N-Benzyl-idenenordehydro-abietylamine.

THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,4aS,10aR,E)-N-benzyl-idene-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthren-1-amine], C(26)H(33)N, has been synthesized from nor-dehydro-abietylamine and benzaldehyde. The two cyclo-hexane rings form a trans ring junction with classic chair and half-chair conformations, respectively, the two methyl groups are on the same side of tricyclic hydro-phenanthrene structure. The dihedral angle between two benzene rings is 44.2 (4)°. The C=N bond is in an E configuration.

Related literature

For the biological activity of dehydro­abietiylamine derivatives, see: n class="Gene">Rao et al. (2006 ▶); Rao, Song & He (2008 ▶); Rao, Song, He & Jia (2008 ▶); Wilkerson et al. (1993 ▶).

Experimental

Crystal data

C26H33N

M = 359.53

Monoclinic,

a = 12.285 (3) Å

b = 5.8940 (12) Å

c = 14.994 (3) Å

β = 95.90 (3)°

V = 1079.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.06 mm−1

T = 293 K

0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.981

2435 measured reflections

2324 independent reflections

1761 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.199

S = 1.04

2324 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.36 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022909/at2811sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022909/at2811Isup2.hkl

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

C26H33N	F(000) = 392
Mr = 359.53	Dx = 1.106 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 12.285 (3) Å	θ = 10–13°
b = 5.8940 (12) Å	µ = 0.06 mm−1
c = 14.994 (3) Å	T = 293 K
β = 95.90 (3)°	Block, white
V = 1079.9 (4) Å3	0.40 × 0.30 × 0.30 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	1761 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 26.0°, θmin = 1.4°
ω/2θ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = 0→7
Tmin = 0.975, Tmax = 0.981	l = 0→18
2435 measured reflections	3 standard reflections every 200 reflections
2324 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.03P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3
2324 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.30 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

Experimental. Although the absolute configuration could not be determined in this case, it has been determined in our previous article which indicated the chiral centers exhibited R,S and R configurations, respectively.

