Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101005455/av1073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005455/av1073Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005455/av1073IIsup3.hkl |
CCDC references: 169939; 169940
1-Ph-1,7-C2B10H12 was prepared by thermal isomerization of 1-Ph-1,2-C2B10H12 (Garrett et al., 1964). 3-Ph-1,2-C2B10H12 was synthesized from phenylborondichloride and the C2B9H112- anion (Hawthorne & Wegner, 1968). Single crystals of both compounds suitable for X-ray analysis were grown from chloroform solution at room temperature by slow evaporation.
Data collection: SMART (Bruker, 1998) for (I); P3 (Siemens, 1989) for (II). Cell refinement: SMART and SAINT (Bruker, 1998) for (I); P3 for (II). Data reduction: SMART and SAINT for (I); XDISK (Siemens, 1991) for (II). For both compounds, program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8H16B10 | F(000) = 456 |
Mr = 220.31 | Dx = 1.157 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.378 (2) Å | Cell parameters from 890 reflections |
b = 9.725 (2) Å | θ = 2–26° |
c = 12.699 (3) Å | µ = 0.05 mm−1 |
β = 99.195 (7)° | T = 110 K |
V = 1265.2 (5) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.30 × 0.25 mm |
Bruker CCD area-detector diffractometer | 14343 independent reflections |
Radiation source: fine-focus sealed tube | 9409 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 52.8°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→22 |
Tmin = 0.981, Tmax = 0.987 | k = −21→21 |
49186 measured reflections | l = −28→28 |
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: difference Fourier map |
wR(F2) = 0.142 | All H-atom parameters refined |
S = 0.96 | w = 1/[σ2(Fo2) + (0.091P)2] where P = (Fo2 + 2Fc2)/3 |
14343 reflections | (Δ/σ)max = 0.002 |
227 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C8H16B10 | V = 1265.2 (5) Å3 |
Mr = 220.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.378 (2) Å | µ = 0.05 mm−1 |
b = 9.725 (2) Å | T = 110 K |
c = 12.699 (3) Å | 0.35 × 0.30 × 0.25 mm |
β = 99.195 (7)° |
Bruker CCD area-detector diffractometer | 14343 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 9409 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.987 | Rint = 0.029 |
49186 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.142 | All H-atom parameters refined |
S = 0.96 | Δρmax = 0.36 e Å−3 |
14343 reflections | Δρmin = −0.33 e Å−3 |
227 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 | 1.24045 (3) | 0.80396 (3) | 0.09214 (2) | 0.01477 (5) | |
C2 | 1.20780 (3) | 0.95720 (3) | 0.13098 (3) | 0.01530 (5) | |
B3 | 1.10964 (3) | 0.82234 (4) | 0.15962 (3) | 0.01400 (5) | |
B4 | 1.22352 (4) | 0.68390 (4) | 0.18512 (3) | 0.01651 (6) | |
B5 | 1.38035 (4) | 0.74066 (4) | 0.16422 (3) | 0.01815 (6) | |
B6 | 1.36813 (4) | 0.91672 (4) | 0.12627 (3) | 0.01795 (6) | |
B7 | 1.16472 (4) | 0.95464 (4) | 0.25411 (3) | 0.01742 (6) | |
B8 | 1.17774 (4) | 0.77874 (4) | 0.29255 (3) | 0.01754 (6) | |
B9 | 1.34401 (4) | 0.72776 (4) | 0.29611 (3) | 0.01902 (6) | |
B10 | 1.43317 (4) | 0.87223 (5) | 0.25915 (3) | 0.01882 (6) | |
B11 | 1.32181 (4) | 1.01233 (4) | 0.23361 (3) | 0.01885 (6) | |
B12 | 1.30759 (4) | 0.89564 (5) | 0.33901 (3) | 0.01945 (6) | |
C13 | 0.96548 (3) | 0.80352 (3) | 0.10199 (2) | 0.01426 (4) | |
C14 | 0.86335 (3) | 0.86694 (4) | 0.14379 (3) | 0.01851 (5) | |
C15 | 0.73308 (3) | 0.84313 (4) | 0.09995 (3) | 0.02150 (6) | |
C16 | 0.70241 (4) | 0.75676 (4) | 0.01237 (3) | 0.02146 (6) | |
C17 | 0.80224 (4) | 0.69433 (4) | −0.03122 (3) | 0.02160 (6) | |
C18 | 0.93247 (3) | 0.71646 (4) | 0.01381 (3) | 0.01801 (5) | |
H1 | 1.2177 (8) | 0.7865 (8) | 0.0213 (6) | 0.0222 (17)* | |
H2 | 1.1684 (8) | 1.0168 (9) | 0.0791 (6) | 0.0247 (18)* | |
H4 | 1.1882 (9) | 0.5821 (10) | 0.1564 (8) | 0.032 (2)* | |
H5 | 1.4354 (8) | 0.6721 (9) | 0.1231 (7) | 0.0283 (19)* | |
H6 | 1.4114 (8) | 0.9573 (9) | 0.0642 (7) | 0.0282 (19)* | |
H7 | 1.0955 (8) | 1.0270 (9) | 0.2715 (7) | 0.0286 (19)* | |
H8 | 1.1161 (9) | 0.7299 (10) | 0.3432 (7) | 0.033 (2)* | |
H9 | 1.3884 (8) | 0.6487 (9) | 0.3515 (7) | 0.0292 (19)* | |
H10 | 1.5416 (10) | 0.8969 (11) | 0.2922 (8) | 0.041 (2)* | |
H11 | 1.3442 (8) | 1.1217 (10) | 0.2343 (7) | 0.034 (2)* | |
H12 | 1.3303 (10) | 0.9245 (12) | 0.4235 (8) | 0.044 (3)* | |
H14 | 0.8766 (9) | 0.9265 (10) | 0.2005 (8) | 0.036 (2)* | |
H15 | 0.6628 (9) | 0.8845 (10) | 0.1300 (8) | 0.034 (2)* | |
H16 | 0.6132 (9) | 0.7400 (10) | −0.0182 (7) | 0.036 (2)* | |
H17 | 0.7829 (9) | 0.6346 (11) | −0.0924 (8) | 0.042 (3)* | |
H18 | 1.0043 (9) | 0.6685 (10) | −0.0176 (7) | 0.031 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.01409 (10) | 0.01814 (11) | 0.01204 (9) | 0.00138 (8) | 0.00195 (7) | −0.00007 (8) |
C2 | 0.01440 (10) | 0.01485 (10) | 0.01605 (10) | 0.00001 (7) | 0.00066 (8) | 0.00212 (8) |
B3 | 0.01407 (11) | 0.01481 (12) | 0.01327 (11) | 0.00044 (8) | 0.00258 (9) | −0.00039 (9) |
B4 | 0.01866 (13) | 0.01454 (12) | 0.01619 (12) | 0.00203 (9) | 0.00236 (10) | 0.00062 (9) |
B5 | 0.01582 (13) | 0.02129 (15) | 0.01707 (13) | 0.00436 (10) | 0.00178 (10) | −0.00009 (11) |
B6 | 0.01406 (12) | 0.02239 (15) | 0.01705 (13) | −0.00064 (10) | 0.00138 (10) | 0.00302 (11) |
B7 | 0.01761 (13) | 0.01739 (13) | 0.01703 (13) | 0.00130 (10) | 0.00203 (10) | −0.00352 (10) |
B8 | 0.02001 (14) | 0.02026 (14) | 0.01261 (11) | 0.00021 (11) | 0.00341 (10) | 0.00108 (10) |
B9 | 0.02036 (15) | 0.02006 (15) | 0.01571 (12) | 0.00318 (11) | 0.00002 (11) | 0.00342 (11) |
B10 | 0.01565 (13) | 0.02271 (16) | 0.01684 (13) | 0.00105 (10) | −0.00125 (10) | 0.00081 (11) |
B11 | 0.01755 (13) | 0.01732 (14) | 0.02036 (14) | −0.00126 (10) | −0.00096 (11) | −0.00093 (11) |
B12 | 0.02049 (15) | 0.02306 (16) | 0.01384 (12) | 0.00072 (11) | −0.00023 (11) | −0.00212 (11) |
C13 | 0.01377 (10) | 0.01490 (10) | 0.01437 (10) | −0.00005 (7) | 0.00302 (8) | −0.00003 (8) |
C14 | 0.01540 (11) | 0.02251 (14) | 0.01806 (12) | 0.00168 (9) | 0.00402 (9) | −0.00252 (10) |
C15 | 0.01455 (11) | 0.02653 (16) | 0.02398 (14) | 0.00172 (10) | 0.00479 (10) | 0.00053 (12) |
C16 | 0.01550 (11) | 0.02233 (14) | 0.02572 (15) | −0.00283 (9) | 0.00075 (11) | 0.00207 (11) |
C17 | 0.01921 (13) | 0.02031 (13) | 0.02405 (14) | −0.00305 (10) | −0.00034 (11) | −0.00406 (11) |
C18 | 0.01683 (11) | 0.01804 (12) | 0.01914 (12) | −0.00088 (8) | 0.00283 (9) | −0.00380 (9) |
C1—C2 | 1.6225 (5) | B9—B10 | 1.7858 (7) |
C1—B4 | 1.6895 (5) | B10—B11 | 1.7825 (6) |
C1—B5 | 1.7030 (6) | B10—B12 | 1.7891 (7) |
C1—B6 | 1.7213 (6) | B11—B12 | 1.7788 (7) |
C1—B3 | 1.7265 (5) | C13—C14 | 1.4019 (5) |
C2—B7 | 1.6937 (6) | C13—C18 | 1.4020 (5) |
C2—B11 | 1.7010 (6) | C14—C15 | 1.3967 (6) |
C2—B6 | 1.7201 (6) | C15—C16 | 1.3895 (6) |
C2—B3 | 1.7345 (5) | C16—C17 | 1.3898 (6) |
B3—C13 | 1.5676 (5) | C17—C18 | 1.3975 (6) |
B3—B8 | 1.7742 (6) | C1—H1 | 0.909 (8) |
B3—B4 | 1.7865 (6) | C2—H2 | 0.922 (8) |
B3—B7 | 1.7896 (6) | B4—H4 | 1.098 (9) |
B4—B8 | 1.7734 (6) | B5—H5 | 1.068 (9) |
B4—B5 | 1.7782 (7) | B6—H6 | 1.045 (9) |
B4—B9 | 1.7801 (6) | B7—H7 | 1.054 (9) |
B5—B6 | 1.7778 (7) | B8—H8 | 1.087 (9) |
