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The title compound, 9-iodo-1,2-di­phenyl-1,2-dicarba-closo-dodecaborane(9), C14H19B10I, has the expected pseudo-icosahedral cluster geometry, with a cage C—C distance of 1.724 (4) Å, comparable to that in the non-iodinated parent. However, the twist angles, θ, of the phenyl rings are 2.1 (6) and 27.6 (5)°, the latter being unusually large.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000743/gd1068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000743/gd1068Isup2.hkl
Contains datablock I

CCDC reference: 144650

Comment top

We are currently investigating the mechanism of the isomerization of closo-12-vertex dicarbametallaboranes (3,1,2-closo-MC2B9), wherein we exploit steric crowding to facilitate isomerization at reduced temperatures. This process models the well known thermal rearrangement (450 °) of the parent ortho-carborane to meta-carborane (Grafstein & Dvorak, 1963).

Our recent isolation and structural characterization of an intermediate in this process (Dunn et al., 1997) combine with our present vertex-labelling studies (Dunn et al., 1998, 1999) to provide evidence whereby a reliable picture of the rearrangement pathway may ultimately be built up.

As part of these labelling experiments, we have prepared the title compound (I) and are embarking upon studies of its metal complexes. However, the structure of the parent carborane reported here serves as a useful reference, and provides confirmation both of the position and of the structural `innocence' of the iodine substituent. [In fact, (I) was briefly reported over 20 years ago (Vasil'eva & Khalfina, 1976), but detailed structural and spectroscopic characterization are only now presented herein.] \sch

A view of a molecule of (I) is shown in Figure 1, along with the atomic numbering scheme. The carborane skeleton clearly has the anticipated pseudo-icosahedral architecture, with the two adjacent Ccage atoms C1 and C2 bearing phenyl substituents, and the molecule overall having the approximate molecular Cs symmetry mirrored in the solution NMR data. The boron atom B9, antipodal to one of the Ccage atoms, has undergone electrophilic substitution and bears the iodine atom I1 [B9—I1 2.178 (4) Å]. Cluster B—B and C—B distances are unremarkable, whilst the Ccage—Ccage separation, 1.724 (4) Å, is comparable to that in the parent 1,2-Ph2-1,2-closo-C2B10H10 (Lewis & Welch, 1993) where the corresponding parameter is 1.733 (4) (molecule A) and 1.720 (4) Å (molecule B).

The major deviation from molecular mirror symmetry in the structure of (I) lies in twisting of the planes of the aryl substitutents away from orthogonality with the notional molecular mirror plane. This twisting may be described by the angle θ, the modulus of the average Ccage—Ccage—CPh(ipso)—CPh(ortho) torsion angles (Cowie et al., 1994). In (I), the phenyl ring bound to C1 has θ = 2.0 (6)° and that at C2 has θ = 27.6 (5)°. The former value compares well with θ values in the parent compound [2.3 and 2.4° (molecule A) and 9.2 and 8.0° (molecule B): Lewis & Welch (1993)]; whereas the latter is quite unusually large. In such compounds, the magnitude of θ appears to be a consequence of weak intermolecular Ph···Ph interactions and/or packing in the solid state. In (I) the phenyl ring bound at C1 has a closest interplanar approach of over 3.3 Å to a neighbouring parallel ring, related to it by an inversion centre; whilst the ring bound at C2 is approximately orthogonal to the phenyl ring at C1 in a neighbouring molecule, with H103 and H104 within 3.0 Å of the plane of the former ring. It has in any case been shown previously that at lower θ different conformations are very similar in energy (Brain et al., 1996), and that in 1,2-Ph2-1,2-closo-C2B10H10 θ values of up to ca 40° can be tolerated without any destabilizing intramolecular Ph···Ph interaction (Lewis & Welch, 1993).

Another molecular feature of interest is that the B9—I1 vector is not symmetrically disposed with respect to the five boron atoms to which B9 is bound, but `bends' slightly towards C1. Thus B4—B9—I1 and B5—B9—I1 are both 119.1 (2)° whilst the other three B—B9—I1 angles lie in the range 121.7 (3) to 123.7 (2)°. (A similar effect can be seen, albeit less reliably, in a bending of the B12—H12 vector towards C2.) This perhaps reveals an interesting structural-electronic effect of the mutual steric crowding between the two phenyl groups. In the unsubstituted parent compound 1,2-closo-C2B10H12, the Ccage—Ccage distance is typically 1.629 (5) Å (Davidson et al., 1996). Thus, as the C···C connectivity extends in compounds such as (I) or its non-halogenated parent, the directions of the exo-radial orbitals forming the Ccage—CPh bonds mutually diverge and this is mirrored in the bending of the antipodal B9—X or B12—X vectors.

