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Volume 68 
Part 11 
Page o3230  
November 2012  

Received 14 October 2012
Accepted 17 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.122
Data-to-parameter ratio = 17.9
Details
Open access

3-Methyl-1,2,3,4,5,6,1',2',3',4'-decahydrospiro[benz[f]isoquinoline-1,2'-naphthalen]-1'-one

aInstitut National Polytechnique Félix HOUPHOUËT-BOIGNY, BP 1093, Yamoussoukro, Côte d'Ivoire,bOrganic Chemistry Department, Peoples' Friendship University of Russia, 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 St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: ssiaka@inphb.edu.ci

The title compound, C23H23NO, is the product of a tandem transformation of the double Mannich base bis(1-oxo-1,2,3,4-tertrahydro-2-naphthoylmethyl)amine hydrochloride in HBr solution upon heating. The tetrahydropyridine ring has a non-symmetrical half-chair conformation, whereas the cyclohexadiene and cyclohexene rings adopt non-symmetrical half-boat conformations. The dihedral angle between the planes of the terminal benzene rings is 62.85 (6)°. The N atom has a trigonal-pyramidal geometry [sum of the bond angles = 332.4 (3)°]. In the crystal, molecules form [001] chains via weak non-classical C-H...N hydrogen bonds. The chains are stacked along the b axis.

Related literature

For general background to the synthesis, chemical properties and probable applications in medicine (including computer program prognosis) 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.]).

[Scheme 1]

Experimental

Crystal data
  • C23H23NO

  • Mr = 329.42

  • Monoclinic, C 2/c

  • a = 27.645 (6) Å

  • b = 8.1613 (15) Å

  • c = 16.741 (3) Å

  • [beta] = 116.037 (5)°

  • V = 3393.8 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.25 × 0.20 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.986

  • 21756 measured reflections

  • 4065 independent reflections

  • 3080 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.122

  • S = 1.00

  • 4065 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...N3i 0.95 2.59 3.534 (2) 171
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS, 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: RK2383 ).


References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS, 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. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [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 (2012). E68, o3230  [ doi:10.1107/S1600536812043309 ]

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