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Crystal structure of trans-1,4-bis­­[(tri­methyl­sil­yl)­­oxy]cyclo­hexa-2,5-diene-1,4-dicarbo­nitrile

aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
*Correspondence e-mail: mweil@mail.zserv.tuwien.ac.at

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 17 June 2014; accepted 17 June 2014; online 19 July 2014)

The asymmetric unit of the title compound, C14H22N2O2Si2, contains one half of the mol­ecule, which is completed by inversion symmetry. The cyclo­hexa-2,5-diene ring is exactly planar and reflects the bond-length distribution of a pair of located double bonds [1.3224 (14) Å] and two pairs of single bonds [1.5121 (13) and 1.5073 (14) Å]. The tetra­hedral angle between the sp3-C atom and the two neighbouring sp2-C atoms in the cyclo­hexa-2,5-diene ring is enlarged by about 3°.

1. Chemical context

Cyano­hydrins (Friedrich, 1983[Friedrich, K. (1983). The Chemistry of Functional Groups, Supplement C, Part 2, edited by S. Patai & Z. Rappoport, pp. 1345-1390, New York: Wiley.]) are an important class of organic compounds. Silylated cyano­hydrins are versatile precursor compounds in organic chemistry because the nitrile functional group can be modified by a variety of reactions such as hydrolysis, reduction or addition of organometallic reagents. The mol­ecular and crystal structure of the title compound, a new silylated cyclo­hexa-2,5-diene with trans nitrile groups in the 1,4 positions, is reported herein.

[Scheme 1]

2. Structural commentary

The mol­ecular structure of the title compound is centrosymmetric, leading to a trans-1,4-configuration of the oxy(tri­methyl­sil­yl) and carbo­nitrile groups (Fig. 1[link]). The cyclo­hexa-2,5-diene ring is exactly planar, but its angles differ from that of an ideal hexa­gon. Whereas the angle between the sp3-C atom (C1) and the neighbouring sp2-C atoms (C2, C3) is reduced to 112.58 (8)°, the other intra-ring angles are enlarged to 123.94 (9)° (C1—C2—C3) and 123.48 (9)° (C1i—C3—C2) [symmetry code: (i) −x + 1, −y + 1, −z]. The tetra­hedral angles around C1 are likewise distorted due to the ring strain. The angles involving the O atom of the oxy(tri­methyl­sil­yl) group and the ring C atoms are enlarged to 110.79 (8)° and 113.26 (8)° while the angle involving the O atom and the C atom of the carbo­nitrile group is reduced to 104.95 (8)°. The backbone of the 1,1-substituents is nearly perpendicular to the cyclo­hexa-2,5-diene ring, with a dihedral angle of 86.05 (7).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 80% probability level. Non-labelled atoms are generated by the symmetry code −x + 1, −y + 1, −z.

3. Supra­molecular features

Notable features in terms of non-classical hydrogen bonding inter­actions are not observed in the crystal structure of the title compound. As a result of the bulky tri­methyl­silyl groups, ππ stacking inter­actions between the rings are not possible. The packing of the mol­ecules (Fig. 2[link]) seems to be dominated mainly by van der Waals forces.

[Figure 2]
Figure 2
A view of the crystal packing of the title compound along [001]. Colour code: O red, C grey, N light-blue, Si off-white, H white.

4. Database survey

In the current Cambridge Structural Database (Version 5.35, last update February 2014; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) only one example of a cyclo­hexa-2,5-diene with trans nitrile groups in the 1,4 positions is listed, namely 3,5-bis­(4-(di­methyl­amino)­phen­yl)cyclo­hexa-2,5-diene-1,1,2,4,4-penta­carbo­nitrile (Jayamurugan et al., 2011[Jayamurugan, G., Gisselbrecht, J.-P., Boudon, C., Schoenebeck, F., Schweizer, W. B., Bernet, B. & Diederich, F. (2011). Chem. Commun. 47, 4510-4522.]). The C—C bond lengths within the cyclo­hexa-2,5-diene are very similar to those of the title compound.

5. Synthesis and crystallization

1,4-Bis[(tri­methyl­sil­yl)­oxy]cyclo­hexa-2,5-diene-1,4-dicarbonitrile was synthesized by a modified protocol reported by Onaka et al. (1989[Onaka, M., Higuchi, K., Sugita, K. & Izumi, Y. (1989). Chem. Lett. 18, 1393-1396.]). The required heterogeneous catalyst Fe-montmorillonite (K10-FeAA) was prepared according to Pai et al. (2000[Pai, S. G., Bajpai, A. R., Deshpande, A. B. & Samant, S. D. (2000). J. Mol. Catal. A Chem. 156, 233-243.]) and activated at 393 K and 5 mbar for 2 h prior to use.

1,4-Benzo­quinone (1.62 g, 15 mmol) was dissolved in 75 ml di­chloro­methane (0.2 M), purged with argon and cooled to 273 K. Tri­methyl­silyl cyanide (2.98 g, 30 mmol) and Fe-montmorillonite (0.75 g) were added sequentially and the mixture stirred for 1 h at 273 K under an argon atmosphere. The Fe-montmorillonite was filtered off (Por 4 glass filter) and the solvent was evaporated in vacuo to yield 4.23 g (13.8 mmol, 92%) of a cis/trans (3/1) isomeric mixture of 1,4-bis­[(tri­methyl­sil­yl)­oxy]cyclo­hexa-2,5-diene-1,4-dicarbo­nitrile (Fig. 3[link]). Crystallization from n-hexane selectively yielded white crystals of the trans-isomer, which were suitable for single-crystal X-ray diffraction analysis. 1H NMR (CDCl3, 200 MHz): δ = 6.19 (s, 4H), 0.23 (s, 18H) p.p.m.; 13C NMR (CDCl3, 50 MHz): δ = 238.3 (s), 129.4 (d), 1.5 (q) p.p.m.

[Figure 3]
Figure 3
Reaction scheme to obtain the title compound.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The H atoms were included in calculated positions (C—H = 0.96 Å) and treated as riding atoms with Uiso(H) = 1.2Ueq(C).

Table 1
Experimental details

Crystal data
Chemical formula C14H22N2O2Si2
Mr 306.5
Crystal system, space group Monoclinic, P21/n
Temperature (K) 100
a, b, c (Å) 8.0770 (5), 11.2234 (6), 9.4377 (6)
β (°) 97.7087 (19)
V3) 847.81 (9)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.21
Crystal size (mm) 0.65 × 0.26 × 0.12
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.94, 0.98
No. of measured, independent and observed [I > 3σ(I)] reflections 15160, 2487, 2123
Rint 0.024
(sin θ/λ)max−1) 0.705
 
Refinement
R[F2 > 3σ(F2)], wR(F2), S 0.030, 0.042, 2.38
No. of reflections 2487
No. of parameters 91
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.38, −0.20
Computer programs: APEX2 and SAINT-Plus (Bruker, 2013[Bruker (2013). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]), JANA2006 (Petříček, et al., 2014[Petříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345-352.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Chemical context top

Cyano­hydrins (Friedrich, 1983) are an important class of organic compounds. Silylated cyano­hydrins are versatile precursor compounds in organic chemistry because the nitrile functional group can be modified by a variety of reactions such as hydrolysis, reduction or addition of organometallic reagents. The molecular and crystal structure of the title compound, a new silylated cyclo­hexa-2,5-diene with trans nitrile groups in the 1,4 positions, is reported herein.

Structural commentary top

The molecular structure of the title compound is centrosymmetric, leading to a trans-1,4-configuration of the oxy(tri­methyl­silyl) and carbo­nitrile groups (Fig. 1). The cyclo­hexa-2,5-diene ring is exactly planar, but its angles differ from that of an ideal hexagon. Whereas the angle between the sp3-C atom (C1) and the neighbouring sp2-C atoms (C2, C3) is reduced to 112.58 (8)°, the other intra-ring angles are enlarged to 123.94 (9)° (C1—C2—C3) and 123.48 (9)° (C1i—C3—C2) [(i) -x+1, -y+1, -z]. The tetra­hedral angles around C1 are likewise distorted due to the ring strain. The angles involving the O atom of the oxy(tri­methyl­silyl) group and the ring C atoms are enlarged to 110.79 (8)° and 113.26 (8)° while the angle involving the O atom and the C atom of the carbo­nitrile group is reduced to 104.95 (8)°. The backbone of the 1,1-substituents is nearly perpendicular to the cyclo­hexa-2,5-diene ring, with a dihedral angle of 86.05 (7) between the mean plane of the Si1—O1—C1—C4—N1 entity and that of the ring.

Supra­molecular features top

Notable features in terms of non-classical hydrogen bonding inter­actions are not observed in the crystal structure of the title compound. As a result of the bulky tri­methyl­silyl groups, ππ stacking inter­actions between the rings are not possible. The packing of the molecules (Fig. 2) seems to be dominated mainly by van der Waals forces.

Database survey top

In the current Cambridge Structural Database (Version 5.35, last update February 2014; Allen, 2002) only one example of a cyclo­hexa-2,5-diene with trans nitrile groups in the 1,4 positions is listed, namely 3,5-bis­(4-(di­methyl­amino)­phenyl)­cyclo­hexa-2,5-diene-1,1,2,4,4-penta­carbo­nitrile (Jayamurugan et al., 2011). The C—C bond lengths within the cyclo­hexa-2,5-diene are very similar to those of the title compound.

Synthesis and crystallization top

1,4-Bis[(tri­methyl­silyl)­oxy]cyclo­hexa-2,5-diene-1,4-dicarbo­nitrile was synthesized by a modified protocol reported by Onaka et al. (1989). The required heterogeneous catalyst Fe-montmorillonite (K10-FeAA) was prepared according to Pai et al. (2000) and activated at 393 K and 5 mbar for 2h prior to use.

1,4-Benzo­quinone (1.62 g, 15 mmol) was dissolved in 75 ml di­chloro­methane (0.2 M), purged with argon and cooled to 273 K. Tri­methyl­silyl cyanide (2.98 g, 30 mmol) and Fe-montmorillonite (0.75 g) were added sequentially and the mixture stirred for 1h at 273 K under an argon atmosphere. The Fe-montmorillonite was filtered off (Por 4 glass filter) and the solvent was evaporated in vacuo to yield 4.23 g (13.8 mmol, 92 %) of a cis/trans (3/1) isomeric mixture of 1,4-bis­[(tri­methyl­silyl)­oxy]cyclo­hexa-2,5-diene-1,4-dicarbo­nitrile (Fig. 3). Crystallization from n-hexane selectively yielded white crystals of the trans-isomer, which were suitable for single-crystal X-ray diffraction analysis. 1H NMR (CDCl3, 200 MHz): δ = 6.19 (s, 4H), 0.23 (s, 18H) p.p.m.; 13C NMR (CDCl3, 50 MHz): δ = 238.3 (s), 129.4 (d), 1.5 (q) p.p.m.

Refinement top

The H atoms were included in calculated positions (C—H = 0.96 Å) and treated as riding atoms with Uiso(H) = 1.2Ueq(C).

