Literature DB >> 24109358

[(4E)-1-Methyl-2,6-diphenyl-3-(propan-2-yl)piperidin-4-yl-idene]amino 3-methyl-benzoate.

T Vinuchakkaravarthy1, R Sivakumar, T Srinivasan, V Thanikachalam, D Velmurugan.   

Abstract

In the title compound, C29H32N2O2, the piperidine ring exists in a chair conformation (the bond-angle sum at the sp (2)-hybridized C atom is 359.79°). The phenyl rings and the methyl group substituted on the heterocyclic ring are in equatorial orientations. In the crystal, pairs of C-H⋯π inter-actions result in the formation of inversion dimers.

Entities:  

Year:  2013        PMID: 24109358      PMCID: PMC3793771          DOI: 10.1107/S160053681301893X

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


Related literature

For the synthesis and the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009 ▶, 2011 ▶). For the crystal structures of related compounds, see: Park et al. (2012a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H32N2O2 M = 440.57 Triclinic, a = 10.7837 (4) Å b = 11.7075 (4) Å c = 12.0586 (4) Å α = 114.352 (3)° β = 96.245 (2)° γ = 109.530 (5)° V = 1252.07 (10) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 293 K 0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.986, T max = 0.986 18725 measured reflections 5163 independent reflections 3847 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.144 S = 1.04 5163 reflections 298 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.20 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301893X/pv2632sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301893X/pv2632Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S160053681301893X/pv2632Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C29H32N2O2Z = 2
Mr = 440.57F(000) = 472
Triclinic, P1Dx = 1.169 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7837 (4) ÅCell parameters from 5207 reflections
b = 11.7075 (4) Åθ = 1.9–26.5°
c = 12.0586 (4) ŵ = 0.07 mm1
α = 114.352 (3)°T = 293 K
β = 96.245 (2)°Block, colorless
γ = 109.530 (5)°0.20 × 0.20 × 0.20 mm
V = 1252.07 (10) Å3
Bruker SMART APEXII CCD diffractometer5163 independent reflections
Radiation source: fine-focus sealed tube3847 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and φ scansθmax = 26.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −13→13
Tmin = 0.986, Tmax = 0.986k = −14→14
18725 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2364P] where P = (Fo2 + 2Fc2)/3
5163 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.20 e Å3
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
C10.85940 (14)0.07747 (14)0.32666 (13)0.0429 (3)
H10.92920.05070.35370.051*
C20.86023 (15)0.20135 (15)0.44415 (13)0.0453 (3)
H20.79280.22790.41250.054*
C30.99781 (15)0.31978 (15)0.48597 (14)0.0467 (3)
C41.02338 (17)0.35945 (15)0.38514 (14)0.0506 (4)
H4A1.11160.43780.41690.061*
H4B0.95270.38560.36100.061*
C51.02226 (15)0.23655 (15)0.26978 (14)0.0441 (3)
H51.09830.21590.29470.053*
C60.72125 (15)−0.04589 (15)0.27061 (14)0.0457 (3)
C70.71016 (18)−0.17315 (17)0.25442 (17)0.0593 (4)
