Literature DB >> 23634054

Ethyl 2,6-bis-(4-chloro-phen-yl)-4-(4-fluoro-anilino)-1-(4-fluoro-phen-yl)-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Sumati Anthal1, Goutam Brahmachari, Suvankar Das, Rajni Kant, Vivek K Gupta.   

Abstract

In the title compound, C32H26Cl2F2N2O2, the tetra-hydro-pyridine ring adopts a distorted boat conformation. The chlorophenyl rings are inclined to one another by 55.2 (1)°, while for the fluorophenyl rings the dihedral angle is 80.7 (1)°. The amino group and carbonyl O atom are involved in an intra-molecular N-H⋯O hydrogen bond. In the crystal, weak C-H⋯O, C-H⋯F and C-H⋯Cl inter-actions link the mol-ecules into a three-dimensional network.

Entities:  

Year:  2013        PMID： 23634054      PMCID： PMC3629536          DOI： 10.1107/S1600536813006090

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


Related literature

For the biological activity of functionalized piperidine derivatives, see: Zhou et al. (2007 ▶); Misra et al. (2009 ▶); Bin et al. (2001 ▶); Agrawal & Somani (2009 ▶); Dekus et al. (2007 ▶). For general applications of densely functionalized piperidines, see: Targum et al. (1995 ▶); Schotte et al. (1996 ▶). For general background to functionalized piperidiones, see: Desai et al. (1992 ▶); Pinder (1992 ▶); Watson et al. (2000 ▶); Breman et al. (2001 ▶); Kamei et al. (2005 ▶). For related structures, see: Sambyal et al. (2011 ▶); Brahmachari & Das (2012 ▶); Anthal et al. (2013 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C32H26Cl2F2N2O2 M = 579.45 Triclinic, a = 10.3074 (7) Å b = 10.7942 (5) Å c = 13.9432 (10) Å α = 103.554 (5)° β = 106.487 (6)° γ = 96.846 (5)° V = 1417.12 (15) Å3 Z = 2 Mo Kα radiation μ = 0.28 mm−1 T = 293 K 0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.881, T max = 1.000 10718 measured reflections 5248 independent reflections 2169 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.062 wR(F 2) = 0.133 S = 0.93 5248 reflections 363 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.26 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006090/bg2498sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006090/bg2498Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813006090/bg2498Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C32H26Cl2F2N2O2Z = 2
Mr = 579.45F(000) = 600
Triclinic, P1Dx = 1.358 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3074 (7) ÅCell parameters from 3771 reflections
b = 10.7942 (5) Åθ = 3.5–29.0°
c = 13.9432 (10) ŵ = 0.28 mm−1
α = 103.554 (5)°T = 293 K
β = 106.487 (6)°Plate, white
γ = 96.846 (5)°0.30 × 0.20 × 0.15 mm
V = 1417.12 (15) Å3
Oxford Diffraction Xcalibur Sapphire3 diffractometer5248 independent reflections
