1,3,5-Tris(N-phenyl-benzimidazol-2-yl)benzene methanol solvate.

The main mol-ecule of the title compound, C(45)H(30)N(6)·CH(3)OH, 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 mol-ecule is connected to the methanol solvent mol-ecule through an O-H⋯N hydrogen bond, forming a 1:1 solvate. In the crystal structure, no significant π-π inter-actions are present, and the mol-ecules 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 = 686.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.142

S = 1.01

8285 reflections

480 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C45H30N6·CH4O	F(000) = 1440
Mr = 686.79	Dx = 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

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

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(Fo2) + (0.0732P)2 + 0.0076P] where P = (Fo2 + 2Fc2)/3
8285 reflections	(Δ/σ)max = 0.001
480 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···Oiv	0.93	2.71	3.605 (3)	161

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⋯Oiv	0.93	2.71	3.605 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .