Literature DB >> 21578368

(3E,5E)-1-Benzyl-3,5-dibenzyl-idenepiperidin-4-one.

N S Karthikeyan, K Sathiyanarayanan, P G Aravindan, R S Rathore.   

Abstract

In the title compound, C(26)H(23)NO, C-H⋯O hydrogen bonds generate a ribbon structure along the a axis. These ribbons further assemble into a one-dimensional sheet parallel to the ac plane via C-H⋯π inter-actions. The piperidin-4-one ring adopts a sofa conformation with the 1-benzyl group in the equatorial position, and the 3- and 5-phenyl substituents stretched out on either side. The benzyl-idene units adopt E configurations and the 1-benzyl group is disposed towards the 3- substituent of the piperidin-4-one ring.

Entities:  

Year:  2009        PMID： 21578368      PMCID： PMC2971257          DOI： 10.1107/S1600536809037659

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


Related literature

For literature related to the synthesis and pharmaceutical activity of 3,5-diaryl­idene-4-piperidone compounds, see Krapcho & Turk (1979 ▶); Sviridenkova et al. (2005 ▶); Das et al. (2007 ▶). The crystal structures of four analogous compounds have been reported (Suresh et al., 2007 ▶). For ring conformations, see Cremer & Pople (1975 ▶); Duax et al. (1976 ▶).

Experimental

Crystal data

C26H23NO M = 365.45 Triclinic, a = 6.3354 (4) Å b = 10.2365 (6) Å c = 15.7885 (9) Å α = 75.245 (2)° β = 87.651 (3)° γ = 88.699 (3)° V = 989.24 (10) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 295 K 0.22 × 0.19 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.896, T max = 0.964 25021 measured reflections 6540 independent reflections 4181 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.202 S = 1.06 6540 reflections 253 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.25 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037659/bq2159sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037659/bq2159Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H23NOZ = 2
Mr = 365.45F(000) = 388
Triclinic, P1Dx = 1.227 Mg m−3
Hall symbol: -P 1Melting point: 427 K
a = 6.3354 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2365 (6) ÅCell parameters from 1089 reflections
c = 15.7885 (9) Åθ = 2.6–22.0°
α = 75.245 (2)°µ = 0.07 mm−1
β = 87.651 (3)°T = 295 K
γ = 88.699 (3)°Block, yellow
V = 989.24 (10) Å30.22 × 0.19 × 0.18 mm
Bruker APEXII CCD area-detector diffractometer6540 independent reflections
Radiation source: fine-focus sealed tube4181 reflections with I > 2σ(I)
graphiteRint = 0.035
φ and ω scansθmax = 31.6°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −9→9
Tmin = 0.896, Tmax = 0.964k = −14→15
25021 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1034P)2 + 0.1348P] where P = (Fo2 + 2Fc2)/3
6540 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
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.
xyzUiso*/Ueq
N10.41574 (19)0.06361 (11)0.29573 (7)0.0388 (3)
O1−0.03961 (17)0.09433 (13)0.13155 (9)0.0607 (3)
C20.4799 (2)0.00037 (14)0.22535 (9)0.0388 (3)
H2A0.5184−0.09340.25040.047*
H2B0.60310.04580.19380.047*
C30.3061 (2)0.00704 (13)0.16274 (9)0.0365 (3)
C40.1269 (2)0.10236 (15)0.16572 (10)0.0409 (3)
C50.1623 (2)0.21277 (14)0.20919 (9)0.0391 (3)
C60.3625 (2)0.20500 (14)0.25728 (10)0.0419 (3)
H6A0.47580.24740.21720.050*
H6B0.34450.25250.30300.050*
C70.5831 (3)0.05303 (15)0.35758 (10)0.0456 (3)
H7A0.55090.11440.39430.055*
H7B0.71450.08180.32520.055*
C80.6140 (2)−0.08686 (15)0.41541 (9)0.0450 (3)
C90.8058 (3)−0.1227 (2)0.45420 (13)0.0654 (5)
H90.9173−0.06250.44090.078*
C100.8331 (4)−0.2468 (3)0.51234 (15)0.0876 (8)
H100.9619−0.26870.53900.105*
C110.6736 (5)−0.3375 (2)0.53127 (14)0.0902 (8)
H110.6938−0.42150.57020.108*
C120.4837 (4)−0.3047 (2)0.49285 (13)0.0769 (6)
H120.3746−0.36680.50540.092*
C130.4529 (3)−0.17936 (17)0.43535 (11)0.0561 (4)
H130.3226−0.15740.41000.067*
C140.3014 (2)−0.06137 (14)0.10079 (9)0.0390 (3)
H140.1813−0.04520.06750.047*
C150.4524 (2)−0.15682 (13)0.07658 (9)0.0388 (3)
C160.3853 (3)−0.22865 (16)0.01835 (10)0.0474 (3)
H160.2505−0.2127−0.00360.057*
C170.5152 (3)−0.32245 (17)−0.00687 (12)0.0589 (4)
H170.4671−0.3696−0.04530.071*
C180.7149 (3)−0.34718 (17)0.02409 (12)0.0604 (5)
H180.8016−0.41160.00750.073*
C190.7858 (3)−0.27558 (18)0.08004 (12)0.0547 (4)
H190.9217−0.29140.10090.066*
C200.6575 (2)−0.18052 (15)0.10546 (10)0.0467 (3)
H200.7088−0.13170.14230.056*
C210.0135 (2)0.30848 (15)0.20503 (10)0.0454 (3)
H21−0.10880.29840.17680.055*
C220.0221 (2)0.42793 (15)0.24022 (10)0.0456 (3)
C23−0.1555 (3)0.46678 (18)0.28275 (12)0.0582 (4)
H23−0.27840.41670.28880.070*
C24−0.1519 (4)0.5785 (2)0.31605 (14)0.0711 (6)
H24−0.27130.60230.34530.085*
C250.0267 (4)0.6549 (2)0.30642 (14)0.0715 (6)
H250.02850.73030.32900.086*
C260.2030 (3)0.61958 (17)0.26319 (13)0.0631 (5)
H260.32380.67190.25590.076*
C270.2011 (3)0.50666 (15)0.23063 (11)0.0520 (4)
H270.32150.48300.20190.062*
U11U22U33U12U13U23
N10.0467 (7)0.0396 (6)0.0315 (6)0.0051 (5)−0.0077 (5)−0.0109 (4)
O10.0388 (6)0.0723 (8)0.0803 (9)0.0045 (5)−0.0156 (6)−0.0349 (7)
C20.0413 (7)0.0429 (7)0.0344 (7)0.0036 (5)−0.0053 (5)−0.0138 (5)
C30.0367 (7)0.0374 (6)0.0342 (7)−0.0019 (5)−0.0018 (5)−0.0071 (5)
C40.0345 (7)0.0462 (7)0.0420 (8)−0.0016 (5)−0.0016 (6)−0.0112 (6)
C50.0396 (7)0.0415 (7)0.0350 (7)0.0005 (5)−0.0003 (5)−0.0078 (5)
C60.0482 (8)0.0384 (6)0.0401 (7)0.0028 (5)−0.0077 (6)−0.0108 (5)
C70.0523 (9)0.0478 (7)0.0398 (8)0.0025 (6)−0.0117 (6)−0.0156 (6)
C80.0563 (9)0.0497 (8)0.0322 (7)0.0127 (6)−0.0089 (6)−0.0162 (6)
C90.0654 (11)0.0815 (12)0.0521 (10)0.0227 (9)−0.0187 (8)−0.0216 (9)
C100.1057 (19)0.0971 (17)0.0605 (13)0.0531 (15)−0.0312 (12)−0.0211 (12)
C110.161 (3)0.0623 (12)0.0441 (10)0.0447 (15)−0.0169 (14)−0.0096 (9)
C120.1278 (19)0.0521 (10)0.0483 (10)0.0019 (11)0.0043 (11)−0.0094 (8)
C130.0736 (11)0.0530 (9)0.0420 (9)0.0042 (8)−0.0071 (8)−0.0123 (7)
C140.0404 (7)0.0416 (6)0.0351 (7)−0.0015 (5)−0.0064 (5)−0.0090 (5)
C150.0473 (8)0.0387 (6)0.0296 (6)−0.0019 (5)−0.0020 (5)−0.0070 (5)
C160.0579 (9)0.0483 (8)0.0381 (8)−0.0040 (6)−0.0061 (6)−0.0139 (6)
C170.0847 (13)0.0495 (8)0.0488 (9)−0.0041 (8)−0.0005 (9)−0.0240 (7)
C180.0781 (13)0.0487 (8)0.0556 (10)0.0084 (8)0.0069 (9)−0.0176 (7)
C190.0548 (10)0.0577 (9)0.0512 (9)0.0107 (7)−0.0018 (7)−0.0141 (7)
C200.0489 (9)0.0516 (8)0.0422 (8)0.0026 (6)−0.0053 (6)−0.0162 (6)
C210.0415 (8)0.0483 (7)0.0461 (8)0.0039 (6)−0.0028 (6)−0.0117 (6)
C220.0500 (8)0.0416 (7)0.0418 (8)0.0091 (6)−0.0039 (6)−0.0048 (6)
C230.0563 (10)0.0592 (9)0.0601 (11)0.0085 (7)0.0023 (8)−0.0186 (8)
C240.0826 (14)0.0709 (12)0.0630 (12)0.0188 (10)0.0070 (10)−0.0261 (10)
C250.1052 (17)0.0520 (9)0.0608 (12)0.0106 (10)−0.0095 (11)−0.0208 (8)
C260.0816 (13)0.0429 (8)0.0612 (11)−0.0042 (8)−0.0094 (9)−0.0049 (7)
C270.0568 (10)0.0423 (7)0.0519 (9)0.0035 (6)0.0001 (7)−0.0033 (6)
N1—C71.4543 (18)C13—H130.9300
N1—C61.4575 (18)C14—C151.4610 (19)
N1—C21.4617 (17)C14—H140.9300
O1—C41.2183 (17)C15—C201.390 (2)
C2—C31.4984 (19)C15—C161.399 (2)
C2—H2A0.9700C16—C171.375 (2)
C2—H2B0.9700C16—H160.9300
C3—C141.3417 (19)C17—C181.370 (3)
C3—C41.4870 (19)C17—H170.9300
C4—C51.489 (2)C18—C191.377 (3)
C5—C211.3354 (19)C18—H180.9300
C5—C61.495 (2)C19—C201.380 (2)
C6—H6A0.9700C19—H190.9300
C6—H6B0.9700C20—H200.9300
C7—C81.503 (2)C21—C221.469 (2)
C7—H7A0.9700C21—H210.9300
C7—H7B0.9700C22—C271.387 (2)
C8—C131.380 (3)C22—C231.389 (2)
C8—C91.383 (2)C23—C241.376 (3)
C9—C101.376 (3)C23—H230.9300
C9—H90.9300C24—C251.371 (3)
C10—C111.360 (4)C24—H240.9300
C10—H100.9300C25—C261.374 (3)
C11—C121.366 (4)C25—H250.9300
C11—H110.9300C26—C271.380 (2)
C12—C131.385 (3)C26—H260.9300
C12—H120.9300C27—H270.9300
C7—N1—C6110.28 (11)C8—C13—C12120.50 (19)
C7—N1—C2111.05 (11)C8—C13—H13119.8
C6—N1—C2108.77 (11)C12—C13—H13119.8
N1—C2—C3111.46 (11)C3—C14—C15131.10 (13)
N1—C2—H2A109.3C3—C14—H14114.4
C3—C2—H2A109.3C15—C14—H14114.4
N1—C2—H2B109.3C20—C15—C16117.51 (13)
C3—C2—H2B109.3C20—C15—C14125.51 (13)
H2A—C2—H2B108.0C16—C15—C14116.97 (13)
C14—C3—C4116.30 (12)C17—C16—C15121.06 (16)
C14—C3—C2125.73 (12)C17—C16—H16119.5
C4—C3—C2117.90 (11)C15—C16—H16119.5
O1—C4—C3121.95 (13)C18—C17—C16120.63 (16)
O1—C4—C5120.88 (13)C18—C17—H17119.7
C3—C4—C5117.12 (12)C16—C17—H17119.7
C21—C5—C4118.78 (13)C17—C18—C19119.27 (15)
C21—C5—C6124.66 (13)C17—C18—H18120.4
C4—C5—C6116.54 (11)C19—C18—H18120.4
N1—C6—C5109.06 (11)C18—C19—C20120.70 (17)
N1—C6—H6A109.9C18—C19—H19119.7
C5—C6—H6A109.9C20—C19—H19119.7
N1—C6—H6B109.9C19—C20—C15120.77 (15)
C5—C6—H6B109.9C19—C20—H20119.6
H6A—C6—H6B108.3C15—C20—H20119.6
N1—C7—C8113.90 (12)C5—C21—C22127.05 (14)
N1—C7—H7A108.8C5—C21—H21116.5
C8—C7—H7A108.8C22—C21—H21116.5
N1—C7—H7B108.8C27—C22—C23118.09 (16)
C8—C7—H7B108.8C27—C22—C21122.26 (14)
H7A—C7—H7B107.7C23—C22—C21119.63 (15)
C13—C8—C9118.31 (16)C24—C23—C22120.79 (18)
C13—C8—C7122.09 (14)C24—C23—H23119.6
C9—C8—C7119.49 (16)C22—C23—H23119.6
C10—C9—C8120.6 (2)C25—C24—C23120.40 (18)
C10—C9—H9119.7C25—C24—H24119.8
C8—C9—H9119.7C23—C24—H24119.8
C11—C10—C9120.7 (2)C24—C25—C26119.73 (18)
C11—C10—H10119.7C24—C25—H25120.1
C9—C10—H10119.7C26—C25—H25120.1
C10—C11—C12119.7 (2)C25—C26—C27120.11 (19)
C10—C11—H11120.2C25—C26—H26119.9
C12—C11—H11120.2C27—C26—H26119.9
C11—C12—C13120.3 (2)C26—C27—C22120.86 (16)
C11—C12—H12119.9C26—C27—H27119.6
C13—C12—H12119.9C22—C27—H27119.6
C7—N1—C2—C3178.28 (12)C7—C8—C13—C12−176.30 (15)
C6—N1—C2—C3−60.18 (15)C11—C12—C13—C80.8 (3)
N1—C2—C3—C14−167.71 (13)C4—C3—C14—C15176.89 (14)
N1—C2—C3—C415.50 (17)C2—C3—C14—C150.1 (2)
C14—C3—C4—O118.9 (2)C3—C14—C15—C20−11.5 (3)
C2—C3—C4—O1−164.04 (14)C3—C14—C15—C16169.52 (15)
C14—C3—C4—C5−158.55 (13)C20—C15—C16—C172.2 (2)
C2—C3—C4—C518.54 (18)C14—C15—C16—C17−178.79 (14)
O1—C4—C5—C21−4.5 (2)C15—C16—C17—C18−0.5 (3)
C3—C4—C5—C21173.00 (13)C16—C17—C18—C19−0.9 (3)
O1—C4—C5—C6173.68 (14)C17—C18—C19—C200.5 (3)
C3—C4—C5—C6−8.87 (19)C18—C19—C20—C151.3 (3)
C7—N1—C6—C5−168.16 (12)C16—C15—C20—C19−2.6 (2)
C2—N1—C6—C569.84 (14)C14—C15—C20—C19178.48 (15)
C21—C5—C6—N1144.04 (14)C4—C5—C21—C22−177.30 (14)
C4—C5—C6—N1−33.97 (17)C6—C5—C21—C224.7 (3)
C6—N1—C7—C8166.64 (12)C5—C21—C22—C2743.6 (2)
C2—N1—C7—C8−72.72 (16)C5—C21—C22—C23−138.13 (17)
N1—C7—C8—C13−26.1 (2)C27—C22—C23—C24−1.4 (3)
N1—C7—C8—C9157.64 (14)C21—C22—C23—C24−179.78 (17)
C13—C8—C9—C10−1.1 (3)C22—C23—C24—C251.1 (3)
C7—C8—C9—C10175.31 (17)C23—C24—C25—C260.0 (3)
C8—C9—C10—C111.4 (3)C24—C25—C26—C27−0.9 (3)
C9—C10—C11—C12−0.7 (3)C25—C26—C27—C220.5 (3)
C10—C11—C12—C13−0.4 (3)C23—C22—C27—C260.6 (2)
C9—C8—C13—C120.0 (2)C21—C22—C27—C26178.91 (15)
D—H···AD—HH···AD···AD—H···A
C13—H13···N10.932.572.885 (2)100
C14—H14···O10.932.362.7560 (18)106
C21—H21···O10.932.402.761 (2)103
C2—H2B···O1i0.972.443.3798 (17)163
C16—H16···O1ii0.932.503.304 (2)145
C7—H7A···Cg2iii0.972.773.6957 (18)159
C19—H19···Cg4iv0.932.913.523 (2)125
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C13—H13⋯N10.932.572.885 (2)100
C14—H14⋯O10.932.362.7560 (18)106
C21—H21⋯O10.932.402.761 (2)103
C2—H2B⋯O1i0.972.443.3798 (17)163
C16—H16⋯O1ii0.932.503.304 (2)145
C7—H7A⋯Cg2iii0.972.773.6957 (18)159
C19—H19⋯Cg4iv0.932.913.523 (2)125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C8–C13 ring and Cg4 is the centroid of the C22–C27 ring.

  4 in total

1.  (R)-3,5-Bis[(E)-benzylidene]-1-(1-phenylethyl)piperidin-4-one, 3,5-bis[(E)-4-chlorobenzylidene]-1-[(R)-1-phenylethyl]piperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-[(R)-1-phenylethyl]piperidin-4-one.

Authors:  J Suresh; R Suresh Kumar; S Perumal; S Natarajan
Journal:  Acta Crystallogr C       Date:  2007-04-28       Impact factor: 1.172

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy)phenylcarbonyl]-3,5-bis(arylidene)-4-piperidones and related compounds.

Authors:  Umashankar Das; Jane Alcorn; Anuraag Shrivastav; Rajendra K Sharma; Erik De Clercq; Jan Balzarini; Jonathan R Dimmock
Journal:  Eur J Med Chem       Date:  2006-09-22       Impact factor: 6.514

4.  Bicyclic pyrazolines, potential central nervous system depressants and antiinflammatory agents.

Authors:  J Krapcho; C F Turk
Journal:  J Med Chem       Date:  1979-02       Impact factor: 7.446
  4 in total
  1 in total

1.  (3E,5E)-3,5-Bis(4-allyl-oxybenzyl-idene)-1-benzyl-piperidin-4-one.

Authors:  N S Karthikeyan; K Sathiyanarayanan; P G Aravindan; H Ghosh; R S Rathore
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-11
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.