The title compound, 1,2-(COOH)2-1,2-closo-C2B10H10·0.5C2H6O or C4H12B10O4·0.5C2H6O, forms a tetramer by incorporating ethanol (solvent) molecules through hydrogen bonding. Two eight-membered rings [graph set R22(8)] are formed by hydrogen bonding between two carboxylic acid groups, whereas two ten-membered rings [R33(10)] are formed by hydrogen bonding between two carboxylic acid groups and the OH group of an ethanol molecule (solvent). Two crystallographically independent tetramers are present in the crystal structure.
Supporting information
CCDC reference: 224654
Compound (I) was prepared according to a local variation of the literature method of Heying et al. (1963) in 85% yield, and crystals were grown by evaporation of an ethanol solution. Analysis calculated for C4H12B10O4: C 20.68, H 5.22%; found: C 19.33, H 5.64%. 11B{1H} FT–NMR (128.4 MHz): δ (p.p.m.) −0.11 (2B), −6.49 (2B), −8.05 (3B), −8.90 (2B), −10.53 (1B). The carboxylic acid H atoms were not observed in the 1H NMR spectrum due to fast intermolecular exchange. NMR spectra were recorded from a CD3CN solution at 293 K on a Bruker DPX400 spectrometer.
Methyl atom C12 of one of the solvent molecules is disordered. Two positions were located (C12A/C12B) and their distances to the more ordered adjacent C atom (C11) was restrained to 1.45 (5) Å. The carboxylic acid H atoms and the hydroxy H atoms of the solvent molecules were located from a difference Fourier map. Their Uisovalues were allowed to refine freely in subsequent refinement cycles. The positions of the cage H atoms and the ethyl H atoms of the solvent molecules were calculated using appropriate HFIX options in SHELXL97 (Sheldrick, 1997).
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
1,2-Dicarboxy-1,2-dicarba-
closo-dodecaborane(12)
top
Crystal data top
C4H12B10O4·0.5C2H6O | Z = 8 |
Mr = 255.27 | F(000) = 1048 |
Triclinic, P1 | Dx = 1.250 Mg m−3 |
a = 12.133 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 12.658 (5) Å | Cell parameters from 40 reflections |
c = 19.104 (5) Å | θ = 9.2–24.9° |
α = 76.390 (5)° | µ = 0.08 mm−1 |
β = 73.260 (5)° | T = 160 K |
γ = 76.620 (5)° | Multifaceted block, colourless |
V = 2688.2 (17) Å3 | 0.5 × 0.5 × 0.5 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.079 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.9° |
Graphite monochromator | h = −14→1 |
ω scans | k = −14→14 |
10856 measured reflections | l = −22→22 |
9408 independent reflections | 3 standard reflections every 97 reflections |
7890 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0661P)2 + 1.6557P] where P = (Fo2 + 2Fc2)/3 |
9408 reflections | (Δ/σ)max = 0.001 |
755 parameters | Δρmax = 0.55 e Å−3 |
2 restraints | Δρmin = −0.47 e Å−3 |
Crystal data top
C4H12B10O4·0.5C2H6O | γ = 76.620 (5)° |
Mr = 255.27 | V = 2688.2 (17) Å3 |
Triclinic, P1 | Z = 8 |
a = 12.133 (5) Å | Mo Kα radiation |
b = 12.658 (5) Å | µ = 0.08 mm−1 |
c = 19.104 (5) Å | T = 160 K |
α = 76.390 (5)° | 0.5 × 0.5 × 0.5 mm |
β = 73.260 (5)° | |
Data collection top
Bruker P4 diffractometer | Rint = 0.079 |
10856 measured reflections | 3 standard reflections every 97 reflections |
9408 independent reflections | intensity decay: none |
7890 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 2 restraints |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.55 e Å−3 |
9408 reflections | Δρmin = −0.47 e Å−3 |
755 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 | Occ. (<1) |
C1A | 0.87949 (16) | 0.41445 (15) | 0.16410 (10) | 0.0216 (4) | |
C3A | 0.84565 (16) | 0.35642 (15) | 0.11406 (10) | 0.0231 (4) | |
O1A | 0.77804 (14) | 0.28518 (13) | 0.15099 (8) | 0.0355 (4) | |
O2A | 0.88703 (12) | 0.37187 (11) | 0.04748 (7) | 0.0279 (3) | |
H1A | 0.764 (3) | 0.249 (3) | 0.1220 (18) | 0.064 (9)* | |
C2A | 0.80143 (16) | 0.53257 (15) | 0.18640 (10) | 0.0235 (4) | |
C4A | 0.69417 (17) | 0.57576 (17) | 0.15617 (11) | 0.0277 (4) | |
O3A | 0.63971 (14) | 0.67026 (13) | 0.17529 (10) | 0.0417 (4) | |
O4A | 0.66511 (13) | 0.52483 (14) | 0.12057 (9) | 0.0402 (4) | |
H2A | 0.572 (3) | 0.695 (3) | 0.1586 (18) | 0.071 (10)* | |
B3A | 0.7940 (2) | 0.41434 (19) | 0.25444 (12) | 0.0262 (5) | |
H3A | 0.7166 | 0.3747 | 0.2794 | 0.031* | |
B4A | 0.9392 (2) | 0.33693 (18) | 0.23435 (12) | 0.0264 (5) | |
H4A | 0.9554 | 0.2461 | 0.2471 | 0.032* | |
B5A | 1.02513 (19) | 0.41123 (18) | 0.15309 (13) | 0.0262 (5) | |
H5A | 1.0965 | 0.3680 | 0.1139 | 0.031* | |
B6A | 0.93440 (19) | 0.53490 (18) | 0.12099 (13) | 0.0253 (4) | |
H6A | 0.9454 | 0.5713 | 0.0617 | 0.030* | |
B7A | 0.8935 (2) | 0.4196 (2) | 0.30508 (13) | 0.0313 (5) | |
H7A | 0.8809 | 0.3825 | 0.3644 | 0.038* | |
B8A | 1.0361 (2) | 0.41717 (19) | 0.24279 (14) | 0.0301 (5) | |
H8A | 1.1158 | 0.3783 | 0.2620 | 0.036* | |
B9A | 1.0324 (2) | 0.53934 (19) | 0.17301 (14) | 0.0295 (5) | |
H9A | 1.1093 | 0.5797 | 0.1471 | 0.035* | |
B10A | 0.8883 (2) | 0.61715 (19) | 0.19235 (14) | 0.0287 (5) | |
H10A | 0.8705 | 0.7079 | 0.1787 | 0.034* | |
B11A | 0.8025 (2) | 0.5435 (2) | 0.27361 (13) | 0.0296 (5) | |
H11A | 0.7297 | 0.5872 | 0.3118 | 0.036* | |
B12A | 0.9515 (2) | 0.5442 (2) | 0.26719 (14) | 0.0312 (5) | |
H12A | 0.9763 | 0.5876 | 0.3023 | 0.037* | |
C1B | 0.80491 (16) | 0.08637 (16) | 0.95305 (10) | 0.0225 (4) | |
C3B | 0.81270 (16) | 0.17023 (16) | 0.99653 (10) | 0.0230 (4) | |
O1B | 0.89922 (12) | 0.22306 (12) | 0.96455 (8) | 0.0277 (3) | |
O2B | 0.74654 (13) | 0.17742 (13) | 1.05716 (8) | 0.0356 (4) | |
H2B | 0.626 (3) | 0.368 (3) | 0.9106 (19) | 0.074 (10)* | |
C2B | 0.71410 (16) | 0.11886 (16) | 0.89773 (10) | 0.0220 (4) | |
C4B | 0.64110 (17) | 0.23362 (17) | 0.88956 (11) | 0.0274 (4) | |
O3B | 0.67653 (14) | 0.30401 (13) | 0.91270 (10) | 0.0414 (4) | |
O4B | 0.55901 (15) | 0.25055 (15) | 0.86251 (11) | 0.0489 (5) | |
H1B | 0.894 (3) | 0.271 (3) | 0.9951 (17) | 0.058 (8)* | |
B3B | 0.86340 (18) | 0.10745 (19) | 0.85806 (12) | 0.0237 (4) | |
H3B | 0.9083 | 0.1764 | 0.8259 | 0.028* | |
B4B | 0.9266 (2) | −0.00301 (19) | 0.91993 (14) | 0.0298 (5) | |
H4B | 1.0141 | −0.0061 | 0.9272 | 0.036* | |
B5B | 0.8120 (2) | −0.04820 (19) | 0.99628 (14) | 0.0331 (5) | |
H5B | 0.8257 | −0.0800 | 1.0524 | 0.040* | |
B6B | 0.6759 (2) | 0.0331 (2) | 0.98241 (12) | 0.0288 (5) | |
H6B | 0.6021 | 0.0552 | 1.0289 | 0.035* | |
B7B | 0.76969 (19) | 0.05344 (19) | 0.82298 (12) | 0.0253 (5) | |
H7B | 0.7549 | 0.0875 | 0.7673 | 0.030* | |
B8B | 0.9052 (2) | −0.0274 (2) | 0.83689 (14) | 0.0308 (5) | |
H8B | 0.9790 | −0.0470 | 0.7898 | 0.037* | |
B9B | 0.8739 (2) | −0.1234 (2) | 0.92234 (15) | 0.0369 (6) | |
H9B | 0.9280 | −0.2058 | 0.9306 | 0.044* | |
B10B | 0.7183 (2) | −0.1013 (2) | 0.96112 (14) | 0.0367 (6) | |
H10B | 0.6716 | −0.1685 | 0.9943 | 0.044* | |
B11B | 0.6554 (2) | 0.0075 (2) | 0.89939 (13) | 0.0288 (5) | |
H11B | 0.5674 | 0.0119 | 0.8924 | 0.035* | |
B12B | 0.7773 (2) | −0.0895 (2) | 0.86255 (14) | 0.0321 (5) | |
H12B | 0.7690 | −0.1498 | 0.8321 | 0.039* | |
C2C | 0.70912 (16) | 0.39817 (15) | 0.57034 (10) | 0.0218 (4) | |
C4C | 0.73714 (17) | 0.30225 (16) | 0.53003 (11) | 0.0264 (4) | |
O3C | 0.65715 (14) | 0.30716 (14) | 0.49585 (9) | 0.0391 (4) | |
O4C | 0.82445 (13) | 0.23312 (13) | 0.53090 (9) | 0.0382 (4) | |
H2C | 0.673 (3) | 0.257 (3) | 0.4698 (17) | 0.055 (8)* | |
C1C | 0.80456 (15) | 0.40454 (15) | 0.61521 (10) | 0.0195 (4) | |
C3C | 0.91227 (16) | 0.31531 (15) | 0.61973 (10) | 0.0211 (4) | |
O1C | 1.00300 (12) | 0.33207 (12) | 0.56445 (8) | 0.0282 (3) | |
O2C | 0.91133 (11) | 0.24312 (11) | 0.67419 (8) | 0.0287 (3) | |
H1C | 1.060 (3) | 0.283 (3) | 0.580 (2) | 0.095 (13)* | |
B3C | 0.67198 (18) | 0.36717 (18) | 0.66678 (12) | 0.0226 (4) | |
H3C | 0.6606 | 0.2851 | 0.7002 | 0.027* | |
B4C | 0.73675 (18) | 0.45991 (18) | 0.69335 (12) | 0.0232 (4) | |
H4C | 0.7666 | 0.4376 | 0.7450 | 0.028* | |
B5C | 0.81527 (19) | 0.53836 (17) | 0.61105 (12) | 0.0229 (4) | |
H5C | 0.8954 | 0.5660 | 0.6099 | 0.027* | |
B6C | 0.79984 (19) | 0.49602 (17) | 0.53189 (12) | 0.0227 (4) | |
H6C | 0.8693 | 0.4953 | 0.4801 | 0.027* | |
B7C | 0.58603 (19) | 0.49152 (19) | 0.69324 (12) | 0.0268 (5) | |
H7C | 0.5168 | 0.4906 | 0.7452 | 0.032* | |
B8C | 0.6741 (2) | 0.59699 (18) | 0.65947 (13) | 0.0265 (5) | |
H8C | 0.6619 | 0.6645 | 0.6897 | 0.032* | |
B9C | 0.7126 (2) | 0.61884 (18) | 0.56019 (12) | 0.0262 (5) | |
H9C | 0.7254 | 0.7002 | 0.5261 | 0.031* | |
B10C | 0.64781 (19) | 0.52730 (18) | 0.53279 (12) | 0.0261 (5) | |
H10C | 0.6191 | 0.5478 | 0.4808 | 0.031* | |
B11C | 0.56992 (19) | 0.44873 (19) | 0.61512 (13) | 0.0263 (5) | |
H11C | 0.4913 | 0.4189 | 0.6158 | 0.032* | |
B12C | 0.57042 (19) | 0.59045 (19) | 0.61114 (13) | 0.0274 (5) | |
H12C | 0.4913 | 0.6536 | 0.6100 | 0.033* | |
C1D | 0.69332 (16) | 0.92239 (15) | 0.32174 (10) | 0.0203 (4) | |
C3D | 0.80831 (16) | 0.85873 (15) | 0.33856 (10) | 0.0230 (4) | |
O1D | 0.89437 (12) | 0.85515 (12) | 0.27919 (8) | 0.0296 (3) | |
O2D | 0.81398 (13) | 0.81450 (14) | 0.40108 (8) | 0.0416 (4) | |
H1D | 0.956 (3) | 0.825 (2) | 0.2946 (15) | 0.049 (8)* | |
C2D | 0.64399 (16) | 1.04748 (15) | 0.34206 (10) | 0.0210 (4) | |
C4D | 0.71751 (18) | 1.09404 (16) | 0.37530 (11) | 0.0280 (4) | |
O3D | 0.82782 (14) | 1.05801 (15) | 0.35447 (10) | 0.0456 (4) | |
O4D | 0.67091 (15) | 1.15799 (15) | 0.41703 (11) | 0.0536 (5) | |
H2D | 0.875 (3) | 1.089 (3) | 0.379 (2) | 0.093 (12)* | |
B3D | 0.69782 (18) | 1.03334 (17) | 0.24879 (11) | 0.0219 (4) | |
H3D | 0.7780 | 1.0601 | 0.2113 | 0.026* | |
B4D | 0.6541 (2) | 0.90980 (19) | 0.24563 (12) | 0.0262 (5) | |
H4D | 0.7061 | 0.8567 | 0.2053 | 0.031* | |
B5D | 0.5814 (2) | 0.85298 (19) | 0.33786 (13) | 0.0289 (5) | |
H5D | 0.5875 | 0.7632 | 0.3567 | 0.035* | |
B6D | 0.57736 (19) | 0.94011 (19) | 0.39952 (12) | 0.0262 (5) | |
H6D | 0.5814 | 0.9078 | 0.4576 | 0.031* | |
B7D | 0.56853 (19) | 1.12896 (18) | 0.28022 (12) | 0.0240 (4) | |
H7D | 0.5655 | 1.2186 | 0.2625 | 0.029* | |
B8D | 0.57080 (19) | 1.04132 (19) | 0.21890 (12) | 0.0268 (5) | |
H8D | 0.5678 | 1.0743 | 0.1607 | 0.032* | |
B9D | 0.4986 (2) | 0.9295 (2) | 0.27327 (14) | 0.0317 (5) | |
H9E | 0.4488 | 0.8897 | 0.2502 | 0.038* | |
B10D | 0.4521 (2) | 0.9483 (2) | 0.36797 (13) | 0.0315 (5) | |
H9D | 0.3728 | 0.9208 | 0.4061 | 0.038* | |
B11D | 0.49473 (19) | 1.07169 (19) | 0.37151 (12) | 0.0270 (5) | |
H10D | 0.4439 | 1.1248 | 0.4120 | 0.032* | |
B12D | 0.44594 (19) | 1.0648 (2) | 0.29399 (12) | 0.0274 (5) | |
H11D | 0.3621 | 1.1129 | 0.2841 | 0.033* | |
C11 | 0.5838 (6) | 0.5891 (3) | 0.8793 (3) | 0.124 (2) | |
H11H | 0.6299 | 0.5896 | 0.8285 | 0.148* | |
H11J | 0.5148 | 0.6456 | 0.8776 | 0.148* | |
C12A | 0.6407 (10) | 0.6175 (10) | 0.9126 (6) | 0.097 (4) | 0.488 (14) |
H12H | 0.7224 | 0.5914 | 0.8934 | 0.146* | 0.488 (14) |
H12I | 0.6181 | 0.5868 | 0.9645 | 0.146* | 0.488 (14) |
H12J | 0.6265 | 0.6966 | 0.9061 | 0.146* | 0.488 (14) |
C12B | 0.5523 (12) | 0.6748 (6) | 0.9092 (6) | 0.105 (5) | 0.512 (14) |
H12K | 0.5827 | 0.6613 | 0.9522 | 0.157* | 0.512 (14) |
H12L | 0.4685 | 0.6918 | 0.9236 | 0.157* | 0.512 (14) |
H12M | 0.5820 | 0.7359 | 0.8742 | 0.157* | 0.512 (14) |
H1S | 0.479 (3) | 0.486 (3) | 0.895 (2) | 0.093 (13)* | |
O1S | 0.54634 (17) | 0.48661 (14) | 0.90531 (12) | 0.0510 (5) | |
C21 | 0.0736 (2) | 0.1041 (3) | 0.39122 (18) | 0.0642 (8) | |
H21B | 0.0890 | 0.1480 | 0.3416 | 0.077* | |
H21A | 0.1081 | 0.0280 | 0.3870 | 0.077* | |
C22 | 0.1303 (3) | 0.1400 (4) | 0.4351 (2) | 0.0775 (11) | |
H22A | 0.2127 | 0.1320 | 0.4124 | 0.116* | |
H22C | 0.1174 | 0.0959 | 0.4841 | 0.116* | |
H22B | 0.0989 | 0.2161 | 0.4383 | 0.116* | |
O2S | −0.04894 (16) | 0.1112 (2) | 0.41903 (14) | 0.0657 (7) | |
H2S | −0.076 (3) | 0.143 (3) | 0.449 (2) | 0.070 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0208 (9) | 0.0197 (9) | 0.0227 (9) | −0.0001 (7) | −0.0041 (7) | −0.0060 (7) |
C3A | 0.0220 (9) | 0.0234 (9) | 0.0240 (10) | −0.0014 (7) | −0.0059 (7) | −0.0065 (7) |
O1A | 0.0460 (9) | 0.0419 (9) | 0.0250 (7) | −0.0245 (7) | −0.0026 (6) | −0.0094 (7) |
O2A | 0.0335 (7) | 0.0295 (7) | 0.0215 (7) | −0.0080 (6) | −0.0037 (6) | −0.0073 (6) |
C2A | 0.0217 (9) | 0.0222 (9) | 0.0261 (10) | 0.0014 (7) | −0.0064 (8) | −0.0080 (7) |
C4A | 0.0227 (9) | 0.0289 (10) | 0.0301 (10) | 0.0005 (8) | −0.0075 (8) | −0.0064 (8) |
O3A | 0.0329 (8) | 0.0315 (8) | 0.0689 (11) | 0.0099 (7) | −0.0280 (8) | −0.0209 (8) |
O4A | 0.0334 (8) | 0.0481 (9) | 0.0456 (9) | 0.0089 (7) | −0.0196 (7) | −0.0247 (8) |
B3A | 0.0289 (11) | 0.0286 (12) | 0.0189 (10) | −0.0024 (9) | −0.0038 (8) | −0.0055 (9) |
B4A | 0.0306 (12) | 0.0227 (11) | 0.0264 (11) | 0.0014 (9) | −0.0118 (9) | −0.0055 (9) |
B5A | 0.0222 (11) | 0.0248 (11) | 0.0326 (12) | 0.0003 (8) | −0.0076 (9) | −0.0102 (9) |
B6A | 0.0235 (11) | 0.0236 (11) | 0.0286 (11) | −0.0044 (8) | −0.0051 (9) | −0.0059 (9) |
B7A | 0.0363 (13) | 0.0332 (13) | 0.0264 (11) | −0.0002 (10) | −0.0121 (10) | −0.0095 (10) |
B8A | 0.0285 (12) | 0.0281 (12) | 0.0382 (13) | 0.0036 (9) | −0.0164 (10) | −0.0125 (10) |
B9A | 0.0256 (11) | 0.0266 (12) | 0.0398 (13) | −0.0019 (9) | −0.0110 (10) | −0.0118 (10) |
B10A | 0.0281 (11) | 0.0244 (11) | 0.0373 (12) | −0.0003 (9) | −0.0122 (10) | −0.0115 (9) |
B11A | 0.0300 (12) | 0.0327 (12) | 0.0284 (12) | 0.0020 (9) | −0.0092 (9) | −0.0149 (10) |
B12A | 0.0323 (12) | 0.0303 (12) | 0.0354 (13) | 0.0025 (10) | −0.0148 (10) | −0.0145 (10) |
C1B | 0.0219 (9) | 0.0254 (10) | 0.0227 (9) | −0.0037 (7) | −0.0105 (7) | −0.0033 (7) |
C3B | 0.0235 (9) | 0.0252 (10) | 0.0223 (9) | −0.0027 (7) | −0.0106 (8) | −0.0033 (7) |
O1B | 0.0287 (7) | 0.0315 (8) | 0.0268 (7) | −0.0105 (6) | −0.0055 (6) | −0.0091 (6) |
O2B | 0.0381 (8) | 0.0473 (9) | 0.0259 (8) | −0.0190 (7) | 0.0002 (6) | −0.0141 (6) |
C2B | 0.0198 (9) | 0.0286 (10) | 0.0198 (9) | −0.0034 (7) | −0.0083 (7) | −0.0052 (7) |
C4B | 0.0228 (10) | 0.0351 (11) | 0.0230 (9) | 0.0002 (8) | −0.0064 (8) | −0.0070 (8) |
O3B | 0.0407 (9) | 0.0292 (8) | 0.0625 (11) | 0.0054 (7) | −0.0303 (8) | −0.0134 (7) |
O4B | 0.0398 (9) | 0.0487 (10) | 0.0689 (12) | 0.0142 (8) | −0.0364 (9) | −0.0239 (9) |
B3B | 0.0196 (10) | 0.0300 (11) | 0.0220 (10) | −0.0029 (8) | −0.0047 (8) | −0.0077 (9) |
B4B | 0.0295 (12) | 0.0249 (11) | 0.0399 (13) | 0.0017 (9) | −0.0180 (10) | −0.0097 (10) |
B5B | 0.0482 (15) | 0.0253 (12) | 0.0323 (12) | −0.0100 (10) | −0.0235 (11) | 0.0025 (9) |
B6B | 0.0314 (12) | 0.0379 (13) | 0.0210 (10) | −0.0165 (10) | −0.0079 (9) | −0.0008 (9) |
B7B | 0.0264 (11) | 0.0312 (12) | 0.0218 (10) | −0.0051 (9) | −0.0082 (8) | −0.0085 (9) |
B8B | 0.0283 (12) | 0.0313 (12) | 0.0370 (13) | 0.0003 (9) | −0.0119 (10) | −0.0148 (10) |
B9B | 0.0495 (15) | 0.0225 (12) | 0.0481 (15) | −0.0011 (10) | −0.0292 (12) | −0.0082 (10) |
B10B | 0.0520 (16) | 0.0332 (13) | 0.0332 (13) | −0.0181 (11) | −0.0205 (11) | 0.0010 (10) |
B11B | 0.0305 (12) | 0.0352 (12) | 0.0259 (11) | −0.0126 (10) | −0.0101 (9) | −0.0050 (9) |
B12B | 0.0396 (13) | 0.0290 (12) | 0.0352 (13) | −0.0078 (10) | −0.0174 (10) | −0.0082 (10) |
C2C | 0.0214 (9) | 0.0232 (9) | 0.0230 (9) | −0.0020 (7) | −0.0104 (7) | −0.0042 (7) |
C4C | 0.0284 (10) | 0.0262 (10) | 0.0283 (10) | −0.0038 (8) | −0.0106 (8) | −0.0084 (8) |
O3C | 0.0405 (9) | 0.0388 (9) | 0.0508 (10) | 0.0052 (7) | −0.0271 (8) | −0.0250 (8) |
O4C | 0.0374 (9) | 0.0336 (8) | 0.0517 (10) | 0.0073 (7) | −0.0217 (7) | −0.0229 (7) |
C1C | 0.0201 (9) | 0.0212 (9) | 0.0183 (8) | −0.0014 (7) | −0.0071 (7) | −0.0049 (7) |
C3C | 0.0202 (9) | 0.0218 (9) | 0.0232 (9) | −0.0013 (7) | −0.0085 (7) | −0.0063 (8) |
O1C | 0.0222 (7) | 0.0314 (8) | 0.0247 (7) | 0.0020 (6) | −0.0041 (6) | −0.0016 (6) |
O2C | 0.0239 (7) | 0.0270 (7) | 0.0296 (7) | −0.0007 (5) | −0.0079 (6) | 0.0034 (6) |
B3C | 0.0191 (10) | 0.0253 (11) | 0.0229 (10) | −0.0021 (8) | −0.0067 (8) | −0.0035 (8) |
B4C | 0.0230 (10) | 0.0265 (11) | 0.0204 (10) | −0.0002 (8) | −0.0068 (8) | −0.0069 (8) |
B5C | 0.0248 (10) | 0.0210 (10) | 0.0247 (10) | −0.0021 (8) | −0.0092 (8) | −0.0059 (8) |
B6C | 0.0254 (10) | 0.0212 (10) | 0.0213 (10) | −0.0019 (8) | −0.0086 (8) | −0.0022 (8) |
B7C | 0.0214 (10) | 0.0302 (12) | 0.0268 (11) | 0.0001 (9) | −0.0056 (8) | −0.0063 (9) |
B8C | 0.0277 (11) | 0.0242 (11) | 0.0288 (11) | 0.0012 (9) | −0.0088 (9) | −0.0105 (9) |
B9C | 0.0281 (11) | 0.0207 (11) | 0.0279 (11) | 0.0001 (9) | −0.0094 (9) | −0.0021 (9) |
B10C | 0.0262 (11) | 0.0253 (11) | 0.0271 (11) | 0.0014 (9) | −0.0121 (9) | −0.0042 (9) |
B11C | 0.0210 (10) | 0.0279 (11) | 0.0308 (11) | −0.0002 (9) | −0.0092 (9) | −0.0074 (9) |
B12C | 0.0250 (11) | 0.0259 (11) | 0.0309 (12) | 0.0038 (9) | −0.0107 (9) | −0.0076 (9) |
C1D | 0.0216 (9) | 0.0193 (9) | 0.0193 (9) | −0.0015 (7) | −0.0045 (7) | −0.0050 (7) |
C3D | 0.0227 (9) | 0.0202 (9) | 0.0248 (10) | −0.0007 (7) | −0.0072 (7) | −0.0030 (7) |
O1D | 0.0213 (7) | 0.0360 (8) | 0.0244 (7) | 0.0049 (6) | −0.0031 (6) | −0.0047 (6) |
O2D | 0.0279 (8) | 0.0545 (10) | 0.0261 (8) | 0.0086 (7) | −0.0052 (6) | 0.0068 (7) |
C2D | 0.0217 (9) | 0.0197 (9) | 0.0204 (9) | 0.0025 (7) | −0.0058 (7) | −0.0069 (7) |
C4D | 0.0332 (11) | 0.0250 (10) | 0.0287 (10) | 0.0013 (8) | −0.0145 (8) | −0.0082 (8) |
O3D | 0.0284 (8) | 0.0620 (11) | 0.0596 (11) | −0.0054 (7) | −0.0125 (7) | −0.0370 (9) |
O4D | 0.0483 (10) | 0.0538 (11) | 0.0776 (13) | 0.0164 (8) | −0.0356 (9) | −0.0478 (10) |
B3D | 0.0250 (10) | 0.0226 (10) | 0.0163 (9) | −0.0013 (8) | −0.0060 (8) | −0.0020 (8) |
B4D | 0.0277 (11) | 0.0279 (11) | 0.0256 (11) | −0.0008 (9) | −0.0088 (9) | −0.0110 (9) |
B5D | 0.0274 (11) | 0.0236 (11) | 0.0356 (12) | −0.0069 (9) | −0.0078 (9) | −0.0028 (9) |
B6D | 0.0224 (10) | 0.0285 (11) | 0.0215 (10) | −0.0005 (9) | −0.0019 (8) | −0.0010 (9) |
B7D | 0.0238 (10) | 0.0226 (11) | 0.0246 (10) | 0.0015 (8) | −0.0096 (8) | −0.0034 (8) |
B8D | 0.0263 (11) | 0.0333 (12) | 0.0217 (10) | −0.0008 (9) | −0.0098 (9) | −0.0062 (9) |
B9D | 0.0271 (12) | 0.0336 (13) | 0.0392 (13) | −0.0063 (10) | −0.0128 (10) | −0.0093 (10) |
B10D | 0.0226 (11) | 0.0339 (13) | 0.0325 (12) | −0.0031 (9) | −0.0057 (9) | 0.0012 (10) |
B11D | 0.0226 (11) | 0.0304 (12) | 0.0237 (11) | 0.0055 (9) | −0.0053 (8) | −0.0070 (9) |
B12D | 0.0210 (10) | 0.0334 (12) | 0.0268 (11) | −0.0012 (9) | −0.0079 (9) | −0.0044 (9) |
C11 | 0.236 (7) | 0.057 (2) | 0.106 (3) | −0.064 (3) | −0.063 (4) | −0.006 (2) |
C12A | 0.075 (7) | 0.092 (8) | 0.134 (8) | −0.038 (6) | −0.020 (5) | −0.021 (6) |
C12B | 0.117 (10) | 0.043 (4) | 0.133 (8) | −0.034 (5) | 0.036 (6) | −0.038 (4) |
O1S | 0.0538 (11) | 0.0297 (9) | 0.0796 (13) | 0.0035 (8) | −0.0336 (10) | −0.0186 (8) |
C21 | 0.0377 (14) | 0.096 (2) | 0.0672 (19) | −0.0103 (15) | −0.0183 (13) | −0.0242 (17) |
C22 | 0.0393 (15) | 0.124 (3) | 0.087 (2) | −0.0177 (17) | −0.0112 (15) | −0.054 (2) |
O2S | 0.0305 (9) | 0.1017 (18) | 0.0877 (16) | −0.0005 (10) | −0.0183 (10) | −0.0672 (15) |
Geometric parameters (Å, º) top
C1A—C2A | 1.651 (3) | C4C—O4C | 1.209 (2) |
C1A—C3A | 1.523 (3) | O3C—H2C | 0.85 (3) |
C1A—B4A | 1.703 (3) | C1C—B4C | 1.707 (3) |
C1A—B5A | 1.710 (3) | C1C—B5C | 1.710 (3) |
C1A—B6A | 1.735 (3) | C1C—B3C | 1.733 (3) |
C1A—B3A | 1.738 (3) | C1C—B6C | 1.741 (3) |
C3A—O1A | 1.301 (2) | O1C—H1C | 0.89 (4) |
C3A—O2A | 1.212 (2) | B3C—B7C | 1.770 (3) |
O1A—H1A | 0.87 (3) | B3C—B4C | 1.786 (3) |
