—B7B63.01 (17)
B12A—B7A—B11A—C2A134.08 (13)B5B—B10B—B11B—C2B1.89 (19)
B8A—B7A—B11A—C2A96.28 (14)B6B—B10B—B11B—C2B39.93 (12)
B3A—B7A—B11A—C2A32.92 (11)B9B—B10B—B11B—C2B61.27 (18)
C2A—B7A—B11A—B12A134.08 (13)B12B—B10B—B11B—C2B98.33 (16)
B8A—B7A—B11A—B12A37.80 (13)B5B—B10B—B11B—B12B100.21 (16)
B3A—B7A—B11A—B12A101.16 (14)B6B—B10B—B11B—B12B138.26 (15)
C2A—B7A—B11A—B10A96.39 (13)B9B—B10B—B11B—B12B37.05 (15)
B12A—B7A—B11A—B10A37.69 (13)B5B—B10B—B11B—B6B38.05 (14)
B8A—B7A—B11A—B10A0.11 (17)B9B—B10B—B11B—B6B101.21 (16)
B3A—B7A—B11A—B10A63.47 (16)B12B—B10B—B11B—B6B138.26 (15)
C2A—B7A—B11A—B6A33.60 (11)B5B—B10B—B11B—B7B62.84 (18)
B12A—B7A—B11A—B6A100.48 (14)B6B—B10B—B11B—B7B100.89 (15)
B8A—B7A—B11A—B6A62.68 (16)B9B—B10B—B11B—B7B0.3 (2)
B3A—B7A—B11A—B6A0.68 (17)B12B—B10B—B11B—B7B37.37 (14)
C1A—B6A—B11A—C2A35.02 (11)B8B—B7B—B11B—C2B96.67 (15)
B10A—B6A—B11A—C2A133.86 (14)B3B—B7B—B11B—C2B33.99 (12)
B5A—B6A—B11A—C2A95.56 (13)B12B—B7B—B11B—C2B134.08 (15)
C2A—B6A—B11A—B12A96.24 (14)C2B—B7B—B11B—B12B134.08 (15)
C1A—B6A—B11A—B12A61.22 (15)B8B—B7B—B11B—B12B37.41 (14)
B10A—B6A—B11A—B12A37.63 (13)B3B—B7B—B11B—B12B100.09 (16)
B5A—B6A—B11A—B12A0.68 (17)C2B—B7B—B11B—B6B33.15 (13)
C2A—B6A—B11A—B10A133.86 (14)B8B—B7B—B11B—B6B63.52 (18)
C1A—B6A—B11A—B10A98.85 (13)B3B—B7B—B11B—B6B0.84 (19)
B5A—B6A—B11A—B10A38.30 (13)B12B—B7B—B11B—B6B100.93 (16)
C2A—B6A—B11A—B7A33.30 (11)C2B—B7B—B11B—B10B96.51 (15)
C1A—B6A—B11A—B7A1.72 (16)B8B—B7B—B11B—B10B0.16 (19)
B10A—B6A—B11A—B7A100.57 (15)B3B—B7B—B11B—B10B62.52 (18)
B5A—B6A—B11A—B7A62.26 (16)B12B—B7B—B11B—B10B37.57 (14)
C2A—B7A—B12A—B11A39.34 (12)C2B—B11B—B12B—B9B61.86 (18)
B8A—B7A—B12A—B11A138.31 (14)B6B—B11B—B12B—B9B0.0 (2)
B3A—B7A—B12A—B11A101.27 (14)B10B—B11B—B12B—B9B37.32 (14)
C2A—B7A—B12A—B9A61.70 (17)B7B—B11B—B12B—B9B100.96 (17)
B8A—B7A—B12A—B9A37.27 (13)C2B—B11B—B12B—B7B39.10 (13)
B3A—B7A—B12A—B9A0.23 (18)B6B—B11B—B12B—B7B100.98 (16)
B11A—B7A—B12A—B9A101.04 (15)B10B—B11B—B12B—B7B138.28 (16)
C2A—B7A—B12A—B8A98.98 (14)C2B—B11B—B12B—B8B1.76 (19)
B3A—B7A—B12A—B8A37.05 (12)B6B—B11B—B12B—B8B63.65 (19)
B11A—B7A—B12A—B8A138.31 (14)B10B—B11B—B12B—B8B100.94 (17)
C2A—B7A—B12A—B10A1.83 (18)B7B—B11B—B12B—B8B37.33 (14)
B8A—B7A—B12A—B10A100.81 (15)C2B—B11B—B12B—B10B99.18 (14)
B3A—B7A—B12A—B10A63.76 (17)B6B—B11B—B12B—B10B37.29 (14)
B11A—B7A—B12A—B10A37.51 (13)B7B—B11B—B12B—B10B138.28 (16)
C2A—B11A—B12A—B7A39.17 (12)B5B—B9B—B12B—B11B0.4 (2)
B10A—B11A—B12A—B7A138.08 (14)B4B—B9B—B12B—B11B63.92 (19)
B6A—B11A—B12A—B7A100.95 (14)B10B—B9B—B12B—B11B37.29 (14)
C2A—B11A—B12A—B9A61.62 (16)B8B—B9B—B12B—B11B101.12 (16)
B10A—B11A—B12A—B9A37.29 (13)B5B—B9B—B12B—B7B63.51 (19)
B7A—B11A—B12A—B9A100.78 (15)B4B—B9B—B12B—B7B0.0 (2)
B6A—B11A—B12A—B9A0.17 (18)B10B—B9B—B12B—B7B101.24 (16)
C2A—B11A—B12A—B8A1.95 (17)B8B—B9B—B12B—B7B37.17 (15)
B10A—B11A—B12A—B8A100.86 (15)B5B—B9B—B12B—B8B100.68 (16)
B7A—B11A—B12A—B8A37.22 (13)B4B—B9B—B12B—B8B37.19 (14)
B6A—B11A—B12A—B8A63.73 (16)B10B—B9B—B12B—B8B138.41 (15)
C2A—B11A—B12A—B10A98.91 (14)B5B—B9B—B12B—B10B37.73 (14)
B7A—B11A—B12A—B10A138.08 (14)B4B—B9B—B12B—B10B101.22 (16)
B6A—B11A—B12A—B10A37.12 (13)B8B—B9B—B12B—B10B138.41 (15)
B5A—B9A—B12A—B7A63.54 (17)C2B—B7B—B12B—B11B39.43 (13)
B4A—B9A—B12A—B7A0.16 (18)B8B—B7B—B12B—B11B138.25 (15)
B8A—B9A—B12A—B7A37.13 (13)B3B—B7B—B12B—B11B101.73 (15)
B10A—B9A—B12A—B7A101.18 (14)C2B—B7B—B12B—B9B61.55 (19)
B5A—B9A—B12A—B11A0.41 (18)B8B—B7B—B12B—B9B37.28 (15)
B4A—B9A—B12A—B11A63.78 (17)B3B—B7B—B12B—B9B0.8 (2)
B8A—B9A—B12A—B11A101.08 (15)B11B—B7B—B12B—B9B100.98 (17)
B10A—B9A—B12A—B11A37.23 (13)C2B—B7B—B12B—B8B98.83 (16)
B5A—B9A—B12A—B8A100.67 (14)B3B—B7B—B12B—B8B36.52 (14)
B4A—B9A—B12A—B8A37.30 (12)B11B—B7B—B12B—B8B138.25 (15)
B10A—B9A—B12A—B8A138.32 (13)C2B—B7B—B12B—B10B2.0 (2)
B5A—B9A—B12A—B10A37.64 (13)B8B—B7B—B12B—B10B100.86 (17)
B4A—B9A—B12A—B10A101.02 (14)B3B—B7B—B12B—B10B64.33 (19)
B8A—B9A—B12A—B10A138.32 (13)B11B—B7B—B12B—B10B37.40 (14)
B3A—B8A—B12A—B7A37.28 (12)B3B—B8B—B12B—B11B0.4 (2)
B4A—B8A—B12A—B7A101.15 (14)B4B—B8B—B12B—B11B63.43 (18)
B9A—B8A—B12A—B7A138.32 (13)B7B—B8B—B12B—B11B37.59 (14)
B3A—B8A—B12A—B11A0.27 (18)B9B—B8B—B12B—B11B100.80 (16)
B7A—B8A—B12A—B11A37.54 (13)B3B—B8B—B12B—B9B101.15 (16)
B4A—B8A—B12A—B11A63.61 (16)B4B—B8B—B12B—B9B37.37 (14)
B9A—B8A—B12A—B11A100.77 (14)B7B—B8B—B12B—B9B138.39 (15)
B3A—B8A—B12A—B9A101.04 (14)B3B—B8B—B12B—B7B37.24 (14)
B7A—B8A—B12A—B9A138.32 (13)B4B—B8B—B12B—B7B101.02 (15)
B4A—B8A—B12A—B9A37.17 (12)B9B—B8B—B12B—B7B138.39 (15)
B3A—B8A—B12A—B10A63.70 (16)B3B—B8B—B12B—B10B63.88 (19)
B7A—B8A—B12A—B10A100.98 (14)B4B—B8B—B12B—B10B0.10 (19)
B4A—B8A—B12A—B10A0.17 (17)B7B—B8B—B12B—B10B101.12 (16)
B9A—B8A—B12A—B10A37.34 (12)B9B—B8B—B12B—B10B37.27 (14)
B6A—B10A—B12A—B7A0.09 (19)B5B—B10B—B12B—B11B100.54 (15)
B5A—B10A—B12A—B7A63.30 (17)B6B—B10B—B12B—B11B37.21 (14)
B11A—B10A—B12A—B7A37.75 (13)B9B—B10B—B12B—B11B138.31 (15)
B9A—B10A—B12A—B7A100.59 (15)B5B—B10B—B12B—B9B37.78 (14)
B6A—B10A—B12A—B11A37.66 (13)B6B—B10B—B12B—B9B101.10 (16)
B5A—B10A—B12A—B11A101.05 (14)B11B—B10B—B12B—B9B138.31 (15)
B9A—B10A—B12A—B11A138.34 (14)B5B—B10B—B12B—B7B62.94 (19)
B6A—B10A—B12A—B9A100.68 (14)B6B—B10B—B12B—B7B0.4 (2)
B5A—B10A—B12A—B9A37.29 (12)B11B—B10B—B12B—B7B37.60 (15)
B11A—B10A—B12A—B9A138.34 (14)B9B—B10B—B12B—B7B100.72 (17)
B6A—B10A—B12A—B8A63.34 (16)B5B—B10B—B12B—B8B0.48 (19)
B5A—B10A—B12A—B8A0.05 (17)B6B—B10B—B12B—B8B63.80 (18)
B11A—B10A—B12A—B8A101.00 (14)B11B—B10B—B12B—B8B101.02 (16)
B9A—B10A—B12A—B8A37.34 (12)B9B—B10B—B12B—B8B37.30 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O3A0.95 (3)1.70 (3)2.6473 (17)174 (2)
O1A—H1A···O2Ai0.96 (2)1.71 (2)2.6707 (17)175 (2)
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC5H16B10O3
Mr232.28
Crystal system, space groupMonoclinic, C2/c
Temperature (K)160
a, b, c (Å)22.746 (2), 9.699 (1), 23.439 (3)
β (°) 102.296 (10)
V3)5052.1 (10)
Z16
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5399, 4418, 3670
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.129, 1.03
No. of reflections4418
No. of parameters334
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.30

Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXTL (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
C1A—C4A1.535 (2)C1B—C4B1.517 (2)
C2A—C3A1.516 (2)C2B—C3B1.526 (2)
C4A—O3A1.411 (2)C4B—O3B1.404 (2)
O3A—C5A1.443 (2)O3B—C5B1.428 (2)
C1A—C2A—C3A120.98 (12)C1B—C2B—C3B119.73 (14)
C2A—C1A—C4A121.82 (12)C2B—C1B—C4B119.28 (14)
C1A—C4A—O3A113.90 (13)C1B—C4B—O3B109.44 (14)
C2A—C3A—O1A114.77 (14)C2B—C3B—O1B112.29 (14)
C2A—C3A—O2A119.79 (14)C2B—C3B—O2B121.40 (16)
O1A—C3A—O2A125.42 (15)O1B—C3B—O2B126.26 (16)
C4A—O3A—C5A115.22 (13)C4B—O3B—C5B111.58 (15)
C4A—C1A—C2A—C3A3.9 (2)C4B—C1B—C2B—C3B1.1 (2)
C1A—C2A—C3A—O1A164.45 (13)C1B—C2B—C3B—O1B53.25 (19)
C1A—C2A—C3A—O2A17.1 (2)C1B—C2B—C3B—O2B129.22 (18)
C2A—C1A—C4A—O3A69.56 (18)C2B—C1B—C4B—O3B55.16 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O3A0.95 (3)1.70 (3)2.6473 (17)174 (2)
O1A—H1A···O2Ai0.96 (2)1.71 (2)2.6707 (17)175 (2)
Symmetry code: (i) x, y+1, z.
 

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