Literature DB >> 22347063

Triphen-yl(prop-2-yn-1-yl)silane.

Björn Nelson1, Michaela Schulte, Carsten Strohmann, Hans Preut, Martin Hiersemann.   

Abstract

In the title compound, C(21)H(18)Si, the coordination geometry around the Si atom is a slightly distorted tetra-hedron with C-Si-C angles in the range 106.05 (11) to 110.58 (10) ° and Si-C bond lengths in the range 1.855 (2) to 1.883 (3) Å. The alkyne C-C bond length is 1.167 (4) Å. The dihedral angles between the three phenyl rings are 63.89 (7), 86.38 (7) and 70.51 (8)°. In the crystal, mol-ecules inter-act only by van der Waals forces.

Entities:  

Year:  2012        PMID： 22347063      PMCID： PMC3275207          DOI： 10.1107/S1600536812001109

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


Related literature

For the first report of the title compound, see: Masson et al. (1967 ▶). For background to silane chemistry, see: Abraham et al. (2001 ▶, 2003 ▶); Helmboldt & Hiersemann (2003 ▶); Hiersemann (1999 ▶, 2000 ▶); Nelson et al. (2011 ▶).

Experimental

Crystal data

C21H18Si M = 298.44 Triclinic, a = 9.6668 (11) Å b = 9.6857 (7) Å c = 10.1178 (10) Å α = 80.289 (7)° β = 65.189 (10)° γ = 72.957 (8)° V = 820.98 (16) Å3 Z = 2 Mo Kα radiation μ = 0.14 mm−1 T = 173 K 0.40 × 0.30 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.973, T max = 0.986 8081 measured reflections 3224 independent reflections 1940 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.086 S = 1.05 3224 reflections 211 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.34 e Å−3 Δρmin = −0.29 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001109/hb6593sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001109/hb6593Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812001109/hb6593Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H18SiZ = 2
Mr = 298.44F(000) = 316
Triclinic, P1Dx = 1.207 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6668 (11) ÅCell parameters from 2879 reflections
b = 9.6857 (7) Åθ = 2.2–29.1°
c = 10.1178 (10) ŵ = 0.14 mm−1
α = 80.289 (7)°T = 173 K
β = 65.189 (10)°Plate, colourless
γ = 72.957 (8)°0.40 × 0.30 × 0.10 mm
V = 820.98 (16) Å3
Oxford Diffraction Xcalibur S CCD diffractometer3224 independent reflections
Radiation source: Enhance (Mo) X-ray Source1940 reflections with I > 2σ(I)
graphiteRint = 0.048
Detector resolution: 16.0560 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −11→11
Tmin = 0.973, Tmax = 0.986l = −12→12
8081 measured 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0228P)2] where P = (Fo2 + 2Fc2)/3
3224 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008) Empirical absorption correction using sperical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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
C10.8154 (3)0.5812 (3)0.1515 (4)0.0418 (7)
C20.7846 (3)0.6191 (2)0.2662 (3)0.0332 (6)
C30.7508 (3)0.6647 (3)0.4086 (3)0.0395 (7)
C40.7985 (2)0.9730 (2)0.3179 (2)0.0257 (6)
C50.8267 (2)0.9789 (2)0.1710 (2)0.0328 (6)
H50.87350.89200.12050.039*
C60.7884 (3)1.1085 (2)0.0958 (3)0.0368 (6)
H60.80731.1101−0.00440.044*
C70.7222 (3)1.2353 (2)0.1697 (3)0.0382 (7)
H70.69581.32460.11950.046*
C80.6944 (2)1.2329 (2)0.3138 (3)0.0378 (7)
H80.64931.32060.36310.045*
C90.7317 (2)1.1033 (2)0.3891 (3)0.0308 (6)
H90.71181.10280.48940.037*
C100.8073 (2)0.8192 (2)0.6057 (2)0.0256 (5)
C110.6509 (2)0.8669 (2)0.7011 (2)0.0286 (6)
H110.57120.89320.66350.034*
C120.6081 (3)0.8771 (2)0.8479 (3)0.0297 (6)
H120.50030.90820.91020.036*
C130.7231 (3)0.8417 (2)0.9041 (3)0.0314 (6)
H130.69490.84941.00500.038*
C140.8787 (3)0.7953 (2)0.8126 (2)0.0301 (6)
H140.95780.77080.85090.036*
C150.9206 (2)0.7841 (2)0.6660 (2)0.0285 (6)
H151.02850.75200.60460.034*
C161.0757 (2)0.7216 (2)0.3174 (2)0.0247 (5)
C171.1798 (3)0.8035 (2)0.2971 (2)0.0313 (6)
H171.13860.90000.32750.038*
C181.3405 (3)0.7505 (2)0.2347 (3)0.0364 (6)
H181.40860.80870.22460.044*
C191.4016 (3)0.6110 (2)0.1867 (3)0.0417 (7)
H191.51230.57350.14180.050*
C201.3025 (3)0.5280 (2)0.2043 (3)0.0439 (7)
H201.34490.43250.17120.053*
C211.1409 (3)0.5807 (2)0.2696 (2)0.0337 (6)
H211.07380.52070.28200.040*
H10.764 (3)0.588 (2)0.475 (3)0.053 (8)*
H20.646 (3)0.707 (2)0.454 (3)0.049 (8)*
H30.839 (2)0.557 (2)0.066 (2)0.030 (7)*
Si0.85982 (7)0.79610 (6)0.41079 (7)0.02875 (19)
U11U22U33U12U13U23
C10.0559 (19)0.0359 (16)0.042 (2)−0.0082 (13)−0.0273 (18)−0.0081 (14)
C20.0379 (15)0.0241 (13)0.0428 (18)−0.0094 (11)−0.0203 (14)−0.0002 (12)
C30.0437 (18)0.0345 (16)0.042 (2)−0.0121 (13)−0.0166 (16)−0.0017 (14)
C40.0234 (13)0.0262 (12)0.0294 (15)−0.0051 (10)−0.0131 (12)−0.0010 (11)
C50.0318 (14)0.0298 (13)0.0381 (17)−0.0064 (11)−0.0155 (13)−0.0025 (12)
C60.0373 (15)0.0431 (15)0.0328 (16)−0.0103 (12)−0.0193 (13)0.0060 (13)
C70.0341 (15)0.0307 (14)0.0495 (19)−0.0038 (11)−0.0221 (14)0.0065 (13)
C80.0314 (14)0.0225 (13)0.0586 (19)−0.0033 (10)−0.0188 (14)−0.0031 (13)
C90.0296 (13)0.0282 (13)0.0349 (16)−0.0050 (10)−0.0127 (12)−0.0063 (11)
C100.0317 (13)0.0150 (11)0.0314 (14)−0.0049 (10)−0.0148 (12)0.0008 (10)
C110.0287 (14)0.0243 (13)0.0360 (16)−0.0046 (10)−0.0175 (13)−0.0004 (11)
C120.0279 (13)0.0227 (12)0.0366 (16)−0.0030 (10)−0.0118 (12)−0.0046 (11)
C130.0400 (15)0.0281 (13)0.0281 (15)−0.0059 (11)−0.0156 (13)−0.0050 (11)
C140.0344 (15)0.0265 (13)0.0333 (16)−0.0044 (11)−0.0195 (13)−0.0008 (11)
C150.0277 (13)0.0214 (12)0.0345 (16)−0.0028 (10)−0.0126 (12)−0.0018 (11)
C160.0330 (14)0.0165 (11)0.0244 (14)−0.0034 (10)−0.0139 (12)0.0017 (10)
C170.0359 (15)0.0203 (12)0.0355 (16)−0.0002 (11)−0.0153 (13)−0.0048 (11)
C180.0364 (15)0.0315 (14)0.0398 (17)−0.0081 (11)−0.0144 (13)−0.0003 (12)
C190.0339 (15)0.0321 (15)0.0471 (19)0.0036 (12)−0.0117 (14)−0.0038 (13)
C200.0463 (17)0.0218 (13)0.0550 (19)0.0059 (12)−0.0190 (15)−0.0086 (12)
C210.0415 (15)0.0189 (12)0.0422 (17)−0.0070 (11)−0.0187 (14)0.0002 (11)
Si0.0332 (4)0.0224 (3)0.0325 (4)−0.0035 (3)−0.0166 (3)−0.0020 (3)
C1—C21.167 (4)C11—C121.377 (3)
C1—H30.85 (2)C11—H110.9500
C2—C31.453 (4)C12—C131.386 (3)
C3—Si1.883 (3)C12—H120.9500
C3—H10.93 (2)C13—C141.377 (3)
C3—H20.92 (2)C13—H130.9500
C4—C51.388 (3)C14—C151.379 (3)
C4—C91.402 (3)C14—H140.9500
C4—Si1.871 (2)C15—H150.9500
C5—C61.390 (3)C16—C171.387 (3)
C5—H50.9500C16—C211.399 (3)
C6—C71.387 (3)C16—Si1.860 (2)
C6—H60.9500C17—C181.376 (3)
C7—C81.366 (3)C17—H170.9500
C7—H70.9500C18—C191.387 (3)
C8—C91.388 (3)C18—H180.9500
C8—H80.9500C19—C201.363 (3)
C9—H90.9500C19—H190.9500
C10—C111.396 (3)C20—C211.385 (3)
C10—C151.399 (3)C20—H200.9500
C10—Si1.855 (2)C21—H210.9500
C2—C1—H3177.5 (15)C13—C12—H12120.2
C1—C2—C3178.4 (3)C14—C13—C12119.5 (2)
C2—C3—Si116.24 (19)C14—C13—H13120.2
C2—C3—H1113.5 (15)C12—C13—H13120.2
Si—C3—H1107.8 (14)C13—C14—C15120.6 (2)
C2—C3—H2110.3 (15)C13—C14—H14119.7
Si—C3—H2106.5 (14)C15—C14—H14119.7
H1—C3—H2101 (2)C14—C15—C10121.3 (2)
C5—C4—C9117.8 (2)C14—C15—H15119.3
C5—C4—Si119.61 (16)C10—C15—H15119.3
C9—C4—Si122.45 (18)C17—C16—C21117.0 (2)
C4—C5—C6121.8 (2)C17—C16—Si120.64 (16)
C4—C5—H5119.1C21—C16—Si122.34 (17)
C6—C5—H5119.1C18—C17—C16122.6 (2)
C7—C6—C5118.8 (2)C18—C17—H17118.7
C7—C6—H6120.6C16—C17—H17118.7
C5—C6—H6120.6C17—C18—C19119.1 (2)
C8—C7—C6120.6 (2)C17—C18—H18120.5
C8—C7—H7119.7C19—C18—H18120.5
C6—C7—H7119.7C20—C19—C18119.8 (2)
C7—C8—C9120.5 (2)C20—C19—H19120.1
C7—C8—H8119.8C18—C19—H19120.1
C9—C8—H8119.8C19—C20—C21121.0 (2)
C8—C9—C4120.4 (2)C19—C20—H20119.5
C8—C9—H9119.8C21—C20—H20119.5
C4—C9—H9119.8C20—C21—C16120.5 (2)
C11—C10—C15116.7 (2)C20—C21—H21119.7
C11—C10—Si121.16 (16)C16—C21—H21119.7
C15—C10—Si122.11 (17)C10—Si—C16110.12 (10)
C12—C11—C10122.3 (2)C10—Si—C4110.58 (10)
C12—C11—H11118.8C16—Si—C4109.44 (9)
C10—C11—H11118.8C10—Si—C3106.05 (11)
C11—C12—C13119.6 (2)C16—Si—C3110.24 (12)
C11—C12—H12120.2C4—Si—C3110.37 (11)
C9—C4—C5—C6−1.0 (3)Si—C16—C21—C20−178.13 (17)
Si—C4—C5—C6−177.71 (16)C11—C10—Si—C16−176.80 (16)
C4—C5—C6—C70.9 (3)C15—C10—Si—C160.4 (2)
C5—C6—C7—C8−0.3 (4)C11—C10—Si—C462.13 (19)
C6—C7—C8—C9−0.2 (4)C15—C10—Si—C4−120.69 (17)
C7—C8—C9—C40.1 (3)C11—C10—Si—C3−57.54 (19)
C5—C4—C9—C80.5 (3)C15—C10—Si—C3119.65 (19)
Si—C4—C9—C8177.12 (16)C17—C16—Si—C10−67.59 (18)
C15—C10—C11—C12−1.1 (3)C21—C16—Si—C10110.05 (19)
Si—C10—C11—C12176.23 (17)C17—C16—Si—C454.2 (2)
C10—C11—C12—C131.2 (3)C21—C16—Si—C4−128.19 (19)
C11—C12—C13—C14−0.7 (3)C17—C16—Si—C3175.74 (17)
C12—C13—C14—C150.1 (3)C21—C16—Si—C3−6.6 (2)
C13—C14—C15—C100.0 (3)C5—C4—Si—C10−179.73 (17)
C11—C10—C15—C140.5 (3)C9—C4—Si—C103.7 (2)
Si—C10—C15—C14−176.79 (16)C5—C4—Si—C1658.8 (2)
C21—C16—C17—C18−0.8 (3)C9—C4—Si—C16−117.74 (18)
Si—C16—C17—C18176.96 (17)C5—C4—Si—C3−62.7 (2)
C16—C17—C18—C191.6 (4)C9—C4—Si—C3120.76 (19)
C17—C18—C19—C20−1.2 (4)C2—C3—Si—C10−174.65 (19)
C18—C19—C20—C210.0 (4)C2—C3—Si—C16−55.5 (2)
C19—C20—C21—C160.8 (4)C2—C3—Si—C465.6 (2)
C17—C16—C21—C20−0.4 (3)
  4 in total

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4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
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  4 in total

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