Bases, solvates and salts: new benzimidazole- and pyridine-scaffolded ligands

The inter­molecular inter­actions in the structures of a series of Schiff base ligands have been thoroughly studied. These ligands can be obtained in different forms, namely, as the free base 2-[(2E)-2-(1H-imidazol-4-yl­methyl­idene)-1-methyl­hydrazin­yl]pyridine, C₁₀H₁₁N₅, 1, the hydrates 2-[(2E)-2-(1H-imidazol-2-yl­methyl­idene)-1-methyl­hydrazin­yl]-1H-benzimidazole monohydrate, C₁₂H₁₂N₆·H₂O, 2, and 2-{(2E)-1-methyl-2-[(1-methyl-1H-imidazol-2-yl)methyl­idene]hydrazin­yl}-1H-benz­imidazole 1.25-hydrate, C₁₃H₁₄N₆·1.25H₂O, 3, the monocationic hydrate 5-{(1E)-[2-(1H-1,3-benzo­diazol-2-yl)-2-methyl­hydrazinyl­idene]meth­yl}-1H-imidazol-3-ium tri­fluoro­methane­sulfonate monohydrate, C₁₂H₁₃N₆⁺·CF₃O₃S⁻·H₂O, 5, and the dicationic 2-{(2E)-1-methyl-2-[(1H-imidazol-3-ium-2-yl)methyl­idene]hydrazin­yl}pyridinium bis­(tri­fluoro­methane­sulfonate), C₁₀H₁₃N₅²⁺·2CF₃O₃S⁻, 6. The connection between the forms and the preferred inter­molecular inter­actions is described and further studied by means of the calculation of the inter­action energies between the neutral and charged components of the crystal structures. These studies show that, in general, the most important contribution to the stabilization energy of the crystal is provided by π–π inter­actions, especially between charged ligands, while the details of the crystal architecture are influenced by directional inter­actions, especially relatively strong hydrogen bonds. In one of the structures, a very inter­esting example of the nontypical F...O inter­action was found and its length, 2.859 (2) Å, is one of the shortest ever reported.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020).

2-[(2E)-2-(1H-Imidazol-4-ylmethylidene)-1-methylhydrazinyl]pyridine (1)

Crystal data

C10H11N5	F(000) = 848
Mr = 201.24	Dx = 1.268 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 10.1953 (4) Å	Cell parameters from 3131 reflections
b = 14.2866 (5) Å	θ = 3.4–26.5°
c = 14.9027 (5) Å	µ = 0.08 mm^−1
β = 103.845 (3)°	T = 295 K
V = 2107.60 (13) Å^3	Prism, colourless
Z = 8	0.35 × 0.2 × 0.2 mm

Data collection

Agilent Xcalibur Eos diffractometer	4041 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.5°, θmin = 3.4°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→12
Tmin = 0.906, Tmax = 1.000	l = −17→18
8099 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.3264P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4041 reflections	Δρmax = 0.16 e Å^−3
281 parameters	Δρmin = −0.18 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.29100 (14)	0.55930 (9)	0.56620 (9)	0.0595 (4)
C2A	0.3758 (2)	0.61528 (12)	0.53505 (13)	0.0685 (5)
H2A	0.4173	0.6634	0.5736	0.082*
C3A	0.40551 (18)	0.60682 (12)	0.45105 (13)	0.0643 (5)
H3A	0.4652	0.6477	0.4328	0.077*
C4A	0.34390 (16)	0.53550 (12)	0.39410 (12)	0.0600 (4)
H4A	0.3620	0.5273	0.3363	0.072*
C5A	0.25616 (16)	0.47675 (11)	0.42275 (11)	0.0541 (4)
H5A	0.2137	0.4284	0.3850	0.065*
C6A	0.23184 (14)	0.49111 (10)	0.50992 (10)	0.0464 (3)
N7A	0.14372 (13)	0.43413 (9)	0.54394 (9)	0.0528 (3)
C7A	0.11997 (19)	0.44791 (13)	0.63509 (11)	0.0652 (5)
H7A	0.0266	0.4630	0.6295	0.098*
H7B	0.1755	0.4983	0.6656	0.098*
H7C	0.1421	0.3916	0.6706	0.098*
N8A	0.07932 (12)	0.36620 (8)	0.48537 (8)	0.0460 (3)
C9A	−0.00148 (15)	0.30931 (10)	0.51143 (11)	0.0472 (3)
H9A	−0.0168	0.3142	0.5703	0.057*
C10A	−0.06858 (13)	0.23755 (9)	0.44859 (10)	0.0411 (3)
N11A	−0.06041 (11)	0.23075 (8)	0.35855 (8)	0.0411 (3)
H11A	−0.0116 (17)	0.2686 (12)	0.3266 (12)	0.064 (5)*
C12A	−0.13159 (14)	0.15517 (10)	0.32253 (11)	0.0463 (3)
H12A	−0.1413	0.1355	0.2618	0.056*
N13A	−0.18627 (13)	0.11179 (9)	0.38249 (9)	0.0517 (3)
C14A	−0.14698 (15)	0.16375 (10)	0.46165 (11)	0.0498 (4)
H14A	−0.1706	0.1505	0.5169	0.060*
N1B	0.76134 (11)	0.50517 (9)	0.11245 (8)	0.0478 (3)
C2B	0.79490 (16)	0.57779 (12)	0.06520 (11)	0.0550 (4)
H2B	0.8812	0.5784	0.0547	0.066*
C3B	0.71148 (17)	0.65028 (12)	0.03179 (11)	0.0574 (4)
H3B	0.7398	0.6991	−0.0003	0.069*
C4B	0.58293 (17)	0.64901 (11)	0.04708 (11)	0.0554 (4)
H4B	0.5231	0.6975	0.0250	0.066*
C5B	0.54352 (14)	0.57650 (10)	0.09463 (10)	0.0477 (4)
H5B	0.4576	0.5749	0.1058	0.057*
C6B	0.63668 (13)	0.50498 (10)	0.12588 (9)	0.0391 (3)
N7B	0.60307 (11)	0.42776 (8)	0.17296 (8)	0.0446 (3)
C7B	0.69653 (14)	0.35214 (11)	0.20626 (12)	0.0529 (4)
H7D	0.7012	0.3414	0.2705	0.079*
H7E	0.7845	0.3686	0.1986	0.079*
H7F	0.6659	0.2963	0.1718	0.079*
N8B	0.47252 (10)	0.42396 (8)	0.17907 (8)	0.0407 (3)
C9B	0.42794 (13)	0.35244 (10)	0.21386 (9)	0.0416 (3)
H9B	0.4848	0.3028	0.2373	0.050*
C10B	0.28703 (13)	0.35056 (9)	0.21593 (9)	0.0386 (3)
N11B	0.19760 (11)	0.42037 (9)	0.17942 (8)	0.0396 (3)
H11B	0.2133 (16)	0.4736 (12)	0.1521 (11)	0.055 (5)*
C12B	0.07718 (14)	0.39654 (11)	0.19431 (10)	0.0459 (3)
H12B	−0.0003	0.4329	0.1762	0.055*
N13B	0.08147 (12)	0.31597 (9)	0.23748 (9)	0.0510 (3)
C14B	0.21332 (15)	0.28725 (11)	0.25122 (10)	0.0476 (4)
H14B	0.2476	0.2320	0.2807	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0704 (9)	0.0473 (8)	0.0561 (8)	−0.0145 (7)	0.0061 (7)	−0.0095 (6)
C2A	0.0822 (12)	0.0505 (10)	0.0670 (11)	−0.0253 (9)	0.0063 (9)	−0.0091 (9)
C3A	0.0661 (11)	0.0537 (10)	0.0694 (11)	−0.0170 (8)	0.0093 (9)	0.0027 (9)
C4A	0.0592 (10)	0.0600 (10)	0.0596 (10)	−0.0096 (8)	0.0118 (8)	−0.0036 (8)
C5A	0.0535 (9)	0.0511 (9)	0.0562 (9)	−0.0121 (7)	0.0102 (7)	−0.0125 (7)
C6A	0.0450 (8)	0.0383 (8)	0.0512 (8)	−0.0018 (6)	0.0020 (6)	−0.0038 (6)
N7A	0.0622 (8)	0.0462 (7)	0.0497 (7)	−0.0135 (6)	0.0128 (6)	−0.0121 (6)
C7A	0.0868 (13)	0.0579 (10)	0.0503 (9)	−0.0145 (9)	0.0152 (9)	−0.0076 (8)
N8A	0.0471 (7)	0.0376 (6)	0.0518 (7)	−0.0047 (5)	0.0087 (5)	−0.0065 (5)
C9A	0.0519 (8)	0.0421 (8)	0.0491 (8)	−0.0016 (7)	0.0151 (7)	−0.0032 (7)
C10A	0.0411 (7)	0.0343 (7)	0.0503 (8)	0.0004 (6)	0.0159 (6)	0.0018 (6)
N11A	0.0388 (6)	0.0375 (6)	0.0483 (7)	−0.0051 (5)	0.0131 (5)	0.0046 (5)
C12A	0.0451 (8)	0.0449 (8)	0.0500 (8)	−0.0059 (7)	0.0134 (6)	−0.0033 (7)
N13A	0.0531 (7)	0.0424 (7)	0.0646 (8)	−0.0117 (6)	0.0237 (6)	−0.0042 (6)
C14A	0.0560 (9)	0.0439 (8)	0.0564 (9)	−0.0074 (7)	0.0268 (7)	−0.0008 (7)
N1B	0.0361 (6)	0.0583 (8)	0.0513 (7)	−0.0034 (6)	0.0148 (5)	−0.0047 (6)
C2B	0.0467 (8)	0.0675 (11)	0.0545 (9)	−0.0137 (8)	0.0195 (7)	−0.0062 (8)
C3B	0.0676 (11)	0.0551 (10)	0.0520 (9)	−0.0172 (8)	0.0190 (8)	−0.0012 (8)
C4B	0.0620 (10)	0.0444 (9)	0.0593 (9)	0.0012 (7)	0.0135 (8)	0.0025 (7)
C5B	0.0420 (8)	0.0448 (8)	0.0575 (9)	0.0023 (7)	0.0146 (7)	−0.0004 (7)
C6B	0.0354 (7)	0.0428 (8)	0.0384 (7)	−0.0025 (6)	0.0077 (5)	−0.0065 (6)
N7B	0.0307 (6)	0.0472 (7)	0.0571 (7)	0.0058 (5)	0.0130 (5)	0.0073 (6)
C7B	0.0390 (8)	0.0521 (9)	0.0684 (10)	0.0102 (7)	0.0146 (7)	0.0057 (8)
N8B	0.0315 (6)	0.0452 (7)	0.0463 (6)	0.0020 (5)	0.0112 (5)	0.0017 (5)
C9B	0.0401 (7)	0.0416 (8)	0.0428 (7)	0.0044 (6)	0.0089 (6)	0.0029 (6)
C10B	0.0404 (7)	0.0390 (7)	0.0371 (7)	−0.0006 (6)	0.0104 (5)	0.0028 (6)
N11B	0.0372 (6)	0.0404 (7)	0.0435 (6)	−0.0009 (5)	0.0143 (5)	0.0061 (5)
C12B	0.0370 (7)	0.0548 (9)	0.0475 (8)	−0.0033 (7)	0.0131 (6)	0.0023 (7)
N13B	0.0470 (7)	0.0585 (8)	0.0500 (7)	−0.0128 (6)	0.0164 (6)	0.0054 (6)
C14B	0.0523 (9)	0.0436 (8)	0.0468 (8)	−0.0040 (7)	0.0119 (6)	0.0074 (7)

Geometric parameters (Å, º)

N1A—C6A	1.3319 (18)	N1B—C6B	1.3330 (16)
N1A—C2A	1.339 (2)	N1B—C2B	1.343 (2)
C2A—C3A	1.362 (3)	C2B—C3B	1.357 (2)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.378 (2)	C3B—C4B	1.383 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.367 (2)	C4B—C5B	1.369 (2)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.395 (2)	C5B—C6B	1.3969 (19)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—N7A	1.3946 (19)	C6B—N7B	1.3934 (17)
N7A—N8A	1.3640 (16)	N7B—N8B	1.3567 (14)
N7A—C7A	1.449 (2)	N7B—C7B	1.4475 (18)
C7A—H7A	0.9600	C7B—H7D	0.9600
C7A—H7B	0.9600	C7B—H7E	0.9600
C7A—H7C	0.9600	C7B—H7F	0.9600
N8A—C9A	1.2819 (18)	N8B—C9B	1.2776 (17)
C9A—C10A	1.445 (2)	C9B—C10B	1.4445 (18)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C14A	1.3649 (19)	C10B—C14B	1.3596 (19)
C10A—N11A	1.3677 (18)	C10B—N11B	1.3728 (18)
N11A—C12A	1.3395 (18)	N11B—C12B	1.3427 (17)
N11A—H11A	0.938 (17)	N11B—H11B	0.895 (17)
C12A—N13A	1.3160 (18)	C12B—N13B	1.3143 (19)
C12A—H12A	0.9300	C12B—H12B	0.9300
N13A—C14A	1.370 (2)	N13B—C14B	1.3732 (19)
C14A—H14A	0.9300	C14B—H14B	0.9300
C6A—N1A—C2A	116.81 (15)	C6B—N1B—C2B	116.86 (13)
N1A—C2A—C3A	124.72 (16)	N1B—C2B—C3B	124.46 (14)
N1A—C2A—H2A	117.6	N1B—C2B—H2B	117.8
C3A—C2A—H2A	117.6	C3B—C2B—H2B	117.8
C2A—C3A—C4A	117.57 (16)	C2B—C3B—C4B	117.71 (15)
C2A—C3A—H3A	121.2	C2B—C3B—H3B	121.1
C4A—C3A—H3A	121.2	C4B—C3B—H3B	121.1
C5A—C4A—C3A	119.83 (17)	C5B—C4B—C3B	120.16 (15)
C5A—C4A—H4A	120.1	C5B—C4B—H4B	119.9
C3A—C4A—H4A	120.1	C3B—C4B—H4B	119.9
C4A—C5A—C6A	118.42 (14)	C4B—C5B—C6B	117.76 (14)
C4A—C5A—H5A	120.8	C4B—C5B—H5B	121.1
C6A—C5A—H5A	120.8	C6B—C5B—H5B	121.1
N1A—C6A—N7A	115.60 (14)	N1B—C6B—N7B	115.81 (12)
N1A—C6A—C5A	122.65 (14)	N1B—C6B—C5B	123.03 (13)
N7A—C6A—C5A	121.75 (13)	N7B—C6B—C5B	121.16 (12)
N8A—N7A—C6A	115.85 (12)	N8B—N7B—C6B	115.40 (11)
N8A—N7A—C7A	122.26 (13)	N8B—N7B—C7B	121.53 (11)
C6A—N7A—C7A	121.88 (13)	C6B—N7B—C7B	122.86 (11)
N7A—C7A—H7A	109.5	N7B—C7B—H7D	109.5
N7A—C7A—H7B	109.5	N7B—C7B—H7E	109.5
H7A—C7A—H7B	109.5	H7D—C7B—H7E	109.5
N7A—C7A—H7C	109.5	N7B—C7B—H7F	109.5
H7A—C7A—H7C	109.5	H7D—C7B—H7F	109.5
H7B—C7A—H7C	109.5	H7E—C7B—H7F	109.5
C9A—N8A—N7A	120.21 (13)	C9B—N8B—N7B	120.61 (12)
N8A—C9A—C10A	119.50 (13)	N8B—C9B—C10B	118.40 (12)
N8A—C9A—H9A	120.3	N8B—C9B—H9B	120.8
C10A—C9A—H9A	120.3	C10B—C9B—H9B	120.8
C14A—C10A—N11A	105.08 (12)	C14B—C10B—N11B	105.10 (12)
C14A—C10A—C9A	131.16 (14)	C14B—C10B—C9B	131.69 (13)
N11A—C10A—C9A	123.74 (12)	N11B—C10B—C9B	123.21 (12)
C12A—N11A—C10A	107.22 (12)	C12B—N11B—C10B	107.29 (12)
C12A—N11A—H11A	124.4 (10)	C12B—N11B—H11B	124.1 (10)
C10A—N11A—H11A	128.4 (10)	C10B—N11B—H11B	128.6 (10)
N13A—C12A—N11A	112.61 (13)	N13B—C12B—N11B	112.23 (13)
N13A—C12A—H12A	123.7	N13B—C12B—H12B	123.9
N11A—C12A—H12A	123.7	N11B—C12B—H12B	123.9
C12A—N13A—C14A	104.20 (12)	C12B—N13B—C14B	104.56 (12)
C10A—C14A—N13A	110.88 (13)	C10B—C14B—N13B	110.82 (13)
C10A—C14A—H14A	124.6	C10B—C14B—H14B	124.6
N13A—C14A—H14A	124.6	N13B—C14B—H14B	124.6

2-[(2E)-2-(1H-Imidazol-2-ylmethylidene)-1-methylhydrazinyl]-1H-benzimidazole monohydrate (2)

Crystal data

C12H12N6·H2O	F(000) = 1088
Mr = 258.29	Dx = 1.341 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2711 (7) Å	Cell parameters from 1351 reflections
b = 14.0773 (12) Å	θ = 3.8–22.0°
c = 22.2655 (16) Å	µ = 0.09 mm^−1
β = 99.373 (8)°	T = 295 K
V = 2557.9 (4) Å^3	Block, colourless
Z = 8	0.25 × 0.2 × 0.2 mm

Data collection

Rigaku Xcalibur Eos diffractometer	4502 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.2413 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −16→14
Tmin = 0.987, Tmax = 1.000	l = −26→24
9720 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0345P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
4502 reflections	Δρmax = 0.14 e Å^−3
377 parameters	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.8016 (2)	0.55051 (14)	0.51023 (9)	0.0557 (5)
C2A	0.7451 (3)	0.49279 (18)	0.54771 (10)	0.0498 (6)
N3A	0.6744 (2)	0.41254 (15)	0.52159 (9)	0.0546 (5)
H3A	0.620 (3)	0.3708 (19)	0.5396 (11)	0.084 (10)*
C4A	0.6854 (3)	0.41917 (18)	0.46037 (10)	0.0516 (6)
C5A	0.6353 (3)	0.35981 (19)	0.41178 (11)	0.0649 (7)
H5A	0.5818	0.3029	0.4167	0.078*
C6A	0.6672 (3)	0.3877 (2)	0.35545 (11)	0.0751 (8)
H6A	0.6358	0.3490	0.3217	0.090*
C7A	0.7455 (3)	0.4729 (3)	0.34887 (12)	0.0775 (9)
H7A	0.7649	0.4904	0.3104	0.093*
C8A	0.7960 (3)	0.5330 (2)	0.39729 (12)	0.0701 (8)
H8A	0.8487	0.5900	0.3921	0.084*
C9A	0.7647 (3)	0.50469 (19)	0.45402 (10)	0.0537 (6)
N10A	0.7565 (2)	0.50712 (15)	0.60928 (8)	0.0555 (5)
C10A	0.8294 (3)	0.59270 (18)	0.63762 (11)	0.0709 (8)
H10A	0.8902	0.6243	0.6103	0.106*
H10B	0.9017	0.5766	0.6744	0.106*
H10C	0.7446	0.6341	0.6470	0.106*
N11A	0.6686 (2)	0.44424 (13)	0.63728 (8)	0.0511 (5)
C12A	0.6511 (2)	0.45719 (17)	0.69275 (10)	0.0540 (6)
H12A	0.7012	0.5082	0.7150	0.065*
C13A	0.5519 (3)	0.39091 (19)	0.71978 (10)	0.0515 (6)
N14A	0.4845 (2)	0.31230 (15)	0.69140 (10)	0.0599 (6)
H14A	0.493 (3)	0.2927 (19)	0.6481 (11)	0.096 (9)*
C15A	0.3926 (3)	0.2704 (2)	0.72949 (12)	0.0766 (8)
H15A	0.3303	0.2154	0.7222	0.092*
C16A	0.4108 (3)	0.3254 (2)	0.78018 (11)	0.0734 (8)
H16A	0.3623	0.3133	0.8143	0.088*
N17A	0.5105 (2)	0.40146 (16)	0.77419 (8)	0.0608 (6)
N1B	0.37852 (18)	−0.06562 (13)	0.43343 (7)	0.0435 (5)
C2B	0.2985 (2)	−0.00740 (16)	0.46394 (9)	0.0386 (5)
N3B	0.2820 (2)	0.08276 (14)	0.44092 (8)	0.0431 (5)
H3B	0.239 (3)	0.1329 (17)	0.4589 (10)	0.082 (9)*
C4B	0.3597 (2)	0.08246 (17)	0.39025 (9)	0.0414 (5)
C5B	0.3825 (3)	0.15232 (18)	0.34914 (9)	0.0540 (6)
H5B	0.3406	0.2132	0.3519	0.065*
C6B	0.4701 (3)	0.1283 (2)	0.30377 (10)	0.0634 (7)
H6B	0.4892	0.1740	0.2756	0.076*
C7B	0.5302 (3)	0.0370 (2)	0.29952 (10)	0.0656 (8)
H7B	0.5890	0.0227	0.2685	0.079*
C8B	0.5050 (2)	−0.03307 (19)	0.34020 (10)	0.0571 (7)
H8B	0.5451	−0.0942	0.3368	0.068*
C9B	0.4183 (2)	−0.00962 (17)	0.38616 (9)	0.0425 (5)
N10B	0.23477 (18)	−0.03130 (13)	0.51470 (7)	0.0428 (4)
C10B	0.2359 (3)	−0.12909 (15)	0.53573 (9)	0.0508 (6)
H10D	0.2869	−0.1688	0.5092	0.076*
H10E	0.1253	−0.1500	0.5356	0.076*
H10F	0.2961	−0.1330	0.5763	0.076*
N11B	0.16643 (18)	0.04169 (13)	0.54156 (7)	0.0424 (5)
C12B	0.1063 (2)	0.02586 (16)	0.59005 (9)	0.0434 (5)
H12B	0.1101	−0.0348	0.6067	0.052*
C13B	0.0330 (2)	0.10253 (17)	0.61852 (9)	0.0429 (6)
N14B	−0.0372 (2)	0.08652 (17)	0.66841 (8)	0.0498 (5)
H14B	−0.040 (3)	0.022 (2)	0.6875 (11)	0.106 (10)*
C15B	−0.1010 (3)	0.1710 (2)	0.68290 (10)	0.0595 (7)
H15B	−0.1576	0.1824	0.7150	0.071*
C16B	−0.0661 (3)	0.23489 (18)	0.64171 (10)	0.0595 (7)
H16B	−0.0954	0.2987	0.6410	0.071*
N17B	0.0186 (2)	0.19240 (14)	0.60106 (8)	0.0516 (5)
O1W	0.5012 (3)	0.25241 (13)	0.56776 (8)	0.0585 (5)
H1W1	0.553 (4)	0.189 (3)	0.5662 (14)	0.172 (16)*
H1W2	0.405 (3)	0.252 (2)	0.5505 (13)	0.107 (13)*
O2W	0.1769 (2)	0.25006 (14)	0.50022 (8)	0.0627 (5)
H2W1	0.168 (3)	0.317 (3)	0.4924 (13)	0.130 (13)*
H2W2	0.118 (3)	0.233 (2)	0.5328 (14)	0.138 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0576 (12)	0.0437 (14)	0.0681 (14)	0.0025 (10)	0.0172 (11)	0.0103 (11)
C2A	0.0549 (14)	0.0365 (16)	0.0594 (15)	0.0043 (12)	0.0136 (12)	0.0023 (13)
N3A	0.0755 (14)	0.0383 (14)	0.0515 (13)	−0.0017 (11)	0.0146 (11)	0.0059 (11)
C4A	0.0616 (14)	0.0452 (17)	0.0485 (15)	0.0130 (13)	0.0109 (12)	0.0087 (13)
C5A	0.0802 (17)	0.0561 (19)	0.0566 (16)	0.0104 (14)	0.0055 (14)	0.0040 (15)
C6A	0.0832 (19)	0.089 (3)	0.0520 (17)	0.0272 (18)	0.0091 (14)	0.0015 (16)
C7A	0.0688 (18)	0.106 (3)	0.0610 (18)	0.0223 (18)	0.0217 (15)	0.022 (2)
C8A	0.0605 (16)	0.078 (2)	0.0752 (18)	0.0080 (14)	0.0204 (15)	0.0220 (18)
C9A	0.0515 (13)	0.0547 (18)	0.0579 (16)	0.0117 (13)	0.0177 (12)	0.0144 (14)
N10A	0.0697 (12)	0.0419 (14)	0.0564 (12)	−0.0050 (11)	0.0145 (10)	−0.0026 (11)
C10A	0.0758 (17)	0.0509 (19)	0.0847 (19)	−0.0077 (14)	0.0087 (14)	−0.0133 (15)
N11A	0.0601 (12)	0.0417 (13)	0.0527 (12)	0.0042 (10)	0.0134 (10)	0.0007 (10)
C12A	0.0555 (14)	0.0502 (17)	0.0557 (15)	0.0079 (12)	0.0071 (12)	−0.0090 (13)
C13A	0.0570 (14)	0.0479 (17)	0.0506 (15)	0.0087 (13)	0.0115 (12)	−0.0034 (13)
N14A	0.0787 (14)	0.0479 (15)	0.0580 (13)	0.0031 (12)	0.0251 (12)	−0.0074 (12)
C15A	0.100 (2)	0.061 (2)	0.0788 (19)	−0.0112 (16)	0.0441 (17)	−0.0135 (16)
C16A	0.0907 (19)	0.070 (2)	0.0686 (18)	0.0028 (17)	0.0392 (16)	−0.0031 (17)
N17A	0.0697 (13)	0.0662 (17)	0.0497 (12)	0.0062 (12)	0.0192 (10)	−0.0082 (11)
N1B	0.0479 (10)	0.0380 (12)	0.0460 (11)	0.0014 (9)	0.0124 (9)	−0.0044 (9)
C2B	0.0391 (11)	0.0370 (15)	0.0396 (12)	−0.0006 (11)	0.0059 (10)	−0.0031 (11)
N3B	0.0504 (11)	0.0348 (13)	0.0454 (11)	0.0032 (10)	0.0120 (9)	−0.0002 (10)
C4B	0.0444 (12)	0.0433 (15)	0.0370 (12)	−0.0044 (11)	0.0082 (10)	−0.0008 (11)
C5B	0.0638 (14)	0.0488 (17)	0.0494 (14)	−0.0037 (12)	0.0092 (12)	0.0058 (13)
C6B	0.0718 (16)	0.071 (2)	0.0480 (15)	−0.0102 (15)	0.0129 (13)	0.0096 (14)
C7B	0.0724 (16)	0.082 (2)	0.0472 (15)	−0.0089 (16)	0.0231 (13)	−0.0077 (16)
C8B	0.0616 (14)	0.0564 (18)	0.0569 (14)	−0.0010 (13)	0.0205 (12)	−0.0128 (14)
C9B	0.0440 (12)	0.0406 (15)	0.0427 (12)	−0.0037 (11)	0.0064 (10)	−0.0068 (12)
N10B	0.0522 (10)	0.0349 (12)	0.0437 (10)	0.0039 (9)	0.0158 (9)	0.0015 (9)
C10B	0.0646 (14)	0.0339 (15)	0.0555 (14)	0.0020 (12)	0.0148 (12)	0.0065 (12)
N11B	0.0478 (10)	0.0392 (12)	0.0416 (10)	0.0036 (9)	0.0112 (9)	−0.0015 (9)
C12B	0.0482 (12)	0.0408 (15)	0.0416 (12)	0.0000 (11)	0.0080 (10)	0.0035 (11)
C13B	0.0467 (12)	0.0460 (16)	0.0373 (12)	−0.0014 (12)	0.0112 (10)	−0.0022 (12)
N14B	0.0576 (11)	0.0520 (15)	0.0424 (11)	0.0004 (11)	0.0162 (9)	−0.0026 (11)
C15B	0.0691 (15)	0.064 (2)	0.0509 (15)	−0.0029 (14)	0.0246 (13)	−0.0120 (14)
C16B	0.0711 (16)	0.0467 (17)	0.0637 (16)	0.0043 (13)	0.0203 (14)	−0.0062 (14)
N17B	0.0625 (11)	0.0422 (13)	0.0533 (12)	0.0011 (10)	0.0190 (10)	0.0005 (10)
O1W	0.0702 (13)	0.0425 (12)	0.0637 (11)	0.0022 (10)	0.0136 (10)	−0.0049 (9)
O2W	0.0830 (11)	0.0410 (12)	0.0703 (12)	0.0000 (10)	0.0306 (10)	0.0030 (10)

Geometric parameters (Å, º)

