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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1692–o1693.
Published online 2009 June 27. doi:  10.1107/S1600536809023848
PMCID: PMC2969294

1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone

Abstract

In the title moleclue, C25H23NO2, the 4-piperidone ring adopts a boat conformation. The mol­ecular conformation is stabilized by an intra­molecular C—H(...)O hydrogen bond. In the crystal, mol­ecules are connected through weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For general background, see: Grishina et al. (1994 [triangle]); Nalanishi et al. (1974 [triangle]); Perumal et al. (2001 [triangle]); Ponnuswamy et al. (2002 [triangle]). For related structures, see: Gayathri et al. (2008 [triangle]); Nithya et al. (2009 [triangle]). For details of the synthesis, see: Noller & Baliah (1948 [triangle]).

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Object name is e-65-o1692-scheme1.jpg

Experimental

Crystal data

  • C25H23NO2
  • M r = 369.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1692-efi1.jpg
  • a = 11.7602 (6) Å
  • b = 9.2404 (3) Å
  • c = 19.1722 (9) Å
  • β = 98.797 (4)°
  • V = 2058.93 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 290 K
  • 0.36 × 0.24 × 0.18 mm

Data collection

  • Oxford Xcalibur Eos(Nova) CCD detector diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.942, T max = 0.987
  • 22931 measured reflections
  • 3831 independent reflections
  • 2515 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.105
  • S = 1.00
  • 3831 reflections
  • 254 parameters
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023848/bt2975sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023848/bt2975Isup2.hkl

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

Acknowledgments

We thank the Department of Science and Technology, India for the use of the CCD facility setup under the FIST–DST program at SSCU, IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

4-piperidones and their derivatives present potential medical applications (Grishina et al., 1994, Ponnuswamy et al., 2002, Nalanishi et al., 1974). Piperidones are also reported to possess analgesic,anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al., 2001). In continouus of our interest in piperidones (Nithya et al., 2009), the crystal structure of title compound is discussed in this paper.

In the title molecule, C25H23NO2 (Fig. 1), the piperidine ring adopts a boat conformation. In the related crystal structure, the piperidine ring also adopts a chair conformation (Gayathri et al., 2008) but the three substituents on the C atoms of the ring are in axial orientations. In the crystal, the molecules are connected through weak intermolecular C—H···O hydrogen bonds. (Fig. 2).

Experimental

To a well stirred solution of 3 methyl-2,6-bis(phenyl)piperidin-4-one (1 equiv.) and triethylamine (1 equiv.) in freshly distilled benzene, benzoyl chloride (1 equiv.) in benzene was added dropwise. Stirring was continued until the completion of reaction. Later, it was poured into water and extracted with DCM, washed well with sodium bicarbonate solution and dried over anhydrous sodium sulfate. This upon evaporation and subsequent recrystallization in distilled ethanol furnished the diffraction-quality crystals of the title compound.

Refinement

All H atoms in were positioned geometrically and refined using a riding model with C—H bond lenghts of 0.93, 0.97 and 0.96Å for aromatic, methylene and methyl H atoms respectively and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
ORTEP diagram of the title compound with 50% probability displacement ellipsoids. Dotted bond indicates the intramolecular C—H···O hydrogen bond.
Fig. 2.
Crystal packing diagram of the title compound. The dotted lines indicate intermolecular C—H···O hydrogen bonds.

Crystal data

C25H23NO2F(000) = 784
Mr = 369.44Dx = 1.192 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 983 reflections
a = 11.7602 (6) Åθ = 2.0–21.3°
b = 9.2404 (3) ŵ = 0.08 mm1
c = 19.1722 (9) ÅT = 290 K
β = 98.797 (4)°Block, colorless
V = 2058.93 (16) Å30.36 × 0.24 × 0.18 mm
Z = 4

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer3831 independent reflections
Radiation source: Enhance (Mo) X-ray Source2515 reflections with I > 2σ(I)
graphiteRint = 0.044
ω scansθmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −14→14
Tmin = 0.942, Tmax = 0.987k = −11→11
22931 measured reflectionsl = −23→23

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
3831 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = −0.15 e Å3

Special details

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.

