Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010204/gd1160sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010204/gd1160Isup2.hkl |
CCDC reference: 175078
For related literature, see: Centore et al. (1994); Davidson et al. (1996); Desiraju & Steiner (1999); Douek & Welch (1993); Etter (1990); Etter & MacDonald (1990); Hosmane et al. (1998); Lee et al. (2000); Leiserowitz (1976); Wade (1976); Zakharkin & Grebennikov (1967).
Compound (I) was prepared based on the literature method of Zakharkin & Grebennikov (1967) in 73% yield and crystals were grown by evaporation of an acetonitrile solution. Analysis: calculated for C3H12B10O2: C 19.1, H 6.4%; found: C 18.3, H 6.90%; 1H FT-NMR (400.1 MHz, TMS, δ, p.p.m.): 10.40 (1H, br, O—H), 4.00 (1H, s, C—H); 11B-{1H} FT-NMR (128.4 MHz, BF3·OEt2, δ, p.p.m.): 0.77 (2B), -5.97 (2B), -8.79 (2B), -10.52(2B), -11.65(2B). NMR spectra were recorded from solution in CDCl3 at 293 K on a Bruker DPX400 spectrometer.
All H atoms (both cage H atoms and COOH) were located from the difference Fourier map and refined, but cage H atoms were restrained, with B—H = 1.10 (2) Å.
Data collection: XSCANS (Bruker, 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.
C3H12B10O2 | F(000) = 384 |
Mr = 188.23 | Dx = 1.188 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.988 (2) Å | Cell parameters from 46 reflections |
b = 12.031 (3) Å | θ = 3.2–12.5° |
c = 12.869 (4) Å | µ = 0.07 mm−1 |
β = 103.33 (2)° | T = 160 K |
V = 1052.8 (5) Å3 | Needle, colourless |
Z = 4 | 0.82 × 0.24 × 0.20 mm |
Bruker P4 diffractometer | Rint = 0.041 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.4° |
Graphite monochromator | h = −1→8 |
ω scans | k = −14→1 |
2577 measured reflections | l = −15→15 |
1849 independent reflections | 3 standard reflections every 97 reflections |
1557 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.3182P] where P = (Fo2 + 2Fc2)/3 |
1849 reflections | (Δ/σ)max = 0.013 |
184 parameters | Δρmax = 0.21 e Å−3 |
10 restraints | Δρmin = −0.23 e Å−3 |
C3H12B10O2 | V = 1052.8 (5) Å3 |
Mr = 188.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.988 (2) Å | µ = 0.07 mm−1 |
b = 12.031 (3) Å | T = 160 K |
c = 12.869 (4) Å | 0.82 × 0.24 × 0.20 mm |
β = 103.33 (2)° |
Bruker P4 diffractometer | Rint = 0.041 |
2577 measured reflections | 3 standard reflections every 97 reflections |
1849 independent reflections | intensity decay: none |
1557 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.043 | 10 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.21 e Å−3 |
1849 reflections | Δρmin = −0.23 e Å−3 |
184 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2990 (2) | 0.09740 (12) | 0.19910 (11) | 0.0205 (3) | |
C2 | 0.1608 (2) | 0.00725 (13) | 0.24206 (13) | 0.0258 (4) | |
H2 | 0.156 (3) | −0.0617 (16) | 0.2103 (15) | 0.030 (5)* | |
B3 | 0.3853 (3) | 0.04007 (16) | 0.32434 (14) | 0.0281 (4) | |
H3 | 0.503 (2) | −0.0211 (14) | 0.3317 (15) | 0.036 (5)* | |
B4 | 0.4129 (3) | 0.18515 (15) | 0.29881 (14) | 0.0252 (4) | |
H4 | 0.561 (2) | 0.2158 (15) | 0.2983 (15) | 0.035 (5)* | |
B5 | 0.2059 (3) | 0.22885 (14) | 0.19796 (13) | 0.0224 (4) | |
H5 | 0.227 (3) | 0.2857 (14) | 0.1351 (13) | 0.032 (5)* | |
B6 | 0.0466 (3) | 0.11200 (15) | 0.15923 (14) | 0.0243 (4) | |
H6 | −0.021 (3) | 0.0895 (15) | 0.0762 (11) | 0.031 (5)* | |
B7 | 0.1689 (3) | 0.02422 (16) | 0.37368 (16) | 0.0328 (5) | |
H7 | 0.151 (3) | −0.0493 (14) | 0.4200 (15) | 0.046 (6)* | |
B8 | 0.3270 (3) | 0.14071 (17) | 0.41208 (14) | 0.0293 (4) | |
H8 | 0.419 (3) | 0.1497 (16) | 0.4917 (12) | 0.037 (5)* | |
