Acta Cryst. (2009). E65, o1237 [ doi:10.1107/S1600536809015864 ]
In the crystal structure of the title compound, C26H32ClNO8, the piperidine ring is in a twist-chair conformation, with puckering parameters Q = 0.655 (4) Å, ![[theta]](/logos/entities/thetas_rmgif.gif)
= 93.1 (1) and ![[varphi]](/logos/entities/phiv_rmgif.gif)
= 254.4 (3)°. The ortho C atoms of the piperidine ring deviate from the plane defined by the remaining ring atoms by 0.380 (3) and -0.250 (3) Å.
To a well stirred solution of 3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one (Baliah et al., 1983) (5 mmol) and triethylamine(5 mmol) in 30 ml of benzene, chloroacetyl chloride (5 mmol) in 20 ml benzene was added dropwise within about an hour. The resulting mixture was stirred for about 4 hours at room temperature. Afterwards the mixture was quenched in cold water and the organic layer was extracted with ethyl acetate, washed with 5% sodium bicarbonate solution and dried over anhydrous sodium sulphate. Slow evaporation of the solvent leads to crystals of 1-(2-chloroacetyl)-3-methyl-2,6-bis(3,4,5-trimethoxyphenyl) piperidine-4-one.
H atoms were placed at idealized positions and allowed to ride on their parent atoms with C–H distances in the range 0.93–0.98 Å and Uiso(H) = 1.2Ueq(carrier atom; 1.5 for methyl H atoms).
Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2009).
![[Figure 1]](./nc2143fig1thm.gif)
| Fig. 1. Crystal structure of the title compound with labelling and 50% probability displacement ellipsoids. |
| C26H32ClNO8 | F000 = 2208 |
| Mr = 521.98 | Dx = 1.327 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 8214 reflections |
| a = 13.8720 (8) Å | θ = 2.9–25.0º |
| b = 16.5110 (11) Å | µ = 0.20 mm−1 |
| c = 22.8120 (16) Å | T = 293 K |
| V = 5224.9 (6) Å3 | Block, white |
| Z = 8 | 0.30 × 0.27 × 0.25 mm |
| MacScience DIPLabo 32001 diffractometer | 4464 independent reflections |
| Radiation source: fine-focus sealed tube | 3146 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.027 |
| Detector resolution: 10.0 pixels mm-1 | θmax = 25.0º |
| T = 293 K | θmin = 2.9º |
| ω scans | h = −16→16 |
| Absorption correction: none | k = −19→19 |
| 8214 measured reflections | l = −27→26 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
| wR(F2) = 0.186 | w = 1/[σ2(Fo2) + (0.0931P)2 + 2.926P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 4464 reflections | Δρmax = 0.47 e Å−3 |
| 332 parameters | Δρmin = −0.39 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C26H32ClNO8 | V = 5224.9 (6) Å3 |
| Mr = 521.98 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 13.8720 (8) Å | µ = 0.20 mm−1 |
| b = 16.5110 (11) Å | T = 293 K |
| c = 22.8120 (16) Å | 0.30 × 0.27 × 0.25 mm |
| MacScience DIPLabo 32001 diffractometer | 4464 independent reflections |
| Absorption correction: none | 3146 reflections with I > 2σ(I) |
| 8214 measured reflections | Rint = 0.027 |
| R[F2 > 2σ(F2)] = 0.062 | 332 parameters |
| wR(F2) = 0.186 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.47 e Å−3 |
| 4464 reflections | Δρmin = −0.39 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
| Cl12 | 0.14569 (9) | −0.00580 (6) | 0.36264 (6) | 0.1014 (5) | |
| O7 | 0.0245 (3) | −0.4484 (3) | 0.28056 (17) | 0.1467 (19) | |
| O10 | 0.07651 (19) | −0.14395 (16) | 0.42507 (10) | 0.0742 (9) | |
| O19 | 0.49642 (15) | −0.28235 (15) | 0.40351 (9) | 0.0623 (8) | |
| O21 | 0.57332 (13) | −0.19912 (15) | 0.31391 (9) | 0.0584 (8) | |
| O23 | 0.46432 (15) | −0.15115 (15) | 0.22323 (9) | 0.0595 (8) | |
| O31 | 0.27178 (17) | −0.31372 (15) | 0.56956 (9) | 0.0649 (8) | |
| O33 | 0.26328 (19) | −0.47563 (15) | 0.57353 (9) | 0.0725 (9) | |
| O35 | 0.1596 (2) | −0.55902 (15) | 0.49519 (11) | 0.0847 (10) | |
| N1 | 0.12281 (16) | −0.24570 (15) | 0.36489 (10) | 0.0473 (8) | |
| C2 | 0.0590 (2) | −0.3025 (2) | 0.39713 (13) | 0.0524 (10) | |
| C3 | −0.0007 (3) | −0.3497 (2) | 0.35294 (16) | 0.0690 (14) | |
| C4 | 0.0569 (3) | −0.3931 (2) | 0.30853 (16) | 0.0760 (16) | |
| C5 | 0.1608 (3) | −0.3656 (2) | 0.30122 (14) | 0.0603 (11) | |
| C6 | 0.1732 (2) | −0.27421 (18) | 0.31092 (12) | 0.0476 (10) | |
| C8 | 0.2024 (4) | −0.3910 (3) | 0.24254 (19) | 0.0953 (19) | |
| C9 | 0.1181 (2) | −0.1667 (2) | 0.38063 (14) | 0.0537 (11) | |
| C11 | 0.1658 (3) | −0.10579 (19) | 0.34041 (16) | 0.0613 (12) | |
| C13 | 0.2804 (2) | −0.25428 (18) | 0.31204 (12) | 0.0447 (9) | |
| C14 | 0.3213 (2) | −0.21277 (19) | 0.26566 (12) | 0.0488 (10) | |
| C15 | 0.4183 (2) | −0.19340 (19) | 0.26646 (12) | 0.0485 (10) | |
| C16 | 0.4755 (2) | −0.21760 (19) | 0.31333 (13) | 0.0497 (10) | |
| C17 | 0.4349 (2) | −0.26141 (19) | 0.35897 (12) | 0.0482 (10) | |
| C18 | 0.3374 (2) | −0.27934 (18) | 0.35895 (12) | 0.0466 (9) | |
| C20 | 0.4600 (3) | −0.3312 (2) | 0.44945 (14) | 0.0661 (11) | |
| C22 | 0.5942 (2) | −0.1200 (2) | 0.33503 (18) | 0.0742 (14) | |
| C24 | 0.4061 (3) | −0.1076 (2) | 0.18305 (15) | 0.0661 (11) | |
| C25 | 0.1140 (2) | −0.3524 (2) | 0.44265 (13) | 0.0507 (10) | |
| C26 | 0.1100 (2) | −0.4354 (2) | 0.44530 (14) | 0.0576 (11) | |
| C27 | 0.1605 (3) | −0.4770 (2) | 0.48873 (14) | 0.0593 (11) | |
| C28 | 0.2159 (2) | −0.4349 (2) | 0.52945 (12) | 0.0551 (11) | |
| C29 | 0.2184 (2) | −0.3514 (2) | 0.52730 (12) | 0.0520 (10) | |
| C30 | 0.1675 (2) | −0.3100 (2) | 0.48416 (13) | 0.0521 (10) | |
