organic compounds
2,4-Bis(4-ethoxyphenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one
aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
*Correspondence e-mail: parthisivam@yahoo.co.in
In the title compound, C25H30NO3, a crystallographic mirror plane bisects the molecule. Although it is a positional isomer of 2,4-bis(4-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one [C25H31NO3, Mr = 393.51; Park et al. (2012c). Acta Cryst. E68, o779–780], its molecular weight is 392.50 due to the 50:50 ratio of the methyl group at bridgehead C atoms. However, the title compound exists in the same twin-chair conformation as its 7-methyl isomer. Also, the 4-ethoxyphenyl groups are equatorially oriented on the bicycle as in its isomer. In the title compound, the cyclohexanone ring deviates from an ideal chair (total puckering amplitude QT = 0.5390 Å) and the piperidone ring is closer to an ideal chair (QT = 0.6064 Å). These QT values are very similar to those of its isomer. Even though a center of symmetry passes through the 7-methyl analog, the benzene rings are oriented 26.11 (3)° with respect to each other, whereas the orientation is 53.10 (3)° for the title compound. The title compound exhibits intermolecular N—H⋯O interactions [H⋯A = 2.25 (2) Å, versus 2.26 (2) Å for the analog].
Related literature
For the synthesis, stereochemistry and biological activities of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011a, 2012a). For analogous structures, see: Park et al. (2012b, 2012c); Parthiban et al. (2011b, 2011c). For ring puckering parameters, see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812039840/bq2375sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039840/bq2375Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039840/bq2375Isup3.cml
The title compound was synthesized by a modified and an optimized Mannich condensation in one-pot, using 4-ethoxybenzaldehyde (0.1 mol, 15.018 g/13.91 ml), 2-methylcyclohexanone (0.05 mol, 5.61 g/6.07 ml) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol (Park et al., 2011a). The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. At the end, the crude azabicyclic ketone was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. X-ray diffraction quality crystals of the title compound were obtained by slow evaporation from ethanol.
The nitrogen H atom was located in a difference Fourier map and refined isotropically. Other hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms with aromatic C—H = 0.93 Å, aliphatic C—H = 0.98 Å and methylene C—H = 0.97 Å. The displacement parameters were set for phenyl, methylene and aliphatic H atoms at Uiso(H) = 1.2Ueq(C) and for methyl H atoms at Uiso(H) = 1.5Ueq(C).
Synthesis and stereochemical analysis of the 3-azabicyclononanes are interesting due to their biological actions (Park et al., 2012a). Stereochemical analysis of the biologically active molecules are crucial in drug-design and drug-development programs. Hence, we synthesized the title compound by a modified and an optimized successive double Mannich condensation in one-pot in order to explore its stereochemistry in solid-state.
The detailed analysis and comparison of the torsion angles clearly indicates that the title molecule, C25H30NO3, exists in a twin-chair conformation with an equatorial orientation of the 4-ethoxyphenyl groups on both sides of the secondary amino group.
Further, the Cremer & Pople (Cremer & Pople, 1975) ring puckering parameters calculated for the title compound shows that the piperidone ring adopts a near ideal chair conformation [The total puckering amplitude, QT is 0.6064 Å, the phase angle θ is 175.10° and phi is 359.99°], and the cyclohexane exist in a distorted chair conformation [QT = 0.5390, θ = 9.52° and phi = 60.00°]
The crystal packing of the title compound, 2,4-Bis(4-ethoxyphenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one is stabilized by intermolecular N—H···O interaction (Table 1) as its 7-methyl analog of 2.26 (2) Å (Park et al., 2012c).
For the synthesis, stereochemistry and biological activities of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011a, 2012a). For analogous structures, see: Park et al. (2012b, 2012c); Parthiban et al. (2011b, 2011c). For ring puckering parameters, see: Cremer & Pople (1975).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Anisotropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids. | |
Fig. 2. Intermolecular N—H···O interactions present in the molecule. |
C25H30NO3 | F(000) = 844 |
Mr = 392.50 | Dx = 1.199 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 3421 reflections |
a = 11.9280 (4) Å | θ = 3.0–27.7° |
b = 26.1702 (14) Å | µ = 0.08 mm−1 |
c = 6.9656 (3) Å | T = 298 K |
V = 2174.37 (17) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.28 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 2396 independent reflections |
Radiation source: fine-focus sealed tube | 1689 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
phi and ω scans | θmax = 28.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −15→14 |
Tmin = 0.973, Tmax = 0.988 | k = −33→25 |
7809 measured reflections | l = −8→8 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.3421P] where P = (Fo2 + 2Fc2)/3 |
2396 reflections | (Δ/σ)max < 0.001 |
147 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C25H30NO3 | V = 2174.37 (17) Å3 |
Mr = 392.50 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 11.9280 (4) Å | µ = 0.08 mm−1 |
b = 26.1702 (14) Å | T = 298 K |
c = 6.9656 (3) Å | 0.35 × 0.28 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 2396 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1689 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.988 | Rint = 0.029 |
7809 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.22 e Å−3 |
2396 reflections | Δρmin = −0.17 e Å−3 |
147 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.55634 (11) | 0.70312 (5) | 0.13583 (19) | 0.0350 (4) | |
H1 | 0.5180 | 0.7037 | 0.2603 | 0.042* | |
C2 | 0.46403 (11) | 0.70192 (6) | −0.0240 (2) | 0.0419 (4) | |
C3 | 0.39793 (16) | 0.7500 | 0.0051 (3) | 0.0444 (6) | |
C4 | 0.57166 (18) | 0.7500 | −0.2899 (3) | 0.0487 (6) | |
H4A | 0.5826 | 0.7500 | −0.4279 | 0.058* | |
H4B | 0.6450 | 0.7500 | −0.2296 | 0.058* | |
C5 | 0.50932 (12) | 0.70215 (7) | −0.2323 (2) | 0.0511 (5) | |
H5A | 0.5591 | 0.6731 | −0.2482 | 0.061* | |
H5B | 0.4467 | 0.6975 | −0.3195 | 0.061* | |
C6 | 0.63304 (11) | 0.65729 (5) | 0.1344 (2) | 0.0360 (4) | |
C7 | 0.72669 (13) | 0.65458 (6) | 0.0151 (2) | 0.0445 (4) | |
H7 | 0.7415 | 0.6814 | −0.0687 | 0.053* | |
C8 | 0.79747 (13) | 0.61325 (6) | 0.0183 (2) | 0.0464 (4) | |
H8 | 0.8589 | 0.6123 | −0.0638 | 0.056* | |
C9 | 0.77820 (12) | 0.57292 (6) | 0.1430 (2) | 0.0415 (4) | |
