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

The imine residue [C=N = 1.268 (3) Å; conformation = E] is twisted [N-N-C-N = 87.8 (2)°] out of the plane (r.m.s. deviation = 0.016 Å) of the central 1,2,4-triazole ring in the title compound, C(30)H(34)F(2)N(6)S. A small twist also occurs between the imine and terminal benzene rings [N-C-C-C = -169.8 (2)°]. The piperazine ring (chair conformation) occupies a position almost normal to the central plane [N-N-C-N = 87.8 (2)°]. In the crystal, the mol-ecules are consolidated into a three-dimensional architecture via C-H⋯S, C-H⋯π and π-π inter-actions, the latter between centrosymmetrically related difluoro-benzene rings [inter-centroid distance = 3.9389 (18) Å].

Related literature

For a related structure and background to the biological activity of adamantane derivatives, see: n class="Chemical">El-Emam et al. (2012 ▶). For further synthetic details, see: Al-Omar et al. (2010 ▶).

Experimental

Crystal data

C30H34F2N6S

M = 548.69

Monoclinic,

a = 17.2712 (3) Å

b = 7.7141 (1) Å

c = 21.3157 (4) Å

β = 95.245 (2)°

V = 2828.04 (8) Å3

Z = 4

Cu Kα radiation

μ = 1.38 mm−1

T = 294 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.702, T max = 1.000

20801 measured reflections

5884 independent reflections

4712 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.161

S = 1.04

5884 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025135/hb6828sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025135/hb6828Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025135/hb6828Isup3.cml

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

C30H34F2N6S	F(000) = 1160
Mr = 548.69	Dx = 1.289 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6884 reflections
a = 17.2712 (3) Å	θ = 3.2–76.4°
b = 7.7141 (1) Å	µ = 1.38 mm−1
c = 21.3157 (4) Å	T = 294 K
β = 95.245 (2)°	Prism, light-yellow
V = 2828.04 (8) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	5884 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4712 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 3.2°
ω scan	h = −21→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→9
Tmin = 0.702, Tmax = 1.000	l = −24→26
20801 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) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0841P)2 + 0.8642P] where P = (Fo2 + 2Fc2)/3
5884 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.42 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	0.71076 (3)	0.89349 (8)	0.68065 (3)	0.06427 (19)
N1	0.70514 (9)	0.6526 (2)	0.55097 (8)	0.0518 (4)
N2	0.76034 (9)	0.6366 (2)	0.60276 (8)	0.0454 (4)
N3	0.87099 (9)	0.5541 (2)	0.65262 (8)	0.0471 (4)
N4	0.83637 (9)	0.6826 (2)	0.68561 (8)	0.0479 (4)
N5	0.93244 (10)	0.8605 (2)	0.75009 (8)	0.0501 (4)
N6	1.03325 (10)	1.1263 (2)	0.71401 (8)	0.0502 (4)
F1	0.49418 (9)	0.7917 (3)	0.59319 (7)	0.1000 (6)
F2	0.64051 (11)	0.6213 (4)	0.43092 (8)	0.1399 (11)
C1	0.83845 (10)	0.3955 (2)	0.55331 (9)	0.0443 (4)
C2	0.84385 (14)	0.4736 (3)	0.48742 (10)	0.0599 (5)
H2A	0.7959	0.5337	0.4738	0.072*
H2B	0.8862	0.5566	0.4888	0.072*
C3	0.85804 (18)	0.3275 (4)	0.44079 (11)	0.0759 (8)
H3	0.8606	0.3768	0.3987	0.091*
C4	0.79106 (18)	0.1981 (4)	0.43920 (15)	0.0944 (11)
H4A	0.7985	0.1080	0.4086	0.113*
H4B	0.7424	0.2567	0.4266	0.113*
C5	0.78757 (15)	0.1172 (3)	0.50410 (15)	0.0760 (8)
H5	0.7452	0.0325	0.5025	0.091*
C6	0.86387 (16)	0.0277 (3)	0.52427 (14)	0.0707 (7)
H6A	0.8729	−0.0644	0.4948	0.085*
H6B	0.8617	−0.0234	0.5656	0.085*
C7	0.92952 (13)	0.1579 (3)	0.52613 (11)	0.0577 (5)
H7	0.9786	0.0994	0.5395	0.069*
