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

Glöcklhofer, F.; Fröhlich, J.; Stöger, B.; Weil, M.

doi:10.1107/S1600536814014251

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Volume 70| Part 8| August 2014| Pages 77-79

doi:10.1107/S1600536814014251

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

Florian Glöcklhofer,^a Johannes Fröhlich,^a Berthold Stöger ^b and Matthias Weil ^b ^*

^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°.

Keywords: Cyanohydrin; cyclohexa-2,5-diene; crystal structure.

CCDC reference: 1008752

1. Chemical context

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.

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). 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
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, π–π 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.

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 ) 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.

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 ). 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 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). 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
Reaction scheme to obtain the title compound.

6. Refinement

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

Table 1
Experimental details

Crystal data
Chemical formula	C₁₄H₂₂N₂O₂Si₂
M_r	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)
V (Å³)	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 )
T_min, T_max	0.94, 0.98
No. of measured, independent and observed [I > 3σ(I)] reflections	15160, 2487, 2123
R_int	0.024
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.20
Computer programs: APEX2 and SAINT-Plus (Bruker, 2013), SUPERFLIP (Palatinus & Chapuis, 2007 ), JANA2006 (Petříček, et al., 2014 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1008752

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536814014251/su0009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814014251/su0009Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814014251/su0009Isup3.cml

checkCIF report

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

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 U_iso(H) = 1.2U_eq(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

	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.
	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.
	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

C₁₄H₂₂N₂O₂Si₂	F(000) = 328
M_r = 306.5	D_x = 1.200 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7267 reflections
a = 8.0770 (5) Å	θ = 2.8–29.9°
b = 11.2234 (6) Å	µ = 0.21 mm⁻¹
c = 9.4377 (6) Å	T = 100 K
β = 97.7087 (19)°	Block, clear colourless
V = 847.81 (9) Å³	0.65 × 0.26 × 0.12 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	2487 independent reflections
Radiation source: X-ray tube	2123 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ–scans	θ_max = 30.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −11→11
T_min = 0.94, T_max = 0.98	k = −15→15
15160 measured reflections	l = −13→13

Refinement top

Refinement on F	44 constraints
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.042	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 2.38	(Δ/σ)_max = 0.023
2487 reflections	Δρ_max = 0.38 e Å⁻³
91 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

Crystal data top

C₁₄H₂₂N₂O₂Si₂	V = 847.81 (9) Å³
M_r = 306.5	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0770 (5) Å	µ = 0.21 mm⁻¹
b = 11.2234 (6) Å	T = 100 K
c = 9.4377 (6) Å	0.65 × 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)
T_min = 0.94, T_max = 0.98	R_int = 0.024
15160 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.042	H-atom parameters constrained
S = 2.38	Δρ_max = 0.38 e Å⁻³
2487 reflections	Δρ_min = −0.20 e Å⁻³
91 parameters

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

	x	y	z	U_iso*/U_eq
Si1	0.21973 (4)	0.48658 (3)	0.25729 (3)	0.01515 (9)
O1	0.34897 (9)	0.59176 (6)	0.20989 (8)	0.0151 (2)
N1	0.66734 (12)	0.77227 (8)	0.18067 (10)	0.0203 (3)
C1	0.47262 (12)	0.58514 (9)	0.11702 (10)	0.0118 (3)
C2	0.39530 (12)	0.59953 (9)	−0.03704 (10)	0.0130 (3)
C3	0.41937 (12)	0.52449 (9)	−0.14034 (11)	0.0125 (3)
C4	0.58275 (13)	0.69117 (9)	0.15441 (10)	0.0136 (3)
C5	0.04800 (15)	0.57505 (11)	0.31580 (13)	0.0244 (4)
C6	0.32433 (16)	0.39773 (11)	0.40911 (13)	0.0303 (4)
C7	0.14743 (14)	0.38628 (10)	0.10522 (12)	0.0208 (3)
H1c2	0.324479	0.667221	−0.061301	0.0155*
H1c3	0.365173	0.540694	−0.235238	0.015*
H1c5	−0.036613	0.522349	0.341718	0.0293*
H2c5	0.09082	0.622785	0.396915	0.0293*
H3c5	0.000656	0.625942	0.239152	0.0293*
H1c6	0.246714	0.341141	0.438738	0.0363*
H2c6	0.417964	0.356223	0.379805	0.0363*
H3c6	0.362472	0.449816	0.487404	0.0363*
H1c7	0.049234	0.344384	0.124438	0.0249*
H2c7	0.121741	0.432548	0.019545	0.0249*
H3c7	0.233911	0.330007	0.093019	0.0249*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.01621 (16)	0.01632 (17)	0.01325 (15)	−0.00379 (11)	0.00316 (11)	−0.00069 (11)
O1	0.0166 (4)	0.0138 (4)	0.0161 (4)	−0.0014 (3)	0.0071 (3)	−0.0023 (3)
N1	0.0220 (5)	0.0178 (5)	0.0210 (5)	−0.0034 (4)	0.0026 (4)	−0.0036 (4)
C1	0.0132 (4)	0.0106 (5)	0.0118 (4)	−0.0006 (3)	0.0026 (3)	−0.0006 (3)
C2	0.0126 (4)	0.0112 (5)	0.0147 (5)	0.0009 (4)	0.0001 (4)	0.0016 (4)
C3	0.0126 (5)	0.0121 (5)	0.0122 (4)	0.0000 (4)	−0.0005 (4)	0.0017 (4)
C4	0.0151 (5)	0.0143 (5)	0.0115 (4)	0.0018 (4)	0.0021 (3)	−0.0004 (4)
C5	0.0226 (6)	0.0291 (7)	0.0236 (6)	−0.0046 (5)	0.0102 (5)	−0.0070 (5)
C6	0.0327 (7)	0.0314 (7)	0.0249 (6)	−0.0108 (5)	−0.0029 (5)	0.0105 (5)
C7	0.0215 (6)	0.0219 (6)	0.0198 (5)	−0.0064 (4)	0.0058 (4)	−0.0038 (4)

Geometric parameters (Å, º) top

Si1—C5	1.8495 (13)	C3—H1c3	0.96
Si1—C6	1.8537 (13)	C5—H1c5	0.96
Si1—C7	1.8555 (11)	C5—H2c5	0.96
O1—C1	1.4163 (13)	C5—H3c5	0.96
N1—C4	1.1451 (14)	C6—H1c6	0.96
C1—C2	1.5121 (13)	C6—H2c6	0.96
C1—C3ⁱ	1.5073 (14)	C6—H3c6	0.96
C1—C4	1.4993 (14)	C7—H1c7	0.96
C2—C3	1.3224 (14)	C7—H2c7	0.96
C2—H1c2	0.96	C7—H3c7	0.96

C5—Si1—C6	109.89 (6)	Si1—C5—H2c5	109.47
C5—Si1—C7	112.70 (5)	Si1—C5—H3c5	109.47
C6—Si1—C7	109.57 (5)	H1c5—C5—H2c5	109.47
O1—C1—C2	110.79 (8)	H1c5—C5—H3c5	109.47
O1—C1—C3ⁱ	113.26 (8)	H2c5—C5—H3c5	109.47
O1—C1—C4	104.95 (8)	Si1—C6—H1c6	109.47
C2—C1—C3ⁱ	112.58 (8)	Si1—C6—H2c6	109.47
C2—C1—C4	107.28 (8)	Si1—C6—H3c6	109.47
C3ⁱ—C1—C4	107.46 (8)	H1c6—C6—H2c6	109.47
C1—C2—C3	123.94 (9)	H1c6—C6—H3c6	109.47
C1—C2—H1c2	118.03	H2c6—C6—H3c6	109.47
C3—C2—H1c2	118.03	Si1—C7—H1c7	109.47
C1ⁱ—C3—C2	123.48 (9)	Si1—C7—H2c7	109.47
C1ⁱ—C3—H1c3	118.26	Si1—C7—H3c7	109.47
C2—C3—H1c3	118.26	H1c7—C7—H2c7	109.47
N1—C4—C1	178.87 (11)	H1c7—C7—H3c7	109.47
Si1—C5—H1c5	109.47	H2c7—C7—H3c7	109.47

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₂N₂O₂Si₂
M_r	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)
V (Å³)	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 diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.94, 0.98
No. of measured, independent and observed [I > 3σ(I)] reflections	15160, 2487, 2123
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(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
Δρ_max, Δρ_min (e Å⁻³)	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

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2013). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Friedrich, 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
Jayamurugan, 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
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Pai, 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
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Petříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345–352. Google Scholar
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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

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

3. Supramolecular features