10,10-Bis­(tri­methyl­silyl­ethynyl)-9-methyl­enefluorene

Jones, P.G.; Berger, H.; Bubenitschek, P.; Hopf, H.

doi:10.1107/S1600536804004428

10,10-Bis(trimethylsilylethynyl)-9-methylenefluorene

P. G. Jones, H. Berger, P. Bubenitschek and H. Hopf

In the title compound {systematic name: 9-[bis(trimethylsilylethynyl)methylene]fluorene}, C₂₄H₂₆Si₂, the molecules are planar (except for the methyl groups) and pack in layers parallel to the bc plane at x $\simeq$ $1\over4$ and $3\over 4$ . The mean distance between neighbouring layers, which are related by inversion, is 3.50 Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004428/bt6415sup1.cif Contains datablocks 3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004428/bt64153sup2.hkl Contains datablock 3

CCDC reference: 238700

checkCIF report

Key indicators

Single-crystal X-ray study
T = 203 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.137
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         Si
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Si'
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11    ...       1.45 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11'   ...       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

   0 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
   1 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.

9-[bis(trimethylsilylethynyl)methylene]fluorene top

Crystal data top

C₂₄H₂₆Si₂	F(000) = 792
M_r = 370.63	D_x = 1.119 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.003 (2) Å	Cell parameters from 48 reflections
b = 13.219 (2) Å	θ = 10–11.5°
c = 23.779 (4) Å	µ = 0.17 mm⁻¹
β = 91.64 (3)°	T = 203 K
V = 2200.4 (8) Å³	Tablet, yellow
Z = 4	0.4 × 0.4 × 0.2 mm

Data collection top

Stoe Stadi-4 diffractometer	R_int = 0.071
Radiation source: fine-focus sealed tube	θ_max = 25.1°, θ_min = 3.0°
Graphite monochromator	h = −8→8
ω/θ scans	k = −15→0
8747 measured reflections	l = −28→28
3894 independent reflections	3 standard reflections every 60 min
2212 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0398P)² + 0.8683P] where P = (F_o² + 2F_c²)/3
3894 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.18 e Å⁻³
209 restraints	Δρ_min = −0.26 e Å⁻³

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)

6.9641 (0.0037) x + 1.0879 (0.0039) y + 0.8827 (0.0069) z = 2.7123 (0.0041)

* 0.0235 (0.0031) C1 * 0.0177 (0.0031) C2 * 0.0052 (0.0032) C3 * 0.0024 (0.0032) C4 * -0.0238 (0.0033) C5 * -0.0334 (0.0033) C6 * -0.0191 (0.0032) C7 * 0.0030 (0.0032) C8 * 0.0093 (0.0028) C9 * 0.0124 (0.0029) C1A * 0.0092 (0.0029) C4A * 0.0049 (0.0031) C5A * 0.0124 (0.0029) C8A * 0.0036 (0.0028) C10 * 0.0389 (0.0017) Si * -0.0251 (0.0018) Si' * 0.0093 (0.0028) C9 * 0.0036 (0.0028) C10 * -0.0012 (0.0030) C11 * 0.0005 (0.0030) C12 * -0.0193 (0.0032) C11' * -0.0340 (0.0033) C12'

