A third polymorph of 1,4-bis-(1H-benzimid-azol-2-yl)benzene.

The title compound, C20H14N4, is a new polymorph of the previously reported structures, which were ortho-rhom-bic, space group Pbca [Bei et al. (2000). Acta Cryst. C56, 718-719] and monoclinic, space group P21/c [Dudd et al. (2003). Green Chem. 5, 187-192]. The asymmetric unit consists of two independent mol-ecules in which the dihedral angels between the central benzene ring and the outer benzimidazole ring systems are 16.81 (10) and 14.23 (10)° in one molecule and 26.09 (10) and 37.29 (10)° in the other. In the crystal, mol-ecules are linked by N-H⋯N and C-H⋯N hydrogen bonds into a tape running along the c-axis direction.

Related literature

For the synthesis of the title compound, see: Alcalde et al. (1992 ▶); Zhao et al. (2012 ▶); Zhuang et al. (2011 ▶). For the previously reported structures of the title compound, see: Bei et al. (2000 ▶); Dudd et al. (2003 ▶). For the structures of the title compound with solvent mol­ecules, see: Wu & Hu (2009 ▶); Su et al. (2011 ▶).

Experimental

Crystal data

C20H14N4

M = 310.35

Monoclinic,

a = 16.196 (3) Å

b = 20.174 (3) Å

c = 9.9010 (16) Å

β = 106.733 (3)°

V = 3098.1 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.26 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.979, T max = 0.986

15697 measured reflections

5451 independent reflections

3197 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.126

S = 1.02

5451 reflections

450 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814011179/is5361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011179/is5361Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011179/is5361Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H14N4	F(000) = 1296
Mr = 310.35	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1697 reflections
a = 16.196 (3) Å	θ = 2.4–22.0°
b = 20.174 (3) Å	µ = 0.08 mm−1
c = 9.9010 (16) Å	T = 296 K
β = 106.733 (3)°	Block, yellow
V = 3098.1 (8) Å3	0.26 × 0.22 × 0.17 mm
Z = 8

Bruker APEXII CCD diffractometer	5451 independent reflections
Radiation source: fine-focus sealed tube	3197 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→19
Tmin = 0.979, Tmax = 0.986	k = −23→23
15697 measured reflections	l = −11→8

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5451 reflections	Δρmax = 0.21 e Å−3
450 parameters	Δρmin = −0.21 e Å−3
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (3)

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.

	x	y	z	Uiso*/Ueq
N1	0.29247 (12)	−0.04939 (9)	0.8970 (2)	0.0422 (5)
N2	0.27746 (13)	−0.04637 (9)	0.6655 (2)	0.0449 (5)
N3	0.07524 (11)	0.26679 (8)	0.8390 (2)	0.0400 (5)
N4	0.06709 (12)	0.27094 (9)	0.6109 (2)	0.0409 (5)
N5	0.21368 (12)	−0.03614 (9)	0.3559 (2)	0.0457 (5)
N6	0.25379 (13)	−0.06306 (9)	0.1650 (2)	0.0447 (5)
N7	0.38516 (11)	0.29079 (8)	0.3466 (2)	0.0429 (5)
N8	0.39950 (13)	0.27194 (9)	0.1317 (2)	0.0430 (5)
C1	0.32991 (14)	−0.10557 (10)	0.8589 (3)	0.0419 (6)
C2	0.37149 (15)	−0.15816 (11)	0.9408 (3)	0.0523 (7)
H2A	0.3776	−0.1599	1.0371	0.063*
C3	0.40316 (16)	−0.20745 (12)	0.8745 (3)	0.0572 (7)
H3	0.4315	−0.2432	0.9273	0.069*
C4	0.39416 (16)	−0.20559 (12)	0.7306 (3)	0.0585 (7)
H4A	0.4166	−0.2401	0.6897	0.070*
C5	0.35302 (15)	−0.15420 (12)	0.6475 (3)	0.0551 (7)
H5	0.3469	−0.1529	0.5512	0.066*
C6	0.32114 (14)	−0.10441 (10)	0.7147 (3)	0.0416 (6)
C7	0.26227 (14)	−0.01539 (10)	0.7780 (3)	0.0404 (6)
C8	0.22036 (14)	0.04919 (10)	0.7669 (2)	0.0380 (6)
C9	0.18877 (15)	0.07285 (10)	0.8733 (3)	0.0463 (6)
H9	0.1941	0.0470	0.9531	0.056*
C10	0.14979 (15)	0.13358 (11)	0.8634 (3)	0.0483 (6)
H10	0.1300	0.1486	0.9372	0.058*
C11	0.13940 (13)	0.17303 (10)	0.7452 (2)	0.0366 (5)
C12	0.17413 (15)	0.15063 (11)	0.6412 (3)	0.0504 (7)
H12	0.1704	0.1770	0.5627	0.061*
C13	0.21410 (16)	0.08991 (12)	0.6522 (3)	0.0549 (7)
H13	0.2373	0.0760	0.5813	0.066*
C14	0.09418 (14)	0.23666 (10)	0.7334 (2)	0.0379 (6)
C15	0.03436 (14)	0.32525 (11)	0.7812 (3)	0.0425 (6)
C16	0.00158 (16)	0.37657 (12)	0.8445 (3)	0.0597 (7)
H16	0.0040	0.3748	0.9395	0.072*
C17	−0.03427 (19)	0.42969 (13)	0.7627 (4)	0.0739 (9)
H17	−0.0555	0.4650	0.8032	0.089*
C18	−0.03965 (18)	0.43187 (13)	0.6192 (4)	0.0740 (9)
H18	−0.0648	0.4686	0.5665	0.089*
C19	−0.00906 (15)	0.38159 (12)	0.5539 (3)	0.0579 (7)
H19	−0.0133	0.3830	0.4582	0.069*
C20	0.02871 (14)	0.32833 (11)	0.6384 (3)	0.0428 (6)
C21	0.19204 (14)	−0.10180 (11)	0.3204 (3)	0.0441 (6)
C22	0.15135 (16)	−0.14810 (12)	0.3834 (3)	0.0582 (7)
H22	0.1335	−0.1371	0.4619	0.070*
C23	0.13831 (17)	−0.21025 (13)	0.3267 (3)	0.0627 (8)
H23	0.1110	−0.2419	0.3670	0.075*
C24	0.16497 (17)	−0.22720 (12)	0.2103 (3)	0.0637 (8)
H24	0.1561	−0.2703	0.1756	0.076*
C25	0.20405 (16)	−0.18225 (11)	0.1449 (3)	0.0587 (7)
H25	0.2210	−0.1936	0.0658	0.070*
C26	0.21713 (14)	−0.11937 (11)	0.2019 (3)	0.0440 (6)
C27	0.24929 (14)	−0.01533 (10)	0.2595 (2)	0.0396 (6)
C28	0.28177 (14)	0.05166 (10)	0.2531 (2)	0.0371 (6)
C29	0.34685 (14)	0.06484 (10)	0.1920 (3)	0.0447 (6)
H29	0.3704	0.0302	0.1531	0.054*
C30	0.37728 (15)	0.12830 (11)	0.1877 (3)	0.0458 (6)
H30	0.4212	0.1362	0.1466	0.055*
C31	0.34253 (14)	0.18036 (10)	0.2446 (2)	0.0372 (5)
C32	0.27666 (14)	0.16773 (10)	0.3045 (2)	0.0428 (6)
H32	0.2529	0.2024	0.3427	0.051*
C33	0.24615 (14)	0.10442 (10)	0.3080 (2)	0.0427 (6)
H33	0.2013	0.0967	0.3473	0.051*
C34	0.37521 (14)	0.24779 (10)	0.2431 (3)	0.0391 (6)
C35	0.41685 (14)	0.34739 (10)	0.2989 (3)	0.0400 (6)
C36	0.43613 (14)	0.40958 (11)	0.3605 (3)	0.0493 (6)
H36	0.4292	0.4183	0.4488	0.059*
C37	0.46551 (16)	0.45757 (11)	0.2884 (3)	0.0559 (7)
H37	0.4784	0.4995	0.3281	0.067*
C38	0.47638 (18)	0.44489 (13)	0.1577 (3)	0.0677 (8)
H38	0.4973	0.4783	0.1118	0.081*
C39	0.45718 (16)	0.38443 (12)	0.0935 (3)	0.0606 (7)
H39	0.4645	0.3762	0.0052	0.073*
C40	0.42666 (14)	0.33628 (10)	0.1652 (3)	0.0412 (6)
H2	0.2599 (15)	−0.0344 (12)	0.5728 (19)	0.069 (9)*
H4	0.0751 (15)	0.2586 (10)	0.5247 (19)	0.059 (8)*
H6	0.2687 (15)	−0.0543 (12)	0.084 (2)	0.070 (8)*
H8	0.3954 (16)	0.2505 (11)	0.051 (2)	0.069 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0531 (12)	0.0402 (11)	0.0389 (13)	0.0030 (9)	0.0219 (11)	0.0027 (9)
N2	0.0578 (13)	0.0460 (12)	0.0346 (14)	0.0063 (10)	0.0192 (12)	−0.0028 (11)
N3	0.0488 (11)	0.0394 (11)	0.0365 (12)	0.0025 (9)	0.0195 (10)	−0.0018 (9)
N4	0.0485 (12)	0.0412 (11)	0.0381 (14)	0.0025 (9)	0.0204 (11)	−0.0002 (10)
N5	0.0574 (12)	0.0460 (12)	0.0421 (13)	−0.0083 (10)	0.0277 (11)	−0.0020 (10)
N6	0.0608 (13)	0.0405 (11)	0.0409 (14)	−0.0066 (10)	0.0277 (12)	−0.0020 (10)
N7	0.0562 (12)	0.0356 (10)	0.0433 (13)	−0.0040 (9)	0.0249 (11)	−0.0006 (9)
N8	0.0548 (12)	0.0417 (12)	0.0379 (14)	−0.0039 (9)	0.0217 (11)	−0.0011 (10)
C1	0.0443 (13)	0.0400 (13)	0.0443 (17)	0.0018 (11)	0.0175 (13)	−0.0019 (12)
C2	0.0614 (15)	0.0470 (15)	0.0520 (18)	0.0081 (13)	0.0218 (15)	0.0081 (13)
C3	0.0599 (16)	0.0444 (15)	0.069 (2)	0.0109 (13)	0.0207 (17)	0.0033 (14)
C4	0.0586 (16)	0.0531 (16)	0.066 (2)	0.0107 (13)	0.0209 (17)	−0.0101 (15)
C5	0.0618 (16)	0.0547 (16)	0.0511 (19)	0.0094 (13)	0.0197 (15)	−0.0104 (14)
C6	0.0454 (13)	0.0388 (13)	0.0437 (16)	0.0015 (11)	0.0178 (13)	−0.0022 (12)
C7	0.0473 (14)	0.0398 (13)	0.0382 (16)	−0.0010 (11)	0.0190 (13)	−0.0013 (12)
C8	0.0439 (13)	0.0386 (13)	0.0350 (15)	0.0021 (10)	0.0167 (12)	0.0023 (11)
C9	0.0632 (15)	0.0428 (14)	0.0396 (16)	0.0090 (12)	0.0257 (14)	0.0068 (11)
