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Acta Cryst. (2009). E65, o2984    [ doi:10.1107/S1600536809045346 ]

2,6-Bis(3-methoxyphenyl)-3-methylpiperidin-4-one

P. Nithya, F. N. Khan, M. Novanna, V. R. Hathwar and S. W. Ng

Abstract top

In the molecule of the title compound, C20H23NO3, the bulky methoxyphenyl substituents at the equatorial 2,6-positions crowd the vicinity of the equatorial amino H atom and prevent it from forming intermolecular hydrogen bonds. The piperidine ring adopts a distorted chair conformation.

Related literature top

For the crystal structure of a related piperidinone compound, see: Nithya et al. (2009).

Experimental top

Ammonium acetate (1 mmol), m-methoxybenzaldehyde (2 mmol) and ethylmethyl ketone (1 mmol) was heated until the colour of the solution turned yellow. After the completion of the reaction (as monitored by TLC), the product was dissolved in ether (10 ml). The solution was treated with aqueous hydrochloric acid [20 ml, 1:1 (v/v)]. The hydrochloride salt of the piperidin-4-one was collected and washed with ether. The base was liberated from an alcohol solution of the hydrochloride by the addition of a slight excess of aqueous ammonia at 273 K. The product was collected and recrystallized from ethanol.

Refinement top

C-bound H-atoms were placed in calculated positions (C-H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C20H23NO3 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
2,6-Bis(3-methoxyphenyl)-3-methylpiperidin-4-one top
Crystal data top
C20H23NO3F(000) = 1392
Mr = 325.39Dx = 1.210 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1065 reflections
a = 28.695 (3) Åθ = 2.0–20.8°
b = 10.9717 (12) ŵ = 0.08 mm−1
c = 11.3946 (13) ÅT = 290 K
β = 95.078 (2)°Plate, colourless
V = 3573.3 (7) Å30.35 × 0.12 × 0.08 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer		1751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
graphiteθmax = 25.0°, θmin = 1.4°
φ and ω scansh = −33→34
12581 measured reflectionsk = −13→11
3148 independent reflectionsl = −13→13
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0658P)2 + 0.6442P]
where P = (Fo2 + 2Fc2)/3
3148 reflections(Δ/σ)max = 0.001
224 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C20H23NO3V = 3573.3 (7) Å3
Mr = 325.39Z = 8
Monoclinic, C2/cMo Kα radiation
a = 28.695 (3) ŵ = 0.08 mm−1
b = 10.9717 (12) ÅT = 290 K
c = 11.3946 (13) Å0.35 × 0.12 × 0.08 mm
β = 95.078 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1751 reflections with I > 2σ(I)
12581 measured reflectionsRint = 0.058
3148 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154Δρmax = 0.18 e Å−3
S = 1.04Δρmin = −0.14 e Å−3
3148 reflectionsAbsolute structure: ?
224 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58419 (9)0.8518 (2)0.9145 (2)0.1002 (10)
O20.76371 (8)0.5426 (2)0.51929 (18)0.0750 (7)
O30.57121 (8)0.17943 (18)1.10361 (17)0.0647 (6)
N10.65515 (8)0.5548 (2)0.83450 (19)0.0438 (6)
H1N0.6737 (9)0.493 (2)0.850 (2)0.042 (8)*
C10.68070 (10)0.6693 (3)0.8526 (2)0.0460 (7)
H10.69100.67720.93660.055*
C20.64767 (11)0.7743 (3)0.8172 (3)0.0585 (9)
H2A0.66270.85050.84190.070*
H2B0.64200.77600.73200.070*
C30.60185 (12)0.7651 (3)0.8696 (3)0.0588 (9)
C40.57864 (10)0.6416 (3)0.8627 (2)0.0488 (8)
H40.56970.62510.77920.059*
C50.61533 (9)0.5452 (2)0.9056 (2)0.0405 (7)
H50.62620.56300.98780.049*
C60.59593 (9)0.4172 (2)0.8989 (2)0.0392 (7)
C70.59208 (9)0.3507 (2)1.0002 (2)0.0429 (7)
H70.60190.38501.07290.051*
C80.57388 (10)0.2338 (3)0.9957 (2)0.0456 (7)
C90.56020 (11)0.1801 (3)0.8898 (3)0.0573 (8)
H90.54870.10090.88640.069*
C100.56400 (11)0.2471 (3)0.7879 (3)0.0646 (9)
H100.55440.21230.71530.078*
C110.58152 (10)0.3632 (3)0.7912 (2)0.0525 (8)
H110.58380.40610.72160.063*
C120.72330 (10)0.6733 (3)0.7837 (2)0.0445 (7)
C130.72600 (10)0.6065 (3)0.6817 (2)0.0500 (8)
H130.70130.55580.65500.060*
C140.76509 (11)0.6143 (3)0.6189 (3)0.0549 (8)
C150.80184 (12)0.6882 (3)0.6568 (3)0.0686 (10)
H150.82840.69220.61550.082*
C160.79871 (12)0.7568 (3)0.7577 (3)0.0716 (10)
H160.82320.80850.78340.086*
C170.76009 (11)0.7498 (3)0.8206 (3)0.0597 (9)
H170.75870.79670.88820.072*
C180.80099 (13)0.5566 (3)0.4451 (3)0.0848 (12)
H18A0.80210.63960.41890.127*
H18B0.79580.50360.37820.127*
H18C0.83010.53590.48850.127*
C190.55104 (15)0.0625 (3)1.1084 (3)0.0877 (12)
H19A0.51920.06541.07460.132*
H19B0.55180.03651.18900.132*
H19C0.56840.00601.06500.132*
C200.53454 (12)0.6374 (3)0.9252 (3)0.0826 (11)
H20A0.54210.65111.00790.124*
H20B0.52010.55890.91360.124*
H20C0.51340.69940.89390.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.119 (2)0.0536 (16)0.135 (2)0.0140 (15)0.0511 (19)−0.0246 (15)
O20.0798 (17)0.0788 (16)0.0713 (14)−0.0245 (13)0.0343 (13)−0.0180 (13)
O30.0959 (17)0.0445 (13)0.0538 (13)−0.0223 (12)0.0074 (11)0.0049 (10)
N10.0422 (15)0.0342 (15)0.0560 (15)0.0009 (13)0.0100 (12)0.0041 (12)
C10.0515 (19)0.0455 (18)0.0403 (15)−0.0075 (16)0.0001 (14)−0.0005 (13)
C20.069 (2)0.0394 (19)0.068 (2)−0.0052 (16)0.0137 (17)−0.0052 (15)
C30.071 (2)0.042 (2)0.064 (2)0.0102 (18)0.0113 (17)−0.0019 (15)
C40.0485 (19)0.051 (2)0.0485 (17)0.0065 (16)0.0123 (14)−0.0005 (14)
C50.0421 (17)0.0418 (17)0.0381 (14)−0.0016 (14)0.0074 (12)−0.0017 (12)
C60.0373 (16)0.0382 (17)0.0431 (16)0.0028 (13)0.0092 (13)−0.0022 (13)
C70.0485 (18)0.0393 (18)0.0410 (16)−0.0024 (14)0.0049 (13)−0.0036 (13)
C80.0482 (19)0.0446 (19)0.0447 (16)−0.0016 (15)0.0075 (13)−0.0012 (14)
C90.068 (2)0.0440 (19)0.060 (2)−0.0164 (16)0.0096 (16)−0.0051 (15)
C100.086 (3)0.060 (2)0.0469 (18)−0.019 (2)0.0026 (16)−0.0138 (16)
C110.063 (2)0.055 (2)0.0407 (17)−0.0082 (17)0.0069 (14)−0.0025 (14)
C120.0453 (18)0.0438 (17)0.0438 (16)−0.0059 (15)0.0006 (14)0.0074 (13)
C130.0480 (19)0.0487 (19)0.0536 (18)−0.0162 (15)0.0067 (15)−0.0026 (14)
C140.057 (2)0.053 (2)0.0560 (19)−0.0118 (17)0.0130 (16)0.0019 (16)
C150.060 (2)0.077 (2)0.072 (2)−0.019 (2)0.0216 (18)0.0035 (19)
C160.062 (2)0.077 (2)0.077 (2)−0.032 (2)0.0088 (19)−0.002 (2)
C170.061 (2)0.064 (2)0.0535 (18)−0.0187 (19)0.0034 (16)−0.0029 (16)
C180.089 (3)0.094 (3)0.077 (2)−0.020 (2)0.042 (2)−0.012 (2)
C190.140 (4)0.054 (2)0.071 (2)−0.031 (2)0.021 (2)0.0032 (18)
C200.074 (3)0.076 (3)0.103 (3)0.017 (2)0.039 (2)0.011 (2)
Geometric parameters (Å, °) top
O1—C31.212 (3)C9—C101.388 (4)
O2—C141.379 (3)C9—H90.93
O2—C181.429 (3)C10—C111.368 (4)
O3—C81.375 (3)C10—H100.93
O3—C191.411 (3)C11—H110.93
N1—C11.460 (3)C12—C131.382 (4)
N1—C51.462 (3)C12—C171.384 (4)
N1—H1N0.87 (3)C13—C141.385 (4)
C1—C121.511 (4)C13—H130.93
C1—C21.524 (4)C14—C151.369 (4)
C1—H10.98C15—C161.384 (4)
C2—C31.495 (4)C15—H150.93
C2—H2A0.97C16—C171.374 (4)
C2—H2B0.97C16—H160.93
C3—C41.509 (4)C17—H170.93
C4—C201.507 (4)C18—H18A0.96
C4—C51.541 (4)C18—H18B0.96
C4—H40.98C18—H18C0.96
C5—C61.511 (3)C19—H19A0.96
C5—H50.98C19—H19B0.96
C6—C71.379 (3)C19—H19C0.96
C6—C111.392 (3)C20—H20A0.96
C7—C81.384 (4)C20—H20B0.96
C7—H70.93C20—H20C0.96
C8—C91.368 (4)
C14—O2—C18117.2 (2)C10—C9—H9120.9
C8—O3—C19119.0 (2)C11—C10—C9121.7 (3)
C1—N1—C5113.0 (2)C11—C10—H10119.2
C1—N1—H1N110.2 (17)C9—C10—H10119.2
C5—N1—H1N109.0 (16)C10—C11—C6120.0 (3)
N1—C1—C12111.8 (2)C10—C11—H11120.0
N1—C1—C2108.7 (2)C6—C11—H11120.0
C12—C1—C2110.7 (2)C13—C12—C17118.6 (3)
N1—C1—H1108.5C13—C12—C1122.0 (3)
C12—C1—H1108.5C17—C12—C1119.4 (3)
C2—C1—H1108.5C12—C13—C14120.6 (3)
C3—C2—C1113.0 (2)C12—C13—H13119.7
C3—C2—H2A109.0C14—C13—H13119.7
C1—C2—H2A109.0C15—C14—O2124.2 (3)
C3—C2—H2B109.0C15—C14—C13120.7 (3)
C1—C2—H2B109.0O2—C14—C13115.1 (3)
H2A—C2—H2B107.8C14—C15—C16118.6 (3)
O1—C3—C2122.1 (3)C14—C15—H15120.7
O1—C3—C4121.8 (3)C16—C15—H15120.7
C2—C3—C4116.1 (3)C17—C16—C15121.2 (3)
C20—C4—C3112.9 (3)C17—C16—H16119.4
C20—C4—C5114.0 (2)C15—C16—H16119.4
C3—C4—C5108.3 (2)C16—C17—C12120.3 (3)
C20—C4—H4107.1C16—C17—H17119.9
C3—C4—H4107.1C12—C17—H17119.9
C5—C4—H4107.1O2—C18—H18A109.5
N1—C5—C6110.0 (2)O2—C18—H18B109.5
N1—C5—C4108.7 (2)H18A—C18—H18B109.5
C6—C5—C4112.6 (2)O2—C18—H18C109.5
N1—C5—H5108.5H18A—C18—H18C109.5
C6—C5—H5108.5H18B—C18—H18C109.5
C4—C5—H5108.5O3—C19—H19A109.5
C7—C6—C11118.3 (3)O3—C19—H19B109.5
C7—C6—C5120.4 (2)H19A—C19—H19B109.5
C11—C6—C5121.3 (2)O3—C19—H19C109.5
C6—C7—C8121.1 (3)H19A—C19—H19C109.5
C6—C7—H7119.4H19B—C19—H19C109.5
C8—C7—H7119.4C4—C20—H20A109.5
C9—C8—O3124.5 (3)C4—C20—H20B109.5
C9—C8—C7120.7 (3)H20A—C20—H20B109.5
O3—C8—C7114.8 (2)C4—C20—H20C109.5
C8—C9—C10118.2 (3)H20A—C20—H20C109.5
C8—C9—H9120.9H20B—C20—H20C109.5
C5—N1—C1—C12176.5 (2)C6—C7—C8—C91.5 (4)
C5—N1—C1—C2−61.0 (3)C6—C7—C8—O3−178.7 (2)
N1—C1—C2—C348.7 (3)O3—C8—C9—C10178.6 (3)
C12—C1—C2—C3171.8 (2)C7—C8—C9—C10−1.6 (4)
C1—C2—C3—O1134.6 (3)C8—C9—C10—C111.0 (5)
C1—C2—C3—C4−45.8 (4)C9—C10—C11—C6−0.2 (5)
O1—C3—C4—C20−4.6 (4)C7—C6—C11—C100.1 (4)
C2—C3—C4—C20175.7 (3)C5—C6—C11—C10−179.9 (3)
O1—C3—C4—C5−131.9 (3)N1—C1—C12—C1326.1 (4)
C2—C3—C4—C548.5 (3)C2—C1—C12—C13−95.1 (3)
C1—N1—C5—C6−170.0 (2)N1—C1—C12—C17−156.6 (3)
C1—N1—C5—C466.3 (3)C2—C1—C12—C1782.1 (3)
C20—C4—C5—N1177.2 (3)C17—C12—C13—C141.2 (4)
C3—C4—C5—N1−56.3 (3)C1—C12—C13—C14178.5 (3)
C20—C4—C5—C655.1 (3)C18—O2—C14—C15−6.7 (5)
C3—C4—C5—C6−178.3 (2)C18—O2—C14—C13173.8 (3)
N1—C5—C6—C7124.1 (3)C12—C13—C14—C150.1 (5)
C4—C5—C6—C7−114.6 (3)C12—C13—C14—O2179.5 (3)
N1—C5—C6—C11−56.0 (3)O2—C14—C15—C16179.3 (3)
C4—C5—C6—C1165.4 (3)C13—C14—C15—C16−1.3 (5)
C11—C6—C7—C8−0.7 (4)C14—C15—C16—C171.2 (5)
C5—C6—C7—C8179.2 (2)C15—C16—C17—C120.0 (5)
C19—O3—C8—C9−3.2 (4)C13—C12—C17—C16−1.2 (4)
C19—O3—C8—C7177.0 (3)C1—C12—C17—C16−178.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.972.453.170 (4)131
C19—H19C···O1ii0.962.483.392 (4)159
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y−1, z.
Acknowledgements top

The authors thank the Department of Science and Technology, India, for use of the diffraction facility set up under the IRHPA–DST programme at IISc. FNK thanks the DST for Fast Track Proposal funding. The authors also thank VIT University and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Nithya, P., Hathwar, V. R., Kone, S., Malathi, N. & Khan, F. N. (2009). Acta Cryst. E65, o1692–o1693.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.