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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o251-o252

Crystal structure of (2E,3E)-N2,N3-bis­­(3-ethyl-[1,1′-biphen­yl]-4-yl)butane-2,3-di­imine

CROSSMARK_Color_square_no_text.svg

aKey Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: jianchaoyuan@nwnu.edu.cn

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 March 2015; accepted 12 March 2015; online 21 March 2015)

In the title compound, C32H32N2, synthesized by the con­densation reaction of 2-ethyl-4-phenyl­aniline and 2,3-butane­dione, the conformation about the C=N bonds is E and the substituted biphenyl units are trans to one another. In the two biphenyl ring systems, the planes of the two rings are inclined to one another by 25.25 (19) and 28.01 (19)°. The planes of the ethyl-substituted benzene rings are inclined to one another by 20.23 (19)° and to the mean plane of the butane-2,3-di­imine unit [maximum deviation = 0.014 (4) Å] by 83.19 (19) and 63.38 (19)°. In the crystal, mol­ecules are linked by C—H⋯π inter­actions, forming sheets lying parallel to (101).

1. Related literature

For literature on α-di­imine palladium and nickel complex catalysts for the polymerization of α-olefins, see: Johnson et al. (1995[Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414-6415.]); Gates et al. (2000[Gates, D. P., Svejda, S. A., Oñate, E., Killian, C. M., Johnson, L. K., White, P. S. & Brookhart, M. (2000). Macromolecules, 33 2320-2334.]). For the crystal structure of a similar compound, see: Chen et al. (2014[Chen, J., Yuan, J., Zhao, J., Xu, W. & Mu, Y. (2014). Acta Cryst. E70, o455.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C32H32N2

  • Mr = 444.60

  • Triclinic, [P \overline 1]

  • a = 9.622 (4) Å

  • b = 9.707 (5) Å

  • c = 14.666 (7) Å

  • α = 77.288 (5)°

  • β = 86.934 (4)°

  • γ = 74.736 (4)°

  • V = 1289.1 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.28 × 0.26 × 0.25 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.984

  • 9264 measured reflections

  • 4719 independent reflections

  • 2323 reflections with I > 2σ(I)

  • Rint = 0.042

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.245

  • S = 1.03

  • 4719 reflections

  • 311 parameters

  • 62 restraints

  • H-atom parameters constrained

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of rings C7-C12 and C23-C28, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯Cg4i 0.93 2.83 3.625 (5) 144
C11—H11⋯Cg4ii 0.93 2.92 3.639 (5) 135
C24—H24⋯Cg2iii 0.93 2.98 3.730 (5) 139
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) x+1, y, z-1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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


Experimental top

2-ethyl-4-phenyl­aniline was prepared by dissolving 2-ethyl-4-bromo-aniline (2 mmol, 0.41 g) in PEG-400 (10 ml) containing phenyl­boronic acid (0.293g, 2.4 mmol), K2CO3 (0.828 g, 0.6 mmol) and PdCl2 (50 mg) in a round-bottomed flask and stirred at room temperature for 12 h. On completion of the reaction the solution was purified by column chromatography with ethyl acetate/petroleum ether (v/v = 1:15) as eluent. Pure 2-ethyl-4-phenyl­aniline was obtained as a colourless liquid (yield: 0.385 g, 87%). Formic acid (0.5 ml) was then added to a stirred solution of 2,3-butane­dione (0.043 g, 0.5 mmol) and 2-methyl-4-phenyl­aniline (0.198 g, 1.0 mmol) in ethanol (20 ml). The solid that precipitated was recrystallized from di­chloro­methane/cyclo­hexane (v/v = 30:1), washed with cold cyclo­hexane and dried under vacuum to give the title compound (yield 0.15 g, 84%). Yellow block-like crystals were grown by slow evaporation of a solution of the title compound in a mixture of cyclo­hexane/di­chloro­methane (1:2, v/v).