C10	0.0663 (16)	0.0468 (14)	0.0414 (16)	0.0093 (12)	0.0304 (14)	0.0006 (12)
C11	0.0411 (12)	0.0356 (12)	0.0361 (15)	0.0007 (10)	0.0161 (12)	0.0001 (11)
C12	0.0674 (16)	0.0507 (15)	0.0415 (17)	0.0156 (13)	0.0288 (15)	0.0092 (12)
C13	0.0757 (18)	0.0563 (16)	0.0413 (17)	0.0196 (14)	0.0305 (15)	0.0058 (13)
C14	0.0443 (13)	0.0396 (13)	0.0340 (15)	−0.0063 (11)	0.0177 (12)	0.0005 (11)
C15	0.0432 (13)	0.0404 (13)	0.0476 (17)	0.0009 (11)	0.0191 (13)	−0.0013 (12)
C16	0.0655 (17)	0.0596 (17)	0.062 (2)	0.0130 (14)	0.0310 (16)	−0.0032 (15)
C17	0.084 (2)	0.0598 (18)	0.083 (3)	0.0289 (16)	0.033 (2)	−0.0013 (18)
C18	0.081 (2)	0.0575 (18)	0.084 (3)	0.0277 (15)	0.026 (2)	0.0120 (17)
C19	0.0630 (16)	0.0552 (16)	0.059 (2)	0.0122 (13)	0.0232 (15)	0.0148 (14)
C20	0.0419 (13)	0.0395 (13)	0.0504 (18)	0.0022 (11)	0.0185 (13)	0.0022 (12)
C21	0.0498 (14)	0.0458 (14)	0.0390 (16)	−0.0079 (11)	0.0162 (13)	0.0009 (12)
C22	0.0701 (17)	0.0579 (16)	0.0534 (19)	−0.0156 (14)	0.0287 (15)	0.0026 (14)
C23	0.0642 (17)	0.0567 (17)	0.069 (2)	−0.0192 (14)	0.0215 (17)	0.0094 (15)
C24	0.0701 (18)	0.0433 (15)	0.081 (2)	−0.0116 (13)	0.0264 (18)	−0.0039 (15)
C25	0.0723 (17)	0.0469 (15)	0.064 (2)	−0.0089 (13)	0.0310 (16)	−0.0103 (14)
C26	0.0479 (14)	0.0420 (14)	0.0440 (17)	−0.0039 (11)	0.0164 (13)	0.0019 (12)
C27	0.0466 (14)	0.0399 (13)	0.0353 (15)	−0.0014 (11)	0.0166 (12)	−0.0011 (11)
C28	0.0436 (13)	0.0394 (13)	0.0331 (14)	0.0002 (10)	0.0189 (12)	0.0015 (11)
C29	0.0536 (14)	0.0385 (13)	0.0516 (17)	−0.0020 (11)	0.0304 (14)	−0.0060 (12)
C30	0.0518 (14)	0.0473 (14)	0.0487 (17)	−0.0041 (11)	0.0309 (13)	−0.0061 (12)
C31	0.0420 (13)	0.0383 (13)	0.0346 (15)	0.0028 (10)	0.0163 (12)	0.0023 (11)
C32	0.0497 (14)	0.0408 (13)	0.0448 (16)	0.0074 (11)	0.0245 (13)	0.0008 (11)
C33	0.0453 (13)	0.0430 (14)	0.0465 (16)	0.0001 (11)	0.0240 (13)	0.0009 (12)
C34	0.0441 (13)	0.0407 (13)	0.0363 (15)	0.0014 (11)	0.0174 (12)	0.0005 (12)
C35	0.0455 (13)	0.0384 (13)	0.0398 (16)	0.0005 (11)	0.0180 (12)	0.0021 (11)
C36	0.0610 (16)	0.0428 (14)	0.0475 (17)	−0.0050 (12)	0.0210 (14)	−0.0061 (12)
C37	0.0678 (17)	0.0432 (14)	0.059 (2)	−0.0135 (13)	0.0220 (16)	−0.0018 (14)
C38	0.094 (2)	0.0559 (17)	0.059 (2)	−0.0259 (15)	0.0307 (19)	0.0058 (15)
C39	0.0809 (19)	0.0634 (17)	0.0452 (18)	−0.0196 (15)	0.0305 (16)	−0.0002 (14)
C40	0.0458 (13)	0.0400 (13)	0.0415 (16)	−0.0051 (11)	0.0183 (13)	0.0008 (11)

N1—C7	1.329 (3)	C15—C16	1.392 (3)
N1—C1	1.388 (3)	C16—C17	1.368 (3)
N2—H2	0.912 (17)	C16—H16	0.9300
N3—C14	1.319 (3)	C17—H17	0.9300
N3—C15	1.392 (3)	C18—C17	1.400 (4)
N4—C14	1.355 (3)	C18—H18	0.9300
N4—C20	1.378 (3)	C19—C18	1.370 (3)
N4—H4	0.933 (16)	C19—H19	0.9300
N5—C27	1.318 (3)	C20—C19	1.391 (3)
N5—C21	1.389 (3)	C20—C15	1.392 (3)
N6—C27	1.359 (3)	C21—C22	1.391 (3)
N6—C26	1.379 (3)	C21—C26	1.393 (3)
N6—H6	0.916 (16)	C22—C23	1.365 (3)
N7—C34	1.316 (3)	C22—H22	0.9300
N7—C35	1.389 (3)	C23—H23	0.9300
N8—C34	1.363 (3)	C24—C23	1.385 (4)
N8—C40	1.380 (3)	C24—H24	0.9300
N8—H8	0.898 (16)	C25—C24	1.370 (3)
C1—C2	1.386 (3)	C25—H25	0.9300
C2—C3	1.370 (3)	C26—C25	1.380 (3)
C2—H2A	0.9300	C28—C29	1.384 (3)
C3—C4	1.391 (4)	C28—C33	1.393 (3)
C3—H3	0.9300	C28—C27	1.458 (3)
C4—H4A	0.9300	C29—H29	0.9300
C5—C4	1.371 (3)	C30—C29	1.377 (3)
C5—H5	0.9300	C30—H30	0.9300
C6—N2	1.382 (3)	C31—C30	1.385 (3)
C6—C5	1.384 (3)	C31—C32	1.386 (3)
C6—C1	1.393 (3)	C32—H32	0.9300
C7—N2	1.360 (3)	C33—C32	1.373 (3)
C7—C8	1.459 (3)	C33—H33	0.9300
C8—C13	1.381 (3)	C34—C31	1.461 (3)
C9—C10	1.369 (3)	C35—C36	1.391 (3)
C9—C8	1.381 (3)	C35—C40	1.396 (3)
C9—H9	0.9300	C36—C37	1.367 (3)
C10—H10	0.9300	C36—H36	0.9300
C11—C12	1.384 (3)	C37—C38	1.379 (4)
C11—C10	1.385 (3)	C37—H37	0.9300
C11—C14	1.466 (3)	C38—H38	0.9300
C12—C13	1.375 (3)	C39—C38	1.369 (3)
C12—H12	0.9300	C39—H39	0.9300
C13—H13	0.9300	C40—C39	1.376 (3)
C7—N1—C1	104.99 (19)	C29—C30—H30	120.0
C7—N2—C6	107.2 (2)	C31—C30—H30	120.0
C7—N2—H2	128.7 (16)	N6—C26—C25	132.6 (2)
C6—N2—H2	123.9 (16)	N6—C26—C21	105.4 (2)
C14—N3—C15	104.86 (19)	C25—C26—C21	122.0 (2)
C14—N4—C20	107.5 (2)	N5—C27—N6	113.21 (19)
C14—N4—H4	126.0 (14)	N5—C27—C28	124.4 (2)
C20—N4—H4	126.5 (14)	N6—C27—C28	122.4 (2)
C27—N6—C26	106.80 (19)	C20—C15—N3	109.85 (19)
C27—N6—H6	122.9 (15)	C20—C15—C16	120.2 (2)
C26—N6—H6	129.2 (16)	N3—C15—C16	130.0 (2)
C34—N7—C35	104.58 (19)	C12—C13—C8	121.1 (2)
C34—N8—C40	106.7 (2)	C12—C13—H13	119.4
C34—N8—H8	126.0 (16)	C8—C13—H13	119.4
C40—N8—H8	127.2 (16)	C3—C2—C1	117.5 (2)
N1—C7—N2	112.4 (2)	C3—C2—H2A	121.3
N1—C7—C8	124.9 (2)	C1—C2—H2A	121.3
N2—C7—C8	122.6 (2)	C33—C32—C31	120.6 (2)
N7—C34—N8	113.25 (19)	C33—C32—H32	119.7
N7—C34—C31	124.7 (2)	C31—C32—H32	119.7
N8—C34—C31	122.0 (2)	C30—C29—C28	121.1 (2)
C12—C11—C10	117.7 (2)	C30—C29—H29	119.5
C12—C11—C14	121.8 (2)	C28—C29—H29	119.5
C10—C11—C14	120.5 (2)	C38—C39—C40	117.2 (2)
C27—N5—C21	104.58 (18)	C38—C39—H39	121.4
C10—C9—C8	121.3 (2)	C40—C39—H39	121.4
C10—C9—H9	119.4	C4—C5—C6	116.4 (2)
C8—C9—H9	119.4	C4—C5—H5	121.8
N4—C20—C19	132.5 (2)	C6—C5—H5	121.8
N4—C20—C15	105.2 (2)	C37—C36—C35	118.5 (2)
C19—C20—C15	122.3 (2)	C37—C36—H36	120.7
N2—C6—C5	132.0 (2)	C35—C36—H36	120.7
N2—C6—C1	105.44 (19)	C36—C37—C38	121.1 (2)
C5—C6—C1	122.6 (2)	C36—C37—H37	119.5
C9—C10—C11	121.1 (2)	C38—C37—H37	119.5
C9—C10—H10	119.5	C2—C3—C4	121.9 (2)
C11—C10—H10	119.5	C2—C3—H3	119.1
C29—C28—C33	118.47 (19)	C4—C3—H3	119.1
C29—C28—C27	121.76 (19)	C18—C19—C20	116.4 (3)
C33—C28—C27	119.76 (19)	C18—C19—H19	121.8
C2—C1—N1	130.0 (2)	C20—C19—H19	121.8
C2—C1—C6	120.1 (2)	C5—C4—C3	121.6 (2)
N1—C1—C6	109.9 (2)	C5—C4—H4A	119.2
C13—C8—C9	117.7 (2)	C3—C4—H4A	119.2
C13—C8—C7	121.0 (2)	C17—C16—C15	117.9 (3)
C9—C8—C7	121.2 (2)	C17—C16—H16	121.0
N7—C35—C36	130.6 (2)	C15—C16—H16	121.0
N7—C35—C40	110.15 (19)	C23—C22—C21	118.0 (2)
C36—C35—C40	119.2 (2)	C23—C22—H22	121.0
N3—C14—N4	112.65 (19)	C21—C22—H22	121.0
N3—C14—C11	124.4 (2)	C24—C25—C26	116.9 (2)
N4—C14—C11	122.9 (2)	C24—C25—H25	121.5
C13—C12—C11	121.0 (2)	C26—C25—H25	121.5
C13—C12—H12	119.5	C25—C24—C23	121.8 (2)
C11—C12—H12	119.5	C25—C24—H24	119.1
C32—C33—C28	120.6 (2)	C23—C24—H24	119.1
C32—C33—H33	119.7	C19—C18—C17	122.1 (3)
C28—C33—H33	119.7	C19—C18—H18	119.0
C30—C31—C32	119.19 (19)	C17—C18—H18	119.0
C30—C31—C34	120.74 (19)	C22—C23—C24	121.4 (2)
C32—C31—C34	120.06 (19)	C22—C23—H23	119.3
N5—C21—C22	130.1 (2)	C24—C23—H23	119.3
N5—C21—C26	110.01 (19)	C39—C38—C37	121.8 (2)
C22—C21—C26	119.9 (2)	C39—C38—H38	119.1
C39—C40—N8	132.6 (2)	C37—C38—H38	119.1
C39—C40—C35	122.1 (2)	C16—C17—C18	121.2 (3)
N8—C40—C35	105.26 (19)	C16—C17—H17	119.4
C29—C30—C31	120.1 (2)	C18—C17—H17	119.4
C1—N1—C7—N2	0.4 (3)	C27—N6—C26—C21	−0.1 (3)
C1—N1—C7—C8	−177.3 (2)	N5—C21—C26—N6	−0.5 (3)
C35—N7—C34—N8	1.0 (3)	C22—C21—C26—N6	179.2 (2)
C35—N7—C34—C31	−179.7 (2)	N5—C21—C26—C25	179.3 (2)
C40—N8—C34—N7	−0.7 (3)	C22—C21—C26—C25	−0.9 (4)
C40—N8—C34—C31	179.96 (19)	C21—N5—C27—N6	−1.1 (3)
C14—N4—C20—C19	179.1 (2)	C21—N5—C27—C28	179.4 (2)
C14—N4—C20—C15	−0.4 (2)	C26—N6—C27—N5	0.8 (3)
C8—C9—C10—C11	1.1 (4)	C26—N6—C27—C28	−179.7 (2)
C12—C11—C10—C9	−3.6 (4)	C29—C28—C27—N5	153.5 (2)
C14—C11—C10—C9	177.3 (2)	C33—C28—C27—N5	−27.4 (3)
C7—N1—C1—C2	179.8 (2)	C29—C28—C27—N6	−26.0 (3)
C7—N1—C1—C6	−0.2 (2)	C33—C28—C27—N6	153.2 (2)
N2—C6—C1—C2	179.97 (19)	N4—C20—C15—N3	−0.2 (2)
C5—C6—C1—C2	−0.4 (4)	C19—C20—C15—N3	−179.8 (2)
N2—C6—C1—N1	−0.1 (2)	N4—C20—C15—C16	179.6 (2)
C5—C6—C1—N1	179.6 (2)	C19—C20—C15—C16	0.0 (4)