H70.7883−0.18280.28170.071*
C80.5842 (2)−0.28672 (18)0.19804 (19)0.0709 (5)
H80.5786−0.37210.18650.085*
C90.4681 (2)−0.27374 (19)0.15942 (19)0.0715 (5)
H90.3836−0.34990.12190.086*
C100.47680 (18)−0.1480 (2)0.17625 (18)0.0676 (5)
H100.3977−0.13860.15130.081*
C110.60263 (16)−0.03497 (17)0.23022 (16)0.0555 (4)
H110.60760.04950.23950.067*
C120.81213 (17)0.16674 (17)0.54654 (15)0.0562 (4)
H120.71930.09240.50430.067*
C130.7980 (2)0.2888 (2)0.64964 (19)0.0817 (6)
H13A0.74370.32010.61080.123*
H13B0.88740.36260.69810.123*
H13C0.75400.26060.70480.123*
C140.8961 (2)0.1127 (2)0.60377 (19)0.0763 (6)
H14A0.90180.03520.53700.114*
H14B0.85280.08450.65920.114*
H14C0.98680.18430.65130.114*
C151.29265 (17)0.54898 (17)0.72791 (15)0.0541 (4)
C161.41632 (16)0.65991 (17)0.73437 (15)0.0533 (4)
C171.49678 (19)0.7698 (2)0.85301 (18)0.0671 (5)
H171.47520.77130.92610.081*
C181.6094 (2)0.8772 (2)0.8616 (2)0.0790 (6)
H181.66260.95210.94080.095*
C191.64325 (19)0.8744 (2)0.7553 (2)0.0780 (6)
H191.71970.94750.76320.094*
C201.56626 (19)0.7648 (2)0.6353 (2)0.0734 (5)
C211.45135 (18)0.65867 (19)0.62697 (18)0.0629 (4)
H211.39670.58520.54740.075*
C221.6026 (3)0.7604 (3)0.5167 (3)0.1156 (9)
H22A1.68470.84080.53960.173*
H22B1.52870.75860.46290.173*
H22C1.61760.67900.47220.173*
C231.04536 (16)0.27730 (15)0.16717 (14)0.0480 (4)
C241.17432 (18)0.31908 (16)0.15031 (17)0.0592 (4)
H241.24610.31810.19960.071*
C251.1978 (3)0.36252 (19)0.0605 (2)0.0777 (6)
H251.28510.38950.04960.093*
C261.0947 (3)0.3661 (2)−0.0117 (2)0.0870 (7)
H261.11110.3957−0.07150.104*
C270.9668 (3)0.3257 (2)0.0046 (2)0.0851 (6)
H270.89590.3280−0.04460.102*
C280.9410 (2)0.28125 (19)0.09366 (17)0.0653 (5)
H280.85330.25410.10370.078*
C290.90196 (18)−0.00294 (16)0.12275 (16)0.0566 (4)
H29A0.8183−0.08410.09310.085*
H29B0.9777−0.01820.15340.085*
H29C0.91590.01680.05410.085*
N10.89281 (12)0.11408 (12)0.22587 (11)0.0422 (3)
N21.08029 (13)0.36687 (14)0.59413 (12)0.0536 (3)
O11.20675 (11)0.47558 (12)0.60903 (10)0.0601 (3)
O21.26989 (15)0.52897 (16)0.81397 (12)0.0881 (5)
U11U22U33U12U13U23
C10.0428 (8)0.0407 (8)0.0444 (8)0.0152 (6)0.0146 (6)0.0211 (6)
C20.0459 (8)0.0444 (8)0.0426 (8)0.0152 (6)0.0162 (6)0.0203 (7)
C30.0517 (9)0.0385 (8)0.0429 (8)0.0140 (7)0.0173 (7)0.0163 (6)
C40.0594 (9)0.0396 (8)0.0441 (8)0.0118 (7)0.0155 (7)0.0194 (7)
C50.0428 (8)0.0427 (8)0.0460 (8)0.0145 (6)0.0150 (6)0.0227 (7)
C60.0480 (8)0.0413 (8)0.0422 (8)0.0128 (6)0.0169 (6)0.0189 (6)
C70.0619 (10)0.0486 (9)0.0650 (10)0.0182 (8)0.0192 (8)0.0288 (8)
C80.0805 (13)0.0423 (9)0.0783 (12)0.0124 (9)0.0245 (10)0.0287 (9)
C90.0611 (11)0.0523 (10)0.0703 (12)−0.0010 (8)0.0195 (9)0.0215 (9)
C100.0495 (10)0.0627 (11)0.0708 (11)0.0123 (8)0.0141 (8)0.0241 (9)
C110.0523 (9)0.0457 (9)0.0584 (9)0.0144 (7)0.0149 (7)0.0212 (8)
C120.0529 (9)0.0560 (9)0.0473 (8)0.0091 (7)0.0193 (7)0.0235 (8)
C130.0864 (14)0.0854 (14)0.0633 (12)0.0285 (12)0.0426 (11)0.0278 (11)
C140.0871 (14)0.0762 (13)0.0683 (12)0.0196 (11)0.0222 (10)0.0485 (11)
C150.0545 (9)0.0547 (9)0.0462 (8)0.0158 (8)0.0118 (7)0.0243 (8)
C160.0471 (9)0.0518 (9)0.0548 (9)0.0148 (7)0.0074 (7)0.0264 (8)
C170.0614 (11)0.0642 (11)0.0579 (10)0.0168 (9)0.0018 (8)0.0247 (9)
C180.0592 (12)0.0597 (12)0.0859 (14)0.0090 (9)−0.0089 (10)0.0263 (11)
C190.0489 (10)0.0653 (12)0.1112 (18)0.0103 (9)0.0090 (11)0.0490 (13)
C200.0564 (11)0.0755 (13)0.0951 (15)0.0183 (10)0.0231 (10)0.0537 (12)
C210.0554 (10)0.0626 (11)0.0613 (10)0.0130 (8)0.0128 (8)0.0318 (9)
C220.1013 (19)0.129 (2)0.124 (2)0.0219 (16)0.0543 (16)0.082 (2)
C230.0588 (9)0.0370 (7)0.0433 (8)0.0151 (7)0.0197 (7)0.0176 (6)
C240.0669 (11)0.0436 (9)0.0646 (10)0.0175 (8)0.0323 (8)0.0250 (8)
C250.1038 (16)0.0482 (10)0.0805 (13)0.0213 (10)0.0577 (13)0.0311 (10)
C260.146 (2)0.0545 (11)0.0625 (12)0.0292 (13)0.0480 (14)0.0356 (10)
C270.1183 (19)0.0780 (14)0.0636 (12)0.0364 (13)0.0173 (12)0.0436 (11)
C280.0720 (12)0.0676 (11)0.0576 (10)0.0244 (9)0.0169 (9)0.0355 (9)
C290.0635 (10)0.0456 (9)0.0530 (9)0.0194 (8)0.0279 (8)0.0170 (7)
N10.0444 (7)0.0371 (6)0.0409 (6)0.0132 (5)0.0170 (5)0.0168 (5)
N20.0506 (8)0.0492 (7)0.0468 (7)0.0062 (6)0.0148 (6)0.0218 (6)
O10.0528 (6)0.0585 (7)0.0453 (6)0.0001 (5)0.0095 (5)0.0236 (5)
O20.0826 (9)0.0981 (11)0.0548 (8)0.0003 (8)0.0104 (7)0.0431 (8)
C1—N11.4874 (17)C14—H14C0.9600
C1—C61.516 (2)C15—O21.1872 (19)
C1—C21.551 (2)C15—O11.3470 (19)
C1—H10.9800C15—C161.486 (2)
C2—C31.504 (2)C16—C211.384 (2)
C2—C121.5391 (19)C16—C171.386 (2)
C2—H20.9800C17—C181.383 (3)
C3—N21.274 (2)C17—H170.9300
C3—C41.491 (2)C18—C191.361 (3)
C4—C51.530 (2)C18—H180.9300
C4—H4A0.9700C19—C201.387 (3)
C4—H4B0.9700C19—H190.9300
C5—N11.4696 (18)C20—C211.389 (2)
C5—C231.5150 (19)C20—C221.509 (3)
C5—H50.9800C21—H210.9300
C6—C71.381 (2)C22—H22A0.9600
C6—C111.384 (2)C22—H22B0.9600
C7—C81.386 (2)C22—H22C0.9600
C7—H70.9300C23—C241.380 (2)
C8—C91.365 (3)C23—C281.381 (2)
C8—H80.9300C24—C251.386 (3)
C9—C101.369 (3)C24—H240.9300
C9—H90.9300C25—C261.359 (3)
C10—C111.383 (2)C25—H250.9300
C10—H100.9300C26—C271.366 (3)
C11—H110.9300C26—H260.9300
C12—C141.517 (3)C27—C281.389 (3)
C12—C131.528 (3)C27—H270.9300
C12—H120.9800C28—H280.9300
C13—H13A0.9600C29—N11.4646 (19)
C13—H13B0.9600C29—H29A0.9600
C13—H13C0.9600C29—H29B0.9600
C14—H14A0.9600C29—H29C0.9600
C14—H14B0.9600N2—O11.4524 (16)
N1—C1—C6108.67 (11)C12—C14—H14C109.5
N1—C1—C2111.65 (11)H14A—C14—H14C109.5
C6—C1—C2111.47 (11)H14B—C14—H14C109.5
N1—C1—H1108.3O2—C15—O1124.53 (15)
C6—C1—H1108.3O2—C15—C16125.98 (15)
C2—C1—H1108.3O1—C15—C16109.46 (13)
C3—C2—C12117.24 (12)C21—C16—C17119.46 (16)
C3—C2—C1106.81 (11)C21—C16—C15122.52 (15)
C12—C2—C1114.42 (12)C17—C16—C15118.00 (15)
C3—C2—H2105.8C18—C17—C16119.28 (19)
C12—C2—H2105.8C18—C17—H17120.4
C1—C2—H2105.8C16—C17—H17120.4
N2—C3—C4127.95 (14)C19—C18—C17120.68 (19)
N2—C3—C2119.25 (13)C19—C18—H18119.7
C4—C3—C2112.59 (12)C17—C18—H18119.7
C3—C4—C5108.92 (12)C18—C19—C20121.45 (18)
C3—C4—H4A109.9C18—C19—H19119.3
C5—C4—H4A109.9C20—C19—H19119.3
C3—C4—H4B109.9C19—C20—C21117.63 (19)
C5—C4—H4B109.9C19—C20—C22122.0 (2)
H4A—C4—H4B108.3C21—C20—C22120.4 (2)
N1—C5—C23112.04 (12)C16—C21—C20121.47 (18)
N1—C5—C4110.59 (11)C16—C21—H21119.3
C23—C5—C4108.34 (11)C20—C21—H21119.3
N1—C5—H5108.6C20—C22—H22A109.5
C23—C5—H5108.6C20—C22—H22B109.5
C4—C5—H5108.6H22A—C22—H22B109.5
C7—C6—C11117.98 (14)C20—C22—H22C109.5
C7—C6—C1121.36 (14)H22A—C22—H22C109.5
C11—C6—C1120.62 (13)H22B—C22—H22C109.5
C6—C7—C8120.91 (17)C24—C23—C28118.47 (15)
C6—C7—H7119.5C24—C23—C5120.19 (15)
C8—C7—H7119.5C28—C23—C5121.24 (14)
C9—C8—C7120.25 (17)C23—C24—C25120.61 (19)
C9—C8—H8119.9C23—C24—H24119.7
C7—C8—H8119.9C25—C24—H24119.7
C8—C9—C10119.67 (17)C26—C25—C24120.70 (19)
C8—C9—H9120.2C26—C25—H25119.6
C10—C9—H9120.2C24—C25—H25119.6
C9—C10—C11120.31 (18)C25—C26—C27119.22 (18)
C9—C10—H10119.8C25—C26—H26120.4
C11—C10—H10119.8C27—C26—H26120.4
C10—C11—C6120.85 (16)C26—C27—C28120.9 (2)
C10—C11—H11119.6C26—C27—H27119.5
C6—C11—H11119.6C28—C27—H27119.5
C14—C12—C13111.31 (16)C23—C28—C27120.04 (19)
C14—C12—C2115.51 (14)C23—C28—H28120.0
C13—C12—C2110.75 (14)C27—C28—H28120.0
C14—C12—H12106.2N1—C29—H29A109.5
C13—C12—H12106.2N1—C29—H29B109.5
C2—C12—H12106.2H29A—C29—H29B109.5
C12—C13—H13A109.5N1—C29—H29C109.5
C12—C13—H13B109.5H29A—C29—H29C109.5
H13A—C13—H13B109.5H29B—C29—H29C109.5
C12—C13—H13C109.5C29—N1—C5108.29 (11)
H13A—C13—H13C109.5C29—N1—C1108.89 (11)
H13B—C13—H13C109.5C5—N1—C1114.03 (11)
C12—C14—H14A109.5C3—N2—O1108.37 (11)
C12—C14—H14B109.5C15—O1—N2113.56 (11)
H14A—C14—H14B109.5
N1—C1—C2—C3−54.46 (15)C16—C17—C18—C19−1.4 (3)
C6—C1—C2—C3−176.20 (12)C17—C18—C19—C200.3 (3)
N1—C1—C2—C12174.07 (12)C18—C19—C20—C211.2 (3)
C6—C1—C2—C1252.32 (16)C18—C19—C20—C22180.0 (2)
C12—C2—C3—N214.7 (2)C17—C16—C21—C200.5 (3)
C1—C2—C3—N2−115.22 (15)C15—C16—C21—C20178.90 (16)
C12—C2—C3—C4−170.18 (13)C19—C20—C21—C16−1.6 (3)
C1—C2—C3—C459.93 (15)C22—C20—C21—C16179.6 (2)
N2—C3—C4—C5113.23 (18)N1—C5—C23—C24−138.77 (14)
C2—C3—C4—C5−61.40 (16)C4—C5—C23—C2498.96 (16)
C3—C4—C5—N155.67 (16)N1—C5—C23—C2844.96 (19)
C3—C4—C5—C23178.82 (12)C4—C5—C23—C28−77.31 (18)
N1—C1—C6—C7112.12 (15)C28—C23—C24—C25−0.7 (2)
C2—C1—C6—C7−124.42 (15)C5—C23—C24—C25−177.07 (14)
N1—C1—C6—C11−65.75 (16)C23—C24—C25—C260.7 (3)
C2—C1—C6—C1157.72 (17)C24—C25—C26—C27−0.3 (3)
C11—C6—C7—C80.7 (2)C25—C26—C27—C280.0 (3)
C1—C6—C7—C8−177.18 (15)C24—C23—C28—C270.4 (3)
C6—C7—C8—C9−1.1 (3)C5—C23—C28—C27176.73 (16)
C7—C8—C9—C100.2 (3)C26—C27—C28—C230.0 (3)
C8—C9—C10—C111.0 (3)C23—C5—N1—C2963.82 (15)
C9—C10—C11—C6−1.4 (3)C4—C5—N1—C29−175.21 (12)
C7—C6—C11—C100.5 (2)C23—C5—N1—C1−174.80 (11)
C1—C6—C11—C10178.44 (15)C4—C5—N1—C1−53.82 (15)
C3—C2—C12—C14−66.36 (19)C6—C1—N1—C29−61.46 (14)
C1—C2—C12—C1459.87 (19)C2—C1—N1—C29175.18 (12)
C3—C2—C12—C1361.33 (19)C6—C1—N1—C5177.49 (11)
C1—C2—C12—C13−172.45 (14)C2—C1—N1—C554.13 (15)
O2—C15—C16—C21164.88 (19)C4—C3—N2—O13.2 (2)
O1—C15—C16—C21−16.9 (2)C2—C3—N2—O1177.53 (12)
O2—C15—C16—C17−16.7 (3)O2—C15—O1—N20.0 (2)
O1—C15—C16—C17161.50 (15)C16—C15—O1—N2−178.20 (12)
C21—C16—C17—C181.0 (3)C3—N2—O1—C15169.28 (14)
C15—C16—C17—C18−177.46 (16)
D—H···AD—HH···AD···AD—H···A
C11—H11···Cg1i0.932.953.778 (2)149
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A D—HH⋯A DA D—H⋯A
C11—H11⋯Cg1i 0.932.953.778 (2)149

Symmetry code: (i) .

  6 in total

1.  A short history of SHELX.

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

2.  Synthesis of polyfunctionalized piperidone oxime ethers and their cytotoxicity on HeLa cells.

Authors:  Paramasivam Parthiban; Ramjee Pallela; Se-Kwon Kim; Dong Ho Park; Yeon Tae Jeong
Journal:  Bioorg Med Chem Lett       Date:  2011-09-21       Impact factor: 2.823

3.  Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles.

Authors:  Paramasivam Parthiban; Gopalakrishnan Aridoss; Paramasivam Rathika; Venkatachalam Ramkumar; Senthamaraikannan Kabilan
Journal:  Bioorg Med Chem Lett       Date:  2009-04-18       Impact factor: 2.823

4.  2,6-Bis(4-chloro-phen-yl)-1,3-dimethyl-piperidin-4-one O-benzyl-oxime.

Authors:  Dong Ho Park; V Ramkumar; P Parthiban
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-25

5.  2,6-Bis(4-meth-oxy-phen-yl)-1,3-dimethyl-piperidin-4-one O-benzyl-oxime.

Authors:  Dong Ho Park; V Ramkumar; P Parthiban
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-25

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  (E)-3-Isopropyl-1-methyl-2,6-di-phenyl-piperidin-4-one O-nicotinoyl oxime.

Authors:  T Vinuchakkaravarthy; R Sivakumar; T Srinivasan; V Thanikachalam; D Velmurugan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-12
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.