Bis(2-naphthyl­meth­yl)diphenyl­silane

Monroe, T.B.; Thomas, A.A.; Jones, D.S.; Ogle, C.A.

doi:10.1107/S1600536809047412

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o132

doi:10.1107/S1600536809047412

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Bis(2-naphthylmethyl)diphenylsilane

Thomas Blake Monroe,^a Andy A. Thomas,^a Daniel S. Jones ^a ^* and Craig A. Ogle ^a ^*

^aDepartment of Chemistry, The University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223, USA
^*Correspondence e-mail: djones@uncc.edu, cogle@uncc.edu

(Received 13 August 2009; accepted 9 November 2009; online 12 December 2009)

The title compound, C₃₄H₂₈Si, was prepared as an internal standard for diffusion-ordered NMR spectroscopy. The four ligands are arranged tetrahedrally around the Si atom. The two naphthalene systems are nearly perpendicular, making an angle of 86.42 (4)° with one another. A naphthalene system and a phenyl ring are also nearly perpendicular, making an angle of 86.18 (6)° with one another. In the crystal, the molecules pack in columns parallel to the a axis, and exhibit arene C—H⋯π(arene) interactions both within and between columns.

Related literature

For applications of the title compound related to NMR spectroscopy, see: Li et al. (2009 ). A search of the Cambridge Structural Database (Allen, 2002 ; CONQUEST; Bruno et al., 2002 ) yielded no comparable structures.

Experimental

Crystal data

C₃₄H₂₈Si
M_r = 464.65
Triclinic, $[P \overline 1]$
a = 9.4884 (14) Å
b = 11.0673 (13) Å
c = 13.3450 (15) Å
α = 75.820 (9)°
β = 83.767 (11)°
γ = 70.575 (11)°
V = 1280.8 (3) Å³
Z = 2
Cu Kα radiation
μ = 0.94 mm⁻¹
T = 295 K
0.36 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: analytical (Alcock, 1970 ) T_min = 0.814, T_max = 0.954
9101 measured reflections
4618 independent reflections
3060 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 165 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.01
4618 reflections
333 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Arene C—H⋯π (arene) packing interactions (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ⁱ	0.93	2.66	3.569 (2)	166
C5—H5⋯Cg2ⁱⁱ	0.93	2.88	3.664 (2)	143
C9—H9⋯Cg3ⁱⁱⁱ	0.93	2.76	3.577 (2)	148
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+2. Cg1, Cg2, and Cg3 are the centroids of the C7–C12, C14–C17/C22/C23 and C27–C32 rings, respectively.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047412/fl2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047412/fl2263Isup2.hkl

checkCIF report

Comment top

The title compound was prepared as an internal standard for diffusion-ordered NMR spectroscopy. A recent paper on this subject (Li et al., 2009) suggests an internal standard method for correlating diffusion coefficients with formula weights. The title compound was chosen because its shape both approximates that of a spheroid and is similar to that of the species being studied. In addition, it neither reacts with the species under study nor gives interfering NMR signals.

The ligands are arranged tetrahedrally around the silicon atom. The two naphthalene rings of the title compound are nearly perpendicular, making an angle of 86.42 (4)° with one another. A naphthalene ring and a phenyl ring are also nearly perpendicular, making an angle of 86.18 (6)° with one another. The angle between the phenyl rings is 74.35 (7)°. The molecules pack in columns parallel to the a axis and exhibit arene C—H··· arene π interactions both within and between columns. These interactions between a phenyl of one molecule and a proximal aromatic ring of a naphthyl on a molecule in an adjacent column are 2.879 (3) Å in length (Figure 2). The interactions between two phenyls of two adjacent molecules in the same column are 2.659 (2) Å in length (Figure 2). The interactions between a phenyl of one molecule and a distal aromatic ring of a naphthyl on an adjacent molecule in the same column are 2.757 (2) Å in length (Figure 3).

A search of the Cambridge Structural Database [Version 5.30 (Allen, 2002); CONQUEST (Bruno et al., 2002)] yielded no comparable structures. The search fragment used consisted of two naphthalene rings coordinated to Si, both with and without the methylene bridges.

Related literature top

For applications of the title compound related to NMR spectroscopy, see: Li et al. (2009). A search of the Cambridge Structural Database (Allen, 2002; CONQUEST; Bruno et al., 2002) yielded no comparable structures.