C2A—C4A | 1.510 (3) | B3C—B11C | 1.791 (3) |
C2A—B11A | 1.708 (3) | B3C—H3C | 1.1000 |
C2A—B10A | 1.708 (3) | B4C—B8C | 1.775 (3) |
C2A—B6A | 1.735 (3) | B4C—B7C | 1.780 (3) |
C2A—B3A | 1.737 (3) | B4C—B5C | 1.791 (3) |
C4A—O3A | 1.304 (3) | B4C—H4C | 1.1000 |
C4A—O4A | 1.205 (3) | B5C—B8C | 1.778 (3) |
O3A—H2A | 0.93 (3) | B5C—B9C | 1.782 (3) |
B3A—B7A | 1.771 (3) | B5C—B6C | 1.789 (3) |
B3A—B4A | 1.788 (3) | B5C—H5C | 1.1000 |
B3A—B11A | 1.789 (3) | B6C—B9C | 1.770 (3) |
B3A—H3A | 1.1000 | B6C—B10C | 1.791 (3) |
B4A—B8A | 1.783 (3) | B6C—H6C | 1.1000 |
B4A—B7A | 1.787 (3) | B7C—B11C | 1.777 (3) |
B4A—B5A | 1.793 (3) | B7C—B8C | 1.788 (3) |
B4A—H4A | 1.1000 | B7C—B12C | 1.789 (3) |
B5A—B8A | 1.777 (3) | B7C—H7C | 1.1000 |
B5A—B9A | 1.777 (3) | B8C—B12C | 1.787 (3) |
B5A—B6A | 1.783 (3) | B8C—B9C | 1.787 (3) |
B5A—H5A | 1.1000 | B8C—H8C | 1.1000 |
B6A—B9A | 1.773 (3) | B9C—B10C | 1.783 (3) |
B6A—B10A | 1.793 (3) | B9C—B12C | 1.791 (3) |
B6A—H6A | 1.1000 | B9C—H9C | 1.1000 |
B7A—B11A | 1.783 (3) | B10C—B12C | 1.780 (3) |
B7A—B12A | 1.786 (4) | B10C—B11C | 1.788 (3) |
B7A—B8A | 1.793 (3) | B10C—H10C | 1.1000 |
B7A—H7A | 1.1000 | B11C—B12C | 1.779 (3) |
B8A—B12A | 1.781 (3) | B11C—H11C | 1.1000 |
B8A—B9A | 1.790 (3) | B12C—H12C | 1.1000 |
B8A—H8A | 1.1000 | C1D—C2D | 1.653 (2) |
B9A—B10A | 1.780 (3) | C1D—B5D | 1.701 (3) |
B9A—B12A | 1.792 (3) | C1D—C3D | 1.522 (3) |
B9A—H9A | 1.1000 | C1D—B4D | 1.706 (3) |
B10A—B12A | 1.779 (3) | C1D—B3D | 1.729 (3) |
B10A—B11A | 1.789 (3) | C1D—B6D | 1.745 (3) |
B10A—H10A | 1.1000 | C3D—O1D | 1.304 (2) |
B11A—B12A | 1.778 (3) | C3D—O2D | 1.208 (2) |
B11A—H11A | 1.1000 | O1D—H1D | 0.85 (3) |
B12A—H12A | 1.1000 | C2D—C4D | 1.514 (3) |
C1B—C2B | 1.660 (2) | C2D—B7D | 1.706 (3) |
C1B—C3B | 1.527 (3) | C2D—B11D | 1.711 (3) |
C1B—B4B | 1.699 (3) | C2D—B6D | 1.732 (3) |
C1B—B5B | 1.704 (3) | C2D—B3D | 1.749 (3) |
C1B—B3B | 1.728 (3) | C4D—O3D | 1.286 (3) |
C1B—B6B | 1.740 (3) | C4D—O4D | 1.201 (3) |
C3B—O1B | 1.298 (2) | O3D—H2D | 1.03 (4) |
C3B—O2B | 1.214 (2) | B3D—B8D | 1.766 (3) |
O1B—H1B | 0.91 (3) | B3D—B4D | 1.783 (3) |
C2B—C4B | 1.516 (3) | B3D—B7D | 1.791 (3) |
C2B—B7B | 1.710 (3) | B3D—H3D | 1.1000 |
C2B—B11B | 1.711 (3) | B4D—B9D | 1.780 (3) |
C2B—B6B | 1.728 (3) | B4D—B8D | 1.781 (3) |
C2B—B3B | 1.737 (3) | B4D—B5D | 1.789 (3) |
C4B—O3B | 1.283 (3) | B4D—H4D | 1.1000 |
C4B—O4B | 1.204 (2) | B5D—B6D | 1.778 (3) |
O3B—H2B | 0.90 (4) | B5D—B9D | 1.781 (3) |
B3B—B8B | 1.772 (3) | B5D—B10D | 1.783 (3) |
B3B—B4B | 1.786 (3) | B5D—H5D | 1.1000 |
B3B—B7B | 1.795 (3) | B6D—B10D | 1.763 (3) |
B3B—H3B | 1.1000 | B6D—B11D | 1.784 (3) |
B4B—B9B | 1.770 (3) | B6D—H6D | 1.1000 |
B4B—B8B | 1.784 (3) | B7D—B12D | 1.782 (3) |
B4B—B5B | 1.788 (4) | B7D—B11D | 1.782 (3) |
B4B—H4B | 1.1000 | B7D—B8D | 1.784 (3) |
B5B—B9B | 1.777 (4) | B7D—H7D | 1.1000 |
B5B—B6B | 1.787 (3) | B8D—B12D | 1.784 (3) |
B5B—B10B | 1.788 (3) | B8D—B9D | 1.791 (3) |
B5B—H5B | 1.1000 | B8D—H8D | 1.1000 |
B6B—B10B | 1.767 (4) | B9D—B12D | 1.779 (3) |
B6B—B11B | 1.786 (3) | B9D—B10D | 1.789 (3) |
B6B—H6B | 1.1000 | B9D—H9E | 1.1000 |
B7B—B8B | 1.779 (3) | B10D—B11D | 1.776 (4) |
B7B—B12B | 1.781 (3) | B10D—B12D | 1.791 (3) |
B7B—B11B | 1.789 (3) | B10D—H9D | 1.1000 |
B7B—H7B | 1.1000 | B11D—B12D | 1.772 (3) |
B8B—B9B | 1.791 (4) | B11D—H10D | 1.1000 |
B8B—B12B | 1.792 (3) | B12D—H11D | 1.1000 |
B8B—H8B | 1.1000 | C11—C12A | 1.218 (9) |
B9B—B12B | 1.780 (3) | C11—C12B | 1.274 (8) |
B9B—B10B | 1.799 (4) | C11—O1S | 1.406 (4) |
B9B—H9B | 1.1000 | C11—H11H | 0.9700 |
B10B—B11B | 1.771 (3) | C11—H11J | 0.9700 |
B10B—B12B | 1.795 (4) | C12A—H12H | 0.9600 |
B10B—H10B | 1.1000 | C12A—H12I | 0.9600 |
B11B—B12B | 1.777 (4) | C12A—H12J | 0.9600 |
B11B—H11B | 1.1000 | C12B—H12K | 0.9600 |
B12B—H12B | 1.1000 | C12B—H12L | 0.9600 |
C1C—C2C | 1.652 (2) | C12B—H12M | 0.9600 |
C1C—C3C | 1.525 (2) | O1S—H1S | 0.90 (4) |
C2C—B11C | 1.708 (3) | C21—O2S | 1.416 (3) |
C2C—B10C | 1.712 (3) | C21—C22 | 1.428 (4) |
C2C—B3C | 1.736 (3) | C21—H21B | 0.9700 |
C3C—O1C | 1.306 (2) | C21—H21A | 0.9700 |
C3C—O2C | 1.212 (2) | C22—H22A | 0.9600 |
C2C—B6C | 1.738 (3) | C22—H22C | 0.9600 |
C2C—C4C | 1.510 (3) | C22—H22B | 0.9600 |
C4C—O3C | 1.300 (2) | O2S—H2S | 0.73 (4) |
| | | |
C3A—C1A—C2A | 121.07 (15) | O4C—C4C—O3C | 127.21 (19) |
C3A—C1A—B4A | 119.05 (15) | O4C—C4C—C2C | 121.85 (17) |
C2A—C1A—B4A | 111.26 (14) | O3C—C4C—C2C | 110.94 (16) |
C3A—C1A—B5A | 117.61 (15) | C4C—O3C—H2C | 113 (2) |
C2A—C1A—B5A | 110.91 (14) | C3C—C1C—B4C | 116.25 (14) |
B4A—C1A—B5A | 63.39 (13) | C2C—C1C—B4C | 111.20 (14) |
C3A—C1A—B6A | 115.83 (15) | C3C—C1C—B5C | 118.46 (15) |
C2A—C1A—B6A | 61.57 (12) | C2C—C1C—B5C | 111.18 (14) |
B4A—C1A—B6A | 115.18 (15) | B4C—C1C—B5C | 63.19 (12) |
B5A—C1A—B6A | 62.32 (12) | C3C—C1C—B3C | 115.69 (15) |
C3A—C1A—B3A | 118.51 (16) | C2C—C1C—B3C | 61.67 (11) |
C2A—C1A—B3A | 61.59 (12) | B4C—C1C—B3C | 62.56 (12) |
B4A—C1A—B3A | 62.61 (12) | B5C—C1C—B3C | 115.12 (14) |
B5A—C1A—B3A | 115.10 (15) | C3C—C1C—B6C | 119.53 (15) |
B6A—C1A—B3A | 115.19 (15) | C2C—C1C—B6C | 61.57 (11) |
O2A—C3A—C1A | 121.00 (17) | B4C—C1C—B6C | 114.87 (14) |
O1A—C3A—C1A | 112.97 (16) | B5C—C1C—B6C | 62.43 (12) |
C3A—O1A—H1A | 112 (2) | B3C—C1C—B6C | 115.14 (14) |
C4A—C2A—C1A | 115.75 (15) | O2C—C3C—C1C | 120.21 (16) |
O2A—C3A—O1A | 125.80 (18) | O1C—C3C—C1C | 113.65 (16) |
C4A—C2A—B11A | 122.20 (16) | C3C—O1C—H1C | 102 (3) |
C1A—C2A—B11A | 111.34 (15) | C1C—B3C—C2C | 56.88 (10) |
C4A—C2A—B10A | 122.59 (16) | C1C—B3C—B7C | 103.92 (15) |
C1A—C2A—B10A | 111.34 (15) | C2C—B3C—B7C | 103.76 (14) |
B11A—C2A—B10A | 63.15 (13) | C1C—B3C—B4C | 58.03 (11) |
C4A—C2A—B6A | 115.58 (16) | C2C—B3C—B4C | 103.80 (14) |
C1A—C2A—B6A | 61.59 (11) | B7C—B3C—B4C | 60.06 (12) |
B11A—C2A—B6A | 115.27 (15) | C1C—B3C—B11C | 103.75 (15) |
B10A—C2A—B6A | 62.76 (13) | C2C—B3C—B11C | 57.92 (11) |
C4A—C2A—B3A | 115.14 (16) | B7C—B3C—B11C | 59.87 (12) |
C1A—C2A—B3A | 61.68 (11) | B4C—B3C—B11C | 107.55 (15) |
B11A—C2A—B3A | 62.56 (13) | C1C—B3C—H3C | 125.1 |
B10A—C2A—B3A | 115.06 (15) | C2C—B3C—H3C | 125.2 |
B6A—C2A—B3A | 115.29 (15) | B7C—B3C—H3C | 123.3 |
O4A—C4A—O3A | 126.73 (19) | B4C—B3C—H3C | 122.4 |
O4A—C4A—C2A | 121.93 (18) | B11C—B3C—H3C | 122.6 |
O3A—C4A—C2A | 111.32 (17) | C1C—B4C—B8C | 104.34 (14) |
C4A—O3A—H2A | 111 (2) | C1C—B4C—B7C | 104.55 (14) |
C2A—B3A—C1A | 56.73 (11) | B8C—B4C—B7C | 60.39 (12) |
C2A—B3A—B7A | 103.86 (16) | C1C—B4C—B3C | 59.41 (11) |