C10 | 0.68483 (13) | 0.57420 (6) | 0.2607 (2) | 0.0468 (4) | |
H10 | 0.6697 | 0.5471 | 0.3433 | 0.056* | |
C11 | 0.61410 (12) | 0.61616 (6) | 0.2545 (2) | 0.0440 (4) | |
H11 | 0.5515 | 0.6167 | 0.3341 | 0.053* | |
C12 | 0.84722 (15) | 0.49538 (6) | 0.2799 (2) | 0.0564 (5) | |
H12A | 0.7787 | 0.4760 | 0.2626 | 0.068* | |
H12B | 0.8457 | 0.5107 | 0.4066 | 0.068* | |
C13 | 0.94628 (17) | 0.46091 (7) | 0.2622 (3) | 0.0651 (5) | |
H13A | 0.9492 | 0.4471 | 0.1347 | 0.098* | |
H13B | 0.9398 | 0.4335 | 0.3533 | 0.098* | |
H13C | 1.0135 | 0.4799 | 0.2873 | 0.098* | |
C14 | 0.3844 (2) | 0.66095 (12) | −0.0007 (4) | 0.0431 (7) | 0.50 |
H14A | 0.3580 | 0.6604 | 0.1295 | 0.065* | 0.50 |
H14B | 0.4199 | 0.6290 | −0.0301 | 0.065* | 0.50 |
H14C | 0.3222 | 0.6662 | −0.0860 | 0.065* | 0.50 |
N1 | 0.62172 (13) | 0.7500 | 0.1205 (2) | 0.0327 (4) | |
O1 | 0.29964 (12) | 0.7500 | 0.0541 (3) | 0.0738 (6) | |
O2 | 0.85487 (9) | 0.53399 (4) | 0.13792 (16) | 0.0533 (3) | |
H1N | 0.6708 (19) | 0.7500 | 0.211 (3) | 0.039 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0331 (6) | 0.0380 (9) | 0.0340 (8) | −0.0042 (7) | 0.0035 (5) | 0.0000 (6) |
C2 | 0.0309 (7) | 0.0523 (11) | 0.0425 (8) | −0.0109 (7) | −0.0005 (6) | −0.0055 (7) |
C3 | 0.0272 (9) | 0.0715 (17) | 0.0343 (11) | 0.000 | −0.0034 (7) | 0.000 |
C4 | 0.0385 (10) | 0.0767 (17) | 0.0310 (11) | 0.000 | 0.0012 (8) | 0.000 |
C5 | 0.0407 (7) | 0.0714 (12) | 0.0411 (9) | −0.0051 (9) | −0.0045 (6) | −0.0121 (8) |
C6 | 0.0358 (7) | 0.0327 (9) | 0.0394 (8) | −0.0046 (6) | 0.0022 (6) | 0.0006 (6) |
C7 | 0.0460 (8) | 0.0342 (9) | 0.0534 (9) | −0.0021 (7) | 0.0130 (7) | 0.0109 (7) |
C8 | 0.0432 (8) | 0.0413 (10) | 0.0545 (9) | 0.0028 (8) | 0.0149 (7) | 0.0096 (7) |
C9 | 0.0458 (8) | 0.0326 (8) | 0.0462 (9) | 0.0019 (7) | 0.0037 (6) | 0.0032 (7) |
C10 | 0.0517 (9) | 0.0389 (9) | 0.0498 (9) | −0.0017 (8) | 0.0087 (7) | 0.0134 (7) |
C11 | 0.0420 (8) | 0.0440 (10) | 0.0459 (9) | −0.0016 (7) | 0.0109 (6) | 0.0079 (7) |
C12 | 0.0664 (11) | 0.0465 (11) | 0.0563 (10) | 0.0091 (9) | 0.0037 (8) | 0.0147 (8) |
C13 | 0.0728 (12) | 0.0554 (12) | 0.0672 (12) | 0.0188 (10) | −0.0016 (9) | 0.0133 (9) |
C14 | 0.0435 (15) | 0.0369 (18) | 0.0488 (17) | −0.0060 (14) | 0.0005 (13) | −0.0014 (14) |
N1 | 0.0284 (8) | 0.0319 (10) | 0.0379 (9) | 0.000 | −0.0063 (7) | 0.000 |
O1 | 0.0278 (7) | 0.1163 (17) | 0.0774 (12) | 0.000 | 0.0094 (7) | 0.000 |
O2 | 0.0591 (7) | 0.0415 (7) | 0.0594 (7) | 0.0129 (6) | 0.0127 (5) | 0.0146 (5) |
C1—N1 | 1.4577 (16) | C8—C9 | 1.386 (2) |
C1—C6 | 1.5084 (19) | C8—H8 | 0.9300 |
C1—C2 | 1.5661 (19) | C9—O2 | 1.3696 (18) |
C1—H1 | 0.9800 | C9—C10 | 1.383 (2) |
C2—C14 | 1.442 (3) | C10—C11 | 1.385 (2) |
C2—C3 | 1.4986 (19) | C10—H10 | 0.9300 |
C2—C5 | 1.549 (2) | C11—H11 | 0.9300 |
C3—O1 | 1.221 (2) | C12—O2 | 1.4169 (18) |
C3—C2i | 1.4986 (19) | C12—C13 | 1.492 (2) |
C4—C5 | 1.511 (2) | C12—H12A | 0.9700 |
C4—C5i | 1.511 (2) | C12—H12B | 0.9700 |
C4—H4A | 0.9700 | C13—H13A | 0.9600 |
C4—H4B | 0.9700 | C13—H13B | 0.9600 |
C5—H5A | 0.9700 | C13—H13C | 0.9600 |
C5—H5B | 0.9700 | C14—H14A | 0.9600 |
C6—C11 | 1.3817 (19) | C14—H14B | 0.9600 |
C6—C7 | 1.394 (2) | C14—H14C | 0.9600 |
C7—C8 | 1.372 (2) | N1—C1i | 1.4577 (16) |
C7—H7 | 0.9300 | N1—H1N | 0.86 (2) |
N1—C1—C6 | 110.13 (11) | C7—C8—H8 | 119.7 |
N1—C1—C2 | 109.94 (12) | C9—C8—H8 | 119.7 |
C6—C1—C2 | 113.94 (11) | O2—C9—C10 | 124.82 (13) |
N1—C1—H1 | 107.5 | O2—C9—C8 | 116.07 (12) |
C6—C1—H1 | 107.5 | C10—C9—C8 | 119.11 (14) |
C2—C1—H1 | 107.5 | C9—C10—C11 | 119.40 (14) |
C14—C2—C3 | 105.22 (16) | C9—C10—H10 | 120.3 |
C14—C2—C5 | 109.76 (16) | C11—C10—H10 | 120.3 |
C3—C2—C5 | 107.89 (14) | C6—C11—C10 | 122.48 (13) |
C14—C2—C1 | 113.46 (17) | C6—C11—H11 | 118.8 |
C3—C2—C1 | 104.89 (12) | C10—C11—H11 | 118.8 |
C5—C2—C1 | 114.89 (11) | O2—C12—C13 | 108.82 (14) |
O1—C3—C2 | 122.89 (8) | O2—C12—H12A | 109.9 |
O1—C3—C2i | 122.89 (8) | C13—C12—H12A | 109.9 |
C2—C3—C2i | 114.19 (16) | O2—C12—H12B | 109.9 |
C5—C4—C5i | 112.00 (17) | C13—C12—H12B | 109.9 |
C5—C4—H4A | 109.2 | H12A—C12—H12B | 108.3 |
C5i—C4—H4A | 109.2 | C12—C13—H13A | 109.5 |
C5—C4—H4B | 109.2 | C12—C13—H13B | 109.5 |
C5i—C4—H4B | 109.2 | H13A—C13—H13B | 109.5 |
H4A—C4—H4B | 107.9 | C12—C13—H13C | 109.5 |
C4—C5—C2 | 115.05 (14) | H13A—C13—H13C | 109.5 |
C4—C5—H5A | 108.5 | H13B—C13—H13C | 109.5 |
C2—C5—H5A | 108.5 | C2—C14—H14A | 109.5 |
C4—C5—H5B | 108.5 | C2—C14—H14B | 109.5 |
C2—C5—H5B | 108.5 | H14A—C14—H14B | 109.5 |
H5A—C5—H5B | 107.5 | C2—C14—H14C | 109.5 |
C11—C6—C7 | 116.88 (13) | H14A—C14—H14C | 109.5 |
C11—C6—C1 | 121.07 (12) | H14B—C14—H14C | 109.5 |
C7—C6—C1 | 122.04 (12) | C1—N1—C1i | 114.64 (14) |
C8—C7—C6 | 121.55 (14) | C1—N1—H1N | 108.1 (7) |
C8—C7—H7 | 119.2 | C1i—N1—H1N | 108.1 (7) |
C6—C7—H7 | 119.2 | C9—O2—C12 | 117.99 (12) |
C7—C8—C9 | 120.56 (13) | ||
N1—C1—C2—C14 | −170.69 (17) | N1—C1—C6—C7 | −39.74 (18) |
C6—C1—C2—C14 | 65.14 (19) | C2—C1—C6—C7 | 84.32 (17) |
N1—C1—C2—C3 | −56.39 (15) | C11—C6—C7—C8 | −0.7 (2) |
C6—C1—C2—C3 | 179.44 (11) | C1—C6—C7—C8 | 178.36 (14) |
N1—C1—C2—C5 | 61.89 (17) | C6—C7—C8—C9 | −0.7 (2) |
C6—C1—C2—C5 | −62.28 (17) | C7—C8—C9—O2 | −178.74 (14) |
C14—C2—C3—O1 | 5.4 (3) | C7—C8—C9—C10 | 1.8 (2) |
C5—C2—C3—O1 | 122.6 (2) | O2—C9—C10—C11 | 179.14 (14) |
C1—C2—C3—O1 | −114.5 (2) | C8—C9—C10—C11 | −1.4 (2) |
C14—C2—C3—C2i | −176.73 (16) | C7—C6—C11—C10 | 1.1 (2) |
C5—C2—C3—C2i | −59.60 (19) | C1—C6—C11—C10 | −178.02 (14) |
C1—C2—C3—C2i | 63.32 (19) | C9—C10—C11—C6 | 0.0 (2) |
C5i—C4—C5—C2 | −46.7 (2) | C6—C1—N1—C1i | −175.39 (10) |
C14—C2—C5—C4 | 166.11 (18) | C2—C1—N1—C1i | 58.26 (18) |
C3—C2—C5—C4 | 51.97 (17) | C10—C9—O2—C12 | −8.8 (2) |
C1—C2—C5—C4 | −64.62 (19) | C8—C9—O2—C12 | 171.71 (15) |
N1—C1—C6—C11 | 139.30 (14) | C13—C12—O2—C9 | −173.00 (14) |
C2—C1—C6—C11 | −96.64 (16) |
Symmetry code: (i) x, −y+3/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1ii | 0.86 (2) | 2.25 (2) | 3.105 (2) | 180 (2) |
Symmetry code: (ii) x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H30NO3 |
Mr | 392.50 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 298 |
a, b, c (Å) | 11.9280 (4), 26.1702 (14), 6.9656 (3) |
V (Å3) | 2174.37 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.28 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.973, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7809, 2396, 1689 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.133, 1.06 |
No. of reflections | 2396 |
No. of parameters | 147 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.17 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 (2) | 2.25 (2) | 3.105 (2) | 179.7 (19) |
Symmetry code: (i) x+1/2, y, −z+1/2. |
Acknowledgements
The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.
References
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Synthesis and stereochemical analysis of the 3-azabicyclononanes are interesting due to their biological actions (Park et al., 2012a). Stereochemical analysis of the biologically active molecules are crucial in drug-design and drug-development programs. Hence, we synthesized the title compound by a modified and an optimized successive double Mannich condensation in one-pot in order to explore its stereochemistry in solid-state.
The detailed analysis and comparison of the torsion angles clearly indicates that the title molecule, C25H30NO3, exists in a twin-chair conformation with an equatorial orientation of the 4-ethoxyphenyl groups on both sides of the secondary amino group.
Further, the Cremer & Pople (Cremer & Pople, 1975) ring puckering parameters calculated for the title compound shows that the piperidone ring adopts a near ideal chair conformation [The total puckering amplitude, QT is 0.6064 Å, the phase angle θ is 175.10° and phi is 359.99°], and the cyclohexane exist in a distorted chair conformation [QT = 0.5390, θ = 9.52° and phi = 60.00°]
The crystal packing of the title compound, 2,4-Bis(4-ethoxyphenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one is stabilized by intermolecular N—H···O interaction (Table 1) as its 7-methyl analog of 2.26 (2) Å (Park et al., 2012c).