B9 | 0.2149 (3) | 0.25692 (15) | 0.33484 (14) | 0.0247 (4) | |
H9 | 0.234 (3) | 0.3438 (12) | 0.3654 (14) | 0.033 (5)* | |
B10 | −0.0095 (3) | 0.21156 (15) | 0.24783 (14) | 0.0253 (4) | |
H10 | −0.135 (2) | 0.2662 (14) | 0.2222 (14) | 0.038 (5)* | |
B11 | −0.0369 (3) | 0.06777 (16) | 0.27325 (16) | 0.0298 (4) | |
H11 | −0.172 (3) | 0.0199 (16) | 0.2630 (18) | 0.050 (6)* | |
B12 | 0.0656 (3) | 0.15804 (16) | 0.38111 (15) | 0.0291 (4) | |
H12 | −0.016 (2) | 0.1772 (15) | 0.4428 (13) | 0.031 (5)* | |
O1 | 0.50751 (17) | 0.12697 (9) | 0.08288 (9) | 0.0296 (3) | |
O2 | 0.35818 (18) | −0.03929 (9) | 0.07678 (9) | 0.0316 (3) | |
C3 | 0.3924 (2) | 0.05412 (13) | 0.11255 (11) | 0.0222 (3) | |
H1 | 0.552 (4) | 0.094 (2) | 0.026 (2) | 0.072 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0248 (8) | 0.0207 (7) | 0.0175 (7) | 0.0011 (6) | 0.0078 (6) | 0.0017 (6) |
C2 | 0.0351 (9) | 0.0188 (8) | 0.0280 (8) | −0.0008 (7) | 0.0167 (7) | 0.0015 (6) |
B3 | 0.0360 (10) | 0.0300 (10) | 0.0197 (8) | 0.0100 (8) | 0.0095 (7) | 0.0052 (7) |
B4 | 0.0270 (9) | 0.0294 (9) | 0.0190 (8) | −0.0002 (7) | 0.0048 (7) | −0.0025 (7) |
B5 | 0.0278 (9) | 0.0193 (8) | 0.0214 (8) | 0.0013 (7) | 0.0083 (7) | −0.0001 (7) |
B6 | 0.0229 (9) | 0.0247 (9) | 0.0254 (9) | 0.0011 (7) | 0.0059 (7) | −0.0027 (7) |
B7 | 0.0505 (12) | 0.0262 (9) | 0.0286 (10) | 0.0053 (9) | 0.0235 (9) | 0.0058 (7) |
B8 | 0.0370 (11) | 0.0342 (10) | 0.0179 (8) | 0.0066 (8) | 0.0086 (8) | 0.0014 (7) |
B9 | 0.0307 (10) | 0.0233 (9) | 0.0215 (8) | 0.0004 (7) | 0.0092 (7) | −0.0023 (7) |
B10 | 0.0267 (9) | 0.0220 (8) | 0.0290 (9) | 0.0015 (7) | 0.0098 (7) | −0.0029 (7) |
B11 | 0.0332 (10) | 0.0244 (9) | 0.0375 (10) | −0.0043 (8) | 0.0198 (8) | −0.0054 (8) |
B12 | 0.0375 (10) | 0.0283 (9) | 0.0267 (9) | 0.0017 (8) | 0.0180 (8) | −0.0012 (7) |
O1 | 0.0377 (7) | 0.0303 (6) | 0.0260 (6) | −0.0037 (5) | 0.0178 (5) | −0.0032 (5) |
O2 | 0.0412 (7) | 0.0282 (6) | 0.0313 (6) | −0.0028 (5) | 0.0205 (5) | −0.0067 (5) |
C3 | 0.0249 (8) | 0.0251 (8) | 0.0175 (7) | 0.0035 (6) | 0.0065 (6) | 0.0016 (6) |
C1—C2 | 1.631 (2) | B6—B10 | 1.759 (2) |
C1—C3 | 1.507 (2) | B6—B11 | 1.781 (3) |
C1—B3 | 1.729 (2) | B6—H6 | 1.099 (14) |
C1—B4 | 1.710 (2) | B7—B8 | 1.782 (3) |
C1—B5 | 1.709 (2) | B7—B11 | 1.777 (3) |
C1—B6 | 1.728 (2) | B7—B12 | 1.776 (3) |
C2—B3 | 1.724 (3) | B7—H7 | 1.091 (15) |
C2—B6 | 1.723 (2) | B8—B9 | 1.788 (3) |
C2—B7 | 1.694 (2) | B8—B12 | 1.790 (3) |
C2—B11 | 1.690 (2) | B8—H8 | 1.083 (14) |
C2—H2 | 0.922 (19) | B9—B10 | 1.789 (3) |
B3—B4 | 1.795 (3) | B9—B12 | 1.774 (3) |
B3—B7 | 1.780 (3) | B9—H9 | 1.114 (14) |
B3—B8 | 1.766 (3) | B10—B11 | 1.779 (3) |
B3—H3 | 1.093 (14) | B10—B12 | 1.794 (3) |
B4—B5 | 1.785 (2) | B10—H10 | 1.087 (14) |
B4—B8 | 1.782 (2) | B11—B12 | 1.778 (3) |
B4—B9 | 1.780 (3) | B11—H11 | 1.090 (15) |
B4—H4 | 1.102 (14) | B12—H12 | 1.103 (14) |
B5—B6 | 1.791 (2) | O1—C3 | 1.3051 (19) |
B5—B9 | 1.780 (2) | O1—H1 | 0.95 (3) |
B5—B10 | 1.779 (3) | O2—C3 | 1.2170 (19) |
B5—H5 | 1.097 (14) | ||
C3—C1—C2 | 114.31 (12) | B12—B7—B11 | 60.06 (11) |
C3—C1—B5 | 122.84 (12) | C2—B7—B3 | 59.43 (10) |
C2—C1—B5 | 111.34 (12) | B12—B7—B3 | 108.15 (13) |
C3—C1—B4 | 124.21 (13) | B11—B7—B3 | 108.71 (13) |
C2—C1—B4 | 111.44 (11) | C2—B7—B8 | 104.34 (12) |
B5—C1—B4 | 62.96 (10) | B12—B7—B8 | 60.40 (11) |
C3—C1—B6 | 113.67 (12) | B11—B7—B8 | 108.42 (13) |
C2—C1—B6 | 61.63 (10) | B3—B7—B8 | 59.44 (11) |
B5—C1—B6 | 62.78 (10) | C2—B7—H7 | 117.9 (11) |
B4—C1—B6 | 115.23 (12) | B12—B7—H7 | 127.4 (11) |
C3—C1—B3 | 115.72 (12) | B11—B7—H7 | 117.5 (11) |
C2—C1—B3 | 61.64 (10) | B3—B7—H7 | 119.7 (11) |
B5—C1—B3 | 115.30 (11) | B8—B7—H7 | 128.9 (11) |
B4—C1—B3 | 62.93 (10) | B3—B8—B4 | 60.78 (10) |
B6—C1—B3 | 115.45 (12) | B3—B8—B7 | 60.21 (11) |
C1—C2—B11 | 111.99 (12) | B4—B8—B7 | 108.26 (12) |
C1—C2—B7 | 111.89 (13) | B3—B8—B9 | 108.46 (12) |
B11—C2—B7 | 63.33 (11) | B4—B8—B9 | 59.83 (10) |
C1—C2—B6 | 61.96 (10) | B7—B8—B9 | 107.26 (13) |
B11—C2—B6 | 62.90 (11) | B3—B8—B12 | 108.15 (14) |
B7—C2—B6 | 115.74 (13) | B4—B8—B12 | 107.58 (12) |
C1—C2—B3 | 61.96 (10) | B7—B8—B12 | 59.63 (11) |
B11—C2—B3 | 115.69 (13) | B9—B8—B12 | 59.44 (10) |
B7—C2—B3 | 62.76 (11) | B3—B8—H8 | 119.9 (10) |
B6—C2—B3 | 116.01 (12) | B4—B8—H8 | 120.3 (10) |
C1—C2—H2 | 114.3 (12) | B7—B8—H8 | 122.4 (10) |
B11—C2—H2 | 123.0 (12) | B9—B8—H8 | 122.5 (10) |
B7—C2—H2 | 122.8 (12) | B12—B8—H8 | 123.6 (10) |
B6—C2—H2 | 114.8 (12) | B12—B9—B5 | 108.39 (12) |
B3—C2—H2 | 114.4 (12) | B12—B9—B4 | 108.35 (13) |
C2—B3—C1 | 56.39 (9) | B5—B9—B4 | 60.19 (10) |
C2—B3—B8 | 103.80 (13) | B12—B9—B8 | 60.33 (11) |
C1—B3—B8 | 103.91 (12) | B5—B9—B8 | 108.23 (12) |
C2—B3—B7 | 57.81 (11) | B4—B9—B8 | 59.91 (10) |
C1—B3—B7 | 103.49 (13) | B12—B9—B10 | 60.45 (11) |
B8—B3—B7 | 60.35 (11) | B5—B9—B10 | 59.79 (10) |
C2—B3—B4 | 103.38 (12) | B4—B9—B10 | 108.10 (12) |
C1—B3—B4 | 58.02 (9) | B8—B9—B10 | 108.52 (13) |
B8—B3—B4 | 60.04 (10) | B12—B9—H9 | 122.9 (9) |
B7—B3—B4 | 107.79 (13) | B5—B9—H9 | 120.1 (9) |
C2—B3—H3 | 117.4 (10) | B4—B9—H9 | 120.6 (10) |
C1—B3—H3 | 116.2 (10) | B8—B9—H9 | 122.4 (9) |
B8—B3—H3 | 133.5 (10) | B10—B9—H9 | 121.6 (10) |
B7—B3—H3 | 125.7 (10) | B6—B10—B5 | 60.80 (10) |
B4—B3—H3 | 124.0 (10) | B6—B10—B11 | 60.44 (10) |
C1—B4—B9 | 103.88 (12) | B5—B10—B11 | 108.41 (12) |
C1—B4—B8 | 104.03 (13) | B6—B10—B9 | 108.60 (13) |
B9—B4—B8 | 60.26 (10) | B5—B10—B9 | 59.86 (10) |
C1—B4—B5 | 58.50 (9) | B11—B10—B9 | 107.31 (13) |
B9—B4—B5 | 59.90 (10) | B6—B10—B12 | 108.39 (13) |
B8—B4—B5 | 108.28 (13) | B5—B10—B12 | 107.56 (13) |
C1—B4—B3 | 59.05 (9) | B11—B10—B12 | 59.68 (10) |
B9—B4—B3 | 107.53 (13) | B9—B10—B12 | 59.34 (10) |
B8—B4—B3 | 59.18 (10) | B6—B10—H10 | 120.1 (10) |
B5—B4—B3 | 108.43 (13) | B5—B10—H10 | 120.9 (10) |
C1—B4—H4 | 118.5 (10) | B11—B10—H10 | 122.0 (10) |
B9—B4—H4 | 128.9 (10) | B9—B10—H10 | 122.5 (10) |
B8—B4—H4 | 126.9 (10) | B12—B10—H10 | 123.0 (10) |
B5—B4—H4 | 120.2 (10) | C2—B11—B7 | 58.44 (10) |
B3—B4—H4 | 117.9 (10) | C2—B11—B12 | 104.13 (14) |
C1—B5—B10 | 103.95 (12) | B7—B11—B12 | 59.95 (11) |
C1—B5—B9 | 103.91 (11) | C2—B11—B10 | 104.28 (13) |
B10—B5—B9 | 60.36 (10) | B7—B11—B10 | 108.48 (14) |
C1—B5—B4 | 58.54 (9) | B12—B11—B10 | 60.56 (10) |
B10—B5—B4 | 108.32 (12) | C2—B11—B6 | 59.45 (10) |
B9—B5—B4 | 59.90 (10) | B7—B11—B6 | 108.85 (13) |
C1—B5—B6 | 59.14 (9) | B12—B11—B6 | 108.12 (13) |
B10—B5—B6 | 59.05 (10) | B10—B11—B6 | 59.23 (10) |
B9—B5—B6 | 107.61 (12) | C2—B11—H11 | 118.5 (11) |
B4—B5—B6 | 108.57 (12) | B7—B11—H11 | 117.8 (12) |
C1—B5—H5 | 117.8 (10) | B12—B11—H11 | 126.9 (12) |
B10—B5—H5 | 127.7 (9) | B10—B11—H11 | 128.3 (11) |
B9—B5—H5 | 129.3 (9) | B6—B11—H11 | 119.9 (12) |
B4—B5—H5 | 119.6 (9) | B9—B12—B7 | 108.17 (13) |
B6—B5—H5 | 117.8 (9) | B9—B12—B11 | 108.06 (12) |
C2—B6—C1 | 56.41 (9) | B7—B12—B11 | 59.99 (11) |
C2—B6—B10 | 103.75 (12) | B9—B12—B8 | 60.23 (11) |
C1—B6—B10 | 103.98 (12) | B7—B12—B8 | 59.98 (11) |
C2—B6—B11 | 57.65 (10) | B11—B12—B8 | 108.03 (13) |
C1—B6—B11 | 103.36 (12) | B9—B12—B10 | 60.21 (10) |
B10—B6—B11 | 60.33 (10) | B7—B12—B10 | 107.87 (12) |
C2—B6—B5 | 103.45 (12) | B11—B12—B10 | 59.76 (10) |
C1—B6—B5 | 58.08 (9) | B8—B12—B10 | 108.25 (13) |
B10—B6—B5 | 60.14 (10) | B9—B12—H12 | 122.9 (9) |
B11—B6—B5 | 107.82 (12) | B7—B12—H12 | 120.7 (9) |
C2—B6—H6 | 117.1 (10) | B11—B12—H12 | 120.5 (9) |
C1—B6—H6 | 116.4 (9) | B8—B12—H12 | 122.2 (9) |
B10—B6—H6 | 133.5 (9) | B10—B12—H12 | 121.9 (9) |
B11—B6—H6 | 125.4 (9) | C3—O1—H1 | 106.0 (16) |
B5—B6—H6 | 124.4 (9) | O2—C3—O1 | 126.15 (14) |
C2—B7—B12 | 104.06 (13) | O2—C3—C1 | 121.19 (14) |
C2—B7—B11 | 58.23 (11) | O1—C3—C1 | 112.66 (13) |
C3—C1—C2—B11 | −144.37 (13) | B11—B7—B8—B9 | 0.49 (16) |
B5—C1—C2—B11 | 0.24 (17) | B3—B7—B8—B9 | 101.79 (13) |
B4—C1—C2—B11 | 68.47 (16) | C2—B7—B8—B12 | 98.23 (14) |
B6—C1—C2—B11 | −39.49 (12) | B11—B7—B8—B12 | 37.42 (12) |
B3—C1—C2—B11 | 108.33 (14) | B3—B7—B8—B12 | 138.72 (13) |
C3—C1—C2—B7 | 146.69 (13) | C1—B5—B9—B12 | −60.98 (15) |
B5—C1—C2—B7 | −68.70 (16) | B10—B5—B9—B12 | 37.35 (12) |
B4—C1—C2—B7 | −0.47 (17) | B4—B5—B9—B12 | −101.06 (14) |
B6—C1—C2—B7 | −108.43 (14) | B6—B5—B9—B12 | 0.61 (17) |
B3—C1—C2—B7 | 39.39 (13) | C1—B5—B9—B4 | 40.08 (11) |
C3—C1—C2—B6 | −104.88 (13) | B10—B5—B9—B4 | 138.41 (13) |
B5—C1—C2—B6 | 39.73 (12) | B6—B5—B9—B4 | 101.67 (13) |
B4—C1—C2—B6 | 107.97 (13) | C1—B5—B9—B8 | 2.93 (16) |
B3—C1—C2—B6 | 147.82 (12) | B10—B5—B9—B8 | 101.26 (14) |
C3—C1—C2—B3 | 107.30 (14) | B4—B5—B9—B8 | −37.15 (12) |
B5—C1—C2—B3 | −108.09 (13) | B6—B5—B9—B8 | 64.52 (15) |
B4—C1—C2—B3 | −39.86 (12) | C1—B5—B9—B10 | −98.33 (12) |
B6—C1—C2—B3 | −147.82 (12) | B4—B5—B9—B10 | −138.41 (13) |
B11—C2—B3—C1 | −102.40 (14) | B6—B5—B9—B10 | −36.74 (11) |
B7—C2—B3—C1 | −138.53 (13) | C1—B4—B9—B12 | 61.07 (15) |
B6—C2—B3—C1 | −31.53 (12) | B8—B4—B9—B12 | −37.35 (12) |
C1—C2—B3—B8 | 97.70 (13) | B5—B4—B9—B12 | 101.13 (14) |
B11—C2—B3—B8 | −4.70 (17) | B3—B4—B9—B12 | −0.41 (16) |
B7—C2—B3—B8 | −40.83 (12) | C1—B4—B9—B5 | −40.06 (11) |
B6—C2—B3—B8 | 66.16 (16) | B8—B4—B9—B5 | −138.48 (13) |
C1—C2—B3—B7 | 138.53 (13) | B3—B4—B9—B5 | −101.54 (13) |
B11—C2—B3—B7 | 36.13 (13) | C1—B4—B9—B8 | 98.42 (13) |
B6—C2—B3—B7 | 106.99 (14) | B5—B4—B9—B8 | 138.48 (13) |
C1—C2—B3—B4 | 35.74 (11) | B3—B4—B9—B8 | 36.94 (12) |
B11—C2—B3—B4 | −66.66 (16) | C1—B4—B9—B10 | −2.94 (15) |
B7—C2—B3—B4 | −102.79 (13) | B8—B4—B9—B10 | −101.36 (14) |
B6—C2—B3—B4 | 4.21 (17) | B5—B4—B9—B10 | 37.12 (12) |
C3—C1—B3—C2 | −105.02 (14) | B3—B4—B9—B10 | −64.42 (15) |
B5—C1—B3—C2 | 101.67 (14) | B3—B8—B9—B12 | 100.61 (15) |
B4—C1—B3—C2 | 137.94 (13) | B4—B8—B9—B12 | 138.49 (13) |
B6—C1—B3—C2 | 31.26 (12) | B7—B8—B9—B12 | 37.02 (12) |
C3—C1—B3—B8 | 157.48 (13) | B3—B8—B9—B5 | −0.60 (17) |
C2—C1—B3—B8 | −97.50 (14) | B4—B8—B9—B5 | 37.27 (12) |
B5—C1—B3—B8 | 4.17 (17) | B7—B8—B9—B5 | −64.20 (15) |
B4—C1—B3—B8 | 40.44 (12) | B12—B8—B9—B5 | −101.22 (14) |
B6—C1—B3—B8 | −66.24 (16) | B3—B8—B9—B4 | −37.88 (13) |
C3—C1—B3—B7 | −140.22 (13) | B7—B8—B9—B4 | −101.47 (13) |
C2—C1—B3—B7 | −35.19 (12) | B12—B8—B9—B4 | −138.49 (13) |
B5—C1—B3—B7 | 66.47 (16) | B3—B8—B9—B10 | 62.75 (16) |
B4—C1—B3—B7 | 102.74 (13) | B4—B8—B9—B10 | 100.63 (13) |
B6—C1—B3—B7 | −3.93 (17) | B7—B8—B9—B10 | −0.84 (16) |
C3—C1—B3—B4 | 117.04 (14) | B12—B8—B9—B10 | −37.86 (12) |
C2—C1—B3—B4 | −137.94 (13) | C2—B6—B10—B5 | 97.80 (13) |
B5—C1—B3—B4 | −36.27 (13) | C1—B6—B10—B5 | 39.54 (11) |
B6—C1—B3—B4 | −106.68 (14) | B11—B6—B10—B5 | 137.13 (13) |
C3—C1—B4—B9 | 153.68 (13) | C2—B6—B10—B11 | −39.34 (12) |
C2—C1—B4—B9 | −63.03 (15) | C1—B6—B10—B11 | −97.60 (13) |
B5—C1—B4—B9 | 40.77 (11) | B5—B6—B10—B11 | −137.13 (13) |
B6—C1—B4—B9 | 4.68 (16) | C2—B6—B10—B9 | 60.45 (15) |
B3—C1—B4—B9 | −102.33 (13) | C1—B6—B10—B9 | 2.19 (15) |
C3—C1—B4—B8 | −144.03 (14) | B11—B6—B10—B9 | 99.79 (14) |
