(E)-2-{3-[4-(Diphenyl­amino)styr­yl]-5,5-dimethyl­cyclo­hex-2-enyl­idene}­malono­nitrile

Ju, H.-D.; Tao, X.-T.; Xu, S.-Q.; Yu, W.-T.

doi:10.1107/S1600536809014378

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1135

doi:10.1107/S1600536809014378

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(E)-2-{3-[4-(Diphenylamino)styryl]-5,5-dimethylcyclohex-2-enylidene}malononitrile

Hai-Dong Ju,^a ^* Xu-Tang Tao,^b Shi-Qing Xu ^a and Wen-Tao Yu ^b

^aCollege of Materials Science and Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China, and ^bState Key Laboratory of Crystalline Materials, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: hdju1977@hotmail.com

(Received 31 March 2009; accepted 17 April 2009; online 25 April 2009)

In the title compound, C₃₁H₂₇N₃, the cyclohexene ring has an envelope configuration. In the crystal structure, there is an 34 Å³ void around the inversion center, but the low electron density (0.13 e Å⁻³) in the difference Fourier map suggests no solvent molecule occupying this void. No hydrogen bonding is found in the crystal structure.

Related literature

For background to organic compounds with light emitting properties, see: Tang et al. (1998 ); Li et al. (2003 ); Hye et al. (2004 ). For the synthesis, see: Lemke (1974 ); Tao & Miyata (2001 ). For related crystal structures, see: Kia et al. (2009 ); Ju et al. (2006 ).

Experimental

Crystal data

C₃₁H₂₇N₃
M_r = 441.56
Monoclinic, P 2₁ /c
a = 13.239 (5) Å
b = 16.757 (8) Å
c = 11.886 (3) Å
β = 104.073 (5)°
V = 2557.7 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.48 × 0.19 × 0.16 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: none
20681 measured reflections
5879 independent reflections
3554 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.167
S = 0.92
5879 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014378/xu2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014378/xu2505Isup2.hkl

checkCIF report

Comment top

The organic compounds with donor-π-acceptor (D-π-A) structure have special light-emitting properties, and show potential application in organic light-emitting diodes (Tang et al., 1998; Hye et al., 2004). However, these molecules easily aggregate, which usually reduces their fluorescence intensity (Li et al., 2003). Therefore, it is important to study their intermolecular interaction in the solid state. Recently we synthesized the title compound and studied its crystal structure.

The molecular structure is shown in Fig. 1. Three benzenes of triphenyl amine group show a three-bladed propeller configuration due to repulsion force. The bond lengths of C13—N1 are shorter than the single C—N distance (1.47–1.50 Å) and longer than double C=N bond distance (1.34–1.38 Å), which is due to the conjugation of p-π in triphenyl amine group. Because of long conjugation length, all atoms are roughly coplanar (Kia et al., 2009). However, the cyclohexene group shows an envelope configuration due to its ring tension, which atoms are partly out of the plane (Ju et al., 2006). The triphenyl amine and cyclohexene groups could hold back farther gather of these molecules in the solid state, which is due to their non-coplanar conjugation. No hydrogen bonding is found in the crystal structure (Fig. 2).

Related literature top

For general background, see: Tang et al. (1998); Li et al. (2003); Hye et al. (2004). For the synthesis, see: Lemke (1974); Tao & Miyata (2001). For related crystal structures, see: Kia et al. (2009); Ju et al. (2006).

Experimental top

Hexahydropyridine (1 ml) and acetic acid (2 ml) were respectively added dropwise to a stirred benzene (100 ml) solution with 4-diphenylamino-benzaldehyde (1.1 g, 4 mmol) and 2-(3,5,5-Trimethylcyclohex-2-enylidene)-malononitrile (0.92 g, 5 mmol). The mixture was stirred at room temperature for 1 h, then separated water at refluxing temperature for another 5 h. Cooled to room temperature, the title compound was gotten (Lemke, 1974; Tao & Miyata, 2001). Single crystal suitable for X-ray diffraction analysis were obtained by slow evaporation of its ethanol saturated solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the molecular structure of (I) showing the atom labels. Displacement ellipsoids are shown at the 50%.
	Fig. 2. The packing of (I), viewed down the b axis. H atoms not involved in hydrogen bonding have been omitted.

(E)-2-{3-[4-(Diphenylamino)styryl]-5,5-dimethylcyclohex-2- enylidene}malononitrile top

Crystal data top

C₃₁H₂₇N₃	F(000) = 936
M_r = 441.56	D_x = 1.147 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 962 reflections
a = 13.239 (5) Å	θ = 2.4–20.0°
b = 16.757 (8) Å	µ = 0.07 mm⁻¹
c = 11.886 (3) Å	T = 293 K
β = 104.073 (5)°	Block, red
V = 2557.7 (17) Å³	0.48 × 0.19 × 0.16 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	3554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 1.6°
ϕ and ω scans	h = −17→17
20681 measured reflections	k = −21→20
5879 independent reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.1P)² + 0.187P] where P = (F_o² + 2F_c²)/3
5879 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₃₁H₂₇N₃	V = 2557.7 (17) Å³
M_r = 441.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.239 (5) Å	µ = 0.07 mm⁻¹
b = 16.757 (8) Å	T = 293 K
c = 11.886 (3) Å	0.48 × 0.19 × 0.16 mm
β = 104.073 (5)°

Data collection top

Bruker SMART area-detector diffractometer	3554 reflections with I > 2σ(I)
20681 measured reflections	R_int = 0.027
5879 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 0.92	Δρ_max = 0.13 e Å⁻³
5879 reflections	Δρ_min = −0.18 e Å⁻³
309 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 > 2sigma (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	0.81570 (11)	0.18274 (8)	0.93407 (11)	0.0627 (4)
N2	0.43530 (17)	0.55197 (11)	0.20566 (18)	0.1061 (6)
N3	0.21605 (14)	0.45416 (10)	−0.09927 (15)	0.0845 (5)
C1	0.7581 (2)	0.01018 (13)	1.1028 (2)	0.0974 (7)
H1	0.7009	−0.0186	1.1131	0.117*
C2	0.8549 (3)	−0.01085 (14)	1.1632 (2)	0.1187 (10)
H2	0.8641	−0.0534	1.2148	0.142*
C3	0.9377 (2)	0.03051 (15)	1.1477 (2)	0.1226 (10)
H3	1.0043	0.0163	1.1891	0.147*
C4	0.92488 (17)	0.09351 (13)	1.07133 (19)	0.0943 (7)
H4	0.9830	0.1213	1.0615	0.113*
C5	0.82738 (14)	0.11594 (10)	1.00942 (13)	0.0585 (4)
C6	0.74278 (16)	0.07411 (11)	1.02576 (16)	0.0741 (5)
H6	0.6758	0.0884	0.9856	0.089*
C7	0.86935 (13)	0.28927 (10)	1.07559 (14)	0.0600 (4)
H7	0.8285	0.2669	1.1209	0.072*
C8	0.92347 (14)	0.35847 (11)	1.11063 (15)	0.0692 (5)
H8	0.9191	0.3828	1.1796	0.083*
C9	0.98393 (15)	0.39192 (11)	1.04424 (17)	0.0719 (5)
H9	1.0205	0.4388	1.0682	0.086*
C10	0.99010 (14)	0.35617 (12)	0.94293 (16)	0.0742 (5)
H10	1.0304	0.3791	0.8975	0.089*
C11	0.93693 (14)	0.28622 (11)	0.90749 (15)	0.0670 (5)
H11	0.9425	0.2616	0.8392	0.080*
C12	0.87536 (12)	0.25291 (9)	0.97371 (13)	0.0531 (4)
C13	0.73979 (12)	0.18623 (9)	0.82857 (12)	0.0521 (4)
C14	0.69523 (13)	0.25939 (9)	0.78731 (13)	0.0543 (4)
H14	0.7134	0.3051	0.8321	0.065*
C15	0.62532 (12)	0.26470 (9)	0.68204 (14)	0.0532 (4)
H15	0.5975	0.3143	0.6563	0.064*
C16	0.59430 (11)	0.19754 (9)	0.61181 (13)	0.0504 (4)
C17	0.63661 (12)	0.12448 (10)	0.65608 (13)	0.0571 (4)
H17	0.6158	0.0784	0.6131	0.069*
C18	0.70818 (13)	0.11848 (10)	0.76140 (14)	0.0578 (4)
H18	0.7355	0.0689	0.7878	0.069*
C19	0.52268 (12)	0.20214 (10)	0.49796 (13)	0.0533 (4)
H19	0.4978	0.1541	0.4626	0.064*
C20	0.48912 (12)	0.26930 (10)	0.43923 (14)	0.0552 (4)
H20	0.5141	0.3171	0.4753	0.066*
C21	0.41880 (11)	0.27527 (9)	0.32670 (13)	0.0501 (4)
C22	0.40255 (12)	0.34749 (9)	0.27357 (13)	0.0549 (4)
H22	0.4357	0.3918	0.3131	0.066*
C23	0.33747 (12)	0.35870 (9)	0.16069 (13)	0.0512 (4)
C24	0.28127 (13)	0.28808 (9)	0.09855 (13)	0.0561 (4)
H24A	0.3210	0.2671	0.0465	0.067*
H24B	0.2144	0.3056	0.0515	0.067*
C25	0.26297 (12)	0.22075 (9)	0.17857 (13)	0.0520 (4)
C26	0.36565 (12)	0.20259 (9)	0.26656 (14)	0.0545 (4)
H26A	0.3521	0.1660	0.3243	0.065*
H26B	0.4123	0.1761	0.2269	0.065*
C27	0.17984 (13)	0.24505 (11)	0.24035 (16)	0.0686 (5)
H27A	0.1163	0.2569	0.1840	0.103*
H27B	0.2026	0.2915	0.2869	0.103*
H27C	0.1681	0.2021	0.2891	0.103*
C28	0.22779 (15)	0.14665 (11)	0.10523 (16)	0.0787 (6)
H28A	0.2813	0.1307	0.0679	0.118*
H28B	0.1651	0.1584	0.0475	0.118*
H28C	0.2148	0.1042	0.1541	0.118*
C29	0.32897 (13)	0.43195 (9)	0.10715 (14)	0.0590 (4)
C30	0.38730 (16)	0.49914 (11)	0.16151 (17)	0.0730 (5)
C31	0.26565 (15)	0.44413 (10)	−0.00723 (17)	0.0649 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0691 (9)	0.0547 (8)	0.0565 (8)	−0.0110 (7)	−0.0001 (7)	0.0077 (6)
N2	0.1275 (16)	0.0607 (11)	0.1231 (15)	−0.0240 (11)	0.0169 (12)	−0.0041 (10)
N3	0.1009 (13)	0.0683 (11)	0.0790 (11)	−0.0048 (9)	0.0118 (9)	0.0167 (8)
C1	0.141 (2)	0.0771 (15)	0.0818 (15)	−0.0301 (15)	0.0420 (15)	0.0037 (11)
C2	0.190 (3)	0.0671 (15)	0.0774 (15)	−0.0170 (18)	−0.0100 (18)	0.0142 (11)
C3	0.133 (2)	0.0778 (16)	0.122 (2)	−0.0014 (16)	−0.0367 (17)	0.0290 (15)
C4	0.0822 (14)	0.0771 (14)	0.1062 (16)	−0.0069 (11)	−0.0110 (12)	0.0232 (12)
C5	0.0716 (11)	0.0487 (9)	0.0526 (9)	−0.0029 (8)	0.0101 (8)	0.0012 (7)
C6	0.0856 (13)	0.0656 (12)	0.0772 (12)	−0.0033 (10)	0.0315 (10)	0.0035 (9)
C7	0.0588 (10)	0.0628 (11)	0.0595 (9)	−0.0036 (8)	0.0162 (8)	0.0009 (8)
C8	0.0745 (12)	0.0604 (11)	0.0696 (11)	0.0016 (9)	0.0112 (9)	−0.0073 (8)
C9	0.0724 (12)	0.0521 (10)	0.0809 (12)	−0.0102 (9)	−0.0011 (9)	0.0066 (9)
C10	0.0684 (12)	0.0802 (13)	0.0709 (12)	−0.0198 (10)	0.0111 (9)	0.0164 (10)
C11	0.0672 (11)	0.0787 (12)	0.0552 (9)	−0.0115 (9)	0.0149 (8)	0.0008 (8)
C12	0.0512 (9)	0.0529 (9)	0.0517 (8)	−0.0048 (7)	0.0059 (7)	0.0057 (7)
C13	0.0522 (9)	0.0521 (9)	0.0507 (8)	−0.0033 (7)	0.0099 (7)	0.0008 (7)
C14	0.0576 (9)	0.0484 (9)	0.0559 (9)	−0.0010 (7)	0.0117 (7)	−0.0049 (7)
C15	0.0517 (9)	0.0481 (9)	0.0597 (9)	0.0047 (7)	0.0132 (7)	0.0000 (7)
C16	0.0429 (8)	0.0542 (9)	0.0544 (9)	0.0022 (7)	0.0126 (6)	−0.0010 (7)
C17	0.0558 (9)	0.0525 (10)	0.0606 (9)	−0.0009 (8)	0.0092 (7)	−0.0085 (7)
C18	0.0595 (10)	0.0469 (9)	0.0635 (10)	0.0054 (7)	0.0080 (8)	0.0017 (7)
C19	0.0437 (8)	0.0570 (10)	0.0589 (9)	−0.0002 (7)	0.0118 (7)	−0.0057 (7)
C20	0.0462 (9)	0.0565 (10)	0.0612 (9)	−0.0058 (7)	0.0098 (7)	−0.0016 (7)
C21	0.0413 (8)	0.0512 (9)	0.0588 (9)	−0.0006 (7)	0.0141 (7)	−0.0009 (7)
C22	0.0528 (9)	0.0501 (9)	0.0619 (9)	−0.0073 (7)	0.0139 (7)	−0.0040 (7)
C23	0.0491 (8)	0.0484 (9)	0.0592 (9)	−0.0017 (7)	0.0193 (7)	−0.0003 (7)
C24	0.0558 (9)	0.0552 (10)	0.0573 (9)	−0.0034 (7)	0.0135 (7)	−0.0001 (7)
C25	0.0471 (8)	0.0459 (8)	0.0597 (9)	−0.0019 (7)	0.0068 (7)	0.0021 (7)
C26	0.0476 (8)	0.0490 (9)	0.0646 (9)	0.0025 (7)	0.0089 (7)	−0.0003 (7)
C27	0.0488 (9)	0.0758 (12)	0.0828 (12)	−0.0002 (8)	0.0192 (8)	0.0162 (9)
C28	0.0809 (13)	0.0588 (11)	0.0841 (13)	−0.0143 (9)	−0.0039 (10)	−0.0047 (9)
C29	0.0636 (10)	0.0501 (9)	0.0652 (10)	−0.0030 (8)	0.0189 (8)	0.0023 (7)
C30	0.0869 (14)	0.0490 (10)	0.0813 (12)	−0.0072 (10)	0.0173 (10)	0.0056 (9)
C31	0.0738 (12)	0.0497 (10)	0.0730 (12)	−0.0035 (9)	0.0215 (9)	0.0079 (8)

Geometric parameters (Å, º) top

N1—C13	1.405 (2)	C15—H15	0.9300
N1—C5	1.418 (2)	C16—C17	1.395 (2)
N1—C12	1.431 (2)	C16—C19	1.453 (2)
N2—C30	1.141 (2)	C17—C18	1.378 (2)
N3—C31	1.143 (2)	C17—H17	0.9300
C1—C2	1.354 (4)	C18—H18	0.9300
C1—C6	1.392 (3)	C19—C20	1.342 (2)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.347 (4)	C20—C21	1.435 (2)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.375 (3)	C21—C22	1.358 (2)
C3—H3	0.9300	C21—C26	1.498 (2)
C4—C5	1.374 (3)	C22—C23	1.420 (2)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.374 (2)	C23—C29	1.375 (2)
C6—H6	0.9300	C23—C24	1.494 (2)
C7—C8	1.373 (2)	C24—C25	1.533 (2)
C7—C12	1.375 (2)	C24—H24A	0.9700
C7—H7	0.9300	C24—H24B	0.9700
C8—C9	1.373 (3)	C25—C27	1.520 (2)
C8—H8	0.9300	C25—C28	1.524 (2)
C9—C10	1.365 (3)	C25—C26	1.531 (2)
C9—H9	0.9300	C26—H26A	0.9700
C10—C11	1.379 (2)	C26—H26B	0.9700
C10—H10	0.9300	C27—H27A	0.9600
C11—C12	1.381 (2)	C27—H27B	0.9600
C11—H11	0.9300	C27—H27C	0.9600
C13—C18	1.392 (2)	C28—H28A	0.9600
C13—C14	1.397 (2)	C28—H28B	0.9600
C14—C15	1.366 (2)	C28—H28C	0.9600
C14—H14	0.9300	C29—C31	1.428 (3)
C15—C16	1.402 (2)	C29—C30	1.428 (3)

C13—N1—C5	122.75 (13)	C17—C18—C13	120.40 (15)
C13—N1—C12	118.53 (12)	C17—C18—H18	119.8
C5—N1—C12	118.29 (13)	C13—C18—H18	119.8
C2—C1—C6	121.1 (2)	C20—C19—C16	125.98 (15)
C2—C1—H1	119.4	C20—C19—H19	117.0
C6—C1—H1	119.4	C16—C19—H19	117.0
C3—C2—C1	119.4 (2)	C19—C20—C21	126.94 (15)
C3—C2—H2	120.3	C19—C20—H20	116.5
C1—C2—H2	120.3	C21—C20—H20	116.5
C2—C3—C4	120.8 (2)	C22—C21—C20	119.28 (14)
C2—C3—H3	119.6	C22—C21—C26	119.98 (14)
C4—C3—H3	119.6	C20—C21—C26	120.72 (14)
C5—C4—C3	120.8 (2)	C21—C22—C23	123.27 (14)
C5—C4—H4	119.6	C21—C22—H22	118.4
C3—C4—H4	119.6	C23—C22—H22	118.4
C4—C5—C6	118.46 (17)	C29—C23—C22	121.22 (14)
C4—C5—N1	119.87 (17)	C29—C23—C24	120.23 (14)
C6—C5—N1	121.62 (16)	C22—C23—C24	118.50 (13)
C5—C6—C1	119.5 (2)	C23—C24—C25	114.28 (13)
C5—C6—H6	120.3	C23—C24—H24A	108.7
C1—C6—H6	120.3	C25—C24—H24A	108.7
C8—C7—C12	120.24 (16)	C23—C24—H24B	108.7
C8—C7—H7	119.9	C25—C24—H24B	108.7
C12—C7—H7	119.9	H24A—C24—H24B	107.6
C9—C8—C7	120.29 (17)	C27—C25—C28	109.77 (14)
C9—C8—H8	119.9	C27—C25—C26	110.51 (14)
C7—C8—H8	119.9	C28—C25—C26	109.03 (13)
C10—C9—C8	119.75 (17)	C27—C25—C24	110.18 (13)
C10—C9—H9	120.1	C28—C25—C24	108.51 (13)
C8—C9—H9	120.1	C26—C25—C24	108.80 (13)
C9—C10—C11	120.45 (17)	C21—C26—C25	113.60 (12)
C9—C10—H10	119.8	C21—C26—H26A	108.8
C11—C10—H10	119.8	C25—C26—H26A	108.8
C10—C11—C12	119.83 (17)	C21—C26—H26B	108.8
C10—C11—H11	120.1	C25—C26—H26B	108.8
C12—C11—H11	120.1	H26A—C26—H26B	107.7
C7—C12—C11	119.43 (15)	C25—C27—H27A	109.5
C7—C12—N1	120.57 (14)	C25—C27—H27B	109.5
C11—C12—N1	119.96 (14)	H27A—C27—H27B	109.5
C18—C13—C14	118.16 (14)	C25—C27—H27C	109.5
C18—C13—N1	121.87 (14)	H27A—C27—H27C	109.5
C14—C13—N1	119.96 (14)	H27B—C27—H27C	109.5
C15—C14—C13	120.86 (14)	C25—C28—H28A	109.5
C15—C14—H14	119.6	C25—C28—H28B	109.5
C13—C14—H14	119.6	H28A—C28—H28B	109.5
C14—C15—C16	121.88 (14)	C25—C28—H28C	109.5
C14—C15—H15	119.1	H28A—C28—H28C	109.5
C16—C15—H15	119.1	H28B—C28—H28C	109.5
C17—C16—C15	116.57 (14)	C23—C29—C31	122.11 (15)
C17—C16—C19	120.59 (14)	C23—C29—C30	121.35 (15)
C15—C16—C19	122.84 (14)	C31—C29—C30	116.48 (15)
C18—C17—C16	122.08 (15)	N2—C30—C29	178.8 (2)
C18—C17—H17	119.0	N3—C31—C29	179.1 (2)
C16—C17—H17	119.0

C6—C1—C2—C3	−0.5 (4)	C14—C15—C16—C17	1.5 (2)
C1—C2—C3—C4	−0.1 (4)	C14—C15—C16—C19	−177.95 (14)
C2—C3—C4—C5	0.2 (4)	C15—C16—C17—C18	−2.3 (2)
C3—C4—C5—C6	0.2 (3)	C19—C16—C17—C18	177.10 (14)
C3—C4—C5—N1	177.9 (2)	C16—C17—C18—C13	0.9 (2)
C13—N1—C5—C4	144.71 (18)	C14—C13—C18—C17	1.4 (2)
C12—N1—C5—C4	−42.9 (2)	N1—C13—C18—C17	−177.36 (14)
C13—N1—C5—C6	−37.7 (2)	C17—C16—C19—C20	−169.57 (15)
C12—N1—C5—C6	134.71 (17)	C15—C16—C19—C20	9.8 (2)
C4—C5—C6—C1	−0.7 (3)	C16—C19—C20—C21	179.76 (14)
N1—C5—C6—C1	−178.40 (17)	C19—C20—C21—C22	−172.13 (15)
C2—C1—C6—C5	0.9 (3)	C19—C20—C21—C26	6.3 (2)
C12—C7—C8—C9	0.0 (3)	C20—C21—C22—C23	177.62 (13)
C7—C8—C9—C10	0.1 (3)	C26—C21—C22—C23	−0.8 (2)
C8—C9—C10—C11	−0.7 (3)	C21—C22—C23—C29	−175.45 (14)
C9—C10—C11—C12	1.3 (3)	C21—C22—C23—C24	2.0 (2)
C8—C7—C12—C11	0.5 (3)	C29—C23—C24—C25	−158.00 (14)
C8—C7—C12—N1	−177.28 (15)	C22—C23—C24—C25	24.5 (2)
C10—C11—C12—C7	−1.2 (3)	C23—C24—C25—C27	72.25 (18)
C10—C11—C12—N1	176.63 (15)	C23—C24—C25—C28	−167.55 (13)
C13—N1—C12—C7	116.95 (17)	C23—C24—C25—C26	−49.05 (18)
C5—N1—C12—C7	−55.8 (2)	C22—C21—C26—C25	−26.7 (2)
C13—N1—C12—C11	−60.8 (2)	C20—C21—C26—C25	154.85 (14)
C5—N1—C12—C11	126.46 (17)	C27—C25—C26—C21	−71.15 (17)
C5—N1—C13—C18	−33.5 (2)	C28—C25—C26—C21	168.12 (13)
C12—N1—C13—C18	154.15 (15)	C24—C25—C26—C21	49.95 (18)
C5—N1—C13—C14	147.73 (15)	C22—C23—C29—C31	178.69 (14)
C12—N1—C13—C14	−24.6 (2)	C24—C23—C29—C31	1.2 (2)
C18—C13—C14—C15	−2.3 (2)	C22—C23—C29—C30	1.7 (2)
N1—C13—C14—C15	176.54 (14)	C24—C23—C29—C30	−175.73 (15)
C13—C14—C15—C16	0.8 (2)

Experimental details

Crystal data
Chemical formula	C₃₁H₂₇N₃
M_r	441.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.239 (5), 16.757 (8), 11.886 (3)
β (°)	104.073 (5)
V (Å³)	2557.7 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.48 × 0.19 × 0.16

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20681, 5879, 3554
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.167, 0.92
No. of reflections	5879
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (grant Nos. 50590403, 50402018 and 50603011).

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