Literature DB >> 21577671

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

G Aridoss, D Gayathri, D Velmurugan, M S Kim, Yeon Tae Jeong.   

Abstract

The piperidone ring in the title compound, C(23)H(26)ClNO(4), adopts a boat conformation with its two out-of-plane C atoms deviating by 0.597 (2) and 0.630 (2) Å from the least-squares plane of the rest of atoms in the ring. The two aromatic rings are roughly perpendicular to each other, making a dihedral angle of 75.1 (1)°, and a C-H⋯π intra-molecular inter-action is observed. The crystal packing is stabilized by a C-H⋯O inter-molecular inter-action, generating a chain with a C(9) motif along the a axis.

Entities:  

Year:  2009        PMID： 21577671      PMCID： PMC2970045          DOI： 10.1107/S1600536809033674

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


Related literature

For the biological activity of the piperidine nucleus, see: Weintraub et al. (2003 ▶). For the biological activity of piperidones and their N-acyl derivatives, see: Perumal et al. (2001 ▶); Weintraub et al. (2003 ▶); Aridoss et al. (2008 ▶, 2009 ▶); Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007 ▶). For a related structure, see: Ramachandran et al. (2008 ▶). For the synthesis, see: Aridoss, Balasubramanian, Parthiban & Kabilan (2007 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C23H26ClNO4 M = 415.90 Triclinic, a = 8.9921 (6) Å b = 11.3725 (8) Å c = 11.9373 (8) Å α = 71.630 (1)° β = 68.465 (1)° γ = 72.903 (1)° V = 1055.45 (12) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 293 K 0.27 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: none 11114 measured reflections 4603 independent reflections 4054 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.145 S = 1.05 4603 reflections 266 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.35 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033674/is2452sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033674/is2452Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H26ClNO4Z = 2
Mr = 415.90F(000) = 440
Triclinic, P1Dx = 1.309 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9921 (6) ÅCell parameters from 3104 reflections
b = 11.3725 (8) Åθ = 1.9–28.0°
c = 11.9373 (8) ŵ = 0.21 mm−1
α = 71.630 (1)°T = 293 K
β = 68.465 (1)°Block, colourless
γ = 72.903 (1)°0.27 × 0.22 × 0.20 mm
V = 1055.45 (12) Å3
Bruker SMART APEX CCD area-detector diffractometer4054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 28.0°, θmin = 1.9°
ω scansh = −11→11
11114 measured reflectionsk = −15→14
4603 independent 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0778P)2 + 0.248P] where P = (Fo2 + 2Fc2)/3
4603 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.35 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
C10.62492 (17)0.76769 (12)0.18450 (12)0.0365 (3)
H10.58870.78130.11250.044*
C20.75304 (18)0.84927 (13)0.14741 (13)0.0409 (3)
H20.79830.82640.21640.049*
C30.6724 (2)0.98870 (15)0.13142 (15)0.0493 (4)
C40.51873 (19)1.02296 (13)0.23286 (14)0.0435 (3)
H40.53331.08700.26480.052*
C50.47941 (17)0.90843 (12)0.34028 (13)0.0376 (3)
H50.36550.93440.38790.045*
C60.33625 (18)0.76953 (14)0.31911 (14)0.0415 (3)
C70.3312 (2)0.6876 (2)0.2420 (2)0.0677 (5)
H7A0.41390.61080.24940.081*
H7B0.35720.73270.15560.081*
C80.70453 (17)0.62802 (13)0.21844 (13)0.0391 (3)
C90.7535 (2)0.57969 (14)0.32461 (14)0.0457 (3)
H90.73220.63230.37690.055*
C100.8335 (2)0.45490 (16)0.35465 (17)0.0557 (4)
H100.86530.42420.42610.067*
C110.8647 (2)0.37779 (16)0.27738 (19)0.0609 (5)
H110.91860.29420.29680.073*
C120.8177 (2)0.42187 (16)0.17127 (19)0.0591 (4)
H120.83920.36810.12010.071*
C130.73780 (19)0.54777 (15)0.14083 (15)0.0465 (3)
C140.7241 (3)0.5234 (2)−0.0467 (2)0.0764 (6)
H14A0.84040.4997−0.08000.115*
H14B0.67820.5702−0.11280.115*
H14C0.67920.4486−0.00450.115*
C150.8945 (2)0.82148 (18)0.03379 (16)0.0550 (4)
H15A0.85360.8374−0.03450.083*
H15B0.94880.73450.05160.083*
H15C0.97040.87510.01280.083*
C160.3767 (2)1.08034 (17)0.17668 (17)0.0568 (4)
H16A0.40101.15350.11130.085*
H16B0.27841.10450.23970.085*
H16C0.36211.01880.14400.085*
C170.57351 (18)0.85534 (13)0.43542 (13)0.0380 (3)
C180.51132 (19)0.76226 (14)0.53789 (13)0.0431 (3)
H180.41290.74320.54750.052*
C190.5920 (2)0.69789 (16)0.62510 (15)0.0516 (4)
H190.54770.63720.69300.062*
C200.7387 (2)0.72462 (17)0.61039 (16)0.0541 (4)
H200.79660.67820.66620.065*
C210.8006 (2)0.81951 (16)0.51375 (15)0.0491 (4)
H210.89820.83860.50600.059*
C220.71660 (18)0.88681 (13)0.42754 (13)0.0400 (3)
C230.9135 (3)1.0185 (2)0.3189 (2)0.0691 (5)
H23A0.90011.04480.39150.104*
H23B0.93481.08720.24750.104*
H23C1.00340.94790.30920.104*
N10.48009 (14)0.80640 (11)0.28696 (11)0.0365 (3)
O10.21671 (13)0.80127 (12)0.40297 (11)0.0529 (3)
O20.68636 (18)0.59924 (13)0.03773 (12)0.0640 (4)
O30.7251 (2)1.06760 (13)0.04061 (15)0.0806 (5)
O40.76967 (14)0.98287 (11)0.33137 (11)0.0502 (3)
Cl10.14021 (6)0.64709 (5)0.28760 (5)0.06999 (18)
U11U22U33U12U13U23
C10.0373 (7)0.0359 (6)0.0342 (6)−0.0015 (5)−0.0113 (5)−0.0103 (5)
C20.0401 (7)0.0400 (7)0.0398 (7)−0.0062 (6)−0.0100 (6)−0.0097 (5)
C30.0534 (9)0.0401 (7)0.0506 (8)−0.0103 (7)−0.0156 (7)−0.0050 (6)
C40.0497 (8)0.0330 (6)0.0496 (8)−0.0015 (6)−0.0221 (7)−0.0102 (6)
C50.0380 (7)0.0351 (6)0.0411 (7)0.0000 (5)−0.0148 (6)−0.0141 (5)
C60.0367 (7)0.0406 (7)0.0468 (7)−0.0039 (5)−0.0136 (6)−0.0123 (6)
C70.0475 (9)0.0809 (13)0.0896 (14)−0.0185 (9)−0.0085 (9)−0.0493 (11)
C80.0366 (7)0.0360 (7)0.0405 (7)−0.0016 (5)−0.0091 (6)−0.0116 (5)
C90.0485 (8)0.0411 (7)0.0434 (7)−0.0006 (6)−0.0147 (6)−0.0111 (6)
C100.0561 (10)0.0452 (8)0.0555 (9)−0.0002 (7)−0.0205 (8)−0.0028 (7)
C110.0588 (10)0.0362 (8)0.0769 (12)0.0015 (7)−0.0197 (9)−0.0103 (8)
C120.0591 (10)0.0432 (8)0.0741 (11)−0.0007 (7)−0.0146 (9)−0.0279 (8)
C130.0449 (8)0.0453 (8)0.0484 (8)−0.0033 (6)−0.0105 (6)−0.0194 (6)
C140.0947 (16)0.0851 (14)0.0634 (12)−0.0154 (12)−0.0221 (11)−0.0406 (11)
C150.0466 (9)0.0614 (10)0.0490 (9)−0.0118 (7)−0.0026 (7)−0.0154 (7)
C160.0626 (11)0.0490 (9)0.0594 (10)0.0032 (8)−0.0331 (9)−0.0098 (7)
C170.0393 (7)0.0368 (6)0.0383 (7)−0.0021 (5)−0.0119 (6)−0.0139 (5)
C180.0432 (8)0.0455 (7)0.0399 (7)−0.0105 (6)−0.0098 (6)−0.0111 (6)
C190.0613 (10)0.0489 (8)0.0395 (7)−0.0107 (7)−0.0135 (7)−0.0059 (6)
C200.0576 (10)0.0576 (9)0.0464 (8)−0.0006 (8)−0.0244 (7)−0.0109 (7)
C210.0462 (8)0.0541 (9)0.0503 (8)−0.0037 (7)−0.0206 (7)−0.0154 (7)
C220.0411 (7)0.0388 (7)0.0406 (7)−0.0053 (6)−0.0115 (6)−0.0134 (5)
C230.0613 (11)0.0673 (12)0.0800 (13)−0.0300 (9)−0.0246 (10)0.0006 (10)
N10.0355 (6)0.0358 (5)0.0386 (6)−0.0020 (4)−0.0116 (5)−0.0134 (4)
O10.0377 (6)0.0646 (7)0.0567 (7)−0.0090 (5)−0.0075 (5)−0.0240 (6)
O20.0806 (9)0.0622 (7)0.0563 (7)0.0056 (7)−0.0293 (7)−0.0315 (6)
O30.0860 (11)0.0505 (7)0.0731 (9)−0.0167 (7)−0.0029 (8)0.0063 (6)
O40.0521 (7)0.0488 (6)0.0535 (6)−0.0188 (5)−0.0211 (5)−0.0029 (5)
Cl10.0555 (3)0.0834 (4)0.0871 (4)−0.0249 (2)−0.0184 (2)−0.0350 (3)
C1—N11.4896 (17)C12—C131.399 (2)
C1—C81.5291 (18)C12—H120.9300
C1—C21.542 (2)C13—O21.370 (2)
C1—H10.9800C14—O21.414 (2)
C2—C31.520 (2)C14—H14A0.9600
C2—C151.525 (2)C14—H14B0.9600
C2—H20.9800C14—H14C0.9600
C3—O31.210 (2)C15—H15A0.9600
C3—C41.510 (2)C15—H15B0.9600
C4—C51.533 (2)C15—H15C0.9600
C4—C161.539 (2)C16—H16A0.9600
C4—H40.9800C16—H16B0.9600
C5—N11.4866 (17)C16—H16C0.9600
C5—C171.5308 (18)C17—C221.397 (2)
C5—H50.9800C17—C181.400 (2)
C6—O11.2238 (18)C18—C191.381 (2)
C6—N11.3598 (19)C18—H180.9300
C6—C71.521 (2)C19—C201.377 (3)
C7—Cl11.755 (2)C19—H190.9300
C7—H7A0.9700C20—C211.379 (3)
C7—H7B0.9700C20—H200.9300
C8—C91.390 (2)C21—C221.397 (2)
C8—C131.396 (2)C21—H210.9300
C9—C101.389 (2)C22—O41.3612 (18)
C9—H90.9300C23—O41.410 (2)
C10—C111.369 (3)C23—H23A0.9600
C10—H100.9300C23—H23B0.9600
C11—C121.379 (3)C23—H23C0.9600
C11—H110.9300
N1—C1—C8112.28 (11)O2—C13—C8116.34 (13)
N1—C1—C2110.76 (11)O2—C13—C12123.70 (15)
C8—C1—C2109.21 (11)C8—C13—C12119.96 (15)
N1—C1—H1108.2O2—C14—H14A109.5
C8—C1—H1108.2O2—C14—H14B109.5
C2—C1—H1108.2H14A—C14—H14B109.5
C3—C2—C15112.61 (13)O2—C14—H14C109.5
C3—C2—C1110.45 (12)H14A—C14—H14C109.5
C15—C2—C1111.99 (12)H14B—C14—H14C109.5
C3—C2—H2107.2C2—C15—H15A109.5
C15—C2—H2107.2C2—C15—H15B109.5
C1—C2—H2107.2H15A—C15—H15B109.5
O3—C3—C4121.64 (15)C2—C15—H15C109.5
O3—C3—C2122.00 (16)H15A—C15—H15C109.5
C4—C3—C2116.32 (13)H15B—C15—H15C109.5
C3—C4—C5112.21 (11)C4—C16—H16A109.5
C3—C4—C16108.41 (13)C4—C16—H16B109.5
C5—C4—C16110.13 (14)H16A—C16—H16B109.5
C3—C4—H4108.7C4—C16—H16C109.5
C5—C4—H4108.7H16A—C16—H16C109.5
C16—C4—H4108.7H16B—C16—H16C109.5
N1—C5—C17110.48 (10)C22—C17—C18117.60 (13)
N1—C5—C4107.60 (11)C22—C17—C5126.74 (13)
C17—C5—C4121.40 (12)C18—C17—C5115.61 (13)
N1—C5—H5105.4C19—C18—C17121.83 (15)
C17—C5—H5105.4C19—C18—H18119.1
C4—C5—H5105.4C17—C18—H18119.1
O1—C6—N1122.87 (14)C20—C19—C18119.29 (15)
O1—C6—C7121.45 (14)C20—C19—H19120.4
N1—C6—C7115.66 (13)C18—C19—H19120.4
C6—C7—Cl1112.67 (13)C19—C20—C21120.68 (15)
C6—C7—H7A109.1C19—C20—H20119.7
Cl1—C7—H7A109.1C21—C20—H20119.7
C6—C7—H7B109.1C20—C21—C22119.85 (16)
Cl1—C7—H7B109.1C20—C21—H21120.1
H7A—C7—H7B107.8C22—C21—H21120.1
C9—C8—C13118.37 (13)O4—C22—C21122.75 (14)
C9—C8—C1120.37 (12)O4—C22—C17116.74 (13)
C13—C8—C1121.17 (13)C21—C22—C17120.49 (14)
C10—C9—C8121.73 (15)O4—C23—H23A109.5
C10—C9—H9119.1O4—C23—H23B109.5
C8—C9—H9119.1H23A—C23—H23B109.5
C11—C10—C9118.96 (16)O4—C23—H23C109.5
C11—C10—H10120.5H23A—C23—H23C109.5
C9—C10—H10120.5H23B—C23—H23C109.5
C10—C11—C12121.17 (15)C6—N1—C5117.12 (11)
C10—C11—H11119.4C6—N1—C1122.55 (11)
C12—C11—H11119.4C5—N1—C1119.22 (11)
C11—C12—C13119.81 (16)C13—O2—C14118.37 (15)
C11—C12—H12120.1C22—O4—C23119.13 (13)
C13—C12—H12120.1
N1—C1—C2—C3−47.55 (15)C11—C12—C13—C8−0.6 (3)
C8—C1—C2—C3−171.71 (12)N1—C5—C17—C22116.22 (15)
N1—C1—C2—C15−173.93 (12)C4—C5—C17—C22−11.1 (2)
C8—C1—C2—C1561.92 (15)N1—C5—C17—C18−61.14 (16)
C15—C2—C3—O3−4.8 (2)C4—C5—C17—C18171.55 (12)
C1—C2—C3—O3−130.78 (19)C22—C17—C18—C19−3.6 (2)
C15—C2—C3—C4172.96 (14)C5—C17—C18—C19173.98 (13)
C1—C2—C3—C446.93 (18)C17—C18—C19—C20−0.8 (2)
O3—C3—C4—C5−177.97 (18)C18—C19—C20—C213.7 (3)
C2—C3—C4—C54.31 (19)C19—C20—C21—C22−2.0 (2)
O3—C3—C4—C1660.2 (2)C20—C21—C22—O4178.85 (14)
C2—C3—C4—C16−117.54 (16)C20—C21—C22—C17−2.6 (2)
C3—C4—C5—N1−52.29 (16)C18—C17—C22—O4−176.08 (12)
C16—C4—C5—N168.57 (14)C5—C17—C22—O46.6 (2)
C3—C4—C5—C1776.29 (16)C18—C17—C22—C215.3 (2)
C16—C4—C5—C17−162.84 (12)C5—C17—C22—C21−171.99 (13)
O1—C6—C7—Cl10.0 (2)O1—C6—N1—C5−12.0 (2)
N1—C6—C7—Cl1−178.78 (13)C7—C6—N1—C5166.80 (14)
N1—C1—C8—C9−54.71 (18)O1—C6—N1—C1−179.81 (13)
C2—C1—C8—C968.55 (17)C7—C6—N1—C1−1.0 (2)
N1—C1—C8—C13128.78 (15)C17—C5—N1—C6109.92 (14)
C2—C1—C8—C13−107.96 (16)C4—C5—N1—C6−115.50 (13)
C13—C8—C9—C10−0.1 (2)C17—C5—N1—C1−81.81 (14)
C1—C8—C9—C10−176.73 (15)C4—C5—N1—C152.77 (15)
C8—C9—C10—C110.0 (3)C8—C1—N1—C6−72.11 (16)
C9—C10—C11—C12−0.2 (3)C2—C1—N1—C6165.51 (12)
C10—C11—C12—C130.5 (3)C8—C1—N1—C5120.29 (13)
C9—C8—C13—O2179.59 (15)C2—C1—N1—C5−2.09 (15)
C1—C8—C13—O2−3.8 (2)C8—C13—O2—C14177.07 (18)
C9—C8—C13—C120.4 (2)C12—C13—O2—C14−3.7 (3)
C1—C8—C13—C12176.96 (15)C21—C22—O4—C23−1.4 (2)
C11—C12—C13—O2−179.72 (18)C17—C22—O4—C23−179.98 (15)
D—H···AD—HH···AD···AD—H···A
C23—H23C···O1i0.962.503.321 (3)144
C9—H9···Cg0.932.693.621 (2)177
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C23—H23C⋯O1i0.962.503.321 (3)144
C9—H9⋯Cg0.932.693.621 (2)177

Symmetry code: (i) . Cg is the centroid of the C17–C22 ring.

  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.  A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives.

Authors:  Gopalakrishnan Aridoss; Shanmugasundaram Amirthaganesan; Nanjundan Ashok Kumar; Jong Tae Kim; Kwon Taek Lim; Senthamaraikannan Kabilan; Yeon Tae Jeong
Journal:  Bioorg Med Chem Lett       Date:  2008-10-14       Impact factor: 2.823

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

Authors:  R Ramachandran; G Aridoss; D Velmurugan; S Kabilan; Y T Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-27

4.  Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: antimicrobial, analgesic and antipyretic studies.

Authors:  G Aridoss; P Parthiban; R Ramachandran; M Prakash; S Kabilan; Yeon Tae Jeong
Journal:  Eur J Med Chem       Date:  2008-04-07       Impact factor: 6.514

5.  Synthesis and NMR spectral studies of N-chloroacetyl-2,6-diarylpiperidin-4-ones.

Authors:  G Aridoss; S Balasubramanian; P Parthiban; S Kabilan
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2007-01-20       Impact factor: 4.098

6.  Structure validation in chemical crystallography.

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

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

Authors:  G Aridoss; S Sundaramoorthy; D Velmurugan; K S Park; Y T Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-29

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

Authors:  G Aridoss; S Sundaramoorthy; D Velmurugan; K S Park; Y T Jeong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-22
  2 in total

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