1,3,5-Tris(N-phenyl­benzimidazol-2-yl)benzene methanol solvate

Song, W.-F.; Wu, Y.; Fan, Y.; Wang, Y.; Liu, Y.

doi:10.1107/S1600536809036046

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2461

doi:10.1107/S1600536809036046

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1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene methanol solvate

Wei-Feng Song,^a Ying Wu,^a Yan Fan,^a Yue Wang ^a and Yu Liu ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: yuliu@jlu.edu.cn

(Received 9 July 2009; accepted 7 September 2009; online 12 September 2009)

The main molecule of the title compound, C₄₅H₃₀N₆·CH₃OH, has a non-planar core: the dihedral angles between the benzimidazole rings and the central benzene ring are 20.19 (10), 34.57 (8), and 44.59 (8)°, while the dihedral angles between the peripheral phenyl rings and the attached benzimidazole rings are 84.57 (7), 62.71 (6) and 51.73 (6)°. The tri-substituted benzene molecule is connected to the methanol solvent molecule through an O—H⋯N hydrogen bond, forming a 1:1 solvate. In the crystal structure, no significant π–π interactions are present, and the molecules are associated through weak C—H⋯N and C—H⋯O(methanol) contacts.

Related literature

For OLEDs (organic light emitting diodes), see: Adachi et al. (2001 ); Gao et al. (1999 ); Shi et al. (1997 ); Lo et al. (2002 ). For the structure of a related solvate, see: Totsatitpaisan et al. (2008 ).

Experimental

Crystal data

C₄₅H₃₀N₆·CH₄O
M_r = 686.79
Monoclinic, P 2₁ /c
a = 11.253 (2) Å
b = 18.692 (4) Å
c = 17.763 (4) Å
β = 101.58 (3)°
V = 3660.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.981, T_max = 0.986
35250 measured reflections
8285 independent reflections
4831 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.142
S = 1.01
8285 reflections
480 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0⋯N1ⁱ	0.82	2.12	2.936 (2)	170
C25—H25⋯N5ⁱⁱ	0.93	2.69	3.603 (3)	169
C37—H37⋯N4ⁱⁱⁱ	0.93	2.43	3.338 (3)	164
C32—H32⋯O^iv	0.93	2.71	3.605 (3)	161
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036046/bh2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036046/bh2239Isup2.hkl

checkCIF report

Comment top

For many years there has been extensive research on OLED because of their high luminance, low drive voltage, fast response time, wide viewing angle and a variety of emission color in flat-panel displays. To achieve highly efficient organic electroluminescence, it is essential to confine the excitons within the emitting layer and prevent the excitons and holes to approach the cathode. Therefore, an electron transporting/hole blocking layer is often introduced between the emitting layer and the cathode in some organic electroluminescent diodes (OLEDs). Due to its almost omnipotent properties, TPBI, 1,3,5-tris(2-N-phenylbenzimidazolyl)benzene, is an excellent electroluminescent (EL) material, which has been used as an electron-transporting layer for OLEDs based on fluorescent emitters (Gao et al., 1999), as host (Adachi et al., 2001) or electron-transporting/hole-blocking layer (Lo et al., 2002) for phosphorescent emitters, and enhanced the efficiency of OLEDs. For these reasons, it has attracted considerable interest for years. However, its crystal structure has not been reported until now.

As shown in Fig. 1, the molecular skeleton is non-planar. The dihedral angles between the benzimidazole rings and the central benzene ring, and between the peripheral phenyl rings and the benzimidazole rings, are 20.19 (10), 34.57 (8), 44.59 (8)° and 84.57 (7), 62.71 (6), 51.73 (6)°, respectively. The bond lengths and angles are all in normal ranges. The TPBI molecule forms a 1:1 solvate with methanol, a situation reminiscent of that reported for an other TPBI derivative, stabilized with 2-propanol (Totsatitpaisan et al., 2008).

The packing of the title compound (Fig. 2) shows that there is no π···π interactions. Instead, the molecules are connected with hydrogen bonds.

Related literature top

For OLEDs (organic light emitting diodes), see: Adachi et al. (2001); Gao et al. (1999); Shi et al. (1997); Lo et al. (2002). For the structure of a related solvate, see: Totsatitpaisan et al. (2008).

Experimental top

To a solution of N-phenyl-1,2-phenylenediamine (16.6 g, 0.09 mol) in 100 ml of N-methyl pyrrolidinone was added 1,3,5-benzenetricarbonyl chloride (8.0 g, 0.03 mol) in portion at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 2 h, then raise temperature to 50 for another 0.5 h. After cooling, the mixture was poured into 300 ml of cool water with stirring. The resulted precipitates were filtered and washed with water. After drying, the tribenzamide was collected to give 19.5 g. The TPBI [1,3,5-tris(2-N-phenylbenzimidazolyl)benzene)] was obtained by heating the tribenzamide in 0.3 atm, nitrogen pressure, at 553–568 K for about one hour. The pure TPBI was obtained by sublimation twice at 588 K at 2 Torr pressure. Colorless crystals suitable for X-ray diffraction study were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of title compound along the a axis.

1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene methanol solvate top

Crystal data top

C₄₅H₃₀N₆·CH₄O	F(000) = 1440
M_r = 686.79	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20230 reflections
a = 11.253 (2) Å	θ = 3.2–27.4°
b = 18.692 (4) Å	µ = 0.08 mm⁻¹
c = 17.763 (4) Å	T = 293 K
β = 101.58 (3)°	Block, white
V = 3660.1 (13) Å³	0.26 × 0.20 × 0.19 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	8285 independent reflections
Radiation source: fine-focus sealed tube	4831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→14
T_min = 0.981, T_max = 0.986	k = −24→24
35250 measured reflections	l = −22→21

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0732P)² + 0.0076P] where P = (F_o² + 2F_c²)/3
8285 reflections	(Δ/σ)_max = 0.001
480 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₄₅H₃₀N₆·CH₄O	V = 3660.1 (13) Å³
M_r = 686.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.253 (2) Å	µ = 0.08 mm⁻¹
b = 18.692 (4) Å	T = 293 K
c = 17.763 (4) Å	0.26 × 0.20 × 0.19 mm
β = 101.58 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	8285 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4831 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.058
35250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
8285 reflections	Δρ_min = −0.19 e Å⁻³
480 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.67816 (14)	0.26248 (9)	0.59902 (9)	0.0395 (4)
C2	0.76343 (16)	0.18804 (10)	0.53310 (9)	0.0458 (4)
C3	0.84043 (18)	0.15308 (11)	0.49281 (11)	0.0593 (5)
H3	0.9179	0.1704	0.4928	0.071*
C4	0.7980 (2)	0.09211 (12)	0.45300 (12)	0.0679 (6)
H4	0.8478	0.0678	0.4257	0.081*
C5	0.6827 (2)	0.06613 (11)	0.45271 (11)	0.0623 (6)
H5	0.6572	0.0246	0.4253	0.075*
C6	0.60416 (18)	0.09983 (10)	0.49185 (11)	0.0540 (5)
H6	0.5264	0.0826	0.4911	0.065*
C7	0.64802 (15)	0.16091 (9)	0.53243 (9)	0.0431 (4)
C8	0.46769 (15)	0.20601 (9)	0.57811 (10)	0.0448 (4)
C9	0.42339 (19)	0.14782 (11)	0.61197 (13)	0.0623 (5)
H9	0.4751	0.1114	0.6341	0.075*
C10	0.3007 (2)	0.14498 (14)	0.61229 (15)	0.0766 (7)
H10	0.2692	0.1057	0.6337	0.092*
C11	0.2254 (2)	0.19923 (16)	0.58148 (16)	0.0827 (8)
H11	0.1433	0.1971	0.5830	0.099*
C12	0.26996 (19)	0.25670 (14)	0.54838 (14)	0.0765 (7)
H12	0.2184	0.2939	0.5283	0.092*
C13	0.39177 (16)	0.25975 (11)	0.54466 (11)	0.0580 (5)
H13	0.4216	0.2976	0.5199	0.070*
C14	0.47156 (15)	0.39957 (9)	0.78240 (9)	0.0405 (4)
C15	0.31701 (16)	0.38001 (11)	0.84005 (10)	0.0493 (4)
C16	0.22712 (19)	0.35362 (13)	0.87530 (13)	0.0697 (6)
H16	0.2223	0.3053	0.8870	0.084*
C17	0.1447 (2)	0.40314 (16)	0.89222 (15)	0.0861 (8)
H17	0.0829	0.3878	0.9161	0.103*
C18	0.1520 (2)	0.47526 (16)	0.87438 (14)	0.0808 (7)
H18	0.0937	0.5067	0.8854	0.097*
C19	0.24308 (19)	0.50124 (12)	0.84088 (12)	0.0654 (6)
H19	0.2483	0.5496	0.8298	0.078*
