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
CCDC reference: 224668
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 (C═O); 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.
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).
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.
2-carboxy-1,2-dicarba-1-methoxymethyl-
closo-dodecaborane(12)
top
Crystal data top
C5H16B10O3 | F(000) = 1920 |
Mr = 232.28 | Dx = 1.222 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 41 reflections |
a = 22.746 (2) Å | θ = 3.6–16.7° |
b = 9.699 (1) Å | µ = 0.07 mm−1 |
c = 23.439 (3) Å | T = 160 K |
β = 102.296 (10)° | Block, colourless |
V = 5052.1 (10) Å3 | 0.24 × 0.20 × 0.18 mm |
Z = 16 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −1→26 |
ω scans | k = −1→11 |
5399 measured reflections | l = −27→27 |
4418 independent reflections | 3 standard reflections every 97 reflections |
3670 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H 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 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.30 e Å−3 |
Crystal data top
C5H16B10O3 | V = 5052.1 (10) Å3 |
Mr = 232.28 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.746 (2) Å | µ = 0.07 mm−1 |
b = 9.699 (1) Å | T = 160 K |
c = 23.439 (3) Å | 0.24 × 0.20 × 0.18 mm |
β = 102.296 (10)° | |
Data collection top
Bruker P4 diffractometer | Rint = 0.027 |
5399 measured reflections | 3 standard reflections every 97 reflections |
4418 independent reflections | intensity decay: none |
3670 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.27 e Å−3 |
4418 reflections | Δρmin = −0.30 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1A | 0.00055 (5) | 0.60029 (13) | 0.06038 (5) | 0.0311 (3) | |
H1A | −0.0274 (10) | 0.576 (2) | 0.0250 (10) | 0.047* | |
O2A | 0.07239 (6) | 0.46186 (13) | 0.04153 (5) | 0.0340 (3) | |
O3A | 0.13373 (5) | 0.25680 (12) | 0.12789 (5) | 0.0275 (3) | |
C1A | 0.15047 (7) | 0.49657 (16) | 0.16314 (6) | 0.0185 (3) | |
C2A | 0.08986 (7) | 0.58734 (16) | 0.13164 (6) | 0.0184 (3) | |
C3A | 0.05167 (7) | 0.54434 (16) | 0.07319 (7) | 0.0195 (3) | |
C4A | 0.17225 (7) | 0.37224 (17) | 0.13281 (7) | 0.0243 (4) | |
H41 | 0.1763 | 0.4003 | 0.0932 | 0.029* | |
H42 | 0.2126 | 0.3450 | 0.1550 | 0.029* | |
C5A | 0.14700 (10) | 0.1606 (2) | 0.17587 (9) | 0.0403 (5) | |
H51 | 0.1891 | 0.1316 | 0.1819 | 0.060* | |
H52 | 0.1208 | 0.0798 | 0.1669 | 0.060* | |
H53 | 0.1401 | 0.2051 | 0.2114 | 0.060* | |
B3A | 0.08559 (8) | 0.4863 (2) | 0.19134 (8) | 0.0216 (4) | |
H3A | 0.0570 | 0.3918 | 0.1899 | 0.026* | |
B4A | 0.15891 (8) | 0.5003 (2) | 0.23734 (8) | 0.0233 (4) | |
H4A | 0.1787 | 0.4142 | 0.2671 | 0.028* | |
B5A | 0.20416 (8) | 0.6037 (2) | 0.20129 (8) | 0.0232 (4) | |
H5A | 0.2537 | 0.5851 | 0.2075 | 0.028* | |
B6A | 0.16037 (8) | 0.65600 (19) | 0.13251 (8) | 0.0225 (4) | |
H6A | 0.1802 | 0.6710 | 0.0931 | 0.027* | |
B7A | 0.05432 (8) | 0.6558 (2) | 0.18247 (8) | 0.0248 (4) | |
H7A | 0.0046 | 0.6728 | 0.1757 | 0.030* | |
B8A | 0.09856 (9) | 0.6032 (2) | 0.25079 (8) | 0.0279 (4) | |
H8A | 0.0784 | 0.5856 | 0.2898 | 0.033* | |
B9A | 0.17178 (9) | 0.6767 (2) | 0.25694 (8) | 0.0268 (4) | |
H9A | 0.1999 | 0.7082 | 0.3002 | 0.032* | |
B10A | 0.17283 (9) | 0.7726 (2) | 0.19198 (9) | 0.0273 (4) | |
H10A | 0.2015 | 0.8666 | 0.1923 | 0.033* | |
B11A | 0.09967 (8) | 0.75995 (19) | 0.14596 (8) | 0.0247 (4) | |
H11A | 0.0797 | 0.8444 | 0.1153 | 0.030* | |
B12A | 0.10707 (9) | 0.7725 (2) | 0.22282 (9) | 0.0298 (4) | |
H12A | 0.0924 | 0.8670 | 0.2435 | 0.036* | |
O1B | 0.10315 (6) | 0.13197 (14) | 0.02540 (6) | 0.0366 (3) | |
H1B | 0.1170 (12) | 0.177 (3) | 0.0619 (13) | 0.070 (8)* | |
O2B | 0.17922 (6) | −0.01391 (15) | 0.05931 (6) | 0.0412 (3) | |
O3B | 0.17993 (6) | 0.21967 (13) | −0.06254 (7) | 0.0402 (3) | |
C1B | 0.11232 (7) | 0.03599 (17) | −0.09825 (7) | 0.0225 (4) | |
C2B | 0.12003 (7) | −0.05047 (17) | −0.03617 (7) | 0.0232 (4) | |
C3B | 0.13840 (8) | 0.02565 (18) | 0.02187 (7) | 0.0265 (4) | |
C4B | 0.12256 (8) | 0.19061 (17) | −0.09643 (8) | 0.0287 (4) | |
H43A | 0.1194 | 0.2262 | −0.1366 | 0.034* | |
H44A | 0.0915 | 0.2366 | −0.0794 | 0.034* | |
C5B | 0.18878 (11) | 0.3644 (2) | −0.05319 (12) | 0.0533 (6) | |
H54A | 0.1844 | 0.4112 | −0.0909 | 0.080* | |
H55A | 0.2292 | 0.3811 | −0.0297 | 0.080* | |
H56A | 0.1588 | 0.4001 | −0.0326 | 0.080* | |
B3B | 0.04804 (8) | −0.0213 (2) | −0.07700 (9) | 0.0277 (4) | |
H3B | 0.0137 | 0.0472 | −0.0636 | 0.033* | |
B4B | 0.05624 (9) | −0.0326 (2) | −0.15040 (9) | 0.0305 (5) | |
H4B | 0.0269 | 0.0287 | −0.1859 | 0.037* | |
B5B | 0.13352 (9) | −0.0643 (2) | −0.15013 (9) | 0.0287 (4) | |
H5B | 0.1549 | −0.0233 | −0.1855 | 0.034* | |
B6B | 0.17443 (9) | −0.0720 (2) | −0.07676 (8) | 0.0253 (4) | |
H6B | 0.2222 | −0.0360 | −0.0631 | 0.030* | |
B7B | 0.06934 (10) | −0.1823 (2) | −0.04241 (9) | 0.0342 (5) | |
H7B | 0.0487 | −0.2202 | −0.0060 | 0.041* | |
B8B | 0.02888 (10) | −0.1750 (2) | −0.11616 (10) | 0.0372 (5) | |
H8B | −0.0191 | −0.2098 | −0.1292 | 0.045* | |
B9B | 0.08116 (10) | −0.2025 (2) | −0.16202 (9) | 0.0362 (5) | |
H9B | 0.0677 | −0.2551 | −0.2054 | 0.043* | |
B10B | 0.15412 (10) | −0.2261 (2) | −0.11671 (9) | 0.0319 (5) | |
H10B | 0.1887 | −0.2937 | −0.1302 | 0.038* | |
B11B | 0.14664 (10) | −0.2141 (2) | −0.04283 (9) | 0.0317 (5) | |
H11B | 0.1764 | −0.2731 | −0.0068 | 0.038* | |
B12B | 0.08923 (11) | −0.2947 (2) | −0.09521 (10) | 0.0395 (5) | |
H12B | 0.0810 | −0.4085 | −0.0943 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0229 (6) | 0.0420 (7) | 0.0248 (6) | 0.0036 (6) | −0.0034 (5) | −0.0032 (6) |
O2A | 0.0389 (7) | 0.0373 (7) | 0.0224 (6) | 0.0090 (6) | −0.0010 (5) | −0.0100 (5) |
O3A | 0.0346 (7) | 0.0201 (6) | 0.0253 (6) | 0.0010 (5) | 0.0008 (5) | −0.0023 (5) |
C1A | 0.0173 (7) | 0.0207 (8) | 0.0166 (7) | 0.0005 (6) | 0.0016 (6) | −0.0006 (6) |
C2A | 0.0177 (7) | 0.0185 (7) | 0.0189 (7) | 0.0009 (6) | 0.0033 (6) | −0.0012 (6) |
C3A | 0.0213 (8) | 0.0197 (8) | 0.0173 (7) | −0.0012 (6) | 0.0036 (6) | 0.0009 (6) |
C4A | 0.0240 (8) | 0.0237 (8) | 0.0251 (8) | 0.0031 (7) | 0.0047 (6) | −0.0049 (7) |
C5A | 0.0541 (12) | 0.0247 (10) | 0.0377 (11) | 0.0013 (9) | 0.0002 (9) | 0.0060 (8) |
B3A | 0.0201 (9) | 0.0279 (10) | 0.0173 (8) | −0.0011 (7) | 0.0052 (7) | −0.0006 (7) |
B4A | 0.0233 (9) | 0.0303 (10) | 0.0154 (8) | −0.0004 (8) | 0.0021 (7) | −0.0013 (7) |
B5A | 0.0183 (8) | 0.0269 (10) | 0.0231 (9) | −0.0023 (7) | 0.0017 (7) | −0.0042 (8) |
B6A | 0.0208 (9) | 0.0233 (9) | 0.0234 (9) | −0.0027 (7) | 0.0046 (7) | 0.0005 (7) |
B7A | 0.0211 (9) | 0.0299 (10) | 0.0239 (9) | 0.0021 (8) | 0.0054 (7) | −0.0089 (8) |
B8A | 0.0248 (9) | 0.0396 (11) | 0.0200 (9) | 0.0006 (8) | 0.0066 (7) | −0.0082 (8) |
B9A | 0.0242 (9) | 0.0317 (10) | 0.0227 (9) | −0.0004 (8) | 0.0007 (7) | −0.0080 (8) |
B10A | 0.0251 (9) | 0.0243 (10) | 0.0303 (10) | −0.0033 (8) | 0.0009 (8) | −0.0060 (8) |
B11A | 0.0230 (9) | 0.0197 (9) | 0.0297 (10) | 0.0003 (7) | 0.0016 (7) | −0.0042 (8) |
B12A | 0.0277 (10) | 0.0314 (11) | 0.0288 (10) | 0.0022 (8) | 0.0024 (8) | −0.0126 (8) |
O1B | 0.0451 (8) | 0.0340 (7) | 0.0276 (7) | 0.0062 (6) | 0.0008 (6) | −0.0100 (6) |
O2B | 0.0458 (8) | 0.0455 (8) | 0.0282 (7) | 0.0076 (7) | −0.0011 (6) | −0.0038 (6) |
O3B | 0.0301 (7) | 0.0248 (7) | 0.0613 (9) | −0.0059 (5) | 0.0000 (6) | 0.0020 (6) |
C1B | 0.0211 (8) | 0.0262 (9) | 0.0208 (8) | 0.0005 (7) | 0.0062 (6) | 0.0021 (7) |
C2B | 0.0262 (8) | 0.0232 (8) | 0.0217 (8) | −0.0042 (7) | 0.0084 (7) | 0.0002 (6) |
C3B | 0.0298 (9) | 0.0273 (9) | 0.0232 (8) | −0.0037 (7) | 0.0075 (7) | −0.0004 (7) |
C4B | 0.0285 (9) | 0.0246 (9) | 0.0329 (9) | 0.0027 (7) | 0.0061 (7) | 0.0071 (7) |
C5B | 0.0517 (13) | 0.0287 (11) | 0.0769 (17) | −0.0117 (10) | 0.0079 (12) | −0.0044 (11) |
B3B | 0.0207 (9) | 0.0365 (11) | 0.0271 (10) | −0.0066 (8) | 0.0077 (8) | −0.0066 (8) |
B4B | 0.0254 (10) | 0.0404 (12) | 0.0244 (10) | −0.0001 (9) | 0.0025 (8) | −0.0061 (8) |
B5B | 0.0293 (10) | 0.0353 (11) | 0.0238 (9) | 0.0052 (8) | 0.0109 (8) | 0.0021 (8) |
B6B | 0.0250 (9) | 0.0264 (10) | 0.0262 (9) | 0.0047 (8) | 0.0089 (8) | 0.0036 (8) |
B7B | 0.0436 (12) | 0.0289 (11) | 0.0347 (11) | −0.0141 (9) | 0.0189 (9) | −0.0048 (9) |
B8B | 0.0339 (11) | 0.0408 (12) | 0.0388 (12) | −0.0138 (10) | 0.0117 (9) | −0.0156 (10) |
B9B | 0.0399 (12) | 0.0392 (12) | 0.0302 (11) | −0.0022 (10) | 0.0092 (9) | −0.0111 (9) |
B10B | 0.0401 (12) | 0.0299 (11) | 0.0282 (10) | 0.0071 (9) | 0.0128 (9) | −0.0013 (8) |
B11B | 0.0458 (12) | 0.0226 (10) | 0.0283 (10) | 0.0013 (9) | 0.0118 (9) | 0.0038 (8) |
B12B | 0.0542 (14) | 0.0270 (11) | 0.0411 (12) | −0.0101 (10) | 0.0191 (11) | −0.0089 (9) |
Geometric parameters (Å, º) top
O1A—C3A | 1.2601 (19) | O1B—C3B | 1.320 (2) |
O1A—H1A | 0.96 (2) | O1B—H1B | 0.95 (3) |
O2A—C3A | 1.250 (2) | O2B—C3B | 1.197 (2) |
C1A—C4A | 1.535 (2) | C1B—C4B | 1.517 (2) |
C2A—C3A | 1.516 (2) | C1B—C2B | 1.656 (2) |
C4A—O3A | 1.411 (2) | C1B—B4B | 1.703 (2) |
O3A—C5A | 1.443 (2) | C1B—B5B | 1.705 (2) |
C1A—C2A | 1.669 (2) | C1B—B3B | 1.734 (2) |
C1A—B5A | 1.705 (2) | C1B—B6B | 1.744 (2) |
C1A—B4A | 1.709 (2) | C2B—C3B | 1.526 (2) |
C1A—B6A | 1.740 (2) | C4B—O3B | 1.404 (2) |
C1A—B3A | 1.743 (2) | O3B—C5B | 1.428 (2) |
C2A—B7A | 1.710 (2) | C2B—B7B | 1.707 (2) |
C2A—B11A | 1.713 (2) | C2B—B11B | 1.718 (3) |
C2A—B3A | 1.728 (2) | C2B—B6B | 1.727 (2) |
C2A—B6A | 1.733 (2) | C2B—B3B | 1.735 (3) |
C4A—H41 | 0.9900 | C4B—H43A | 0.9900 |
C4A—H42 | 0.9900 | C4B—H44A | 0.9900 |
C5A—H51 | 0.9800 | C5B—H54A | 0.9800 |
C5A—H52 | 0.9800 | C5B—H55A | 0.9800 |
C5A—H53 | 0.9800 | C5B—H56A | 0.9800 |
B3A—B8A | 1.772 (3) | B3B—B8B | 1.756 (3) |
B3A—B7A | 1.786 (3) | B3B—B4B | 1.773 (3) |
B3A—B4A | 1.788 (3) | B3B—B7B | 1.778 (3) |
B3A—H3A | 1.1200 | B3B—H3B | 1.1200 |
B4A—B5A | 1.775 (3) | B4B—B8B | 1.776 (3) |
B4A—B8A | 1.779 (3) | B4B—B9B | 1.783 (3) |
B4A—B9A | 1.779 (3) | B4B—B5B | 1.783 (3) |
B4A—H4A | 1.1200 | B4B—H4B | 1.1200 |
B5A—B9A | 1.776 (3) | B5B—B10B | 1.772 (3) |
B5A—B6A | 1.779 (3) | B5B—B6B | 1.774 (3) |
B5A—B10A | 1.781 (3) | B5B—B9B | 1.776 (3) |
B5A—H5A | 1.1200 | B5B—H5B | 1.1200 |
B6A—B10A | 1.771 (3) | B6B—B10B | 1.772 (3) |
B6A—B11A | 1.791 (3) | B6B—B11B | 1.774 (3) |
B6A—H6A | 1.1200 | B6B—H6B | 1.1200 |
B7A—B12A | 1.770 (3) | B7B—B8B | 1.778 (3) |
B7A—B8A | 1.775 (3) | B7B—B12B | 1.779 (3) |
B7A—B11A | 1.787 (3) | B7B—B11B | 1.787 (3) |
B7A—H7A | 1.1200 | B7B—H7B | 1.1200 |
B8A—B9A | 1.789 (3) | B8B—B9B | 1.785 (3) |
B8A—B12A | 1.794 (3) | B8B—B12B | 1.785 (3) |
B8A—H8A | 1.1200 | B8B—H8B | 1.1200 |
B9A—B12A | 1.780 (3) | B9B—B12B | 1.779 (3) |
B9A—B10A | 1.789 (3) | B9B—B10B | 1.784 (3) |
B9A—H9A | 1.1200 | B9B—H9B | 1.1200 |
B10A—B11A | 1.784 (3) | B10B—B11B | 1.779 (3) |
B10A—B12A | 1.795 (3) | B10B—B12B | 1.787 (3) |
B10A—H10A | 1.1200 | B10B—H10B | 1.1200 |
B11A—B12A | 1.778 (3) | B11B—B12B | 1.772 (3) |
B11A—H11A | 1.1200 | B11B—H11B | 1.1200 |
B12A—H12A | 1.1200 | B12B—H12B | 1.1200 |
| | | |
C3A—O1A—H1A | 120.6 (13) | C3B—O1B—H1B | 108.8 (16) |
C1A—C2A—C3A | 120.98 (12) | C1B—C2B—C3B | 119.73 (14) |
C2A—C1A—C4A | 121.82 (12) | C2B—C1B—C4B | 119.28 (14) |
C1A—C4A—O3A | 113.90 (13) | C1B—C4B—O3B | 109.44 (14) |
C2A—C3A—O1A | 114.77 (14) | C2B—C3B—O1B | 112.29 (14) |
C2A—C3A—O2A | 119.79 (14) | C2B—C3B—O2B | 121.40 (16) |
O1A—C3A—O2A | 125.42 (15) | O1B—C3B—O2B | 126.26 (16) |
C4A—O3A—C5A | 115.22 (13) | C4B—O3B—C5B | 111.58 (15) |
C4A—C1A—B5A | 117.14 (12) | C4B—C1B—B4B | 119.56 (14) |
C2A—C1A—B5A | 110.02 (12) | C2B—C1B—B4B | 110.84 (13) |
C4A—C1A—B4A | 120.72 (13) | C4B—C1B—B5B | 121.26 (14) |
C2A—C1A—B4A | 109.99 (12) | C2B—C1B—B5B | 110.17 (13) |
B5A—C1A—B4A | 62.65 (10) | B4B—C1B—B5B | 63.11 (11) |
C4A—C1A—B6A | 115.11 (12) | C4B—C1B—B3B | 116.28 (14) |
C2A—C1A—B6A | 61.06 (9) | C2B—C1B—B3B | 61.52 (10) |
B5A—C1A—B6A | 62.18 (10) | B4B—C1B—B3B | 62.10 (11) |
B4A—C1A—B6A | 113.87 (12) | B5B—C1B—B3B | 113.95 (13) |
C4A—C1A—B3A | 120.90 (13) | C4B—C1B—B6B | 118.39 (13) |
C2A—C1A—B3A | 60.78 (9) | C2B—C1B—B6B | 60.97 (10) |
B5A—C1A—B3A | 113.93 (12) | B4B—C1B—B6B | 114.19 (14) |
B4A—C1A—B3A | 62.36 (10) | B5B—C1B—B6B | 61.89 (11) |
B6A—C1A—B3A | 113.68 (12) | B3B—C1B—B6B | 113.91 (13) |
C3A—C2A—B7A | 118.13 (13) | C3B—C2B—B7B | 119.38 (14) |
C1A—C2A—B7A | 111.42 (12) | C1B—C2B—B7B | 111.16 (13) |
C3A—C2A—B11A | 118.14 (13) | C3B—C2B—B11B | 119.55 (14) |
C1A—C2A—B11A | 111.60 (12) | C1B—C2B—B11B | 111.19 (13) |
B7A—C2A—B11A | 62.93 (11) | B7B—C2B—B11B | 62.92 (12) |
C3A—C2A—B3A | 117.10 (13) | C3B—C2B—B6B | 117.21 (13) |
C1A—C2A—B3A | 61.73 (9) | C1B—C2B—B6B | 62.04 (10) |
B7A—C2A—B3A | 62.60 (10) | B7B—C2B—B6B | 114.37 (13) |
B11A—C2A—B3A | 115.04 (12) | B11B—C2B—B6B | 62.00 (11) |
C3A—C2A—B6A | 117.84 (12) | C3B—C2B—B3B | 117.40 (14) |
C1A—C2A—B6A | 61.47 (9) | C1B—C2B—B3B | 61.44 (10) |
B7A—C2A—B6A | 114.60 (12) | B7B—C2B—B3B | 62.22 (12) |
B11A—C2A—B6A | 62.64 (10) | B11B—C2B—B3B | 114.20 (14) |
B3A—C2A—B6A | 114.84 (12) | B6B—C2B—B3B | 114.75 (13) |
O3A—C4A—H41 | 108.8 | O3B—C4B—H43A | 109.8 |
C1A—C4A—H41 | 108.8 | C1B—C4B—H43A | 109.8 |
O3A—C4A—H42 | 108.8 | O3B—C4B—H44A | 109.8 |
C1A—C4A—H42 | 108.8 | C1B—C4B—H44A | 109.8 |
H41—C4A—H42 | 107.7 | H43A—C4B—H44A | 108.2 |
O3A—C5A—H51 | 109.5 | O3B—C5B—H54A | 109.5 |
O3A—C5A—H52 | 109.5 | O3B—C5B—H55A | 109.5 |
H51—C5A—H52 | 109.5 | H54A—C5B—H55A | 109.5 |
O3A—C5A—H53 | 109.5 | O3B—C5B—H56A | 109.5 |
H51—C5A—H53 | 109.5 | H54A—C5B—H56A | 109.5 |
H52—C5A—H53 | 109.5 | H55A—C5B—H56A | 109.5 |
C2A—B3A—C1A | 57.49 (9) | C1B—B3B—C2B | 57.04 (9) |
C2A—B3A—B8A | 104.20 (13) | C1B—B3B—B8B | 104.64 (14) |
C1A—B3A—B8A | 104.42 (12) | C2B—B3B—B8B | 104.48 (15) |
C2A—B3A—B7A | 58.22 (10) | C1B—B3B—B4B | 58.10 (10) |
C1A—B3A—B7A | 104.57 (12) | C2B—B3B—B4B | 104.09 (13) |
B8A—B3A—B7A | 59.86 (11) | B8B—B3B—B4B | 60.42 (12) |
C2A—B3A—B4A | 103.84 (12) | C1B—B3B—B7B | 104.36 (14) |
C1A—B3A—B4A | 57.87 (9) | C2B—B3B—B7B | 58.13 (11) |
B8A—B3A—B4A | 59.95 (10) | B8B—B3B—B7B | 60.41 (13) |
B7A—B3A—B4A | 107.30 (13) | B4B—B3B—B7B | 108.28 (15) |
C2A—B3A—H3A | 124.9 | C1B—B3B—H3B | 124.9 |
C1A—B3A—H3A | 124.6 | C2B—B3B—H3B | 125.0 |
B8A—B3A—H3A | 123.1 | B8B—B3B—H3B | 122.7 |
B7A—B3A—H3A | 122.4 | B4B—B3B—H3B | 122.2 |
B4A—B3A—H3A | 122.8 | B7B—B3B—H3B | 122.1 |
C1A—B4A—B5A | 58.56 (10) | C1B—B4B—B3B | 59.80 (10) |
C1A—B4A—B8A | 105.58 (12) | C1B—B4B—B8B | 105.11 (14) |
B5A—B4A—B8A | 108.37 (14) | B3B—B4B—B8B | 59.33 (12) |
C1A—B4A—B9A | 105.07 (13) | C1B—B4B—B9B | 104.88 (14) |
B5A—B4A—B9A | 59.96 (11) | B3B—B4B—B9B | 107.93 (15) |
B8A—B4A—B9A | 60.38 (11) | B8B—B4B—B9B | 60.21 (12) |
C1A—B4A—B3A | 59.76 (9) | C1B—B4B—B5B | 58.50 (10) |
B5A—B4A—B3A | 108.48 (13) | B3B—B4B—B5B | 108.33 (14) |
B8A—B4A—B3A | 59.58 (10) | B8B—B4B—B5B | 107.72 (15) |
B9A—B4A—B3A | 108.06 (13) | B9B—B4B—B5B | 59.73 (12) |
C1A—B4A—H4A | 124.1 | C1B—B4B—H4B | 124.2 |
B5A—B4A—H4A | 121.4 | B3B—B4B—H4B | 121.3 |
B8A—B4A—H4A | 122.1 | B8B—B4B—H4B | 122.5 |
B9A—B4A—H4A | 122.3 | B9B—B4B—H4B | 122.4 |
B3A—B4A—H4A | 121.2 | B5B—B4B—H4B | 121.7 |
C1A—B5A—B4A | 58.79 (10) | C1B—B5B—B10B | 106.15 (13) |
C1A—B5A—B9A | 105.39 (12) | C1B—B5B—B6B | 60.15 (10) |
B4A—B5A—B9A | 60.14 (11) | B10B—B5B—B6B | 59.96 (11) |
C1A—B5A—B6A | 59.87 (10) | C1B—B5B—B9B | 105.10 (13) |
B4A—B5A—B6A | 108.84 (13) | B10B—B5B—B9B | 60.39 (12) |
B9A—B5A—B6A | 108.21 (13) | B6B—B5B—B9B | 108.43 (14) |
C1A—B5A—B10A | 105.86 (12) | C1B—B5B—B4B | 58.39 (10) |
B4A—B5A—B10A | 108.70 (13) | B10B—B5B—B4B | 108.77 (15) |
B9A—B5A—B10A | 60.39 (11) | B6B—B5B—B4B | 108.90 (13) |
B6A—B5A—B10A | 59.65 (10) | B9B—B5B—B4B | 60.12 (12) |
C1A—B5A—H5A | 123.9 | C1B—B5B—H5B | 124.0 |
B4A—B5A—H5A | 121.1 | B10B—B5B—H5B | 121.7 |
B9A—B5A—H5A | 122.2 | B6B—B5B—H5B | 120.8 |
B6A—B5A—H5A | 121.1 | B9B—B5B—H5B | 122.3 |
B10A—B5A—H5A | 122.0 | B4B—B5B—H5B | 121.3 |
C2A—B6A—C1A | 57.47 (9) | C2B—B6B—C1B | 56.99 (9) |
C2A—B6A—B10A | 104.32 (13) | C2B—B6B—B10B | 104.84 (14) |
C1A—B6A—B10A | 104.84 (13) | C1B—B6B—B10B | 104.46 (13) |
C2A—B6A—B5A | 103.84 (12) | C2B—B6B—B11B | 58.75 (11) |
C1A—B6A—B5A | 57.95 (10) | C1B—B6B—B11B | 104.60 (13) |
B10A—B6A—B5A | 60.25 (11) | B10B—B6B—B11B | 60.24 (11) |
C2A—B6A—B11A | 58.13 (10) | C2B—B6B—B5B | 103.86 (13) |
C1A—B6A—B11A | 104.79 (12) | C1B—B6B—B5B | 57.96 (10) |
B10A—B6A—B11A | 60.12 (11) | B10B—B6B—B5B | 59.96 (11) |
B5A—B6A—B11A | 107.74 (13) | B11B—B6B—B5B | 107.69 (14) |
C2A—B6A—H6A | 125.0 | C2B—B6B—H6B | 124.7 |
C1A—B6A—H6A | 124.4 | C1B—B6B—H6B | 124.9 |
B10A—B6A—H6A | 122.8 | B10B—B6B—H6B | 122.8 |
B5A—B6A—H6A | 122.6 | B11B—B6B—H6B | 122.0 |
B11A—B6A—H6A | 122.2 | B5B—B6B—H6B | 122.7 |
C2A—B7A—B12A | 104.69 (13) | C2B—B7B—B8B | 104.70 (14) |
C2A—B7A—B8A | 104.80 (13) | C2B—B7B—B3B | 59.65 (10) |
B12A—B7A—B8A | 60.81 (11) | B8B—B7B—B3B | 59.18 (12) |
C2A—B7A—B3A | 59.19 (10) | C2B—B7B—B12B | 104.57 (14) |
B12A—B7A—B3A | 108.59 (13) | B8B—B7B—B12B | 60.24 (13) |
B8A—B7A—B3A | 59.67 (10) | B3B—B7B—B12B | 107.81 (15) |
C2A—B7A—B11A | 58.61 (10) | C2B—B7B—B11B | 58.83 (11) |
B12A—B7A—B11A | 59.98 (11) | B8B—B7B—B11B | 107.91 (15) |
B8A—B7A—B11A | 108.69 (13) | B3B—B7B—B11B | 108.77 (14) |
B3A—B7A—B11A | 108.66 (13) | B12B—B7B—B11B | 59.60 (12) |
C2A—B7A—H7A | 124.8 | C2B—B7B—H7B | 124.5 |
B12A—B7A—H7A | 122.1 | B8B—B7B—H7B | 122.7 |
B8A—B7A—H7A | 122.1 | B3B—B7B—H7B | 121.2 |
B3A—B7A—H7A | 121.1 | B12B—B7B—H7B | 122.6 |
B11A—B7A—H7A | 121.2 | B11B—B7B—H7B | 121.3 |
B3A—B8A—B7A | 60.47 (10) | B3B—B8B—B4B | 60.25 (12) |
B3A—B8A—B4A | 60.47 (10) | B3B—B8B—B7B | 60.41 (12) |
B7A—B8A—B4A | 108.19 (13) | B4B—B8B—B7B | 108.15 (14) |
B3A—B8A—B9A | 108.33 (13) | B3B—B8B—B9B | 108.56 (15) |
B7A—B8A—B9A | 107.30 (14) | B4B—B8B—B9B | 60.09 (12) |
B4A—B8A—B9A | 59.82 (11) | B7B—B8B—B9B | 107.83 (16) |
B3A—B8A—B12A | 108.14 (13) | B3B—B8B—B12B | 108.52 (15) |
B7A—B8A—B12A | 59.45 (11) | B4B—B8B—B12B | 107.90 (15) |
B4A—B8A—B12A | 107.55 (14) | B7B—B8B—B12B | 59.89 (13) |
B9A—B8A—B12A | 59.59 (11) | B9B—B8B—B12B | 59.77 (13) |
B3A—B8A—H8A | 121.1 | B3B—B8B—H8B | 121.1 |
B7A—B8A—H8A | 121.9 | B4B—B8B—H8B | 121.7 |
B4A—B8A—H8A | 121.7 | B7B—B8B—H8B | 121.7 |
B9A—B8A—H8A | 122.0 | B9B—B8B—H8B | 121.7 |
B12A—B8A—H8A | 122.2 | B12B—B8B—H8B | 121.8 |
B5A—B9A—B4A | 59.90 (10) | B5B—B9B—B12B | 107.56 (15) |
B5A—B9A—B12A | 108.10 (13) | B5B—B9B—B4B | 60.16 (12) |
B4A—B9A—B12A | 108.13 (13) | B12B—B9B—B4B | 107.88 (14) |
B5A—B9A—B8A | 107.86 (13) | B5B—B9B—B10B | 59.70 (12) |
B4A—B9A—B8A | 59.80 (11) | B12B—B9B—B10B | 60.21 (13) |
B12A—B9A—B8A | 60.35 (11) | B4B—B9B—B10B | 108.25 (15) |
B5A—B9A—B10A | 59.96 (11) | B5B—B9B—B8B | 107.67 (14) |
B4A—B9A—B10A | 108.16 (13) | B12B—B9B—B8B | 60.12 (13) |
B12A—B9A—B10A | 60.37 (11) | B4B—B9B—B8B | 59.71 (12) |
B8A—B9A—B10A | 108.63 (13) | B10B—B9B—B8B | 108.37 (15) |
B5A—B9A—H9A | 121.9 | B5B—B9B—H9B | 122.1 |
B4A—B9A—H9A | 121.8 | B12B—B9B—H9B | 121.8 |
B12A—B9A—H9A | 121.4 | B4B—B9B—H9B | 121.7 |
B8A—B9A—H9A | 121.6 | B10B—B9B—H9B | 121.5 |
B10A—B9A—H9A | 121.4 | B8B—B9B—H9B | 121.7 |
B6A—B10A—B5A | 60.11 (10) | B5B—B10B—B6B | 60.08 (11) |
B6A—B10A—B11A | 60.50 (10) | B5B—B10B—B11B | 107.55 (14) |
B5A—B10A—B11A | 107.93 (13) | B6B—B10B—B11B | 59.94 (11) |
B6A—B10A—B9A | 107.98 (13) | B5B—B10B—B9B | 59.91 (12) |
B5A—B10A—B9A | 59.65 (11) | B6B—B10B—B9B | 108.14 (14) |
B11A—B10A—B9A | 107.39 (14) | B11B—B10B—B9B | 107.54 (15) |
B6A—B10A—B12A | 108.02 (13) | B5B—B10B—B12B | 107.36 (15) |
B5A—B10A—B12A | 107.22 (14) | B6B—B10B—B12B | 107.67 (14) |
B11A—B10A—B12A | 59.56 (11) | B11B—B10B—B12B | 59.60 (12) |
B9A—B10A—B12A | 59.57 (11) | B9B—B10B—B12B | 59.75 (13) |
B6A—B10A—H10A | 121.3 | B5B—B10B—H10B | 122.0 |
B5A—B10A—H10A | 122.0 | B6B—B10B—H10B | 121.6 |
B11A—B10A—H10A | 121.8 | B11B—B10B—H10B | 122.1 |
B9A—B10A—H10A | 122.1 | B9B—B10B—H10B | 121.8 |
B12A—B10A—H10A | 122.2 | B12B—B10B—H10B | 122.2 |
C2A—B11A—B12A | 104.23 (13) | C2B—B11B—B12B | 104.40 (15) |
C2A—B11A—B10A | 104.58 (13) | C2B—B11B—B6B | 59.25 (10) |
B12A—B11A—B10A | 60.51 (11) | B12B—B11B—B6B | 108.22 (15) |
C2A—B11A—B7A | 58.46 (10) | C2B—B11B—B10B | 104.90 (14) |
B12A—B11A—B7A | 59.54 (11) | B12B—B11B—B10B | 60.41 (12) |
B10A—B11A—B7A | 107.98 (14) | B6B—B11B—B10B | 59.82 (11) |
C2A—B11A—B6A | 59.23 (10) | C2B—B11B—B7B | 58.25 (11) |
B12A—B11A—B6A | 107.87 (13) | B12B—B11B—B7B | 59.96 (12) |
B10A—B11A—B6A | 59.37 (10) | B6B—B11B—B7B | 108.25 (14) |
B7A—B11A—B6A | 108.15 (13) | B10B—B11B—B7B | 108.34 (15) |
C2A—B11A—H11A | 124.8 | C2B—B11B—H11B | 124.9 |
B12A—B11A—H11A | 122.5 | B12B—B11B—H11B | 122.3 |
