1,4-Bis[(2-ethyl-1H-benzimidazol-1-yl)meth­yl]benzene

Wang, Q.; Zhao, X.; Lou, H.; Wang, M.

doi:10.1107/S1600536811025402

organic compounds

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Volume 67| Part 8| August 2011| Page o1899

doi:10.1107/S1600536811025402

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1,4-Bis[(2-ethyl-1H-benzimidazol-1-yl)methyl]benzene

Qiang Wang,^a ^* Xing Zhao,^a Haipeng Lou ^a and Mengyan Wang ^a

^aThe Department of Physics–Chemistry, Henan Polytechnic University, Jiao Zuo, 454000, People's Republic of China
^*Correspondence e-mail: wangqiang@hpu.edu.cn

(Received 20 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title molecule, C₂₆H₂₆N₄, the central benzene ring forms dihedral angles of 89.9 (2) and 85.4 (2)° with the two benzimidazole rings.

Related literature

The title compound is a precursor of N,NN′-benzimidazolium ionic liquids (ILs). For background to the use of ILs as solvents or ligands in the synthesis of new metal-organic frameworks (MOFs), see: Fei et al. (2006 ); Wang et al. (2009 ); Xu et al. (2009 ). For properties of metal-containing ILs, see: Lee et al. (2004 ); Sasaki et al. (2005 ); Wang et al. (2009). For details of the synthesis, see Rajakannu et al. (2011 ).

Experimental

Crystal data

C₂₆H₂₆N₄
M_r = 394.51
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.300 (2) Å
b = 11.437 (2) Å
c = 17.809 (4) Å
V = 2098.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.986, T_max = 0.989
16782 measured reflections
2829 independent reflections
2488 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.153
S = 1.04
2829 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025402/ng5188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025402/ng5188Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025402/ng5188Isup3.cml

checkCIF report

Comment top

Ionic liquids (ILs) have attracted great interest as solvents or ligands in the synthesis of new metal-organic frameworks (MOFs)(Fei et al.,2006; Wang et al., 2009; Xu et al., 2009). By incorporating metal ions to the ILs, metal-containing ILs can be formed. the presence of metal ions in ILs provided many additional properties such as color, geometry, and magnetism (Lee et al., 2004; Sasaki et al., 2005; Wang et al., 2009). As a part of our program devoted to the new applications of the ILs ligands in coordination polymer, we report herein the crystal structure of the title compound as the precursor of the N,N'-benzimidazolium ILs.

The molecule structure of title compound was shown in the Fig.1, all bond lengths and angles are in normal range. In the crystal structure, the central benzene ring forms dihedral angles of 88.9 (0)° and 84.4 (2)° with the two benzimidazole rings, respectively. The N2 atom are nearly co-planar with benzene ring by 0.055 (4) Å derivation. The crystal packing is stabilized by van der Waals forces.

Related literature top

For background to the use of ionic liquids (ILs) as solvents or ligands in the synthesis of new metal-organic frameworks (MOFs), see: Fei et al. (2006); Wang et al. (2009); Xu et al. (2009). For properties of metal-containing ILs, see: Lee et al. (2004); Sasaki et al. (2005); Wang et al. (2009). For details of the synthesis, see Rajakannu et al. (2011).

Experimental top

(type here to add preparation details)

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1,4-Bis[(2-ethyl-1H-benzimidazol-1-yl)methyl]benzene top

Crystal data top

C₂₆H₂₆N₄	F(000) = 840
M_r = 394.51	D_x = 1.249 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.300 (2) Å	θ = 2.1–25.0°
b = 11.437 (2) Å	µ = 0.08 mm⁻¹
c = 17.809 (4) Å	T = 298 K
V = 2098.0 (7) Å³	Block, colorless
Z = 4	0.20 × 0.16 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	2829 independent reflections
Radiation source: fine-focus sealed tube	2488 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→11
T_min = 0.986, T_max = 0.989	k = −13→15
16782 measured reflections	l = −23→23

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0508P)² + 1.P] where P = (F_o² + 2F_c²)/3
2829 reflections	(Δ/σ)_max = 0.002
273 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₆H₂₆N₄	V = 2098.0 (7) Å³
M_r = 394.51	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.300 (2) Å	µ = 0.08 mm⁻¹
b = 11.437 (2) Å	T = 298 K
c = 17.809 (4) Å	0.20 × 0.16 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	2829 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2488 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.989	R_int = 0.053
16782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.04	Δρ_max = 0.13 e Å⁻³
2829 reflections	Δρ_min = −0.19 e Å⁻³
273 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
C1	0.7649 (6)	0.2700 (5)	0.3958 (3)	0.0931 (19)
H1A	0.7571	0.1868	0.4012	0.140*
H1B	0.7173	0.3081	0.4351	0.140*
H1C	0.8547	0.2919	0.3988	0.140*
C2	0.8228 (5)	0.9074 (4)	0.3524 (3)	0.0684 (13)
H2A	0.8441	0.9889	0.3563	0.103*
H2B	0.8855	0.8621	0.3796	0.103*
H2C	0.7380	0.8942	0.3730	0.103*
C3	0.7113 (5)	0.3063 (4)	0.3214 (3)	0.0656 (12)
H3A	0.6210	0.2828	0.3188	0.079*
H3B	0.7142	0.3909	0.3180	0.079*
C4	0.4406 (5)	1.0546 (4)	0.0497 (3)	0.0729 (14)
H4	0.4007	1.0658	0.0034	0.087*
C5	0.3894 (5)	1.1102 (4)	0.1121 (3)	0.0676 (13)
H5	0.3159	1.1567	0.1068	0.081*
C6	0.9239 (5)	0.1282 (4)	0.0326 (3)	0.0688 (13)
H6	0.9285	0.1148	−0.0188	0.083*
C7	1.0183 (5)	0.0806 (4)	0.0793 (3)	0.0681 (13)
H7	1.0848	0.0364	0.0582	0.082*
C8	0.5478 (5)	0.9837 (4)	0.0534 (3)	0.0648 (12)
H8	0.5806	0.9463	0.0111	0.078*
C9	0.8237 (4)	0.1949 (4)	0.0606 (2)	0.0586 (11)
H9	0.7607	0.2275	0.0296	0.070*
C10	0.8240 (4)	0.8715 (4)	0.2708 (2)	0.0567 (11)
H10A	0.9077	0.8915	0.2494	0.068*
H10B	0.8145	0.7872	0.2679	0.068*
C11	1.0161 (4)	0.0968 (4)	0.1559 (3)	0.0586 (11)
H11	1.0800	0.0649	0.1866	0.070*
C12	0.7925 (4)	0.8299 (3)	0.1041 (2)	0.0528 (10)
H12A	0.8825	0.8395	0.1190	0.063*
H12B	0.7856	0.8511	0.0515	0.063*
C13	0.6274 (4)	0.6663 (3)	0.1021 (2)	0.0473 (9)
H13	0.5662	0.7196	0.0847	0.057*
C14	0.8429 (4)	0.6215 (3)	0.1381 (2)	0.0494 (10)
H14	0.9287	0.6438	0.1459	0.059*
C15	0.5904 (4)	0.5521 (3)	0.1160 (2)	0.0463 (9)
H15	0.5044	0.5301	0.1085	0.056*
C16	0.4456 (4)	1.0978 (3)	0.1817 (3)	0.0551 (10)
H16	0.4118	1.1361	0.2234	0.066*
C17	0.6048 (4)	0.9707 (3)	0.1238 (2)	0.0481 (10)
C18	0.7536 (4)	0.7026 (3)	0.1137 (2)	0.0429 (9)
C19	0.8053 (4)	0.5061 (3)	0.1511 (2)	0.0479 (9)
H19	0.8670	0.4522	0.1671	0.058*
N4	0.6289 (3)	0.9968 (3)	0.25067 (19)	0.0487 (8)
C20	0.8219 (4)	0.2108 (3)	0.1384 (2)	0.0438 (9)
C21	0.7811 (4)	0.2564 (3)	0.2563 (2)	0.0450 (9)
