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

Zhao, Y.; Yuan, J.; Zhao, J.; Zhao, S.

doi:10.1107/S2056989015005071

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S2056989015005071

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

Yan Zhao,^a Jianchao Yuan,^a ^* Jie Zhao ^a and Shenglan Zhao ^a

^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).

Keywords: crystal structure; α-diimine; catalyst; C—H⋯π interactions.

CCDC reference: 1053619

1. Related literature

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 ).

2. Experimental

2.1. Crystal data

C₃₂H₃₂N₂
M_r = 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 ) T_min = 0.982, T_max = 0.984
9264 measured reflections
4719 independent reflections
2323 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.42 e Å⁻³
Δρ_min = −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	D⋯A	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); cell refinement: SAINT (Bruker, 2007); 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

CCDC reference: 1053619

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2056989015005071/su5091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015005071/su5091Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015005071/su5091Isup3.cml

checkCIF report

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 U_iso(H) = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(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 C═N bonds (C15═N1 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

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 U_iso(H) = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(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

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

C₃₂H₃₂N₂	Z = 2
M_r = 444.60	F(000) = 476
Triclinic, P1	D_x = 1.145 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.622 (4) Å	Cell parameters from 1713 reflections
b = 9.707 (5) Å	θ = 2.2–23.0°
c = 14.666 (7) Å	µ = 0.07 mm⁻¹
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 tube	2323 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
T_min = 0.982, T_max = 0.984	k = −11→11
9264 measured reflections	l = −17→17

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.245	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0989P)² + 0.5812P] where P = (F_o² + 2F_c²)/3
4719 reflections	(Δ/σ)_max = 0.001
311 parameters	Δρ_max = 0.42 e Å⁻³
62 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₃₂H₃₂N₂	γ = 74.736 (4)°
M_r = 444.60	V = 1289.1 (10) Å³
Triclinic, P1	Z = 2
a = 9.622 (4) Å	Mo Kα radiation
b = 9.707 (5) Å	µ = 0.07 mm⁻¹
c = 14.666 (7) Å	T = 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)
T_min = 0.982, T_max = 0.984	R_int = 0.042
9264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	62 restraints
wR(F²) = 0.245	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
4719 reflections	Δρ_min = −0.32 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C4	0.2795 (3)	0.7460 (4)	0.3800 (2)	0.0475 (9)
C7	0.2487 (3)	0.7538 (4)	0.4796 (2)	0.0447 (8)
C24	0.8794 (4)	0.7005 (4)	−0.4998 (2)	0.0547 (9)
H24	0.9548	0.6738	−0.4571	0.066*
C23	0.7383 (3)	0.7411 (4)	−0.4689 (2)	0.0447 (8)
C20	0.7041 (4)	0.7451 (4)	−0.3690 (2)	0.0474 (9)
N1	0.3646 (4)	0.7226 (4)	0.0967 (2)	0.0691 (10)
C2	0.4010 (4)	0.6174 (4)	0.2631 (2)	0.0600 (10)
H2	0.4631	0.5342	0.2484	0.072*
N2	0.6087 (4)	0.7552 (4)	−0.08534 (19)	0.0677 (9)
C25	0.9095 (4)	0.6991 (4)	−0.5925 (2)	0.0606 (10)
H25	1.0046	0.6703	−0.6114	0.073*
C28	0.6287 (4)	0.7801 (4)	−0.5354 (2)	0.0524 (9)
H28	0.5332	0.8061	−0.5166	0.063*
C27	0.6588 (4)	0.7807 (4)	−0.6286 (2)	0.0575 (10)
H27	0.5841	0.8086	−0.6719	0.069*
C21	0.5806 (4)	0.8396 (4)	−0.3438 (2)	0.0624 (10)
H21	0.5183	0.9033	−0.3901	0.075*
C8	0.2624 (4)	0.6280 (4)	0.5489 (2)	0.0532 (9)
H8	0.2903	0.5372	0.5328	0.064*
C3	0.3721 (4)	0.6228 (4)	0.3557 (2)	0.0556 (9)
H3	0.4149	0.5432	0.4023	0.067*
C17	0.6367 (4)	0.7479 (4)	−0.1810 (2)	0.0577 (10)
C12	0.2056 (4)	0.8868 (4)	0.5063 (2)	0.0588 (10)
H12	0.1960	0.9726	0.4611	0.071*
C9	0.2352 (4)	0.6355 (5)	0.6412 (2)	0.0638 (11)
H9	0.2464	0.5499	0.6869	0.077*
C1	0.3390 (4)	0.7335 (5)	0.1921 (2)	0.0586 (10)
C15	0.4766 (4)	0.7491 (4)	0.0550 (2)	0.0616 (10)
C16	0.4957 (4)	0.7297 (4)	−0.0440 (2)	0.0602 (10)
C22	0.5486 (4)	0.8406 (5)	−0.2514 (2)	0.0705 (12)
H22	0.4653	0.9056	−0.2363	0.085*
C11	0.1765 (4)	0.8947 (5)	0.5984 (3)	0.0692 (11)
H11	0.1466	0.9853	0.6147	0.083*
C5	0.2159 (4)	0.8603 (4)	0.3076 (2)	0.0571 (10)
H5	0.1526	0.9429	0.3223	0.069*
C19	0.7939 (4)	0.6534 (4)	−0.2969 (2)	0.0576 (10)
H19	0.8780	0.5898	−0.3121	0.069*
C6	0.2429 (4)	0.8566 (5)	0.2135 (2)	0.0655 (10)
C18	0.7635 (4)	0.6525 (5)	−0.2029 (2)	0.0655 (11)
C26	0.7997 (4)	0.7401 (4)	−0.6574 (2)	0.0625 (11)
H26	0.8204	0.7404	−0.7201	0.075*
C32	0.3837 (5)	0.6771 (5)	−0.0834 (3)	0.0817 (13)
H32A	0.2988	0.7562	−0.0990	0.123*
H32B	0.3602	0.5992	−0.0379	0.123*
H32C	0.4203	0.6424	−0.1387	0.123*
C10	0.1917 (4)	0.7683 (5)	0.6659 (3)	0.0724 (12)
H10	0.1726	0.7731	0.7281	0.087*
C31	0.5890 (5)	0.7985 (6)	0.0961 (3)	0.1001 (17)
H31A	0.5484	0.8434	0.1470	0.150*
H31B	0.6226	0.8680	0.0490	0.150*
H31C	0.6682	0.7159	0.1186	0.150*
C29	0.8580 (5)	0.5493 (6)	−0.1247 (3)	0.0996 (15)
H29A	0.8701	0.6061	−0.0804	0.119*
H29B	0.8051	0.4804	−0.0930	0.119*
C13	0.1671 (5)	0.9816 (6)	0.1373 (3)	0.0957 (14)
H13A	0.1878	1.0705	0.1459	0.115*
H13B	0.2072	0.9637	0.0776	0.115*
C30	0.9944 (7)	0.4688 (9)	−0.1444 (4)	0.187 (3)
H30A	0.9911	0.4376	−0.2018	0.281*
H30B	1.0250	0.3847	−0.0945	0.281*
H30C	1.0611	0.5284	−0.1504	0.281*
C14	0.0125 (7)	1.0059 (9)	0.1331 (5)	0.199 (4)
H14A	−0.0101	0.9417	0.0981	0.298*
H14B	−0.0302	1.1055	0.1030	0.298*
H14C	−0.0248	0.9865	0.1953	0.298*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0409 (19)	0.061 (2)	0.0438 (19)	−0.0161 (17)	0.0055 (15)	−0.0145 (17)
C7	0.0345 (18)	0.056 (2)	0.0490 (19)	−0.0165 (16)	0.0058 (14)	−0.0174 (17)
C24	0.047 (2)	0.071 (3)	0.049 (2)	−0.0169 (19)	0.0011 (16)	−0.0179 (18)
C23	0.043 (2)	0.051 (2)	0.0425 (18)	−0.0159 (17)	0.0024 (15)	−0.0124 (15)
C20	0.044 (2)	0.057 (2)	0.0420 (19)	−0.0141 (17)	0.0059 (15)	−0.0122 (16)
N1	0.073 (2)	0.099 (3)	0.0452 (18)	−0.031 (2)	0.0112 (16)	−0.0270 (17)
C2	0.058 (2)	0.069 (3)	0.056 (2)	−0.012 (2)	0.0103 (18)	−0.028 (2)
N2	0.072 (2)	0.091 (3)	0.0439 (17)	−0.0216 (19)	0.0090 (16)	−0.0229 (16)
C25	0.050 (2)	0.079 (3)	0.057 (2)	−0.020 (2)	0.0148 (18)	−0.025 (2)
C28	0.046 (2)	0.063 (2)	0.050 (2)	−0.0159 (18)	0.0015 (16)	−0.0123 (17)
C27	0.059 (2)	0.069 (3)	0.046 (2)	−0.019 (2)	−0.0073 (17)	−0.0099 (17)
C21	0.058 (2)	0.072 (3)	0.046 (2)	−0.002 (2)	0.0077 (17)	−0.0098 (18)
C8	0.051 (2)	0.060 (2)	0.048 (2)	−0.0113 (18)	0.0052 (16)	−0.0161 (17)
C3	0.054 (2)	0.063 (2)	0.051 (2)	−0.0141 (19)	0.0057 (17)	−0.0186 (18)
C17	0.060 (2)	0.075 (3)	0.042 (2)	−0.019 (2)	0.0078 (17)	−0.0194 (18)
C12	0.063 (2)	0.060 (2)	0.057 (2)	−0.021 (2)	0.0075 (18)	−0.0177 (18)
C9	0.064 (3)	0.075 (3)	0.050 (2)	−0.016 (2)	−0.0011 (18)	−0.010 (2)
C1	0.058 (2)	0.080 (3)	0.047 (2)	−0.027 (2)	0.0107 (17)	−0.024 (2)
C15	0.064 (3)	0.081 (3)	0.043 (2)	−0.018 (2)	0.0062 (18)	−0.0205 (19)
C16	0.061 (2)	0.076 (3)	0.044 (2)	−0.015 (2)	0.0052 (18)	−0.0185 (18)
C22	0.065 (3)	0.082 (3)	0.053 (2)	0.001 (2)	0.0136 (19)	−0.017 (2)
C11	0.078 (3)	0.071 (3)	0.066 (3)	−0.021 (2)	0.013 (2)	−0.032 (2)
C5	0.055 (2)	0.064 (2)	0.052 (2)	−0.0144 (19)	0.0105 (17)	−0.0154 (18)
C19	0.050 (2)	0.073 (3)	0.048 (2)	−0.0078 (19)	0.0029 (16)	−0.0181 (18)
C6	0.067 (2)	0.079 (3)	0.049 (2)	−0.021 (2)	0.0078 (18)	−0.0092 (18)
C18	0.059 (2)	0.093 (3)	0.0417 (19)	−0.014 (2)	−0.0026 (16)	−0.0144 (19)
C26	0.075 (3)	0.076 (3)	0.045 (2)	−0.029 (2)	0.0101 (19)	−0.0212 (19)
C32	0.084 (3)	0.120 (4)	0.053 (2)	−0.037 (3)	0.008 (2)	−0.033 (2)
C10	0.074 (3)	0.102 (4)	0.049 (2)	−0.024 (3)	0.008 (2)	−0.032 (2)
C31	0.092 (3)	0.176 (5)	0.060 (3)	−0.065 (4)	0.016 (2)	−0.050 (3)
C29	0.085 (3)	0.142 (4)	0.053 (2)	0.001 (3)	−0.009 (2)	−0.017 (2)
C13	0.095 (3)	0.104 (3)	0.070 (3)	−0.011 (3)	0.000 (2)	0.002 (2)
C30	0.137 (5)	0.249 (7)	0.089 (4)	0.063 (5)	−0.009 (4)	0.009 (4)
C14	0.137 (5)	0.234 (7)	0.137 (5)	0.028 (6)	−0.017 (4)	0.057 (5)

Geometric parameters (Å, º) top

C4—C5	1.388 (5)	C9—H9	0.9300
C4—C3	1.395 (5)	C1—C6	1.391 (5)
C4—C7	1.489 (4)	C15—C31	1.494 (6)
C7—C12	1.384 (5)	C15—C16	1.501 (5)
C7—C8	1.387 (5)	C16—C32	1.497 (5)
C24—C25	1.377 (4)	C22—H22	0.9300
C24—C23	1.391 (4)	C11—C10	1.377 (6)
C24—H24	0.9300	C11—H11	0.9300
C23—C28	1.394 (4)	C5—C6	1.396 (5)
C23—C20	1.491 (4)	C5—H5	0.9300
C20—C21	1.386 (5)	C19—C18	1.392 (5)
C20—C19	1.392 (5)	C19—H19	0.9300
N1—C15	1.269 (4)	C6—C13	1.510 (6)
N1—C1	1.430 (4)	C18—C29	1.506 (5)
C2—C3	1.380 (4)	C26—H26	0.9300
C2—C1	1.381 (5)	C32—H32A	0.9600
C2—H2	0.9300	C32—H32B	0.9600
N2—C16	1.272 (4)	C32—H32C	0.9600
N2—C17	1.428 (4)	C10—H10	0.9300
C25—C26	1.379 (5)	C31—H31A	0.9600
C25—H25	0.9300	C31—H31B	0.9600
C28—C27	1.380 (4)	C31—H31C	0.9600
C28—H28	0.9300	C29—C30	1.391 (6)
C27—C26	1.379 (5)	C29—H29A	0.9700
C27—H27	0.9300	C29—H29B	0.9700
C21—C22	1.375 (5)	C13—C14	1.446 (7)
C21—H21	0.9300	C13—H13A	0.9700
C8—C9	1.379 (5)	C13—H13B	0.9700
C8—H8	0.9300	C30—H30A	0.9600
C3—H3	0.9300	C30—H30B	0.9600
C17—C22	1.370 (5)	C30—H30C	0.9600
C17—C18	1.394 (5)	C14—H14A	0.9600
C12—C11	1.379 (5)	C14—H14B	0.9600
C12—H12	0.9300	C14—H14C	0.9600
C9—C10	1.369 (6)

C5—C4—C3	117.2 (3)	C21—C22—H22	119.3
C5—C4—C7	121.4 (3)	C10—C11—C12	119.8 (4)
C3—C4—C7	121.3 (3)	C10—C11—H11	120.1
C12—C7—C8	117.7 (3)	C12—C11—H11	120.1
C12—C7—C4	121.1 (3)	C4—C5—C6	122.8 (4)
C8—C7—C4	121.2 (3)	C4—C5—H5	118.6
C25—C24—C23	121.2 (3)	C6—C5—H5	118.6
C25—C24—H24	119.4	C20—C19—C18	123.0 (3)
C23—C24—H24	119.4	C20—C19—H19	118.5
C24—C23—C28	117.4 (3)	C18—C19—H19	118.5
C24—C23—C20	121.8 (3)	C1—C6—C5	118.2 (4)
C28—C23—C20	120.8 (3)	C1—C6—C13	121.0 (4)
C21—C20—C19	117.0 (3)	C5—C6—C13	120.7 (4)
C21—C20—C23	121.4 (3)	C19—C18—C17	117.9 (3)
C19—C20—C23	121.7 (3)	C19—C18—C29	122.9 (4)
C15—N1—C1	120.7 (3)	C17—C18—C29	119.1 (3)
C3—C2—C1	121.0 (4)	C25—C26—C27	119.4 (3)
C3—C2—H2	119.5	C25—C26—H26	120.3
C1—C2—H2	119.5	C27—C26—H26	120.3
C16—N2—C17	122.1 (3)	C16—C32—H32A	109.5
C24—C25—C26	120.5 (3)	C16—C32—H32B	109.5
C24—C25—H25	119.8	H32A—C32—H32B	109.5
C26—C25—H25	119.8	C16—C32—H32C	109.5
C27—C28—C23	121.4 (3)	H32A—C32—H32C	109.5
C27—C28—H28	119.3	H32B—C32—H32C	109.5
C23—C28—H28	119.3	C9—C10—C11	119.8 (4)
C26—C27—C28	120.1 (3)	C9—C10—H10	120.1
C26—C27—H27	120.0	C11—C10—H10	120.1
C28—C27—H27	120.0	C15—C31—H31A	109.5
C22—C21—C20	121.0 (4)	C15—C31—H31B	109.5
C22—C21—H21	119.5	H31A—C31—H31B	109.5
C20—C21—H21	119.5	C15—C31—H31C	109.5
C9—C8—C7	121.1 (4)	H31A—C31—H31C	109.5
C9—C8—H8	119.5	H31B—C31—H31C	109.5
C7—C8—H8	119.5	C30—C29—C18	119.9 (4)
C2—C3—C4	120.8 (3)	C30—C29—H29A	107.3
C2—C3—H3	119.6	C18—C29—H29A	107.3
C4—C3—H3	119.6	C30—C29—H29B	107.3
C22—C17—C18	119.8 (3)	C18—C29—H29B	107.3
C22—C17—N2	121.5 (3)	H29A—C29—H29B	106.9
C18—C17—N2	118.5 (3)	C14—C13—C6	115.4 (4)
C11—C12—C7	121.4 (4)	C14—C13—H13A	108.4
C11—C12—H12	119.3	C6—C13—H13A	108.4
C7—C12—H12	119.3	C14—C13—H13B	108.4
C10—C9—C8	120.3 (4)	C6—C13—H13B	108.4
C10—C9—H9	119.9	H13A—C13—H13B	107.5
C8—C9—H9	119.9	C29—C30—H30A	109.5
C2—C1—C6	119.8 (3)	C29—C30—H30B	109.5
C2—C1—N1	120.1 (4)	H30A—C30—H30B	109.5
C6—C1—N1	119.9 (4)	C29—C30—H30C	109.5
N1—C15—C31	125.4 (3)	H30A—C30—H30C	109.5
N1—C15—C16	116.5 (4)	H30B—C30—H30C	109.5
C31—C15—C16	118.1 (3)	C13—C14—H14A	109.5
N2—C16—C32	126.3 (3)	C13—C14—H14B	109.5
N2—C16—C15	116.3 (4)	H14A—C14—H14B	109.5
C32—C16—C15	117.3 (3)	C13—C14—H14C	109.5
C17—C22—C21	121.4 (4)	H14A—C14—H14C	109.5
C17—C22—H22	119.3	H14B—C14—H14C	109.5

C5—C4—C7—C12	−25.7 (5)	C17—N2—C16—C15	−176.9 (4)
C3—C4—C7—C12	155.0 (3)	N1—C15—C16—N2	−179.4 (4)
C5—C4—C7—C8	154.3 (3)	C31—C15—C16—N2	1.0 (6)
C3—C4—C7—C8	−24.9 (5)	N1—C15—C16—C32	−1.7 (6)
C25—C24—C23—C28	0.1 (5)	C31—C15—C16—C32	178.8 (4)
C25—C24—C23—C20	−179.2 (3)	C18—C17—C22—C21	1.6 (6)
C24—C23—C20—C21	151.7 (4)	N2—C17—C22—C21	175.9 (4)
C28—C23—C20—C21	−27.6 (5)	C20—C21—C22—C17	−0.5 (6)
C24—C23—C20—C19	−28.9 (5)	C7—C12—C11—C10	0.7 (6)
C28—C23—C20—C19	151.8 (3)	C3—C4—C5—C6	−1.0 (5)
C23—C24—C25—C26	0.9 (6)	C7—C4—C5—C6	179.7 (3)
C24—C23—C28—C27	−1.1 (5)	C21—C20—C19—C18	0.7 (6)
C20—C23—C28—C27	178.2 (3)	C23—C20—C19—C18	−178.7 (3)
C23—C28—C27—C26	1.1 (5)	C2—C1—C6—C5	2.1 (6)
C19—C20—C21—C22	−0.6 (6)	N1—C1—C6—C5	177.1 (3)
C23—C20—C21—C22	178.8 (3)	C2—C1—C6—C13	−176.5 (4)
C12—C7—C8—C9	−0.6 (5)	N1—C1—C6—C13	−1.5 (6)
C4—C7—C8—C9	179.3 (3)	C4—C5—C6—C1	−0.8 (6)
C1—C2—C3—C4	−0.1 (6)	C4—C5—C6—C13	177.9 (4)
C5—C4—C3—C2	1.4 (5)	C20—C19—C18—C17	0.3 (6)
C7—C4—C3—C2	−179.3 (3)	C20—C19—C18—C29	177.7 (4)
C16—N2—C17—C22	63.3 (6)	C22—C17—C18—C19	−1.4 (6)
C16—N2—C17—C18	−122.3 (4)	N2—C17—C18—C19	−175.9 (3)
C8—C7—C12—C11	−0.3 (5)	C22—C17—C18—C29	−178.9 (4)
C4—C7—C12—C11	179.8 (3)	N2—C17—C18—C29	6.6 (6)
C7—C8—C9—C10	1.0 (6)	C24—C25—C26—C27	−0.9 (6)
C3—C2—C1—C6	−1.7 (6)	C28—C27—C26—C25	0.0 (6)
C3—C2—C1—N1	−176.7 (3)	C8—C9—C10—C11	−0.6 (6)
C15—N1—C1—C2	−84.0 (5)	C12—C11—C10—C9	−0.2 (6)
C15—N1—C1—C6	100.9 (5)	C19—C18—C29—C30	12.0 (9)
C1—N1—C15—C31	−2.4 (7)	C17—C18—C29—C30	−170.6 (6)
C1—N1—C15—C16	178.0 (4)	C1—C6—C13—C14	114.5 (6)
C17—N2—C16—C32	5.6 (6)	C5—C6—C13—C14	−64.1 (7)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	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.

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	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.

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

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, J., Yuan, J., Zhao, J., Xu, W. & Mu, Y. (2014). Acta Cryst. E70, o455. CSD CrossRef IUCr Journals Google Scholar
Gates, 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
Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414–6415. CrossRef CAS Web of Science Google Scholar
Sheldrick, 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

doi:10.1107/S2056989015005071

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