B10A—B11A—H11A | 122.4 | B6B—B11B—H11B | 121.2 |
B7A—B11A—H11A | 121.6 | B10B—B11B—H11B | 122.1 |
B6A—B11A—H11A | 121.4 | B7B—B11B—H11B | 121.5 |
B7A—B12A—B11A | 60.48 (11) | B11B—B12B—B9B | 108.09 (15) |
B7A—B12A—B9A | 107.91 (14) | B11B—B12B—B7B | 60.44 (12) |
B11A—B12A—B9A | 108.07 (13) | B9B—B12B—B7B | 108.08 (16) |
B7A—B12A—B8A | 59.75 (11) | B11B—B12B—B8B | 108.28 (15) |
B11A—B12A—B8A | 108.25 (13) | B9B—B12B—B8B | 60.11 (13) |
B9A—B12A—B8A | 60.06 (11) | B7B—B12B—B8B | 59.87 (13) |
B7A—B12A—B10A | 108.27 (13) | B11B—B12B—B10B | 59.99 (12) |
B11A—B12A—B10A | 59.93 (11) | B9B—B12B—B10B | 60.04 (12) |
B9A—B12A—B10A | 60.06 (11) | B7B—B12B—B10B | 108.39 (15) |
B8A—B12A—B10A | 108.16 (14) | B8B—B12B—B10B | 108.24 (15) |
B7A—B12A—H12A | 121.6 | B11B—B12B—H12B | 121.5 |
B11A—B12A—H12A | 121.5 | B9B—B12B—H12B | 121.7 |
B9A—B12A—H12A | 121.8 | B7B—B12B—H12B | 121.5 |
B8A—B12A—H12A | 121.7 | B8B—B12B—H12B | 121.6 |
B10A—B12A—H12A | 121.6 | B10B—B12B—H12B | 121.6 |
| | | |
C4A—C1A—C2A—C3A | 3.9 (2) | C4B—C1B—C2B—C3B | −1.1 (2) |
B5A—C1A—C2A—C3A | 146.81 (14) | B4B—C1B—C2B—C3B | −146.10 (15) |
B4A—C1A—C2A—C3A | −146.01 (14) | B5B—C1B—C2B—C3B | 145.97 (15) |
B6A—C1A—C2A—C3A | 107.08 (15) | B3B—C1B—C2B—C3B | −107.01 (16) |
B3A—C1A—C2A—C3A | −106.28 (15) | B6B—C1B—C2B—C3B | 107.04 (16) |
C4A—C1A—C2A—B7A | 149.65 (14) | C4B—C1B—C2B—B7B | 144.63 (15) |
B5A—C1A—C2A—B7A | −67.47 (15) | B4B—C1B—C2B—B7B | −0.32 (18) |
B4A—C1A—C2A—B7A | −0.29 (17) | B5B—C1B—C2B—B7B | −68.26 (17) |
B6A—C1A—C2A—B7A | −107.20 (14) | B3B—C1B—C2B—B7B | 38.77 (14) |
B3A—C1A—C2A—B7A | 39.44 (12) | B6B—C1B—C2B—B7B | −107.19 (15) |
C4A—C1A—C2A—B11A | −142.09 (14) | C4B—C1B—C2B—B11B | −147.31 (15) |
B5A—C1A—C2A—B11A | 0.79 (16) | B4B—C1B—C2B—B11B | 67.74 (17) |
B4A—C1A—C2A—B11A | 67.97 (15) | B5B—C1B—C2B—B11B | −0.19 (18) |
B6A—C1A—C2A—B11A | −38.94 (12) | B3B—C1B—C2B—B11B | 106.83 (15) |
B3A—C1A—C2A—B11A | 107.70 (14) | B6B—C1B—C2B—B11B | −39.12 (13) |
C4A—C1A—C2A—B3A | 110.21 (15) | C4B—C1B—C2B—B6B | −108.19 (16) |
B5A—C1A—C2A—B3A | −106.91 (13) | B4B—C1B—C2B—B6B | 106.86 (15) |
B4A—C1A—C2A—B3A | −39.73 (12) | B5B—C1B—C2B—B6B | 38.93 (13) |
B6A—C1A—C2A—B3A | −146.64 (12) | B3B—C1B—C2B—B6B | 145.95 (14) |
C4A—C1A—C2A—B6A | −103.15 (15) | C4B—C1B—C2B—B3B | 105.86 (16) |
B5A—C1A—C2A—B6A | 39.73 (12) | B4B—C1B—C2B—B3B | −39.09 (13) |
B4A—C1A—C2A—B6A | 106.91 (13) | B5B—C1B—C2B—B3B | −107.02 (15) |
B3A—C1A—C2A—B6A | 146.64 (12) | B6B—C1B—C2B—B3B | −145.95 (14) |
C1A—C2A—C3A—O1A | 164.45 (13) | C1B—C2B—C3B—O1B | 53.25 (19) |
C1A—C2A—C3A—O2A | −17.1 (2) | C1B—C2B—C3B—O2B | −129.22 (18) |
B7A—C2A—C3A—O2A | −160.66 (15) | C2B—C1B—C4B—O3B | 55.16 (19) |
B11A—C2A—C3A—O2A | 126.75 (16) | B7B—C2B—C3B—O2B | 87.8 (2) |
B3A—C2A—C3A—O2A | −88.88 (18) | B11B—C2B—C3B—O2B | 14.1 (2) |
B6A—C2A—C3A—O2A | 54.6 (2) | B6B—C2B—C3B—O2B | −57.5 (2) |
B7A—C2A—C3A—O1A | 20.9 (2) | B3B—C2B—C3B—O2B | 159.69 (16) |
B11A—C2A—C3A—O1A | −51.65 (19) | B7B—C2B—C3B—O1B | −89.74 (19) |
B3A—C2A—C3A—O1A | 92.72 (17) | B11B—C2B—C3B—O1B | −163.39 (14) |
B6A—C2A—C3A—O1A | −123.78 (15) | B6B—C2B—C3B—O1B | 124.99 (15) |
C5A—O3A—C4A—C1A | −90.62 (18) | B3B—C2B—C3B—O1B | −17.8 (2) |
C2A—C1A—C4A—O3A | −69.56 (18) | C5B—O3B—C4B—C1B | −172.45 (17) |
B5A—C1A—C4A—O3A | 150.01 (13) | B4B—C1B—C4B—O3B | −162.94 (14) |
B4A—C1A—C4A—O3A | 77.23 (18) | B5B—C1B—C4B—O3B | −88.24 (19) |
B6A—C1A—C4A—O3A | −139.80 (13) | B3B—C1B—C4B—O3B | 125.71 (15) |
B3A—C1A—C4A—O3A | 3.1 (2) | B6B—C1B—C4B—O3B | −15.6 (2) |
C3A—C2A—B3A—C1A | 112.42 (14) | C4B—C1B—B3B—C2B | −110.65 (16) |
B7A—C2A—B3A—C1A | −138.23 (12) | B4B—C1B—B3B—C2B | 138.18 (14) |
B11A—C2A—B3A—C1A | −102.13 (13) | B5B—C1B—B3B—C2B | 100.85 (15) |
B6A—C2A—B3A—C1A | −32.17 (12) | B6B—C1B—B3B—C2B | 32.38 (13) |
C3A—C2A—B3A—B8A | −149.34 (13) | C4B—C1B—B3B—B8B | 151.38 (16) |
C1A—C2A—B3A—B8A | 98.24 (12) | C2B—C1B—B3B—B8B | −97.97 (15) |
B7A—C2A—B3A—B8A | −39.99 (12) | B4B—C1B—B3B—B8B | 40.22 (14) |
B11A—C2A—B3A—B8A | −3.88 (17) | B5B—C1B—B3B—B8B | 2.88 (19) |
B6A—C2A—B3A—B8A | 66.07 (15) | B6B—C1B—B3B—B8B | −65.59 (17) |
C3A—C2A—B3A—B7A | −109.35 (15) | C4B—C1B—B3B—B4B | 111.17 (16) |
C1A—C2A—B3A—B7A | 138.23 (12) | C2B—C1B—B3B—B4B | −138.18 (14) |
B11A—C2A—B3A—B7A | 36.11 (13) | B5B—C1B—B3B—B4B | −37.33 (14) |
B6A—C2A—B3A—B7A | 106.07 (14) | B6B—C1B—B3B—B4B | −105.81 (15) |
C3A—C2A—B3A—B4A | 148.67 (13) | C4B—C1B—B3B—B7B | −146.00 (14) |
C1A—C2A—B3A—B4A | 36.25 (11) | C2B—C1B—B3B—B7B | −35.35 (12) |
B7A—C2A—B3A—B4A | −101.98 (13) | B4B—C1B—B3B—B7B | 102.83 (15) |
B11A—C2A—B3A—B4A | −65.87 (15) | B5B—C1B—B3B—B7B | 65.50 (17) |
B6A—C2A—B3A—B4A | 4.08 (17) | B6B—C1B—B3B—B7B | −2.98 (18) |
C4A—C1A—B3A—C2A | −111.67 (15) | C3B—C2B—B3B—C1B | 110.72 (16) |
B5A—C1A—B3A—C2A | 100.42 (13) | B7B—C2B—B3B—C1B | −138.70 (14) |
B4A—C1A—B3A—C2A | 137.32 (13) | B11B—C2B—B3B—C1B | −101.92 (14) |
B6A—C1A—B3A—C2A | 31.70 (12) | B6B—C2B—B3B—C1B | −32.99 (13) |
C4A—C1A—B3A—B8A | 150.49 (14) | C3B—C2B—B3B—B8B | −151.01 (14) |
C2A—C1A—B3A—B8A | −97.84 (13) | C1B—C2B—B3B—B8B | 98.26 (14) |
B5A—C1A—B3A—B8A | 2.58 (17) | B7B—C2B—B3B—B8B | −40.43 (13) |
B4A—C1A—B3A—B8A | 39.47 (12) | B11B—C2B—B3B—B8B | −3.66 (18) |
B6A—C1A—B3A—B8A | −66.14 (15) | B6B—C2B—B3B—B8B | 65.27 (17) |
C4A—C1A—B3A—B7A | −147.48 (14) | C3B—C2B—B3B—B4B | 146.43 (15) |
C2A—C1A—B3A—B7A | −35.80 (11) | C1B—C2B—B3B—B4B | 35.70 (12) |
B5A—C1A—B3A—B7A | 64.62 (15) | B7B—C2B—B3B—B4B | −102.99 (15) |
B4A—C1A—B3A—B7A | 101.51 (13) | B11B—C2B—B3B—B4B | −66.22 (17) |
B6A—C1A—B3A—B7A | −4.10 (16) | B6B—C2B—B3B—B4B | 2.71 (19) |
C4A—C1A—B3A—B4A | 111.01 (16) | C3B—C2B—B3B—B7B | −110.58 (16) |
C2A—C1A—B3A—B4A | −137.32 (13) | C1B—C2B—B3B—B7B | 138.70 (14) |
B5A—C1A—B3A—B4A | −36.89 (13) | B11B—C2B—B3B—B7B | 36.78 (13) |
B6A—C1A—B3A—B4A | −105.61 (14) | B6B—C2B—B3B—B7B | 105.70 (15) |
C4A—C1A—B4A—B5A | 106.86 (15) | C4B—C1B—B4B—B3B | −106.01 (17) |
C2A—C1A—B4A—B5A | −102.82 (13) | C2B—C1B—B4B—B3B | 38.84 (13) |
B6A—C1A—B4A—B5A | −36.53 (12) | B5B—C1B—B4B—B3B | 141.58 (15) |
B3A—C1A—B4A—B5A | −141.84 (13) | B6B—C1B—B4B—B3B | 105.37 (15) |
C4A—C1A—B4A—B8A | −150.85 (14) | C4B—C1B—B4B—B8B | −145.79 (16) |
C2A—C1A—B4A—B8A | −0.53 (17) | C2B—C1B—B4B—B8B | −0.95 (18) |
B5A—C1A—B4A—B8A | 102.29 (14) | B5B—C1B—B4B—B8B | 101.79 (15) |
B6A—C1A—B4A—B8A | 65.76 (16) | B3B—C1B—B4B—B8B | −39.79 (13) |
B3A—C1A—B4A—B8A | −39.55 (12) | B6B—C1B—B4B—B8B | 65.58 (17) |
C4A—C1A—B4A—B9A | 146.31 (14) | C4B—C1B—B4B—B9B | 151.64 (15) |
C2A—C1A—B4A—B9A | −63.37 (15) | C2B—C1B—B4B—B9B | −63.51 (16) |
B5A—C1A—B4A—B9A | 39.44 (12) | B5B—C1B—B4B—B9B | 39.23 (13) |
B6A—C1A—B4A—B9A | 2.91 (17) | B3B—C1B—B4B—B9B | −102.35 (16) |
B3A—C1A—B4A—B9A | −102.40 (14) | B6B—C1B—B4B—B9B | 3.02 (18) |
C4A—C1A—B4A—B3A | −111.30 (15) | C4B—C1B—B4B—B5B | 112.41 (17) |
C2A—C1A—B4A—B3A | 39.02 (12) | C2B—C1B—B4B—B5B | −102.75 (14) |