B5—B9 | 1.7791 (7) | B9—H9 | 1.093 (9) |
B5—B10 | 1.7833 (6) | B10—H10 | 1.162 (10) |
B6—B10 | 1.7683 (7) | B11—H11 | 1.089 (9) |
B6—B11 | 1.7785 (7) | B12—H12 | 1.097 (10) |
B7—B8 | 1.7782 (7) | C14—H14 | 0.917 (10) |
B7—B11 | 1.7820 (7) | C15—H15 | 0.963 (9) |
B7—B12 | 1.7830 (6) | C16—H16 | 0.959 (9) |
B8—B12 | 1.7896 (6) | C17—H17 | 0.965 (10) |
B8—B9 | 1.7889 (7) | C18—H18 | 1.013 (9) |
B9—B12 | 1.7807 (7) | ||
C2—C1—B4 | 111.85 (3) | B11—B10—B9 | 107.52 (3) |
C2—C1—B5 | 111.72 (3) | B5—B10—B9 | 59.80 (3) |
B4—C1—B5 | 63.22 (2) | B6—B10—B12 | 107.95 (3) |
C2—C1—B6 | 61.83 (2) | B11—B10—B12 | 59.74 (3) |
B4—C1—B6 | 115.22 (3) | B5—B10—B12 | 107.55 (3) |
B5—C1—B6 | 62.55 (3) | B9—B10—B12 | 59.75 (3) |
C2—C1—B3 | 62.29 (2) | C2—B11—B6 | 59.20 (2) |
B4—C1—B3 | 63.06 (2) | C2—B11—B12 | 104.14 (3) |
B5—C1—B3 | 116.17 (3) | B6—B11—B12 | 107.96 (3) |
B6—C1—B3 | 116.34 (3) | C2—B11—B7 | 58.14 (2) |
C1—C2—B7 | 111.46 (3) | B6—B11—B7 | 108.24 (3) |
C1—C2—B11 | 111.65 (3) | B12—B11—B7 | 60.10 (2) |
B7—C2—B11 | 63.33 (3) | C2—B11—B10 | 104.47 (3) |
C1—C2—B6 | 61.91 (2) | B6—B11—B10 | 59.54 (3) |
B7—C2—B6 | 115.35 (3) | B12—B11—B10 | 60.32 (3) |
B11—C2—B6 | 62.65 (3) | B7—B11—B10 | 108.33 (3) |
C1—C2—B3 | 61.79 (2) | B11—B12—B9 | 107.91 (3) |
B7—C2—B3 | 62.92 (2) | B11—B12—B7 | 60.04 (3) |
B11—C2—B3 | 115.95 (3) | B9—B12—B7 | 107.85 (3) |
B6—C2—B3 | 115.98 (3) | B11—B12—B10 | 59.95 (3) |
C13—B3—C1 | 121.57 (3) | B9—B12—B10 | 60.03 (2) |
C13—B3—C2 | 122.61 (3) | B7—B12—B10 | 107.99 (3) |
C1—B3—C2 | 55.91 (2) | B11—B12—B8 | 107.81 (3) |
C13—B3—B8 | 128.44 (3) | B9—B12—B8 | 60.14 (3) |
C1—B3—B8 | 102.85 (3) | B7—B12—B8 | 59.70 (3) |
C2—B3—B8 | 102.84 (3) | B10—B12—B8 | 108.10 (3) |
C13—B3—B4 | 123.43 (3) | C14—C13—C18 | 117.71 (3) |
C1—B3—B4 | 57.46 (2) | C14—C13—B3 | 119.65 (3) |
C2—B3—B4 | 102.37 (3) | C18—C13—B3 | 122.45 (3) |
B8—B3—B4 | 59.74 (2) | C15—C14—C13 | 121.22 (4) |
C13—B3—B7 | 125.15 (3) | C16—C15—C14 | 120.17 (3) |
C1—B3—B7 | 102.42 (3) | C17—C16—C15 | 119.54 (4) |
C2—B3—B7 | 57.43 (2) | C16—C17—C18 | 120.23 (4) |
B8—B3—B7 | 59.86 (2) | C17—C18—C13 | 121.12 (3) |
B4—B3—B7 | 106.80 (3) | C2—C1—H1 | 116.0 (5) |
C1—B4—B8 | 104.41 (3) | B4—C1—H1 | 121.5 (5) |
C1—B4—B5 | 58.76 (2) | B5—C1—H1 | 121.9 (5) |
B8—B4—B5 | 108.52 (3) | B6—C1—H1 | 115.9 (5) |
C1—B4—B9 | 104.45 (3) | B3—C1—H1 | 114.2 (5) |
B8—B4—B9 | 60.45 (3) | C1—C2—H2 | 116.8 (5) |
B5—B4—B9 | 60.00 (3) | B7—C2—H2 | 121.1 (5) |
C1—B4—B3 | 59.48 (2) | B11—C2—H2 | 121.6 (5) |
B8—B4—B3 | 59.78 (2) | B6—C2—H2 | 116.1 (5) |
B5—B4—B3 | 109.50 (3) | B3—C2—H2 | 114.6 (5) |
B9—B4—B3 | 108.88 (3) | C1—B4—H4 | 117.3 (5) |
C1—B5—B6 | 59.23 (2) | B8—B4—H4 | 127.4 (5) |
C1—B5—B4 | 58.02 (2) | B5—B4—H4 | 119.7 (5) |
B6—B5—B4 | 108.18 (3) | B9—B4—H4 | 129.4 (5) |
C1—B5—B9 | 103.93 (3) | B3—B4—H4 | 116.3 (5) |
B6—B5—B9 | 107.84 (3) | C1—B5—H5 | 116.1 (5) |
B4—B5—B9 | 60.05 (2) | B6—B5—H5 | 119.3 (5) |
C1—B5—B10 | 104.34 (3) | B4—B5—H5 | 117.0 (5) |
B6—B5—B10 | 59.54 (3) | B9—B5—H5 | 128.9 (5) |
B4—B5—B10 | 108.15 (3) | B10—B5—H5 | 130.4 (5) |
B9—B5—B10 | 60.17 (3) | C2—B6—H6 | 118.3 (5) |
C2—B6—C1 | 56.26 (2) | C1—B6—H6 | 117.2 (5) |
C2—B6—B10 | 104.28 (3) | B10—B6—H6 | 131.9 (5) |
C1—B6—B10 | 104.21 (3) | B5—B6—H6 | 123.2 (5) |
C2—B6—B5 | 103.80 (3) | B11—B6—H6 | 125.6 (5) |
C1—B6—B5 | 58.22 (2) | C2—B7—H7 | 118.2 (5) |
B10—B6—B5 | 60.38 (2) | B8—B7—H7 | 127.6 (5) |
C2—B6—B11 | 58.15 (2) | B11—B7—H7 | 119.3 (5) |
C1—B6—B11 | 103.57 (3) | B12—B7—H7 | 128.1 (5) |
B10—B6—B11 | 60.34 (3) | B3—B7—H7 | 117.7 (5) |
B5—B6—B11 | 108.18 (3) | B4—B8—H8 | 118.9 (5) |
C2—B7—B8 | 104.36 (3) | B3—B8—H8 | 119.0 (5) |
C2—B7—B11 | 58.53 (2) | B7—B8—H8 | 123.9 (5) |
B8—B7—B11 | 108.17 (3) | B12—B8—H8 | 124.5 (5) |
C2—B7—B12 | 104.26 (3) | B9—B8—H8 | 121.4 (5) |
B8—B7—B12 | 60.33 (2) | B4—B9—H9 | 120.8 (5) |
B11—B7—B12 | 59.86 (3) | B5—B9—H9 | 121.6 (5) |
C2—B7—B3 | 59.65 (2) | B12—B9—H9 | 122.4 (5) |
B8—B7—B3 | 59.64 (2) | B10—B9—H9 | 122.7 (5) |
B11—B7—B3 | 109.27 (3) | B8—B9—H9 | 121.1 (5) |
B12—B7—B3 | 108.65 (3) | B6—B10—H10 | 119.6 (5) |
B4—B8—B3 | 60.48 (2) | B11—B10—H10 | 118.0 (5) |
B4—B8—B7 | 107.88 (3) | B5—B10—H10 | 124.6 (5) |
B3—B8—B7 | 60.50 (2) | B9—B10—H10 | 125.5 (5) |
B4—B8—B12 | 107.68 (3) | B12—B10—H10 | 121.4 (5) |
B3—B8—B12 | 109.04 (3) | C2—B11—H11 | 115.8 (5) |
B7—B8—B12 | 59.97 (2) | B6—B11—H11 | 115.7 (5) |
B4—B8—B9 | 59.96 (2) | B12—B11—H11 | 131.3 (5) |
B3—B8—B9 | 109.04 (3) | B7—B11—H11 | 120.4 (5) |
B7—B8—B9 | 107.71 (3) | B10—B11—H11 | 127.9 (5) |
B12—B8—B9 | 59.68 (3) | B11—B12—H12 | 122.8 (6) |
B4—B9—B5 | 59.95 (3) | B9—B12—H12 | 120.7 (6) |
B4—B9—B12 | 107.78 (3) | B7—B12—H12 | 122.5 (5) |
B5—B9—B12 | 108.10 (3) | B10—B12—H12 | 121.6 (5) |
B4—B9—B10 | 107.96 (3) | B8—B12—H12 | 121.2 (6) |
B5—B9—B10 | 60.03 (2) | C15—C14—H14 | 115.6 (6) |
B12—B9—B10 | 60.22 (3) | C13—C14—H14 | 123.2 (6) |
B4—B9—B8 | 59.59 (2) | C16—C15—H15 | 118.6 (5) |
B5—B9—B8 | 107.79 (3) | C14—C15—H15 | 121.2 (5) |
B12—B9—B8 | 60.18 (2) | C17—C16—H16 | 119.8 (6) |
B10—B9—B8 | 108.28 (3) | C15—C16—H16 | 120.6 (6) |
B6—B10—B11 | 60.12 (2) | C16—C17—H17 | 120.7 (6) |
B6—B10—B5 | 60.07 (3) | C18—C17—H17 | 119.0 (6) |
B11—B10—B5 | 107.76 (3) | C17—C18—H18 | 119.5 (5) |
B6—B10—B9 | 107.97 (3) | C13—C18—H18 | 119.4 (5) |
C8H16B10 | F(000) = 456 |
Mr = 220.31 | Dx = 1.131 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.350 (2) Å | Cell parameters from 24 reflections |
b = 9.449 (2) Å | θ = 10–14° |
c = 13.763 (3) Å | µ = 0.05 mm−1 |
β = 106.07 (3)° | T = 163 K |
V = 1293.4 (5) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Syntex P21 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 33.1°, θmin = 2.1° |
Graphite monochromator | h = 0→15 |
θ/2θ scans | k = 0→14 |
5094 measured reflections | l = −21→20 |
4872 independent reflections | 2 standard reflections every 98 reflections |
2765 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.049 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.115 | All H-atom parameters refined |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0599P)2] where P = (Fo2 + 2Fc2)/3 |
4872 reflections | (Δ/σ)max = 0.013 |
227 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C8H16B10 | V = 1293.4 (5) Å3 |
Mr = 220.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.350 (2) Å | µ = 0.05 mm−1 |
b = 9.449 (2) Å | T = 163 K |
c = 13.763 (3) Å | 0.30 × 0.25 × 0.20 mm |
β = 106.07 (3)° |
Syntex P21 diffractometer | Rint = 0.027 |
5094 measured reflections | 2 standard reflections every 98 reflections |
4872 independent reflections | intensity decay: 2% |
2765 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.115 | All H-atom parameters refined |
S = 0.88 | Δρmax = 0.24 e Å−3 |
4872 reflections | Δρmin = −0.19 e Å−3 |
227 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 | 0.11330 (9) | 0.79918 (10) | 0.15227 (7) | 0.01994 (18) | |
B2 | 0.18872 (12) | 0.93738 (12) | 0.10912 (10) | 0.0299 (3) | |
B3 | 0.17182 (12) | 0.93599 (12) | 0.23484 (10) | 0.0306 (3) | |
B4 | 0.18679 (12) | 0.75911 (13) | 0.27811 (8) | 0.0258 (2) | |
B5 | 0.21528 (11) | 0.65235 (11) | 0.18036 (8) | 0.0218 (2) | |
