3-(Adamantan-1-yl)-4-[(E)-(2,6-di-fluoro-benzyl-idene)amino]-1-[(4-ethyl-piperazin-1-yl)meth-yl]-4,5-di-hydro-1H-1,2,4-triazole-5-thione.

In the title compound, C26H34F2N6S, the triazole ring is linked to a benzene ring via an imine bond [N=C = 1.255 (2) Å; conformation: E], with a dihedral angle of 25.21 (11)° between the rings. The 4-ethyl-piperazinyl residue is folded away from the thione-S atom. In the crystal, helical supra-molecular chains propagating along [010] and sustained by weak C-S⋯π(triazole) inter-actions occur [S⋯centroid distance = 3.2872 (10) Å]. Links between these chains are of the type benzene-C-H⋯N(imine) and π-π [between centrosymmetrically related benzene rings with an inter-centroid distance of 3.9241 (15) Å] and result in a three-dimensional architecture.

Related literature

For background to the pharmacological properties of adamantane derivatives, see: Al-Omar et al. (2010 ▶). For related structures, see: Almutairi et al. (2012 ▶); El-Emam et al. (2012 ▶).

Experimental

Crystal data

C26H34F2N6S

M = 500.65

Monoclinic,

a = 17.0824 (11) Å

b = 7.8212 (6) Å

c = 19.6691 (14) Å

β = 92.249 (6)°

V = 2625.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 295 K

0.40 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.656, T max = 1.000

16764 measured reflections

6063 independent reflections

3908 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.138

S = 1.01

6063 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009264/hb7065sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009264/hb7065Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009264/hb7065Isup3.cml

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

C26H34F2N6S	F(000) = 1064
Mr = 500.65	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3864 reflections
a = 17.0824 (11) Å	θ = 2.9–27.5°
b = 7.8212 (6) Å	µ = 0.16 mm−1
c = 19.6691 (14) Å	T = 295 K
β = 92.249 (6)°	Prism, yellow
V = 2625.9 (3) Å3	0.40 × 0.30 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	6063 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3908 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −22→20
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
Tmin = 0.656, Tmax = 1.000	l = −25→25
16764 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.6004P] where P = (Fo2 + 2Fc2)/3
6063 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−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
S1	0.74938 (3)	0.92905 (8)	0.71719 (3)	0.05854 (19)
F1	0.51929 (7)	0.8699 (2)	0.63956 (7)	0.0759 (4)
F2	0.64752 (8)	0.6197 (2)	0.45778 (7)	0.0901 (5)
N1	0.86739 (9)	0.6995 (2)	0.71058 (7)	0.0417 (4)
N2	0.89390 (8)	0.5649 (2)	0.67246 (8)	0.0419 (4)
N3	0.78219 (8)	0.6639 (2)	0.62927 (7)	0.0382 (4)
N4	0.72072 (9)	0.6716 (2)	0.58085 (8)	0.0447 (4)
N5	0.97927 (9)	0.8412 (2)	0.77067 (8)	0.0483 (4)
N6	1.10661 (11)	1.0150 (3)	0.71147 (10)	0.0668 (6)
C1	0.79839 (10)	0.7645 (3)	0.68619 (9)	0.0408 (4)
C2	0.84230 (10)	0.5462 (2)	0.62267 (9)	0.0370 (4)
C3	0.84653 (10)	0.4095 (2)	0.56948 (9)	0.0382 (4)
C4	0.92160 (11)	0.3045 (3)	0.58368 (11)	0.0501 (5)
H4A	0.9670	0.3785	0.5816	0.060*
H4B	0.9209	0.2559	0.6290	0.060*
C5	0.92751 (13)	0.1613 (3)	0.53147 (11)	0.0568 (6)
H5A	0.9755	0.0957	0.5413	0.068*
C6	0.93019 (13)	0.2356 (3)	0.46007 (12)	0.0627 (6)
H6A	0.9342	0.1441	0.4271	0.075*
H6B	0.9757	0.3090	0.4568	0.075*
C7	0.85525 (13)	0.3389 (3)	0.44517 (11)	0.0576 (6)
H7A	0.8566	0.3872	0.3993	0.069*
C8	0.78406 (14)	0.2228 (3)	0.44952 (12)	0.0661 (7)
H8A	0.7868	0.1323	0.4160	0.079*
H8B	0.7366	0.2881	0.4399	0.079*
C9	0.78190 (13)	0.1457 (3)	0.52052 (12)	0.0594 (6)
H9A	0.7364	0.0698	0.5229	0.071*
C10	0.77556 (11)	0.2883 (3)	0.57310 (11)	0.0502 (5)
H10A	0.7739	0.2391	0.6183	0.060*
H10B	0.7275	0.3520	0.5643	0.060*
C11	0.85704 (14)	0.0427 (3)	0.53560 (13)	0.0660 (6)
H11A	0.8558	−0.0072	0.5807	0.079*
H11B	0.8610	−0.0492	0.5028	0.079*
C12	0.84933 (12)	0.4845 (3)	0.49680 (9)	0.0466 (5)
H12A	0.8024	0.5510	0.4867	0.056*
H12B	0.8943	0.5597	0.4939	0.056*
C13	0.65661 (11)	0.7314 (3)	0.59892 (10)	0.0502 (5)
H13A	0.6525	0.7697	0.6434	0.060*
C14	0.58792 (11)	0.7427 (3)	0.55192 (10)	0.0464 (5)
C15	0.51815 (12)	0.8099 (3)	0.57474 (11)	0.0533 (5)
C16	0.44989 (12)	0.8209 (3)	0.53597 (14)	0.0657 (7)
H16A	0.4048	0.8667	0.5538	0.079*
C17	0.44969 (14)	0.7628 (4)	0.47009 (14)	0.0707 (7)
H17A	0.4039	0.7686	0.4430	0.085*
C18	0.51624 (14)	0.6963 (3)	0.44379 (12)	0.0681 (7)
H18A	0.5162	0.6582	0.3990	0.082*
C19	0.58297 (12)	0.6868 (3)	0.48466 (11)	0.0575 (6)
C20	0.90864 (11)	0.7436 (3)	0.77544 (9)	0.0502 (5)
H20A	0.8729	0.8074	0.8029	0.060*
H20B	0.9213	0.6382	0.7995	0.060*
C21	0.96781 (13)	1.0051 (3)	0.73711 (14)	0.0649 (6)
H21A	0.9265	1.0680	0.7586	0.078*
H21B	0.9519	0.9872	0.6898	0.078*
C22	1.04327 (14)	1.1080 (3)	0.74151 (15)	0.0741 (7)
H22A	1.0354	1.2160	0.7179	0.089*
H22B	1.0571	1.1326	0.7888	0.089*
C23	1.11758 (13)	0.8541 (4)	0.74629 (13)	0.0683 (7)
H23A	1.1315	0.8749	0.7939	0.082*
H23B	1.1602	0.7918	0.7266	0.082*
C24	1.04390 (12)	0.7486 (3)	0.74069 (12)	0.0600 (6)
H24A	1.0309	0.7244	0.6932	0.072*
H24B	1.0521	0.6407	0.7642	0.072*
C25	1.17960 (16)	1.1158 (4)	0.71267 (15)	0.0885 (9)
H25A	1.2226	1.0420	0.7008	0.106*
H25B	1.1905	1.1577	0.7585	0.106*
C26	1.1755 (2)	1.2638 (5)	0.6647 (2)	0.1292 (15)
H26A	1.2245	1.3238	0.6667	0.194*
H26B	1.1343	1.3398	0.6774	0.194*
H26C	1.1648	1.2231	0.6193	0.194*

	U11	U22	U33	U12	U13	U23
S1	0.0632 (3)	0.0571 (4)	0.0552 (3)	0.0145 (3)	0.0015 (3)	−0.0143 (3)
F1	0.0556 (7)	0.0991 (12)	0.0733 (9)	0.0090 (7)	0.0078 (6)	−0.0235 (8)
F2	0.0756 (9)	0.1407 (15)	0.0533 (8)	0.0358 (9)	−0.0064 (6)	−0.0250 (9)
N1	0.0439 (8)	0.0442 (10)	0.0368 (8)	0.0010 (7)	−0.0019 (6)	−0.0016 (8)
N2	0.0426 (8)	0.0421 (10)	0.0410 (8)	0.0024 (7)	−0.0006 (7)	−0.0006 (8)
N3	0.0387 (8)	0.0404 (9)	0.0354 (8)	0.0036 (7)	−0.0007 (6)	−0.0004 (7)
N4	0.0427 (9)	0.0483 (11)	0.0426 (9)	0.0081 (8)	−0.0062 (7)	−0.0041 (8)
N5	0.0498 (9)	0.0526 (11)	0.0417 (9)	−0.0019 (8)	−0.0072 (7)	0.0020 (8)
N6	0.0611 (12)	0.0748 (15)	0.0635 (12)	−0.0167 (11)	−0.0089 (9)	0.0042 (11)
C1	0.0444 (10)	0.0418 (11)	0.0362 (9)	−0.0007 (9)	0.0023 (8)	−0.0001 (9)
C2	0.0373 (9)	0.0354 (11)	0.0384 (9)	0.0020 (8)	0.0035 (7)	0.0034 (8)
C3	0.0381 (9)	0.0368 (11)	0.0398 (10)	0.0030 (8)	0.0014 (7)	−0.0004 (9)
C4	0.0517 (11)	0.0468 (13)	0.0517 (12)	0.0105 (10)	0.0013 (9)	0.0010 (10)
C5	0.0631 (13)	0.0478 (14)	0.0599 (13)	0.0173 (11)	0.0045 (10)	−0.0031 (11)
C6	0.0699 (14)	0.0596 (16)	0.0600 (14)	0.0107 (12)	0.0193 (11)	−0.0089 (12)
C7	0.0789 (15)	0.0544 (14)	0.0401 (11)	0.0126 (12)	0.0087 (10)	0.0014 (10)
C8	0.0753 (15)	0.0613 (16)	0.0606 (14)	0.0078 (13)	−0.0098 (11)	−0.0209 (13)
C9	0.0603 (13)	0.0469 (14)	0.0712 (15)	−0.0106 (11)	0.0064 (11)	−0.0105 (12)
C10	0.0508 (11)	0.0447 (13)	0.0559 (12)	−0.0036 (10)	0.0114 (9)	−0.0031 (10)
C11	0.0965 (18)	0.0390 (13)	0.0629 (14)	0.0051 (12)	0.0092 (13)	−0.0024 (12)
C12	0.0545 (11)	0.0438 (12)	0.0420 (10)	0.0049 (9)	0.0067 (8)	0.0045 (9)
C13	0.0485 (11)	0.0614 (14)	0.0404 (10)	0.0051 (10)	−0.0012 (8)	−0.0058 (10)
C14	0.0428 (10)	0.0470 (13)	0.0488 (11)	0.0028 (9)	−0.0039 (8)	0.0010 (10)
C15	0.0485 (12)	0.0530 (14)	0.0582 (13)	−0.0008 (10)	0.0000 (9)	−0.0024 (11)
C16	0.0401 (11)	0.0701 (17)	0.0865 (18)	0.0023 (11)	−0.0024 (11)	0.0072 (15)
C17	0.0515 (14)	0.0808 (19)	0.0779 (17)	−0.0066 (13)	−0.0202 (12)	0.0120 (15)
C18	0.0685 (15)	0.0814 (18)	0.0531 (13)	−0.0028 (14)	−0.0168 (11)	0.0013 (13)
C19	0.0555 (12)	0.0675 (16)	0.0489 (12)	0.0103 (12)	−0.0052 (10)	−0.0026 (12)
C20	0.0562 (12)	0.0604 (14)	0.0335 (10)	−0.0021 (11)	−0.0046 (8)	0.0004 (10)
C21	0.0625 (14)	0.0539 (15)	0.0767 (16)	−0.0021 (12)	−0.0164 (11)	0.0048 (13)
C22	0.0722 (16)	0.0556 (16)	0.0923 (19)	−0.0100 (13)	−0.0243 (14)	0.0042 (15)
C23	0.0545 (13)	0.0802 (19)	0.0695 (16)	−0.0003 (13)	−0.0037 (11)	0.0011 (14)
C24	0.0553 (13)	0.0628 (16)	0.0616 (14)	0.0002 (11)	−0.0027 (10)	0.0017 (12)
C25	0.0774 (17)	0.105 (2)	0.0817 (19)	−0.0353 (17)	−0.0109 (14)	0.0082 (18)
C26	0.125 (3)	0.132 (3)	0.128 (3)	−0.066 (2)	−0.029 (2)	0.055 (3)

S1—C1	1.664 (2)	C9—C11	1.534 (3)
F1—C15	1.358 (2)	C9—H9A	0.9800
F2—C19	1.348 (2)	C10—H10A	0.9700
N1—C1	1.354 (2)	C10—H10B	0.9700
N1—N2	1.379 (2)	C11—H11A	0.9700
N1—C20	1.474 (2)	C11—H11B	0.9700
N2—C2	1.300 (2)	C12—H12A	0.9700
N3—C1	1.387 (2)	C12—H12B	0.9700
N3—C2	1.389 (2)	C13—C14	1.468 (3)
N3—N4	1.391 (2)	C13—H13A	0.9300
N4—C13	1.255 (2)	C14—C19	1.393 (3)
N5—C20	1.434 (3)	C14—C15	1.393 (3)
N5—C21	1.452 (3)	C15—C16	1.371 (3)
N5—C24	1.464 (3)	C16—C17	1.373 (3)
N6—C23	1.442 (3)	C16—H16A	0.9300
N6—C22	1.449 (3)	C17—C18	1.370 (3)
N6—C25	1.474 (3)	C17—H17A	0.9300
C2—C3	1.500 (3)	C18—C19	1.371 (3)
C3—C4	1.540 (3)	C18—H18A	0.9300
C3—C10	1.543 (3)	C20—H20A	0.9700
C3—C12	1.548 (3)	C20—H20B	0.9700
C4—C5	1.526 (3)	C21—C22	1.519 (3)
C4—H4A	0.9700	C21—H21A	0.9700
C4—H4B	0.9700	C21—H21B	0.9700
C5—C11	1.524 (3)	C22—H22A	0.9700
C5—C6	1.522 (3)	C22—H22B	0.9700
C5—H5A	0.9800	C23—C24	1.505 (3)
C6—C7	1.532 (3)	C23—H23A	0.9700
C6—H6A	0.9700	C23—H23B	0.9700
C6—H6B	0.9700	C24—H24A	0.9700
C7—C8	1.523 (3)	C24—H24B	0.9700
C7—C12	1.532 (3)	C25—C26	1.493 (4)
C7—H7A	0.9800	C25—H25A	0.9700
C8—C9	1.523 (3)	C25—H25B	0.9700
C8—H8A	0.9700	C26—H26A	0.9600
C8—H8B	0.9700	C26—H26B	0.9600
C9—C10	1.528 (3)	C26—H26C	0.9600
C1—N1—N2	113.17 (15)	C9—C11—H11B	109.9
C1—N1—C20	126.80 (16)	H11A—C11—H11B	108.3
N2—N1—C20	119.55 (15)	C7—C12—C3	109.61 (17)
C2—N2—N1	105.55 (14)	C7—C12—H12A	109.7
C1—N3—C2	109.05 (14)	C3—C12—H12A	109.7
C1—N3—N4	130.48 (15)	C7—C12—H12B	109.7
C2—N3—N4	120.39 (15)	C3—C12—H12B	109.7
C13—N4—N3	117.78 (16)	H12A—C12—H12B	108.2
C20—N5—C21	113.64 (16)	N4—C13—C14	121.94 (18)
C20—N5—C24	114.37 (17)	N4—C13—H13A	119.0
C21—N5—C24	110.13 (18)	C14—C13—H13A	119.0
C23—N6—C22	109.3 (2)	C19—C14—C15	113.81 (18)
C23—N6—C25	111.4 (2)	C19—C14—C13	126.64 (18)
C22—N6—C25	111.7 (2)	C15—C14—C13	119.52 (18)
N1—C1—N3	102.50 (15)	F1—C15—C16	118.7 (2)
N1—C1—S1	127.14 (14)	F1—C15—C14	116.88 (18)
N3—C1—S1	130.32 (14)	C16—C15—C14	124.4 (2)
N2—C2—N3	109.69 (16)	C15—C16—C17	118.3 (2)
N2—C2—C3	123.79 (16)	C15—C16—H16A	120.8
N3—C2—C3	126.41 (15)	C17—C16—H16A	120.8
C2—C3—C4	108.45 (15)	C18—C17—C16	120.7 (2)
C2—C3—C10	110.28 (14)	C18—C17—H17A	119.6
C4—C3—C10	108.29 (17)	C16—C17—H17A	119.6
C2—C3—C12	112.22 (16)	C17—C18—C19	118.8 (2)
C4—C3—C12	108.32 (15)	C17—C18—H18A	120.6
C10—C3—C12	109.18 (16)	C19—C18—H18A	120.6
C5—C4—C3	110.26 (17)	F2—C19—C18	117.7 (2)
C5—C4—H4A	109.6	F2—C19—C14	118.34 (17)
C3—C4—H4A	109.6	C18—C19—C14	123.9 (2)
C5—C4—H4B	109.6	N5—C20—N1	116.29 (16)
C3—C4—H4B	109.6	N5—C20—H20A	108.2
H4A—C4—H4B	108.1	N1—C20—H20A	108.2
C11—C5—C6	109.5 (2)	N5—C20—H20B	108.2
C11—C5—C4	109.72 (18)	N1—C20—H20B	108.2
C6—C5—C4	110.23 (19)	H20A—C20—H20B	107.4
C11—C5—H5A	109.1	N5—C21—C22	110.05 (18)
C6—C5—H5A	109.1	N5—C21—H21A	109.7
C4—C5—H5A	109.1	C22—C21—H21A	109.7
C5—C6—C7	108.82 (17)	N5—C21—H21B	109.7
C5—C6—H6A	109.9	C22—C21—H21B	109.7
C7—C6—H6A	109.9	H21A—C21—H21B	108.2
C5—C6—H6B	109.9	N6—C22—C21	110.9 (2)
C7—C6—H6B	109.9	N6—C22—H22A	109.5
H6A—C6—H6B	108.3	C21—C22—H22A	109.5
C8—C7—C6	109.7 (2)	N6—C22—H22B	109.5
C8—C7—C12	109.42 (17)	C21—C22—H22B	109.5
C6—C7—C12	109.98 (19)	H22A—C22—H22B	108.1
C8—C7—H7A	109.2	N6—C23—C24	110.55 (19)
C6—C7—H7A	109.2	N6—C23—H23A	109.5
C12—C7—H7A	109.2	C24—C23—H23A	109.5
C7—C8—C9	109.63 (18)	N6—C23—H23B	109.5
C7—C8—H8A	109.7	C24—C23—H23B	109.5
C9—C8—H8A	109.7	H23A—C23—H23B	108.1
C7—C8—H8B	109.7	N5—C24—C23	109.9 (2)
C9—C8—H8B	109.7	N5—C24—H24A	109.7
H8A—C8—H8B	108.2	C23—C24—H24A	109.7
C8—C9—C10	109.67 (19)	N5—C24—H24B	109.7
C8—C9—C11	109.57 (19)	C23—C24—H24B	109.7
C10—C9—C11	109.46 (19)	H24A—C24—H24B	108.2
C8—C9—H9A	109.4	N6—C25—C26	112.6 (2)
C10—C9—H9A	109.4	N6—C25—H25A	109.1
C11—C9—H9A	109.4	C26—C25—H25A	109.1
C9—C10—C3	109.92 (16)	N6—C25—H25B	109.1
C9—C10—H10A	109.7	C26—C25—H25B	109.1
C3—C10—H10A	109.7	H25A—C25—H25B	107.8
C9—C10—H10B	109.7	C25—C26—H26A	109.5
C3—C10—H10B	109.7	C25—C26—H26B	109.5
H10A—C10—H10B	108.2	H26A—C26—H26B	109.5
C5—C11—C9	109.09 (19)	C25—C26—H26C	109.5
C5—C11—H11A	109.9	H26A—C26—H26C	109.5
C9—C11—H11A	109.9	H26B—C26—H26C	109.5
C5—C11—H11B	109.9
C1—N1—N2—C2	1.3 (2)	C6—C5—C11—C9	−60.9 (2)
C20—N1—N2—C2	173.83 (16)	C4—C5—C11—C9	60.2 (2)
C1—N3—N4—C13	−28.1 (3)	C8—C9—C11—C5	59.9 (2)
C2—N3—N4—C13	155.49 (19)	C10—C9—C11—C5	−60.4 (2)
N2—N1—C1—N3	−0.5 (2)	C8—C7—C12—C3	60.1 (2)
C20—N1—C1—N3	−172.39 (17)	C6—C7—C12—C3	−60.6 (2)
N2—N1—C1—S1	−178.51 (14)	C2—C3—C12—C7	178.87 (16)
C20—N1—C1—S1	9.6 (3)	C4—C3—C12—C7	59.2 (2)
C2—N3—C1—N1	−0.44 (19)	C10—C3—C12—C7	−58.5 (2)
N4—N3—C1—N1	−177.17 (17)	N3—N4—C13—C14	−179.08 (18)
C2—N3—C1—S1	177.48 (15)	N4—C13—C14—C19	2.1 (4)
N4—N3—C1—S1	0.7 (3)	N4—C13—C14—C15	179.9 (2)
N1—N2—C2—N3	−1.50 (19)	C19—C14—C15—F1	−178.7 (2)
N1—N2—C2—C3	−178.02 (16)	C13—C14—C15—F1	3.2 (3)
C1—N3—C2—N2	1.3 (2)	C19—C14—C15—C16	0.3 (3)
N4—N3—C2—N2	178.40 (15)	C13—C14—C15—C16	−177.7 (2)
C1—N3—C2—C3	177.68 (17)	F1—C15—C16—C17	178.8 (2)
N4—N3—C2—C3	−5.2 (3)	C14—C15—C16—C17	−0.2 (4)
N2—C2—C3—C4	−1.6 (2)	C15—C16—C17—C18	−0.4 (4)
N3—C2—C3—C4	−177.49 (17)	C16—C17—C18—C19	0.8 (4)
N2—C2—C3—C10	116.9 (2)	C17—C18—C19—F2	179.5 (2)
N3—C2—C3—C10	−59.1 (2)	C17—C18—C19—C14	−0.7 (4)
N2—C2—C3—C12	−121.18 (19)	C15—C14—C19—F2	179.9 (2)
N3—C2—C3—C12	62.9 (2)	C13—C14—C19—F2	−2.2 (4)
C2—C3—C4—C5	178.88 (16)	C15—C14—C19—C18	0.1 (3)
C10—C3—C4—C5	59.2 (2)	C13—C14—C19—C18	178.0 (2)
C12—C3—C4—C5	−59.1 (2)	C21—N5—C20—N1	59.6 (3)
C3—C4—C5—C11	−60.4 (2)	C24—N5—C20—N1	−68.1 (2)
C3—C4—C5—C6	60.3 (2)	C1—N1—C20—N5	−109.1 (2)
C11—C5—C6—C7	61.0 (2)	N2—N1—C20—N5	79.5 (2)
C4—C5—C6—C7	−59.8 (2)	C20—N5—C21—C22	173.51 (19)
C5—C6—C7—C8	−60.3 (2)	C24—N5—C21—C22	−56.7 (3)
C5—C6—C7—C12	60.1 (2)	C23—N6—C22—C21	−58.7 (3)
C6—C7—C8—C9	59.7 (2)	C25—N6—C22—C21	177.6 (2)
C12—C7—C8—C9	−61.1 (2)	N5—C21—C22—N6	57.6 (3)
C7—C8—C9—C10	60.8 (2)	C22—N6—C23—C24	59.7 (3)
C7—C8—C9—C11	−59.3 (2)	C25—N6—C23—C24	−176.4 (2)
C8—C9—C10—C3	−59.6 (2)	C20—N5—C24—C23	−172.79 (18)
C11—C9—C10—C3	60.6 (2)	C21—N5—C24—C23	57.8 (2)
C2—C3—C10—C9	−177.92 (17)	N6—C23—C24—N5	−59.5 (3)
C4—C3—C10—C9	−59.4 (2)	C23—N6—C25—C26	167.4 (3)
C12—C3—C10—C9	58.3 (2)	C22—N6—C25—C26	−70.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N5i	0.93	2.58	3.451 (3)	157
C1—S1···Cg1ii	1.66 (1)	3.29 (1)	4.849 (2)	155 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1–N3,C1,C2 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N5i	0.93	2.58	3.451 (3)	157
C1—S1⋯Cg1ii	1.66 (1)	3.29 (1)	4.849 (2)	155 (1)

Symmetry codes: (i) ; (ii) .