B5A—C1A—B4A—B3A | 141.84 (13) | B3B—C1B—B4B—B5B | −141.58 (15) |
B6A—C1A—B4A—B3A | 105.31 (13) | B6B—C1B—B4B—B5B | −36.22 (14) |
C2A—B3A—B4A—C1A | −36.07 (11) | C2B—B3B—B4B—C1B | −35.23 (12) |
B8A—B3A—B4A—C1A | −134.66 (14) | B8B—B3B—B4B—C1B | −134.09 (15) |
B7A—B3A—B4A—C1A | −96.64 (13) | B7B—B3B—B4B—C1B | −95.86 (14) |
C2A—B3A—B4A—B5A | −2.31 (16) | C1B—B3B—B4B—B8B | 134.09 (15) |
C1A—B3A—B4A—B5A | 33.76 (11) | C2B—B3B—B4B—B8B | 98.86 (15) |
B8A—B3A—B4A—B5A | −100.90 (15) | B7B—B3B—B4B—B8B | 38.23 (14) |
B7A—B3A—B4A—B5A | −62.87 (15) | C1B—B3B—B4B—B9B | 97.12 (15) |
C2A—B3A—B4A—B8A | 98.59 (14) | C2B—B3B—B4B—B9B | 61.89 (17) |
C1A—B3A—B4A—B8A | 134.66 (14) | B8B—B3B—B4B—B9B | −36.97 (14) |
B7A—B3A—B4A—B8A | 38.02 (13) | B7B—B3B—B4B—B9B | 1.26 (18) |
C2A—B3A—B4A—B9A | 61.19 (15) | C1B—B3B—B4B—B5B | 33.93 (13) |
C1A—B3A—B4A—B9A | 97.26 (14) | C2B—B3B—B4B—B5B | −1.30 (19) |
B8A—B3A—B4A—B9A | −37.40 (13) | B8B—B3B—B4B—B5B | −100.16 (17) |
B7A—B3A—B4A—B9A | 0.63 (16) | B7B—B3B—B4B—B5B | −61.93 (18) |
C4A—C1A—B5A—B4A | −112.40 (15) | C4B—C1B—B5B—B10B | 147.75 (15) |
C2A—C1A—B5A—B4A | 102.78 (13) | C2B—C1B—B5B—B10B | 1.39 (18) |
B6A—C1A—B5A—B4A | 142.01 (13) | B4B—C1B—B5B—B10B | −102.42 (16) |
B3A—C1A—B5A—B4A | 36.78 (13) | B3B—C1B—B5B—B10B | −65.49 (17) |
C4A—C1A—B5A—B9A | −152.00 (14) | B6B—C1B—B5B—B10B | 39.91 (13) |
C2A—C1A—B5A—B9A | 63.18 (15) | C4B—C1B—B5B—B6B | 107.83 (16) |
B4A—C1A—B5A—B9A | −39.60 (12) | C2B—C1B—B5B—B6B | −38.53 (13) |
B6A—C1A—B5A—B9A | 102.41 (14) | B4B—C1B—B5B—B6B | −142.34 (15) |
B3A—C1A—B5A—B9A | −2.82 (17) | B3B—C1B—B5B—B6B | −105.40 (15) |
C4A—C1A—B5A—B6A | 105.59 (15) | C4B—C1B—B5B—B9B | −149.30 (15) |
C2A—C1A—B5A—B6A | −39.23 (12) | C2B—C1B—B5B—B9B | 64.34 (16) |
B4A—C1A—B5A—B6A | −142.01 (13) | B4B—C1B—B5B—B9B | −39.47 (14) |
B3A—C1A—B5A—B6A | −105.23 (14) | B3B—C1B—B5B—B9B | −2.53 (19) |
C4A—C1A—B5A—B10A | 145.03 (14) | B6B—C1B—B5B—B9B | 102.87 (15) |
C2A—C1A—B5A—B10A | 0.22 (16) | C4B—C1B—B5B—B4B | −109.83 (17) |
B4A—C1A—B5A—B10A | −102.57 (14) | C2B—C1B—B5B—B4B | 103.81 (14) |
B6A—C1A—B5A—B10A | 39.45 (12) | B3B—C1B—B5B—B4B | 36.94 (14) |
B3A—C1A—B5A—B10A | −65.78 (16) | B6B—C1B—B5B—B4B | 142.34 (15) |
B8A—B4A—B5A—C1A | −97.40 (13) | B3B—B4B—B5B—C1B | −34.45 (13) |
B9A—B4A—B5A—C1A | −134.87 (13) | B8B—B4B—B5B—C1B | −97.18 (15) |
B3A—B4A—B5A—C1A | −34.25 (12) | B9B—B4B—B5B—C1B | −134.94 (15) |
C1A—B4A—B5A—B9A | 134.87 (13) | C1B—B4B—B5B—B10B | 97.81 (15) |
B8A—B4A—B5A—B9A | 37.47 (12) | B3B—B4B—B5B—B10B | 63.35 (18) |
B3A—B4A—B5A—B9A | 100.62 (14) | B8B—B4B—B5B—B10B | 0.63 (19) |
C1A—B4A—B5A—B6A | 34.23 (12) | B9B—B4B—B5B—B10B | −37.14 (14) |
B8A—B4A—B5A—B6A | −63.17 (16) | C1B—B4B—B5B—B6B | 34.07 (13) |
B9A—B4A—B5A—B6A | −100.65 (14) | B3B—B4B—B5B—B6B | −0.4 (2) |
B3A—B4A—B5A—B6A | −0.02 (17) | B8B—B4B—B5B—B6B | −63.12 (18) |
C1A—B4A—B5A—B10A | 97.60 (13) | B9B—B4B—B5B—B6B | −100.88 (16) |
B8A—B4A—B5A—B10A | 0.20 (17) | C1B—B4B—B5B—B9B | 134.94 (15) |
B9A—B4A—B5A—B10A | −37.28 (12) | B3B—B4B—B5B—B9B | 100.49 (17) |
B3A—B4A—B5A—B10A | 63.35 (16) | B8B—B4B—B5B—B9B | 37.76 (14) |
C3A—C2A—B6A—C1A | −112.05 (14) | C3B—C2B—B6B—C1B | −111.00 (16) |
B7A—C2A—B6A—C1A | 102.02 (14) | B7B—C2B—B6B—C1B | 102.01 (15) |
B11A—C2A—B6A—C1A | 138.85 (12) | B11B—C2B—B6B—C1B | 138.22 (14) |
B3A—C2A—B6A—C1A | 32.26 (12) | B3B—C2B—B6B—C1B | 32.78 (13) |
C3A—C2A—B6A—B10A | 149.28 (14) | C3B—C2B—B6B—B10B | 151.19 (15) |
C1A—C2A—B6A—B10A | −98.67 (13) | C1B—C2B—B6B—B10B | −97.81 (14) |
B7A—C2A—B6A—B10A | 3.35 (17) | B7B—C2B—B6B—B10B | 4.20 (18) |
B11A—C2A—B6A—B10A | 40.18 (12) | B11B—C2B—B6B—B10B | 40.41 (13) |
B3A—C2A—B6A—B10A | −66.41 (16) | B3B—C2B—B6B—B10B | −65.02 (17) |
C3A—C2A—B6A—B5A | −148.41 (13) | C3B—C2B—B6B—B11B | 110.78 (16) |
C1A—C2A—B6A—B5A | −36.35 (11) | C1B—C2B—B6B—B11B | −138.22 (14) |
B7A—C2A—B6A—B5A | 65.67 (16) | B7B—C2B—B6B—B11B | −36.21 (15) |
B11A—C2A—B6A—B5A | 102.50 (13) | B3B—C2B—B6B—B11B | −105.44 (16) |
B3A—C2A—B6A—B5A | −4.10 (17) | C3B—C2B—B6B—B5B | −146.72 (15) |
C3A—C2A—B6A—B11A | 109.09 (15) | C1B—C2B—B6B—B5B | −35.72 (12) |
C1A—C2A—B6A—B11A | −138.85 (12) | B7B—C2B—B6B—B5B | 66.30 (17) |
B7A—C2A—B6A—B11A | −36.83 (13) | B11B—C2B—B6B—B5B | 102.50 (15) |
B3A—C2A—B6A—B11A | −106.60 (14) | B3B—C2B—B6B—B5B | −2.93 (18) |
C4A—C1A—B6A—C2A | 113.97 (14) | C4B—C1B—B6B—C2B | 109.63 (16) |
B5A—C1A—B6A—C2A | −137.23 (12) | B4B—C1B—B6B—C2B | −101.35 (15) |
B4A—C1A—B6A—C2A | −100.52 (13) | B5B—C1B—B6B—C2B | −138.04 (14) |
B3A—C1A—B6A—C2A | −31.61 (11) | B3B—C1B—B6B—C2B | −32.57 (13) |
C4A—C1A—B6A—B10A | −148.31 (13) | C4B—C1B—B6B—B10B | −151.86 (15) |
C2A—C1A—B6A—B10A | 97.73 (13) | C2B—C1B—B6B—B10B | 98.51 (14) |
B5A—C1A—B6A—B10A | −39.50 (12) | B4B—C1B—B6B—B10B | −2.84 (18) |
B4A—C1A—B6A—B10A | −2.79 (16) | B5B—C1B—B6B—B10B | −39.53 (13) |
B3A—C1A—B6A—B10A | 66.12 (15) | B3B—C1B—B6B—B10B | 65.94 (16) |
C4A—C1A—B6A—B5A | −108.80 (14) | C4B—C1B—B6B—B11B | 145.69 (15) |
C2A—C1A—B6A—B5A | 137.23 (12) | C2B—C1B—B6B—B11B | 36.06 (12) |
B4A—C1A—B6A—B5A | 36.71 (13) | B4B—C1B—B6B—B11B | −65.29 (17) |
B3A—C1A—B6A—B5A | 105.62 (13) | B5B—C1B—B6B—B11B | −101.98 (15) |
C4A—C1A—B6A—B11A | 149.27 (13) | B3B—C1B—B6B—B11B | 3.49 (18) |
C2A—C1A—B6A—B11A | 35.31 (11) | C4B—C1B—B6B—B5B | −112.34 (17) |
B5A—C1A—B6A—B11A | −101.92 (13) | C2B—C1B—B6B—B5B | 138.04 (14) |
B4A—C1A—B6A—B11A | −65.21 (15) | B4B—C1B—B6B—B5B | 36.68 (14) |
B3A—C1A—B6A—B11A | 3.70 (16) | B3B—C1B—B6B—B5B | 105.47 (15) |
C1A—B5A—B6A—C2A | 36.13 (11) | C1B—B5B—B6B—C2B | 35.28 (12) |
B4A—B5A—B6A—C2A | 2.34 (16) | B10B—B5B—B6B—C2B | −99.33 (14) |
B9A—B5A—B6A—C2A | −61.46 (15) | B9B—B5B—B6B—C2B | −61.92 (16) |
B10A—B5A—B6A—C2A | −98.77 (13) | B4B—B5B—B6B—C2B | 1.91 (18) |
B4A—B5A—B6A—C1A | −33.80 (12) | B10B—B5B—B6B—C1B | −134.61 (14) |
B9A—B5A—B6A—C1A | −97.59 (13) | B9B—B5B—B6B—C1B | −97.20 (14) |
B10A—B5A—B6A—C1A | −134.91 (13) | B4B—B5B—B6B—C1B | −33.37 (13) |
C1A—B5A—B6A—B10A | 134.91 (13) | C1B—B5B—B6B—B10B | 134.61 (14) |
B4A—B5A—B6A—B10A | 101.11 (14) | B9B—B5B—B6B—B10B | 37.41 (14) |
B9A—B5A—B6A—B10A | 37.32 (13) | B4B—B5B—B6B—B10B | 101.24 (16) |
C1A—B5A—B6A—B11A | 96.66 (13) | C1B—B5B—B6B—B11B | 96.46 (14) |
B4A—B5A—B6A—B11A | 62.86 (16) | B10B—B5B—B6B—B11B | −38.16 (14) |
B9A—B5A—B6A—B11A | −0.93 (17) | B9B—B5B—B6B—B11B | −0.75 (18) |
B10A—B5A—B6A—B11A | −38.25 (12) | B4B—B5B—B6B—B11B | 63.09 (18) |
C3A—C2A—B7A—B12A | −149.12 (14) | C3B—C2B—B7B—B8B | 147.36 (15) |
C1A—C2A—B7A—B12A | 64.08 (16) | C1B—C2B—B7B—B8B | 1.44 (19) |
B11A—C2A—B7A—B12A | −40.02 (13) | B11B—C2B—B7B—B8B | −102.29 (16) |
B3A—C2A—B7A—B12A | 103.14 (14) | B6B—C2B—B7B—B8B | −66.43 (18) |
B6A—C2A—B7A—B12A | −3.30 (18) | B3B—C2B—B7B—B8B | 39.88 (13) |
C3A—C2A—B7A—B8A | 147.77 (14) | C3B—C2B—B7B—B3B | 107.48 (17) |
C1A—C2A—B7A—B8A | 0.97 (17) | C1B—C2B—B7B—B3B | −38.44 (13) |
