Crystal structure of 1,1,2,2-tetra­methyl-1,2-bis­(2,3,4,5-tetra­methyl­cyclo­penta-2,4-dien-1-yl)disilane

Godemann, C.; Spannenberg, A.; Beweries, T.

doi:10.1107/S2056989015019891

organic compounds

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Volume 71| Part 11| November 2015| Page o888

https://doi.org/10.1107/S2056989015019891

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Crystal structure of 1,1,2,2-tetramethyl-1,2-bis(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)disilane

Christian Godemann,^a Anke Spannenberg ^a and Torsten Beweries ^a ^*

^aLeibniz-Institut für Katalyse e. V. der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: torsten.beweries@catalysis.de

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 21 October 2015; accepted 21 October 2015; online 28 October 2015)

The molecular structure of the title compound, C₂₂H₃₈Si₂, features a trans arrangement of the cyclopentadienyl rings to avoid steric strain [C—Si—Si—C torsion angle = −179.0 (5)°]. The Si—Si bond length is 2.3444 (4) Å. The most notable intermolecular interactions in the molecular packing are C—H⋯π contacts that lead to the formation of wave-like supramolecular chains along the b axis.

Keywords: crystal structure; disilane; ansa ligand.

CCDC reference: 1432476

1. Related literature

For synthesis of the title compound, see: Kessler et al. (2013 ). For group 4 complexes with this ligand, see: Godemann et al. (2014 , 2015 ); Pinkas et al. (2011 ); Xu et al. (1997 ); Horáček et al. (2008 ).

2. Experimental

2.1. Crystal data

C₂₂H₃₈Si₂
M_r = 358.70
Monoclinic P 2₁ /n
a = 8.7790 (2) Å
b = 15.3039 (4) Å
c = 16.4355 (4) Å
β = 93.678 (1)°
V = 2203.61 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 150 K
0.55 × 0.41 × 0.29 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.92, T_max = 0.95
46817 measured reflections
5318 independent reflections
4636 reflections with I > 2σ(I)
R_int = 0.035

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.06
5318 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1ⁱ	1.00	2.76	3.7350 (13)	166
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2009 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1432476

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015019891/tk5400sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019891/tk5400Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019891/tk5400Isup3.cml

checkCIF report

Synthesis and crystallization top

The synthesis of the title compound has been described previously (Kessler et al., 2013). A saturated solution of the title compound in n-hexane was very slowly cooled from 60 °C to room temperature resulting in precipitation of colourless crystals.

Refinement top

H atoms were placed in idealized positions with d(C—H) = 1.00 Å (CH) & 0.98 Å (CH₃), and refined using a riding model with U_iso(H) fixed at 1.2 U_eq(C) for CH & 1.5 U_eq(C) for CH₃.

Related literature top

For synthesis of the title compound, see: Kessler et al. (2013). For group 4 complexes with this ligand, see: Godemann et al. (2014, 2015); Pinkas et al. (2011); Xu et al. (1997); Horáček et al. (2008).

Structure description top

For synthesis of the title compound, see: Kessler et al. (2013). For group 4 complexes with this ligand, see: Godemann et al. (2014, 2015); Pinkas et al. (2011); Xu et al. (1997); Horáček et al. (2008).

Synthesis and crystallization top

Refinement details top

H atoms were placed in idealized positions with d(C—H) = 1.00 Å (CH) & 0.98 Å (CH₃), and refined using a riding model with U_iso(H) fixed at 1.2 U_eq(C) for CH & 1.5 U_eq(C) for CH₃.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with atom labelling scheme and displacement ellipsoids drawn at 30% probability level.