Radiation source: fine-focus sealed tube2169 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 16.1049 pixels mm-1θmax = 25.5°, θmin = 3.5°
ω scansh = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −13→12
Tmin = 0.881, Tmax = 1.000l = −16→16
10718 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)] = 0.062H-atom parameters constrained
wR(F2) = 0.133w = 1/[σ2(Fo2) + (0.029P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
5248 reflectionsΔρmax = 0.28 e Å−3
363 parametersΔρmin = −0.26 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (8)
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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
Cl10.08233 (15)0.65481 (11)0.39945 (11)0.1144 (6)
Cl20.37360 (13)−0.49679 (12)0.06250 (10)0.0983 (5)
F10.7899 (3)0.5548 (3)0.2179 (2)0.1196 (11)
F2−0.4881 (2)−0.1674 (2)0.0483 (2)0.0936 (9)
O10.4233 (3)0.1728 (3)0.5195 (2)0.0778 (9)
O20.2475 (3)0.0078 (3)0.4821 (2)0.0726 (9)
N10.0762 (3)0.0160 (2)0.1940 (2)0.0424 (7)
N20.4685 (3)0.2445 (3)0.3589 (2)0.0608 (9)
H20.49060.25990.42550.073*
C20.1699 (3)−0.0372 (3)0.2673 (2)0.0421 (9)
H2A0.1179−0.06840.30880.051*
C30.2907 (4)0.0690 (3)0.3426 (3)0.0466 (10)
C40.3580 (4)0.1479 (3)0.3018 (3)0.0436 (9)
C50.2907 (4)0.1349 (3)0.1887 (3)0.0517 (10)
H5A0.30690.05700.14640.062*
H5B0.32970.20920.17080.062*
C60.1341 (4)0.1273 (3)0.1672 (3)0.0451 (10)
H60.09100.11360.09220.054*
C70.3280 (4)0.0887 (4)0.4538 (3)0.0576 (11)
C80.2793 (6)0.0239 (5)0.5942 (3)0.117 (2)
H8A0.37240.01070.62290.141*
H8B0.27520.11170.62880.141*
C90.1875 (6)−0.0635 (5)0.6127 (4)0.133 (2)
H9A0.0965−0.04530.59010.200*
H9B0.2143−0.05590.68600.200*
H9C0.1874−0.15020.57500.200*
C100.2196 (3)−0.1527 (3)0.2129 (3)0.0431 (9)
C110.3258 (4)−0.1993 (3)0.2690 (3)0.0543 (11)
H110.3661−0.15890.34000.065*
C120.3748 (4)−0.3026 (4)0.2244 (3)0.0618 (12)
H120.4473−0.33110.26450.074*
C130.3155 (4)−0.3634 (3)0.1200 (3)0.0593 (11)
C140.2075 (4)−0.3228 (4)0.0607 (3)0.0593 (11)
H140.1665−0.3651−0.00990.071*
C150.1605 (4)−0.2175 (3)0.1079 (3)0.0501 (10)
H150.0873−0.18960.06790.060*
C16−0.0649 (4)−0.0309 (3)0.1574 (2)0.0378 (9)
C17−0.1231 (4)−0.1478 (3)0.1688 (3)0.0465 (10)
H17−0.0655−0.19670.20090.056*
C18−0.2644 (4)−0.1928 (3)0.1334 (3)0.0536 (10)
H18−0.3017−0.26960.14360.064*
C19−0.3481 (4)−0.1232 (4)0.0837 (3)0.0565 (11)
C20−0.2965 (4)−0.0084 (4)0.0697 (3)0.0510 (10)
H20−0.35570.03840.03650.061*
C21−0.1567 (4)0.0368 (3)0.1052 (2)0.0414 (9)
H21−0.12150.11400.09450.050*
C220.1100 (4)0.2574 (3)0.2241 (3)0.0455 (9)
C230.0850 (4)0.2775 (4)0.3179 (3)0.0568 (11)
H230.07460.20770.34530.068*
C240.0751 (4)0.3986 (4)0.3724 (3)0.0686 (13)
H240.06040.41090.43650.082*
C250.0871 (4)0.4993 (4)0.3305 (4)0.0681 (13)
C260.1069 (4)0.4825 (4)0.2349 (4)0.0714 (13)
H260.11260.55180.20620.086*
C270.1183 (4)0.3608 (3)0.1825 (3)0.0593 (11)
H270.13170.34840.11800.071*
C280.5515 (4)0.3228 (4)0.3226 (3)0.0526 (10)
C290.5940 (4)0.4541 (4)0.3719 (3)0.0732 (13)
H290.56650.49090.42830.088*
C300.6777 (5)0.5317 (4)0.3375 (4)0.0826 (16)
H300.70900.62000.37150.099*
C310.7127 (5)0.4760 (5)0.2533 (5)0.0763 (14)
C320.6739 (4)0.3486 (5)0.2043 (4)0.0796 (14)
H320.70080.31330.14720.095*
C330.5942 (4)0.2713 (4)0.2393 (3)0.0679 (12)
H330.56830.18240.20640.082*
U11U22U33U12U13U23
Cl10.1493 (13)0.0584 (8)0.1198 (12)0.0113 (8)0.0527 (10)−0.0108 (7)
Cl20.1033 (10)0.0923 (9)0.1124 (10)0.0470 (8)0.0568 (8)0.0128 (7)
F10.094 (2)0.123 (2)0.158 (3)−0.0029 (18)0.0331 (19)0.092 (2)
F20.0473 (16)0.0999 (19)0.126 (2)−0.0009 (14)0.0046 (15)0.0539 (16)
O10.080 (2)0.082 (2)0.0453 (17)−0.0184 (17)0.0000 (16)0.0110 (15)
O20.094 (2)0.0760 (19)0.0384 (16)−0.0104 (17)0.0182 (16)0.0153 (14)
N10.0394 (19)0.0418 (17)0.0472 (19)0.0047 (15)0.0096 (15)0.0216 (14)
N20.059 (2)0.068 (2)0.0428 (19)−0.0132 (19)0.0114 (17)0.0100 (16)
C20.041 (2)0.050 (2)0.038 (2)0.0097 (18)0.0127 (17)0.0156 (16)
C30.048 (2)0.056 (2)0.034 (2)0.008 (2)0.0128 (18)0.0104 (17)
C40.042 (2)0.056 (2)0.033 (2)0.0074 (19)0.0128 (18)0.0122 (17)
C50.054 (3)0.060 (2)0.045 (2)0.010 (2)0.0209 (19)0.0164 (18)
C60.048 (2)0.051 (2)0.036 (2)0.0056 (19)0.0142 (18)0.0134 (17)
C70.066 (3)0.061 (3)0.049 (3)0.010 (2)0.019 (2)0.019 (2)
C80.174 (6)0.116 (4)0.035 (3)−0.050 (4)0.028 (3)0.017 (3)
C90.223 (7)0.105 (4)0.069 (4)−0.015 (4)0.070 (4)0.014 (3)
C100.039 (2)0.047 (2)0.041 (2)0.0086 (18)0.0096 (18)0.0126 (17)
C110.055 (3)0.051 (2)0.051 (2)0.021 (2)0.008 (2)0.0102 (19)
C120.047 (3)0.065 (3)0.071 (3)0.022 (2)0.010 (2)0.020 (2)
C130.060 (3)0.059 (3)0.072 (3)0.023 (2)0.038 (2)0.015 (2)
C140.061 (3)0.069 (3)0.047 (2)0.012 (2)0.024 (2)0.007 (2)
C150.047 (2)0.058 (2)0.050 (2)0.014 (2)0.0183 (19)0.0178 (19)
C160.045 (2)0.0358 (19)0.0293 (19)0.0044 (18)0.0107 (17)0.0060 (15)
C170.043 (2)0.043 (2)0.051 (2)0.0158 (19)0.0120 (19)0.0102 (17)
C180.058 (3)0.048 (2)0.053 (2)0.004 (2)0.012 (2)0.0206 (18)
C190.038 (3)0.066 (3)0.056 (3)0.003 (2)0.005 (2)0.015 (2)
C200.047 (3)0.059 (3)0.046 (2)0.014 (2)0.007 (2)0.0209 (19)
C210.045 (2)0.039 (2)0.041 (2)0.0075 (18)0.0148 (18)0.0139 (16)
C220.048 (2)0.044 (2)0.048 (2)0.0048 (18)0.0212 (19)0.0164 (18)
C230.064 (3)0.059 (3)0.055 (3)0.010 (2)0.024 (2)0.024 (2)
C240.092 (4)0.066 (3)0.049 (3)0.019 (3)0.028 (2)0.010 (2)
C250.077 (3)0.048 (3)0.071 (3)0.003 (2)0.025 (3)0.003 (2)
C260.076 (3)0.052 (3)0.092 (4)0.003 (2)0.035 (3)0.026 (2)
C270.071 (3)0.048 (2)0.061 (3)0.001 (2)0.029 (2)0.016 (2)
C280.043 (2)0.054 (3)0.061 (3)0.007 (2)0.015 (2)0.019 (2)
C290.068 (3)0.059 (3)0.084 (3)0.008 (3)0.024 (3)0.007 (2)
C300.074 (4)0.052 (3)0.104 (4)−0.004 (3)0.014 (3)0.017 (3)
C310.058 (3)0.075 (4)0.108 (4)0.005 (3)0.022 (3)0.058 (3)
