1-Methyl-2-({[(1-methyl-1H-benzimid-azol-2-yl)meth-yl](phen-yl)amino}-meth-yl)1H-benzimidazol-3-ium picrate.

In the title molecular salt, C(24)H(24)N(5) (+)·C(6)H(2)N(3)O(7) (-), the dihedral angle between the benzimidazole rings of the cation is 5.041 (2)°. In the anion, the three nitro groups make dihedral angles of 2.468 (3), 12.795 (3) and 24.958 (4)° with respect to the central ring. In the crystal, weak aromatic π-π stacking [centroid-centroid distance = 3.599 (15) Å] consolidates the packing. In addition, an intra-molecular N-H⋯N hydrogen bond is observed.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ▶) and to benzimidazoles, see: Ram et al. (1992 ▶). For the biological activivity of n class="Chemical">benzimidazoles, see: Baraldi et al. (2004 ▶); Göker et al. (2002 ▶); Jayasekera et al. (2005 ▶); Starčević et al. (2007 ▶).

Experimental

Crystal data

C24H24N5 +·C6n class="Species">H2N3O7 −

M = 610.59

Triclinic,

a = 9.4233 (5) Å

b = 12.3523 (7) Å

c = 12.5772 (7) Å

α = 92.007 (1)°

β = 98.497 (1)°

γ = 103.685 (1)°

V = 1403.07 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.31 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.968, T max = 0.970

11689 measured reflections

5217 independent reflections

3567 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.221

S = 1.19

5217 reflections

411 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024275/lr2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024275/lr2014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024275/lr2014Isup3.cml

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

C30H26N8O7	Z = 2
Mr = 610.59	F(000) = 636
Triclinic, P1	Dx = 1.445 Mg m−3
a = 9.4233 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3523 (7) Å	Cell parameters from 5217 reflections
c = 12.5772 (7) Å	θ = 3.0–25.5°
α = 92.007 (1)°	µ = 0.11 mm−1
β = 98.497 (1)°	T = 293 K
γ = 103.685 (1)°	Block, yellow
V = 1403.07 (13) Å3	0.31 × 0.30 × 0.29 mm

Bruker SMART APEX diffractometer	5217 independent reflections
Radiation source: fine-focus sealed tube	3567 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.968, Tmax = 0.970	k = −14→14
11689 measured reflections	l = −15→13

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.221	w = 1/[σ2(Fo2) + (0.1022P)2 + 0.6611P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max < 0.001
5217 reflections	Δρmax = 0.60 e Å−3
411 parameters	Δρmin = −0.50 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

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
O1	0.4994 (3)	−0.13472 (19)	0.29886 (19)	0.0706 (7)
O2	0.2431 (4)	−0.2821 (4)	0.2686 (4)	0.172 (2)
O3	0.0611 (3)	−0.2466 (3)	0.1765 (3)	0.1027 (10)
O4	0.1139 (3)	0.0278 (2)	−0.0786 (2)	0.0864 (8)
O5	0.3145 (3)	0.1577 (2)	−0.0626 (2)	0.0874 (9)
O6	0.7374 (3)	0.1381 (3)	0.1867 (3)	0.1111 (12)
O7	0.7036 (3)	0.0635 (3)	0.3324 (3)	0.1153 (13)
N1	0.5570 (3)	0.6424 (2)	0.67349 (18)	0.0486 (6)
N2	0.7671 (2)	0.7189 (2)	0.78335 (18)	0.0474 (6)
N3	0.3314 (3)	0.4630 (2)	0.59716 (19)	0.0518 (6)
N4	0.2023 (3)	0.2910 (2)	0.6013 (2)	0.0530 (6)
N5	0.4792 (3)	0.46665 (19)	0.81228 (19)	0.0481 (6)
N6	0.1909 (3)	−0.2216 (2)	0.2111 (3)	0.0674 (8)
N7	0.2401 (3)	0.0720 (2)	−0.0337 (2)	0.0610 (7)
N8	0.6589 (3)	0.0772 (2)	0.2407 (2)	0.0643 (7)
C1	0.6137 (3)	0.7487 (2)	0.6418 (2)	0.0465 (7)
C2	0.5602 (4)	0.8062 (3)	0.5586 (2)	0.0570 (8)
H2A	0.4724	0.7746	0.5123	0.068*
C3	0.6420 (4)	0.9119 (3)	0.5471 (3)	0.0650 (9)
H3A	0.6086	0.9527	0.4922	0.078*
C4	0.7734 (4)	0.9591 (3)	0.6158 (3)	0.0658 (9)
H4A	0.8254	1.0309	0.6056	0.079*
C5	0.8294 (4)	0.9035 (3)	0.6984 (3)	0.0593 (8)
H5A	0.9181	0.9353	0.7436	0.071*
C6	0.7461 (3)	0.7972 (2)	0.7104 (2)	0.0476 (7)
C7	0.6516 (3)	0.6286 (2)	0.7579 (2)	0.0467 (7)
C8	0.6330 (3)	0.5244 (3)	0.8170 (2)	0.0506 (7)
H8A	0.6844	0.4747	0.7862	0.061*
H8B	0.6782	0.5435	0.8918	0.061*
C9	0.4206 (3)	0.3610 (2)	0.7497 (2)	0.0542 (7)
H9A	0.3671	0.3075	0.7934	0.065*
H9B	0.5019	0.3328	0.7306	0.065*
C10	0.3194 (3)	0.3709 (2)	0.6493 (2)	0.0496 (7)
C11	0.1347 (3)	0.3364 (3)	0.5125 (2)	0.0532 (7)
C12	0.0087 (4)	0.2915 (3)	0.4368 (3)	0.0662 (9)
H12A	−0.0465	0.2185	0.4375	0.079*
C13	−0.0292 (4)	0.3618 (4)	0.3608 (3)	0.0736 (11)
H13A	−0.1131	0.3356	0.3090	0.088*
C14	0.0544 (4)	0.4711 (3)	0.3591 (3)	0.0696 (9)
H14A	0.0251	0.5157	0.3062	0.084*
C15	0.1784 (4)	0.5142 (3)	0.4334 (2)	0.0593 (8)
H15A	0.2341	0.5870	0.4321	0.071*
C16	0.2174 (3)	0.4447 (3)	0.5106 (2)	0.0506 (7)
C17	0.8923 (3)	0.7329 (3)	0.8698 (3)	0.0642 (9)
H17A	0.8817	0.6669	0.9089	0.096*
H17B	0.8956	0.7960	0.9178	0.096*
H17C	0.9823	0.7452	0.8399	0.096*
C18	0.1542 (4)	0.1791 (3)	0.6371 (3)	0.0715 (10)
H18A	0.2203	0.1705	0.7003	0.107*