1,1,2,2-Tetramethyl-1,2-bis(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)disilane top

Crystal data top

C₂₂H₃₈Si₂	F(000) = 792
M_r = 358.70	D_x = 1.081 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.7790 (2) Å	Cell parameters from 9858 reflections
b = 15.3039 (4) Å	θ = 2.5–28.6°
c = 16.4355 (4) Å	µ = 0.16 mm⁻¹
β = 93.678 (1)°	T = 150 K
V = 2203.61 (9) Å³	Prism, colourless
Z = 4	0.55 × 0.41 × 0.29 mm

Data collection top

Bruker APEXII CCD diffractometer	5318 independent reflections
Radiation source: fine-focus sealed tube	4636 reflections with I > 2σ(I)
Curved graphite monochromator	R_int = 0.035
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.0°, θ_min = 1.8°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −20→19
T_min = 0.92, T_max = 0.95	l = −21→21
46817 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.047P)² + 0.8183P] where P = (F_o² + 2F_c²)/3
5318 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₃₈Si₂	V = 2203.61 (9) Å³
M_r = 358.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7790 (2) Å	µ = 0.16 mm⁻¹
b = 15.3039 (4) Å	T = 150 K
c = 16.4355 (4) Å	0.55 × 0.41 × 0.29 mm
β = 93.678 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5318 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4636 reflections with I > 2σ(I)
T_min = 0.92, T_max = 0.95	R_int = 0.035
46817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
5318 reflections	Δρ_min = −0.23 e Å⁻³
229 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

	x	y	z	U_iso*/U_eq
C1	0.85658 (13)	0.71127 (8)	0.10459 (7)	0.0212 (2)
H1	0.8437	0.6501	0.1244	0.025*
C2	1.01814 (13)	0.72631 (8)	0.08367 (8)	0.0227 (2)
C3	1.01837 (14)	0.75224 (8)	0.00516 (8)	0.0243 (2)
C4	0.86221 (14)	0.75132 (8)	−0.03149 (7)	0.0234 (2)
C5	0.76715 (14)	0.72439 (8)	0.02488 (7)	0.0228 (2)
C6	1.15522 (16)	0.71322 (10)	0.14202 (9)	0.0349 (3)
H6A	1.2403	0.6908	0.1123	0.052*
H6B	1.1304	0.6712	0.1842	0.052*
H6C	1.1843	0.7691	0.1676	0.052*
C7	1.15333 (17)	0.77834 (11)	−0.04066 (10)	0.0374 (3)
H7A	1.2463	0.7744	−0.0045	0.056*
H7B	1.1400	0.8385	−0.0601	0.056*
H7C	1.1620	0.7392	−0.0873	0.056*
C8	0.81945 (17)	0.77582 (10)	−0.11828 (8)	0.0332 (3)
H8A	0.8533	0.7299	−0.1546	0.050*
H8B	0.8687	0.8312	−0.1311	0.050*
H8C	0.7084	0.7823	−0.1259	0.050*
C9	0.59858 (16)	0.70960 (11)	0.01139 (9)	0.0359 (3)
H9A	0.5448	0.7653	0.0159	0.054*
H9B	0.5648	0.6688	0.0525	0.054*
H9C	0.5760	0.6850	−0.0431	0.054*
C10	0.59182 (15)	0.77168 (9)	0.20801 (9)	0.0298 (3)
H10A	0.5796	0.7097	0.2212	0.045*
H10B	0.5237	0.7867	0.1605	0.045*
H10C	0.5661	0.8075	0.2546	0.045*
C11	0.91263 (16)	0.77522 (9)	0.28252 (8)	0.0283 (3)
H11A	0.8710	0.8103	0.3258	0.042*
H11B	1.0184	0.7928	0.2756	0.042*
H11C	0.9099	0.7132	0.2973	0.042*
C12	0.69980 (16)	0.95635 (9)	0.04136 (7)	0.0275 (3)
H12A	0.6950	1.0192	0.0299	0.041*
H12B	0.5966	0.9340	0.0475	0.041*
H12C	0.7448	0.9260	−0.0038	0.041*
C13	1.02293 (15)	0.96094 (9)	0.11437 (8)	0.0281 (3)
H13A	1.0465	0.9302	0.0644	0.042*
H13B	1.0925	0.9412	0.1597	0.042*
H13C	1.0353	1.0240	0.1066	0.042*
C14	0.76149 (13)	1.01788 (8)	0.21979 (7)	0.0205 (2)
H14	0.7769	1.0788	0.1999	0.025*
C15	0.59856 (13)	1.00765 (8)	0.24095 (7)	0.0223 (2)
C16	0.59561 (14)	0.98747 (8)	0.32073 (8)	0.0236 (2)
C17	0.75209 (14)	0.98656 (8)	0.35759 (7)	0.0228 (2)
C18	0.84985 (13)	1.00645 (8)	0.30048 (7)	0.0222 (2)
C19	0.46292 (15)	1.01960 (10)	0.18157 (9)	0.0334 (3)
H19A	0.4372	0.9637	0.1550	0.050*
H19B	0.4872	1.0627	0.1403	0.050*
H19C	0.3758	1.0402	0.2107	0.050*
C20	0.45939 (16)	0.97111 (10)	0.36880 (10)	0.0367 (3)
H20A	0.4494	1.0185	0.4082	0.055*
H20B	0.4722	0.9155	0.3979	0.055*
H20C	0.3674	0.9686	0.3318	0.055*
C21	0.78832 (18)	0.96916 (10)	0.44647 (8)	0.0346 (3)
H21A	0.8990	0.9635	0.4570	0.052*
H21B	0.7385	0.9149	0.4620	0.052*
H21C	0.7511	1.0177	0.4786	0.052*
C22	1.01980 (15)	1.01596 (10)	0.31332 (9)	0.0324 (3)
H22A	1.0463	1.0338	0.3697	0.049*
H22B	1.0554	1.0604	0.2760	0.049*
H22C	1.0687	0.9599	0.3026	0.049*
Si1	0.79503 (4)	0.79312 (2)	0.184414 (19)	0.01845 (9)
Si2	0.82065 (4)	0.93696 (2)	0.138159 (18)	0.01799 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0224 (6)	0.0182 (5)	0.0231 (6)	−0.0005 (4)	0.0010 (4)	0.0000 (4)
C2	0.0193 (6)	0.0207 (5)	0.0281 (6)	0.0035 (4)	0.0009 (5)	−0.0026 (5)
C3	0.0220 (6)	0.0228 (6)	0.0287 (6)	0.0019 (4)	0.0058 (5)	−0.0031 (5)
C4	0.0253 (6)	0.0226 (6)	0.0223 (6)	0.0024 (5)	0.0009 (5)	−0.0038 (5)
C5	0.0219 (6)	0.0223 (6)	0.0239 (6)	−0.0014 (4)	−0.0015 (4)	−0.0046 (5)
C6	0.0237 (6)	0.0428 (8)	0.0373 (7)	0.0086 (6)	−0.0046 (5)	−0.0002 (6)
C7	0.0292 (7)	0.0442 (8)	0.0402 (8)	0.0019 (6)	0.0139 (6)	0.0004 (6)
C8	0.0373 (7)	0.0390 (8)	0.0231 (6)	0.0037 (6)	0.0014 (5)	−0.0008 (5)
C9	0.0250 (7)	0.0465 (8)	0.0354 (7)	−0.0099 (6)	−0.0042 (5)	−0.0049 (6)
C10	0.0259 (6)	0.0287 (7)	0.0359 (7)	−0.0050 (5)	0.0114 (5)	−0.0005 (5)
C11	0.0353 (7)	0.0288 (6)	0.0204 (6)	0.0030 (5)	−0.0022 (5)	0.0033 (5)
C12	0.0346 (7)	0.0277 (6)	0.0200 (6)	0.0040 (5)	−0.0011 (5)	0.0023 (5)
C13	0.0264 (6)	0.0264 (6)	0.0328 (7)	−0.0051 (5)	0.0113 (5)	−0.0022 (5)
C14	0.0195 (5)	0.0203 (5)	0.0215 (5)	0.0016 (4)	0.0004 (4)	−0.0023 (4)
C15	0.0176 (5)	0.0216 (6)	0.0273 (6)	0.0035 (4)	−0.0006 (4)	−0.0049 (5)
C16	0.0217 (6)	0.0203 (5)	0.0290 (6)	0.0012 (4)	0.0040 (5)	−0.0033 (5)
C17	0.0260 (6)	0.0199 (5)	0.0222 (6)	0.0033 (4)	−0.0003 (5)	−0.0028 (4)
C18	0.0201 (6)	0.0215 (5)	0.0244 (6)	0.0021 (4)	−0.0024 (4)	−0.0060 (5)
C19	0.0222 (6)	0.0429 (8)	0.0342 (7)	0.0080 (6)	−0.0059 (5)	−0.0073 (6)
C20	0.0292 (7)	0.0395 (8)	0.0427 (8)	−0.0005 (6)	0.0126 (6)	0.0018 (6)
C21	0.0422 (8)	0.0362 (7)	0.0249 (6)	0.0042 (6)	−0.0009 (6)	0.0012 (6)
C22	0.0205 (6)	0.0409 (8)	0.0351 (7)	0.0000 (5)	−0.0042 (5)	−0.0099 (6)
Si1	0.01894 (16)	0.01846 (16)	0.01803 (16)	−0.00115 (11)	0.00177 (11)	0.00206 (11)
Si2	0.01903 (16)	0.01773 (16)	0.01736 (15)	−0.00037 (11)	0.00222 (11)	0.00092 (11)

Geometric parameters (Å, º) top

C1—C5	1.4969 (16)	C12—H12A	0.9800
C1—C2	1.4985 (16)	C12—H12B	0.9800
C1—Si1	1.9166 (12)	C12—H12C	0.9800
C1—H1	1.0000	C13—Si2	1.8789 (13)
C2—C3	1.3501 (18)	C13—H13A	0.9800
C2—C6	1.5033 (17)	C13—H13B	0.9800
C3—C4	1.4617 (17)	C13—H13C	0.9800
C3—C7	1.4984 (18)	C14—C15	1.5017 (16)
C4—C5	1.3505 (17)	C14—C18	1.5031 (16)
C4—C8	1.4993 (17)	C14—Si2	1.9216 (12)
C5—C9	1.4994 (17)	C14—H14	1.0000
C6—H6A	0.9800	C15—C16	1.3490 (17)
C6—H6B	0.9800	C15—C19	1.5016 (17)
C6—H6C	0.9800	C16—C17	1.4655 (17)
C7—H7A	0.9800	C16—C20	1.4961 (17)
C7—H7B	0.9800	C17—C18	1.3467 (17)
C7—H7C	0.9800	C17—C21	1.4989 (17)
C8—H8A	0.9800	C18—C22	1.5004 (17)
C8—H8B	0.9800	C19—H19A	0.9800
C8—H8C	0.9800	C19—H19B	0.9800
C9—H9A	0.9800	C19—H19C	0.9800
C9—H9B	0.9800	C20—H20A	0.9800
C9—H9C	0.9800	C20—H20B	0.9800
C10—Si1	1.8787 (13)	C20—H20C	0.9800
C10—H10A	0.9800	C21—H21A	0.9800
C10—H10B	0.9800	C21—H21B	0.9800
C10—H10C	0.9800	C21—H21C	0.9800
C11—Si1	1.8780 (13)	C22—H22A	0.9800
C11—H11A	0.9800	C22—H22B	0.9800
C11—H11B	0.9800	C22—H22C	0.9800
C11—H11C	0.9800	Si1—Si2	2.3444 (4)
C12—Si2	1.8783 (13)

C5—C1—C2	103.28 (10)	Si2—C13—H13A	109.5
C5—C1—Si1	110.87 (8)	Si2—C13—H13B	109.5
C2—C1—Si1	111.67 (8)	H13A—C13—H13B	109.5
C5—C1—H1	110.3	Si2—C13—H13C	109.5
C2—C1—H1	110.3	H13A—C13—H13C	109.5
Si1—C1—H1	110.3	H13B—C13—H13C	109.5
C3—C2—C1	108.89 (11)	C15—C14—C18	103.23 (10)
C3—C2—C6	126.77 (12)	C15—C14—Si2	113.49 (8)
C1—C2—C6	124.33 (11)	C18—C14—Si2	113.19 (8)
C2—C3—C4	109.40 (11)	C15—C14—H14	108.9
C2—C3—C7	127.48 (12)	C18—C14—H14	108.9
C4—C3—C7	123.12 (12)	Si2—C14—H14	108.9
C5—C4—C3	108.95 (11)	C16—C15—C19	126.57 (12)
C5—C4—C8	126.95 (12)	C16—C15—C14	109.08 (10)
C3—C4—C8	124.10 (12)	C19—C15—C14	124.35 (11)
C4—C5—C1	109.19 (11)	C15—C16—C17	109.15 (11)
C4—C5—C9	126.30 (12)	C15—C16—C20	128.13 (12)
C1—C5—C9	124.51 (11)	C17—C16—C20	122.68 (12)
C2—C6—H6A	109.5	C18—C17—C16	109.40 (11)
C2—C6—H6B	109.5	C18—C17—C21	127.92 (12)
H6A—C6—H6B	109.5	C16—C17—C21	122.63 (11)
C2—C6—H6C	109.5	C17—C18—C22	126.61 (12)
H6A—C6—H6C	109.5	C17—C18—C14	108.99 (10)
H6B—C6—H6C	109.5	C22—C18—C14	124.40 (11)
C3—C7—H7A	109.5	C15—C19—H19A	109.5
C3—C7—H7B	109.5	C15—C19—H19B	109.5
H7A—C7—H7B	109.5	H19A—C19—H19B	109.5
C3—C7—H7C	109.5	C15—C19—H19C	109.5
H7A—C7—H7C	109.5	H19A—C19—H19C	109.5
H7B—C7—H7C	109.5	H19B—C19—H19C	109.5
C4—C8—H8A	109.5	C16—C20—H20A	109.5
C4—C8—H8B	109.5	C16—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
C4—C8—H8C	109.5	C16—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
C5—C9—H9A	109.5	C17—C21—H21A	109.5
C5—C9—H9B	109.5	C17—C21—H21B	109.5
H9A—C9—H9B	109.5	H21A—C21—H21B	109.5
C5—C9—H9C	109.5	C17—C21—H21C	109.5
H9A—C9—H9C	109.5	H21A—C21—H21C	109.5
H9B—C9—H9C	109.5	H21B—C21—H21C	109.5
Si1—C10—H10A	109.5	C18—C22—H22A	109.5
Si1—C10—H10B	109.5	C18—C22—H22B	109.5
H10A—C10—H10B	109.5	H22A—C22—H22B	109.5
Si1—C10—H10C	109.5	C18—C22—H22C	109.5
H10A—C10—H10C	109.5	H22A—C22—H22C	109.5
H10B—C10—H10C	109.5	H22B—C22—H22C	109.5
Si1—C11—H11A	109.5	C11—Si1—C10	105.92 (6)
Si1—C11—H11B	109.5	C11—Si1—C1	109.20 (6)
H11A—C11—H11B	109.5	C10—Si1—C1	109.90 (6)
Si1—C11—H11C	109.5	C11—Si1—Si2	110.88 (4)
H11A—C11—H11C	109.5	C10—Si1—Si2	110.06 (5)
H11B—C11—H11C	109.5	C1—Si1—Si2	110.77 (4)
Si2—C12—H12A	109.5	C12—Si2—C13	106.44 (6)
Si2—C12—H12B	109.5	C12—Si2—C14	109.04 (6)
H12A—C12—H12B	109.5	C13—Si2—C14	108.71 (6)
Si2—C12—H12C	109.5	C12—Si2—Si1	111.24 (4)
H12A—C12—H12C	109.5	C13—Si2—Si1	111.25 (4)
H12B—C12—H12C	109.5	C14—Si2—Si1	110.05 (4)

C5—C1—C2—C3	4.99 (13)	C20—C16—C17—C21	−0.01 (19)
Si1—C1—C2—C3	−114.20 (10)	C16—C17—C18—C22	177.49 (12)
C5—C1—C2—C6	−174.52 (12)	C21—C17—C18—C22	−0.1 (2)
Si1—C1—C2—C6	66.29 (14)	C16—C17—C18—C14	−2.63 (14)
C1—C2—C3—C4	−3.13 (14)	C21—C17—C18—C14	179.77 (12)
C6—C2—C3—C4	176.37 (12)	C15—C14—C18—C17	3.78 (13)
C1—C2—C3—C7	177.06 (12)	Si2—C14—C18—C17	−119.32 (10)
C6—C2—C3—C7	−3.4 (2)	C15—C14—C18—C22	−176.33 (11)
C2—C3—C4—C5	−0.26 (15)	Si2—C14—C18—C22	60.57 (14)
C7—C3—C4—C5	179.56 (12)	C5—C1—Si1—C11	−179.05 (8)
C2—C3—C4—C8	−179.61 (12)	C2—C1—Si1—C11	−64.46 (10)
C7—C3—C4—C8	0.2 (2)	C5—C1—Si1—C10	65.17 (10)
C3—C4—C5—C1	3.55 (14)	C2—C1—Si1—C10	179.76 (9)
C8—C4—C5—C1	−177.13 (12)	C5—C1—Si1—Si2	−56.66 (9)
C3—C4—C5—C9	−176.51 (12)	C2—C1—Si1—Si2	57.93 (9)
C8—C4—C5—C9	2.8 (2)	C15—C14—Si2—C12	61.62 (10)
C2—C1—C5—C4	−5.18 (13)	C18—C14—Si2—C12	178.86 (9)
Si1—C1—C5—C4	114.56 (10)	C15—C14—Si2—C13	177.27 (9)
C2—C1—C5—C9	174.88 (12)	C18—C14—Si2—C13	−65.49 (10)
Si1—C1—C5—C9	−65.38 (14)	C15—C14—Si2—Si1	−60.65 (9)
C18—C14—C15—C16	−3.64 (13)	C18—C14—Si2—Si1	56.59 (9)
Si2—C14—C15—C16	119.27 (10)	C11—Si1—Si2—C12	−178.64 (6)
C18—C14—C15—C19	175.62 (11)	C10—Si1—Si2—C12	−61.77 (7)
Si2—C14—C15—C19	−61.48 (14)	C1—Si1—Si2—C12	59.96 (6)
C19—C15—C16—C17	−176.98 (12)	C11—Si1—Si2—C13	62.88 (7)
C14—C15—C16—C17	2.25 (14)	C10—Si1—Si2—C13	179.74 (6)
C19—C15—C16—C20	0.9 (2)	C1—Si1—Si2—C13	−58.52 (6)
C14—C15—C16—C20	−179.88 (12)	C11—Si1—Si2—C14	−57.68 (6)
C15—C16—C17—C18	0.24 (14)	C10—Si1—Si2—C14	59.19 (6)
C20—C16—C17—C18	−177.76 (12)	C1—Si1—Si2—C14	−179.08 (5)
C15—C16—C17—C21	177.99 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	1.00	2.65	3.646	173

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	1.00	2.65	3.646	173

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

Financial support by the BMBF (project `Light2Hydrogen') is gratefully acknowledged.

References

Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Godemann, C., Barsch, E., Spannenberg, A., Ludwig, R. & Beweries, T. (2014). Eur. J. Inorg. Chem. 25, 4068–4072. CSD CrossRef Google Scholar
Godemann, C., Dura, L., Hollmann, D., Grabow, K., Bentrup, U., Jiao, H., Schulz, A., Brückner, A. & Beweries, T. (2015). Chem. Commun. 51, 3065–3068. CSD CrossRef CAS Google Scholar
Horáček, M., Pinkas, J., Gyepes, R., Kubišta, J. & Mach, K. (2008). Organometallics, 27, 2635–2642. Google Scholar
Kessler, M., Hansen, S., Godemann, C., Spannenberg, A. & Beweries, T. (2013). Chem. Eur. J. 19, 6350–6357. CSD CrossRef CAS PubMed Google Scholar
Pinkas, J., Gyepes, R., Císařovà, I., Kubišta, J., Mach, K. & Horáček, M. (2011). Collect. Czech. Chem. Commun. 76, 177–191. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, S.-S., Deng, X.-B., Wang, B.-Q. & Zhou, X.-Z. (1997). Acta Chim. Sin. 55, 829–832. CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1,1,2,2-tetra­methyl-1,2-bis­­(2,3,4,5-tetra­methyl­cyclo­penta-2,4-dien-1-yl)disilane

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1,1,2,2-tetramethyl-1,2-bis(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)disilane