B6 | 0.21632 (11) | 0.76201 (13) | 0.07613 (8) | 0.0243 (2) | |
C7 | 0.31989 (11) | 0.97321 (11) | 0.21124 (9) | 0.0326 (3) | |
B8 | 0.32415 (13) | 0.87657 (14) | 0.31775 (9) | 0.0318 (3) | |
B9 | 0.35190 (12) | 0.70096 (13) | 0.28417 (9) | 0.0271 (2) | |
B10 | 0.36966 (12) | 0.70236 (13) | 0.15896 (9) | 0.0262 (2) | |
B11 | 0.35348 (12) | 0.87972 (14) | 0.11519 (10) | 0.0310 (3) | |
B12 | 0.43674 (12) | 0.84214 (13) | 0.24368 (9) | 0.0283 (2) | |
C13 | −0.03650 (9) | 0.77803 (9) | 0.11114 (7) | 0.02143 (19) | |
C14 | −0.08867 (11) | 0.68737 (11) | 0.03010 (9) | 0.0295 (2) | |
C15 | −0.22652 (11) | 0.66869 (12) | −0.00695 (9) | 0.0356 (3) | |
C16 | −0.31412 (11) | 0.73960 (12) | 0.03500 (9) | 0.0345 (3) | |
C17 | −0.26324 (11) | 0.82824 (13) | 0.11603 (10) | 0.0379 (3) | |
C18 | −0.12520 (11) | 0.84732 (12) | 0.15398 (9) | 0.0317 (2) | |
H2 | 0.1344 (13) | 1.0149 (15) | 0.0611 (9) | 0.044 (4)* | |
H3 | 0.1099 (13) | 1.0152 (15) | 0.2538 (10) | 0.046 (4)* | |
H4 | 0.1232 (13) | 0.7210 (14) | 0.3219 (9) | 0.043 (4)* | |
H5 | 0.1683 (11) | 0.5488 (13) | 0.1685 (8) | 0.029 (3)* | |
H6 | 0.1721 (12) | 0.7259 (13) | 0.0002 (9) | 0.032 (3)* | |
H7 | 0.3498 (12) | 1.0689 (14) | 0.2189 (9) | 0.039 (3)* | |
H8 | 0.3610 (13) | 0.9281 (14) | 0.3913 (10) | 0.046 (4)* | |
H9 | 0.4044 (12) | 0.6251 (14) | 0.3424 (9) | 0.038 (3)* | |
H10 | 0.4335 (12) | 0.6257 (13) | 0.1320 (9) | 0.038 (3)* | |
H11 | 0.4063 (13) | 0.9318 (14) | 0.0653 (10) | 0.045 (4)* | |
H12 | 0.5409 (12) | 0.8710 (14) | 0.2736 (9) | 0.042 (4)* | |
H14 | −0.0284 (13) | 0.6428 (14) | −0.0007 (10) | 0.040 (4)* | |
H15 | −0.2622 (13) | 0.6083 (15) | −0.0682 (10) | 0.048 (4)* | |
H16 | −0.4081 (13) | 0.7236 (13) | 0.0110 (9) | 0.037 (3)* | |
H17 | −0.3205 (14) | 0.8783 (16) | 0.1505 (11) | 0.056 (4)* | |
H18 | −0.0924 (12) | 0.9114 (14) | 0.2080 (10) | 0.040 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0214 (4) | 0.0172 (4) | 0.0208 (4) | 0.0001 (3) | 0.0051 (3) | −0.0002 (3) |
B2 | 0.0246 (5) | 0.0232 (5) | 0.0382 (7) | −0.0009 (4) | 0.0022 (5) | 0.0099 (5) |
B3 | 0.0266 (6) | 0.0229 (5) | 0.0393 (7) | 0.0001 (4) | 0.0042 (5) | −0.0093 (5) |
B4 | 0.0291 (5) | 0.0293 (5) | 0.0186 (5) | −0.0005 (5) | 0.0059 (4) | −0.0029 (4) |
B5 | 0.0252 (5) | 0.0196 (5) | 0.0203 (5) | 0.0023 (4) | 0.0059 (4) | 0.0000 (4) |
B6 | 0.0224 (5) | 0.0310 (6) | 0.0196 (5) | −0.0004 (4) | 0.0059 (4) | 0.0040 (4) |
C7 | 0.0255 (5) | 0.0202 (5) | 0.0467 (7) | −0.0024 (4) | 0.0010 (4) | 0.0008 (4) |
B8 | 0.0298 (6) | 0.0332 (6) | 0.0286 (6) | −0.0014 (5) | 0.0019 (5) | −0.0097 (5) |
B9 | 0.0285 (6) | 0.0269 (5) | 0.0228 (5) | 0.0019 (4) | 0.0020 (4) | 0.0024 (4) |
B10 | 0.0236 (5) | 0.0282 (5) | 0.0262 (5) | 0.0028 (4) | 0.0057 (4) | 0.0005 (4) |
B11 | 0.0227 (5) | 0.0351 (6) | 0.0336 (6) | −0.0021 (5) | 0.0050 (5) | 0.0111 (5) |
B12 | 0.0226 (5) | 0.0267 (5) | 0.0317 (6) | 0.0004 (4) | 0.0009 (4) | 0.0008 (5) |
C13 | 0.0215 (4) | 0.0182 (4) | 0.0240 (4) | −0.0005 (3) | 0.0053 (3) | 0.0006 (3) |
C14 | 0.0250 (5) | 0.0259 (5) | 0.0365 (6) | 0.0011 (4) | 0.0067 (4) | −0.0086 (4) |
C15 | 0.0266 (5) | 0.0341 (6) | 0.0422 (6) | −0.0036 (4) | 0.0032 (5) | −0.0122 (5) |
C16 | 0.0218 (5) | 0.0333 (5) | 0.0462 (7) | −0.0016 (4) | 0.0059 (4) | −0.0012 (5) |
C17 | 0.0254 (5) | 0.0417 (6) | 0.0496 (7) | 0.0014 (5) | 0.0153 (5) | −0.0096 (5) |
C18 | 0.0270 (5) | 0.0340 (5) | 0.0355 (6) | −0.0012 (4) | 0.0107 (4) | −0.0105 (5) |
C1—C13 | 1.5095 (13) | B9—B10 | 1.7829 (18) |
C1—B2 | 1.7100 (15) | B10—B12 | 1.7714 (17) |
C1—B3 | 1.7170 (15) | B10—B11 | 1.7731 (18) |
C1—B5 | 1.7212 (14) | B11—B12 | 1.7755 (18) |
C1—B6 | 1.7254 (15) | C13—C18 | 1.3852 (14) |
C1—B4 | 1.7297 (15) | C13—C14 | 1.3913 (14) |
B2—C7 | 1.6961 (17) | C14—C15 | 1.3872 (15) |
B2—B6 | 1.7622 (18) | C15—C16 | 1.3762 (17) |
B2—B11 | 1.7699 (18) | C16—C17 | 1.3775 (17) |
B2—B3 | 1.787 (2) | C17—C18 | 1.3905 (16) |
B3—C7 | 1.6893 (18) | B2—H2 | 1.041 (13) |
B3—B8 | 1.7628 (18) | B3—H3 | 1.064 (14) |
B3—B4 | 1.7666 (17) | B4—H4 | 1.070 (13) |
B4—B8 | 1.7667 (18) | B5—H5 | 1.085 (12) |
B4—B5 | 1.7703 (16) | B6—H6 | 1.074 (12) |
B4—B9 | 1.7749 (18) | C7—H7 | 0.952 (13) |
B5—B10 | 1.7675 (17) | B8—H8 | 1.092 (13) |
B5—B9 | 1.7702 (17) | B9—H9 | 1.100 (12) |
B5—B6 | 1.7720 (15) | B10—H10 | 1.111 (12) |
B6—B11 | 1.7661 (17) | B11—H11 | 1.104 (13) |
B6—B10 | 1.7705 (16) | B12—H12 | 1.078 (12) |
C7—B12 | 1.7020 (16) | C14—H14 | 0.945 (13) |
C7—B11 | 1.7038 (19) | C15—H15 | 1.000 (14) |
C7—B8 | 1.7173 (18) | C16—H16 | 0.949 (12) |
B8—B9 | 1.7671 (18) | C17—H17 | 0.978 (15) |
B8—B12 | 1.7778 (19) | C18—H18 | 0.946 (13) |
B9—B12 | 1.7697 (18) | ||
C13—C1—B2 | 119.41 (8) | B6—B10—B11 | 59.79 (7) |
C13—C1—B3 | 119.04 (8) | B12—B10—B11 | 60.12 (7) |
B2—C1—B3 | 62.84 (8) | B5—B10—B9 | 59.81 (7) |
C13—C1—B5 | 118.68 (8) | B6—B10—B9 | 108.11 (9) |
B2—C1—B5 | 112.52 (8) | B12—B10—B9 | 59.72 (7) |
B3—C1—B5 | 112.10 (8) | B11—B10—B9 | 108.06 (9) |
C13—C1—B6 | 119.25 (8) | C7—B11—B6 | 104.08 (9) |
B2—C1—B6 | 61.72 (7) | C7—B11—B2 | 58.42 (7) |
B3—C1—B6 | 113.02 (8) | B6—B11—B2 | 59.78 (7) |
B5—C1—B6 | 61.88 (6) | C7—B11—B10 | 104.29 (9) |
C13—C1—B4 | 117.90 (8) | B6—B11—B10 | 60.03 (7) |
B2—C1—B4 | 113.48 (8) | B2—B11—B10 | 107.83 (9) |
B3—C1—B4 | 61.67 (7) | C7—B11—B12 | 58.53 (7) |
B5—C1—B4 | 61.73 (6) | B6—B11—B12 | 107.75 (9) |
B6—C1—B4 | 112.90 (8) | B2—B11—B12 | 107.71 (10) |
C7—B2—C1 | 101.67 (8) | B10—B11—B12 | 59.89 (7) |
C7—B2—B6 | 104.57 (8) | C7—B12—B9 | 104.63 (9) |
C1—B2—B6 | 59.57 (6) | C7—B12—B10 | 104.44 (8) |
C7—B2—B11 | 58.84 (7) | B9—B12—B10 | 60.46 (7) |
C1—B2—B11 | 105.97 (8) | C7—B12—B8 | 59.09 (7) |
B6—B2—B11 | 60.00 (7) | B9—B12—B8 | 59.75 (7) |
C7—B2—B3 | 57.96 (7) | B10—B12—B8 | 108.31 (9) |
C1—B2—B3 | 58.77 (7) | C7—B12—B11 | 58.63 (7) |
B6—B2—B3 | 107.99 (8) | B9—B12—B11 | 108.55 (8) |
B11—B2—B3 | 107.66 (9) | B10—B12—B11 | 59.99 (7) |
C7—B3—C1 | 101.66 (9) | B8—B12—B11 | 108.67 (9) |
C7—B3—B8 | 59.62 (7) | C18—C13—C14 | 118.45 (10) |
C1—B3—B8 | 106.08 (8) | C18—C13—C1 | 120.71 (9) |
C7—B3—B4 | 105.20 (8) | C14—C13—C1 | 120.83 (9) |
C1—B3—B4 | 59.52 (6) | C15—C14—C13 | 120.30 (11) |
B8—B3—B4 | 60.07 (7) | C16—C15—C14 | 120.92 (10) |
C7—B3—B2 | 58.33 (8) | C15—C16—C17 | 119.15 (11) |
C1—B3—B2 | 58.39 (6) | C16—C17—C18 | 120.38 (11) |
B8—B3—B2 | 108.63 (9) | C13—C18—C17 | 120.80 (10) |
B4—B3—B2 | 108.08 (8) | C7—B2—H2 | 123.6 (7) |
C1—B4—B3 | 58.81 (6) | C1—B2—H2 | 122.6 (7) |
C1—B4—B8 | 105.37 (9) | B6—B2—H2 | 126.6 (7) |
B3—B4—B8 | 59.86 (7) | B11—B2—H2 | 126.2 (7) |
C1—B4—B5 | 58.90 (6) | B3—B2—H2 | 116.0 (7) |
B3—B4—B5 | 107.49 (8) | C7—B3—H3 | 122.7 (7) |
B8—B4—B5 | 107.67 (9) | C1—B3—H3 | 124.5 (7) |
C1—B4—B9 | 105.41 (8) | B8—B3—H3 | 123.8 (7) |
B3—B4—B9 | 107.59 (9) | B4—B3—H3 | 125.8 (7) |
B8—B4—B9 | 59.86 (7) | B2—B3—H3 | 117.4 (7) |
B5—B4—B9 | 59.91 (7) | C1—B4—H4 | 118.0 (7) |
C1—B5—B4 | 59.37 (6) | B3—B4—H4 | 119.8 (7) |
C1—B5—B10 | 105.88 (8) | B8—B4—H4 | 127.2 (7) |
B4—B5—B10 | 108.82 (8) | B5—B4—H4 | 119.6 (7) |
C1—B5—B9 | 105.98 (8) | B9—B4—H4 | 127.1 (7) |
B4—B5—B9 | 60.17 (7) | C1—B5—H5 | 118.1 (6) |
B10—B5—B9 | 60.53 (7) | B4—B5—H5 | 117.8 (6) |
