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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o263.
Published online 2010 January 9. doi:  10.1107/S1600536809054725
PMCID: PMC2979939

1-Dichloro­acetyl-r-2,c-6-bis­(4-methoxy­phen­yl)-t-3,t-5-dimethyl­piperidin-4-one

Abstract

In the title compound, C23H25Cl2NO4, the piperidine ring adopts a distorted boat conformation. The dihedral angle between the benzene rings is 54.8 (1)°. In the crystal, the mol­ecules are linked into a two-dimensional network parallel to the ab plane by C—H(...)O hydrogen bonds.

Related literature

For the biological properties of piperidin-4-one compounds, see: El-Subbagh et al. (2000 [triangle]); Jerom & Spencer (1988 [triangle]); Perumal et al. (2001 [triangle]); Hagenbach & Gysin (1952 [triangle]); Mobio et al. (1989 [triangle]); Katritzky & Fan (1990 [triangle]); Ganellin & Spickett (1965 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]). For asymmetry parameters, see: Nardelli (1983 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o263-scheme1.jpg

Experimental

Crystal data

  • C23H25Cl2NO4
  • M r = 450.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o263-efi1.jpg
  • a = 8.1251 (7) Å
  • b = 9.9702 (9) Å
  • c = 27.649 (2) Å
  • β = 92.265 (5)°
  • V = 2238.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 293 K
  • 0.27 × 0.26 × 0.23 mm

Data collection

  • Bruker SMART APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2008 [triangle]) T min = 0.917, T max = 0.929
  • 19833 measured reflections
  • 5379 independent reflections
  • 3699 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.123
  • S = 1.03
  • 5379 reflections
  • 276 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054725/ci2992sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054725/ci2992Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar’s College, Velur, Namakkal, Tamil Nadu, India, for the encouragement to pursue the programme.

supplementary crystallographic information

Comment

Piperidin-4-one derivatives possess varied biological properties such as antiviral, antitumour (El-Subbagh et al., 2000), analgesic (Jerom & Spencer, 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), antimicrobial, bactericidal, fungicidal, herbicidal, insecticidal, antihistaminic, anti-inflammatory, anticancer, CNS stimulant and depressant activities (Mobio et al., 1989; Katritzky & Fan, 1990; Ganellin & Spickett, 1965). In view of these importance and to ascertain the molecular conformation, a crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. The piperidine ring adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q2 = 0.737 (2) Å, q3 = 0.013 (2) Å, [var phi]2 = 285.4 (1)° and Δs(C3 or C6) = 19.0 (2)°. The sum of the bond angles around the atom N1 (359.1°) of the piperidine ring is in accordance with sp2 hybridization.

The crystal packing is stabilized by C—H···O intermolecular interactions. Atom C2 of the molecule at (x, y, z) donates a proton to atom O3 of the molecule at (1 - x, 1/2 + y, 1/2 - z), forming a C5 (Bernstein et al., 1995) zigzag chain running along the b axis. The chains are cross linked via C5—H5···O1 intermolecular interactions, forming a two-dimensional network parallel to the ab plane.

Experimental

To a solution of r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one (1.69 g) in anhydrous benzene (60 ml) was added triethylamine (2.08 ml) and dichloroacetylchloride (1.42 ml). The reaction mixture was allowed to stir at room temperature for 8 hr and the solution was washed with water (4 × 25 ml). The organic layer was dried over anhydrous sodium sulfate, passed through a short column of silica, evaporated and crystallized from benzene-petroleum ether (60–80° C) (9:1 v/v).

