Literature DB >> 21588764

Tetra-kis(4-tert-butyl-benz-yl)silane.

Lauren E Burnham¹, Rulla M Kachlan, Andy A Thomas, Craig A Ogle, Daniel S Jones.

Abstract

The title compound, C(44)H(60)Si, was prepared as an inter-nal standard for diffusion-ordered NMR spectroscopy. The Si atom lies on a special position with site symmetry.

Entities: Chemical Disease Gene Species

Year: 2010 PMID： 21588764 PMCID： PMC3007930 DOI： 10.1107/S1600536810034173

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

Related literature

For applications of the title compound in NMR spectroscopy, see: Li et al. (2009 ▶). For similar structures in the same space group, see: Liao et al. (2002 ▶); Laliberté et al. (2004 ▶). For a previously reported NMR standard, see: Monroe et al. (2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C44H60Si M = 617.01 Tetragonal, a = 17.394 (2) Å c = 6.3613 (6) Å V = 1924.7 (4) Å3 Z = 2 Cu Kα radiation μ = 0.72 mm−1 T = 295 K 0.31 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer 5204 measured reflections 1738 independent reflections 1056 reflections with I > 2σ(I) R int = 0.036 3 standard reflections every 113 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.135 S = 1.02 1738 reflections 106 parameters H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.11 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034173/su2206sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034173/su2206Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₄₄H₆₀Si	D_x = 1.065 Mg m⁻³
M_r = 617.01	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P4₂/n	Cell parameters from 25 reflections
Hall symbol: -P 4bc	θ = 7.8–35.3°
a = 17.394 (2) Å	µ = 0.72 mm⁻¹
c = 6.3613 (6) Å	T = 295 K
V = 1924.7 (4) Å³	Prism, colorless
Z = 2	0.31 × 0.15 × 0.12 mm
F(000) = 676

Enraf–Nonius CAD-4 diffractometer	θ_max = 67.4°, θ_min = 3.6°
non–profiled ω/2θ scans	h = −20→20
5204 measured reflections	k = −20→15
1738 independent reflections	l = −7→0
1056 reflections with I > 2σ(I)	3 standard reflections every 113 reflections
R_int = 0.036	intensity decay: 2%

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0761P)² + 0.1124P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.135	Δρ_max = 0.13 e Å⁻³
S = 1.02	Δρ_min = −0.11 e Å⁻³
1738 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
106 parameters	Extinction coefficient: 0.0033 (6)
0 restraints

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.

	x	y	z	U_iso*/U_eq
Si	0.25	0.25	0.25	0.0599 (4)
C4	0.50538 (12)	0.30509 (12)	0.4293 (4)	0.0780 (7)
H4	0.5263	0.2856	0.5529	0.094*
C1	0.33661 (10)	0.25820 (11)	0.0742 (4)	0.0674 (7)
H1A	0.3507	0.2069	0.0288	0.081*
H1B	0.3217	0.2868	−0.0502	0.081*
C5	0.54015 (10)	0.36783 (10)	0.3360 (3)	0.0535 (5)
C7	0.44050 (11)	0.35854 (12)	0.0714 (4)	0.0668 (6)
H7	0.4193	0.3779	−0.0519	0.08*
C8	0.61357 (11)	0.40291 (11)	0.4257 (4)	0.0624 (6)
C2	0.40700 (10)	0.29575 (10)	0.1652 (4)	0.0580 (5)
C6	0.50509 (12)	0.39375 (12)	0.1556 (4)	0.0674 (6)
H6	0.5255	0.4365	0.0876	0.081*
C3	0.44105 (12)	0.27021 (12)	0.3468 (4)	0.0837 (8)
H3	0.42	0.2281	0.4163	0.1*
C9	0.62982 (15)	0.48273 (14)	0.3328 (5)	0.0951 (9)
H9A	0.634	0.4789	0.1827	0.143*
H9B	0.6771	0.5023	0.3896	0.143*
H9C	0.5885	0.517	0.3682	0.143*
C10	0.68066 (12)	0.35026 (15)	0.3687 (5)	0.0992 (9)
H10A	0.672	0.3001	0.4269	0.149*
H10B	0.7275	0.3711	0.4249	0.149*
H10C	0.6848	0.3465	0.2186	0.149*
C11	0.60896 (17)	0.41111 (18)	0.6619 (5)	0.1047 (9)
H11A	0.5674	0.445	0.6977	0.157*
H11B	0.6564	0.432	0.714	0.157*
H11C	0.6002	0.3616	0.7241	0.157*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0473 (4)	0.0473 (4)	0.0852 (9)	0	0	0
C4	0.0612 (12)	0.0722 (13)	0.101 (2)	−0.0089 (11)	−0.0143 (12)	0.0413 (13)
C1	0.0543 (11)	0.0616 (11)	0.0863 (18)	0.0010 (9)	0.0016 (11)	0.0004 (11)
C5	0.0496 (10)	0.0501 (10)	0.0609 (12)	0.0033 (8)	0.0116 (10)	0.0070 (9)
C7	0.0658 (12)	0.0750 (13)	0.0596 (15)	−0.0063 (10)	0.0042 (10)	0.0141 (11)
C8	0.0584 (11)	0.0644 (12)	0.0645 (15)	−0.0057 (9)	0.0067 (10)	0.0059 (10)
C2	0.0477 (10)	0.0504 (10)	0.0759 (14)	0.0042 (8)	0.0086 (10)	0.0056 (10)
C6	0.0688 (12)	0.0698 (13)	0.0638 (14)	−0.0169 (10)	0.0105 (12)	0.0169 (11)
C3	0.0617 (12)	0.0677 (13)	0.122 (2)	−0.0127 (10)	−0.0093 (14)	0.0472 (14)
C9	0.0946 (17)	0.0790 (15)	0.112 (2)	−0.0315 (13)	−0.0090 (16)	0.0155 (15)
C10	0.0538 (12)	0.111 (2)	0.133 (3)	0.0025 (13)	0.0030 (14)	−0.0136 (19)
C11	0.118 (2)	0.120 (2)	0.0760 (19)	−0.0328 (17)	0.0054 (17)	−0.0061 (17)

