(E)-N-[2-(Benzyl­iminometh­yl)phen­yl]-2,6-diisopropyl­aniline

Liu, Y.-C.; Lin, C.-H.; Chen, H.-L.; Ko, B.-T.

doi:10.1107/S1600536809042202

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2791

https://doi.org/10.1107/S1600536809042202

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(E)-N-[2-(Benzyliminomethyl)phenyl]-2,6-diisopropylaniline

Yi-Chang Liu,^a Chia-Her Lin,^a Hsiao-Li Chen ^b and Bao-Tsan Ko ^a ^*

^aDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 320, Taiwan, and ^bDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
^*Correspondence e-mail: btko@cycu.edu.tw

(Received 12 October 2009; accepted 14 October 2009; online 17 October 2009)

The molecular conformation of the title compound, C₂₆H₃₀N₂, is reinforced by an intramolecular N—H⋯N hydrogen bond, resulting in an almost planar [mean deviation of 0.023 (2) Å] S(6) ring. The dihedral angles between the central benzene ring and the terminal unsubstituted and substituted aromatic rings are 64.45 (9) and 89.40 (8)°, respectively.

Related literature

For background information on anilido-aldimine ligands, see: Lee et al. (2005 ); Yao et al. (2008 ). For related structures: see: Gao et al. (2008 ); Tsai et al. (2009 ).

Experimental

Crystal data

C₂₆H₃₀N₂
M_r = 370.52
Triclinic, $[P \overline 1]$
a = 8.0583 (3) Å
b = 10.9186 (4) Å
c = 13.5974 (5) Å
α = 75.823 (2)°
β = 77.933 (2)°
γ = 82.709 (2)°
V = 1130.68 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 296 K
0.53 × 0.46 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.965, T_max = 0.979
24959 measured reflections
5557 independent reflections
3150 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.178
S = 1.00
5557 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.86	2.03	2.7113 (15)	136

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; 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 I, global. DOI: https://doi.org/10.1107/S1600536809042202/hb5139sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042202/hb5139Isup2.hkl

checkCIF report

Comment top

Recently, anilido-aldimine (AA) metal compounds have been attracting considerable attention, mainly due to their applications in the catalytic polymerization (Lee et al., 2005 & Yao et al., 2008). These AA ligands can be designed to control the steric or electronic effect to provide a single active metal center for minimizing the side reaction. For instance, a series of NNN-tridentate AA rare-earth metal complexes has been demonstrated that the pendant arm of the quinolinyl group can coordinate with the metal to increase the sterics and coordination sites of the ligand, creating a single active site nature to initiate the polymerization of ε-caprolactone (ε-CL). (Gao et al., 2008). Most recently, Tsai et al., (2009) have successfully synthesized and structural characterized the Mg (II) and Zn (II) complexes supported from a novel NNN-tridentate AA with the pendant arm on the imine nitrogen and have demonstrated their catalytic studies of ring-opening polymerization of ε-CL and L-lactide. Therefore, our group is interested in developing new approaches for the synthesis of bi- or multi-dentate AA from the substituted benzaldehyde derivatives. Herein, we report the synthesis and crystal structure of the title compound, (I), a potential NN-bidentate AA ligand for the preparation of aluminium, magnesium and zinc complexes (Scheme 1).

The solid structure of (I) reveals the phenyl configuration containing one 2,6-diisopropylphenylamino functionalized group and one benzyl substituted imine group on the ortho position (Fig. 1). It was found that there is an intramolecular N—H···N hydrogen bond between the amine and imine groups (Table 1). It is interesting to note that the six-member ring (N1, C7, C2, C1, N2, H2A) formed from the N—H···N hydrogen-bond is almost planar with a mean deviation of 0.023 (2) Å.

Related literature top

For background information on anilido-aldimine ligands, see: Lee et al. (2005); Yao et al. (2008). For related structures: see: Gao et al. (2008); Tsai et al. (2009).