C20	0.32741 (16)	0.45222 (10)	0.82405 (10)	0.0490 (5)
C21	0.44315 (15)	0.27268 (9)	0.82388 (10)	0.0440 (4)
C22	0.55981 (17)	0.25387 (11)	0.85886 (11)	0.0539 (5)
H22	0.6175	0.2888	0.8765	0.065*
C23	0.5890 (2)	0.18240 (13)	0.86714 (15)	0.0784 (7)
H23	0.6675	0.1687	0.8897	0.094*
C24	0.5018 (2)	0.13114 (13)	0.84194 (18)	0.0949 (9)
H24	0.5219	0.0829	0.8475	0.114*
C25	0.3868 (2)	0.15060 (12)	0.80906 (16)	0.0817 (7)
H25	0.3284	0.1156	0.7930	0.098*
C26	0.35646 (18)	0.22138 (11)	0.79942 (12)	0.0606 (5)
H26	0.2778	0.2347	0.7765	0.073*
C27	0.81789 (15)	0.50360 (9)	0.69485 (10)	0.0417 (4)
C28	0.93525 (15)	0.59210 (9)	0.73459 (10)	0.0473 (4)
C29	1.00798 (17)	0.64426 (11)	0.77757 (12)	0.0608 (5)
H29	1.0202	0.6451	0.8309	0.073*
C30	1.0609 (2)	0.69445 (12)	0.73781 (14)	0.0711 (6)
H30	1.1105	0.7293	0.7652	0.085*
C31	1.04256 (19)	0.69455 (12)	0.65845 (14)	0.0702 (6)
H31	1.0788	0.7300	0.6340	0.084*
C32	0.97182 (17)	0.64332 (11)	0.61455 (12)	0.0584 (5)
H32	0.9596	0.6429	0.5612	0.070*
C33	0.92006 (15)	0.59245 (9)	0.65505 (10)	0.0464 (4)
C34	0.79088 (15)	0.52221 (9)	0.55055 (10)	0.0446 (4)
C35	0.6804 (2)	0.55176 (12)	0.52083 (12)	0.0724 (6)
H35	0.6375	0.5760	0.5525	0.087*
C36	0.6330 (2)	0.54512 (14)	0.44293 (14)	0.0873 (8)
H36	0.5576	0.5649	0.4222	0.105*
C37	0.6958 (2)	0.51002 (13)	0.39669 (13)	0.0755 (7)
H37	0.6653	0.5077	0.3441	0.091*
C38	0.8029 (2)	0.47839 (15)	0.42712 (13)	0.0808 (7)
H38	0.8443	0.4527	0.3956	0.097*
C39	0.85137 (18)	0.48410 (13)	0.50520 (11)	0.0637 (6)
H39	0.9246	0.4620	0.5262	0.076*
C40	0.66199 (14)	0.32475 (9)	0.64708 (9)	0.0388 (4)
C41	0.57686 (15)	0.32759 (9)	0.69462 (9)	0.0402 (4)
H41	0.5252	0.2890	0.6962	0.048*
C42	0.56899 (14)	0.38813 (9)	0.73976 (9)	0.0392 (4)
C43	0.64966 (15)	0.44444 (9)	0.73921 (9)	0.0421 (4)
H43	0.6464	0.4840	0.7705	0.051*
C44	0.73500 (14)	0.44234 (9)	0.69252 (9)	0.0405 (4)
C45	0.73934 (15)	0.38286 (9)	0.64583 (9)	0.0420 (4)
H45	0.7947	0.3819	0.6133	0.050*
C46	0.0678 (2)	0.15090 (15)	0.15807 (17)	0.0937 (8)
H46A	0.1492	0.1359	0.1572	0.141*
H46B	0.0246	0.1122	0.1759	0.141*
H46C	0.0700	0.1911	0.1919	0.141*
N1	0.78056 (12)	0.25108 (8)	0.57557 (8)	0.0449 (4)
N2	0.59401 (12)	0.20906 (7)	0.57505 (8)	0.0413 (3)
N3	0.41101 (12)	0.34643 (8)	0.81320 (8)	0.0439 (3)
N4	0.42540 (13)	0.46350 (8)	0.78866 (8)	0.0478 (4)
N5	0.86992 (13)	0.53606 (8)	0.75867 (8)	0.0470 (4)
N6	0.84508 (12)	0.53411 (8)	0.63005 (8)	0.0444 (4)
O	0.00881 (14)	0.17053 (11)	0.08356 (10)	0.0876 (5)
H0	−0.0508	0.1950	0.0860	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (9)	0.0382 (9)	0.0378 (9)	0.0012 (7)	0.0090 (7)	−0.0003 (7)
C2	0.0497 (10)	0.0482 (11)	0.0393 (9)	0.0079 (8)	0.0083 (8)	−0.0039 (8)
C3	0.0529 (11)	0.0696 (14)	0.0574 (12)	0.0098 (10)	0.0159 (9)	−0.0125 (10)
C4	0.0722 (14)	0.0721 (15)	0.0609 (13)	0.0191 (12)	0.0172 (10)	−0.0184 (11)
C5	0.0797 (14)	0.0491 (12)	0.0553 (12)	0.0111 (10)	0.0070 (10)	−0.0160 (10)
C6	0.0656 (12)	0.0432 (11)	0.0517 (11)	0.0025 (9)	0.0079 (9)	−0.0076 (9)
C7	0.0504 (10)	0.0390 (10)	0.0396 (9)	0.0066 (8)	0.0081 (8)	−0.0035 (7)
C8	0.0450 (9)	0.0417 (10)	0.0480 (10)	−0.0021 (8)	0.0104 (8)	−0.0098 (8)
C9	0.0621 (12)	0.0505 (12)	0.0782 (14)	−0.0035 (10)	0.0235 (11)	−0.0029 (11)
C10	0.0691 (14)	0.0708 (16)	0.0987 (18)	−0.0202 (13)	0.0377 (13)	−0.0130 (14)
C11	0.0488 (12)	0.101 (2)	0.0994 (19)	−0.0136 (13)	0.0188 (12)	−0.0282 (16)
C12	0.0515 (12)	0.0854 (18)	0.0883 (16)	0.0151 (12)	0.0035 (12)	−0.0079 (14)
C13	0.0526 (11)	0.0559 (13)	0.0625 (12)	0.0068 (9)	0.0047 (9)	−0.0037 (10)
C14	0.0487 (9)	0.0375 (10)	0.0355 (8)	0.0019 (7)	0.0090 (7)	0.0006 (7)
C15	0.0490 (10)	0.0567 (12)	0.0448 (10)	0.0118 (9)	0.0162 (8)	0.0046 (9)
C16	0.0631 (12)	0.0756 (16)	0.0783 (15)	0.0110 (11)	0.0332 (11)	0.0179 (12)
C17	0.0706 (15)	0.108 (2)	0.0917 (18)	0.0232 (14)	0.0456 (13)	0.0166 (16)
C18	0.0734 (15)	0.095 (2)	0.0805 (16)	0.0333 (14)	0.0306 (12)	−0.0024 (14)
C19	0.0694 (13)	0.0643 (14)	0.0638 (13)	0.0213 (11)	0.0167 (10)	−0.0074 (11)
C20	0.0521 (10)	0.0548 (12)	0.0401 (9)	0.0109 (9)	0.0092 (8)	−0.0036 (8)
C21	0.0508 (10)	0.0389 (10)	0.0453 (10)	0.0034 (8)	0.0168 (8)	0.0070 (8)
C22	0.0520 (10)	0.0542 (12)	0.0542 (11)	0.0034 (9)	0.0080 (9)	0.0081 (9)
C23	0.0648 (14)	0.0624 (15)	0.1063 (19)	0.0190 (12)	0.0131 (13)	0.0255 (14)
C24	0.0898 (18)	0.0445 (14)	0.153 (3)	0.0073 (13)	0.0306 (18)	0.0264 (15)
C25	0.0733 (15)	0.0480 (14)	0.123 (2)	−0.0111 (11)	0.0184 (14)	0.0130 (13)
C26	0.0525 (11)	0.0520 (12)	0.0763 (14)	−0.0045 (9)	0.0106 (10)	0.0096 (10)
C27	0.0444 (9)	0.0367 (9)	0.0432 (9)	0.0019 (7)	0.0067 (7)	−0.0011 (7)
C28	0.0455 (9)	0.0422 (10)	0.0514 (11)	−0.0022 (8)	0.0027 (8)	−0.0037 (8)
C29	0.0599 (12)	0.0555 (13)	0.0618 (12)	−0.0063 (10)	−0.0002 (10)	−0.0134 (10)
C30	0.0667 (13)	0.0565 (14)	0.0844 (16)	−0.0214 (11)	0.0019 (12)	−0.0125 (12)
C31	0.0676 (13)	0.0555 (14)	0.0853 (16)	−0.0236 (10)	0.0098 (12)	0.0035 (12)
C32	0.0594 (11)	0.0550 (12)	0.0596 (12)	−0.0132 (10)	0.0089 (9)	0.0046 (10)
C33	0.0445 (9)	0.0410 (10)	0.0509 (10)	−0.0046 (8)	0.0033 (8)	−0.0010 (8)
C34	0.0504 (10)	0.0397 (10)	0.0419 (9)	−0.0089 (8)	0.0052 (8)	0.0012 (8)
C35	0.0753 (14)	0.0689 (15)	0.0637 (13)	0.0202 (12)	−0.0081 (11)	−0.0104 (11)
C36	0.0959 (18)	0.0762 (17)	0.0717 (16)	0.0146 (14)	−0.0263 (14)	−0.0019 (13)
C37	0.1030 (18)	0.0703 (16)	0.0457 (11)	−0.0252 (14)	−0.0027 (12)	0.0053 (11)
C38	0.0850 (16)	0.106 (2)	0.0542 (13)	−0.0097 (15)	0.0204 (12)	−0.0130 (13)
C39	0.0561 (11)	0.0835 (16)	0.0517 (11)	−0.0008 (11)	0.0110 (9)	−0.0060 (11)
C40	0.0441 (9)	0.0354 (9)	0.0363 (8)	0.0021 (7)	0.0067 (7)	−0.0008 (7)
C41	0.0470 (9)	0.0348 (9)	0.0387 (9)	−0.0035 (7)	0.0081 (7)	−0.0006 (7)
C42	0.0457 (9)	0.0369 (9)	0.0349 (8)	0.0022 (7)	0.0076 (7)	0.0013 (7)
C43	0.0517 (10)	0.0348 (9)	0.0390 (9)	0.0007 (8)	0.0071 (8)	−0.0014 (7)
C44	0.0445 (9)	0.0359 (9)	0.0402 (9)	0.0003 (7)	0.0065 (7)	0.0018 (7)
C45	0.0453 (9)	0.0398 (10)	0.0420 (9)	0.0020 (8)	0.0116 (7)	0.0005 (8)
C46	0.0745 (16)	0.098 (2)	0.105 (2)	0.0080 (14)	0.0076 (15)	−0.0065 (16)
N1	0.0444 (8)	0.0489 (9)	0.0424 (8)	0.0005 (7)	0.0111 (6)	−0.0057 (7)
N2	0.0437 (7)	0.0356 (8)	0.0454 (8)	0.0015 (6)	0.0110 (6)	−0.0041 (6)
N3	0.0468 (8)	0.0423 (9)	0.0453 (8)	0.0048 (7)	0.0154 (6)	0.0039 (7)
N4	0.0598 (9)	0.0402 (9)	0.0437 (8)	0.0059 (7)	0.0107 (7)	−0.0026 (7)
N5	0.0520 (8)	0.0434 (9)	0.0436 (8)	−0.0005 (7)	0.0045 (7)	−0.0029 (7)
N6	0.0494 (8)	0.0406 (8)	0.0414 (8)	−0.0096 (6)	0.0052 (6)	0.0006 (6)
O	0.0620 (10)	0.1121 (15)	0.0919 (12)	0.0045 (9)	0.0231 (9)	−0.0123 (10)

