Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041475/ci2447sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041475/ci2447Isup2.hkl |
CCDC reference: 663710
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.066
- wR factor = 0.220
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The condensation reaction involving anisaldehyde (24.3 ml, 200 mmol), ammonium acetate (7.7 g, 100 mmol) and pentan-2-one (10.7 ml, 100 mmol) afforded the title compound. Single crystals of the title compound were obtained by slow evaporation of a benzene-petroleum ether (8:1) solution.
The N-bound H atom was located in a difference map and refined isotropically. C-bound H atoms were included in calculated positions [C—H = 0.93–0.98 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Nitrogen heterocycles, in particular piperidone alkaloids, occur in both plants and animals and some of them possess a variety of biological activities, including cytotoxic and anti-cancer properties (Dimmock et al., 1990; Mutus et al., 1989). In view of the above importance, the X-ray crystal structure determination of the title compound has been undertaken.
Bond lengths and angles (Fig. 1) are comparable to those observed for 3-methyl-2,6-diphenyl-4-piperidone (Sekar et al., 1990). The piperidine ring adopts a chair conformation, with a puckering amplitude QT of 0.577 (3) Å (Nardelli, 1995). The two benzene rings are in equatorial orientation with respect to the piperidine ring which is evidenced from the torsion angles C15—C6—C5—C4 of 174.7 (3)° and C4—C3—C2—C9 of -178.6 (2)°. The ethyl group substitued at C3 is also oriented equatorially with the N1—C2—C3—C7 torsion angle being 178.4 (2)°. The dihedral angle between the two benzene rings is 48.4 (1)°. The methoxy groups are almost coplanar with the attached benzene rings.
The molecular structure is stabilized by a C—H···π interaction involving the C9—C14 benzene ring (centroid Cg1). The crystal structure is stabilized by C—H···π interactions (Desiraju, 1989) involving the C15—C20 benzene ring (centroid Cg2). The packing of the molecules viewed down the a axis is shown in Fig.2. In addition to the above-mentioned interactions, the structure is also stabilized by van der Waals forces
For related literature, see: Desiraju (1989); Dimmock et al. (1990); Sekar et al. (1990); Mutus et al. (1989).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
C21H25NO3 | F(000) = 728 |
Mr = 339.42 | Dx = 1.246 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3270 reflections |
a = 14.012 (2) Å | θ = 1.6–25.3° |
b = 7.8060 (14) Å | µ = 0.08 mm−1 |
