N'-Benzoyl-N-tert-butyl-2-chloro-N'-{[3-(6-chloro-3-pyrid-ylmethyl)-2-nitrimino-imidazolidin-1-yl]sulfan-yl}benzo-hydrazide.

In the title compound, C(27)H(27)Cl(2)N(7)O(4)S, the amide groups bearing the N-S group and the tert-butyl group have s-trans conformations. The steric size of the tert-butyl and [(6-chloro-3-pyrid-yl)meth-yl]imidazolidin-2-yl-idene groups cause the 2-chloro-benzoyl group and the benzyol group to be directed away from one another, forming a dihedral angle of 60.62 (17)°. The central N-N bond adopts a gauche conformation with a C-N-N-C torsion angle of -79.1 (2)°.

Related literature

1-tert-Butyl-1,2-diacyl­hydrazines are a new class of insect growth regulators, which have been found to mimic the action of 20-hydroxyecdysone in activating the ecdysone receptor, which leads to lethal premature moulting, see: Wing (1988 ▶, 1995 ▶); Wing et al. (1988 ▶). 1-tert–Butyl-2-(4-ethyl­benzo­yl)-1-(3,5-dimethyl­benzo­yl) hydrazine (tebufenozide, RH-5992) was the first non-steroidal ecdysone agonist to be available commercially as a lepidopteran-specific insecticide, see: Dhadialla & Jansson (1999 ▶). At present, three further structural analogues are available, viz. methoxy­fenozide (RH-2485), halofenozide (RH-0345) and chromafenozide (ANS-118), see: Carlson et al. (2001 ▶); Yanagi et al. (2000 ▶). The gauche conformation of the N—N bond has been observed in other hydrazine derivatives, see: Chan et al. (1990 ▶); Wolfe (1972 ▶).

Experimental

Crystal data

C27H27Cl2N7O4S

M = 616.52

Monoclinic,

a = 11.2271 (19) Å

b = 10.1360 (17) Å

c = 25.660 (4) Å

β = 102.233 (2)°

V = 2853.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.32 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.771, T max = 1.000 (expected range = 0.745–0.966)

15046 measured reflections

5028 independent reflections

3977 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.06

5028 reflections

373 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028943/su2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028943/su2122Isup2.hkl

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

C27H27Cl2N7O4S	F(000) = 1280
Mr = 616.52	Dx = 1.435 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4468 reflections
a = 11.2271 (19) Å	θ = 2.6–24.9°
b = 10.1360 (17) Å	µ = 0.35 mm−1
c = 25.660 (4) Å	T = 293 K
β = 102.233 (2)°	Prism, colorless
V = 2853.7 (8) Å3	0.32 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5028 independent reflections
Radiation source: fine-focus sealed tube	3977 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.771, Tmax = 1.000	k = −12→9
15046 measured reflections	l = −30→30

