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Acta Cryst. (2009). E65, o786    [ doi:10.1107/S1600536809009040 ]

N-(2-Pyridylmethyleneamino)dehydroabietylamine

Y. Wu, X.-P. Rao, Z.-D. Wang, Z.-Q. Song and X.-J. Yao

Abstract top

The title compound {systematic name: 1-[(1R,4aS,10aR)-7-isopropyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]-N-[(E)-2-pyridylmethyleneamino]methanamine}, C26H33N2, has been synthesized from dehydroabietylamine. The two cyclohexane rings form a trans ring junction with classic chair and half-chair conformations, respectively, whereas the benzene and pyridine rings are almost planar, and the dihedral angle between them is 80.4°. The two methyl groups directly attached to the tricyclic nucleus are on the same side of the tricyclic hydrophenanthrene structure.

Comment top

Dehydroabietylamine is a highly interesting compound for its special structure and wide range of applications (Rao, Song, He & Jia, 2008). As an excellent chiral resolving agent, dehydroabietylamine is successful applied in the coalescent of Penicillin (Cannon,1952) and the synthesis of dihydroxyphenylalanine (Kalser et al., 1976). Dehydroabietylamine derivatives exhibited broad spectrum of biological properties including antibacterial, antifungal, and antipenetrant activities (Heinrich, 1981; Wilkerson et al., 1991; Wilkerson et al., 1993; Rao et al., 2007; Rao, Song, & He, 2008; Rao, Song, Jia & Shang, 2008)). Although much attention has been paid to dehydroabietylamine derivatives, the crystal structure of the title compound has not yet been reported. In this paper, we present the crystal structure of the title compound.

The title structure is compared with previously found structure 4-chloro-2-{(E)-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2, 3,4,4a,9,10,10a-octahydrophenanthren-1-yl] methyliminomethyl} phenol (Rao et al., 2006). They exhibited the same configurations with each other. As shown in Fig.1, the title compound contains four crystrallographically rings, the two cyclohexane rings (rings C and B) form a trans ring junction with classic chair and half-chair conformations, respectively. The benzene ring and the pyridine ring (rings A and D) are almost planar. The two methyl groups directly attached to the tricyclic nucleus are on the same side of the tricyclic hydrophenanthrene structure, and the two methyl groups are in the axis position of the cyclohexane ring, the bond lengths and bond angles in the molecule are in normal ranges.

Related literature top

For related literature, see: Cannon (1952); Heinrich (1981); Kalser & Scheer (1976); Rao et al. (2006, 2007); Rao, Song & He (2008); Rao, Song, He & Jia (2008); Rao, Song, Jia & Shang (2008); Wilkerson et al. (1991, 1993).

Experimental top

The title compound was prepared by the reaction of dehydroabietylamine (0.1 mol) and pyridylaldehyde (0.1 mol) in ethanol (100 ml) under 353.5 K for 4 h. Single crystals of the title compound were obtained by solvent evaporation [m.p. 372K].

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.97–0.98Å and Uiso(H) = 1.2Ueq(C) for all other H atoms. The high Flack value was resulted by the crystal quality.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
1-[(1R,4aS,10aR)-7-isopropyl-1,2,3,4,4a,9,10,10a- octahydrophenanthren-1-yl]-N-[(E)-2- pyridylmethyleneamino]methanamine top
Crystal data top
C26H33N2F(000) = 406
Mr = 373.54Dx = 1.132 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 11.294 (2) Åθ = 10–13°
b = 6.0870 (12) ŵ = 0.07 mm−1
c = 16.129 (3) ÅT = 293 K
β = 98.71 (3)°Block, white
V = 1096.0 (4) Å30.30 × 0.20 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer		1434 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 26.0°, θmin = 1.3°
ω/2θ scansh = 0→13
Absorption correction: ψ scan
(North et al., 1968)		k = 0→7
Tmin = 0.951, Tmax = 0.974l = −19→19
2478 measured reflections3 standard reflections every 200 reflections
2357 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2357 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.19 e Å−3
1 restraintΔρmin = −0.20 e Å−3
Crystal data top
C26H33N2V = 1096.0 (4) Å3
Mr = 373.54Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.294 (2) ŵ = 0.07 mm−1
b = 6.0870 (12) ÅT = 293 K
c = 16.129 (3) Å0.30 × 0.20 × 0.10 mm
β = 98.71 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1434 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.045
Tmin = 0.951, Tmax = 0.974θmax = 26.0°
2478 measured reflections3 standard reflections every 200 reflections
2357 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.19 e Å−3
S = 1.00Δρmin = −0.20 e Å−3
2357 reflectionsAbsolute structure: ?
253 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2116 (4)0.1781 (8)−0.1368 (2)0.0616 (12)
N20.0270 (5)0.4047 (9)−0.3125 (3)0.0814 (15)
C10.6341 (7)0.9761 (12)0.3876 (4)0.108 (3)
H1B0.56471.05190.35980.162*
H1C0.68610.94070.34770.162*
H1D0.67581.06840.43070.162*
C20.7016 (5)0.6441 (12)0.4723 (4)0.088 (2)
H2B0.67500.51390.49750.132*
H2C0.74360.73690.51510.132*
H2D0.75430.60410.43330.132*
C30.5953 (5)0.7653 (10)0.4268 (3)0.0653 (15)
H3A0.54690.80990.46950.078*
C40.5153 (5)0.6250 (9)0.3642 (3)0.0560 (14)
C50.3996 (4)0.5769 (10)0.3732 (3)0.0602 (15)
H5A0.36900.63030.41970.072*
C60.3280 (4)0.4524 (9)0.3157 (3)0.0541 (13)
H6A0.24950.42610.32390.065*
C70.3671 (4)0.3638 (8)0.2458 (3)0.0455 (11)
C80.4870 (4)0.4045 (9)0.2362 (3)0.0519 (12)
C90.5572 (4)0.5346 (10)0.2954 (3)0.0604 (14)
H9A0.63600.56230.28830.072*
C100.2857 (4)0.2215 (8)0.1825 (3)0.0444 (11)
C110.3278 (4)0.2466 (8)0.0964 (2)0.0433 (10)
H11A0.32900.40540.08650.052*
C120.4589 (4)0.1745 (10)0.1029 (3)0.0636 (15)
H12A0.46580.02180.12000.076*
H12B0.48400.18630.04820.076*
C130.5392 (5)0.3102 (14)0.1640 (3)0.092 (2)
H13A0.61850.33560.15760.110*
C140.1547 (4)0.2973 (9)0.1759 (3)0.0534 (13)
H14A0.12600.26720.22840.064*
H14B0.15070.45470.16660.064*
C150.0736 (4)0.1820 (11)0.1046 (3)0.0639 (15)
H15A0.07390.02510.11520.077*
H15B−0.00780.23490.10220.077*
C160.1160 (4)0.2251 (9)0.0222 (3)0.0538 (13)
H16A0.10990.38140.01060.065*
H16B0.06290.1501−0.02170.065*
C170.2442 (4)0.1517 (8)0.0188 (3)0.0482 (12)
C180.2950 (5)−0.0156 (9)0.2187 (3)0.0686 (16)
H18A0.2672−0.01710.27210.103*
H18B0.3769−0.06330.22560.103*
H18C0.2466−0.11280.18080.103*
C190.2519 (5)−0.1014 (9)0.0118 (3)0.0617 (15)
H19A0.2274−0.16780.06040.093*
H19B0.3329−0.14320.00820.093*
H19C0.2002−0.1500−0.03760.093*
C200.2829 (4)0.2563 (10)−0.0602 (3)0.0568 (13)
H20A0.27530.4147−0.05710.068*
H20B0.36650.2223−0.06150.068*
C210.1584 (5)0.3134 (10)−0.1878 (3)0.0612 (14)
H21A0.16540.4626−0.17560.073*
C220.0852 (4)0.2423 (10)−0.2665 (3)0.0559 (13)
C23−0.0394 (6)0.3452 (14)−0.3848 (4)0.094 (2)
H23A−0.08070.4544−0.41760.113*
C24−0.0503 (6)0.1341 (14)−0.4132 (4)0.085 (2)
H24A−0.09810.1010−0.46380.102*
C250.0104 (6)−0.0273 (12)−0.3659 (4)0.0780 (18)
H25A0.0054−0.1723−0.38430.094*
C260.0784 (5)0.0259 (11)−0.2916 (3)0.0672 (15)
H26A0.1196−0.0824−0.25820.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.074 (3)0.052 (3)0.055 (2)−0.001 (2)0.000 (2)−0.007 (2)
N20.091 (4)0.069 (4)0.079 (3)0.008 (3)−0.008 (3)0.003 (3)
C10.152 (7)0.067 (5)0.095 (5)−0.038 (5)−0.014 (4)−0.001 (4)
C20.084 (4)0.077 (5)0.092 (4)−0.001 (4)−0.027 (3)−0.013 (4)
C30.073 (4)0.058 (4)0.062 (3)−0.005 (3)0.003 (3)−0.007 (3)
C40.067 (3)0.047 (3)0.049 (3)0.006 (3)−0.006 (2)−0.003 (2)
C50.066 (3)0.063 (4)0.051 (3)0.004 (3)0.008 (3)−0.001 (3)
C60.056 (3)0.052 (3)0.054 (3)−0.001 (3)0.005 (2)0.007 (3)
C70.055 (3)0.037 (3)0.043 (2)0.002 (2)0.004 (2)0.009 (2)
C80.050 (3)0.053 (3)0.051 (3)−0.002 (3)0.001 (2)−0.005 (3)
C90.049 (3)0.066 (4)0.064 (3)−0.012 (3)0.002 (2)0.005 (3)
C100.044 (2)0.033 (3)0.054 (2)−0.001 (2)0.003 (2)0.009 (2)
C110.046 (2)0.033 (2)0.050 (2)−0.001 (2)0.0013 (19)0.001 (2)
C120.049 (3)0.075 (4)0.066 (3)−0.001 (3)0.006 (2)−0.016 (3)
C130.049 (3)0.146 (7)0.083 (4)−0.026 (4)0.020 (3)−0.055 (5)
C140.050 (3)0.052 (3)0.060 (3)0.000 (2)0.013 (2)0.004 (3)
C150.043 (2)0.078 (4)0.069 (3)−0.001 (3)0.000 (2)0.001 (3)
C160.049 (3)0.047 (3)0.061 (3)0.000 (3)−0.005 (2)0.005 (3)
C170.055 (3)0.030 (2)0.059 (3)−0.002 (2)0.005 (2)−0.001 (2)
C180.087 (4)0.046 (3)0.068 (3)−0.012 (3)−0.002 (3)0.019 (3)
C190.067 (3)0.041 (3)0.073 (3)−0.003 (3)−0.002 (3)−0.004 (3)
C200.067 (3)0.050 (3)0.053 (3)−0.008 (3)0.005 (2)−0.002 (3)
C210.068 (3)0.054 (3)0.061 (3)−0.001 (3)0.008 (3)−0.006 (3)
C220.061 (3)0.053 (3)0.053 (3)0.002 (3)0.007 (2)0.006 (3)
C230.089 (5)0.088 (6)0.094 (5)0.014 (4)−0.021 (4)0.016 (5)
C240.087 (4)0.098 (6)0.065 (4)−0.029 (4)−0.001 (3)0.001 (4)
C250.102 (5)0.063 (4)0.067 (4)−0.014 (4)0.008 (3)−0.005 (4)
C260.076 (4)0.060 (4)0.064 (3)−0.005 (3)0.007 (3)0.003 (3)
Geometric parameters (Å, °) top
N1—C211.251 (6)C12—H12A0.9700
N1—C201.449 (6)C12—H12B0.9700
N2—C231.337 (8)C13—H13A0.9300
N2—C221.345 (7)C14—C151.528 (7)
C1—C31.523 (9)C14—H14A0.9700
C1—H1B0.9600C14—H14B0.9700
C1—H1C0.9600C15—C161.501 (6)
C1—H1D0.9600C15—H15A0.9700
C2—C31.502 (8)C15—H15B0.9700
C2—H2B0.9600C16—C171.524 (6)
C2—H2C0.9600C16—H16A0.9700
C2—H2D0.9600C16—H16B0.9700
C3—C41.513 (7)C17—C201.545 (7)
C3—H3A0.9800C17—C191.548 (7)
C4—C51.368 (7)C18—H18A0.9600
C4—C91.386 (7)C18—H18B0.9600
C5—C61.364 (7)C18—H18C0.9600
C5—H5A0.9300C19—H19A0.9600
C6—C71.381 (6)C19—H19B0.9600
C6—H6A0.9300C19—H19C0.9600
C7—C81.407 (6)C20—H20A0.9700
C7—C101.534 (6)C20—H20B0.9700
C8—C91.392 (7)C21—C221.473 (7)
C8—C131.498 (7)C21—H21A0.9300
C9—H9A0.9300C22—C261.376 (8)
C10—C141.537 (6)C23—C241.363 (10)
C10—C111.543 (6)C23—H23A0.9300
C10—C181.555 (7)C24—C251.363 (9)
C11—C121.532 (6)C24—H24A0.9300
C11—C171.560 (6)C25—C261.361 (8)
C11—H11A0.9800C25—H25A0.9300
C12—C131.485 (7)C26—H26A0.9300
C21—N1—C20119.6 (5)C15—C14—H14A109.2
C23—N2—C22116.4 (6)C10—C14—H14A109.2
C3—C1—H1B109.5C15—C14—H14B109.2
C3—C1—H1C109.5C10—C14—H14B109.2
H1B—C1—H1C109.5H14A—C14—H14B107.9
C3—C1—H1D109.5C16—C15—C14110.5 (4)
H1B—C1—H1D109.5C16—C15—H15A109.5
H1C—C1—H1D109.5C14—C15—H15A109.5
C3—C2—H2B109.5C16—C15—H15B109.5
C3—C2—H2C109.5C14—C15—H15B109.5
H2B—C2—H2C109.5H15A—C15—H15B108.1
C3—C2—H2D109.5C15—C16—C17114.4 (4)
H2B—C2—H2D109.5C15—C16—H16A108.7
H2C—C2—H2D109.5C17—C16—H16A108.7
C2—C3—C4113.7 (5)C15—C16—H16B108.7
C2—C3—C1110.9 (6)C17—C16—H16B108.7
C4—C3—C1112.2 (4)H16A—C16—H16B107.6
C2—C3—H3A106.5C16—C17—C20107.4 (4)
C4—C3—H3A106.5C16—C17—C19111.0 (4)
C1—C3—H3A106.5C20—C17—C19108.9 (4)
C5—C4—C9116.6 (5)C16—C17—C11108.9 (4)
C5—C4—C3122.3 (5)C20—C17—C11107.2 (4)
C9—C4—C3121.1 (5)C19—C17—C11113.1 (4)
C6—C5—C4121.6 (5)C10—C18—H18A109.5
C6—C5—H5A119.2C10—C18—H18B109.5
C4—C5—H5A119.2H18A—C18—H18B109.5
C5—C6—C7122.8 (5)C10—C18—H18C109.5
C5—C6—H6A118.6H18A—C18—H18C109.5
C7—C6—H6A118.6H18B—C18—H18C109.5
C6—C7—C8116.9 (4)C17—C19—H19A109.5
C6—C7—C10122.0 (4)C17—C19—H19B109.5
C8—C7—C10121.1 (4)H19A—C19—H19B109.5
C9—C8—C7118.9 (4)C17—C19—H19C109.5
C9—C8—C13120.0 (4)H19A—C19—H19C109.5
C7—C8—C13121.1 (4)H19B—C19—H19C109.5
C4—C9—C8123.2 (5)N1—C20—C17112.2 (4)
C4—C9—H9A118.4N1—C20—H20A109.2
C8—C9—H9A118.4C17—C20—H20A109.2
C7—C10—C14110.5 (4)N1—C20—H20B109.2
C7—C10—C11107.9 (3)C17—C20—H20B109.2
C14—C10—C11109.4 (3)H20A—C20—H20B107.9
C7—C10—C18105.9 (3)N1—C21—C22121.6 (5)
C14—C10—C18108.3 (4)N1—C21—H21A119.2
C11—C10—C18114.7 (4)C22—C21—H21A119.2
C12—C11—C10109.6 (4)N2—C22—C26122.7 (5)
C12—C11—C17114.2 (4)N2—C22—C21115.0 (5)
C10—C11—C17117.0 (4)C26—C22—C21122.2 (5)
C12—C11—H11A104.9N2—C23—C24123.9 (7)
C10—C11—H11A104.9N2—C23—H23A118.0
C17—C11—H11A104.9C24—C23—H23A118.0
C13—C12—C11111.9 (5)C25—C24—C23118.6 (6)
C13—C12—H12A109.2C25—C24—H24A120.7
C11—C12—H12A109.2C23—C24—H24A120.7
C13—C12—H12B109.2C26—C25—C24119.4 (7)
C11—C12—H12B109.2C26—C25—H25A120.3
H12A—C12—H12B107.9C24—C25—H25A120.3
C12—C13—C8117.2 (4)C25—C26—C22119.0 (6)
C12—C13—H13A121.4C25—C26—H26A120.5
C8—C13—H13A121.4C22—C26—H26A120.5
C15—C14—C10112.1 (4)
C2—C3—C4—C5115.6 (6)C9—C8—C13—C12−179.5 (6)
C1—C3—C4—C5−117.5 (6)C7—C8—C13—C120.5 (9)
C2—C3—C4—C9−63.0 (7)C7—C10—C14—C15171.7 (4)
C1—C3—C4—C963.9 (7)C11—C10—C14—C1553.0 (5)
C9—C4—C5—C6−2.2 (8)C18—C10—C14—C15−72.6 (5)
C3—C4—C5—C6179.2 (5)C10—C14—C15—C16−58.8 (6)
C4—C5—C6—C71.1 (8)C14—C15—C16—C1758.4 (6)
C5—C6—C7—C80.9 (7)C15—C16—C17—C20−166.7 (4)
C5—C6—C7—C10179.1 (5)C15—C16—C17—C1974.4 (6)
C6—C7—C8—C9−1.8 (7)C15—C16—C17—C11−50.8 (6)
C10—C7—C8—C9180.0 (5)C12—C11—C17—C16176.9 (4)
C6—C7—C8—C13178.2 (5)C10—C11—C17—C1646.9 (5)
C10—C7—C8—C130.0 (8)C12—C11—C17—C20−67.1 (5)
C5—C4—C9—C81.3 (8)C10—C11—C17—C20162.8 (4)
C3—C4—C9—C8179.9 (5)C12—C11—C17—C1952.9 (6)
C7—C8—C9—C40.7 (8)C10—C11—C17—C19−77.1 (5)
C13—C8—C9—C4−179.2 (6)C21—N1—C20—C17124.8 (5)
C6—C7—C10—C1432.6 (6)C16—C17—C20—N1−63.6 (5)
C8—C7—C10—C14−149.3 (4)C19—C17—C20—N156.7 (6)
C6—C7—C10—C11152.2 (4)C11—C17—C20—N1179.5 (4)
C8—C7—C10—C11−29.7 (6)C20—N1—C21—C22179.8 (4)
C6—C7—C10—C18−84.5 (5)C23—N2—C22—C260.3 (9)
C8—C7—C10—C1893.6 (5)C23—N2—C22—C21179.4 (5)
C7—C10—C11—C1258.8 (5)N1—C21—C22—N2175.8 (5)
C14—C10—C11—C12179.2 (4)N1—C21—C22—C26−5.1 (8)
C18—C10—C11—C12−59.0 (5)C22—N2—C23—C24−0.2 (11)
C7—C10—C11—C17−169.0 (4)N2—C23—C24—C25−0.4 (12)
C14—C10—C11—C17−48.7 (5)C23—C24—C25—C260.9 (10)
C18—C10—C11—C1773.2 (5)C24—C25—C26—C22−0.7 (9)
C10—C11—C12—C13−60.7 (6)N2—C22—C26—C250.1 (9)
C17—C11—C12—C13165.7 (5)C21—C22—C26—C25−178.9 (5)
C11—C12—C13—C829.8 (8)
Acknowledgements top

This research was supported by grants from the National Natural Science Foundation of China (grant No. 30771690) and the Forestry Common Wealth Industry Special.

references
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