(Butane-1,3-diyne-1,4-diyl)bis­(tri­isopropyl­silane)

Raza Shah, M.; Ng, S.W.

doi:10.1107/S160053681002725X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2028

https://doi.org/10.1107/S160053681002725X

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(Butane-1,3-diyne-1,4-diyl)bis(triisopropylsilane)

Muhammad Raza Shah ^a and Seik Weng Ng ^b ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 July 2010; accepted 9 July 2010; online 17 July 2010)

The molecule of the title compound, C₂₂H₄₂Si₂, lies on a center of inversion, and the triisopropylsilyl groups are staggered.

Related literature

For the crystal structures of the trimethyl and tris-tert-butyl analogs, see: Bruckmann & Krüger (1997 ); Vitze et al. (2009 ).

Experimental

Crystal data

C₂₂H₄₂Si₂
M_r = 362.74
Triclinic, $[P \overline 1]$
a = 7.1213 (10) Å
b = 7.9057 (11) Å
c = 10.6937 (14) Å
α = 89.139 (2)°
β = 81.823 (2)°
γ = 79.449 (2)°
V = 585.81 (14) Å³
Z = 1
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.941, T_max = 0.985
5560 measured reflections
2674 independent reflections
2190 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.06
2674 reflections
115 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681002725X/jh2179sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002725X/jh2179Isup2.hkl

checkCIF report

Comment top

The compound (Scheme I) was obtained in an unsuccessful attempt at the Sonogoshira coupling of 2,9-dichloro-1,10-phenanthroline with trisisopropylsilylacetylene. The carbon–carbon triple-bond is 1.210 (2) Å long; the distance is indistinguisahble from that [1.208 (3) Å] for bis(trimethylsilyl)acetylene (Bruckmann & Krüger, 1997) as well as that [1.22 (2) Å] found in the t-butyl analog (Vitze et al. (2009). The molecule lies on a center of inversion, and the trisisopropylsilyl groups are staggered (Fig. 1).

Related literature top

For the crystal structures of the trimethyl and tris-tert-butyl analogs, see: Bruckmann & Krüger (1997); Vitze et al. (2009).

Experimental top

Copper(I) iodide (70 mg, 0.36 mmol) and dichlorobis(triphenylphosphine)palladium (10 mg, 0.014 mmol) were added to a pyridine solution (10 ml) of triisopropylsilylacetylene (440 mg, 2.4 mmol) and 2,9-dichloro-1,10-phenanthroline (200 mg, 0.8 mmol). The solution was stirred for 4 h. The pyridine was removed under vacuum and the residue dissolved in dichloromethane (10 ml). The solution was washed with 2 N hydrochloric acid (10 ml). The solvent was evaporated and the solid recrystallized from dichloromethane to afford colorless crystals.

Structure description top

For the crystal structures of the trimethyl and tris-tert-butyl analogs, see: Bruckmann & Krüger (1997); Vitze et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2009); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₄H₄₂Si₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(Butane-1,3-diyne-1,4-diyl)bis(triisopropylsilane) top

Crystal data top

C₂₂H₄₂Si₂	Z = 1
M_r = 362.74	F(000) = 202
Triclinic, P1	D_x = 1.028 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1213 (10) Å	Cell parameters from 1787 reflections
b = 7.9057 (11) Å	θ = 2.6–27.7°
c = 10.6937 (14) Å	µ = 0.15 mm⁻¹
α = 89.139 (2)°	T = 100 K
β = 81.823 (2)°	Prism, colorless
γ = 79.449 (2)°	0.40 × 0.10 × 0.10 mm
V = 585.81 (14) Å³

Data collection top

Bruker SMART APEX diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	2190 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.941, T_max = 0.985	k = −10→10
5560 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0577P)² + 0.057P] where P = (F_o² + 2F_c²)/3
2674 reflections	(Δ/σ)_max = 0.001
115 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₂H₄₂Si₂	γ = 79.449 (2)°
M_r = 362.74	V = 585.81 (14) Å³
Triclinic, P1	Z = 1
a = 7.1213 (10) Å	Mo Kα radiation
b = 7.9057 (11) Å	µ = 0.15 mm⁻¹
c = 10.6937 (14) Å	T = 100 K
α = 89.139 (2)°	0.40 × 0.10 × 0.10 mm
β = 81.823 (2)°

Data collection top

Bruker SMART APEX diffractometer	2674 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2190 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.985	R_int = 0.036
5560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
2674 reflections	Δρ_min = −0.34 e Å⁻³
115 parameters

