Acta Cryst. (2009). E65, o10 [ doi:10.1107/S1600536808040051 ]
In the title compound, C21H21Cl2NO2, the piperidine ring adopts a distorted boat conformation. The two phenyl rings are approximately perpendicular to each other, with a dihedral angle of 86.12 (7)°. Molecules are linked into centrosymmetric dimers by pairs of bifurcated C-H
O hydrogen bonds, forming R22(10) and R22(14) ring motifs, and an intramolecular C-HO link also occurs.
A mixture of 3,3-dimethyl-cis-2,6-diphenylpiperidin-4-one (1.4 g, 5 mmol), dichloroacetylchloride (1 ml, 10 mmol) and triethylamine (2 ml, 14.4 mmol) in anhydrous benzene (20 ml) was stirred at room temperature for 7 h. The benzene solution was dried over anhydrous Na2SO4 and concentrated. The pasty mass obtained was purified by crystallization from benzene-petroleum ether (333–353 K) in the ratio of 95:5.
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(C) for methyl H and 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./ci2724fig1thm.gif)
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
![[Figure 2]](./ci2724fig2thm.gif)
| Fig. 2. The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) dimers. Atom H16A and H atoms not involved in hydrogen bonding have been omitted. |
| C21H21Cl2NO2 | Z = 2 |
| Mr = 390.29 | F(000) = 408 |
| Triclinic, P1 | Dx = 1.348 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.1084 (2) Å | Cell parameters from 7709 reflections |
| b = 10.8992 (3) Å | θ = 2.1–34.0° |
| c = 10.9918 (3) Å | µ = 0.35 mm−1 |
| α = 63.879 (1)° | T = 293 K |
| β = 85.343 (2)° | Block, colourless |
| γ = 79.029 (1)° | 0.30 × 0.26 × 0.20 mm |
| V = 961.84 (4) Å3 |
| Bruker Kappa APEXII area-detector diffractometer | 7709 independent reflections |
| Radiation source: fine-focus sealed tube | 5516 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| ω and φ scans | θmax = 34.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −14→14 |
| Tmin = 0.902, Tmax = 0.933 | k = −16→17 |
| 26977 measured reflections | l = −17→15 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.180 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0854P)2 + 0.3205P] where P = (Fo2 + 2Fc2)/3 |
| 7709 reflections | (Δ/σ)max = 0.001 |
| 235 parameters | Δρmax = 0.80 e Å−3 |
| 0 restraints | Δρmin = −0.73 e Å−3 |
| C21H21Cl2NO2 | γ = 79.029 (1)° |
| Mr = 390.29 | V = 961.84 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.1084 (2) Å | Mo Kα radiation |
| b = 10.8992 (3) Å | µ = 0.35 mm−1 |
| c = 10.9918 (3) Å | T = 293 K |
| α = 63.879 (1)° | 0.30 × 0.26 × 0.20 mm |
| β = 85.343 (2)° |
| Bruker Kappa APEXII area-detector diffractometer | 7709 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 5516 reflections with I > 2σ(I) |
| Tmin = 0.902, Tmax = 0.933 | Rint = 0.021 |
| 26977 measured reflections | θmax = 34.0° |
| R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.180 | Δρmax = 0.80 e Å−3 |
| S = 1.03 | Δρmin = −0.73 e Å−3 |
| 7709 reflections | Absolute structure: ? |
| 235 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| C2 | 0.16315 (15) | 0.26040 (13) | 0.64530 (13) | 0.0320 (2) | |
| H2 | 0.1059 | 0.3371 | 0.5691 | 0.038* | |
| C3 | 0.07185 (16) | 0.14160 (15) | 0.69561 (15) | 0.0363 (3) | |
| C4 | 0.12824 (17) | 0.02567 (15) | 0.83179 (16) | 0.0394 (3) | |
| C5 | 0.22508 (18) | 0.06135 (14) | 0.91179 (15) | 0.0392 (3) | |
| H5A | 0.3283 | 0.0437 | 0.8854 | 0.047* | |
| H5B | 0.2169 | −0.0007 | 1.0070 | 0.047* | |
| C6 | 0.18871 (15) | 0.21096 (13) | 0.89554 (13) | 0.0315 (2) | |
| H6 | 0.0976 | 0.2204 | 0.9469 | 0.038* | |
| C7 | 0.11626 (15) | 0.44855 (13) | 0.71233 (13) | 0.0330 (2) | |
| C8 | 0.06652 (16) | 0.49415 (14) | 0.82515 (15) | 0.0369 (3) | |
| H8 | 0.1194 | 0.4282 | 0.9094 | 0.044* | |
| C9 | 0.32045 (16) | 0.23856 (15) | 0.59084 (14) | 0.0362 (3) | |
| C10 | 0.4137 (2) | 0.11132 (19) | 0.62714 (19) | 0.0521 (4) | |
| H10 | 0.3796 | 0.0306 | 0.6872 | 0.062* | |
| C11 | 0.5572 (2) | 0.1029 (3) | 0.5750 (2) | 0.0641 (5) | |
| H11 | 0.6186 | 0.0167 | 0.6012 | 0.077* | |
| C12 | 0.6095 (2) | 0.2197 (3) | 0.4854 (2) | 0.0646 (5) | |
| H12 | 0.7062 | 0.2136 | 0.4516 | 0.078* | |
| C13 | 0.5178 (3) | 0.3460 (3) | 0.4460 (2) | 0.0683 (6) | |
| H13 | 0.5521 | 0.4258 | 0.3842 | 0.082* | |
| C14 | 0.3742 (2) | 0.35549 (19) | 0.49753 (19) | 0.0522 (4) | |
| H14 | 0.3129 | 0.4419 | 0.4690 | 0.063* | |
| C15 | 0.0667 (2) | 0.0880 (2) | 0.5892 (2) | 0.0554 (4) | |
| H15A | 0.0305 | 0.1640 | 0.5050 | 0.083* | |
| H15B | 0.0010 | 0.0210 | 0.6192 | 0.083* | |
| H15C | 0.1654 | 0.0452 | 0.5765 | 0.083* | |
| C16 | −0.09026 (17) | 0.19822 (18) | 0.72274 (18) | 0.0458 (3) | |
| H16A | −0.1334 | 0.2725 | 0.6403 | 0.069* | |
| H16B | −0.0895 | 0.2320 | 0.7899 | 0.069* | |
| H16C | −0.1485 | 0.1252 | 0.7549 | 0.069* | |
| C17 | 0.31594 (16) | 0.23865 (14) | 0.95568 (15) | 0.0377 (3) | |
| C18 | 0.4438 (2) | 0.2760 (2) | 0.8816 (2) | 0.0564 (4) | |
| H18 | 0.4525 | 0.2854 | 0.7932 | 0.068* | |
| C19 | 0.5588 (3) | 0.2993 (3) | 0.9398 (3) | 0.0812 (8) | |