Geometric parameters (Å, º) top

C1—N1	1.319 (2)	C23—H23	0.9300
C1—N2	1.383 (2)	C24—C25	1.357 (3)
C1—C40	1.476 (2)	C24—H24	0.9300
C2—N1	1.392 (2)	C25—C26	1.369 (3)
C2—C7	1.392 (2)	C25—H25	0.9300
C2—C3	1.393 (3)	C26—H26	0.9300
C3—C4	1.375 (3)	C27—N5	1.315 (2)
C3—H3	0.9300	C27—N6	1.373 (2)
C4—C5	1.385 (3)	C27—C44	1.472 (2)
C4—H4	0.9300	C28—C33	1.389 (3)
C5—C6	1.381 (3)	C28—N5	1.395 (2)
C5—H5	0.9300	C28—C29	1.397 (2)
C6—C7	1.387 (2)	C29—C30	1.379 (3)
C6—H6	0.9300	C29—H29	0.9300
C7—N2	1.392 (2)	C30—C31	1.383 (3)
C8—C13	1.374 (3)	C30—H30	0.9300
C8—C9	1.383 (3)	C31—C32	1.382 (3)
C8—N2	1.434 (2)	C31—H31	0.9300
C9—C10	1.383 (3)	C32—C33	1.389 (3)
C9—H9	0.9300	C32—H32	0.9300
C10—C11	1.364 (4)	C33—N6	1.396 (2)
C10—H10	0.9300	C34—C39	1.356 (3)
C11—C12	1.367 (3)	C34—C35	1.366 (3)
C11—H11	0.9300	C34—N6	1.439 (2)
C12—C13	1.387 (3)	C35—C36	1.385 (3)
C12—H12	0.9300	C35—H35	0.9300
C13—H13	0.9300	C36—C37	1.356 (4)
C14—N4	1.316 (2)	C36—H36	0.9300
C14—N3	1.378 (2)	C37—C38	1.354 (3)
C14—C42	1.468 (2)	C37—H37	0.9300
C15—C16	1.383 (3)	C38—C39	1.389 (3)
C15—C20	1.389 (3)	C38—H38	0.9300
C15—N3	1.394 (2)	C39—H39	0.9300
C16—C17	1.385 (3)	C40—C45	1.395 (2)
C16—H16	0.9300	C40—C41	1.400 (2)
C17—C18	1.391 (4)	C41—C42	1.400 (2)
C17—H17	0.9300	C41—H41	0.9300
C18—C19	1.373 (3)	C42—C43	1.391 (2)
C18—H18	0.9300	C43—C44	1.390 (2)
C19—C20	1.394 (3)	C43—H43	0.9300
C19—H19	0.9300	C44—C45	1.394 (2)
C20—N4	1.391 (2)	C45—H45	0.9300
C21—C26	1.375 (3)	C46—O	1.405 (3)
C21—C22	1.380 (2)	C46—H46A	0.9600
C21—N3	1.428 (2)	C46—H46B	0.9600
C22—C23	1.377 (3)	C46—H46C	0.9600
C22—H22	0.9300	O—H0	0.8200
C23—C24	1.381 (3)

N1—C1—N2	111.94 (14)	C21—C26—H26	120.3
N1—C1—C40	121.80 (15)	N5—C27—N6	113.30 (15)
N2—C1—C40	126.23 (15)	N5—C27—C44	123.57 (16)
N1—C2—C7	109.91 (15)	N6—C27—C44	123.10 (14)
N1—C2—C3	130.03 (17)	C33—C28—N5	110.53 (15)
C7—C2—C3	120.03 (17)	C33—C28—C29	119.45 (18)
C4—C3—C2	117.74 (19)	N5—C28—C29	130.02 (17)
C4—C3—H3	121.1	C30—C29—C28	117.4 (2)
C2—C3—H3	121.1	C30—C29—H29	121.3
C3—C4—C5	121.40 (19)	C28—C29—H29	121.3
C3—C4—H4	119.3	C29—C30—C31	122.09 (19)
C5—C4—H4	119.3	C29—C30—H30	119.0
C6—C5—C4	122.13 (19)	C31—C30—H30	119.0
C6—C5—H5	118.9	C32—C31—C30	121.7 (2)
C4—C5—H5	118.9	C32—C31—H31	119.2
C5—C6—C7	116.12 (18)	C30—C31—H31	119.2
C5—C6—H6	121.9	C31—C32—C33	115.9 (2)
C7—C6—H6	121.9	C31—C32—H32	122.1
C6—C7—N2	131.78 (17)	C33—C32—H32	122.1
C6—C7—C2	122.57 (17)	C28—C33—C32	123.47 (17)
N2—C7—C2	105.56 (14)	C28—C33—N6	105.26 (15)
C13—C8—C9	121.05 (18)	C32—C33—N6	131.27 (17)
C13—C8—N2	119.30 (17)	C39—C34—C35	120.61 (17)
C9—C8—N2	119.61 (16)	C39—C34—N6	119.98 (16)
C10—C9—C8	118.6 (2)	C35—C34—N6	119.37 (17)
C10—C9—H9	120.7	C34—C35—C36	119.2 (2)
C8—C9—H9	120.7	C34—C35—H35	120.4
C11—C10—C9	120.7 (2)	C36—C35—H35	120.4
C11—C10—H10	119.7	C37—C36—C35	120.4 (2)
C9—C10—H10	119.7	C37—C36—H36	119.8
C10—C11—C12	120.3 (2)	C35—C36—H36	119.8
C10—C11—H11	119.9	C38—C37—C36	120.0 (2)
C12—C11—H11	119.9	C38—C37—H37	120.0
C11—C12—C13	120.3 (2)	C36—C37—H37	120.0
C11—C12—H12	119.9	C37—C38—C39	120.3 (2)
C13—C12—H12	119.9	C37—C38—H38	119.8
C8—C13—C12	119.0 (2)	C39—C38—H38	119.8
C8—C13—H13	120.5	C34—C39—C38	119.4 (2)
C12—C13—H13	120.5	C34—C39—H39	120.3
N4—C14—N3	112.69 (15)	C38—C39—H39	120.3
N4—C14—C42	121.61 (15)	C45—C40—C41	119.02 (15)
N3—C14—C42	125.42 (15)	C45—C40—C1	117.07 (15)
C16—C15—C20	122.57 (18)	C41—C40—C1	123.89 (15)
C16—C15—N3	131.95 (19)	C40—C41—C42	120.39 (15)
C20—C15—N3	105.47 (16)	C40—C41—H41	119.8
C15—C16—C17	116.3 (2)	C42—C41—H41	119.8
C15—C16—H16	121.9	C43—C42—C41	119.42 (16)
C17—C16—H16	121.9	C43—C42—C14	116.70 (15)
C16—C17—C18	121.7 (2)	C41—C42—C14	123.57 (15)
C16—C17—H17	119.2	C44—C43—C42	120.85 (16)
C18—C17—H17	119.2	C44—C43—H43	119.6
C19—C18—C17	121.7 (2)	C42—C43—H43	119.6
C19—C18—H18	119.2	C43—C44—C45	119.25 (15)
C17—C18—H18	119.2	C43—C44—C27	118.10 (15)
C18—C19—C20	117.4 (2)	C45—C44—C27	122.66 (16)
C18—C19—H19	121.3	C44—C45—C40	121.01 (16)
C20—C19—H19	121.3	C44—C45—H45	119.5
C15—C20—N4	110.29 (15)	C40—C45—H45	119.5
C15—C20—C19	120.39 (19)	O—C46—H46A	109.5
N4—C20—C19	129.27 (19)	O—C46—H46B	109.5
C26—C21—C22	120.99 (17)	H46A—C46—H46B	109.5
C26—C21—N3	119.12 (16)	O—C46—H46C	109.5
C22—C21—N3	119.88 (16)	H46A—C46—H46C	109.5
C23—C22—C21	118.72 (19)	H46B—C46—H46C	109.5
C23—C22—H22	120.6	C1—N1—C2	105.86 (14)
C21—C22—H22	120.6	C1—N2—C7	106.72 (14)
C22—C23—C24	120.0 (2)	C1—N2—C8	129.74 (14)
C22—C23—H23	120.0	C7—N2—C8	122.62 (13)
C24—C23—H23	120.0	C14—N3—C15	106.30 (14)
C25—C24—C23	120.5 (2)	C14—N3—C21	128.04 (15)
C25—C24—H24	119.7	C15—N3—C21	125.35 (15)
C23—C24—H24	119.7	C14—N4—C20	105.23 (15)
C24—C25—C26	120.3 (2)	C27—N5—C28	104.64 (14)
C24—C25—H25	119.8	C27—N6—C33	106.26 (14)
C26—C25—H25	119.8	C27—N6—C34	129.54 (14)
C25—C26—C21	119.42 (19)	C33—N6—C34	122.91 (14)
C25—C26—H26	120.3	C46—O—H0	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0···N1ⁱ	0.82	2.12	2.936 (2)	170
C25—H25···N5ⁱⁱ	0.93	2.69	3.603 (3)	169
C37—H37···N4ⁱⁱⁱ	0.93	2.43	3.338 (3)	164
C32—H32···O^iv	0.93	2.71	3.605 (3)	161

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₄₅H₃₀N₆·CH₄O
M_r	686.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.253 (2), 18.692 (4), 17.763 (4)
β (°)	101.58 (3)
V (Å³)	3660.1 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.20 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	35250, 8285, 4831
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.142, 1.01
No. of reflections	8285
No. of parameters	480
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0···N1ⁱ	0.82	2.12	2.936 (2)	170.4
C25—H25···N5ⁱⁱ	0.93	2.69	3.603 (3)	169.0
C37—H37···N4ⁱⁱⁱ	0.93	2.43	3.338 (3)	164.1
C32—H32···O^iv	0.93	2.71	3.605 (3)	160.6

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 50733002) and the Jilin Provincial Science and Technology Bureau (grant No. 20070107).

References

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