Refinement top

All H atoms were placed in calculated positions and treated as riding: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Comment top

In the past few decades, there has been a rapid development of a series of α-diimine palladium and nickel complex catalysts for the polymerization of α-olefins since the discovery of the highly active α-diimine nickel catalysts (Johnson et al., 1995). The study found that nickel metal complex catalysts has a high catalytic activity for ethylene polymerization and high molecular weight polyethylene can be obtained. Palladium metal complex catalysts give highly branched polyethylene and the copolymerization of ethylene and polar monomers have also high catalytically active (Gates et al., 2000). The title compound has been designed to be used as a bidentate ligand for such catalysis.

The molecular structure of the title compound is illustrated in Fig. 1. The molecule is pseudo-centrosymmetric about the central Csp2-Csp2 bond (C15-C16). The conformation about the CN bonds (C15N1 and C16 N2) is E and the substituted biphenyl units are trans to one another. In the two biphenyl ring systems the two rings are inclined to one another by 25.25 (19) ° for C1-C6 and C7-C12, and by 28.01 (19) ° for C17-C22 and C23-C28. The ethyl substituted benzene rings (C1-C6 and C17-C22) are inclined to one another by 20.23 (19) ° and to the mean plane of the butane-2,3-diimine unit (maximum deviation = 0.014 (4) Å) by 83.19 (19) and 63.38 (19) °, respectively.

In the crystal, molecules are linked by C-H···π interactions forming sheets lying parallel to (101); see Table 1.

Related literature top

For literature on α-diimine palladium and nickel complex catalysts for the polymerization of α-olefins, see: Johnson et al. (1995); Gates et al. (2000). For the crystal structure of a similar compound, see: Chen et al. (2014).

Structure description top

2-ethyl-4-phenyl­aniline was prepared by dissolving 2-ethyl-4-bromo-aniline (2 mmol, 0.41 g) in PEG-400 (10 ml) containing phenyl­boronic acid (0.293g, 2.4 mmol), K2CO3 (0.828 g, 0.6 mmol) and PdCl2 (50 mg) in a round-bottomed flask and stirred at room temperature for 12 h. On completion of the reaction the solution was purified by column chromatography with ethyl acetate/petroleum ether (v/v = 1:15) as eluent. Pure 2-ethyl-4-phenyl­aniline was obtained as a colourless liquid (yield: 0.385 g, 87%). Formic acid (0.5 ml) was then added to a stirred solution of 2,3-butane­dione (0.043 g, 0.5 mmol) and 2-methyl-4-phenyl­aniline (0.198 g, 1.0 mmol) in ethanol (20 ml). The solid that precipitated was recrystallized from di­chloro­methane/cyclo­hexane (v/v = 30:1), washed with cold cyclo­hexane and dried under vacuum to give the title compound (yield 0.15 g, 84%). Yellow block-like crystals were grown by slow evaporation of a solution of the title compound in a mixture of cyclo­hexane/di­chloro­methane (1:2, v/v).

In the past few decades, there has been a rapid development of a series of α-diimine palladium and nickel complex catalysts for the polymerization of α-olefins since the discovery of the highly active α-diimine nickel catalysts (Johnson et al., 1995). The study found that nickel metal complex catalysts has a high catalytic activity for ethylene polymerization and high molecular weight polyethylene can be obtained. Palladium metal complex catalysts give highly branched polyethylene and the copolymerization of ethylene and polar monomers have also high catalytically active (Gates et al., 2000). The title compound has been designed to be used as a bidentate ligand for such catalysis.

The molecular structure of the title compound is illustrated in Fig. 1. The molecule is pseudo-centrosymmetric about the central Csp2-Csp2 bond (C15-C16). The conformation about the CN bonds (C15N1 and C16 N2) is E and the substituted biphenyl units are trans to one another. In the two biphenyl ring systems the two rings are inclined to one another by 25.25 (19) ° for C1-C6 and C7-C12, and by 28.01 (19) ° for C17-C22 and C23-C28. The ethyl substituted benzene rings (C1-C6 and C17-C22) are inclined to one another by 20.23 (19) ° and to the mean plane of the butane-2,3-diimine unit (maximum deviation = 0.014 (4) Å) by 83.19 (19) and 63.38 (19) °, respectively.

In the crystal, molecules are linked by C-H···π interactions forming sheets lying parallel to (101); see Table 1.

For literature on α-diimine palladium and nickel complex catalysts for the polymerization of α-olefins, see: Johnson et al. (1995); Gates et al. (2000). For the crystal structure of a similar compound, see: Chen et al. (2014).

Refinement details top

All H atoms were placed in calculated positions and treated as riding: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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
[Figure 1] Fig. 1. Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
(2E,3E)-N2,N3-Bis(3-ethyl-[1,1'-biphenyl]-4-yl)butane-2,3-diimine top
Crystal data top
C32H32N2Z = 2
Mr = 444.60F(000) = 476
Triclinic, P1Dx = 1.145 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.622 (4) ÅCell parameters from 1713 reflections
b = 9.707 (5) Åθ = 2.2–23.0°
c = 14.666 (7) ŵ = 0.07 mm1
α = 77.288 (5)°T = 296 K
β = 86.934 (4)°Block, yellow
γ = 74.736 (4)°0.28 × 0.26 × 0.25 mm
V = 1289.1 (10) Å3
Data collection top
Bruker APEXII CCD
diffractometer
4719 independent reflections
Radiation source: fine-focus sealed tube2323 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1011
Tmin = 0.982, Tmax = 0.984k = 1111
9264 measured reflectionsl = 1717
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0989P)2 + 0.5812P]
where P = (Fo2 + 2Fc2)/3
4719 reflections(Δ/σ)max = 0.001
311 parametersΔρmax = 0.42 e Å3
62 restraintsΔρmin = 0.32 e Å3
Crystal data top
C32H32N2γ = 74.736 (4)°
Mr = 444.60V = 1289.1 (10) Å3
Triclinic, P1Z = 2
a = 9.622 (4) ÅMo Kα radiation
b = 9.707 (5) ŵ = 0.07 mm1
c = 14.666 (7) ÅT = 296 K
α = 77.288 (5)°0.28 × 0.26 × 0.25 mm
β = 86.934 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
4719 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2323 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.984Rint = 0.042
9264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06962 restraints
wR(F2) = 0.245H-atom parameters constrained
S = 1.03Δρmax = 0.42 e Å3
4719 reflectionsΔρmin = 0.32 e Å3
311 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
C40.2795 (3)0.7460 (4)0.3800 (2)0.0475 (9)
C70.2487 (3)0.7538 (4)0.4796 (2)0.0447 (8)
C240.8794 (4)0.7005 (4)0.4998 (2)0.0547 (9)
H240.95480.67380.45710.066*
C230.7383 (3)0.7411 (4)0.4689 (2)0.0447 (8)
C200.7041 (4)0.7451 (4)0.3690 (2)0.0474 (9)
N10.3646 (4)0.7226 (4)0.0967 (2)0.0691 (10)
C20.4010 (4)0.6174 (4)0.2631 (2)0.0600 (10)
H20.46310.53420.24840.072*
N20.6087 (4)0.7552 (4)0.08534 (19)0.0677 (9)
C250.9095 (4)0.6991 (4)0.5925 (2)0.0606 (10)
H251.00460.67030.61140.073*
C280.6287 (4)0.7801 (4)0.5354 (2)0.0524 (9)
H280.53320.80610.51660.063*
C270.6588 (4)0.7807 (4)0.6286 (2)0.0575 (10)
H270.58410.80860.67190.069*
C210.5806 (4)0.8396 (4)0.3438 (2)0.0624 (10)
H210.51830.90330.39010.075*
C80.2624 (4)0.6280 (4)0.5489 (2)0.0532 (9)
H80.29030.53720.53280.064*
C30.3721 (4)0.6228 (4)0.3557 (2)0.0556 (9)
H30.41490.54320.40230.067*
C170.6367 (4)0.7479 (4)0.1810 (2)0.0577 (10)
C120.2056 (4)0.8868 (4)0.5063 (2)0.0588 (10)
H120.19600.97260.46110.071*
C90.2352 (4)0.6355 (5)0.6412 (2)0.0638 (11)
H90.24640.54990.68690.077*
C10.3390 (4)0.7335 (5)0.1921 (2)0.0586 (10)
C150.4766 (4)0.7491 (4)0.0550 (2)0.0616 (10)
C160.4957 (4)0.7297 (4)0.0440 (2)0.0602 (10)
C220.5486 (4)0.8406 (5)0.2514 (2)0.0705 (12)
H220.46530.90560.23630.085*
C110.1765 (4)0.8947 (5)0.5984 (3)0.0692 (11)
H110.14660.98530.61470.083*
C50.2159 (4)0.8603 (4)0.3076 (2)0.0571 (10)
H50.15260.94290.32230.069*
C190.7939 (4)0.6534 (4)0.2969 (2)0.0576 (10)
H190.87800.58980.31210.069*
C60.2429 (4)0.8566 (5)0.2135 (2)0.0655 (10)
C180.7635 (4)0.6525 (5)0.2029 (2)0.0655 (11)
C260.7997 (4)0.7401 (4)0.6574 (2)0.0625 (11)
H260.82040.74040.72010.075*
C320.3837 (5)0.6771 (5)0.0834 (3)0.0817 (13)
H32A0.29880.75620.09900.123*
H32B0.36020.59920.03790.123*
H32C0.42030.64240.13870.123*
C100.1917 (4)0.7683 (5)0.6659 (3)0.0724 (12)
H100.17260.77310.72810.087*
C310.5890 (5)0.7985 (6)0.0961 (3)0.1001 (17)
H31A0.54840.84340.14700.150*
H31B0.62260.86800.04900.150*
H31C0.66820.71590.11860.150*
C290.8580 (5)0.5493 (6)0.1247 (3)0.0996 (15)
H29A0.87010.60610.08040.119*
H29B0.80510.48040.09300.119*
C130.1671 (5)0.9816 (6)0.1373 (3)0.0957 (14)
H13A0.18781.07050.14590.115*
H13B0.20720.96370.07760.115*
C300.9944 (7)0.4688 (9)0.1444 (4)0.187 (3)
H30A0.99110.43760.20180.281*
H30B1.02500.38470.09450.281*
H30C1.06110.52840.15040.281*
C140.0125 (7)1.0059 (9)0.1331 (5)0.199 (4)
H14A0.01010.94170.09810.298*
H14B0.03021.10550.10300.298*
H14C0.02480.98650.19530.298*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C40.0409 (19)0.061 (2)0.0438 (19)0.0161 (17)0.0055 (15)0.0145 (17)
C70.0345 (18)0.056 (2)0.0490 (19)0.0165 (16)0.0058 (14)0.0174 (17)
C240.047 (2)0.071 (3)0.049 (2)0.0169 (19)0.0011 (16)0.0179 (18)
C230.043 (2)0.051 (2)0.0425 (18)0.0159 (17)0.0024 (15)0.0124 (15)
C200.044 (2)0.057 (2)0.0420 (19)0.0141 (17)0.0059 (15)0.0122 (16)
N10.073 (2)0.099 (3)0.0452 (18)0.031 (2)0.0112 (16)0.0270 (17)
C20.058 (2)0.069 (3)0.056 (2)0.012 (2)0.0103 (18)0.028 (2)
N20.072 (2)0.091 (3)0.0439 (17)0.0216 (19)0.0090 (16)0.0229 (16)
C250.050 (2)0.079 (3)0.057 (2)0.020 (2)0.0148 (18)0.025 (2)
C280.046 (2)0.063 (2)0.050 (2)0.0159 (18)0.0015 (16)0.0123 (17)
C270.059 (2)0.069 (3)0.046 (2)0.019 (2)0.0073 (17)0.0099 (17)
C210.058 (2)0.072 (3)0.046 (2)0.002 (2)0.0077 (17)0.0098 (18)
C80.051 (2)0.060 (2)0.048 (2)0.0113 (18)0.0052 (16)0.0161 (17)
C30.054 (2)0.063 (2)0.051 (2)0.0141 (19)0.0057 (17)0.0186 (18)
C170.060 (2)0.075 (3)0.042 (2)0.019 (2)0.0078 (17)0.0194 (18)
C120.063 (2)0.060 (2)0.057 (2)0.021 (2)0.0075 (18)0.0177 (18)
C90.064 (3)0.075 (3)0.050 (2)0.016 (2)0.0011 (18)0.010 (2)
C10.058 (2)0.080 (3)0.047 (2)0.027 (2)0.0107 (17)0.024 (2)
C150.064 (3)0.081 (3)0.043 (2)0.018 (2)0.0062 (18)0.0205 (19)
C160.061 (2)0.076 (3)0.044 (2)0.015 (2)0.0052 (18)0.0185 (18)
C220.065 (3)0.082 (3)0.053 (2)0.001 (2)0.0136 (19)0.017 (2)
C110.078 (3)0.071 (3)0.066 (3)0.021 (2)0.013 (2)0.032 (2)
C50.055 (2)0.064 (2)0.052 (2)0.0144 (19)0.0105 (17)0.0154 (18)
C190.050 (2)0.073 (3)0.048 (2)0.0078 (19)0.0029 (16)0.0181 (18)
C60.067 (2)0.079 (3)0.049 (2)0.021 (2)0.0078 (18)0.0092 (18)
C180.059 (2)0.093 (3)0.0417 (19)0.014 (2)0.0026 (16)0.0144 (19)
C260.075 (3)0.076 (3)0.045 (2)0.029 (2)0.0101 (19)0.0212 (19)
C320.084 (3)0.120 (4)0.053 (2)0.037 (3)0.008 (2)0.033 (2)
C100.074 (3)0.102 (4)0.049 (2)0.024 (3)0.008 (2)0.032 (2)
C310.092 (3)0.176 (5)0.060 (3)0.065 (4)0.016 (2)0.050 (3)
C290.085 (3)0.142 (4)0.053 (2)0.001 (3)0.009 (2)0.017 (2)
C130.095 (3)0.104 (3)0.070 (3)0.011 (3)0.000 (2)0.002 (2)
C300.137 (5)0.249 (7)0.089 (4)0.063 (5)0.009 (4)0.009 (4)
C140.137 (5)0.234 (7)0.137 (5)0.028 (6)0.017 (4)0.057 (5)
Geometric parameters (Å, º) top
C4—C51.388 (5)C9—H90.9300
C4—C31.395 (5)C1—C61.391 (5)
C4—C71.489 (4)C15—C311.494 (6)
C7—C121.384 (5)C15—C161.501 (5)
C7—C81.387 (5)C16—C321.497 (5)
C24—C251.377 (4)C22—H220.9300
C24—C231.391 (4)C11—C101.377 (6)
C24—H240.9300C11—H110.9300
C23—C281.394 (4)C5—C61.396 (5)
C23—C201.491 (4)C5—H50.9300
C20—C211.386 (5)C19—C181.392 (5)
C20—C191.392 (5)C19—H190.9300
N1—C151.269 (4)C6—C131.510 (6)
N1—C11.430 (4)C18—C291.506 (5)
C2—C31.380 (4)C26—H260.9300
C2—C11.381 (5)C32—H32A0.9600
C2—H20.9300C32—H32B0.9600
N2—C161.272 (4)C32—H32C0.9600
N2—C171.428 (4)C10—H100.9300
C25—C261.379 (5)C31—H31A0.9600
C25—H250.9300C31—H31B0.9600
C28—C271.380 (4)C31—H31C0.9600
C28—H280.9300C29—C301.391 (6)
C27—C261.379 (5)C29—H29A0.9700
C27—H270.9300C29—H29B0.9700
C21—C221.375 (5)C13—C141.446 (7)
C21—H210.9300C13—H13A0.9700
C8—C91.379 (5)C13—H13B0.9700
C8—H80.9300C30—H30A0.9600
C3—H30.9300C30—H30B0.9600
C17—C221.370 (5)C30—H30C0.9600
C17—C181.394 (5)C14—H14A0.9600
C12—C111.379 (5)C14—H14B0.9600
C12—H120.9300C14—H14C0.9600
C9—C101.369 (6)
C5—C4—C3117.2 (3)C21—C22—H22119.3
C5—C4—C7121.4 (3)C10—C11—C12119.8 (4)
C3—C4—C7121.3 (3)C10—C11—H11120.1
C12—C7—C8117.7 (3)C12—C11—H11120.1
C12—C7—C4121.1 (3)C4—C5—C6122.8 (4)
C8—C7—C4121.2 (3)C4—C5—H5118.6
C25—C24—C23121.2 (3)C6—C5—H5118.6
C25—C24—H24119.4C20—C19—C18123.0 (3)
C23—C24—H24119.4C20—C19—H19118.5
C24—C23—C28117.4 (3)C18—C19—H19118.5
C24—C23—C20121.8 (3)C1—C6—C5118.2 (4)
C28—C23—C20120.8 (3)C1—C6—C13121.0 (4)
C21—C20—C19117.0 (3)C5—C6—C13120.7 (4)
C21—C20—C23121.4 (3)C19—C18—C17117.9 (3)
C19—C20—C23121.7 (3)C19—C18—C29122.9 (4)
C15—N1—C1120.7 (3)C17—C18—C29119.1 (3)
C3—C2—C1121.0 (4)C25—C26—C27119.4 (3)
C3—C2—H2119.5C25—C26—H26120.3
C1—C2—H2119.5C27—C26—H26120.3
C16—N2—C17122.1 (3)C16—C32—H32A109.5
C24—C25—C26120.5 (3)C16—C32—H32B109.5
C24—C25—H25119.8H32A—C32—H32B109.5
C26—C25—H25119.8C16—C32—H32C109.5
C27—C28—C23121.4 (3)H32A—C32—H32C109.5
C27—C28—H28119.3H32B—C32—H32C109.5
C23—C28—H28119.3C9—C10—C11119.8 (4)
C26—C27—C28120.1 (3)C9—C10—H10120.1
C26—C27—H27120.0C11—C10—H10120.1
C28—C27—H27120.0C15—C31—H31A109.5
C22—C21—C20121.0 (4)C15—C31—H31B109.5
C22—C21—H21119.5H31A—C31—H31B109.5
C20—C21—H21119.5C15—C31—H31C109.5
C9—C8—C7121.1 (4)H31A—C31—H31C109.5
C9—C8—H8119.5H31B—C31—H31C109.5
C7—C8—H8119.5C30—C29—C18119.9 (4)
C2—C3—C4120.8 (3)C30—C29—H29A107.3
C2—C3—H3119.6C18—C29—H29A107.3
C4—C3—H3119.6C30—C29—H29B107.3
C22—C17—C18119.8 (3)C18—C29—H29B107.3
C22—C17—N2121.5 (3)H29A—C29—H29B106.9
C18—C17—N2118.5 (3)C14—C13—C6115.4 (4)
C11—C12—C7121.4 (4)C14—C13—H13A108.4
C11—C12—H12119.3C6—C13—H13A108.4
C7—C12—H12119.3C14—C13—H13B108.4
C10—C9—C8120.3 (4)C6—C13—H13B108.4
C10—C9—H9119.9H13A—C13—H13B107.5
C8—C9—H9119.9C29—C30—H30A109.5
C2—C1—C6119.8 (3)C29—C30—H30B109.5
C2—C1—N1120.1 (4)H30A—C30—H30B109.5
C6—C1—N1119.9 (4)C29—C30—H30C109.5
N1—C15—C31125.4 (3)H30A—C30—H30C109.5
N1—C15—C16116.5 (4)H30B—C30—H30C109.5
C31—C15—C16118.1 (3)C13—C14—H14A109.5
N2—C16—C32126.3 (3)C13—C14—H14B109.5
N2—C16—C15116.3 (4)H14A—C14—H14B109.5
C32—C16—C15117.3 (3)C13—C14—H14C109.5
C17—C22—C21121.4 (4)H14A—C14—H14C109.5
C17—C22—H22119.3H14B—C14—H14C109.5
C5—C4—C7—C1225.7 (5)C17—N2—C16—C15176.9 (4)
C3—C4—C7—C12155.0 (3)N1—C15—C16—N2179.4 (4)
C5—C4—C7—C8154.3 (3)C31—C15—C16—N21.0 (6)
C3—C4—C7—C824.9 (5)N1—C15—C16—C321.7 (6)
C25—C24—C23—C280.1 (5)C31—C15—C16—C32178.8 (4)
C25—C24—C23—C20179.2 (3)C18—C17—C22—C211.6 (6)
C24—C23—C20—C21151.7 (4)N2—C17—C22—C21175.9 (4)
C28—C23—C20—C2127.6 (5)C20—C21—C22—C170.5 (6)
C24—C23—C20—C1928.9 (5)C7—C12—C11—C100.7 (6)
C28—C23—C20—C19151.8 (3)C3—C4—C5—C61.0 (5)
C23—C24—C25—C260.9 (6)C7—C4—C5—C6179.7 (3)
C24—C23—C28—C271.1 (5)C21—C20—C19—C180.7 (6)
C20—C23—C28—C27178.2 (3)C23—C20—C19—C18178.7 (3)
C23—C28—C27—C261.1 (5)C2—C1—C6—C52.1 (6)
C19—C20—C21—C220.6 (6)N1—C1—C6—C5177.1 (3)
C23—C20—C21—C22178.8 (3)C2—C1—C6—C13176.5 (4)
C12—C7—C8—C90.6 (5)N1—C1—C6—C131.5 (6)
C4—C7—C8—C9179.3 (3)C4—C5—C6—C10.8 (6)
C1—C2—C3—C40.1 (6)C4—C5—C6—C13177.9 (4)
C5—C4—C3—C21.4 (5)C20—C19—C18—C170.3 (6)
C7—C4—C3—C2179.3 (3)C20—C19—C18—C29177.7 (4)
C16—N2—C17—C2263.3 (6)C22—C17—C18—C191.4 (6)
C16—N2—C17—C18122.3 (4)N2—C17—C18—C19175.9 (3)
C8—C7—C12—C110.3 (5)C22—C17—C18—C29178.9 (4)
C4—C7—C12—C11179.8 (3)N2—C17—C18—C296.6 (6)
C7—C8—C9—C101.0 (6)C24—C25—C26—C270.9 (6)
C3—C2—C1—C61.7 (6)C28—C27—C26—C250.0 (6)
C3—C2—C1—N1176.7 (3)C8—C9—C10—C110.6 (6)
C15—N1—C1—C284.0 (5)C12—C11—C10—C90.2 (6)
C15—N1—C1—C6100.9 (5)C19—C18—C29—C3012.0 (9)
C1—N1—C15—C312.4 (7)C17—C18—C29—C30170.6 (6)
C1—N1—C15—C16178.0 (4)C1—C6—C13—C14114.5 (6)
C17—N2—C16—C325.6 (6)C5—C6—C13—C1464.1 (7)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of rings C7-C12 and C23-C28, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg4i0.932.833.625 (5)144
C11—H11···Cg4ii0.932.923.639 (5)135
C24—H24···Cg2iii0.932.983.730 (5)139
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y, z1.
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of rings C7-C12 and C23-C28, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg4i0.932.833.625 (5)144
C11—H11···Cg4ii0.932.923.639 (5)135
C24—H24···Cg2iii0.932.983.730 (5)139
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+2, z; (iii) x+1, y, z1.
 

Acknowledgements

We are grateful to the Key Laboratory of Eco Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University), and the National Natural Science Foundation of China (grant No. 20964003), for financial support.

References

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First citationGates, D. P., Svejda, S. A., Oñate, E., Killian, C. M., Johnson, L. K., White, P. S. & Brookhart, M. (2000). Macromolecules, 33 2320–2334.  CSD CrossRef CAS Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 71| Part 4| April 2015| Pages o251-o252
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