organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S.-I., Yun, H., Lee, H. & Park, Y.-W. (2005). J. Am. Chem. Soc. 127, 3031-3037.]); Yao et al. (2008[Yao, W., Mu, Y., Gao, A., Gao, W. & Ye, L. (2008). Dalton Trans. pp. 3199-3206.]). For related structures: see: Gao et al. (2008[Gao, W., Cui, D., Liu, X., Zhang, Y. & Mu, Y. (2008). Organometallics, 27, 5889-5893.]); Tsai et al. (2009[Tsai, Y.-H., Lin, C.-H., Lin, C.-C. & Ko, B.-T. (2009). J. Polym. Sci. Part. A: Polym. Chem. 47, 4927-4936.]).

[Scheme 1]

Experimental

Crystal data
  • C26H30N2

  • Mr = 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.979

  • 24959 measured reflections

  • 5557 independent reflections

  • 3150 reflections with I > 2σ(I)

  • Rint = 0.061

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.178

  • S = 1.00

  • 5557 reflections

  • 253 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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).

Refinement top

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å with Uiso(H) = 1.2 Ueq(C) for phenyl hydrogen; 0.96 Å with Uiso(H) = 1.5 Ueq(C) for CH3 group; 0.97 Å with Uiso(H) = 1.2 Ueq(C) for CH2 group; 0.98 Å with Uiso(H) = 1.2 Ueq(C) for CH group; N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(C).

Structure description 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.