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

	x	y	z	U_iso*/U_eq
Si1	0.75095 (6)	0.77829 (5)	0.27093 (4)	0.01479 (15)
C1	0.7369 (2)	0.7104 (2)	0.10482 (15)	0.0195 (4)
H1	0.7950	0.5852	0.0980	0.023*
C2	0.5337 (3)	0.7257 (2)	0.07088 (18)	0.0295 (4)
H2A	0.5401	0.6716	−0.0118	0.044*
H2B	0.4745	0.8475	0.0677	0.044*
H2C	0.4559	0.6679	0.1349	0.044*
C3	0.8628 (3)	0.8009 (2)	0.00649 (16)	0.0269 (4)
H3A	0.8642	0.7528	−0.0776	0.040*
H3B	0.9947	0.7831	0.0271	0.040*
H3C	0.8096	0.9244	0.0074	0.040*
C4	0.6408 (2)	1.0072 (2)	0.31850 (16)	0.0185 (4)
H4	0.6446	1.0147	0.4113	0.022*
C5	0.4277 (3)	1.0599 (2)	0.30187 (18)	0.0264 (4)
H5A	0.3746	1.1712	0.3438	0.040*
H5B	0.3558	0.9728	0.3395	0.040*
H5C	0.4165	1.0693	0.2116	0.040*
C6	0.7578 (3)	1.1395 (2)	0.25767 (18)	0.0282 (4)
H6A	0.7061	1.2526	0.2972	0.042*
H6B	0.7489	1.1459	0.1671	0.042*
H6C	0.8932	1.1044	0.2699	0.042*
C7	1.0093 (2)	0.7272 (2)	0.30172 (16)	0.0178 (4)
H7	1.0807	0.8091	0.2514	0.021*
C8	1.0237 (3)	0.7550 (2)	0.44066 (17)	0.0233 (4)
H8A	1.1598	0.7363	0.4527	0.035*
H8B	0.9585	0.6737	0.4923	0.035*
H8C	0.9620	0.8730	0.4662	0.035*
C9	1.1074 (2)	0.5444 (2)	0.25796 (17)	0.0233 (4)
H9A	1.2368	0.5190	0.2827	0.035*
H9B	1.1173	0.5358	0.1658	0.035*
H9C	1.0307	0.4617	0.2973	0.035*
C10	0.6199 (2)	0.64130 (19)	0.37986 (15)	0.0161 (3)
C11	0.5440 (2)	0.55159 (19)	0.45656 (14)	0.0152 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0163 (3)	0.0141 (2)	0.0141 (3)	−0.00465 (17)	−0.00050 (17)	0.00352 (16)
C1	0.0248 (9)	0.0177 (8)	0.0167 (9)	−0.0068 (7)	−0.0015 (7)	0.0022 (6)
C2	0.0319 (11)	0.0371 (11)	0.0229 (10)	−0.0123 (9)	−0.0080 (8)	0.0002 (8)
C3	0.0355 (11)	0.0301 (10)	0.0170 (9)	−0.0146 (8)	0.0009 (8)	0.0004 (7)
C4	0.0228 (9)	0.0173 (8)	0.0146 (8)	−0.0041 (7)	0.0006 (7)	0.0028 (6)
C5	0.0269 (10)	0.0230 (9)	0.0266 (10)	0.0029 (7)	−0.0043 (8)	0.0015 (7)
C6	0.0361 (11)	0.0163 (8)	0.0302 (11)	−0.0070 (8)	0.0051 (9)	0.0005 (7)
C7	0.0171 (8)	0.0166 (8)	0.0200 (9)	−0.0055 (6)	−0.0010 (7)	0.0022 (6)
C8	0.0192 (9)	0.0254 (9)	0.0263 (10)	−0.0034 (7)	−0.0077 (7)	0.0010 (7)
C9	0.0198 (9)	0.0215 (9)	0.0273 (10)	−0.0009 (7)	−0.0029 (7)	0.0016 (7)
C10	0.0159 (8)	0.0150 (7)	0.0174 (9)	−0.0017 (6)	−0.0041 (7)	0.0021 (6)
C11	0.0148 (8)	0.0142 (7)	0.0168 (9)	−0.0010 (6)	−0.0049 (7)	0.0001 (6)

Geometric parameters (Å, º) top

Si1—C10	1.8504 (16)	C5—H5B	0.9800
Si1—C4	1.8822 (17)	C5—H5C	0.9800
Si1—C1	1.8848 (17)	C6—H6A	0.9800
Si1—C7	1.8849 (17)	C6—H6B	0.9800
C1—C2	1.524 (2)	C6—H6C	0.9800
C1—C3	1.538 (2)	C7—C8	1.526 (2)
C1—H1	1.0000	C7—C9	1.533 (2)
C2—H2A	0.9800	C7—H7	1.0000
C2—H2B	0.9800	C8—H8A	0.9800
C2—H2C	0.9800	C8—H8B	0.9800
C3—H3A	0.9800	C8—H8C	0.9800
C3—H3B	0.9800	C9—H9A	0.9800
C3—H3C	0.9800	C9—H9B	0.9800
C4—C5	1.533 (2)	C9—H9C	0.9800
C4—C6	1.535 (2)	C10—C11	1.210 (2)
C4—H4	1.0000	C11—C11ⁱ	1.385 (3)
C5—H5A	0.9800

C10—Si1—C4	106.04 (7)	C4—C5—H5B	109.5
C10—Si1—C1	107.42 (7)	H5A—C5—H5B	109.5
C4—Si1—C1	117.06 (8)	C4—C5—H5C	109.5
C10—Si1—C7	105.69 (7)	H5A—C5—H5C	109.5
C4—Si1—C7	110.41 (7)	H5B—C5—H5C	109.5
C1—Si1—C7	109.52 (8)	C4—C6—H6A	109.5
C2—C1—C3	110.85 (14)	C4—C6—H6B	109.5
C2—C1—Si1	115.47 (12)	H6A—C6—H6B	109.5
C3—C1—Si1	111.67 (11)	C4—C6—H6C	109.5
C2—C1—H1	106.0	H6A—C6—H6C	109.5
C3—C1—H1	106.0	H6B—C6—H6C	109.5
Si1—C1—H1	106.0	C8—C7—C9	110.89 (14)
C1—C2—H2A	109.5	C8—C7—Si1	111.21 (11)
C1—C2—H2B	109.5	C9—C7—Si1	111.98 (11)
H2A—C2—H2B	109.5	C8—C7—H7	107.5
C1—C2—H2C	109.5	C9—C7—H7	107.5
H2A—C2—H2C	109.5	Si1—C7—H7	107.5
H2B—C2—H2C	109.5	C7—C8—H8A	109.5
C1—C3—H3A	109.5	C7—C8—H8B	109.5
C1—C3—H3B	109.5	H8A—C8—H8B	109.5
H3A—C3—H3B	109.5	C7—C8—H8C	109.5
C1—C3—H3C	109.5	H8A—C8—H8C	109.5
H3A—C3—H3C	109.5	H8B—C8—H8C	109.5
H3B—C3—H3C	109.5	C7—C9—H9A	109.5
C5—C4—C6	110.60 (14)	C7—C9—H9B	109.5
C5—C4—Si1	114.57 (11)	H9A—C9—H9B	109.5
C6—C4—Si1	113.60 (11)	C7—C9—H9C	109.5
C5—C4—H4	105.7	H9A—C9—H9C	109.5
C6—C4—H4	105.7	H9B—C9—H9C	109.5
Si1—C4—H4	105.7	C11—C10—Si1	175.41 (14)
C4—C5—H5A	109.5	C10—C11—C11ⁱ	179.4 (2)

C10—Si1—C1—C2	59.25 (14)	C1—Si1—C4—C6	−72.44 (15)
C4—Si1—C1—C2	−59.79 (14)	C7—Si1—C4—C6	53.75 (15)
C7—Si1—C1—C2	173.58 (12)	C10—Si1—C7—C8	−56.07 (12)
C10—Si1—C1—C3	−172.91 (12)	C4—Si1—C7—C8	58.19 (13)
C4—Si1—C1—C3	68.05 (14)	C1—Si1—C7—C8	−171.50 (11)
C7—Si1—C1—C3	−58.59 (14)	C10—Si1—C7—C9	68.62 (13)
C10—Si1—C4—C5	−63.77 (14)	C4—Si1—C7—C9	−177.12 (11)
C1—Si1—C4—C5	56.00 (14)	C1—Si1—C7—C9	−46.81 (13)
C7—Si1—C4—C5	−177.80 (12)	C1—Si1—C10—C11	142.3 (18)
C10—Si1—C4—C6	167.78 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₄₂Si₂
M_r	362.74
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.1213 (10), 7.9057 (11), 10.6937 (14)
α, β, γ (°)	89.139 (2), 81.823 (2), 79.449 (2)
V (Å³)	585.81 (14)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.941, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5560, 2674, 2190
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.06
No. of reflections	2674
No. of parameters	115
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

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