Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C24H28Si2, the interplanar angle between the groups on the ends of the central double bond is 7.3 (4)° and the length of this bond is 1.361 (3) Å. The mol­ecules form layers parallel to (\overline 112).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027448/bt6559sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027448/bt65593sup2.hkl
Contains datablock 3

CCDC reference: 259107

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.124
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for Si1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for Si1' PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3' ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

1,1-Diphenyl-2,2-bis(trimethylsilylethynyl)ethene top
Crystal data top
C24H28Si2Z = 2
Mr = 372.64F(000) = 400
Triclinic, P1Dx = 1.055 Mg m3
a = 10.026 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.123 (3) ÅCell parameters from 54 reflections
c = 12.363 (4) Åθ = 10–11.5°
α = 95.51 (3)°µ = 0.16 mm1
β = 107.26 (3)°T = 143 K
γ = 98.19 (3)°Tablet, colourless
V = 1173.3 (6) Å30.5 × 0.5 × 0.2 mm
Data collection top
Stoe Stadi-4
diffractometer
Rint = 0.043
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 3.2°
Graphite monochromatorh = 1111
ω/θ scansk = 1211
8570 measured reflectionsl = 1414
4131 independent reflections3 standard reflections every 60 min
3165 reflections with I > 2σ(I) intensity decay: none
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.5199P]
where P = (Fo2 + 2Fc2)/3
4131 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.5545 (0.0102) x + 10.0801 (0.0054) y - 1.8548 (0.0129) z = 2.3843 (0.0074)

* 0.0029 (0.0016) C5 * 0.0021 (0.0018) C6 * -0.0032 (0.0019) C7 * -0.0007 (0.0018) C8 * 0.0057 (0.0017) C9 * -0.0068 (0.0016) C10

Rms deviation of fitted atoms = 0.0041

- 5.1189 (0.0082) x + 6.2721 (0.0070) y + 8.6134 (0.0079) z = 2.7305 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 55.89 (0.08)

* 0.0111 (0.0018) C1 * -0.0009 (0.0019) C2 * 0.0787 (0.0013) C3 * -0.0812 (0.0013) C5 * -0.0800 (0.0013) C3' * 0.0723 (0.0013) C5'

Rms deviation of fitted atoms = 0.0639

0.9526 (0.0101) x + 2.1148 (0.0100) y + 10.5896 (0.0084) z = 4.6147 (0.0027)

Angle to previous plane (with approximate e.s.d.) = 44.39 (0.08)

* -0.0130 (0.0016) C5' * 0.0071 (0.0017) C6' * 0.0035 (0.0018) C7' * -0.0082 (0.0018) C8' * 0.0020 (0.0018) C9' * 0.0086 (0.0017) C10'

