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Two phenyl-substituted carboranes, 3-phenyl-1,2-dicarba-closo-dodecaborane(12), C8H16B10, (I), and 1-phenyl-1,7-dicarba-closo-dodecaborane(12), C8H16B10, (II), were found to be isostructural. Comparison of the bond angles at the ipso-C atoms of the phenyl substituent for (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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101005455/av1073sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005455/av1073Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005455/av1073IIsup3.hkl
Contains datablock II

CCDC references: 169939; 169940

Comment top

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).

Experimental top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The molecular structure of (II) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. A view of the unit cell of (I) along the b direction.
[Figure 4] Fig. 4. A view of the unit cell of (II) along the b direction.
(I) 3-phenyl-1,2-dicarba-closo-dodecaborane(12) top
Crystal data top
C8H16B10F(000) = 456
Mr = 220.31Dx = 1.157 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.378 (2) ÅCell parameters from 890 reflections
b = 9.725 (2) Åθ = 2–26°
c = 12.699 (3) ŵ = 0.05 mm1
β = 99.195 (7)°T = 110 K
V = 1265.2 (5) Å3Prism, colourless
Z = 40.35 × 0.30 × 0.25 mm
Data collection top
Bruker CCD area-detector
diffractometer
14343 independent reflections
Radiation source: fine-focus sealed tube9409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 52.8°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.981, Tmax = 0.987k = 2121
49186 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.142All 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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C8H16B10V = 1265.2 (5) Å3
Mr = 220.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.378 (2) ŵ = 0.05 mm1
b = 9.725 (2) ÅT = 110 K
c = 12.699 (3) Å0.35 × 0.30 × 0.25 mm
β = 99.195 (7)°
Data collection top
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 = 0.987Rint = 0.029
49186 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.142All H-atom parameters refined
S = 0.96Δρmax = 0.36 e Å3
14343 reflectionsΔρmin = 0.33 e Å3
227 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.24045 (3)0.80396 (3)0.09214 (2)0.01477 (5)
C21.20780 (3)0.95720 (3)0.13098 (3)0.01530 (5)
B31.10964 (3)0.82234 (4)0.15962 (3)0.01400 (5)
B41.22352 (4)0.68390 (4)0.18512 (3)0.01651 (6)
B51.38035 (4)0.74066 (4)0.16422 (3)0.01815 (6)
B61.36813 (4)0.91672 (4)0.12627 (3)0.01795 (6)
B71.16472 (4)0.95464 (4)0.25411 (3)0.01742 (6)
B81.17774 (4)0.77874 (4)0.29255 (3)0.01754 (6)
B91.34401 (4)0.72776 (4)0.29611 (3)0.01902 (6)
B101.43317 (4)0.87223 (5)0.25915 (3)0.01882 (6)
B111.32181 (4)1.01233 (4)0.23361 (3)0.01885 (6)
B121.30759 (4)0.89564 (5)0.33901 (3)0.01945 (6)
C130.96548 (3)0.80352 (3)0.10199 (2)0.01426 (4)
C140.86335 (3)0.86694 (4)0.14379 (3)0.01851 (5)
C150.73308 (3)0.84313 (4)0.09995 (3)0.02150 (6)
C160.70241 (4)0.75676 (4)0.01237 (3)0.02146 (6)
C170.80224 (4)0.69433 (4)0.03122 (3)0.02160 (6)
C180.93247 (3)0.71646 (4)0.01381 (3)0.01801 (5)
H11.2177 (8)0.7865 (8)0.0213 (6)0.0222 (17)*
H21.1684 (8)1.0168 (9)0.0791 (6)0.0247 (18)*
H41.1882 (9)0.5821 (10)0.1564 (8)0.032 (2)*
H51.4354 (8)0.6721 (9)0.1231 (7)0.0283 (19)*
H61.4114 (8)0.9573 (9)0.0642 (7)0.0282 (19)*
H71.0955 (8)1.0270 (9)0.2715 (7)0.0286 (19)*
H81.1161 (9)0.7299 (10)0.3432 (7)0.033 (2)*
H91.3884 (8)0.6487 (9)0.3515 (7)0.0292 (19)*
H101.5416 (10)0.8969 (11)0.2922 (8)0.041 (2)*
H111.3442 (8)1.1217 (10)0.2343 (7)0.034 (2)*
H121.3303 (10)0.9245 (12)0.4235 (8)0.044 (3)*
H140.8766 (9)0.9265 (10)0.2005 (8)0.036 (2)*
H150.6628 (9)0.8845 (10)0.1300 (8)0.034 (2)*
H160.6132 (9)0.7400 (10)0.0182 (7)0.036 (2)*
H170.7829 (9)0.6346 (11)0.0924 (8)0.042 (3)*
H181.0043 (9)0.6685 (10)0.0176 (7)0.031 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.01409 (10)0.01814 (11)0.01204 (9)0.00138 (8)0.00195 (7)0.00007 (8)
C20.01440 (10)0.01485 (10)0.01605 (10)0.00001 (7)0.00066 (8)0.00212 (8)
B30.01407 (11)0.01481 (12)0.01327 (11)0.00044 (8)0.00258 (9)0.00039 (9)
B40.01866 (13)0.01454 (12)0.01619 (12)0.00203 (9)0.00236 (10)0.00062 (9)
B50.01582 (13)0.02129 (15)0.01707 (13)0.00436 (10)0.00178 (10)0.00009 (11)
B60.01406 (12)0.02239 (15)0.01705 (13)0.00064 (10)0.00138 (10)0.00302 (11)
B70.01761 (13)0.01739 (13)0.01703 (13)0.00130 (10)0.00203 (10)0.00352 (10)
B80.02001 (14)0.02026 (14)0.01261 (11)0.00021 (11)0.00341 (10)0.00108 (10)
B90.02036 (15)0.02006 (15)0.01571 (12)0.00318 (11)0.00002 (11)0.00342 (11)
B100.01565 (13)0.02271 (16)0.01684 (13)0.00105 (10)0.00125 (10)0.00081 (11)
B110.01755 (13)0.01732 (14)0.02036 (14)0.00126 (10)0.00096 (11)0.00093 (11)
B120.02049 (15)0.02306 (16)0.01384 (12)0.00072 (11)0.00023 (11)0.00212 (11)
C130.01377 (10)0.01490 (10)0.01437 (10)0.00005 (7)0.00302 (8)0.00003 (8)
C140.01540 (11)0.02251 (14)0.01806 (12)0.00168 (9)0.00402 (9)0.00252 (10)
C150.01455 (11)0.02653 (16)0.02398 (14)0.00172 (10)0.00479 (10)0.00053 (12)
C160.01550 (11)0.02233 (14)0.02572 (15)0.00283 (9)0.00075 (11)0.00207 (11)
C170.01921 (13)0.02031 (13)0.02405 (14)0.00305 (10)0.00034 (11)0.00406 (11)
C180.01683 (11)0.01804 (12)0.01914 (12)0.00088 (8)0.00283 (9)0.00380 (9)
Geometric parameters (Å, º) top
C1—C21.6225 (5)B9—B101.7858 (7)
C1—B41.6895 (5)B10—B111.7825 (6)
C1—B51.7030 (6)B10—B121.7891 (7)
C1—B61.7213 (6)B11—B121.7788 (7)
C1—B31.7265 (5)C13—C141.4019 (5)
C2—B71.6937 (6)C13—C181.4020 (5)
C2—B111.7010 (6)C14—C151.3967 (6)
C2—B61.7201 (6)C15—C161.3895 (6)
C2—B31.7345 (5)C16—C171.3898 (6)
B3—C131.5676 (5)C17—C181.3975 (6)
B3—B81.7742 (6)C1—H10.909 (8)
B3—B41.7865 (6)C2—H20.922 (8)
B3—B71.7896 (6)B4—H41.098 (9)
B4—B81.7734 (6)B5—H51.068 (9)
B4—B51.7782 (7)B6—H61.045 (9)
B4—B91.7801 (6)B7—H71.054 (9)
B5—B61.7778 (7)B8—H81.087 (9)
B5—B91.7791 (7)B9—H91.093 (9)
B5—B101.7833 (6)B10—H101.162 (10)
B6—B101.7683 (7)B11—H111.089 (9)
B6—B111.7785 (7)B12—H121.097 (10)
B7—B81.7782 (7)C14—H140.917 (10)
B7—B111.7820 (7)C15—H150.963 (9)
B7—B121.7830 (6)C16—H160.959 (9)
B8—B121.7896 (6)C17—H170.965 (10)
B8—B91.7889 (7)C18—H181.013 (9)
B9—B121.7807 (7)
C2—C1—B4111.85 (3)B11—B10—B9107.52 (3)
C2—C1—B5111.72 (3)B5—B10—B959.80 (3)
B4—C1—B563.22 (2)B6—B10—B12107.95 (3)
C2—C1—B661.83 (2)B11—B10—B1259.74 (3)
B4—C1—B6115.22 (3)B5—B10—B12107.55 (3)
B5—C1—B662.55 (3)B9—B10—B1259.75 (3)
C2—C1—B362.29 (2)C2—B11—B659.20 (2)
B4—C1—B363.06 (2)C2—B11—B12104.14 (3)
B5—C1—B3116.17 (3)B6—B11—B12107.96 (3)
B6—C1—B3116.34 (3)C2—B11—B758.14 (2)
C1—C2—B7111.46 (3)B6—B11—B7108.24 (3)
C1—C2—B11111.65 (3)B12—B11—B760.10 (2)
B7—C2—B1163.33 (3)C2—B11—B10104.47 (3)
C1—C2—B661.91 (2)B6—B11—B1059.54 (3)
B7—C2—B6115.35 (3)B12—B11—B1060.32 (3)
B11—C2—B662.65 (3)B7—B11—B10108.33 (3)
C1—C2—B361.79 (2)B11—B12—B9107.91 (3)
B7—C2—B362.92 (2)B11—B12—B760.04 (3)
B11—C2—B3115.95 (3)B9—B12—B7107.85 (3)
B6—C2—B3115.98 (3)B11—B12—B1059.95 (3)
C13—B3—C1121.57 (3)B9—B12—B1060.03 (2)
C13—B3—C2122.61 (3)B7—B12—B10107.99 (3)
C1—B3—C255.91 (2)B11—B12—B8107.81 (3)
C13—B3—B8128.44 (3)B9—B12—B860.14 (3)
C1—B3—B8102.85 (3)B7—B12—B859.70 (3)
C2—B3—B8102.84 (3)B10—B12—B8108.10 (3)
C13—B3—B4123.43 (3)C14—C13—C18117.71 (3)
C1—B3—B457.46 (2)C14—C13—B3119.65 (3)
C2—B3—B4102.37 (3)C18—C13—B3122.45 (3)
B8—B3—B459.74 (2)C15—C14—C13121.22 (4)
C13—B3—B7125.15 (3)C16—C15—C14120.17 (3)
C1—B3—B7102.42 (3)C17—C16—C15119.54 (4)
C2—B3—B757.43 (2)C16—C17—C18120.23 (4)
B8—B3—B759.86 (2)C17—C18—C13121.12 (3)
B4—B3—B7106.80 (3)C2—C1—H1116.0 (5)
C1—B4—B8104.41 (3)B4—C1—H1121.5 (5)
C1—B4—B558.76 (2)B5—C1—H1121.9 (5)
B8—B4—B5108.52 (3)B6—C1—H1115.9 (5)
C1—B4—B9104.45 (3)B3—C1—H1114.2 (5)
B8—B4—B960.45 (3)C1—C2—H2116.8 (5)
B5—B4—B960.00 (3)B7—C2—H2121.1 (5)
C1—B4—B359.48 (2)B11—C2—H2121.6 (5)
B8—B4—B359.78 (2)B6—C2—H2116.1 (5)
B5—B4—B3109.50 (3)B3—C2—H2114.6 (5)
B9—B4—B3108.88 (3)C1—B4—H4117.3 (5)
C1—B5—B659.23 (2)B8—B4—H4127.4 (5)