| C32 | 0.2524 (3) | −0.2308 (2) | 0.58099 (17) | 0.0713 (12) | |
| C34 | 0.3539 (3) | −0.5089 (3) | 0.55613 (19) | 0.0890 (17) | |
| C36 | 0.1045 (4) | −0.6052 (2) | 0.4561 (2) | 0.0960 (18) | |
| H2 | 0.01350 | −0.26880 | 0.41910 | 0.0630* | |
| H3A | −0.04010 | −0.38860 | 0.37390 | 0.0830* | |
| H3B | −0.04380 | −0.31240 | 0.33310 | 0.0830* | |
| H5 | 0.19860 | −0.39300 | 0.33160 | 0.0720* | |
| H6 | 0.14450 | −0.24620 | 0.27730 | 0.0570* | |
| H8A | 0.18970 | −0.44750 | 0.23610 | 0.1420* | |
| H8B | 0.27080 | −0.38190 | 0.24250 | 0.1420* | |
| H8C | 0.17310 | −0.35970 | 0.21190 | 0.1420* | |
| H11A | 0.14120 | −0.11290 | 0.30100 | 0.0740* | |
| H11B | 0.23470 | −0.11600 | 0.33950 | 0.0740* | |
| H14 | 0.28350 | −0.19780 | 0.23380 | 0.0590* | |
| H18 | 0.31020 | −0.30790 | 0.39000 | 0.0560* | |
| H20A | 0.40750 | −0.30360 | 0.46830 | 0.0990* | |
| H20B | 0.51010 | −0.34130 | 0.47750 | 0.0990* | |
| H20C | 0.43750 | −0.38170 | 0.43370 | 0.0990* | |
| H22A | 0.56350 | −0.08060 | 0.31040 | 0.1120* | |
| H22B | 0.66270 | −0.11150 | 0.33460 | 0.1120* | |
| H22C | 0.57060 | −0.11460 | 0.37440 | 0.1120* | |
| H24A | 0.37270 | −0.14500 | 0.15800 | 0.0990* | |
| H24B | 0.44600 | −0.07280 | 0.15970 | 0.0990* | |
| H24C | 0.36010 | −0.07550 | 0.20420 | 0.0990* | |
| H26 | 0.07340 | −0.46390 | 0.41810 | 0.0690* | |
| H30 | 0.16930 | −0.25370 | 0.48300 | 0.0630* | |
| H32A | 0.27190 | −0.19880 | 0.54790 | 0.1070* | |
| H32B | 0.28760 | −0.21390 | 0.61510 | 0.1070* | |
| H32C | 0.18460 | −0.22360 | 0.58770 | 0.1070* | |
| H34A | 0.34540 | −0.54120 | 0.52150 | 0.1340* | |
| H34B | 0.37900 | −0.54200 | 0.58710 | 0.1340* | |
| H34C | 0.39830 | −0.46570 | 0.54800 | 0.1340* | |
| H36A | 0.03760 | −0.59130 | 0.46030 | 0.1440* | |
| H36B | 0.11310 | −0.66170 | 0.46460 | 0.1440* | |
| H36C | 0.12490 | −0.59440 | 0.41670 | 0.1440* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl12 | 0.1112 (9) | 0.0590 (6) | 0.1341 (10) | −0.0100 (6) | 0.0317 (8) | −0.0153 (6) |
| O7 | 0.159 (3) | 0.153 (4) | 0.128 (3) | −0.093 (3) | 0.024 (3) | −0.062 (3) |
| O10 | 0.0898 (18) | 0.0728 (17) | 0.0599 (14) | 0.0103 (14) | 0.0180 (14) | 0.0001 (12) |
| O19 | 0.0498 (12) | 0.0887 (18) | 0.0483 (12) | 0.0076 (11) | −0.0098 (10) | 0.0087 (11) |
| O21 | 0.0394 (11) | 0.0803 (16) | 0.0554 (12) | 0.0056 (10) | 0.0030 (10) | −0.0077 (11) |
| O23 | 0.0507 (12) | 0.0819 (16) | 0.0460 (11) | 0.0024 (11) | 0.0044 (10) | 0.0106 (11) |
| O31 | 0.0698 (14) | 0.0686 (15) | 0.0563 (13) | 0.0078 (12) | −0.0193 (12) | −0.0053 (11) |
| O33 | 0.0930 (18) | 0.0727 (16) | 0.0519 (12) | 0.0264 (14) | −0.0143 (12) | 0.0041 (11) |
| O35 | 0.123 (2) | 0.0532 (15) | 0.0780 (17) | 0.0040 (14) | −0.0279 (16) | 0.0027 (13) |
| N1 | 0.0439 (13) | 0.0544 (15) | 0.0437 (13) | −0.0017 (11) | −0.0038 (11) | 0.0064 (11) |
| C2 | 0.0450 (16) | 0.065 (2) | 0.0471 (17) | −0.0039 (14) | −0.0004 (14) | 0.0133 (14) |
| C3 | 0.0561 (19) | 0.082 (3) | 0.069 (2) | −0.0179 (18) | −0.0134 (18) | 0.0181 (19) |
| C4 | 0.091 (3) | 0.078 (3) | 0.059 (2) | −0.032 (2) | −0.010 (2) | −0.0022 (19) |
| C5 | 0.074 (2) | 0.059 (2) | 0.0480 (17) | −0.0071 (16) | −0.0056 (16) | −0.0033 (15) |
| C6 | 0.0459 (16) | 0.0573 (19) | 0.0395 (14) | −0.0012 (13) | −0.0030 (13) | 0.0037 (13) |
| C8 | 0.122 (4) | 0.084 (3) | 0.080 (3) | −0.014 (3) | 0.013 (3) | −0.028 (2) |
| C9 | 0.0534 (18) | 0.059 (2) | 0.0488 (17) | 0.0052 (14) | −0.0093 (15) | 0.0025 (15) |
| C11 | 0.063 (2) | 0.053 (2) | 0.068 (2) | −0.0030 (15) | 0.0041 (17) | 0.0006 (16) |
| C13 | 0.0458 (15) | 0.0477 (16) | 0.0405 (14) | 0.0050 (13) | −0.0035 (13) | −0.0027 (12) |
| C14 | 0.0482 (16) | 0.0592 (19) | 0.0391 (15) | 0.0065 (13) | −0.0035 (13) | 0.0010 (13) |
| C15 | 0.0464 (16) | 0.0610 (19) | 0.0382 (15) | 0.0056 (14) | 0.0041 (13) | −0.0047 (13) |
| C16 | 0.0434 (16) | 0.0617 (19) | 0.0440 (16) | 0.0083 (13) | 0.0020 (13) | −0.0080 (14) |
| C17 | 0.0460 (16) | 0.0606 (19) | 0.0381 (15) | 0.0123 (14) | −0.0033 (13) | −0.0044 (13) |
| C18 | 0.0491 (16) | 0.0526 (18) | 0.0382 (14) | 0.0045 (13) | −0.0007 (13) | 0.0010 (13) |
| C20 | 0.074 (2) | 0.072 (2) | 0.0524 (19) | 0.0114 (18) | −0.0165 (18) | 0.0106 (17) |
| C22 | 0.0535 (19) | 0.091 (3) | 0.078 (2) | −0.0043 (19) | 0.0008 (19) | −0.019 (2) |
| C24 | 0.065 (2) | 0.078 (2) | 0.0553 (19) | 0.0018 (18) | 0.0036 (17) | 0.0149 (17) |
| C25 | 0.0483 (16) | 0.060 (2) | 0.0438 (16) | −0.0018 (14) | −0.0009 (14) | 0.0072 (14) |
| C26 | 0.066 (2) | 0.058 (2) | 0.0489 (17) | −0.0037 (16) | −0.0071 (16) | 0.0021 (15) |
| C27 | 0.075 (2) | 0.0498 (19) | 0.0531 (18) | 0.0052 (16) | −0.0015 (17) | 0.0044 (15) |
| C28 | 0.066 (2) | 0.059 (2) | 0.0404 (15) | 0.0137 (16) | −0.0069 (15) | 0.0030 (14) |
| C29 | 0.0525 (17) | 0.061 (2) | 0.0424 (16) | 0.0044 (14) | −0.0017 (14) | −0.0024 (14) |
| C30 | 0.0540 (17) | 0.0533 (18) | 0.0491 (16) | 0.0016 (14) | −0.0026 (15) | 0.0063 (14) |
| C32 | 0.080 (2) | 0.064 (2) | 0.070 (2) | −0.0091 (18) | −0.011 (2) | −0.0067 (18) |
| C34 | 0.096 (3) | 0.085 (3) | 0.086 (3) | 0.038 (2) | −0.026 (2) | −0.012 (2) |
| C36 | 0.147 (4) | 0.056 (2) | 0.085 (3) | −0.007 (3) | −0.022 (3) | −0.010 (2) |
| Cl12—C11 | 1.749 (3) | C27—C28 | 1.392 (5) |
| O7—C4 | 1.201 (6) | C28—C29 | 1.380 (5) |
| O10—C9 | 1.225 (4) | C29—C30 | 1.391 (4) |
| O19—C17 | 1.371 (3) | C2—H2 | 0.9800 |
| O19—C20 | 1.416 (4) | C3—H3A | 0.9700 |
| O21—C16 | 1.391 (3) | C3—H3B | 0.9700 |
| O21—C22 | 1.422 (4) | C5—H5 | 0.9800 |
| O23—C15 | 1.366 (4) | C6—H6 | 0.9800 |
| O23—C24 | 1.418 (4) | C8—H8A | 0.9600 |
| O31—C29 | 1.366 (4) | C8—H8B | 0.9600 |
| O31—C32 | 1.419 (4) | C8—H8C | 0.9600 |
| O33—C28 | 1.377 (4) | C11—H11A | 0.9700 |
| O33—C34 | 1.428 (5) | C11—H11B | 0.9700 |
| O35—C27 | 1.362 (4) | C14—H14 | 0.9300 |
| O35—C36 | 1.400 (5) | C18—H18 | 0.9300 |
| N1—C2 | 1.485 (4) | C20—H20A | 0.9600 |
| N1—C6 | 1.492 (4) | C20—H20B | 0.9600 |
| N1—C9 | 1.355 (4) | C20—H20C | 0.9600 |
| C2—C3 | 1.520 (5) | C22—H22A | 0.9600 |
| C2—C25 | 1.529 (4) | C22—H22B | 0.9600 |
| C3—C4 | 1.476 (5) | C22—H22C | 0.9600 |
| C4—C5 | 1.520 (6) | C24—H24A | 0.9600 |
| C5—C6 | 1.535 (4) | C24—H24B | 0.9600 |
| C5—C8 | 1.517 (6) | C24—H24C | 0.9600 |
| C6—C13 | 1.523 (4) | C26—H26 | 0.9300 |
| C9—C11 | 1.514 (5) | C30—H30 | 0.9300 |
| C13—C14 | 1.382 (4) | C32—H32A | 0.9600 |
| C13—C18 | 1.393 (4) | C32—H32B | 0.9600 |
| C14—C15 | 1.383 (4) | C32—H32C | 0.9600 |
| C15—C16 | 1.390 (4) | C34—H34A | 0.9600 |
| C16—C17 | 1.387 (4) | C34—H34B | 0.9600 |
| C17—C18 | 1.385 (4) | C34—H34C | 0.9600 |
| C25—C26 | 1.373 (5) | C36—H36A | 0.9600 |
| C25—C30 | 1.392 (4) | C36—H36B | 0.9600 |
| C26—C27 | 1.394 (5) | C36—H36C | 0.9600 |
| C17—O19—C20 | 118.0 (3) | C4—C5—H5 | 107.00 |
| C16—O21—C22 | 113.8 (2) | C6—C5—H5 | 107.00 |
| C15—O23—C24 | 117.4 (2) | C8—C5—H5 | 107.00 |
| C29—O31—C32 | 117.8 (3) | N1—C6—H6 | 108.00 |
| C28—O33—C34 | 113.9 (3) | C5—C6—H6 | 108.00 |
| C27—O35—C36 | 118.5 (3) | C13—C6—H6 | 108.00 |
| C2—N1—C6 | 119.3 (2) | C5—C8—H8A | 109.00 |
| C2—N1—C9 | 116.6 (2) | C5—C8—H8B | 109.00 |
| C6—N1—C9 | 123.0 (2) | C5—C8—H8C | 109.00 |
| N1—C2—C3 | 108.7 (2) | H8A—C8—H8B | 109.00 |
| N1—C2—C25 | 112.3 (2) | H8A—C8—H8C | 110.00 |
| C3—C2—C25 | 116.5 (3) | H8B—C8—H8C | 109.00 |
| C2—C3—C4 | 114.2 (3) | Cl12—C11—H11A | 109.00 |
| O7—C4—C3 | 122.1 (4) | Cl12—C11—H11B | 109.00 |
| O7—C4—C5 | 121.6 (4) | C9—C11—H11A | 109.00 |
| C3—C4—C5 | 116.3 (3) | C9—C11—H11B | 109.00 |
| C4—C5—C6 | 112.6 (3) | H11A—C11—H11B | 108.00 |
| C4—C5—C8 | 112.0 (3) | C13—C14—H14 | 120.00 |
| C6—C5—C8 | 110.9 (3) | C15—C14—H14 | 120.00 |
| N1—C6—C5 | 112.1 (2) | C13—C18—H18 | 120.00 |
| N1—C6—C13 | 112.1 (2) | C17—C18—H18 | 120.00 |
| C5—C6—C13 | 108.9 (3) | O19—C20—H20A | 109.00 |
| O10—C9—N1 | 122.5 (3) | O19—C20—H20B | 110.00 |
| O10—C9—C11 | 120.2 (3) | O19—C20—H20C | 109.00 |
| N1—C9—C11 | 117.3 (3) | H20A—C20—H20B | 109.00 |
| Cl12—C11—C9 | 112.4 (3) | H20A—C20—H20C | 109.00 |
| C6—C13—C14 | 119.7 (2) | H20B—C20—H20C | 110.00 |
| C6—C13—C18 | 120.2 (2) | O21—C22—H22A | 110.00 |
| C14—C13—C18 | 120.1 (3) | O21—C22—H22B | 109.00 |
| C13—C14—C15 | 120.3 (3) | O21—C22—H22C | 109.00 |
| O23—C15—C14 | 124.3 (3) | H22A—C22—H22B | 110.00 |
| O23—C15—C16 | 115.8 (2) | H22A—C22—H22C | 109.00 |
| C14—C15—C16 | 119.9 (3) | H22B—C22—H22C | 109.00 |
| O21—C16—C15 | 120.1 (3) | O23—C24—H24A | 109.00 |
| O21—C16—C17 | 120.2 (3) | O23—C24—H24B | 110.00 |
| C15—C16—C17 | 119.7 (3) | O23—C24—H24C | 110.00 |
| O19—C17—C16 | 115.8 (2) | H24A—C24—H24B | 109.00 |
| O19—C17—C18 | 123.7 (3) | H24A—C24—H24C | 109.00 |
| C16—C17—C18 | 120.5 (3) | H24B—C24—H24C | 109.00 |
| C13—C18—C17 | 119.4 (3) | C25—C26—H26 | 120.00 |
| C2—C25—C26 | 123.2 (3) | C27—C26—H26 | 120.00 |
| C2—C25—C30 | 117.2 (3) | C25—C30—H30 | 120.00 |
| C26—C25—C30 | 119.6 (3) | C29—C30—H30 | 120.00 |
| C25—C26—C27 | 120.2 (3) | O31—C32—H32A | 109.00 |
| O35—C27—C26 | 124.2 (3) | O31—C32—H32B | 109.00 |
| O35—C27—C28 | 115.4 (3) | O31—C32—H32C | 110.00 |
| C26—C27—C28 | 120.4 (3) | H32A—C32—H32B | 110.00 |
| O33—C28—C27 | 120.5 (3) | H32A—C32—H32C | 109.00 |
| O33—C28—C29 | 120.1 (3) | H32B—C32—H32C | 109.00 |
| C27—C28—C29 | 119.3 (3) | O33—C34—H34A | 110.00 |
| O31—C29—C28 | 116.3 (3) | O33—C34—H34B | 110.00 |
| O31—C29—C30 | 123.4 (3) | O33—C34—H34C | 109.00 |
| C28—C29—C30 | 120.2 (3) | H34A—C34—H34B | 110.00 |
| C25—C30—C29 | 120.3 (3) | H34A—C34—H34C | 109.00 |
| N1—C2—H2 | 106.00 | H34B—C34—H34C | 109.00 |
| C3—C2—H2 | 106.00 | O35—C36—H36A | 109.00 |
| C25—C2—H2 | 106.00 | O35—C36—H36B | 109.00 |
| C2—C3—H3A | 109.00 | O35—C36—H36C | 110.00 |
| C2—C3—H3B | 109.00 | H36A—C36—H36B | 109.00 |
| C4—C3—H3A | 109.00 | H36A—C36—H36C | 110.00 |
| C4—C3—H3B | 109.00 | H36B—C36—H36C | 109.00 |
| H3A—C3—H3B | 108.00 | ||
| C20—O19—C17—C18 | 5.9 (4) | C4—C5—C6—C13 | 171.4 (3) |
| C20—O19—C17—C16 | −176.3 (3) | C5—C6—C13—C18 | −69.9 (3) |
| C22—O21—C16—C17 | −97.6 (3) | N1—C6—C13—C18 | 54.7 (4) |
| C22—O21—C16—C15 | 83.5 (4) | N1—C6—C13—C14 | −126.7 (3) |
| C24—O23—C15—C14 | 16.4 (4) | C5—C6—C13—C14 | 108.6 (3) |
| C24—O23—C15—C16 | −163.9 (3) | N1—C9—C11—Cl12 | 175.0 (2) |
| C32—O31—C29—C30 | 19.2 (4) | O10—C9—C11—Cl12 | −4.3 (4) |
| C32—O31—C29—C28 | −160.1 (3) | C6—C13—C18—C17 | 179.4 (3) |
| C34—O33—C28—C29 | −100.9 (4) | C18—C13—C14—C15 | −2.3 (5) |
| C34—O33—C28—C27 | 82.9 (4) | C14—C13—C18—C17 | 0.8 (4) |
| C36—O35—C27—C28 | 179.3 (3) | C6—C13—C14—C15 | 179.2 (3) |
| C36—O35—C27—C26 | −0.2 (5) | C13—C14—C15—C16 | 1.7 (5) |
| C9—N1—C2—C25 | −103.5 (3) | C13—C14—C15—O23 | −178.6 (3) |
| C6—N1—C9—C11 | 0.7 (4) | O23—C15—C16—O21 | −0.6 (4) |
| C2—N1—C6—C5 | −7.8 (3) | O23—C15—C16—C17 | −179.5 (3) |
| C2—N1—C9—O10 | 11.9 (4) | C14—C15—C16—O21 | 179.2 (3) |
| C9—N1—C2—C3 | 126.2 (3) | C14—C15—C16—C17 | 0.3 (5) |
| C6—N1—C2—C3 | −42.4 (3) | C15—C16—C17—O19 | −179.6 (3) |
| C2—N1—C9—C11 | −167.4 (3) | C15—C16—C17—C18 | −1.7 (5) |
| C6—N1—C9—O10 | −180.0 (3) | O21—C16—C17—C18 | 179.4 (3) |
| C9—N1—C6—C5 | −175.6 (3) | O21—C16—C17—O19 | 1.5 (4) |
| C6—N1—C2—C25 | 88.0 (3) | O19—C17—C18—C13 | 178.9 (3) |
| C9—N1—C6—C13 | 61.6 (3) | C16—C17—C18—C13 | 1.2 (4) |
| C2—N1—C6—C13 | −130.7 (3) | C2—C25—C30—C29 | 179.2 (3) |
| C3—C2—C25—C26 | −1.1 (4) | C30—C25—C26—C27 | −1.0 (5) |
| C3—C2—C25—C30 | −178.8 (3) | C26—C25—C30—C29 | 1.4 (4) |
| N1—C2—C3—C4 | 55.7 (4) | C2—C25—C26—C27 | −178.7 (3) |
| N1—C2—C25—C26 | −127.3 (3) | C25—C26—C27—C28 | −0.5 (5) |
| C25—C2—C3—C4 | −72.3 (4) | C25—C26—C27—O35 | 179.0 (3) |
| N1—C2—C25—C30 | 55.0 (3) | O35—C27—C28—O33 | −1.7 (5) |
| C2—C3—C4—C5 | −17.8 (4) | O35—C27—C28—C29 | −177.9 (3) |
| C2—C3—C4—O7 | 160.5 (4) | C26—C27—C28—C29 | 1.6 (5) |
| C3—C4—C5—C8 | −159.8 (3) | C26—C27—C28—O33 | 177.9 (3) |
| O7—C4—C5—C6 | 147.7 (4) | O33—C28—C29—O31 | 1.8 (4) |
| C3—C4—C5—C6 | −34.0 (4) | C27—C28—C29—C30 | −1.2 (4) |
| O7—C4—C5—C8 | 21.9 (5) | O33—C28—C29—C30 | −177.5 (3) |
| C8—C5—C6—C13 | −62.2 (4) | C27—C28—C29—O31 | 178.1 (3) |
| C8—C5—C6—N1 | 173.2 (3) | O31—C29—C30—C25 | −179.6 (3) |
| C4—C5—C6—N1 | 46.8 (3) | C28—C29—C30—C25 | −0.3 (4) |
The authors are grateful to the DST and Government of India project SP/I2/FOO/93 and the University of Mysore for financial assistance.
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Piperidines are an important group of compounds in the field of medicinal chemistry owing to the fact that they can frequently be recognized in the structures of numerous naturally occurring alkaloid and synthetic compounds with interesting biological and pharmacological properties (Prostakov et al., 1978). Furthermore, the significant biological activities of piperridones were associated with aryl substituents at 2 and 6 positions (Ganellin & Spickett, 1965; Mobio et al., 1989). In view of the importance of such compounds the crystal structure of the title compound is reported.
The substituent at C2 is in an equatorial position as indicated by the dihedral angle of 85.18 (2)° between the piperidine and the phenyl ring. The methyl group at C5 reflects C8 and is oriented in an anti-periplanar conformation as indicated by the torsion angle of N1—C6—C5—C8 = -173.25°. The torsion angle of 180.0 (3)° for C6—N1—C9—O10 shows that O10 is also in an anti-periplanar conformation. The methoxy groups at C27, C25, C17 and C15 are nearly planar with the phenyl ring whereas the methoxy group at C26 and C16 is nearly orthogonal to the phenyl rings.