(1R,6R)-1-Methyl-8-aza­spiro­[5.6]dodecan-7-one

Guéret, S.M.; Choi, K.W.; O'Connor, P.D.; Boyd, P.D.W.; Brimble, M.A.

doi:10.1107/S1600536808015158

Volume 64
Part 6
Page o1151
June 2008

Received 12 May 2008
Accepted 20 May 2008
Online 24 May 2008

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.104
Data-to-parameter ratio = 10.1
Details

(1R,6R)-1-Methyl-8-azaspiro[5.6]dodecan-7-one

Stéphanie M. Guéret,^a Ka Wai Choi,^a Patrick D. O'Connor,^a Peter D. W. Boyd ^a and Margaret A. Brimble ^a ^*

^aDepartment of Chemistry, Univerisity of Auckland, Private Bag 92019, Auckland, New Zealand
Correspondence e-mail: m.brimble@auckland.ac.nz

The crystal structure of the title compound, C₁₂H₂₁NO, has been investigated to establish the absolute stereochemistry at position 1. The absolute stereochemistry at the quaternary centre at position 6 is established to be R using an asymmetric Birch reductive alkylation reaction for which the stereochemical outcome is known. The crystal structure indicates the presence of two conformers of the bicyclic (1R,6R)-spirolactam ring system that differ in the conformation adopted by the six-membered ring. In one conformer, the methyl group adopts an axial position whereas in the other conformer, the same methyl group adopts an equatorial position. In both conformers, the seven-membered ring adopts a chair conformation. The two conformers of the bicyclic spirolactam are connected to each other via intermolecular N-HO hydrogen bonds forming a heterodimer. The asymmetric unit contains two such dimers.

Related literature

For related literature, see: Brimble & Trzoss (2004); Brimble et al. (2005); Ciminiello et al. (2007); Hu et al. (2001); MacKinnon et al. (2006); Schultz & Pettus (1997); Schultz et al. (1988).

Experimental

Crystal data

C₁₂H₂₁NO
M_r = 195.30
Triclinic, P 1
a = 8.5417 (2) Å
b = 10.2807 (2) Å
c = 12.6400 (3) Å
= 102.850 (1)°
= 90.091 (1)°
= 91.488 (1)°
V = 1081.78 (4) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 90 (2) K
0.34 × 0.26 × 0.23 mm

Data collection

Bruker SMART diffractometer with APEX2 CCD detector
Absorption correction: none
25392 measured reflections
5160 independent reflections
4784 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.104
S = 1.02
5160 reflections
509 parameters
3 restraints
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N8-H8O1B	0.86	2.11	2.967 (2)	173
N8B-H8BO1	0.86	2.03	2.868 (2)	166
N8A-H8AO1C	0.86	2.03	2.872 (2)	165
N8C-H8CO1A	0.86	2.10	2.959 (2)	172

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2350 ).

Acknowledgements

We thank Tania Groutso for help with the data collection.

References

Brimble, M. A., Crimmins, D. & Trzoss, M. (2005). ARKIVOC, (i), 39-52.
Brimble, M. A. & Trzoss, M. (2004). Tetrahedron, 60, 5613-5622.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Ciminiello, P., Dell'Aversano, C., Fattorusso, E., Forino, M., Grauso, L., Tartaglione, L., Guerrini, F. & Pistocchi, R. (2007). J. Nat. Prod. 70, 1878-1883.
Hu, T. M., Burton, I. W., Cembella, A. D., Curtis, J. M., Quilliam, M. A., Walter, J. A. & Wright, J. L. C. (2001). J. Nat. Prod. 64, 308-312.
MacKinnon, S. L., Walter, J. A., Quilliam, M. A., Cembella, A. D., Leblanc, P., Burton, I. W., Hardstaff, W. R. & Lewis, N. I. (2006). J. Nat. Prod. 69, 983-987.
Schultz, A. G., Macielag, M., Padmanabhan, S., Taveras, A. G. & Welch, M. (1988). J. Am. Chem. Soc. 110, 7828-7841.
Schultz, A. G. & Pettus, L. (1997). Tetrahedron Lett. 38, 5433-5436.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds