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Volume 69 
Part 5 
Page o628  
May 2013  

Received 7 March 2013
Accepted 13 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 23.1
Details
Open access

rac-(1S*,4aS*,8aS*)-4a-Hydroxy-2-methylperhydrospiro[isoquinoline-4,1'-cyclohexan]-2'-one

aInstitut National Polytechnique Félix Houphouët-Boigny, Enseignant-Chercheur à l'INP-HB de Yamoussoukro, BP 991 Yamoussoukro, Côte d'Ivoire,bOrganic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklaya St. 6, Moscow 117198, Russia, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: ssiaka@inphb.edu.ci

In the title compound, C15H25NO2, all three six-membered rings adopt chair conformations. The cyclohexane and piperidine rings within the perhydroisoquinoline are trans-trans fused. The N atom has a trigonal-pyramidal geometry (the sum of the bond angles is 328.0°). The methyl substituent occupies the sterically preferrable equatorial position. In the crystal, molecules form infinite [100] chains via O-H...N hydrogen bonds.

Related literature

For general background to the synthesis, chemical properties and applications in medicine of the title compound, see: Plati & Wenner (1949[Plati, J. N. & Wenner, W. (1949). J. Org. Chem. 14, 543-549.]); Ellefson et al. (1978[Ellefson, C. R., Woo, C. M. & Cusic, J. W. (1978). J. Med. Chem. 21, 340-343.]); Soldatenkov et al. (2009[Soldatenkov, A. T., Soldatova, S. A., Malkova, A. V., Kolyadina, N. M. & Khrustalev, V. N. (2009). Chem. Heterocycl. Compd, 45, 1398-1400.]). For related compounds, see: Plati & Wenner (1950[Plati, J. N. & Wenner, W. (1950). J. Org. Chem. 15, 209-215.]); Soldatenkov et al. (2008[Soldatenkov, A. T., Volkov, S. V., Polyanskii, K. B. & Soldatova, S. A. (2008). Chem. Heterocycl. Compd, 44, 630-631.]); Soldatova et al. (2010[Soldatova, S. A., Soldatenkov, A. T., Kotsuba, V. E. & Khrustalev, V. N. (2010). Chem. Heterocycl. Compd, 46, 123-124.]); Siaka et al. (2012[Siaka, S., Soldatenkov, A. T., Malkova, A. V., Sorokina, E. A. & Khrustalev, V. N. (2012). Acta Cryst. E68, o3230.]).

[Scheme 1]

Experimental

Crystal data
  • C15H25NO2

  • Mr = 251.36

  • Monoclinic, P 21 /n

  • a = 5.8438 (2) Å

  • b = 18.5756 (7) Å

  • c = 12.2148 (5) Å

  • [beta] = 95.116 (1)°

  • V = 1320.66 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.984

  • 17142 measured reflections

  • 3852 independent reflections

  • 3221 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.00

  • 3852 reflections

  • 167 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N3i 0.830 (12) 2.195 (12) 2.8967 (10) 142.3 (12)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2397 ).


References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Ellefson, C. R., Woo, C. M. & Cusic, J. W. (1978). J. Med. Chem. 21, 340-343.  [CrossRef] [ChemPort] [PubMed] [ISI]
Plati, J. N. & Wenner, W. (1949). J. Org. Chem. 14, 543-549.  [CrossRef] [ChemPort]
Plati, J. N. & Wenner, W. (1950). J. Org. Chem. 15, 209-215.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Siaka, S., Soldatenkov, A. T., Malkova, A. V., Sorokina, E. A. & Khrustalev, V. N. (2012). Acta Cryst. E68, o3230.  [CSD] [CrossRef] [details]
Soldatenkov, A. T., Soldatova, S. A., Malkova, A. V., Kolyadina, N. M. & Khrustalev, V. N. (2009). Chem. Heterocycl. Compd, 45, 1398-1400.
Soldatenkov, A. T., Volkov, S. V., Polyanskii, K. B. & Soldatova, S. A. (2008). Chem. Heterocycl. Compd, 44, 630-631.  [ISI] [CrossRef] [ChemPort]
Soldatova, S. A., Soldatenkov, A. T., Kotsuba, V. E. & Khrustalev, V. N. (2010). Chem. Heterocycl. Compd, 46, 123-124.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o628  [ doi:10.1107/S1600536813007010 ]

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