N-(2-Pyridylmethyleneamino)dehydro-abietylamine.

The title compound {systematic name: 1-[(1R,4aS,10aR)-7-isopropyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthren-1-yl]-N-[(E)-2-pyridylmethyleneamino]methanamine}, C(26)H(33)N(2), has been synthesized from dehydro-abietylamine. The two cyclo-hexane 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 hydro-phenanthrene structure.

Related literature

For the biological activity of a related compound, , see: Cannon (1952 ▶); Heinrich (1981 ▶); Kalser & Scheer (1976 ▶); Rao, Song & He (2008 ▶); Rao, Song, He & Jia (2008 ▶); Wilkerson et al. (1991 ▶, 1993 ▶). For the crystal structure of a related compound, see: Rao et al. (2006 ▶, 2007 ▶); Rao, Song, Jia & Shang (2008 ▶).

Experimental

Crystal data

C26H33N2

M = 373.54

Monoclinic,

a = 11.294 (2) Å

b = 6.0870 (12) Å

c = 16.129 (3) Å

β = 98.71 (3)°

V = 1096.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.951, T max = 0.974

2478 measured reflections

2357 independent reflections

1434 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.188

S = 1.00

2357 reflections

253 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; 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; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009040/at2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009040/at2704Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H33N2	F(000) = 406
Mr = 373.54	Dx = 1.132 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 11.294 (2) Å	θ = 10–13°
b = 6.0870 (12) Å	µ = 0.07 mm−1
c = 16.129 (3) Å	T = 293 K
β = 98.71 (3)°	Block, white
V = 1096.0 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	1434 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 26.0°, θmin = 1.3°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
Tmin = 0.951, Tmax = 0.974	l = −19→19
2478 measured reflections	3 standard reflections every 200 reflections
2357 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-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 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

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
N1	0.2116 (4)	0.1781 (8)	−0.1368 (2)	0.0616 (12)
N2	0.0270 (5)	0.4047 (9)	−0.3125 (3)	0.0814 (15)
C1	0.6341 (7)	0.9761 (12)	0.3876 (4)	0.108 (3)
H1B	0.5647	1.0519	0.3598	0.162*
H1C	0.6861	0.9407	0.3477	0.162*
H1D	0.6758	1.0684	0.4307	0.162*
C2	0.7016 (5)	0.6441 (12)	0.4723 (4)	0.088 (2)
H2B	0.6750	0.5139	0.4975	0.132*
H2C	0.7436	0.7369	0.5151	0.132*
H2D	0.7543	0.6041	0.4333	0.132*
C3	0.5953 (5)	0.7653 (10)	0.4268 (3)	0.0653 (15)
H3A	0.5469	0.8099	0.4695	0.078*
C4	0.5153 (5)	0.6250 (9)	0.3642 (3)	0.0560 (14)
C5	0.3996 (4)	0.5769 (10)	0.3732 (3)	0.0602 (15)
H5A	0.3690	0.6303	0.4197	0.072*
C6	0.3280 (4)	0.4524 (9)	0.3157 (3)	0.0541 (13)
H6A	0.2495	0.4261	0.3239	0.065*
C7	0.3671 (4)	0.3638 (8)	0.2458 (3)	0.0455 (11)
C8	0.4870 (4)	0.4045 (9)	0.2362 (3)	0.0519 (12)
C9	0.5572 (4)	0.5346 (10)	0.2954 (3)	0.0604 (14)
H9A	0.6360	0.5623	0.2883	0.072*
C10	0.2857 (4)	0.2215 (8)	0.1825 (3)	0.0444 (11)
C11	0.3278 (4)	0.2466 (8)	0.0964 (2)	0.0433 (10)
H11A	0.3290	0.4054	0.0865	0.052*
C12	0.4589 (4)	0.1745 (10)	0.1029 (3)	0.0636 (15)
H12A	0.4658	0.0218	0.1200	0.076*
H12B	0.4840	0.1863	0.0482	0.076*
C13	0.5392 (5)	0.3102 (14)	0.1640 (3)	0.092 (2)
H13A	0.6185	0.3356	0.1576	0.110*
C14	0.1547 (4)	0.2973 (9)	0.1759 (3)	0.0534 (13)
H14A	0.1260	0.2672	0.2284	0.064*
H14B	0.1507	0.4547	0.1666	0.064*
C15	0.0736 (4)	0.1820 (11)	0.1046 (3)	0.0639 (15)
H15A	0.0739	0.0251	0.1152	0.077*
H15B	−0.0078	0.2349	0.1022	0.077*
C16	0.1160 (4)	0.2251 (9)	0.0222 (3)	0.0538 (13)
H16A	0.1099	0.3814	0.0106	0.065*
H16B	0.0629	0.1501	−0.0217	0.065*
C17	0.2442 (4)	0.1517 (8)	0.0188 (3)	0.0482 (12)
C18	0.2950 (5)	−0.0156 (9)	0.2187 (3)	0.0686 (16)
H18A	0.2672	−0.0171	0.2721	0.103*
H18B	0.3769	−0.0633	0.2256	0.103*
H18C	0.2466	−0.1128	0.1808	0.103*
C19	0.2519 (5)	−0.1014 (9)	0.0118 (3)	0.0617 (15)
H19A	0.2274	−0.1678	0.0604	0.093*
H19B	0.3329	−0.1432	0.0082	0.093*
H19C	0.2002	−0.1500	−0.0376	0.093*
C20	0.2829 (4)	0.2563 (10)	−0.0602 (3)	0.0568 (13)
H20A	0.2753	0.4147	−0.0571	0.068*
H20B	0.3665	0.2223	−0.0615	0.068*
C21	0.1584 (5)	0.3134 (10)	−0.1878 (3)	0.0612 (14)
H21A	0.1654	0.4626	−0.1756	0.073*
C22	0.0852 (4)	0.2423 (10)	−0.2665 (3)	0.0559 (13)
C23	−0.0394 (6)	0.3452 (14)	−0.3848 (4)	0.094 (2)
H23A	−0.0807	0.4544	−0.4176	0.113*
C24	−0.0503 (6)	0.1341 (14)	−0.4132 (4)	0.085 (2)
H24A	−0.0981	0.1010	−0.4638	0.102*
C25	0.0104 (6)	−0.0273 (12)	−0.3659 (4)	0.0780 (18)
H25A	0.0054	−0.1723	−0.3843	0.094*
C26	0.0784 (5)	0.0259 (11)	−0.2916 (3)	0.0672 (15)
H26A	0.1196	−0.0824	−0.2582	0.081*

	U11	U22	U33	U12	U13	U23
N1	0.074 (3)	0.052 (3)	0.055 (2)	−0.001 (2)	0.000 (2)	−0.007 (2)
N2	0.091 (4)	0.069 (4)	0.079 (3)	0.008 (3)	−0.008 (3)	0.003 (3)
C1	0.152 (7)	0.067 (5)	0.095 (5)	−0.038 (5)	−0.014 (4)	−0.001 (4)
C2	0.084 (4)	0.077 (5)	0.092 (4)	−0.001 (4)	−0.027 (3)	−0.013 (4)
C3	0.073 (4)	0.058 (4)	0.062 (3)	−0.005 (3)	0.003 (3)	−0.007 (3)
C4	0.067 (3)	0.047 (3)	0.049 (3)	0.006 (3)	−0.006 (2)	−0.003 (2)
C5	0.066 (3)	0.063 (4)	0.051 (3)	0.004 (3)	0.008 (3)	−0.001 (3)
C6	0.056 (3)	0.052 (3)	0.054 (3)	−0.001 (3)	0.005 (2)	0.007 (3)
C7	0.055 (3)	0.037 (3)	0.043 (2)	0.002 (2)	0.004 (2)	0.009 (2)
C8	0.050 (3)	0.053 (3)	0.051 (3)	−0.002 (3)	0.001 (2)	−0.005 (3)
C9	0.049 (3)	0.066 (4)	0.064 (3)	−0.012 (3)	0.002 (2)	0.005 (3)
C10	0.044 (2)	0.033 (3)	0.054 (2)	−0.001 (2)	0.003 (2)	0.009 (2)
C11	0.046 (2)	0.033 (2)	0.050 (2)	−0.001 (2)	0.0013 (19)	0.001 (2)
C12	0.049 (3)	0.075 (4)	0.066 (3)	−0.001 (3)	0.006 (2)	−0.016 (3)
C13	0.049 (3)	0.146 (7)	0.083 (4)	−0.026 (4)	0.020 (3)	−0.055 (5)
C14	0.050 (3)	0.052 (3)	0.060 (3)	0.000 (2)	0.013 (2)	0.004 (3)
C15	0.043 (2)	0.078 (4)	0.069 (3)	−0.001 (3)	0.000 (2)	0.001 (3)
C16	0.049 (3)	0.047 (3)	0.061 (3)	0.000 (3)	−0.005 (2)	0.005 (3)
C17	0.055 (3)	0.030 (2)	0.059 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C18	0.087 (4)	0.046 (3)	0.068 (3)	−0.012 (3)	−0.002 (3)	0.019 (3)
C19	0.067 (3)	0.041 (3)	0.073 (3)	−0.003 (3)	−0.002 (3)	−0.004 (3)
C20	0.067 (3)	0.050 (3)	0.053 (3)	−0.008 (3)	0.005 (2)	−0.002 (3)
C21	0.068 (3)	0.054 (3)	0.061 (3)	−0.001 (3)	0.008 (3)	−0.006 (3)
C22	0.061 (3)	0.053 (3)	0.053 (3)	0.002 (3)	0.007 (2)	0.006 (3)
C23	0.089 (5)	0.088 (6)	0.094 (5)	0.014 (4)	−0.021 (4)	0.016 (5)
C24	0.087 (4)	0.098 (6)	0.065 (4)	−0.029 (4)	−0.001 (3)	0.001 (4)
C25	0.102 (5)	0.063 (4)	0.067 (4)	−0.014 (4)	0.008 (3)	−0.005 (4)
C26	0.076 (4)	0.060 (4)	0.064 (3)	−0.005 (3)	0.007 (3)	0.003 (3)

N1—C21	1.251 (6)	C12—H12A	0.9700
N1—C20	1.449 (6)	C12—H12B	0.9700
N2—C23	1.337 (8)	C13—H13A	0.9300
N2—C22	1.345 (7)	C14—C15	1.528 (7)
C1—C3	1.523 (9)	C14—H14A	0.9700
C1—H1B	0.9600	C14—H14B	0.9700
C1—H1C	0.9600	C15—C16	1.501 (6)
C1—H1D	0.9600	C15—H15A	0.9700
C2—C3	1.502 (8)	C15—H15B	0.9700
C2—H2B	0.9600	C16—C17	1.524 (6)
C2—H2C	0.9600	C16—H16A	0.9700
C2—H2D	0.9600	C16—H16B	0.9700
C3—C4	1.513 (7)	C17—C20	1.545 (7)
C3—H3A	0.9800	C17—C19	1.548 (7)
C4—C5	1.368 (7)	C18—H18A	0.9600
C4—C9	1.386 (7)	C18—H18B	0.9600
C5—C6	1.364 (7)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.381 (6)	C19—H19B	0.9600
C6—H6A	0.9300	C19—H19C	0.9600
C7—C8	1.407 (6)	C20—H20A	0.9700
C7—C10	1.534 (6)	C20—H20B	0.9700
C8—C9	1.392 (7)	C21—C22	1.473 (7)
C8—C13	1.498 (7)	C21—H21A	0.9300
C9—H9A	0.9300	C22—C26	1.376 (8)
C10—C14	1.537 (6)	C23—C24	1.363 (10)
C10—C11	1.543 (6)	C23—H23A	0.9300
C10—C18	1.555 (7)	C24—C25	1.363 (9)
C11—C12	1.532 (6)	C24—H24A	0.9300
C11—C17	1.560 (6)	C25—C26	1.361 (8)
C11—H11A	0.9800	C25—H25A	0.9300
C12—C13	1.485 (7)	C26—H26A	0.9300
C21—N1—C20	119.6 (5)	C15—C14—H14A	109.2
C23—N2—C22	116.4 (6)	C10—C14—H14A	109.2
C3—C1—H1B	109.5	C15—C14—H14B	109.2
C3—C1—H1C	109.5	C10—C14—H14B	109.2
H1B—C1—H1C	109.5	H14A—C14—H14B	107.9
C3—C1—H1D	109.5	C16—C15—C14	110.5 (4)
H1B—C1—H1D	109.5	C16—C15—H15A	109.5
H1C—C1—H1D	109.5	C14—C15—H15A	109.5
C3—C2—H2B	109.5	C16—C15—H15B	109.5
C3—C2—H2C	109.5	C14—C15—H15B	109.5
H2B—C2—H2C	109.5	H15A—C15—H15B	108.1
C3—C2—H2D	109.5	C15—C16—C17	114.4 (4)
H2B—C2—H2D	109.5	C15—C16—H16A	108.7
H2C—C2—H2D	109.5	C17—C16—H16A	108.7
C2—C3—C4	113.7 (5)	C15—C16—H16B	108.7
C2—C3—C1	110.9 (6)	C17—C16—H16B	108.7
C4—C3—C1	112.2 (4)	H16A—C16—H16B	107.6
C2—C3—H3A	106.5	C16—C17—C20	107.4 (4)
C4—C3—H3A	106.5	C16—C17—C19	111.0 (4)
C1—C3—H3A	106.5	C20—C17—C19	108.9 (4)
C5—C4—C9	116.6 (5)	C16—C17—C11	108.9 (4)
C5—C4—C3	122.3 (5)	C20—C17—C11	107.2 (4)
C9—C4—C3	121.1 (5)	C19—C17—C11	113.1 (4)
C6—C5—C4	121.6 (5)	C10—C18—H18A	109.5
C6—C5—H5A	119.2	C10—C18—H18B	109.5
C4—C5—H5A	119.2	H18A—C18—H18B	109.5
C5—C6—C7	122.8 (5)	C10—C18—H18C	109.5
C5—C6—H6A	118.6	H18A—C18—H18C	109.5
C7—C6—H6A	118.6	H18B—C18—H18C	109.5
C6—C7—C8	116.9 (4)	C17—C19—H19A	109.5
C6—C7—C10	122.0 (4)	C17—C19—H19B	109.5
C8—C7—C10	121.1 (4)	H19A—C19—H19B	109.5
C9—C8—C7	118.9 (4)	C17—C19—H19C	109.5
C9—C8—C13	120.0 (4)	H19A—C19—H19C	109.5
C7—C8—C13	121.1 (4)	H19B—C19—H19C	109.5
C4—C9—C8	123.2 (5)	N1—C20—C17	112.2 (4)
C4—C9—H9A	118.4	N1—C20—H20A	109.2
C8—C9—H9A	118.4	C17—C20—H20A	109.2
C7—C10—C14	110.5 (4)	N1—C20—H20B	109.2
C7—C10—C11	107.9 (3)	C17—C20—H20B	109.2
C14—C10—C11	109.4 (3)	H20A—C20—H20B	107.9
C7—C10—C18	105.9 (3)	N1—C21—C22	121.6 (5)
C14—C10—C18	108.3 (4)	N1—C21—H21A	119.2
C11—C10—C18	114.7 (4)	C22—C21—H21A	119.2
C12—C11—C10	109.6 (4)	N2—C22—C26	122.7 (5)
C12—C11—C17	114.2 (4)	N2—C22—C21	115.0 (5)
C10—C11—C17	117.0 (4)	C26—C22—C21	122.2 (5)
C12—C11—H11A	104.9	N2—C23—C24	123.9 (7)
C10—C11—H11A	104.9	N2—C23—H23A	118.0
C17—C11—H11A	104.9	C24—C23—H23A	118.0
C13—C12—C11	111.9 (5)	C25—C24—C23	118.6 (6)
C13—C12—H12A	109.2	C25—C24—H24A	120.7
C11—C12—H12A	109.2	C23—C24—H24A	120.7
C13—C12—H12B	109.2	C26—C25—C24	119.4 (7)
C11—C12—H12B	109.2	C26—C25—H25A	120.3
H12A—C12—H12B	107.9	C24—C25—H25A	120.3
C12—C13—C8	117.2 (4)	C25—C26—C22	119.0 (6)
C12—C13—H13A	121.4	C25—C26—H26A	120.5
C8—C13—H13A	121.4	C22—C26—H26A	120.5
C15—C14—C10	112.1 (4)
C2—C3—C4—C5	115.6 (6)	C9—C8—C13—C12	−179.5 (6)
C1—C3—C4—C5	−117.5 (6)	C7—C8—C13—C12	0.5 (9)
C2—C3—C4—C9	−63.0 (7)	C7—C10—C14—C15	171.7 (4)
C1—C3—C4—C9	63.9 (7)	C11—C10—C14—C15	53.0 (5)
C9—C4—C5—C6	−2.2 (8)	C18—C10—C14—C15	−72.6 (5)
C3—C4—C5—C6	179.2 (5)	C10—C14—C15—C16	−58.8 (6)
C4—C5—C6—C7	1.1 (8)	C14—C15—C16—C17	58.4 (6)
C5—C6—C7—C8	0.9 (7)	C15—C16—C17—C20	−166.7 (4)
C5—C6—C7—C10	179.1 (5)	C15—C16—C17—C19	74.4 (6)
C6—C7—C8—C9	−1.8 (7)	C15—C16—C17—C11	−50.8 (6)
C10—C7—C8—C9	180.0 (5)	C12—C11—C17—C16	176.9 (4)
C6—C7—C8—C13	178.2 (5)	C10—C11—C17—C16	46.9 (5)
C10—C7—C8—C13	0.0 (8)	C12—C11—C17—C20	−67.1 (5)
C5—C4—C9—C8	1.3 (8)	C10—C11—C17—C20	162.8 (4)
C3—C4—C9—C8	179.9 (5)	C12—C11—C17—C19	52.9 (6)
C7—C8—C9—C4	0.7 (8)	C10—C11—C17—C19	−77.1 (5)
C13—C8—C9—C4	−179.2 (6)	C21—N1—C20—C17	124.8 (5)
C6—C7—C10—C14	32.6 (6)	C16—C17—C20—N1	−63.6 (5)
C8—C7—C10—C14	−149.3 (4)	C19—C17—C20—N1	56.7 (6)
C6—C7—C10—C11	152.2 (4)	C11—C17—C20—N1	179.5 (4)
C8—C7—C10—C11	−29.7 (6)	C20—N1—C21—C22	179.8 (4)
C6—C7—C10—C18	−84.5 (5)	C23—N2—C22—C26	0.3 (9)
C8—C7—C10—C18	93.6 (5)	C23—N2—C22—C21	179.4 (5)
C7—C10—C11—C12	58.8 (5)	N1—C21—C22—N2	175.8 (5)
C14—C10—C11—C12	179.2 (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—C26	0.9 (10)
C18—C10—C11—C17	73.2 (5)	C24—C25—C26—C22	−0.7 (9)
C10—C11—C12—C13	−60.7 (6)	N2—C22—C26—C25	0.1 (9)
C17—C11—C12—C13	165.7 (5)	C21—C22—C26—C25	−178.9 (5)
C11—C12—C13—C8	29.8 (8)