C1A—B3A—B7A | 103.89 (16) | B8C—B4C—B3C | 108.20 (15) |
C2A—B3A—B4A | 103.49 (15) | B7C—B4C—B3C | 59.51 (12) |
C1A—B3A—B4A | 57.72 (11) | C1C—B4C—B5C | 58.49 (11) |
B7A—B3A—B4A | 60.26 (13) | B8C—B4C—B5C | 59.83 (12) |
C2A—B3A—B11A | 57.93 (12) | B7C—B4C—B5C | 108.19 (15) |
C1A—B3A—B11A | 103.70 (15) | B3C—B4C—B5C | 108.66 (15) |
B7A—B3A—B11A | 60.12 (13) | C1C—B4C—H4C | 124.9 |
B4A—B3A—B11A | 107.78 (16) | B8C—B4C—H4C | 122.4 |
C2A—B3A—H3A | 125.4 | B7C—B4C—H4C | 122.4 |
C1A—B3A—H3A | 125.3 | B3C—B4C—H4C | 121.1 |
B7A—B3A—H3A | 123.1 | B5C—B4C—H4C | 121.3 |
B4A—B3A—H3A | 122.5 | C1C—B5C—B8C | 104.09 (15) |
B11A—B3A—H3A | 122.4 | C1C—B5C—B9C | 104.61 (14) |
C1A—B4A—B8A | 104.24 (16) | B8C—B5C—B9C | 60.26 (12) |
C1A—B4A—B7A | 104.71 (15) | C1C—B5C—B6C | 59.63 (11) |
B8A—B4A—B7A | 60.31 (13) | B8C—B5C—B6C | 107.94 (15) |
C1A—B4A—B3A | 59.67 (11) | B9C—B5C—B6C | 59.43 (12) |
B8A—B4A—B3A | 107.98 (16) | C1C—B5C—B4C | 58.32 (11) |
B7A—B4A—B3A | 59.40 (12) | B8C—B5C—B4C | 59.66 (12) |
C1A—B4A—B5A | 58.50 (12) | B9C—B5C—B4C | 107.97 (15) |
B8A—B4A—B5A | 59.58 (13) | B6C—B5C—B4C | 108.58 (15) |
B7A—B4A—B5A | 107.98 (16) | C1C—B5C—H5C | 124.8 |
B3A—B4A—B5A | 108.69 (15) | B8C—B5C—H5C | 122.7 |
C1A—B4A—H4A | 124.7 | B9C—B5C—H5C | 122.5 |
B8A—B4A—H4A | 122.6 | B6C—B5C—H5C | 121.1 |
B7A—B4A—H4A | 122.5 | B4C—B5C—H5C | 121.5 |
B3A—B4A—H4A | 121.1 | C2C—B6C—C1C | 56.69 (10) |
B5A—B4A—H4A | 121.4 | C2C—B6C—B9C | 103.92 (15) |
C1A—B5A—B8A | 104.20 (15) | C1C—B6C—B9C | 103.84 (14) |
C1A—B5A—B9A | 104.81 (15) | C2C—B6C—B5C | 103.71 (14) |
B8A—B5A—B9A | 60.46 (13) | C1C—B6C—B5C | 57.94 (11) |
C1A—B5A—B6A | 59.52 (12) | B9C—B6C—B5C | 60.10 (12) |
B8A—B5A—B6A | 108.35 (15) | C2C—B6C—B10C | 58.03 (12) |
B9A—B5A—B6A | 59.74 (12) | C1C—B6C—B10C | 103.71 (14) |
C1A—B5A—B4A | 58.10 (12) | B9C—B6C—B10C | 60.10 (12) |
B8A—B5A—B4A | 59.93 (13) | B5C—B6C—B10C | 107.78 (15) |
B9A—B5A—B4A | 108.35 (16) | C2C—B6C—H6C | 125.2 |
B6A—B5A—B4A | 108.51 (15) | C1C—B6C—H6C | 125.3 |
C1A—B5A—H5A | 125.0 | B9C—B6C—H6C | 123.2 |
B8A—B5A—H5A | 122.4 | B5C—B6C—H6C | 122.4 |
B9A—B5A—H5A | 122.2 | B10C—B6C—H6C | 122.4 |
B6A—B5A—H5A | 121.0 | B3C—B7C—B11C | 60.65 (12) |
B4A—B5A—H5A | 121.4 | B3C—B7C—B4C | 60.43 (12) |
C2A—B6A—C1A | 56.83 (11) | B11C—B7C—B4C | 108.46 (15) |
C2A—B6A—B9A | 103.77 (16) | B3C—B7C—B8C | 108.37 (15) |
C1A—B6A—B9A | 103.96 (15) | B11C—B7C—B8C | 107.83 (16) |
C2A—B6A—B5A | 103.85 (15) | B4C—B7C—B8C | 59.69 (12) |
C1A—B6A—B5A | 58.16 (12) | B3C—B7C—B12C | 108.72 (15) |
B9A—B6A—B5A | 59.98 (13) | B11C—B7C—B12C | 59.85 (13) |
C2A—B6A—B10A | 57.91 (12) | B4C—B7C—B12C | 107.95 (16) |
C1A—B6A—B10A | 103.70 (15) | B8C—B7C—B12C | 59.94 (13) |
B9A—B6A—B10A | 59.87 (13) | B3C—B7C—H7C | 121.0 |
B5A—B6A—B10A | 107.49 (16) | B11C—B7C—H7C | 121.6 |
C2A—B6A—H6A | 125.2 | B4C—B7C—H7C | 121.7 |
C1A—B6A—H6A | 125.1 | B8C—B7C—H7C | 121.9 |
B9A—B6A—H6A | 123.3 | B12C—B7C—H7C | 121.7 |
B5A—B6A—H6A | 122.4 | B4C—B8C—B5C | 60.51 (12) |
B10A—B6A—H6A | 122.6 | B4C—B8C—B12C | 108.23 (16) |
B3A—B7A—B11A | 60.42 (13) | B5C—B8C—B12C | 108.29 (15) |
B3A—B7A—B12A | 108.36 (16) | B4C—B8C—B9C | 108.42 (15) |
B11A—B7A—B12A | 59.76 (14) | B5C—B8C—B9C | 59.98 (12) |
B3A—B7A—B4A | 60.34 (12) | B12C—B8C—B9C | 60.16 (13) |
B11A—B7A—B4A | 108.08 (16) | B4C—B8C—B7C | 59.92 (12) |
B12A—B7A—B4A | 107.58 (17) | B5C—B8C—B7C | 108.35 (15) |
B3A—B7A—B8A | 108.28 (16) | B12C—B8C—B7C | 60.06 (13) |
B11A—B7A—B8A | 107.54 (17) | B9C—B8C—B7C | 108.19 (15) |
B12A—B7A—B8A | 59.67 (13) | B4C—B8C—H8C | 121.4 |
B4A—B7A—B8A | 59.75 (13) | B5C—B8C—H8C | 121.4 |
B3A—B7A—H7A | 121.1 | B12C—B8C—H8C | 121.6 |
B11A—B7A—H7A | 121.8 | B9C—B8C—H8C | 121.6 |
B12A—B7A—H7A | 121.9 | B7C—B8C—H8C | 121.7 |
B4A—B7A—H7A | 121.8 | B6C—B9C—B5C | 60.47 (12) |
B8A—B7A—H7A | 122.0 | B6C—B9C—B10C | 60.52 (12) |
B5A—B8A—B12A | 108.08 (16) | B5C—B9C—B10C | 108.41 (15) |
B5A—B8A—B4A | 60.49 (12) | B6C—B9C—B8C | 108.38 (15) |
B12A—B8A—B4A | 107.96 (16) | B5C—B9C—B8C | 59.77 (12) |
B5A—B8A—B9A | 59.78 (13) | B10C—B9C—B8C | 107.73 (16) |
B12A—B8A—B9A | 60.27 (13) | B6C—B9C—B12C | 108.49 (16) |
B4A—B8A—B9A | 108.26 (16) | B5C—B9C—B12C | 107.93 (15) |
B5A—B8A—B7A | 108.41 (16) | B10C—B9C—B12C | 59.72 (13) |
B12A—B8A—B7A | 59.95 (14) | B8C—B9C—B12C | 59.92 (13) |
B4A—B8A—B7A | 59.95 (13) | B6C—B9C—H9C | 121.1 |
B9A—B8A—B7A | 108.32 (16) | B5C—B9C—H9C | 121.6 |
B5A—B8A—H8A | 121.5 | B10C—B9C—H9C | 121.7 |
B12A—B8A—H8A | 121.7 | B8C—B9C—H9C | 121.9 |
B4A—B8A—H8A | 121.6 | B12C—B9C—H9C | 121.8 |
B9A—B8A—H8A | 121.6 | C2C—B10C—B12C | 104.30 (15) |
B7A—B8A—H8A | 121.6 | C2C—B10C—B9C | 104.46 (15) |
B6A—B9A—B5A | 60.28 (12) | B12C—B10C—B9C | 60.37 (13) |
B6A—B9A—B10A | 60.62 (13) | C2C—B10C—B11C | 58.37 (12) |
B5A—B9A—B10A | 108.31 (16) | B12C—B10C—B11C | 59.81 (13) |
B6A—B9A—B8A | 108.21 (16) | B9C—B10C—B11C | 108.02 (16) |
B5A—B9A—B8A | 59.76 (13) | C2C—B10C—B6C | 59.46 (11) |
B10A—B9A—B8A | 107.64 (17) | B12C—B10C—B6C | 108.09 (15) |
B6A—B9A—B12A | 108.35 (16) | B9C—B10C—B6C | 59.38 (12) |
B5A—B9A—B12A | 107.55 (17) | B11C—B10C—B6C | 108.51 (15) |
B10A—B9A—B12A | 59.76 (13) | C2C—B10C—H10C | 124.9 |
B8A—B9A—B12A | 59.62 (13) | B12C—B10C—H10C | 122.4 |
B6A—B9A—H9A | 121.1 | B9C—B10C—H10C | 122.6 |
B5A—B9A—H9A | 121.8 | B11C—B10C—H10C | 121.4 |
B10A—B9A—H9A | 121.6 | B6C—B10C—H10C | 121.2 |
B8A—B9A—H9A | 122.0 | C2C—B11C—B7C | 104.62 (15) |
B12A—B9A—H9A | 122.0 | C2C—B11C—B12C | 104.50 (15) |
C2A—B10A—B12A | 104.11 (16) | B7C—B11C—B12C | 60.42 (13) |
C2A—B10A—B9A | 104.58 (15) | C2C—B11C—B10C | 58.59 (12) |
B12A—B10A—B9A | 60.47 (13) | B7C—B11C—B10C | 108.23 (16) |
C2A—B10A—B11A | 58.41 (12) | B12C—B11C—B10C | 59.85 (13) |
B12A—B10A—B11A | 59.78 (14) | C2C—B11C—B3C | 59.45 (11) |
B9A—B10A—B11A | 108.35 (17) | B7C—B11C—B3C | 59.48 (12) |
C2A—B10A—B6A | 59.33 (12) | B12C—B11C—B3C | 108.24 (15) |
B12A—B10A—B6A | 108.04 (16) | B10C—B11C—B3C | 108.74 (15) |
B9A—B10A—B6A | 59.51 (12) | C2C—B11C—H11C | 124.8 |
B11A—B10A—B6A | 108.55 (16) | B7C—B11C—H11C | 122.4 |
C2A—B10A—H10A | 125.0 | B12C—B11C—H11C | 122.4 |
B12A—B10A—H10A | 122.5 | B10C—B11C—H11C | 121.3 |
B9A—B10A—H10A | 122.3 | B3C—B11C—H11C | 121.1 |
B11A—B10A—H10A | 121.3 | B11C—B12C—B10C | 60.34 (13) |
B6A—B10A—H10A | 121.2 | B11C—B12C—B8C | 107.78 (15) |
C2A—B11A—B12A | 104.20 (16) | B10C—B12C—B8C | 107.89 (15) |
C2A—B11A—B7A | 104.57 (15) | B11C—B12C—B7C | 59.73 (13) |
