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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2984.
Published online 2009 November 4. doi:  10.1107/S1600536809045346
PMCID: PMC2972106

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

Abstract

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

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

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Object name is e-65-o2984-scheme1.jpg

Experimental

Crystal data

  • C20H23NO3
  • M r = 325.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2984-efi1.jpg
  • a = 28.695 (3) Å
  • b = 10.9717 (12) Å
  • c = 11.3946 (13) Å
  • β = 95.078 (2)°
  • V = 3573.3 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 290 K
  • 0.35 × 0.12 × 0.08 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 12581 measured reflections
  • 3148 independent reflections
  • 1751 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.154
  • S = 1.04
  • 3148 reflections
  • 224 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.14 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045346/ci2955sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045346/ci2955Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C20H23NO3 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C20H23NO3F(000) = 1392
Mr = 325.39Dx = 1.210 Mg m3
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 mm1
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

Bruker SMART CCD area-detector diffractometer1751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
graphiteθmax = 25.0°, θmin = 1.4°
[var phi] and ω scansh = −33→34
12581 measured reflectionsk = −13→11
3148 independent reflectionsl = −13→13

Refinement

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.14 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2955).

References

  • 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. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

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