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
[Figure 1] 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.
[Figure 2] Fig. 2. Reaction scheme leading to the title compound.
(E)-N-[2-(Benzyliminomethyl)phenyl]-2,6-diisopropylaniline top
Crystal data top
C26H30N2Z = 2
Mr = 370.52F(000) = 400
Triclinic, P1Dx = 1.088 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0583 (3) ÅCell parameters from 9972 reflections
b = 10.9186 (4) Åθ = 2.2–28.2°
c = 13.5974 (5) ŵ = 0.06 mm1
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 tube3150 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 8.3333 pixels mm-1θmax = 28.4°, θmin = 1.6°
phi and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 1414
Tmin = 0.965, Tmax = 0.979l = 1818
24959 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.102P)2]
where P = (Fo2 + 2Fc2)/3
5557 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C26H30N2γ = 82.709 (2)°
Mr = 370.52V = 1130.68 (7) Å3
Triclinic, P1Z = 2
a = 8.0583 (3) ÅMo Kα radiation
b = 10.9186 (4) ŵ = 0.06 mm1
c = 13.5974 (5) ÅT = 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)
Tmin = 0.965, Tmax = 0.979Rint = 0.061
24959 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.00Δρmax = 0.22 e Å3
5557 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
N10.46771 (17)0.32146 (10)0.01875 (8)0.0622 (3)
N20.45207 (13)0.23379 (11)0.22480 (8)0.0585 (3)
H2A0.40230.24820.17250.070*
C10.62287 (15)0.24628 (12)0.20617 (10)0.0514 (3)
C20.70993 (16)0.28903 (12)0.10401 (10)0.0551 (3)
C30.8843 (2)0.29836 (17)0.08793 (13)0.0797 (5)
H3A0.94240.32560.02080.096*
C40.9738 (2)0.26921 (19)0.16647 (15)0.0924 (6)
H4A1.09040.27680.15320.111*
C50.8877 (2)0.22822 (18)0.26596 (15)0.0870 (5)
H5A0.94690.20890.32040.104*
C60.71649 (18)0.21556 (15)0.28577 (12)0.0686 (4)
H6A0.66150.18600.35330.082*
C70.6255 (2)0.32311 (13)0.01581 (11)0.0642 (4)
H7A0.69330.34850.04880.077*
C80.4047 (2)0.35949 (15)0.07799 (12)0.0796 (5)
H8A0.50030.37800.13450.096*
H8B0.33060.43680.07780.096*
C90.30892 (18)0.26118 (13)0.09649 (10)0.0607 (4)
C100.2035 (2)0.29393 (18)0.16839 (13)0.0834 (5)
H10A0.18990.37790.20390.100*
C110.1182 (3)0.2036 (2)0.18815 (17)0.1083 (7)
H11A0.04750.22720.23680.130*
C120.1365 (3)0.0791 (2)0.13670 (17)0.1025 (6)
H12A0.07980.01800.15070.123*
C130.2379 (2)0.04685 (17)0.06566 (15)0.0885 (5)
H13A0.24960.03700.02970.106*
C140.3242 (2)0.13565 (14)0.04556 (11)0.0695 (4)
H14A0.39440.11080.00330.083*
C150.35020 (15)0.19827 (12)0.32539 (9)0.0511 (3)
C160.32423 (16)0.07005 (13)0.36722 (10)0.0559 (3)
C170.22163 (19)0.03899 (15)0.46347 (11)0.0703 (4)
H17A0.20190.04540.49280.084*
C180.1483 (2)0.13004 (18)0.51657 (12)0.0802 (5)
H18A0.07990.10680.58130.096*
C190.1753 (2)0.25461 (17)0.47477 (12)0.0782 (5)
H19A0.12470.31550.51140.094*
C200.27753 (18)0.29204 (14)0.37815 (11)0.0625 (4)
C210.3092 (3)0.43053 (15)0.33367 (15)0.0877 (5)
H21A0.38480.43360.26670.105*
C220.1524 (4)0.5088 (2)0.3115 (3)0.1691 (13)
H22A0.17840.59510.28220.254*
H22B0.07050.50470.37440.254*
H22C0.10640.47750.26360.254*
C230.4053 (6)0.4786 (3)0.3972 (3)0.1996 (18)
H23A0.42560.56570.36640.299*
H23B0.51220.42910.40030.299*
H23C0.34010.47190.46570.299*
C240.40181 (19)0.03072 (14)0.30860 (13)0.0717 (4)
H24A0.50490.00040.26140.086*
C250.4532 (3)0.15552 (19)0.3797 (2)0.1265 (8)
H25A0.52970.14030.42010.190*
H25B0.50870.21450.33880.190*
H25C0.35350.19010.42470.190*
C260.2816 (3)0.0540 (2)0.24438 (15)0.1028 (6)
H26A0.24910.02470.20030.154*
H26B0.18200.08910.28910.154*
H26C0.33750.11230.20300.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0752 (8)0.0591 (7)0.0527 (7)0.0122 (6)0.0189 (6)0.0042 (5)
N20.0467 (6)0.0823 (8)0.0450 (6)0.0171 (5)0.0106 (5)0.0034 (5)
C10.0459 (7)0.0537 (7)0.0546 (8)0.0083 (5)0.0080 (6)0.0113 (6)
C20.0547 (8)0.0551 (7)0.0545 (8)0.0105 (6)0.0037 (6)0.0124 (6)
C30.0557 (9)0.1029 (12)0.0750 (10)0.0197 (8)0.0063 (8)0.0185 (9)
C40.0484 (9)0.1297 (15)0.0985 (14)0.0193 (9)0.0079 (9)0.0231 (12)
C50.0588 (10)0.1167 (14)0.0885 (12)0.0088 (9)0.0277 (9)0.0160 (10)
C60.0541 (9)0.0904 (10)0.0607 (9)0.0129 (7)0.0157 (7)0.0078 (7)
C70.0755 (10)0.0643 (8)0.0498 (8)0.0217 (7)0.0010 (7)0.0079 (6)
C80.1094 (13)0.0708 (9)0.0597 (9)0.0189 (9)0.0332 (9)0.0041 (7)
C90.0649 (9)0.0695 (9)0.0463 (7)0.0001 (6)0.0108 (6)0.0130 (6)
C100.0935 (12)0.0892 (11)0.0719 (10)0.0053 (9)0.0353 (9)0.0155 (9)
C110.1071 (16)0.1313 (19)0.1084 (16)0.0040 (13)0.0600 (13)0.0408 (14)
C120.0989 (15)0.1114 (16)0.1186 (17)0.0122 (12)0.0366 (13)0.0503 (13)
C130.0992 (13)0.0763 (11)0.0974 (13)0.0104 (9)0.0261 (11)0.0250 (10)
C140.0754 (10)0.0696 (9)0.0664 (9)0.0040 (7)0.0203 (8)0.0155 (7)
C150.0411 (6)0.0669 (8)0.0459 (7)0.0101 (5)0.0108 (5)0.0083 (6)
C160.0439 (7)0.0666 (8)0.0578 (8)0.0123 (6)0.0102 (6)0.0102 (6)
C170.0667 (9)0.0768 (10)0.0618 (9)0.0243 (7)0.0055 (7)0.0009 (7)
C180.0742 (10)0.1087 (14)0.0527 (9)0.0260 (9)0.0057 (7)0.0138 (9)
C190.0754 (10)0.0944 (12)0.0675 (10)0.0056 (8)0.0022 (8)0.0332 (9)
C200.0596 (8)0.0686 (8)0.0609 (8)0.0075 (6)0.0127 (7)0.0148 (7)
C210.1018 (13)0.0631 (9)0.0948 (12)0.0060 (9)0.0115 (10)0.0175 (9)
C220.152 (2)0.0931 (16)0.229 (3)0.0249 (16)0.043 (2)0.0145 (19)
C230.305 (5)0.0993 (17)0.238 (4)0.079 (2)0.137 (4)0.013 (2)
C240.0598 (9)0.0696 (9)0.0848 (11)0.0114 (7)0.0024 (8)0.0220 (8)
C250.147 (2)0.0824 (13)0.158 (2)0.0248 (12)0.0558 (17)0.0354 (14)
C260.0970 (13)0.1335 (17)0.0957 (13)0.0102 (11)0.0151 (11)0.0607 (12)
Geometric parameters (Å, º) top
N1—C71.2659 (18)C14—H14A0.9300
N1—C81.4557 (17)C15—C201.3921 (19)
N2—C11.3646 (16)C15—C161.4006 (18)
N2—C151.4307 (16)C16—C171.3831 (19)
N2—H2A0.8600C16—C241.511 (2)
C1—C61.3973 (18)C17—C181.372 (2)
C1—C21.4134 (18)C17—H17A0.9300
C2—C31.389 (2)C18—C191.366 (2)
C2—C71.449 (2)C18—H18A0.9300
C3—C41.364 (2)C19—C201.393 (2)
C3—H3A0.9300C19—H19A0.9300
C4—C51.379 (2)C20—C211.517 (2)
C4—H4A0.9300C21—C221.475 (3)
C5—C61.367 (2)C21—C231.492 (3)
C5—H5A0.9300C21—H21A0.9800
C6—H6A0.9300C22—H22A0.9600
C7—H7A0.9300C22—H22B0.9600
C8—C91.495 (2)C22—H22C0.9600
C8—H8A0.9700C23—H23A0.9600
C8—H8B0.9700C23—H23B0.9600
C9—C141.379 (2)C23—H23C0.9600
C9—C101.380 (2)C24—C261.513 (2)
C10—C111.377 (3)C24—C251.530 (3)
C10—H10A0.9300C24—H24A0.9800
C11—C121.374 (3)C25—H25A0.9600
C11—H11A0.9300C25—H25B0.9600
C12—C131.348 (3)C25—H25C0.9600
C12—H12A0.9300C26—H26A0.9600
C13—C141.371 (2)C26—H26B0.9600
C13—H13A0.9300C26—H26C0.9600
C7—N1—C8118.36 (13)C17—C16—C15117.56 (13)
C1—N2—C15124.45 (11)C17—C16—C24120.99 (13)
C1—N2—H2A117.8C15—C16—C24121.43 (12)
C15—N2—H2A117.8C18—C17—C16121.44 (14)
N2—C1—C6121.68 (12)C18—C17—H17A119.3
N2—C1—C2119.94 (12)C16—C17—H17A119.3
C6—C1—C2118.37 (12)C19—C18—C17120.24 (14)
C3—C2—C1118.26 (13)C19—C18—H18A119.9
C3—C2—C7118.80 (13)C17—C18—H18A119.9
C1—C2—C7122.93 (12)C18—C19—C20121.11 (15)
C4—C3—C2122.75 (15)C18—C19—H19A119.4
C4—C3—H3A118.6C20—C19—H19A119.4
C2—C3—H3A118.6C15—C20—C19117.74 (14)
C3—C4—C5118.60 (15)C15—C20—C21121.76 (13)
C3—C4—H4A120.7C19—C20—C21120.49 (14)
C5—C4—H4A120.7C22—C21—C23114.9 (2)
C6—C5—C4120.95 (16)C22—C21—C20112.11 (18)
C6—C5—H5A119.5C23—C21—C20111.35 (17)
C4—C5—H5A119.5C22—C21—H21A105.9
C5—C6—C1121.06 (14)C23—C21—H21A105.9
C5—C6—H6A119.5C20—C21—H21A105.9
C1—C6—H6A119.5C21—C22—H22A109.5
N1—C7—C2125.85 (13)C21—C22—H22B109.5
N1—C7—H7A117.1H22A—C22—H22B109.5
C2—C7—H7A117.1C21—C22—H22C109.5
N1—C8—C9113.42 (12)H22A—C22—H22C109.5
N1—C8—H8A108.9H22B—C22—H22C109.5
C9—C8—H8A108.9C21—C23—H23A109.5
N1—C8—H8B108.9C21—C23—H23B109.5
C9—C8—H8B108.9H23A—C23—H23B109.5
H8A—C8—H8B107.7C21—C23—H23C109.5
C14—C9—C10117.49 (14)H23A—C23—H23C109.5
C14—C9—C8122.37 (13)H23B—C23—H23C109.5
C10—C9—C8120.13 (13)C16—C24—C26110.94 (13)
C11—C10—C9120.70 (17)C16—C24—C25112.51 (15)
C11—C10—H10A119.7C26—C24—C25109.81 (16)
C9—C10—H10A119.7C16—C24—H24A107.8
C12—C11—C10120.62 (18)C26—C24—H24A107.8
C12—C11—H11A119.7C25—C24—H24A107.8
C10—C11—H11A119.7C24—C25—H25A109.5
C13—C12—C11118.89 (18)C24—C25—H25B109.5
C13—C12—H12A120.6H25A—C25—H25B109.5
C11—C12—H12A120.6C24—C25—H25C109.5
C12—C13—C14121.10 (18)H25A—C25—H25C109.5
C12—C13—H13A119.5H25B—C25—H25C109.5
C14—C13—H13A119.5C24—C26—H26A109.5
C13—C14—C9121.20 (15)C24—C26—H26B109.5
C13—C14—H14A119.4H26A—C26—H26B109.5
C9—C14—H14A119.4C24—C26—H26C109.5
C20—C15—C16121.90 (12)H26A—C26—H26C109.5
C20—C15—N2119.19 (12)H26B—C26—H26C109.5
C16—C15—N2118.90 (12)
C15—N2—C1—C64.9 (2)C8—C9—C14—C13178.51 (16)
C15—N2—C1—C2176.32 (12)C1—N2—C15—C2088.21 (16)
N2—C1—C2—C3178.86 (12)C1—N2—C15—C1692.83 (15)
C6—C1—C2—C30.01 (19)C20—C15—C16—C170.5 (2)
N2—C1—C2—C71.0 (2)N2—C15—C16—C17178.38 (11)
C6—C1—C2—C7179.87 (12)C20—C15—C16—C24179.15 (13)
C1—C2—C3—C40.6 (2)N2—C15—C16—C240.22 (18)
C7—C2—C3—C4179.48 (16)C15—C16—C17—C180.3 (2)
C2—C3—C4—C50.3 (3)C24—C16—C17—C18178.90 (14)
C3—C4—C5—C60.7 (3)C16—C17—C18—C190.1 (3)
C4—C5—C6—C11.4 (3)C17—C18—C19—C200.2 (3)
N2—C1—C6—C5179.82 (14)C16—C15—C20—C190.6 (2)
C2—C1—C6—C51.0 (2)N2—C15—C20—C19178.32 (12)
C8—N1—C7—C2179.73 (13)C16—C15—C20—C21178.58 (13)
C3—C2—C7—N1178.73 (13)N2—C15—C20—C212.5 (2)
C1—C2—C7—N11.4 (2)C18—C19—C20—C150.4 (2)
C7—N1—C8—C9124.20 (15)C18—C19—C20—C21178.78 (15)
N1—C8—C9—C1419.0 (2)C15—C20—C21—C22115.1 (2)
N1—C8—C9—C10162.48 (14)C19—C20—C21—C2265.7 (3)
C14—C9—C10—C110.3 (2)C15—C20—C21—C23114.7 (3)
C8—C9—C10—C11178.24 (18)C19—C20—C21—C2364.5 (3)
C9—C10—C11—C120.1 (3)C17—C16—C24—C2687.45 (18)
C10—C11—C12—C130.7 (3)C15—C16—C24—C2691.11 (17)
C11—C12—C13—C141.0 (3)C17—C16—C24—C2536.0 (2)
C12—C13—C14—C90.7 (3)C15—C16—C24—C25145.44 (16)
C10—C9—C14—C130.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.862.032.7113 (15)136

Experimental details

Crystal data
Chemical formulaC26H30N2
Mr370.52
Crystal system, space groupTriclinic, 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)
V3)1130.68 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.53 × 0.46 × 0.32
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.965, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
24959, 5557, 3150
Rint0.061
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.178, 1.00
No. of reflections5557
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2A···N10.862.032.7113 (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

First citationBruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGao, W., Cui, D., Liu, X., Zhang, Y. & Mu, Y. (2008). Organometallics, 27, 5889–5893.  Web of Science CSD CrossRef CAS Google Scholar
First citationLee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S.-I., Yun, H., Lee, H. & Park, Y.-W. (2005). J. Am. Chem. Soc. 127, 3031–3037.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTsai, Y.-H., Lin, C.-H., Lin, C.-C. & Ko, B.-T. (2009). J. Polym. Sci. Part. A: Polym. Chem. 47, 4927–4936.  Google Scholar
First citationYao, W., Mu, Y., Gao, A., Gao, W. & Ye, L. (2008). Dalton Trans. pp. 3199–3206.  Web of Science CSD CrossRef Google Scholar

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