B12A—B11A—B7A | 60.19 (14) | B10C—B12C—B7C | 108.07 (15) |
C2A—B11A—B3A | 59.52 (12) | B8C—B12C—B7C | 60.00 (13) |
B12A—B11A—B3A | 107.93 (16) | B11C—B12C—B9C | 108.08 (15) |
B7A—B11A—B3A | 59.46 (13) | B10C—B12C—B9C | 59.91 (13) |
C2A—B11A—B10A | 58.44 (12) | B8C—B12C—B9C | 59.93 (13) |
B12A—B11A—B10A | 59.85 (13) | B7C—B12C—B9C | 107.96 (15) |
B7A—B11A—B10A | 108.15 (16) | B11C—B12C—H12C | 121.7 |
B3A—B11A—B10A | 108.70 (15) | B10C—B12C—H12C | 121.6 |
C2A—B11A—H11A | 124.9 | B8C—B12C—H12C | 121.9 |
B12A—B11A—H11A | 122.6 | B7C—B12C—H12C | 121.8 |
B7A—B11A—H11A | 122.5 | B9C—B12C—H12C | 121.7 |
B3A—B11A—H11A | 121.1 | C3D—C1D—C2D | 118.93 (15) |
B10A—B11A—H11A | 121.3 | C4D—C2D—C1D | 117.91 (15) |
B11A—B12A—B10A | 60.37 (13) | C3D—C1D—B5D | 118.74 (16) |
B11A—B12A—B8A | 108.34 (16) | C2D—C1D—B5D | 110.94 (15) |
B10A—B12A—B8A | 108.04 (16) | C3D—C1D—B4D | 120.85 (15) |
B11A—B12A—B7A | 60.05 (14) | C2D—C1D—B4D | 111.71 (14) |
B10A—B12A—B7A | 108.45 (16) | B5D—C1D—B4D | 63.35 (13) |
B8A—B12A—B7A | 60.38 (14) | C3D—C1D—B3D | 118.24 (15) |
B11A—B12A—B9A | 108.26 (16) | C2D—C1D—B3D | 62.24 (11) |
B10A—B12A—B9A | 59.77 (13) | B5D—C1D—B3D | 115.15 (15) |
B8A—B12A—B9A | 60.12 (13) | B4D—C1D—B3D | 62.54 (12) |
B7A—B12A—B9A | 108.54 (16) | C3D—C1D—B6D | 115.17 (15) |
B11A—B12A—H12A | 121.5 | C2D—C1D—B6D | 61.23 (11) |
B10A—B12A—H12A | 121.6 | B5D—C1D—B6D | 62.09 (13) |
B8A—B12A—H12A | 121.6 | B4D—C1D—B6D | 114.75 (15) |
B7A—B12A—H12A | 121.3 | B3D—C1D—B6D | 115.15 (14) |
B9A—B12A—H12A | 121.6 | O2D—C3D—O1D | 125.75 (18) |
C3B—C1B—C2B | 120.41 (15) | O2D—C3D—C1D | 121.30 (17) |
C3B—C1B—B4B | 119.86 (15) | O1D—C3D—C1D | 112.90 (16) |
C2B—C1B—B4B | 111.27 (15) | C3D—O1D—H1D | 106.0 (19) |
C3B—C1B—B5B | 117.81 (15) | C4D—C2D—B7D | 121.56 (16) |
C2B—C1B—B5B | 110.91 (15) | C1D—C2D—B7D | 110.76 (14) |
B4B—C1B—B5B | 63.40 (14) | C4D—C2D—B11D | 120.74 (15) |
C3B—C1B—B3B | 118.47 (16) | C1D—C2D—B11D | 111.13 (15) |
C2B—C1B—B3B | 61.63 (11) | B7D—C2D—B11D | 62.86 (12) |
B4B—C1B—B3B | 62.80 (13) | C4D—C2D—B6D | 115.58 (15) |
B5B—C1B—B3B | 115.42 (16) | C1D—C2D—B6D | 61.99 (12) |
C3B—C1B—B6B | 115.62 (16) | B7D—C2D—B6D | 114.68 (15) |
C2B—C1B—B6B | 61.03 (11) | B11D—C2D—B6D | 62.41 (12) |
B4B—C1B—B6B | 115.01 (16) | C4D—C2D—B3D | 117.30 (15) |
B5B—C1B—B6B | 62.51 (14) | C1D—C2D—B3D | 61.00 (11) |
B3B—C1B—B6B | 114.78 (14) | B7D—C2D—B3D | 62.43 (12) |
O2B—C3B—C1B | 120.25 (17) | B11D—C2D—B3D | 114.39 (14) |
O1B—C3B—C1B | 113.37 (16) | B6D—C2D—B3D | 114.73 (14) |
C3B—O1B—H1B | 104.9 (19) | O4D—C4D—O3D | 126.7 (2) |
C4B—C2B—C1B | 119.17 (15) | O4D—C4D—C2D | 119.74 (18) |
O2B—C3B—O1B | 126.20 (18) | O3D—C4D—C2D | 113.61 (17) |
C4B—C2B—B7B | 120.23 (15) | C4D—O3D—H2D | 112 (2) |
C1B—C2B—B7B | 110.99 (14) | C1D—B3D—C2D | 56.76 (10) |
C4B—C2B—B11B | 119.73 (16) | C1D—B3D—B8D | 104.06 (15) |
C1B—C2B—B11B | 111.13 (15) | C2D—B3D—B8D | 103.81 (14) |
B7B—C2B—B11B | 63.07 (13) | C1D—B3D—B4D | 58.11 (11) |
C4B—C2B—B6B | 116.08 (16) | C2D—B3D—B4D | 103.84 (14) |
C1B—C2B—B6B | 61.75 (12) | B8D—B3D—B4D | 60.23 (12) |
B7B—C2B—B6B | 115.03 (16) | C1D—B3D—B7D | 103.52 (14) |
B11B—C2B—B6B | 62.56 (12) | C2D—B3D—B7D | 57.61 (11) |
C4B—C2B—B3B | 117.11 (16) | B8D—B3D—B7D | 60.20 (12) |
C1B—C2B—B3B | 61.11 (11) | B4D—B3D—B7D | 107.87 (15) |
B7B—C2B—B3B | 62.78 (12) | C1D—B3D—H3D | 125.2 |
B11B—C2B—B3B | 115.00 (15) | C2D—B3D—H3D | 125.4 |
B6B—C2B—B3B | 114.95 (15) | B8D—B3D—H3D | 123.0 |
O4B—C4B—O3B | 126.8 (2) | B4D—B3D—H3D | 122.2 |
O4B—C4B—C2B | 119.10 (19) | B7D—B3D—H3D | 122.6 |
O3B—C4B—C2B | 114.06 (17) | C1D—B4D—B9D | 104.21 (15) |
C4B—O3B—H2B | 110 (2) | C1D—B4D—B8D | 104.38 (15) |
C1B—B3B—C2B | 57.26 (10) | B9D—B4D—B8D | 60.38 (13) |
C1B—B3B—B8B | 104.09 (16) | C1D—B4D—B3D | 59.35 (11) |
C2B—B3B—B8B | 103.85 (15) | B9D—B4D—B3D | 108.10 (15) |
C1B—B3B—B4B | 57.81 (12) | B8D—B4D—B3D | 59.42 (12) |
C2B—B3B—B4B | 103.85 (15) | C1D—B4D—B5D | 58.20 (12) |
B8B—B3B—B4B | 60.21 (13) | B9D—B4D—B5D | 59.86 (13) |
C1B—B3B—B7B | 104.02 (15) | B8D—B4D—B5D | 108.00 (16) |
C2B—B3B—B7B | 57.87 (11) | B3D—B4D—B5D | 108.30 (15) |
B8B—B3B—B7B | 59.85 (13) | C1D—B4D—H4D | 125.0 |
B4B—B3B—B7B | 107.55 (16) | B9D—B4D—H4D | 122.4 |
C1B—B3B—H3B | 125.0 | B8D—B4D—H4D | 122.5 |
C2B—B3B—H3B | 125.1 | B3D—B4D—H4D | 121.2 |
B8B—B3B—H3B | 123.2 | B5D—B4D—H4D | 121.5 |
B4B—B3B—H3B | 122.5 | C1D—B5D—B6D | 60.15 (12) |
B7B—B3B—H3B | 122.5 | C1D—B5D—B9D | 104.37 (16) |
C1B—B4B—B9B | 104.39 (17) | B6D—B5D—B9D | 108.01 (16) |
C1B—B4B—B8B | 104.77 (15) | C1D—B5D—B10D | 105.11 (16) |
B9B—B4B—B8B | 60.52 (14) | B6D—B5D—B10D | 59.36 (13) |
C1B—B4B—B3B | 59.39 (12) | B9D—B5D—B10D | 60.27 (13) |
B9B—B4B—B3B | 108.13 (16) | C1D—B5D—B4D | 58.45 (12) |
B8B—B4B—B3B | 59.51 (13) | B6D—B5D—B4D | 109.14 (16) |
C1B—B4B—B5B | 58.42 (13) | B9D—B5D—B4D | 59.83 (13) |
B9B—B4B—B5B | 59.90 (14) | B10D—B5D—B4D | 108.35 (16) |
B8B—B4B—B5B | 108.43 (17) | C1D—B5D—H5D | 124.5 |
B3B—B4B—B5B | 108.53 (16) | B6D—B5D—H5D | 120.9 |
C1B—B4B—H4B | 124.8 | B9D—B5D—H5D | 122.6 |
B9B—B4B—H4B | 122.4 | B10D—B5D—H5D | 122.4 |
B8B—B4B—H4B | 122.2 | B4D—B5D—H5D | 121.2 |
B3B—B4B—H4B | 121.2 | C2D—B6D—C1D | 56.78 (11) |
B5B—B4B—H4B | 121.3 | C2D—B6D—B10D | 104.48 (15) |
C1B—B5B—B9B | 103.94 (17) | C1D—B6D—B10D | 104.13 (15) |
C1B—B5B—B6B | 59.73 (12) | C2D—B6D—B5D | 103.89 (15) |
B9B—B5B—B6B | 107.81 (16) | C1D—B6D—B5D | 57.76 (12) |
C1B—B5B—B4B | 58.18 (12) | B10D—B6D—B5D | 60.46 (13) |
B9B—B5B—B4B | 59.56 (14) | C2D—B6D—B11D | 58.21 (12) |
B6B—B5B—B4B | 108.45 (16) | C1D—B6D—B11D | 103.69 (14) |
C1B—B5B—B10B | 104.82 (16) | B10D—B6D—B11D | 60.09 (13) |
B9B—B5B—B10B | 60.62 (15) | B5D—B6D—B11D | 107.84 (16) |
B6B—B5B—B10B | 59.24 (14) | C2D—B6D—H6D | 125.0 |
B4B—B5B—B10B | 108.29 (17) | C1D—B6D—H6D | 125.4 |
C1B—B5B—H5B | 124.8 | B10D—B6D—H6D | 122.8 |
B9B—B5B—H5B | 122.7 | B5D—B6D—H6D | 122.4 |
B6B—B5B—H5B | 121.2 | B11D—B6D—H6D | 122.4 |
B4B—B5B—H5B | 121.5 | C2D—B7D—B12D | 104.42 (15) |
B10B—B5B—H5B | 122.2 | C2D—B7D—B11D | 58.71 (11) |
C2B—B6B—C1B | 57.21 (11) | B12D—B7D—B11D | 59.65 (13) |
C2B—B6B—B10B | 104.29 (16) | C2D—B7D—B8D | 104.85 (15) |
C1B—B6B—B10B | 104.21 (17) | B12D—B7D—B8D | 60.03 (13) |
C2B—B6B—B11B | 58.26 (12) | B11D—B7D—B8D | 107.91 (16) |
C1B—B6B—B11B | 104.14 (15) | C2D—B7D—B3D | 59.97 (11) |
B10B—B6B—B11B | 59.81 (13) | B12D—B7D—B3D | 107.71 (16) |
C2B—B6B—B5B | 104.05 (16) | B11D—B7D—B3D | 108.99 (15) |
C1B—B6B—B5B | 57.75 (12) | B8D—B7D—B3D | 59.21 (12) |