Rms deviation of fitted atoms = 0.0079

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
Si10.62665 (7)0.74540 (7)0.18909 (6)0.03427 (19)
C10.4085 (2)0.3152 (2)0.33153 (17)0.0270 (5)
C20.3535 (2)0.3861 (2)0.24585 (18)0.0284 (5)
C30.4385 (2)0.5002 (2)0.22252 (18)0.0302 (5)
C40.5074 (2)0.5985 (2)0.20527 (18)0.0326 (5)
C50.5629 (2)0.3403 (2)0.39430 (18)0.0288 (5)
C60.6612 (2)0.3349 (3)0.3358 (2)0.0402 (6)
H60.63000.31850.25450.048*
C70.8049 (3)0.3533 (3)0.3959 (2)0.0492 (7)
H70.87170.34900.35540.059*
C80.8513 (3)0.3777 (3)0.5133 (2)0.0471 (7)
H80.94980.39040.55400.057*
C90.7550 (3)0.3839 (2)0.5721 (2)0.0412 (6)
H90.78710.40190.65340.049*
C100.6108 (2)0.3638 (2)0.51295 (19)0.0325 (5)
H100.54450.36620.55400.039*
C110.5760 (3)0.8993 (3)0.2471 (3)0.0616 (8)
H11A0.47930.90540.20150.074*
H11B0.64200.97890.24380.074*
H11C0.57970.89500.32680.074*
C120.8084 (3)0.7327 (3)0.2754 (3)0.0618 (8)
H12A0.87580.80890.26820.074*
H12B0.83240.64800.24790.074*
H12C0.81340.73450.35590.074*
C130.6105 (3)0.7435 (3)0.0361 (2)0.0514 (7)
H13A0.68870.80830.02880.062*
H13B0.51980.76830.00440.062*
H13C0.61450.65280.00280.062*
Si1'0.10141 (7)0.27322 (8)0.02839 (6)0.0419 (2)
C3'0.2076 (2)0.3531 (2)0.17396 (19)0.0321 (5)
C4'0.0867 (2)0.3244 (2)0.1120 (2)0.0370 (6)
C5'0.3193 (2)0.2068 (2)0.36452 (18)0.0294 (5)
C6'0.1869 (2)0.2208 (3)0.3755 (2)0.0379 (6)
H6'0.15300.30290.36370.045*
C7'0.1051 (3)0.1159 (3)0.4035 (2)0.0470 (7)
H7'0.01500.12600.41010.056*
C8'0.1536 (3)0.0034 (3)0.4219 (2)0.0473 (7)
H8'0.09650.07570.44000.057*
C9'0.2850 (3)0.0173 (3)0.4138 (2)0.0458 (6)
H9'0.31930.09900.42730.055*
C10'0.3671 (2)0.0874 (2)0.3861 (2)0.0358 (5)
H10'0.45820.07720.38180.043*
C11'0.1670 (4)0.1131 (3)0.0713 (4)0.0832 (12)
H11D0.11780.04280.05000.100*
H11E0.26930.08620.03230.100*
H11F0.14870.12520.15430.100*
C12'0.1210 (3)0.2577 (4)0.1255 (2)0.0719 (10)
H12D0.22200.23680.17010.086*
H12E0.07380.18510.14570.086*
H12F0.07760.34290.14250.086*
C13'0.1952 (3)0.4074 (3)0.0664 (3)0.0575 (8)
H13D0.29620.38400.02200.069*
H13E0.15440.49350.04890.069*
H13F0.18440.41550.14830.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0301 (3)0.0326 (4)0.0379 (4)0.0031 (3)0.0137 (3)0.0022 (3)
C10.0269 (11)0.0281 (12)0.0270 (11)0.0064 (9)0.0099 (9)0.0015 (9)
C20.0250 (11)0.0321 (12)0.0277 (11)0.0035 (9)0.0083 (9)0.0046 (9)
C30.0252 (11)0.0373 (13)0.0258 (11)0.0061 (10)0.0041 (9)0.0055 (10)
C40.0262 (12)0.0375 (13)0.0310 (12)0.0010 (10)0.0065 (10)0.0055 (10)
C50.0295 (11)0.0246 (11)0.0327 (12)0.0066 (9)0.0080 (9)0.0086 (9)
C60.0319 (13)0.0512 (16)0.0386 (13)0.0111 (11)0.0096 (11)0.0116 (12)
C70.0290 (13)0.0602 (18)0.0624 (18)0.0120 (12)0.0146 (12)0.0218 (14)
C80.0275 (13)0.0380 (15)0.0662 (18)0.0032 (10)0.0014 (12)0.0168 (13)
C90.0436 (14)0.0295 (13)0.0381 (13)0.0023 (11)0.0044 (11)0.0063 (10)
C100.0367 (12)0.0259 (12)0.0330 (12)0.0065 (9)0.0066 (10)0.0077 (9)
C110.071 (2)0.0435 (17)0.076 (2)0.0070 (15)0.0367 (17)0.0036 (15)
C120.0335 (14)0.074 (2)0.0668 (19)0.0025 (14)0.0102 (13)0.0101 (16)
C130.0603 (17)0.0452 (16)0.0492 (16)0.0069 (13)0.0259 (14)0.0062 (13)
Si1'0.0271 (3)0.0486 (4)0.0426 (4)0.0043 (3)0.0025 (3)0.0146 (3)
C3'0.0319 (13)0.0337 (13)0.0315 (12)0.0040 (10)0.0102 (10)0.0114 (10)
C4'0.0316 (13)0.0388 (14)0.0378 (13)0.0005 (10)0.0060 (11)0.0164 (11)
C5'0.0286 (11)0.0320 (12)0.0251 (11)0.0034 (9)0.0063 (9)0.0030 (9)
C6'0.0349 (13)0.0456 (15)0.0408 (14)0.0123 (11)0.0175 (11)0.0167 (11)
C7'0.0373 (14)0.0630 (18)0.0468 (15)0.0053 (13)0.0202 (12)0.0199 (13)
C8'0.0488 (16)0.0445 (16)0.0404 (14)0.0126 (12)0.0098 (12)0.0111 (12)
C9'0.0519 (16)0.0274 (13)0.0514 (16)0.0020 (11)0.0080 (13)0.0072 (11)
C10'0.0340 (13)0.0299 (13)0.0406 (13)0.0045 (10)0.0088 (10)0.0020 (10)
C11'0.057 (2)0.057 (2)0.119 (3)0.0144 (16)0.010 (2)0.033 (2)
C12'0.0479 (18)0.104 (3)0.0469 (18)0.0051 (17)0.0027 (14)0.0036 (18)
C13'0.0372 (15)0.074 (2)0.0615 (18)0.0083 (14)0.0133 (13)0.0214 (16)
Geometric parameters (Å, º) top
Si1—C41.837 (2)C13—H13B0.9800
Si1—C131.848 (3)C13—H13C0.9800
Si1—C121.848 (3)Si1'—C4'1.832 (2)
Si1—C111.851 (3)Si1'—C12'1.842 (3)
C1—C21.361 (3)Si1'—C11'1.847 (3)
C1—C5'1.480 (3)Si1'—C13'1.859 (3)
C1—C51.484 (3)C3'—C4'1.202 (3)
C2—C3'1.440 (3)C5'—C10'1.384 (3)
C2—C31.441 (3)C5'—C6'1.399 (3)
C3—C41.202 (3)C6'—C7'1.382 (3)
C5—C101.386 (3)C6'—H6'0.9500
C5—C61.388 (3)C7'—C8'1.378 (4)
C6—C71.387 (3)C7'—H7'0.9500
C6—H60.9500C8'—C9'1.377 (4)
C7—C81.373 (4)C8'—H8'0.9500
C7—H70.9500C9'—C10'1.380 (3)
C8—C91.374 (4)C9'—H9'0.9500
C8—H80.9500C10'—H10'0.9500
C9—C101.388 (3)C11'—H11D0.9800
C9—H90.9500C11'—H11E0.9800
C10—H100.9500C11'—H11F0.9800
C11—H11A0.9800C12'—H12D0.9800
C11—H11B0.9800C12'—H12E0.9800
C11—H11C0.9800C12'—H12F0.9800
C12—H12A0.9800C13'—H13D0.9800
C12—H12B0.9800C13'—H13E0.9800
C12—H12C0.9800C13'—H13F0.9800
C13—H13A0.9800
C4—Si1—C13109.35 (12)Si1—C13—H13C109.5
C4—Si1—C12106.87 (13)H13A—C13—H13C109.5
C13—Si1—C12111.59 (14)H13B—C13—H13C109.5
C4—Si1—C11107.99 (13)C4'—Si1'—C12'109.50 (13)
C13—Si1—C11111.20 (15)C4'—Si1'—C11'107.34 (14)
C12—Si1—C11109.67 (15)C12'—Si1'—C11'112.70 (19)
C2—C1—C5'122.22 (19)C4'—Si1'—C13'107.29 (13)
C2—C1—C5121.17 (19)C12'—Si1'—C13'109.69 (16)
C5'—C1—C5116.58 (18)C11'—Si1'—C13'110.14 (16)
C1—C2—C3'122.5 (2)C4'—C3'—C2178.6 (3)
C1—C2—C3121.56 (19)C3'—C4'—Si1'174.7 (2)
C3'—C2—C3115.91 (19)C10'—C5'—C6'118.1 (2)
C4—C3—C2177.6 (2)C10'—C5'—C1119.7 (2)
C3—C4—Si1174.7 (2)C6'—C5'—C1122.2 (2)
C10—C5—C6118.9 (2)C7'—C6'—C5'120.5 (2)
C10—C5—C1120.2 (2)C7'—C6'—H6'119.8
C6—C5—C1120.8 (2)C5'—C6'—H6'119.8
C7—C6—C5120.2 (2)C8'—C7'—C6'120.4 (2)
C7—C6—H6119.9C8'—C7'—H7'119.8
C5—C6—H6119.9C6'—C7'—H7'119.8
C8—C7—C6120.4 (2)C9'—C8'—C7'119.8 (2)
C8—C7—H7119.8C9'—C8'—H8'120.1
C6—C7—H7119.8C7'—C8'—H8'120.1
C7—C8—C9120.0 (2)C8'—C9'—C10'120.0 (2)
C7—C8—H8120.0C8'—C9'—H9'120.0
C9—C8—H8120.0C10'—C9'—H9'120.0
C8—C9—C10120.1 (2)C9'—C10'—C5'121.3 (2)
C8—C9—H9120.0C9'—C10'—H10'119.4
C10—C9—H9120.0C5'—C10'—H10'119.4
C5—C10—C9120.4 (2)Si1'—C11'—H11D109.5
C5—C10—H10119.8Si1'—C11'—H11E109.5
C9—C10—H10119.8H11D—C11'—H11E109.5
Si1—C11—H11A109.5Si1'—C11'—H11F109.5
Si1—C11—H11B109.5H11D—C11'—H11F109.5
H11A—C11—H11B109.5H11E—C11'—H11F109.5
Si1—C11—H11C109.5Si1'—C12'—H12D109.5
H11A—C11—H11C109.5Si1'—C12'—H12E109.5
H11B—C11—H11C109.5H12D—C12'—H12E109.5
Si1—C12—H12A109.5Si1'—C12'—H12F109.5
Si1—C12—H12B109.5H12D—C12'—H12F109.5
H12A—C12—H12B109.5H12E—C12'—H12F109.5
Si1—C12—H12C109.5Si1'—C13'—H13D109.5
H12A—C12—H12C109.5Si1'—C13'—H13E109.5
H12B—C12—H12C109.5H13D—C13'—H13E109.5
Si1—C13—H13A109.5Si1'—C13'—H13F109.5
Si1—C13—H13B109.5H13D—C13'—H13F109.5
H13A—C13—H13B109.5H13E—C13'—H13F109.5
C5'—C1—C2—C3'5.9 (3)C1—C5—C10—C9178.3 (2)
C5—C1—C2—C3'172.1 (2)C8—C9—C10—C51.4 (3)
C5'—C1—C2—C3173.49 (19)C2—C1—C5'—C10'136.7 (2)
C5—C1—C2—C38.5 (3)C5—C1—C5'—C10'41.3 (3)
C2—C1—C5—C10128.7 (2)C2—C1—C5'—C6'43.6 (3)
C5'—C1—C5—C1053.2 (3)C5—C1—C5'—C6'138.3 (2)
C2—C1—C5—C654.1 (3)C10'—C5'—C6'—C7'2.1 (3)
C5'—C1—C5—C6124.0 (2)C1—C5'—C6'—C7'178.2 (2)
C10—C5—C6—C70.2 (4)C5'—C6'—C7'—C8'0.6 (4)
C1—C5—C6—C7177.4 (2)C6'—C7'—C8'—C9'0.9 (4)
C5—C6—C7—C80.3 (4)C7'—C8'—C9'—C10'0.7 (4)
C6—C7—C8—C90.1 (4)C8'—C9'—C10'—C5'0.9 (4)
C7—C8—C9—C100.8 (4)C6'—C5'—C10'—C9'2.3 (3)
C6—C5—C10—C91.1 (3)C1—C5'—C10'—C9'178.1 (2)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds