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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

(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[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

  • 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[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 > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.122

  • S = 1.00

  • 4065 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Supporting information


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, Harom), 7.29, 7.36, 7.53 and 8.16 (ABCD–system spectrum, 1H for each signal, 3J = 7.7, 7.6 and 7.1, Harom). 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.

Refinement top

The hydrogen atoms were placed in calculated positions with C—H = 0.95Å–0.99Å and refined in the riding model with fixed isotropic displacement parameters (Uiso(H) = 1.5Ueq(C) for the methyl group and 1.2Ueq(C) for the other groups).

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
[Figure 1] 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.
[Figure 2] 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.
[Figure 3] 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
C23H23NOF(000) = 1408
Mr = 329.42Dx = 1.289 Mg m3
Monoclinic, C2/cMelting point = 432–434 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 27.645 (6) ÅCell parameters from 4458 reflections
b = 8.1613 (15) Åθ = 2.5–27.6°
c = 16.741 (3) ŵ = 0.08 mm1
β = 116.037 (5)°T = 100 K
V = 3393.8 (11) Å3Prism, yellow
Z = 80.25 × 0.20 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
4065 independent reflections
Radiation source: fine–focus sealed tube3080 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ– and ω–scansθmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 3636
Tmin = 0.981, Tmax = 0.986k = 1010
21756 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0573P)2 + 3.1P]
where P = (Fo2 + 2Fc2)/3
4065 reflections(Δ/σ)max < 0.001
227 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C23H23NOV = 3393.8 (11) Å3
Mr = 329.42Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.645 (6) ŵ = 0.08 mm1
b = 8.1613 (15) ÅT = 100 K
c = 16.741 (3) Å0.25 × 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)
Tmin = 0.981, Tmax = 0.986Rint = 0.048
21756 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.00Δρmax = 0.34 e Å3
4065 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
C10.38819 (6)0.38415 (17)0.63564 (9)0.0186 (3)
C20.41181 (6)0.31889 (18)0.73225 (9)0.0209 (3)
H2A0.43360.21960.73750.025*
H2B0.43570.40290.77340.025*
N30.36865 (5)0.27950 (15)0.75652 (8)0.0218 (3)
C40.33687 (6)0.14322 (18)0.70326 (10)0.0221 (3)
H4A0.30160.14280.70540.027*
H4B0.35550.03960.73040.027*
C4A0.32718 (6)0.14692 (17)0.60802 (9)0.0195 (3)
C50.28684 (6)0.02231 (18)0.54966 (10)0.0228 (3)
H5A0.25040.07130.52360.027*
H5B0.28670.07310.58610.027*
C60.30040 (6)0.03436 (18)0.47565 (10)0.0233 (3)
H6A0.33350.10180.50090.028*
H6B0.27070.10300.43320.028*
C6A0.30877 (6)0.11093 (18)0.42766 (10)0.0210 (3)
C70.29174 (6)0.10844 (19)0.33643 (10)0.0247 (3)
H70.27310.01520.30320.030*
C80.30145 (6)0.2397 (2)0.29267 (10)0.0257 (3)
H80.28950.23610.23010.031*
C90.32863 (6)0.37597 (19)0.34078 (10)0.0245 (3)
H90.33580.46590.31150.029*
C100.34541 (6)0.38049 (18)0.43231 (10)0.0220 (3)
H100.36390.47450.46480.026*
C10A0.33571 (6)0.24990 (18)0.47763 (9)0.0190 (3)
C10B0.35079 (6)0.25256 (17)0.57463 (9)0.0187 (3)
C110.38899 (7)0.2413 (2)0.85111 (10)0.0274 (3)
H11A0.35870.22000.86510.041*
H11B0.40990.33440.88650.041*
H11C0.41210.14410.86520.041*
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)
H3A0.33510.57090.56350.024*
H3B0.33040.52580.65290.024*
C4'0.39224 (6)0.68881 (18)0.67422 (10)0.0216 (3)
H4C0.36990.78860.66410.026*
H4D0.41040.66760.73900.026*
C4'A0.43388 (6)0.71699 (18)0.64079 (10)0.0210 (3)
C5'0.45125 (6)0.87444 (19)0.63298 (11)0.0259 (3)
H5C0.43630.96660.64870.031*
C6'0.48995 (7)0.89823 (19)0.60268 (11)0.0286 (4)
H6C0.50081.00630.59690.034*
C7'0.51303 (6)0.7651 (2)0.58076 (10)0.0263 (3)
H7A0.54000.78140.56090.032*
C8'0.49630 (6)0.60865 (19)0.58814 (10)0.0225 (3)
H8A0.51220.51720.57360.027*
C8'A0.45636 (6)0.58295 (18)0.61671 (9)0.0201 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0219 (7)0.0156 (7)0.0175 (7)0.0003 (5)0.0080 (6)0.0009 (5)
C20.0237 (7)0.0184 (7)0.0182 (7)0.0011 (6)0.0071 (6)0.0007 (5)
N30.0268 (6)0.0213 (6)0.0169 (6)0.0007 (5)0.0092 (5)0.0014 (5)
C40.0277 (8)0.0184 (7)0.0220 (7)0.0002 (6)0.0126 (6)0.0007 (6)
C4A0.0216 (7)0.0162 (7)0.0199 (7)0.0018 (5)0.0082 (6)0.0016 (5)
C50.0249 (7)0.0187 (7)0.0236 (8)0.0014 (6)0.0095 (6)0.0005 (6)
C60.0266 (8)0.0173 (7)0.0233 (7)0.0011 (6)0.0086 (6)0.0024 (6)
C6A0.0230 (7)0.0179 (7)0.0209 (7)0.0031 (5)0.0085 (6)0.0015 (6)
C70.0275 (8)0.0219 (7)0.0217 (7)0.0011 (6)0.0081 (6)0.0051 (6)
C80.0309 (8)0.0277 (8)0.0181 (7)0.0039 (6)0.0105 (6)0.0010 (6)
C90.0297 (8)0.0233 (8)0.0217 (7)0.0023 (6)0.0125 (6)0.0024 (6)
C100.0254 (7)0.0191 (7)0.0213 (7)0.0003 (6)0.0100 (6)0.0021 (6)
C10A0.0198 (7)0.0180 (7)0.0185 (7)0.0023 (5)0.0077 (6)0.0010 (5)
C10B0.0202 (7)0.0161 (6)0.0183 (7)0.0018 (5)0.0069 (6)0.0011 (5)
C110.0352 (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'A0.0219 (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'A0.0218 (7)0.0188 (7)0.0170 (7)0.0001 (5)0.0060 (6)0.0001 (5)
Geometric parameters (Å, º) top
C1—C10B1.5292 (19)C9—C101.393 (2)
C1—C1'1.531 (2)C9—H90.9500
C1—C21.549 (2)C10—C10A1.401 (2)
C1—C3'1.5491 (19)C10—H100.9500
C2—N31.4554 (19)C10A—C10B1.4889 (19)
C2—H2A0.9900C11—H11A0.9800
C2—H2B0.9900C11—H11B0.9800
N3—C41.4548 (19)C11—H11C0.9800
N3—C111.4626 (19)O1'—C1'1.2207 (17)
C4—C4A1.497 (2)C1'—C8'A1.495 (2)
C4—H4A0.9900C3'—C4'1.524 (2)
C4—H4B0.9900C3'—H3A0.9900
C4A—C10B1.343 (2)C3'—H3B0.9900
C4A—C51.509 (2)C4'—C4'A1.502 (2)
C5—C61.516 (2)C4'—H4C0.9900
C5—H5A0.9900C4'—H4D0.9900
C5—H5B0.9900C4'A—C5'1.398 (2)
C6—C6A1.506 (2)C4'A—C8'A1.402 (2)
C6—H6A0.9900C5'—C6'1.384 (2)
C6—H6B0.9900C5'—H5C0.9500
C6A—C71.387 (2)C6'—C7'1.389 (2)
C6A—C10A1.412 (2)C6'—H6C0.9500
C7—C81.389 (2)C7'—C8'1.382 (2)
C7—H70.9500C7'—H7A0.9500
C8—C91.385 (2)C8'—C8'A1.398 (2)
C8—H80.9500C8'—H8A0.9500
C10B—C1—C1'111.72 (11)C9—C10—C10A121.69 (14)
C10B—C1—C2107.91 (11)C9—C10—H10119.2
C1'—C1—C2104.59 (11)C10A—C10—H10119.2
C10B—C1—C3'109.80 (11)C10—C10A—C6A117.82 (13)
C1'—C1—C3'112.35 (12)C10—C10A—C10B123.45 (13)
C2—C1—C3'110.26 (11)C6A—C10A—C10B118.70 (13)
N3—C2—C1110.24 (12)C4A—C10B—C10A119.36 (13)
N3—C2—H2A109.6C4A—C10B—C1118.86 (13)
C1—C2—H2A109.6C10A—C10B—C1121.48 (12)
N3—C2—H2B109.6N3—C11—H11A109.5
C1—C2—H2B109.6N3—C11—H11B109.5
H2A—C2—H2B108.1H11A—C11—H11B109.5
C4—N3—C2110.27 (11)N3—C11—H11C109.5
C4—N3—C11110.03 (12)H11A—C11—H11C109.5
C2—N3—C11112.12 (12)H11B—C11—H11C109.5
N3—C4—C4A114.52 (12)O1'—C1'—C8'A121.05 (13)
N3—C4—H4A108.6O1'—C1'—C1119.84 (13)
C4A—C4—H4A108.6C8'A—C1'—C1119.10 (12)
N3—C4—H4B108.6C4'—C3'—C1112.75 (12)
C4A—C4—H4B108.6C4'—C3'—H3A109.0
H4A—C4—H4B107.6C1—C3'—H3A109.0
C10B—C4A—C4124.35 (13)C4'—C3'—H3B109.0
C10B—C4A—C5121.30 (13)C1—C3'—H3B109.0
C4—C4A—C5114.34 (12)H3A—C3'—H3B107.8
C4A—C5—C6110.93 (12)C4'A—C4'—C3'111.25 (12)
C4A—C5—H5A109.5C4'A—C4'—H4C109.4
C6—C5—H5A109.5C3'—C4'—H4C109.4
C4A—C5—H5B109.5C4'A—C4'—H4D109.4
C6—C5—H5B109.5C3'—C4'—H4D109.4
H5A—C5—H5B108.0H4C—C4'—H4D108.0
C6A—C6—C5110.29 (12)C5'—C4'A—C8'A118.47 (14)
C6A—C6—H6A109.6C5'—C4'A—C4'121.76 (13)
C5—C6—H6A109.6C8'A—C4'A—C4'119.77 (13)
C6A—C6—H6B109.6C6'—C5'—C4'A121.04 (14)
C5—C6—H6B109.6C6'—C5'—H5C119.5
H6A—C6—H6B108.1C4'A—C5'—H5C119.5
C7—C6A—C10A120.00 (14)C5'—C6'—C7'120.39 (14)
C7—C6A—C6121.23 (13)C5'—C6'—H6C119.8
C10A—C6A—C6118.75 (13)C7'—C6'—H6C119.8
C6A—C7—C8121.25 (14)C8'—C7'—C6'119.26 (14)
C6A—C7—H7119.4C8'—C7'—H7A120.4
C8—C7—H7119.4C6'—C7'—H7A120.4
C9—C8—C7119.58 (14)C7'—C8'—C8'A120.98 (14)
C9—C8—H8120.2C7'—C8'—H8A119.5
C7—C8—H8120.2C8'A—C8'—H8A119.5
C8—C9—C10119.64 (14)C8'—C8'A—C4'A119.83 (14)
C8—C9—H9120.2C8'—C8'A—C1'118.57 (13)
C10—C9—H9120.2C4'A—C8'A—C1'121.56 (13)
C10B—C1—C2—N358.09 (15)C1'—C1—C10B—C4A141.08 (13)
C1'—C1—C2—N3177.18 (11)C2—C1—C10B—C4A26.64 (17)
C3'—C1—C2—N361.83 (15)C3'—C1—C10B—C4A93.57 (15)
C1—C2—N3—C465.76 (15)C1'—C1—C10B—C10A45.28 (17)
C1—C2—N3—C11171.26 (12)C2—C1—C10B—C10A159.72 (12)
C2—N3—C4—C4A39.30 (17)C3'—C1—C10B—C10A80.07 (16)
C11—N3—C4—C4A163.49 (13)C10B—C1—C1'—O1'43.04 (18)
N3—C4—C4A—C10B8.3 (2)C2—C1—C1'—O1'73.43 (16)
N3—C4—C4A—C5170.33 (12)C3'—C1—C1'—O1'166.97 (13)
C10B—C4A—C5—C632.90 (19)C10B—C1—C1'—C8'A138.38 (13)
C4—C4A—C5—C6148.37 (13)C2—C1—C1'—C8'A105.15 (14)
C4A—C5—C6—C6A50.93 (16)C3'—C1—C1'—C8'A14.45 (17)
C5—C6—C6A—C7142.78 (14)C10B—C1—C3'—C4'170.57 (12)
C5—C6—C6A—C10A38.82 (18)C1'—C1—C3'—C4'45.58 (16)
C10A—C6A—C7—C81.1 (2)C2—C1—C3'—C4'70.66 (15)
C6—C6A—C7—C8177.28 (14)C1—C3'—C4'—C4'A56.09 (16)
C6A—C7—C8—C90.0 (2)C3'—C4'—C4'A—C5'144.85 (14)
C7—C8—C9—C100.7 (2)C3'—C4'—C4'A—C8'A35.28 (19)
C8—C9—C10—C10A0.3 (2)C8'A—C4'A—C5'—C6'0.4 (2)
C9—C10—C10A—C6A0.8 (2)C4'—C4'A—C5'—C6'179.52 (14)
C9—C10—C10A—C10B177.23 (14)C4'A—C5'—C6'—C7'1.1 (2)
C7—C6A—C10A—C101.5 (2)C5'—C6'—C7'—C8'1.0 (2)
C6—C6A—C10A—C10176.93 (13)C6'—C7'—C8'—C8'A0.4 (2)
C7—C6A—C10A—C10B176.67 (13)C7'—C8'—C8'A—C4'A1.9 (2)
C6—C6A—C10A—C10B4.9 (2)C7'—C8'—C8'A—C1'176.02 (13)
C4—C4A—C10B—C10A176.81 (13)C5'—C4'A—C8'A—C8'1.8 (2)
C5—C4A—C10B—C10A1.8 (2)C4'—C4'A—C8'A—C8'178.06 (13)
C4—C4A—C10B—C13.0 (2)C5'—C4'A—C8'A—C1'176.02 (13)
C5—C4A—C10B—C1175.55 (13)C4'—C4'A—C8'A—C1'4.1 (2)
C10—C10A—C10B—C4A161.01 (14)O1'—C1'—C8'A—C8'10.3 (2)
C6A—C10A—C10B—C4A17.0 (2)C1—C1'—C8'A—C8'171.18 (12)
C10—C10A—C10B—C112.6 (2)O1'—C1'—C8'A—C4'A171.88 (14)
C6A—C10A—C10B—C1169.35 (13)C1—C1'—C8'A—C4'A6.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···N3i0.952.593.534 (2)171
Symmetry code: (i) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC23H23NO
Mr329.42
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)27.645 (6), 8.1613 (15), 16.741 (3)
β (°) 116.037 (5)
V3)3393.8 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.981, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
21756, 4065, 3080
Rint0.048
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.122, 1.00
No. of reflections4065
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.21

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···N3i0.952.593.534 (2)171
Symmetry code: (i) x, y+1, z1/2.
 

References

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

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