Experimental top

The title compound (I) was synthesized by the following procedures (Fig. 2):

2-(2-Bromophenyl)-1, 3-dioxolane (2). In a 50 ml two-necked round-bottomed flask, a solution of 2-bromobenzaldehyde, 1 (20.0 g, 108.0 mmol) in 40 ml of toluene was added in one portion anhydrous ethylene glycol (8.69 g, 140.0 mmol) and p-toluenesulfonic acid (186 mg, 1.08 mmol). The resulting solution mixture was refluxed until the theoretical yield of water had been collected in a Dean–Stark trap. After 16 h, the mixture was cooled, washed with 10% aqueous sodium hydroxide (2 x 30 ml), followed by deionized water (2 x 30 ml), brine (1 x 30 ml) and the organic layer was dried over anhydrous MgSO₄. The solvent was removed in vacuo to give 24.18 g (94%) of a clear yellow viscous oil, 2. ¹H NMR (CDCl₃, p.p.m.): δ 7.18 - 7.60 (m, 4H, PhH), 6.09 (s, 1H, PhCH), 4.03–4.17 (m, 4H, OCH₂CH₂O).

2-(2, 6-Diisopropyl-phenylamino)benzaldehyde (3). In a 250 ml two-necked round-bottom flask equipped with a magnetic stir bar and a condenser, Pd(OAc)₂ (71 mg, 0.32 mmol), sodium tert-butoxide (6.15 g, 64.0 mmol) and 2-(2-bromophenyl)-1, 3-dioxolane, 2 (7.30 g, 32.0 mmol) was degassed by vacuum. Under N₂ atmosphere, tri-tert-butylphosphane (129 mg, 0.64 mmol), 2, 6-diisopropylaniline (6.29 g, 35.0 mmol) and anhydrous tetrahydrofuran (50 ml) were added and refluxed for 16 h. The reaction mixture were then cooled to ambient temperature, filtered the resulting solution. The solution portion was extracted with ethyl acetate and deionized water washing twice, and the organic layer was dried over magnesium sulfate and the solvent was evaporated under vacuum. The crude product was dissolved in hexane (100 ml) and was cooled in 253 K overnight to obtain the brown solids (8.11 g, 78%)..¹H NMR (CDCl₃, p.p.m.): δ 7.39 (d, J = 7.5 Hz, 1H, PhH), 7.30–7.20 (m, 3H, PhH), 7.05 (t, J = 7.5 Hz, 1H, PhH), 6.71 (t, J = 7.5 Hz, 1H, PhH), 6.33 (s, 1H, PhNH), 6.18 (d, J = 8.1 Hz, 1H, PhH), 5.99 (s, 1H, PhCH), 4.07–4.18 (m, 4H, OCH₂CH₂O), 3.14 (m, J = 6.9 Hz, 2H, CH(CH₃)₂), 1.16 (d, J = 6.9 Hz, 6H, CH(CH₃)₂), 1.12 (d, J = 6.9 Hz, 6H, CH(CH₃)₂). The above brown solids, 2-[2-(2, 6-diisopropylanilino)phenyl]-1,3-dioxolane (5.34 g, 16.4 mmol), trifluoroacetic acid (1.14 g, 10.0 mmol) and MeOH (30 ml) were added in the 100 ml round-bottom and the mixture was stirred at ambient temperature. After 1 h, the resulting solution was removed the solvent in vacuo. The residue was then extracted with ethyl acetate and deionized water washing twice. The final organic layer was dried over anhydrous MgSO₄ and the solvent was removed under vacuum to give white solids (4.33 g, 94%). ¹H NMR (CDCl₃, p.p.m.): δ 9.97 (s, 1H, PhNH), 9.57 (s, 1H, PhC(O)H), 7.57 (d, J = 7.8 Hz, 1H, PhH), 7.23–7.38 (m, 4H, PhH), 6.74 (t, J = 7.5 Hz, 1H, PhH), 6.25 (d, J = 8.4 Hz, 1H, PhH), 3.08 (m, J = 6.9 Hz, 2H, CH(CH₃)₂), 1.18 (d, J = 6.9 Hz, 6H, CH(CH₃)₂), 1.12 (d, J = 6.9 Hz, 6H, CH(CH₃)₂).

(E)—N-(2-((benzylimino)methyl)phenyl)-2,6-diisopropylaniline (I). A mixture of benzylamine (0.33 ml, 3.0 mmol), 2-(2, 6-diisopropyl-phenylamino)benzaldehyde, 3 (0.76 g, 2.7 mmol) and anhydrous MgSO₄(2.0 g) were stirred in reflux hexane (20 ml) for 12 h. Volatile materials were removed under vacuum to give the white solids. Yield: 0.75 g (75%). Colourless crystals were obtained from the saturated Et₂O solution. ¹H NMR (CDCl₃, p.p.m.): δ 10.60 (s, 1H, PhNH), 8.61 (s, 1H, HC=N), 6.24–7.37 (m, 12H, PhH), 4.87(s, 2H, CH₂Ph), 3.14 (m,J = 6.9 Hz, 2H, CH(CH₃)₂), 1.20 (d, J = 6.9 Hz, 6H, CH(CH₃)₂), 1.10 (d,J = 6.9 Hz, 6H, CH(CH₃)₂).

Structure description top

For background information on anilido-aldimine ligands, see: Lee et al. (2005); Yao et al. (2008). For related structures: see: Gao et al. (2008); Tsai et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as the small spheres of arbitrary radius.
	Fig. 2. Reaction scheme leading to the title compound.