Experimental top

Compound (I) was prepared by an improvement upon the method of Vasil'eva & Khalfina (1976). Typically, 1,2-Ph2-1,2-closo-C2B10H10 (2.96 g, 10 mmol) and sublimed I2 (1.27 g, 5 mmol) were dissolved in glacial acetic acid (40 ml) at 313 K. A mixture of concentrated nitric acid and concentrated sulfuric acid (1:1 volume ratio, 20 ml) was added very slowly to the mixture (1 ml min-1). A brown vapour was observed above the purple solution and within 90 min the solution became pale brown and then decolorized. The colourless mixture was poured into a beaker containing distilled water (300 ml), resulting in a white precipitate which was isolated by filtration, washed with distilled water, dissolved in diethyl ether and dried over MgSO4. The dried ethereal solution was evaporated and the resulting off-white residue recrystallized from hexane to give the title compound (3.02 g, 7.15 mmol, 71.5%). Found: C 39.3, H 4.3%. C14H19B10I requires C 39.8, H 4.5%. IR (KBr disc): 3060 (w, νCH) and 2597 (s, νBH) cm-1. MS (EI): (m/z)max 424 (12C141H1911B10127I). NMR (CDCl3, 298 K): δ(11B) -0.9 (1B, B12), -8.6 (6B, B4,5,7,11,8,10), -11.0 (2B, B3,6), -15.2 (1B, B9); δ(1H) 7.39 (4H, m; ortho or meta C6H5), 7.26 (2H, m; para C6H5), 7.15 (4H, m; meta or ortho C6H5), 3.33 (2H, H3,6), 3.00 (3H, H12 and H4,5 or H7,11 or H8,10), 2.83 (2H, H8,10 or H7,11 or H4,5), 2.62 (2H, H7,11 or H8,10 or H4,5); δ(13C) 130.8 (2 para C, ortho C), 130.7 (ortho C), 130.2 (ipso C), 129.8 (ipso C), 128.7 (2 meta C), 86.1 (carboranyl C), 82.2 (carboranyl C). Diffraction-quality single crystals were obtained by slow mutual diffusion of a dichloromethane solution and petroleum ether (60–80) at 243 K.

