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In the title mol­ecule, C17H19NO, the piperidine ring adopts a chair conformation. The acetyl group in the 1-position and ethyl group in the 3-position each have an equatorial orientation. The furyl rings at positions 2 and 6 have axial orientations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013407/cv2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013407/cv2019Isup2.hkl
Contains datablock I

CCDC reference: 608406

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.166
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg. PLAT230_ALERT_2_B Hirshfeld Test Diff for O62 - C61 .. 8.34 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O62 - C63 .. 8.11 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C61 - C65 .. 8.30 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C64 - C65 .. 12.72 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C61
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

1-Acetyl-3-ethyl-r-2,c-6-di-2-furylpiperidin-4-one top
Crystal data top
C17H19NO4F(000) = 640
Mr = 301.33Dx = 1.312 Mg m3
Monoclinic, P21/nMelting point: 353 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.036 (4) ÅCell parameters from 25 reflections
b = 8.5608 (15) Åθ = 10–12°
c = 22.180 (7) ŵ = 0.09 mm1
β = 91.05 (3)°T = 293 K
V = 1525.5 (9) Å3Prism, colourless
Z = 40.30 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω–2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.973, Tmax = 0.982l = 2626
2881 measured reflections2 standard reflections every 60 min
2676 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.095P)2 + 0.4568P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2676 reflectionsΔρmax = 0.36 e Å3
200 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
Special details top

Experimental. Absorption correction details: number of psi-scan sets used was 3, theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.5699 (0.0076) x - 1.2641 (0.0136) y + 12.6750 (0.0270) z = 7.6687 (0.0270)

* 0.0114 (0.0016) C61 * -0.0019 (0.0017) O62 * -0.0088 (0.0021) C63 * 0.0147 (0.0021) C64 * -0.0155 (0.0017) C65 - 0.0157 (0.0042) C6

Rms deviation of fitted atoms = 0.0115

- 6.9825 (0.0067) x + 2.3474 (0.0109) y + 9.4913 (0.0274) z = 8.8709 (0.0276)

Angle to previous plane (with approximate e.s.d.) = 25.94 (0.14)

* -0.0046 (0.0014) C21 * 0.0071 (0.0014) O22 * -0.0071 (0.0017) C23 * 0.0041 (0.0017) C24 * 0.0004 (0.0016) C25 - 0.0313 (0.0038) C2

Rms deviation of fitted atoms = 0.0053

1.3488 (0.0083) x - 7.2705 (0.0075) y + 11.0315 (0.0250) z = 6.6018 (0.0234)

Angle to previous plane (with approximate e.s.d.) = 80.07 (0.10)

* -0.0104 (0.0011) C2 * 0.0104 (0.0011) C3 * -0.0105 (0.0011) C5 * 0.0105 (0.0011) C6 - 0.5646 (0.0026) N1 0.6087 (0.0031) C4

Rms deviation of fitted atoms = 0.0105

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
O10.5520 (2)0.3051 (2)0.14369 (8)0.0688 (7)
O40.9429 (2)0.89106 (18)0.19819 (8)0.0686 (7)
O220.7862 (2)0.5678 (2)0.01420 (7)0.0683 (6)
O620.5474 (3)0.8580 (2)0.14634 (10)0.0842 (8)
N10.7578 (2)0.48403 (19)0.14229 (8)0.0460 (6)
C10.6939 (3)0.3393 (2)0.12944 (10)0.0515 (7)
C20.9098 (3)0.5463 (2)0.11449 (9)0.0475 (7)
C31.0172 (3)0.6390 (3)0.16055 (10)0.0504 (7)
C40.9096 (3)0.7526 (3)0.19437 (10)0.0510 (7)
C50.7591 (3)0.6821 (3)0.22242 (10)0.0534 (7)
C60.6524 (3)0.5941 (2)0.17555 (9)0.0474 (7)
C110.8048 (4)0.2215 (3)0.10041 (13)0.0736 (10)
C210.8714 (3)0.6420 (3)0.05976 (10)0.0502 (7)
C230.7597 (4)0.6762 (4)0.03060 (13)0.0799 (13)
C240.8281 (4)0.8110 (4)0.01475 (14)0.0806 (11)
C250.9008 (3)0.7909 (3)0.04404 (12)0.0651 (9)
C311.1125 (3)0.5303 (3)0.20426 (11)0.0598 (8)
C321.2161 (3)0.6179 (4)0.25053 (13)0.0735 (10)
C610.5567 (3)0.7029 (2)0.13466 (10)0.0494 (7)
C630.4479 (4)0.9212 (4)0.10166 (17)0.0913 (14)
C640.4010 (4)0.8147 (5)0.06484 (14)0.0948 (13)
C650.4673 (3)0.6663 (3)0.08677 (13)0.0683 (9)
H20.975900.456570.101530.0570*
H31.099140.699390.138120.0605*
H5A0.793890.610570.254150.0641*
H5B0.693130.763980.240470.0641*
H60.570980.532030.197580.0569*
H11A0.839230.260130.061970.1105*
H11B0.900960.203690.125790.1105*
H11C0.745150.125230.094860.1105*
H230.702260.657710.066680.0957*
H240.828870.901980.037640.0966*
H250.957130.865860.066860.0781*
H31A1.184650.462760.181300.0718*
H31B1.033370.464630.224900.0718*
H32A1.272790.544690.276490.1102*
H32B1.296410.681500.230450.1102*
H32C1.145170.683150.274100.1102*
H630.419061.026180.098650.1094*
H640.336000.829150.030170.1138*
H650.449880.567490.070390.0820*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0690 (12)0.0531 (10)0.0846 (12)0.0196 (8)0.0085 (9)0.0077 (9)
O40.0694 (11)0.0429 (10)0.0930 (13)0.0047 (8)0.0102 (9)0.0119 (9)
O220.0740 (11)0.0725 (11)0.0582 (10)0.0048 (9)0.0007 (8)0.0028 (9)
O620.0835 (14)0.0554 (11)0.1130 (16)0.0072 (9)0.0142 (12)0.0084 (10)
N10.0483 (10)0.0340 (9)0.0558 (10)0.0019 (7)0.0060 (8)0.0022 (8)
C10.0630 (14)0.0377 (11)0.0536 (12)0.0060 (10)0.0001 (10)0.0010 (9)
C20.0453 (11)0.0403 (11)0.0572 (12)0.0017 (9)0.0082 (9)0.0026 (9)
C30.0458 (11)0.0426 (11)0.0629 (13)0.0015 (9)0.0012 (10)0.0011 (10)
C40.0503 (12)0.0439 (12)0.0582 (13)0.0021 (10)0.0113 (10)0.0043 (10)
C50.0584 (13)0.0488 (12)0.0531 (12)0.0071 (10)0.0007 (10)0.0079 (10)
C60.0472 (11)0.0410 (11)0.0542 (12)0.0011 (9)0.0073 (9)0.0030 (9)
C110.091 (2)0.0410 (13)0.0891 (19)0.0030 (13)0.0131 (15)0.0126 (13)
C210.0445 (11)0.0522 (12)0.0542 (12)0.0001 (10)0.0068 (9)0.0018 (10)
C230.0703 (18)0.112 (3)0.0574 (15)0.0072 (17)0.0028 (13)0.0150 (16)
C240.0719 (18)0.086 (2)0.0842 (19)0.0106 (16)0.0129 (15)0.0324 (17)
C250.0597 (14)0.0575 (15)0.0783 (17)0.0018 (12)0.0079 (12)0.0137 (13)
C310.0515 (13)0.0555 (14)0.0724 (15)0.0099 (11)0.0004 (11)0.0021 (12)
C320.0538 (15)0.0861 (19)0.0800 (17)0.0134 (13)0.0114 (13)0.0036 (15)
C610.0437 (11)0.0394 (11)0.0653 (14)0.0005 (9)0.0086 (10)0.0034 (10)
C630.078 (2)0.071 (2)0.124 (3)0.0185 (16)0.0187 (19)0.0262 (19)
C640.0636 (17)0.149 (3)0.0712 (18)0.021 (2)0.0157 (14)0.002 (2)
C650.0541 (14)0.0679 (16)0.0822 (17)0.0053 (12)0.0187 (12)0.0299 (14)
Geometric parameters (Å, º) top
O1—C11.224 (3)C63—C641.276 (5)
O4—C41.218 (3)C64—C651.458 (5)
O22—C211.367 (3)C2—H20.9800
O22—C231.373 (4)C3—H30.9800
O62—C611.355 (3)C5—H5A0.9700
O62—C631.373 (4)C5—H5B0.9700
N1—C11.369 (3)C6—H60.9800
N1—C21.478 (3)C11—H11A0.9600
N1—C61.474 (3)C11—H11B0.9600
C1—C111.499 (4)C11—H11C0.9600
C2—C31.545 (3)C23—H230.9300
C2—C211.492 (3)C24—H240.9300
C3—C41.510 (4)C25—H250.9300
C3—C311.538 (4)C31—H31A0.9700
C4—C51.497 (3)C31—H31B0.9700
C5—C61.533 (3)C32—H32A0.9600
C6—C611.502 (3)C32—H32B0.9600
C21—C251.344 (4)C32—H32C0.9600
C23—C241.323 (5)C63—H630.9300
C24—C251.429 (4)C64—H640.9300
C31—C321.509 (4)C65—H650.9300
C61—C651.309 (4)
O1···C613.412 (3)C24···H11Avi2.9500
O1···C653.404 (4)C24···H63vii3.0400
O4···C6i3.395 (3)C25···H32.7200
O4···C323.397 (4)C31···H5A2.8900
O22···C13.314 (3)C61···H32Bviii3.0100
O22···N12.943 (3)C63···H24vii3.0200
O22···C653.166 (3)C63···H11Cix2.9700
O62···C43.211 (4)H2···C112.4400
O1···H63ii2.7900H2···H11A2.1800
O1···H652.8800H2···H11B2.3100
O1···H32Ciii2.6500H2···H31A2.4200
O1···H62.2800H2···C23vi2.9000
O1···H23iv2.6600H3···C252.7200
O4···H5Ai2.8900H3···H252.4000
O4···H32Av2.6900H3···H32B2.5700
O4···H6i2.6100H5A···C312.8900
O22···H11A2.8700H5A···H31B2.3900
O22···H65iv2.8900H5A···O4iii2.8900
O62···H5B2.5100H5B···O622.5100
N1···O222.943 (3)H5B···C1i3.0800
N1···H31B2.8500H6···O12.2800
C1···O223.314 (3)H6···O4iii2.6100
C1···C653.462 (4)H11A···O222.8700
C1···C5iii3.564 (4)H11A···C22.7700
C4···C253.350 (4)H11A···H22.1800
C4···O623.211 (4)H11A···C24vi2.9500
C5···C1i3.564 (4)H11A···H64iv2.5800
C6···O4iii3.395 (3)H11B···C22.9400
C11···C24vi3.549 (5)H11B···H22.3100
C21···C653.320 (4)H11C···C63ii2.9700
C21···C613.095 (4)H23···O1iv2.6600
C23···C653.540 (4)H23···H65iv2.2800
C24···C11vi3.549 (5)H24···C63vii3.0200
C25···C613.530 (4)H24···H63vii2.4700
C25···C43.350 (4)H25···C32.8800
C32···O43.397 (4)H25···C43.0200
C61···C253.530 (4)H25···H32.4000
C61···O13.412 (3)H31A···H22.4200
C61···C213.095 (4)H31B···N12.8500
C65···O13.404 (4)H31B···C52.8800
C65···O223.166 (3)H31B···H5A2.3900
C65···C13.462 (4)H32A···O4x2.6900
C65···C233.540 (4)H32B···C61xi3.0100
C65···C213.320 (4)H32B···H32.5700
C1···H5Biii3.0800H32C···C42.6300
C1···H653.0500H32C···O1i2.6500
C2···H11A2.7700H63···O1ix2.7900
C2···H11B2.9400H63···C24vii3.0400
C3···H252.8800H63···H24vii2.4700
C4···H32C2.6300H64···H11Aiv2.5800
C4···H253.0200H65···O12.8800
C5···H31B2.8800H65···C13.0500
C11···H22.4400H65···O22iv2.8900
C23···H2vi2.9000H65···C23iv2.8100
C23···H65iv2.8100H65···H23iv2.2800
C21—O22—C23106.9 (2)C31—C3—H3108.00
C61—O62—C63106.4 (2)C4—C5—H5A109.00
C1—N1—C2123.32 (17)C4—C5—H5B109.00
C1—N1—C6117.77 (17)C6—C5—H5A109.00
C2—N1—C6117.72 (15)C6—C5—H5B109.00
O1—C1—N1120.67 (19)H5A—C5—H5B108.00
O1—C1—C11120.92 (19)N1—C6—H6107.00
N1—C1—C11118.3 (2)C5—C6—H6107.00
N1—C2—C3111.44 (17)C61—C6—H6107.00
N1—C2—C21112.17 (19)C1—C11—H11A109.00
C3—C2—C21111.14 (18)C1—C11—H11B109.00
C2—C3—C4109.96 (19)C1—C11—H11C109.00
C2—C3—C31111.8 (2)H11A—C11—H11B109.00
C4—C3—C31111.08 (19)H11A—C11—H11C109.00
O4—C4—C3122.3 (2)H11B—C11—H11C109.00
O4—C4—C5122.8 (2)O22—C23—H23125.00
C3—C4—C5114.9 (2)C24—C23—H23125.00
C4—C5—C6111.24 (19)C23—C24—H24126.00
N1—C6—C5109.52 (19)C25—C24—H24126.00
N1—C6—C61112.76 (17)C21—C25—H25127.00
C5—C6—C61112.24 (16)C24—C25—H25127.00
O22—C21—C2116.1 (2)C3—C31—H31A109.00
O22—C21—C25109.7 (2)C3—C31—H31B109.00
C2—C21—C25134.2 (2)C32—C31—H31A109.00
O22—C23—C24109.8 (3)C32—C31—H31B109.00
C23—C24—C25107.4 (3)H31A—C31—H31B108.00
C21—C25—C24106.3 (2)C31—C32—H32A109.00
C3—C31—C32113.0 (2)C31—C32—H32B109.00
O62—C61—C6121.4 (2)C31—C32—H32C110.00
O62—C61—C65111.0 (2)H32A—C32—H32B109.00
C6—C61—C65127.49 (19)H32A—C32—H32C109.00
O62—C63—C64110.0 (3)H32B—C32—H32C109.00
C63—C64—C65107.9 (3)O62—C63—H63125.00
C61—C65—C64104.7 (2)C64—C63—H63125.00
N1—C2—H2107.00C63—C64—H64126.00
C3—C2—H2107.00C65—C64—H64126.00
C21—C2—H2107.00C61—C65—H65128.00
C2—C3—H3108.00C64—C65—H65128.00
C4—C3—H3108.00
C21—O22—C23—C241.4 (3)N1—C2—C21—C25120.6 (3)
C23—O22—C21—C251.2 (3)N1—C2—C3—C448.1 (2)
C23—O22—C21—C2178.3 (2)C4—C3—C31—C3255.7 (3)
C63—O62—C61—C651.3 (3)C2—C3—C31—C32178.9 (2)
C61—O62—C63—C640.8 (4)C31—C3—C4—C572.1 (3)
C63—O62—C61—C6178.3 (2)C2—C3—C4—C552.3 (3)
C6—N1—C1—O12.1 (3)C31—C3—C4—O4108.2 (3)
C1—N1—C6—C6194.9 (2)C2—C3—C4—O4127.5 (2)
C2—N1—C1—C1118.0 (3)O4—C4—C5—C6124.9 (2)
C1—N1—C6—C5139.38 (19)C3—C4—C5—C654.8 (3)
C1—N1—C2—C2193.6 (2)C4—C5—C6—N151.5 (2)
C6—N1—C2—C351.7 (2)C4—C5—C6—C6174.6 (3)
C2—N1—C1—O1165.1 (2)C5—C6—C61—O6210.6 (3)
C2—N1—C6—C552.7 (2)N1—C6—C61—O62134.8 (2)
C6—N1—C2—C2173.6 (2)N1—C6—C61—C6548.7 (3)
C1—N1—C2—C3141.0 (2)C5—C6—C61—C65173.0 (2)
C2—N1—C6—C6173.1 (2)C2—C21—C25—C24178.9 (3)
C6—N1—C1—C11174.8 (2)O22—C21—C25—C240.5 (3)
C21—C2—C3—C31158.3 (2)O22—C23—C24—C251.1 (4)
N1—C2—C3—C3175.8 (2)C23—C24—C25—C210.3 (3)
N1—C2—C21—O2258.7 (2)C6—C61—C65—C64179.3 (2)
C21—C2—C3—C477.9 (2)O62—C61—C65—C642.6 (3)
C3—C2—C21—O22175.77 (19)O62—C63—C64—C652.3 (4)
C3—C2—C21—C254.9 (4)C63—C64—C65—C613.0 (3)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x, y1, z; (iii) x+3/2, y1/2, z+1/2; (iv) x+1, y+1, z; (v) x+5/2, y+1/2, z+1/2; (vi) x+2, y+1, z; (vii) x+1, y+2, z; (viii) x1, y, z; (ix) x, y+1, z; (x) x+5/2, y1/2, z+1/2; (xi) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.982.282.693 (3)104
 

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