Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200065X/ci6074sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680200065X/ci6074Isup2.hkl |
CCDC reference: 182595
The title compound was synthesized by condensation of 9.90 g (0.100 mol) piperidin-4-one and 10.7 ml (0.100 ml) ethyl acetate in the presence of 0.05 g benzaldehyde and the appropriate aliphatic ketone. The reaction mixture was heated for about 16 h. The solvent was evaporated and the crystals were purified by recrystallization from methanol (m.p. 433 K, yield 70%).
Atoms C32 and C33 of the ethoxycarbonyl group were found to be disordered. The occupancies of the disordered positions C32/C32' and C33/C33' were initially refined and later fixed at 55/45. The corresponding O—C and C—C distances in the major and minor conformers were restrained to be equal. The H atom attached to N1 was located from a difference map and isotropically refined. All other H atoms were geometrically positioned and allowed to ride on their parent atoms.
Data collection: CAD-4 Software (Frenz, 1989); cell refinement: MolEN (Fair,1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. For clarity, only the major (55%) conformer of the ethoxycarbonyl group is shown. |
C20H21NO3 | F(000) = 688 |
Mr = 323.38 | Dx = 1.208 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.124 (2) Å | Cell parameters from 25 reflections |
b = 7.801 (3) Å | θ = 2–25° |
c = 22.896 (3) Å | µ = 0.08 mm−1 |
β = 100.39 (1)° | T = 293 K |
V = 1778.6 (8) Å3 | Needle, colourless |
Z = 4 | 0.30 × 0.17 × 0.09 mm |
Enraf-Nonius CAD-4 diffractometer | 2629 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 25.3°, θmin = 1.8° |
ω–2θ scans | h = 0→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.972, Tmax = 0.986 | l = −27→27 |
3430 measured reflections | 2 standard reflections every 60 reflections |
3236 independent reflections | intensity decay: none |
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)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.206 | w = 1/[σ2(Fo2) + (0.1093P)2 + 0.5001P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3236 reflections | Δρmax = 0.44 e Å−3 |
240 parameters | Δρmin = −0.41 e Å−3 |
11 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (1) |
C20H21NO3 | V = 1778.6 (8) Å3 |
Mr = 323.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.124 (2) Å | µ = 0.08 mm−1 |
b = 7.801 (3) Å | T = 293 K |
c = 22.896 (3) Å | 0.30 × 0.17 × 0.09 mm |
β = 100.39 (1)° |
Enraf-Nonius CAD-4 diffractometer | 2629 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.047 |
Tmin = 0.972, Tmax = 0.986 | 2 standard reflections every 60 reflections |
3430 measured reflections | intensity decay: none |
3236 independent reflections |
R[F2 > 2σ(F2)] = 0.069 | 11 restraints |
wR(F2) = 0.206 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.44 e Å−3 |
3236 reflections | Δρmin = −0.41 e Å−3 |
240 parameters |
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 | Occ. (<1) | |
N1 | 0.22618 (16) | 0.8041 (2) | 0.05357 (7) | 0.0533 (5) | |
H1 | 0.1648 (19) | 0.874 (3) | 0.0662 (10) | 0.067 (7)* | |
C2 | 0.35533 (19) | 0.8391 (3) | 0.09144 (9) | 0.0545 (5) | |
H2 | 0.3805 | 0.9584 | 0.0858 | 0.065* | |
C3 | 0.46244 (19) | 0.7192 (3) | 0.07300 (9) | 0.0561 (6) | |
H3 | 0.4429 | 0.6019 | 0.0842 | 0.067* | |
O4 | 0.56073 (18) | 0.7240 (3) | −0.01393 (9) | 0.1000 (8) | |
C4 | 0.4587 (2) | 0.7226 (3) | 0.00661 (11) | 0.0653 (6) | |
C5 | 0.3229 (2) | 0.7190 (3) | −0.03089 (10) | 0.0654 (6) | |
H5A | 0.2875 | 0.6033 | −0.0314 | 0.078* | |
H5B | 0.3300 | 0.7492 | −0.0713 | 0.078* | |
C6 | 0.22469 (19) | 0.8419 (3) | −0.00888 (9) | 0.0534 (5) | |
H6 | 0.2553 | 0.9600 | −0.0125 | 0.064* | |
C7 | 0.0858 (2) | 0.8217 (3) | −0.04577 (9) | 0.0540 (5) | |
C8 | −0.0148 (2) | 0.7309 (3) | −0.02593 (11) | 0.0690 (7) | |
H8 | 0.0014 | 0.6824 | 0.0118 | 0.083* | |
C9 | −0.1395 (3) | 0.7118 (4) | −0.06175 (14) | 0.0823 (8) | |
H9 | −0.2066 | 0.6517 | −0.0476 | 0.099* | |
C10 | −0.1651 (3) | 0.7796 (4) | −0.11737 (14) | 0.0816 (8) | |
H10 | −0.2486 | 0.7643 | −0.1415 | 0.098* | |
C11 | −0.0666 (3) | 0.8706 (4) | −0.13741 (13) | 0.0852 (8) | |
H11 | −0.0835 | 0.9189 | −0.1752 | 0.102* | |
C12 | 0.0573 (2) | 0.8908 (4) | −0.10199 (11) | 0.0715 (7) | |
H12 | 0.1233 | 0.9526 | −0.1163 | 0.086* | |
C13 | 0.3464 (2) | 0.8118 (3) | 0.15574 (9) | 0.0593 (6) | |
C14 | 0.4162 (3) | 0.9160 (4) | 0.19945 (11) | 0.0830 (8) | |
H14 | 0.4671 | 1.0060 | 0.1888 | 0.100* | |
C15 | 0.4119 (4) | 0.8897 (6) | 0.25807 (14) | 0.1067 (12) | |
H15 | 0.4605 | 0.9609 | 0.2868 | 0.128* | |
C16 | 0.3372 (4) | 0.7603 (7) | 0.27461 (13) | 0.1133 (14) | |
H16 | 0.3337 | 0.7438 | 0.3145 | 0.136* | |
C17 | 0.2670 (3) | 0.6540 (5) | 0.23251 (14) | 0.1010 (11) | |
H17 | 0.2160 | 0.5649 | 0.2438 | 0.121* | |
C18 | 0.2719 (3) | 0.6797 (4) | 0.17266 (11) | 0.0762 (7) | |
H18 | 0.2246 | 0.6070 | 0.1441 | 0.091* | |
O31 | 0.64336 (17) | 0.9081 (3) | 0.11099 (10) | 0.0892 (7) | |
C31 | 0.6011 (2) | 0.7650 (3) | 0.10495 (11) | 0.0673 (6) | |
O32 | 0.67255 (18) | 0.6267 (3) | 0.12460 (11) | 0.1024 (8) | |
C32 | 0.7934 (6) | 0.6683 (10) | 0.1695 (3) | 0.104 (2) | 0.55 |
H32A | 0.7921 | 0.6105 | 0.2069 | 0.125* | 0.55 |
H32B | 0.8025 | 0.7908 | 0.1763 | 0.125* | 0.55 |
C33 | 0.9020 (8) | 0.5997 (19) | 0.1393 (6) | 0.253 (9) | 0.55 |
H33A | 0.9876 | 0.6406 | 0.1595 | 0.379* | 0.55 |
H33B | 0.8870 | 0.6379 | 0.0988 | 0.379* | 0.55 |
H33C | 0.9010 | 0.4767 | 0.1403 | 0.379* | 0.55 |
C32' | 0.8205 (5) | 0.6432 (12) | 0.1322 (4) | 0.096 (2) | 0.45 |
H32C | 0.8465 | 0.7332 | 0.1073 | 0.115* | 0.45 |
H32D | 0.8623 | 0.5362 | 0.1239 | 0.115* | 0.45 |
C33' | 0.8541 (11) | 0.6893 (18) | 0.1973 (4) | 0.158 (5) | 0.45 |
H33D | 0.9369 | 0.7521 | 0.2049 | 0.237* | 0.45 |
H33E | 0.8632 | 0.5864 | 0.2207 | 0.237* | 0.45 |
H33F | 0.7834 | 0.7586 | 0.2077 | 0.237* | 0.45 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0440 (9) | 0.0658 (11) | 0.0518 (10) | 0.0002 (8) | 0.0135 (7) | −0.0015 (8) |
C2 | 0.0473 (11) | 0.0584 (12) | 0.0580 (12) | −0.0022 (9) | 0.0100 (9) | 0.0005 (9) |
C3 | 0.0444 (11) | 0.0628 (12) | 0.0628 (12) | 0.0005 (9) | 0.0143 (9) | 0.0060 (10) |
O4 | 0.0555 (10) | 0.166 (2) | 0.0865 (13) | 0.0164 (11) | 0.0340 (9) | 0.0159 (13) |
C4 | 0.0513 (12) | 0.0811 (16) | 0.0682 (14) | 0.0077 (10) | 0.0233 (10) | 0.0058 (11) |
C5 | 0.0563 (12) | 0.0884 (16) | 0.0548 (12) | 0.0081 (11) | 0.0190 (10) | −0.0010 (11) |
C6 | 0.0480 (11) | 0.0597 (12) | 0.0542 (11) | −0.0023 (8) | 0.0136 (8) | 0.0029 (9) |
C7 | 0.0489 (11) | 0.0563 (11) | 0.0580 (12) | 0.0013 (9) | 0.0130 (9) | −0.0031 (9) |
C8 | 0.0554 (13) | 0.0803 (16) | 0.0724 (14) | −0.0084 (11) | 0.0141 (11) | 0.0037 (12) |
C9 | 0.0530 (13) | 0.0913 (19) | 0.102 (2) | −0.0125 (13) | 0.0134 (13) | −0.0056 (16) |
C10 | 0.0571 (14) | 0.0824 (18) | 0.097 (2) | 0.0028 (12) | −0.0094 (13) | −0.0090 (15) |
C11 | 0.0822 (18) | 0.093 (2) | 0.0725 (16) | 0.0014 (15) | −0.0063 (13) | 0.0071 (14) |
C12 | 0.0629 (14) | 0.0831 (16) | 0.0662 (14) | −0.0061 (12) | 0.0058 (11) | 0.0089 (12) |
C13 | 0.0523 (11) | 0.0704 (14) | 0.0549 (12) | 0.0072 (10) | 0.0089 (9) | −0.0029 (10) |
C14 | 0.0745 (16) | 0.100 (2) | 0.0703 (16) | 0.0022 (14) | 0.0024 (12) | −0.0185 (14) |
C15 | 0.107 (2) | 0.144 (3) | 0.0644 (18) | 0.020 (2) | 0.0005 (16) | −0.0282 (19) |
C16 | 0.122 (3) | 0.168 (4) | 0.0509 (16) | 0.049 (3) | 0.0182 (17) | 0.005 (2) |
C17 | 0.106 (2) | 0.128 (3) | 0.0745 (19) | 0.014 (2) | 0.0326 (17) | 0.0280 (19) |
C18 | 0.0809 (16) | 0.0873 (18) | 0.0622 (14) | −0.0003 (14) | 0.0179 (12) | 0.0067 (12) |
O31 | 0.0558 (10) | 0.0805 (13) | 0.1287 (17) | −0.0132 (9) | 0.0096 (10) | 0.0093 (11) |
C31 | 0.0496 (12) | 0.0720 (15) | 0.0805 (16) | −0.0031 (11) | 0.0126 (11) | 0.0102 (12) |
O32 | 0.0609 (11) | 0.0856 (14) | 0.145 (2) | 0.0002 (9) | −0.0239 (11) | 0.0235 (12) |
C32 | 0.082 (4) | 0.119 (5) | 0.096 (5) | 0.002 (4) | −0.028 (4) | 0.010 (4) |
C33 | 0.054 (4) | 0.326 (17) | 0.360 (18) | 0.010 (6) | −0.010 (6) | −0.234 (15) |
C32' | 0.061 (4) | 0.106 (6) | 0.112 (7) | 0.016 (4) | −0.004 (4) | 0.009 (5) |
C33' | 0.101 (7) | 0.239 (14) | 0.114 (7) | −0.045 (8) | −0.036 (6) | 0.049 (8) |
N1—C6 | 1.457 (3) | C13—C18 | 1.374 (4) |
N1—C2 | 1.458 (3) | C13—C14 | 1.381 (3) |
N1—H1 | 0.91 (2) | C14—C15 | 1.366 (4) |
C2—C13 | 1.506 (3) | C14—H14 | 0.93 |
C2—C3 | 1.547 (3) | C15—C16 | 1.355 (6) |
C2—H2 | 0.98 | C15—H15 | 0.93 |
C3—C31 | 1.505 (3) | C16—C17 | 1.370 (6) |
C3—C4 | 1.514 (3) | C16—H16 | 0.93 |
C3—H3 | 0.98 | C17—C18 | 1.395 (4) |
O4—C4 | 1.209 (3) | C17—H17 | 0.93 |
C4—C5 | 1.485 (3) | C18—H18 | 0.93 |
C5—C6 | 1.530 (3) | O31—C31 | 1.194 (3) |
C5—H5A | 0.97 | C31—O32 | 1.331 (3) |
C5—H5B | 0.97 | O32—C32' | 1.482 (5) |
C6—C7 | 1.512 (3) | O32—C32 | 1.485 (4) |
C6—H6 | 0.98 | C32—C33 | 1.500 (5) |
C7—C12 | 1.378 (3) | C32—H32A | 0.97 |
C7—C8 | 1.383 (3) | C32—H32B | 0.97 |
C8—C9 | 1.383 (4) | C33—H33A | 0.96 |
C8—H8 | 0.93 | C33—H33B | 0.96 |
C9—C10 | 1.360 (4) | C33—H33C | 0.96 |
C9—H9 | 0.93 | C32'—C33' | 1.512 (5) |
C10—C11 | 1.370 (4) | C32'—H32C | 0.97 |
C10—H10 | 0.93 | C32'—H32D | 0.97 |
C11—C12 | 1.374 (3) | C33'—H33D | 0.96 |
C11—H11 | 0.93 | C33'—H33E | 0.96 |
C12—H12 | 0.93 | C33'—H33F | 0.96 |
C6—N1—C2 | 113.26 (15) | C18—C13—C14 | 118.2 (2) |
C6—N1—H1 | 107.6 (14) | C18—C13—C2 | 121.0 (2) |
C2—N1—H1 | 106.8 | C14—C13—C2 | 120.8 (2) |
N1—C2—C13 | 110.44 (16) | C15—C14—C13 | 121.4 (3) |
N1—C2—C3 | 108.77 (17) | C15—C14—H14 | 119.3 |
C13—C2—C3 | 110.46 (17) | C13—C14—H14 | 119.3 |
N1—C2—H2 | 109.0 | C16—C15—C14 | 120.3 (3) |
C13—C2—H2 | 109.0 | C16—C15—H15 | 119.9 |
C3—C2—H2 | 109.0 | C14—C15—H15 | 119.9 |
C31—C3—C4 | 109.62 (18) | C15—C16—C17 | 120.0 (3) |
C31—C3—C2 | 111.22 (18) | C15—C16—H16 | 120.0 |
C4—C3—C2 | 111.82 (17) | C17—C16—H16 | 120.0 |
C31—C3—H3 | 108.0 | C16—C17—C18 | 119.9 (3) |
C4—C3—H3 | 108.0 | C16—C17—H17 | 120.1 |
C2—C3—H3 | 108.0 | C18—C17—H17 | 120.1 |
O4—C4—C5 | 122.8 (2) | C13—C18—C17 | 120.2 (3) |
O4—C4—C3 | 121.5 (2) | C13—C18—H18 | 119.9 |
C5—C4—C3 | 115.65 (17) | C17—C18—H18 | 119.9 |
C4—C5—C6 | 112.75 (19) | O31—C31—O32 | 123.9 (2) |
C4—C5—H5A | 109.0 | O31—C31—C3 | 124.2 (2) |
C6—C5—H5A | 109.0 | O32—C31—C3 | 112.0 (2) |
C4—C5—H5B | 109.0 | C31—O32—C32' | 116.4 (4) |
C6—C5—H5B | 109.0 | C31—O32—C32 | 112.7 (4) |
H5A—C5—H5B | 107.8 | C32'—O32—C32 | 37.9 (3) |
N1—C6—C7 | 111.77 (16) | O32—C32—C33 | 100.6 (6) |
N1—C6—C5 | 107.68 (17) | O32—C32—H32A | 111.7 |
C7—C6—C5 | 110.13 (17) | C33—C32—H32A | 111.7 |
N1—C6—H6 | 109.1 | O32—C32—H32B | 111.7 |
C7—C6—H6 | 109.1 | C33—C32—H32B | 111.7 |
C5—C6—H6 | 109.1 | H32A—C32—H32B | 109.4 |
C12—C7—C8 | 117.7 (2) | C32—C33—H33A | 109.5 |
C12—C7—C6 | 119.87 (19) | C32—C33—H33B | 109.5 |
C8—C7—C6 | 122.4 (2) | H33A—C33—H33B | 109.5 |
C9—C8—C7 | 120.5 (2) | C32—C33—H33C | 109.5 |
C9—C8—H8 | 119.7 | H33A—C33—H33C | 109.5 |
C7—C8—H8 | 119.7 | H33B—C33—H33C | 109.5 |
C10—C9—C8 | 120.9 (3) | O32—C32'—C33' | 100.3 (6) |
C10—C9—H9 | 119.6 | O32—C32'—H32C | 111.7 |
C8—C9—H9 | 119.6 | C33'—C32'—H32C | 111.7 |
C9—C10—C11 | 119.2 (2) | O32—C32'—H32D | 111.7 |
C9—C10—H10 | 120.4 | C33'—C32'—H32D | 111.7 |
C11—C10—H10 | 120.4 | H32C—C32'—H32D | 109.5 |
C10—C11—C12 | 120.3 (3) | C32'—C33'—H33D | 109.5 |
C10—C11—H11 | 119.9 | C32'—C33'—H33E | 109.5 |
C12—C11—H11 | 119.9 | H33D—C33'—H33E | 109.5 |
C11—C12—C7 | 121.4 (2) | C32'—C33'—H33F | 109.5 |
C11—C12—H12 | 119.3 | H33D—C33'—H33F | 109.5 |
C7—C12—H12 | 119.3 | H33E—C33'—H33F | 109.5 |
C6—N1—C2—C13 | 175.15 (17) | C8—C7—C12—C11 | −0.1 (4) |
C6—N1—C2—C3 | −63.5 (2) | C6—C7—C12—C11 | 178.1 (2) |
N1—C2—C3—C31 | 172.47 (17) | N1—C2—C13—C18 | 38.2 (3) |
C13—C2—C3—C31 | −66.2 (2) | C3—C2—C13—C18 | −82.2 (3) |
N1—C2—C3—C4 | 49.5 (2) | N1—C2—C13—C14 | −143.7 (2) |
C13—C2—C3—C4 | 170.91 (18) | C3—C2—C13—C14 | 95.9 (3) |
C31—C3—C4—O4 | 15.0 (3) | C18—C13—C14—C15 | 0.0 (4) |
C2—C3—C4—O4 | 138.8 (3) | C2—C13—C14—C15 | −178.2 (2) |
C31—C3—C4—C5 | −166.7 (2) | C13—C14—C15—C16 | −0.7 (5) |
C2—C3—C4—C5 | −42.9 (3) | C14—C15—C16—C17 | 0.8 (6) |
O4—C4—C5—C6 | −136.6 (3) | C15—C16—C17—C18 | −0.3 (5) |
C3—C4—C5—C6 | 45.1 (3) | C14—C13—C18—C17 | 0.5 (4) |
C2—N1—C6—C7 | −174.10 (17) | C2—C13—C18—C17 | 178.7 (2) |
C2—N1—C6—C5 | 64.8 (2) | C16—C17—C18—C13 | −0.4 (5) |
C4—C5—C6—N1 | −53.3 (2) | C4—C3—C31—O31 | 79.3 (3) |
C4—C5—C6—C7 | −175.37 (18) | C2—C3—C31—O31 | −44.9 (3) |
N1—C6—C7—C12 | 164.2 (2) | C4—C3—C31—O32 | −99.3 (3) |
C5—C6—C7—C12 | −76.2 (3) | C2—C3—C31—O32 | 136.5 (2) |
N1—C6—C7—C8 | −17.7 (3) | O31—C31—O32—C32' | −24.7 (6) |
C5—C6—C7—C8 | 101.9 (2) | C3—C31—O32—C32' | 153.9 (4) |
C12—C7—C8—C9 | −0.2 (4) | O31—C31—O32—C32 | 17.0 (5) |
C6—C7—C8—C9 | −178.3 (2) | C3—C31—O32—C32 | −164.4 (4) |
C7—C8—C9—C10 | 0.9 (4) | C31—O32—C32—C33 | −120.6 (8) |
C8—C9—C10—C11 | −1.3 (5) | C32'—O32—C32—C33 | −16.2 (9) |
C9—C10—C11—C12 | 1.0 (5) | C31—O32—C32'—C33' | 94.7 (7) |
C10—C11—C12—C7 | −0.3 (4) | C32—O32—C32'—C33' | 1.1 (8) |
Experimental details
Crystal data | |
Chemical formula | C20H21NO3 |
Mr | 323.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.124 (2), 7.801 (3), 22.896 (3) |
β (°) | 100.39 (1) |
V (Å3) | 1778.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.17 × 0.09 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.972, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3430, 3236, 2629 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.206, 1.10 |
No. of reflections | 3236 |
No. of parameters | 240 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.44, −0.41 |
Computer programs: CAD-4 Software (Frenz, 1989), MolEN (Fair,1990), MolEN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP97 (Zsolnai, 1997), SHELXL97.
C6—N1—C2—C13 | 175.15 (17) | C3—C4—C5—C6 | 45.1 (3) |
C6—N1—C2—C3 | −63.5 (2) | C2—N1—C6—C5 | 64.8 (2) |
N1—C2—C3—C4 | 49.5 (2) | C4—C5—C6—N1 | −53.3 (2) |
C2—C3—C4—C5 | −42.9 (3) | C4—C5—C6—C7 | −175.37 (18) |
The preferred conformation of the piperidine ring has been explained by chemical and physical methods, and in most of the derivatives it is found to exist in a chair conformation (Ramalingam et al., 1979). Also, investigations based on photoelectron spectroscopy and semi-empirical calculations show a pyrimidal N atom for the piperidine ring (Woydt et al., 1991). With a view to determining the conformational preference of the piperidine ring when it is substituted with bulky groups like the phenyl group and the ethoxycarbonyl group, the structure determination of the title compound, (I), was undertaken.
The piperidine ring of (I) adopts a slightly distorted chair conformation, with puckering amplitude Q = 0.543 (2) Å, θ = 13.9 (2)° and ϕ = 351.7 (10)° (Cremer & Pople, 1975). The puckering is enhanced at N1 and decreased at C4 (Sekar, Parthasarathy & Rajalingam, 1990; Sekar, Parthasarathy & Radhakrishnan, 1990; Sekar et al., 1993; Ianelli & Nardelli, 1992; Kooijman et al., 1997). The sum of bond angles around N1 (327.7°) indicates sp3 hybridization for N1. The two phenyl rings are equatorially attached to the piperidine ring. The phenyl rings at C2 and C6 form dihedral angles of 72.7 (1) and 53.8 (1)°, respectively, with the piperidine ring. The dihedral angle between the two phenyl ring planes is 37.9 (2)°.