| H19 | 0.6448 | 0.3239 | 0.8903 | 0.097* | |
| C20 | 0.5464 (3) | 0.2865 (3) | 1.0703 (3) | 0.0855 (9) | |
| H20 | 0.6232 | 0.3041 | 1.1080 | 0.103* | |
| C21 | 0.4221 (3) | 0.2479 (3) | 1.1444 (3) | 0.0749 (7) | |
| H21 | 0.4148 | 0.2384 | 1.2329 | 0.090* | |
| C22 | 0.3049 (2) | 0.22256 (19) | 1.08834 (19) | 0.0523 (4) | |
| H22 | 0.2206 | 0.1952 | 1.1396 | 0.063* | |
| Cl1 | 0.09918 (6) | 0.66177 (5) | 0.78274 (6) | 0.06072 (15) | |
| Cl2 | −0.12724 (6) | 0.49086 (7) | 0.84645 (7) | 0.07096 (18) | |
| N1 | 0.16105 (12) | 0.31050 (11) | 0.75154 (11) | 0.0301 (2) | |
| O1 | 0.09414 (17) | −0.08818 (13) | 0.87624 (15) | 0.0596 (4) | |
| O2 | 0.10590 (15) | 0.53523 (11) | 0.59509 (11) | 0.0479 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.0360 (6) | 0.0327 (5) | 0.0303 (5) | −0.0091 (5) | 0.0005 (4) | −0.0151 (5) |
| C3 | 0.0389 (7) | 0.0372 (6) | 0.0392 (6) | −0.0133 (5) | 0.0001 (5) | −0.0198 (5) |
| C4 | 0.0407 (7) | 0.0324 (6) | 0.0470 (7) | −0.0117 (5) | 0.0009 (6) | −0.0170 (5) |
| C5 | 0.0463 (7) | 0.0291 (6) | 0.0386 (7) | −0.0096 (5) | −0.0051 (6) | −0.0094 (5) |
| C6 | 0.0327 (6) | 0.0314 (5) | 0.0299 (5) | −0.0085 (4) | −0.0015 (4) | −0.0113 (4) |
| C7 | 0.0356 (6) | 0.0300 (5) | 0.0337 (6) | −0.0068 (5) | −0.0007 (5) | −0.0134 (5) |
| C8 | 0.0397 (7) | 0.0334 (6) | 0.0399 (7) | −0.0043 (5) | −0.0015 (5) | −0.0186 (5) |
| C9 | 0.0390 (7) | 0.0403 (6) | 0.0343 (6) | −0.0114 (5) | 0.0046 (5) | −0.0196 (5) |
| C10 | 0.0480 (9) | 0.0468 (8) | 0.0557 (9) | −0.0050 (7) | 0.0120 (7) | −0.0203 (7) |
| C11 | 0.0477 (10) | 0.0720 (13) | 0.0679 (12) | 0.0016 (9) | 0.0097 (9) | −0.0323 (10) |
| C12 | 0.0434 (9) | 0.0902 (16) | 0.0660 (12) | −0.0188 (10) | 0.0178 (8) | −0.0393 (11) |
| C13 | 0.0647 (12) | 0.0741 (13) | 0.0692 (13) | −0.0349 (11) | 0.0304 (10) | −0.0298 (11) |
| C14 | 0.0571 (10) | 0.0460 (8) | 0.0521 (9) | −0.0181 (7) | 0.0171 (8) | −0.0193 (7) |
| C15 | 0.0692 (12) | 0.0611 (10) | 0.0551 (10) | −0.0264 (9) | 0.0026 (8) | −0.0368 (9) |
| C16 | 0.0356 (7) | 0.0511 (8) | 0.0496 (8) | −0.0138 (6) | −0.0013 (6) | −0.0183 (7) |
| C17 | 0.0371 (6) | 0.0323 (6) | 0.0439 (7) | −0.0035 (5) | −0.0108 (5) | −0.0158 (5) |
| C18 | 0.0418 (8) | 0.0620 (11) | 0.0710 (12) | −0.0179 (7) | −0.0038 (8) | −0.0296 (9) |
| C19 | 0.0471 (11) | 0.0829 (16) | 0.128 (2) | −0.0202 (10) | −0.0174 (12) | −0.0520 (16) |
| C20 | 0.0652 (14) | 0.0734 (14) | 0.136 (2) | 0.0039 (11) | −0.0552 (16) | −0.0588 (16) |
| C21 | 0.0874 (16) | 0.0676 (12) | 0.0810 (14) | 0.0157 (11) | −0.0504 (13) | −0.0454 (11) |
| C22 | 0.0588 (10) | 0.0522 (9) | 0.0486 (9) | 0.0007 (7) | −0.0185 (7) | −0.0254 (7) |
| Cl1 | 0.0769 (3) | 0.0499 (2) | 0.0729 (3) | −0.0258 (2) | 0.0075 (2) | −0.0378 (2) |
| Cl2 | 0.0479 (3) | 0.0867 (4) | 0.1055 (5) | −0.0242 (2) | 0.0255 (3) | −0.0656 (4) |
| N1 | 0.0339 (5) | 0.0282 (4) | 0.0290 (5) | −0.0072 (4) | −0.0003 (4) | −0.0124 (4) |
| O1 | 0.0717 (9) | 0.0355 (5) | 0.0709 (8) | −0.0231 (6) | −0.0097 (7) | −0.0151 (6) |
| O2 | 0.0706 (8) | 0.0324 (5) | 0.0350 (5) | −0.0071 (5) | −0.0009 (5) | −0.0102 (4) |
| C2—N1 | 1.4886 (17) | C11—C12 | 1.367 (3) |
| C2—C9 | 1.525 (2) | C11—H11 | 0.93 |
| C2—C3 | 1.5424 (19) | C12—C13 | 1.369 (3) |
| C2—H2 | 0.98 | C12—H12 | 0.93 |
| C3—C4 | 1.521 (2) | C13—C14 | 1.387 (3) |
| C3—C15 | 1.528 (2) | C13—H13 | 0.93 |
| C3—C16 | 1.547 (2) | C14—H14 | 0.93 |
| C4—O1 | 1.2096 (18) | C15—H15A | 0.96 |
| C4—C5 | 1.503 (2) | C15—H15B | 0.96 |
| C5—C6 | 1.5324 (19) | C15—H15C | 0.96 |
| C5—H5A | 0.97 | C16—H16A | 0.96 |
| C5—H5B | 0.97 | C16—H16B | 0.96 |
| C6—N1 | 1.4814 (16) | C16—H16C | 0.96 |
| C6—C17 | 1.5179 (18) | C17—C18 | 1.385 (3) |
| C6—H6 | 0.98 | C17—C22 | 1.387 (2) |
| C7—O2 | 1.2149 (17) | C18—C19 | 1.387 (3) |
| C7—N1 | 1.3564 (16) | C18—H18 | 0.93 |
| C7—C8 | 1.535 (2) | C19—C20 | 1.375 (4) |
| C8—Cl1 | 1.7544 (15) | C19—H19 | 0.93 |
| C8—Cl2 | 1.7664 (16) | C20—C21 | 1.361 (4) |
| C8—H8 | 0.98 | C20—H20 | 0.93 |
| C9—C14 | 1.386 (2) | C21—C22 | 1.401 (3) |
| C9—C10 | 1.387 (2) | C21—H21 | 0.93 |
| C10—C11 | 1.388 (3) | C22—H22 | 0.93 |
| C10—H10 | 0.93 | ||
| N1—C2—C9 | 111.62 (11) | C10—C11—H11 | 119.6 |
| N1—C2—C3 | 108.79 (10) | C11—C12—C13 | 119.27 (18) |
| C9—C2—C3 | 119.05 (12) | C11—C12—H12 | 120.4 |
| N1—C2—H2 | 105.4 | C13—C12—H12 | 120.4 |
| C9—C2—H2 | 105.4 | C12—C13—C14 | 120.42 (19) |
| C3—C2—H2 | 105.4 | C12—C13—H13 | 119.8 |
| C4—C3—C15 | 112.03 (13) | C14—C13—H13 | 119.8 |
| C4—C3—C2 | 111.80 (11) | C9—C14—C13 | 121.16 (18) |
| C15—C3—C2 | 111.26 (13) | C9—C14—H14 | 119.4 |
| C4—C3—C16 | 104.84 (12) | C13—C14—H14 | 119.4 |
| C15—C3—C16 | 108.17 (14) | C3—C15—H15A | 109.5 |
| C2—C3—C16 | 108.41 (12) | C3—C15—H15B | 109.5 |
| O1—C4—C5 | 121.20 (14) | H15A—C15—H15B | 109.5 |
| O1—C4—C3 | 122.41 (14) | C3—C15—H15C | 109.5 |
| C5—C4—C3 | 116.35 (11) | H15A—C15—H15C | 109.5 |
| C4—C5—C6 | 115.68 (12) | H15B—C15—H15C | 109.5 |
| C4—C5—H5A | 108.4 | C3—C16—H16A | 109.5 |
| C6—C5—H5A | 108.4 | C3—C16—H16B | 109.5 |
| C4—C5—H5B | 108.4 | H16A—C16—H16B | 109.5 |
| C6—C5—H5B | 108.4 | C3—C16—H16C | 109.5 |
| H5A—C5—H5B | 107.4 | H16A—C16—H16C | 109.5 |
| N1—C6—C17 | 112.02 (11) | H16B—C16—H16C | 109.5 |
| N1—C6—C5 | 110.99 (11) | C18—C17—C22 | 119.73 (16) |
| C17—C6—C5 | 108.73 (11) | C18—C17—C6 | 121.13 (14) |
| N1—C6—H6 | 108.3 | C22—C17—C6 | 119.12 (15) |
| C17—C6—H6 | 108.3 | C17—C18—C19 | 119.8 (2) |
| C5—C6—H6 | 108.3 | C17—C18—H18 | 120.1 |
| O2—C7—N1 | 124.28 (13) | C19—C18—H18 | 120.1 |
| O2—C7—C8 | 119.02 (12) | C20—C19—C18 | 120.5 (3) |
| N1—C7—C8 | 116.59 (11) | C20—C19—H19 | 119.8 |
| C7—C8—Cl1 | 111.99 (10) | C18—C19—H19 | 119.8 |
| C7—C8—Cl2 | 106.14 (10) | C21—C20—C19 | 120.06 (19) |
| Cl1—C8—Cl2 | 109.75 (8) | C21—C20—H20 | 120.0 |
| C7—C8—H8 | 109.6 | C19—C20—H20 | 120.0 |
| Cl1—C8—H8 | 109.6 | C20—C21—C22 | 120.6 (2) |
| Cl2—C8—H8 | 109.6 | C20—C21—H21 | 119.7 |
| C14—C9—C10 | 117.55 (15) | C22—C21—H21 | 119.7 |
| C14—C9—C2 | 117.21 (14) | C17—C22—C21 | 119.4 (2) |
| C10—C9—C2 | 125.24 (13) | C17—C22—H22 | 120.3 |
| C9—C10—C11 | 120.81 (18) | C21—C22—H22 | 120.3 |
| C9—C10—H10 | 119.6 | C7—N1—C6 | 122.10 (11) |
| C11—C10—H10 | 119.6 | C7—N1—C2 | 116.79 (10) |
| C12—C11—C10 | 120.7 (2) | C6—N1—C2 | 120.69 (10) |
| C12—C11—H11 | 119.6 | ||
| N1—C2—C3—C4 | −55.28 (15) | C11—C12—C13—C14 | 0.8 (4) |
| C9—C2—C3—C4 | 74.08 (15) | C10—C9—C14—C13 | −2.2 (3) |
| N1—C2—C3—C15 | 178.63 (13) | C2—C9—C14—C13 | 177.88 (18) |
| C9—C2—C3—C15 | −52.01 (18) | C12—C13—C14—C9 | 0.7 (3) |
| N1—C2—C3—C16 | 59.80 (14) | N1—C6—C17—C18 | −39.86 (19) |
| C9—C2—C3—C16 | −170.84 (12) | C5—C6—C17—C18 | 83.18 (17) |
| C15—C3—C4—O1 | −38.8 (2) | N1—C6—C17—C22 | 141.83 (14) |
| C2—C3—C4—O1 | −164.51 (16) | C5—C6—C17—C22 | −95.13 (16) |
| C16—C3—C4—O1 | 78.24 (19) | C22—C17—C18—C19 | −1.1 (3) |
| C15—C3—C4—C5 | 143.33 (15) | C6—C17—C18—C19 | −179.38 (18) |
| C2—C3—C4—C5 | 17.66 (18) | C17—C18—C19—C20 | −0.4 (4) |
| C16—C3—C4—C5 | −99.59 (15) | C18—C19—C20—C21 | 1.3 (4) |
| O1—C4—C5—C6 | −144.98 (16) | C19—C20—C21—C22 | −0.7 (4) |
| C3—C4—C5—C6 | 32.88 (19) | C18—C17—C22—C21 | 1.6 (3) |
| C4—C5—C6—N1 | −43.61 (17) | C6—C17—C22—C21 | 179.98 (15) |
| C4—C5—C6—C17 | −167.26 (13) | C20—C21—C22—C17 | −0.7 (3) |
| O2—C7—C8—Cl1 | −33.06 (17) | O2—C7—N1—C6 | 172.74 (13) |
| N1—C7—C8—Cl1 | 150.79 (10) | C8—C7—N1—C6 | −11.34 (18) |
| O2—C7—C8—Cl2 | 86.69 (15) | O2—C7—N1—C2 | −14.7 (2) |
| N1—C7—C8—Cl2 | −89.46 (13) | C8—C7—N1—C2 | 161.25 (11) |
| N1—C2—C9—C14 | −78.53 (17) | C17—C6—N1—C7 | −63.04 (16) |
| C3—C2—C9—C14 | 153.41 (15) | C5—C6—N1—C7 | 175.21 (12) |
| N1—C2—C9—C10 | 101.51 (17) | C17—C6—N1—C2 | 124.65 (13) |
| C3—C2—C9—C10 | −26.6 (2) | C5—C6—N1—C2 | 2.90 (16) |
| C14—C9—C10—C11 | 2.2 (3) | C9—C2—N1—C7 | 99.87 (13) |
| C2—C9—C10—C11 | −177.88 (17) | C3—C2—N1—C7 | −126.77 (12) |
| C9—C10—C11—C12 | −0.7 (3) | C9—C2—N1—C6 | −87.43 (14) |
| C10—C11—C12—C13 | −0.8 (4) | C3—C2—N1—C6 | 45.93 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C14—H14···O2 | 0.93 | 2.57 | 3.250 (2) | 130 |
| C2—H2···O2i | 0.98 | 2.50 | 3.4264 (18) | 158 |
| C16—H16A···O2i | 0.96 | 2.54 | 3.413 (2) | 151 |
| Symmetry codes: (i) −x, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C14—H14···O2 | 0.93 | 2.57 | 3.250 (2) | 130 |
| C2—H2···O2i | 0.98 | 2.50 | 3.4264 (18) | 158 |
| C16—H16A···O2i | 0.96 | 2.54 | 3.413 (2) | 151 |
| Symmetry codes: (i) −x, −y+1, −z+1. |
TK thanks Dr Babu Varghese, SAIF, IIT–Madras, Chennai, India, for his help with the data collection. SP thanks UGC, India, for financial support.
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & &Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142.
Ponnuswamy, S., Venkatraj, M., Jeyaraman, R., Suresh Kumar, M., Kumaran, D. & Ponnuswamy, M. N. (2002). Indian J. Chem. Sect. B, 41, 614–627.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
The design and synthesis of conformationally anchored molecules are important due its potency and selectivity for designing drugs. The piperidin-4-ones are one such class of compounds to be investigated to understand the stereodynamics and other structural features (Ponnuswamy et al., 2002).
The sum of bond angles around atom N1 (359.6°) indicates sp2 hybridization (Beddoes et al., 1986). The N1—C7 [1.3564 (16) Å] and C7—O2 [1.2149 (17) Å] distances indicate electron delocalization. The piperidine ring adopts a distorted boat conformation, with puckering parameters (Cremer & Pople, 1975) q2 = 0.638 (1) Å, q3 = -0.067 (2) Å and φ2 = 253.4 (1)°, and the asymmetry parameters ΔCs(C2)= 14.4 (1)° (Nardelli, 1983). The best plane through the piperidine ring, N1/C3/C4/C6, forms dihedral angles of 89.31 (6)° and 63.47 (7)°, respectively, with the C9—C4 and C17—C22 phenyl rings. The two phenyl rings are approximately perpendicular to each other, with a dihedral angle of 86.12 (7)°.
The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds. Each atoms C2 and C16 at (x, y, z) donate one proton to bifurcated acceptor O2 at (-x, 1 - y, 1 - z), forming a centrosymmetric dimer (Fig. 2) with R22(10) and R22(14) ring motifs (Bernstein et al., 1995).