Experimental top

A dry, 250 ml Schlenk flask, equipped with a magnetic stir bar, was charged with 2-methylnaphthalene (I) (4.26 g, 300 mmol) and potassium tert-butoxide (3.92 g, 350 mmol). The Schlenk flask was purged with nitrogen. Freshly distilled THF (100 ml) was added and the reaction was cooled to -78 °C. n-BuLi (15.2 ml, 2.3 M) was then added dropwise. The Schlenk flask was then capped and kept at -40 °C overnight. The solution was again cooled to -78 °C and 2.09 ml (2.52 g, 100 mmol) of dichlorodiphenylsilane was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was then quenched with deionized water and extracted three times with hexanes. The combined organic layers were dried with magnesium sulfate, filtered, and evaporated. Bulb-to-bulb distillation gave a tan solid, which was recrystallized from hexanes to yield colorless crystals of the title compound (II) (2.56 g, 55% recovery).

mp 98 - 100 °C; ¹H NMR (DMSO-d₆, 300 MHz): 2.86(s), 6.97 (d), 7.32 (m), 7.41(m), 7.58 (m), 7.75 (d) p.p.m.. ¹³C NMR (DMSO-d₆, 300 MHz): 21.92, 125.83, 126.27, 126.73, 127.10, 127.36, 127.71, 128.19, 129.59, 130.65, 133.06, 134.18, 135.14, 136.11 p.p.m.. GC/MS (70ev) m/z: 464.3, 323.2, 245.1, 215.1,193.1, 167.1, 141.1, 105.0.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of title compound (50% probability displacement ellipsoids)
	Fig. 2. Diagram showing how molecules of the title compound form columns parallel to the a axis. Naphthyl-phenyl C—H···π interactions between columns and phenyl-phenyl C—H···π interactions within columns are illustrated
	Fig. 3. Diagram showing naphthyl-phenyl C—H···π interactions within columns
	Fig. 4. Synthesis scheme

Bis(2-naphthylmethyl)diphenylsilane top

Crystal data top

C₃₄H₂₈Si	Z = 2
M_r = 464.65	F(000) = 492
Triclinic, P1	D_x = 1.205 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.4884 (14) Å	Cell parameters from 25 reflections
b = 11.0673 (13) Å	θ = 9.7–40.3°
c = 13.3450 (15) Å	µ = 0.94 mm⁻¹
α = 75.820 (9)°	T = 295 K
β = 83.767 (11)°	Prism, colorless
γ = 70.575 (11)°	0.36 × 0.20 × 0.05 mm
V = 1280.8 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.045
Non–profiled ω/2θ scans	θ_max = 67.4°, θ_min = 3.4°
Absorption correction: analytical (see. N.W. Alcock (1970))	h = −11→11
T_min = 0.814, T_max = 0.954	k = −13→13
9101 measured reflections	l = −15→15
4618 independent reflections	3 standard reflections every 165 reflections
3060 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0422P)² + 0.1595P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4618 reflections	Δρ_max = 0.17 e Å⁻³
333 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (4)

Crystal data top

C₃₄H₂₈Si	γ = 70.575 (11)°
M_r = 464.65	V = 1280.8 (3) Å³
Triclinic, P1	Z = 2
a = 9.4884 (14) Å	Cu Kα radiation
b = 11.0673 (13) Å	µ = 0.94 mm⁻¹
c = 13.3450 (15) Å	T = 295 K
α = 75.820 (9)°	0.36 × 0.20 × 0.05 mm
β = 83.767 (11)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3060 reflections with I > 2σ(I)
Absorption correction: analytical (see. N.W. Alcock (1970))	R_int = 0.045
T_min = 0.814, T_max = 0.954	3 standard reflections every 165 reflections
9101 measured reflections	intensity decay: 1%
4618 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.17 e Å⁻³
4618 reflections	Δρ_min = −0.20 e Å⁻³
333 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H24B	0.231 (2)	0.353 (2)	0.7647 (17)	0.069 (7)*
H13A	0.348 (2)	0.458 (2)	0.5907 (16)	0.067 (7)*
H24A	0.117 (3)	0.479 (2)	0.7954 (16)	0.063 (6)*
H13B	0.422 (3)	0.572 (2)	0.5734 (18)	0.085 (8)*
Si	0.34325 (6)	0.51722 (5)	0.74770 (4)	0.04382 (15)
C1	0.5414 (2)	0.42670 (17)	0.78451 (14)	0.0431 (4)
C7	0.2828 (2)	0.67956 (18)	0.78528 (13)	0.0429 (4)
C14	0.1897 (2)	0.64223 (19)	0.55711 (14)	0.0484 (5)
C25	0.2299 (2)	0.34952 (18)	0.91925 (15)	0.0468 (5)
C12	0.3864 (2)	0.73768 (19)	0.80112 (15)	0.0507 (5)
H12	0.4880	0.6936	0.7945	0.061*
C22	−0.0752 (2)	0.7066 (2)	0.52307 (14)	0.0500 (5)
C27	0.2921 (2)	0.15022 (19)	1.05667 (16)	0.0489 (5)
C32	0.2569 (2)	0.22750 (19)	1.13133 (15)	0.0481 (5)
C34	0.1945 (2)	0.42439 (19)	0.99582 (16)	0.0554 (5)
H34	0.1610	0.5156	0.9760	0.067*
C26	0.2781 (2)	0.21659 (19)	0.94994 (16)	0.0520 (5)
H26	0.3030	0.1668	0.8999	0.062*
C23	0.0584 (2)	0.6132 (2)	0.56567 (15)	0.0511 (5)
H23	0.0574	0.5296	0.6005	0.061*
C24	0.2150 (3)	0.4184 (2)	0.80615 (17)	0.0561 (5)
C6	0.6578 (2)	0.3999 (2)	0.71170 (16)	0.0559 (5)
H6	0.6359	0.4249	0.6419	0.067*
C33	0.2086 (2)	0.3654 (2)	1.09779 (16)	0.0556 (5)
H33	0.1859	0.4171	1.1465	0.067*
C8	0.1324 (2)	0.75053 (19)	0.79637 (16)	0.0533 (5)
H8	0.0602	0.7154	0.7860	0.064*
C2	0.5820 (2)	0.38502 (19)	0.88809 (15)	0.0534 (5)
H2	0.5081	0.4005	0.9395	0.064*
C17	−0.0733 (2)	0.8326 (2)	0.46839 (15)	0.0538 (5)
C11	0.3415 (2)	0.8586 (2)	0.82632 (17)	0.0610 (6)
H11	0.4128	0.8951	0.8359	0.073*
C13	0.3323 (2)	0.5450 (2)	0.60306 (15)	0.0533 (5)
C5	0.8042 (2)	0.3374 (2)	0.73991 (18)	0.0667 (6)
H5	0.8793	0.3220	0.6892	0.080*
C9	0.0876 (2)	0.8709 (2)	0.82220 (17)	0.0610 (6)
H9	−0.0138	0.9155	0.8294	0.073*
C31	0.2693 (2)	0.1627 (2)	1.23757 (16)	0.0594 (5)
H31	0.2464	0.2119	1.2880	0.071*
C10	0.1923 (2)	0.9257 (2)	0.83749 (17)	0.0608 (6)
H10	0.1623	1.0070	0.8551	0.073*
C3	0.7281 (2)	0.3218 (2)	0.91611 (17)	0.0593 (5)
H3	0.7513	0.2951	0.9857	0.071*
C4	0.8400 (2)	0.2979 (2)	0.84222 (18)	0.0630 (6)
H4	0.9389	0.2554	0.8613	0.076*
C15	0.1884 (2)	0.7688 (2)	0.50217 (16)	0.0590 (5)
H15	0.2761	0.7905	0.4955	0.071*
C21	−0.2121 (3)	0.6793 (2)	0.5334 (2)	0.0698 (6)
H21	−0.2162	0.5970	0.5690	0.084*
C16	0.0625 (3)	0.8597 (2)	0.45870 (17)	0.0627 (6)
H16	0.0662	0.9416	0.4217	0.075*
C28	0.3387 (2)	0.0136 (2)	1.08931 (19)	0.0642 (6)
H28	0.3629	−0.0377	1.0403	0.077*
C30	0.3144 (2)	0.0290 (2)	1.26605 (18)	0.0678 (7)
H30	0.3221	−0.0127	1.3357	0.081*
