Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040998/om2152sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040998/om2152Isup2.hkl |
CCDC reference: 660348
All chemicals purchased were of reagent grade and used without further purification. A mixture of (+)dehydroabietic acid (0.1 mol), phosphorus trichloride (6 ml) and chloroform (40 ml) were stirred at 333 K for 3 h, then the solvent was distilled off. The residue was slowly added to piperidine (0.2 mol) in toluene (60 ml) solution. After a further 24 h stirring at room temperature, the resulting mixture was filtered. The precipitate was washed with hydrochloric acid (5%) and water and the solvent was distilled off. Upon recrystallization from acetone, colorless crystals of the title compound were obtained (yield 54.7%, m.p. 342.5 K). Single crystals were grown from acetone.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.97–0.98 Å and Uiso(H) = 1.2Ueq(C) for all other H atoms. In the absence of significant anomalous scattering effects, all Friedel pairs were merged.
(+)Dehydroabietic acid is an abietane diterpenic resin acid which can be easily obtained from Pinus resin or commercial rosin (Halbrook & Lawrence, 1966). It is widely used as a starting material for the design and synthesis of biological compounds. Biological activities, such as anti-tumor (Wada et al., 1985), antimicrobial (Savluchinske et al., 1999), anti-inflammatory (Fernandez et al., 2001) and gastroprotective (Sepulveda et al., 2005) effects of dehydroabietic acid derivatives have been reported. Heterocyclic chemistry has attracted great interest in recent years, for those compounds containing heterocyclic rings often exhibit higher biological activities. Heterocyclic rings fused to the aromatic ring of dehydroabietic acid (Fonseca et al., 2004) have been successfully synthesized, and they exhibit antiviral activities against DNA and RNA. Considerable efforts have been devoted to the biological activities of heterocyclic derivatives of dehydroabietic acid, yet the crystal structure of such compounds have seldom been reported. In this work, we describe the crystal structure of the title compound. The overall geometry is comparable to that found for dehydroabietic N-methyl anilide (Rao et al., 2006). The tricyclic phenanthrene structure of the title compound exhibits the same conformation as dehydroabietic N-methyl anilide, which exhibited planar, classic chair and half-chair conformations, respectively. The two cyclohexane rings form a trans ring junction with two methyl groups on the same side of the tricyclic phenanthrene structure (Hamodrakas, et al., 1978). Apart from the planar conformation of the benzene ring, the piperidine ring of the title compound forms a classic chair conformation. The bond lengths and bond angles in the molecule are in normal ranges.
For related literature, see: Fernandez et al. (2001); Fonseca et al. (2004); Halbrook & Lawrence (1966); Hamodrakas et al. (1978); Rao et al. (2006); Savluchinske et al. (1999); Sepulveda et al. (2005); Wada et al. (1985).
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).
Fig. 1. The molecular structure of the title compound, with H atoms represented by small spheres of arbitrary radius and displacement ellipsoids at the 30% probability level. |
C25H37NO | Dx = 1.165 Mg m−3 |
Mr = 367.56 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 10.612 (2) Å | θ = 10–13° |
b = 11.566 (2) Å | µ = 0.07 mm−1 |
c = 17.067 (3) Å | T = 293 K |
V = 2094.8 (7) Å3 | Block, white |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
F(000) = 808 |
Enraf–Nonius CAD-4 diffractometer | 1756 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω/2θ scans | h = 0→13 |
Absorption correction: ψ scans (North et al., 1968) | k = 0→14 |
Tmin = 0.932, Tmax = 0.966 | l = −21→21 |
4522 measured reflections | 3 standard reflections every 200 reflections |
2339 independent reflections | intensity decay: none |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.08P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
2339 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C25H37NO | V = 2094.8 (7) Å3 |
Mr = 367.56 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.612 (2) Å | µ = 0.07 mm−1 |
b = 11.566 (2) Å | T = 293 K |
c = 17.067 (3) Å | 0.40 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1756 reflections with I > 2σ(I) |
Absorption correction: ψ scans (North et al., 1968) | Rint = 0.043 |
Tmin = 0.932, Tmax = 0.966 | 3 standard reflections every 200 reflections |
4522 measured reflections | intensity decay: none |
2339 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.17 e Å−3 |
2339 reflections | Δρmin = −0.19 e Å−3 |
245 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 | ||
O1 | 0.6299 (2) | 0.8464 (2) | 0.82631 (14) | 0.0531 (6) | |
N1 | 0.7308 (3) | 0.9998 (2) | 0.77919 (15) | 0.0441 (7) | |
C1 | 0.7437 (5) | 0.1750 (3) | 1.1017 (3) | 0.0815 (14) | |
H1A | 0.7027 | 0.1077 | 1.1227 | 0.122* | |
H1B | 0.8050 | 0.2027 | 1.1386 | 0.122* | |
H1C | 0.7848 | 0.1553 | 1.0535 | 0.122* | |
C2 | 0.5402 (4) | 0.2221 (4) | 1.0376 (3) | 0.0845 (14) | |
H2A | 0.5062 | 0.1541 | 1.0620 | 0.127* | |
H2B | 0.5712 | 0.2028 | 0.9864 | 0.127* | |
H2C | 0.4754 | 0.2796 | 1.0331 | 0.127* | |
C3 | 0.6465 (4) | 0.2686 (3) | 1.0868 (2) | 0.0586 (10) | |
H3 | 0.6106 | 0.2895 | 1.1377 | 0.070* | |
C4 | 0.7086 (3) | 0.3767 (3) | 1.0541 (2) | 0.0455 (8) | |
C5 | 0.7801 (4) | 0.4453 (3) | 1.1025 (2) | 0.0549 (9) | |
H5 | 0.7889 | 0.4248 | 1.1550 | 0.066* | |
C6 | 0.8393 (3) | 0.5436 (3) | 1.07563 (19) | 0.0484 (8) | |
H6 | 0.8881 | 0.5871 | 1.1101 | 0.058* | |
C7 | 0.8278 (3) | 0.5796 (3) | 0.99782 (17) | 0.0361 (7) | |
C8 | 0.8948 (3) | 0.6890 (2) | 0.96851 (17) | 0.0351 (7) | |
C9 | 0.9003 (3) | 0.7812 (3) | 1.03387 (18) | 0.0416 (8) | |
H9A | 0.8172 | 0.7902 | 1.0567 | 0.050* | |
H9B | 0.9570 | 0.7551 | 1.0748 | 0.050* | |
C10 | 0.9451 (3) | 0.8968 (3) | 1.00311 (19) | 0.0450 (8) | |
H10A | 1.0296 | 0.8886 | 0.9821 | 0.054* | |
H10B | 0.9483 | 0.9520 | 1.0459 | 0.054* | |
C11 | 0.8584 (3) | 0.9420 (3) | 0.93971 (18) | 0.0394 (7) | |
H11A | 0.8898 | 1.0162 | 0.9217 | 0.047* | |
H11B | 0.7754 | 0.9545 | 0.9620 | 0.047* | |
C12 | 0.8463 (3) | 0.8601 (2) | 0.86874 (16) | 0.0342 (7) | |
C13 | 0.8157 (3) | 0.7368 (2) | 0.89906 (15) | 0.0315 (6) | |
H13A | 0.7299 | 0.7428 | 0.9199 | 0.038* | |
C14 | 0.8065 (3) | 0.6461 (3) | 0.83505 (17) | 0.0399 (7) | |
H14A | 0.7647 | 0.6789 | 0.7897 | 0.048* | |
H14B | 0.8905 | 0.6225 | 0.8194 | 0.048* | |
C15 | 0.7339 (4) | 0.5422 (3) | 0.86324 (19) | 0.0516 (9) | |
H15A | 0.6446 | 0.5572 | 0.8566 | 0.062* | |
H15B | 0.7554 | 0.4766 | 0.8305 | 0.062* | |
C16 | 0.7576 (3) | 0.5105 (3) | 0.94744 (17) | 0.0360 (7) | |
C17 | 0.6993 (3) | 0.4097 (3) | 0.97657 (19) | 0.0422 (7) | |
H17A | 0.6530 | 0.3638 | 0.9423 | 0.051* | |
C18 | 1.0309 (3) | 0.6521 (3) | 0.9484 (2) | 0.0503 (9) | |
H18A | 1.0721 | 0.6245 | 0.9948 | 0.076* | |
H18B | 1.0764 | 0.7172 | 0.9279 | 0.076* | |
H18C | 1.0290 | 0.5916 | 0.9098 | 0.076* | |
C19 | 0.9654 (3) | 0.8588 (3) | 0.8168 (2) | 0.0470 (8) | |
H19A | 0.9961 | 0.7810 | 0.8121 | 0.071* | |
H19B | 1.0293 | 0.9065 | 0.8402 | 0.071* | |
H19C | 0.9450 | 0.8882 | 0.7657 | 0.071* | |
C20 | 0.7282 (3) | 0.9018 (3) | 0.82255 (18) | 0.0374 (7) | |
C21 | 0.8260 (3) | 1.0905 (3) | 0.7773 (2) | 0.0471 (8) | |
H21A | 0.8521 | 1.1040 | 0.7236 | 0.057* | |
H21B | 0.8994 | 1.0659 | 0.8069 | 0.057* | |
C22 | 0.7745 (3) | 1.2020 (3) | 0.8121 (2) | 0.0547 (9) | |
H22A | 0.7576 | 1.1907 | 0.8674 | 0.066* | |
H22B | 0.8372 | 1.2626 | 0.8071 | 0.066* | |
C23 | 0.6547 (4) | 1.2390 (3) | 0.7712 (2) | 0.0635 (11) | |
H23A | 0.6193 | 1.3057 | 0.7978 | 0.076* | |
H23B | 0.6737 | 1.2612 | 0.7177 | 0.076* | |
C24 | 0.5606 (3) | 1.1423 (3) | 0.7712 (2) | 0.0590 (10) | |
H24A | 0.4873 | 1.1648 | 0.7409 | 0.071* | |
H24B | 0.5335 | 1.1269 | 0.8244 | 0.071* | |
C25 | 0.6176 (4) | 1.0337 (3) | 0.7364 (2) | 0.0557 (10) | |
H25A | 0.5564 | 0.9715 | 0.7384 | 0.067* | |
H25B | 0.6387 | 1.0474 | 0.6818 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0383 (12) | 0.0497 (13) | 0.0714 (15) | −0.0063 (11) | −0.0142 (11) | 0.0160 (13) |
N1 | 0.0447 (15) | 0.0370 (13) | 0.0505 (15) | −0.0036 (13) | −0.0108 (13) | 0.0038 (13) |
C1 | 0.088 (3) | 0.050 (2) | 0.106 (3) | −0.001 (2) | −0.003 (3) | 0.029 (2) |
C2 | 0.067 (3) | 0.065 (3) | 0.121 (4) | −0.021 (2) | −0.008 (3) | 0.026 (3) |
C3 | 0.066 (2) | 0.0497 (19) | 0.060 (2) | −0.006 (2) | 0.009 (2) | 0.0077 (18) |
C4 | 0.0407 (17) | 0.0417 (17) | 0.0540 (18) | 0.0018 (16) | 0.0019 (16) | 0.0101 (16) |
C5 | 0.064 (2) | 0.058 (2) | 0.0425 (18) | −0.003 (2) | −0.0047 (18) | 0.0130 (17) |
C6 | 0.050 (2) | 0.0485 (18) | 0.0466 (18) | −0.0065 (17) | −0.0117 (16) | 0.0032 (15) |
C7 | 0.0294 (14) | 0.0360 (16) | 0.0431 (16) | 0.0071 (13) | −0.0007 (13) | 0.0017 (14) |
C8 | 0.0269 (14) | 0.0385 (16) | 0.0398 (16) | 0.0006 (13) | 0.0003 (13) | 0.0000 (14) |
C9 | 0.0381 (16) | 0.0468 (18) | 0.0397 (16) | −0.0040 (15) | −0.0073 (14) | −0.0008 (15) |
C10 | 0.0404 (17) | 0.0468 (19) | 0.0477 (19) | −0.0090 (16) | −0.0051 (14) | −0.0069 (16) |
C11 | 0.0351 (15) | 0.0358 (16) | 0.0473 (17) | −0.0049 (14) | 0.0016 (14) | 0.0003 (14) |
C12 | 0.0309 (15) | 0.0362 (15) | 0.0355 (15) | 0.0002 (14) | 0.0016 (12) | 0.0005 (13) |
C13 | 0.0268 (13) | 0.0336 (14) | 0.0340 (14) | −0.0010 (13) | 0.0000 (12) | −0.0028 (12) |
C14 | 0.0442 (17) | 0.0371 (16) | 0.0383 (15) | 0.0017 (15) | 0.0046 (14) | 0.0002 (13) |
C15 | 0.070 (2) | 0.0382 (17) | 0.0464 (17) | −0.0110 (18) | −0.0088 (17) | −0.0014 (15) |
C16 | 0.0329 (14) | 0.0341 (15) | 0.0409 (15) | 0.0065 (13) | 0.0006 (13) | 0.0006 (13) |
C17 | 0.0388 (17) | 0.0361 (16) | 0.0517 (18) | 0.0029 (15) | −0.0046 (15) | 0.0004 (14) |
C18 | 0.0271 (15) | 0.057 (2) | 0.067 (2) | 0.0074 (16) | −0.0019 (15) | 0.0048 (19) |
C19 | 0.0370 (16) | 0.0455 (18) | 0.058 (2) | 0.0024 (16) | 0.0118 (15) | 0.0059 (17) |
C20 | 0.0398 (16) | 0.0333 (15) | 0.0392 (16) | −0.0008 (14) | −0.0012 (13) | −0.0039 (13) |
C21 | 0.0485 (19) | 0.0438 (18) | 0.0490 (18) | −0.0056 (16) | 0.0081 (16) | 0.0087 (15) |
C22 | 0.057 (2) | 0.0395 (18) | 0.067 (2) | −0.0076 (18) | −0.0050 (19) | −0.0012 (17) |
C23 | 0.078 (3) | 0.0381 (19) | 0.074 (2) | 0.007 (2) | −0.021 (2) | −0.0046 (18) |
C24 | 0.051 (2) | 0.057 (2) | 0.069 (2) | 0.009 (2) | −0.0193 (19) | 0.002 (2) |
C25 | 0.063 (2) | 0.0461 (19) | 0.058 (2) | −0.0042 (18) | −0.0235 (19) | 0.0049 (18) |
O1—C20 | 1.226 (4) | C12—C19 | 1.544 (4) |
N1—C20 | 1.354 (4) | C12—C13 | 1.552 (4) |
N1—C21 | 1.457 (4) | C12—C20 | 1.557 (4) |
N1—C25 | 1.461 (4) | C13—C14 | 1.517 (4) |
C1—C3 | 1.517 (6) | C13—H13A | 0.9800 |
C1—H1A | 0.9600 | C14—C15 | 1.507 (4) |
C1—H1B | 0.9600 | C14—H14A | 0.9700 |
C1—H1C | 0.9600 | C14—H14B | 0.9700 |
C2—C3 | 1.505 (6) | C15—C16 | 1.504 (4) |
C2—H2A | 0.9600 | C15—H15A | 0.9700 |
C2—H2B | 0.9600 | C15—H15B | 0.9700 |
C2—H2C | 0.9600 | C16—C17 | 1.410 (4) |
C3—C4 | 1.518 (5) | C17—H17A | 0.9300 |
C3—H3 | 0.9800 | C18—H18A | 0.9600 |
C4—C5 | 1.375 (5) | C18—H18B | 0.9600 |
C4—C17 | 1.382 (4) | C18—H18C | 0.9600 |
C5—C6 | 1.378 (5) | C19—H19A | 0.9600 |
C5—H5 | 0.9300 | C19—H19B | 0.9600 |
C6—C7 | 1.397 (4) | C19—H19C | 0.9600 |
C6—H6 | 0.9300 | C21—C22 | 1.521 (5) |
C7—C16 | 1.391 (4) | C21—H21A | 0.9700 |
C7—C8 | 1.535 (4) | C21—H21B | 0.9700 |
C8—C9 | 1.544 (4) | C22—C23 | 1.511 (5) |
C8—C18 | 1.546 (4) | C22—H22A | 0.9700 |
C8—C13 | 1.554 (4) | C22—H22B | 0.9700 |
C9—C10 | 1.514 (4) | C23—C24 | 1.500 (5) |
C9—H9A | 0.9700 | C23—H23A | 0.9700 |
C9—H9B | 0.9700 | C23—H23B | 0.9700 |
C10—C11 | 1.514 (4) | C24—C25 | 1.514 (5) |
C10—H10A | 0.9700 | C24—H24A | 0.9700 |
C10—H10B | 0.9700 | C24—H24B | 0.9700 |
C11—C12 | 1.543 (4) | C25—H25A | 0.9700 |
C11—H11A | 0.9700 | C25—H25B | 0.9700 |
C11—H11B | 0.9700 | ||
C20—N1—C21 | 129.0 (3) | C14—C13—H13A | 104.5 |
C20—N1—C25 | 118.8 (3) | C12—C13—H13A | 104.5 |
C21—N1—C25 | 111.5 (3) | C8—C13—H13A | 104.5 |
C3—C1—H1A | 109.5 | C15—C14—C13 | 110.7 (2) |
C3—C1—H1B | 109.5 | C15—C14—H14A | 109.5 |
H1A—C1—H1B | 109.5 | C13—C14—H14A | 109.5 |
C3—C1—H1C | 109.5 | C15—C14—H14B | 109.5 |
H1A—C1—H1C | 109.5 | C13—C14—H14B | 109.5 |
H1B—C1—H1C | 109.5 | H14A—C14—H14B | 108.1 |
C3—C2—H2A | 109.5 | C16—C15—C14 | 114.4 (3) |
C3—C2—H2B | 109.5 | C16—C15—H15A | 108.6 |
H2A—C2—H2B | 109.5 | C14—C15—H15A | 108.6 |
C3—C2—H2C | 109.5 | C16—C15—H15B | 108.6 |
H2A—C2—H2C | 109.5 | C14—C15—H15B | 108.6 |
H2B—C2—H2C | 109.5 | H15A—C15—H15B | 107.6 |
C2—C3—C1 | 110.4 (3) | C7—C16—C17 | 119.5 (3) |
C2—C3—C4 | 114.5 (3) | C7—C16—C15 | 122.7 (3) |
C1—C3—C4 | 110.8 (3) | C17—C16—C15 | 117.7 (3) |
C2—C3—H3 | 106.9 | C4—C17—C16 | 122.4 (3) |
C1—C3—H3 | 106.9 | C4—C17—H17A | 118.8 |
C4—C3—H3 | 106.9 | C16—C17—H17A | 118.8 |
C5—C4—C17 | 117.1 (3) | C8—C18—H18A | 109.5 |
C5—C4—C3 | 119.7 (3) | C8—C18—H18B | 109.5 |
C17—C4—C3 | 123.2 (3) | H18A—C18—H18B | 109.5 |
C4—C5—C6 | 121.9 (3) | C8—C18—H18C | 109.5 |
C4—C5—H5 | 119.1 | H18A—C18—H18C | 109.5 |
C6—C5—H5 | 119.1 | H18B—C18—H18C | 109.5 |
C5—C6—C7 | 121.5 (3) | C12—C19—H19A | 109.5 |
C5—C6—H6 | 119.2 | C12—C19—H19B | 109.5 |
C7—C6—H6 | 119.2 | H19A—C19—H19B | 109.5 |
C16—C7—C6 | 117.6 (3) | C12—C19—H19C | 109.5 |
C16—C7—C8 | 121.4 (3) | H19A—C19—H19C | 109.5 |
C6—C7—C8 | 121.0 (3) | H19B—C19—H19C | 109.5 |
C7—C8—C9 | 110.6 (2) | O1—C20—N1 | 118.9 (3) |
C7—C8—C18 | 106.1 (2) | O1—C20—C12 | 119.8 (3) |
C9—C8—C18 | 108.4 (3) | N1—C20—C12 | 121.3 (3) |
C7—C8—C13 | 106.9 (2) | N1—C21—C22 | 110.7 (3) |
C9—C8—C13 | 109.1 (2) | N1—C21—H21A | 109.5 |
C18—C8—C13 | 115.7 (3) | C22—C21—H21A | 109.5 |
C10—C9—C8 | 111.8 (2) | N1—C21—H21B | 109.5 |
C10—C9—H9A | 109.3 | C22—C21—H21B | 109.5 |
C8—C9—H9A | 109.3 | H21A—C21—H21B | 108.1 |
C10—C9—H9B | 109.3 | C23—C22—C21 | 111.3 (3) |
C8—C9—H9B | 109.3 | C23—C22—H22A | 109.4 |
H9A—C9—H9B | 107.9 | C21—C22—H22A | 109.4 |