Refinement

H atoms were positioned geometrically (C-H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(Cmethyl) and 1.2 Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C23H25Cl2NO4F(000) = 944
Mr = 450.34Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2335 reflections
a = 8.1251 (7) Åθ = 1.5–28.4°
b = 9.9702 (9) ŵ = 0.32 mm1
c = 27.649 (2) ÅT = 293 K
β = 92.265 (5)°Block, colourless
V = 2238.0 (3) Å30.27 × 0.26 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEXII area-detector diffractometer5379 independent reflections
Radiation source: fine-focus sealed tube3699 reflections with I > 2σ(I)
graphiteRint = 0.026
ω and [var phi] scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −8→10
Tmin = 0.917, Tmax = 0.929k = −13→13
19833 measured reflectionsl = −36→36

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.123w = 1/[σ2(Fo2) + (0.0497P)2 + 0.6929P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5379 reflectionsΔρmax = 0.27 e Å3
276 parametersΔρmin = −0.36 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0028 (7)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.25916 (8)1.01921 (6)0.20873 (3)0.0839 (2)
Cl20.26208 (12)0.94382 (8)0.10863 (3)0.1095 (3)
O10.03043 (18)0.80082 (15)0.18222 (7)0.0785 (5)
O20.7057 (2)0.78446 (18)0.00094 (6)0.0835 (5)
O30.42430 (17)0.31447 (14)0.24506 (5)0.0588 (4)
O4−0.1564 (2)0.25273 (19)0.03205 (6)0.0880 (5)
N10.23306 (16)0.64601 (13)0.17753 (5)0.0373 (3)
C20.41000 (18)0.60777 (16)0.17209 (6)0.0347 (3)
H20.47470.64620.19940.042*
C30.42732 (19)0.45310 (16)0.17457 (6)0.0375 (4)
H30.35930.41650.14760.045*
C40.3566 (2)0.40055 (17)0.22066 (6)0.0400 (4)
C50.1976 (2)0.46357 (18)0.23518 (6)0.0429 (4)
H50.12270.39160.24430.051*
C60.1163 (2)0.54088 (17)0.19306 (6)0.0407 (4)
H60.02210.58820.20610.049*
C70.1748 (2)0.77330 (18)0.17704 (7)0.0466 (4)
C80.2948 (2)0.88677 (18)0.16834 (7)0.0536 (5)
H80.40820.85440.17310.064*
C90.48157 (19)0.65819 (16)0.12568 (6)0.0367 (4)
C100.4080 (2)0.63098 (19)0.08098 (6)0.0451 (4)
H100.30860.58460.07930.054*
C110.4787 (2)0.6711 (2)0.03850 (7)0.0530 (5)
H110.42740.65140.00870.064*
C120.6256 (3)0.7404 (2)0.04089 (8)0.0563 (5)
C130.7005 (2)0.76910 (19)0.08502 (8)0.0561 (5)
H130.79920.81650.08660.067*
C140.6297 (2)0.72769 (18)0.12718 (7)0.0471 (4)
H140.68210.74670.15690.056*
C150.6402 (4)0.7474 (3)−0.04496 (10)0.1007 (10)
H15A0.62370.6521−0.04600.151*
H15B0.71550.7728−0.06930.151*
H15C0.53680.7921−0.05100.151*
C160.6029 (2)0.4058 (2)0.16746 (8)0.0572 (5)
H16A0.67620.44960.19050.086*
H16B0.63410.42760.13530.086*
H16C0.60910.31050.17210.086*
C170.2310 (3)0.5525 (2)0.27953 (7)0.0608 (5)
H17A0.27330.49860.30600.091*
H17B0.13040.59470.28840.091*
H17C0.31030.62000.27210.091*
C180.04865 (18)0.45810 (17)0.15056 (6)0.0401 (4)
C190.0299 (2)0.32074 (18)0.15241 (7)0.0477 (4)
H190.06350.27540.18050.057*
C20−0.0373 (2)0.2483 (2)0.11393 (7)0.0546 (5)
H20−0.04820.15570.11620.066*
C21−0.0879 (2)0.3135 (2)0.07232 (7)0.0572 (5)
C22−0.0711 (2)0.4514 (2)0.06939 (7)0.0582 (5)
H22−0.10490.49630.04120.070*
C23−0.0045 (2)0.5217 (2)0.10811 (7)0.0489 (4)
H230.00530.61440.10580.059*
C24−0.1684 (5)0.1120 (3)0.03207 (13)0.1282 (14)
H24A−0.06020.07380.03570.192*
H24B−0.21970.08250.00210.192*
H24C−0.23350.08380.05840.192*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0931 (5)0.0454 (3)0.1115 (5)0.0192 (3)−0.0188 (4)−0.0273 (3)
Cl20.1680 (8)0.0806 (5)0.0815 (5)0.0454 (5)0.0254 (5)0.0328 (4)
O10.0488 (8)0.0526 (9)0.1349 (15)0.0178 (7)0.0149 (9)−0.0099 (9)
O20.0905 (12)0.0833 (12)0.0795 (11)−0.0124 (10)0.0404 (9)0.0208 (9)
O30.0665 (9)0.0521 (8)0.0577 (8)0.0080 (7)0.0027 (7)0.0194 (7)
O40.0982 (13)0.0853 (12)0.0777 (11)0.0069 (10)−0.0324 (9)−0.0231 (9)
N10.0331 (7)0.0329 (7)0.0461 (7)0.0036 (6)0.0056 (6)−0.0005 (6)
C20.0295 (8)0.0346 (8)0.0400 (8)0.0026 (7)0.0028 (6)−0.0002 (7)
C30.0368 (8)0.0347 (8)0.0411 (8)0.0054 (7)0.0052 (6)0.0028 (7)
C40.0446 (9)0.0355 (9)0.0399 (8)−0.0032 (8)−0.0004 (7)0.0005 (7)
C50.0448 (9)0.0443 (10)0.0403 (9)−0.0049 (8)0.0108 (7)0.0001 (8)
C60.0327 (8)0.0413 (9)0.0489 (9)0.0009 (7)0.0107 (7)−0.0014 (8)
C70.0437 (10)0.0386 (9)0.0574 (10)0.0089 (8)0.0025 (8)−0.0050 (8)
C80.0599 (12)0.0335 (9)0.0675 (12)0.0111 (9)0.0015 (9)0.0006 (9)
C90.0332 (8)0.0314 (8)0.0457 (9)0.0030 (7)0.0047 (7)0.0042 (7)
C100.0386 (9)0.0488 (10)0.0484 (9)−0.0037 (8)0.0052 (7)0.0056 (8)
C110.0550 (11)0.0589 (12)0.0455 (10)0.0019 (10)0.0078 (8)0.0089 (9)
C120.0575 (12)0.0486 (11)0.0645 (12)0.0050 (10)0.0234 (10)0.0158 (10)
C130.0415 (10)0.0453 (11)0.0824 (14)−0.0057 (9)0.0143 (10)0.0102 (10)
C140.0397 (9)0.0403 (9)0.0612 (11)−0.0019 (8)0.0021 (8)0.0049 (8)
C150.132 (3)0.105 (2)0.0691 (17)0.0001 (19)0.0486 (17)0.0209 (16)
C160.0496 (11)0.0542 (11)0.0691 (12)0.0199 (9)0.0174 (9)0.0149 (10)
C170.0735 (14)0.0637 (13)0.0459 (10)0.0017 (11)0.0100 (9)−0.0107 (9)
C180.0269 (8)0.0437 (9)0.0500 (9)0.0019 (7)0.0051 (7)0.0009 (8)
C190.0434 (10)0.0448 (10)0.0549 (10)0.0009 (8)−0.0001 (8)0.0033 (8)
C200.0490 (11)0.0443 (10)0.0701 (13)0.0017 (9)−0.0040 (9)−0.0066 (10)
C210.0456 (11)0.0642 (13)0.0613 (12)0.0067 (10)−0.0060 (9)−0.0129 (10)
C220.0495 (11)0.0697 (14)0.0545 (11)0.0055 (10)−0.0087 (9)0.0068 (10)
C230.0390 (9)0.0470 (10)0.0606 (11)0.0019 (8)0.0002 (8)0.0063 (9)
C240.163 (3)0.085 (2)0.131 (3)0.030 (2)−0.063 (2)−0.055 (2)

Geometric parameters (Å, °)

