A rare case of a 2:2:1 ternary cocrystal of pyri­dine sulfides and tri­thio­cyanuric acid

We report a rare case of a 2:2:1 ternary cocrystal consisting of two tri­­thio­cyanuric acid mol­ecules, two bis­(pyri­din-4-yl) sulfide mol­ecules and 1,4-bis­(pyri­din-4-yl)tetra­sulfane, namely, 1,3,5-triazinane-2,4,6-tri­thione–4-(pyri­din-4-ylsulfan­yl)pyri­dine–1,4-bis­(pyri­din-4-yl)tetra­sulfane (2/2/1), 2C₃H₃N₃S₃·2C₁₀H₈N₂S·C₁₀H₈N₂S₄. This inter­esting crystal structure with five neutral mol­ecules per asym­metric unit was synthesized and characterized by means of X-ray dif­fraction (XRD) experiments and quantum-chemical modelling. Among various specific inter­actions, hydrogen and halogen bridges have a significant role in stabilizing the crystal structure. In particular, the role played by stacking inter­actions has been revealed by structure analysis and theoretical calculations. Crystallization was spontaneous and reproducible. One of the com­ponents, 1,4-bis­(pyri­din-4-yl)tetra­sulfane, has been characterized by XRD for the first time.

Computing details

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: SHELXL2018 (Sheldrick, 2015b) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

1,3,5-Triazinane-2,4,6-trithione–4-(pyridin-4-ylsulfanyl)pyridine–1,4-bis(pyridin-4-yl)tetrasulfane (2/2/1)

Crystal data

2C3H3N3S3·2C10H8N2S·C10H8N2S4	Z = 2
Mr = 1015.44	F(000) = 1044
Triclinic, P1	Dx = 1.526 Mg m^−3
a = 9.8898 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 15.8351 (2) Å	Cell parameters from 62113 reflections
c = 16.4327 (1) Å	θ = 3.0–76.1°
α = 111.840 (1)°	µ = 5.88 mm^−1
β = 99.655 (1)°	T = 150 K
γ = 104.689 (1)°	Block, yellow
V = 2210.08 (4) Å^3	0.21 × 0.19 × 0.11 mm