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

xyzUiso*/Ueq
N10.84703 (9)0.33889 (11)0.02444 (6)0.0410 (3)
O10.85789 (10)0.57741 (11)−0.00176 (6)0.0660 (3)
O21.02467 (10)0.01000 (12)0.12851 (6)0.0696 (4)
C10.89524 (13)0.34406 (15)−0.13261 (8)0.0502 (4)
H10.96160.3060−0.10640.060*
C20.87411 (16)0.32413 (18)−0.20472 (9)0.0660 (5)
H20.92680.2739−0.22710.079*
C30.77585 (19)0.3780 (2)−0.24350 (10)0.0777 (6)
H30.76100.3623−0.29200.093*
C40.69948 (17)0.4549 (2)−0.21091 (11)0.0813 (6)
H40.63270.4913−0.23730.098*
C50.72094 (15)0.47875 (17)−0.13942 (10)0.0644 (5)
H50.67010.5342−0.11790.077*
C60.81811 (12)0.42043 (14)−0.09919 (8)0.0444 (4)
C70.84216 (12)0.45127 (15)−0.02206 (8)0.0458 (4)
C80.89332 (12)0.36834 (15)0.09936 (7)0.0446 (4)
H80.92860.46450.10030.053*
C90.99148 (12)0.26268 (15)0.12180 (8)0.0509 (4)
H9A1.05530.28730.09740.061*
H9B1.01750.27390.17200.061*
C100.95985 (13)0.10771 (16)0.10705 (8)0.0460 (4)
C110.84348 (12)0.07997 (14)0.06341 (7)0.0423 (4)
H110.78540.09680.09410.051*
C120.81844 (11)0.18755 (14)0.00098 (7)0.0397 (3)
H120.86850.1616−0.03350.048*
C130.69509 (12)0.17244 (14)−0.03516 (8)0.0437 (4)
C140.60407 (14)0.21590 (17)−0.00264 (9)0.0575 (4)
H140.61820.25900.04170.069*
C150.49176 (15)0.1960 (2)−0.03526 (11)0.0741 (5)
H150.43120.2270−0.01300.089*
C160.46924 (17)0.1311 (2)−0.09994 (12)0.0814 (6)
H160.39370.1163−0.12130.098*
C170.55856 (18)0.0882 (2)−0.13305 (10)0.0820 (6)
H170.54370.0454−0.17740.098*
C180.67089 (15)0.10815 (17)−0.10088 (9)0.0627 (5)
H180.73100.0779−0.12380.075*
C190.80010 (13)0.37833 (15)0.14586 (8)0.0467 (4)
C200.71183 (14)0.47793 (16)0.12868 (9)0.0580 (4)
H200.71100.53620.08910.070*
C210.62531 (16)0.49192 (18)0.16932 (10)0.0708 (5)
H210.56650.55850.15680.085*
C220.62607 (17)0.4075 (2)0.22834 (11)0.0751 (5)
H220.56810.41720.25600.090*
C230.71230 (17)0.3091 (2)0.24616 (10)0.0790 (6)
H230.71270.25120.28590.095*
C240.79907 (15)0.29535 (18)0.20530 (9)0.0651 (5)
H240.85780.22870.21830.078*
C250.83049 (14)−0.07659 (16)0.03829 (9)0.0588 (4)
H25A0.8866−0.09720.00820.088*
H25B0.7547−0.09090.01260.088*
H25C0.8421−0.14020.07830.088*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0435 (7)0.0352 (6)0.0436 (7)−0.0058 (5)0.0047 (6)−0.0012 (5)
O10.0943 (9)0.0367 (6)0.0664 (8)−0.0083 (6)0.0106 (6)0.0005 (5)
O20.0658 (8)0.0648 (7)0.0731 (8)0.0187 (6)−0.0059 (6)0.0089 (6)
C10.0486 (10)0.0461 (8)0.0549 (10)0.0004 (7)0.0054 (8)0.0059 (7)
C20.0783 (13)0.0635 (11)0.0584 (12)−0.0004 (9)0.0178 (10)0.0029 (9)
C30.0997 (16)0.0817 (13)0.0488 (11)−0.0026 (12)0.0016 (11)0.0111 (10)
C40.0782 (14)0.0880 (14)0.0684 (14)0.0109 (11)−0.0188 (11)0.0197 (11)
C50.0589 (11)0.0628 (10)0.0694 (13)0.0128 (8)0.0032 (9)0.0124 (9)
C60.0434 (9)0.0375 (7)0.0514 (10)−0.0046 (7)0.0042 (7)0.0080 (7)
C70.0429 (9)0.0381 (8)0.0570 (10)−0.0028 (6)0.0096 (7)0.0036 (7)
C80.0457 (9)0.0403 (8)0.0462 (9)−0.0068 (6)0.0025 (7)−0.0035 (6)
C90.0448 (9)0.0571 (9)0.0501 (10)−0.0043 (7)0.0051 (7)−0.0005 (7)
C100.0459 (9)0.0530 (9)0.0412 (9)0.0058 (7)0.0132 (7)0.0062 (7)
C110.0409 (8)0.0381 (7)0.0499 (9)−0.0006 (6)0.0134 (7)0.0033 (6)
C120.0402 (8)0.0341 (7)0.0455 (8)−0.0030 (6)0.0082 (6)−0.0006 (6)
C130.0448 (9)0.0357 (7)0.0495 (9)−0.0065 (6)0.0039 (7)0.0023 (6)
C140.0470 (10)0.0558 (9)0.0681 (11)−0.0046 (8)0.0037 (9)−0.0043 (8)
C150.0456 (11)0.0762 (12)0.0989 (15)−0.0021 (9)0.0056 (10)−0.0002 (11)
C160.0551 (13)0.0854 (14)0.0945 (16)−0.0163 (10)−0.0178 (11)0.0089 (12)
C170.0756 (14)0.0943 (14)0.0688 (13)−0.0248 (12)−0.0122 (11)−0.0089 (11)
C180.0601 (11)0.0669 (11)0.0595 (11)−0.0134 (9)0.0036 (9)−0.0088 (9)
C190.0495 (9)0.0436 (8)0.0463 (9)−0.0037 (7)0.0048 (7)−0.0075 (7)
C200.0656 (12)0.0479 (9)0.0615 (11)0.0058 (8)0.0131 (9)−0.0020 (8)
C210.0699 (13)0.0615 (11)0.0843 (14)0.0134 (9)0.0221 (11)−0.0084 (10)
C220.0775 (14)0.0742 (12)0.0812 (14)−0.0013 (11)0.0370 (11)−0.0141 (11)
C230.0956 (15)0.0831 (13)0.0641 (12)0.0116 (12)0.0309 (11)0.0071 (10)
C240.0705 (12)0.0706 (11)0.0567 (11)0.0142 (9)0.0179 (9)0.0043 (9)
C250.0631 (11)0.0419 (9)0.0715 (12)−0.0009 (7)0.0102 (9)0.0042 (8)

Geometric parameters (Å, °)

N1—C71.3641 (17)C12—C131.5154 (19)
N1—C81.4813 (17)C12—H120.9800
N1—C121.4916 (16)C13—C141.378 (2)
O1—C71.2338 (16)C13—C181.383 (2)
O2—C101.2123 (16)C14—C151.385 (2)
C1—C21.379 (2)C14—H140.9300
C1—C61.3818 (19)C15—C161.366 (3)
C1—H10.9300C15—H150.9300
C2—C31.369 (2)C16—C171.367 (3)
C2—H20.9300C16—H160.9300
C3—C41.369 (3)C17—C181.382 (2)
C3—H30.9300C17—H170.9300
C4—C51.373 (2)C18—H180.9300
C4—H40.9300C19—C241.375 (2)
C5—C61.386 (2)C19—C201.389 (2)
C5—H50.9300C20—C211.379 (2)
C6—C71.490 (2)C20—H200.9300
C8—C191.5179 (19)C21—C221.374 (2)
C8—C91.523 (2)C21—H210.9300
C8—H80.9800C22—C231.366 (3)
C9—C101.496 (2)C22—H220.9300
C9—H9A0.9700C23—C241.384 (2)
C9—H9B0.9700C23—H230.9300
C10—C111.513 (2)C24—H240.9300
C11—C251.525 (2)C25—H25A0.9600
C11—C121.5491 (19)C25—H25B0.9600
C11—H110.9800C25—H25C0.9600
C7—N1—C8117.80 (11)C13—C12—C11110.48 (10)
C7—N1—C12122.12 (11)N1—C12—H12107.5
C8—N1—C12119.80 (10)C13—C12—H12107.5
C2—C1—C6120.18 (15)C11—C12—H12107.5
C2—C1—H1119.9C14—C13—C18118.13 (14)
C6—C1—H1119.9C14—C13—C12121.44 (13)
C3—C2—C1120.25 (17)C18—C13—C12120.37 (13)
C3—C2—H2119.9C13—C14—C15120.67 (16)
C1—C2—H2119.9C13—C14—H14119.7
C2—C3—C4119.96 (18)C15—C14—H14119.7
C2—C3—H3120.0C16—C15—C14120.49 (17)
C4—C3—H3120.0C16—C15—H15119.8
C3—C4—C5120.37 (17)C14—C15—H15119.8
C3—C4—H4119.8C15—C16—C17119.53 (17)
C5—C4—H4119.8C15—C16—H16120.2
C4—C5—C6120.21 (17)C17—C16—H16120.2
C4—C5—H5119.9C16—C17—C18120.27 (18)
C6—C5—H5119.9C16—C17—H17119.9
C1—C6—C5118.97 (15)C18—C17—H17119.9
C1—C6—C7121.30 (13)C17—C18—C13120.90 (17)
C5—C6—C7119.54 (14)C17—C18—H18119.6
O1—C7—N1121.58 (14)C13—C18—H18119.6
O1—C7—C6119.37 (12)C24—C19—C20117.71 (14)
N1—C7—C6119.05 (12)C24—C19—C8123.47 (14)
N1—C8—C19112.91 (11)C20—C19—C8118.81 (13)
N1—C8—C9107.85 (11)C21—C20—C19121.17 (16)
C19—C8—C9117.22 (12)C21—C20—H20119.4
N1—C8—H8106.0C19—C20—H20119.4
C19—C8—H8106.0C22—C21—C20119.99 (17)
C9—C8—H8106.0C22—C21—H21120.0
C10—C9—C8113.86 (12)C20—C21—H21120.0
C10—C9—H9A108.8C23—C22—C21119.69 (17)
C8—C9—H9A108.8C23—C22—H22120.2
C10—C9—H9B108.8C21—C22—H22120.2
C8—C9—H9B108.8C22—C23—C24120.21 (17)
H9A—C9—H9B107.7C22—C23—H23119.9