Refinement top

Phenyl-H atoms were set riding with C—H 0.95 Å and with isotropic displacement parameters equal to 1.2 times Ueq of the corresponding C atom. Cluster H atoms were allowed free positional refinement, but were assigned isotropic temperature factors equal to 1.2 times Ueq of the corresponding B atom.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1999); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Perspective view of (I) with displacement ellipsoids shown at the 50% probability level for non-H atoms. H atoms are drawn as small circles of arbitrary radii.
9-iodo-1,2-diphenyl-1,2-closo-dicarbadodecaborane(9) top
Crystal data top
C14H19B10IDx = 1.497 Mg m3
Mr = 422.29Melting point: 176 - 177 °C K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.0913 (9) ÅCell parameters from 32 reflections
b = 11.4168 (11) Åθ = 4.8–12.5°
c = 18.0817 (17) ŵ = 1.70 mm1
β = 93.460 (7)°T = 160 K
V = 1873.3 (3) Å3Block, colourless
Z = 40.40 × 0.15 × 0.12 mm
F(000) = 824
Data collection top
Bruker P4
diffractometer
2628 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω scansh = 110
Absorption correction: empirical (using intensity measurements)
(SHELXTL; Sheldrick, 1999)
k = 131
Tmin = 0.746, Tmax = 0.815l = 2121
4407 measured reflections3 standard reflections every 97 reflections
3304 independent reflections intensity decay: 1.2%
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0259P)2 + 1.7031P]
where P = (Fo2 + 2Fc2)/3
3304 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
C14H19B10IV = 1873.3 (3) Å3
Mr = 422.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.0913 (9) ŵ = 1.70 mm1
b = 11.4168 (11) ÅT = 160 K
c = 18.0817 (17) Å0.40 × 0.15 × 0.12 mm
β = 93.460 (7)°
Data collection top
Bruker P4
diffractometer
2628 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(SHELXTL; Sheldrick, 1999)
Rint = 0.033
Tmin = 0.746, Tmax = 0.8153 standard reflections every 97 reflections
4407 measured reflections intensity decay: 1.2%
3304 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.77 e Å3
3304 reflectionsΔρmin = 0.58 e Å3
253 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
C11.0902 (4)0.6085 (3)0.27551 (18)0.0218 (7)
C20.9113 (4)0.6240 (3)0.23945 (18)0.0226 (7)
B31.0333 (4)0.7399 (4)0.2348 (2)0.0259 (8)
H31.019 (4)0.815 (3)0.267 (2)0.031*
B41.2090 (5)0.6780 (4)0.2200 (2)0.0274 (8)
H41.308 (4)0.715 (3)0.244 (2)0.033*
B51.1870 (4)0.5219 (4)0.2183 (2)0.0263 (8)
H51.270 (4)0.472 (4)0.245 (2)0.032*
B60.9994 (5)0.4896 (3)0.2330 (2)0.0253 (8)
H60.959 (4)0.422 (3)0.264 (2)0.030*
B70.9093 (5)0.7029 (4)0.1588 (2)0.0290 (9)
H70.819 (4)0.761 (4)0.147 (2)0.035*
B81.0976 (5)0.7370 (4)0.1442 (2)0.0309 (9)
H81.131 (4)0.817 (4)0.117 (2)0.037*
B91.1913 (5)0.6012 (4)0.1344 (2)0.0291 (9)
I11.38279 (3)0.58482 (3)0.068280 (15)0.04696 (11)
B101.0638 (5)0.4837 (4)0.1427 (2)0.0292 (9)
H101.080 (4)0.399 (3)0.113 (2)0.035*
B110.8893 (5)0.5485 (4)0.1569 (2)0.0279 (8)
H110.786 (4)0.515 (4)0.141 (2)0.033*
B121.0079 (5)0.6166 (4)0.0958 (2)0.0320 (9)
H120.968 (5)0.617 (4)0.032 (2)0.038*
C1011.1231 (4)0.6047 (3)0.35857 (18)0.0244 (7)
C1021.1340 (4)0.4973 (3)0.3946 (2)0.0333 (9)
H1021.11540.42700.36750.040*
C1031.1719 (5)0.4922 (4)0.4703 (2)0.0466 (11)
H1031.17950.41880.49500.056*
C1041.1985 (5)0.5953 (4)0.5093 (2)0.0447 (10)
H1041.22310.59230.56110.054*
C1051.1898 (4)0.7016 (4)0.4741 (2)0.0397 (10)
H1051.20900.77160.50150.048*
C1061.1527 (4)0.7071 (4)0.3983 (2)0.0318 (8)
H1061.14760.78070.37380.038*
C2010.7898 (4)0.6314 (3)0.29228 (18)0.0234 (7)
C2020.6820 (4)0.5448 (3)0.2902 (2)0.0300 (8)
H2020.68600.48200.25590.036*
C2030.5680 (4)0.5498 (4)0.3383 (2)0.0373 (9)
H2030.49420.49080.33630.045*
C2040.5615 (4)0.6401 (4)0.3889 (2)0.0365 (9)
H2040.48370.64320.42170.044*
C2050.6691 (4)0.7258 (3)0.39156 (19)0.0316 (8)
H2050.66520.78790.42640.038*
C2060.7829 (4)0.7220 (3)0.34364 (18)0.0276 (7)
H2060.85630.78130.34590.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0196 (15)0.0217 (18)0.0243 (16)0.0008 (13)0.0024 (13)0.0004 (13)
C20.0219 (16)0.0205 (16)0.0251 (16)0.0004 (14)0.0010 (13)0.0004 (14)
B30.0257 (19)0.022 (2)0.0297 (19)0.0018 (17)0.0038 (16)0.0032 (17)
B40.025 (2)0.026 (2)0.031 (2)0.0039 (17)0.0042 (17)0.0020 (17)
B50.025 (2)0.028 (2)0.0266 (19)0.0045 (17)0.0040 (16)0.0030 (17)
B60.027 (2)0.021 (2)0.0276 (19)0.0011 (16)0.0006 (16)0.0025 (16)
B70.031 (2)0.030 (2)0.0260 (19)0.0058 (18)0.0042 (16)0.0042 (17)
B80.033 (2)0.030 (2)0.031 (2)0.0025 (19)0.0091 (17)0.0074 (18)
B90.027 (2)0.033 (2)0.0288 (19)0.0001 (18)0.0078 (16)0.0015 (17)
I10.04321 (17)0.05530 (19)0.04485 (16)0.00590 (14)0.02312 (12)0.00002 (14)
B100.028 (2)0.028 (2)0.031 (2)0.0006 (18)0.0014 (17)0.0038 (17)
B110.029 (2)0.027 (2)0.0274 (19)0.0003 (17)0.0011 (16)0.0016 (16)
B120.034 (2)0.035 (2)0.026 (2)0.0061 (19)0.0008 (17)0.0033 (17)
C1010.0198 (16)0.0286 (19)0.0247 (16)0.0032 (14)0.0007 (13)0.0000 (14)
C1020.037 (2)0.036 (2)0.0264 (18)0.0048 (17)0.0046 (16)0.0007 (16)
C1030.054 (3)0.051 (3)0.033 (2)0.004 (2)0.007 (2)0.0096 (19)
C1040.043 (2)0.065 (3)0.0253 (18)0.002 (2)0.0053 (16)0.004 (2)
C1050.031 (2)0.051 (3)0.036 (2)0.0044 (19)0.0042 (17)0.0154 (19)
C1060.0249 (17)0.036 (2)0.0346 (19)0.0029 (16)0.0003 (15)0.0060 (17)
C2010.0207 (16)0.0233 (16)0.0261 (16)0.0035 (14)0.0003 (13)0.0045 (14)
C2020.0249 (18)0.0282 (19)0.0369 (19)0.0020 (15)0.0027 (15)0.0007 (16)
C2030.0250 (18)0.038 (2)0.048 (2)0.0064 (17)0.0021 (17)0.0046 (18)
C2040.0275 (19)0.044 (2)0.039 (2)0.0071 (18)0.0088 (16)0.0067 (19)
C2050.0293 (18)0.037 (2)0.0286 (17)0.0073 (17)0.0029 (15)0.0015 (16)
C2060.0236 (17)0.0283 (19)0.0307 (17)0.0005 (15)0.0006 (14)0.0018 (15)
Geometric parameters (Å, º) top
C1—C1011.514 (4)B8—H81.08 (4)
C1—B51.713 (5)B9—B121.777 (6)
C1—B41.713 (5)B9—B101.786 (6)
C1—C21.724 (4)B9—I12.178 (4)
C1—B31.736 (5)B10—B111.784 (6)
C1—B61.744 (5)B10—B121.797 (6)
C2—C2011.506 (5)B10—H101.12 (4)
C2—B71.714 (5)B11—B121.769 (6)