c = 17.655 (3) Å | T = 293 K |
β = 110.401 (5)° | Block, colourless |
V = 1810.0 (5) Å3 | 0.15 × 0.13 × 0.10 mm |
Z = 4 |
Bruker Kappa APEX II area-detector diffractometer | 2348 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 25.3°, θmin = 1.6° |
ω and φ scans | h = −15→16 |
15103 measured reflections | k = −9→9 |
3270 independent reflections | l = −21→21 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.220 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1169P)2 + 0.8076P] where P = (Fo2 + 2Fc2)/3 |
3270 reflections | (Δ/σ)max = 0.001 |
230 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C21H25NO3 | V = 1810.0 (5) Å3 |
Mr = 339.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.012 (2) Å | µ = 0.08 mm−1 |
b = 7.8060 (14) Å | T = 293 K |
c = 17.655 (3) Å | 0.15 × 0.13 × 0.10 mm |
β = 110.401 (5)° |
Bruker Kappa APEX II area-detector diffractometer | 2348 reflections with I > 2σ(I) |
15103 measured reflections | Rint = 0.060 |
3270 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.220 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.26 e Å−3 |
3270 reflections | Δρmin = −0.27 e Å−3 |
230 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. |
x | y | z | Uiso*/Ueq | ||
H1 | 0.465 (2) | 0.530 (5) | 0.1687 (19) | 0.057 (9)* | |
C2 | 0.54806 (18) | 0.3215 (4) | 0.17902 (16) | 0.0411 (7) | |
H2 | 0.5470 | 0.2782 | 0.2308 | 0.049* | |
C3 | 0.54152 (19) | 0.1662 (4) | 0.12238 (16) | 0.0422 (7) | |
H3 | 0.5390 | 0.2119 | 0.0700 | 0.051* | |
C4 | 0.4410 (2) | 0.0763 (4) | 0.10928 (18) | 0.0462 (7) | |
C5 | 0.3484 (2) | 0.1890 (4) | 0.08452 (18) | 0.0492 (7) | |
H5A | 0.2904 | 0.1234 | 0.0863 | 0.059* | |
H5B | 0.3337 | 0.2270 | 0.0293 | 0.059* | |
C6 | 0.36336 (19) | 0.3454 (4) | 0.13980 (17) | 0.0418 (7) | |
H6 | 0.3705 | 0.3066 | 0.1943 | 0.050* | |
C7 | 0.6321 (2) | 0.0451 (4) | 0.1516 (2) | 0.0544 (8) | |
H7A | 0.6594 | 0.0486 | 0.2102 | 0.065* | |
H7B | 0.6082 | −0.0706 | 0.1358 | 0.065* | |
C8 | 0.7175 (3) | 0.0832 (5) | 0.1204 (2) | 0.0678 (10) | |
H8A | 0.7712 | 0.0011 | 0.1421 | 0.102* | |
H8B | 0.7433 | 0.1963 | 0.1368 | 0.102* | |
H8C | 0.6923 | 0.0763 | 0.0625 | 0.102* | |
C9 | 0.64449 (19) | 0.4237 (4) | 0.19468 (16) | 0.0400 (6) | |
C10 | 0.7234 (2) | 0.4118 (4) | 0.26803 (16) | 0.0427 (7) | |
H10 | 0.7151 | 0.3450 | 0.3089 | 0.051* | |
C11 | 0.81529 (19) | 0.4977 (4) | 0.28201 (16) | 0.0446 (7) | |
H11 | 0.8680 | 0.4867 | 0.3314 | 0.054* | |
C12 | 0.8272 (2) | 0.5987 (4) | 0.22232 (17) | 0.0429 (7) | |
C13 | 0.7491 (2) | 0.6126 (4) | 0.14879 (17) | 0.0484 (7) | |
H13 | 0.7576 | 0.6795 | 0.1080 | 0.058* | |
C14 | 0.6584 (2) | 0.5277 (4) | 0.13550 (17) | 0.0472 (7) | |
H14 | 0.6057 | 0.5402 | 0.0862 | 0.057* | |
C15 | 0.27395 (19) | 0.4669 (4) | 0.11000 (16) | 0.0399 (6) | |
C16 | 0.2672 (2) | 0.5889 (4) | 0.05091 (17) | 0.0478 (7) | |
H16 | 0.3198 | 0.5993 | 0.0306 | 0.057* | |
C17 | 0.1835 (2) | 0.6948 (4) | 0.02204 (17) | 0.0481 (7) | |
H17 | 0.1804 | 0.7759 | −0.0173 | 0.058* | |
C18 | 0.10395 (19) | 0.6814 (4) | 0.05126 (16) | 0.0422 (7) | |
C19 | 0.10883 (19) | 0.5612 (4) | 0.10976 (17) | 0.0447 (7) | |
H19 | 0.0558 | 0.5508 | 0.1297 | 0.054* | |
C20 | 0.1939 (2) | 0.4555 (4) | 0.13862 (17) | 0.0438 (7) | |
H20 | 0.1970 | 0.3750 | 0.1782 | 0.053* | |
C21 | 0.9997 (2) | 0.6714 (5) | 0.3003 (2) | 0.0695 (10) | |
H21A | 1.0539 | 0.7436 | 0.2977 | 0.104* | |
H21B | 1.0213 | 0.5540 | 0.3051 | 0.104* | |
H21C | 0.9822 | 0.7024 | 0.3465 | 0.104* | |
C22 | −0.0592 (2) | 0.7846 (5) | 0.0444 (2) | 0.0583 (9) | |
H22A | −0.1079 | 0.8711 | 0.0175 | 0.087* | |
H22B | −0.0376 | 0.8016 | 0.1018 | 0.087* | |
H22C | −0.0899 | 0.6735 | 0.0311 | 0.087* | |
N1 | 0.45796 (16) | 0.4296 (3) | 0.14268 (15) | 0.0451 (6) | |
O1 | 0.43561 (17) | −0.0761 (3) | 0.12028 (19) | 0.0785 (8) | |
O2 | 0.91367 (15) | 0.6923 (3) | 0.22939 (13) | 0.0614 (6) | |
O3 | 0.02622 (15) | 0.7956 (3) | 0.01916 (13) | 0.0572 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0278 (13) | 0.0504 (16) | 0.0437 (14) | 0.0004 (12) | 0.0109 (11) | 0.0018 (12) |
C3 | 0.0321 (14) | 0.0487 (16) | 0.0465 (15) | 0.0016 (12) | 0.0145 (12) | 0.0041 (12) |
C4 | 0.0365 (15) | 0.0428 (17) | 0.0587 (18) | −0.0027 (12) | 0.0160 (13) | −0.0059 (13) |
C5 | 0.0323 (15) | 0.0490 (17) | 0.0615 (18) | −0.0029 (12) | 0.0102 (13) | −0.0046 (14) |
C6 | 0.0290 (13) | 0.0486 (16) | 0.0475 (15) | 0.0016 (11) | 0.0129 (11) | −0.0004 (12) |
C7 | 0.0368 (15) | 0.0480 (18) | 0.080 (2) | 0.0054 (13) | 0.0223 (15) | 0.0078 (15) |
C8 | 0.0468 (18) | 0.060 (2) | 0.107 (3) | 0.0027 (15) | 0.0401 (19) | −0.0070 (19) |
C9 | 0.0292 (13) | 0.0446 (15) | 0.0437 (14) | 0.0004 (11) | 0.0094 (11) | −0.0019 (12) |
C10 | 0.0336 (14) | 0.0506 (16) | 0.0433 (15) | −0.0004 (12) | 0.0124 (11) | 0.0045 (12) |
C11 | 0.0280 (13) | 0.0567 (18) | 0.0435 (15) | 0.0014 (12) | 0.0056 (11) | 0.0035 (13) |
C12 | 0.0317 (14) | 0.0445 (16) | 0.0511 (16) | −0.0017 (12) | 0.0125 (12) | −0.0010 (13) |
C13 | 0.0435 (16) | 0.0490 (17) | 0.0496 (16) | −0.0021 (13) | 0.0124 (13) | 0.0087 (13) |
C14 | 0.0346 (15) | 0.0544 (18) | 0.0449 (15) | 0.0006 (13) | 0.0040 (12) | 0.0060 (13) |
C15 | 0.0266 (13) | 0.0485 (16) | 0.0428 (14) | −0.0004 (11) | 0.0099 (11) | −0.0020 (12) |
C16 | 0.0325 (14) | 0.0616 (19) | 0.0550 (17) | −0.0008 (13) | 0.0226 (13) | 0.0010 (14) |
C17 | 0.0392 (15) | 0.0566 (18) | 0.0528 (16) | 0.0026 (13) | 0.0213 (13) | 0.0106 (14) |
C18 | 0.0303 (14) | 0.0456 (15) | 0.0490 (15) | −0.0002 (12) | 0.0118 (11) | −0.0025 (12) |
C19 | 0.0274 (13) | 0.0550 (17) | 0.0561 (17) | −0.0013 (12) | 0.0201 (12) | −0.0013 (14) |
C20 | 0.0329 (14) | 0.0506 (17) | 0.0496 (16) | −0.0029 (12) | 0.0165 (12) | 0.0033 (13) |
C21 | 0.0327 (16) | 0.082 (2) | 0.081 (2) | −0.0140 (16) | 0.0043 (15) | 0.0105 (19) |
C22 | 0.0329 (15) | 0.066 (2) | 0.076 (2) | 0.0050 (14) | 0.0195 (14) | −0.0070 (17) |
N1 | 0.0272 (12) | 0.0445 (14) | 0.0599 (15) | −0.0008 (10) | 0.0106 (10) | −0.0070 (12) |
O1 | 0.0477 (14) | 0.0490 (15) | 0.141 (2) | −0.0038 (11) | 0.0357 (14) | −0.0003 (14) |
O2 | 0.0366 (11) | 0.0731 (16) | 0.0672 (14) | −0.0154 (10) | 0.0090 (10) | 0.0132 (11) |
O3 | 0.0362 (11) | 0.0648 (14) | 0.0737 (14) | 0.0122 (10) | 0.0231 (10) | 0.0125 (11) |
C2—N1 | 1.468 (3) | C11—H11 | 0.93 |
C2—C9 | 1.509 (4) | C12—C13 | 1.380 (4) |
C2—C3 | 1.554 (4) | C12—O2 | 1.382 (3) |
C2—H2 | 0.98 | C13—C14 | 1.379 (4) |
C3—C4 | 1.517 (4) | C13—H13 | 0.93 |
C3—C7 | 1.521 (4) | C14—H14 | 0.93 |
C3—H3 | 0.98 | C15—C20 | 1.384 (4) |
C4—O1 | 1.212 (4) | C15—C16 | 1.391 (4) |
C4—C5 | 1.502 (4) | C16—C17 | 1.379 (4) |
C5—C6 | 1.531 (4) | C16—H16 | 0.93 |
C5—H5A | 0.97 | C17—C18 | 1.385 (4) |
C5—H5B | 0.97 | C17—H17 | 0.93 |
C6—N1 | 1.464 (3) | C18—O3 | 1.368 (3) |
C6—C15 | 1.512 (4) | C18—C19 | 1.379 (4) |
C6—H6 | 0.98 | C19—C20 | 1.392 (4) |
C7—C8 | 1.511 (4) | C19—H19 | 0.93 |
C7—H7A | 0.97 | C20—H20 | 0.93 |
C7—H7B | 0.97 | C21—O2 | 1.413 (4) |
C8—H8A | 0.96 | C21—H21A | 0.96 |
C8—H8B | 0.96 | C21—H21B | 0.96 |
C8—H8C | 0.96 | C21—H21C | 0.96 |
C9—C10 | 1.382 (4) | C22—O3 | 1.418 (3) |
C9—C14 | 1.389 (4) | C22—H22A | 0.96 |
C10—C11 | 1.395 (4) | C22—H22B | 0.96 |
C10—H10 | 0.93 | C22—H22C | 0.96 |
C11—C12 | 1.372 (4) | N1—H1 | 0.90 (3) |
N1—C2—C9 | 110.8 (2) | C12—C11—H11 | 120.3 |
N1—C2—C3 | 108.6 (2) | C10—C11—H11 | 120.3 |
C9—C2—C3 | 112.2 (2) | C11—C12—C13 | 119.9 (3) |
N1—C2—H2 | 108.4 | C11—C12—O2 | 124.9 (2) |
C9—C2—H2 | 108.4 | C13—C12—O2 | 115.2 (2) |
C3—C2—H2 | 108.4 | C14—C13—C12 | 120.3 (3) |
C4—C3—C7 | 112.6 (2) | C14—C13—H13 | 119.9 |
C4—C3—C2 | 107.6 (2) | C12—C13—H13 | 119.9 |
C7—C3—C2 | 114.3 (2) | C13—C14—C9 | 121.0 (2) |
C4—C3—H3 | 107.3 | C13—C14—H14 | 119.5 |
C7—C3—H3 | 107.3 | C9—C14—H14 | 119.5 |
C2—C3—H3 | 107.3 | C20—C15—C16 | 117.7 (2) |
O1—C4—C5 | 121.7 (3) | C20—C15—C6 | 120.7 (2) |
O1—C4—C3 | 122.4 (3) | C16—C15—C6 | 121.5 (2) |
C5—C4—C3 | 115.8 (2) | C17—C16—C15 | 121.0 (3) |
C4—C5—C6 | 111.7 (2) | C17—C16—H16 | 119.5 |
C4—C5—H5A | 109.3 | C15—C16—H16 | 119.5 |
C6—C5—H5A | 109.3 | C16—C17—C18 | 120.5 (3) |
C4—C5—H5B | 109.3 | C16—C17—H17 | 119.7 |
C6—C5—H5B | 109.3 | C18—C17—H17 | 119.7 |
H5A—C5—H5B | 107.9 | O3—C18—C19 | 125.3 (2) |
N1—C6—C15 | 111.1 (2) | O3—C18—C17 | 115.1 (3) |
N1—C6—C5 | 107.5 (2) | C19—C18—C17 | 119.6 (3) |
C15—C6—C5 | 111.4 (2) | C18—C19—C20 | 119.3 (2) |
N1—C6—H6 | 108.9 | C18—C19—H19 | 120.3 |
C15—C6—H6 | 108.9 | C20—C19—H19 | 120.3 |
C5—C6—H6 | 108.9 | C15—C20—C19 | 121.9 (3) |
C8—C7—C3 | 115.3 (3) | C15—C20—H20 | 119.1 |
C8—C7—H7A | 108.5 | C19—C20—H20 | 119.1 |
C3—C7—H7A | 108.5 | O2—C21—H21A | 109.5 |
C8—C7—H7B | 108.5 | O2—C21—H21B | 109.5 |
C3—C7—H7B | 108.5 | H21A—C21—H21B | 109.5 |
H7A—C7—H7B | 107.5 | O2—C21—H21C | 109.5 |
C7—C8—H8A | 109.5 | H21A—C21—H21C | 109.5 |
C7—C8—H8B | 109.5 | H21B—C21—H21C | 109.5 |
H8A—C8—H8B | 109.5 | O3—C22—H22A | 109.5 |
C7—C8—H8C | 109.5 | O3—C22—H22B | 109.5 |
H8A—C8—H8C | 109.5 | H22A—C22—H22B | 109.5 |
H8B—C8—H8C | 109.5 | O3—C22—H22C | 109.5 |
C10—C9—C14 | 117.9 (2) | H22A—C22—H22C | 109.5 |
C10—C9—C2 | 120.6 (2) | H22B—C22—H22C | 109.5 |
C14—C9—C2 | 121.5 (2) | C6—N1—C2 | 112.8 (2) |
C9—C10—C11 | 121.4 (3) | C6—N1—H1 | 110 (2) |
C9—C10—H10 | 119.3 | C2—N1—H1 | 111 (2) |
C11—C10—H10 | 119.3 | C12—O2—C21 | 117.9 (2) |
C12—C11—C10 | 119.5 (2) | C18—O3—C22 | 117.9 (2) |
N1—C2—C3—C4 | −55.8 (3) | C12—C13—C14—C9 | −1.5 (5) |
C9—C2—C3—C4 | −178.6 (2) | C10—C9—C14—C13 | 1.7 (4) |
N1—C2—C3—C7 | 178.4 (2) | C2—C9—C14—C13 | −176.1 (3) |
C9—C2—C3—C7 | 55.5 (3) | N1—C6—C15—C20 | −146.8 (3) |
C7—C3—C4—O1 | −1.0 (4) | C5—C6—C15—C20 | 93.3 (3) |
C2—C3—C4—O1 | −127.8 (3) | N1—C6—C15—C16 | 35.8 (4) |
C7—C3—C4—C5 | 176.9 (3) | C5—C6—C15—C16 | −84.1 (3) |
C2—C3—C4—C5 | 50.1 (3) | C20—C15—C16—C17 | 0.1 (4) |
O1—C4—C5—C6 | 128.2 (3) | C6—C15—C16—C17 | 177.6 (3) |
C3—C4—C5—C6 | −49.7 (3) | C15—C16—C17—C18 | −0.2 (5) |
C4—C5—C6—N1 | 52.6 (3) | C16—C17—C18—O3 | 178.7 (3) |
C4—C5—C6—C15 | 174.6 (2) | C16—C17—C18—C19 | 0.1 (4) |
C4—C3—C7—C8 | 144.8 (3) | O3—C18—C19—C20 | −178.4 (3) |
C2—C3—C7—C8 | −92.0 (3) | C17—C18—C19—C20 | 0.2 (4) |
N1—C2—C9—C10 | 133.4 (3) | C16—C15—C20—C19 | 0.2 (4) |
C3—C2—C9—C10 | −105.0 (3) | C6—C15—C20—C19 | −177.3 (2) |
N1—C2—C9—C14 | −48.8 (4) | C18—C19—C20—C15 | −0.3 (4) |
C3—C2—C9—C14 | 72.8 (3) | C15—C6—N1—C2 | 174.2 (2) |
C14—C9—C10—C11 | −1.5 (4) | C5—C6—N1—C2 | −63.6 (3) |
C2—C9—C10—C11 | 176.3 (3) | C9—C2—N1—C6 | −169.6 (2) |
C9—C10—C11—C12 | 1.1 (4) | C3—C2—N1—C6 | 66.7 (3) |
C10—C11—C12—C13 | −0.9 (4) | C11—C12—O2—C21 | 5.9 (5) |
C10—C11—C12—O2 | 178.8 (3) | C13—C12—O2—C21 | −174.3 (3) |
C11—C12—C13—C14 | 1.1 (5) | C19—C18—O3—C22 | −3.6 (4) |
O2—C12—C13—C14 | −178.6 (3) | C17—C18—O3—C22 | 177.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Cg1 | 0.96 | 2.79 | 3.662 (4) | 152 |
C10—H10···Cg2i | 0.93 | 2.87 | 3.647 (3) | 142 |
C22—H22C···Cg2ii | 0.96 | 2.77 | 3.637 (4) | 151 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H25NO3 |
Mr | 339.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.012 (2), 7.8060 (14), 17.655 (3) |
β (°) | 110.401 (5) |
V (Å3) | 1810.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.15 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEX II area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15103, 3270, 2348 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.220, 1.10 |
No. of reflections | 3270 |
No. of parameters | 230 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.27 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Cg1 | 0.960 | 2.79 | 3.662 (4) | 152 |
C10—H10···Cg2i | 0.930 | 2.87 | 3.647 (3) | 142 |
C22—H22C···Cg2ii | 0.960 | 2.77 | 3.637 (4) | 151 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z. |
Nitrogen heterocycles, in particular piperidone alkaloids, occur in both plants and animals and some of them possess a variety of biological activities, including cytotoxic and anti-cancer properties (Dimmock et al., 1990; Mutus et al., 1989). In view of the above importance, the X-ray crystal structure determination of the title compound has been undertaken.
Bond lengths and angles (Fig. 1) are comparable to those observed for 3-methyl-2,6-diphenyl-4-piperidone (Sekar et al., 1990). The piperidine ring adopts a chair conformation, with a puckering amplitude QT of 0.577 (3) Å (Nardelli, 1995). The two benzene rings are in equatorial orientation with respect to the piperidine ring which is evidenced from the torsion angles C15—C6—C5—C4 of 174.7 (3)° and C4—C3—C2—C9 of -178.6 (2)°. The ethyl group substitued at C3 is also oriented equatorially with the N1—C2—C3—C7 torsion angle being 178.4 (2)°. The dihedral angle between the two benzene rings is 48.4 (1)°. The methoxy groups are almost coplanar with the attached benzene rings.
The molecular structure is stabilized by a C—H···π interaction involving the C9—C14 benzene ring (centroid Cg1). The crystal structure is stabilized by C—H···π interactions (Desiraju, 1989) involving the C15—C20 benzene ring (centroid Cg2). The packing of the molecules viewed down the a axis is shown in Fig.2. In addition to the above-mentioned interactions, the structure is also stabilized by van der Waals forces