B10B—B6B—B5B | 60.42 (14) | C2D—B7D—H7D | 124.4 |
B11B—B6B—B5B | 107.73 (17) | B12D—B7D—H7D | 122.8 |
C2B—B6B—H6B | 124.8 | B11D—B7D—H7D | 121.3 |
C1B—B6B—H6B | 125.0 | B8D—B7D—H7D | 122.7 |
B10B—B6B—H6B | 123.0 | B3D—B7D—H7D | 121.0 |
B11B—B6B—H6B | 122.4 | B3D—B8D—B4D | 60.35 (12) |
B5B—B6B—H6B | 122.4 | B3D—B8D—B12D | 108.71 (15) |
C2B—B7B—B8B | 104.65 (15) | B4D—B8D—B12D | 107.81 (16) |
C2B—B7B—B12B | 104.26 (15) | B3D—B8D—B7D | 60.58 (12) |
B8B—B7B—B12B | 60.45 (14) | B4D—B8D—B7D | 108.26 (15) |
C2B—B7B—B11B | 58.51 (12) | B12D—B8D—B7D | 59.92 (12) |
B8B—B7B—B11B | 108.18 (17) | B3D—B8D—B9D | 108.37 (15) |
B12B—B7B—B11B | 59.69 (14) | B4D—B8D—B9D | 59.80 (13) |
C2B—B7B—B3B | 59.34 (11) | B12D—B8D—B9D | 59.69 (13) |
B8B—B7B—B3B | 59.42 (12) | B7D—B8D—B9D | 107.64 (16) |
B12B—B7B—B3B | 107.94 (15) | B3D—B8D—H8D | 121.0 |
B11B—B7B—B3B | 108.44 (15) | B4D—B8D—H8D | 121.7 |
C2B—B7B—H7B | 124.8 | B12D—B8D—H8D | 121.7 |
B8B—B7B—H7B | 122.4 | B7D—B8D—H8D | 121.7 |
B12B—B7B—H7B | 122.5 | B9D—B8D—H8D | 122.0 |
B11B—B7B—H7B | 121.4 | B12D—B9D—B4D | 108.03 (16) |
B3B—B7B—H7B | 121.3 | B12D—B9D—B5D | 107.95 (16) |
B3B—B8B—B7B | 60.73 (12) | B4D—B9D—B5D | 60.31 (13) |
B3B—B8B—B4B | 60.28 (12) | B12D—B9D—B10D | 60.25 (13) |
B7B—B8B—B4B | 108.31 (16) | B4D—B9D—B10D | 108.45 (16) |
B3B—B8B—B9B | 107.82 (17) | B5D—B9D—B10D | 59.91 (13) |
B7B—B8B—B9B | 107.42 (17) | B12D—B9D—B8D | 59.95 (13) |
B4B—B8B—B9B | 59.36 (14) | B4D—B9D—B8D | 59.82 (13) |
B3B—B8B—B12B | 108.48 (16) | B5D—B9D—B8D | 107.91 (16) |
B7B—B8B—B12B | 59.82 (13) | B10D—B9D—B8D | 108.24 (16) |
B4B—B8B—B12B | 107.40 (17) | B12D—B9D—H9E | 121.7 |
B9B—B8B—B12B | 59.57 (14) | B4D—B9D—H9E | 121.5 |
B3B—B8B—H8B | 121.1 | B5D—B9D—H9E | 121.8 |
B7B—B8B—H8B | 121.6 | B10D—B9D—H9E | 121.4 |
B4B—B8B—H8B | 121.9 | B8D—B9D—H9E | 121.8 |
B9B—B8B—H8B | 122.4 | B6D—B10D—B11D | 60.55 (13) |
B12B—B8B—H8B | 121.9 | B6D—B10D—B5D | 60.18 (13) |
B4B—B9B—B5B | 60.54 (14) | B11D—B10D—B5D | 107.97 (16) |
B4B—B9B—B12B | 108.54 (17) | B6D—B10D—B9D | 108.31 (16) |
B5B—B9B—B12B | 108.43 (18) | B11D—B10D—B9D | 107.49 (16) |
B4B—B9B—B8B | 60.12 (14) | B5D—B10D—B9D | 59.82 (13) |
B5B—B9B—B8B | 108.62 (17) | B6D—B10D—B12D | 108.22 (16) |
B12B—B9B—B8B | 60.24 (14) | B11D—B10D—B12D | 59.59 (13) |
B4B—B9B—B10B | 108.59 (17) | B5D—B10D—B12D | 107.37 (16) |
B5B—B9B—B10B | 60.02 (14) | B9D—B10D—B12D | 59.60 (13) |
B12B—B9B—B10B | 60.18 (14) | B6D—B10D—H9D | 121.1 |
B8B—B9B—B10B | 108.46 (17) | B11D—B10D—H9D | 121.8 |
B4B—B9B—H9B | 121.3 | B5D—B10D—H9D | 121.9 |
B5B—B9B—H9B | 121.4 | B9D—B10D—H9D | 122.0 |
B12B—B9B—H9B | 121.4 | B12D—B10D—H9D | 122.1 |
B8B—B9B—H9B | 121.4 | C2D—B11D—B12D | 104.61 (15) |
B10B—B9B—H9B | 121.5 | C2D—B11D—B10D | 104.81 (15) |
B6B—B10B—B11B | 60.61 (13) | B12D—B11D—B10D | 60.62 (13) |
B6B—B10B—B5B | 60.34 (14) | C2D—B11D—B7D | 58.43 (11) |
B11B—B10B—B5B | 108.29 (17) | B12D—B11D—B7D | 60.17 (12) |
B6B—B10B—B12B | 108.24 (17) | B10D—B11D—B7D | 108.72 (16) |
B11B—B10B—B12B | 59.76 (13) | C2D—B11D—B6D | 59.38 (11) |
B5B—B10B—B12B | 107.28 (18) | B12D—B11D—B6D | 108.10 (16) |
B6B—B10B—B9B | 107.69 (17) | B10D—B11D—B6D | 59.36 (13) |
B11B—B10B—B9B | 107.21 (17) | B7D—B11D—B6D | 108.54 (15) |
B5B—B10B—B9B | 59.37 (14) | C2D—B11D—H10D | 124.8 |
B12B—B10B—B9B | 59.39 (14) | B12D—B11D—H10D | 122.2 |
B6B—B10B—H10B | 121.2 | B10D—B11D—H10D | 122.2 |
B11B—B10B—H10B | 121.6 | B7D—B11D—H10D | 121.1 |
B5B—B10B—H10B | 121.9 | B6D—B11D—H10D | 121.3 |
B12B—B10B—H10B | 122.1 | B11D—B12D—B9D | 108.09 (16) |
B9B—B10B—H10B | 122.5 | B11D—B12D—B7D | 60.18 (12) |
C2B—B11B—B10B | 104.82 (15) | B9D—B12D—B7D | 108.27 (16) |
C2B—B11B—B12B | 104.40 (16) | B11D—B12D—B8D | 108.35 (15) |
B10B—B11B—B12B | 60.77 (14) | B9D—B12D—B8D | 60.36 (13) |
C2B—B11B—B6B | 59.18 (12) | B7D—B12D—B8D | 60.05 (13) |
B10B—B11B—B6B | 59.58 (14) | B11D—B12D—B10D | 59.79 (13) |
B12B—B11B—B6B | 108.23 (16) | B9D—B12D—B10D | 60.15 (14) |
C2B—B11B—B7B | 58.43 (12) | B7D—B12D—B10D | 108.07 (15) |
B10B—B11B—B7B | 108.73 (17) | B8D—B12D—B10D | 108.48 (16) |
B12B—B11B—B7B | 59.93 (13) | B11D—B12D—H11D | 121.7 |
B6B—B11B—B7B | 108.41 (15) | B9D—B12D—H11D | 121.5 |
C2B—B11B—H11B | 124.9 | B7D—B12D—H11D | 121.6 |
B10B—B11B—H11B | 122.0 | B8D—B12D—H11D | 121.4 |
B12B—B11B—H11B | 122.3 | B10D—B12D—H11D | 121.7 |
B6B—B11B—H11B | 121.3 | C12A—C11—C12B | 55.3 (6) |
B7B—B11B—H11B | 121.2 | C12A—C11—O1S | 119.6 (6) |
B11B—B12B—B9B | 107.80 (17) | C12B—C11—O1S | 129.0 (6) |
B11B—B12B—B7B | 60.38 (13) | C12A—C11—H11H | 107.4 |
B9B—B12B—B7B | 107.83 (16) | C12B—C11—H11H | 122.8 |
B11B—B12B—B8B | 108.16 (16) | O1S—C11—H11H | 107.4 |
B9B—B12B—B8B | 60.18 (14) | C12A—C11—H11J | 107.4 |
B7B—B12B—B8B | 59.73 (13) | C12B—C11—H11J | 52.2 |
B11B—B12B—B10B | 59.47 (14) | O1S—C11—H11J | 107.4 |
B9B—B12B—B10B | 60.43 (15) | H11H—C11—H11J | 107.0 |
B7B—B12B—B10B | 108.04 (17) | C11—C12A—H12H | 109.5 |
B8B—B12B—B10B | 108.61 (16) | C11—C12A—H12I | 109.5 |
B11B—B12B—H12B | 121.8 | C11—C12A—H12J | 109.5 |
B9B—B12B—H12B | 121.7 | C11—C12B—H12K | 109.5 |
B7B—B12B—H12B | 121.8 | C11—C12B—H12L | 109.5 |
B8B—B12B—H12B | 121.5 | H12K—C12B—H12L | 109.5 |
B10B—B12B—H12B | 121.5 | C11—C12B—H12M | 109.5 |
C3C—C1C—C2C | 122.21 (15) | H12K—C12B—H12M | 109.5 |
C4C—C2C—C1C | 116.56 (15) | H12L—C12B—H12M | 109.5 |
O2C—C3C—O1C | 125.83 (17) | C11—O1S—H1S | 113 (3) |
C4C—C2C—B11C | 122.52 (16) | O2S—C21—C22 | 115.1 (3) |
C1C—C2C—B11C | 111.12 (14) | O2S—C21—H21B | 108.5 |
C4C—C2C—B10C | 121.31 (15) | C22—C21—H21B | 108.5 |
C1C—C2C—B10C | 111.29 (14) | O2S—C21—H21A | 108.5 |
B11C—C2C—B10C | 63.04 (13) | C22—C21—H21A | 108.5 |
C4C—C2C—B3C | 116.61 (15) | H21B—C21—H21A | 107.5 |
C1C—C2C—B3C | 61.45 (11) | C21—C22—H22A | 109.5 |
B11C—C2C—B3C | 62.63 (12) | C21—C22—H22C | 109.5 |
B10C—C2C—B3C | 115.02 (15) | H22A—C22—H22C | 109.5 |
C4C—C2C—B6C | 114.92 (15) | C21—C22—H22B | 109.5 |
C1C—C2C—B6C | 61.73 (11) | H22A—C22—H22B | 109.5 |
B11C—C2C—B6C | 114.86 (15) | H22C—C22—H22B | 109.5 |
B10C—C2C—B6C | 62.52 (12) | C21—O2S—H2S | 116 (3) |
B3C—C2C—B6C | 115.09 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2Bi | 0.87 (3) | 1.78 (3) | 2.647 (2) | 175 (3) |
O1B—H1B···O2Aii | 0.91 (3) | 1.78 (3) | 2.687 (2) | 175 (3) |
O1S—H1S···O4Aiii | 0.90 (4) | 1.89 (4) | 2.790 (3) | 175 (4) |
O3A—H2A···O4Biii | 0.93 (3) | 1.70 (3) | 2.624 (2) | 172 (3) |
O3B—H2B···O1S | 0.90 (4) | 1.58 (4) | 2.478 (2) | 175 (3) |
O1C—H1C···O2Div | 0.89 (4) | 1.79 (4) | 2.677 (2) | 172 (4) |
O1D—H1D···O2Civ | 0.85 (3) | 1.83 (3) | 2.689 (2) | 178 (3) |
O2S—H2S···O4Cv | 0.73 (4) | 2.08 (4) | 2.806 (3) | 172 (4) |
O3C—H2C···O4Dvi | 0.85 (3) | 1.79 (3) | 2.628 (2) | 167 (3) |
O3D—H2D···O2Svii | 1.03 (4) | 1.46 (4) | 2.476 (2) | 169 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) x, y−1, z; (vii) x+1, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C4H12B10O4·0.5C2H6O |
Mr | 255.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 160 |
a, b, c (Å) | 12.133 (5), 12.658 (5), 19.104 (5) |
α, β, γ (°) | 76.390 (5), 73.260 (5), 76.620 (5) |
V (Å3) | 2688.2 (17) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.5 × 0.5 × 0.5 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10856, 9408, 7890 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.144, 1.03 |
No. of reflections | 9408 |
No. of parameters | 755 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.47 |
Selected geometric parameters (Å, º) topC1A—C2A | 1.651 (3) | C1C—C2C | 1.652 (2) |
C1A—C3A | 1.523 (3) | C1C—C3C | 1.525 (2) |
C3A—O1A | 1.301 (2) | C3C—O1C | 1.306 (2) |
C3A—O2A | 1.212 (2) | C3C—O2C | 1.212 (2) |
C2A—C4A | 1.510 (3) | C2C—C4C | 1.510 (3) |
C4A—O3A | 1.304 (3) | C4C—O3C | 1.300 (2) |
C4A—O4A | 1.205 (3) | C4C—O4C | 1.209 (2) |
C1B—C2B | 1.660 (2) | C1D—C2D | 1.653 (2) |
C1B—C3B | 1.527 (3) | C1D—C3D | 1.522 (3) |
C3B—O1B | 1.298 (2) | C1D—B6D | 1.745 (3) |
C3B—O2B | 1.214 (2) | C3D—O1D | 1.304 (2) |
C2B—C4B | 1.516 (3) | C2D—C4D | 1.514 (3) |
C4B—O3B | 1.283 (3) | C4D—O3D | 1.286 (3) |
C4B—O4B | 1.204 (2) | C4D—O4D | 1.201 (3) |
| | | |
C3A—C1A—C2A | 121.07 (15) | C3C—C1C—C2C | 122.21 (15) |
C4A—C2A—C1A | 115.75 (15) | C4C—C2C—C1C | 116.56 (15) |
O2A—C3A—O1A | 125.80 (18) | O2C—C3C—O1C | 125.83 (17) |
O4A—C4A—O3A | 126.73 (19) | O4C—C4C—O3C | 127.21 (19) |
C3B—C1B—C2B | 120.41 (15) | C3D—C1D—C2D | 118.93 (15) |
C4B—C2B—C1B | 119.17 (15) | C4D—C2D—C1D | 117.91 (15) |
O2B—C3B—O1B | 126.20 (18) | O2D—C3D—O1D | 125.75 (18) |
O4B—C4B—O3B | 126.8 (2) | O4D—C4D—O3D | 126.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2Bi | 0.87 (3) | 1.78 (3) | 2.647 (2) | 175 (3) |
O1B—H1B···O2Aii | 0.91 (3) | 1.78 (3) | 2.687 (2) | 175 (3) |
O1S—H1S···O4Aiii | 0.90 (4) | 1.89 (4) | 2.790 (3) | 175 (4) |
O3A—H2A···O4Biii | 0.93 (3) | 1.70 (3) | 2.624 (2) | 172 (3) |
O3B—H2B···O1S | 0.90 (4) | 1.58 (4) | 2.478 (2) | 175 (3) |
O1C—H1C···O2Div | 0.89 (4) | 1.79 (4) | 2.677 (2) | 172 (4) |
O1D—H1D···O2Civ | 0.85 (3) | 1.83 (3) | 2.689 (2) | 178 (3) |
O2S—H2S···O4Cv | 0.73 (4) | 2.08 (4) | 2.806 (3) | 172 (4) |
O3C—H2C···O4Dvi | 0.85 (3) | 1.79 (3) | 2.628 (2) | 167 (3) |
O3D—H2D···O2Svii | 1.03 (4) | 1.46 (4) | 2.476 (2) | 169 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) x, y−1, z; (vii) x+1, y+1, z. |
Crystal engineering is an emerging interdisciplinary research area which has many applications in pure and applied chemistry. The use of heteroboranes in studies of crystal engineering has only recently begun to be exploited (Centore et al., 1994; Hosmane et al., 1998; Lee et al., 2000; Hardie, Raston & Wells, 2000; Hardy & Raston, 2000, 2001; Welch et al., 2001; O'Dowd et al., 2002), yet such compounds have a number of potential advantages in this respect. Within the field of crystal engineering, the carboxylic acid group is frequently used to afford supramolecular assemblies through intermolecular H···O bonding (Leiserowitz, 1976). Accordingly, we have begun a systematic study of the crystal structures of carborane carboxylic acids. The monocarboxylic acid, 1-COOH-1,2-closo-C2B10H11, forms discrete dimers (Welch et al., 2001) and the 1,12-dicarboxylic acid, 1,12-(COOH)2-1,12-closo-C2B10H10, forms infinite chains (Centore et al., 1994) via intermolecular eight-membered hydrogen-bonded rings. In this paper, we report the crystal and molecular structure of 1,2-(COOH)2-1,2-closo-C2B10H10, (I).
Compound (I) crystallizes from ethanol with half a molecule of ethanol of solvation. There are four different carborane molecules in the asymmetric unit. The crystal structure reveals two crystallographically independent tetramer units each arranged about a inversion centre. The tetramers are constructed from two sorts of hydrogen-bonding interactions, viz. two conventional eight-membered ring carboxylic acid dimers and two ten-membered rings involving two carboxylic acid groups and an ethanol molecule. In graph-set terminology (Etter, 1990; Etter & MacDonald, 1990), the former is denoted as R22(8) and the latter is represented as R33(10). In each of the four crystallographically independent cages, the two carboxylic acid groups lie perpendicular to each other, preventing the formation of the cyclic trimer that might have been expected if the carboxylic acid groups were in the same plane. Thus, within each cage one pair of Ccage—Ccage—C—O torsion angles are close to +90 and −90°, with the other pair close to 0 and 180°. For the second kind of carboxylic acid group, the OH group is syn to the first kind of carboxylic acid group in half the cages in each tetrameric unit, and anti to it in the other half.
Hydrogen-bond dimensions are H···O = 1.46 (4)–2.08 (4) Å, O···O = 2.476 (2)–2.806 (3) Å and O—H···O = 167 (3)–178 (3)°. The hydrogen bonds formed between the carboxylic acid H atom and the solvent molecule O atom (O3B—H2B···O1S and O3D—H2D····O2S) are the strongest of all the hydrogen bonds [H···O = 1.58 (4) and 1.46 (4) Å]. They are classified as `very strong' hydrogen bonds, while all the other hydrogen bonds are classified as strong hydrogen bonds (Desiraju & Steiner, 1999). The hydrogen bonds involving the H atoms of the solvent molecule and the O atoms of the carboxylic acid groups are the weakest hydrogen bonds.
The C1—C2 bond distances [1.651 (3)–1.660 (2) Å] are somewhat longer than in the parent compound 1,2-closo-C2B10H12 (Davidson et al., 1996) [1.629 (6) and 1.630 (6) Å] and the monocarboxylic acid 1-COOH-1,2-closo-C2B10H11 [1.631 (2) Å; Welch et al., 2001]. The B—C distances lie between 1.701 (3) and 1.749 (3) Å, while the B—B distances range from 1.763 (3) to 1.799 (4) Å. There appears to be a correlation between the C—COOH distance and orientation of C—COOH group, with lengths of 1.510 (3)–1.516 (3) Å when C—C—C—O is 0 or 180°, and 1.522 (3)–1.527 (3) Å when the C—C—C—O torsion angle is +90 or −90°.