Data collection

XtaLAB Synergy Dualflex HyPix diffractometer	8117 independent reflections
Radiation source: micro-focus sealed X-ray tube	7622 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.053
ω scans	θmax = 68.5°, θmin = 3.0°
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015) based on expressions derived by Clark & Reid (1995)]	h = −11→11
Tmin = 0.905, Tmax = 0.949	k = −18→19
97687 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 2.1831P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
8117 reflections	Δρmax = 0.90 e Å^−3
541 parameters	Δρmin = −0.54 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
S14A	0.45301 (7)	0.72754 (5)	0.51736 (4)	0.03680 (14)
S6A	0.11717 (7)	0.08688 (5)	0.47154 (4)	0.03876 (15)
S4	0.64345 (8)	0.47550 (5)	0.09540 (4)	0.04126 (16)
S4A	0.19866 (7)	0.30095 (5)	0.29083 (4)	0.03966 (15)
S6	0.67670 (7)	0.28206 (5)	0.29409 (4)	0.03959 (15)
S214	0.51010 (7)	0.78854 (5)	0.13003 (4)	0.04105 (15)
S14	0.93259 (8)	0.51217 (5)	0.72259 (4)	0.04151 (15)
S2	0.89149 (8)	0.20942 (5)	0.00995 (5)	0.04610 (17)
S2A	0.38249 (9)	0.00076 (5)	0.21551 (5)	0.04830 (18)
S215	0.60762 (9)	0.70169 (5)	0.16163 (5)	0.05069 (18)
S114	0.94467 (9)	0.84802 (6)	0.21324 (5)	0.0555 (2)
S115	0.79305 (11)	0.79720 (6)	0.27025 (5)	0.0605 (2)
N1A	0.2510 (2)	0.05711 (14)	0.34230 (13)	0.0320 (4)
H1A	0.263049	0.010298	0.353718	0.038*
N3A	0.2798 (2)	0.14637 (14)	0.25888 (12)	0.0319 (4)
H3A	0.306569	0.155519	0.214779	0.038*
N5A	0.1704 (2)	0.18672 (14)	0.37471 (13)	0.0327 (4)
H5A	0.129874	0.223509	0.406897	0.039*
N5	0.6707 (2)	0.37086 (14)	0.18696 (12)	0.0321 (4)
H5	0.625246	0.401656	0.220621	0.039*
N1	0.7795 (2)	0.25407 (14)	0.15023 (13)	0.0327 (4)
H1	0.804766	0.209897	0.160291	0.039*
N3	0.7685 (2)	0.34177 (14)	0.06562 (13)	0.0326 (4)
H3	0.788665	0.355047	0.021897	0.039*
N11A	0.5505 (2)	0.48681 (15)	0.30347 (14)	0.0363 (4)
N211	0.6627 (2)	0.83718 (16)	−0.10083 (13)	0.0378 (5)
N21A	0.3125 (2)	0.91838 (15)	0.39551 (14)	0.0385 (5)
N21	0.8222 (2)	0.39099 (15)	0.92374 (14)	0.0379 (5)
N11	1.0759 (2)	0.31365 (15)	0.49983 (14)	0.0367 (4)
N111	0.8457 (2)	1.10050 (15)	0.17649 (15)	0.0403 (5)
C6A	0.1828 (3)	0.11167 (17)	0.39294 (15)	0.0311 (5)
C4A	0.2181 (3)	0.20796 (17)	0.30836 (15)	0.0324 (5)
C14A	0.4914 (3)	0.63826 (17)	0.43071 (15)	0.0321 (5)
C2	0.8102 (3)	0.27077 (17)	0.07846 (15)	0.0333 (5)
C14	0.9889 (3)	0.43199 (17)	0.63876 (17)	0.0350 (5)
C2A	0.3019 (3)	0.07154 (17)	0.27423 (15)	0.0331 (5)
C25	0.8759 (3)	0.36327 (19)	0.78098 (16)	0.0368 (5)
H25	0.886205	0.320460	0.727471	0.044*
C15	1.0842 (3)	0.38746 (18)	0.65830 (17)	0.0361 (5)
H15	1.122352	0.397300	0.718120	0.043*
C24	0.8960 (3)	0.45905 (18)	0.79758 (16)	0.0347 (5)
C4	0.6970 (3)	0.39323 (17)	0.11726 (15)	0.0321 (5)
C213	0.5455 (3)	0.87480 (19)	0.01797 (17)	0.0393 (5)
H213	0.494653	0.911561	0.048994	0.047*
C15A	0.5600 (3)	0.58280 (18)	0.45825 (16)	0.0369 (5)
H15A	0.588410	0.595649	0.519771	0.044*
C24A	0.4011 (3)	0.79975 (17)	0.46653 (15)	0.0333 (5)
C214	0.5790 (3)	0.80605 (18)	0.04220 (15)	0.0347 (5)
C6	0.7114 (3)	0.30303 (17)	0.20706 (15)	0.0322 (5)
C16	1.1217 (3)	0.32803 (19)	0.58717 (16)	0.0366 (5)
H16	1.182565	0.295790	0.600416	0.044*