H18B	0.1548	0.1247	0.5809	0.107*
H18C	0.0558	0.1685	0.6537	0.107*
C19	0.3877 (3)	0.5143 (2)	0.8665 (2)	0.0434 (6)
C20	0.4428 (3)	0.6143 (2)	0.9302 (2)	0.0495 (7)
H20A	0.5427	0.6500	0.9368	0.059*
C21	0.3521 (4)	0.6609 (3)	0.9831 (2)	0.0564 (8)
H21A	0.3918	0.7272	1.0260	0.068*
C22	0.2039 (4)	0.6114 (3)	0.9739 (3)	0.0590 (8)
H22A	0.1425	0.6441	1.0088	0.071*
C23	0.1481 (3)	0.5121 (3)	0.9119 (2)	0.0601 (8)
H23A	0.0478	0.4776	0.9052	0.072*
C24	0.2373 (3)	0.4627 (3)	0.8597 (2)	0.0530 (7)
H24A	0.1975	0.3947	0.8197	0.064*
C25	0.4378 (3)	−0.0849 (2)	0.2298 (2)	0.0489 (7)
C26	0.2853 (3)	−0.1251 (2)	0.1753 (2)	0.0482 (7)
C27	0.2223 (3)	−0.0748 (2)	0.0922 (2)	0.0504 (7)
H27A	0.1246	−0.1048	0.0603	0.060*
C28	0.3037 (3)	0.0202 (2)	0.0560 (2)	0.0498 (7)
C29	0.4476 (3)	0.0692 (2)	0.1063 (2)	0.0515 (7)
H29A	0.5011	0.1347	0.0827	0.062*
C30	0.5096 (3)	0.0199 (2)	0.1907 (2)	0.0483 (7)
H3N	0.398 (2)	0.5313 (13)	0.606 (2)	0.046 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0762 (15)	0.0589 (14)	0.0696 (15)	0.0146 (12)	−0.0099 (12)	0.0146 (11)
O2	0.103 (3)	0.148 (4)	0.237 (5)	−0.016 (2)	−0.012 (3)	0.137 (4)
O3	0.0588 (17)	0.091 (2)	0.148 (3)	−0.0060 (15)	0.0184 (17)	0.032 (2)
O4	0.0647 (16)	0.102 (2)	0.0810 (18)	0.0148 (15)	−0.0184 (13)	0.0133 (15)
O5	0.0880 (19)	0.0789 (18)	0.0841 (18)	0.0042 (15)	−0.0026 (15)	0.0349 (15)
O6	0.0684 (18)	0.127 (3)	0.109 (2)	−0.0245 (18)	−0.0051 (16)	0.034 (2)
O7	0.089 (2)	0.126 (3)	0.090 (2)	−0.0287 (18)	−0.0357 (17)	0.0316 (19)
N1	0.0416 (12)	0.0545 (14)	0.0457 (13)	0.0069 (10)	0.0007 (10)	0.0083 (11)
N2	0.0387 (12)	0.0566 (14)	0.0438 (12)	0.0090 (11)	0.0010 (10)	0.0047 (11)
N3	0.0533 (14)	0.0481 (14)	0.0470 (13)	0.0038 (12)	0.0006 (11)	0.0011 (11)
N4	0.0505 (14)	0.0464 (14)	0.0586 (15)	0.0070 (11)	0.0069 (11)	−0.0036 (11)
N5	0.0462 (13)	0.0451 (13)	0.0483 (13)	0.0065 (10)	0.0004 (10)	0.0049 (10)
N6	0.0639 (19)	0.0519 (16)	0.083 (2)	0.0054 (14)	0.0122 (15)	0.0138 (14)
N7	0.0594 (17)	0.0658 (18)	0.0556 (15)	0.0177 (14)	−0.0016 (13)	0.0062 (13)
N8	0.0553 (16)	0.0602 (17)	0.0666 (18)	0.0007 (13)	−0.0038 (14)	0.0076 (14)
C1	0.0437 (15)	0.0498 (16)	0.0436 (14)	0.0078 (12)	0.0049 (12)	0.0041 (12)
C2	0.0579 (18)	0.0584 (19)	0.0509 (17)	0.0108 (15)	0.0004 (14)	0.0092 (14)
C3	0.076 (2)	0.062 (2)	0.0574 (19)	0.0149 (17)	0.0125 (16)	0.0160 (16)
C4	0.074 (2)	0.0530 (19)	0.065 (2)	0.0019 (16)	0.0152 (17)	0.0096 (16)
C5	0.0535 (18)	0.0581 (19)	0.0586 (18)	0.0002 (15)	0.0077 (14)	−0.0010 (15)
C6	0.0457 (15)	0.0509 (16)	0.0445 (15)	0.0085 (13)	0.0080 (12)	0.0009 (12)
C7	0.0410 (14)	0.0563 (17)	0.0422 (14)	0.0107 (13)	0.0059 (12)	0.0055 (12)
C8	0.0403 (15)	0.0588 (18)	0.0517 (16)	0.0119 (13)	0.0034 (12)	0.0088 (13)
C9	0.0579 (18)	0.0468 (16)	0.0562 (17)	0.0133 (14)	0.0033 (14)	0.0039 (13)
C10	0.0512 (16)	0.0458 (16)	0.0497 (16)	0.0097 (13)	0.0051 (13)	0.0010 (13)
C11	0.0478 (16)	0.0621 (19)	0.0482 (16)	0.0119 (14)	0.0077 (13)	−0.0079 (14)
C12	0.0513 (18)	0.072 (2)	0.068 (2)	0.0075 (16)	0.0015 (16)	−0.0176 (18)
C13	0.0528 (19)	0.104 (3)	0.056 (2)	0.016 (2)	−0.0061 (15)	−0.016 (2)
C14	0.063 (2)	0.091 (3)	0.0509 (18)	0.0170 (19)	0.0001 (15)	−0.0035 (17)
C15	0.0578 (18)	0.069 (2)	0.0472 (16)	0.0122 (16)	0.0023 (14)	0.0031 (15)
C16	0.0464 (15)	0.0592 (18)	0.0426 (15)	0.0085 (14)	0.0041 (12)	−0.0008 (13)
C17	0.0467 (17)	0.077 (2)	0.0596 (19)	0.0074 (16)	−0.0080 (14)	0.0044 (16)
C18	0.065 (2)	0.054 (2)	0.088 (3)	−0.0007 (16)	0.0122 (18)	0.0033 (18)
C19	0.0437 (14)	0.0461 (15)	0.0377 (13)	0.0076 (12)	0.0016 (11)	0.0093 (11)
C20	0.0467 (15)	0.0487 (16)	0.0499 (16)	0.0047 (13)	0.0078 (13)	0.0104 (13)
C21	0.066 (2)	0.0519 (17)	0.0505 (17)	0.0102 (15)	0.0121 (14)	0.0113 (14)
C22	0.0565 (18)	0.074 (2)	0.0513 (17)	0.0221 (16)	0.0133 (14)	0.0115 (16)
C23	0.0446 (16)	0.081 (2)	0.0498 (17)	0.0056 (16)	0.0070 (13)	0.0132 (16)
C24	0.0460 (16)	0.0573 (18)	0.0478 (16)	0.0000 (14)	0.0015 (13)	0.0084 (13)
C25	0.0546 (17)	0.0440 (15)	0.0469 (15)	0.0132 (13)	0.0029 (13)	0.0018 (12)
C26	0.0486 (16)	0.0398 (15)	0.0540 (16)	0.0061 (12)	0.0086 (13)	0.0040 (12)
C27	0.0421 (15)	0.0465 (16)	0.0571 (17)	0.0052 (12)	0.0022 (13)	−0.0050 (13)
C28	0.0486 (16)	0.0528 (17)	0.0463 (15)	0.0130 (13)	0.0006 (12)	0.0049 (13)
C29	0.0535 (17)	0.0479 (16)	0.0508 (16)	0.0087 (13)	0.0069 (13)	0.0049 (13)
C30	0.0422 (15)	0.0466 (16)	0.0519 (16)	0.0073 (12)	0.0008 (12)	0.0022 (13)