N1A—C2A	1.304 (3)	C2B—N10B	1.365 (2)
N1A—C9A	1.397 (3)	C2B—N3B	1.367 (3)
C2A—N3A	1.359 (3)	N3B—C4B	1.386 (2)
C2A—N10A	1.374 (3)	N3B—H3B	0.91 (2)
N3A—C4A	1.384 (3)	C4B—C5B	1.377 (3)
N3A—H3A	0.88 (2)	C4B—C9B	1.392 (3)
C4A—C5A	1.376 (3)	C5B—C6B	1.377 (3)
C4A—C9A	1.389 (3)	C5B—H5B	0.9300
C5A—C6A	1.380 (3)	C6B—C7B	1.388 (3)
C5A—H5A	0.9300	C6B—H6B	0.9300
C6A—C7A	1.381 (4)	C7B—C8B	1.377 (3)
C6A—H6A	0.9300	C7B—H7B	0.9300
C7A—C8A	1.381 (4)	C8B—C9B	1.382 (3)
C7A—H7A	0.9300	C8B—H8B	0.9300
C8A—C9A	1.388 (3)	N10B—N11B	1.357 (2)
C8A—H8A	0.9300	N10B—C10B	1.454 (2)
N10A—N11A	1.360 (2)	C10B—H10D	0.9600
N10A—C10A	1.445 (3)	C10B—H10E	0.9600
C10A—H10A	0.9600	C10B—H10F	0.9600
C10A—H10B	0.9600	N11B—C12B	1.280 (2)
C10A—H10C	0.9600	C12B—C13B	1.435 (3)
N11A—C12A	1.280 (2)	C12B—H12B	0.9300
C12A—C13A	1.438 (3)	C13B—N17B	1.323 (3)
C12A—H12A	0.9300	C13B—N14B	1.354 (2)
C13A—N17A	1.320 (2)	N14B—C15B	1.360 (3)
C13A—N14A	1.349 (3)	N14B—H14B	1.00 (3)
N14A—C15A	1.362 (3)	C15B—C16B	1.349 (3)
N14A—H14A	1.02 (2)	C15B—H15B	0.9300
C15A—C16A	1.357 (3)	C16B—N17B	1.369 (2)
C15A—H15A	0.9300	C16B—H16B	0.9300
C16A—N17A	1.371 (3)	O1W—H1W1	1.00 (4)
C16A—H16A	0.9300	O1W—H1W2	0.82 (3)
N1B—C2B	1.311 (2)	O2W—H2W1	0.96 (4)
N1B—C9B	1.396 (2)	O2W—H2W2	0.97 (3)
C2A—N1A—C9A	103.7 (2)	N1B—C2B—N10B	124.8 (2)
N1A—C2A—N3A	114.7 (2)	N1B—C2B—N3B	114.47 (18)
N1A—C2A—N10A	125.0 (2)	N10B—C2B—N3B	120.72 (19)
N3A—C2A—N10A	120.3 (2)	C2B—N3B—C4B	105.72 (19)
C2A—N3A—C4A	105.8 (2)	C2B—N3B—H3B	125.2 (14)
C2A—N3A—H3A	125.4 (16)	C4B—N3B—H3B	128.6 (14)
C4A—N3A—H3A	128.1 (17)	C5B—C4B—N3B	132.1 (2)
C5A—C4A—N3A	132.3 (2)	C5B—C4B—C9B	122.3 (2)
C5A—C4A—C9A	122.2 (2)	N3B—C4B—C9B	105.57 (19)
N3A—C4A—C9A	105.5 (2)	C4B—C5B—C6B	117.2 (2)
C4A—C5A—C6A	117.6 (3)	C4B—C5B—H5B	121.4
C4A—C5A—H5A	121.2	C6B—C5B—H5B	121.4
C6A—C5A—H5A	121.2	C5B—C6B—C7B	120.9 (2)
C5A—C6A—C7A	120.4 (3)	C5B—C6B—H6B	119.5
C5A—C6A—H6A	119.8	C7B—C6B—H6B	119.5
C7A—C6A—H6A	119.8	C8B—C7B—C6B	121.6 (2)
C8A—C7A—C6A	122.5 (3)	C8B—C7B—H7B	119.2
C8A—C7A—H7A	118.8	C6B—C7B—H7B	119.2
C6A—C7A—H7A	118.8	C7B—C8B—C9B	117.9 (2)
C7A—C8A—C9A	117.2 (3)	C7B—C8B—H8B	121.0
C7A—C8A—H8A	121.4	C9B—C8B—H8B	121.0
C9A—C8A—H8A	121.4	C8B—C9B—C4B	119.9 (2)
C8A—C9A—C4A	120.1 (3)	C8B—C9B—N1B	129.6 (2)
C8A—C9A—N1A	129.6 (3)	C4B—C9B—N1B	110.45 (18)
C4A—C9A—N1A	110.30 (19)	N11B—N10B—C2B	115.02 (18)
N11A—N10A—C2A	114.03 (19)	N11B—N10B—C10B	123.78 (16)
N11A—N10A—C10A	123.95 (18)	C2B—N10B—C10B	121.15 (18)
C2A—N10A—C10A	120.9 (2)	N10B—C10B—H10D	109.5
N10A—C10A—H10A	109.5	N10B—C10B—H10E	109.5
N10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
H10A—C10A—H10B	109.5	N10B—C10B—H10F	109.5
N10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10E—C10B—H10F	109.5
H10B—C10A—H10C	109.5	C12B—N11B—N10B	119.13 (18)
C12A—N11A—N10A	120.2 (2)	N11B—C12B—C13B	119.5 (2)
N11A—C12A—C13A	118.3 (2)	N11B—C12B—H12B	120.3
N11A—C12A—H12A	120.9	C13B—C12B—H12B	120.3
C13A—C12A—H12A	120.9	N17B—C13B—N14B	111.7 (2)
N17A—C13A—N14A	111.9 (2)	N17B—C13B—C12B	127.85 (19)
N17A—C13A—C12A	124.2 (2)	N14B—C13B—C12B	120.4 (2)
N14A—C13A—C12A	123.8 (2)	C13B—N14B—C15B	106.5 (2)
C13A—N14A—C15A	107.1 (2)	C13B—N14B—H14B	122.7 (14)
C13A—N14A—H14A	125.4 (15)	C15B—N14B—H14B	130.8 (14)
C15A—N14A—H14A	127.2 (14)	C16B—C15B—N14B	106.7 (2)
C16A—C15A—N14A	105.9 (2)	C16B—C15B—H15B	126.6
C16A—C15A—H15A	127.1	N14B—C15B—H15B	126.6
N14A—C15A—H15A	127.1	C15B—C16B—N17B	110.3 (2)
C15A—C16A—N17A	110.6 (2)	C15B—C16B—H16B	124.8
C15A—C16A—H16A	124.7	N17B—C16B—H16B	124.8
N17A—C16A—H16A	124.7	C13B—N17B—C16B	104.75 (19)
C13A—N17A—C16A	104.6 (2)	H1W1—O1W—H1W2	111 (3)
C2B—N1B—C9B	103.79 (18)	H2W1—O2W—H2W2	111 (2)
C9A—N1A—C2A—N3A	0.2 (3)	C9B—N1B—C2B—N10B	179.95 (17)
C9A—N1A—C2A—N10A	178.6 (2)	C9B—N1B—C2B—N3B	−0.1 (2)
N1A—C2A—N3A—C4A	−0.3 (3)	N1B—C2B—N3B—C4B	0.0 (2)
N10A—C2A—N3A—C4A	−178.80 (19)	N10B—C2B—N3B—C4B	179.92 (16)
C2A—N3A—C4A—C5A	−179.9 (2)	C2B—N3B—C4B—C5B	−180.0 (2)
C2A—N3A—C4A—C9A	0.3 (2)	C2B—N3B—C4B—C9B	0.2 (2)
N3A—C4A—C5A—C6A	−179.4 (2)	N3B—C4B—C5B—C6B	178.7 (2)
C9A—C4A—C5A—C6A	0.4 (3)	C9B—C4B—C5B—C6B	−1.5 (3)
C4A—C5A—C6A—C7A	−0.6 (3)	C4B—C5B—C6B—C7B	0.9 (3)
C5A—C6A—C7A—C8A	0.5 (4)	C5B—C6B—C7B—C8B	0.0 (4)
C6A—C7A—C8A—C9A	−0.1 (4)	C6B—C7B—C8B—C9B	−0.5 (3)
C7A—C8A—C9A—C4A	−0.1 (3)	C7B—C8B—C9B—C4B	−0.1 (3)
C7A—C8A—C9A—N1A	179.9 (2)	C7B—C8B—C9B—N1B	−178.65 (19)
C5A—C4A—C9A—C8A	0.0 (3)	C5B—C4B—C9B—C8B	1.1 (3)
N3A—C4A—C9A—C8A	179.79 (19)	N3B—C4B—C9B—C8B	−179.06 (17)
C5A—C4A—C9A—N1A	180.0 (2)	C5B—C4B—C9B—N1B	179.90 (18)
N3A—C4A—C9A—N1A	−0.2 (2)	N3B—C4B—C9B—N1B	−0.2 (2)
C2A—N1A—C9A—C8A	−180.0 (2)	C2B—N1B—C9B—C8B	178.9 (2)
C2A—N1A—C9A—C4A	0.1 (2)	C2B—N1B—C9B—C4B	0.2 (2)
N1A—C2A—N10A—N11A	171.11 (19)	N1B—C2B—N10B—N11B	175.63 (17)
N3A—C2A—N10A—N11A	−10.6 (3)	N3B—C2B—N10B—N11B	−4.3 (2)
N1A—C2A—N10A—C10A	2.5 (3)	N1B—C2B—N10B—C10B	−6.8 (3)
N3A—C2A—N10A—C10A	−179.1 (2)	N3B—C2B—N10B—C10B	173.23 (18)
C2A—N10A—N11A—C12A	−170.73 (19)	C2B—N10B—N11B—C12B	−178.78 (17)
C10A—N10A—N11A—C12A	−2.6 (3)	C10B—N10B—N11B—C12B	3.7 (3)
N10A—N11A—C12A—C13A	177.65 (18)	N10B—N11B—C12B—C13B	−179.63 (16)
N11A—C12A—C13A—N17A	−172.8 (2)	N11B—C12B—C13B—N17B	−0.5 (3)
N11A—C12A—C13A—N14A	4.4 (3)	N11B—C12B—C13B—N14B	177.31 (18)
N17A—C13A—N14A—C15A	0.8 (3)	N17B—C13B—N14B—C15B	0.6 (2)
C12A—C13A—N14A—C15A	−176.7 (2)	C12B—C13B—N14B—C15B	−177.46 (18)
C13A—N14A—C15A—C16A	−0.9 (3)	C13B—N14B—C15B—C16B	−0.5 (2)
N14A—C15A—C16A—N17A	0.7 (3)	N14B—C15B—C16B—N17B	0.2 (3)
N14A—C13A—N17A—C16A	−0.3 (3)	N14B—C13B—N17B—C16B	−0.5 (2)
C12A—C13A—N17A—C16A	177.2 (2)	C12B—C13B—N17B—C16B	177.40 (19)
C15A—C16A—N17A—C13A	−0.3 (3)	C15B—C16B—N17B—C13B	0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O1W	0.88 (2)	2.08 (2)	2.944 (3)	168 (2)
N14A—H14A···O1W	1.02 (2)	1.89 (2)	2.904 (3)	177 (2)
N3B—H3B···O2W	0.91 (2)	2.00 (2)	2.902 (3)	172 (2)
N14B—H14B···N17A^i	1.00 (3)	1.90 (3)	2.894 (3)	172 (2)
O1W—H1W1···N1B^ii	1.00 (4)	1.82 (4)	2.813 (3)	172 (3)
O1W—H1W2···O2W	0.82 (3)	2.03 (3)	2.854 (3)	175 (3)
O2W—H2W1···N1A^iii	0.96 (4)	1.88 (4)	2.825 (3)	167 (3)
O2W—H2W2···N17B	0.97 (3)	1.93 (3)	2.893 (2)	175 (3)

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

2-{(2E)-1-Methyl-2-[(1-methyl-1H-imidazol-2-yl)methylidene]hydrazinyl}-1H-benzimidazole hydrate (3)

Crystal data

4C13H14N6·5H2O	Z = 2
Mr = 1107.28	F(000) = 1172
Triclinic, P1	Dx = 1.277 Mg m^−3
a = 9.1836 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 16.5814 (4) Å	Cell parameters from 24014 reflections
c = 20.8041 (6) Å	θ = 2.9–75.9°
α = 106.760 (2)°	µ = 0.72 mm^−1
β = 97.854 (2)°	T = 130 K
γ = 103.408 (2)°	Plate, yellow
V = 2879.43 (15) Å^3	0.25 × 0.25 × 0.08 mm

Data collection

Rigaku SuperNova diffractometer with an Atlas detector	11893 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	9917 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
ω scans	θmax = 77.2°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −11→11
Tmin = 0.702, Tmax = 1.000	k = −20→20
51173 measured reflections	l = −26→26

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0801P)^2 + 0.6386P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.37 e Å^−3
11893 reflections	Δρmin = −0.27 e Å^−3
739 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00062 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.1006 (2)	0.65283 (9)	0.30680 (7)	0.0529 (4)
C2A	0.2002 (2)	0.70535 (10)	0.36361 (8)	0.0439 (4)
N3A	0.31496 (17)	0.67284 (8)	0.38354 (8)	0.0476 (3)
H3A	0.3911	0.6988	0.4199	0.057*
C4A	0.2878 (2)	0.59034 (10)	0.33486 (10)	0.0527 (5)
C5A	0.3646 (3)	0.52657 (11)	0.32779 (13)	0.0681 (6)
H5A	0.4545	0.5343	0.3603	0.082*
C6A	0.3036 (3)	0.45072 (12)	0.27088 (15)	0.0802 (8)
H6A	0.3537	0.4058	0.2641	0.096*
C7A	0.1718 (4)	0.43884 (13)	0.22374 (13)	0.0802 (8)
H7A	0.1339	0.3859	0.1856	0.096*
C8A	0.0938 (3)	0.50202 (12)	0.23071 (10)	0.0696 (6)
H8A	0.0032	0.4935	0.1983	0.084*
C9A	0.1543 (3)	0.57897 (11)	0.28765 (9)	0.0557 (5)
N10A	0.19294 (16)	0.78744 (8)	0.39994 (7)	0.0433 (3)
C10A	0.0724 (2)	0.82248 (11)	0.37705 (9)	0.0489 (4)
H10A	0.0169	0.8378	0.4137	0.073*
H10B	0.0012	0.7782	0.3360	0.073*
H10C	0.1178	0.8751	0.3660	0.073*
N11A	0.30574 (15)	0.83167 (8)	0.45715 (7)	0.0405 (3)
C12A	0.30878 (17)	0.90948 (9)	0.49366 (8)	0.0392 (3)
H12A	0.2353	0.9367	0.4800	0.047*
C13A	0.42641 (17)	0.95447 (9)	0.55576 (8)	0.0388 (3)
N14A	0.43848 (15)	1.03703 (8)	0.59762 (7)	0.0390 (3)
C14A	0.3458 (2)	1.09420 (10)	0.58572 (9)	0.0445 (4)
H14A	0.3602	1.1071	0.5435	0.067*
H14B	0.3776	1.1492	0.6247	0.067*
H14C	0.2373	1.0646	0.5809	0.067*
C15A	0.55619 (18)	1.05772 (10)	0.65305 (8)	0.0424 (3)
H15A	0.5916	1.1107	0.6912	0.051*
C16A	0.61218 (19)	0.98671 (10)	0.64232 (9)	0.0442 (3)
H16A	0.6952	0.9825	0.6726	0.053*
N17A	0.53181 (15)	0.92211 (8)	0.58154 (7)	0.0426 (3)
N1B	−0.12074 (14)	0.77801 (8)	0.50452 (7)	0.0394 (3)
C2B	−0.03609 (17)	0.72259 (10)	0.49817 (8)	0.0377 (3)
N3B	0.09466 (14)	0.75019 (8)	0.54767 (6)	0.0368 (3)
H3B	0.1639	0.7220	0.5513	0.044*
C4B	0.09702 (16)	0.83176 (9)	0.59129 (8)	0.0350 (3)
C5B	0.19983 (17)	0.89038 (10)	0.65015 (8)	0.0390 (3)
H5B	0.2907	0.8787	0.6680	0.047*
C6B	0.16441 (17)	0.96739 (10)	0.68222 (8)	0.0399 (3)
H6B	0.2323	1.0091	0.7229	0.048*
C7B	0.03097 (18)	0.98443 (10)	0.65567 (8)	0.0402 (3)
H7B	0.0095	1.0373	0.6789	0.048*
C8B	−0.07084 (17)	0.92560 (10)	0.59604 (8)	0.0397 (3)
H8B	−0.1607	0.9379	0.5778	0.048*
C9B	−0.03759 (16)	0.84811 (9)	0.56367 (8)	0.0367 (3)
N10B	−0.07246 (15)	0.64388 (8)	0.44646 (7)	0.0423 (3)
C10B	−0.2115 (2)	0.61264 (12)	0.39344 (10)	0.0536 (4)
H10D	−0.1855	0.5991	0.3481	0.080*
H10E	−0.2648	0.6582	0.3991	0.080*
H10F	−0.2783	0.5595	0.3971	0.080*
N11B	0.02528 (15)	0.59472 (8)	0.45275 (7)	0.0409 (3)
C12B	−0.00486 (19)	0.51711 (10)	0.40921 (9)	0.0432 (3)
H12B	−0.0940	0.4937	0.3731	0.052*
C13B	0.10147 (18)	0.46625 (10)	0.41691 (9)	0.0431 (4)
N14B	0.07809 (16)	0.38259 (8)	0.37481 (7)	0.0455 (3)
C14B	−0.0531 (2)	0.33053 (11)	0.31835 (9)	0.0534 (4)
H14D	−0.1476	0.3261	0.3357	0.080*
H14E	−0.0425	0.2716	0.2982	0.080*
H14F	−0.0575	0.3590	0.2831	0.080*
C15B	0.2000 (2)	0.35555 (11)	0.39614 (10)	0.0513 (4)
H15B	0.2165	0.3000	0.3767	0.062*
C16B	0.2936 (2)	0.42408 (11)	0.45094 (10)	0.0520 (4)
H16B	0.3876	0.4238	0.4763	0.062*
N17B	0.23158 (16)	0.49358 (9)	0.46407 (8)	0.0478 (3)
N1C	0.90144 (15)	0.77482 (8)	0.91446 (7)	0.0429 (3)
C2C	0.77356 (17)	0.73583 (9)	0.92967 (8)	0.0392 (3)
N3C	0.64301 (15)	0.72889 (8)	0.88699 (7)	0.0422 (3)
H3C	0.5486	0.7052	0.8895	0.051*
C4C	0.68662 (19)	0.76641 (9)	0.83840 (9)	0.0423 (3)
C5C	0.6040 (2)	0.77749 (11)	0.78278 (10)	0.0509 (4)
H5C	0.4951	0.7593	0.7721	0.061*
C6C	0.6872 (2)	0.81654 (11)	0.74279 (10)	0.0563 (4)
H6C	0.6339	0.8249	0.7039	0.068*
C7C	0.8469 (2)	0.84344 (11)	0.75901 (10)	0.0562 (5)
H7C	0.9005	0.8697	0.7308	0.067*
C8C	0.9292 (2)	0.83277 (10)	0.81533 (9)	0.0507 (4)
H8C	1.0382	0.8514	0.8261	0.061*
C9C	0.84778 (19)	0.79387 (9)	0.85592 (8)	0.0426 (3)
N10C	0.77001 (15)	0.70443 (8)	0.98395 (7)	0.0429 (3)
C10C	0.90810 (19)	0.71395 (11)	1.03182 (9)	0.0487 (4)
H10G	0.9090	0.7529	1.0775	0.073*
H10H	0.9981	0.7392	1.0160	0.073*
H10I	0.9107	0.6562	1.0344	0.073*
N11C	0.62613 (15)	0.66466 (8)	0.98822 (7)	0.0424 (3)
C12C	0.60595 (19)	0.63293 (10)	1.03705 (9)	0.0438 (4)
H12C	0.6889	0.6368	1.0716	0.053*
C13C	0.4465 (2)	0.59059 (10)	1.03555 (9)	0.0467 (4)
N14C	0.40234 (17)	0.55088 (9)	1.08143 (8)	0.0496 (3)
C14C	0.4992 (2)	0.53727 (12)	1.13622 (10)	0.0565 (5)
H14G	0.5441	0.4901	1.1165	0.085*
H14H	0.4375	0.5208	1.1678	0.085*
H14I	0.5813	0.5916	1.1614	0.085*
C15C	0.2457 (2)	0.52005 (11)	1.06339 (11)	0.0570 (5)
H15C	0.1807	0.4896	1.0859	0.068*
C16C	0.2012 (2)	0.54155 (12)	1.00693 (11)	0.0577 (5)
H16C	0.0980	0.5279	0.9831	0.069*
N17C	0.32713 (16)	0.58581 (9)	0.98952 (8)	0.0508 (3)
N1D	0.69809 (15)	0.84644 (8)	1.14451 (7)	0.0399 (3)
C2D	0.62430 (17)	0.85759 (9)	1.09017 (8)	0.0370 (3)
N3D	0.46901 (14)	0.82471 (8)	1.07649 (7)	0.0382 (3)
H3D	0.4022	0.8257	1.0423	0.046*
C4D	0.43775 (19)	0.78909 (9)	1.12775 (8)	0.0405 (3)
C5D	0.3007 (2)	0.74768 (10)	1.14076 (9)	0.0480 (4)
H5D	0.2043	0.7397	1.1127	0.058*
C6D	0.3122 (2)	0.71870 (11)	1.19686 (10)	0.0535 (4)
H6D	0.2212	0.6900	1.2076	0.064*
C7D	0.4533 (2)	0.73041 (11)	1.23789 (9)	0.0531 (4)
H7D	0.4561	0.7089	1.2756	0.064*
C8D	0.5903 (2)	0.77276 (10)	1.22529 (8)	0.0477 (4)
H8D	0.6864	0.7810	1.2538	0.057*
C9D	0.58099 (19)	0.80276 (10)	1.16908 (8)	0.0412 (3)
N10D	0.69364 (14)	0.89884 (8)	1.04912 (6)	0.0378 (3)
C10D	0.85700 (17)	0.94191 (11)	1.06742 (8)	0.0431 (3)
H10J	0.9040	0.9174	1.0296	0.065*
H10K	0.9028	0.9324	1.1090	0.065*
H10L	0.8748	1.0051	1.0761	0.065*
N11D	0.59626 (14)	0.90323 (8)	0.99588 (6)	0.0362 (3)
C12D	0.65110 (16)	0.94564 (9)	0.95770 (7)	0.0357 (3)
H12D	0.7577	0.9746	0.9672	0.043*
C13D	0.54862 (16)	0.94869 (9)	0.90029 (7)	0.0346 (3)
N14D	0.59963 (13)	0.99073 (7)	0.85647 (6)	0.0346 (2)
C14D	0.75707 (17)	1.03912 (10)	0.86089 (9)	0.0414 (3)
H14J	0.7978	1.0841	0.9064	0.062*
H14K	0.7590	1.0673	0.8255	0.062*
H14L	0.8202	0.9984	0.8537	0.062*
C15D	0.47602 (17)	0.97874 (10)	0.80676 (8)	0.0390 (3)
H15D	0.4755	1.0001	0.7690	0.047*
C16D	0.35309 (18)	0.92978 (11)	0.82211 (8)	0.0421 (3)
H16D	0.2508	0.9112	0.7960	0.051*
N17D	0.39775 (14)	0.91102 (8)	0.88071 (6)	0.0385 (3)
O1W	0.99057 (19)	0.83613 (13)	0.20951 (8)	0.0822 (5)
H1WA	0.9140	0.8453	0.1911	0.123*
H1WB	0.9686	0.7696	0.2074	0.123*
O2W	0.32669 (13)	0.66353 (8)	0.56699 (7)	0.0546 (3)
H2WA	0.4146	0.6897	0.5630	0.082*
H2WB	0.2992	0.6084	0.5292	0.082*
O3W	0.32990 (14)	0.66653 (8)	0.88886 (7)	0.0541 (3)
H3WA	0.2933	0.7092	0.9038	0.081*
H3WB	0.3377	0.6452	0.9214	0.081*
O4W	0.23582 (13)	0.81835 (8)	0.95918 (6)	0.0492 (3)
H4WA	0.2838	0.8587	0.9373	0.074*
H4WB	0.1391	0.8096	0.9460	0.074*
O5W	0.55630 (13)	0.74966 (7)	0.50868 (7)	0.0528 (3)
H5WA	0.6494	0.7521	0.5115	0.079*
H5WB	0.5606	0.7994	0.5341	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0857 (11)	0.0338 (7)	0.0463 (8)	0.0178 (7)	0.0292 (7)	0.0166 (6)
C2A	0.0623 (10)	0.0308 (7)	0.0482 (8)	0.0151 (7)	0.0314 (8)	0.0169 (6)
N3A	0.0567 (8)	0.0304 (6)	0.0658 (9)	0.0154 (6)	0.0360 (7)	0.0182 (6)
C4A	0.0728 (11)	0.0304 (7)	0.0678 (11)	0.0162 (7)	0.0478 (10)	0.0194 (7)
C5A	0.0727 (12)	0.0368 (9)	0.1093 (17)	0.0200 (8)	0.0616 (13)	0.0235 (10)
C6A	0.1079 (19)	0.0349 (9)	0.117 (2)	0.0263 (11)	0.0828 (18)	0.0220 (11)
C7A	0.138 (2)	0.0357 (9)	0.0785 (15)	0.0215 (12)	0.0734 (17)	0.0164 (9)
C8A	0.1266 (19)	0.0381 (9)	0.0511 (10)	0.0200 (10)	0.0447 (12)	0.0165 (8)
C9A	0.0928 (14)	0.0335 (8)	0.0522 (10)	0.0187 (8)	0.0430 (10)	0.0183 (7)
N10A	0.0543 (8)	0.0304 (6)	0.0493 (7)	0.0144 (6)	0.0208 (6)	0.0132 (5)
C10A	0.0623 (10)	0.0378 (8)	0.0537 (9)	0.0200 (7)	0.0205 (8)	0.0177 (7)
N11A	0.0474 (7)	0.0321 (6)	0.0490 (7)	0.0131 (5)	0.0246 (6)	0.0161 (5)
C12A	0.0446 (8)	0.0314 (7)	0.0510 (8)	0.0144 (6)	0.0260 (7)	0.0176 (6)
C13A	0.0452 (8)	0.0312 (7)	0.0500 (8)	0.0147 (6)	0.0281 (7)	0.0172 (6)
N14A	0.0472 (7)	0.0320 (6)	0.0466 (7)	0.0154 (5)	0.0250 (6)	0.0160 (5)
C14A	0.0563 (9)	0.0339 (7)	0.0512 (9)	0.0200 (7)	0.0234 (7)	0.0150 (7)
C15A	0.0487 (8)	0.0393 (8)	0.0451 (8)	0.0144 (7)	0.0227 (7)	0.0157 (6)
C16A	0.0481 (8)	0.0436 (8)	0.0491 (8)	0.0170 (7)	0.0238 (7)	0.0182 (7)
N17A	0.0470 (7)	0.0373 (6)	0.0537 (8)	0.0179 (6)	0.0260 (6)	0.0188 (6)
N1B	0.0380 (6)	0.0386 (6)	0.0448 (7)	0.0147 (5)	0.0145 (5)	0.0130 (5)
C2B	0.0371 (7)	0.0368 (7)	0.0445 (8)	0.0121 (6)	0.0189 (6)	0.0156 (6)
N3B	0.0345 (6)	0.0359 (6)	0.0467 (7)	0.0142 (5)	0.0171 (5)	0.0171 (5)
C4B	0.0339 (7)	0.0342 (7)	0.0430 (7)	0.0106 (5)	0.0178 (6)	0.0171 (6)
C5B	0.0361 (7)	0.0404 (7)	0.0471 (8)	0.0118 (6)	0.0163 (6)	0.0204 (6)
C6B	0.0411 (8)	0.0373 (7)	0.0439 (8)	0.0098 (6)	0.0151 (6)	0.0157 (6)
C7B	0.0447 (8)	0.0350 (7)	0.0468 (8)	0.0151 (6)	0.0180 (7)	0.0159 (6)
C8B	0.0397 (7)	0.0404 (8)	0.0467 (8)	0.0174 (6)	0.0150 (6)	0.0186 (6)
C9B	0.0361 (7)	0.0358 (7)	0.0437 (8)	0.0115 (6)	0.0162 (6)	0.0170 (6)
N10B	0.0389 (6)	0.0400 (7)	0.0496 (7)	0.0156 (5)	0.0158 (6)	0.0110 (6)
C10B	0.0473 (9)	0.0523 (10)	0.0553 (10)	0.0194 (8)	0.0095 (8)	0.0058 (8)
N11B	0.0415 (7)	0.0373 (6)	0.0522 (7)	0.0153 (5)	0.0242 (6)	0.0178 (6)
C12B	0.0443 (8)	0.0390 (8)	0.0513 (9)	0.0128 (6)	0.0248 (7)	0.0148 (7)
C13B	0.0466 (8)	0.0350 (7)	0.0556 (9)	0.0129 (6)	0.0289 (7)	0.0174 (7)
N14B	0.0519 (8)	0.0362 (6)	0.0560 (8)	0.0143 (6)	0.0292 (6)	0.0172 (6)
C14B	0.0652 (11)	0.0413 (8)	0.0557 (10)	0.0169 (8)	0.0256 (9)	0.0121 (7)
C15B	0.0597 (10)	0.0385 (8)	0.0695 (11)	0.0212 (8)	0.0333 (9)	0.0241 (8)
C16B	0.0515 (9)	0.0433 (9)	0.0744 (12)	0.0196 (7)	0.0283 (9)	0.0275 (8)
N17B	0.0467 (7)	0.0388 (7)	0.0657 (9)	0.0142 (6)	0.0262 (7)	0.0211 (6)
N1C	0.0437 (7)	0.0318 (6)	0.0513 (7)	0.0060 (5)	0.0253 (6)	0.0080 (5)
C2C	0.0421 (8)	0.0282 (6)	0.0487 (8)	0.0101 (6)	0.0235 (7)	0.0085 (6)
N3C	0.0419 (7)	0.0350 (6)	0.0569 (8)	0.0123 (5)	0.0269 (6)	0.0176 (6)
C4C	0.0497 (8)	0.0296 (7)	0.0545 (9)	0.0154 (6)	0.0283 (7)	0.0134 (6)
C5C	0.0585 (10)	0.0418 (8)	0.0637 (10)	0.0231 (8)	0.0288 (9)	0.0202 (8)
C6C	0.0801 (13)	0.0415 (9)	0.0617 (11)	0.0271 (9)	0.0353 (10)	0.0218 (8)
C7C	0.0781 (12)	0.0381 (8)	0.0626 (11)	0.0177 (8)	0.0421 (10)	0.0192 (8)
C8C	0.0581 (10)	0.0336 (7)	0.0591 (10)	0.0060 (7)	0.0336 (8)	0.0097 (7)
C9C	0.0500 (8)	0.0269 (6)	0.0520 (9)	0.0090 (6)	0.0278 (7)	0.0089 (6)
N10C	0.0409 (7)	0.0378 (6)	0.0537 (7)	0.0088 (5)	0.0235 (6)	0.0165 (6)
C10C	0.0460 (9)	0.0451 (9)	0.0572 (10)	0.0098 (7)	0.0215 (8)	0.0181 (7)
N11C	0.0428 (7)	0.0318 (6)	0.0579 (8)	0.0108 (5)	0.0278 (6)	0.0147 (6)
C12C	0.0486 (8)	0.0333 (7)	0.0563 (9)	0.0140 (6)	0.0279 (7)	0.0158 (7)
C13C	0.0530 (9)	0.0334 (7)	0.0633 (10)	0.0149 (7)	0.0349 (8)	0.0181 (7)
N14C	0.0601 (9)	0.0349 (6)	0.0644 (9)	0.0154 (6)	0.0378 (7)	0.0197 (6)
C14C	0.0726 (12)	0.0430 (9)	0.0648 (11)	0.0184 (8)	0.0378 (10)	0.0222 (8)
C15C	0.0588 (10)	0.0420 (9)	0.0774 (12)	0.0100 (8)	0.0433 (10)	0.0209 (8)
C16C	0.0489 (9)	0.0494 (9)	0.0805 (13)	0.0090 (8)	0.0366 (9)	0.0238 (9)
N17C	0.0468 (8)	0.0436 (7)	0.0705 (9)	0.0130 (6)	0.0323 (7)	0.0228 (7)
N1D	0.0497 (7)	0.0363 (6)	0.0413 (6)	0.0182 (5)	0.0178 (6)	0.0161 (5)
C2D	0.0440 (8)	0.0318 (7)	0.0418 (7)	0.0159 (6)	0.0183 (6)	0.0139 (6)
N3D	0.0420 (6)	0.0354 (6)	0.0439 (7)	0.0135 (5)	0.0179 (5)	0.0171 (5)
C4D	0.0541 (9)	0.0310 (7)	0.0448 (8)	0.0180 (6)	0.0241 (7)	0.0144 (6)
C5D	0.0574 (10)	0.0379 (8)	0.0574 (9)	0.0169 (7)	0.0292 (8)	0.0186 (7)
C6D	0.0730 (12)	0.0408 (8)	0.0581 (10)	0.0181 (8)	0.0390 (9)	0.0206 (8)
C7D	0.0852 (13)	0.0400 (8)	0.0485 (9)	0.0243 (8)	0.0361 (9)	0.0212 (7)
C8D	0.0711 (11)	0.0387 (8)	0.0433 (8)	0.0241 (8)	0.0244 (8)	0.0166 (7)
C9D	0.0569 (9)	0.0337 (7)	0.0424 (8)	0.0201 (7)	0.0231 (7)	0.0152 (6)
N10D	0.0381 (6)	0.0393 (6)	0.0412 (6)	0.0119 (5)	0.0132 (5)	0.0185 (5)
C10D	0.0393 (8)	0.0453 (8)	0.0480 (8)	0.0112 (6)	0.0143 (7)	0.0191 (7)
N11D	0.0395 (6)	0.0335 (6)	0.0401 (6)	0.0135 (5)	0.0134 (5)	0.0143 (5)
C12D	0.0366 (7)	0.0310 (6)	0.0425 (7)	0.0105 (5)	0.0152 (6)	0.0129 (6)
C13D	0.0392 (7)	0.0306 (6)	0.0400 (7)	0.0125 (5)	0.0179 (6)	0.0146 (6)
N14D	0.0359 (6)	0.0322 (6)	0.0419 (6)	0.0119 (5)	0.0169 (5)	0.0159 (5)
C14D	0.0386 (7)	0.0387 (7)	0.0534 (9)	0.0112 (6)	0.0200 (7)	0.0201 (7)
C15D	0.0400 (7)	0.0428 (8)	0.0427 (8)	0.0156 (6)	0.0162 (6)	0.0204 (6)
C16D	0.0374 (7)	0.0501 (9)	0.0451 (8)	0.0129 (6)	0.0152 (6)	0.0219 (7)
N17D	0.0369 (6)	0.0407 (6)	0.0430 (7)	0.0106 (5)	0.0166 (5)	0.0184 (5)
O1W	0.0844 (11)	0.1240 (14)	0.0628 (9)	0.0657 (10)	0.0238 (8)	0.0355 (9)
O2W	0.0435 (6)	0.0457 (6)	0.0804 (9)	0.0159 (5)	0.0200 (6)	0.0241 (6)
O3W	0.0498 (7)	0.0516 (7)	0.0680 (8)	0.0170 (5)	0.0280 (6)	0.0218 (6)
O4W	0.0419 (6)	0.0533 (7)	0.0596 (7)	0.0092 (5)	0.0178 (5)	0.0294 (6)
O5W	0.0424 (6)	0.0343 (5)	0.0878 (9)	0.0150 (5)	0.0277 (6)	0.0200 (6)

Geometric parameters (Å, º)

N1A—C2A	1.317 (2)	N3C—H3C	0.8800
N1A—C9A	1.398 (2)	C4C—C5C	1.377 (3)
C2A—N3A	1.359 (2)	C4C—C9C	1.405 (2)
C2A—N10A	1.3753 (19)	C5C—C6C	1.396 (2)
N3A—C4A	1.390 (2)	C5C—H5C	0.9500
N3A—H3A	0.8800	C6C—C7C	1.393 (3)
C4A—C5A	1.386 (3)	C6C—H6C	0.9500
C4A—C9A	1.400 (3)	C7C—C8C	1.384 (3)
C5A—C6A	1.389 (3)	C7C—H7C	0.9500
C5A—H5A	0.9500	C8C—C9C	1.397 (2)
C6A—C7A	1.385 (4)	C8C—H8C	0.9500
C6A—H6A	0.9500	N10C—N11C	1.3603 (17)
C7A—C8A	1.386 (3)	N10C—C10C	1.448 (2)
C7A—H7A	0.9500	C10C—H10G	0.9800
C8A—C9A	1.400 (3)	C10C—H10H	0.9800
C8A—H8A	0.9500	C10C—H10I	0.9800
N10A—N11A	1.354 (2)	N11C—C12C	1.287 (2)
N10A—C10A	1.450 (2)	C12C—C13C	1.462 (2)
C10A—H10A	0.9800	C12C—H12C	0.9500
C10A—H10B	0.9800	C13C—N17C	1.324 (2)
C10A—H10C	0.9800	C13C—N14C	1.361 (2)
N11A—C12A	1.2863 (19)	N14C—C15C	1.368 (2)
C12A—C13A	1.443 (2)	N14C—C14C	1.451 (3)
C12A—H12A	0.9500	C14C—H14G	0.9800
C13A—N17A	1.333 (2)	C14C—H14H	0.9800
C13A—N14A	1.3639 (18)	C14C—H14I	0.9800
N14A—C15A	1.369 (2)	C15C—C16C	1.361 (3)
N14A—C14A	1.462 (2)	C15C—H15C	0.9500
C14A—H14A	0.9800	C16C—N17C	1.372 (2)
C14A—H14B	0.9800	C16C—H16C	0.9500
C14A—H14C	0.9800	N1D—C2D	1.319 (2)
C15A—C16A	1.364 (2)	N1D—C9D	1.395 (2)
C15A—H15A	0.9500	C2D—N3D	1.3605 (19)
C16A—N17A	1.374 (2)	C2D—N10D	1.3734 (18)
C16A—H16A	0.9500	N3D—C4D	1.3915 (19)
N1B—C2B	1.3250 (19)	N3D—H3D	0.8800
N1B—C9B	1.398 (2)	C4D—C5D	1.388 (2)
C2B—N3B	1.359 (2)	C4D—C9D	1.400 (2)
C2B—N10B	1.365 (2)	C5D—C6D	1.385 (2)
N3B—C4B	1.3879 (18)	C5D—H5D	0.9500
N3B—H3B	0.8800	C6D—C7D	1.389 (3)
C4B—C5B	1.381 (2)	C6D—H6D	0.9500
C4B—C9B	1.408 (2)	C7D—C8D	1.390 (3)
C5B—C6B	1.394 (2)	C7D—H7D	0.9500
C5B—H5B	0.9500	C8D—C9D	1.397 (2)
C6B—C7B	1.397 (2)	C8D—H8D	0.9500
C6B—H6B	0.9500	N10D—N11D	1.3556 (17)
C7B—C8B	1.388 (2)	N10D—C10D	1.4477 (19)
C7B—H7B	0.9500	C10D—H10J	0.9800
C8B—C9B	1.392 (2)	C10D—H10K	0.9800
C8B—H8B	0.9500	C10D—H10L	0.9800
N10B—N11B	1.3624 (18)	N11D—C12D	1.2832 (18)
N10B—C10B	1.447 (2)	C12D—C13D	1.437 (2)
C10B—H10D	0.9800	C12D—H12D	0.9500
C10B—H10E	0.9800	C13D—N17D	1.3317 (19)
C10B—H10F	0.9800	C13D—N14D	1.3669 (17)
N11B—C12B	1.283 (2)	N14D—C15D	1.362 (2)
C12B—C13B	1.452 (2)	N14D—C14D	1.4580 (18)
C12B—H12B	0.9500	C14D—H14J	0.9800
C13B—N17B	1.330 (2)	C14D—H14K	0.9800
C13B—N14B	1.359 (2)	C14D—H14L	0.9800
N14B—C15B	1.365 (2)	C15D—C16D	1.363 (2)
N14B—C14B	1.457 (2)	C15D—H15D	0.9500
C14B—H14D	0.9800	C16D—N17D	1.376 (2)
C14B—H14E	0.9800	C16D—H16D	0.9500
C14B—H14F	0.9800	O1W—H1WA	0.8215
C15B—C16B	1.364 (3)	O1W—H1WB	1.0606
C15B—H15B	0.9500	O2W—H2WA	0.8501
C16B—N17B	1.375 (2)	O2W—H2WB	0.9702
C16B—H16B	0.9500	O3W—H3WA	0.8500
N1C—C2C	1.3285 (18)	O3W—H3WB	0.8501
N1C—C9C	1.398 (2)	O4W—H4WA	0.9715
C2C—N3C	1.351 (2)	O4W—H4WB	0.8580
C2C—N10C	1.374 (2)	O5W—H5WA	0.8398
N3C—C4C	1.3882 (19)	O5W—H5WB	0.8301
C2A—N1A—C9A	103.78 (16)	N3C—C2C—N10C	121.28 (13)
N1A—C2A—N3A	114.56 (14)	C2C—N3C—C4C	106.68 (13)
N1A—C2A—N10A	123.71 (16)	C2C—N3C—H3C	126.7
N3A—C2A—N10A	121.71 (16)	C4C—N3C—H3C	126.7
C2A—N3A—C4A	106.10 (16)	C5C—C4C—N3C	132.55 (15)
C2A—N3A—H3A	127.0	C5C—C4C—C9C	122.48 (15)
C4A—N3A—H3A	127.0	N3C—C4C—C9C	104.96 (15)
C5A—C4A—N3A	132.7 (2)	C4C—C5C—C6C	117.20 (18)
C5A—C4A—C9A	121.98 (18)	C4C—C5C—H5C	121.4
N3A—C4A—C9A	105.29 (15)	C6C—C5C—H5C	121.4
C4A—C5A—C6A	116.7 (2)	C7C—C6C—C5C	121.11 (19)
C4A—C5A—H5A	121.6	C7C—C6C—H6C	119.4
C6A—C5A—H5A	121.6	C5C—C6C—H6C	119.4
C7A—C6A—C5A	121.8 (2)	C8C—C7C—C6C	121.40 (16)
C7A—C6A—H6A	119.1	C8C—C7C—H7C	119.3
C5A—C6A—H6A	119.1	C6C—C7C—H7C	119.3
C6A—C7A—C8A	121.8 (2)	C7C—C8C—C9C	118.23 (17)
C6A—C7A—H7A	119.1	C7C—C8C—H8C	120.9
C8A—C7A—H7A	119.1	C9C—C8C—H8C	120.9
C7A—C8A—C9A	117.0 (3)	C8C—C9C—N1C	129.92 (16)
C7A—C8A—H8A	121.5	C8C—C9C—C4C	119.58 (17)
C9A—C8A—H8A	121.5	N1C—C9C—C4C	110.50 (13)
N1A—C9A—C4A	110.27 (16)	N11C—N10C—C2C	113.81 (14)
N1A—C9A—C8A	129.0 (2)	N11C—N10C—C10C	123.92 (13)
C4A—C9A—C8A	120.69 (19)	C2C—N10C—C10C	122.27 (13)
N11A—N10A—C2A	115.08 (14)	N10C—C10C—H10G	109.5
N11A—N10A—C10A	123.70 (12)	N10C—C10C—H10H	109.5
C2A—N10A—C10A	121.21 (15)	H10G—C10C—H10H	109.5
N10A—C10A—H10A	109.5	N10C—C10C—H10I	109.5
N10A—C10A—H10B	109.5	H10G—C10C—H10I	109.5
H10A—C10A—H10B	109.5	H10H—C10C—H10I	109.5
N10A—C10A—H10C	109.5	C12C—N11C—N10C	120.35 (15)
H10A—C10A—H10C	109.5	N11C—C12C—C13C	115.28 (16)
H10B—C10A—H10C	109.5	N11C—C12C—H12C	122.4
C12A—N11A—N10A	119.16 (13)	C13C—C12C—H12C	122.4
N11A—C12A—C13A	118.48 (14)	N17C—C13C—N14C	111.55 (15)
N11A—C12A—H12A	120.8	N17C—C13C—C12C	124.43 (15)
C13A—C12A—H12A	120.8	N14C—C13C—C12C	124.02 (17)
N17A—C13A—N14A	111.08 (14)	C13C—N14C—C15C	106.53 (16)
N17A—C13A—C12A	126.33 (13)	C13C—N14C—C14C	128.00 (15)
N14A—C13A—C12A	122.54 (14)	C15C—N14C—C14C	125.34 (15)
C13A—N14A—C15A	107.26 (13)	N14C—C14C—H14G	109.5
C13A—N14A—C14A	126.95 (14)	N14C—C14C—H14H	109.5
C15A—N14A—C14A	125.78 (13)	H14G—C14C—H14H	109.5
N14A—C14A—H14A	109.5	N14C—C14C—H14I	109.5
N14A—C14A—H14B	109.5	H14G—C14C—H14I	109.5
H14A—C14A—H14B	109.5	H14H—C14C—H14I	109.5
N14A—C14A—H14C	109.5	C16C—C15C—N14C	106.55 (15)
H14A—C14A—H14C	109.5	C16C—C15C—H15C	126.7
H14B—C14A—H14C	109.5	N14C—C15C—H15C	126.7
C16A—C15A—N14A	105.98 (14)	C15C—C16C—N17C	110.05 (18)
C16A—C15A—H15A	127.0	C15C—C16C—H16C	125.0
N14A—C15A—H15A	127.0	N17C—C16C—H16C	125.0
C15A—C16A—N17A	110.56 (15)	C13C—N17C—C16C	105.31 (16)
C15A—C16A—H16A	124.7	C2D—N1D—C9D	103.61 (13)
N17A—C16A—H16A	124.7	N1D—C2D—N3D	114.82 (13)
C13A—N17A—C16A	105.12 (13)	N1D—C2D—N10D	124.58 (14)
C2B—N1B—C9B	103.44 (12)	N3D—C2D—N10D	120.60 (13)
N1B—C2B—N3B	114.71 (13)	C2D—N3D—C4D	105.70 (13)
N1B—C2B—N10B	124.31 (14)	C2D—N3D—H3D	127.1
N3B—C2B—N10B	120.97 (13)	C4D—N3D—H3D	127.1
C2B—N3B—C4B	106.24 (12)	C5D—C4D—N3D	131.83 (16)
C2B—N3B—H3B	126.9	C5D—C4D—C9D	122.71 (15)
C4B—N3B—H3B	126.9	N3D—C4D—C9D	105.46 (13)
C5B—C4B—N3B	132.40 (13)	C6D—C5D—C4D	116.41 (18)
C5B—C4B—C9B	122.38 (13)	C6D—C5D—H5D	121.8
N3B—C4B—C9B	105.22 (13)	C4D—C5D—H5D	121.8
C4B—C5B—C6B	117.05 (14)	C5D—C6D—C7D	121.78 (16)
C4B—C5B—H5B	121.5	C5D—C6D—H6D	119.1
C6B—C5B—H5B	121.5	C7D—C6D—H6D	119.1
C5B—C6B—C7B	121.28 (15)	C6D—C7D—C8D	121.77 (16)
C5B—C6B—H6B	119.4	C6D—C7D—H7D	119.1
C7B—C6B—H6B	119.4	C8D—C7D—H7D	119.1
C8B—C7B—C6B	121.28 (14)	C7D—C8D—C9D	117.27 (17)
C8B—C7B—H7B	119.4	C7D—C8D—H8D	121.4
C6B—C7B—H7B	119.4	C9D—C8D—H8D	121.4
C7B—C8B—C9B	118.12 (14)	N1D—C9D—C8D	129.54 (16)
C7B—C8B—H8B	120.9	N1D—C9D—C4D	110.42 (13)
C9B—C8B—H8B	120.9	C8D—C9D—C4D	120.04 (15)
C8B—C9B—N1B	129.71 (14)	N11D—N10D—C2D	114.96 (12)
C8B—C9B—C4B	119.89 (14)	N11D—N10D—C10D	123.91 (12)
N1B—C9B—C4B	110.40 (12)	C2D—N10D—C10D	120.79 (13)
N11B—N10B—C2B	114.33 (13)	N10D—C10D—H10J	109.5
N11B—N10B—C10B	123.33 (13)	N10D—C10D—H10K	109.5
C2B—N10B—C10B	122.09 (13)	H10J—C10D—H10K	109.5
N10B—C10B—H10D	109.5	N10D—C10D—H10L	109.5
N10B—C10B—H10E	109.5	H10J—C10D—H10L	109.5
H10D—C10B—H10E	109.5	H10K—C10D—H10L	109.5
N10B—C10B—H10F	109.5	C12D—N11D—N10D	118.81 (13)
H10D—C10B—H10F	109.5	N11D—C12D—C13D	118.92 (13)
H10E—C10B—H10F	109.5	N11D—C12D—H12D	120.5
C12B—N11B—N10B	119.05 (14)	C13D—C12D—H12D	120.5
N11B—C12B—C13B	117.95 (16)	N17D—C13D—N14D	110.93 (13)
N11B—C12B—H12B	121.0	N17D—C13D—C12D	126.99 (12)
C13B—C12B—H12B	121.0	N14D—C13D—C12D	122.06 (13)
N17B—C13B—N14B	111.38 (14)	C15D—N14D—C13D	107.45 (12)
N17B—C13B—C12B	125.96 (15)	C15D—N14D—C14D	125.57 (12)
N14B—C13B—C12B	122.66 (16)	C13D—N14D—C14D	126.98 (13)
C13B—N14B—C15B	106.99 (15)	N14D—C14D—H14J	109.5
C13B—N14B—C14B	126.85 (14)	N14D—C14D—H14K	109.5
C15B—N14B—C14B	126.15 (14)	H14J—C14D—H14K	109.5
N14B—C14B—H14D	109.5	N14D—C14D—H14L	109.5
N14B—C14B—H14E	109.5	H14J—C14D—H14L	109.5
H14D—C14B—H14E	109.5	H14K—C14D—H14L	109.5
N14B—C14B—H14F	109.5	N14D—C15D—C16D	106.04 (13)
H14D—C14B—H14F	109.5	N14D—C15D—H15D	127.0
H14E—C14B—H14F	109.5	C16D—C15D—H15D	127.0
C16B—C15B—N14B	106.48 (15)	C15D—C16D—N17D	110.57 (14)
C16B—C15B—H15B	126.8	C15D—C16D—H16D	124.7
N14B—C15B—H15B	126.8	N17D—C16D—H16D	124.7
C15B—C16B—N17B	109.95 (17)	C13D—N17D—C16D	105.01 (12)
C15B—C16B—H16B	125.0	H1WA—O1W—H1WB	111.3
N17B—C16B—H16B	125.0	H2WA—O2W—H2WB	102.5
C13B—N17B—C16B	105.20 (15)	H3WA—O3W—H3WB	104.5
C2C—N1C—C9C	103.35 (14)	H4WA—O4W—H4WB	104.9
N1C—C2C—N3C	114.51 (14)	H5WA—O5W—H5WB	102.2
N1C—C2C—N10C	124.21 (15)
C9A—N1A—C2A—N3A	0.13 (17)	C9C—N1C—C2C—N3C	−0.70 (16)
C9A—N1A—C2A—N10A	178.88 (13)	C9C—N1C—C2C—N10C	179.37 (13)
N1A—C2A—N3A—C4A	−0.10 (17)	N1C—C2C—N3C—C4C	0.17 (17)
N10A—C2A—N3A—C4A	−178.88 (13)	N10C—C2C—N3C—C4C	−179.90 (13)
C2A—N3A—C4A—C5A	−179.95 (17)	C2C—N3C—C4C—C5C	179.59 (16)
C2A—N3A—C4A—C9A	0.03 (16)	C2C—N3C—C4C—C9C	0.44 (15)
N3A—C4A—C5A—C6A	−179.32 (16)	N3C—C4C—C5C—C6C	−178.06 (15)
C9A—C4A—C5A—C6A	0.7 (2)	C9C—C4C—C5C—C6C	1.0 (2)
C4A—C5A—C6A—C7A	−0.5 (3)	C4C—C5C—C6C—C7C	−0.4 (2)
C5A—C6A—C7A—C8A	0.1 (3)	C5C—C6C—C7C—C8C	−0.2 (3)
C6A—C7A—C8A—C9A	0.2 (3)	C6C—C7C—C8C—C9C	0.1 (2)
C2A—N1A—C9A—C4A	−0.10 (17)	C7C—C8C—C9C—N1C	179.37 (15)
C2A—N1A—C9A—C8A	−179.59 (17)	C7C—C8C—C9C—C4C	0.4 (2)
C5A—C4A—C9A—N1A	−179.97 (15)	C2C—N1C—C9C—C8C	−178.03 (15)
N3A—C4A—C9A—N1A	0.05 (17)	C2C—N1C—C9C—C4C	0.97 (16)
C5A—C4A—C9A—C8A	−0.4 (2)	C5C—C4C—C9C—C8C	−1.0 (2)
N3A—C4A—C9A—C8A	179.58 (14)	N3C—C4C—C9C—C8C	178.23 (13)
C7A—C8A—C9A—N1A	179.40 (16)	C5C—C4C—C9C—N1C	179.86 (14)
C7A—C8A—C9A—C4A	0.0 (2)	N3C—C4C—C9C—N1C	−0.89 (16)
N1A—C2A—N10A—N11A	179.94 (13)	N1C—C2C—N10C—N11C	−178.11 (13)
N3A—C2A—N10A—N11A	−1.39 (19)	N3C—C2C—N10C—N11C	1.96 (19)
N1A—C2A—N10A—C10A	−0.5 (2)	N1C—C2C—N10C—C10C	2.2 (2)
N3A—C2A—N10A—C10A	178.18 (13)	N3C—C2C—N10C—C10C	−177.72 (14)
C2A—N10A—N11A—C12A	179.05 (12)	C2C—N10C—N11C—C12C	−179.37 (13)
C10A—N10A—N11A—C12A	−0.5 (2)	C10C—N10C—N11C—C12C	0.3 (2)
N10A—N11A—C12A—C13A	177.81 (12)	N10C—N11C—C12C—C13C	−179.06 (12)
N11A—C12A—C13A—N17A	−2.7 (2)	N11C—C12C—C13C—N17C	−1.9 (2)
N11A—C12A—C13A—N14A	179.99 (12)	N11C—C12C—C13C—N14C	177.93 (14)
N17A—C13A—N14A—C15A	−0.67 (15)	N17C—C13C—N14C—C15C	−0.56 (18)
C12A—C13A—N14A—C15A	176.96 (12)	C12C—C13C—N14C—C15C	179.57 (14)
N17A—C13A—N14A—C14A	178.36 (13)	N17C—C13C—N14C—C14C	175.50 (15)
C12A—C13A—N14A—C14A	−4.0 (2)	C12C—C13C—N14C—C14C	−4.4 (3)
C13A—N14A—C15A—C16A	0.48 (15)	C13C—N14C—C15C—C16C	0.56 (19)
C14A—N14A—C15A—C16A	−178.57 (13)	C14C—N14C—C15C—C16C	−175.63 (16)
N14A—C15A—C16A—N17A	−0.15 (16)	N14C—C15C—C16C—N17C	−0.4 (2)
N14A—C13A—N17A—C16A	0.57 (15)	N14C—C13C—N17C—C16C	0.32 (19)
C12A—C13A—N17A—C16A	−176.95 (13)	C12C—C13C—N17C—C16C	−179.81 (15)
C15A—C16A—N17A—C13A	−0.25 (16)	C15C—C16C—N17C—C13C	0.0 (2)
C9B—N1B—C2B—N3B	−0.10 (16)	C9D—N1D—C2D—N3D	−0.35 (16)
C9B—N1B—C2B—N10B	−179.47 (13)	C9D—N1D—C2D—N10D	179.53 (13)
N1B—C2B—N3B—C4B	0.18 (16)	N1D—C2D—N3D—C4D	0.69 (16)
N10B—C2B—N3B—C4B	179.58 (12)	N10D—C2D—N3D—C4D	−179.20 (12)
C2B—N3B—C4B—C5B	179.54 (14)	C2D—N3D—C4D—C5D	179.21 (15)
C2B—N3B—C4B—C9B	−0.18 (14)	C2D—N3D—C4D—C9D	−0.69 (15)
N3B—C4B—C5B—C6B	−179.12 (14)	N3D—C4D—C5D—C6D	179.11 (15)
C9B—C4B—C5B—C6B	0.6 (2)	C9D—C4D—C5D—C6D	−1.0 (2)
C4B—C5B—C6B—C7B	−0.3 (2)	C4D—C5D—C6D—C7D	0.0 (2)
C5B—C6B—C7B—C8B	−0.5 (2)	C5D—C6D—C7D—C8D	0.8 (3)
C6B—C7B—C8B—C9B	0.9 (2)	C6D—C7D—C8D—C9D	−0.5 (2)
C7B—C8B—C9B—N1B	178.78 (14)	C2D—N1D—C9D—C8D	179.11 (15)
C7B—C8B—C9B—C4B	−0.6 (2)	C2D—N1D—C9D—C4D	−0.13 (16)
C2B—N1B—C9B—C8B	−179.44 (15)	C7D—C8D—C9D—N1D	−179.68 (14)
C2B—N1B—C9B—C4B	−0.03 (15)	C7D—C8D—C9D—C4D	−0.5 (2)
C5B—C4B—C9B—C8B	−0.2 (2)	C5D—C4D—C9D—N1D	−179.39 (13)
N3B—C4B—C9B—C8B	179.61 (12)	N3D—C4D—C9D—N1D	0.52 (16)
C5B—C4B—C9B—N1B	−179.63 (12)	C5D—C4D—C9D—C8D	1.3 (2)
N3B—C4B—C9B—N1B	0.13 (15)	N3D—C4D—C9D—C8D	−178.80 (13)
N1B—C2B—N10B—N11B	−175.56 (13)	N1D—C2D—N10D—N11D	−179.96 (13)
N3B—C2B—N10B—N11B	5.11 (19)	N3D—C2D—N10D—N11D	−0.09 (19)
N1B—C2B—N10B—C10B	−1.1 (2)	N1D—C2D—N10D—C10D	−6.3 (2)
N3B—C2B—N10B—C10B	179.51 (14)	N3D—C2D—N10D—C10D	173.53 (13)
C2B—N10B—N11B—C12B	175.37 (13)	C2D—N10D—N11D—C12D	175.60 (12)
C10B—N10B—N11B—C12B	1.0 (2)	C10D—N10D—N11D—C12D	2.2 (2)
N10B—N11B—C12B—C13B	179.75 (12)	N10D—N11D—C12D—C13D	178.58 (12)
N11B—C12B—C13B—N17B	−2.3 (2)	N11D—C12D—C13D—N17D	−0.4 (2)
N11B—C12B—C13B—N14B	178.10 (13)	N11D—C12D—C13D—N14D	−178.31 (12)
N17B—C13B—N14B—C15B	−0.30 (17)	N17D—C13D—N14D—C15D	−0.39 (16)
C12B—C13B—N14B—C15B	179.38 (13)	C12D—C13D—N14D—C15D	177.77 (13)
N17B—C13B—N14B—C14B	178.65 (14)	N17D—C13D—N14D—C14D	−179.85 (13)
C12B—C13B—N14B—C14B	−1.7 (2)	C12D—C13D—N14D—C14D	−1.7 (2)
C13B—N14B—C15B—C16B	0.18 (17)	C13D—N14D—C15D—C16D	0.18 (16)
C14B—N14B—C15B—C16B	−178.78 (15)	C14D—N14D—C15D—C16D	179.65 (13)
N14B—C15B—C16B—N17B	−0.01 (19)	N14D—C15D—C16D—N17D	0.08 (18)
N14B—C13B—N17B—C16B	0.29 (17)	N14D—C13D—N17D—C16D	0.43 (16)
C12B—C13B—N17B—C16B	−179.38 (14)	C12D—C13D—N17D—C16D	−177.63 (14)
C15B—C16B—N17B—C13B	−0.17 (18)	C15D—C16D—N17D—C13D	−0.31 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O5W	0.88	2.04	2.918 (2)	174
N3B—H3B···O2W	0.88	2.00	2.8786 (17)	176
N3C—H3C···O3W	0.88	1.96	2.8309 (17)	171
C10C—H10G···O1W^i	0.98	2.60	3.542 (2)	160
N3D—H3D···O4W	0.88	2.10	2.9787 (18)	176
O1W—H1WA···N1D^ii	0.82	2.09	2.903 (2)	170
O2W—H2WA···O5W	0.85	2.10	2.8738 (17)	151
O2W—H2WB···N17B	0.97	1.89	2.8558 (19)	172
O3W—H3WA···O4W	0.85	2.07	2.9076 (17)	168
O3W—H3WB···N17C	0.85	1.95	2.792 (2)	172
O4W—H4WA···N17D	0.97	1.93	2.8789 (16)	164
O4W—H4WB···N1C^iii	0.86	2.08	2.9361 (18)	174
O5W—H5WA···N1B^iv	0.84	2.09	2.9107 (16)	166
O5W—H5WB···N17A	0.83	2.08	2.9012 (17)	168