C8	0.91554 (11)	0.3024 (3)	0.57298 (10)	0.0511 (5)
H8A	0.9580	0.3850	0.5744	0.061*
H8B	0.9139	0.2536	0.6148	0.061*
C9	0.77257 (13)	0.2608 (3)	0.55135 (13)	0.0616 (6)
H9A	0.7700	0.2110	0.5929	0.074*
H9B	0.7232	0.3165	0.5389	0.074*
C10	0.93432 (16)	0.2354 (3)	0.46118 (12)	0.0699 (7)
H10A	0.9436	0.1446	0.4313	0.084*
H10B	0.9771	0.3172	0.4622	0.084*
C11	0.82487 (10)	0.5307 (2)	0.60164 (9)	0.0437 (4)
C12	0.76867 (11)	0.7375 (2)	0.65675 (9)	0.0467 (4)
C13	0.63618 (11)	0.6808 (3)	0.56417 (10)	0.0531 (5)
H13	0.6258	0.6842	0.6062	0.064*
C14	0.57280 (11)	0.7082 (3)	0.51524 (10)	0.0519 (5)
C15	0.50136 (12)	0.7655 (3)	0.53143 (11)	0.0598 (5)
C16	0.43828 (14)	0.8010 (4)	0.48995 (13)	0.0734 (7)
H16	0.3922	0.8421	0.5039	0.088*
C17	0.44493 (16)	0.7743 (4)	0.42783 (13)	0.0836 (8)
H17	0.4028	0.7972	0.3986	0.100*
C18	0.51275 (19)	0.7141 (5)	0.40770 (13)	0.0967 (11)
H18	0.5169	0.6949	0.3651	0.116*
C19	0.57489 (15)	0.6823 (5)	0.45122 (12)	0.0794 (8)
C20	0.87344 (13)	0.7298 (3)	0.74837 (9)	0.0529 (5)
H20A	0.8332	0.7690	0.7739	0.064*
H20B	0.8962	0.6260	0.7680	0.064*
C21	0.99593 (13)	0.8207 (3)	0.71174 (11)	0.0560 (5)
H21A	0.9773	0.8259	0.6675	0.067*
H21B	1.0148	0.7042	0.7210	0.067*
C22	1.06122 (12)	0.9487 (3)	0.72533 (11)	0.0566 (5)
H22A	1.0825	0.9371	0.7688	0.068*
H22B	1.1024	0.9241	0.6986	0.068*
C23	0.96833 (13)	1.1645 (3)	0.75066 (11)	0.0582 (5)
H23A	0.9493	1.2806	0.7409	0.070*
H23B	0.9857	1.1601	0.7952	0.070*
C24	0.90366 (12)	1.0356 (3)	0.73619 (11)	0.0546 (5)
H24A	0.8611	1.0613	0.7614	0.066*
H24B	0.8844	1.0439	0.6921	0.066*
C25	1.09395 (12)	1.2508 (3)	0.71727 (10)	0.0525 (5)
C26	1.14778 (15)	1.2456 (3)	0.67281 (12)	0.0653 (6)
H26	1.1430	1.1623	0.6412	0.078*
C27	1.20870 (15)	1.3638 (4)	0.67517 (14)	0.0754 (7)
H27	1.2447	1.3573	0.6454	0.090*
C28	1.21662 (16)	1.4893 (4)	0.72056 (15)	0.0796 (8)
H28	1.2574	1.5683	0.7217	0.096*
C29	1.16349 (17)	1.4969 (4)	0.76432 (16)	0.0864 (8)
H29	1.1682	1.5821	0.7953	0.104*
C30	1.10264 (15)	1.3788 (3)	0.76298 (13)	0.0705 (6)
H30	1.0672	1.3857	0.7932	0.085*

	U11	U22	U33	U12	U13	U23
S1	0.0526 (3)	0.0593 (3)	0.0821 (4)	0.0057 (2)	0.0122 (3)	−0.0215 (3)
N1	0.0425 (8)	0.0561 (9)	0.0551 (9)	0.0104 (7)	−0.0041 (7)	−0.0122 (8)
N2	0.0376 (7)	0.0450 (8)	0.0528 (9)	0.0048 (6)	0.0006 (6)	−0.0087 (7)
N3	0.0449 (8)	0.0433 (8)	0.0526 (9)	0.0020 (6)	0.0018 (7)	−0.0036 (7)
N4	0.0469 (8)	0.0469 (8)	0.0496 (9)	−0.0021 (7)	0.0022 (7)	−0.0059 (7)
N5	0.0538 (9)	0.0519 (9)	0.0444 (8)	−0.0070 (7)	0.0029 (7)	−0.0015 (7)
N6	0.0504 (9)	0.0468 (9)	0.0533 (9)	−0.0008 (7)	0.0035 (7)	−0.0014 (7)
F1	0.0608 (9)	0.179 (2)	0.0605 (9)	0.0320 (10)	0.0098 (7)	−0.0038 (10)
F2	0.0842 (12)	0.269 (3)	0.0661 (10)	0.0617 (16)	0.0053 (8)	−0.0370 (14)
C1	0.0386 (9)	0.0411 (9)	0.0530 (10)	0.0057 (7)	0.0039 (7)	−0.0042 (8)
C2	0.0686 (13)	0.0560 (12)	0.0551 (12)	0.0226 (10)	0.0052 (10)	0.0066 (9)
C3	0.0965 (19)	0.0818 (17)	0.0489 (12)	0.0411 (16)	0.0042 (12)	−0.0001 (11)
C4	0.0862 (19)	0.103 (2)	0.088 (2)	0.0409 (18)	−0.0264 (15)	−0.0497 (18)
C5	0.0591 (13)	0.0621 (14)	0.106 (2)	−0.0035 (11)	0.0020 (13)	−0.0342 (14)
C6	0.0834 (17)	0.0453 (11)	0.0852 (17)	0.0111 (11)	0.0181 (13)	−0.0101 (11)
C7	0.0553 (12)	0.0524 (11)	0.0657 (13)	0.0215 (9)	0.0073 (10)	−0.0006 (9)
C8	0.0457 (10)	0.0487 (10)	0.0583 (11)	0.0123 (8)	0.0016 (8)	0.0008 (9)
C9	0.0464 (11)	0.0537 (11)	0.0856 (16)	−0.0028 (9)	0.0116 (10)	−0.0178 (11)
C10	0.0753 (15)	0.0689 (14)	0.0686 (14)	0.0246 (12)	0.0234 (12)	0.0017 (11)
C11	0.0358 (8)	0.0400 (9)	0.0552 (10)	0.0021 (7)	0.0037 (7)	−0.0018 (8)
C12	0.0416 (9)	0.0453 (9)	0.0536 (10)	−0.0048 (7)	0.0060 (8)	−0.0056 (8)
C13	0.0437 (10)	0.0663 (12)	0.0486 (10)	0.0059 (9)	0.0002 (8)	−0.0017 (9)
C14	0.0420 (10)	0.0614 (12)	0.0512 (11)	0.0073 (9)	−0.0018 (8)	−0.0035 (9)
C15	0.0465 (11)	0.0773 (15)	0.0548 (12)	0.0054 (10)	0.0005 (9)	−0.0012 (10)
C16	0.0440 (11)	0.0945 (19)	0.0794 (16)	0.0116 (12)	−0.0074 (11)	−0.0006 (14)
C17	0.0622 (15)	0.112 (2)	0.0715 (17)	0.0029 (15)	−0.0201 (12)	0.0101 (15)
C18	0.0803 (19)	0.155 (3)	0.0513 (14)	0.012 (2)	−0.0112 (12)	−0.0078 (17)
C19	0.0598 (14)	0.122 (2)	0.0553 (13)	0.0187 (15)	0.0008 (11)	−0.0115 (14)
C20	0.0589 (12)	0.0555 (11)	0.0440 (10)	−0.0103 (9)	0.0031 (8)	0.0012 (8)
C21	0.0549 (11)	0.0461 (10)	0.0672 (13)	0.0014 (9)	0.0068 (10)	−0.0027 (9)
C22	0.0515 (11)	0.0505 (11)	0.0674 (13)	0.0014 (9)	0.0035 (9)	0.0008 (9)
C23	0.0590 (12)	0.0504 (11)	0.0662 (13)	−0.0052 (9)	0.0113 (10)	−0.0125 (10)
C24	0.0531 (11)	0.0497 (11)	0.0622 (12)	−0.0033 (9)	0.0113 (9)	−0.0086 (9)
C25	0.0506 (11)	0.0503 (10)	0.0551 (11)	−0.0004 (8)	−0.0028 (9)	0.0073 (9)
C26	0.0664 (14)	0.0652 (14)	0.0647 (13)	−0.0024 (11)	0.0084 (11)	0.0098 (11)
C27	0.0595 (14)	0.0806 (17)	0.0866 (18)	−0.0024 (12)	0.0090 (13)	0.0292 (15)
C28	0.0610 (15)	0.0745 (17)	0.100 (2)	−0.0154 (13)	−0.0108 (14)	0.0199 (15)
C29	0.0782 (18)	0.0761 (17)	0.103 (2)	−0.0223 (15)	−0.0043 (16)	−0.0118 (16)
C30	0.0657 (14)	0.0648 (14)	0.0804 (16)	−0.0138 (11)	0.0038 (12)	−0.0098 (12)

