2,6-Bis[1-(2,6-diethyl­phenyl­imino)eth­yl]pyridine

Yang, Y.; Fan, R.; Li, W.

doi:10.1107/S1600536808036842

organic compounds

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Volume 64| Part 12| December 2008| Page o2368

doi:10.1107/S1600536808036842

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2,6-Bis[1-(2,6-diethylphenylimino)ethyl]pyridine

Yu-lin Yang,^a ^* Rui-qing Fan ^a and Wen-hui Li ^b

^aDepartment of Chemistry, Harbin Institute of Technology, Harbin 150001, People's Republic of China, and ^bCollege of Materials Science and Engineering, Harbin University of Science & Technology, Harbin 150040, People's Republic of China
^*Correspondence e-mail: yangyulin2000@163.com

(Received 21 October 2008; accepted 8 November 2008; online 20 November 2008)

The title compound, C₂₉H₃₅N₃, is the product of the condensation reaction between 2,6-diacetylpyridine and 2,6-diethylaniline. In the molecule, the pyridyl ring is coplanar with the imino functional groups [torsion angles in the range 177.1 (2)–179.9 (2)°. The two 2,6-diethyl-substituted benzene rings are approximately perpendicular to the ethylidenepyridine central core, the dihedral angles being 88.7 (1) and 88.4 (1)°, respectively.

Related literature

For applications of pyridine derivatives, see: Tang & VanSlyke (1987 ); Wang (2001 ). For the synthesis of the title molecule, see: Fan et al. (2004 ). For structures of other imino derivatives, see: Mentes et al. (2001 ); Huang et al. (2006 ).

Experimental

Crystal data

C₂₉H₃₅N₃
M_r = 425.60
Monoclinic, P 2₁ /c
a = 7.9390 (8) Å
b = 12.3208 (13) Å
c = 25.998 (3) Å
β = 96.234 (2)°
V = 2528.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 (2) K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.983, T_max = 0.987
13906 measured reflections
4938 independent reflections
2362 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.101
S = 0.95
4938 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—C1	1.272 (3)
N1—C10	1.431 (3)
N2—C2	1.333 (2)
N2—C6	1.348 (2)
N3—C7	1.275 (2)
N3—C20	1.424 (3)

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036842/bh2205sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036842/bh2205Isup2.hkl

checkCIF report

Comment top

Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential application in areas of sensor technologies and electro-luminescent devices (Tang & VanSlyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we prepared a series of bis(iminoalkyl)pyridine ligands by the condensation of 2,6-diacetylpyridine with the corresponding aniline in methanol (Fan et al., 2004). We report here the crystal structure of one of them, (I).

The molecular structure of (I) is shown in Fig. 1 and selected bond distances are given in Table 1. The pyridyl ring is coplanar with the two imino functional groups. The two imino C═N bonds have typical double-bond characteristics, with bond lengths of 1.272 (3) and 1.275 (2) Å, which are similar to that in BIP1, 1.266 (4) (Mentes et al., 2001) and in 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine, 1.265 (2) and 1.271 (2) Å (Huang et al., 2006). Compound (I) possesses a structure which approximates C_s symmetry about a plane bisecting the central pyridyl ring. The two 2,6-diethyl-substituted phenyl rings are approximately perpendicular to the ethylidenepyridine ring, with the dihedral angles being 88.7° and 88.4°.

Related literature top

For applications of pyridine derivatives, see: Tang & VanSlyke (1987); Wang (2001). For the synthesis of the title molecule, see: Fan et al. (2004). For structures of other imino derivatives, see: Mentes et al. (2001); Huang et al. (2006).

Experimental top

The title compound was synthesized according to the literature method of Fan et al. (2004). To a solution of 2,6-diethylpyridine (1.5 g, 9.2 mmol) in absolute methanol (40 ml) was added 2,6-diethylaniline (4.6 ml, 27.7 mmol). After the addition of several drops of formic acid, the reaction mixture was refluxed for 24 h and then allowed to cool down to room temperature. The crude product precipitated as a yellow powder. Pure (I) was obtained as yellow block crystals in 84% yield (3.3 g) upon recrystallization from methanol, giving single crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of (I) along a cell axis direction.

2,6-Bis[1-(2,6-diethylphenylimino)ethyl]pyridine top

Crystal data top

C₂₉H₃₅N₃	F(000) = 920
M_r = 425.60	D_x = 1.118 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13906 reflections
a = 7.9390 (8) Å	θ = 1.6–26.0°
b = 12.3208 (13) Å	µ = 0.07 mm⁻¹
c = 25.998 (3) Å	T = 193 K
β = 96.234 (2)°	Block, yellow
V = 2528.0 (5) Å³	0.26 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4938 independent reflections
Radiation source: fine-focus sealed tube	2362 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.983, T_max = 0.987	k = −15→12
13906 measured reflections	l = −31→32

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
4938 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₉H₃₅N₃	V = 2528.0 (5) Å³
M_r = 425.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9390 (8) Å	µ = 0.07 mm⁻¹
b = 12.3208 (13) Å	T = 193 K
c = 25.998 (3) Å	0.26 × 0.24 × 0.20 mm
β = 96.234 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4938 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2362 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.987	R_int = 0.077
13906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.95	Δρ_max = 0.30 e Å⁻³
4938 reflections	Δρ_min = −0.19 e Å⁻³
289 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	−0.5544 (2)	0.61937 (15)	−0.15400 (7)	0.0377 (5)
N2	−0.2647 (2)	0.69242 (15)	−0.04651 (7)	0.0342 (5)
N3	0.0206 (2)	0.83861 (14)	0.04282 (7)	0.0328 (5)
C1	−0.4636 (3)	0.60967 (19)	−0.11083 (9)	0.0353 (6)
C2	−0.3645 (3)	0.70650 (19)	−0.09065 (9)	0.0315 (6)
C3	−0.3771 (3)	0.80441 (18)	−0.11695 (9)	0.0379 (7)
H3B	−0.4480	0.8113	−0.1477	0.045*
C4	−0.2830 (3)	0.89137 (19)	−0.09692 (9)	0.0401 (7)
H4A	−0.2893	0.9580	−0.1139	0.048*
C5	−0.1790 (3)	0.87807 (18)	−0.05110 (9)	0.0346 (6)
H5A	−0.1140	0.9355	−0.0367	0.041*
C6	−0.1734 (3)	0.77816 (18)	−0.02709 (9)	0.0321 (6)
C7	−0.0646 (3)	0.75836 (19)	0.02294 (9)	0.0328 (6)
C8	−0.4473 (3)	0.50849 (18)	−0.07891 (9)	0.0551 (8)
H8A	−0.5166	0.4524	−0.0959	0.083*
H8B	−0.4837	0.5227	−0.0455	0.083*
H8C	−0.3311	0.4854	−0.0748	0.083*
C9	−0.0684 (3)	0.64705 (18)	0.04624 (9)	0.0516 (8)
H9A	0.0057	0.6450	0.0780	0.077*
H9B	−0.0314	0.5947	0.0225	0.077*
H9C	−0.1818	0.6302	0.0531	0.077*
C10	−0.6522 (3)	0.52973 (18)	−0.17576 (9)	0.0350 (6)
C11	−0.5797 (3)	0.46024 (19)	−0.20928 (9)	0.0354 (6)
C12	−0.6793 (3)	0.3774 (2)	−0.23284 (9)	0.0460 (7)
H12A	−0.6339	0.3312	−0.2560	0.055*
C13	−0.8439 (4)	0.3630 (2)	−0.22238 (10)	0.0529 (8)
H13A	−0.9089	0.3071	−0.2382	0.063*
C14	−0.9118 (3)	0.4313 (2)	−0.18850 (10)	0.0531 (8)
H14A	−1.0227	0.4202	−0.1813	0.064*
C15	−0.8197 (3)	0.5162 (2)	−0.16479 (10)	0.0442 (7)
C16	−0.3966 (3)	0.4759 (2)	−0.21860 (9)	0.0542 (8)
H16A	−0.3738	0.5533	−0.2186	0.065*
H16B	−0.3261	0.4447	−0.1895	0.065*
C17	−0.3415 (3)	0.4290 (2)	−0.26723 (10)	0.0677 (9)
H17A	−0.2233	0.4437	−0.2685	0.102*
H17B	−0.4061	0.4613	−0.2967	0.102*
H17C	−0.3599	0.3520	−0.2677	0.102*
C18	−0.8989 (3)	0.5920 (2)	−0.12862 (10)	0.0595 (8)
H18A	−0.9946	0.5565	−0.1155	0.071*
H18B	−0.8167	0.6094	−0.0994	0.071*
C19	−0.9567 (4)	0.6936 (2)	−0.15592 (11)	0.0843 (11)
H19A	−1.0065	0.7408	−0.1324	0.126*
H19B	−1.0392	0.6764	−0.1845	0.126*
H19C	−0.8616	0.7292	−0.1685	0.126*
C20	0.1215 (3)	0.82874 (17)	0.09135 (9)	0.0314 (6)
C21	0.2917 (3)	0.79922 (18)	0.09253 (10)	0.0366 (6)
C22	0.3912 (3)	0.80093 (19)	0.14006 (11)	0.0481 (7)
H22A	0.5045	0.7806	0.1417	0.058*
C23	0.3256 (4)	0.8321 (2)	0.18473 (11)	0.0512 (8)
H23A	0.3947	0.8347	0.2160	0.061*
C24	0.1569 (4)	0.85952 (19)	0.18268 (10)	0.0466 (7)
H24A	0.1129	0.8799	0.2130	0.056*
C25	0.0504 (3)	0.85759 (18)	0.13639 (9)	0.0367 (6)
C26	0.3694 (3)	0.76989 (19)	0.04370 (9)	0.0458 (7)
H26A	0.2924	0.7225	0.0227	0.055*
H26B	0.4738	0.7302	0.0530	0.055*
C27	0.4070 (3)	0.86848 (19)	0.01206 (10)	0.0595 (8)
H27A	0.4547	0.8456	−0.0185	0.089*
H27B	0.4862	0.9146	0.0323	0.089*
H27C	0.3040	0.9077	0.0024	0.089*
C28	−0.1336 (3)	0.8865 (2)	0.13489 (9)	0.0482 (7)
H28A	−0.1670	0.8812	0.1696	0.058*
H28B	−0.1999	0.8342	0.1134	0.058*
C29	−0.1747 (4)	0.9995 (2)	0.11419 (10)	0.0685 (9)
H29A	−0.2938	1.0131	0.1142	0.103*
H29B	−0.1447	1.0051	0.0795	0.103*
H29C	−0.1117	1.0520	0.1357	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0406 (14)	0.0347 (13)	0.0358 (13)	−0.0017 (10)	−0.0047 (11)	−0.0046 (10)
N2	0.0406 (14)	0.0297 (12)	0.0312 (12)	−0.0026 (10)	−0.0010 (10)	−0.0022 (10)
N3	0.0371 (13)	0.0301 (12)	0.0309 (12)	−0.0024 (10)	0.0030 (10)	−0.0034 (10)
C1	0.0411 (17)	0.0318 (15)	0.0320 (15)	0.0018 (12)	−0.0001 (13)	−0.0012 (12)
C2	0.0369 (16)	0.0278 (15)	0.0293 (15)	0.0002 (12)	0.0020 (12)	−0.0022 (12)
C3	0.0455 (18)	0.0329 (15)	0.0340 (15)	−0.0013 (13)	−0.0009 (13)	−0.0007 (13)
C4	0.0536 (18)	0.0265 (15)	0.0396 (16)	−0.0012 (13)	0.0026 (14)	0.0026 (12)
C5	0.0408 (16)	0.0291 (15)	0.0337 (15)	−0.0042 (12)	0.0029 (13)	−0.0028 (12)
C6	0.0357 (16)	0.0269 (14)	0.0337 (15)	−0.0014 (12)	0.0044 (12)	−0.0011 (12)
C7	0.0369 (16)	0.0295 (15)	0.0318 (15)	−0.0001 (12)	0.0039 (13)	0.0007 (12)
C8	0.072 (2)	0.0370 (16)	0.0509 (18)	−0.0122 (15)	−0.0163 (16)	0.0078 (14)
C9	0.064 (2)	0.0381 (16)	0.0479 (17)	−0.0114 (14)	−0.0170 (15)	0.0096 (14)
C10	0.0386 (17)	0.0332 (15)	0.0311 (15)	−0.0026 (13)	−0.0057 (13)	0.0008 (12)
C11	0.0316 (16)	0.0389 (16)	0.0344 (15)	−0.0021 (13)	−0.0021 (13)	−0.0005 (13)
C12	0.053 (2)	0.0466 (17)	0.0372 (16)	−0.0019 (15)	−0.0017 (14)	−0.0079 (13)
C13	0.052 (2)	0.055 (2)	0.0492 (18)	−0.0161 (16)	−0.0035 (16)	−0.0064 (15)
C14	0.0335 (18)	0.071 (2)	0.0537 (19)	−0.0119 (16)	0.0004 (15)	−0.0030 (17)
C15	0.0375 (18)	0.0504 (18)	0.0439 (17)	0.0016 (14)	0.0000 (14)	−0.0038 (14)
C16	0.0444 (19)	0.071 (2)	0.0471 (18)	0.0011 (15)	0.0047 (14)	−0.0214 (15)
C17	0.063 (2)	0.087 (2)	0.054 (2)	0.0008 (18)	0.0091 (16)	−0.0043 (17)
C18	0.049 (2)	0.061 (2)	0.070 (2)	0.0079 (16)	0.0126 (16)	0.0072 (17)
C19	0.110 (3)	0.054 (2)	0.096 (3)	0.007 (2)	0.042 (2)	0.006 (2)
C20	0.0345 (16)	0.0256 (14)	0.0327 (15)	−0.0062 (12)	−0.0028 (13)	0.0009 (11)
C21	0.0391 (17)	0.0291 (15)	0.0410 (16)	−0.0041 (12)	0.0016 (14)	0.0062 (12)
C22	0.0389 (18)	0.0431 (17)	0.060 (2)	−0.0043 (13)	−0.0057 (16)	0.0111 (15)
C23	0.056 (2)	0.0497 (18)	0.0442 (19)	−0.0110 (16)	−0.0113 (16)	0.0052 (15)
C24	0.062 (2)	0.0439 (17)	0.0340 (16)	−0.0109 (15)	0.0035 (15)	−0.0012 (13)
C25	0.0407 (17)	0.0341 (15)	0.0351 (16)	−0.0057 (13)	0.0038 (14)	0.0008 (12)
C26	0.0416 (18)	0.0397 (16)	0.0567 (18)	0.0045 (13)	0.0072 (14)	0.0047 (14)
C27	0.070 (2)	0.0473 (18)	0.066 (2)	0.0092 (15)	0.0282 (17)	0.0120 (15)
C28	0.051 (2)	0.0554 (19)	0.0396 (16)	−0.0051 (15)	0.0118 (14)	−0.0067 (14)
C29	0.064 (2)	0.076 (2)	0.068 (2)	0.0192 (17)	0.0232 (17)	0.0168 (18)

Geometric parameters (Å, º) top

N1—C1	1.272 (3)	C16—H16A	0.9700
N1—C10	1.431 (3)	C16—H16B	0.9700
N2—C2	1.333 (2)	C17—H17A	0.9600
N2—C6	1.348 (2)	C17—H17B	0.9600
N3—C7	1.275 (2)	C17—H17C	0.9600
N3—C20	1.424 (3)	C18—C19	1.486 (3)
C1—C2	1.493 (3)	C18—H18A	0.9700
C1—C8	1.495 (3)	C18—H18B	0.9700
C2—C3	1.385 (3)	C19—H19A	0.9600
C3—C4	1.376 (3)	C19—H19B	0.9600
C3—H3B	0.9300	C19—H19C	0.9600
C4—C5	1.383 (3)	C20—C21	1.397 (3)
C4—H4A	0.9300	C20—C25	1.400 (3)
C5—C6	1.379 (3)	C21—C22	1.393 (3)
C5—H5A	0.9300	C21—C26	1.514 (3)
C6—C7	1.501 (3)	C22—C23	1.378 (3)
C7—C9	1.501 (3)	C22—H22A	0.9300
C8—H8A	0.9600	C23—C24	1.376 (3)
C8—H8B	0.9600	C23—H23A	0.9300
C8—H8C	0.9600	C24—C25	1.394 (3)
C9—H9A	0.9600	C24—H24A	0.9300
C9—H9B	0.9600	C25—C28	1.500 (3)
C9—H9C	0.9600	C26—C27	1.515 (3)
C10—C11	1.390 (3)	C26—H26A	0.9700
C10—C15	1.399 (3)	C26—H26B	0.9700
C11—C12	1.391 (3)	C27—H27A	0.9600
C11—C16	1.511 (3)	C27—H27B	0.9600
C12—C13	1.375 (3)	C27—H27C	0.9600
C12—H12A	0.9300	C28—C29	1.515 (3)
C13—C14	1.370 (3)	C28—H28A	0.9700
C13—H13A	0.9300	C28—H28B	0.9700
C14—C15	1.383 (3)	C29—H29A	0.9600
C14—H14A	0.9300	C29—H29B	0.9600
C15—C18	1.511 (3)	C29—H29C	0.9600
C16—C17	1.498 (3)

C1—N1—C10	120.5 (2)	C16—C17—H17A	109.5
C2—N2—C6	117.7 (2)	C16—C17—H17B	109.5
C7—N3—C20	121.0 (2)	H17A—C17—H17B	109.5
N1—C1—C2	117.5 (2)	C16—C17—H17C	109.5
N1—C1—C8	125.1 (2)	H17A—C17—H17C	109.5
C2—C1—C8	117.4 (2)	H17B—C17—H17C	109.5
N2—C2—C3	122.9 (2)	C19—C18—C15	110.6 (2)
N2—C2—C1	116.1 (2)	C19—C18—H18A	109.5
C3—C2—C1	121.0 (2)	C15—C18—H18A	109.5
C4—C3—C2	119.0 (2)	C19—C18—H18B	109.5
C4—C3—H3B	120.5	C15—C18—H18B	109.5
C2—C3—H3B	120.5	H18A—C18—H18B	108.1
C3—C4—C5	118.8 (2)	C18—C19—H19A	109.5
C3—C4—H4A	120.6	C18—C19—H19B	109.5
C5—C4—H4A	120.6	H19A—C19—H19B	109.5
C6—C5—C4	118.9 (2)	C18—C19—H19C	109.5
C6—C5—H5A	120.6	H19A—C19—H19C	109.5
C4—C5—H5A	120.6	H19B—C19—H19C	109.5
N2—C6—C5	122.7 (2)	C21—C20—C25	121.7 (2)
N2—C6—C7	115.6 (2)	C21—C20—N3	119.4 (2)
C5—C6—C7	121.7 (2)	C25—C20—N3	118.7 (2)
N3—C7—C6	117.1 (2)	C22—C21—C20	118.0 (2)
N3—C7—C9	125.3 (2)	C22—C21—C26	120.3 (2)
C6—C7—C9	117.6 (2)	C20—C21—C26	121.7 (2)
C1—C8—H8A	109.5	C23—C22—C21	121.5 (3)
C1—C8—H8B	109.5	C23—C22—H22A	119.3
H8A—C8—H8B	109.5	C21—C22—H22A	119.3
C1—C8—H8C	109.5	C24—C23—C22	119.4 (3)
H8A—C8—H8C	109.5	C24—C23—H23A	120.3
H8B—C8—H8C	109.5	C22—C23—H23A	120.3
C7—C9—H9A	109.5	C23—C24—C25	121.7 (3)
C7—C9—H9B	109.5	C23—C24—H24A	119.1
H9A—C9—H9B	109.5	C25—C24—H24A	119.1
C7—C9—H9C	109.5	C24—C25—C20	117.7 (2)
H9A—C9—H9C	109.5	C24—C25—C28	121.1 (2)
H9B—C9—H9C	109.5	C20—C25—C28	121.2 (2)
C11—C10—C15	121.4 (2)	C21—C26—C27	112.7 (2)
C11—C10—N1	118.6 (2)	C21—C26—H26A	109.0
C15—C10—N1	119.9 (2)	C27—C26—H26A	109.0
C10—C11—C12	118.2 (2)	C21—C26—H26B	109.0
C10—C11—C16	119.5 (2)	C27—C26—H26B	109.0
C12—C11—C16	122.2 (2)	H26A—C26—H26B	107.8
C13—C12—C11	121.0 (3)	C26—C27—H27A	109.5
C13—C12—H12A	119.5	C26—C27—H27B	109.5
C11—C12—H12A	119.5	H27A—C27—H27B	109.5
C14—C13—C12	119.8 (3)	C26—C27—H27C	109.5
C14—C13—H13A	120.1	H27A—C27—H27C	109.5
C12—C13—H13A	120.1	H27B—C27—H27C	109.5
C13—C14—C15	121.7 (3)	C25—C28—C29	113.5 (2)
C13—C14—H14A	119.2	C25—C28—H28A	108.9
C15—C14—H14A	119.2	C29—C28—H28A	108.9
C14—C15—C10	117.9 (2)	C25—C28—H28B	108.9
C14—C15—C18	120.7 (3)	C29—C28—H28B	108.9
C10—C15—C18	121.4 (2)	H28A—C28—H28B	107.7
C17—C16—C11	117.4 (2)	C28—C29—H29A	109.5
C17—C16—H16A	108.0	C28—C29—H29B	109.5
C11—C16—H16A	108.0	H29A—C29—H29B	109.5
C17—C16—H16B	108.0	C28—C29—H29C	109.5
C11—C16—H16B	108.0	H29A—C29—H29C	109.5
H16A—C16—H16B	107.2	H29B—C29—H29C	109.5

C10—N1—C1—C2	179.8 (2)	C12—C13—C14—C15	1.0 (4)
C10—N1—C1—C8	0.3 (4)	C13—C14—C15—C10	−1.0 (4)
C6—N2—C2—C3	0.2 (3)	C13—C14—C15—C18	178.4 (2)
C6—N2—C2—C1	−179.9 (2)	C11—C10—C15—C14	−0.2 (4)
N1—C1—C2—N2	−177.1 (2)	N1—C10—C15—C14	177.2 (2)
C8—C1—C2—N2	2.4 (3)	C11—C10—C15—C18	−179.6 (2)
N1—C1—C2—C3	2.8 (3)	N1—C10—C15—C18	−2.3 (4)
C8—C1—C2—C3	−177.7 (2)	C10—C11—C16—C17	−158.5 (2)
N2—C2—C3—C4	0.0 (4)	C12—C11—C16—C17	22.1 (4)
C1—C2—C3—C4	−179.9 (2)	C14—C15—C18—C19	−98.9 (3)
C2—C3—C4—C5	0.0 (4)	C10—C15—C18—C19	80.6 (3)
C3—C4—C5—C6	−0.1 (3)	C7—N3—C20—C21	91.8 (3)
C2—N2—C6—C5	−0.3 (3)	C7—N3—C20—C25	−93.3 (3)
C2—N2—C6—C7	179.4 (2)	C25—C20—C21—C22	−1.1 (3)
C4—C5—C6—N2	0.3 (3)	N3—C20—C21—C22	173.6 (2)
C4—C5—C6—C7	−179.4 (2)	C25—C20—C21—C26	−178.9 (2)
C20—N3—C7—C6	177.2 (2)	N3—C20—C21—C26	−4.2 (3)
C20—N3—C7—C9	−1.0 (4)	C20—C21—C22—C23	−0.9 (4)
N2—C6—C7—N3	−178.6 (2)	C26—C21—C22—C23	177.0 (2)
C5—C6—C7—N3	1.1 (3)	C21—C22—C23—C24	1.7 (4)
N2—C6—C7—C9	−0.2 (3)	C22—C23—C24—C25	−0.6 (4)
C5—C6—C7—C9	179.5 (2)	C23—C24—C25—C20	−1.3 (4)
C1—N1—C10—C11	−91.4 (3)	C23—C24—C25—C28	179.4 (2)
C1—N1—C10—C15	91.2 (3)	C21—C20—C25—C24	2.1 (3)
C15—C10—C11—C12	1.4 (3)	N3—C20—C25—C24	−172.6 (2)
N1—C10—C11—C12	−175.95 (19)	C21—C20—C25—C28	−178.5 (2)
C15—C10—C11—C16	−178.0 (2)	N3—C20—C25—C28	6.8 (3)
N1—C10—C11—C16	4.6 (3)	C22—C21—C26—C27	−100.8 (3)
C10—C11—C12—C13	−1.5 (4)	C20—C21—C26—C27	77.0 (3)
C16—C11—C12—C13	177.9 (2)	C24—C25—C28—C29	102.6 (3)
C11—C12—C13—C14	0.3 (4)	C20—C25—C28—C29	−76.7 (3)

Experimental details

Crystal data
Chemical formula	C₂₉H₃₅N₃
M_r	425.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	7.9390 (8), 12.3208 (13), 25.998 (3)
β (°)	96.234 (2)
V (Å³)	2528.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.983, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	13906, 4938, 2362
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.101, 0.95
No. of reflections	4938
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

N1—C1	1.272 (3)	N2—C6	1.348 (2)
N1—C10	1.431 (3)	N3—C7	1.275 (2)
N2—C2	1.333 (2)	N3—C20	1.424 (3)

Acknowledgements

This work was supported by the National Natural Science Foundation of China (20671025 and 20771030), the Young Foundation of Heilongjiang Province in China (QC06C029), Heilongjiang Natural Science Foundation (B200603) and the Science Innovation Special Foundation of Harbin City, China (2006RFQXG037).

References

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