C1—B5—B6 | 59.18 (6) | B10—B5—H5 | 127.2 (6) |
B4—B5—B6 | 108.76 (8) | B9—B5—H5 | 125.5 (6) |
B10—B5—B6 | 60.03 (7) | B6—B5—H5 | 120.6 (6) |
B9—B5—B6 | 108.61 (8) | C1—B6—H6 | 119.2 (6) |
C1—B6—B2 | 58.71 (6) | B2—B6—H6 | 119.6 (6) |
C1—B6—B11 | 105.47 (8) | B11—B6—H6 | 125.9 (7) |
B2—B6—B11 | 60.22 (7) | B10—B6—H6 | 126.2 (6) |
C1—B6—B10 | 105.56 (8) | B5—B6—H6 | 120.4 (7) |
B2—B6—B10 | 108.29 (8) | B3—C7—H7 | 117.4 (8) |
B11—B6—B10 | 60.18 (7) | B2—C7—H7 | 116.3 (7) |
C1—B6—B5 | 58.94 (6) | B12—C7—H7 | 118.5 (7) |
B2—B6—B5 | 107.67 (8) | B11—C7—H7 | 116.7 (8) |
B11—B6—B5 | 107.84 (8) | B8—C7—H7 | 118.7 (8) |
B10—B6—B5 | 59.86 (7) | C7—B8—H8 | 118.3 (7) |
B3—C7—B2 | 63.71 (8) | B3—B8—H8 | 118.5 (7) |
B3—C7—B12 | 114.50 (9) | B4—B8—H8 | 127.7 (7) |
B2—C7—B12 | 114.82 (9) | B9—B8—H8 | 128.4 (7) |
B3—C7—B11 | 115.60 (9) | B12—B8—H8 | 119.8 (7) |
B2—C7—B11 | 62.74 (7) | B8—B9—H9 | 120.3 (7) |
B12—C7—B11 | 62.84 (7) | B12—B9—H9 | 122.2 (7) |
B3—C7—B8 | 62.32 (8) | B5—B9—H9 | 122.8 (7) |
B2—C7—B8 | 115.26 (9) | B4—B9—H9 | 120.7 (6) |
B12—C7—B8 | 62.66 (8) | B10—B9—H9 | 123.2 (7) |
B11—C7—B8 | 115.09 (9) | B5—B10—H10 | 122.0 (6) |
C7—B8—B3 | 58.06 (7) | B6—B10—H10 | 120.2 (6) |
C7—B8—B4 | 104.01 (8) | B12—B10—H10 | 123.0 (6) |
B3—B8—B4 | 60.07 (7) | B11—B10—H10 | 120.8 (6) |
C7—B8—B9 | 104.10 (9) | B9—B10—H10 | 123.2 (6) |
B3—B8—B9 | 108.11 (8) | C7—B11—H11 | 119.6 (7) |
B4—B8—B9 | 60.30 (7) | B6—B11—H11 | 125.9 (7) |
C7—B8—B12 | 58.25 (7) | B2—B11—H11 | 118.0 (7) |
B3—B8—B12 | 107.33 (9) | B10—B11—H11 | 128.0 (7) |
B4—B8—B12 | 107.89 (8) | B12—B11—H11 | 121.4 (7) |
B9—B8—B12 | 59.90 (7) | C7—B12—H12 | 118.7 (7) |
B8—B9—B12 | 60.35 (7) | B9—B12—H12 | 127.0 (7) |
B8—B9—B5 | 107.66 (8) | B10—B12—H12 | 127.5 (7) |
B12—B9—B5 | 107.25 (8) | B8—B12—H12 | 118.7 (7) |
B8—B9—B4 | 59.84 (7) | B11—B12—H12 | 119.3 (7) |
B12—B9—B4 | 107.88 (8) | C15—C14—H14 | 121.2 (8) |
B5—B9—B4 | 59.92 (7) | C13—C14—H14 | 118.4 (8) |
B8—B9—B10 | 108.27 (9) | C16—C15—H15 | 119.9 (8) |
B12—B9—B10 | 59.81 (7) | C14—C15—H15 | 119.0 (8) |
B5—B9—B10 | 59.66 (7) | C15—C16—H16 | 120.5 (8) |
B4—B9—B10 | 107.92 (8) | C17—C16—H16 | 120.3 (8) |
B5—B10—B6 | 60.11 (6) | C16—C17—H17 | 122.7 (9) |
B5—B10—B12 | 107.30 (9) | C18—C17—H17 | 116.9 (9) |
B6—B10—B12 | 107.73 (9) | C13—C18—H18 | 120.1 (8) |
B5—B10—B11 | 107.73 (8) | C17—C18—H18 | 119.1 (8) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C8H16B10 | C8H16B10 |
Mr | 220.31 | 220.31 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 110 | 163 |
a, b, c (Å) | 10.378 (2), 9.725 (2), 12.699 (3) | 10.350 (2), 9.449 (2), 13.763 (3) |
β (°) | 99.195 (7) | 106.07 (3) |
V (Å3) | 1265.2 (5) | 1293.4 (5) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.05 | 0.05 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 | 0.30 × 0.25 × 0.20 |
Data collection | ||
Diffractometer | Bruker CCD area-detector diffractometer | Syntex P21 diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | – |
Tmin, Tmax | 0.981, 0.987 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49186, 14343, 9409 | 5094, 4872, 2765 |
Rint | 0.029 | 0.027 |
(sin θ/λ)max (Å−1) | 1.121 | 0.768 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.142, 0.96 | 0.049, 0.115, 0.88 |
No. of reflections | 14343 | 4872 |
No. of parameters | 227 | 227 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.36, −0.33 | 0.24, −0.19 |
Computer programs: SMART (Bruker, 1998), P3 (Siemens, 1989), SMART and SAINT (Bruker, 1998), P3, SMART and SAINT, XDISK (Siemens, 1991), SHELXTL (Bruker, 1998), SHELXTL.
C1—C2 | 1.6225 (5) | B4—B8 | 1.7734 (6) |
C1—B4 | 1.6895 (5) | B5—B6 | 1.7778 (7) |
C1—B5 | 1.7030 (6) | B5—B10 | 1.7833 (6) |
C1—B6 | 1.7213 (6) | B6—B10 | 1.7683 (7) |
C1—B3 | 1.7265 (5) | B6—B11 | 1.7785 (7) |
C2—B7 | 1.6937 (6) | B7—B8 | 1.7782 (7) |
C2—B11 | 1.7010 (6) | B10—B11 | 1.7825 (6) |
C2—B6 | 1.7201 (6) | C13—C14 | 1.4019 (5) |
C2—B3 | 1.7345 (5) | C13—C18 | 1.4020 (5) |
B3—C13 | 1.5676 (5) | C14—C15 | 1.3967 (6) |
B3—B8 | 1.7742 (6) | C15—C16 | 1.3895 (6) |
B3—B4 | 1.7865 (6) | C16—C17 | 1.3898 (6) |
B3—B7 | 1.7896 (6) | C17—C18 | 1.3975 (6) |
C14—C13—C18 | 117.71 (3) | C16—C15—C14 | 120.17 (3) |
C14—C13—B3 | 119.65 (3) | C17—C16—C15 | 119.54 (4) |
C18—C13—B3 | 122.45 (3) | C16—C17—C18 | 120.23 (4) |
C15—C14—C13 | 121.22 (4) | C17—C18—C13 | 121.12 (3) |
C1—C13 | 1.5095 (13) | B4—B5 | 1.7703 (16) |
C1—B2 | 1.7100 (15) | B5—B6 | 1.7720 (15) |
C1—B3 | 1.7170 (15) | C7—B12 | 1.7020 (16) |
C1—B5 | 1.7212 (14) | C7—B11 | 1.7038 (19) |
C1—B6 | 1.7254 (15) | C7—B8 | 1.7173 (18) |
C1—B4 | 1.7297 (15) | B8—B12 | 1.7778 (19) |
B2—C7 | 1.6961 (17) | B11—B12 | 1.7755 (18) |
B2—B6 | 1.7622 (18) | C13—C18 | 1.3852 (14) |
B2—B11 | 1.7699 (18) | C13—C14 | 1.3913 (14) |
B2—B3 | 1.787 (2) | C14—C15 | 1.3872 (15) |
B3—C7 | 1.6893 (18) | C15—C16 | 1.3762 (17) |
B3—B8 | 1.7628 (18) | C16—C17 | 1.3775 (17) |
B3—B4 | 1.7666 (17) | C17—C18 | 1.3905 (16) |
C18—C13—C14 | 118.45 (10) | C16—C15—C14 | 120.92 (10) |
C18—C13—C1 | 120.71 (9) | C15—C16—C17 | 119.15 (11) |
C14—C13—C1 | 120.83 (9) | C16—C17—C18 | 120.38 (11) |
C15—C14—C13 | 120.30 (11) | C13—C18—C17 | 120.80 (10) |
The carboranes are of great interest for the study of chemical bonding. In particular, carboranes are interesting compounds for high resolution X-ray analysis of electron-density distribution (Antipin et al., 1997; Lyssenko et al., 1998). The most attractive objects for such investigation are isostructural compounds, because in such a case most differences in the electron-density distribution features may be attributed to intramolecular electronic effects. We found an interesting example of isostructural compounds in two monosubstituted carboranes, namely (I) and (II). \sch
The molecular structures of (I) and (II) are shown in Figs. 1 and 2, and selected geometric parameters are given in Tables 1 and 2. The X-ray investigation of (I) and (II) reveals that the two compounds are indeed isostructural and crystallize in the monoclinic space group P21/c (Z = 4) with quite similar crystal packing. The crystal structures of (I) (Fig. 3) and (II) (Fig. 4) consist of layers of carborane molecules parallel to the bc plane. In both crystals, the arrangement of molecules in the layers is such that the phenyl group of each molecule is surrounded by four carborane cages of neighbouring molecules and vice versa, without formation of intermolecular contacts within or between the layers. It is noteworthy that previously published structures of mono phenyl-substituted carboranes, namely 1-Ph-1,2-C2B10H11 (α form; Brain et al., 1996), 1-Ph-1,2-C2B10H11 (β form; Thomas et al., 1996) and 9-Ph-1,7-C2B10H11 (Kabachii et al., 1985) are characterized by different crystal packing.
Consideration of the molecular geometry reveals that the carborane cages have near-icosahedral architecture, with C—B distances in the range 1.6895 (5)–1.7345 (5) Å, B—B distances in the range 1.7683 (7)–1.7896 (6) Å and a C—C bond length of 1.6225 (5) Å in (I), and C—B distances in the range 1.6893 (18)–1.7297 (15) Å and B—B in the range 1.7622 (18)–1.787 (2) Å for (II).
The presence of the phenyl substituent in (I) and (II) has a notable influence on the geometry of the carborane cages. This is manifested in the lengthening of the B3—B4, B3—B8 and B3—B7 distances by approximately 0.01 Å with respect to the B5—B6, B6—B10 and B10—B11 bonds in (I), and of the C1—B2 and C1—B3 distances by 0.02 Å with respect to the C7—B2 and C7—B3 bonds in (II). Thus, the displacement of atom C1 in (II) by 0.8305 (11) Å from the B2/B3/B4/B5/B6 pentagonal plane results in the decrease of the deviation of atom C7 to 0.7855 (13) Å from the corresponding B2//B3/B8/B11/B12 plane.
In turn, the carborane cage affects the phenyl geometry. Comparison of the bond angles at the ipso-carbons of the phenyl substituent in (I) and (II) [117.71 (3) and 118.45 (10)°, respectively] indicates that electron donation of the carborane cage for B– and C-substituted carboranes is different (Domenicano & Hargittai, 1992). The increase of the ipso-angle in (II) means that the electron donation of the carborane cage in (I) is more pronounced than in (II). For comparison, the corresponding angles in 9-Ph-1,7-C2B10H11 and in the α and β forms of 1-Ph-1,2-C2B10H11 are 117.1 (5), 119.14 (14) and 120.0 (3)°, respectively.
The orientation of the phenyl rings in phenyl-substituted carboranes may be described by means of the minimal torsion angle between the plane of the phenyl and the edge of the carborane cage. The minimal torsion angles are B7—B3—C13—C14 = 18.16 (5)° in (I) and B3—C1—C13—C18 = 13.28 (14)° in (II).