Related literature top

For related literature, see: Allen (2002); Friedrich (1983); Jayamurugan et al. (2011); Onaka et al. (1989); Pai et al. (2000).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus (Bruker, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček, et al., 2014); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 80% probability level. Non-labelled atoms are generated by the symmetry code -x + 1, -y + 1, -z.
[Figure 2] Fig. 2. A view of the crystal packing of the title compound along [001]. Colour code: O red, C grey, N light-blue, Si off-white, H white.
[Figure 3] Fig. 3. Reaction scheme to obtain the title compound.
trans-1,4-Bis[(trimethylsilyl)oxy]cyclohexa-2,5-diene-1,4-dicarbonitrile top
Crystal data top
C14H22N2O2Si2F(000) = 328
Mr = 306.5Dx = 1.200 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7267 reflections
a = 8.0770 (5) Åθ = 2.8–29.9°
b = 11.2234 (6) ŵ = 0.21 mm1
c = 9.4377 (6) ÅT = 100 K
β = 97.7087 (19)°Block, clear colourless
V = 847.81 (9) Å30.65 × 0.26 × 0.12 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2487 independent reflections
Radiation source: X-ray tube2123 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.024
ω and ϕ–scansθmax = 30.1°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
h = 1111
Tmin = 0.94, Tmax = 0.98k = 1515
15160 measured reflectionsl = 1313
Refinement top
Refinement on F44 constraints
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.042Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2)
S = 2.38(Δ/σ)max = 0.023
2487 reflectionsΔρmax = 0.38 e Å3
91 parametersΔρmin = 0.20 e Å3
0 restraints
Crystal data top
C14H22N2O2Si2V = 847.81 (9) Å3
Mr = 306.5Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.0770 (5) ŵ = 0.21 mm1
b = 11.2234 (6) ÅT = 100 K
c = 9.4377 (6) Å0.65 × 0.26 × 0.12 mm
β = 97.7087 (19)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2487 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
2123 reflections with I > 3σ(I)
Tmin = 0.94, Tmax = 0.98Rint = 0.024
15160 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.042H-atom parameters constrained
S = 2.38Δρmax = 0.38 e Å3
2487 reflectionsΔρmin = 0.20 e Å3
91 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.21973 (4)0.48658 (3)0.25729 (3)0.01515 (9)
O10.34897 (9)0.59176 (6)0.20989 (8)0.0151 (2)
N10.66734 (12)0.77227 (8)0.18067 (10)0.0203 (3)
C10.47262 (12)0.58514 (9)0.11702 (10)0.0118 (3)
C20.39530 (12)0.59953 (9)0.03704 (10)0.0130 (3)
C30.41937 (12)0.52449 (9)0.14034 (11)0.0125 (3)
C40.58275 (13)0.69117 (9)0.15441 (10)0.0136 (3)
C50.04800 (15)0.57505 (11)0.31580 (13)0.0244 (4)
C60.32433 (16)0.39773 (11)0.40911 (13)0.0303 (4)
C70.14743 (14)0.38628 (10)0.10522 (12)0.0208 (3)
H1c20.3244790.6672210.0613010.0155*
H1c30.3651730.5406940.2352380.015*
H1c50.0366130.5223490.3417180.0293*
H2c50.090820.6227850.3969150.0293*
H3c50.0006560.6259420.2391520.0293*
H1c60.2467140.3411410.4387380.0363*
H2c60.4179640.3562230.3798050.0363*
H3c60.3624720.4498160.4874040.0363*
H1c70.0492340.3443840.1244380.0249*
H2c70.1217410.4325480.0195450.0249*
H3c70.2339110.3300070.0930190.0249*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.01621 (16)0.01632 (17)0.01325 (15)0.00379 (11)0.00316 (11)0.00069 (11)
O10.0166 (4)0.0138 (4)0.0161 (4)0.0014 (3)0.0071 (3)0.0023 (3)
N10.0220 (5)0.0178 (5)0.0210 (5)0.0034 (4)0.0026 (4)0.0036 (4)
C10.0132 (4)0.0106 (5)0.0118 (4)0.0006 (3)0.0026 (3)0.0006 (3)
C20.0126 (4)0.0112 (5)0.0147 (5)0.0009 (4)0.0001 (4)0.0016 (4)
C30.0126 (5)0.0121 (5)0.0122 (4)0.0000 (4)0.0005 (4)0.0017 (4)
C40.0151 (5)0.0143 (5)0.0115 (4)0.0018 (4)0.0021 (3)0.0004 (4)
C50.0226 (6)0.0291 (7)0.0236 (6)0.0046 (5)0.0102 (5)0.0070 (5)
C60.0327 (7)0.0314 (7)0.0249 (6)0.0108 (5)0.0029 (5)0.0105 (5)
C70.0215 (6)0.0219 (6)0.0198 (5)0.0064 (4)0.0058 (4)0.0038 (4)
Geometric parameters (Å, º) top
Si1—C51.8495 (13)C3—H1c30.96
Si1—C61.8537 (13)C5—H1c50.96
Si1—C71.8555 (11)C5—H2c50.96
O1—C11.4163 (13)C5—H3c50.96
N1—C41.1451 (14)C6—H1c60.96
C1—C21.5121 (13)C6—H2c60.96
C1—C3i1.5073 (14)C6—H3c60.96
C1—C41.4993 (14)C7—H1c70.96
C2—C31.3224 (14)C7—H2c70.96
C2—H1c20.96C7—H3c70.96
C5—Si1—C6109.89 (6)Si1—C5—H2c5109.47
C5—Si1—C7112.70 (5)Si1—C5—H3c5109.47
C6—Si1—C7109.57 (5)H1c5—C5—H2c5109.47
O1—C1—C2110.79 (8)H1c5—C5—H3c5109.47
O1—C1—C3i113.26 (8)H2c5—C5—H3c5109.47
O1—C1—C4104.95 (8)Si1—C6—H1c6109.47
C2—C1—C3i112.58 (8)Si1—C6—H2c6109.47
C2—C1—C4107.28 (8)Si1—C6—H3c6109.47
C3i—C1—C4107.46 (8)H1c6—C6—H2c6109.47
C1—C2—C3123.94 (9)H1c6—C6—H3c6109.47
C1—C2—H1c2118.03H2c6—C6—H3c6109.47
C3—C2—H1c2118.03Si1—C7—H1c7109.47
C1i—C3—C2123.48 (9)Si1—C7—H2c7109.47
C1i—C3—H1c3118.26Si1—C7—H3c7109.47
C2—C3—H1c3118.26H1c7—C7—H2c7109.47
N1—C4—C1178.87 (11)H1c7—C7—H3c7109.47
Si1—C5—H1c5109.47H2c7—C7—H3c7109.47
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H22N2O2Si2
Mr306.5
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)8.0770 (5), 11.2234 (6), 9.4377 (6)
β (°) 97.7087 (19)
V3)847.81 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.65 × 0.26 × 0.12
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2013)
Tmin, Tmax0.94, 0.98
No. of measured, independent and
observed [I > 3σ(I)] reflections
15160, 2487, 2123
Rint0.024
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.042, 2.38
No. of reflections2487
No. of parameters91
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.20

Computer programs: APEX2 (Bruker, 2013), SAINT-Plus (Bruker, 2013), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček, et al., 2014), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

 

Acknowledgements

The X-ray centre of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBruker (2013). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFriedrich, K. (1983). The Chemistry of Functional Groups, Supplement C, Part 2, edited by S. Patai & Z. Rappoport, pp. 1345–1390, New York: Wiley.  Google Scholar
First citationJayamurugan, G., Gisselbrecht, J.-P., Boudon, C., Schoenebeck, F., Schweizer, W. B., Bernet, B. & Diederich, F. (2011). Chem. Commun. 47, 4510–4522.  Web of Science CSD CrossRef Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationOnaka, M., Higuchi, K., Sugita, K. & Izumi, Y. (1989). Chem. Lett. 18, 1393–1396.  CrossRef Web of Science Google Scholar
First citationPai, S. G., Bajpai, A. R., Deshpande, A. B. & Samant, S. D. (2000). J. Mol. Catal. A Chem. 156, 233–243.  Web of Science CrossRef CAS Google Scholar
First citationPalatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationPetříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345–352.  Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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