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In the title mol­ecule, C17H19NO4, the piperidine ring adopts a twist-boat conformation. The acetyl group at position 1 has a bis­ectional orientation. The planar furyl rings at positions 2 and 6 have axial and bis­ectional orientations, respectively. The methyl groups at positions 3 and 5 have bis­ectional and equatorial orientations, respectively. In the crystal structure, the mol­ecules are stabilized by inter- and intra­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001936/at2205sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001936/at2205Isup2.hkl
Contains datablock I

CCDC reference: 636122

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.164
  • Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O62 - C61 .. 6.43 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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-r-2,c-6-di-2-furyl-3,5-dimethylpiperidin-4-one top
Crystal data top
C17H19NO4F(000) = 640
Mr = 301.33Dx = 1.280 Mg m3
Monoclinic, P21/cMelting point: 389 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.1342 (7) ÅCell parameters from 6242 reflections
b = 15.726 (1) Åθ = 2.3–27.3°
c = 11.1749 (8) ŵ = 0.09 mm1
β = 103.055 (3)°T = 293 K
V = 1563.72 (19) Å3Plate, colourless
Z = 40.20 × 0.15 × 0.15 mm
Data collection top
Bruker SMART
diffractometer
4676 independent reflections
Radiation source: fine-focus sealed tube3038 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 30.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.982, Tmax = 0.986k = 2222
20527 measured reflectionsl = 1515
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0737P)2 + 0.2676P]
where P = (Fo2 + 2Fc2)/3
4676 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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. 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
O40.47459 (16)0.13627 (10)0.06897 (12)0.0874 (5)
O110.53975 (16)0.10815 (9)0.41221 (12)0.0774 (5)
O220.86987 (14)0.21802 (10)0.39494 (12)0.0808 (5)
O620.93782 (15)0.00012 (11)0.33444 (11)0.0857 (5)
N10.65381 (12)0.10529 (7)0.25387 (9)0.0416 (3)
C20.64212 (15)0.19815 (9)0.24175 (13)0.0461 (4)
C30.55209 (18)0.22048 (9)0.11146 (14)0.0546 (5)
C40.57230 (18)0.15217 (10)0.02120 (13)0.0535 (5)
C50.72026 (17)0.10586 (10)0.05017 (12)0.0489 (4)
C60.74067 (15)0.06111 (9)0.17609 (11)0.0432 (4)
C110.59485 (15)0.06621 (10)0.34150 (12)0.0492 (4)
C120.5941 (2)0.02894 (11)0.34692 (14)0.0596 (5)
C210.79151 (18)0.24001 (10)0.27919 (16)0.0595 (5)
C231.0007 (3)0.2617 (2)0.4150 (3)0.1130 (10)
C241.0080 (3)0.30889 (19)0.3199 (4)0.1204 (13)
C250.8703 (3)0.29585 (14)0.2284 (3)0.0905 (8)
C310.3874 (2)0.23573 (15)0.1082 (2)0.0867 (8)
C510.7401 (2)0.04315 (13)0.04883 (15)0.0706 (6)
C610.90431 (17)0.05356 (11)0.23654 (13)0.0538 (5)
C631.0906 (3)0.0043 (2)0.3776 (2)0.0965 (9)
C641.1509 (2)0.05743 (18)0.3123 (2)0.0905 (9)
C651.0303 (2)0.08906 (14)0.2198 (2)0.0776 (7)
H20.582340.217580.299110.0553*
H30.593450.273450.086710.0655*
H50.799860.148630.057730.0586*
H60.700130.003410.161170.0518*
H12A0.545450.047040.410290.0895*
H12B0.695550.049610.364650.0895*
H12C0.540620.051160.269290.0895*
H231.075480.258570.486800.1355*
H241.087190.344230.312600.1446*
H250.842380.320780.151140.1085*
H31A0.337010.254350.027560.1300*
H31B0.378330.278620.167220.1300*
H31C0.342380.183880.127680.1300*
H51A0.661620.001330.060380.1059*
H51B0.835930.015530.023990.1059*
H51C0.735360.073060.124500.1059*
H631.144290.026310.444460.1156*
H641.252000.071530.324080.1085*
H651.037970.127680.158480.0931*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0871 (9)0.1003 (10)0.0588 (7)0.0066 (8)0.0168 (7)0.0138 (7)
O110.1005 (10)0.0783 (8)0.0709 (8)0.0033 (7)0.0561 (8)0.0065 (6)
O220.0526 (7)0.1121 (10)0.0708 (8)0.0071 (6)0.0005 (6)0.0317 (8)
O620.0649 (8)0.1320 (12)0.0542 (7)0.0103 (8)0.0011 (6)0.0145 (8)
N10.0426 (5)0.0472 (6)0.0368 (5)0.0006 (4)0.0130 (4)0.0027 (4)
C20.0460 (7)0.0465 (7)0.0472 (7)0.0018 (5)0.0132 (6)0.0077 (6)
C30.0577 (9)0.0457 (7)0.0571 (9)0.0034 (6)0.0062 (7)0.0038 (6)
C40.0624 (9)0.0553 (8)0.0398 (7)0.0094 (6)0.0050 (6)0.0052 (6)
C50.0564 (8)0.0572 (8)0.0349 (6)0.0090 (6)0.0142 (6)0.0029 (6)
C60.0481 (7)0.0492 (7)0.0336 (6)0.0011 (5)0.0119 (5)0.0046 (5)
C110.0467 (7)0.0634 (8)0.0384 (7)0.0057 (6)0.0118 (5)0.0010 (6)
C120.0702 (10)0.0635 (9)0.0454 (8)0.0126 (7)0.0137 (7)0.0051 (7)
C210.0528 (8)0.0584 (9)0.0675 (10)0.0086 (7)0.0141 (7)0.0234 (8)
C230.0569 (12)0.143 (2)0.132 (2)0.0243 (14)0.0066 (14)0.070 (2)
C240.0729 (15)0.1074 (19)0.187 (3)0.0478 (14)0.0423 (18)0.067 (2)
C250.0871 (14)0.0683 (11)0.1223 (18)0.0318 (10)0.0370 (13)0.0248 (12)
C310.0638 (11)0.0927 (14)0.0940 (15)0.0219 (10)0.0025 (10)0.0051 (12)
C510.0920 (13)0.0822 (12)0.0432 (8)0.0032 (10)0.0269 (8)0.0117 (8)
C610.0518 (8)0.0699 (9)0.0407 (7)0.0090 (7)0.0127 (6)0.0099 (7)
C630.0624 (12)0.155 (2)0.0615 (12)0.0276 (13)0.0083 (9)0.0106 (14)
C640.0461 (9)0.141 (2)0.0831 (14)0.0128 (11)0.0118 (9)0.0308 (14)
C650.0521 (9)0.1000 (14)0.0831 (13)0.0046 (9)0.0206 (9)0.0001 (11)
Geometric parameters (Å, º) top
O4—C41.212 (2)C63—C641.310 (4)
O11—C111.222 (2)C64—C651.420 (3)
O22—C211.374 (2)C2—H20.9800
O22—C231.353 (3)C3—H30.9800
O62—C611.361 (2)C5—H50.9800
O62—C631.371 (3)C6—H60.9800
N1—C21.4682 (18)C12—H12A0.9600
N1—C61.4762 (17)C12—H12B0.9600
N1—C111.3656 (17)C12—H12C0.9600
C2—C31.542 (2)C23—H230.9300
C2—C211.487 (2)C24—H240.9300
C3—C41.513 (2)C25—H250.9300
C3—C311.516 (3)C31—H31A0.9600
C4—C51.505 (2)C31—H31B0.9600
C5—C61.5465 (19)C31—H31C0.9600
C5—C511.523 (2)C51—H51A0.9600
C6—C611.500 (2)C51—H51B0.9600
C11—C121.498 (2)C51—H51C0.9600
C21—C251.340 (3)C63—H630.9300
C23—C241.310 (5)C64—H640.9300
C24—C251.445 (5)C65—H650.9300
C61—C651.330 (3)
O22···N12.8491 (18)C25···H52.9800
O22···C113.419 (2)C25···H51Civ3.0600
O22···C613.190 (2)C31···H23x2.8700
O22···C653.374 (3)C61···H12B3.0900
O62···C123.206 (2)C61···H51B2.9000
O62···C113.320 (2)C63···H25vii2.9800
O62···N13.0386 (19)C65···H52.6200
O62···C63i3.287 (3)H2···O112.2200
O4···H51A2.7100H2···H31B2.3100
O4···H31A2.6100H3···C252.6900
O4···H31C2.8400H3···H252.3500
O4···H6ii2.7700H3···O11xi2.6600
O4···H12Cii2.5800H5···C22.8700
O4···H51C2.7800H5···C212.8800
O11···H22.2200H5···C252.9800
O11···H64iii2.6500H5···C652.6200
O11···H3iv2.6600H5···H652.2400
O11···H12Av2.4800H5···C23xi3.0400
O62···H12B2.4400H6···C122.5300
O62···H63i2.7700H6···H12B2.4300
N1···O222.8491 (18)H6···H12C2.2600
N1···O623.0386 (19)H6···H51A2.4200
C5···C213.267 (2)H6···O4ii2.7700
C11···O623.320 (2)H12A···O11v2.4800
C11···O223.419 (2)H12B···O622.4400
C12···C613.580 (2)H12B···C62.8300
C12···O623.206 (2)H12B···C613.0900
C21···C613.179 (2)H12B···H62.4300
C21···C53.267 (2)H12B···H63i2.5900
C21···C653.389 (3)H12C···C62.9000
C23···C653.531 (4)H12C···H62.2600
C25···C653.576 (3)H12C···O4ii2.5800
C25···C63vi3.531 (4)H23···C31ix2.8700
C61···C123.580 (2)H23···H31Aix2.3400
C61···C213.179 (2)H25···C33.0300
C61···O223.190 (2)H25···H32.3500
C63···C63i3.505 (3)H25···C63vi2.9800
C63···O62i3.287 (3)H31A···O42.6100
C63···C25vii3.531 (4)H31A···C23x3.0600
C65···C213.389 (3)H31A···H23x2.3400
C65···C253.576 (3)H31B···H22.3100
C65···C233.531 (4)H31B···C12xii3.0400
C65···O223.374 (3)H31C···O42.8400
C2···H52.8700H51A···O42.7100
C3···H253.0300H51A···H62.4200
C5···H652.9000H51B···C612.9000
C6···H12B2.8300H51C···O42.7800
C6···H12C2.9000H51C···C25xi3.0600
C11···H64iii3.0900H63···O62i2.7700
C11···H63i3.0400H63···C11i3.0400
C12···H62.5300H63···C12i3.0600
C12···H63i3.0600H63···H12Bi2.5900
C12···H31Bviii3.0400H64···O11xiii2.6500
C21···H52.8800H64···C11xiii3.0900
C23···H5iv3.0400H65···C52.9000
C23···H31Aix3.0600H65···H52.2400
C25···H32.6900
C21—O22—C23106.33 (18)C4—C3—H3108.00
C61—O62—C63106.11 (16)C31—C3—H3108.00
C2—N1—C6116.83 (10)C4—C5—H5107.00
C2—N1—C11118.78 (11)C6—C5—H5107.00
C6—N1—C11124.19 (11)C51—C5—H5107.00
N1—C2—C3109.01 (11)N1—C6—H6108.00
N1—C2—C21111.79 (12)C5—C6—H6108.00
C3—C2—C21115.11 (13)C61—C6—H6108.00
C2—C3—C4110.39 (12)C11—C12—H12A109.00
C2—C3—C31111.93 (14)C11—C12—H12B109.00
C4—C3—C31111.48 (14)C11—C12—H12C109.00
O4—C4—C3121.53 (15)H12A—C12—H12B109.00
O4—C4—C5122.42 (15)H12A—C12—H12C109.00
C3—C4—C5116.05 (13)H12B—C12—H12C109.00
C4—C5—C6109.50 (12)O22—C23—H23124.00
C4—C5—C51113.93 (12)C24—C23—H23125.00
C6—C5—C51110.89 (13)C23—C24—H24126.00
N1—C6—C5110.56 (11)C25—C24—H24126.00
N1—C6—C61112.68 (11)C21—C25—H25127.00
C5—C6—C61110.42 (12)C24—C25—H25128.00
O11—C11—N1120.51 (15)C3—C31—H31A109.00
O11—C11—C12120.46 (14)C3—C31—H31B110.00
N1—C11—C12119.00 (13)C3—C31—H31C109.00
O22—C21—C2113.78 (14)H31A—C31—H31B109.00
O22—C21—C25110.39 (19)H31A—C31—H31C109.00
C2—C21—C25135.83 (19)H31B—C31—H31C109.00
O22—C23—C24111.0 (3)C5—C51—H51A109.00
C23—C24—C25107.3 (3)C5—C51—H51B109.00
C21—C25—C24105.0 (3)C5—C51—H51C109.00
O62—C61—C6115.57 (13)H51A—C51—H51B109.00
O62—C61—C65109.20 (15)H51A—C51—H51C109.00
C6—C61—C65135.21 (16)H51B—C51—H51C109.00
O62—C63—C64111.0 (2)O62—C63—H63124.00
C63—C64—C65105.93 (19)C64—C63—H63124.00
C61—C65—C64107.72 (18)C63—C64—H64127.00
N1—C2—H2107.00C65—C64—H64127.00
C3—C2—H2107.00C61—C65—H65126.00
C21—C2—H2107.00C64—C65—H65126.00
C2—C3—H3108.00
N1—C2—C3—C428.97 (16)C21—C2—C3—C497.55 (15)
C2—C3—C4—C530.22 (18)C21—C2—C3—C31137.65 (15)
C3—C4—C5—C660.09 (17)N1—C2—C21—O2254.08 (17)
C4—C5—C6—N125.83 (16)C3—C2—C21—O22179.16 (13)
C5—C6—N1—C234.76 (15)C31—C3—C4—O424.9 (2)
C6—N1—C2—C365.28 (15)C2—C3—C4—O4149.93 (16)
C23—O22—C21—C250.2 (2)C31—C3—C4—C5155.27 (15)
C21—O22—C23—C240.1 (3)O4—C4—C5—C6120.06 (16)
C23—O22—C21—C2179.36 (18)C3—C4—C5—C51175.09 (14)
C61—O62—C63—C640.3 (3)O4—C4—C5—C514.8 (2)
C63—O62—C61—C6178.26 (17)C51—C5—C6—C6182.22 (16)
C63—O62—C61—C650.3 (2)C51—C5—C6—N1152.39 (13)
C2—N1—C11—O113.4 (2)H5—C5—C6—H6152.1 (1)
C11—N1—C2—C21111.94 (14)C4—C5—C6—C61151.22 (13)
C11—N1—C6—C6185.42 (16)C5—C6—C61—C6515.4 (3)
C6—N1—C11—C1210.75 (19)C5—C6—C61—O62166.55 (13)
C11—N1—C2—C3119.66 (13)N1—C6—C61—O6269.27 (17)
C6—N1—C11—O11171.27 (13)N1—C6—C61—C65108.7 (2)
C2—N1—C6—C6189.34 (14)C2—C21—C25—C24179.2 (2)
C11—N1—C6—C5150.47 (12)O22—C21—C25—C240.2 (3)
C6—N1—C2—C2163.12 (15)O22—C23—C24—C250.1 (3)
C2—N1—C11—C12174.58 (12)C23—C24—C25—C210.2 (3)
N1—C2—C21—C25127.0 (2)O62—C61—C65—C640.7 (2)
C3—C2—C21—C252.0 (3)C6—C61—C65—C64177.44 (19)
N1—C2—C3—C3195.83 (15)O62—C63—C64—C650.7 (3)
H2—C2—C3—H398.8 (2)C63—C64—C65—C610.8 (3)
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z; (iii) x1, y, z; (iv) x, y+1/2, z+1/2; (v) x+1, y, z+1; (vi) x+2, y+1/2, z+1/2; (vii) x+2, y1/2, z+1/2; (viii) x+1, y1/2, z+1/2; (ix) x+1, y+1/2, z+1/2; (x) x1, y+1/2, z1/2; (xi) x, y+1/2, z1/2; (xii) x+1, y+1/2, z+1/2; (xiii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O110.982.222.704 (2)109
C12—H12A···O11v0.962.483.432 (2)170
C12—H12B···O620.962.443.206 (2)137
C12—H12C···O4ii0.962.583.466 (2)153
Symmetry codes: (ii) x+1, y, z; (v) x+1, y, z+1.
 

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