O1—C25	1.236 (3)	C9—H9A	0.9700
O2—N6	1.196 (4)	C9—H9B	0.9700
O3—N6	1.198 (4)	C11—C16	1.383 (4)
O4—N7	1.227 (3)	C11—C12	1.393 (4)
O5—N7	1.222 (4)	C12—C13	1.378 (5)
O6—N8	1.223 (4)	C12—H12A	0.9300
O7—N8	1.199 (4)	C13—C14	1.395 (5)
N1—C7	1.326 (3)	C13—H13A	0.9300
N1—C1	1.391 (4)	C14—C15	1.368 (4)
N2—C7	1.353 (4)	C14—H14A	0.9300
N2—C6	1.384 (4)	C15—C16	1.385 (4)
N2—C17	1.455 (4)	C15—H15A	0.9300
N3—C10	1.322 (4)	C17—H17A	0.9600
N3—C16	1.383 (4)	C17—H17B	0.9600
N3—H3N	0.916 (10)	C17—H17C	0.9600
N4—C10	1.343 (4)	C18—H18A	0.9600
N4—C11	1.403 (4)	C18—H18B	0.9600
N4—C18	1.458 (4)	C18—H18C	0.9600
N5—C19	1.393 (4)	C19—C20	1.393 (4)
N5—C9	1.444 (4)	C19—C24	1.398 (4)
N5—C8	1.447 (4)	C20—C21	1.371 (4)
N6—C26	1.438 (4)	C20—H20A	0.9300
N7—C28	1.440 (4)	C21—C22	1.372 (4)
N8—C30	1.453 (4)	C21—H21A	0.9300
C1—C2	1.385 (4)	C22—C23	1.377 (5)
C1—C6	1.397 (4)	C22—H22A	0.9300
C2—C3	1.374 (5)	C23—C24	1.373 (5)
C2—H2A	0.9300	C23—H23A	0.9300
C3—C4	1.388 (5)	C24—H24A	0.9300
C3—H3A	0.9300	C25—C30	1.450 (4)
C4—C5	1.374 (5)	C25—C26	1.460 (4)
C4—H4A	0.9300	C26—C27	1.366 (4)
C5—C6	1.387 (4)	C27—C28	1.374 (4)
C5—H5A	0.9300	C27—H27A	0.9300
C7—C8	1.495 (4)	C28—C29	1.392 (4)
C8—H8A	0.9700	C29—C30	1.368 (4)
C8—H8B	0.9700	C29—H29A	0.9300
C9—C10	1.494 (4)
C7—N1—C1	106.1 (2)	C13—C12—H12A	122.0
C7—N2—C6	107.3 (2)	C11—C12—H12A	122.0
C7—N2—C17	127.3 (3)	C12—C13—C14	122.0 (3)
C6—N2—C17	125.4 (3)	C12—C13—H13A	119.0
C10—N3—C16	108.6 (3)	C14—C13—H13A	119.0
C10—N3—H3N	133.7 (18)	C15—C14—C13	121.5 (3)
C16—N3—H3N	117.7 (18)	C15—C14—H14A	119.2
C10—N4—C11	107.1 (2)	C13—C14—H14A	119.2
C10—N4—C18	125.8 (3)	C14—C15—C16	117.1 (3)
C11—N4—C18	127.1 (3)	C14—C15—H15A	121.5
C19—N5—C9	120.3 (2)	C16—C15—H15A	121.5
C19—N5—C8	119.8 (2)	C11—C16—N3	107.0 (3)
C9—N5—C8	119.9 (3)	C11—C16—C15	121.5 (3)
O2—N6—O3	119.6 (3)	N3—C16—C15	131.5 (3)
O2—N6—C26	120.2 (3)	N2—C17—H17A	109.5
O3—N6—C26	120.0 (3)	N2—C17—H17B	109.5
O5—N7—O4	122.7 (3)	H17A—C17—H17B	109.5
O5—N7—C28	118.7 (3)	N2—C17—H17C	109.5
O4—N7—C28	118.6 (3)	H17A—C17—H17C	109.5