O2—C10—C9121.58 (14)C24—C23—H23119.9
O2—C10—C11122.02 (13)C19—C24—C23121.23 (16)
C9—C10—C11116.40 (12)C19—C24—H24119.4
C10—C11—C25111.95 (12)C23—C24—H24119.4
C10—C11—C12111.57 (11)C11—C25—H25A109.5
C25—C11—C12111.51 (12)C11—C25—H25B109.5
C10—C11—H11107.2H25A—C25—H25B109.5
C25—C11—H11107.2C11—C25—H25C109.5
C12—C11—H11107.2H25A—C25—H25C109.5
N1—C12—C13112.34 (11)H25B—C25—H25C109.5
N1—C12—C11111.18 (11)
C6—C1—C2—C3−1.0 (2)C7—N1—C12—C11173.99 (12)
C1—C2—C3—C41.6 (3)C8—N1—C12—C110.20 (16)
C2—C3—C4—C50.1 (3)C10—C11—C12—N1−46.08 (15)
C3—C4—C5—C6−2.4 (3)C25—C11—C12—N1−172.09 (11)
C2—C1—C6—C5−1.3 (2)C10—C11—C12—C13−171.51 (11)
C2—C1—C6—C7−176.24 (13)C25—C11—C12—C1362.48 (15)
C4—C5—C6—C13.0 (2)N1—C12—C13—C14−54.97 (17)
C4—C5—C6—C7178.01 (15)C11—C12—C13—C1469.80 (16)
C8—N1—C7—O1−11.4 (2)N1—C12—C13—C18127.97 (14)
C12—N1—C7—O1174.69 (12)C11—C12—C13—C18−107.26 (15)
C8—N1—C7—C6168.16 (12)C18—C13—C14—C15−0.3 (2)
C12—N1—C7—C6−5.76 (19)C12—C13—C14—C15−177.39 (14)
C1—C6—C7—O1113.48 (16)C13—C14—C15—C160.9 (3)
C5—C6—C7—O1−61.43 (19)C14—C15—C16—C17−1.2 (3)
C1—C6—C7—N1−66.08 (18)C15—C16—C17—C181.0 (3)
C5—C6—C7—N1119.00 (16)C16—C17—C18—C13−0.4 (3)
C7—N1—C8—C19103.78 (14)C14—C13—C18—C170.1 (2)
C12—N1—C8—C19−82.15 (15)C12—C13—C18—C17177.22 (15)
C7—N1—C8—C9−125.09 (13)N1—C8—C19—C24124.75 (15)
C12—N1—C8—C948.98 (15)C9—C8—C19—C24−1.5 (2)
N1—C8—C9—C10−52.73 (15)N1—C8—C19—C20−56.42 (17)
C19—C8—C9—C1076.00 (16)C9—C8—C19—C20177.30 (13)
C8—C9—C10—O2−172.09 (13)C24—C19—C20—C21−0.8 (2)
C8—C9—C10—C118.52 (17)C8—C19—C20—C21−179.69 (14)
O2—C10—C11—C25−11.66 (19)C19—C20—C21—C220.6 (3)
C9—C10—C11—C25167.74 (12)C20—C21—C22—C23−0.5 (3)
O2—C10—C11—C12−137.43 (14)C21—C22—C23—C240.5 (3)
C9—C10—C11—C1241.97 (16)C20—C19—C24—C230.8 (2)
C7—N1—C12—C13−61.62 (16)C8—C19—C24—C23179.67 (15)
C8—N1—C12—C13124.58 (13)C22—C23—C24—C19−0.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···O10.982.262.7235 (17)108
C9—H9A···O1i0.972.563.4446 (19)152

Symmetry codes: (i) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2975).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
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