Si—C1ⁱ	1.882 (2)	C8—C11	1.512 (3)
Si—C1ⁱⁱ	1.882 (2)	C8—C10	1.527 (3)
Si—C1ⁱⁱⁱ	1.882 (2)	C8—C9	1.535 (3)
Si—C1	1.882 (2)	C2—C3	1.372 (3)
C4—C3	1.377 (3)	C6—H6	0.93
C4—C5	1.382 (3)	C3—H3	0.93
C4—H4	0.93	C9—H9A	0.96
C1—C2	1.504 (3)	C9—H9B	0.96
C1—H1A	0.97	C9—H9C	0.96
C1—H1B	0.97	C10—H10A	0.96
C5—C6	1.375 (3)	C10—H10B	0.96
C5—C8	1.526 (3)	C10—H10C	0.96
C7—C2	1.374 (3)	C11—H11A	0.96
C7—C6	1.387 (3)	C11—H11B	0.96
C7—H7	0.93	C11—H11C	0.96

C1ⁱ—Si—C1ⁱⁱ	110.68 (7)	C3—C2—C7	116.09 (19)
C1ⁱ—Si—C1ⁱⁱⁱ	107.08 (14)	C3—C2—C1	122.34 (18)
C1ⁱⁱ—Si—C1ⁱⁱⁱ	110.68 (7)	C7—C2—C1	121.6 (2)
C1ⁱ—Si—C1	110.68 (7)	C5—C6—C7	122.44 (19)
C1ⁱⁱ—Si—C1	107.08 (14)	C5—C6—H6	118.8
C1ⁱⁱⁱ—Si—C1	110.68 (7)	C7—C6—H6	118.8
C3—C4—C5	122.7 (2)	C2—C3—C4	121.94 (19)
C3—C4—H4	118.7	C2—C3—H3	119
C5—C4—H4	118.7	C4—C3—H3	119
C2—C1—Si	117.14 (16)	C8—C9—H9A	109.5
C2—C1—H1A	108	C8—C9—H9B	109.5
Si—C1—H1A	108	H9A—C9—H9B	109.5
C2—C1—H1B	108	C8—C9—H9C	109.5
Si—C1—H1B	108	H9A—C9—H9C	109.5
H1A—C1—H1B	107.3	H9B—C9—H9C	109.5
C6—C5—C4	115.05 (19)	C8—C10—H10A	109.5
C6—C5—C8	123.50 (17)	C8—C10—H10B	109.5
C4—C5—C8	121.4 (2)	H10A—C10—H10B	109.5
C2—C7—C6	121.8 (2)	C8—C10—H10C	109.5
C2—C7—H7	119.1	H10A—C10—H10C	109.5
C6—C7—H7	119.1	H10B—C10—H10C	109.5
C11—C8—C5	111.41 (19)	C8—C11—H11A	109.5
C11—C8—C10	109.4 (2)	C8—C11—H11B	109.5
C5—C8—C10	108.13 (17)	H11A—C11—H11B	109.5
C11—C8—C9	107.9 (2)	C8—C11—H11C	109.5
C5—C8—C9	111.83 (18)	H11A—C11—H11C	109.5
C10—C8—C9	108.09 (19)	H11B—C11—H11C	109.5

5 in total

Tetra-kis(4-tert-butyl-benz-yl)silane.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. The Cambridge Structural Database: a quarter of a million crystal structures and rising.

2. A short history of SHELX.

3. Structure and exchange in silicon-linked tetraradicals.

4. Formula weight prediction by internal reference diffusion-ordered NMR spectroscopy (DOSY).

5. Bis(2-naphthyl-meth-yl)diphenyl-silane.