C9—C10—C11 | 111.3 (3) | C23—C22—H22B | 109.4 |
C9—C10—H10A | 109.4 | C21—C22—H22B | 109.4 |
C11—C10—H10A | 109.4 | H22A—C22—H22B | 108.0 |
C9—C10—H10B | 109.4 | C24—C23—C22 | 110.4 (3) |
C11—C10—H10B | 109.4 | C24—C23—H23A | 109.6 |
H10A—C10—H10B | 108.0 | C22—C23—H23A | 109.6 |
C10—C11—C12 | 113.5 (3) | C24—C23—H23B | 109.6 |
C10—C11—H11A | 108.9 | C22—C23—H23B | 109.6 |
C12—C11—H11A | 108.9 | H23A—C23—H23B | 108.1 |
C10—C11—H11B | 108.9 | C23—C24—C25 | 110.7 (3) |
C12—C11—H11B | 108.9 | C23—C24—H24A | 109.5 |
H11A—C11—H11B | 107.7 | C25—C24—H24A | 109.5 |
C11—C12—C19 | 112.9 (3) | C23—C24—H24B | 109.5 |
C11—C12—C13 | 108.7 (2) | C25—C24—H24B | 109.5 |
C19—C12—C13 | 110.8 (2) | H24A—C24—H24B | 108.1 |
C11—C12—C20 | 105.9 (2) | N1—C25—C24 | 110.8 (3) |
C19—C12—C20 | 111.8 (2) | N1—C25—H25A | 109.5 |
C13—C12—C20 | 106.6 (2) | C24—C25—H25A | 109.5 |
C14—C13—C12 | 114.1 (2) | N1—C25—H25B | 109.5 |
C14—C13—C8 | 109.8 (2) | C24—C25—H25B | 109.5 |
C12—C13—C8 | 117.9 (2) | H25A—C25—H25B | 108.1 |
C2—C3—C4—C5 | 161.6 (4) | C9—C8—C13—C12 | 48.4 (3) |
C1—C3—C4—C5 | −72.8 (4) | C18—C8—C13—C12 | −74.0 (3) |
C2—C3—C4—C17 | −19.8 (5) | C12—C13—C14—C15 | −160.0 (3) |
C1—C3—C4—C17 | 105.8 (4) | C8—C13—C14—C15 | 65.1 (3) |
C17—C4—C5—C6 | 0.7 (5) | C13—C14—C15—C16 | −37.4 (4) |
C3—C4—C5—C6 | 179.4 (3) | C6—C7—C16—C17 | 1.4 (4) |
C4—C5—C6—C7 | 1.1 (5) | C8—C7—C16—C17 | 179.0 (2) |
C5—C6—C7—C16 | −2.1 (5) | C6—C7—C16—C15 | 177.4 (3) |
C5—C6—C7—C8 | −179.7 (3) | C8—C7—C16—C15 | −4.9 (5) |
C16—C7—C8—C9 | 148.5 (3) | C14—C15—C16—C7 | 7.9 (5) |
C6—C7—C8—C9 | −34.0 (4) | C14—C15—C16—C17 | −176.0 (3) |
C16—C7—C8—C18 | −94.2 (3) | C5—C4—C17—C16 | −1.4 (5) |
C6—C7—C8—C18 | 83.4 (3) | C3—C4—C17—C16 | 180.0 (3) |
C16—C7—C8—C13 | 29.9 (4) | C7—C16—C17—C4 | 0.3 (5) |
C6—C7—C8—C13 | −152.6 (3) | C15—C16—C17—C4 | −175.9 (3) |
C7—C8—C9—C10 | −170.1 (2) | C21—N1—C20—O1 | 167.1 (3) |
C18—C8—C9—C10 | 73.9 (3) | C25—N1—C20—O1 | −2.1 (4) |
C13—C8—C9—C10 | −52.8 (3) | C21—N1—C20—C12 | −11.6 (5) |
C8—C9—C10—C11 | 59.8 (3) | C25—N1—C20—C12 | 179.3 (3) |
C9—C10—C11—C12 | −58.9 (3) | C11—C12—C20—O1 | −104.9 (3) |
C10—C11—C12—C19 | −73.1 (3) | C19—C12—C20—O1 | 131.8 (3) |
C10—C11—C12—C13 | 50.1 (3) | C13—C12—C20—O1 | 10.7 (4) |
C10—C11—C12—C20 | 164.3 (2) | C11—C12—C20—N1 | 73.8 (3) |
C11—C12—C13—C14 | −177.6 (2) | C19—C12—C20—N1 | −49.5 (4) |
C19—C12—C13—C14 | −53.1 (3) | C13—C12—C20—N1 | −170.6 (2) |
C20—C12—C13—C14 | 68.7 (3) | C20—N1—C21—C22 | −111.6 (4) |
C11—C12—C13—C8 | −46.6 (3) | C25—N1—C21—C22 | 58.3 (4) |
C19—C12—C13—C8 | 77.9 (3) | N1—C21—C22—C23 | −55.3 (4) |
C20—C12—C13—C8 | −160.3 (2) | C21—C22—C23—C24 | 53.5 (4) |
C7—C8—C13—C14 | −59.0 (3) | C22—C23—C24—C25 | −54.2 (4) |
C9—C8—C13—C14 | −178.6 (2) | C20—N1—C25—C24 | 111.5 (3) |
C18—C8—C13—C14 | 58.9 (3) | C21—N1—C25—C24 | −59.5 (4) |
C7—C8—C13—C12 | 168.0 (2) | C23—C24—C25—N1 | 57.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C25H37NO |
Mr | 367.56 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 10.612 (2), 11.566 (2), 17.067 (3) |
V (Å3) | 2094.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scans (North et al., 1968) |
Tmin, Tmax | 0.932, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4522, 2339, 1756 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.134, 1.00 |
No. of reflections | 2339 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), CAD-4 Software (Enraf–Nonius, 1985, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
O1—C20 | 1.226 (4) | N1—C25 | 1.461 (4) |
N1—C20 | 1.354 (4) | C4—C5 | 1.375 (5) |
N1—C21 | 1.457 (4) | C11—C12 | 1.543 (4) |
C20—N1—C21 | 129.0 (3) | C5—C4—C3 | 119.7 (3) |
C21—N1—C25 | 111.5 (3) | C6—C7—C8 | 121.0 (3) |
C8—C7—C16—C17 | 179.0 (2) | N1—C21—C22—C23 | −55.3 (4) |
(+)Dehydroabietic acid is an abietane diterpenic resin acid which can be easily obtained from Pinus resin or commercial rosin (Halbrook & Lawrence, 1966). It is widely used as a starting material for the design and synthesis of biological compounds. Biological activities, such as anti-tumor (Wada et al., 1985), antimicrobial (Savluchinske et al., 1999), anti-inflammatory (Fernandez et al., 2001) and gastroprotective (Sepulveda et al., 2005) effects of dehydroabietic acid derivatives have been reported. Heterocyclic chemistry has attracted great interest in recent years, for those compounds containing heterocyclic rings often exhibit higher biological activities. Heterocyclic rings fused to the aromatic ring of dehydroabietic acid (Fonseca et al., 2004) have been successfully synthesized, and they exhibit antiviral activities against DNA and RNA. Considerable efforts have been devoted to the biological activities of heterocyclic derivatives of dehydroabietic acid, yet the crystal structure of such compounds have seldom been reported. In this work, we describe the crystal structure of the title compound. The overall geometry is comparable to that found for dehydroabietic N-methyl anilide (Rao et al., 2006). The tricyclic phenanthrene structure of the title compound exhibits the same conformation as dehydroabietic N-methyl anilide, which exhibited planar, classic chair and half-chair conformations, respectively. The two cyclohexane rings form a trans ring junction with two methyl groups on the same side of the tricyclic phenanthrene structure (Hamodrakas, et al., 1978). Apart from the planar conformation of the benzene ring, the piperidine ring of the title compound forms a classic chair conformation. The bond lengths and bond angles in the molecule are in normal ranges.