S1—C12	1.6735 (19)	C8—H8B	0.9700
N1—C13	1.268 (3)	C9—H9A	0.9700
N1—N2	1.397 (2)	C9—H9B	0.9700
N2—C11	1.384 (2)	C10—H10A	0.9700
N2—C12	1.386 (2)	C10—H10B	0.9700
N3—C11	1.300 (2)	C13—C14	1.457 (3)
N3—N4	1.382 (2)	C13—H13	0.9300
N4—C12	1.339 (3)	C14—C19	1.383 (3)
N4—C20	1.475 (2)	C14—C15	1.384 (3)
N5—C20	1.431 (3)	C15—C16	1.366 (3)
N5—C21	1.459 (3)	C16—C17	1.355 (4)
N5—C24	1.461 (3)	C16—H16	0.9300
N6—C25	1.419 (3)	C17—C18	1.365 (4)
N6—C23	1.454 (3)	C17—H17	0.9300
N6—C22	1.465 (3)	C18—C19	1.375 (4)
F1—C15	1.349 (3)	C18—H18	0.9300
F2—C19	1.335 (3)	C20—H20A	0.9700
C1—C11	1.500 (3)	C20—H20B	0.9700
C1—C8	1.537 (2)	C21—C22	1.507 (3)
C1—C2	1.539 (3)	C21—H21A	0.9700
C1—C9	1.539 (3)	C21—H21B	0.9700
C2—C3	1.537 (3)	C22—H22A	0.9700
C2—H2A	0.9700	C22—H22B	0.9700
C2—H2B	0.9700	C23—C24	1.506 (3)
C3—C4	1.526 (5)	C23—H23A	0.9700
C3—C10	1.525 (3)	C23—H23B	0.9700
C3—H3	0.9800	C24—H24A	0.9700
C4—C5	1.524 (5)	C24—H24B	0.9700
C4—H4A	0.9700	C25—C26	1.387 (3)
C4—H4B	0.9700	C25—C30	1.386 (3)
C5—C6	1.515 (4)	C26—C27	1.390 (4)
C5—C9	1.535 (3)	C26—H26	0.9300
C5—H5	0.9800	C27—C28	1.367 (4)
C6—C7	1.512 (4)	C27—H27	0.9300
C6—H6A	0.9700	C28—C29	1.368 (4)
C6—H6B	0.9700	C28—H28	0.9300
C7—C10	1.517 (3)	C29—C30	1.389 (4)
C7—C8	1.531 (3)	C29—H29	0.9300
C7—H7	0.9800	C30—H30	0.9300
C8—H8A	0.9700
C13—N1—N2	115.28 (17)	N3—C11—C1	123.27 (16)
C11—N2—C12	108.85 (15)	N2—C11—C1	126.81 (16)
C11—N2—N1	122.08 (15)	N4—C12—N2	102.93 (16)
C12—N2—N1	128.21 (15)	N4—C12—S1	127.49 (15)
C11—N3—N4	105.32 (15)	N2—C12—S1	129.57 (15)
C12—N4—N3	113.15 (16)	N1—C13—C14	121.72 (19)
C12—N4—C20	128.81 (17)	N1—C13—H13	119.1
N3—N4—C20	117.80 (16)	C14—C13—H13	119.1
C20—N5—C21	114.03 (17)	C19—C14—C15	113.36 (19)
C20—N5—C24	114.70 (17)	C19—C14—C13	126.9 (2)
C21—N5—C24	109.89 (16)	C15—C14—C13	119.77 (19)
C25—N6—C23	116.06 (16)	F1—C15—C16	117.5 (2)
C25—N6—C22	113.18 (16)	F1—C15—C14	117.06 (19)
C23—N6—C22	111.08 (17)	C16—C15—C14	125.4 (2)
C11—C1—C8	108.87 (16)	C17—C16—C15	117.9 (2)
C11—C1—C2	112.39 (16)	C17—C16—H16	121.1
C8—C1—C2	107.97 (16)	C15—C16—H16	121.1
C11—C1—C9	109.08 (15)	C16—C17—C18	120.7 (2)
C8—C1—C9	108.18 (16)	C16—C17—H17	119.7
C2—C1—C9	110.24 (18)	C18—C17—H17	119.7
C3—C2—C1	109.26 (18)	C17—C18—C19	119.2 (3)
C3—C2—H2A	109.8	C17—C18—H18	120.4
C1—C2—H2A	109.8	C19—C18—H18	120.4
C3—C2—H2B	109.8	F2—C19—C18	118.5 (2)
C1—C2—H2B	109.8	F2—C19—C14	118.0 (2)
H2A—C2—H2B	108.3	C18—C19—C14	123.4 (2)
C4—C3—C10	109.6 (2)	N5—C20—N4	116.50 (16)
C4—C3—C2	109.2 (2)	N5—C20—H20A	108.2
C10—C3—C2	110.0 (2)	N4—C20—H20A	108.2
C4—C3—H3	109.4	N5—C20—H20B	108.2
C10—C3—H3	109.4	N4—C20—H20B	108.2
C2—C3—H3	109.4	H20A—C20—H20B	107.3
C3—C4—C5	109.9 (2)	N5—C21—C22	109.98 (18)
C3—C4—H4A	109.7	N5—C21—H21A	109.7
C5—C4—H4A	109.7	C22—C21—H21A	109.7
C3—C4—H4B	109.7	N5—C21—H21B	109.7
C5—C4—H4B	109.7	C22—C21—H21B	109.7
H4A—C4—H4B	108.2	H21A—C21—H21B	108.2
C6—C5—C4	109.8 (2)	N6—C22—C21	110.58 (17)
C6—C5—C9	109.7 (2)	N6—C22—H22A	109.5
C4—C5—C9	108.9 (2)	C21—C22—H22A	109.5
C6—C5—H5	109.5	N6—C22—H22B	109.5
C4—C5—H5	109.5	C21—C22—H22B	109.5
C9—C5—H5	109.5	H22A—C22—H22B	108.1
C5—C6—C7	109.6 (2)	N6—C23—C24	110.50 (17)
C5—C6—H6A	109.8	N6—C23—H23A	109.6
C7—C6—H6A	109.8	C24—C23—H23A	109.6
C5—C6—H6B	109.8	N6—C23—H23B	109.6
C7—C6—H6B	109.8	C24—C23—H23B	109.6
H6A—C6—H6B	108.2	H23A—C23—H23B	108.1
C6—C7—C10	110.0 (2)	N5—C24—C23	109.68 (18)
C6—C7—C8	109.76 (18)	N5—C24—H24A	109.7
C10—C7—C8	109.45 (19)	C23—C24—H24A	109.7
C6—C7—H7	109.2	N5—C24—H24B	109.7
C10—C7—H7	109.2	C23—C24—H24B	109.7
C8—C7—H7	109.2	H24A—C24—H24B	108.2
C7—C8—C1	110.28 (17)	C26—C25—C30	117.7 (2)
C7—C8—H8A	109.6	C26—C25—N6	119.0 (2)
C1—C8—H8A	109.6	C30—C25—N6	123.3 (2)
C7—C8—H8B	109.6	C25—C26—C27	120.6 (3)
C1—C8—H8B	109.6	C25—C26—H26	119.7
H8A—C8—H8B	108.1	C27—C26—H26	119.7
C5—C9—C1	109.66 (18)	C28—C27—C26	121.1 (3)
C5—C9—H9A	109.7	C28—C27—H27	119.4
C1—C9—H9A	109.7	C26—C27—H27	119.4
C5—C9—H9B	109.7	C27—C28—C29	118.9 (3)
C1—C9—H9B	109.7	C27—C28—H28	120.6
H9A—C9—H9B	108.2	C29—C28—H28	120.6
C7—C10—C3	109.02 (19)	C28—C29—C30	120.7 (3)
C7—C10—H10A	109.9	C28—C29—H29	119.6
C3—C10—H10A	109.9	C30—C29—H29	119.6
C7—C10—H10B	109.9	C29—C30—C25	121.0 (3)
C3—C10—H10B	109.9	C29—C30—H30	119.5
H10A—C10—H10B	108.3	C25—C30—H30	119.5
N3—C11—N2	109.67 (16)
C13—N1—N2—C11	148.49 (19)	C11—N2—C12—N4	−1.8 (2)
C13—N1—N2—C12	−43.3 (3)	N1—N2—C12—N4	−171.19 (18)
C11—N3—N4—C12	1.3 (2)	C11—N2—C12—S1	176.97 (15)
C11—N3—N4—C20	176.19 (16)	N1—N2—C12—S1	7.5 (3)
C11—C1—C2—C3	179.79 (19)	N2—N1—C13—C14	177.22 (19)
C8—C1—C2—C3	59.7 (2)	N1—C13—C14—C19	10.4 (4)
C9—C1—C2—C3	−58.3 (2)	N1—C13—C14—C15	−169.8 (2)
C1—C2—C3—C4	59.4 (3)	C19—C14—C15—F1	179.2 (3)
C1—C2—C3—C10	−60.8 (3)	C13—C14—C15—F1	−0.7 (4)
C10—C3—C4—C5	58.8 (3)	C19—C14—C15—C16	−2.3 (4)
C2—C3—C4—C5	−61.7 (3)	C13—C14—C15—C16	177.9 (3)
C3—C4—C5—C6	−58.6 (3)	F1—C15—C16—C17	−179.7 (3)
C3—C4—C5—C9	61.6 (3)	C14—C15—C16—C17	1.7 (5)
C4—C5—C6—C7	59.2 (3)	C15—C16—C17—C18	−0.1 (5)
C9—C5—C6—C7	−60.4 (3)	C16—C17—C18—C19	−0.7 (6)
C5—C6—C7—C10	−60.6 (2)	C17—C18—C19—F2	179.1 (4)
C5—C6—C7—C8	59.9 (3)	C17—C18—C19—C14	0.0 (6)
C6—C7—C8—C1	−59.9 (2)	C15—C14—C19—F2	−177.8 (3)
C10—C7—C8—C1	60.9 (2)	C13—C14—C19—F2	2.0 (5)
C11—C1—C8—C7	177.53 (17)	C15—C14—C19—C18	1.4 (5)
C2—C1—C8—C7	−60.2 (2)	C13—C14—C19—C18	−178.8 (3)
C9—C1—C8—C7	59.1 (2)	C21—N5—C20—N4	−56.1 (2)
C6—C5—C9—C1	60.6 (3)	C24—N5—C20—N4	71.8 (2)
C4—C5—C9—C1	−59.6 (3)	C12—N4—C20—N5	−98.2 (2)
C11—C1—C9—C5	−177.6 (2)	N3—N4—C20—N5	87.8 (2)
C8—C1—C9—C5	−59.3 (3)	C20—N5—C21—C22	−170.14 (18)
C2—C1—C9—C5	58.6 (2)	C24—N5—C21—C22	59.5 (2)
C6—C7—C10—C3	60.6 (3)	C25—N6—C22—C21	−171.53 (18)
C8—C7—C10—C3	−60.0 (3)	C23—N6—C22—C21	55.8 (2)
C4—C3—C10—C7	−59.5 (3)	N5—C21—C22—N6	−57.1 (2)
C2—C3—C10—C7	60.5 (3)	C25—N6—C23—C24	172.32 (18)
N4—N3—C11—N2	−2.3 (2)	C22—N6—C23—C24	−56.5 (2)
N4—N3—C11—C1	−176.97 (16)	C20—N5—C24—C23	169.94 (17)
C12—N2—C11—N3	2.7 (2)	C21—N5—C24—C23	−60.0 (2)
N1—N2—C11—N3	172.89 (17)	N6—C23—C24—N5	58.5 (2)
C12—N2—C11—C1	177.08 (18)	C23—N6—C25—C26	−164.6 (2)
N1—N2—C11—C1	−12.7 (3)	C22—N6—C25—C26	65.2 (3)
C8—C1—C11—N3	−3.0 (3)	C23—N6—C25—C30	15.4 (3)
C2—C1—C11—N3	−122.6 (2)	C22—N6—C25—C30	−114.7 (2)
C9—C1—C11—N3	114.9 (2)	C30—C25—C26—C27	1.0 (3)
C8—C1—C11—N2	−176.68 (18)	N6—C25—C26—C27	−179.0 (2)
C2—C1—C11—N2	63.7 (2)	C25—C26—C27—C28	−1.0 (4)
C9—C1—C11—N2	−58.8 (3)	C26—C27—C28—C29	0.3 (4)
N3—N4—C12—N2	0.4 (2)	C27—C28—C29—C30	0.3 (5)
C20—N4—C12—N2	−173.89 (18)	C28—C29—C30—C25	−0.2 (5)
N3—N4—C12—S1	−178.41 (14)	C26—C25—C30—C29	−0.4 (4)
C20—N4—C12—S1	7.3 (3)	N6—C25—C30—C29	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···S1i	0.97	2.86	3.397 (2)	116
C28—H28···Cg1ii	0.93	2.99	3.832 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C25–C30 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯S1i	0.97	2.86	3.397 (2)	116
C28—H28⋯Cg1ii	0.93	2.99	3.832 (3)	151

Symmetry codes: (i) ; (ii) .