C320.068 (3)0.075 (3)0.101 (4)0.005 (3)0.038 (3)0.026 (3)
C330.065 (3)0.057 (3)0.092 (4)0.004 (2)0.043 (3)0.022 (2)
Cl1—C251.742 (4)C12—H120.9300
Cl2—C131.735 (3)C13—C141.371 (5)
F1—C311.364 (5)C14—C151.386 (4)
F2—C191.369 (4)C14—H140.9300
O1—C71.230 (4)C15—H150.9300
O2—C71.335 (5)C16—C171.395 (4)
O2—C81.466 (5)C16—C211.407 (4)
N1—C161.384 (4)C17—C181.383 (4)
N1—C61.450 (4)C17—H170.9300
N1—C21.468 (4)C18—C191.359 (4)
N2—C41.353 (4)C18—H180.9300
N2—C281.406 (5)C19—C201.368 (5)
N2—H20.8600C20—C211.369 (4)
C2—C31.523 (4)C20—H200.9300
C2—C101.524 (4)C21—H210.9300
C2—H2A0.9800C22—C231.377 (5)
C3—C41.356 (5)C22—C271.377 (5)
C3—C71.444 (5)C23—C241.381 (4)
C4—C51.497 (4)C23—H230.9300
C5—C61.545 (4)C24—C251.358 (5)
C5—H5A0.9700C24—H240.9300
C5—H5B0.9700C25—C261.379 (5)
C6—C221.529 (4)C26—C271.382 (4)
C6—H60.9800C26—H260.9300
C8—C91.376 (6)C27—H270.9300
C8—H8A0.9700C28—C291.377 (5)
C8—H8B0.9700C28—C331.378 (5)
C9—H9A0.9600C29—C301.388 (6)
C9—H9B0.9600C29—H290.9300
C9—H9C0.9600C30—C311.353 (6)
C10—C111.376 (4)C30—H300.9300
C10—C151.385 (4)C31—C321.338 (5)
C11—C121.368 (4)C32—C331.366 (5)
C11—H110.9300C32—H320.9300
C12—C131.369 (5)C33—H330.9300
C7—O2—C8116.7 (3)C13—C14—H14120.6
C16—N1—C6120.2 (3)C15—C14—H14120.6
C16—N1—C2121.6 (3)C10—C15—C14121.7 (3)
C6—N1—C2118.1 (3)C10—C15—H15119.1
C4—N2—C28127.9 (3)C14—C15—H15119.1
C4—N2—H2116.0N1—C16—C17121.9 (3)
C28—N2—H2116.0N1—C16—C21121.3 (3)
N1—C2—C3110.7 (3)C17—C16—C21116.8 (3)
N1—C2—C10112.9 (3)C18—C17—C16121.5 (3)
C3—C2—C10111.4 (3)C18—C17—H17119.3
N1—C2—H2A107.2C16—C17—H17119.3
C3—C2—H2A107.2C19—C18—C17119.1 (4)
C10—C2—H2A107.2C19—C18—H18120.5
C4—C3—C7121.2 (3)C17—C18—H18120.5
C4—C3—C2117.7 (3)C18—C19—C20121.8 (4)
C7—C3—C2121.1 (4)C18—C19—F2119.4 (4)
N2—C4—C3124.2 (3)C20—C19—F2118.8 (3)
N2—C4—C5119.8 (3)C19—C20—C21119.2 (3)
C3—C4—C5115.5 (3)C19—C20—H20120.4
C4—C5—C6108.9 (3)C21—C20—H20120.4
C4—C5—H5A109.9C20—C21—C16121.6 (3)
C6—C5—H5A109.9C20—C21—H21119.2
C4—C5—H5B109.9C16—C21—H21119.2
C6—C5—H5B109.9C23—C22—C27118.1 (3)
H5A—C5—H5B108.3C23—C22—C6122.6 (3)
N1—C6—C22114.4 (3)C27—C22—C6119.2 (3)
N1—C6—C5109.7 (3)C22—C23—C24121.8 (4)
C22—C6—C5109.1 (3)C22—C23—H23119.1
N1—C6—H6107.8C24—C23—H23119.1
C22—C6—H6107.8C25—C24—C23118.7 (4)
C5—C6—H6107.8C25—C24—H24120.7
O1—C7—O2121.0 (4)C23—C24—H24120.7
O1—C7—C3124.9 (4)C24—C25—C26121.5 (4)
O2—C7—C3114.1 (4)C24—C25—Cl1120.0 (4)
C9—C8—O2110.8 (4)C26—C25—Cl1118.5 (4)
C9—C8—H8A109.5C25—C26—C27118.7 (4)
O2—C8—H8A109.5C25—C26—H26120.7
C9—C8—H8B109.5C27—C26—H26120.7
O2—C8—H8B109.5C22—C27—C26121.2 (4)
H8A—C8—H8B108.1C22—C27—H27119.4
C8—C9—H9A109.5C26—C27—H27119.4
C8—C9—H9B109.5C29—C28—C33118.5 (4)
H9A—C9—H9B109.5C29—C28—N2119.9 (4)
C8—C9—H9C109.5C33—C28—N2121.6 (4)
H9A—C9—H9C109.5C28—C29—C30120.2 (4)
H9B—C9—H9C109.5C28—C29—H29119.9
C11—C10—C15116.8 (3)C30—C29—H29119.9
C11—C10—C2120.1 (3)C31—C30—C29118.5 (4)
C15—C10—C2123.1 (3)C31—C30—H30120.8
C12—C11—C10122.7 (3)C29—C30—H30120.8
C12—C11—H11118.7C32—C31—C30122.7 (5)
C10—C11—H11118.7C32—C31—F1119.7 (5)
C11—C12—C13119.1 (3)C30—C31—F1117.6 (5)
C11—C12—H12120.4C31—C32—C33119.1 (5)
C13—C12—H12120.4C31—C32—H32120.5
C12—C13—C14120.7 (3)C33—C32—H32120.5
C12—C13—Cl2119.9 (3)C32—C33—C28121.0 (4)
C14—C13—Cl2119.4 (3)C32—C33—H33119.5
C13—C14—C15118.9 (3)C28—C33—H33119.5
C16—N1—C2—C3−145.8 (3)C13—C14—C15—C100.0 (6)
C6—N1—C2—C329.1 (4)C6—N1—C16—C17170.8 (3)
C16—N1—C2—C1088.6 (4)C2—N1—C16—C17−14.4 (5)
C6—N1—C2—C10−96.4 (3)C6—N1—C16—C21−8.2 (5)
N1—C2—C3—C4−48.0 (4)C2—N1—C16—C21166.6 (3)
C10—C2—C3—C478.4 (4)N1—C16—C17—C18178.9 (3)
N1—C2—C3—C7129.1 (3)C21—C16—C17—C18−2.1 (5)
C10—C2—C3—C7−104.5 (4)C16—C17—C18—C192.0 (5)
C28—N2—C4—C3173.8 (3)C17—C18—C19—C20−1.6 (6)
C28—N2—C4—C5−14.8 (5)C17—C18—C19—F2179.9 (3)
C7—C3—C4—N24.2 (5)C18—C19—C20—C211.1 (6)
C2—C3—C4—N2−178.7 (3)F2—C19—C20—C21179.7 (3)
C7—C3—C4—C5−167.5 (3)C19—C20—C21—C16−1.2 (5)
C2—C3—C4—C59.6 (4)N1—C16—C21—C20−179.3 (3)
N2—C4—C5—C6−128.3 (3)C17—C16—C21—C201.7 (5)
C3—C4—C5—C643.7 (4)N1—C6—C22—C2323.6 (5)
C16—N1—C6—C2273.7 (4)C5—C6—C22—C23−99.8 (4)
C2—N1—C6—C22−101.3 (3)N1—C6—C22—C27−158.9 (3)
C16—N1—C6—C5−163.3 (3)C5—C6—C22—C2777.8 (4)
C2—N1—C6—C521.7 (4)C27—C22—C23—C24−3.2 (6)
C4—C5—C6—N1−59.6 (4)C6—C22—C23—C24174.4 (3)
C4—C5—C6—C2266.5 (4)C22—C23—C24—C251.6 (6)
C8—O2—C7—O1−0.5 (6)C23—C24—C25—C260.9 (7)
C8—O2—C7—C3−179.5 (4)C23—C24—C25—Cl1−177.3 (3)
C4—C3—C7—O1−2.5 (6)C24—C25—C26—C27−1.7 (7)
C2—C3—C7—O1−179.5 (3)Cl1—C25—C26—C27176.6 (3)
C4—C3—C7—O2176.5 (3)C23—C22—C27—C262.3 (6)
C2—C3—C7—O2−0.5 (5)C6—C22—C27—C26−175.4 (3)
C7—O2—C8—C9178.9 (4)C25—C26—C27—C220.1 (6)
N1—C2—C10—C11168.6 (3)C4—N2—C28—C29138.4 (4)
C3—C2—C10—C1143.4 (5)C4—N2—C28—C33−42.7 (6)
N1—C2—C10—C15−12.9 (5)C33—C28—C29—C300.1 (6)
C3—C2—C10—C15−138.2 (4)N2—C28—C29—C30179.0 (4)
C15—C10—C11—C121.4 (6)C28—C29—C30—C311.9 (7)
C2—C10—C11—C12180.0 (4)C29—C30—C31—C32−2.4 (7)
C10—C11—C12—C13−0.5 (6)C29—C30—C31—F1177.2 (4)
C11—C12—C13—C14−0.7 (6)C30—C31—C32—C330.9 (7)
C11—C12—C13—Cl2−178.7 (3)F1—C31—C32—C33−178.7 (4)
C12—C13—C14—C151.0 (6)C31—C32—C33—C281.2 (7)
Cl2—C13—C14—C15179.0 (3)C29—C28—C33—C32−1.7 (6)
C11—C10—C15—C14−1.1 (6)N2—C28—C33—C32179.4 (4)
C2—C10—C15—C14−179.6 (3)
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.862.012.674 (4)134
C9—H9C···Cl1i0.962.673.523 (5)148
C11—H11···O1ii0.932.523.250 (5)135
C18—H18···F1iii0.932.523.259 (5)137
C20—H20···F2iv0.932.483.411 (4)179
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N2—H2⋯O10.862.012.674 (4)134
C9—H9C⋯Cl1i 0.962.673.523 (5)148
C11—H11⋯O1ii 0.932.523.250 (5)135
C18—H18⋯F1iii 0.932.523.259 (5)137
C20—H20⋯F2iv 0.932.483.411 (4)179

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  11 in total

1.  A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery.

Authors:  P S Watson; B Jiang; B Scott
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

2.  The intolerable burden of malaria: a new look at the numbers.

Authors:  J G Breman; A Egan; G T Keusch
Journal:  Am J Trop Med Hyg       Date:  2001 Jan-Feb       Impact factor: 2.345

3.  Discovery of a potent substance P antagonist: recognition of the key molecular determinant.

Authors:  M C Desai; S L Lefkowitz; P F Thadeio; K P Longo; R M Snider
Journal:  J Med Chem       Date:  1992-12-25       Impact factor: 7.446

4.  Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials.

Authors:  Mridul Misra; Swaroop Kumar Pandey; Vivek Parashar Pandey; Jyoti Pandey; Renu Tripathi; Rama Pati Tripathi
Journal:  Bioorg Med Chem       Date:  2008-12-03       Impact factor: 3.641

Review 5.  Farnesyltransferase inhibitor as anticancer agent.

Authors:  Anuj G Agrawal; Rakesh R Somani
Journal:  Mini Rev Med Chem       Date:  2009-06       Impact factor: 3.862

6.  Synthesis and SAR of 3,5-diamino-piperidine derivatives: novel antibacterial translation inhibitors as aminoglycoside mimetics.

Authors:  Yuefen Zhou; Vlad E Gregor; Benjamin K Ayida; Geoffrey C Winters; Zhongxiang Sun; Douglas Murphy; Greg Haley; Dwight Bailey; Jamie M Froelich; Sarah Fish; Stephen E Webber; Thomas Hermann; Daniel Wall
Journal:  Bioorg Med Chem Lett       Date:  2006-12-12       Impact factor: 2.823

7.  New piperidinyl- and 1,2,3,6-tetrahydropyridinyl-pyrimidine derivatives as selective 5-HT1A receptor agonists with highly potent anti-ischemic effects.

Authors:  Katsuhide Kamei; Noriko Maeda; Ryoko Katsuragi-Ogino; Makoto Koyama; Mika Nakajima; Toshio Tatsuoka; Tomochika Ohno; Teruyoshi Inoue
Journal:  Bioorg Med Chem Lett       Date:  2005-06-15       Impact factor: 2.823

8.  Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors.

Authors:  Jeffrey A Deskus; James R Epperson; Charles P Sloan; Joseph A Cipollina; Pierre Dextraze; Jingfang Qian-Cutrone; Qi Gao; Baoqing Ma; Brett R Beno; Gail K Mattson; Thaddeus F Molski; Rudolph G Krause; Matthew T Taber; Nicholas J Lodge; Ronald J Mattson
Journal:  Bioorg Med Chem Lett       Date:  2007-03-16       Impact factor: 2.823

9.  Ethyl 4-anilino-2,6-bis-(4-fluoro-phen-yl)-1-phenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Authors:  Sumati Anthal; Goutam Brahmachari; Suvankar Das; Rajni Kant; Vivek K Gupta
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-01-26

10.  Structure validation in chemical crystallography.

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

1.  Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies.

Authors:  Bilal Ahmad Khan; Muhammad Ashfaq; Shabbir Muhammad; Khurram Shahzad Munawar; Muhammad Nawaz Tahir; Abdullah G Al-Sehemi; Saleh S Alarfaji
Journal:  ACS Omega       Date:  2022-08-11
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.