Cl1—C81.7609 (19)C10—H100.93
Cl2—C81.757 (2)C11—C121.379 (3)
O1—C71.218 (2)C11—H110.93
O2—C121.376 (2)C12—C131.372 (3)
O2—C151.406 (3)C13—C141.383 (3)
O3—C41.210 (2)C13—H130.93
O4—C211.367 (2)C14—H140.93
O4—C241.406 (4)C15—H15A0.96
N1—C71.354 (2)C15—H15B0.96
N1—C61.489 (2)C15—H15C0.96
N1—C21.501 (2)C16—H16A0.96
C2—C91.516 (2)C16—H16B0.96
C2—C31.550 (2)C16—H16C0.96
C2—H20.98C17—H17A0.96
C3—C41.512 (2)C17—H17B0.96
C3—C161.523 (2)C17—H17C0.96
C3—H30.98C18—C191.379 (2)
C4—C51.506 (2)C18—C231.388 (2)
C5—C61.525 (2)C19—C201.380 (3)
C5—C171.529 (2)C19—H190.93
C5—H50.98C20—C211.370 (3)
C6—C181.521 (2)C20—H200.93
C6—H60.98C21—C221.384 (3)
C7—O11.218 (2)C22—C231.373 (3)
C7—C81.519 (3)C22—H220.93
C8—H80.98C23—H230.93
C9—C101.378 (2)C24—H24A0.96
C9—C141.388 (2)C24—H24B0.96
C10—C111.386 (2)C24—H24C0.96
C12—O2—C15117.82 (19)C13—C12—C11119.99 (17)
C21—O4—C24117.9 (2)O2—C12—C11123.9 (2)
C7—N1—C6115.85 (14)C12—C13—C14120.19 (18)
C7—N1—C2124.96 (14)C12—C13—H13119.9
C6—N1—C2118.31 (12)C14—C13—H13119.9
N1—C2—C9113.69 (12)C13—C14—C9120.84 (18)
N1—C2—C3109.51 (12)C13—C14—H14119.6
C9—C2—C3109.29 (13)C9—C14—H14119.6
N1—C2—H2108.1O2—C15—H15A109.5
C9—C2—H2108.1O2—C15—H15B109.5
C3—C2—H2108.1H15A—C15—H15B109.5
C4—C3—C16113.00 (14)O2—C15—H15C109.5
C4—C3—C2110.20 (13)H15A—C15—H15C109.5
C16—C3—C2112.72 (14)H15B—C15—H15C109.5
C4—C3—H3106.8C3—C16—H16A109.5
C16—C3—H3106.8C3—C16—H16B109.5
C2—C3—H3106.8H16A—C16—H16B109.5
O3—C4—C5121.55 (15)C3—C16—H16C109.5
O3—C4—C3122.41 (16)H16A—C16—H16C109.5
C5—C4—C3116.02 (14)H16B—C16—H16C109.5
C4—C5—C6110.96 (13)C5—C17—H17A109.5
C4—C5—C17109.19 (14)C5—C17—H17B109.5
C6—C5—C17112.17 (15)H17A—C17—H17B109.5
C4—C5—H5108.1C5—C17—H17C109.5
C6—C5—H5108.1H17A—C17—H17C109.5
C17—C5—H5108.1H17B—C17—H17C109.5
N1—C6—C18111.99 (13)C19—C18—C23116.98 (17)
N1—C6—C5108.31 (13)C19—C18—C6123.20 (16)
C18—C6—C5116.62 (14)C23—C18—C6119.76 (16)
N1—C6—H6106.4C18—C19—C20122.15 (18)
C18—C6—H6106.4C18—C19—H19118.9
C5—C6—H6106.4C20—C19—H19118.9
O1—C7—N1123.20 (17)C21—C20—C19119.69 (19)
O1—C7—C8118.56 (16)C21—C20—H20120.2
N1—C7—C8118.22 (15)C19—C20—H20120.2
C7—C8—Cl2108.39 (14)O4—C21—C20125.0 (2)
C7—C8—Cl1109.58 (13)O4—C21—C22115.48 (19)
