Literature DB >> 21579545

1-(2-Bromo-acet-yl)-3-methyl-2,6-diphenyl-piperidin-4-one.

G Aridoss, S Sundaramoorthy, D Velmurugan, K S Park, Y T Jeong.   

Abstract

In the title compound, C(20)H(20)BrNO(2), the piperidone ring adopts a boat conformation. The phenyl rings are oriented at dihedral angles of 97.8 (2) and 96.0 (1)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 49.7 (1)°. In the crystal, bifurcated C-H⋯O hydrogen bonds form a R(2) (1)(7) ring motif, linking the mol-ecules into centrosymmetric dimers.

Entities:  

Year:  2010        PMID： 21579545      PMCID： PMC2979607          DOI： 10.1107/S160053681001901X

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


Related literature

For the biological activity of functionalized piperidines, see: Richardo et al. (1979 ▶); Schneider (1996 ▶); Mukhtar & Wright (2005 ▶); Aridoss et al. (2007 ▶); Winkler & Holan (1989 ▶). For related structures see: Aridoss et al. (2009a ▶,b ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C20H20BrNO2 M = 386.28 Monoclinic, a = 21.4006 (8) Å b = 14.5873 (6) Å c = 13.8107 (5) Å β = 125.368 (2)° V = 3515.7 (2) Å3 Z = 8 Mo Kα radiation μ = 2.35 mm−1 T = 292 K 0.3 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.499, T max = 0.596 17094 measured reflections 4398 independent reflections 2725 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.213 S = 1.02 4398 reflections 218 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.77 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001901X/bt5275sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681001901X/bt5275Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H20BrNO2F(000) = 1584
Mr = 386.28Dx = 1.460 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2025 reflections
a = 21.4006 (8) Åθ = 0.5–0.6°
b = 14.5873 (6) ŵ = 2.35 mm−1
c = 13.8107 (5) ÅT = 292 K
β = 125.368 (2)°Block, colorless
V = 3515.7 (2) Å30.3 × 0.26 × 0.22 mm
Z = 8
Bruker SMART APEXII area-detector diffractometer4398 independent reflections
Radiation source: fine-focus sealed tube2725 reflections with I > 2σ(I)
graphiteRint = 0.035
ω and φ scansθmax = 28.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −27→28
Tmin = 0.499, Tmax = 0.596k = −19→19
17094 measured reflectionsl = −18→18
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) = 0.213H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.1259P)2 + 4.1414P] where P = (Fo2 + 2Fc2)/3
4398 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.77 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.00908 (18)0.2545 (2)0.0494 (3)0.0355 (7)
H10.05550.23170.12290.043*
C20.0317 (2)0.3418 (3)0.0168 (4)0.0517 (10)
H2A0.04320.38890.07450.062*
H2B0.07800.33030.02140.062*
C3−0.0287 (3)0.3764 (3)−0.1039 (4)0.0581 (11)
C4−0.0933 (2)0.3111 (3)−0.1867 (3)0.0463 (8)
H4−0.13070.3148−0.16740.056*
C5−0.06703 (18)0.2104 (2)−0.1692 (3)0.0359 (7)
H5−0.03930.2039−0.20560.043*
C6−0.13640 (19)0.1469 (2)−0.2373 (3)0.0355 (7)
C7−0.1502 (2)0.0969 (3)−0.3328 (3)0.0502 (9)
H7−0.11500.0987−0.35180.060*
C8−0.2159 (3)0.0440 (3)−0.4008 (3)0.0605 (11)
H8−0.22490.0115−0.46570.073*
C9−0.2672 (2)0.0396 (3)−0.3726 (4)0.0622 (12)
H9−0.31100.0038−0.41790.075*
C10−0.2541 (2)0.0881 (3)−0.2772 (4)0.0526 (10)
H10−0.28910.0848−0.25770.063*
C11−0.1889 (2)0.1421 (2)−0.2096 (3)0.0408 (8)
H11−0.18050.1752−0.14550.049*
C12−0.05143 (17)0.2656 (2)0.0741 (3)0.0334 (7)
C13−0.0720 (2)0.3505 (2)0.0908 (4)0.0470 (9)
H13−0.05100.40340.08310.056*
C14−0.1253 (3)0.3567 (3)0.1196 (4)0.0584 (11)
H14−0.13880.41400.13150.070*
C15−0.1573 (2)0.2800 (3)0.1301 (4)0.0566 (11)
H15−0.19340.28500.14690.068*
C16−0.1354 (2)0.1944 (3)0.1156 (3)0.0508 (9)
H16−0.15660.14170.12330.061*
C17−0.0820 (2)0.1873 (3)0.0896 (3)0.0408 (8)
H17−0.06650.12970.08250.049*
C18−0.1349 (3)0.3390 (3)−0.3166 (5)0.0706 (14)
H18A−0.14950.4023−0.32550.106*
H18B−0.18000.3019−0.36480.106*
H18C−0.10160.3302−0.34120.106*
C190.02886 (17)0.1079 (2)−0.0205 (3)0.0353 (7)
C200.09463 (19)0.0844 (3)0.1063 (3)0.0432 (8)
H20A0.10630.01950.11250.052*
H20B0.08030.09820.15980.052*
N1−0.01254 (14)0.18526 (19)−0.0422 (2)0.0328 (6)
O1−0.0265 (3)0.4523 (2)−0.1361 (4)0.1037 (15)
O20.01584 (14)0.05669 (18)−0.1000 (2)0.0472 (6)
Br10.18249 (2)0.15486 (4)0.14906 (5)0.0736 (3)
U11U22U33U12U13U23
C10.0316 (14)0.0321 (16)0.0404 (17)−0.0039 (12)0.0195 (13)−0.0042 (13)
C20.048 (2)0.040 (2)0.076 (3)−0.0124 (15)0.041 (2)−0.0081 (18)
C30.080 (3)0.041 (2)0.074 (3)−0.008 (2)0.056 (3)0.003 (2)
C40.050 (2)0.0399 (19)0.055 (2)0.0067 (16)0.0333 (18)0.0140 (17)
C50.0375 (16)0.0403 (18)0.0344 (16)0.0051 (13)0.0234 (14)0.0063 (14)
C60.0326 (15)0.0386 (17)0.0287 (14)0.0096 (12)0.0140 (13)0.0056 (13)
C70.051 (2)0.059 (2)0.0373 (18)0.0107 (18)0.0239 (17)0.0013 (17)
C80.059 (2)0.061 (3)0.0353 (18)0.009 (2)0.0120 (17)−0.0110 (18)
C90.042 (2)0.058 (3)0.050 (2)−0.0027 (18)0.0060 (17)−0.011 (2)
C100.0347 (18)0.061 (3)0.054 (2)0.0003 (16)0.0205 (16)−0.0042 (19)
C110.0352 (16)0.046 (2)0.0372 (17)0.0049 (14)0.0187 (14)−0.0013 (15)
C120.0284 (13)0.0383 (17)0.0270 (14)−0.0006 (12)0.0124 (12)−0.0013 (13)
C130.053 (2)0.0346 (18)0.054 (2)0.0059 (15)0.0313 (19)0.0036 (16)
C140.066 (3)0.057 (3)0.064 (3)0.021 (2)0.044 (2)0.007 (2)
C150.043 (2)0.086 (3)0.046 (2)0.013 (2)0.0288 (17)0.009 (2)
C160.047 (2)0.064 (2)0.0411 (19)−0.0131 (19)0.0259 (17)−0.0015 (18)
C170.0459 (19)0.0381 (18)0.0377 (17)−0.0052 (15)0.0237 (15)−0.0045 (15)
C180.077 (3)0.066 (3)0.063 (3)0.011 (2)0.037 (3)0.030 (2)
C190.0279 (14)0.0363 (17)0.0400 (17)0.0017 (12)0.0187 (13)0.0006 (14)
C200.0322 (15)0.0412 (19)0.0468 (19)0.0022 (13)0.0175 (14)0.0030 (15)
N10.0313 (13)0.0331 (13)0.0329 (13)0.0013 (10)0.0179 (11)−0.0002 (11)
O10.161 (4)0.047 (2)0.096 (3)−0.030 (2)0.071 (3)0.0106 (18)
O20.0424 (13)0.0498 (15)0.0456 (14)0.0084 (11)0.0233 (11)−0.0064 (12)
Br10.0406 (3)0.0898 (5)0.0780 (4)−0.0045 (2)0.0272 (3)−0.0027 (3)
C1—N11.468 (4)C10—C111.391 (5)
C1—C21.521 (5)C10—H100.9300
C1—C121.527 (4)C11—H110.9300
C1—H10.9800C12—C131.378 (5)
C2—C31.486 (7)C12—C171.394 (5)
C2—H2A0.9700C13—C141.411 (6)
C2—H2B0.9700C13—H130.9300
C3—O11.204 (5)C14—C151.362 (7)
C3—C41.516 (6)C14—H140.9300
C4—C181.525 (6)C15—C161.389 (6)
C4—C51.541 (5)C15—H150.9300
C4—H40.9800C16—C171.384 (5)
C5—N11.485 (4)C16—H160.9300
C5—C61.527 (5)C17—H170.9300
C5—H50.9800C18—H18A0.9600
C6—C71.382 (5)C18—H18B0.9600
C6—C111.381 (5)C18—H18C0.9600
C7—C81.387 (6)C19—O21.219 (4)
C7—H70.9300C19—N11.357 (4)
C8—C91.362 (7)C19—C201.520 (5)
C8—H80.9300C20—Br11.912 (4)
C9—C101.375 (6)C20—H20A0.9700
C9—H90.9300C20—H20B0.9700
N1—C1—C2108.5 (3)C11—C10—H10119.9
N1—C1—C12112.4 (2)C6—C11—C10120.3 (3)
C2—C1—C12115.7 (3)C6—C11—H11119.8
N1—C1—H1106.6C10—C11—H11119.8
C2—C1—H1106.6C13—C12—C17119.2 (3)
C12—C1—H1106.6C13—C12—C1121.9 (3)
C3—C2—C1113.4 (3)C17—C12—C1118.8 (3)
C3—C2—H2A108.9C12—C13—C14119.5 (4)
C1—C2—H2A108.9C12—C13—H13120.2
C3—C2—H2B108.9C14—C13—H13120.2
C1—C2—H2B108.9C15—C14—C13121.0 (4)
H2A—C2—H2B107.7C15—C14—H14119.5
O1—C3—C2122.2 (5)C13—C14—H14119.5
O1—C3—C4120.8 (5)C14—C15—C16119.4 (4)
C2—C3—C4117.0 (3)C14—C15—H15120.3
C3—C4—C18112.1 (3)C16—C15—H15120.3
C3—C4—C5112.9 (3)C17—C16—C15120.2 (4)
C18—C4—C5110.5 (3)C17—C16—H16119.9
C3—C4—H4107.0C15—C16—H16119.9
C18—C4—H4107.0C16—C17—C12120.6 (4)
C5—C4—H4107.0C16—C17—H17119.7
N1—C5—C6113.4 (3)C12—C17—H17119.7
N1—C5—C4112.7 (3)C4—C18—H18A109.5
C6—C5—C4110.2 (3)C4—C18—H18B109.5
N1—C5—H5106.7H18A—C18—H18B109.5
C6—C5—H5106.7C4—C18—H18C109.5
C4—C5—H5106.7H18A—C18—H18C109.5
C7—C6—C11118.6 (3)H18B—C18—H18C109.5
C7—C6—C5120.2 (3)O2—C19—N1122.1 (3)
C11—C6—C5121.1 (3)O2—C19—C20118.4 (3)
C6—C7—C8120.8 (4)N1—C19—C20119.5 (3)
C6—C7—H7119.6C19—C20—Br1108.9 (2)
C8—C7—H7119.6C19—C20—H20A109.9
C9—C8—C7120.1 (4)Br1—C20—H20A109.9
C9—C8—H8120.0C19—C20—H20B109.9
C7—C8—H8120.0Br1—C20—H20B109.9
C8—C9—C10120.0 (4)H20A—C20—H20B108.3
C8—C9—H9120.0C19—N1—C1122.8 (3)
C10—C9—H9120.0C19—N1—C5115.6 (3)
C9—C10—C11120.1 (4)C1—N1—C5119.2 (3)
C9—C10—H10119.9
N1—C1—C2—C355.3 (4)C2—C1—C12—C13−13.3 (5)
C12—C1—C2—C3−72.0 (4)N1—C1—C12—C1746.6 (4)
C1—C2—C3—O1166.4 (5)C2—C1—C12—C17172.0 (3)
C1—C2—C3—C4−14.4 (5)C17—C12—C13—C14−1.9 (5)
O1—C3—C4—C1819.2 (6)C1—C12—C13—C14−176.7 (3)
C2—C3—C4—C18−159.9 (4)C12—C13—C14—C15−0.6 (7)
O1—C3—C4—C5144.8 (5)C13—C14—C15—C161.8 (7)
C2—C3—C4—C5−34.4 (5)C14—C15—C16—C17−0.5 (6)
C3—C4—C5—N141.5 (4)C15—C16—C17—C12−2.0 (5)
C18—C4—C5—N1167.9 (3)C13—C12—C17—C163.2 (5)
C3—C4—C5—C6169.2 (3)C1—C12—C17—C16178.1 (3)
C18—C4—C5—C6−64.3 (4)O2—C19—C20—Br198.6 (3)
N1—C5—C6—C7−119.1 (3)N1—C19—C20—Br1−80.3 (3)
C4—C5—C6—C7113.5 (3)O2—C19—N1—C1−170.7 (3)
N1—C5—C6—C1164.7 (4)C20—C19—N1—C18.1 (5)
C4—C5—C6—C11−62.7 (4)O2—C19—N1—C5−8.3 (5)
C11—C6—C7—C80.9 (5)C20—C19—N1—C5170.5 (3)
C5—C6—C7—C8−175.3 (3)C2—C1—N1—C19113.0 (3)
C6—C7—C8—C9−1.1 (6)C12—C1—N1—C19−117.8 (3)
C7—C8—C9—C100.4 (7)C2—C1—N1—C5−48.8 (4)
C8—C9—C10—C110.4 (6)C12—C1—N1—C580.3 (3)
C7—C6—C11—C10−0.1 (5)C6—C5—N1—C1971.5 (3)
C5—C6—C11—C10176.1 (3)C4—C5—N1—C19−162.4 (3)
C9—C10—C11—C6−0.5 (6)C6—C5—N1—C1−125.4 (3)
N1—C1—C12—C13−138.6 (3)C4—C5—N1—C10.7 (4)
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.972.563.458 (6)154
C13—H13···O1i0.932.513.404 (5)161
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2A⋯O1i0.972.563.458 (6)154
C13—H13⋯O1i0.932.513.404 (5)161

Symmetry code: (i) .

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Authors:  G Aridoss; D Gayathri; D Velmurugan; M S Kim; Yeon Tae Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-29

5.  1-Chloro-acetyl-2,6-bis-(3-fluoro-phen-yl)piperidin-4-one.

Authors:  G Aridoss; D Gayathri; D Velmurugan; M S Kim; Yeon Tae Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-25

6.  Structure validation in chemical crystallography.

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1.  1-Chloro-acetyl-2,6-bis-(2-chloro-phen-yl)-3,5-dimethyl-piperidin-4-one.

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