2-(Trimethyl­siloxy)adamantane-2-carbonitrile

Betz, R.; Klüfers, P.; Mayer, P.

doi:10.1107/S1600536808043559

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o207

doi:10.1107/S1600536808043559

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2-(Trimethylsiloxy)adamantane-2-carbonitrile

Richard Betz,^a Peter Klüfers ^a ^* and Peter Mayer ^a

^aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
^*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 7 November 2008; accepted 22 December 2008; online 24 December 2008)

In the crystal structure of the title compound, C₁₄H₂₃NOSi, cyclic dimeric units are established by two very weak hydrogen bonds of the type C—H⋯N with an H⋯N distance which is only slightly shorter than the sum of the van der Waals radii of 2.75 Å. The graph-set descriptor on the unitary level is R₂²(14) for the cyclic dimer.

Related literature

For a general synthesis of trimethylsilanyloxy-substituted cyanohydrines, see Evans et al. (1974 ). For the crystal structure of a related compound, see Hickmott et al. (1985 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₁₄H₂₃NOSi
M_r = 249.42
Triclinic, $[P \overline 1]$
a = 6.712 (2) Å
b = 9.440 (3) Å
c = 12.439 (2) Å
α = 106.19 (2)°
β = 102.35 (2)°
γ = 100.34 (3)°
V = 715.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 200 (2) K
0.38 × 0.34 × 0.18 mm

Data collection

Oxford Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, United Kingdom.]$ ) T_min = 0.91, T_max = 0.97
5687 measured reflections
2872 independent reflections
2097 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.06
2872 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Nⁱ	1.00	2.68	3.516 (3)	141
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, United Kingdom.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, United Kingdom.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043559/lh2736sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043559/lh2736Isup2.hkl

checkCIF report

Comment top

2-Trimethylsilanyloxy-adamantane-2-carbonitrile was prepared as an intermediate in the synthesis of (2-adamantyl)-glycolic acid.

In the crystal packing of the title compound, C₁₄H₂₃NOSi, dimeric units are established by two very weak hydrogen bonds of the type C–H···N with an H···N distance of 2.68 Å, which is only slightly shorter than the sum of the van-der-Waals radii of 2.75 Å (see Fig. 2).

The graph-set descriptor on the unitary level for the cyclic dimer is R²₂(14) (Etter et al., 1990; Bernstein et al., 1995).

The packing of the title compound is shown in Figure 3.

In the molecule the cyano group and the trimethylsilanyloxy group reside on the same C atom resembling a similar compound apparent in the literature (Hickmott et al., 1985). The methyl groups on the silicon atom adopt a nearly staggered conformation with respect to the substituents on the functionalized carbon atom. Bond lengths and angles in the carbocycle are in good agreement with the ones observed for other adamantane-derived compounds.

Related literature top

For a general synthesis of trimethylsilanyloxy-substituted cyanohydrines, see Evans et al. (1974). For the crystal structure of a related compound, see Hickmott et al. (1985). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

The title compound was prepared in adoption of a published procedure (Evans et al., 1974) upon Lewis-acid catalyzed addition of trimethylsilylcyanide to 2-adamantanone.

Crystals suitable for X-ray analysis were obtained directly from the crystallized reaction product obtained after distillation under reduced pressure.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. Intermolecular interactions in the crystal structure of the title compound, viewed approximately along [-1 0 0].
	Fig. 3. The packing of the title compound, viewed along [-1 0 0].

2-(Trimethylsiloxy)adamantane-2-carbonitrile top

Crystal data top

C₁₄H₂₃NOSi	Z = 2
M_r = 249.42	F(000) = 272
Triclinic, P1	D_x = 1.159 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.712 (2) Å	Cell parameters from 3060 reflections
b = 9.440 (3) Å	θ = 4.1–26.3°
c = 12.439 (2) Å	µ = 0.15 mm⁻¹
α = 106.19 (2)°	T = 200 K
β = 102.35 (2)°	Block, colourless
γ = 100.34 (3)°	0.38 × 0.34 × 0.18 mm
V = 715.0 (4) Å³

Data collection top

Oxford Xcalibur diffractometer	2872 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 26.3°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	h = −8→8
T_min = 0.91, T_max = 0.97	k = −11→8
5687 measured reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
2872 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₂₃NOSi	γ = 100.34 (3)°
M_r = 249.42	V = 715.0 (4) Å³
Triclinic, P1	Z = 2
a = 6.712 (2) Å	Mo Kα radiation
b = 9.440 (3) Å	µ = 0.15 mm⁻¹
c = 12.439 (2) Å	T = 200 K
α = 106.19 (2)°	0.38 × 0.34 × 0.18 mm
β = 102.35 (2)°

Data collection top

Oxford Xcalibur diffractometer	2872 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	2097 reflections with I > 2σ(I)
T_min = 0.91, T_max = 0.97	R_int = 0.019
5687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
2872 reflections	Δρ_min = −0.18 e Å⁻³
157 parameters

Special details top

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
Si	0.23305 (7)	0.50326 (5)	0.26051 (3)	0.03296 (15)
O	0.32961 (14)	0.66707 (11)	0.24268 (8)	0.0301 (3)
N	0.6710 (3)	0.7967 (2)	0.51049 (13)	0.0652 (5)
C1	0.6875 (2)	0.72644 (17)	0.22407 (13)	0.0330 (4)
H1	0.7090	0.6266	0.2304	0.040*
C2	0.5289 (2)	0.77526 (16)	0.29081 (12)	0.0284 (3)
C3	0.5002 (2)	0.93025 (16)	0.28158 (13)	0.0345 (4)
H3	0.3995	0.9644	0.3256	0.041*
C4	0.4126 (2)	0.91123 (17)	0.15282 (13)	0.0363 (4)
H41	0.2755	0.8337	0.1198	0.044*
H42	0.3888	1.0090	0.1454	0.044*
C5	0.5668 (3)	0.86187 (18)	0.08534 (14)	0.0407 (4)
H5	0.5084	0.8500	0.0014	0.049*
C6	0.5977 (3)	0.70911 (17)	0.09590 (13)	0.0380 (4)
H61	0.4608	0.6313	0.0629	0.046*
H62	0.6956	0.6746	0.0512	0.046*
C7	0.8992 (2)	0.8475 (2)	0.27499 (16)	0.0479 (4)
H71	0.9567	0.8602	0.3583	0.057*
H72	1.0016	0.8142	0.2332	0.057*
C8	0.7134 (3)	1.04922 (18)	0.33150 (16)	0.0516 (5)
H81	0.7719	1.0612	0.4146	0.062*
H82	0.6941	1.1490	0.3267	0.062*
C9	0.7790 (3)	0.9803 (2)	0.13533 (18)	0.0560 (5)
H91	0.8784	0.9473	0.0912	0.067*
H92	0.7608	1.0792	0.1279	0.067*
C10	0.8675 (3)	0.9988 (2)	0.26269 (17)	0.0536 (5)
H10	1.0058	1.0774	0.2954	0.064*
C11	0.6099 (2)	0.78913 (19)	0.41541 (14)	0.0416 (4)
C12	0.4270 (3)	0.38626 (19)	0.26501 (15)	0.0512 (5)
H121	0.4627	0.3606	0.1908	0.077*
H122	0.3660	0.2922	0.2781	0.077*
H123	0.5549	0.4441	0.3286	0.077*
C13	0.0044 (3)	0.40872 (19)	0.13013 (14)	0.0471 (4)
H131	−0.0928	0.4746	0.1273	0.071*
H132	−0.0687	0.3114	0.1341	0.071*
H133	0.0533	0.3901	0.0599	0.071*
C14	0.1455 (3)	0.5381 (2)	0.39525 (15)	0.0545 (5)
H141	0.2677	0.5922	0.4633	0.082*
H142	0.0794	0.4404	0.4014	0.082*
H143	0.0434	0.6002	0.3923	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0365 (3)	0.0333 (3)	0.0339 (3)	0.00931 (19)	0.01383 (19)	0.01512 (19)
O	0.0236 (5)	0.0318 (6)	0.0344 (6)	0.0042 (4)	0.0052 (4)	0.0141 (5)
N	0.0664 (11)	0.0837 (12)	0.0349 (9)	0.0152 (9)	−0.0005 (8)	0.0168 (8)
C1	0.0293 (8)	0.0309 (8)	0.0452 (9)	0.0136 (7)	0.0133 (7)	0.0164 (7)
C2	0.0249 (7)	0.0287 (8)	0.0268 (7)	0.0055 (6)	0.0017 (6)	0.0066 (6)
C3	0.0319 (8)	0.0254 (8)	0.0398 (9)	0.0106 (7)	0.0049 (7)	0.0027 (7)
C4	0.0312 (8)	0.0272 (8)	0.0483 (10)	0.0073 (7)	0.0021 (7)	0.0161 (7)
C5	0.0407 (9)	0.0429 (10)	0.0436 (9)	0.0084 (8)	0.0121 (8)	0.0235 (8)
C6	0.0413 (9)	0.0375 (9)	0.0408 (9)	0.0128 (7)	0.0209 (7)	0.0127 (7)
C7	0.0267 (8)	0.0544 (11)	0.0670 (12)	0.0122 (8)	0.0097 (8)	0.0280 (9)
C8	0.0480 (11)	0.0279 (9)	0.0594 (12)	0.0033 (8)	−0.0066 (9)	0.0050 (8)
C9	0.0388 (10)	0.0535 (12)	0.0840 (14)	0.0039 (9)	0.0149 (10)	0.0419 (11)
C10	0.0253 (8)	0.0424 (10)	0.0826 (14)	−0.0048 (7)	−0.0007 (9)	0.0251 (10)
C11	0.0385 (9)	0.0457 (10)	0.0362 (10)	0.0126 (8)	0.0051 (8)	0.0095 (8)
C12	0.0609 (12)	0.0443 (10)	0.0617 (12)	0.0231 (9)	0.0235 (10)	0.0273 (9)
C13	0.0434 (10)	0.0402 (10)	0.0525 (11)	−0.0013 (8)	0.0119 (8)	0.0158 (8)
C14	0.0629 (12)	0.0661 (12)	0.0489 (11)	0.0169 (10)	0.0317 (10)	0.0285 (9)

Geometric parameters (Å, º) top

Si—O	1.6594 (11)	C6—H61	0.9900
Si—C13	1.8491 (19)	C6—H62	0.9900
Si—C12	1.8540 (17)	C7—C10	1.526 (2)
Si—C14	1.8562 (16)	C7—H71	0.9900
O—C2	1.4200 (17)	C7—H72	0.9900
N—C11	1.143 (2)	C8—C10	1.535 (2)
C1—C6	1.530 (2)	C8—H81	0.9900
C1—C7	1.535 (2)	C8—H82	0.9900
C1—C2	1.5411 (19)	C9—C10	1.516 (3)
C1—H1	1.0000	C9—H91	0.9900
C2—C11	1.489 (2)	C9—H92	0.9900
C2—C3	1.5415 (19)	C10—H10	1.0000
C3—C4	1.531 (2)	C12—H121	0.9800
C3—C8	1.532 (2)	C12—H122	0.9800
C3—H3	1.0000	C12—H123	0.9800
C4—C5	1.523 (2)	C13—H131	0.9800
C4—H41	0.9900	C13—H132	0.9800
C4—H42	0.9900	C13—H133	0.9800
C5—C9	1.525 (2)	C14—H141	0.9800
C5—C6	1.530 (2)	C14—H142	0.9800
C5—H5	1.0000	C14—H143	0.9800

O—Si—C13	102.98 (7)	C10—C7—C1	109.55 (13)
O—Si—C12	111.91 (7)	C10—C7—H71	109.8
C13—Si—C12	110.75 (8)	C1—C7—H71	109.8
O—Si—C14	110.55 (7)	C10—C7—H72	109.8
C13—Si—C14	110.49 (9)	C1—C7—H72	109.8
C12—Si—C14	109.99 (8)	H71—C7—H72	108.2
C2—O—Si	133.06 (9)	C3—C8—C10	109.94 (13)
C6—C1—C7	109.53 (13)	C3—C8—H81	109.7
C6—C1—C2	108.61 (11)	C10—C8—H81	109.7
C7—C1—C2	110.13 (13)	C3—C8—H82	109.7
C6—C1—H1	109.5	C10—C8—H82	109.7
C7—C1—H1	109.5	H81—C8—H82	108.2
C2—C1—H1	109.5	C10—C9—C5	109.63 (15)
O—C2—C11	108.81 (12)	C10—C9—H91	109.7
O—C2—C1	111.04 (11)	C5—C9—H91	109.7
C11—C2—C1	109.74 (12)	C10—C9—H92	109.7
O—C2—C3	108.61 (11)	C5—C9—H92	109.7
C11—C2—C3	109.88 (12)	H91—C9—H92	108.2
C1—C2—C3	108.74 (12)	C9—C10—C7	110.15 (16)
C4—C3—C8	109.24 (14)	C9—C10—C8	110.01 (14)
C4—C3—C2	108.53 (12)	C7—C10—C8	108.35 (15)
C8—C3—C2	109.88 (12)	C9—C10—H10	109.4
C4—C3—H3	109.7	C7—C10—H10	109.4
C8—C3—H3	109.7	C8—C10—H10	109.4
C2—C3—H3	109.7	N—C11—C2	178.65 (18)
C5—C4—C3	110.11 (12)	Si—C12—H121	109.5
C5—C4—H41	109.6	Si—C12—H122	109.5
C3—C4—H41	109.6	H121—C12—H122	109.5
C5—C4—H42	109.6	Si—C12—H123	109.5
C3—C4—H42	109.6	H121—C12—H123	109.5
H41—C4—H42	108.2	H122—C12—H123	109.5
C4—C5—C9	110.22 (14)	Si—C13—H131	109.5
C4—C5—C6	108.75 (12)	Si—C13—H132	109.5
C9—C5—C6	109.20 (14)	H131—C13—H132	109.5
C4—C5—H5	109.6	Si—C13—H133	109.5
C9—C5—H5	109.6	H131—C13—H133	109.5
C6—C5—H5	109.6	H132—C13—H133	109.5
C1—C6—C5	109.87 (12)	Si—C14—H141	109.5
C1—C6—H61	109.7	Si—C14—H142	109.5
C5—C6—H61	109.7	H141—C14—H142	109.5
C1—C6—H62	109.7	Si—C14—H143	109.5
C5—C6—H62	109.7	H141—C14—H143	109.5
H61—C6—H62	108.2	H142—C14—H143	109.5

C13—Si—O—C2	−160.82 (12)	C3—C4—C5—C6	60.43 (16)
C12—Si—O—C2	−41.84 (13)	C7—C1—C6—C5	−59.17 (16)
C14—Si—O—C2	81.13 (13)	C2—C1—C6—C5	61.14 (16)
Si—O—C2—C11	−37.90 (16)	C4—C5—C6—C1	−60.41 (17)
Si—O—C2—C1	83.00 (14)	C9—C5—C6—C1	59.90 (18)
Si—O—C2—C3	−157.48 (10)	C6—C1—C7—C10	58.48 (17)
C6—C1—C2—O	58.21 (15)	C2—C1—C7—C10	−60.90 (18)
C7—C1—C2—O	178.15 (11)	C4—C3—C8—C10	−58.61 (17)
C6—C1—C2—C11	178.56 (12)	C2—C3—C8—C10	60.35 (18)
C7—C1—C2—C11	−61.50 (17)	C4—C5—C9—C10	59.23 (18)
C6—C1—C2—C3	−61.23 (15)	C6—C5—C9—C10	−60.17 (18)
C7—C1—C2—C3	58.71 (15)	C5—C9—C10—C7	60.26 (19)
O—C2—C3—C4	−59.91 (15)	C5—C9—C10—C8	−59.12 (19)
C11—C2—C3—C4	−178.82 (12)	C1—C7—C10—C9	−59.28 (19)
C1—C2—C3—C4	61.05 (15)	C1—C7—C10—C8	61.10 (18)
O—C2—C3—C8	−179.29 (12)	C3—C8—C10—C9	59.34 (19)
C11—C2—C3—C8	61.79 (17)	C3—C8—C10—C7	−61.12 (18)
C1—C2—C3—C8	−58.34 (16)	O—C2—C11—N	44 (7)
C8—C3—C4—C5	58.71 (16)	C1—C2—C11—N	−77 (7)
C2—C3—C4—C5	−61.09 (16)	C3—C2—C11—N	163 (7)
C3—C4—C5—C9	−59.25 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Nⁱ	1.00	2.68	3.516 (3)	141

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₃NOSi
M_r	249.42
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	6.712 (2), 9.440 (3), 12.439 (2)
α, β, γ (°)	106.19 (2), 102.35 (2), 100.34 (3)
V (Å³)	715.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.38 × 0.34 × 0.18

Data collection
Diffractometer	Oxford Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2005)
T_min, T_max	0.91, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	5687, 2872, 2097
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.06
No. of reflections	2872
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Nⁱ	1.00	2.68	3.516 (3)	141

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

The authors thank Professor Thomas M. Klapötke for generous allocation of diffractometer time.

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