Rms deviation of fitted atoms = 0.0181

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

	x	y	z	U_iso*/U_eq
Si	0.26759 (15)	0.24467 (8)	0.70408 (4)	0.0506 (3)
C1A	0.2649 (4)	0.4489 (2)	0.44376 (12)	0.0358 (7)
C1	0.2808 (5)	0.3979 (3)	0.39318 (13)	0.0439 (9)
H1	0.2936	0.3272	0.3925	0.053*
C2	0.2776 (5)	0.4535 (3)	0.34357 (14)	0.0502 (9)
H2	0.2879	0.4197	0.3090	0.060*
C3	0.2595 (5)	0.5575 (3)	0.34401 (14)	0.0549 (10)
H3	0.2572	0.5936	0.3099	0.066*
C4	0.2447 (5)	0.6087 (3)	0.39429 (14)	0.0508 (9)
H4	0.2327	0.6795	0.3947	0.061*
C4A	0.2479 (4)	0.5542 (2)	0.44403 (13)	0.0388 (8)
C9	0.2627 (4)	0.4122 (2)	0.50257 (13)	0.0343 (7)
C10	0.2748 (4)	0.3146 (2)	0.52079 (12)	0.0353 (7)
C11	0.2708 (5)	0.2881 (2)	0.57969 (14)	0.0395 (8)
C12	0.2686 (5)	0.2647 (2)	0.62818 (14)	0.0448 (9)
C13	0.2404 (7)	0.3697 (3)	0.73835 (15)	0.0819 (14)
H13A	0.3505	0.4115	0.7307	0.115*
H13B	0.2309	0.3605	0.7786	0.115*
H13C	0.1255	0.4024	0.7236	0.115*
C14	0.0660 (6)	0.1610 (4)	0.72020 (17)	0.0906 (16)
H14A	0.0576	0.1538	0.7607	0.127*
H14B	0.0860	0.0950	0.7035	0.127*
H14C	−0.0518	0.1899	0.7050	0.127*
C15	0.4978 (5)	0.1871 (3)	0.72729 (15)	0.0658 (11)
H15A	0.5054	0.1847	0.7681	0.092*
H15B	0.6024	0.2275	0.7136	0.092*
H15C	0.5062	0.1190	0.7123	0.092*
Si'	0.32664 (18)	0.04947 (8)	0.40619 (4)	0.0564 (3)
C8A	0.2444 (4)	0.5038 (2)	0.53777 (12)	0.0353 (7)
C8	0.2337 (5)	0.5169 (2)	0.59543 (13)	0.0443 (9)
H8	0.2405	0.4611	0.6199	0.053*
C7	0.2127 (5)	0.6139 (3)	0.61637 (15)	0.0542 (10)
H7	0.2055	0.6234	0.6554	0.065*
C6	0.2021 (5)	0.6966 (3)	0.58146 (16)	0.0583 (10)
H6	0.1877	0.7616	0.5968	0.070*
C5	0.2127 (5)	0.6848 (3)	0.52368 (16)	0.0540 (10)
H5	0.2051	0.7412	0.4997	0.065*
C5A	0.2346 (5)	0.5887 (2)	0.50208 (14)	0.0404 (8)
C11'	0.2895 (5)	0.2294 (2)	0.48372 (13)	0.0404 (8)
C12'	0.3025 (5)	0.1558 (3)	0.45515 (14)	0.0493 (9)
C13'	0.5811 (6)	0.0134 (3)	0.40555 (18)	0.0875 (14)
H13D	0.5969	−0.0436	0.3804	0.123*
H13E	0.6242	−0.0053	0.4433	0.123*
H13F	0.6559	0.0702	0.3926	0.123*
C14'	0.1795 (8)	−0.0574 (3)	0.42999 (17)	0.1019 (17)
H14D	0.1939	−0.1142	0.4047	0.143*
H14E	0.0464	−0.0370	0.4301	0.143*
H14F	0.2209	−0.0770	0.4677	0.143*
C15'	0.2445 (7)	0.0940 (3)	0.33562 (14)	0.0800 (14)
H15D	0.2551	0.0393	0.3087	0.112*
H15E	0.3230	0.1504	0.3242	0.112*
H15F	0.1123	0.1155	0.3370	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0496 (6)	0.0636 (7)	0.0385 (5)	0.0006 (5)	−0.0007 (4)	0.0071 (5)
C1A	0.0324 (19)	0.0366 (18)	0.0382 (17)	−0.0023 (15)	−0.0014 (14)	0.0004 (15)
C1	0.047 (2)	0.042 (2)	0.0426 (19)	−0.0045 (17)	−0.0007 (16)	0.0030 (16)
C2	0.047 (2)	0.062 (2)	0.042 (2)	−0.0070 (19)	0.0011 (17)	−0.0042 (18)
C3	0.061 (3)	0.060 (2)	0.044 (2)	−0.009 (2)	0.0013 (18)	0.0155 (19)
C4	0.051 (2)	0.043 (2)	0.058 (2)	−0.0057 (18)	−0.0020 (19)	0.0124 (18)
C4A	0.035 (2)	0.0369 (18)	0.0442 (18)	−0.0068 (15)	−0.0005 (15)	0.0054 (16)
C9	0.0291 (19)	0.0348 (17)	0.0389 (17)	−0.0023 (14)	−0.0018 (14)	−0.0009 (14)
C10	0.0346 (19)	0.0346 (18)	0.0365 (18)	−0.0013 (14)	−0.0011 (14)	−0.0015 (14)
C11	0.041 (2)	0.0326 (19)	0.0446 (19)	0.0000 (15)	−0.0032 (16)	−0.0032 (15)
C12	0.050 (2)	0.040 (2)	0.0445 (19)	0.0011 (16)	−0.0007 (17)	0.0033 (16)
C13	0.098 (4)	0.096 (3)	0.051 (2)	0.023 (3)	−0.005 (2)	−0.017 (2)
C14	0.069 (3)	0.136 (4)	0.066 (3)	−0.027 (3)	−0.003 (2)	0.036 (3)
C15	0.065 (3)	0.075 (3)	0.057 (2)	0.005 (2)	−0.002 (2)	0.010 (2)
Si'	0.0929 (9)	0.0313 (6)	0.0442 (6)	0.0032 (6)	−0.0087 (6)	−0.0022 (5)
C8A	0.0306 (19)	0.0344 (17)	0.0407 (17)	−0.0021 (14)	−0.0038 (14)	−0.0030 (15)
C8	0.049 (2)	0.041 (2)	0.0421 (19)	−0.0010 (16)	−0.0040 (16)	−0.0025 (16)
C7	0.061 (3)	0.050 (2)	0.052 (2)	−0.0029 (19)	−0.0007 (19)	−0.0160 (18)
C6	0.064 (3)	0.036 (2)	0.075 (3)	−0.0043 (19)	0.000 (2)	−0.0173 (19)
C5	0.058 (3)	0.034 (2)	0.069 (2)	−0.0039 (18)	−0.002 (2)	−0.0003 (18)
C5A	0.038 (2)	0.0320 (17)	0.0513 (19)	−0.0012 (15)	0.0002 (16)	−0.0027 (15)
C11'	0.049 (2)	0.0323 (18)	0.0390 (19)	−0.0010 (16)	−0.0035 (16)	0.0039 (15)
C12'	0.067 (3)	0.034 (2)	0.047 (2)	0.0006 (17)	−0.0033 (18)	−0.0008 (16)
C13'	0.113 (4)	0.067 (3)	0.081 (3)	0.031 (3)	−0.019 (3)	−0.025 (2)
C14'	0.184 (5)	0.050 (3)	0.072 (3)	−0.039 (3)	0.002 (3)	−0.005 (2)
C15'	0.120 (4)	0.068 (3)	0.051 (2)	0.020 (3)	−0.013 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Si—C12	1.824 (3)	C15—H15A	0.9700
Si—C14	1.843 (4)	C15—H15B	0.9700
Si—C15	1.852 (4)	C15—H15C	0.9700
Si—C13	1.855 (4)	Si'—C12'	1.836 (4)
C1A—C1	1.386 (4)	Si'—C13'	1.845 (4)
C1A—C4A	1.397 (4)	Si'—C14'	1.847 (4)
C1A—C9	1.481 (4)	Si'—C15'	1.854 (4)
C1—C2	1.389 (4)	C8A—C8	1.386 (4)
C1—H1	0.9400	C8A—C5A	1.407 (4)
C2—C3	1.380 (5)	C8—C7	1.384 (4)
C2—H2	0.9400	C8—H8	0.9400
C3—C4	1.381 (4)	C7—C6	1.373 (5)
C3—H3	0.9400	C7—H7	0.9400
C4—C4A	1.385 (4)	C6—C5	1.387 (5)
C4—H4	0.9400	C6—H6	0.9400
C4A—C5A	1.459 (4)	C5—C5A	1.380 (4)
C9—C10	1.363 (4)	C5—H5	0.9400
C9—C8A	1.480 (4)	C11'—C12'	1.192 (4)
C10—C11'	1.435 (4)	C13'—H13D	0.9700
C10—C11	1.445 (4)	C13'—H13E	0.9700
C11—C12	1.194 (4)	C13'—H13F	0.9700
C13—H13A	0.9700	C14'—H14D	0.9700
C13—H13B	0.9700	C14'—H14E	0.9700
C13—H13C	0.9700	C14'—H14F	0.9700
C14—H14A	0.9700	C15'—H15D	0.9700
C14—H14B	0.9700	C15'—H15E	0.9700
C14—H14C	0.9700	C15'—H15F	0.9700

C12—Si—C14	108.52 (17)	Si—C15—H15C	109.5
C12—Si—C15	109.05 (17)	H15A—C15—H15C	109.5
C14—Si—C15	110.91 (19)	H15B—C15—H15C	109.5
C12—Si—C13	107.98 (17)	C12'—Si'—C13'	108.02 (18)
C14—Si—C13	110.8 (2)	C12'—Si'—C14'	109.22 (18)
C15—Si—C13	109.54 (19)	C13'—Si'—C14'	110.6 (2)
C1—C1A—C4A	119.9 (3)	C12'—Si'—C15'	107.40 (17)
C1—C1A—C9	131.5 (3)	C13'—Si'—C15'	110.4 (2)
C4A—C1A—C9	108.6 (3)	C14'—Si'—C15'	111.0 (2)
C1A—C1—C2	118.7 (3)	C8—C8A—C5A	119.6 (3)
C1A—C1—H1	120.7	C8—C8A—C9	132.1 (3)
C2—C1—H1	120.7	C5A—C8A—C9	108.4 (3)
C3—C2—C1	121.3 (3)	C7—C8—C8A	118.7 (3)
C3—C2—H2	119.4	C7—C8—H8	120.6
C1—C2—H2	119.4	C8A—C8—H8	120.6
C2—C3—C4	120.3 (3)	C6—C7—C8	121.6 (3)
C2—C3—H3	119.9	C6—C7—H7	119.2
C4—C3—H3	119.9	C8—C7—H7	119.2
C3—C4—C4A	119.0 (3)	C7—C6—C5	120.4 (3)
C3—C4—H4	120.5	C7—C6—H6	119.8
C4A—C4—H4	120.5	C5—C6—H6	119.8
C4—C4A—C1A	120.9 (3)	C5A—C5—C6	118.8 (3)
C4—C4A—C5A	130.2 (3)	C5A—C5—H5	120.6
C1A—C4A—C5A	108.9 (3)	C6—C5—H5	120.6
C10—C9—C8A	126.9 (3)	C5—C5A—C8A	120.9 (3)
C10—C9—C1A	127.5 (3)	C5—C5A—C4A	130.5 (3)
C8A—C9—C1A	105.6 (3)	C8A—C5A—C4A	108.6 (3)
C9—C10—C11'	123.5 (3)	C12'—C11'—C10	176.9 (3)
C9—C10—C11	122.4 (3)	C11'—C12'—Si'	175.2 (3)
C11'—C10—C11	114.1 (3)	Si'—C13'—H13D	109.5
C12—C11—C10	179.0 (4)	Si'—C13'—H13E	109.5
C11—C12—Si	173.3 (3)	H13D—C13'—H13E	109.5
Si—C13—H13A	109.5	Si'—C13'—H13F	109.5
Si—C13—H13B	109.5	H13D—C13'—H13F	109.5
H13A—C13—H13B	109.5	H13E—C13'—H13F	109.5
Si—C13—H13C	109.5	Si'—C14'—H14D	109.5
H13A—C13—H13C	109.5	Si'—C14'—H14E	109.5
H13B—C13—H13C	109.5	H14D—C14'—H14E	109.5
Si—C14—H14A	109.5	Si'—C14'—H14F	109.5
Si—C14—H14B	109.5	H14D—C14'—H14F	109.5
H14A—C14—H14B	109.5	H14E—C14'—H14F	109.5
Si—C14—H14C	109.5	Si'—C15'—H15D	109.5
H14A—C14—H14C	109.5	Si'—C15'—H15E	109.5
H14B—C14—H14C	109.5	H15D—C15'—H15E	109.5
Si—C15—H15A	109.5	Si'—C15'—H15F	109.5
Si—C15—H15B	109.5	H15D—C15'—H15F	109.5
H15A—C15—H15B	109.5	H15E—C15'—H15F	109.5