C2—C1—B4—B8 | −0.74 (15) | B5—B6—B10—B9 | −37.34 (12) |
B5—C1—B4—B8 | 103.06 (13) | C2—B6—B10—B12 | −2.48 (16) |
B6—C1—B4—B8 | 66.98 (15) | C1—B6—B10—B12 | −60.74 (15) |
B3—C1—B4—B8 | −40.04 (11) | B11—B6—B10—B12 | 36.86 (13) |
C3—C1—B4—B5 | 112.91 (15) | B5—B6—B10—B12 | −100.28 (14) |
C2—C1—B4—B5 | −103.80 (13) | C1—B5—B10—B6 | −40.07 (11) |
B6—C1—B4—B5 | −36.09 (12) | B9—B5—B10—B6 | −138.33 (13) |
B3—C1—B4—B5 | −143.10 (13) | B4—B5—B10—B6 | −101.10 (13) |
C3—C1—B4—B3 | −104.00 (15) | C1—B5—B10—B11 | −1.48 (16) |
C2—C1—B4—B3 | 39.30 (12) | B9—B5—B10—B11 | −99.75 (14) |
B5—C1—B4—B3 | 143.10 (13) | B4—B5—B10—B11 | −62.52 (16) |
B6—C1—B4—B3 | 107.01 (13) | B6—B5—B10—B11 | 38.59 (12) |
C2—B3—B4—C1 | −35.00 (10) | C1—B5—B10—B9 | 98.26 (12) |
B8—B3—B4—C1 | −133.39 (13) | B4—B5—B10—B9 | 37.23 (12) |
B7—B3—B4—C1 | −95.07 (14) | B6—B5—B10—B9 | 138.33 (13) |
C2—B3—B4—B9 | 60.98 (14) | C1—B5—B10—B12 | 61.60 (14) |
C1—B3—B4—B9 | 95.97 (13) | B9—B5—B10—B12 | −36.66 (11) |
B8—B3—B4—B9 | −37.41 (12) | B4—B5—B10—B12 | 0.57 (16) |
B7—B3—B4—B9 | 0.90 (16) | B6—B5—B10—B12 | 101.67 (13) |
C2—B3—B4—B8 | 98.39 (13) | B12—B9—B10—B6 | −100.81 (13) |
C1—B3—B4—B8 | 133.39 (13) | B5—B9—B10—B6 | 37.76 (12) |
B7—B3—B4—B8 | 38.31 (12) | B4—B9—B10—B6 | 0.46 (17) |
C2—B3—B4—B5 | −2.34 (15) | B8—B9—B10—B6 | −63.00 (15) |
C1—B3—B4—B5 | 32.66 (11) | B12—B9—B10—B5 | −138.57 (13) |
B8—B3—B4—B5 | −100.73 (14) | B4—B9—B10—B5 | −37.30 (12) |
B7—B3—B4—B5 | −62.42 (15) | B8—B9—B10—B5 | −100.76 (13) |
C3—C1—B5—B10 | 141.88 (14) | B12—B9—B10—B11 | −36.93 (12) |
C2—C1—B5—B10 | 0.79 (15) | B5—B9—B10—B11 | 101.63 (13) |
B4—C1—B5—B10 | −103.17 (13) | B4—B9—B10—B11 | 64.34 (15) |
B6—C1—B5—B10 | 40.03 (11) | B8—B9—B10—B11 | 0.87 (16) |
B3—C1—B5—B10 | −66.91 (15) | B5—B9—B10—B12 | 138.57 (13) |
C3—C1—B5—B9 | −155.73 (13) | B4—B9—B10—B12 | 101.27 (14) |
C2—C1—B5—B9 | 63.18 (15) | B8—B9—B10—B12 | 37.81 (12) |
B4—C1—B5—B9 | −40.78 (11) | C1—C2—B11—B7 | −104.31 (14) |
B6—C1—B5—B9 | 102.41 (13) | B6—C2—B11—B7 | −143.40 (13) |
B3—C1—B5—B9 | −4.52 (17) | B3—C2—B11—B7 | −35.92 (13) |
C3—C1—B5—B4 | −114.96 (16) | C1—C2—B11—B12 | −63.84 (15) |
C2—C1—B5—B4 | 103.96 (13) | B7—C2—B11—B12 | 40.47 (12) |
B6—C1—B5—B4 | 143.19 (12) | B6—C2—B11—B12 | −102.94 (13) |
B3—C1—B5—B4 | 36.25 (13) | B3—C2—B11—B12 | 4.55 (17) |
C3—C1—B5—B6 | 101.85 (15) | C1—C2—B11—B10 | −1.16 (17) |
C2—C1—B5—B6 | −39.23 (12) | B7—C2—B11—B10 | 103.15 (14) |
B4—C1—B5—B6 | −143.19 (12) | B6—C2—B11—B10 | −40.25 (12) |
B3—C1—B5—B6 | −106.94 (14) | B3—C2—B11—B10 | 67.23 (16) |
B9—B4—B5—C1 | −132.88 (12) | C1—C2—B11—B6 | 39.09 (12) |
B8—B4—B5—C1 | −95.57 (13) | B7—C2—B11—B6 | 143.40 (13) |
B3—B4—B5—C1 | −32.87 (11) | B3—C2—B11—B6 | 107.49 (14) |
C1—B4—B5—B10 | 95.46 (12) | B12—B7—B11—C2 | 133.35 (13) |
B9—B4—B5—B10 | −37.43 (12) | B3—B7—B11—C2 | 32.72 (12) |
B8—B4—B5—B10 | −0.11 (16) | B8—B7—B11—C2 | 95.78 (14) |
B3—B4—B5—B10 | 62.58 (15) | C2—B7—B11—B12 | −133.35 (13) |
C1—B4—B5—B9 | 132.88 (12) | B3—B7—B11—B12 | −100.64 (14) |
B8—B4—B5—B9 | 37.31 (12) | B8—B7—B11—B12 | −37.57 (12) |
B3—B4—B5—B9 | 100.01 (13) | C2—B7—B11—B10 | −95.73 (13) |
C1—B4—B5—B6 | 32.86 (11) | B12—B7—B11—B10 | 37.62 (12) |
B9—B4—B5—B6 | −100.03 (13) | B3—B7—B11—B10 | −63.01 (16) |
B8—B4—B5—B6 | −62.71 (15) | B8—B7—B11—B10 | 0.05 (17) |
B3—B4—B5—B6 | −0.02 (16) | C2—B7—B11—B6 | −32.86 (12) |
B11—C2—B6—C1 | 138.52 (12) | B12—B7—B11—B6 | 100.50 (13) |
B7—C2—B6—C1 | 102.26 (15) | B3—B7—B11—B6 | −0.14 (17) |
B3—C2—B6—C1 | 31.53 (12) | B8—B7—B11—B6 | 62.93 (16) |
C1—C2—B6—B10 | −97.82 (12) | B6—B10—B11—C2 | 40.37 (12) |
B11—C2—B6—B10 | 40.69 (12) | B5—B10—B11—C2 | 1.62 (17) |
B7—C2—B6—B10 | 4.43 (18) | B9—B10—B11—C2 | −61.60 (15) |
B3—C2—B6—B10 | −66.29 (16) | B12—B10—B11—C2 | −98.38 (14) |
C1—C2—B6—B11 | −138.52 (12) | B6—B10—B11—B7 | 101.40 (14) |
B7—C2—B6—B11 | −36.26 (14) | B5—B10—B11—B7 | 62.65 (16) |
B3—C2—B6—B11 | −106.98 (15) | B9—B10—B11—B7 | −0.57 (16) |
C1—C2—B6—B5 | −35.75 (10) | B12—B10—B11—B7 | −37.35 (12) |
B11—C2—B6—B5 | 102.76 (13) | B6—B10—B11—B12 | 138.75 (13) |
B7—C2—B6—B5 | 66.50 (16) | B5—B10—B11—B12 | 100.00 (14) |
B3—C2—B6—B5 | −4.22 (17) | B9—B10—B11—B12 | 36.78 (12) |
C3—C1—B6—C2 | 105.91 (14) | B5—B10—B11—B6 | −38.75 (12) |
B5—C1—B6—C2 | −137.97 (12) | B9—B10—B11—B6 | −101.97 (14) |
B4—C1—B6—C2 | −101.82 (13) | B12—B10—B11—B6 | −138.75 (13) |
B3—C1—B6—C2 | −31.26 (12) | C1—B6—B11—C2 | −34.55 (11) |
C3—C1—B6—B10 | −156.70 (12) | B10—B6—B11—C2 | −133.21 (14) |
C2—C1—B6—B10 | 97.39 (13) | B5—B6—B11—C2 | −94.91 (13) |
B5—C1—B6—B10 | −40.58 (11) | C2—B6—B11—B7 | 32.47 (12) |
B4—C1—B6—B10 | −4.42 (16) | C1—B6—B11—B7 | −2.08 (15) |
B3—C1—B6—B10 | 66.13 (16) | B10—B6—B11—B7 | −100.74 (14) |
C3—C1—B6—B11 | 141.02 (13) | B5—B6—B11—B7 | −62.45 (15) |
C2—C1—B6—B11 | 35.11 (11) | C2—B6—B11—B12 | 96.04 (15) |
B5—C1—B6—B11 | −102.86 (12) | C1—B6—B11—B12 | 61.49 (15) |
B4—C1—B6—B11 | −66.71 (15) | B10—B6—B11—B12 | −37.17 (12) |
B3—C1—B6—B11 | 3.85 (16) | B5—B6—B11—B12 | 1.13 (17) |
C3—C1—B6—B5 | −116.13 (13) | C2—B6—B11—B10 | 133.21 (14) |
C2—C1—B6—B5 | 137.97 (12) | C1—B6—B11—B10 | 98.66 (13) |
B4—C1—B6—B5 | 36.15 (12) | B5—B6—B11—B10 | 38.30 (12) |
B3—C1—B6—B5 | 106.71 (13) | B5—B9—B12—B7 | 63.56 (17) |
C1—B5—B6—C2 | 34.99 (10) | B4—B9—B12—B7 | −0.23 (17) |
B10—B5—B6—C2 | −98.31 (13) | B8—B9—B12—B7 | −37.39 (13) |
B9—B5—B6—C2 | −61.00 (14) | B10—B9—B12—B7 | 100.62 (14) |
B4—B5—B6—C2 | 2.37 (15) | B5—B9—B12—B11 | 0.09 (17) |
B10—B5—B6—C1 | −133.30 (12) | B4—B9—B12—B11 | −63.70 (16) |
B9—B5—B6—C1 | −95.99 (12) | B8—B9—B12—B11 | −100.87 (14) |
B4—B5—B6—C1 | −32.62 (11) | B10—B9—B12—B11 | 37.15 (12) |
C1—B5—B6—B10 | 133.30 (12) | B5—B9—B12—B8 | 100.96 (14) |
B9—B5—B6—B10 | 37.32 (12) | B4—B9—B12—B8 | 37.17 (12) |
B4—B5—B6—B10 | 100.68 (13) | B10—B9—B12—B8 | 138.01 (13) |
C1—B5—B6—B11 | 94.92 (13) | B5—B9—B12—B10 | −37.06 (12) |
B10—B5—B6—B11 | −38.38 (12) | B4—B9—B12—B10 | −100.85 (13) |
B9—B5—B6—B11 | −1.07 (16) | B8—B9—B12—B10 | −138.01 (13) |
B4—B5—B6—B11 | 62.29 (15) | C2—B7—B12—B9 | −61.20 (17) |
C1—C2—B7—B12 | 63.96 (17) | B11—B7—B12—B9 | −100.79 (14) |
B11—C2—B7—B12 | −40.51 (12) | B3—B7—B12—B9 | 0.79 (18) |
B6—C2—B7—B12 | −4.41 (19) | B8—B7—B12—B9 | 37.51 (12) |
B3—C2—B7—B12 | 103.01 (14) | C2—B7—B12—B11 | 39.59 (12) |
C1—C2—B7—B11 | 104.47 (14) | B3—B7—B12—B11 | 101.58 (14) |
B6—C2—B7—B11 | 36.10 (13) | B8—B7—B12—B11 | 138.29 (13) |
B3—C2—B7—B11 | 143.52 (13) | C2—B7—B12—B8 | −98.71 (14) |
C1—C2—B7—B3 | −39.05 (12) | B11—B7—B12—B8 | −138.29 (13) |
B11—C2—B7—B3 | −143.52 (13) | B3—B7—B12—B8 | −36.72 (12) |
B6—C2—B7—B3 | −107.42 (15) | C2—B7—B12—B10 | 2.47 (18) |
C1—C2—B7—B8 | 1.45 (17) | B11—B7—B12—B10 | −37.12 (13) |
B11—C2—B7—B8 | −103.02 (14) | B3—B7—B12—B10 | 64.46 (17) |
B6—C2—B7—B8 | −66.92 (17) | B8—B7—B12—B10 | 101.17 (14) |
B3—C2—B7—B8 | 40.50 (12) | C2—B11—B12—B9 | 61.28 (16) |
C1—B3—B7—C2 | 34.56 (11) | B7—B11—B12—B9 | 100.99 (14) |
B8—B3—B7—C2 | 133.06 (13) | B10—B11—B12—B9 | −37.34 (12) |
B4—B3—B7—C2 | 94.88 (13) | B6—B11—B12—B9 | −0.75 (17) |
C2—B3—B7—B12 | −95.93 (14) | C2—B11—B12—B7 | −39.71 (12) |
C1—B3—B7—B12 | −61.37 (16) | B10—B11—B12—B7 | −138.33 (14) |
B8—B3—B7—B12 | 37.13 (13) | B6—B11—B12—B7 | −101.74 (14) |
B4—B3—B7—B12 | −1.04 (17) | C2—B11—B12—B8 | −2.42 (16) |
C2—B3—B7—B11 | −32.25 (12) | B7—B11—B12—B8 | 37.29 (12) |
C1—B3—B7—B11 | 2.30 (17) | B10—B11—B12—B8 | −101.04 (14) |
B8—B3—B7—B11 | 100.80 (14) | B6—B11—B12—B8 | −64.45 (16) |
B4—B3—B7—B11 | 62.63 (16) | C2—B11—B12—B10 | 98.62 (13) |
C2—B3—B7—B8 | −133.06 (13) | B7—B11—B12—B10 | 138.33 (14) |
C1—B3—B7—B8 | −98.50 (13) | B6—B11—B12—B10 | 36.59 (12) |
B4—B3—B7—B8 | −38.18 (12) | B3—B8—B12—B9 | −101.16 (13) |
C2—B3—B8—B4 | −97.67 (13) | B4—B8—B12—B9 | −36.94 (12) |
C1—B3—B8—B4 | −39.42 (11) | B7—B8—B12—B9 | −138.21 (13) |
B7—B3—B8—B4 | −137.21 (13) | B3—B8—B12—B7 | 37.05 (12) |
C2—B3—B8—B7 | 39.55 (12) | B4—B8—B12—B7 | 101.26 (14) |
C1—B3—B8—B7 | 97.79 (14) | B9—B8—B12—B7 | 138.21 (13) |
B4—B3—B8—B7 | 137.21 (13) | B3—B8—B12—B11 | −0.24 (17) |
C2—B3—B8—B9 | −60.21 (16) | B4—B8—B12—B11 | 63.97 (16) |
C1—B3—B8—B9 | −1.96 (17) | B7—B8—B12—B11 | −37.29 (12) |
B7—B3—B8—B9 | −99.75 (15) | B9—B8—B12—B11 | 100.91 (14) |
B4—B3—B8—B9 | 37.46 (12) | B3—B8—B12—B10 | −63.48 (16) |
C2—B3—B8—B12 | 2.75 (16) | B4—B8—B12—B10 | 0.74 (17) |
C1—B3—B8—B12 | 60.99 (16) | B7—B8—B12—B10 | −100.53 (13) |
B7—B3—B8—B12 | −36.80 (13) | B9—B8—B12—B10 | 37.68 (12) |
B4—B3—B8—B12 | 100.42 (14) | B6—B10—B12—B9 | 101.17 (14) |
C1—B4—B8—B3 | 39.97 (11) | B5—B10—B12—B9 | 36.89 (11) |
B9—B4—B8—B3 | 138.14 (14) | B11—B10—B12—B9 | 138.35 (13) |
B5—B4—B8—B3 | 100.98 (14) | B6—B10—B12—B7 | 0.04 (18) |
C1—B4—B8—B7 | 1.60 (16) | B5—B10—B12—B7 | −64.24 (16) |
B9—B4—B8—B7 | 99.77 (14) | B11—B10—B12—B7 | 37.22 (13) |
B5—B4—B8—B7 | 62.61 (16) | B9—B10—B12—B7 | −101.13 (15) |
B3—B4—B8—B7 | −38.37 (13) | B6—B10—B12—B11 | −37.19 (12) |
C1—B4—B8—B9 | −98.17 (13) | B5—B10—B12—B11 | −101.47 (13) |
B5—B4—B8—B9 | −37.16 (12) | B9—B10—B12—B11 | −138.35 (13) |
B3—B4—B8—B9 | −138.14 (14) | B6—B10—B12—B8 | 63.47 (16) |
C1—B4—B8—B12 | −61.40 (15) | B5—B10—B12—B8 | −0.81 (17) |
B9—B4—B8—B12 | 36.77 (12) | B11—B10—B12—B8 | 100.66 (14) |
B5—B4—B8—B12 | −0.39 (17) | B9—B10—B12—B8 | −37.69 (12) |
B3—B4—B8—B12 | −101.37 (14) | C2—C1—C3—O2 | 2.6 (2) |
C2—B7—B8—B3 | −40.49 (12) | B5—C1—C3—O2 | −137.41 (15) |
B12—B7—B8—B3 | −138.72 (13) | B4—C1—C3—O2 | 145.03 (15) |
B11—B7—B8—B3 | −101.30 (14) | B6—C1—C3—O2 | −65.56 (18) |
C2—B7—B8—B4 | −1.86 (17) | B3—C1—C3—O2 | 71.49 (19) |
B12—B7—B8—B4 | −100.09 (14) | C2—C1—C3—O1 | −177.63 (12) |
B11—B7—B8—B4 | −62.67 (16) | B5—C1—C3—O1 | 42.31 (19) |
B3—B7—B8—B4 | 38.63 (12) | B4—C1—C3—O1 | −35.25 (19) |
C2—B7—B8—B9 | 61.29 (16) | B6—C1—C3—O1 | 114.16 (14) |
B12—B7—B8—B9 | −36.94 (12) | B3—C1—C3—O1 | −108.79 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.95 (3) | 1.72 (3) | 2.6655 (16) | 177 (2) |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C3H12B10O2 |
Mr | 188.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 160 |
a, b, c (Å) | 6.988 (2), 12.031 (3), 12.869 (4) |
β (°) | 103.33 (2) |
V (Å3) | 1052.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.82 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2577, 1849, 1557 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.119, 1.02 |
No. of reflections | 1849 |
No. of parameters | 184 |
No. of restraints | 10 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
C1—C2 | 1.631 (2) | B6—B10 | 1.759 (2) |
C1—C3 | 1.507 (2) | B6—B11 | 1.781 (3) |
C1—B3 | 1.729 (2) | B6—H6 | 1.099 (14) |
C1—B4 | 1.710 (2) | B7—B8 | 1.782 (3) |
C1—B5 | 1.709 (2) | B7—B11 | 1.777 (3) |
C1—B6 | 1.728 (2) | B7—B12 | 1.776 (3) |
C2—B3 | 1.724 (3) | B7—H7 | 1.091 (15) |
C2—B6 | 1.723 (2) | B8—B9 | 1.788 (3) |
C2—B7 | 1.694 (2) | B8—B12 | 1.790 (3) |
C2—B11 | 1.690 (2) | B8—H8 | 1.083 (14) |
C2—H2 | 0.922 (19) | B9—B10 | 1.789 (3) |
B3—B4 | 1.795 (3) | B9—B12 | 1.774 (3) |
B3—B7 | 1.780 (3) | B9—H9 | 1.114 (14) |
B3—B8 | 1.766 (3) | B10—B11 | 1.779 (3) |
B3—H3 | 1.093 (14) | B10—B12 | 1.794 (3) |
B4—B5 | 1.785 (2) | B10—H10 | 1.087 (14) |
B4—B8 | 1.782 (2) | B11—B12 | 1.778 (3) |
B4—B9 | 1.780 (3) | B11—H11 | 1.090 (15) |
B4—H4 | 1.102 (14) | B12—H12 | 1.103 (14) |
B5—B6 | 1.791 (2) | O1—C3 | 1.3051 (19) |
B5—B9 | 1.780 (2) | O1—H1 | 0.95 (3) |
B5—B10 | 1.779 (3) | O2—C3 | 1.2170 (19) |
B5—H5 | 1.097 (14) | ||
C3—C1—C2 | 114.31 (12) | C3—O1—H1 | 106.0 (16) |
C3—C1—B5 | 122.84 (12) | O2—C3—O1 | 126.15 (14) |
C2—C1—B4 | 111.44 (11) | O2—C3—C1 | 121.19 (14) |
C3—C1—B6 | 113.67 (12) | O1—C3—C1 | 112.66 (13) |
C3—C1—B3 | 115.72 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.95 (3) | 1.72 (3) | 2.6655 (16) | 177 (2) |
Symmetry code: (i) −x+1, −y, −z. |
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The usefulness of heteroboranes in studies of crystal engineering has only recently begun to be exploited (Centore et al., 1994; Davidson et al., 1996; Hosmane et al., 1998; Lee et al., 2000), yet such compounds have a number of potential advantages in this respect. Heteroboranes are generally thermally and chemically stable compounds. They exist as polyhedra or fragments of polyhedra of differing size and shape, but have architectures that are well understood (Wade, 1976). Isomeric possibilities mean that C-substituted (hetero)carboranes have the potential to function as supramolecular building blocks with differing directionalities. Significant variation is also possible in the number and nature of the substituents that can be attached to the B atoms of heteroboranes, affording these species the potential to act as supramolecular building blocks in three dimensions. Finally, heteroboranes are usually neutral or anionic, but can also be cationic (see e.g. Douek & Welch, 1993).
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 chemistry of carboxylic acid carboranes and their derivatives. Herein, we describe the structure of the simplest carboxylic acid carborane, 1,2-dicarba-closo-dodecaborane(12)–1-carboxylic acid, (I). \sch
Compound (I) crystallizes as a dimer, linked by two O—H···O hydrogen bonds about a centre of inversion (Fig. 1), typical of the packing of carboxylic acid units (Leiserowitz, 1976). In graph-set terminology (Etter, 1990; Etter & MacDonald, 1990), this motif is denoted R22(8). The only other carboxylic acid carborane to be structurally characterized so far is 1,12-closo-C2B10H10-1,12-(COOH)2, (II) (Centore et al., 1994). In (II), the molecules pack as linear hydrogen-bonded chains. The dimensions of the hydrogen bond in (I) (Table 2) identify it as `strong' (Desiraju & Steiner, 1999) and bear good comparison with the corresponding O···O distance in (II) (2.639 Å).
In carboxylic acid derivatives of 1,2-dicarbaborane, we may define the orientation of the carboxylic acid group by θ, the C2—C1—C3—O2 dihedral angle. In compound (I), θ = 2.6 (2)°. This is complemented by a C1—C2 connectivity of length 1.632 (2) Å, in excellent agreement with that in the parent compound 1,2-closo-C2B10H12 [1.630 (6) Å; Davidson et al., 1996], and by a C1—C3 bond of 1.507 (2) Å.
The C—B distances span the range 1.690 (2)–1.729 (2) Å and the B—B distances 1.759 (2)–1.795 (3) Å. There is no evidence for disorder of the C2 vertex, identified on the twin bases of refined (as B) isotropic displacement parameters and intra-cage distances.