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0698P)2 + 1.7665P] where P = (Fo2 + 2Fc2)/3
5028 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.45 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
Cl1	−0.00213 (9)	0.49776 (9)	0.40638 (4)	0.0728 (3)
Cl2	−0.11702 (9)	0.58796 (9)	0.15026 (4)	0.0810 (3)
S1	0.14276 (6)	0.07999 (6)	0.09665 (2)	0.03344 (17)
O1	0.06429 (15)	0.32169 (19)	0.17809 (6)	0.0420 (4)
O2	0.11152 (17)	0.45234 (18)	0.07819 (8)	0.0491 (5)
O3	0.0674 (2)	−0.1707 (2)	0.14149 (9)	0.0608 (6)
O4	−0.1101 (2)	−0.0950 (2)	0.14492 (11)	0.0752 (7)
N1	−0.03379 (17)	0.2563 (2)	0.09591 (7)	0.0325 (4)
N2	0.08279 (17)	0.23245 (19)	0.08582 (7)	0.0310 (4)
N3	0.21131 (18)	0.0735 (2)	0.16139 (7)	0.0333 (4)
N4	0.2211 (2)	0.0837 (2)	0.24814 (8)	0.0418 (5)
N5	0.0473 (2)	−0.0140 (2)	0.20121 (8)	0.0439 (5)
N6	0.0006 (2)	−0.0955 (2)	0.15925 (9)	0.0476 (6)
N7	0.1465 (2)	0.3052 (3)	0.40109 (9)	0.0525 (6)
C1	−0.1896 (3)	0.4535 (3)	0.17016 (13)	0.0583 (8)
C2	−0.2914 (3)	0.4740 (5)	0.19289 (16)	0.0796 (11)
H2	−0.3207	0.5589	0.1958	0.095*
C3	−0.3459 (4)	0.3701 (5)	0.21039 (17)	0.0872 (13)
H3	−0.4121	0.3841	0.2262	0.105*
C4	−0.3057 (3)	0.2426 (5)	0.20542 (15)	0.0795 (11)
H4	−0.3468	0.1727	0.2171	0.095*
C5	−0.2077 (2)	0.2171 (4)	0.18388 (12)	0.0620 (9)
H5	−0.1792	0.1314	0.1820	0.074*
C6	−0.1483 (2)	0.3285 (3)	0.16371 (10)	0.0429 (6)
C7	−0.0311 (2)	0.3051 (2)	0.14593 (9)	0.0333 (5)
C8	−0.1401 (2)	0.2467 (3)	0.04779 (9)	0.0387 (6)
C9	−0.2336 (3)	0.1494 (4)	0.05798 (15)	0.0883 (14)
H9A	−0.2744	0.1846	0.0842	0.132*
H9B	−0.1941	0.0681	0.0708	0.132*
H9C	−0.2920	0.1334	0.0254	0.132*
C10	−0.1969 (3)	0.3813 (3)	0.03440 (14)	0.0670 (9)
H10A	−0.2587	0.3756	0.0023	0.100*
H10B	−0.1352	0.4427	0.0293	0.100*
H10C	−0.2327	0.4110	0.0631	0.100*
C11	−0.0898 (3)	0.2030 (5)	−0.00012 (13)	0.0930 (15)
H11A	−0.0538	0.1171	0.0066	0.139*
H11B	−0.0292	0.2647	−0.0060	0.139*
H11C	−0.1549	0.1996	−0.0311	0.139*
C12	0.1470 (2)	0.3426 (2)	0.07288 (9)	0.0345 (5)
C13	0.2546 (2)	0.3156 (3)	0.04891 (10)	0.0387 (6)
C14	0.2425 (3)	0.2453 (3)	0.00197 (12)	0.0538 (7)
H14	0.1692	0.2035	−0.0124	0.065*
C15	0.3376 (3)	0.2368 (4)	−0.02354 (13)	0.0677 (9)
H15	0.3278	0.1915	−0.0557	0.081*
C16	0.4471 (3)	0.2949 (4)	−0.00196 (15)	0.0699 (10)
H16	0.5123	0.2870	−0.0188	0.084*
C17	0.4599 (3)	0.3646 (4)	0.04451 (15)	0.0670 (9)
H17	0.5342	0.4041	0.0592	0.080*
C18	0.3636 (2)	0.3768 (3)	0.06963 (12)	0.0504 (7)
H18	0.3724	0.4265	0.1007	0.061*
C19	0.3185 (2)	0.1561 (3)	0.18253 (10)	0.0453 (6)
H19A	0.3066	0.2453	0.1687	0.054*
H19B	0.3912	0.1195	0.1733	0.054*
C20	0.3281 (3)	0.1541 (4)	0.24168 (12)	0.0633 (9)
H20A	0.4015	0.1088	0.2596	0.076*
H20B	0.3286	0.2429	0.2558	0.076*
C21	0.1539 (2)	0.0411 (2)	0.20220 (9)	0.0346 (5)
C22	0.1974 (3)	0.0529 (3)	0.30041 (10)	0.0506 (7)
H22A	0.2731	0.0267	0.3240	0.061*
H22B	0.1417	−0.0212	0.2971	0.061*
C23	0.1436 (2)	0.1681 (3)	0.32484 (9)	0.0400 (6)
C24	0.1910 (3)	0.2073 (3)	0.37612 (10)	0.0467 (7)
H24	0.2590	0.1626	0.3949	0.056*
C25	0.0517 (3)	0.3670 (3)	0.37382 (11)	0.0464 (7)
C26	−0.0045 (3)	0.3379 (4)	0.32266 (13)	0.0657 (9)
H26	−0.0724	0.3849	0.3051	0.079*
C27	0.0435 (3)	0.2360 (3)	0.29801 (12)	0.0628 (9)
H27	0.0079	0.2132	0.2631	0.075*

	U11	U22	U33	U12	U13	U23
Cl1	0.0906 (6)	0.0576 (5)	0.0834 (6)	0.0160 (4)	0.0483 (5)	−0.0003 (4)
Cl2	0.0914 (7)	0.0443 (5)	0.1006 (7)	−0.0010 (4)	0.0053 (5)	−0.0035 (4)
S1	0.0415 (3)	0.0298 (3)	0.0286 (3)	0.0009 (3)	0.0063 (2)	−0.0033 (2)
O1	0.0343 (9)	0.0553 (12)	0.0340 (9)	0.0017 (8)	0.0014 (7)	−0.0058 (8)
O2	0.0548 (11)	0.0321 (11)	0.0659 (13)	−0.0003 (9)	0.0254 (10)	−0.0003 (9)
O3	0.0806 (15)	0.0374 (12)	0.0652 (13)	−0.0030 (11)	0.0173 (11)	−0.0078 (10)
O4	0.0554 (14)	0.0655 (16)	0.0953 (18)	−0.0118 (11)	−0.0055 (13)	−0.0019 (13)
N1	0.0277 (10)	0.0387 (11)	0.0301 (10)	−0.0007 (9)	0.0041 (8)	−0.0005 (8)
N2	0.0311 (10)	0.0308 (11)	0.0314 (10)	−0.0001 (8)	0.0074 (8)	0.0010 (8)
N3	0.0355 (10)	0.0325 (11)	0.0309 (10)	0.0015 (9)	0.0043 (8)	−0.0018 (8)
N4	0.0521 (13)	0.0433 (13)	0.0282 (10)	0.0020 (10)	0.0045 (9)	−0.0005 (9)
N5	0.0522 (14)	0.0419 (13)	0.0392 (12)	−0.0072 (11)	0.0133 (10)	0.0006 (10)
N6	0.0571 (15)	0.0339 (13)	0.0494 (13)	−0.0090 (11)	0.0056 (12)	0.0077 (10)
N7	0.0586 (15)	0.0557 (15)	0.0410 (12)	0.0078 (12)	0.0057 (11)	−0.0084 (11)
C1	0.0517 (17)	0.059 (2)	0.0607 (19)	0.0063 (15)	0.0032 (14)	−0.0145 (15)
C2	0.063 (2)	0.097 (3)	0.079 (2)	0.018 (2)	0.0165 (19)	−0.030 (2)
C3	0.062 (2)	0.121 (4)	0.085 (3)	0.017 (2)	0.029 (2)	−0.018 (3)
C4	0.063 (2)	0.109 (3)	0.070 (2)	−0.012 (2)	0.0231 (18)	0.011 (2)
C5	0.0303 (14)	0.093 (3)	0.0626 (19)	−0.0023 (15)	0.0103 (13)	−0.0202 (18)
C6	0.0368 (14)	0.0541 (17)	0.0365 (13)	0.0026 (12)	0.0052 (11)	−0.0059 (12)
C7	0.0357 (13)	0.0306 (13)	0.0335 (12)	−0.0004 (10)	0.0071 (10)	0.0015 (10)
C8	0.0350 (13)	0.0464 (15)	0.0307 (12)	−0.0004 (11)	−0.0019 (10)	0.0003 (11)
C9	0.080 (2)	0.093 (3)	0.073 (2)	−0.048 (2)	−0.0287 (19)	0.026 (2)
C10	0.0602 (19)	0.063 (2)	0.066 (2)	0.0062 (16)	−0.0140 (16)	0.0131 (16)
C11	0.064 (2)	0.161 (4)	0.0438 (18)	0.030 (2)	−0.0115 (16)	−0.039 (2)
C12	0.0366 (13)	0.0347 (14)	0.0323 (12)	−0.0034 (11)	0.0071 (10)	−0.0013 (10)
C13	0.0420 (14)	0.0359 (14)	0.0407 (13)	−0.0006 (11)	0.0141 (11)	0.0046 (11)
C14	0.0537 (18)	0.060 (2)	0.0520 (17)	−0.0064 (14)	0.0199 (14)	−0.0092 (14)
C15	0.071 (2)	0.084 (3)	0.0565 (19)	0.0039 (19)	0.0341 (17)	−0.0095 (17)
C16	0.060 (2)	0.081 (3)	0.081 (2)	0.0067 (18)	0.0424 (18)	0.005 (2)
C17	0.0424 (17)	0.079 (2)	0.084 (2)	−0.0078 (16)	0.0235 (16)	−0.003 (2)
C18	0.0431 (15)	0.0540 (18)	0.0561 (17)	−0.0040 (13)	0.0150 (13)	−0.0050 (14)
C19	0.0390 (14)	0.0513 (17)	0.0442 (15)	−0.0039 (12)	0.0054 (11)	−0.0089 (12)
C20	0.062 (2)	0.078 (2)	0.0435 (16)	−0.0180 (17)	−0.0028 (14)	−0.0057 (15)
C21	0.0444 (14)	0.0271 (12)	0.0311 (12)	0.0074 (10)	0.0054 (10)	0.0025 (9)
C22	0.076 (2)	0.0428 (16)	0.0308 (13)	0.0079 (14)	0.0067 (13)	0.0051 (11)
C23	0.0505 (15)	0.0385 (15)	0.0303 (12)	0.0006 (12)	0.0072 (11)	0.0032 (10)
C24	0.0507 (16)	0.0485 (17)	0.0375 (14)	0.0095 (13)	0.0020 (12)	−0.0009 (12)
C25	0.0529 (16)	0.0415 (15)	0.0501 (16)	0.0011 (13)	0.0228 (13)	0.0040 (12)
C26	0.063 (2)	0.073 (2)	0.0566 (19)	0.0275 (17)	0.0018 (15)	0.0078 (17)
C27	0.072 (2)	0.073 (2)	0.0358 (15)	0.0169 (17)	−0.0070 (14)	−0.0010 (14)

Cl1—C25	1.742 (3)	C9—H9B	0.9600
Cl2—C1	1.721 (4)	C9—H9C	0.9600
S1—N3	1.6777 (19)	C10—H10A	0.9600
S1—N2	1.685 (2)	C10—H10B	0.9600
O1—C7	1.218 (3)	C10—H10C	0.9600
O2—C12	1.199 (3)	C11—H11A	0.9600
O3—N6	1.224 (3)	C11—H11B	0.9600
O4—N6	1.218 (3)	C11—H11C	0.9600
N1—C7	1.370 (3)	C12—C13	1.493 (3)
N1—N2	1.408 (3)	C13—C18	1.375 (4)
N1—C8	1.527 (3)	C13—C14	1.381 (4)
N2—C12	1.407 (3)	C14—C15	1.368 (4)
N3—C21	1.381 (3)	C14—H14	0.9300
N3—C19	1.471 (3)	C15—C16	1.370 (5)
N4—C21	1.330 (3)	C15—H15	0.9300
N4—C20	1.435 (4)	C16—C17	1.367 (5)
N4—C22	1.456 (3)	C16—H16	0.9300
N5—C21	1.315 (3)	C17—C18	1.377 (4)
N5—N6	1.370 (3)	C17—H17	0.9300
N7—C25	1.304 (4)	C18—H18	0.9300
N7—C24	1.334 (4)	C19—C20	1.499 (4)
C1—C6	1.371 (4)	C19—H19A	0.9700
C1—C2	1.403 (5)	C19—H19B	0.9700
C2—C3	1.342 (6)	C20—H20A	0.9700
C2—H2	0.9300	C20—H20B	0.9700
C3—C4	1.384 (6)	C22—C23	1.510 (4)
C3—H3	0.9300	C22—H22A	0.9700
C4—C5	1.356 (5)	C22—H22B	0.9700
C4—H4	0.9300	C23—C24	1.370 (4)
C5—C6	1.461 (5)	C23—C27	1.372 (4)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.500 (3)	C25—C26	1.363 (4)
C8—C9	1.503 (4)	C26—C27	1.379 (5)
C8—C10	1.515 (4)	C26—H26	0.9300
C8—C11	1.523 (4)	C27—H27	0.9300
C9—H9A	0.9600
N3—S1—N2	106.41 (10)	C8—C11—H11C	109.5
C7—N1—N2	113.44 (18)	H11A—C11—H11C	109.5
C7—N1—C8	129.7 (2)	H11B—C11—H11C	109.5
N2—N1—C8	115.95 (18)	O2—C12—N2	120.7 (2)
C12—N2—N1	116.74 (19)	O2—C12—C13	122.3 (2)
C12—N2—S1	124.08 (16)	N2—C12—C13	116.8 (2)
N1—N2—S1	118.79 (15)	C18—C13—C14	119.0 (3)
C21—N3—C19	109.44 (19)	C18—C13—C12	119.3 (2)
C21—N3—S1	124.76 (16)	C14—C13—C12	121.0 (2)
C19—N3—S1	120.71 (17)	C15—C14—C13	120.5 (3)
C21—N4—C20	113.0 (2)	C15—C14—H14	119.7
C21—N4—C22	124.5 (2)	C13—C14—H14	119.7
C20—N4—C22	122.2 (2)	C14—C15—C16	120.3 (3)
C21—N5—N6	117.8 (2)	C14—C15—H15	119.9
O4—N6—O3	123.8 (3)	C16—C15—H15	119.9
O4—N6—N5	115.5 (3)	C17—C16—C15	119.7 (3)
O3—N6—N5	120.4 (2)	C17—C16—H16	120.2
C25—N7—C24	116.5 (2)	C15—C16—H16	120.2
C6—C1—C2	120.9 (3)	C16—C17—C18	120.4 (3)
C6—C1—Cl2	120.2 (2)	C16—C17—H17	119.8
C2—C1—Cl2	119.0 (3)	C18—C17—H17	119.8
C3—C2—C1	119.5 (4)	C13—C18—C17	120.1 (3)
C3—C2—H2	120.3	C13—C18—H18	119.9
C1—C2—H2	120.3	C17—C18—H18	119.9
C2—C3—C4	121.4 (4)	N3—C19—C20	104.1 (2)
C2—C3—H3	119.3	N3—C19—H19A	110.9
C4—C3—H3	119.3	C20—C19—H19A	110.9
C5—C4—C3	121.6 (4)	N3—C19—H19B	110.9
C5—C4—H4	119.2	C20—C19—H19B	110.9
C3—C4—H4	119.2	H19A—C19—H19B	109.0
C4—C5—C6	117.9 (3)	N4—C20—C19	104.0 (2)
C4—C5—H5	121.1	N4—C20—H20A	111.0
C6—C5—H5	121.1	C19—C20—H20A	111.0
C1—C6—C5	118.7 (3)	N4—C20—H20B	111.0
C1—C6—C7	121.6 (3)	C19—C20—H20B	111.0
C5—C6—C7	118.8 (2)	H20A—C20—H20B	109.0
O1—C7—N1	121.8 (2)	N5—C21—N4	119.9 (2)
O1—C7—C6	118.3 (2)	N5—C21—N3	131.0 (2)
N1—C7—C6	119.7 (2)	N4—C21—N3	109.0 (2)
C9—C8—C10	110.7 (3)	N4—C22—C23	112.6 (2)
C9—C8—C11	110.0 (3)	N4—C22—H22A	109.1
C10—C8—C11	106.8 (3)	C23—C22—H22A	109.1
C9—C8—N1	110.9 (2)	N4—C22—H22B	109.1
C10—C8—N1	110.2 (2)	C23—C22—H22B	109.1
C11—C8—N1	108.2 (2)	H22A—C22—H22B	107.8
C8—C9—H9A	109.5	C24—C23—C27	116.5 (3)
C8—C9—H9B	109.5	C24—C23—C22	121.0 (2)
H9A—C9—H9B	109.5	C27—C23—C22	122.5 (2)
C8—C9—H9C	109.5	N7—C24—C23	124.7 (3)
H9A—C9—H9C	109.5	N7—C24—H24	117.7
H9B—C9—H9C	109.5	C23—C24—H24	117.7
C8—C10—H10A	109.5	N7—C25—C26	124.9 (3)
C8—C10—H10B	109.5	N7—C25—Cl1	115.8 (2)
H10A—C10—H10B	109.5	C26—C25—Cl1	119.3 (2)
C8—C10—H10C	109.5	C25—C26—C27	117.2 (3)
H10A—C10—H10C	109.5	C25—C26—H26	121.4
H10B—C10—H10C	109.5	C27—C26—H26	121.4
C8—C11—H11A	109.5	C23—C27—C26	120.3 (3)
C8—C11—H11B	109.5	C23—C27—H27	119.9
H11A—C11—H11B	109.5	C26—C27—H27	119.9
C7—N1—N2—C12	−79.1 (2)	N2—C12—C13—C18	−130.5 (3)
C8—N1—N2—C12	91.0 (2)	O2—C12—C13—C14	−116.9 (3)
C7—N1—N2—S1	94.0 (2)	N2—C12—C13—C14	58.8 (3)
C8—N1—N2—S1	−95.8 (2)	C18—C13—C14—C15	0.0 (5)
N3—S1—N2—C12	86.82 (19)	C12—C13—C14—C15	170.8 (3)
N3—S1—N2—N1	−85.75 (17)	C13—C14—C15—C16	1.8 (5)
N2—S1—N3—C21	86.2 (2)	C14—C15—C16—C17	−1.8 (6)
N2—S1—N3—C19	−65.8 (2)	C15—C16—C17—C18	−0.1 (6)
C21—N5—N6—O4	−146.8 (2)	C14—C13—C18—C17	−1.8 (4)
C21—N5—N6—O3	39.2 (3)	C12—C13—C18—C17	−172.8 (3)
C6—C1—C2—C3	2.6 (5)	C16—C17—C18—C13	1.9 (5)
Cl2—C1—C2—C3	−177.5 (3)	C21—N3—C19—C20	7.4 (3)
C1—C2—C3—C4	−1.5 (6)	S1—N3—C19—C20	163.2 (2)
C2—C3—C4—C5	1.7 (6)	C21—N4—C20—C19	2.2 (3)
C3—C4—C5—C6	−2.7 (5)	C22—N4—C20—C19	176.7 (2)
C2—C1—C6—C5	−3.6 (4)	N3—C19—C20—N4	−5.6 (3)
Cl2—C1—C6—C5	176.5 (2)	N6—N5—C21—N4	−157.9 (2)
C2—C1—C6—C7	−172.2 (3)	N6—N5—C21—N3	27.1 (4)
Cl2—C1—C6—C7	7.8 (4)	C20—N4—C21—N5	−173.5 (3)
C4—C5—C6—C1	3.6 (4)	C22—N4—C21—N5	12.1 (4)
C4—C5—C6—C7	172.6 (3)	C20—N4—C21—N3	2.5 (3)
N2—N1—C7—O1	−1.8 (3)	C22—N4—C21—N3	−171.9 (2)
C8—N1—C7—O1	−170.3 (2)	C19—N3—C21—N5	169.1 (3)
N2—N1—C7—C6	−176.7 (2)	S1—N3—C21—N5	14.4 (4)
C8—N1—C7—C6	14.9 (4)	C19—N3—C21—N4	−6.3 (3)
C1—C6—C7—O1	75.6 (3)	S1—N3—C21—N4	−160.98 (17)
C5—C6—C7—O1	−93.0 (3)	C21—N4—C22—C23	−105.2 (3)
C1—C6—C7—N1	−109.4 (3)	C20—N4—C22—C23	80.9 (3)
C5—C6—C7—N1	82.0 (3)	N4—C22—C23—C24	−130.6 (3)
C7—N1—C8—C9	−67.4 (4)	N4—C22—C23—C27	51.4 (4)
N2—N1—C8—C9	124.4 (3)	C25—N7—C24—C23	−0.5 (5)
C7—N1—C8—C10	55.6 (3)	C27—C23—C24—N7	0.2 (5)
N2—N1—C8—C10	−112.7 (3)	C22—C23—C24—N7	−177.9 (3)
C7—N1—C8—C11	172.0 (3)	C24—N7—C25—C26	0.6 (5)
N2—N1—C8—C11	3.7 (3)	C24—N7—C25—Cl1	−178.1 (2)
N1—N2—C12—O2	10.9 (3)	N7—C25—C26—C27	−0.4 (5)
S1—N2—C12—O2	−161.8 (2)	Cl1—C25—C26—C27	178.2 (3)
N1—N2—C12—C13	−164.91 (19)	C24—C23—C27—C26	−0.1 (5)
S1—N2—C12—C13	22.4 (3)	C22—C23—C27—C26	178.0 (3)
O2—C12—C13—C18	53.8 (4)	C25—C26—C27—C23	0.1 (5)