N-(2-Pyridylmethyleneamino)dehydro­abietylamine

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

doi:10.1107/S1600536809009040

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o786

doi:10.1107/S1600536809009040

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N-(2-Pyridylmethyleneamino)dehydroabietylamine

Yong Wu,^a,^b Xiao-Ping Rao,^a ^* Zong-De Wang,^b Zhan-Qian Song ^a and Xu-Jie Yao ^b

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China, and ^bCollege of Landscape Architecture and Art, Jiangxi Agriculture University, Nanchang 330045, People's Republic of China
^*Correspondence e-mail: rxping2001@163.com

(Received 31 December 2008; accepted 12 March 2009; online 19 March 2009)

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.

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_r = 373.54
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.188
S = 1.00
2357 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

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].

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

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

C₂₆H₃₃N₂	F(000) = 406
M_r = 373.54	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1434 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 26.0°, θ_min = 1.3°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.951, T_max = 0.974	l = −19→19
2478 measured reflections	3 standard reflections every 200 reflections
2357 independent reflections	intensity decay: none

Refinement top

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(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2357 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₃₃N₂	V = 1096.0 (4) Å³
M_r = 373.54	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.294 (2) Å	µ = 0.07 mm⁻¹
b = 6.0870 (12) Å	T = 293 K
c = 16.129 (3) Å	0.30 × 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)	R_int = 0.045
T_min = 0.951, T_max = 0.974	3 standard reflections every 200 reflections
2478 measured reflections	intensity decay: none
2357 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.188	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
2357 reflections	Δρ_min = −0.20 e Å⁻³
253 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₆H₃₃N₂
M_r	373.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.294 (2), 6.0870 (12), 16.129 (3)
β (°)	98.71 (3)
V (Å³)	1096.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.951, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	2478, 2357, 1434
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.188, 1.00
No. of reflections	2357
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Acknowledgements

This research was supported by grants from the National Natural Science Foundation of China (grant No. 30771690) and the Forestry Commonwealth Industry Special Foundation of China (grant No. 200704008).

References

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