C1—B5—B458.02 (2)B5—B4—H4119.7 (5)
B6—B5—B4108.18 (3)B9—B4—H4129.4 (5)
C1—B5—B9103.93 (3)B3—B4—H4116.3 (5)
B6—B5—B9107.84 (3)C1—B5—H5116.1 (5)
B4—B5—B960.05 (2)B6—B5—H5119.3 (5)
C1—B5—B10104.34 (3)B4—B5—H5117.0 (5)
B6—B5—B1059.54 (3)B9—B5—H5128.9 (5)
B4—B5—B10108.15 (3)B10—B5—H5130.4 (5)
B9—B5—B1060.17 (3)C2—B6—H6118.3 (5)
C2—B6—C156.26 (2)C1—B6—H6117.2 (5)
C2—B6—B10104.28 (3)B10—B6—H6131.9 (5)
C1—B6—B10104.21 (3)B5—B6—H6123.2 (5)
C2—B6—B5103.80 (3)B11—B6—H6125.6 (5)
C1—B6—B558.22 (2)C2—B7—H7118.2 (5)
B10—B6—B560.38 (2)B8—B7—H7127.6 (5)
C2—B6—B1158.15 (2)B11—B7—H7119.3 (5)
C1—B6—B11103.57 (3)B12—B7—H7128.1 (5)
B10—B6—B1160.34 (3)B3—B7—H7117.7 (5)
B5—B6—B11108.18 (3)B4—B8—H8118.9 (5)
C2—B7—B8104.36 (3)B3—B8—H8119.0 (5)
C2—B7—B1158.53 (2)B7—B8—H8123.9 (5)
B8—B7—B11108.17 (3)B12—B8—H8124.5 (5)
C2—B7—B12104.26 (3)B9—B8—H8121.4 (5)
B8—B7—B1260.33 (2)B4—B9—H9120.8 (5)
B11—B7—B1259.86 (3)B5—B9—H9121.6 (5)
C2—B7—B359.65 (2)B12—B9—H9122.4 (5)
B8—B7—B359.64 (2)B10—B9—H9122.7 (5)
B11—B7—B3109.27 (3)B8—B9—H9121.1 (5)
B12—B7—B3108.65 (3)B6—B10—H10119.6 (5)
B4—B8—B360.48 (2)B11—B10—H10118.0 (5)
B4—B8—B7107.88 (3)B5—B10—H10124.6 (5)
B3—B8—B760.50 (2)B9—B10—H10125.5 (5)
B4—B8—B12107.68 (3)B12—B10—H10121.4 (5)
B3—B8—B12109.04 (3)C2—B11—H11115.8 (5)
B7—B8—B1259.97 (2)B6—B11—H11115.7 (5)
B4—B8—B959.96 (2)B12—B11—H11131.3 (5)
B3—B8—B9109.04 (3)B7—B11—H11120.4 (5)
B7—B8—B9107.71 (3)B10—B11—H11127.9 (5)
B12—B8—B959.68 (3)B11—B12—H12122.8 (6)
B4—B9—B559.95 (3)B9—B12—H12120.7 (6)
B4—B9—B12107.78 (3)B7—B12—H12122.5 (5)
B5—B9—B12108.10 (3)B10—B12—H12121.6 (5)
B4—B9—B10107.96 (3)B8—B12—H12121.2 (6)
B5—B9—B1060.03 (2)C15—C14—H14115.6 (6)
B12—B9—B1060.22 (3)C13—C14—H14123.2 (6)
B4—B9—B859.59 (2)C16—C15—H15118.6 (5)
B5—B9—B8107.79 (3)C14—C15—H15121.2 (5)
B12—B9—B860.18 (2)C17—C16—H16119.8 (6)
B10—B9—B8108.28 (3)C15—C16—H16120.6 (6)
B6—B10—B1160.12 (2)C16—C17—H17120.7 (6)
B6—B10—B560.07 (3)C18—C17—H17119.0 (6)
B11—B10—B5107.76 (3)C17—C18—H18119.5 (5)
B6—B10—B9107.97 (3)C13—C18—H18119.4 (5)
(II) 1-phenyl-1,7-dicarba-closo-dodecaborane(12) top
Crystal data top
C8H16B10F(000) = 456
Mr = 220.31Dx = 1.131 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.350 (2) ÅCell parameters from 24 reflections
b = 9.449 (2) Åθ = 10–14°
c = 13.763 (3) ŵ = 0.05 mm1
β = 106.07 (3)°T = 163 K
V = 1293.4 (5) Å3Prism, colourless
Z = 40.30 × 0.25 × 0.20 mm
Data collection top
Syntex P21
diffractometer
Rint = 0.027
Radiation source: fine-focus sealed tubeθmax = 33.1°, θmin = 2.1°
Graphite monochromatorh = 015
θ/2θ scansk = 014
5094 measured reflectionsl = 2120
4872 independent reflections2 standard reflections every 98 reflections
2765 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: difference Fourier map
wR(F2) = 0.115All 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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C8H16B10V = 1293.4 (5) Å3
Mr = 220.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.350 (2) ŵ = 0.05 mm1
b = 9.449 (2) ÅT = 163 K
c = 13.763 (3) Å0.30 × 0.25 × 0.20 mm
β = 106.07 (3)°
Data collection top
Syntex P21
diffractometer
Rint = 0.027
5094 measured reflections2 standard reflections every 98 reflections
4872 independent reflections intensity decay: 2%
2765 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.115All H-atom parameters refined
S = 0.88Δρmax = 0.24 e Å3
4872 reflectionsΔρmin = 0.19 e Å3
227 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.11330 (9)0.79918 (10)0.15227 (7)0.01994 (18)
B20.18872 (12)0.93738 (12)0.10912 (10)0.0299 (3)
B30.17182 (12)0.93599 (12)0.23484 (10)0.0306 (3)
B40.18679 (12)0.75911 (13)0.27811 (8)0.0258 (2)
B50.21528 (11)0.65235 (11)0.18036 (8)0.0218 (2)
B60.21632 (11)0.76201 (13)0.07613 (8)0.0243 (2)
C70.31989 (11)0.97321 (11)0.21124 (9)0.0326 (3)
B80.32415 (13)0.87657 (14)0.31775 (9)0.0318 (3)
B90.35190 (12)0.70096 (13)0.28417 (9)0.0271 (2)
B100.36966 (12)0.70236 (13)0.15896 (9)0.0262 (2)
B110.35348 (12)0.87972 (14)0.11519 (10)0.0310 (3)
B120.43674 (12)0.84214 (13)0.24368 (9)0.0283 (2)
C130.03650 (9)0.77803 (9)0.11114 (7)0.02143 (19)
C140.08867 (11)0.68737 (11)0.03010 (9)0.0295 (2)
C150.22652 (11)0.66869 (12)0.00695 (9)0.0356 (3)
C160.31412 (11)0.73960 (12)0.03500 (9)0.0345 (3)
C170.26324 (11)0.82824 (13)0.11603 (10)0.0379 (3)
C180.12520 (11)0.84732 (12)0.15398 (9)0.0317 (2)
H20.1344 (13)1.0149 (15)0.0611 (9)0.044 (4)*
H30.1099 (13)1.0152 (15)0.2538 (10)0.046 (4)*
H40.1232 (13)0.7210 (14)0.3219 (9)0.043 (4)*
H50.1683 (11)0.5488 (13)0.1685 (8)0.029 (3)*
H60.1721 (12)0.7259 (13)0.0002 (9)0.032 (3)*
H70.3498 (12)1.0689 (14)0.2189 (9)0.039 (3)*
H80.3610 (13)0.9281 (14)0.3913 (10)0.046 (4)*
H90.4044 (12)0.6251 (14)0.3424 (9)0.038 (3)*
H100.4335 (12)0.6257 (13)0.1320 (9)0.038 (3)*
H110.4063 (13)0.9318 (14)0.0653 (10)0.045 (4)*
H120.5409 (12)0.8710 (14)0.2736 (9)0.042 (4)*
H140.0284 (13)0.6428 (14)0.0007 (10)0.040 (4)*
H150.2622 (13)0.6083 (15)0.0682 (10)0.048 (4)*
H160.4081 (13)0.7236 (13)0.0110 (9)0.037 (3)*
H170.3205 (14)0.8783 (16)0.1505 (11)0.056 (4)*
H180.0924 (12)0.9114 (14)0.2080 (10)0.040 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0214 (4)0.0172 (4)0.0208 (4)0.0001 (3)0.0051 (3)0.0002 (3)
B20.0246 (5)0.0232 (5)0.0382 (7)0.0009 (4)0.0022 (5)0.0099 (5)
B30.0266 (6)0.0229 (5)0.0393 (7)0.0001 (4)0.0042 (5)0.0093 (5)
B40.0291 (5)0.0293 (5)0.0186 (5)0.0005 (5)0.0059 (4)0.0029 (4)
B50.0252 (5)0.0196 (5)0.0203 (5)0.0023 (4)0.0059 (4)0.0000 (4)
B60.0224 (5)0.0310 (6)0.0196 (5)0.0004 (4)0.0059 (4)0.0040 (4)
C70.0255 (5)0.0202 (5)0.0467 (7)0.0024 (4)0.0010 (4)0.0008 (4)
B80.0298 (6)0.0332 (6)0.0286 (6)0.0014 (5)0.0019 (5)0.0097 (5)
B90.0285 (6)0.0269 (5)0.0228 (5)0.0019 (4)0.0020 (4)0.0024 (4)
B100.0236 (5)0.0282 (5)0.0262 (5)0.0028 (4)0.0057 (4)0.0005 (4)
B110.0227 (5)0.0351 (6)0.0336 (6)0.0021 (5)0.0050 (5)0.0111 (5)
B120.0226 (5)0.0267 (5)0.0317 (6)0.0004 (4)0.0009 (4)0.0008 (5)
C130.0215 (4)0.0182 (4)0.0240 (4)0.0005 (3)0.0053 (3)0.0006 (3)
C140.0250 (5)0.0259 (5)0.0365 (6)0.0011 (4)0.0067 (4)0.0086 (4)
C150.0266 (5)0.0341 (6)0.0422 (6)0.0036 (4)0.0032 (5)0.0122 (5)
C160.0218 (5)0.0333 (5)0.0462 (7)0.0016 (4)0.0059 (4)0.0012 (5)
C170.0254 (5)0.0417 (6)0.0496 (7)0.0014 (5)0.0153 (5)0.0096 (5)
C180.0270 (5)0.0340 (5)0.0355 (6)0.0012 (4)0.0107 (4)0.0105 (5)
Geometric parameters (Å, º) top
C1—C131.5095 (13)B9—B101.7829 (18)
C1—B21.7100 (15)B10—B121.7714 (17)
C1—B31.7170 (15)B10—B111.7731 (18)
C1—B51.7212 (14)B11—B121.7755 (18)
C1—B61.7254 (15)C13—C181.3852 (14)
C1—B41.7297 (15)C13—C141.3913 (14)
B2—C71.6961 (17)C14—C151.3872 (15)
B2—B61.7622 (18)C15—C161.3762 (17)
B2—B111.7699 (18)C16—C171.3775 (17)
B2—B31.787 (2)C17—C181.3905 (16)
B3—C71.6893 (18)B2—H21.041 (13)
B3—B81.7628 (18)B3—H31.064 (14)
B3—B41.7666 (17)B4—H41.070 (13)
B4—B81.7667 (18)B5—H51.085 (12)
B4—B51.7703 (16)B6—H61.074 (12)
B4—B91.7749 (18)C7—H70.952 (13)
B5—B101.7675 (17)B8—H81.092 (13)
B5—B91.7702 (17)B9—H91.100 (12)
B5—B61.7720 (15)B10—H101.111 (12)
B6—B111.7661 (17)B11—H111.104 (13)
B6—B101.7705 (16)B12—H121.078 (12)
C7—B121.7020 (16)C14—H140.945 (13)
C7—B111.7038 (19)C15—H151.000 (14)
C7—B81.7173 (18)C16—H160.949 (12)
B8—B91.7671 (18)C17—H170.978 (15)
B8—B121.7778 (19)C18—H180.946 (13)
B9—B121.7697 (18)
C13—C1—B2119.41 (8)B6—B10—B1159.79 (7)
C13—C1—B3119.04 (8)B12—B10—B1160.12 (7)
B2—C1—B362.84 (8)B5—B10—B959.81 (7)
C13—C1—B5118.68 (8)B6—B10—B9108.11 (9)
B2—C1—B5112.52 (8)B12—B10—B959.72 (7)
B3—C1—B5112.10 (8)B11—B10—B9108.06 (9)
C13—C1—B6119.25 (8)C7—B11—B6104.08 (9)
B2—C1—B661.72 (7)C7—B11—B258.42 (7)
B3—C1—B6113.02 (8)B6—B11—B259.78 (7)
B5—C1—B661.88 (6)C7—B11—B10104.29 (9)
C13—C1—B4117.90 (8)B6—B11—B1060.03 (7)
B2—C1—B4113.48 (8)B2—B11—B10107.83 (9)
B3—C1—B461.67 (7)C7—B11—B1258.53 (7)
B5—C1—B461.73 (6)B6—B11—B12107.75 (9)
B6—C1—B4112.90 (8)B2—B11—B12107.71 (10)
C7—B2—C1101.67 (8)B10—B11—B1259.89 (7)
C7—B2—B6104.57 (8)C7—B12—B9104.63 (9)
C1—B2—B659.57 (6)C7—B12—B10104.44 (8)
C7—B2—B1158.84 (7)B9—B12—B1060.46 (7)
C1—B2—B11105.97 (8)C7—B12—B859.09 (7)
B6—B2—B1160.00 (7)B9—B12—B859.75 (7)
C7—B2—B357.96 (7)B10—B12—B8108.31 (9)
C1—B2—B358.77 (7)C7—B12—B1158.63 (7)
B6—B2—B3107.99 (8)B9—B12—B11108.55 (8)
B11—B2—B3107.66 (9)B10—B12—B1159.99 (7)
C7—B3—C1101.66 (9)B8—B12—B11108.67 (9)
C7—B3—B859.62 (7)C18—C13—C14118.45 (10)
C1—B3—B8106.08 (8)C18—C13—C1120.71 (9)
C7—B3—B4105.20 (8)C14—C13—C1120.83 (9)
C1—B3—B459.52 (6)C15—C14—C13120.30 (11)
B8—B3—B460.07 (7)C16—C15—C14120.92 (10)
C7—B3—B258.33 (8)C15—C16—C17119.15 (11)
C1—B3—B258.39 (6)C16—C17—C18120.38 (11)
B8—B3—B2108.63 (9)C13—C18—C17120.80 (10)
B4—B3—B2108.08 (8)C7—B2—H2123.6 (7)
C1—B4—B358.81 (6)C1—B2—H2122.6 (7)
C1—B4—B8105.37 (9)B6—B2—H2126.6 (7)
B3—B4—B859.86 (7)B11—B2—H2126.2 (7)
C1—B4—B558.90 (6)B3—B2—H2116.0 (7)
B3—B4—B5107.49 (8)C7—B3—H3122.7 (7)
B8—B4—B5107.67 (9)C1—B3—H3124.5 (7)
C1—B4—B9105.41 (8)B8—B3—H3123.8 (7)
B3—B4—B9107.59 (9)B4—B3—H3125.8 (7)
B8—B4—B959.86 (7)B2—B3—H3117.4 (7)
B5—B4—B959.91 (7)C1—B4—H4118.0 (7)
C1—B5—B459.37 (6)B3—B4—H4119.8 (7)
C1—B5—B10105.88 (8)B8—B4—H4127.2 (7)
B4—B5—B10108.82 (8)B5—B4—H4119.6 (7)
C1—B5—B9105.98 (8)B9—B4—H4127.1 (7)
B4—B5—B960.17 (7)C1—B5—H5118.1 (6)
B10—B5—B960.53 (7)B4—B5—H5117.8 (6)
C1—B5—B659.18 (6)B10—B5—H5127.2 (6)
B4—B5—B6108.76 (8)B9—B5—H5125.5 (6)
B10—B5—B660.03 (7)B6—B5—H5120.6 (6)
B9—B5—B6108.61 (8)C1—B6—H6119.2 (6)
C1—B6—B258.71 (6)B2—B6—H6119.6 (6)
C1—B6—B11105.47 (8)B11—B6—H6125.9 (7)
B2—B6—B1160.22 (7)B10—B6—H6126.2 (6)
C1—B6—B10105.56 (8)B5—B6—H6120.4 (7)
B2—B6—B10108.29 (8)B3—C7—H7117.4 (8)
B11—B6—B1060.18 (7)B2—C7—H7116.3 (7)
C1—B6—B558.94 (6)B12—C7—H7118.5 (7)
B2—B6—B5107.67 (8)B11—C7—H7116.7 (8)
B11—B6—B5107.84 (8)B8—C7—H7118.7 (8)
B10—B6—B559.86 (7)C7—B8—H8118.3 (7)
B3—C7—B263.71 (8)B3—B8—H8118.5 (7)
B3—C7—B12114.50 (9)B4—B8—H8127.7 (7)
B2—C7—B12114.82 (9)B9—B8—H8128.4 (7)
B3—C7—B11115.60 (9)B12—B8—H8119.8 (7)
B2—C7—B1162.74 (7)B8—B9—H9120.3 (7)
B12—C7—B1162.84 (7)B12—B9—H9122.2 (7)
B3—C7—B862.32 (8)B5—B9—H9122.8 (7)
B2—C7—B8115.26 (9)B4—B9—H9120.7 (6)
B12—C7—B862.66 (8)B10—B9—H9123.2 (7)
B11—C7—B8115.09 (9)B5—B10—H10122.0 (6)
C7—B8—B358.06 (7)B6—B10—H10120.2 (6)
C7—B8—B4104.01 (8)B12—B10—H10123.0 (6)
B3—B8—B460.07 (7)B11—B10—H10120.8 (6)
C7—B8—B9104.10 (9)B9—B10—H10123.2 (6)
B3—B8—B9108.11 (8)C7—B11—H11119.6 (7)
B4—B8—B960.30 (7)B6—B11—H11125.9 (7)
C7—B8—B1258.25 (7)B2—B11—H11118.0 (7)
B3—B8—B12107.33 (9)B10—B11—H11128.0 (7)
B4—B8—B12107.89 (8)B12—B11—H11121.4 (7)
B9—B8—B1259.90 (7)C7—B12—H12118.7 (7)
B8—B9—B1260.35 (7)B9—B12—H12127.0 (7)
B8—B9—B5107.66 (8)B10—B12—H12127.5 (7)
B12—B9—B5107.25 (8)B8—B12—H12118.7 (7)
B8—B9—B459.84 (7)B11—B12—H12119.3 (7)
B12—B9—B4107.88 (8)C15—C14—H14121.2 (8)
B5—B9—B459.92 (7)C13—C14—H14118.4 (8)
B8—B9—B10108.27 (9)C16—C15—H15119.9 (8)
B12—B9—B1059.81 (7)C14—C15—H15119.0 (8)
B5—B9—B1059.66 (7)C15—C16—H16120.5 (8)
B4—B9—B10107.92 (8)C17—C16—H16120.3 (8)
B5—B10—B660.11 (6)C16—C17—H17122.7 (9)
B5—B10—B12107.30 (9)C18—C17—H17116.9 (9)
B6—B10—B12107.73 (9)C13—C18—H18120.1 (8)
B5—B10—B11107.73 (8)C17—C18—H18119.1 (8)

Experimental details

(I)(II)
Crystal data
Chemical formulaC8H16B10C8H16B10
Mr220.31220.31
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)110163
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)
V3)1265.2 (5)1293.4 (5)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.050.05
Crystal size (mm)0.35 × 0.30 × 0.250.30 × 0.25 × 0.20
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Syntex P21
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.981, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
49186, 14343, 9409 5094, 4872, 2765
Rint0.0290.027
(sin θ/λ)max1)1.1210.768
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.142, 0.96 0.049, 0.115, 0.88
No. of reflections143434872
No. of parameters227227
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.36, 0.330.24, 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.

Selected geometric parameters (Å, º) for (I) top
C1—C21.6225 (5)B4—B81.7734 (6)
C1—B41.6895 (5)B5—B61.7778 (7)
C1—B51.7030 (6)B5—B101.7833 (6)
C1—B61.7213 (6)B6—B101.7683 (7)
C1—B31.7265 (5)B6—B111.7785 (7)
C2—B71.6937 (6)B7—B81.7782 (7)
C2—B111.7010 (6)B10—B111.7825 (6)
C2—B61.7201 (6)C13—C141.4019 (5)
C2—B31.7345 (5)C13—C181.4020 (5)
B3—C131.5676 (5)C14—C151.3967 (6)
B3—B81.7742 (6)C15—C161.3895 (6)
B3—B41.7865 (6)C16—C171.3898 (6)
B3—B71.7896 (6)C17—C181.3975 (6)
C14—C13—C18117.71 (3)C16—C15—C14120.17 (3)
C14—C13—B3119.65 (3)C17—C16—C15119.54 (4)
C18—C13—B3122.45 (3)C16—C17—C18120.23 (4)
C15—C14—C13121.22 (4)C17—C18—C13121.12 (3)
Selected geometric parameters (Å, º) for (II) top
C1—C131.5095 (13)B4—B51.7703 (16)
C1—B21.7100 (15)B5—B61.7720 (15)
C1—B31.7170 (15)C7—B121.7020 (16)
C1—B51.7212 (14)C7—B111.7038 (19)
C1—B61.7254 (15)C7—B81.7173 (18)
C1—B41.7297 (15)B8—B121.7778 (19)
B2—C71.6961 (17)B11—B121.7755 (18)
B2—B61.7622 (18)C13—C181.3852 (14)
B2—B111.7699 (18)C13—C141.3913 (14)
B2—B31.787 (2)C14—C151.3872 (15)
B3—C71.6893 (18)C15—C161.3762 (17)
B3—B81.7628 (18)C16—C171.3775 (17)
B3—B41.7666 (17)C17—C181.3905 (16)
C18—C13—C14118.45 (10)C16—C15—C14120.92 (10)
C18—C13—C1120.71 (9)C15—C16—C17119.15 (11)
C14—C13—C1120.83 (9)C16—C17—C18120.38 (11)
C15—C14—C13120.30 (11)C13—C18—C17120.80 (10)
 

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