B11A—C2A—B7A—B8A | −103.13 (14) | B11B—C2B—B7B—B3B | −142.17 (14) |
B3A—C2A—B7A—B8A | 40.03 (12) | B6B—C2B—B7B—B3B | −106.31 (15) |
B6A—C2A—B7A—B8A | −66.41 (17) | C3B—C2B—B7B—B12B | −150.16 (16) |
C3A—C2A—B7A—B3A | 107.74 (15) | C1B—C2B—B7B—B12B | 63.93 (18) |
C1A—C2A—B7A—B3A | −39.06 (12) | B11B—C2B—B7B—B12B | −39.81 (14) |
B11A—C2A—B7A—B3A | −143.16 (13) | B6B—C2B—B7B—B12B | −3.9 (2) |
B6A—C2A—B7A—B3A | −106.44 (14) | B3B—C2B—B7B—B12B | 102.36 (16) |
C3A—C2A—B7A—B11A | −109.10 (15) | C3B—C2B—B7B—B11B | −110.35 (17) |
C1A—C2A—B7A—B11A | 104.10 (13) | C1B—C2B—B7B—B11B | 103.73 (14) |
B3A—C2A—B7A—B11A | 143.16 (13) | B6B—C2B—B7B—B11B | 35.86 (14) |
B6A—C2A—B7A—B11A | 36.72 (13) | B3B—C2B—B7B—B11B | 142.17 (14) |
C1A—B3A—B7A—C2A | 35.48 (10) | C1B—B3B—B7B—C2B | 34.87 (11) |
B8A—B3A—B7A—C2A | 133.91 (13) | B8B—B3B—B7B—C2B | 133.77 (14) |
B4A—B3A—B7A—C2A | 95.84 (13) | B4B—B3B—B7B—C2B | 95.53 (14) |
C2A—B3A—B7A—B12A | −96.37 (14) | C1B—B3B—B7B—B8B | −98.90 (14) |
C1A—B3A—B7A—B12A | −60.89 (15) | C2B—B3B—B7B—B8B | −133.77 (14) |
B8A—B3A—B7A—B12A | 37.54 (13) | B4B—B3B—B7B—B8B | −38.23 (14) |
B4A—B3A—B7A—B12A | −0.53 (17) | C1B—B3B—B7B—B12B | −61.91 (17) |
C2A—B3A—B7A—B8A | −133.91 (13) | C2B—B3B—B7B—B12B | −96.78 (15) |
C1A—B3A—B7A—B8A | −98.43 (13) | B8B—B3B—B7B—B12B | 36.99 (14) |
B4A—B3A—B7A—B8A | −38.07 (12) | B4B—B3B—B7B—B12B | −1.25 (19) |
C2A—B3A—B7A—B11A | −32.70 (11) | C1B—B3B—B7B—B11B | 1.21 (18) |
C1A—B3A—B7A—B11A | 2.78 (16) | C2B—B3B—B7B—B11B | −33.66 (13) |
B8A—B3A—B7A—B11A | 101.21 (14) | B8B—B3B—B7B—B11B | 100.11 (16) |
B4A—B3A—B7A—B11A | 63.14 (15) | B4B—B3B—B7B—B11B | 61.87 (17) |
C2A—B3A—B8A—B7A | 39.18 (12) | C1B—B3B—B8B—B4B | −39.07 (13) |
C1A—B3A—B8A—B7A | 98.69 (13) | C2B—B3B—B8B—B4B | −98.19 (14) |
B4A—B3A—B8A—B7A | 137.15 (14) | B7B—B3B—B8B—B4B | −137.49 (15) |
C2A—B3A—B8A—B4A | −97.97 (13) | C1B—B3B—B8B—B7B | 98.42 (15) |
C1A—B3A—B8A—B4A | −38.46 (12) | C2B—B3B—B8B—B7B | 39.30 (13) |
B7A—B3A—B8A—B4A | −137.15 (14) | B4B—B3B—B8B—B7B | 137.49 (15) |
C2A—B3A—B8A—B9A | −60.75 (16) | C1B—B3B—B8B—B9B | −2.0 (2) |
C1A—B3A—B8A—B9A | −1.24 (17) | C2B—B3B—B8B—B9B | −61.12 (18) |
B7A—B3A—B8A—B9A | −99.93 (15) | B4B—B3B—B8B—B9B | 37.07 (15) |
B4A—B3A—B8A—B9A | 37.22 (13) | B7B—B3B—B8B—B9B | −100.42 (17) |
C2A—B3A—B8A—B12A | 2.34 (16) | C1B—B3B—B8B—B12B | 61.41 (18) |
C1A—B3A—B8A—B12A | 61.86 (15) | C2B—B3B—B8B—B12B | 2.29 (18) |
B7A—B3A—B8A—B12A | −36.83 (12) | B4B—B3B—B8B—B12B | 100.48 (16) |
B4A—B3A—B8A—B12A | 100.32 (14) | B7B—B3B—B8B—B12B | −37.01 (14) |
C2A—B7A—B8A—B3A | −39.79 (12) | C1B—B4B—B8B—B3B | 40.02 (13) |
B12A—B7A—B8A—B3A | −138.58 (13) | B9B—B4B—B8B—B3B | 138.75 (16) |
B11A—B7A—B8A—B3A | −101.15 (14) | B5B—B4B—B8B—B3B | 101.21 (15) |
C2A—B7A—B8A—B4A | −1.27 (18) | C1B—B4B—B8B—B7B | 1.82 (19) |
B12A—B7A—B8A—B4A | −100.06 (15) | B3B—B4B—B8B—B7B | −38.20 (14) |
B3A—B7A—B8A—B4A | 38.53 (13) | B9B—B4B—B8B—B7B | 100.56 (17) |
B11A—B7A—B8A—B4A | −62.62 (17) | B5B—B4B—B8B—B7B | 63.01 (18) |
C2A—B7A—B8A—B9A | 61.87 (16) | C1B—B4B—B8B—B9B | −98.74 (15) |
B12A—B7A—B8A—B9A | −36.92 (12) | B3B—B4B—B8B—B9B | −138.75 (16) |
B3A—B7A—B8A—B9A | 101.66 (14) | B5B—B4B—B8B—B9B | −37.55 (14) |
B11A—B7A—B8A—B9A | 0.52 (17) | C1B—B4B—B8B—B12B | −61.51 (17) |
C2A—B7A—B8A—B12A | 98.79 (14) | B3B—B4B—B8B—B12B | −101.53 (16) |
B3A—B7A—B8A—B12A | 138.58 (13) | B9B—B4B—B8B—B12B | 37.23 (14) |
B11A—B7A—B8A—B12A | 37.44 (13) | B5B—B4B—B8B—B12B | −0.32 (19) |
C1A—B4A—B8A—B3A | 39.64 (12) | C2B—B7B—B8B—B3B | −40.11 (13) |
B5A—B4A—B8A—B3A | 101.09 (14) | B12B—B7B—B8B—B3B | −138.72 (15) |
B9A—B4A—B8A—B3A | 138.38 (14) | B11B—B7B—B8B—B3B | −101.59 (15) |
C1A—B4A—B8A—B7A | 1.12 (18) | C2B—B7B—B8B—B4B | −2.0 (2) |
B5A—B4A—B8A—B7A | 62.56 (16) | B3B—B7B—B8B—B4B | 38.12 (14) |
B9A—B4A—B8A—B7A | 99.85 (15) | B12B—B7B—B8B—B4B | −100.59 (16) |
B3A—B4A—B8A—B7A | −38.52 (13) | B11B—B7B—B8B—B4B | −63.47 (18) |
C1A—B4A—B8A—B9A | −98.74 (14) | C2B—B7B—B8B—B9B | 61.53 (19) |
B5A—B4A—B8A—B9A | −37.29 (12) | B3B—B7B—B8B—B9B | 101.65 (16) |
B3A—B4A—B8A—B9A | −138.38 (14) | B12B—B7B—B8B—B9B | −37.07 (15) |
C1A—B4A—B8A—B12A | −61.67 (16) | B11B—B7B—B8B—B9B | 0.1 (2) |
B5A—B4A—B8A—B12A | −0.23 (16) | C2B—B7B—B8B—B12B | 98.60 (15) |
B9A—B4A—B8A—B12A | 37.06 (12) | B3B—B7B—B8B—B12B | 138.72 (15) |
B3A—B4A—B8A—B12A | −101.31 (14) | B11B—B7B—B8B—B12B | 37.12 (14) |
C1A—B5A—B9A—B4A | 38.95 (11) | C1B—B5B—B9B—B12B | −62.30 (18) |
B6A—B5A—B9A—B4A | 101.72 (14) | B10B—B5B—B9B—B12B | 37.96 (14) |
B10A—B5A—B9A—B4A | 138.71 (13) | B6B—B5B—B9B—B12B | 0.73 (19) |
C1A—B5A—B9A—B12A | −61.94 (16) | B4B—B5B—B9B—B12B | −100.93 (16) |
B4A—B5A—B9A—B12A | −100.89 (14) | C1B—B5B—B9B—B4B | 38.63 (13) |
B6A—B5A—B9A—B12A | 0.83 (18) | B10B—B5B—B9B—B4B | 138.89 (15) |
B10A—B5A—B9A—B12A | 37.82 (13) | B6B—B5B—B9B—B4B | 101.67 (15) |
C1A—B5A—B9A—B8A | 1.86 (17) | C1B—B5B—B9B—B10B | −100.26 (14) |
B4A—B5A—B9A—B8A | −37.09 (13) | B6B—B5B—B9B—B10B | −37.22 (13) |
B6A—B5A—B9A—B8A | 64.63 (17) | B4B—B5B—B9B—B10B | −138.89 (15) |
B10A—B5A—B9A—B8A | 101.62 (15) | C1B—B5B—B9B—B8B | 1.11 (19) |
C1A—B5A—B9A—B10A | −99.76 (13) | B10B—B5B—B9B—B8B | 101.36 (17) |
B4A—B5A—B9A—B10A | −138.71 (13) | B6B—B5B—B9B—B8B | 64.14 (19) |
B6A—B5A—B9A—B10A | −36.99 (12) | B4B—B5B—B9B—B8B | −37.53 (15) |
C1A—B4A—B9A—B5A | −38.77 (11) | C1B—B4B—B9B—B5B | −38.64 (12) |
B8A—B4A—B9A—B5A | −138.38 (13) | B3B—B4B—B9B—B5B | −101.18 (14) |
B3A—B4A—B9A—B5A | −101.33 (13) | B8B—B4B—B9B—B5B | −137.76 (15) |
C1A—B4A—B9A—B12A | 62.07 (16) | C1B—B4B—B9B—B12B | 61.75 (18) |
B5A—B4A—B9A—B12A | 100.84 (15) | B3B—B4B—B9B—B12B | −0.79 (19) |
B8A—B4A—B9A—B12A | −37.54 (13) | B8B—B4B—B9B—B12B | −37.37 (15) |
B3A—B4A—B9A—B12A | −0.49 (17) | B5B—B4B—B9B—B12B | 100.39 (16) |
C1A—B4A—B9A—B8A | 99.61 (13) | C1B—B4B—B9B—B10B | −1.93 (18) |
B5A—B4A—B9A—B8A | 138.38 (13) | B3B—B4B—B9B—B10B | −64.47 (17) |
B3A—B4A—B9A—B8A | 37.05 (12) | B8B—B4B—B9B—B10B | −101.05 (16) |
C1A—B4A—B9A—B10A | −1.81 (16) | B5B—B4B—B9B—B10B | 36.71 (14) |
B5A—B4A—B9A—B10A | 36.95 (12) | C1B—B4B—B9B—B8B | 99.13 (15) |
B8A—B4A—B9A—B10A | −101.42 (14) | B3B—B4B—B9B—B8B | 36.59 (14) |
B3A—B4A—B9A—B10A | −64.38 (16) | B5B—B4B—B9B—B8B | 137.76 (15) |
B3A—B8A—B9A—B5A | −0.37 (18) | B3B—B8B—B9B—B5B | 0.6 (2) |
B7A—B8A—B9A—B5A | −64.22 (17) | B4B—B8B—B9B—B5B | 37.73 (14) |
B4A—B8A—B9A—B5A | 37.14 (12) | B7B—B8B—B9B—B5B | −63.37 (19) |
B12A—B8A—B9A—B5A | −101.08 (14) | B12B—B8B—B9B—B5B | −100.49 (16) |
B3A—B8A—B9A—B4A | −37.51 (13) | B3B—B8B—B9B—B12B | 101.08 (17) |
B7A—B8A—B9A—B4A | −101.36 (14) | B4B—B8B—B9B—B12B | 138.22 (15) |
B12A—B8A—B9A—B4A | −138.22 (13) | B7B—B8B—B9B—B12B | 37.12 (14) |
B3A—B8A—B9A—B12A | 100.71 (14) | B3B—B8B—B9B—B4B | −37.14 (15) |
B7A—B8A—B9A—B12A | 36.86 (12) | B7B—B8B—B9B—B4B | −101.10 (16) |
B4A—B8A—B9A—B12A | 138.22 (13) | B12B—B8B—B9B—B4B | −138.22 (15) |
B3A—B8A—B9A—B10A | 63.12 (17) | B3B—B8B—B9B—B10B | 63.7 (2) |
B7A—B8A—B9A—B10A | −0.74 (17) | B4B—B8B—B9B—B10B | 100.85 (16) |
B4A—B8A—B9A—B10A | 100.63 (14) | B7B—B8B—B9B—B10B | −0.3 (2) |
B12A—B8A—B9A—B10A | −37.59 (13) | B12B—B8B—B9B—B10B | −37.37 (15) |
C2A—B6A—B10A—B5A | 97.96 (13) | C1B—B5B—B10B—B6B | −40.00 (13) |
C1A—B6A—B10A—B5A | 38.39 (11) | B9B—B5B—B10B—B6B | −138.48 (14) |
B11A—B6A—B10A—B5A | 137.16 (14) | B4B—B5B—B10B—B6B | −101.46 (15) |
C2A—B6A—B10A—B11A | −39.19 (12) | C1B—B5B—B10B—B11B | −2.02 (19) |
C1A—B6A—B10A—B11A | −98.77 (13) | B6B—B5B—B10B—B11B | 37.98 (14) |
B5A—B6A—B10A—B11A | −137.16 (14) | B9B—B5B—B10B—B11B | −100.50 (16) |
C2A—B6A—B10A—B9A | 61.03 (15) | B4B—B5B—B10B—B11B | −63.47 (18) |
C1A—B6A—B10A—B9A | 1.46 (16) | C1B—B5B—B10B—B9B | 98.47 (14) |
B5A—B6A—B10A—B9A | −36.93 (12) | B6B—B5B—B10B—B9B | 138.48 (14) |
B11A—B6A—B10A—B9A | 100.22 (14) | B4B—B5B—B10B—B9B | 37.02 (13) |
C2A—B6A—B10A—B12A | −1.95 (17) | C1B—B5B—B10B—B12B | 60.77 (17) |
C1A—B6A—B10A—B12A | −61.52 (16) | B6B—B5B—B10B—B12B | 100.77 (15) |
B5A—B6A—B10A—B12A | −99.91 (15) | B9B—B5B—B10B—B12B | −37.70 (14) |
B11A—B6A—B10A—B12A | 37.25 (13) | B4B—B5B—B10B—B12B | −0.68 (19) |
C1A—B5A—B10A—B6A | −39.55 (12) | C2B—B6B—B10B—B5B | 97.64 (14) |
B4A—B5A—B10A—B6A | −101.36 (14) | C1B—B6B—B10B—B5B | 38.55 (12) |
B9A—B5A—B10A—B6A | −138.52 (13) | B11B—B6B—B10B—B5B | 137.31 (15) |
C1A—B5A—B10A—B11A | −1.09 (17) | C2B—B6B—B10B—B11B | −39.67 (13) |
B4A—B5A—B10A—B11A | −62.89 (16) | C1B—B6B—B10B—B11B | −98.77 (14) |
B9A—B5A—B10A—B11A | −100.05 (15) | B5B—B6B—B10B—B11B | −137.31 (15) |
B6A—B5A—B10A—B11A | 38.47 (13) | C2B—B6B—B10B—B9B | 60.52 (17) |
C1A—B5A—B10A—B9A | 98.97 (13) | C1B—B6B—B10B—B9B | 1.42 (18) |
B4A—B5A—B10A—B9A | 37.16 (12) | B11B—B6B—B10B—B9B | 100.19 (16) |
B6A—B5A—B10A—B9A | 138.52 (13) | B5B—B6B—B10B—B9B | −37.13 (13) |
C1A—B5A—B10A—B12A | 61.71 (15) | C2B—B6B—B10B—B12B | −2.61 (18) |
B4A—B5A—B10A—B12A | −0.09 (17) | C1B—B6B—B10B—B12B | −61.70 (17) |
B9A—B5A—B10A—B12A | −37.25 (12) | B11B—B6B—B10B—B12B | 37.06 (14) |
B6A—B5A—B10A—B12A | 101.27 (14) | B5B—B6B—B10B—B12B | −100.25 (16) |
B5A—B9A—B10A—B6A | 37.13 (12) | B12B—B9B—B10B—B5B | −137.49 (15) |
B4A—B9A—B10A—B6A | 0.21 (17) | B4B—B9B—B10B—B5B | −36.91 (14) |
B12A—B9A—B10A—B6A | −100.76 (14) | B8B—B9B—B10B—B5B | −100.15 (16) |
B8A—B9A—B10A—B6A | −63.18 (16) | B5B—B9B—B10B—B6B | 37.20 (13) |
B4A—B9A—B10A—B5A | −36.93 (12) | B12B—B9B—B10B—B6B | −100.29 (16) |
B12A—B9A—B10A—B5A | −137.89 (13) | B4B—B9B—B10B—B6B | 0.29 (19) |
B8A—B9A—B10A—B5A | −100.31 (14) | B8B—B9B—B10B—B6B | −62.95 (19) |
B5A—B9A—B10A—B11A | 100.98 (14) | B5B—B9B—B10B—B11B | 100.50 (15) |
B4A—B9A—B10A—B11A | 64.05 (16) | B12B—B9B—B10B—B11B | −36.99 (14) |
B12A—B9A—B10A—B11A | −36.91 (12) | B4B—B9B—B10B—B11B | 63.60 (19) |
B8A—B9A—B10A—B11A | 0.67 (17) | B8B—B9B—B10B—B11B | 0.4 (2) |
B5A—B9A—B10A—B12A | 137.89 (13) | B5B—B9B—B10B—B12B | 137.49 (15) |
B4A—B9A—B10A—B12A | 100.96 (14) | B4B—B9B—B10B—B12B | 100.58 (16) |
B8A—B9A—B10A—B12A | 37.58 (13) | B8B—B9B—B10B—B12B | 37.34 (15) |
C3A—C2A—B11A—B12A | 148.80 (13) | C3B—C2B—B11B—B12B | 150.03 (15) |
C1A—C2A—B11A—B12A | −64.12 (15) | C1B—C2B—B11B—B12B | −63.74 (16) |
B7A—C2A—B11A—B12A | 39.70 (12) | B7B—C2B—B11B—B12B | 39.94 (13) |
B3A—C2A—B11A—B12A | 3.72 (17) | B6B—C2B—B11B—B12B | −102.88 (15) |
B6A—C2A—B11A—B12A | −102.56 (13) | B3B—C2B—B11B—B12B | 3.43 (18) |
C3A—C2A—B11A—B10A | −148.51 (14) | C3B—C2B—B11B—B6B | −107.09 (16) |
C1A—C2A—B11A—B10A | −1.43 (17) | C1B—C2B—B11B—B6B | 39.14 (13) |
B7A—C2A—B11A—B10A | 102.39 (14) | B7B—C2B—B11B—B6B | 142.82 (14) |
B3A—C2A—B11A—B10A | 66.41 (16) | B3B—C2B—B11B—B6B | 106.31 (15) |
B6A—C2A—B11A—B10A | −39.87 (12) | C3B—C2B—B11B—B10B | −147.31 (15) |
C3A—C2A—B11A—B7A | 109.10 (15) | C1B—C2B—B11B—B10B | −1.08 (18) |
C1A—C2A—B11A—B7A | −103.82 (13) | B7B—C2B—B11B—B10B | 102.60 (16) |
B3A—C2A—B11A—B7A | −35.98 (12) | B6B—C2B—B11B—B10B | −40.22 (13) |
B6A—C2A—B11A—B7A | −142.26 (13) | B3B—C2B—B11B—B10B | 66.10 (17) |
C3A—C2A—B11A—B6A | −108.64 (15) | C3B—C2B—B11B—B7B | 110.09 (16) |
C1A—C2A—B11A—B6A | 38.44 (12) | C1B—C2B—B11B—B7B | −103.68 (14) |
B7A—C2A—B11A—B6A | 142.26 (13) | B6B—C2B—B11B—B7B | −142.82 (14) |
B3A—C2A—B11A—B6A | 106.28 (13) | B3B—C2B—B11B—B7B | −36.51 (14) |
B6A—B10A—B11A—C2A | 39.80 (12) | C1B—B6B—B11B—C2B | −35.27 (11) |
B5A—B10A—B11A—C2A | 1.51 (17) | B10B—B6B—B11B—C2B | −133.80 (15) |
B9A—B10A—B11A—C2A | −61.41 (16) | B5B—B6B—B11B—C2B | −95.77 (14) |
B12A—B10A—B11A—C2A | −98.33 (14) | C2B—B6B—B11B—B12B | 96.24 (16) |
B6A—B10A—B11A—B12A | 138.12 (14) | C1B—B6B—B11B—B12B | 60.98 (17) |
B5A—B10A—B11A—B12A | 99.84 (15) | B10B—B6B—B11B—B12B | −37.55 (14) |
B9A—B10A—B11A—B12A | 36.92 (13) | B5B—B6B—B11B—B12B | 0.47 (19) |
B6A—B10A—B11A—B7A | 100.86 (14) | C2B—B6B—B11B—B10B | 133.80 (15) |
B5A—B10A—B11A—B7A | 62.57 (16) | C1B—B6B—B11B—B10B | 98.53 (14) |
B9A—B10A—B11A—B7A | −0.35 (17) | B5B—B6B—B11B—B10B | 38.03 (14) |
B12A—B10A—B11A—B7A | −37.26 (13) | C2B—B6B—B11B—B7B | 32.76 (13) |
B5A—B10A—B11A—B6A | −38.29 (13) | C1B—B6B—B11B—B7B | −2.51 (18) |
B9A—B10A—B11A—B6A | −101.21 (14) | B10B—B6B—B11B—B7B | −101.04 (16) |
B12A—B10A—B11A—B6A | −138.12 (14) | B5B—B6B—B11B—B7B | −63.01 (17) |
B12A—B7A—B11A—C2A | 134.08 (13) | B5B—B10B—B11B—C2B | 1.89 (19) |
B8A—B7A—B11A—C2A | 96.28 (14) | B6B—B10B—B11B—C2B | 39.93 (12) |
B3A—B7A—B11A—C2A | 32.92 (11) | B9B—B10B—B11B—C2B | −61.27 (18) |
C2A—B7A—B11A—B12A | −134.08 (13) | B12B—B10B—B11B—C2B | −98.33 (16) |
B8A—B7A—B11A—B12A | −37.80 (13) | B5B—B10B—B11B—B12B | 100.21 (16) |
B3A—B7A—B11A—B12A | −101.16 (14) | B6B—B10B—B11B—B12B | 138.26 (15) |
C2A—B7A—B11A—B10A | −96.39 (13) | B9B—B10B—B11B—B12B | 37.05 (15) |
B12A—B7A—B11A—B10A | 37.69 (13) | B5B—B10B—B11B—B6B | −38.05 (14) |
B8A—B7A—B11A—B10A | −0.11 (17) | B9B—B10B—B11B—B6B | −101.21 (16) |
B3A—B7A—B11A—B10A | −63.47 (16) | B12B—B10B—B11B—B6B | −138.26 (15) |
C2A—B7A—B11A—B6A | −33.60 (11) | B5B—B10B—B11B—B7B | 62.84 (18) |
B12A—B7A—B11A—B6A | 100.48 (14) | B6B—B10B—B11B—B7B | 100.89 (15) |
B8A—B7A—B11A—B6A | 62.68 (16) | B9B—B10B—B11B—B7B | −0.3 (2) |
B3A—B7A—B11A—B6A | −0.68 (17) | B12B—B10B—B11B—B7B | −37.37 (14) |
C1A—B6A—B11A—C2A | −35.02 (11) | B8B—B7B—B11B—C2B | 96.67 (15) |
B10A—B6A—B11A—C2A | −133.86 (14) | B3B—B7B—B11B—C2B | 33.99 (12) |
B5A—B6A—B11A—C2A | −95.56 (13) | B12B—B7B—B11B—C2B | 134.08 (15) |
C2A—B6A—B11A—B12A | 96.24 (14) | C2B—B7B—B11B—B12B | −134.08 (15) |
C1A—B6A—B11A—B12A | 61.22 (15) | B8B—B7B—B11B—B12B | −37.41 (14) |
B10A—B6A—B11A—B12A | −37.63 (13) | B3B—B7B—B11B—B12B | −100.09 (16) |
B5A—B6A—B11A—B12A | 0.68 (17) | C2B—B7B—B11B—B6B | −33.15 (13) |
C2A—B6A—B11A—B10A | 133.86 (14) | B8B—B7B—B11B—B6B | 63.52 (18) |
C1A—B6A—B11A—B10A | 98.85 (13) | B3B—B7B—B11B—B6B | 0.84 (19) |
B5A—B6A—B11A—B10A | 38.30 (13) | B12B—B7B—B11B—B6B | 100.93 (16) |
C2A—B6A—B11A—B7A | 33.30 (11) | C2B—B7B—B11B—B10B | −96.51 (15) |
C1A—B6A—B11A—B7A | −1.72 (16) | B8B—B7B—B11B—B10B | 0.16 (19) |
B10A—B6A—B11A—B7A | −100.57 (15) | B3B—B7B—B11B—B10B | −62.52 (18) |
B5A—B6A—B11A—B7A | −62.26 (16) | B12B—B7B—B11B—B10B | 37.57 (14) |
C2A—B7A—B12A—B11A | 39.34 (12) | C2B—B11B—B12B—B9B | 61.86 (18) |
B8A—B7A—B12A—B11A | 138.31 (14) | B6B—B11B—B12B—B9B | 0.0 (2) |
B3A—B7A—B12A—B11A | 101.27 (14) | B10B—B11B—B12B—B9B | −37.32 (14) |
C2A—B7A—B12A—B9A | −61.70 (17) | B7B—B11B—B12B—B9B | 100.96 (17) |
B8A—B7A—B12A—B9A | 37.27 (13) | C2B—B11B—B12B—B7B | −39.10 (13) |
B3A—B7A—B12A—B9A | 0.23 (18) | B6B—B11B—B12B—B7B | −100.98 (16) |
B11A—B7A—B12A—B9A | −101.04 (15) | B10B—B11B—B12B—B7B | −138.28 (16) |
C2A—B7A—B12A—B8A | −98.98 (14) | C2B—B11B—B12B—B8B | −1.76 (19) |
B3A—B7A—B12A—B8A | −37.05 (12) | B6B—B11B—B12B—B8B | −63.65 (19) |
B11A—B7A—B12A—B8A | −138.31 (14) | B10B—B11B—B12B—B8B | −100.94 (17) |
C2A—B7A—B12A—B10A | 1.83 (18) | B7B—B11B—B12B—B8B | 37.33 (14) |
B8A—B7A—B12A—B10A | 100.81 (15) | C2B—B11B—B12B—B10B | 99.18 (14) |
B3A—B7A—B12A—B10A | 63.76 (17) | B6B—B11B—B12B—B10B | 37.29 (14) |
B11A—B7A—B12A—B10A | −37.51 (13) | B7B—B11B—B12B—B10B | 138.28 (16) |
C2A—B11A—B12A—B7A | −39.17 (12) | B5B—B9B—B12B—B11B | −0.4 (2) |
B10A—B11A—B12A—B7A | −138.08 (14) | B4B—B9B—B12B—B11B | −63.92 (19) |
B6A—B11A—B12A—B7A | −100.95 (14) | B10B—B9B—B12B—B11B | 37.29 (14) |
C2A—B11A—B12A—B9A | 61.62 (16) | B8B—B9B—B12B—B11B | −101.12 (16) |
B10A—B11A—B12A—B9A | −37.29 (13) | B5B—B9B—B12B—B7B | 63.51 (19) |
B7A—B11A—B12A—B9A | 100.78 (15) | B4B—B9B—B12B—B7B | 0.0 (2) |
B6A—B11A—B12A—B9A | −0.17 (18) | B10B—B9B—B12B—B7B | 101.24 (16) |
C2A—B11A—B12A—B8A | −1.95 (17) | B8B—B9B—B12B—B7B | −37.17 (15) |
B10A—B11A—B12A—B8A | −100.86 (15) | B5B—B9B—B12B—B8B | 100.68 (16) |
B7A—B11A—B12A—B8A | 37.22 (13) | B4B—B9B—B12B—B8B | 37.19 (14) |
B6A—B11A—B12A—B8A | −63.73 (16) | B10B—B9B—B12B—B8B | 138.41 (15) |
C2A—B11A—B12A—B10A | 98.91 (14) | B5B—B9B—B12B—B10B | −37.73 (14) |
B7A—B11A—B12A—B10A | 138.08 (14) | B4B—B9B—B12B—B10B | −101.22 (16) |
B6A—B11A—B12A—B10A | 37.12 (13) | B8B—B9B—B12B—B10B | −138.41 (15) |
B5A—B9A—B12A—B7A | 63.54 (17) | C2B—B7B—B12B—B11B | 39.43 (13) |
B4A—B9A—B12A—B7A | 0.16 (18) | B8B—B7B—B12B—B11B | 138.25 (15) |
B8A—B9A—B12A—B7A | −37.13 (13) | B3B—B7B—B12B—B11B | 101.73 (15) |
B10A—B9A—B12A—B7A | 101.18 (14) | C2B—B7B—B12B—B9B | −61.55 (19) |
B5A—B9A—B12A—B11A | −0.41 (18) | B8B—B7B—B12B—B9B | 37.28 (15) |
B4A—B9A—B12A—B11A | −63.78 (17) | B3B—B7B—B12B—B9B | 0.8 (2) |
B8A—B9A—B12A—B11A | −101.08 (15) | B11B—B7B—B12B—B9B | −100.98 (17) |
B10A—B9A—B12A—B11A | 37.23 (13) | C2B—B7B—B12B—B8B | −98.83 (16) |
B5A—B9A—B12A—B8A | 100.67 (14) | B3B—B7B—B12B—B8B | −36.52 (14) |
B4A—B9A—B12A—B8A | 37.30 (12) | B11B—B7B—B12B—B8B | −138.25 (15) |
B10A—B9A—B12A—B8A | 138.32 (13) | C2B—B7B—B12B—B10B | 2.0 (2) |
B5A—B9A—B12A—B10A | −37.64 (13) | B8B—B7B—B12B—B10B | 100.86 (17) |
B4A—B9A—B12A—B10A | −101.02 (14) | B3B—B7B—B12B—B10B | 64.33 (19) |
B8A—B9A—B12A—B10A | −138.32 (13) | B11B—B7B—B12B—B10B | −37.40 (14) |
B3A—B8A—B12A—B7A | 37.28 (12) | B3B—B8B—B12B—B11B | −0.4 (2) |
B4A—B8A—B12A—B7A | 101.15 (14) | B4B—B8B—B12B—B11B | 63.43 (18) |
B9A—B8A—B12A—B7A | 138.32 (13) | B7B—B8B—B12B—B11B | −37.59 (14) |
B3A—B8A—B12A—B11A | −0.27 (18) | B9B—B8B—B12B—B11B | 100.80 (16) |
B7A—B8A—B12A—B11A | −37.54 (13) | B3B—B8B—B12B—B9B | −101.15 (16) |
B4A—B8A—B12A—B11A | 63.61 (16) | B4B—B8B—B12B—B9B | −37.37 (14) |
B9A—B8A—B12A—B11A | 100.77 (14) | B7B—B8B—B12B—B9B | −138.39 (15) |
B3A—B8A—B12A—B9A | −101.04 (14) | B3B—B8B—B12B—B7B | 37.24 (14) |
B7A—B8A—B12A—B9A | −138.32 (13) | B4B—B8B—B12B—B7B | 101.02 (15) |
B4A—B8A—B12A—B9A | −37.17 (12) | B9B—B8B—B12B—B7B | 138.39 (15) |
B3A—B8A—B12A—B10A | −63.70 (16) | B3B—B8B—B12B—B10B | −63.88 (19) |
B7A—B8A—B12A—B10A | −100.98 (14) | B4B—B8B—B12B—B10B | −0.10 (19) |
B4A—B8A—B12A—B10A | 0.17 (17) | B7B—B8B—B12B—B10B | −101.12 (16) |
B9A—B8A—B12A—B10A | 37.34 (12) | B9B—B8B—B12B—B10B | 37.27 (14) |
B6A—B10A—B12A—B7A | 0.09 (19) | B5B—B10B—B12B—B11B | −100.54 (15) |
B5A—B10A—B12A—B7A | −63.30 (17) | B6B—B10B—B12B—B11B | −37.21 (14) |
B11A—B10A—B12A—B7A | 37.75 (13) | B9B—B10B—B12B—B11B | −138.31 (15) |
B9A—B10A—B12A—B7A | −100.59 (15) | B5B—B10B—B12B—B9B | 37.78 (14) |
B6A—B10A—B12A—B11A | −37.66 (13) | B6B—B10B—B12B—B9B | 101.10 (16) |
B5A—B10A—B12A—B11A | −101.05 (14) | B11B—B10B—B12B—B9B | 138.31 (15) |
B9A—B10A—B12A—B11A | −138.34 (14) | B5B—B10B—B12B—B7B | −62.94 (19) |
B6A—B10A—B12A—B9A | 100.68 (14) | B6B—B10B—B12B—B7B | 0.4 (2) |
B5A—B10A—B12A—B9A | 37.29 (12) | B11B—B10B—B12B—B7B | 37.60 (15) |
B11A—B10A—B12A—B9A | 138.34 (14) | B9B—B10B—B12B—B7B | −100.72 (17) |
B6A—B10A—B12A—B8A | 63.34 (16) | B5B—B10B—B12B—B8B | 0.48 (19) |
B5A—B10A—B12A—B8A | −0.05 (17) | B6B—B10B—B12B—B8B | 63.80 (18) |
B11A—B10A—B12A—B8A | 101.00 (14) | B11B—B10B—B12B—B8B | 101.02 (16) |
B9A—B10A—B12A—B8A | −37.34 (12) | B9B—B10B—B12B—B8B | −37.30 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O3A | 0.95 (3) | 1.70 (3) | 2.6473 (17) | 174 (2) |
O1A—H1A···O2Ai | 0.96 (2) | 1.71 (2) | 2.6707 (17) | 175 (2) |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C5H16B10O3 |
Mr | 232.28 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 160 |
a, b, c (Å) | 22.746 (2), 9.699 (1), 23.439 (3) |
β (°) | 102.296 (10) |
V (Å3) | 5052.1 (10) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5399, 4418, 3670 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.129, 1.03 |
No. of reflections | 4418 |
No. of parameters | 334 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.30 |
Selected geometric parameters (Å, º) topC1A—C4A | 1.535 (2) | C1B—C4B | 1.517 (2) |
C2A—C3A | 1.516 (2) | C2B—C3B | 1.526 (2) |
C4A—O3A | 1.411 (2) | C4B—O3B | 1.404 (2) |
O3A—C5A | 1.443 (2) | O3B—C5B | 1.428 (2) |
| | | |
C1A—C2A—C3A | 120.98 (12) | C1B—C2B—C3B | 119.73 (14) |
C2A—C1A—C4A | 121.82 (12) | C2B—C1B—C4B | 119.28 (14) |
C1A—C4A—O3A | 113.90 (13) | C1B—C4B—O3B | 109.44 (14) |
C2A—C3A—O1A | 114.77 (14) | C2B—C3B—O1B | 112.29 (14) |
C2A—C3A—O2A | 119.79 (14) | C2B—C3B—O2B | 121.40 (16) |
O1A—C3A—O2A | 125.42 (15) | O1B—C3B—O2B | 126.26 (16) |
C4A—O3A—C5A | 115.22 (13) | C4B—O3B—C5B | 111.58 (15) |
| | | |
C4A—C1A—C2A—C3A | 3.9 (2) | C4B—C1B—C2B—C3B | −1.1 (2) |
C1A—C2A—C3A—O1A | 164.45 (13) | C1B—C2B—C3B—O1B | 53.25 (19) |
C1A—C2A—C3A—O2A | −17.1 (2) | C1B—C2B—C3B—O2B | −129.22 (18) |
C2A—C1A—C4A—O3A | −69.56 (18) | C2B—C1B—C4B—O3B | 55.16 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O3A | 0.95 (3) | 1.70 (3) | 2.6473 (17) | 174 (2) |
O1A—H1A···O2Ai | 0.96 (2) | 1.71 (2) | 2.6707 (17) | 175 (2) |
Symmetry code: (i) −x, −y+1, −z. |
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 C═O 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.