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
N	0.5943 (4)	0.1064 (10)	0.6722 (3)	0.0555 (15)
C1	0.9610 (7)	−0.212 (2)	0.6297 (5)	0.083 (3)
H1A	1.0249	−0.2959	0.6287	0.100*
C2	0.8832 (7)	−0.2846 (18)	0.6812 (5)	0.080 (2)
H2A	0.8933	−0.4180	0.7142	0.096*
C3	0.7893 (7)	−0.1591 (15)	0.6841 (4)	0.067 (2)
H3A	0.7358	−0.2059	0.7197	0.080*
C4	0.7749 (5)	0.0366 (14)	0.6340 (4)	0.061 (2)
C5	0.8544 (7)	0.1063 (16)	0.5820 (5)	0.072 (2)
H5A	0.8454	0.2385	0.5482	0.087*
C6	0.9483 (7)	−0.024 (2)	0.5807 (6)	0.091 (3)
H6A	1.0027	0.0210	0.5455	0.109*
C7	0.6712 (5)	0.1704 (15)	0.6342 (4)	0.065 (2)
H7A	0.6656	0.3083	0.6040	0.078*
C8	0.4875 (7)	0.2395 (12)	0.6683 (4)	0.0573 (19)
C9	0.4313 (5)	0.1432 (11)	0.7462 (3)	0.0460 (15)
H9A	0.4370	−0.0218	0.7401	0.055*
C10	0.3056 (5)	0.1900 (11)	0.7458 (4)	0.0436 (14)
C11	0.2496 (5)	0.1195 (14)	0.6530 (4)	0.0552 (17)
H11A	0.1732	0.1639	0.6486	0.066*
H11B	0.2524	−0.0443	0.6476	0.066*
C12	0.3039 (6)	0.2281 (15)	0.5748 (4)	0.068 (2)
H12A	0.2670	0.1766	0.5181	0.082*
H12B	0.2970	0.3919	0.5774	0.082*
C13	0.4198 (5)	0.1662 (15)	0.5803 (4)	0.0613 (19)
H13A	0.4517	0.2347	0.5302	0.074*
H13B	0.4254	0.0029	0.5743	0.074*
C14	0.4894 (5)	0.1957 (14)	0.8384 (4)	0.0567 (17)
H14A	0.5680	0.1840	0.8368	0.068*
H14B	0.4726	0.3494	0.8556	0.068*
C15	0.4526 (5)	0.0303 (16)	0.9058 (4)	0.061 (2)
H15A	0.4719	0.0913	0.9654	0.073*
H15B	0.4928	−0.1102	0.9015	0.073*
C16	0.3317 (4)	−0.0234 (11)	0.8955 (3)	0.0389 (13)
C17	0.2618 (5)	0.0468 (10)	0.8206 (3)	0.0412 (14)
C18	0.2886 (5)	−0.1458 (12)	0.9632 (4)	0.0501 (16)
H18A	0.3349	−0.1858	1.0137	0.060*
C19	0.1794 (5)	−0.2108 (11)	0.9587 (4)	0.0452 (14)
C20	0.1139 (5)	−0.1380 (13)	0.8849 (4)	0.0527 (17)
H20A	0.0400	−0.1755	0.8800	0.063*
C21	0.1526 (5)	−0.0118 (13)	0.8179 (4)	0.0544 (17)
H21A	0.1043	0.0352	0.7697	0.065*
C22	0.5043 (8)	0.4935 (13)	0.6724 (5)	0.079 (3)
H22A	0.4345	0.5680	0.6689	0.118*
H22B	0.5428	0.5409	0.6231	0.118*
H22C	0.5462	0.5328	0.7279	0.118*
C23	0.2709 (7)	0.4386 (12)	0.7645 (5)	0.068 (2)
H23A	0.1926	0.4468	0.7627	0.103*
H23B	0.2952	0.5373	0.7196	0.103*
H23C	0.3034	0.4848	0.8226	0.103*
C24	0.1371 (6)	−0.3531 (14)	1.0319 (4)	0.0597 (19)
H24A	0.0603	−0.3865	1.0122	0.072*
C25	0.1949 (7)	−0.5788 (13)	1.0437 (6)	0.080 (3)
H25A	0.1657	−0.6626	1.0908	0.120*
H25B	0.2717	−0.5541	1.0592	0.120*
H25C	0.1839	−0.6633	0.9888	0.120*
C26	0.1383 (7)	−0.2230 (16)	1.1198 (4)	0.082 (3)
H26A	0.1122	−0.3194	1.1646	0.123*
H26B	0.0919	−0.0922	1.1111	0.123*
H26C	0.2117	−0.1755	1.1392	0.123*

	U11	U22	U33	U12	U13	U23
N	0.066 (3)	0.048 (3)	0.056 (3)	−0.002 (3)	0.022 (3)	−0.004 (3)
C1	0.070 (5)	0.115 (9)	0.063 (5)	0.016 (6)	0.002 (4)	−0.023 (6)
C2	0.100 (6)	0.076 (6)	0.063 (4)	−0.008 (6)	0.004 (4)	0.004 (5)
C3	0.087 (5)	0.065 (5)	0.048 (4)	−0.012 (5)	0.006 (4)	−0.012 (4)
C4	0.067 (4)	0.070 (5)	0.044 (3)	−0.018 (4)	−0.001 (3)	−0.007 (4)
C5	0.088 (5)	0.068 (6)	0.062 (4)	−0.010 (5)	0.011 (4)	0.007 (4)
C6	0.075 (6)	0.127 (10)	0.069 (5)	−0.022 (7)	0.003 (4)	0.000 (7)
C7	0.070 (4)	0.073 (5)	0.055 (4)	−0.017 (4)	0.020 (3)	0.004 (4)
C8	0.095 (5)	0.036 (4)	0.041 (3)	−0.001 (4)	0.008 (3)	−0.003 (3)
C9	0.076 (4)	0.030 (3)	0.031 (3)	−0.013 (3)	0.000 (3)	−0.001 (3)
C10	0.061 (4)	0.033 (3)	0.036 (3)	0.011 (3)	0.002 (2)	0.004 (3)
C11	0.062 (4)	0.063 (5)	0.040 (3)	0.005 (4)	0.002 (3)	0.006 (3)
C12	0.096 (5)	0.066 (5)	0.040 (3)	−0.002 (5)	0.000 (3)	0.013 (4)
C13	0.078 (4)	0.073 (5)	0.034 (3)	−0.012 (5)	0.012 (3)	0.004 (4)
C14	0.067 (4)	0.056 (4)	0.044 (3)	−0.014 (4)	−0.005 (3)	−0.001 (3)
C15	0.054 (4)	0.091 (6)	0.038 (3)	−0.022 (4)	0.000 (3)	0.005 (4)
C16	0.044 (3)	0.038 (3)	0.035 (3)	0.000 (3)	0.005 (2)	−0.003 (3)
C17	0.059 (4)	0.035 (3)	0.031 (3)	0.001 (3)	0.008 (2)	−0.002 (3)
C18	0.060 (4)	0.051 (4)	0.037 (3)	−0.003 (3)	−0.006 (3)	0.005 (3)
C19	0.057 (3)	0.040 (4)	0.041 (3)	−0.002 (3)	0.012 (3)	−0.007 (3)
C20	0.046 (3)	0.063 (5)	0.048 (3)	−0.004 (4)	0.003 (3)	−0.008 (4)
C21	0.063 (4)	0.058 (5)	0.041 (3)	0.013 (4)	−0.004 (3)	−0.004 (3)
C22	0.134 (8)	0.036 (4)	0.069 (5)	−0.022 (5)	0.022 (5)	0.004 (4)
C23	0.105 (6)	0.037 (4)	0.068 (4)	0.019 (4)	0.030 (4)	0.001 (4)
C24	0.062 (4)	0.067 (5)	0.052 (3)	−0.015 (4)	0.015 (3)	−0.006 (4)
C25	0.109 (6)	0.038 (4)	0.099 (6)	−0.006 (5)	0.031 (5)	0.010 (4)
C26	0.135 (7)	0.069 (6)	0.045 (4)	−0.015 (6)	0.024 (4)	0.005 (4)

N—C7	1.212 (7)	C14—C15	1.508 (9)
N—C8	1.524 (9)	C14—H14A	0.9700
C1—C6	1.331 (14)	C14—H14B	0.9700
C1—C2	1.359 (11)	C15—C16	1.510 (8)
C1—H1A	0.9300	C15—H15A	0.9700
C2—C3	1.375 (11)	C15—H15B	0.9700
C2—H2A	0.9300	C16—C18	1.393 (8)
C3—C4	1.378 (11)	C16—C17	1.405 (7)
C3—H3A	0.9300	C17—C21	1.381 (8)
C4—C5	1.374 (9)	C18—C19	1.389 (8)
C4—C7	1.499 (7)	C18—H18A	0.9300
C5—C6	1.387 (12)	C19—C20	1.368 (8)
C5—H5A	0.9300	C19—C24	1.515 (9)
C6—H6A	0.9300	C20—C21	1.374 (9)
C7—H7A	0.9300	C20—H20A	0.9300
C8—C22	1.512 (10)	C21—H21A	0.9300
C8—C9	1.525 (9)	C22—H22A	0.9600
C8—C13	1.547 (9)	C22—H22B	0.9600
C9—C14	1.522 (7)	C22—H22C	0.9600
C9—C10	1.568 (8)	C23—H23A	0.9600
C9—H9A	0.9800	C23—H23B	0.9600
C10—C17	1.544 (8)	C23—H23C	0.9600
C10—C11	1.545 (8)	C24—C25	1.509 (11)
C10—C23	1.559 (9)	C24—C26	1.524 (10)
C11—C12	1.546 (9)	C24—H24A	0.9800
C11—H11A	0.9700	C25—H25A	0.9600
C11—H11B	0.9700	C25—H25B	0.9600
C12—C13	1.464 (9)	C25—H25C	0.9600
C12—H12A	0.9700	C26—H26A	0.9600
C12—H12B	0.9700	C26—H26B	0.9600
C13—H13A	0.9700	C26—H26C	0.9600
C13—H13B	0.9700
C7—N—C8	122.1 (7)	C15—C14—H14A	109.8
C6—C1—C2	121.9 (10)	C9—C14—H14A	109.8
C6—C1—H1A	119.1	C15—C14—H14B	109.8
C2—C1—H1A	119.1	C9—C14—H14B	109.8
C1—C2—C3	119.3 (10)	H14A—C14—H14B	108.2
C1—C2—H2A	120.4	C14—C15—C16	115.3 (5)
C3—C2—H2A	120.4	C14—C15—H15A	108.5
C2—C3—C4	119.7 (8)	C16—C15—H15A	108.5
C2—C3—H3A	120.2	C14—C15—H15B	108.5
C4—C3—H3A	120.2	C16—C15—H15B	108.5
C5—C4—C3	120.0 (7)	H15A—C15—H15B	107.5
C5—C4—C7	119.9 (7)	C18—C16—C17	119.2 (5)
C3—C4—C7	120.1 (7)	C18—C16—C15	118.5 (5)
C4—C5—C6	119.0 (8)	C17—C16—C15	122.3 (5)
C4—C5—H5A	120.5	C21—C17—C16	117.5 (5)
C6—C5—H5A	120.5	C21—C17—C10	121.7 (5)
C1—C6—C5	120.2 (9)	C16—C17—C10	120.8 (5)
C1—C6—H6A	119.9	C19—C18—C16	123.0 (5)
C5—C6—H6A	119.9	C19—C18—H18A	118.5
N—C7—C4	122.8 (8)	C16—C18—H18A	118.5
N—C7—H7A	118.6	C20—C19—C18	115.9 (6)
C4—C7—H7A	118.6	C20—C19—C24	122.8 (6)
C22—C8—N	113.3 (7)	C18—C19—C24	121.3 (6)
C22—C8—C9	114.1 (6)	C19—C20—C21	122.8 (6)
N—C8—C9	103.6 (5)	C19—C20—H20A	118.6
C22—C8—C13	111.7 (7)	C21—C20—H20A	118.6
N—C8—C13	105.9 (5)	C20—C21—C17	121.5 (6)
C9—C8—C13	107.6 (6)	C20—C21—H21A	119.3
C14—C9—C8	114.3 (5)	C17—C21—H21A	119.3
C14—C9—C10	109.7 (5)	C8—C22—H22A	109.5
C8—C9—C10	117.1 (5)	C8—C22—H22B	109.5
C14—C9—H9A	104.8	H22A—C22—H22B	109.5
C8—C9—H9A	104.8	C8—C22—H22C	109.5
C10—C9—H9A	104.8	H22A—C22—H22C	109.5
C17—C10—C11	110.6 (5)	H22B—C22—H22C	109.5
C17—C10—C23	105.2 (5)	C10—C23—H23A	109.5
C11—C10—C23	108.1 (6)	C10—C23—H23B	109.5
C17—C10—C9	108.5 (5)	H23A—C23—H23B	109.5
C11—C10—C9	107.6 (5)	C10—C23—H23C	109.5
C23—C10—C9	116.9 (6)	H23A—C23—H23C	109.5
C10—C11—C12	112.6 (6)	H23B—C23—H23C	109.5
C10—C11—H11A	109.1	C25—C24—C19	112.4 (6)
C12—C11—H11A	109.1	C25—C24—C26	112.2 (7)
C10—C11—H11B	109.1	C19—C24—C26	112.0 (6)
C12—C11—H11B	109.1	C25—C24—H24A	106.6
H11A—C11—H11B	107.8	C19—C24—H24A	106.6
C13—C12—C11	110.3 (6)	C26—C24—H24A	106.6
C13—C12—H12A	109.6	C24—C25—H25A	109.5
C11—C12—H12A	109.6	C24—C25—H25B	109.5
C13—C12—H12B	109.6	H25A—C25—H25B	109.5
C11—C12—H12B	109.6	C24—C25—H25C	109.5
H12A—C12—H12B	108.1	H25A—C25—H25C	109.5
C12—C13—C8	114.4 (6)	H25B—C25—H25C	109.5
C12—C13—H13A	108.7	C24—C26—H26A	109.5
C8—C13—H13A	108.7	C24—C26—H26B	109.5
C12—C13—H13B	108.7	H26A—C26—H26B	109.5
C8—C13—H13B	108.7	C24—C26—H26C	109.5
H13A—C13—H13B	107.6	H26A—C26—H26C	109.5
C15—C14—C9	109.4 (5)	H26B—C26—H26C	109.5
C6—C1—C2—C3	−1.0 (13)	C22—C8—C13—C12	−71.4 (9)
C1—C2—C3—C4	0.9 (12)	N—C8—C13—C12	164.8 (7)
C2—C3—C4—C5	−0.5 (10)	C9—C8—C13—C12	54.6 (9)
C2—C3—C4—C7	177.9 (7)	C8—C9—C14—C15	−160.1 (6)
C3—C4—C5—C6	0.3 (11)	C10—C9—C14—C15	66.1 (7)
C7—C4—C5—C6	−178.2 (7)	C9—C14—C15—C16	−41.1 (8)
C2—C1—C6—C5	0.8 (14)	C14—C15—C16—C18	−170.0 (6)
C4—C5—C6—C1	−0.4 (13)	C14—C15—C16—C17	9.6 (9)
C8—N—C7—C4	−177.2 (6)	C18—C16—C17—C21	−0.4 (9)
C5—C4—C7—N	173.2 (7)	C15—C16—C17—C21	179.9 (6)
C3—C4—C7—N	−5.3 (11)	C18—C16—C17—C10	177.8 (6)
C7—N—C8—C22	−38.6 (9)	C15—C16—C17—C10	−1.9 (9)
C7—N—C8—C9	−162.7 (6)	C11—C10—C17—C21	−39.0 (8)
C7—N—C8—C13	84.1 (8)	C23—C10—C17—C21	77.4 (8)
C22—C8—C9—C14	−56.7 (9)	C9—C10—C17—C21	−156.8 (6)
N—C8—C9—C14	66.8 (7)	C11—C10—C17—C16	142.8 (6)
C13—C8—C9—C14	178.7 (6)	C23—C10—C17—C16	−100.8 (7)
C22—C8—C9—C10	73.6 (9)	C9—C10—C17—C16	25.0 (7)
N—C8—C9—C10	−162.9 (5)	C17—C16—C18—C19	2.7 (10)
C13—C8—C9—C10	−51.0 (7)	C15—C16—C18—C19	−177.6 (7)
C14—C9—C10—C17	−56.7 (7)	C16—C18—C19—C20	−3.0 (10)
C8—C9—C10—C17	170.8 (5)	C16—C18—C19—C24	177.1 (7)
C14—C9—C10—C11	−176.4 (6)	C18—C19—C20—C21	1.2 (10)
C8—C9—C10—C11	51.2 (7)	C24—C19—C20—C21	−179.0 (7)
C14—C9—C10—C23	61.9 (7)	C19—C20—C21—C17	1.0 (11)
C8—C9—C10—C23	−70.5 (7)	C16—C17—C21—C20	−1.3 (10)
C17—C10—C11—C12	−170.3 (6)	C10—C17—C21—C20	−179.5 (6)
C23—C10—C11—C12	75.1 (7)	C20—C19—C24—C25	120.6 (7)
C9—C10—C11—C12	−51.9 (7)	C18—C19—C24—C25	−59.6 (9)
C10—C11—C12—C13	58.1 (9)	C20—C19—C24—C26	−112.0 (8)
C11—C12—C13—C8	−59.1 (9)	C18—C19—C24—C26	67.9 (8)