O7—N8—O6	121.3 (3)	H17B—C17—H17C	109.5
O7—N8—C30	120.3 (3)	N4—C18—H18A	109.5
O6—N8—C30	118.4 (3)	N4—C18—H18B	109.5
C2—C1—N1	130.7 (3)	H18A—C18—H18B	109.5
C2—C1—C6	120.7 (3)	N4—C18—H18C	109.5
N1—C1—C6	108.6 (2)	H18A—C18—H18C	109.5
C3—C2—C1	117.4 (3)	H18B—C18—H18C	109.5
C3—C2—H2A	121.3	N5—C19—C20	121.3 (2)
C1—C2—H2A	121.3	N5—C19—C24	121.1 (3)
C2—C3—C4	121.4 (3)	C20—C19—C24	117.6 (3)
C2—C3—H3A	119.3	C21—C20—C19	121.1 (3)
C4—C3—H3A	119.3	C21—C20—H20A	119.5
C5—C4—C3	122.4 (3)	C19—C20—H20A	119.5
C5—C4—H4A	118.8	C20—C21—C22	121.1 (3)
C3—C4—H4A	118.8	C20—C21—H21A	119.5
C4—C5—C6	116.2 (3)	C22—C21—H21A	119.5
C4—C5—H5A	121.9	C21—C22—C23	118.5 (3)
C6—C5—H5A	121.9	C21—C22—H22A	120.7
N2—C6—C5	132.0 (3)	C23—C22—H22A	120.7
N2—C6—C1	106.0 (2)	C24—C23—C22	121.5 (3)
C5—C6—C1	122.0 (3)	C24—C23—H23A	119.3
N1—C7—N2	112.1 (2)	C22—C23—H23A	119.3
N1—C7—C8	123.7 (3)	C23—C24—C19	120.3 (3)
N2—C7—C8	124.2 (2)	C23—C24—H24A	119.9
N5—C8—C7	112.6 (2)	C19—C24—H24A	119.9
N5—C8—H8A	109.1	O1—C25—C30	124.1 (3)
C7—C8—H8A	109.1	O1—C25—C26	124.5 (3)
N5—C8—H8B	109.1	C30—C25—C26	111.4 (2)
C7—C8—H8B	109.1	C27—C26—N6	116.3 (3)
H8A—C8—H8B	107.8	C27—C26—C25	124.1 (3)
N5—C9—C10	112.1 (2)	N6—C26—C25	119.6 (3)
N5—C9—H9A	109.2	C26—C27—C28	119.8 (3)
C10—C9—H9A	109.2	C26—C27—H27A	120.1
N5—C9—H9B	109.2	C28—C27—H27A	120.1
C10—C9—H9B	109.2	C27—C28—C29	120.8 (3)
H9A—C9—H9B	107.9	C27—C28—N7	120.4 (3)
N3—C10—N4	110.6 (3)	C29—C28—N7	118.8 (3)
N3—C10—C9	123.7 (3)	C30—C29—C28	119.3 (3)
N4—C10—C9	125.7 (3)	C30—C29—H29A	120.4
C16—C11—C12	121.9 (3)	C28—C29—H29A	120.4
C16—C11—N4	106.7 (2)	C29—C30—C25	124.3 (3)
C12—C11—N4	131.4 (3)	C29—C30—N8	116.1 (3)
C13—C12—C11	116.0 (3)	C25—C30—N8	119.5 (2)
C7—N1—C1—C2	−179.9 (3)	N4—C11—C16—N3	−0.3 (3)
C7—N1—C1—C6	0.3 (3)	C12—C11—C16—C15	0.3 (5)
N1—C1—C2—C3	180.0 (3)	N4—C11—C16—C15	−178.7 (3)
C6—C1—C2—C3	−0.3 (5)	C10—N3—C16—C11	0.0 (3)
C1—C2—C3—C4	0.3 (5)	C10—N3—C16—C15	178.2 (3)
C2—C3—C4—C5	0.2 (6)	C14—C15—C16—C11	0.1 (5)
C3—C4—C5—C6	−0.7 (5)	C14—C15—C16—N3	−177.9 (3)
C7—N2—C6—C5	−179.6 (3)	C9—N5—C19—C20	177.9 (2)
C17—N2—C6—C5	−0.2 (5)	C8—N5—C19—C20	−3.3 (4)
C7—N2—C6—C1	0.1 (3)	C9—N5—C19—C24	−1.5 (4)
C17—N2—C6—C1	179.4 (3)	C8—N5—C19—C24	177.3 (2)
C4—C5—C6—N2	−179.6 (3)	N5—C19—C20—C21	179.8 (3)
C4—C5—C6—C1	0.8 (5)	C24—C19—C20—C21	−0.8 (4)
C2—C1—C6—N2	180.0 (3)	C19—C20—C21—C22	−0.9 (4)
N1—C1—C6—N2	−0.2 (3)	C20—C21—C22—C23	1.3 (4)
C2—C1—C6—C5	−0.3 (5)	C21—C22—C23—C24	−0.1 (5)
N1—C1—C6—C5	179.5 (3)	C22—C23—C24—C19	−1.6 (4)
C1—N1—C7—N2	−0.2 (3)	N5—C19—C24—C23	−178.6 (3)
C1—N1—C7—C8	−179.6 (3)	C20—C19—C24—C23	2.0 (4)
C6—N2—C7—N1	0.1 (3)	O2—N6—C26—C27	166.1 (4)
C17—N2—C7—N1	−179.2 (3)	O3—N6—C26—C27	−8.0 (5)
C6—N2—C7—C8	179.5 (3)	O2—N6—C26—C25	−15.6 (6)
C17—N2—C7—C8	0.1 (5)	O3—N6—C26—C25	170.3 (3)
C19—N5—C8—C7	−68.7 (3)	O1—C25—C26—C27	−173.8 (3)
C9—N5—C8—C7	110.1 (3)	C30—C25—C26—C27	4.8 (4)
N1—C7—C8—N5	−29.1 (4)	O1—C25—C26—N6	8.0 (5)
N2—C7—C8—N5	151.6 (3)	C30—C25—C26—N6	−173.4 (3)
C19—N5—C9—C10	70.9 (3)	N6—C26—C27—C28	177.7 (3)
C8—N5—C9—C10	−107.9 (3)	C25—C26—C27—C28	−0.6 (5)
C16—N3—C10—N4	0.3 (3)	C26—C27—C28—C29	−3.1 (5)
C16—N3—C10—C9	−177.8 (3)	C26—C27—C28—N7	178.0 (3)
C11—N4—C10—N3	−0.4 (3)	O5—N7—C28—C27	178.6 (3)
C18—N4—C10—N3	−179.3 (3)	O4—N7—C28—C27	−2.1 (5)
C11—N4—C10—C9	177.6 (3)	O5—N7—C28—C29	−0.3 (4)
C18—N4—C10—C9	−1.3 (5)	O4—N7—C28—C29	179.1 (3)
N5—C9—C10—N3	29.2 (4)	C27—C28—C29—C30	1.9 (5)
N5—C9—C10—N4	−148.6 (3)	N7—C28—C29—C30	−179.2 (3)
C10—N4—C11—C16	0.4 (3)	C28—C29—C30—C25	3.1 (5)
C18—N4—C11—C16	179.3 (3)	C28—C29—C30—N8	−178.6 (3)
C10—N4—C11—C12	−178.4 (3)	O1—C25—C30—C29	172.5 (3)
C18—N4—C11—C12	0.4 (5)	C26—C25—C30—C29	−6.1 (4)
C16—C11—C12—C13	−0.6 (5)	O1—C25—C30—N8	−5.7 (5)
N4—C11—C12—C13	178.1 (3)	C26—C25—C30—N8	175.7 (3)
C11—C12—C13—C14	0.6 (5)	O7—N8—C30—C29	155.6 (4)
C12—C13—C14—C15	−0.2 (6)	O6—N8—C30—C29	−25.2 (5)
C13—C14—C15—C16	−0.1 (5)	O7—N8—C30—C25	−26.1 (5)
C12—C11—C16—N3	178.7 (3)	O6—N8—C30—C25	153.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1	0.92	1.85	2.715 (8)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N1	0.92	1.85	2.715 (8)	157