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

5-{(1E)-[2-(1H-1,3-Benzodiazol-2-yl)-2-methylhydrazinylidene]methyl}-1H-imidazol-3-ium trifluoromethanesulfonate monohydrate (5)

Crystal data

C12H13N6^+·CF3O3S^−·H2O	F(000) = 840
Mr = 408.37	Dx = 1.500 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.9818 (5) Å	Cell parameters from 2227 reflections
b = 9.5704 (5) Å	θ = 3.8–25.6°
c = 21.1278 (12) Å	µ = 0.24 mm^−1
β = 95.383 (5)°	T = 295 K
V = 1808.12 (17) Å^3	Prism, colourless
Z = 4	0.4 × 0.25 × 0.2 mm

Data collection

Rigaku Xcalibur Eos diffractometer	3603 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2782 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.0°, θmin = 3.2°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→12
Tmin = 0.936, Tmax = 1.000	l = −24→26
7345 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.0748P)^2 + 1.3789P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3603 reflections	Δρmax = 0.56 e Å^−3
293 parameters	Δρmin = −0.38 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.8811 (3)	0.5516 (3)	0.41351 (11)	0.0539 (6)
C2	0.8038 (3)	0.5451 (3)	0.46349 (12)	0.0459 (6)
N3	0.7686 (3)	0.4143 (3)	0.48062 (12)	0.0490 (6)
H3	0.725 (3)	0.391 (3)	0.5096 (14)	0.046 (8)*
C4	0.8295 (3)	0.3244 (3)	0.43831 (13)	0.0504 (7)
C5	0.8274 (4)	0.1801 (4)	0.43244 (17)	0.0651 (9)
H5	0.777 (4)	0.122 (4)	0.4631 (18)	0.083 (12)*
C6	0.9011 (5)	0.1249 (4)	0.3836 (2)	0.0761 (10)
H6	0.895 (4)	0.030 (5)	0.381 (2)	0.098 (14)*
C7	0.9746 (4)	0.2101 (5)	0.34283 (19)	0.0761 (11)
H7	1.028 (4)	0.166 (4)	0.3117 (18)	0.078 (11)*
C8	0.9750 (4)	0.3534 (4)	0.34858 (17)	0.0682 (9)
H8	1.025 (4)	0.414 (4)	0.3194 (18)	0.078 (11)*
C9	0.9003 (3)	0.4112 (3)	0.39720 (13)	0.0530 (7)
N10	0.7609 (3)	0.6599 (2)	0.49611 (11)	0.0512 (6)
C10	0.8070 (4)	0.8006 (3)	0.48028 (15)	0.0615 (8)
H10A	0.7209	0.8535	0.4641	0.092*
H10B	0.8768	0.7957	0.4486	0.092*
H10C	0.8536	0.8452	0.5177	0.092*
N11	0.6765 (3)	0.6323 (2)	0.54464 (10)	0.0464 (5)
C12	0.6314 (3)	0.7334 (3)	0.57690 (14)	0.0497 (7)
H12	0.656 (3)	0.820 (3)	0.5692 (14)	0.054 (8)*
C13	0.5439 (3)	0.7007 (3)	0.62923 (13)	0.0452 (6)
N14	0.5057 (3)	0.5664 (3)	0.64411 (12)	0.0491 (6)
H14	0.527 (4)	0.501 (4)	0.6236 (17)	0.077 (12)*
C15	0.4250 (3)	0.5691 (3)	0.69324 (14)	0.0521 (7)
H15	0.381 (3)	0.492 (3)	0.7137 (14)	0.060 (9)*
N16	0.4099 (3)	0.6999 (3)	0.71078 (12)	0.0531 (6)
H16	0.353 (4)	0.729 (4)	0.7424 (17)	0.068 (10)*
C17	0.4832 (3)	0.7837 (3)	0.67137 (14)	0.0534 (7)
H17	0.483 (3)	0.883 (4)	0.6767 (15)	0.064 (9)*
C1A	0.7593 (5)	0.1925 (5)	0.6715 (2)	0.0921 (13)
F1A	0.7374 (6)	0.2944 (4)	0.71194 (18)	0.1793 (18)
F2A	0.8792 (3)	0.2204 (5)	0.6460 (3)	0.203 (2)
F3A	0.7821 (4)	0.0780 (4)	0.70420 (18)	0.1551 (14)
S1A	0.59941 (9)	0.17915 (7)	0.61386 (4)	0.0550 (3)
O1A	0.6403 (5)	0.0741 (3)	0.57192 (16)	0.1230 (13)
O2A	0.4833 (3)	0.1407 (4)	0.65088 (18)	0.1133 (12)
O3A	0.5863 (3)	0.3149 (2)	0.58571 (11)	0.0691 (7)
O1W	0.2707 (3)	0.7781 (3)	0.81181 (12)	0.0745 (7)
H1W1	0.310 (5)	0.824 (5)	0.843 (2)	0.120 (18)*
H1W2	0.178 (5)	0.743 (5)	0.8232 (19)	0.096 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0561 (14)	0.0583 (15)	0.0485 (13)	−0.0001 (11)	0.0119 (11)	0.0012 (11)
C2	0.0481 (14)	0.0464 (15)	0.0429 (14)	0.0020 (12)	0.0025 (11)	0.0014 (11)
N3	0.0600 (14)	0.0461 (13)	0.0419 (13)	0.0053 (11)	0.0107 (11)	0.0043 (10)
C4	0.0532 (16)	0.0530 (16)	0.0446 (14)	0.0112 (13)	0.0034 (12)	0.0009 (12)
C5	0.081 (2)	0.0513 (18)	0.0631 (19)	0.0162 (16)	0.0071 (17)	−0.0040 (15)
C6	0.088 (3)	0.060 (2)	0.080 (2)	0.021 (2)	0.006 (2)	−0.0157 (19)
C7	0.073 (2)	0.085 (3)	0.071 (2)	0.023 (2)	0.0118 (18)	−0.020 (2)
C8	0.061 (2)	0.086 (3)	0.0595 (19)	0.0084 (18)	0.0153 (16)	−0.0058 (18)
C9	0.0470 (15)	0.0630 (18)	0.0488 (15)	0.0080 (13)	0.0031 (12)	−0.0021 (13)
N10	0.0647 (15)	0.0418 (12)	0.0487 (13)	−0.0028 (11)	0.0142 (11)	0.0013 (10)
C10	0.077 (2)	0.0484 (17)	0.0599 (18)	−0.0154 (15)	0.0120 (16)	−0.0013 (14)
N11	0.0546 (13)	0.0422 (12)	0.0431 (11)	0.0005 (10)	0.0080 (10)	0.0009 (10)
C12	0.0614 (17)	0.0370 (15)	0.0510 (16)	−0.0009 (13)	0.0067 (13)	−0.0020 (12)
C13	0.0520 (15)	0.0365 (13)	0.0467 (14)	0.0024 (11)	0.0025 (11)	−0.0032 (11)
N14	0.0587 (14)	0.0394 (13)	0.0495 (13)	0.0022 (11)	0.0061 (11)	−0.0061 (11)
C15	0.0589 (17)	0.0487 (16)	0.0492 (16)	−0.0014 (13)	0.0073 (13)	−0.0021 (13)
N16	0.0560 (14)	0.0540 (15)	0.0502 (13)	0.0013 (11)	0.0101 (11)	−0.0105 (11)
C17	0.0640 (18)	0.0407 (15)	0.0560 (17)	0.0014 (13)	0.0081 (14)	−0.0083 (13)
C1A	0.074 (3)	0.093 (3)	0.105 (3)	0.004 (2)	−0.009 (2)	0.015 (3)
F1A	0.234 (5)	0.155 (3)	0.132 (3)	0.008 (3)	−0.075 (3)	−0.045 (2)
F2A	0.0641 (17)	0.268 (5)	0.273 (5)	−0.040 (2)	0.001 (2)	0.096 (4)
F3A	0.133 (2)	0.145 (3)	0.176 (3)	0.022 (2)	−0.047 (2)	0.073 (2)
S1A	0.0621 (5)	0.0394 (4)	0.0640 (5)	0.0011 (3)	0.0082 (3)	0.0052 (3)
O1A	0.211 (4)	0.0481 (15)	0.109 (2)	0.0202 (19)	0.010 (2)	−0.0251 (15)
O2A	0.0668 (16)	0.124 (3)	0.153 (3)	0.0063 (16)	0.0326 (18)	0.064 (2)
O3A	0.1047 (18)	0.0394 (11)	0.0649 (13)	0.0120 (11)	0.0166 (12)	0.0039 (10)
O1W	0.0820 (18)	0.0836 (18)	0.0609 (14)	−0.0136 (14)	0.0227 (13)	−0.0227 (13)

Geometric parameters (Å, º)

N1—C2	1.319 (3)	N11—C12	1.272 (3)
N1—C9	1.402 (4)	C12—C13	1.450 (4)
C2—N3	1.349 (4)	C12—H12	0.88 (3)
C2—N10	1.371 (3)	C13—C17	1.346 (4)
N3—C4	1.390 (4)	C13—N14	1.374 (3)
N3—H3	0.79 (3)	N14—C15	1.321 (4)
C4—C5	1.386 (4)	N14—H14	0.79 (4)
C4—C9	1.398 (4)	C15—N16	1.316 (4)
C5—C6	1.383 (5)	C15—H15	0.96 (3)
C5—H5	0.99 (4)	N16—C17	1.369 (4)
C6—C7	1.395 (6)	N16—H16	0.92 (4)
C6—H6	0.91 (4)	C17—H17	0.96 (3)
C7—C8	1.376 (5)	C1A—F2A	1.276 (6)
C7—H7	0.95 (4)	C1A—F3A	1.301 (5)
C8—C9	1.393 (4)	C1A—F1A	1.324 (6)
C8—H8	0.99 (4)	C1A—S1A	1.798 (4)
N10—N11	1.357 (3)	S1A—O2A	1.410 (3)
N10—C10	1.456 (4)	S1A—O1A	1.411 (3)
C10—H10A	0.9600	S1A—O3A	1.429 (2)
C10—H10B	0.9600	O1W—H1W1	0.85 (5)
C10—H10C	0.9600	O1W—H1W2	0.95 (5)
C2—N1—C9	103.8 (2)	H10B—C10—H10C	109.5
N1—C2—N3	114.4 (2)	C12—N11—N10	119.0 (2)
N1—C2—N10	124.0 (3)	N11—C12—C13	117.8 (3)
N3—C2—N10	121.7 (2)	N11—C12—H12	122 (2)
C2—N3—C4	106.6 (2)	C13—C12—H12	120 (2)
C2—N3—H3	128 (2)	C17—C13—N14	106.0 (3)
C4—N3—H3	125 (2)	C17—C13—C12	131.2 (3)
C5—C4—N3	132.2 (3)	N14—C13—C12	122.8 (2)
C5—C4—C9	122.7 (3)	C15—N14—C13	109.2 (2)
N3—C4—C9	105.1 (3)	C15—N14—H14	129 (3)
C6—C5—C4	116.4 (4)	C13—N14—H14	122 (3)
C6—C5—H5	124 (2)	N16—C15—N14	108.6 (3)
C4—C5—H5	120 (2)	N16—C15—H15	123.1 (19)
C5—C6—C7	121.6 (4)	N14—C15—H15	128.4 (19)
C5—C6—H6	113 (3)	C15—N16—C17	108.5 (3)
C7—C6—H6	125 (3)	C15—N16—H16	125 (2)
C8—C7—C6	121.7 (4)	C17—N16—H16	126 (2)
C8—C7—H7	120 (2)	C13—C17—N16	107.7 (3)
C6—C7—H7	118 (2)	C13—C17—H17	132.2 (19)
C7—C8—C9	117.6 (4)	N16—C17—H17	120.1 (19)
C7—C8—H8	122 (2)	F2A—C1A—F3A	107.6 (4)
C9—C8—H8	120 (2)	F2A—C1A—F1A	107.5 (5)
C8—C9—C4	120.0 (3)	F3A—C1A—F1A	107.6 (5)
C8—C9—N1	129.9 (3)	F2A—C1A—S1A	112.4 (4)
C4—C9—N1	110.1 (2)	F3A—C1A—S1A	112.1 (3)
N11—N10—C2	115.3 (2)	F1A—C1A—S1A	109.4 (3)
N11—N10—C10	123.0 (2)	O2A—S1A—O1A	114.3 (2)
C2—N10—C10	121.7 (2)	O2A—S1A—O3A	115.59 (17)
N10—C10—H10A	109.5	O1A—S1A—O3A	113.71 (17)
N10—C10—H10B	109.5	O2A—S1A—C1A	103.2 (2)
H10A—C10—H10B	109.5	O1A—S1A—C1A	103.7 (2)
N10—C10—H10C	109.5	O3A—S1A—C1A	104.28 (19)
H10A—C10—H10C	109.5	H1W1—O1W—H1W2	107 (4)

2-{(2E)-1-Methyl-2-[(1H-imidazol-3-ium-2-yl)methylidene]hydrazinyl}pyridinium bis(trifluoromethanesulfonate) (6)

Crystal data

C10H13N5^2+·2CF3O3S^−	F(000) = 1016
Mr = 501.39	Dx = 1.732 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.2524 (5) Å	Cell parameters from 4019 reflections
b = 14.0242 (5) Å	θ = 3.1–27.8°
c = 11.4488 (5) Å	µ = 0.38 mm^−1
β = 102.259 (4)°	T = 295 K
V = 1922.39 (14) Å^3	Prism, colourless
Z = 4	0.45 × 0.2 × 0.15 mm