C4A—C1A—C1—C2	−0.6 (5)	C10—C9—C8A—C8	−0.4 (6)
C9—C1A—C1—C2	179.7 (3)	C1A—C9—C8A—C8	179.5 (3)
C1A—C1—C2—C3	0.2 (5)	C10—C9—C8A—C5A	−179.4 (3)
C1—C2—C3—C4	0.2 (6)	C1A—C9—C8A—C5A	0.5 (3)
C2—C3—C4—C4A	−0.2 (5)	C5A—C8A—C8—C7	0.3 (5)
C3—C4—C4A—C1A	−0.3 (5)	C9—C8A—C8—C7	−178.7 (3)
C3—C4—C4A—C5A	−179.8 (3)	C8A—C8—C7—C6	0.1 (5)
C1—C1A—C4A—C4	0.7 (5)	C8—C7—C6—C5	−0.1 (6)
C9—C1A—C4A—C4	−179.6 (3)	C7—C6—C5—C5A	−0.2 (6)
C1—C1A—C4A—C5A	−179.7 (3)	C6—C5—C5A—C8A	0.6 (5)
C9—C1A—C4A—C5A	0.0 (4)	C6—C5—C5A—C4A	179.4 (3)
C1—C1A—C9—C10	−0.7 (6)	C8—C8A—C5A—C5	−0.6 (5)
C4A—C1A—C9—C10	179.6 (3)	C9—C8A—C5A—C5	178.6 (3)
C1—C1A—C9—C8A	179.3 (3)	C8—C8A—C5A—C4A	−179.7 (3)
C4A—C1A—C9—C8A	−0.3 (3)	C9—C8A—C5A—C4A	−0.5 (4)
C8A—C9—C10—C11'	179.0 (3)	C4—C4A—C5A—C5	0.9 (6)
C1A—C9—C10—C11'	−0.9 (5)	C1A—C4A—C5A—C5	−178.7 (4)
C8A—C9—C10—C11	0.1 (5)	C4—C4A—C5A—C8A	179.9 (3)
C1A—C9—C10—C11	−179.9 (3)	C1A—C4A—C5A—C8A	0.3 (4)

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10,10-Bis­(tri­methyl­silyl­ethynyl)-9-methyl­enefluorene

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10,10-Bis(trimethylsilylethynyl)-9-methylenefluorene