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The title compound, C6H18B10, is the first X-ray investigated carborane with a propenyl substituent. The C-C bond length in the carborane cage is 1.688 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020165/na6109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020165/na6109Isup2.hkl
Contains datablock I

CCDC reference: 180530

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.057
  • wR factor = 0.128
  • Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_320 Alert C Check Hybridisation of C(1) in main residue ? PLAT_320 Alert C Check Hybridisation of C(2) in main residue ? PLAT_367 Alert C Long? C(sp?)-C(sp?) Bond C(1) - C(2) = 1.69 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

The propenyl substituent is situated in the bisect plane of C1—B3—B4 triangular face, with a B4—C1—C13—C14 torsion angle of 36.8 (2)°.

The C1—C2 distance of 1.688 (2) Å in (I) is significant longer compared with those in B-substituent carboranes (Grintselev-Knyazev et al., 2001), which agrees with the general tendency of C—C bond elongation in aryl C-substituent carboranes (Lewis & Welch, 1993).

The crystal packing is shown in Fig. 2.

Experimental top

A solution of 1-Me-1,2-C2B10H12 was treated with n-butyllithium in ether to afford the intermediate lithiated species. The mix obtained was added to allyl bromide to give 1-allyl-2-methyl-1,2-C2B10H12 (Heying et al., 1963). 1-Propenyl-2-methyl-1,2-C2B10H12 was obtained by isomerization of 1-allyl-2-methyl-1,2-C2B10H12 with an excess of alkali. The NMR spectra was obtained in d6-acetone (5% solution). 1H (360 MHz, δ, p.p.m.): 6.31 (dq, CHCH3, 1H), 5.88 (dd, B—CH, 1H), 2.00 (s, B—CH3, 3H), 1.81 (dd, CH3—CH, 3H). 13C (90.6 MHz, δ, p.p.m.): 139.55 and 123.50 (HC), 78.75 and 76.02 (Ccarb), 22.68 and 17.24 (CH3). 11B (115.54 MHz, δ, p.p.m.): -3.80, -4.91, -8.52, -9.16, -10.01 (relative intensity 1:1:2:4:2).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SMART and SAINT; 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. View of the crystal packing of (I).
1-propenyl-2-methyl-1,2-dicarba-closo-dodecaborane(12) top
Crystal data top
C6H18B10Dx = 1.075 Mg m3
Mr = 198.30Melting point: 362-364K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.3615 (16) ÅCell parameters from 821 reflections
b = 21.815 (5) Åθ = 3–30°
c = 7.6346 (16) ŵ = 0.05 mm1
β = 91.541 (5)°T = 110 K
V = 1225.6 (5) Å3Prism, colorless
Z = 40.50 × 0.45 × 0.40 mm
F(000) = 416
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3557 independent reflections
Radiation source: fine-focus sealed tube2306 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.976, Tmax = 0.981k = 3030
14366 measured reflectionsl = 1010
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)] = 0.057Hydrogen site location: difference Fourier map
wR(F2) = 0.128All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.028P)2 + 0.70P]
where P = (Fo2 + 2Fc2)/3
3557 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C6H18B10V = 1225.6 (5) Å3
Mr = 198.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.3615 (16) ŵ = 0.05 mm1
b = 21.815 (5) ÅT = 110 K
c = 7.6346 (16) Å0.50 × 0.45 × 0.40 mm
β = 91.541 (5)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3557 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2306 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.981Rint = 0.049
14366 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.128All H-atom parameters refined
S = 1.03Δρmax = 0.34 e Å3
3557 reflectionsΔρmin = 0.22 e Å3
217 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
C10.15700 (17)0.11004 (6)0.90350 (17)0.0173 (3)
C20.03282 (18)0.17498 (6)0.91138 (17)0.0190 (3)
B100.1499 (2)0.09404 (8)0.6897 (2)0.0230 (3)
C130.25511 (19)0.09043 (7)1.06641 (18)0.0220 (3)
C160.0367 (2)0.21027 (8)1.0810 (2)0.0273 (3)
B40.2409 (2)0.10067 (7)0.6996 (2)0.0209 (3)
B80.1589 (2)0.16376 (7)0.5754 (2)0.0217 (3)
B90.0468 (2)0.09157 (8)0.5594 (2)0.0232 (3)
C140.4315 (2)0.09357 (7)1.0946 (2)0.0272 (3)
B60.0763 (2)0.10535 (7)0.9081 (2)0.0202 (3)
B70.0296 (2)0.21101 (7)0.7139 (2)0.0214 (3)
B30.2297 (2)0.17460 (7)0.79539 (19)0.0199 (3)
B110.1592 (2)0.16814 (8)0.7851 (2)0.0226 (3)
B120.0836 (2)0.15988 (8)0.5681 (2)0.0232 (3)
B50.0513 (2)0.05774 (7)0.7703 (2)0.0214 (3)
C150.5269 (2)0.07235 (9)1.2580 (2)0.0334 (4)
H60.131 (2)0.0919 (7)1.031 (2)0.021 (4)*
H30.3422 (19)0.1973 (7)0.8500 (18)0.016 (4)*
H50.068 (2)0.0111 (7)0.809 (2)0.025 (4)*
H40.371 (2)0.0798 (7)0.691 (2)0.026 (4)*
H80.238 (2)0.1811 (7)0.470 (2)0.023 (4)*
H90.050 (2)0.0640 (8)0.439 (2)0.031 (4)*
H100.271 (2)0.0681 (8)0.661 (2)0.037 (5)*
H120.163 (2)0.1754 (8)0.455 (2)0.030 (4)*
H15C0.447 (3)0.0547 (8)1.335 (2)0.038 (5)*
H70.020 (2)0.2605 (9)0.713 (2)0.040 (5)*
H110.281 (2)0.1910 (8)0.827 (2)0.033 (5)*
H16C0.034 (2)0.2517 (9)1.058 (2)0.039 (5)*
H130.187 (2)0.0736 (8)1.149 (2)0.033 (5)*
H140.502 (3)0.1086 (8)1.009 (3)0.040 (5)*
H15B0.589 (3)0.1041 (10)1.308 (3)0.054 (6)*
H15A0.617 (3)0.0430 (9)1.240 (2)0.043 (5)*
H16B0.137 (3)0.2059 (10)1.149 (3)0.054 (6)*
H16A0.064 (3)0.2022 (10)1.146 (3)0.052 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0169 (6)0.0177 (6)0.0175 (6)0.0004 (5)0.0026 (5)0.0015 (5)
C20.0198 (6)0.0200 (6)0.0172 (6)0.0022 (5)0.0011 (5)0.0006 (5)
B100.0212 (7)0.0246 (8)0.0232 (8)0.0054 (6)0.0031 (6)0.0022 (6)
C130.0224 (7)0.0250 (7)0.0188 (6)0.0004 (5)0.0022 (5)0.0051 (5)
C160.0349 (9)0.0273 (8)0.0198 (7)0.0053 (7)0.0007 (6)0.0051 (6)
B40.0227 (7)0.0232 (8)0.0171 (7)0.0001 (6)0.0051 (6)0.0002 (6)
B80.0234 (8)0.0243 (8)0.0175 (7)0.0037 (6)0.0013 (6)0.0025 (6)
B90.0262 (8)0.0246 (8)0.0188 (7)0.0035 (6)0.0003 (6)0.0025 (6)
C140.0239 (7)0.0320 (8)0.0258 (7)0.0000 (6)0.0008 (6)0.0069 (6)
B60.0168 (7)0.0229 (8)0.0212 (7)0.0017 (6)0.0019 (5)0.0035 (6)
B70.0256 (8)0.0192 (7)0.0194 (7)0.0009 (6)0.0005 (6)0.0039 (6)
B30.0202 (7)0.0210 (7)0.0185 (7)0.0032 (6)0.0018 (6)0.0017 (6)