Data collection

Rigaku Xcalibur Eos diffractometer	3929 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.5°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −17→17
Tmin = 0.955, Tmax = 1.000	l = −13→14
19010 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 1.1585P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
3929 reflections	Δρmax = 0.54 e Å^−3
281 parameters	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.20195 (18)	0.84745 (15)	0.5313 (2)	0.0467 (5)
H1	0.2374	0.8141	0.4884	0.056*
C2	0.2058 (3)	0.9428 (2)	0.5228 (3)	0.0572 (7)
H2	0.2451	0.9708	0.4705	0.069*
C3	0.1528 (3)	0.9986 (2)	0.5898 (3)	0.0652 (9)
H3	0.1548	1.0648	0.5848	0.078*
C4	0.0956 (3)	0.9533 (2)	0.6662 (3)	0.0654 (9)
H4	0.0589	0.9903	0.7133	0.078*
C5	0.0912 (2)	0.8571 (2)	0.6748 (3)	0.0570 (8)
H5	0.0527	0.8287	0.7274	0.068*
C6	0.1456 (2)	0.80102 (19)	0.6032 (2)	0.0427 (6)
N7	0.14560 (17)	0.70476 (16)	0.60157 (18)	0.0426 (5)
C7	0.0859 (2)	0.6461 (2)	0.6734 (3)	0.0541 (7)
H7A	0.0369	0.6029	0.6221	0.081*
H7B	0.0430	0.6865	0.7143	0.081*
H7C	0.1388	0.6104	0.7308	0.081*
N8	0.20882 (17)	0.66511 (14)	0.53060 (18)	0.0388 (5)
C9	0.2150 (2)	0.57497 (18)	0.5230 (2)	0.0409 (6)
H9	0.1736	0.5346	0.5613	0.049*
C10	0.2900 (2)	0.53860 (17)	0.4515 (2)	0.0394 (6)
N11	0.31405 (19)	0.44784 (14)	0.43736 (19)	0.0462 (5)
H11	0.2847	0.4002	0.4667	0.055*
C12	0.3925 (2)	0.4414 (2)	0.3690 (3)	0.0524 (7)
H12	0.4241	0.3858	0.3468	0.063*
C13	0.4152 (2)	0.53037 (19)	0.3401 (2)	0.0498 (7)
H13	0.4652	0.5485	0.2935	0.060*
N14	0.35088 (17)	0.58989 (15)	0.39217 (18)	0.0439 (5)
H14	0.3501	0.6511	0.3871	0.053*
S1A	0.11671 (6)	0.32082 (5)	0.61625 (6)	0.0454 (2)
O1A	0.1761 (2)	0.31792 (17)	0.5216 (2)	0.0777 (7)
O2A	0.05228 (18)	0.23784 (15)	0.62733 (19)	0.0670 (6)
O3A	0.06083 (18)	0.40887 (15)	0.6250 (2)	0.0681 (6)
C1A	0.2271 (3)	0.3193 (2)	0.7483 (3)	0.0711 (9)
F1A	0.2736 (2)	0.23723 (19)	0.7680 (3)	0.1312 (11)
F2A	0.3049 (2)	0.3810 (2)	0.7382 (3)	0.1349 (11)
F3A	0.1874 (3)	0.3408 (2)	0.8440 (2)	0.1325 (11)
S1B	0.41086 (6)	0.83315 (5)	0.31694 (6)	0.0444 (2)
O1B	0.4542 (2)	0.77597 (19)	0.2363 (2)	0.0817 (7)
O2B	0.3858 (2)	0.92845 (16)	0.2831 (2)	0.0821 (7)
O3B	0.32475 (16)	0.78518 (13)	0.36507 (18)	0.0537 (5)
C1B	0.5234 (3)	0.8416 (2)	0.4480 (3)	0.0631 (8)
F1B	0.55674 (19)	0.75603 (17)	0.4874 (2)	0.1023 (8)
F2B	0.4907 (2)	0.88692 (19)	0.53512 (18)	0.1051 (8)
F3B	0.60951 (18)	0.88743 (18)	0.4238 (2)	0.1053 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0469 (13)	0.0412 (12)	0.0577 (14)	−0.0014 (10)	0.0237 (11)	−0.0083 (10)
C2	0.0582 (18)	0.0447 (16)	0.074 (2)	−0.0041 (13)	0.0257 (16)	−0.0035 (14)
C3	0.064 (2)	0.0416 (16)	0.091 (2)	0.0023 (14)	0.0184 (18)	−0.0130 (15)
C4	0.0594 (19)	0.064 (2)	0.077 (2)	0.0102 (16)	0.0255 (17)	−0.0204 (16)
C5	0.0541 (17)	0.0612 (18)	0.0621 (18)	0.0056 (14)	0.0271 (15)	−0.0126 (14)
C6	0.0345 (13)	0.0506 (15)	0.0449 (14)	0.0008 (11)	0.0125 (11)	−0.0075 (12)
N7	0.0426 (12)	0.0463 (12)	0.0441 (12)	0.0007 (9)	0.0210 (10)	−0.0039 (9)
C7	0.0563 (17)	0.0630 (18)	0.0518 (16)	−0.0054 (14)	0.0313 (14)	0.0004 (13)
N8	0.0362 (11)	0.0449 (12)	0.0387 (11)	0.0000 (9)	0.0154 (9)	−0.0039 (9)
C9	0.0415 (14)	0.0416 (14)	0.0432 (14)	−0.0021 (11)	0.0172 (11)	−0.0005 (11)
C10	0.0413 (14)	0.0387 (13)	0.0405 (13)	−0.0027 (11)	0.0137 (11)	−0.0015 (10)
N11	0.0558 (14)	0.0352 (11)	0.0537 (13)	−0.0022 (10)	0.0251 (11)	−0.0010 (9)
C12	0.0614 (18)	0.0453 (15)	0.0576 (17)	0.0012 (13)	0.0289 (15)	−0.0090 (13)
C13	0.0535 (16)	0.0494 (15)	0.0550 (16)	−0.0022 (13)	0.0306 (14)	−0.0075 (13)
N14	0.0474 (13)	0.0360 (11)	0.0538 (13)	−0.0038 (9)	0.0232 (11)	−0.0011 (9)
S1A	0.0458 (4)	0.0469 (4)	0.0472 (4)	−0.0047 (3)	0.0180 (3)	0.0049 (3)
O1A	0.0914 (17)	0.0844 (17)	0.0724 (15)	−0.0188 (13)	0.0511 (14)	−0.0056 (12)
O2A	0.0694 (14)	0.0625 (13)	0.0738 (14)	−0.0238 (11)	0.0252 (12)	−0.0023 (11)
O3A	0.0669 (14)	0.0585 (13)	0.0839 (15)	0.0152 (11)	0.0269 (12)	0.0176 (11)
C1A	0.068 (2)	0.062 (2)	0.076 (2)	−0.0011 (18)	0.0008 (19)	0.0078 (17)
F1A	0.1041 (19)	0.0985 (18)	0.171 (3)	0.0359 (15)	−0.0165 (18)	0.0425 (18)
F2A	0.0938 (18)	0.127 (2)	0.158 (3)	−0.0570 (17)	−0.0312 (17)	0.0225 (18)
F3A	0.155 (3)	0.174 (3)	0.0566 (14)	0.018 (2)	−0.0034 (15)	−0.0068 (15)
S1B	0.0468 (4)	0.0423 (4)	0.0480 (4)	−0.0053 (3)	0.0189 (3)	0.0062 (3)
O1B	0.0789 (16)	0.1037 (19)	0.0753 (15)	−0.0141 (14)	0.0452 (13)	−0.0260 (14)
O2B	0.0851 (17)	0.0536 (13)	0.0972 (17)	−0.0062 (12)	−0.0037 (14)	0.0283 (12)
O3B	0.0482 (11)	0.0496 (11)	0.0710 (12)	−0.0050 (9)	0.0298 (10)	−0.0009 (9)
C1B	0.061 (2)	0.064 (2)	0.063 (2)	−0.0101 (16)	0.0091 (16)	0.0114 (16)
F1B	0.0874 (16)	0.0928 (16)	0.1144 (17)	0.0106 (12)	−0.0063 (13)	0.0467 (13)
F2B	0.128 (2)	0.121 (2)	0.0613 (13)	−0.0191 (16)	0.0084 (13)	−0.0195 (13)
F3B	0.0652 (13)	0.128 (2)	0.1133 (17)	−0.0455 (13)	−0.0020 (12)	0.0242 (15)

Geometric parameters (Å, º)

N1—C2	1.343 (3)	N11—C12	1.365 (3)
N1—C6	1.349 (3)	N11—H11	0.8600
N1—H1	0.8600	C12—C13	1.335 (4)
C2—C3	1.354 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—N14	1.368 (3)
C3—C4	1.386 (4)	C13—H13	0.9300
C3—H3	0.9300	N14—H14	0.8600
C4—C5	1.354 (4)	S1A—O3A	1.426 (2)
C4—H4	0.9300	S1A—O2A	1.427 (2)
C5—C6	1.403 (3)	S1A—O1A	1.428 (2)
C5—H5	0.9300	S1A—C1A	1.802 (4)
C6—N7	1.350 (3)	C1A—F1A	1.283 (4)
N7—N8	1.355 (3)	C1A—F2A	1.311 (4)
N7—C7	1.464 (3)	C1A—F3A	1.324 (4)
C7—H7A	0.9600	S1B—O2B	1.407 (2)
C7—H7B	0.9600	S1B—O1B	1.410 (2)
C7—H7C	0.9600	S1B—O3B	1.4548 (18)
N8—C9	1.270 (3)	S1B—C1B	1.813 (3)
C9—C10	1.448 (3)	C1B—F3B	1.315 (4)
C9—H9	0.9300	C1B—F2B	1.315 (4)
C10—N14	1.323 (3)	C1B—F1B	1.316 (4)
C10—N11	1.324 (3)
C2—N1—C6	123.7 (2)	C10—N11—H11	125.2
C2—N1—H1	118.1	C12—N11—H11	125.2
C6—N1—H1	118.1	C13—C12—N11	106.8 (2)
N1—C2—C3	120.4 (3)	C13—C12—H12	126.6
N1—C2—H2	119.8	N11—C12—H12	126.6
C3—C2—H2	119.8	C12—C13—N14	107.0 (2)
C2—C3—C4	117.4 (3)	C12—C13—H13	126.5
C2—C3—H3	121.3	N14—C13—H13	126.5
C4—C3—H3	121.3	C10—N14—C13	109.4 (2)
C5—C4—C3	122.4 (3)	C10—N14—H14	125.3
C5—C4—H4	118.8	C13—N14—H14	125.3
C3—C4—H4	118.8	O3A—S1A—O2A	114.65 (14)
C4—C5—C6	119.0 (3)	O3A—S1A—O1A	114.07 (14)
C4—C5—H5	120.5	O2A—S1A—O1A	115.14 (13)
C6—C5—H5	120.5	O3A—S1A—C1A	103.71 (16)
N1—C6—N7	118.2 (2)	O2A—S1A—C1A	104.28 (15)
N1—C6—C5	117.0 (3)	O1A—S1A—C1A	102.93 (18)
N7—C6—C5	124.8 (2)	F1A—C1A—F2A	107.6 (3)
C6—N7—N8	114.8 (2)	F1A—C1A—F3A	106.6 (3)
C6—N7—C7	123.6 (2)	F2A—C1A—F3A	109.0 (3)
N8—N7—C7	121.6 (2)	F1A—C1A—S1A	112.6 (3)
N7—C7—H7A	109.5	F2A—C1A—S1A	110.4 (3)
N7—C7—H7B	109.5	F3A—C1A—S1A	110.5 (3)
H7A—C7—H7B	109.5	O2B—S1B—O1B	116.78 (17)
N7—C7—H7C	109.5	O2B—S1B—O3B	114.22 (14)
H7A—C7—H7C	109.5	O1B—S1B—O3B	112.95 (13)
H7B—C7—H7C	109.5	O2B—S1B—C1B	104.40 (15)
C9—N8—N7	119.9 (2)	O1B—S1B—C1B	104.66 (16)
N8—C9—C10	116.3 (2)	O3B—S1B—C1B	101.65 (13)
N8—C9—H9	121.8	F3B—C1B—F2B	108.1 (3)
C10—C9—H9	121.8	F3B—C1B—F1B	108.3 (3)
N14—C10—N11	107.2 (2)	F2B—C1B—F1B	107.6 (3)
N14—C10—C9	126.4 (2)	F3B—C1B—S1B	111.1 (2)
N11—C10—C9	126.3 (2)	F2B—C1B—S1B	111.0 (2)
C10—N11—C12	109.6 (2)	F1B—C1B—S1B	110.5 (2)
C6—N1—C2—C3	1.1 (5)	N11—C10—N14—C13	−0.4 (3)
N1—C2—C3—C4	0.0 (5)	C9—C10—N14—C13	177.1 (3)
C2—C3—C4—C5	−0.2 (5)	C12—C13—N14—C10	−0.1 (3)
C3—C4—C5—C6	−0.6 (5)	O3A—S1A—C1A—F1A	167.5 (3)
C2—N1—C6—N7	178.3 (3)	O2A—S1A—C1A—F1A	47.1 (3)
C2—N1—C6—C5	−1.9 (4)	O1A—S1A—C1A—F1A	−73.4 (3)
C4—C5—C6—N1	1.6 (4)	O3A—S1A—C1A—F2A	−72.2 (3)
C4—C5—C6—N7	−178.6 (3)	O2A—S1A—C1A—F2A	167.5 (3)
N1—C6—N7—N8	3.4 (3)	O1A—S1A—C1A—F2A	46.9 (3)
C5—C6—N7—N8	−176.4 (2)	O3A—S1A—C1A—F3A	48.4 (3)
N1—C6—N7—C7	−178.7 (2)	O2A—S1A—C1A—F3A	−71.9 (3)
C5—C6—N7—C7	1.5 (4)	O1A—S1A—C1A—F3A	167.5 (3)
C6—N7—N8—C9	179.7 (2)	O2B—S1B—C1B—F3B	−58.3 (3)
C7—N7—N8—C9	1.8 (4)	O1B—S1B—C1B—F3B	64.9 (3)
N7—N8—C9—C10	−176.1 (2)	O3B—S1B—C1B—F3B	−177.4 (2)
N8—C9—C10—N14	−1.2 (4)	O2B—S1B—C1B—F2B	62.1 (3)
N8—C9—C10—N11	175.8 (2)	O1B—S1B—C1B—F2B	−174.7 (2)
N14—C10—N11—C12	0.7 (3)	O3B—S1B—C1B—F2B	−57.0 (2)
C9—C10—N11—C12	−176.8 (3)	O2B—S1B—C1B—F1B	−178.6 (2)
C10—N11—C12—C13	−0.8 (3)	O1B—S1B—C1B—F1B	−55.3 (3)
N11—C12—C13—N14	0.5 (3)	O3B—S1B—C1B—F1B	62.4 (3)