(E)-N-[2-(Benzyliminomethyl)phenyl]-2,6-diisopropylaniline top

Crystal data top

C₂₆H₃₀N₂	Z = 2
M_r = 370.52	F(000) = 400
Triclinic, P1	D_x = 1.088 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0583 (3) Å	Cell parameters from 9972 reflections
b = 10.9186 (4) Å	θ = 2.2–28.2°
c = 13.5974 (5) Å	µ = 0.06 mm⁻¹
α = 75.823 (2)°	T = 296 K
β = 77.933 (2)°	Block, colourless
γ = 82.709 (2)°	0.53 × 0.46 × 0.32 mm
V = 1130.68 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	5557 independent reflections
Radiation source: fine-focus sealed tube	3150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.4°, θ_min = 1.6°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −14→14
T_min = 0.965, T_max = 0.979	l = −18→18
24959 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.102P)²] where P = (F_o² + 2F_c²)/3
5557 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₆H₃₀N₂	γ = 82.709 (2)°
M_r = 370.52	V = 1130.68 (7) Å³
Triclinic, P1	Z = 2
a = 8.0583 (3) Å	Mo Kα radiation
b = 10.9186 (4) Å	µ = 0.06 mm⁻¹
c = 13.5974 (5) Å	T = 296 K
α = 75.823 (2)°	0.53 × 0.46 × 0.32 mm
β = 77.933 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5557 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3150 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.979	R_int = 0.061
24959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
5557 reflections	Δρ_min = −0.18 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	0.46771 (17)	0.32146 (10)	0.01875 (8)	0.0622 (3)
N2	0.45207 (13)	0.23379 (11)	0.22480 (8)	0.0585 (3)
H2A	0.4023	0.2482	0.1725	0.070*
C1	0.62287 (15)	0.24628 (12)	0.20617 (10)	0.0514 (3)
C2	0.70993 (16)	0.28903 (12)	0.10401 (10)	0.0551 (3)
C3	0.8843 (2)	0.29836 (17)	0.08793 (13)	0.0797 (5)
H3A	0.9424	0.3256	0.0208	0.096*
C4	0.9738 (2)	0.26921 (19)	0.16647 (15)	0.0924 (6)
H4A	1.0904	0.2768	0.1532	0.111*
C5	0.8877 (2)	0.22822 (18)	0.26596 (15)	0.0870 (5)
H5A	0.9469	0.2089	0.3204	0.104*
C6	0.71649 (18)	0.21556 (15)	0.28577 (12)	0.0686 (4)
H6A	0.6615	0.1860	0.3533	0.082*
C7	0.6255 (2)	0.32311 (13)	0.01581 (11)	0.0642 (4)
H7A	0.6933	0.3485	−0.0488	0.077*
C8	0.4047 (2)	0.35949 (15)	−0.07799 (12)	0.0796 (5)
H8A	0.5003	0.3780	−0.1345	0.096*
H8B	0.3306	0.4368	−0.0778	0.096*
C9	0.30892 (18)	0.26118 (13)	−0.09649 (10)	0.0607 (4)
C10	0.2035 (2)	0.29393 (18)	−0.16839 (13)	0.0834 (5)
H10A	0.1899	0.3779	−0.2039	0.100*
C11	0.1182 (3)	0.2036 (2)	−0.18815 (17)	0.1083 (7)
H11A	0.0475	0.2272	−0.2368	0.130*
C12	0.1365 (3)	0.0791 (2)	−0.13670 (17)	0.1025 (6)
H12A	0.0798	0.0180	−0.1507	0.123*
C13	0.2379 (2)	0.04685 (17)	−0.06566 (15)	0.0885 (5)
H13A	0.2496	−0.0370	−0.0297	0.106*
C14	0.3242 (2)	0.13565 (14)	−0.04556 (11)	0.0695 (4)
H14A	0.3944	0.1108	0.0033	0.083*
C15	0.35020 (15)	0.19827 (12)	0.32539 (9)	0.0511 (3)
C16	0.32423 (16)	0.07005 (13)	0.36722 (10)	0.0559 (3)
C17	0.22163 (19)	0.03899 (15)	0.46347 (11)	0.0703 (4)
H17A	0.2019	−0.0454	0.4928	0.084*
C18	0.1483 (2)	0.13004 (18)	0.51657 (12)	0.0802 (5)
H18A	0.0799	0.1068	0.5813	0.096*
C19	0.1753 (2)	0.25461 (17)	0.47477 (12)	0.0782 (5)
H19A	0.1247	0.3155	0.5114	0.094*
C20	0.27753 (18)	0.29204 (14)	0.37815 (11)	0.0625 (4)
C21	0.3092 (3)	0.43053 (15)	0.33367 (15)	0.0877 (5)
H21A	0.3848	0.4336	0.2667	0.105*
C22	0.1524 (4)	0.5088 (2)	0.3115 (3)	0.1691 (13)
H22A	0.1784	0.5951	0.2822	0.254*
H22B	0.0705	0.5047	0.3744	0.254*
H22C	0.1064	0.4775	0.2636	0.254*
C23	0.4053 (6)	0.4786 (3)	0.3972 (3)	0.1996 (18)
H23A	0.4256	0.5657	0.3664	0.299*
H23B	0.5122	0.4291	0.4003	0.299*
H23C	0.3401	0.4719	0.4657	0.299*
C24	0.40181 (19)	−0.03072 (14)	0.30860 (13)	0.0717 (4)
H24A	0.5049	0.0004	0.2614	0.086*
C25	0.4532 (3)	−0.15552 (19)	0.3797 (2)	0.1265 (8)
H25A	0.5297	−0.1403	0.4201	0.190*
H25B	0.5087	−0.2145	0.3388	0.190*
H25C	0.3535	−0.1901	0.4247	0.190*
C26	0.2816 (3)	−0.0540 (2)	0.24438 (15)	0.1028 (6)
H26A	0.2491	0.0247	0.2003	0.154*
H26B	0.1820	−0.0891	0.2891	0.154*
H26C	0.3375	−0.1123	0.2030	0.154*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0752 (8)	0.0591 (7)	0.0527 (7)	−0.0122 (6)	−0.0189 (6)	−0.0042 (5)
N2	0.0467 (6)	0.0823 (8)	0.0450 (6)	−0.0171 (5)	−0.0106 (5)	−0.0034 (5)
C1	0.0459 (7)	0.0537 (7)	0.0546 (8)	−0.0083 (5)	−0.0080 (6)	−0.0113 (6)
C2	0.0547 (8)	0.0551 (7)	0.0545 (8)	−0.0105 (6)	−0.0037 (6)	−0.0124 (6)
C3	0.0557 (9)	0.1029 (12)	0.0750 (10)	−0.0197 (8)	0.0063 (8)	−0.0185 (9)
C4	0.0484 (9)	0.1297 (15)	0.0985 (14)	−0.0193 (9)	−0.0079 (9)	−0.0231 (12)
C5	0.0588 (10)	0.1167 (14)	0.0885 (12)	−0.0088 (9)	−0.0277 (9)	−0.0160 (10)
C6	0.0541 (9)	0.0904 (10)	0.0607 (9)	−0.0129 (7)	−0.0157 (7)	−0.0078 (7)
C7	0.0755 (10)	0.0643 (8)	0.0498 (8)	−0.0217 (7)	−0.0010 (7)	−0.0079 (6)
C8	0.1094 (13)	0.0708 (9)	0.0597 (9)	−0.0189 (9)	−0.0332 (9)	0.0041 (7)
C9	0.0649 (9)	0.0695 (9)	0.0463 (7)	0.0001 (6)	−0.0108 (6)	−0.0130 (6)
C10	0.0935 (12)	0.0892 (11)	0.0719 (10)	0.0053 (9)	−0.0353 (9)	−0.0155 (9)
C11	0.1071 (16)	0.1313 (19)	0.1084 (16)	0.0040 (13)	−0.0600 (13)	−0.0408 (14)
C12	0.0989 (15)	0.1114 (16)	0.1186 (17)	−0.0122 (12)	−0.0366 (13)	−0.0503 (13)
C13	0.0992 (13)	0.0763 (11)	0.0974 (13)	−0.0104 (9)	−0.0261 (11)	−0.0250 (10)
C14	0.0754 (10)	0.0696 (9)	0.0664 (9)	−0.0040 (7)	−0.0203 (8)	−0.0155 (7)
C15	0.0411 (6)	0.0669 (8)	0.0459 (7)	−0.0101 (5)	−0.0108 (5)	−0.0083 (6)
C16	0.0439 (7)	0.0666 (8)	0.0578 (8)	−0.0123 (6)	−0.0102 (6)	−0.0102 (6)
C17	0.0667 (9)	0.0768 (10)	0.0618 (9)	−0.0243 (7)	−0.0055 (7)	−0.0009 (7)
C18	0.0742 (10)	0.1087 (14)	0.0527 (9)	−0.0260 (9)	0.0057 (7)	−0.0138 (9)
C19	0.0754 (10)	0.0944 (12)	0.0675 (10)	−0.0056 (8)	−0.0022 (8)	−0.0332 (9)
C20	0.0596 (8)	0.0686 (8)	0.0609 (8)	−0.0075 (6)	−0.0127 (7)	−0.0148 (7)
C21	0.1018 (13)	0.0631 (9)	0.0948 (12)	−0.0060 (9)	−0.0115 (10)	−0.0175 (9)
C22	0.152 (2)	0.0931 (16)	0.229 (3)	0.0249 (16)	−0.043 (2)	0.0145 (19)
C23	0.305 (5)	0.0993 (17)	0.238 (4)	−0.079 (2)	−0.137 (4)	−0.013 (2)
C24	0.0598 (9)	0.0696 (9)	0.0848 (11)	−0.0114 (7)	−0.0024 (8)	−0.0220 (8)
C25	0.147 (2)	0.0824 (13)	0.158 (2)	0.0248 (12)	−0.0558 (17)	−0.0354 (14)
C26	0.0970 (13)	0.1335 (17)	0.0957 (13)	−0.0102 (11)	−0.0151 (11)	−0.0607 (12)

Geometric parameters (Å, º) top

N1—C7	1.2659 (18)	C14—H14A	0.9300
N1—C8	1.4557 (17)	C15—C20	1.3921 (19)
N2—C1	1.3646 (16)	C15—C16	1.4006 (18)
N2—C15	1.4307 (16)	C16—C17	1.3831 (19)
N2—H2A	0.8600	C16—C24	1.511 (2)
C1—C6	1.3973 (18)	C17—C18	1.372 (2)
C1—C2	1.4134 (18)	C17—H17A	0.9300
C2—C3	1.389 (2)	C18—C19	1.366 (2)
C2—C7	1.449 (2)	C18—H18A	0.9300
C3—C4	1.364 (2)	C19—C20	1.393 (2)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.379 (2)	C20—C21	1.517 (2)
C4—H4A	0.9300	C21—C22	1.475 (3)
C5—C6	1.367 (2)	C21—C23	1.492 (3)
C5—H5A	0.9300	C21—H21A	0.9800
C6—H6A	0.9300	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C9	1.495 (2)	C22—H22C	0.9600
C8—H8A	0.9700	C23—H23A	0.9600
C8—H8B	0.9700	C23—H23B	0.9600
C9—C14	1.379 (2)	C23—H23C	0.9600
C9—C10	1.380 (2)	C24—C26	1.513 (2)
C10—C11	1.377 (3)	C24—C25	1.530 (3)
C10—H10A	0.9300	C24—H24A	0.9800
C11—C12	1.374 (3)	C25—H25A	0.9600
C11—H11A	0.9300	C25—H25B	0.9600
C12—C13	1.348 (3)	C25—H25C	0.9600
C12—H12A	0.9300	C26—H26A	0.9600
C13—C14	1.371 (2)	C26—H26B	0.9600
C13—H13A	0.9300	C26—H26C	0.9600

C7—N1—C8	118.36 (13)	C17—C16—C15	117.56 (13)
C1—N2—C15	124.45 (11)	C17—C16—C24	120.99 (13)
C1—N2—H2A	117.8	C15—C16—C24	121.43 (12)
C15—N2—H2A	117.8	C18—C17—C16	121.44 (14)
N2—C1—C6	121.68 (12)	C18—C17—H17A	119.3
N2—C1—C2	119.94 (12)	C16—C17—H17A	119.3
C6—C1—C2	118.37 (12)	C19—C18—C17	120.24 (14)
C3—C2—C1	118.26 (13)	C19—C18—H18A	119.9
C3—C2—C7	118.80 (13)	C17—C18—H18A	119.9
C1—C2—C7	122.93 (12)	C18—C19—C20	121.11 (15)
C4—C3—C2	122.75 (15)	C18—C19—H19A	119.4
C4—C3—H3A	118.6	C20—C19—H19A	119.4
C2—C3—H3A	118.6	C15—C20—C19	117.74 (14)
C3—C4—C5	118.60 (15)	C15—C20—C21	121.76 (13)
C3—C4—H4A	120.7	C19—C20—C21	120.49 (14)
C5—C4—H4A	120.7	C22—C21—C23	114.9 (2)
C6—C5—C4	120.95 (16)	C22—C21—C20	112.11 (18)
C6—C5—H5A	119.5	C23—C21—C20	111.35 (17)
C4—C5—H5A	119.5	C22—C21—H21A	105.9
C5—C6—C1	121.06 (14)	C23—C21—H21A	105.9
C5—C6—H6A	119.5	C20—C21—H21A	105.9
C1—C6—H6A	119.5	C21—C22—H22A	109.5
N1—C7—C2	125.85 (13)	C21—C22—H22B	109.5
N1—C7—H7A	117.1	H22A—C22—H22B	109.5
C2—C7—H7A	117.1	C21—C22—H22C	109.5
N1—C8—C9	113.42 (12)	H22A—C22—H22C	109.5
N1—C8—H8A	108.9	H22B—C22—H22C	109.5
C9—C8—H8A	108.9	C21—C23—H23A	109.5
N1—C8—H8B	108.9	C21—C23—H23B	109.5
C9—C8—H8B	108.9	H23A—C23—H23B	109.5
H8A—C8—H8B	107.7	C21—C23—H23C	109.5
C14—C9—C10	117.49 (14)	H23A—C23—H23C	109.5
C14—C9—C8	122.37 (13)	H23B—C23—H23C	109.5
C10—C9—C8	120.13 (13)	C16—C24—C26	110.94 (13)
C11—C10—C9	120.70 (17)	C16—C24—C25	112.51 (15)
C11—C10—H10A	119.7	C26—C24—C25	109.81 (16)
C9—C10—H10A	119.7	C16—C24—H24A	107.8
C12—C11—C10	120.62 (18)	C26—C24—H24A	107.8
C12—C11—H11A	119.7	C25—C24—H24A	107.8
C10—C11—H11A	119.7	C24—C25—H25A	109.5
C13—C12—C11	118.89 (18)	C24—C25—H25B	109.5
C13—C12—H12A	120.6	H25A—C25—H25B	109.5
C11—C12—H12A	120.6	C24—C25—H25C	109.5
C12—C13—C14	121.10 (18)	H25A—C25—H25C	109.5
C12—C13—H13A	119.5	H25B—C25—H25C	109.5
C14—C13—H13A	119.5	C24—C26—H26A	109.5
C13—C14—C9	121.20 (15)	C24—C26—H26B	109.5
C13—C14—H14A	119.4	H26A—C26—H26B	109.5
C9—C14—H14A	119.4	C24—C26—H26C	109.5
C20—C15—C16	121.90 (12)	H26A—C26—H26C	109.5
C20—C15—N2	119.19 (12)	H26B—C26—H26C	109.5
C16—C15—N2	118.90 (12)

C15—N2—C1—C6	4.9 (2)	C8—C9—C14—C13	−178.51 (16)
C15—N2—C1—C2	−176.32 (12)	C1—N2—C15—C20	88.21 (16)
N2—C1—C2—C3	−178.86 (12)	C1—N2—C15—C16	−92.83 (15)
C6—C1—C2—C3	−0.01 (19)	C20—C15—C16—C17	0.5 (2)
N2—C1—C2—C7	1.0 (2)	N2—C15—C16—C17	−178.38 (11)
C6—C1—C2—C7	179.87 (12)	C20—C15—C16—C24	179.15 (13)
C1—C2—C3—C4	−0.6 (2)	N2—C15—C16—C24	0.22 (18)
C7—C2—C3—C4	179.48 (16)	C15—C16—C17—C18	−0.3 (2)
C2—C3—C4—C5	0.3 (3)	C24—C16—C17—C18	−178.90 (14)
C3—C4—C5—C6	0.7 (3)	C16—C17—C18—C19	0.1 (3)
C4—C5—C6—C1	−1.4 (3)	C17—C18—C19—C20	−0.2 (3)
N2—C1—C6—C5	179.82 (14)	C16—C15—C20—C19	−0.6 (2)
C2—C1—C6—C5	1.0 (2)	N2—C15—C20—C19	178.32 (12)
C8—N1—C7—C2	179.73 (13)	C16—C15—C20—C21	178.58 (13)
C3—C2—C7—N1	−178.73 (13)	N2—C15—C20—C21	−2.5 (2)
C1—C2—C7—N1	1.4 (2)	C18—C19—C20—C15	0.4 (2)
C7—N1—C8—C9	124.20 (15)	C18—C19—C20—C21	−178.78 (15)
N1—C8—C9—C14	−19.0 (2)	C15—C20—C21—C22	115.1 (2)
N1—C8—C9—C10	162.48 (14)	C19—C20—C21—C22	−65.7 (3)
C14—C9—C10—C11	−0.3 (2)	C15—C20—C21—C23	−114.7 (3)
C8—C9—C10—C11	178.24 (18)	C19—C20—C21—C23	64.5 (3)
C9—C10—C11—C12	−0.1 (3)	C17—C16—C24—C26	87.45 (18)
C10—C11—C12—C13	0.7 (3)	C15—C16—C24—C26	−91.11 (17)
C11—C12—C13—C14	−1.0 (3)	C17—C16—C24—C25	−36.0 (2)
C12—C13—C14—C9	0.7 (3)	C15—C16—C24—C25	145.44 (16)
C10—C9—C14—C13	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.03	2.7113 (15)	136

Experimental details

Crystal data
Chemical formula	C₂₆H₃₀N₂
M_r	370.52
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0583 (3), 10.9186 (4), 13.5974 (5)
α, β, γ (°)	75.823 (2), 77.933 (2), 82.709 (2)
V (Å³)	1130.68 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.53 × 0.46 × 0.32

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.965, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	24959, 5557, 3150
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.178, 1.00
No. of reflections	5557
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.03	2.7113 (15)	136

Acknowledgements

We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC97–2113-M-033–005-MY2) and in part from the project of specific research fields in Chung Yuan Christian University, Taiwan (No. CYCU-98-CR—CH).

References

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