B110.0200 (7)0.0268 (8)0.0209 (7)0.0025 (6)0.0002 (6)0.0028 (6)
B120.0264 (8)0.0255 (8)0.0176 (7)0.0034 (6)0.0012 (6)0.0024 (6)
B50.0239 (8)0.0179 (7)0.0223 (7)0.0029 (6)0.0003 (6)0.0005 (6)
C150.0253 (8)0.0417 (10)0.0330 (9)0.0014 (7)0.0059 (7)0.0094 (7)
Geometric parameters (Å, º) top
C1—C131.4843 (18)B4—H41.067 (16)
C1—C21.6880 (19)B8—B31.761 (2)
C1—B51.703 (2)B8—B71.772 (2)
C1—B41.702 (2)B8—B91.781 (2)
C1—B61.722 (2)B8—B121.787 (2)
C1—B31.725 (2)B8—H81.072 (15)
C2—C161.5062 (19)B9—B51.771 (2)
C2—B111.696 (2)B9—B121.775 (2)
C2—B71.700 (2)B9—H91.096 (17)
C2—B61.718 (2)C14—C151.489 (2)
C2—B31.718 (2)C14—H140.904 (19)
B10—B61.756 (2)B6—B111.760 (2)
B10—B51.775 (2)B6—B51.766 (2)
B10—B111.775 (2)B6—H61.070 (15)
B10—B91.779 (2)B7—B121.769 (2)
B10—B121.785 (2)B7—B31.771 (2)
B10—H101.073 (18)B7—B111.773 (2)
C13—C141.312 (2)B7—H71.082 (18)
C13—H130.897 (18)B3—H31.042 (14)
C16—H16C0.92 (2)B11—B121.771 (2)
C16—H16B0.89 (2)B11—H111.084 (17)
C16—H16A0.92 (2)B12—H121.086 (17)
B4—B81.768 (2)B5—H51.065 (16)
B4—B91.774 (2)C15—H15C0.923 (19)
B4—B31.774 (2)C15—H15B0.91 (2)
B4—B51.777 (2)C15—H15A0.94 (2)
C13—C1—C2117.63 (11)C13—C14—C15124.34 (14)
C13—C1—B5120.77 (11)C13—C14—H14119.0 (12)
C2—C1—B5110.14 (10)C15—C14—H14116.7 (12)
C13—C1—B4123.46 (11)C2—B6—C158.77 (8)
C2—C1—B4110.09 (10)C2—B6—B10105.68 (11)
B5—C1—B462.91 (9)C1—B6—B10105.75 (11)
C13—C1—B6115.41 (11)C2—B6—B1158.36 (9)
C2—C1—B660.50 (8)C1—B6—B11105.96 (10)
B5—C1—B662.10 (9)B10—B6—B1160.63 (9)
B4—C1—B6113.45 (11)C2—B6—B5105.83 (10)
C13—C1—B3119.09 (11)C1—B6—B558.41 (8)
C2—C1—B360.45 (8)B10—B6—B560.50 (9)
B5—C1—B3113.83 (10)B11—B6—B5108.81 (11)
B4—C1—B362.33 (9)C2—B6—H6114.6 (8)
B6—C1—B3112.36 (10)C1—B6—H6115.7 (8)
C16—C2—C1117.51 (11)B10—B6—H6132.7 (8)
C16—C2—B11121.99 (12)B11—B6—H6123.1 (8)
C1—C2—B11110.48 (10)B5—B6—H6125.3 (8)
C16—C2—B7121.72 (12)C2—B7—B12105.16 (11)
C1—C2—B7110.55 (10)C2—B7—B8105.38 (11)
B11—C2—B762.95 (9)B12—B7—B860.61 (9)
C16—C2—B6117.55 (12)C2—B7—B359.30 (8)
C1—C2—B660.72 (8)B12—B7—B3108.15 (11)
B11—C2—B662.07 (9)B8—B7—B359.60 (9)
B7—C2—B6113.60 (11)C2—B7—B1158.42 (8)
C16—C2—B3116.67 (12)B12—B7—B1160.01 (9)
C1—C2—B360.83 (8)B8—B7—B11108.31 (11)
B11—C2—B3114.10 (10)B3—B7—B11107.87 (11)
B7—C2—B362.41 (9)C2—B7—H7117.9 (10)
B6—C2—B3112.86 (10)B12—B7—H7126.5 (10)
B6—B10—B560.03 (9)B8—B7—H7127.6 (10)
B6—B10—B1159.80 (9)B3—B7—H7120.2 (10)
B5—B10—B11107.78 (11)B11—B7—H7118.6 (9)
B6—B10—B9107.48 (11)C2—B3—C158.72 (8)
B5—B10—B959.78 (9)C2—B3—B8105.08 (11)
B11—B10—B9107.36 (11)C1—B3—B8105.02 (11)
B6—B10—B12107.41 (11)C2—B3—B758.29 (8)
B5—B10—B12107.60 (11)C1—B3—B7105.60 (10)
B11—B10—B1259.67 (9)B8—B3—B760.22 (9)
B9—B10—B1259.72 (9)C2—B3—B4105.44 (10)
B6—B10—H10120.1 (9)C1—B3—B458.22 (8)
B5—B10—H10121.1 (10)B8—B3—B460.03 (9)
B11—B10—H10121.5 (9)B7—B3—B4108.09 (11)
B9—B10—H10123.6 (9)C2—B3—H3117.6 (8)
B12—B10—H10123.7 (9)C1—B3—H3116.8 (8)
C14—C13—C1125.42 (13)B8—B3—H3131.0 (8)
C14—C13—H13118.5 (11)B7—B3—H3124.8 (8)
C1—C13—H13116.0 (11)B4—B3—H3123.5 (8)