C10—C9—C8—C13	2.3 (4)	C14—N3—C15—C20	0.8 (2)
C10—C9—C8—C7	179.7 (2)	C14—N3—C15—C16	−179.0 (2)
N1—C7—C8—C13	160.4 (2)	C11—C12—C13—C8	0.4 (4)
N2—C7—C8—C13	−17.1 (3)	C9—C8—C13—C12	−3.0 (4)
N1—C7—C8—C9	−16.9 (3)	C7—C8—C13—C12	179.6 (2)
N2—C7—C8—C9	165.6 (2)	N1—C1—C2—C3	−179.6 (2)
C34—N7—C35—C36	177.0 (2)	C6—C1—C2—C3	0.4 (3)
C34—N7—C35—C40	−0.9 (3)	C28—C33—C32—C31	1.0 (3)
N1—C7—N2—C6	−0.4 (3)	C30—C31—C32—C33	0.1 (3)
C8—C7—N2—C6	177.33 (19)	C34—C31—C32—C33	−179.2 (2)
C5—C6—N2—C7	−179.4 (2)	C31—C30—C29—C28	−0.3 (4)
C1—C6—N2—C7	0.3 (2)	C33—C28—C29—C30	1.3 (3)
C15—N3—C14—N4	−1.1 (2)	C27—C28—C29—C30	−179.5 (2)
C15—N3—C14—C11	179.01 (19)	N8—C40—C39—C38	178.1 (2)
C20—N4—C14—N3	1.0 (3)	C35—C40—C39—C38	−1.2 (4)
C20—N4—C14—C11	−179.10 (19)	N2—C6—C5—C4	179.7 (2)
C12—C11—C14—N3	−165.6 (2)	C1—C6—C5—C4	0.1 (4)
C10—C11—C14—N3	13.4 (3)	N7—C35—C36—C37	−178.8 (2)
C12—C11—C14—N4	14.5 (3)	C40—C35—C36—C37	−1.0 (3)
C10—C11—C14—N4	−166.5 (2)	C35—C36—C37—C38	−0.3 (4)
C10—C11—C12—C13	2.9 (4)	C1—C2—C3—C4	−0.2 (4)
C14—C11—C12—C13	−178.1 (2)	N4—C20—C19—C18	−178.6 (2)
C29—C28—C33—C32	−1.7 (3)	C15—C20—C19—C18	0.9 (4)
C27—C28—C33—C32	179.2 (2)	C6—C5—C4—C3	0.1 (4)
N7—C34—C31—C30	−141.3 (2)	C2—C3—C4—C5	0.0 (4)
N8—C34—C31—C30	38.0 (3)	C20—C15—C16—C17	−1.2 (4)
N7—C34—C31—C32	38.0 (3)	N3—C15—C16—C17	178.6 (2)
N8—C34—C31—C32	−142.7 (2)	N5—C21—C22—C23	−179.6 (2)
C27—N5—C21—C22	−178.7 (3)	C26—C21—C22—C23	0.8 (4)
C27—N5—C21—C26	1.0 (3)	N6—C26—C25—C24	179.8 (2)
C34—N8—C40—C39	−179.4 (3)	C21—C26—C25—C24	0.0 (4)
C34—N8—C40—C35	0.0 (3)	C26—C25—C24—C23	1.1 (4)
N7—C35—C40—C39	−180.0 (2)	C20—C19—C18—C17	−0.7 (4)
C36—C35—C40—C39	1.8 (4)	C21—C22—C23—C24	0.3 (4)
N7—C35—C40—N8	0.6 (3)	C25—C24—C23—C22	−1.3 (5)
C36—C35—C40—N8	−177.6 (2)	C40—C39—C38—C37	−0.2 (4)
C32—C31—C30—C29	−0.5 (3)	C36—C37—C38—C39	1.0 (5)
C34—C31—C30—C29	178.9 (2)	C15—C16—C17—C18	1.4 (4)
C27—N6—C26—C25	−180.0 (3)	C19—C18—C17—C16	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N5	0.91 (2)	2.06 (2)	2.947 (3)	164 (2)
N4—H4···N3i	0.93 (2)	1.91 (2)	2.837 (3)	172 (2)
N6—H6···N1ii	0.92 (2)	2.00 (2)	2.910 (3)	171 (2)
N8—H8···N7i	0.90 (2)	2.15 (2)	3.041 (3)	174 (2)
C12—H12···N3i	0.93	2.57	3.396 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N5	0.91 (2)	2.06 (2)	2.947 (3)	164 (2)
N4—H4⋯N3i	0.93 (2)	1.91 (2)	2.837 (3)	172 (2)
N6—H6⋯N1ii	0.92 (2)	2.00 (2)	2.910 (3)	171 (2)
N8—H8⋯N7i	0.90 (2)	2.15 (2)	3.041 (3)	174 (2)
C12—H12⋯N3i	0.93	2.57	3.396 (3)	148

Symmetry codes: (i) ; (ii) .