C2—B111.724 (5)B11—H111.04 (4)
C2—B31.732 (5)B12—H121.21 (3)
C2—B61.738 (5)C101—C1021.388 (5)
B3—B81.773 (5)C101—C1061.390 (5)
B3—B71.776 (6)C102—C1031.393 (5)
B3—B41.783 (6)C102—H1020.9500
B3—H31.05 (4)C103—C1041.387 (6)
B4—B91.779 (6)C103—H1030.9500
B4—B81.787 (6)C104—C1051.370 (6)
B4—B51.793 (6)C104—H1040.9500
B4—H41.06 (3)C105—C1061.394 (5)
B5—B101.768 (6)C105—H1050.9500
B5—B91.770 (6)C106—H1060.9500
B5—B61.781 (6)C201—C2021.391 (5)
B5—H51.04 (4)C201—C2061.394 (5)
B6—B101.770 (6)C202—C2031.393 (5)
B6—B111.784 (6)C202—H2020.9500
B6—H61.02 (3)C203—C2041.383 (6)
B7—B111.771 (6)C203—H2030.9500
B7—B121.787 (6)C204—C2051.383 (6)
B7—B81.791 (6)C204—H2040.9500
B7—H71.07 (4)C205—C2061.390 (5)
B8—B91.783 (6)C205—H2050.9500
B8—B121.799 (6)C206—H2060.9500
C101—C1—B5120.3 (3)B3—B8—B759.8 (2)
C101—C1—B4120.0 (3)B9—B8—B7107.0 (3)
B5—C1—B463.1 (2)B4—B8—B7107.9 (3)
C101—C1—C2120.2 (3)B3—B8—B12107.3 (3)
B5—C1—C2109.7 (3)B9—B8—B1259.5 (2)
B4—C1—C2110.2 (3)B4—B8—B12107.7 (3)
C101—C1—B3118.8 (3)B7—B8—B1259.7 (2)
B5—C1—B3113.2 (3)B3—B8—H8121 (2)
B4—C1—B362.2 (2)B9—B8—H8123 (2)
C2—C1—B360.1 (2)B4—B8—H8120 (2)
C101—C1—B6118.3 (3)B7—B8—H8123 (2)
B5—C1—B662.0 (2)B12—B8—H8124 (2)
B4—C1—B6113.6 (3)B5—B9—B12108.6 (3)
C2—C1—B660.2 (2)B5—B9—B460.7 (2)
B3—C1—B6111.4 (3)B12—B9—B4109.1 (3)
C201—C2—B7122.7 (3)B5—B9—B8108.9 (3)
C201—C2—B11121.7 (3)B12—B9—B860.7 (2)
B7—C2—B1162.0 (2)B4—B9—B860.2 (2)
C201—C2—C1118.5 (3)B5—B9—B1059.7 (2)
B7—C2—C1109.7 (3)B12—B9—B1060.6 (2)
B11—C2—C1109.5 (3)B4—B9—B10108.8 (3)
C201—C2—B3118.9 (3)B8—B9—B10109.2 (3)
B7—C2—B362.0 (2)B5—B9—I1119.1 (2)
B11—C2—B3112.4 (3)B12—B9—I1123.7 (2)
C1—C2—B360.3 (2)B4—B9—I1119.1 (2)
C201—C2—B6116.8 (3)B8—B9—I1122.1 (2)
B7—C2—B6112.9 (3)B10—B9—I1121.7 (3)
B11—C2—B662.0 (2)B5—B10—B660.4 (2)
C1—C2—B660.5 (2)B5—B10—B11108.2 (3)
B3—C2—B6111.9 (3)B6—B10—B1160.3 (2)
C2—B3—C159.6 (2)B5—B10—B959.7 (2)
C2—B3—B8106.2 (3)B6—B10—B9107.6 (3)
C1—B3—B8105.6 (3)B11—B10—B9106.7 (3)
C2—B3—B758.5 (2)B5—B10—B12107.7 (3)
C1—B3—B7106.4 (3)B6—B10—B12107.7 (3)
B8—B3—B760.6 (2)B11—B10—B1259.2 (2)
C2—B3—B4106.7 (3)B9—B10—B1259.5 (2)
C1—B3—B458.3 (2)B5—B10—H10119 (2)
B8—B3—B460.4 (2)B6—B10—H10123 (2)
B7—B3—B4108.8 (3)B11—B10—H10125 (2)
C2—B3—H3120 (2)B9—B10—H10120 (2)
C1—B3—H3121 (2)B12—B10—H10123 (2)
B8—B3—H3126 (2)C2—B11—B12106.1 (3)
B7—B3—H3122 (2)C2—B11—B758.7 (2)
B4—B3—H3123 (2)B12—B11—B760.6 (2)
C1—B4—B9104.8 (3)C2—B11—B10105.9 (3)
C1—B4—B359.5 (2)B12—B11—B1060.7 (2)
B9—B4—B3106.9 (3)B7—B11—B10108.9 (3)
C1—B4—B8106.0 (3)C2—B11—B659.3 (2)
B9—B4—B860.0 (2)B12—B11—B6108.2 (3)
B3—B4—B859.6 (2)B7—B11—B6108.0 (3)
C1—B4—B558.4 (2)B10—B11—B659.5 (2)
B9—B4—B559.4 (2)C2—B11—H11119 (2)
B3—B4—B5107.2 (3)B12—B11—H11124 (2)
B8—B4—B5107.7 (3)B7—B11—H11118 (2)
C1—B4—H4119 (2)B10—B11—H11127 (2)
B9—B4—H4126 (2)B6—B11—H11122 (2)
B3—B4—H4121 (2)B11—B12—B9107.7 (3)
B8—B4—H4126 (2)B11—B12—B759.8 (2)
B5—B4—H4120 (2)B9—B12—B7107.4 (3)
C1—B5—B10106.6 (3)B11—B12—B1060.0 (2)
C1—B5—B9105.2 (3)B9—B12—B1060.0 (2)
B10—B5—B960.6 (2)B7—B12—B10107.7 (3)
C1—B5—B659.8 (2)B11—B12—B8107.9 (3)
B10—B5—B659.8 (2)B9—B12—B859.8 (2)
B9—B5—B6107.8 (3)B7—B12—B859.9 (2)
C1—B5—B458.4 (2)B10—B12—B8108.0 (3)
B10—B5—B4108.9 (3)B11—B12—H12117 (2)
B9—B5—B459.9 (2)B9—B12—H12127 (2)
B6—B5—B4108.1 (3)B7—B12—H12119 (2)
C1—B5—H5115 (2)B10—B12—H12122 (2)
B10—B5—H5129 (2)B8—B12—H12125 (2)
B9—B5—H5128 (2)C102—C101—C106119.6 (3)
B6—B5—H5120 (2)C102—C101—C1119.7 (3)
B4—B5—H5117 (2)C106—C101—C1120.5 (3)
C2—B6—C159.36 (19)C101—C102—C103120.3 (4)
C2—B6—B10105.9 (3)C101—C102—H102119.8
C1—B6—B10105.2 (3)C103—C102—H102119.8
C2—B6—B5106.0 (3)C104—C103—C102119.3 (4)
C1—B6—B558.1 (2)C104—C103—H103120.4
B10—B6—B559.8 (2)C102—C103—H103120.4
C2—B6—B1158.6 (2)C105—C104—C103120.9 (3)
C1—B6—B11105.9 (3)C105—C104—H104119.5
B10—B6—B1160.2 (2)C103—C104—H104119.5
B5—B6—B11107.7 (3)C104—C105—C106120.0 (4)
C2—B6—H6116 (2)C104—C105—H105120.0
C1—B6—H6121 (2)C106—C105—H105120.0
B10—B6—H6128 (2)C101—C106—C105119.9 (4)
B5—B6—H6128 (2)C101—C106—H106120.0
B11—B6—H6120 (2)C105—C106—H106120.0
C2—B7—B1159.3 (2)C202—C201—C206119.0 (3)
C2—B7—B359.5 (2)C202—C201—C2119.1 (3)
B11—B7—B3108.1 (3)C206—C201—C2121.9 (3)
C2—B7—B12105.8 (3)C201—C202—C203120.2 (4)
B11—B7—B1259.6 (2)C201—C202—H202119.9
B3—B7—B12107.8 (3)C203—C202—H202119.9
C2—B7—B8106.2 (3)C204—C203—C202120.5 (4)
B11—B7—B8108.2 (3)C204—C203—H203119.8
B3—B7—B859.6 (2)C202—C203—H203119.8
B12—B7—B860.4 (2)C203—C204—C205119.5 (3)
C2—B7—H7118 (2)C203—C204—H204120.3
B11—B7—H7123 (2)C205—C204—H204120.3
B3—B7—H7117 (2)C204—C205—C206120.5 (3)
B12—B7—H7129 (2)C204—C205—H205119.7
B8—B7—H7124 (2)C206—C205—H205119.7
B3—B8—B9107.1 (3)C205—C206—C201120.3 (3)
B3—B8—B460.1 (2)C205—C206—H206119.9
B9—B8—B459.7 (2)C201—C206—H206119.9
C1—C2—C201—C202117.3 (3)C2—C1—C101—C10294.3 (4)
C1—C2—C201—C20662.1 (4)C2—C1—C101—C10690.2 (4)

Experimental details

Crystal data
Chemical formulaC14H19B10I
Mr422.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)160
a, b, c (Å)9.0913 (9), 11.4168 (11), 18.0817 (17)
β (°) 93.460 (7)
V3)1873.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.70
Crystal size (mm)0.40 × 0.15 × 0.12
Data collection
DiffractometerBruker P4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SHELXTL; Sheldrick, 1999)
Tmin, Tmax0.746, 0.815
No. of measured, independent and
observed [I > 2σ(I)] reflections
4407, 3304, 2628
Rint0.033
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.085, 1.02
No. of reflections3304
No. of parameters253
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.77, 0.58

Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXTL (Sheldrick, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
C1—C1011.514 (4)C2—C2011.506 (5)
C1—C21.724 (4)B9—I12.178 (4)
B5—B9—I1119.1 (2)B8—B9—I1122.1 (2)
B12—B9—I1123.7 (2)B10—B9—I1121.7 (3)
B4—B9—I1119.1 (2)
C1—C2—C201—C202117.3 (3)C2—C1—C101—C10294.3 (4)
C1—C2—C201—C20662.1 (4)C2—C1—C101—C10690.2 (4)
 

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