4-Ethynyl-2,2,6,6-tetra­methyl-1,2,5,6-tetra­hydro­pyridine N-oxide

Bats, J.W.; Frolow, O.; Engels, J.W.

doi:10.1107/S1600536809004681

Volume 65
Part 3
Page o529
March 2009

Received 2 February 2009
Accepted 9 February 2009
Online 13 February 2009

Key indicators
Single-crystal X-ray study
T = 167 K
Mean (C-C) = 0.001 Å
R = 0.040
wR = 0.112
Data-to-parameter ratio = 27.3
Details

4-Ethynyl-2,2,6,6-tetramethyl-1,2,5,6-tetrahydropyridine N-oxide

Jan W. Bats,^a ^* Olga Frolow ^a and Joachim W. Engels ^a

^aInstitut für Organische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
Correspondence e-mail: bats@chemie.uni-frankfurt.de

The six-membered ring of the title compound, C₁₁H₁₆NO, has a distorted envelope conformation. The piperidine N atom deviates by 0.128 (1) Å from the plane through its three neighbouring atoms. In the crystal structure, molecules are connected by intermolecular C_ethynyl-HO contacts to form chains extending in the [10 $[\overline{1}]$ ] direction.

Related literature

For the preparation of the title compound, see: Gannett et al. (2001); Frolow et al. (2007). For the crystal structures of related compounds see: Igonin et al. (1990); Wiley et al. (1991); Shklover et al. (1990).

Experimental

Crystal data

C₁₁H₁₆NO
M_r = 178.25
Monoclinic, P 2₁ /c
a = 6.0996 (9) Å
b = 20.800 (3) Å
c = 8.3662 (13) Å
= 97.434 (10)°
V = 1052.5 (3) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 167 K
0.60 × 0.50 × 0.50 mm

Data collection

Siemens SMART 1K CCD diffractometer
Absorption correction: none
18416 measured reflections
3580 independent reflections
3143 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.112
S = 1.09
3580 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7AO1ⁱ	0.944 (14)	2.354 (15)	3.2318 (13)	154.6 (13)
Symmetry code: (i) x+1, y, z+1.

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2096 ).

References

Frolow, O., Bode, B. E. & Engels, J. W. (2007). Nucleosides Nucleotides Nucleic Acids, 26, 655-659.
Gannett, P. M., Darian, E., Powell, J. H. & Johnson, E. M. (2001). Synth. Commun. 31, 2137-2141.
Igonin, V. A., Shklover, V. E., Struchkov, Yu. T., Lazareva, O. L. & Vinogradov, G. A. (1990). Acta Cryst. C46, 776-778.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shklover, V. E., Zamaev, I. A., Struchkov, Y. T., Medvedeva, T. V., Korshak, Y. V., Ovchinnikov, A. A. & Spector, V. N. (1990). Z. Kristallogr. 191, 9-14.
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wiley, D. W., Calabrese, J. C., Harlow, R. L. & Miller, J. S. (1991). Angew. Chem. Int. Ed. 30, 450-452.

organic compounds