1,3-Bis(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane

Wu, H.; Yun, R.; Wang, K.; Huang, X.; Sun, Q.

doi:10.1107/S1600536809012781

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1014

doi:10.1107/S1600536809012781

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1,3-Bis(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane

Huilu Wu,^a ^* Ruirui Yun,^a Kaitong Wang,^a Xingcai Huang ^a and Qingyu Sun ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 28 March 2009; accepted 4 April 2009; online 10 April 2009)

In the title compound, C₃₀H₂₆N₄O, the dihedral angle between the two benzimidazole rings is 69.35 (9)°. The dihedral angles between the benzimidazole ring system and the phenyl ring are 76.79 (12) and 86.10 (11)° in the two benzylbenzimidazole moieties.

Related literature

For the biological activity of the benzimidazole core, see: Horton et al. (2003 ). For the antiprotozoal activity of 2- and 5-substituted benzimidazoles, see: Navarrete-Vázquez et al. (2001 ).

Experimental

Crystal data

C₃₀H₂₆N₄O
M_r = 458.55
Triclinic, $[P \overline 1]$
a = 8.5477 (3) Å
b = 11.8976 (5) Å
c = 12.3961 (5) Å
α = 101.300 (1)°
β = 92.394 (1)°
γ = 107.765 (1)°
V = 1170.28 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.58 × 0.52 × 0.19 mm

Data collection

Rigaku R-AXIS Spider diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.955, T_max = 0.985
11531 measured reflections
5275 independent reflections
4542 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.126
S = 1.09
5275 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 global, I. DOI: 10.1107/S1600536809012781/lh2800sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012781/lh2800Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives, such as mebendazole and albendazole, are used as anthelmintic drugs. More recently, the antiprotozoal activity of 2- and 5-substituted benzimidazoles has been reported (Navarrete-Vázquez et al. 2001). The benzimidazole core is of interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between N3/N4/C10-C16 and C18-C23 is 76.79 (12)° and that between N1/N2/C1-C7 and C25-C30 is 86.10 (11)°.

Related literature top

For the biological activity of the benzimidazole core, see: Horton et al. (2003). For the antiprotozoal activity of 2- and 5-substituted benzimidazoles, see: Navarrete-Vázquez et al. (2001).

Experimental top

A solution of 5.56 (20 mmol) of 1,3-bis(benzimidazol-2-yl)-2-oxopropane with 1.56 g (40 mmol) potassium in 150 ml tetrahydrofuran followed by addition of 5.06 g (40 mmol) benzyl bromide was concentrated and recrystallized from methanol, formimg white block crystals suitable for X-ray diffraction studies. (found: C, 78.51; H, 5.73; N,12.24 Calcd. for C₃₀H₂₆N₄O: C, 78.58; H, 5.71; N, 12.22)

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.

1,3-Bis(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane top

Crystal data top

C₃₀H₂₆N₄O	Z = 2
M_r = 458.55	F(000) = 484
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Melting point = 450–451 K
a = 8.5477 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8976 (5) Å	Cell parameters from 5275 reflections
c = 12.3961 (5) Å	θ = 3.0–27.5°
α = 101.300 (1)°	µ = 0.08 mm⁻¹
β = 92.394 (1)°	T = 153 K
γ = 107.765 (1)°	Block, white
V = 1170.28 (8) Å³	0.58 × 0.52 × 0.19 mm

Data collection top

Rigaku R-AXIS Spider diffractometer	5275 independent reflections
Radiation source: fine-focus sealed tube	4542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→10
T_min = 0.955, T_max = 0.985	k = −15→15
11531 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0736P)² + 0.3041P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
5275 reflections	Δρ_max = 0.50 e Å⁻³
317 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

Crystal data top

C₃₀H₂₆N₄O	γ = 107.765 (1)°
M_r = 458.55	V = 1170.28 (8) Å³
Triclinic, P1	Z = 2
a = 8.5477 (3) Å	Mo Kα radiation
b = 11.8976 (5) Å	µ = 0.08 mm⁻¹
c = 12.3961 (5) Å	T = 153 K
α = 101.300 (1)°	0.58 × 0.52 × 0.19 mm
β = 92.394 (1)°

Data collection top

Rigaku R-AXIS Spider diffractometer	5275 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4542 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.985	R_int = 0.013
11531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	Δρ_max = 0.50 e Å⁻³
5275 reflections	Δρ_min = −0.34 e Å⁻³
317 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
O	0.80479 (11)	0.49510 (8)	0.70677 (7)	0.0252 (2)
N1	0.73219 (13)	0.71312 (9)	0.90708 (8)	0.0233 (2)
N2	0.54296 (12)	0.52783 (9)	0.85764 (8)	0.0214 (2)
N3	0.99857 (12)	0.31236 (9)	0.79071 (8)	0.0231 (2)
N4	0.77779 (12)	0.22141 (9)	0.66368 (8)	0.0231 (2)
C1	0.58038 (15)	0.71864 (10)	0.93941 (9)	0.0213 (2)
C2	0.53783 (16)	0.81685 (11)	0.99680 (10)	0.0256 (3)
H2	0.6172	0.8953	1.0182	0.031*
C3	0.37662 (17)	0.79594 (12)	1.02133 (10)	0.0276 (3)
H3	0.3451	0.8610	1.0611	0.033*
C4	0.25816 (16)	0.68035 (12)	0.98864 (10)	0.0276 (3)
H4	0.1483	0.6695	1.0065	0.033*
C5	0.29667 (15)	0.58181 (11)	0.93114 (10)	0.0247 (3)
H5	0.2164	0.5039	0.9086	0.030*
C6	0.46015 (15)	0.60377 (10)	0.90831 (9)	0.0208 (2)
C7	0.70389 (15)	0.59876 (11)	0.85997 (9)	0.0217 (2)
C8	0.83822 (16)	0.55036 (12)	0.82143 (10)	0.0264 (3)
H8A	0.9446	0.6171	0.8349	0.032*
H8B	0.8481	0.4902	0.8640	0.032*
C9	0.92732 (15)	0.44005 (11)	0.67180 (10)	0.0258 (3)
H9A	1.0385	0.4975	0.7013	0.031*
H9B	0.9208	0.4227	0.5900	0.031*
C10	0.90483 (14)	0.32529 (11)	0.71040 (10)	0.0222 (2)
C11	0.79369 (14)	0.13374 (11)	0.71787 (9)	0.0221 (2)
C12	0.70094 (16)	0.01242 (12)	0.70590 (11)	0.0284 (3)
H12	0.6078	−0.0257	0.6520	0.034*
C13	0.75138 (17)	−0.04945 (12)	0.77646 (11)	0.0295 (3)
H13	0.6919	−0.1325	0.7706	0.035*
C14	0.88820 (17)	0.00726 (12)	0.85663 (11)	0.0283 (3)
H14	0.9187	−0.0382	0.9040	0.034*
C15	0.98002 (15)	0.12805 (12)	0.86844 (10)	0.0258 (3)
H15	1.0722	0.1661	0.9231	0.031*
C16	0.93194 (14)	0.19187 (10)	0.79690 (10)	0.0212 (2)
C17	0.64947 (15)	0.20654 (12)	0.57568 (10)	0.0257 (3)
H17A	0.6159	0.2803	0.5873	0.031*
H17B	0.5516	0.1378	0.5808	0.031*
C18	0.70267 (15)	0.18411 (11)	0.46087 (10)	0.0236 (3)
C19	0.66731 (18)	0.24654 (12)	0.38477 (11)	0.0312 (3)
H19	0.6115	0.3040	0.4057	0.037*
C20	0.7125 (2)	0.22588 (14)	0.27833 (12)	0.0403 (4)
H20	0.6869	0.2686	0.2266	0.048*
C21	0.7950 (2)	0.14290 (14)	0.24755 (12)	0.0393 (3)
H21	0.8275	0.1294	0.1750	0.047*
C22	0.82983 (19)	0.07973 (13)	0.32288 (12)	0.0363 (3)
H22	0.8861	0.0225	0.3020	0.044*
C23	0.78271 (17)	0.09980 (12)	0.42866 (11)	0.0303 (3)
H23	0.8055	0.0553	0.4797	0.036*
C24	0.46863 (16)	0.39871 (10)	0.81196 (10)	0.0250 (3)
H24A	0.3901	0.3635	0.8622	0.030*
H24B	0.5565	0.3603	0.8095	0.030*
C25	0.37816 (14)	0.36798 (10)	0.69711 (10)	0.0214 (2)
C26	0.28424 (15)	0.24803 (12)	0.65272 (12)	0.0289 (3)
H26	0.2773	0.1885	0.6950	0.035*
C27	0.20114 (18)	0.21494 (13)	0.54754 (13)	0.0383 (3)
H27	0.1383	0.1327	0.5179	0.046*
C28	0.20876 (18)	0.30063 (14)	0.48511 (12)	0.0382 (3)
H28	0.1505	0.2778	0.4132	0.046*
C29	0.30168 (19)	0.41940 (14)	0.52837 (12)	0.0352 (3)
H29	0.3079	0.4787	0.4859	0.042*
C30	0.38665 (17)	0.45315 (12)	0.63410 (11)	0.0287 (3)
H30	0.4508	0.5352	0.6631	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0294 (4)	0.0282 (4)	0.0204 (4)	0.0137 (4)	0.0023 (3)	0.0041 (3)
N1	0.0256 (5)	0.0211 (5)	0.0220 (5)	0.0072 (4)	−0.0003 (4)	0.0032 (4)
N2	0.0266 (5)	0.0177 (5)	0.0187 (5)	0.0064 (4)	−0.0011 (4)	0.0031 (4)
N3	0.0228 (5)	0.0223 (5)	0.0224 (5)	0.0066 (4)	0.0023 (4)	0.0019 (4)
N4	0.0236 (5)	0.0234 (5)	0.0208 (5)	0.0060 (4)	−0.0005 (4)	0.0043 (4)
C1	0.0254 (6)	0.0206 (5)	0.0176 (5)	0.0066 (4)	0.0005 (4)	0.0051 (4)
C2	0.0331 (6)	0.0207 (6)	0.0217 (6)	0.0085 (5)	0.0023 (5)	0.0023 (4)
C3	0.0374 (7)	0.0288 (6)	0.0200 (6)	0.0159 (5)	0.0062 (5)	0.0044 (5)
C4	0.0297 (6)	0.0346 (7)	0.0204 (6)	0.0120 (5)	0.0047 (5)	0.0075 (5)
C5	0.0265 (6)	0.0262 (6)	0.0192 (5)	0.0046 (5)	0.0011 (4)	0.0060 (4)
C6	0.0268 (6)	0.0208 (5)	0.0147 (5)	0.0072 (4)	0.0002 (4)	0.0045 (4)
C7	0.0250 (6)	0.0221 (6)	0.0181 (5)	0.0079 (4)	−0.0011 (4)	0.0046 (4)
C8	0.0286 (6)	0.0284 (6)	0.0225 (6)	0.0128 (5)	−0.0019 (5)	0.0015 (5)
C9	0.0272 (6)	0.0257 (6)	0.0260 (6)	0.0094 (5)	0.0086 (5)	0.0065 (5)
C10	0.0217 (5)	0.0223 (6)	0.0217 (5)	0.0071 (4)	0.0051 (4)	0.0021 (4)
C11	0.0240 (6)	0.0232 (6)	0.0182 (5)	0.0071 (5)	0.0030 (4)	0.0034 (4)
C12	0.0294 (6)	0.0251 (6)	0.0243 (6)	0.0019 (5)	−0.0017 (5)	0.0022 (5)
C13	0.0358 (7)	0.0217 (6)	0.0281 (6)	0.0046 (5)	0.0050 (5)	0.0056 (5)
C14	0.0343 (7)	0.0292 (6)	0.0253 (6)	0.0138 (5)	0.0050 (5)	0.0083 (5)
C15	0.0256 (6)	0.0290 (6)	0.0224 (6)	0.0099 (5)	0.0003 (5)	0.0036 (5)
C16	0.0209 (5)	0.0211 (5)	0.0201 (5)	0.0064 (4)	0.0040 (4)	0.0011 (4)
C17	0.0225 (6)	0.0314 (6)	0.0229 (6)	0.0092 (5)	0.0002 (5)	0.0048 (5)
C18	0.0225 (6)	0.0210 (5)	0.0230 (6)	0.0025 (4)	−0.0037 (4)	0.0030 (4)
C19	0.0393 (7)	0.0268 (6)	0.0285 (6)	0.0122 (5)	−0.0017 (5)	0.0070 (5)
C20	0.0543 (9)	0.0395 (8)	0.0271 (7)	0.0124 (7)	−0.0023 (6)	0.0127 (6)
C21	0.0470 (8)	0.0395 (8)	0.0243 (6)	0.0057 (6)	0.0046 (6)	0.0036 (6)
C22	0.0408 (8)	0.0321 (7)	0.0352 (7)	0.0125 (6)	0.0092 (6)	0.0032 (6)
C23	0.0348 (7)	0.0297 (6)	0.0298 (7)	0.0132 (5)	0.0044 (5)	0.0096 (5)
C24	0.0343 (6)	0.0171 (5)	0.0223 (6)	0.0064 (5)	0.0001 (5)	0.0048 (4)
C25	0.0205 (5)	0.0211 (6)	0.0217 (6)	0.0071 (4)	0.0030 (4)	0.0019 (4)
C26	0.0247 (6)	0.0222 (6)	0.0367 (7)	0.0056 (5)	0.0011 (5)	0.0027 (5)
C27	0.0330 (7)	0.0272 (7)	0.0438 (8)	0.0053 (5)	−0.0093 (6)	−0.0076 (6)
C28	0.0369 (7)	0.0422 (8)	0.0285 (7)	0.0121 (6)	−0.0081 (6)	−0.0050 (6)
C29	0.0403 (7)	0.0370 (7)	0.0262 (7)	0.0099 (6)	−0.0040 (6)	0.0077 (6)
C30	0.0337 (7)	0.0238 (6)	0.0245 (6)	0.0044 (5)	−0.0022 (5)	0.0046 (5)

Geometric parameters (Å, º) top

O—C8	1.4211 (14)	C13—H13	0.9500
O—C9	1.4350 (14)	C14—C15	1.3865 (18)
N1—C7	1.3141 (15)	C14—H14	0.9500
N1—C1	1.3907 (16)	C15—C16	1.3985 (17)
N2—C7	1.3726 (15)	C15—H15	0.9500
N2—C6	1.3846 (15)	C17—C18	1.5108 (17)
N2—C24	1.4553 (14)	C17—H17A	0.9900
N3—C10	1.3136 (16)	C17—H17B	0.9900
N3—C16	1.3905 (15)	C18—C23	1.3850 (18)
N4—C10	1.3748 (15)	C18—C19	1.3859 (18)
N4—C11	1.3825 (15)	C19—C20	1.387 (2)
N4—C17	1.4596 (15)	C19—H19	0.9500
C1—C2	1.3996 (17)	C20—C21	1.384 (2)
C1—C6	1.4056 (16)	C20—H20	0.9500
C2—C3	1.3816 (18)	C21—C22	1.383 (2)
C2—H2	0.9500	C21—H21	0.9500
C3—C4	1.4065 (19)	C22—C23	1.385 (2)
C3—H3	0.9500	C22—H22	0.9500
C4—C5	1.3851 (18)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.5134 (16)
C5—C6	1.3929 (17)	C24—H24A	0.9900
C5—H5	0.9500	C24—H24B	0.9900
C7—C8	1.4898 (17)	C25—C30	1.3828 (17)
C8—H8A	0.9900	C25—C26	1.3930 (16)
C8—H8B	0.9900	C26—C27	1.382 (2)
C9—C10	1.4945 (17)	C26—H26	0.9500
C9—H9A	0.9900	C27—C28	1.384 (2)
C9—H9B	0.9900	C27—H27	0.9500
C11—C12	1.3935 (17)	C28—C29	1.378 (2)
C11—C16	1.4049 (16)	C28—H28	0.9500
C12—C13	1.3811 (19)	C29—C30	1.3938 (18)
C12—H12	0.9500	C29—H29	0.9500
C13—C14	1.4033 (19)	C30—H30	0.9500

C8—O—C9	110.65 (9)	C13—C14—H14	119.2
C7—N1—C1	104.47 (10)	C14—C15—C16	117.55 (11)
C7—N2—C6	106.33 (9)	C14—C15—H15	121.2
C7—N2—C24	128.47 (10)	C16—C15—H15	121.2
C6—N2—C24	125.20 (10)	N3—C16—C15	130.02 (11)
C10—N3—C16	104.83 (10)	N3—C16—C11	109.99 (10)
C10—N4—C11	106.39 (10)	C15—C16—C11	119.97 (11)
C10—N4—C17	127.05 (11)	N4—C17—C18	113.67 (10)
C11—N4—C17	126.55 (10)	N4—C17—H17A	108.8
N1—C1—C2	129.86 (11)	C18—C17—H17A	108.8
N1—C1—C6	110.28 (10)	N4—C17—H17B	108.8
C2—C1—C6	119.85 (11)	C18—C17—H17B	108.8
C3—C2—C1	117.78 (11)	H17A—C17—H17B	107.7
C3—C2—H2	121.1	C23—C18—C19	118.91 (12)
C1—C2—H2	121.1	C23—C18—C17	121.38 (11)
C2—C3—C4	121.34 (12)	C19—C18—C17	119.69 (11)
C2—C3—H3	119.3	C18—C19—C20	120.65 (13)
C4—C3—H3	119.3	C18—C19—H19	119.7
C5—C4—C3	122.06 (12)	C20—C19—H19	119.7
C5—C4—H4	119.0	C21—C20—C19	119.97 (13)
C3—C4—H4	119.0	C21—C20—H20	120.0
C4—C5—C6	116.01 (11)	C19—C20—H20	120.0
C4—C5—H5	122.0	C22—C21—C20	119.69 (13)
C6—C5—H5	122.0	C22—C21—H21	120.2
N2—C6—C5	131.85 (11)	C20—C21—H21	120.2
N2—C6—C1	105.17 (10)	C21—C22—C23	120.05 (14)
C5—C6—C1	122.96 (11)	C21—C22—H22	120.0
N1—C7—N2	113.75 (11)	C23—C22—H22	120.0
N1—C7—C8	122.39 (11)	C18—C23—C22	120.71 (12)
N2—C7—C8	123.68 (11)	C18—C23—H23	119.6
O—C8—C7	110.75 (10)	C22—C23—H23	119.6
O—C8—H8A	109.5	N2—C24—C25	114.13 (10)
C7—C8—H8A	109.5	N2—C24—H24A	108.7
O—C8—H8B	109.5	C25—C24—H24A	108.7
C7—C8—H8B	109.5	N2—C24—H24B	108.7
H8A—C8—H8B	108.1	C25—C24—H24B	108.7
O—C9—C10	112.03 (10)	H24A—C24—H24B	107.6
O—C9—H9A	109.2	C30—C25—C26	118.82 (11)
C10—C9—H9A	109.2	C30—C25—C24	122.96 (11)
O—C9—H9B	109.2	C26—C25—C24	118.21 (11)
C10—C9—H9B	109.2	C27—C26—C25	120.48 (13)
H9A—C9—H9B	107.9	C27—C26—H26	119.8
N3—C10—N4	113.39 (11)	C25—C26—H26	119.8
N3—C10—C9	125.14 (11)	C26—C27—C28	120.52 (13)
N4—C10—C9	121.46 (11)	C26—C27—H27	119.7
N4—C11—C12	131.98 (11)	C28—C27—H27	119.7
N4—C11—C16	105.38 (10)	C29—C28—C27	119.31 (13)
C12—C11—C16	122.64 (11)	C29—C28—H28	120.3
C13—C12—C11	116.55 (11)	C27—C28—H28	120.3
C13—C12—H12	121.7	C28—C29—C30	120.41 (13)
C11—C12—H12	121.7	C28—C29—H29	119.8
C12—C13—C14	121.68 (12)	C30—C29—H29	119.8
C12—C13—H13	119.2	C25—C30—C29	120.44 (12)
C14—C13—H13	119.2	C25—C30—H30	119.8
C15—C14—C13	121.61 (12)	C29—C30—H30	119.8
C15—C14—H14	119.2

C7—N1—C1—C2	177.64 (12)	C17—N4—C11—C16	−178.40 (11)
C7—N1—C1—C6	−0.91 (12)	N4—C11—C12—C13	−179.01 (13)
N1—C1—C2—C3	−178.07 (12)	C16—C11—C12—C13	0.11 (19)
C6—C1—C2—C3	0.35 (17)	C11—C12—C13—C14	0.5 (2)
C1—C2—C3—C4	−0.82 (18)	C12—C13—C14—C15	−0.4 (2)
C2—C3—C4—C5	0.42 (19)	C13—C14—C15—C16	−0.32 (19)
C3—C4—C5—C6	0.47 (18)	C10—N3—C16—C15	−178.95 (12)
C7—N2—C6—C5	−178.66 (12)	C10—N3—C16—C11	−0.61 (13)
C24—N2—C6—C5	1.42 (19)	C14—C15—C16—N3	179.09 (12)
C7—N2—C6—C1	−0.40 (12)	C14—C15—C16—C11	0.90 (17)
C24—N2—C6—C1	179.68 (10)	N4—C11—C16—N3	−0.03 (13)
C4—C5—C6—N2	177.04 (12)	C12—C11—C16—N3	−179.35 (11)
C4—C5—C6—C1	−0.95 (17)	N4—C11—C16—C15	178.50 (10)
N1—C1—C6—N2	0.82 (12)	C12—C11—C16—C15	−0.82 (18)
C2—C1—C6—N2	−177.89 (10)	C10—N4—C17—C18	82.90 (15)
N1—C1—C6—C5	179.27 (10)	C11—N4—C17—C18	−98.27 (14)
C2—C1—C6—C5	0.56 (17)	N4—C17—C18—C23	47.20 (16)
C1—N1—C7—N2	0.66 (13)	N4—C17—C18—C19	−134.51 (12)
C1—N1—C7—C8	−174.66 (11)	C23—C18—C19—C20	−0.6 (2)
C6—N2—C7—N1	−0.17 (13)	C17—C18—C19—C20	−178.91 (12)
C24—N2—C7—N1	179.75 (11)	C18—C19—C20—C21	−0.5 (2)
C6—N2—C7—C8	175.08 (10)	C19—C20—C21—C22	0.9 (2)
C24—N2—C7—C8	−5.00 (18)	C20—C21—C22—C23	−0.2 (2)
C9—O—C8—C7	−175.36 (10)	C19—C18—C23—C22	1.3 (2)
N1—C7—C8—O	−122.70 (12)	C17—C18—C23—C22	179.60 (12)
N2—C7—C8—O	62.45 (15)	C21—C22—C23—C18	−0.9 (2)
C8—O—C9—C10	74.56 (13)	C7—N2—C24—C25	−98.23 (14)
C16—N3—C10—N4	1.06 (13)	C6—N2—C24—C25	81.68 (14)
C16—N3—C10—C9	−179.86 (11)	N2—C24—C25—C30	9.57 (17)
C11—N4—C10—N3	−1.10 (14)	N2—C24—C25—C26	−171.39 (11)
C17—N4—C10—N3	177.92 (11)	C30—C25—C26—C27	0.00 (19)
C11—N4—C10—C9	179.78 (10)	C24—C25—C26—C27	−179.08 (12)
C17—N4—C10—C9	−1.20 (18)	C25—C26—C27—C28	−0.6 (2)
O—C9—C10—N3	−106.11 (13)	C26—C27—C28—C29	0.7 (2)
O—C9—C10—N4	72.90 (14)	C27—C28—C29—C30	−0.3 (2)
C10—N4—C11—C12	179.86 (13)	C26—C25—C30—C29	0.43 (19)
C17—N4—C11—C12	0.8 (2)	C24—C25—C30—C29	179.46 (13)
C10—N4—C11—C16	0.63 (13)	C28—C29—C30—C25	−0.3 (2)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆N₄O
M_r	458.55
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	8.5477 (3), 11.8976 (5), 12.3961 (5)
α, β, γ (°)	101.300 (1), 92.394 (1), 107.765 (1)
V (Å³)	1170.28 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.58 × 0.52 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS Spider diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.955, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	11531, 5275, 4542
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.126, 1.09
No. of reflections	5275
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.34

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors acknowledge financial support and a grant from the `Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and `Long Yuan Qing Nian' of Gansu Province is also acknowledged.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–930. Web of Science CrossRef PubMed CAS Google Scholar
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Rigaku/MSC (2004). RAPID-AUTO . Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar