Literature DB >> 21587928

9-Ethynyl-1,2-dimethyl-1,2-dicarba-closo-dodeca-borane (1,2-Me(2)-9-HC C-closo-1,2-C(2)B(10)H(9)).

Maik Finze1, Guido J Reiss.   

Abstract

The asymmetric unit of the title compound, C(6)H(16)B(10), contains one mol-ecule that is close to possessing a non-crystallographic plane of mirror symmetry in the space group Pna2(1). The orientation of the mol-ecules in the ortho-rhom-bic cell shows that the structure can not be described in the space group Pnma, which has the same systematic absence conditions. The long inner-cluster C-C distance of 1.510 (5) Å is typical for {1,2-Me(2)-closo-1,2-C(2)B(10)} derivatives.

Entities:  

Year:  2010        PMID： 21587928      PMCID： PMC3006814          DOI： 10.1107/S1600536810022440

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a general overview of the functionalization of dicarba-closo-dodeca­boranes, see: Bregadze (1992 ▶); Kalinin & Ol’shevskaya (2008 ▶). For the synthesis and properties of {closo-1,2-C2B10} clusters with ethynyl groups bonded to boron, see: Zakharkin et al. (1981 ▶); Himmelspach & Finze (2010a ▶). For structures of related icosa­hedral boron cages with alkynyl groups bonded to boron, see: Finze (2008 ▶); Himmelspach & Finze (2010b ▶). For intensity statistics of Friedel opposites for all non-centrosymmetric space groups, see: Shmueli et al. (2008 ▶).

Experimental

Crystal data

C6H16B10 M = 196.29 Orthorhombic, a = 14.5368 (8) Å b = 7.0085 (3) Å c = 12.5373 (5) Å V = 1277.32 (10) Å3 Z = 4 Mo Kα radiation μ = 0.05 mm−1 T = 290 K 0.4 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer 11327 measured reflections 1181 independent reflections 1049 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.104 S = 1.06 1181 reflections 150 parameters 1 restraint H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022440/si2268sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022440/si2268Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C6H16B10F(000) = 408
Mr = 196.29Dx = 1.021 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 6575 reflections
a = 14.5368 (8) Åθ = 3.2–27.2°
b = 7.0085 (3) ŵ = 0.05 mm−1
c = 12.5373 (5) ÅT = 290 K
V = 1277.32 (10) Å3Prism, colourless
Z = 40.4 × 0.2 × 0.2 mm
Oxford Diffraction Xcalibur Eos diffractometer1049 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.042
graphiteθmax = 25.0°, θmin = 3.2°
Detector resolution: 16.2711 pixels mm-1h = −17→17
ω scansk = −8→8
11327 measured reflectionsl = −14→14
1181 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.005P)2 + 0.630P] where P = (Fo2 + 2Fc2)/3
1181 reflections(Δ/σ)max = 0.010
150 parametersΔρmax = 0.14 e Å−3
1 restraintΔρmin = −0.18 e Å−3
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.
xyzUiso*/Ueq
C10.1554 (3)1.0151 (6)0.6353 (3)0.0654 (11)
C30.0608 (3)1.0836 (9)0.6036 (4)0.1134 (19)
H3A0.03611.16290.65920.175 (15)*
H3B0.02110.97570.59290.175 (15)*
H3C0.06491.15570.53870.175 (15)*
C20.1709 (2)0.9362 (5)0.7606 (3)0.0603 (10)
C40.0899 (3)0.9387 (7)0.8384 (4)0.0973 (16)
H4A0.10760.87720.90370.171 (14)*
H4B0.03880.87210.80740.171 (14)*
H4C0.07261.06830.85290.171 (14)*
B30.1682 (3)0.7752 (7)0.6574 (3)0.0651 (12)
H30.11300.66990.64570.078*
B40.2219 (3)0.8917 (6)0.5497 (3)0.0600 (11)
H40.20230.86130.46670.072*
B50.2525 (3)1.1224 (7)0.5909 (4)0.0641 (12)
H50.25331.24260.53460.077*
B60.2166 (3)1.1519 (6)0.7254 (4)0.0655 (12)
H60.19291.28980.75730.079*
B70.2479 (3)0.7542 (7)0.7621 (4)0.0641 (11)
H70.24580.63350.81820.077*
B80.2840 (3)0.7257 (6)0.6277 (4)0.0618 (11)
H80.30610.58700.59570.074*
B90.3368 (3)0.9424 (6)0.5869 (3)0.0569 (10)
B100.3323 (3)1.1052 (7)0.6967 (4)0.0641 (12)
H100.38591.21340.70980.077*
B110.2770 (3)0.9867 (7)0.8032 (4)0.0634 (11)
H110.29401.01750.88690.076*
B120.3516 (3)0.8587 (7)0.7199 (4)0.0654 (12)
H120.41850.80610.74850.078*
C50.4156 (3)0.9438 (6)0.5044 (4)0.0741 (11)
C60.4772 (3)0.9437 (7)0.4438 (5)0.1044 (17)
H10.52600.94350.39580.15 (2)*
U11U22U33U12U13U23
C10.061 (2)0.078 (3)0.058 (2)0.009 (2)−0.0032 (19)0.000 (2)
C30.082 (3)0.156 (5)0.102 (4)0.045 (3)−0.009 (3)0.001 (4)
C20.063 (2)0.066 (2)0.052 (2)−0.0107 (18)0.0106 (19)−0.007 (2)
C40.090 (3)0.120 (4)0.082 (3)−0.026 (3)0.033 (3)−0.013 (3)
B30.072 (3)0.062 (3)0.061 (3)−0.020 (2)0.001 (2)−0.012 (2)
B40.067 (2)0.070 (3)0.044 (2)−0.003 (2)−0.005 (2)−0.007 (2)
B50.086 (3)0.056 (2)0.051 (2)0.002 (2)0.005 (2)0.004 (2)
B60.081 (3)0.053 (2)0.062 (3)−0.006 (2)0.015 (2)−0.010 (2)
B70.091 (3)0.053 (2)0.048 (2)−0.006 (2)0.002 (2)0.007 (2)
B80.082 (3)0.047 (2)0.057 (2)0.005 (2)0.005 (2)−0.001 (2)
B90.059 (2)0.062 (2)0.050 (2)−0.003 (2)0.003 (2)−0.001 (2)
B100.065 (3)0.067 (3)0.061 (3)−0.023 (2)0.002 (2)−0.007 (3)
B110.075 (3)0.070 (3)0.045 (2)−0.014 (2)−0.002 (2)−0.006 (2)
B120.061 (2)0.080 (3)0.056 (3)0.005 (2)−0.009 (2)0.001 (2)
C50.072 (2)0.081 (3)0.070 (3)−0.002 (2)0.015 (2)−0.002 (2)
C60.094 (3)0.119 (4)0.101 (3)−0.004 (3)0.042 (3)−0.003 (3)
C1—C31.510 (5)B5—B91.759 (6)
C1—C21.680 (5)B5—B101.766 (6)
C1—B41.684 (6)B5—B61.778 (6)
C1—B51.693 (6)B5—H51.1000
C1—B31.714 (6)B6—B111.750 (7)
C1—B61.728 (6)B6—B101.751 (6)
C3—H3A0.9600B6—H61.1000
C3—H3B0.9600B7—B111.760 (6)
C3—H3C0.9600B7—B121.757 (6)
C2—C41.529 (5)B7—B81.776 (6)
C2—B111.670 (6)B7—H71.1000
C2—B71.697 (6)B8—B91.777 (6)
C2—B61.709 (6)B8—B121.781 (6)
C2—B31.717 (5)B8—H81.1000
C4—H4A0.9600B9—C51.544 (5)
C4—H4B0.9600B9—B121.780 (6)
C4—H4C0.9600B9—B101.789 (6)
B3—B71.758 (6)B10—B111.765 (7)
B3—B81.758 (6)B10—B121.774 (7)
B3—B41.760 (6)B10—H101.1000
B3—H31.1000B11—B121.752 (6)
B4—B51.755 (6)B11—H111.1000
B4—B81.767 (6)B12—H121.1000
B4—B91.769 (6)C5—C61.175 (6)
B4—H41.1000C6—H10.9300
C3—C1—C2118.2 (3)C2—B6—H6124.2
C3—C1—B4121.2 (4)C1—B6—H6124.3
C2—C1—B4110.5 (3)B11—B6—H6122.4
C3—C1—B5122.1 (4)B10—B6—H6122.6
C2—C1—B5110.0 (3)B5—B6—H6122.6
B4—C1—B562.6 (2)C2—B7—B1157.7 (2)
C3—C1—B3116.9 (4)C2—B7—B359.6 (2)
C2—C1—B360.8 (2)B11—B7—B3107.4 (3)
B4—C1—B362.4 (3)C2—B7—B12104.4 (3)
B5—C1—B3113.5 (3)B11—B7—B1259.7 (3)
C3—C1—B6117.7 (4)B3—B7—B12107.8 (3)
C2—C1—B660.2 (2)C2—B7—B8105.6 (3)
B4—C1—B6114.0 (3)B11—B7—B8108.1 (3)
B5—C1—B662.6 (3)B3—B7—B859.7 (3)
B3—C1—B6112.5 (3)B12—B7—B860.5 (3)
C1—C3—H3A109.5C2—B7—H7124.5
C1—C3—H3B109.5B11—B7—H7122.1
H3A—C3—H3B109.5B3—B7—H7121.6
C1—C3—H3C109.5B12—B7—H7122.4
H3A—C3—H3C109.5B8—B7—H7121.9
H3B—C3—H3C109.5B3—B8—B459.9 (3)
C4—C2—B11120.3 (3)B3—B8—B9107.8 (3)
C4—C2—C1119.3 (3)B4—B8—B959.9 (2)
B11—C2—C1110.7 (3)B3—B8—B759.6 (2)
C4—C2—B7120.6 (4)B4—B8—B7107.5 (3)
B11—C2—B763.0 (2)B9—B8—B7107.7 (3)
C1—C2—B7110.3 (3)B3—B8—B12106.7 (3)
C4—C2—B6116.9 (3)B4—B8—B12107.2 (3)
B11—C2—B662.4 (3)B9—B8—B1260.1 (2)
C1—C2—B661.3 (2)B7—B8—B1259.2 (3)
B7—C2—B6114.3 (3)B3—B8—H8122.2
C4—C2—B3118.0 (3)B4—B8—H8122.0
B11—C2—B3113.7 (3)B9—B8—H8121.6
C1—C2—B360.6 (2)B7—B8—H8122.1
B7—C2—B362.0 (2)B12—B8—H8122.5
B6—C2—B3113.3 (3)C5—B9—B5122.1 (3)
C2—C4—H4A109.5C5—B9—B4121.7 (3)
C2—C4—H4B109.5B5—B9—B459.7 (2)
H4A—C4—H4B109.5C5—B9—B8121.3 (3)
C2—C4—H4C109.5B5—B9—B8107.7 (3)
H4A—C4—H4C109.5B4—B9—B859.8 (3)
H4B—C4—H4C109.5C5—B9—B12122.6 (3)
C1—B3—C258.6 (2)B5—B9—B12107.1 (3)
C1—B3—B7105.9 (3)B4—B9—B12107.1 (3)
C2—B3—B758.4 (2)B8—B9—B1260.1 (2)
C1—B3—B8105.3 (3)C5—B9—B10122.6 (3)
C2—B3—B8105.5 (3)B5—B9—B1059.7 (3)
B7—B3—B860.7 (3)B4—B9—B10107.3 (3)
C1—B3—B458.0 (2)B8—B9—B10107.9 (3)
C2—B3—B4105.2 (3)B12—B9—B1059.6 (3)
B7—B3—B4108.6 (3)B6—B10—B560.7 (3)
B8—B3—B460.3 (2)B6—B10—B1159.7 (3)
C1—B3—H3123.9B5—B10—B11107.5 (3)
C2—B3—H3124.0B6—B10—B12107.5 (3)
B7—B3—H3121.6B5—B10—B12107.0 (3)
B8—B3—H3122.5B11—B10—B1259.3 (3)
B4—B3—H3122.2B6—B10—B9108.2 (3)
C1—B4—B559.0 (2)B5—B10—B959.3 (3)
C1—B4—B359.6 (3)B11—B10—B9107.4 (3)
B5—B4—B3108.3 (3)B12—B10—B960.0 (2)
C1—B4—B8106.2 (3)B6—B10—H10121.4
B5—B4—B8108.3 (3)B5—B10—H10122.0
B3—B4—B859.8 (3)B11—B10—H10122.3
C1—B4—B9105.7 (3)B12—B10—H10122.3
B5—B4—B959.9 (3)B9—B10—H10121.9
B3—B4—B9108.1 (3)C2—B11—B659.9 (2)
B8—B4—B960.3 (2)C2—B11—B759.2 (3)
C1—B4—H4123.6B6—B11—B7109.2 (3)
B5—B4—H4121.5C2—B11—B12105.8 (3)
B3—B4—H4121.4B6—B11—B12108.5 (3)
B8—B4—H4121.9B7—B11—B1260.0 (3)
B9—B4—H4122.2C2—B11—B10106.2 (3)
C1—B5—B458.4 (2)B6—B11—B1059.8 (3)
C1—B5—B9105.8 (3)B7—B11—B10108.9 (3)
B4—B5—B960.5 (2)B12—B11—B1060.6 (3)
C1—B5—B10105.7 (3)C2—B11—H11123.6
B4—B5—B10109.0 (3)B6—B11—H11121.0
B9—B5—B1061.0 (3)B7—B11—H11121.0
C1—B5—B659.7 (3)B12—B11—H11122.0
B4—B5—B6108.2 (3)B10—B11—H11121.8
B9—B5—B6108.4 (3)B11—B12—B760.2 (3)
B10—B5—B659.2 (3)B11—B12—B1060.1 (3)
C1—B5—H5124.1B7—B12—B10108.6 (3)
B4—B5—H5121.3B11—B12—B9108.3 (3)
B9—B5—H5121.6B7—B12—B9108.4 (3)
B10—B5—H5121.9B10—B12—B960.4 (3)
B6—B5—H5121.5B11—B12—B8108.2 (3)
C2—B6—C158.5 (2)B7—B12—B860.3 (2)
C2—B6—B1157.7 (2)B10—B12—B8108.4 (3)
C1—B6—B11104.8 (3)B9—B12—B859.9 (2)
C2—B6—B10105.1 (3)B11—B12—H12121.6
C1—B6—B10104.8 (3)B7—B12—H12121.3
B11—B6—B1060.5 (3)B10—B12—H12121.3
C2—B6—B5104.8 (3)B9—B12—H12121.5
C1—B6—B557.7 (3)B8—B12—H12121.6
B11—B6—B5107.7 (3)C6—C5—B9178.2 (5)
B10—B6—B560.0 (3)C5—C6—H1180.0
C1—C31.510 (5)
C1—C21.680 (5)
C1—B41.684 (6)
C1—B51.693 (6)
C1—B31.714 (6)
C1—B61.728 (6)
C2—C41.529 (5)
C2—B111.670 (6)
C2—B71.697 (6)
C2—B61.709 (6)
C2—B31.717 (5)
B3—B71.758 (6)
B3—B81.758 (6)
B3—B41.760 (6)
B4—B51.755 (6)
B4—B81.767 (6)
B4—B91.769 (6)
B5—B91.759 (6)
B5—B101.766 (6)
B5—B61.778 (6)
B6—B111.750 (7)
B6—B101.751 (6)
B7—B111.760 (6)
B7—B121.757 (6)
B7—B81.776 (6)
B8—B91.777 (6)
B8—B121.781 (6)
B9—C51.544 (5)
B9—B121.780 (6)
B9—B101.789 (6)
B10—B111.765 (7)
B10—B121.774 (7)
B11—B121.752 (6)
C5—C61.175 (6)
C6—C5—B9178.2 (5)
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Intensity statistics of Friedel opposites.

Authors:  U Shmueli; M Schiltz; H D Flack
Journal:  Acta Crystallogr A       Date:  2008-06-17       Impact factor: 2.290

3.  Carba-closo-dodecaborates with one or two alkynyl substituents bonded to boron.

Authors:  Maik Finze
Journal:  Inorg Chem       Date:  2008-12-15       Impact factor: 5.165
  3 in total

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