Cl2—C8—Cl1109.31 (10)C20—C21—C22119.56 (19)
C7—C8—H8109.8C23—C22—C21119.88 (19)
Cl2—C8—H8109.8C23—C22—H22120.1
Cl1—C8—H8109.8C21—C22—H22120.1
C10—C9—C14118.03 (16)C22—C23—C18121.74 (18)
C10—C9—C2121.78 (14)C22—C23—H23119.1
C14—C9—C2120.10 (15)C18—C23—H23119.1
C9—C10—C11121.56 (17)O4—C24—H24A109.5
C9—C10—H10119.2O4—C24—H24B109.5
C11—C10—H10119.2H24A—C24—H24B109.5
C12—C11—C10119.40 (18)O4—C24—H24C109.5
C12—C11—H11120.3H24A—C24—H24C109.5
C10—C11—H11120.3H24B—C24—H24C109.5
C13—C12—O2116.11 (19)
C7—N1—C2—C9−57.4 (2)N1—C2—C9—C10−54.2 (2)
C6—N1—C2—C9133.76 (14)C3—C2—C9—C1068.44 (19)
C7—N1—C2—C3179.99 (15)N1—C2—C9—C14129.30 (15)
C6—N1—C2—C311.19 (18)C3—C2—C9—C14−108.02 (17)
N1—C2—C3—C4−54.86 (17)C14—C9—C10—C110.1 (3)
C9—C2—C3—C4180.00 (13)C2—C9—C10—C11−176.45 (16)
N1—C2—C3—C16177.88 (14)C9—C10—C11—C12−0.3 (3)
C9—C2—C3—C1652.74 (18)C15—O2—C12—C13174.8 (2)
C16—C3—C4—O3−10.3 (2)C15—O2—C12—C11−5.1 (3)
C2—C3—C4—O3−137.45 (17)C10—C11—C12—C130.0 (3)
C16—C3—C4—C5168.53 (15)C10—C11—C12—O2179.92 (19)
C2—C3—C4—C541.42 (19)O2—C12—C13—C14−179.40 (18)
O3—C4—C5—C6−165.48 (16)C11—C12—C13—C140.5 (3)
C3—C4—C5—C615.6 (2)C12—C13—C14—C9−0.8 (3)
O3—C4—C5—C1770.4 (2)C10—C9—C14—C130.5 (3)
C3—C4—C5—C17−108.51 (17)C2—C9—C14—C13177.04 (16)
C7—N1—C6—C18105.44 (17)N1—C6—C18—C19138.12 (16)
C2—N1—C6—C18−84.76 (17)C5—C6—C18—C1912.6 (2)
C7—N1—C6—C5−124.58 (15)N1—C6—C18—C23−44.8 (2)
C2—N1—C6—C545.23 (18)C5—C6—C18—C23−170.39 (14)
C4—C5—C6—N1−58.81 (17)C23—C18—C19—C200.5 (3)
C17—C5—C6—N163.61 (17)C6—C18—C19—C20177.62 (16)
C4—C5—C6—C1868.56 (18)C18—C19—C20—C21−0.1 (3)
C17—C5—C6—C18−169.01 (14)C24—O4—C21—C20−3.5 (4)
C6—N1—C7—O1−9.9 (3)C24—O4—C21—C22176.7 (3)
C2—N1—C7—O1−178.98 (17)C19—C20—C21—O4−179.80 (19)
C6—N1—C7—C8171.65 (15)C19—C20—C21—C22−0.1 (3)
C2—N1—C7—C82.6 (2)O4—C21—C22—C23179.61 (18)
O1—C7—C8—Cl2−74.4 (2)C20—C21—C22—C23−0.1 (3)
N1—C7—C8—Cl2104.09 (17)C21—C22—C23—C180.6 (3)
O1—C7—C8—Cl144.8 (2)C19—C18—C23—C22−0.7 (3)
N1—C7—C8—Cl1−136.69 (15)C6—C18—C23—C22−177.94 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.982.403.326 (2)158
C5—H5···O1ii0.982.593.408 (2)141

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2992).

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