C29	0.3492 (3)	−0.0456 (2)	1.1907 (2)	0.0709 (7)
H29	0.3799	−0.1368	1.2107	0.085*
C18	−0.2061 (3)	0.9261 (2)	0.42547 (18)	0.0712 (6)
H18	−0.2051	1.0090	0.3891	0.085*
C20	−0.3378 (3)	0.7729 (3)	0.4914 (2)	0.0857 (8)
H20	−0.4274	0.7541	0.4993	0.103*
C19	−0.3347 (3)	0.8966 (3)	0.4365 (2)	0.0856 (8)
H19	−0.4214	0.9590	0.4075	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0394 (3)	0.0496 (3)	0.0420 (3)	−0.0157 (2)	−0.0023 (2)	−0.0067 (2)
C1	0.0433 (11)	0.0416 (10)	0.0431 (10)	−0.0136 (8)	−0.0019 (8)	−0.0067 (8)
C7	0.0369 (10)	0.0512 (10)	0.0399 (10)	−0.0163 (8)	−0.0019 (8)	−0.0052 (8)
C14	0.0488 (12)	0.0609 (12)	0.0367 (10)	−0.0181 (10)	−0.0011 (8)	−0.0121 (8)
C25	0.0392 (11)	0.0510 (11)	0.0520 (11)	−0.0213 (9)	0.0014 (9)	−0.0061 (9)
C12	0.0329 (10)	0.0570 (12)	0.0618 (12)	−0.0129 (9)	0.0000 (9)	−0.0150 (9)
C22	0.0469 (12)	0.0643 (12)	0.0448 (11)	−0.0203 (10)	−0.0008 (9)	−0.0200 (9)
C27	0.0386 (11)	0.0518 (11)	0.0584 (12)	−0.0198 (9)	0.0030 (9)	−0.0104 (9)
C32	0.0334 (10)	0.0538 (11)	0.0573 (12)	−0.0175 (8)	0.0023 (8)	−0.0091 (9)
C34	0.0508 (13)	0.0489 (11)	0.0638 (13)	−0.0159 (9)	0.0040 (10)	−0.0099 (10)
C26	0.0490 (12)	0.0548 (12)	0.0590 (12)	−0.0244 (9)	0.0057 (9)	−0.0172 (10)
C23	0.0532 (12)	0.0548 (11)	0.0481 (11)	−0.0210 (10)	−0.0029 (9)	−0.0106 (9)
C24	0.0560 (14)	0.0611 (13)	0.0546 (13)	−0.0276 (12)	−0.0042 (10)	−0.0055 (10)
C6	0.0466 (12)	0.0663 (13)	0.0483 (11)	−0.0115 (10)	0.0003 (9)	−0.0110 (10)
C33	0.0512 (13)	0.0582 (12)	0.0603 (13)	−0.0190 (10)	0.0083 (10)	−0.0207 (10)
C8	0.0355 (11)	0.0580 (12)	0.0670 (13)	−0.0161 (9)	−0.0042 (9)	−0.0121 (10)
C2	0.0482 (12)	0.0630 (12)	0.0472 (11)	−0.0156 (10)	−0.0017 (9)	−0.0115 (9)
C17	0.0507 (12)	0.0613 (12)	0.0473 (11)	−0.0143 (10)	−0.0038 (9)	−0.0122 (9)
C11	0.0490 (13)	0.0616 (13)	0.0800 (15)	−0.0246 (11)	−0.0027 (11)	−0.0195 (11)
C13	0.0482 (13)	0.0628 (13)	0.0471 (11)	−0.0156 (10)	−0.0037 (9)	−0.0104 (10)
C5	0.0463 (13)	0.0776 (15)	0.0668 (15)	−0.0077 (11)	0.0054 (11)	−0.0188 (12)
C9	0.0388 (12)	0.0584 (13)	0.0793 (16)	−0.0065 (10)	−0.0044 (11)	−0.0151 (11)
C31	0.0437 (12)	0.0820 (15)	0.0564 (13)	−0.0271 (11)	0.0035 (10)	−0.0146 (11)
C10	0.0523 (13)	0.0514 (12)	0.0764 (15)	−0.0097 (10)	−0.0052 (11)	−0.0179 (11)
C3	0.0554 (13)	0.0637 (13)	0.0557 (12)	−0.0169 (11)	−0.0148 (10)	−0.0051 (10)
C4	0.0443 (12)	0.0586 (13)	0.0793 (16)	−0.0061 (10)	−0.0128 (11)	−0.0126 (11)
C15	0.0510 (13)	0.0677 (14)	0.0594 (13)	−0.0259 (11)	0.0018 (10)	−0.0078 (11)
C21	0.0592 (15)	0.0777 (16)	0.0843 (17)	−0.0321 (13)	−0.0011 (13)	−0.0252 (13)
C16	0.0600 (15)	0.0583 (13)	0.0653 (14)	−0.0217 (11)	−0.0031 (11)	−0.0012 (10)
C28	0.0576 (14)	0.0535 (12)	0.0812 (16)	−0.0199 (11)	0.0014 (12)	−0.0130 (11)
C30	0.0491 (13)	0.0839 (17)	0.0618 (14)	−0.0294 (12)	−0.0085 (11)	0.0142 (13)
C29	0.0606 (15)	0.0563 (13)	0.0880 (18)	−0.0216 (11)	−0.0068 (13)	0.0045 (13)
C18	0.0607 (16)	0.0724 (15)	0.0703 (15)	−0.0084 (12)	−0.0149 (12)	−0.0095 (12)
C20	0.0470 (15)	0.106 (2)	0.116 (2)	−0.0242 (14)	−0.0099 (14)	−0.0429 (18)
C19	0.0596 (17)	0.0880 (19)	0.104 (2)	−0.0052 (14)	−0.0254 (15)	−0.0265 (16)

Geometric parameters (Å, º) top

Si—C1	1.868 (2)	C8—H8	0.9300
Si—C7	1.8714 (19)	C2—C3	1.375 (3)
Si—C24	1.883 (2)	C2—H2	0.9300
Si—C13	1.887 (2)	C17—C16	1.402 (3)
C1—C6	1.393 (3)	C17—C18	1.409 (3)
C1—C2	1.399 (3)	C11—C10	1.373 (3)
C7—C8	1.393 (3)	C11—H11	0.9300
C7—C12	1.399 (3)	C13—H13A	0.98 (2)
C14—C23	1.373 (3)	C13—H13B	1.00 (3)
C14—C15	1.409 (3)	C5—C4	1.371 (3)
C14—C13	1.501 (3)	C5—H5	0.9300
C25—C26	1.356 (3)	C9—C10	1.379 (3)
C25—C34	1.414 (3)	C9—H9	0.9300
C25—C24	1.513 (3)	C31—C30	1.362 (3)
C12—C11	1.376 (3)	C31—H31	0.9300
C12—H12	0.9300	C10—H10	0.9300
C22—C17	1.412 (3)	C3—C4	1.372 (3)
C22—C23	1.413 (3)	C3—H3	0.9300
C22—C21	1.415 (3)	C4—H4	0.9300
C27—C28	1.395 (3)	C15—C16	1.357 (3)
C27—C32	1.411 (3)	C15—H15	0.9300
C27—C26	1.432 (3)	C21—C20	1.360 (3)
C32—C33	1.409 (3)	C21—H21	0.9300
C32—C31	1.421 (3)	C16—H16	0.9300
C34—C33	1.357 (3)	C28—C29	1.349 (3)
C34—H34	0.9300	C28—H28	0.9300
C26—H26	0.9300	C30—C29	1.398 (3)
C23—H23	0.9300	C30—H30	0.9300
C24—H24B	0.98 (2)	C29—H29	0.9300
C24—H24A	0.95 (2)	C18—C19	1.348 (3)
C6—C5	1.378 (3)	C18—H18	0.9300
C6—H6	0.9300	C20—C19	1.393 (4)
C33—H33	0.9300	C20—H20	0.9300
C8—C9	1.375 (3)	C19—H19	0.9300

C1—Si—C7	109.26 (8)	C16—C17—C18	122.4 (2)
C1—Si—C24	111.99 (10)	C16—C17—C22	118.1 (2)
C7—Si—C24	111.63 (10)	C18—C17—C22	119.5 (2)
C1—Si—C13	108.42 (9)	C10—C11—C12	120.6 (2)
C7—Si—C13	109.40 (9)	C10—C11—H11	119.7
C24—Si—C13	106.01 (11)	C12—C11—H11	119.7
C6—C1—C2	115.99 (18)	C14—C13—Si	115.41 (14)
C6—C1—Si	122.70 (15)	C14—C13—H13A	111.2 (13)
C2—C1—Si	121.28 (14)	Si—C13—H13A	104.7 (12)
C8—C7—C12	116.43 (17)	C14—C13—H13B	111.9 (14)
C8—C7—Si	121.88 (15)	Si—C13—H13B	105.3 (14)
C12—C7—Si	121.67 (14)	H13A—C13—H13B	107.8 (18)
C23—C14—C15	117.76 (19)	C4—C5—C6	120.4 (2)
C23—C14—C13	122.66 (19)	C4—C5—H5	119.8
C15—C14—C13	119.57 (19)	C6—C5—H5	119.8
C26—C25—C34	118.44 (18)	C8—C9—C10	120.23 (19)
C26—C25—C24	121.77 (19)	C8—C9—H9	119.9
C34—C25—C24	119.78 (18)	C10—C9—H9	119.9
C11—C12—C7	121.53 (18)	C30—C31—C32	120.4 (2)
C11—C12—H12	119.2	C30—C31—H31	119.8
C7—C12—H12	119.2	C32—C31—H31	119.8
C17—C22—C23	119.21 (19)	C11—C10—C9	119.1 (2)
C17—C22—C21	118.3 (2)	C11—C10—H10	120.4
C23—C22—C21	122.5 (2)	C9—C10—H10	120.4
C28—C27—C32	119.16 (19)	C4—C3—C2	120.5 (2)
C28—C27—C26	122.86 (19)	C4—C3—H3	119.7
C32—C27—C26	117.98 (17)	C2—C3—H3	119.7
C33—C32—C27	118.82 (18)	C5—C4—C3	119.1 (2)
C33—C32—C31	122.68 (19)	C5—C4—H4	120.4
C27—C32—C31	118.49 (18)	C3—C4—H4	120.4
C33—C34—C25	121.15 (18)	C16—C15—C14	121.7 (2)
C33—C34—H34	119.4	C16—C15—H15	119.2
C25—C34—H34	119.4	C14—C15—H15	119.2
C25—C26—C27	122.31 (18)	C20—C21—C22	120.2 (2)
C25—C26—H26	118.8	C20—C21—H21	119.9
C27—C26—H26	118.8	C22—C21—H21	119.9
C14—C23—C22	121.84 (19)	C15—C16—C17	121.3 (2)
C14—C23—H23	119.1	C15—C16—H16	119.3
C22—C23—H23	119.1	C17—C16—H16	119.3
C25—C24—Si	118.49 (15)	C29—C28—C27	121.2 (2)
C25—C24—H24B	108.9 (13)	C29—C28—H28	119.4
Si—C24—H24B	106.1 (13)	C27—C28—H28	119.4
C25—C24—H24A	109.2 (13)	C31—C30—C29	120.1 (2)
Si—C24—H24A	104.8 (13)	C31—C30—H30	119.9
H24B—C24—H24A	109.1 (18)	C29—C30—H30	119.9
C5—C6—C1	122.0 (2)	C28—C29—C30	120.6 (2)
C5—C6—H6	119.0	C28—C29—H29	119.7
C1—C6—H6	119.0	C30—C29—H29	119.7
C34—C33—C32	121.29 (19)	C19—C18—C17	120.7 (2)
C34—C33—H33	119.4	C19—C18—H18	119.6
C32—C33—H33	119.4	C17—C18—H18	119.6
C9—C8—C7	122.04 (19)	C21—C20—C19	121.1 (2)
C9—C8—H8	119.0	C21—C20—H20	119.4
C7—C8—H8	119.0	C19—C20—H20	119.4
C3—C2—C1	121.88 (19)	C18—C19—C20	120.2 (3)
C3—C2—H2	119.1	C18—C19—H19	119.9
C1—C2—H2	119.1	C20—C19—H19	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.66	3.569 (2)	166
C5—H5···Cg2ⁱⁱ	0.93	2.88	3.664 (2)	143
C9—H9···Cg3ⁱⁱⁱ	0.93	2.76	3.577 (2)	148

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₈Si
M_r	464.65
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.4884 (14), 11.0673 (13), 13.3450 (15)
α, β, γ (°)	75.820 (9), 83.767 (11), 70.575 (11)
V (Å³)	1280.8 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.36 × 0.20 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Analytical (see. N.W. Alcock (1970))
T_min, T_max	0.814, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	9101, 4618, 3060
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.01
No. of reflections	4618
No. of parameters	333
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.66	3.569 (2)	166
C5—H5···Cg2ⁱⁱ	0.93	2.88	3.664 (2)	143
C9—H9···Cg3ⁱⁱⁱ	0.93	2.76	3.577 (2)	148

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Acknowledgements

This work was supported in part by funds provided by the University of North Carolina at Charlotte. Support for REU participant TBM was provided by the National Science Foundation, award number CHE-0851797.

References

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