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

Siaka, S.; Soldatenkov, A.T.; Malkova, A.V.; Sorokina, E.A.; Khrustalev, V.N.

doi:10.1107/S1600536812043309

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.122
Data-to-parameter ratio = 17.9
Details

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

Sohro Siaka,^a ^* Anatoly T. Soldatenkov,^b Anastasia V. Malkova,^b Elena A. Sorokina ^b and Victor N. Khrustalev ^c

^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-HN 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); Ellefson et al. (1978); Soldatenkov et al. (2009). For related compounds, see: Plati & Wenner (1950); Soldatenkov et al. (2008); Soldatova et al. (2010).

Experimental

Crystal data

C₂₃H₂₃NO
M_r = 329.42
Monoclinic, C 2/c
a = 27.645 (6) Å
b = 8.1613 (15) Å
c = 16.741 (3) Å
= 116.037 (5)°
V = 3393.8 (11) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.981, T_max = 0.986
21756 measured reflections
4065 independent reflections
3080 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.122
S = 1.00
4065 reflections
227 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9N3ⁱ	0.95	2.59	3.534 (2)	171
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Plati, J. N. & Wenner, W. (1949). J. Org. Chem. 14, 543-549.
Plati, J. N. & Wenner, W. (1950). J. Org. Chem. 15, 209-215.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Soldatova, S. A., Soldatenkov, A. T., Kotsuba, V. E. & Khrustalev, V. N. (2010). Chem. Heterocycl. Compd, 46, 123-124.

organic compounds