Literature DB >> 21200935

t-3-Ethyl-r-2,c-6-bis-(2-fur-yl)piperidin-4-one.

S Balamurugan, A Thiruvalluvar, R J Butcher, A Manimekalai, J Jayabharathi.   

Abstract

In the title mol-ecule, C(15)H(17)NO(3), the piperidine ring adopts a chair conformation. The dihedral angle between the two furyl rings is 72.4 (1)°. The ethyl group and the furyl rings have equatorial orientations. Mol-ecules are linked by N-H⋯O hydrogen bonds.

Entities:  

Year:  2007        PMID： 21200935      PMCID： PMC2915017          DOI： 10.1107/S1600536807062204

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a related crystal structure, see Thiruvalluvar et al. (2007 ▶).

Experimental

Crystal data

C15H17NO3 M = 259.30 Monoclinic, a = 5.1620 (2) Å b = 20.2855 (9) Å c = 12.9825 (5) Å β = 91.128 (3)° V = 1359.18 (10) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 200 (2) K 0.41 × 0.36 × 0.18 mm

Data collection

Oxford Diffraction Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.965, T max = 1.000 (expected range = 0.950–0.984) 11183 measured reflections 4354 independent reflections 2961 reflections with I > 2σ(I) R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.194 S = 1.07 4354 reflections 174 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.41 e Å−3 Δρmin = −0.26 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062204/rn2035sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062204/rn2035Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H17NO3F000 = 552
Mr = 259.30Dx = 1.267 Mg m−3
Monoclinic, P21/cMelting point: 320 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 5.1620 (2) ÅCell parameters from 5794 reflections
b = 20.2855 (9) Åθ = 4.7–32.4º
c = 12.9825 (5) ŵ = 0.09 mm−1
β = 91.128 (3)ºT = 200 (2) K
V = 1359.18 (10) Å3Plate, colourless
Z = 40.41 × 0.36 × 0.18 mm
Oxford Diffraction Gemini diffractometer4354 independent reflections
Radiation source: fine-focus sealed tube2961 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.072
Detector resolution: 10.5081 pixels mm-1θmax = 32.4º
T = 200(2) Kθmin = 4.7º
phi and ω scansh = −7→7
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −29→23
Tmin = 0.965, Tmax = 1.000l = −18→18
11183 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.194  w = 1/[σ2(Fo2) + (0.1195P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4354 reflectionsΔρmax = 0.41 e Å−3
174 parametersΔρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
O40.7516 (2)0.19399 (5)0.70845 (7)0.0423 (3)
O220.65339 (19)0.10804 (6)0.32132 (8)0.0390 (3)
O620.43126 (18)0.40669 (5)0.50031 (7)0.0332 (3)
N10.6097 (2)0.24278 (5)0.41720 (8)0.0246 (3)
C20.7958 (2)0.19114 (6)0.44599 (9)0.0236 (3)
C30.6869 (3)0.15193 (6)0.53734 (9)0.0262 (3)
C40.6510 (2)0.20108 (6)0.62400 (9)0.0273 (3)
C50.4922 (3)0.26132 (6)0.59650 (9)0.0278 (3)
C60.5885 (2)0.29338 (6)0.49665 (9)0.0237 (3)
C130.8496 (4)0.09209 (8)0.57028 (12)0.0435 (5)
C140.6945 (5)0.04322 (9)0.63338 (16)0.0622 (7)
C210.8466 (2)0.14932 (6)0.35453 (9)0.0259 (3)
C230.7409 (3)0.07793 (9)0.23394 (12)0.0468 (5)
C240.9769 (4)0.09963 (9)0.21229 (12)0.0485 (5)
C251.0469 (3)0.14554 (8)0.29020 (12)0.0382 (4)
C610.4080 (2)0.34542 (6)0.45684 (9)0.0258 (3)
C630.2484 (2)0.44582 (5)0.45159 (9)0.0374 (4)
C640.1172 (2)0.41118 (5)0.38123 (9)0.0405 (5)
C650.2180 (3)0.34610 (7)0.38376 (11)0.0356 (4)
H10.657 (3)0.2606 (8)0.3599 (13)0.028 (4)*
H20.961890.212500.468730.0282*
H30.511270.135460.516020.0314*
H5A0.504370.293630.653530.0333*
H5B0.308080.248590.587270.0333*
H60.763020.313340.510110.0284*
H13A1.001350.107250.611640.0521*
H13B0.914490.069680.508160.0521*
H14A0.805080.005790.652820.0932*
H14B0.545860.027450.592230.0932*
H14C0.632850.064980.695680.0932*
H230.646570.046190.194610.0561*
H241.078790.086810.155540.0582*
H251.205380.169180.295910.0458*
H630.220220.491110.466250.0449*
H64−0.018590.427000.337410.0486*
H650.162600.310030.342160.0427*
U11U22U33U12U13U23
O40.0628 (7)0.0404 (6)0.0232 (5)0.0127 (5)−0.0095 (4)−0.0034 (4)
O220.0381 (5)0.0437 (6)0.0353 (5)−0.0029 (4)0.0006 (4)−0.0178 (5)
O620.0413 (6)0.0228 (4)0.0352 (5)0.0053 (4)−0.0039 (4)−0.0016 (4)
N10.0316 (5)0.0236 (5)0.0185 (4)0.0023 (4)0.0002 (3)−0.0006 (4)
C20.0274 (6)0.0222 (6)0.0210 (5)0.0013 (4)−0.0016 (4)−0.0024 (4)
C30.0372 (7)0.0208 (6)0.0205 (5)0.0027 (5)−0.0012 (4)0.0015 (4)
C40.0352 (6)0.0271 (6)0.0197 (5)0.0005 (5)0.0015 (4)0.0006 (4)
C50.0369 (7)0.0249 (6)0.0217 (5)0.0054 (5)0.0018 (4)−0.0024 (4)
C60.0285 (6)0.0194 (5)0.0230 (5)0.0009 (4)−0.0026 (4)−0.0022 (4)
C130.0684 (10)0.0324 (7)0.0295 (6)0.0188 (7)0.0000 (6)0.0034 (6)
C140.1052 (16)0.0309 (8)0.0497 (10)−0.0023 (9)−0.0165 (10)0.0132 (8)
C210.0292 (6)0.0262 (6)0.0221 (5)0.0047 (5)−0.0009 (4)−0.0013 (4)
C230.0644 (11)0.0453 (9)0.0303 (7)0.0166 (8)−0.0064 (7)−0.0178 (7)
C240.0660 (11)0.0504 (10)0.0295 (7)0.0227 (8)0.0118 (7)−0.0069 (6)
C250.0408 (8)0.0346 (7)0.0397 (8)0.0044 (6)0.0124 (6)−0.0004 (6)
C610.0324 (6)0.0200 (5)0.0250 (5)0.0007 (5)0.0019 (4)0.0008 (4)
C630.0446 (8)0.0267 (7)0.0410 (8)0.0102 (6)0.0034 (6)0.0049 (5)
C640.0420 (8)0.0370 (8)0.0423 (8)0.0091 (6)−0.0049 (6)0.0100 (6)
C650.0396 (7)0.0304 (7)0.0364 (7)0.0023 (6)−0.0083 (5)0.0008 (5)
O4—C41.2124 (15)C61—C651.3512 (19)
O22—C211.3656 (16)C63—C641.3276 (15)
O22—C231.3727 (19)C64—C651.4192 (18)
O62—C611.3693 (16)C2—H21.0000
O62—C631.3775 (14)C3—H31.0000
N1—C21.4648 (15)C5—H5A0.9900
N1—C61.4608 (16)C5—H5B0.9900
N1—H10.867 (17)C6—H61.0000
C2—C211.4868 (17)C13—H13A0.9900
C2—C31.5432 (17)C13—H13B0.9900
C3—C41.5174 (17)C14—H14A0.9800
C3—C131.532 (2)C14—H14B0.9800
C4—C51.5104 (18)C14—H14C0.9800
C5—C61.5414 (17)C23—H230.9500
C6—C611.4936 (16)C24—H240.9500
C13—C141.523 (3)C25—H250.9500
C21—C251.3440 (19)C63—H630.9500
C23—C241.331 (3)C64—H640.9500
C24—C251.417 (2)C65—H650.9500
O4···C143.222 (2)H1···C652.875 (16)
O4···C65i3.3796 (18)H1···O4vi2.234 (17)
O4···N1ii3.0991 (14)H2···H5Bvii2.4500
O22···C25iii3.2394 (19)H2···H62.3600
O22···C133.3835 (19)H3···O222.7000
O22···N13.0137 (16)H3···H14B2.4100
O62···C23ii3.4148 (18)H5A···C23ii3.0500
O4···H65i2.7200H5A···H25v2.5500
O4···H1ii2.234 (17)H5B···H2iii2.4500
O4···H14C2.6900H6···C65vii2.9700
O4···H13A2.5300H6···H22.3600
O22···H32.7000H13A···O42.5300
O22···H25iii2.6400H13B···O222.8600
O22···H13B2.8600H13B···C212.5900
O62···H63iv2.7700H14A···C24ix2.9700
O62···H23ii2.9000H14B···H32.4100
O62···H24v2.7400H14C···O42.6900
N1···O223.0137 (16)H14C···C42.9200
N1···O4vi3.0991 (14)H14C···H64i2.5500
N1···H652.8400H23···C63xii2.8400
C13···O223.3835 (19)H23···H63xii2.4800
C14···O43.222 (2)H23···O62vi2.9000
C23···O62vi3.4148 (18)H24···O62xiii2.7400
C25···O22vii3.2394 (19)H24···C63xiii2.8800
C65···O4viii3.3796 (18)H25···O22vii2.6400
C4···H14C2.9200H25···H5Axiii2.5500
C14···H64i3.0700H63···H23x2.4800
C21···H13B2.5900H63···O62iv2.7700
C23···H5Avi3.0500H63···C63xi2.9500
C24···H14Aix2.9700H63···H63xi2.4800
C63···H23x2.8400H64···C14viii3.0700
C63···H63xi2.9500H64···H14Cviii2.5500
C63···H24v2.8800H65···N12.8400
C65···H12.875 (16)H65···O4viii2.7200
C65···H6iii2.9700
C21—O22—C23106.48 (11)C2—C3—H3108.00
C61—O62—C63106.26 (9)C4—C3—H3108.00
C2—N1—C6112.35 (9)C13—C3—H3108.00
C2—N1—H1108.8 (10)C4—C5—H5A109.00
C6—N1—H1109.8 (11)C4—C5—H5B109.00
N1—C2—C3108.52 (9)C6—C5—H5A109.00
N1—C2—C21109.23 (9)C6—C5—H5B109.00
C3—C2—C21113.10 (10)H5A—C5—H5B108.00
C2—C3—C4106.43 (10)N1—C6—H6109.00
C4—C3—C13112.82 (11)C5—C6—H6109.00
C2—C3—C13114.64 (12)C61—C6—H6109.00
O4—C4—C5122.04 (11)C3—C13—H13A109.00
O4—C4—C3122.42 (11)C3—C13—H13B109.00
C3—C4—C5115.47 (10)C14—C13—H13A109.00
C4—C5—C6110.96 (11)C14—C13—H13B109.00
N1—C6—C5109.10 (10)H13A—C13—H13B108.00
C5—C6—C61112.33 (10)C13—C14—H14A109.00
N1—C6—C61107.89 (9)C13—C14—H14B109.00
C3—C13—C14112.00 (16)C13—C14—H14C109.00
O22—C21—C25109.56 (11)H14A—C14—H14B109.00
O22—C21—C2117.57 (9)H14A—C14—H14C109.00
C2—C21—C25132.75 (12)H14B—C14—H14C109.00
O22—C23—C24110.18 (14)O22—C23—H23125.00
C23—C24—C25106.76 (15)C24—C23—H23125.00
C21—C25—C24107.02 (14)C23—C24—H24127.00
O62—C61—C65109.68 (11)C25—C24—H24127.00
C6—C61—C65133.59 (12)C21—C25—H25126.00
O62—C61—C6116.74 (10)C24—C25—H25126.00
O62—C63—C64110.28 (9)O62—C63—H63125.00
C63—C64—C65107.13 (10)C64—C63—H63125.00
C61—C65—C64106.65 (12)C63—C64—H64126.00
N1—C2—H2109.00C65—C64—H64126.00
C3—C2—H2109.00C61—C65—H65127.00
C21—C2—H2109.00C64—C65—H65127.00
C21—O22—C23—C24−0.64 (18)C4—C3—C13—C1477.18 (17)
C23—O22—C21—C2176.79 (12)C2—C3—C13—C14−160.78 (13)
C23—O22—C21—C250.33 (16)C2—C3—C4—O4−123.63 (12)
C63—O62—C61—C650.00 (14)C13—C3—C4—C5179.97 (13)
C63—O62—C61—C6179.71 (9)C3—C4—C5—C6−49.62 (14)
C61—O62—C63—C64−0.05 (14)O4—C4—C5—C6127.45 (12)
C6—N1—C2—C21−168.73 (9)C4—C5—C6—N150.06 (13)
C6—N1—C2—C367.56 (12)C4—C5—C6—C61169.65 (10)
C2—N1—C6—C5−61.28 (12)C5—C6—C61—C65−97.83 (16)
C2—N1—C6—C61176.43 (9)C5—C6—C61—O6282.53 (12)
C21—C2—C3—C1353.53 (14)N1—C6—C61—O62−157.19 (10)
C3—C2—C21—O2249.48 (14)N1—C6—C61—C6522.46 (18)
N1—C2—C21—C25103.97 (16)C2—C21—C25—C24−175.66 (14)
N1—C2—C3—C4−59.65 (12)O22—C21—C25—C240.07 (16)
C3—C2—C21—C25−135.07 (15)O22—C23—C24—C250.7 (2)
N1—C2—C3—C13174.89 (11)C23—C24—C25—C21−0.46 (19)
C21—C2—C3—C4178.99 (9)O62—C61—C65—C640.07 (16)
N1—C2—C21—O22−71.49 (13)C6—C61—C65—C64−179.60 (12)
C13—C3—C4—O42.92 (18)O62—C63—C64—C650.09 (13)
C2—C3—C4—C553.42 (14)C63—C64—C65—C61−0.10 (14)
D—H···AD—HH···AD···AD—H···A
N1—H1···O4vi0.867 (17)2.234 (17)3.0991 (14)176.2 (15)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O4i0.867 (17)2.234 (17)3.0991 (14)176.2 (15)

Symmetry code: (i) .

  1 in total

1.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600
  1 in total
  1 in total

1.  r-2,c-6-Bis(3-methoxy-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one.

Authors:  P Parthiban; V Ramkumar; Nanjundan Ashok Kumar; Jong Su Kim; Yeon Tae Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-31
  1 in total

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