C22	0.6790 (4)	0.4702 (3)	0.1407 (2)	0.0409 (8)
C23	0.9151 (4)	0.1625 (3)	0.1859 (2)	0.0460 (9)
C24	0.5549 (4)	1.0261 (3)	0.1880 (2)	0.0462 (9)
N3	0.7116 (3)	0.9081 (3)	0.14849 (19)	0.0469 (8)
C25	0.7199 (4)	0.9271 (3)	0.2246 (2)	0.0462 (9)
N1	0.8875 (3)	0.1927 (3)	0.25983 (19)	0.0512 (8)
N2	0.7370 (3)	0.2705 (2)	0.18419 (18)	0.0431 (7)
C26	0.6341 (4)	0.3469 (3)	0.1584 (2)	0.0476 (9)
H26A	0.5673	0.3506	0.1966	0.057*
H26B	0.5955	0.3134	0.1136	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.117 (5)	0.110 (4)	0.052 (3)	0.041 (4)	0.011 (3)	−0.003 (3)
C2	0.081 (3)	0.068 (3)	0.056 (3)	0.009 (3)	−0.011 (3)	0.004 (2)
C3	0.067 (3)	0.069 (3)	0.061 (3)	0.018 (2)	0.008 (2)	−0.004 (2)
C4	0.090 (4)	0.064 (3)	0.064 (3)	0.000 (3)	−0.021 (3)	0.010 (3)
C5	0.062 (3)	0.056 (3)	0.085 (4)	0.000 (2)	−0.015 (3)	0.014 (3)
C6	0.084 (4)	0.065 (3)	0.058 (3)	−0.004 (3)	0.016 (3)	−0.004 (2)
C7	0.068 (3)	0.059 (3)	0.078 (3)	0.003 (2)	0.020 (3)	−0.011 (2)
C8	0.084 (3)	0.052 (2)	0.058 (3)	0.002 (2)	−0.007 (3)	0.003 (2)
C9	0.060 (3)	0.057 (2)	0.058 (3)	−0.008 (2)	0.000 (2)	0.003 (2)
C10	0.058 (3)	0.054 (2)	0.058 (3)	0.009 (2)	−0.005 (2)	−0.001 (2)
C11	0.049 (2)	0.052 (2)	0.074 (3)	0.005 (2)	0.004 (2)	−0.004 (2)
C12	0.065 (3)	0.037 (2)	0.056 (2)	−0.0053 (19)	0.012 (2)	0.0022 (18)
C13	0.051 (2)	0.041 (2)	0.051 (2)	0.0031 (18)	−0.0063 (19)	0.0059 (17)
C14	0.041 (2)	0.042 (2)	0.065 (3)	−0.0067 (17)	0.0014 (19)	−0.0016 (18)
C15	0.041 (2)	0.044 (2)	0.054 (2)	−0.0034 (17)	−0.0085 (18)	−0.0004 (18)
C16	0.051 (2)	0.044 (2)	0.070 (3)	−0.0003 (19)	−0.001 (2)	0.007 (2)
C17	0.060 (3)	0.0322 (18)	0.052 (2)	−0.0064 (18)	0.000 (2)	0.0065 (16)
C18	0.052 (2)	0.0358 (18)	0.041 (2)	−0.0026 (17)	0.0066 (18)	−0.0046 (15)
C19	0.042 (2)	0.0382 (19)	0.063 (2)	0.0003 (17)	−0.0072 (19)	0.0028 (18)
N4	0.0480 (18)	0.0435 (17)	0.0546 (19)	−0.0018 (15)	0.0026 (16)	−0.0025 (15)
C20	0.050 (2)	0.0317 (17)	0.049 (2)	−0.0045 (16)	0.0024 (19)	0.0028 (16)
C21	0.048 (2)	0.041 (2)	0.045 (2)	−0.0006 (18)	0.0005 (17)	0.0027 (17)
C22	0.044 (2)	0.0409 (19)	0.0380 (18)	0.0006 (16)	−0.0033 (16)	−0.0016 (15)
C23	0.044 (2)	0.0373 (19)	0.057 (2)	−0.0043 (16)	0.0030 (19)	−0.0010 (17)
C24	0.049 (2)	0.0367 (18)	0.054 (2)	−0.0081 (17)	−0.0017 (19)	0.0057 (17)
N3	0.056 (2)	0.0364 (16)	0.0484 (18)	0.0004 (15)	0.0037 (16)	0.0001 (14)
C25	0.051 (2)	0.039 (2)	0.049 (2)	−0.0043 (18)	0.0016 (18)	0.0004 (16)
N1	0.0480 (19)	0.0485 (19)	0.057 (2)	0.0046 (16)	0.0009 (16)	−0.0002 (16)
N2	0.0432 (17)	0.0356 (15)	0.0504 (18)	0.0028 (13)	−0.0008 (15)	0.0022 (14)
C26	0.045 (2)	0.0358 (18)	0.062 (2)	0.0002 (17)	−0.0034 (19)	0.0048 (17)

Geometric parameters (Å, º) top

C1—C3	1.492 (6)	C12—N3	1.456 (5)
C1—H1A	0.9600	C12—C18	1.520 (5)
C1—H1B	0.9600	C12—H12A	0.9700
C1—H1C	0.9600	C12—H12B	0.9700
C2—C10	1.510 (6)	C13—C18	1.380 (5)
C2—H2A	0.9600	C13—C15	1.383 (5)
C2—H2B	0.9600	C13—H13	0.9300
C2—H2C	0.9600	C14—C18	1.376 (5)
C3—C21	1.479 (5)	C14—C19	1.395 (5)
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—C22	1.380 (5)
C4—C8	1.371 (7)	C15—H15	0.9300
C4—C5	1.384 (7)	C16—C24	1.397 (5)
C4—H4	0.9300	C16—H16	0.9300
C5—C16	1.376 (6)	C17—N3	1.384 (5)
C5—H5	0.9300	C17—C24	1.404 (5)
C6—C9	1.377 (6)	C19—C22	1.377 (5)
C6—C7	1.391 (7)	C19—H19	0.9300
C6—H6	0.9300	N4—C25	1.316 (5)
C7—C11	1.378 (6)	N4—C24	1.393 (5)
C7—H7	0.9300	C20—N2	1.377 (5)
C8—C17	1.393 (6)	C20—C23	1.394 (5)
C8—H8	0.9300	C21—N1	1.317 (5)
C9—C20	1.396 (6)	C21—N2	1.372 (5)
C9—H9	0.9300	C22—C26	1.516 (5)
C10—C25	1.495 (5)	C23—N1	1.390 (5)
C10—H10A	0.9700	N3—C25	1.375 (5)
C10—H10B	0.9700	N2—C26	1.449 (4)
C11—C23	1.390 (5)	C26—H26A	0.9700
C11—H11	0.9300	C26—H26B	0.9700

C3—C1—H1A	109.5	C18—C13—H13	119.5
C3—C1—H1B	109.5	C15—C13—H13	119.5
H1A—C1—H1B	109.5	C18—C14—C19	120.3 (4)
C3—C1—H1C	109.5	C18—C14—H14	119.8
H1A—C1—H1C	109.5	C19—C14—H14	119.8
H1B—C1—H1C	109.5	C13—C15—C22	121.1 (4)
C10—C2—H2A	109.5	C13—C15—H15	119.5
C10—C2—H2B	109.5	C22—C15—H15	119.5
H2A—C2—H2B	109.5	C5—C16—C24	118.1 (4)
C10—C2—H2C	109.5	C5—C16—H16	120.9
H2A—C2—H2C	109.5	C24—C16—H16	120.9
H2B—C2—H2C	109.5	N3—C17—C8	132.6 (4)
C21—C3—C1	114.1 (4)	N3—C17—C24	105.4 (3)
C21—C3—H3A	108.7	C8—C17—C24	122.0 (4)
C1—C3—H3A	108.7	C13—C18—C14	118.3 (3)
C21—C3—H3B	108.7	C13—C18—C12	121.3 (4)
C1—C3—H3B	108.7	C14—C18—C12	120.3 (4)
H3A—C3—H3B	107.6	C22—C19—C14	121.5 (4)
C8—C4—C5	122.7 (5)	C22—C19—H19	119.3
C8—C4—H4	118.6	C14—C19—H19	119.3
C5—C4—H4	118.6	C25—N4—C24	104.6 (3)
C16—C5—C4	121.0 (5)	N2—C20—C9	131.3 (4)
C16—C5—H5	119.5	N2—C20—C23	105.9 (3)
C4—C5—H5	119.5	C9—C20—C23	122.8 (4)
C9—C6—C7	121.6 (4)	N1—C21—N2	112.6 (3)
C9—C6—H6	119.2	N1—C21—C3	125.5 (4)
C7—C6—H6	119.2	N2—C21—C3	121.9 (3)
C11—C7—C6	121.9 (4)	C19—C22—C15	117.7 (3)
C11—C7—H7	119.1	C19—C22—C26	122.5 (3)
C6—C7—H7	119.1	C15—C22—C26	119.7 (3)
C4—C8—C17	116.5 (5)	C11—C23—N1	130.6 (4)
C4—C8—H8	121.8	C11—C23—C20	119.8 (4)
C17—C8—H8	121.8	N1—C23—C20	109.6 (3)
C6—C9—C20	116.2 (4)	N4—C24—C16	130.3 (4)
C6—C9—H9	121.9	N4—C24—C17	110.1 (3)
C20—C9—H9	121.9	C16—C24—C17	119.6 (4)
C25—C10—C2	114.1 (4)	C25—N3—C17	106.3 (3)
C25—C10—H10A	108.7	C25—N3—C12	126.6 (4)
C2—C10—H10A	108.7	C17—N3—C12	126.9 (3)
C25—C10—H10B	108.7	N4—C25—N3	113.5 (4)
C2—C10—H10B	108.7	N4—C25—C10	125.1 (4)
H10A—C10—H10B	107.6	N3—C25—C10	121.4 (4)
C7—C11—C23	117.8 (4)	C21—N1—C23	105.2 (3)
C7—C11—H11	121.1	C21—N2—C20	106.6 (3)
C23—C11—H11	121.1	C21—N2—C26	127.6 (3)
N3—C12—C18	112.1 (3)	C20—N2—C26	125.1 (3)
N3—C12—H12A	109.2	N2—C26—C22	113.8 (3)
C18—C12—H12A	109.2	N2—C26—H26A	108.8
N3—C12—H12B	109.2	C22—C26—H26A	108.8
C18—C12—H12B	109.2	N2—C26—H26B	108.8
H12A—C12—H12B	107.9	C22—C26—H26B	108.8
C18—C13—C15	121.1 (4)	H26A—C26—H26B	107.7

C8—C4—C5—C16	0.8 (7)	N3—C17—C24—N4	−0.6 (4)
C9—C6—C7—C11	0.4 (7)	C8—C17—C24—N4	179.1 (4)
C5—C4—C8—C17	−0.6 (7)	N3—C17—C24—C16	179.5 (3)
C7—C6—C9—C20	−0.5 (7)	C8—C17—C24—C16	−0.8 (6)
C6—C7—C11—C23	0.4 (7)	C8—C17—N3—C25	−179.0 (4)
C18—C13—C15—C22	−1.1 (6)	C24—C17—N3—C25	0.7 (4)
C4—C5—C16—C24	−0.9 (6)	C8—C17—N3—C12	−3.7 (7)
C4—C8—C17—N3	−179.8 (4)	C24—C17—N3—C12	176.0 (3)
C4—C8—C17—C24	0.6 (6)	C18—C12—N3—C25	77.0 (5)
C15—C13—C18—C14	1.3 (6)	C18—C12—N3—C17	−97.5 (4)
C15—C13—C18—C12	−175.4 (4)	C24—N4—C25—N3	0.1 (4)
C19—C14—C18—C13	−0.5 (6)	C24—N4—C25—C10	−179.7 (4)
C19—C14—C18—C12	176.3 (4)	C17—N3—C25—N4	−0.5 (4)
N3—C12—C18—C13	53.7 (5)	C12—N3—C25—N4	−175.9 (3)
N3—C12—C18—C14	−123.0 (4)	C17—N3—C25—C10	179.3 (3)
C18—C14—C19—C22	−0.5 (6)	C12—N3—C25—C10	3.9 (6)
C6—C9—C20—N2	−179.5 (4)	C2—C10—C25—N4	−3.5 (6)
C6—C9—C20—C23	−0.2 (6)	C2—C10—C25—N3	176.8 (4)
C1—C3—C21—N1	−5.2 (7)	N2—C21—N1—C23	−0.3 (4)
C1—C3—C21—N2	173.1 (4)	C3—C21—N1—C23	178.1 (4)
C14—C19—C22—C15	0.8 (6)	C11—C23—N1—C21	179.6 (4)
C14—C19—C22—C26	−176.7 (4)	C20—C23—N1—C21	0.3 (4)
C13—C15—C22—C19	0.0 (6)	N1—C21—N2—C20	0.2 (4)
C13—C15—C22—C26	177.6 (4)	C3—C21—N2—C20	−178.3 (4)
C7—C11—C23—N1	179.7 (4)	N1—C21—N2—C26	−171.1 (3)
C7—C11—C23—C20	−1.1 (6)	C3—C21—N2—C26	10.4 (6)
N2—C20—C23—C11	−179.6 (3)	C9—C20—N2—C21	179.4 (4)
C9—C20—C23—C11	1.0 (6)	C23—C20—N2—C21	0.0 (4)
N2—C20—C23—N1	−0.2 (4)	C9—C20—N2—C26	−9.0 (6)
C9—C20—C23—N1	−179.7 (4)	C23—C20—N2—C26	171.6 (3)
C25—N4—C24—C16	−179.8 (4)	C21—N2—C26—C22	86.5 (5)
C25—N4—C24—C17	0.3 (4)	C20—N2—C26—C22	−83.2 (4)
C5—C16—C24—N4	−178.9 (4)	C19—C22—C26—N2	−2.2 (6)
C5—C16—C24—C17	0.9 (5)	C15—C22—C26—N2	−179.6 (3)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₄
M_r	394.51
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	10.300 (2), 11.437 (2), 17.809 (4)
V (Å³)	2098.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.986, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	16782, 2829, 2488
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.153, 1.04
No. of reflections	2829
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.19

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Natural Science Research Program of the Education Department of Henan Province (2011 A150015), Henan Polytechnic University Foundation for Doctoral Teachers (B2010–65) and Henan Polytechnic University Foundation for the Youth (P051102). The authors thank Dr L. Yang and D. Zhao for assistance with the data analysis.

References

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