C2—C16—H16C109.6 (11)C2—B11—B659.58 (9)
C2—C16—H16B116.1 (13)C2—B11—B12105.22 (11)
H16C—C16—H16B103.3 (17)B6—B11—B12107.84 (11)
C2—C16—H16A111.5 (13)C2—B11—B758.63 (8)
H16C—C16—H16A106.2 (17)B6—B11—B7108.08 (11)
H16B—C16—H16A109.4 (18)B12—B11—B759.87 (9)
C1—B4—B8105.64 (11)C2—B11—B10105.80 (11)
C1—B4—B9105.02 (11)B6—B11—B1059.57 (9)
B8—B4—B960.37 (9)B12—B11—B1060.45 (9)
C1—B4—B359.45 (8)B7—B11—B10108.36 (11)
B8—B4—B359.62 (9)C2—B11—H11118.5 (9)
B9—B4—B3107.75 (11)B6—B11—H11118.7 (9)
C1—B4—B558.55 (8)B12—B11—H11127.3 (9)
B8—B4—B5108.27 (11)B7—B11—H11120.7 (9)
B9—B4—B559.84 (9)B10—B11—H11125.6 (9)
B3—B4—B5107.95 (11)B7—B12—B1160.12 (9)
C1—B4—H4117.3 (9)B7—B12—B9107.87 (11)
B8—B4—H4126.3 (9)B11—B12—B9107.72 (11)
B9—B4—H4128.8 (9)B7—B12—B859.77 (9)
B3—B4—H4117.8 (9)B11—B12—B8107.73 (11)
B5—B4—H4120.7 (9)B9—B12—B860.00 (9)
B3—B8—B460.35 (9)B7—B12—B10108.10 (11)
B3—B8—B760.19 (9)B11—B12—B1059.88 (9)
B4—B8—B7108.32 (11)B9—B12—B1059.97 (9)
B3—B8—B9108.01 (11)B8—B12—B10107.96 (11)
B4—B8—B959.97 (9)B7—B12—H12122.6 (9)
B7—B8—B9107.48 (11)B11—B12—H12122.7 (9)
B3—B8—B12107.83 (11)B9—B12—H12120.8 (9)
B4—B8—B12107.85 (11)B8—B12—H12121.6 (9)
B7—B8—B1259.61 (9)B10—B12—H12121.2 (9)
B9—B8—B1259.67 (9)C1—B5—B659.49 (8)
B3—B8—H8121.0 (8)C1—B5—B9105.13 (11)
B4—B8—H8119.5 (8)B6—B5—B9107.40 (11)
B7—B8—H8123.4 (8)C1—B5—B10105.77 (11)
B9—B8—H8121.3 (8)B6—B5—B1059.47 (9)
B12—B8—H8123.6 (8)B9—B5—B1060.24 (9)
B5—B9—B460.17 (9)C1—B5—B458.54 (8)
B5—B9—B12108.22 (11)B6—B5—B4107.80 (11)
B4—B9—B12108.14 (11)B9—B5—B459.98 (9)
B5—B9—B1059.98 (9)B10—B5—B4108.32 (11)
B4—B9—B10108.27 (11)C1—B5—H5115.2 (8)
B12—B9—B1060.31 (9)B6—B5—H5117.3 (8)
B5—B9—B8107.97 (11)B9—B5—H5130.4 (8)
B4—B9—B859.66 (9)B10—B5—H5127.8 (8)
B12—B9—B860.33 (9)B4—B5—H5119.9 (8)
B10—B9—B8108.49 (11)C14—C15—H15C111.6 (11)
B5—B9—H9122.1 (9)C14—C15—H15B109.8 (14)
B4—B9—H9121.9 (9)H15C—C15—H15B111.5 (18)
B12—B9—H9121.1 (9)C14—C15—H15A114.3 (12)
B10—B9—H9121.4 (9)H15C—C15—H15A105.8 (16)
B8—B9—H9121.4 (9)H15B—C15—H15A103.5 (17)

Experimental details

Crystal data
Chemical formulaC6H18B10
Mr198.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)110
a, b, c (Å)7.3615 (16), 21.815 (5), 7.6346 (16)
β (°) 91.541 (5)
V3)1225.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.05
Crystal size (mm)0.50 × 0.45 × 0.40
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.976, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
14366, 3557, 2306
Rint0.049
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.128, 1.03
No. of reflections3557
No. of parameters217
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.34, 0.22

Computer programs: SMART (Bruker, 1998), SMART and SAINT (Bruker, 1999), SMART and SAINT, SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
C1—C131.4843 (18)C13—C141.312 (2)
C1—C21.6880 (19)C14—C151.489 (2)
C2—C161.5062 (19)
C13—C1—C2117.63 (11)C14—C13—C1125.42 (13)
C16—C2—C1117.51 (11)C13—C14—C15124.34 (14)
 

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