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

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3230

doi:10.1107/S1600536812043309

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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

(Received 14 October 2012; accepted 17 October 2012; online 27 October 2012)

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 ); 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
β = 116.037 (5)°
V = 3393.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.00
4065 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_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 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043309/rk2383sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043309/rk2383Isup2.hkl

checkCIF report

Comment top

The double Mannich bases, obtained in the form of hydrochlorides from acetophenones, formaldehyde and alkylamines by heating in HCl solution, can be easily cyclized under action of bases yielding 3–aroyl–4–arylpiperidin–4–ols (Plati & Wenner, 1949). The latter are intermediate products in the synthesis of important antihistaminic agents (Plati & Wenner, 1950; Ellefson et al., 1978). We have synthesized an analogous double Mannich base - bis(1–oxo–1,2,3,4–tertrahydro–2–naphthoylmethyl)amine hydrochloride from α–tetralone and tried to prepare from it the corresponding γ–piperidol derivative by the same way. But, instead, multicomponent mixture was formed which contained only traces of the desirable derivative (as identified by LC—MS method). However, we have found that the expected product of the cyclization in the dehydrated form (Plati & Wenner, 1950; Soldatenkov et al., 2008, 2009; Soldatova et al., 2010) is formed by heating of our double Mannich base in HBr solution (Fig. 1). It can be suggested that the starting reagent undergoes a tandem transformation. The first step of this process is aldol–type intramolecular cycloaddition of the two cyclohexenone moieties to each other, and the second one is dehydration. The structure of the product - spiro–N–methylhexahydrobenzo[f]isoquinoline–1,2'–(tetrahydronaphthalin–1'–one), C₂₃H₂₃NO, (I) was unambiguously established by X–ray diffraction study.

The molecule of I comprises spiro–fused hexahydrobenzo[f]isoquinoline and tetrahydronaphthalinone systems (Fig. 2). The tetrahydropyridine ring has a nonsymmetrical half–chair conformation (the C2 and N3 atoms are out of the plane through the other atoms of the ring by 0.612 (3)Å and -0.136 (3)Å, respectively), whereas the cyclohexadiene and cyclohexene rings adopt nonsymmetrical half–boat conformations (the C4A and C5 carbon atoms are out of the plane through the other atoms of the ring by 0.423 (3) and 0.814 (3) Å, respectively, in the case of the cyclohexadiene ring, and the C1 and C3' carbon atoms are out of the plane through the other atoms of the ring by 0.232 (3)Å and 0.756 (3)Å, respectively, in the case of the cyclohexene ring). The dihedral angle between the planes of the terminal benzene rings is 62.85 (6)°. The nitrogen N3 atom has a trigonal–pyramidal geometry (sum of the bond angles is 332.4 (3)°).

In the crystal, the molecules of I form the chains toward [0 0 1] by the weak non–classical intermolecular C9–H9···N3ⁱ hydrogen bonding interactions (Fig. 3, Table 1). The crystal packing of the chains is stacking along the b axis. Symmetry code: (i) x, 1-y, -1/2+z.

The molecule of I possesses an asymmetric center at the C1 carbon atom. The crystal of I is racemate.

Related literature top

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 top

A solution of bis(1–oxo–1,2,3,4–tertrahydro–2–naphthoylmethyl)amine hydrochloride (2.31 g, 6.0 mmol) in 48% HBr (30 ml) was boiled for 2 h. The reaction mixture was cooled, poured into cold water (200 ml) and stirred at 293 K for 15 h. Then the pH of the mixture was brought upto 9, and the expected product was extracted by ether. The obtained extract was washed with water (50 ml) and dried over disodium sulfate. After the solvent evaporation, the residue was purified on the chromatographic column filled with alumogel (ether–hexane mixture, 1:1 as eluent). The main separated fraction (monitoring by TLC) was recrystallized from ethanol to give 0.72 g of yellow crystals of I. Yield is 24%. M.P. = 432–434 K. IR (KBr), ν/cm^-1: 1673. ¹H NMR (CDCl₃, 400 MHz, 300 K): δ = 2.16–2.27 (m, 3H, C—CH₂), 2.36 (s, 3H, CH₃), 2.72–2.94 (m, 4H, C—CH₂), 2.86 (s, 2H, NCH₂), 3.07–3.28 (m, 3H, NCH₂ and C—CH₂), 6.74, 6.93, 7.01 and 7.10 (ABCD–system spectrum, 1H for each signal, ³J = 7.4, 7.2 and 7.1, H_arom), 7.29, 7.36, 7.53 and 8.16 (ABCD–system spectrum, 1H for each signal, ³J = 7.7, 7.6 and 7.1, H_arom). Mass spectrum (70 eV), m/z (I, %): 329 [M⁺] (97.3), 328 (14.1), 286 (21.7), 285 (40.2), 184 (19.7), 183 (22.1), 182 (18.8), 170 (100), 165 (22.5), 141 (38.3), 128 (23.1),115 (31.9), 91 (20.0), 90 (21.6). Anal. Calcd for C₂₃H₂₃NO: C, 83.85; H, 7.04; N, 4.25. Found: C, 83.92; H, 7.21; N, 4.36.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The preparation of the title product by a tandem transformation of bis(1–oxo–1,2,3,4–tertrahydro–2–naphthoylmethyl)amine hydrochloride.
	Fig. 2. Molecular structure of I with the atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 3. The H–bonded chains of I along the c axis. Dashed lines indicate the intermolecular hydrogen bonding interactions.

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

Crystal data top

C₂₃H₂₃NO	F(000) = 1408
M_r = 329.42	D_x = 1.289 Mg m⁻³
Monoclinic, C2/c	Melting point = 432–434 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 27.645 (6) Å	Cell parameters from 4458 reflections
b = 8.1613 (15) Å	θ = 2.5–27.6°
c = 16.741 (3) Å	µ = 0.08 mm⁻¹
β = 116.037 (5)°	T = 100 K
V = 3393.8 (11) Å³	Prism, yellow
Z = 8	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	4065 independent reflections
Radiation source: fine–focus sealed tube	3080 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ– and ω–scans	θ_max = 28.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −36→36
T_min = 0.981, T_max = 0.986	k = −10→10
21756 measured reflections	l = −22→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0573P)² + 3.1P] where P = (F_o² + 2F_c²)/3
4065 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₃NO	V = 3393.8 (11) Å³
M_r = 329.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.645 (6) Å	µ = 0.08 mm⁻¹
b = 8.1613 (15) Å	T = 100 K
c = 16.741 (3) Å	0.25 × 0.20 × 0.18 mm
β = 116.037 (5)°

Data collection top

Bruker APEXII CCD diffractometer	4065 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3080 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.048
21756 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	Δρ_max = 0.34 e Å⁻³
4065 reflections	Δρ_min = −0.21 e Å⁻³
227 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F², conventional R–factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F² are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.38819 (6)	0.38415 (17)	0.63564 (9)	0.0186 (3)
C2	0.41181 (6)	0.31889 (18)	0.73225 (9)	0.0209 (3)
H2A	0.4336	0.2196	0.7375	0.025*
H2B	0.4357	0.4029	0.7734	0.025*
N3	0.36865 (5)	0.27950 (15)	0.75652 (8)	0.0218 (3)
C4	0.33687 (6)	0.14322 (18)	0.70326 (10)	0.0221 (3)
H4A	0.3016	0.1428	0.7054	0.027*
H4B	0.3555	0.0396	0.7304	0.027*
C4A	0.32718 (6)	0.14692 (17)	0.60802 (9)	0.0195 (3)
C5	0.28684 (6)	0.02231 (18)	0.54966 (10)	0.0228 (3)
H5A	0.2504	0.0713	0.5236	0.027*
H5B	0.2867	−0.0731	0.5861	0.027*
C6	0.30040 (6)	−0.03436 (18)	0.47565 (10)	0.0233 (3)
H6A	0.3335	−0.1018	0.5009	0.028*
H6B	0.2707	−0.1030	0.4332	0.028*
C6A	0.30877 (6)	0.11093 (18)	0.42766 (10)	0.0210 (3)
C7	0.29174 (6)	0.10844 (19)	0.33643 (10)	0.0247 (3)
H7	0.2731	0.0152	0.3032	0.030*
C8	0.30145 (6)	0.2397 (2)	0.29267 (10)	0.0257 (3)
H8	0.2895	0.2361	0.2301	0.031*
C9	0.32863 (6)	0.37597 (19)	0.34078 (10)	0.0245 (3)
H9	0.3358	0.4659	0.3115	0.029*
C10	0.34541 (6)	0.38049 (18)	0.43231 (10)	0.0220 (3)
H10	0.3639	0.4745	0.4648	0.026*
C10A	0.33571 (6)	0.24990 (18)	0.47763 (9)	0.0190 (3)
C10B	0.35079 (6)	0.25256 (17)	0.57463 (9)	0.0187 (3)
C11	0.38899 (7)	0.2413 (2)	0.85111 (10)	0.0274 (3)
H11A	0.3587	0.2200	0.8651	0.041*
H11B	0.4099	0.3344	0.8865	0.041*
H11C	0.4121	0.1441	0.8652	0.041*
O1'	0.46093 (4)	0.29448 (13)	0.60614 (7)	0.0251 (3)
C1'	0.43732 (6)	0.41176 (18)	0.61768 (9)	0.0191 (3)
C3'	0.35611 (6)	0.54404 (17)	0.62726 (10)	0.0203 (3)
H3A	0.3351	0.5709	0.5635	0.024*
H3B	0.3304	0.5258	0.6529	0.024*
C4'	0.39224 (6)	0.68881 (18)	0.67422 (10)	0.0216 (3)
H4C	0.3699	0.7886	0.6641	0.026*
H4D	0.4104	0.6676	0.7390	0.026*
C4'A	0.43388 (6)	0.71699 (18)	0.64079 (10)	0.0210 (3)
C5'	0.45125 (6)	0.87444 (19)	0.63298 (11)	0.0259 (3)
H5C	0.4363	0.9666	0.6487	0.031*
C6'	0.48995 (7)	0.89823 (19)	0.60268 (11)	0.0286 (4)
H6C	0.5008	1.0063	0.5969	0.034*
C7'	0.51303 (6)	0.7651 (2)	0.58076 (10)	0.0263 (3)
H7A	0.5400	0.7814	0.5609	0.032*
C8'	0.49630 (6)	0.60865 (19)	0.58814 (10)	0.0225 (3)
H8A	0.5122	0.5172	0.5736	0.027*
C8'A	0.45636 (6)	0.58295 (18)	0.61671 (9)	0.0201 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0219 (7)	0.0156 (7)	0.0175 (7)	0.0003 (5)	0.0080 (6)	−0.0009 (5)
C2	0.0237 (7)	0.0184 (7)	0.0182 (7)	0.0011 (6)	0.0071 (6)	−0.0007 (5)
N3	0.0268 (6)	0.0213 (6)	0.0169 (6)	−0.0007 (5)	0.0092 (5)	−0.0014 (5)
C4	0.0277 (8)	0.0184 (7)	0.0220 (7)	0.0002 (6)	0.0126 (6)	0.0007 (6)
C4A	0.0216 (7)	0.0162 (7)	0.0199 (7)	0.0018 (5)	0.0082 (6)	−0.0016 (5)
C5	0.0249 (7)	0.0187 (7)	0.0236 (8)	−0.0014 (6)	0.0095 (6)	−0.0005 (6)
C6	0.0266 (8)	0.0173 (7)	0.0233 (7)	−0.0011 (6)	0.0086 (6)	−0.0024 (6)
C6A	0.0230 (7)	0.0179 (7)	0.0209 (7)	0.0031 (5)	0.0085 (6)	−0.0015 (6)
C7	0.0275 (8)	0.0219 (7)	0.0217 (7)	0.0011 (6)	0.0081 (6)	−0.0051 (6)
C8	0.0309 (8)	0.0277 (8)	0.0181 (7)	0.0039 (6)	0.0105 (6)	−0.0010 (6)
C9	0.0297 (8)	0.0233 (8)	0.0217 (7)	0.0023 (6)	0.0125 (6)	0.0024 (6)
C10	0.0254 (7)	0.0191 (7)	0.0213 (7)	0.0003 (6)	0.0100 (6)	−0.0021 (6)
C10A	0.0198 (7)	0.0180 (7)	0.0185 (7)	0.0023 (5)	0.0077 (6)	−0.0010 (5)
C10B	0.0202 (7)	0.0161 (6)	0.0183 (7)	0.0018 (5)	0.0069 (6)	−0.0011 (5)
C11	0.0352 (9)	0.0263 (8)	0.0197 (8)	0.0007 (7)	0.0113 (7)	0.0015 (6)
O1'	0.0272 (6)	0.0189 (5)	0.0299 (6)	0.0037 (4)	0.0132 (5)	−0.0033 (4)
C1'	0.0213 (7)	0.0184 (7)	0.0153 (7)	0.0013 (5)	0.0060 (5)	−0.0005 (5)
C3'	0.0231 (7)	0.0164 (7)	0.0212 (7)	0.0017 (5)	0.0095 (6)	−0.0004 (5)
C4'	0.0261 (7)	0.0166 (7)	0.0220 (7)	0.0023 (6)	0.0105 (6)	−0.0030 (6)
C4'A	0.0219 (7)	0.0185 (7)	0.0184 (7)	0.0007 (5)	0.0049 (6)	−0.0011 (5)
C5'	0.0279 (8)	0.0178 (7)	0.0288 (8)	0.0009 (6)	0.0094 (7)	−0.0018 (6)
C6'	0.0294 (8)	0.0197 (7)	0.0325 (9)	−0.0036 (6)	0.0097 (7)	0.0028 (6)
C7'	0.0259 (8)	0.0276 (8)	0.0255 (8)	−0.0010 (6)	0.0115 (6)	0.0042 (6)
C8'	0.0246 (7)	0.0215 (7)	0.0193 (7)	0.0035 (6)	0.0077 (6)	0.0017 (6)
C8'A	0.0218 (7)	0.0188 (7)	0.0170 (7)	0.0001 (5)	0.0060 (6)	−0.0001 (5)

Geometric parameters (Å, º) top

C1—C10B	1.5292 (19)	C9—C10	1.393 (2)
C1—C1'	1.531 (2)	C9—H9	0.9500
C1—C2	1.549 (2)	C10—C10A	1.401 (2)
C1—C3'	1.5491 (19)	C10—H10	0.9500
C2—N3	1.4554 (19)	C10A—C10B	1.4889 (19)
C2—H2A	0.9900	C11—H11A	0.9800
C2—H2B	0.9900	C11—H11B	0.9800
N3—C4	1.4548 (19)	C11—H11C	0.9800
N3—C11	1.4626 (19)	O1'—C1'	1.2207 (17)
C4—C4A	1.497 (2)	C1'—C8'A	1.495 (2)
C4—H4A	0.9900	C3'—C4'	1.524 (2)
C4—H4B	0.9900	C3'—H3A	0.9900
C4A—C10B	1.343 (2)	C3'—H3B	0.9900
C4A—C5	1.509 (2)	C4'—C4'A	1.502 (2)
C5—C6	1.516 (2)	C4'—H4C	0.9900
C5—H5A	0.9900	C4'—H4D	0.9900
C5—H5B	0.9900	C4'A—C5'	1.398 (2)
C6—C6A	1.506 (2)	C4'A—C8'A	1.402 (2)
C6—H6A	0.9900	C5'—C6'	1.384 (2)
C6—H6B	0.9900	C5'—H5C	0.9500
C6A—C7	1.387 (2)	C6'—C7'	1.389 (2)
C6A—C10A	1.412 (2)	C6'—H6C	0.9500
C7—C8	1.389 (2)	C7'—C8'	1.382 (2)
C7—H7	0.9500	C7'—H7A	0.9500
C8—C9	1.385 (2)	C8'—C8'A	1.398 (2)
C8—H8	0.9500	C8'—H8A	0.9500

C10B—C1—C1'	111.72 (11)	C9—C10—C10A	121.69 (14)
C10B—C1—C2	107.91 (11)	C9—C10—H10	119.2
C1'—C1—C2	104.59 (11)	C10A—C10—H10	119.2
C10B—C1—C3'	109.80 (11)	C10—C10A—C6A	117.82 (13)
C1'—C1—C3'	112.35 (12)	C10—C10A—C10B	123.45 (13)
C2—C1—C3'	110.26 (11)	C6A—C10A—C10B	118.70 (13)
N3—C2—C1	110.24 (12)	C4A—C10B—C10A	119.36 (13)
N3—C2—H2A	109.6	C4A—C10B—C1	118.86 (13)
C1—C2—H2A	109.6	C10A—C10B—C1	121.48 (12)
N3—C2—H2B	109.6	N3—C11—H11A	109.5
C1—C2—H2B	109.6	N3—C11—H11B	109.5
H2A—C2—H2B	108.1	H11A—C11—H11B	109.5
C4—N3—C2	110.27 (11)	N3—C11—H11C	109.5
C4—N3—C11	110.03 (12)	H11A—C11—H11C	109.5
C2—N3—C11	112.12 (12)	H11B—C11—H11C	109.5
N3—C4—C4A	114.52 (12)	O1'—C1'—C8'A	121.05 (13)
N3—C4—H4A	108.6	O1'—C1'—C1	119.84 (13)
C4A—C4—H4A	108.6	C8'A—C1'—C1	119.10 (12)
N3—C4—H4B	108.6	C4'—C3'—C1	112.75 (12)
C4A—C4—H4B	108.6	C4'—C3'—H3A	109.0
H4A—C4—H4B	107.6	C1—C3'—H3A	109.0
C10B—C4A—C4	124.35 (13)	C4'—C3'—H3B	109.0
C10B—C4A—C5	121.30 (13)	C1—C3'—H3B	109.0
C4—C4A—C5	114.34 (12)	H3A—C3'—H3B	107.8
C4A—C5—C6	110.93 (12)	C4'A—C4'—C3'	111.25 (12)
C4A—C5—H5A	109.5	C4'A—C4'—H4C	109.4
C6—C5—H5A	109.5	C3'—C4'—H4C	109.4
C4A—C5—H5B	109.5	C4'A—C4'—H4D	109.4
C6—C5—H5B	109.5	C3'—C4'—H4D	109.4
H5A—C5—H5B	108.0	H4C—C4'—H4D	108.0
C6A—C6—C5	110.29 (12)	C5'—C4'A—C8'A	118.47 (14)
C6A—C6—H6A	109.6	C5'—C4'A—C4'	121.76 (13)
C5—C6—H6A	109.6	C8'A—C4'A—C4'	119.77 (13)
C6A—C6—H6B	109.6	C6'—C5'—C4'A	121.04 (14)
C5—C6—H6B	109.6	C6'—C5'—H5C	119.5
H6A—C6—H6B	108.1	C4'A—C5'—H5C	119.5
C7—C6A—C10A	120.00 (14)	C5'—C6'—C7'	120.39 (14)
C7—C6A—C6	121.23 (13)	C5'—C6'—H6C	119.8
C10A—C6A—C6	118.75 (13)	C7'—C6'—H6C	119.8
C6A—C7—C8	121.25 (14)	C8'—C7'—C6'	119.26 (14)
C6A—C7—H7	119.4	C8'—C7'—H7A	120.4
C8—C7—H7	119.4	C6'—C7'—H7A	120.4
C9—C8—C7	119.58 (14)	C7'—C8'—C8'A	120.98 (14)
C9—C8—H8	120.2	C7'—C8'—H8A	119.5
C7—C8—H8	120.2	C8'A—C8'—H8A	119.5
C8—C9—C10	119.64 (14)	C8'—C8'A—C4'A	119.83 (14)
C8—C9—H9	120.2	C8'—C8'A—C1'	118.57 (13)
C10—C9—H9	120.2	C4'A—C8'A—C1'	121.56 (13)

C10B—C1—C2—N3	−58.09 (15)	C1'—C1—C10B—C4A	141.08 (13)
C1'—C1—C2—N3	−177.18 (11)	C2—C1—C10B—C4A	26.64 (17)
C3'—C1—C2—N3	61.83 (15)	C3'—C1—C10B—C4A	−93.57 (15)
C1—C2—N3—C4	65.76 (15)	C1'—C1—C10B—C10A	−45.28 (17)
C1—C2—N3—C11	−171.26 (12)	C2—C1—C10B—C10A	−159.72 (12)
C2—N3—C4—C4A	−39.30 (17)	C3'—C1—C10B—C10A	80.07 (16)
C11—N3—C4—C4A	−163.49 (13)	C10B—C1—C1'—O1'	−43.04 (18)
N3—C4—C4A—C10B	8.3 (2)	C2—C1—C1'—O1'	73.43 (16)
N3—C4—C4A—C5	−170.33 (12)	C3'—C1—C1'—O1'	−166.97 (13)
C10B—C4A—C5—C6	32.90 (19)	C10B—C1—C1'—C8'A	138.38 (13)
C4—C4A—C5—C6	−148.37 (13)	C2—C1—C1'—C8'A	−105.15 (14)
C4A—C5—C6—C6A	−50.93 (16)	C3'—C1—C1'—C8'A	14.45 (17)
C5—C6—C6A—C7	−142.78 (14)	C10B—C1—C3'—C4'	−170.57 (12)
C5—C6—C6A—C10A	38.82 (18)	C1'—C1—C3'—C4'	−45.58 (16)
C10A—C6A—C7—C8	1.1 (2)	C2—C1—C3'—C4'	70.66 (15)
C6—C6A—C7—C8	−177.28 (14)	C1—C3'—C4'—C4'A	56.09 (16)
C6A—C7—C8—C9	0.0 (2)	C3'—C4'—C4'A—C5'	144.85 (14)
C7—C8—C9—C10	−0.7 (2)	C3'—C4'—C4'A—C8'A	−35.28 (19)
C8—C9—C10—C10A	0.3 (2)	C8'A—C4'A—C5'—C6'	−0.4 (2)
C9—C10—C10A—C6A	0.8 (2)	C4'—C4'A—C5'—C6'	179.52 (14)
C9—C10—C10A—C10B	−177.23 (14)	C4'A—C5'—C6'—C7'	−1.1 (2)
C7—C6A—C10A—C10	−1.5 (2)	C5'—C6'—C7'—C8'	1.0 (2)
C6—C6A—C10A—C10	176.93 (13)	C6'—C7'—C8'—C8'A	0.4 (2)
C7—C6A—C10A—C10B	176.67 (13)	C7'—C8'—C8'A—C4'A	−1.9 (2)
C6—C6A—C10A—C10B	−4.9 (2)	C7'—C8'—C8'A—C1'	176.02 (13)
C4—C4A—C10B—C10A	−176.81 (13)	C5'—C4'A—C8'A—C8'	1.8 (2)
C5—C4A—C10B—C10A	1.8 (2)	C4'—C4'A—C8'A—C8'	−178.06 (13)
C4—C4A—C10B—C1	−3.0 (2)	C5'—C4'A—C8'A—C1'	−176.02 (13)
C5—C4A—C10B—C1	175.55 (13)	C4'—C4'A—C8'A—C1'	4.1 (2)
C10—C10A—C10B—C4A	161.01 (14)	O1'—C1'—C8'A—C8'	10.3 (2)
C6A—C10A—C10B—C4A	−17.0 (2)	C1—C1'—C8'A—C8'	−171.18 (12)
C10—C10A—C10B—C1	−12.6 (2)	O1'—C1'—C8'A—C4'A	−171.88 (14)
C6A—C10A—C10B—C1	169.35 (13)	C1—C1'—C8'A—C4'A	6.7 (2)

Hydrogen-bond geometry (Å, º) top

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−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃NO
M_r	329.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	27.645 (6), 8.1613 (15), 16.741 (3)
β (°)	116.037 (5)
V (Å³)	3393.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	21756, 4065, 3080
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.00
No. of reflections	4065
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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−1/2.

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Ellefson, C. R., Woo, C. M. & Cusic, J. W. (1978). J. Med. Chem. 21, 340–343. CrossRef CAS PubMed Web of Science Google Scholar
Plati, J. N. & Wenner, W. (1949). J. Org. Chem. 14, 543–549. CrossRef CAS Web of Science Google Scholar
Plati, J. N. & Wenner, W. (1950). J. Org. Chem. 15, 209–215. CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soldatenkov, A. T., Soldatova, S. A., Malkova, A. V., Kolyadina, N. M. & Khrustalev, V. N. (2009). Chem. Heterocycl. Compd, 45, 1398–1400. Google Scholar
Soldatenkov, A. T., Volkov, S. V., Polyanskii, K. B. & Soldatova, S. A. (2008). Chem. Heterocycl. Compd, 44, 630–631. Web of Science CrossRef CAS Google Scholar
Soldatova, S. A., Soldatenkov, A. T., Kotsuba, V. E. & Khrustalev, V. N. (2010). Chem. Heterocycl. Compd, 46, 123–124. CrossRef CAS Google Scholar

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Volume 68| Part 11| November 2012| Page o3230

doi:10.1107/S1600536812043309

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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