C25A	0.2794 (3)	0.82454 (18)	0.48064 (17)	0.0377 (5)
H25A	0.224825	0.801202	0.513522	0.045*
C26	0.8400 (3)	0.33326 (19)	0.84614 (17)	0.0380 (5)
H26	0.827702	0.269397	0.835240	0.046*
C12A	0.4852 (3)	0.54177 (19)	0.27839 (16)	0.0382 (5)
H12A	0.460276	0.528501	0.216673	0.046*
C23	0.8768 (3)	0.51929 (19)	0.87732 (18)	0.0405 (6)
H23	0.888841	0.583561	0.890161	0.049*
C22A	0.4308 (3)	0.89441 (19)	0.38293 (17)	0.0381 (5)
H22A	0.482575	0.917830	0.348975	0.046*
C23A	0.4796 (3)	0.83703 (19)	0.41756 (17)	0.0390 (5)
H23A	0.563477	0.823520	0.408336	0.047*
C13	0.9409 (3)	0.41929 (19)	0.54936 (17)	0.0385 (5)
H13	0.877536	0.449263	0.534302	0.046*
C216	0.6955 (3)	0.7717 (2)	−0.07614 (16)	0.0396 (6)
H216	0.747147	0.736386	−0.108066	0.047*
C215	0.6567 (3)	0.75369 (19)	−0.00536 (16)	0.0384 (5)
H215	0.681979	0.707641	0.009907	0.046*
C16A	0.5854 (3)	0.50828 (19)	0.39281 (17)	0.0378 (5)
H16A	0.629422	0.470825	0.412015	0.045*
C13A	0.4527 (3)	0.61623 (19)	0.33782 (17)	0.0384 (5)
H13A	0.405871	0.651196	0.316444	0.046*
C212	0.5894 (3)	0.8874 (2)	−0.05349 (17)	0.0420 (6)
H212	0.566599	0.933685	−0.069591	0.050*
C22	0.8395 (3)	0.4822 (2)	0.93761 (18)	0.0421 (6)
H22	0.825691	0.523023	0.990795	0.051*
C112	0.8022 (3)	1.07305 (19)	0.23815 (18)	0.0424 (6)
H112	0.750865	1.106376	0.272466	0.051*
C116	0.9203 (3)	1.0510 (2)	0.12812 (19)	0.0447 (6)
H116	0.953098	1.069483	0.085403	0.054*
C113	0.8286 (3)	0.99818 (19)	0.25421 (19)	0.0444 (6)
H113	0.797315	0.982397	0.298682	0.053*
C26A	0.2402 (3)	0.88439 (19)	0.44516 (18)	0.0412 (6)
H26A	0.159884	0.901905	0.456289	0.049*
C12	0.9890 (3)	0.36121 (19)	0.48303 (17)	0.0406 (6)
H12	0.959386	0.354903	0.423640	0.049*
C114	0.9031 (3)	0.94725 (19)	0.20220 (18)	0.0444 (6)
C115	0.9506 (3)	0.9747 (2)	0.13823 (19)	0.0458 (6)
H115	1.001858	0.942321	0.102932	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S14A	0.0490 (3)	0.0454 (3)	0.0295 (3)	0.0235 (3)	0.0182 (2)	0.0226 (3)
S6A	0.0541 (4)	0.0466 (3)	0.0366 (3)	0.0253 (3)	0.0268 (3)	0.0290 (3)
S4	0.0650 (4)	0.0458 (4)	0.0363 (3)	0.0328 (3)	0.0269 (3)	0.0279 (3)
S4A	0.0604 (4)	0.0412 (3)	0.0338 (3)	0.0249 (3)	0.0212 (3)	0.0255 (3)
S6	0.0571 (4)	0.0490 (4)	0.0305 (3)	0.0276 (3)	0.0195 (3)	0.0269 (3)
S214	0.0537 (4)	0.0453 (3)	0.0351 (3)	0.0176 (3)	0.0232 (3)	0.0242 (3)
S14	0.0576 (4)	0.0439 (3)	0.0440 (3)	0.0268 (3)	0.0272 (3)	0.0295 (3)
S2	0.0694 (4)	0.0465 (4)	0.0418 (3)	0.0341 (3)	0.0322 (3)	0.0233 (3)
S2A	0.0776 (5)	0.0545 (4)	0.0444 (4)	0.0418 (4)	0.0401 (3)	0.0324 (3)
S215	0.0838 (5)	0.0424 (4)	0.0462 (4)	0.0272 (3)	0.0325 (4)	0.0312 (3)
S114	0.0632 (4)	0.0492 (4)	0.0586 (4)	0.0317 (4)	0.0060 (3)	0.0252 (3)
S115	0.1073 (7)	0.0595 (5)	0.0356 (3)	0.0466 (5)	0.0183 (4)	0.0317 (3)
N1A	0.0432 (11)	0.0344 (10)	0.0295 (9)	0.0175 (9)	0.0172 (8)	0.0201 (8)
N3A	0.0428 (11)	0.0371 (10)	0.0247 (9)	0.0162 (9)	0.0158 (8)	0.0187 (8)
N5A	0.0444 (11)	0.0376 (11)	0.0282 (9)	0.0197 (9)	0.0188 (8)	0.0199 (8)
N5	0.0434 (11)	0.0383 (11)	0.0251 (9)	0.0206 (9)	0.0157 (8)	0.0181 (8)
N1	0.0445 (11)	0.0349 (10)	0.0271 (9)	0.0193 (9)	0.0130 (8)	0.0174 (8)
N3	0.0461 (11)	0.0354 (10)	0.0256 (9)	0.0186 (9)	0.0170 (8)	0.0171 (8)
N11A	0.0440 (11)	0.0408 (11)	0.0330 (10)	0.0181 (9)	0.0170 (9)	0.0206 (9)
N211	0.0473 (12)	0.0459 (12)	0.0288 (10)	0.0184 (10)	0.0161 (9)	0.0215 (9)
N21A	0.0475 (12)	0.0409 (11)	0.0395 (11)	0.0209 (10)	0.0190 (9)	0.0241 (10)
N21	0.0460 (12)	0.0429 (12)	0.0323 (10)	0.0156 (9)	0.0170 (9)	0.0216 (9)
N11	0.0451 (11)	0.0419 (11)	0.0331 (10)	0.0174 (9)	0.0166 (9)	0.0232 (9)
N111	0.0443 (12)	0.0365 (11)	0.0413 (11)	0.0167 (9)	0.0095 (9)	0.0177 (9)
C6A	0.0377 (12)	0.0347 (12)	0.0266 (11)	0.0138 (10)	0.0121 (9)	0.0171 (10)
C4A	0.0389 (12)	0.0373 (12)	0.0253 (10)	0.0128 (10)	0.0108 (9)	0.0176 (10)
C14A	0.0361 (12)	0.0374 (12)	0.0294 (11)	0.0134 (10)	0.0149 (9)	0.0185 (10)
C2	0.0402 (12)	0.0343 (12)	0.0271 (11)	0.0132 (10)	0.0110 (9)	0.0144 (10)
C14	0.0409 (13)	0.0349 (12)	0.0368 (12)	0.0129 (10)	0.0158 (10)	0.0218 (10)
C2A	0.0395 (12)	0.0371 (13)	0.0274 (11)	0.0139 (10)	0.0129 (9)	0.0171 (10)
C25	0.0447 (13)	0.0420 (13)	0.0293 (11)	0.0169 (11)	0.0157 (10)	0.0181 (10)
C15	0.0410 (13)	0.0423 (13)	0.0325 (12)	0.0161 (11)	0.0139 (10)	0.0214 (11)
C24	0.0353 (12)	0.0436 (14)	0.0324 (12)	0.0144 (10)	0.0123 (10)	0.0223 (11)
C4	0.0413 (12)	0.0336 (12)	0.0241 (10)	0.0137 (10)	0.0109 (9)	0.0143 (9)
C213	0.0491 (14)	0.0442 (14)	0.0343 (12)	0.0210 (12)	0.0196 (11)	0.0209 (11)
C15A	0.0462 (13)	0.0416 (14)	0.0314 (12)	0.0154 (11)	0.0149 (10)	0.0230 (11)
C24A	0.0407 (12)	0.0344 (12)	0.0277 (11)	0.0144 (10)	0.0117 (9)	0.0149 (10)
C214	0.0409 (12)	0.0388 (13)	0.0249 (11)	0.0088 (10)	0.0116 (9)	0.0169 (10)
C6	0.0392 (12)	0.0349 (12)	0.0259 (11)	0.0139 (10)	0.0090 (9)	0.0162 (10)
C16	0.0416 (13)	0.0451 (14)	0.0334 (12)	0.0190 (11)	0.0155 (10)	0.0232 (11)
C25A	0.0477 (14)	0.0369 (13)	0.0384 (13)	0.0165 (11)	0.0227 (11)	0.0213 (11)
C26	0.0443 (13)	0.0410 (14)	0.0355 (12)	0.0151 (11)	0.0159 (10)	0.0217 (11)
C12A	0.0432 (13)	0.0506 (15)	0.0293 (12)	0.0206 (11)	0.0133 (10)	0.0222 (11)
C23	0.0461 (14)	0.0382 (13)	0.0454 (14)	0.0160 (11)	0.0195 (11)	0.0232 (12)
C22A	0.0456 (14)	0.0427 (14)	0.0376 (13)	0.0181 (11)	0.0196 (11)	0.0244 (11)
C23A	0.0399 (13)	0.0480 (15)	0.0396 (13)	0.0189 (11)	0.0179 (11)	0.0250 (12)
C13	0.0428 (13)	0.0439 (14)	0.0418 (13)	0.0190 (11)	0.0148 (11)	0.0286 (12)
C216	0.0473 (14)	0.0508 (15)	0.0298 (12)	0.0216 (12)	0.0169 (10)	0.0217 (11)
C215	0.0500 (14)	0.0442 (14)	0.0298 (12)	0.0197 (11)	0.0139 (10)	0.0220 (11)
C16A	0.0486 (14)	0.0422 (14)	0.0350 (12)	0.0197 (11)	0.0169 (11)	0.0250 (11)
C13A	0.0414 (13)	0.0488 (14)	0.0328 (12)	0.0201 (11)	0.0120 (10)	0.0225 (11)
C212	0.0569 (16)	0.0461 (15)	0.0363 (13)	0.0235 (12)	0.0187 (12)	0.0257 (12)
C22	0.0507 (15)	0.0447 (14)	0.0353 (13)	0.0174 (12)	0.0212 (11)	0.0177 (11)
C112	0.0483 (14)	0.0383 (14)	0.0434 (14)	0.0196 (11)	0.0115 (11)	0.0183 (12)
C116	0.0472 (15)	0.0449 (15)	0.0441 (14)	0.0186 (12)	0.0122 (12)	0.0203 (12)
C113	0.0529 (15)	0.0383 (14)	0.0406 (14)	0.0155 (12)	0.0068 (12)	0.0186 (12)
C26A	0.0464 (14)	0.0423 (14)	0.0479 (15)	0.0215 (12)	0.0235 (12)	0.0247 (12)
C12	0.0495 (14)	0.0452 (14)	0.0340 (12)	0.0153 (12)	0.0114 (11)	0.0254 (11)
C114	0.0466 (14)	0.0367 (13)	0.0419 (14)	0.0174 (11)	−0.0023 (11)	0.0133 (11)
C115	0.0448 (14)	0.0453 (15)	0.0451 (15)	0.0213 (12)	0.0092 (12)	0.0152 (12)

Geometric parameters (Å, º)

S14A—C14A	1.768 (2)	C14—C15	1.376 (3)
S14A—C24A	1.770 (2)	C14—C13	1.386 (3)
S6A—C6A	1.665 (2)	C25—C26	1.385 (3)
S4—C4	1.655 (2)	C25—C24	1.391 (4)
S4A—C4A	1.652 (2)	C25—H25	0.9300
S6—C6	1.653 (2)	C15—C16	1.376 (3)
S214—C214	1.777 (2)	C15—H15	0.9300
S214—S215	2.0316 (10)	C24—C23	1.381 (4)
S14—C24	1.767 (2)	C213—C212	1.382 (3)
S14—C14	1.770 (3)	C213—C214	1.384 (4)
S2—C2	1.656 (2)	C213—H213	0.9300
S2A—C2A	1.652 (2)	C15A—C16A	1.381 (4)
S215—S115	2.0792 (12)	C15A—H15A	0.9300
S114—C114	1.785 (3)	C24A—C25A	1.387 (3)
S114—S115	2.0479 (13)	C24A—C23A	1.389 (3)
N1A—C6A	1.357 (3)	C214—C215	1.389 (4)
N1A—C2A	1.370 (3)	C16—H16	0.9300
N1A—H1A	0.8600	C25A—C26A	1.382 (4)
N3A—C2A	1.361 (3)	C25A—H25A	0.9300
N3A—C4A	1.365 (3)	C26—H26	0.9300
N3A—H3A	0.8600	C12A—C13A	1.374 (4)
N5A—C6A	1.358 (3)	C12A—H12A	0.9300
N5A—C4A	1.374 (3)	C23—C22	1.381 (4)
N5A—H5A	0.8600	C23—H23	0.9300
N5—C4	1.364 (3)	C22A—C23A	1.378 (4)
N5—C6	1.365 (3)	C22A—H22A	0.9300
N5—H5	0.8600	C23A—H23A	0.9300
N1—C2	1.365 (3)	C13—C12	1.382 (4)
N1—C6	1.365 (3)	C13—H13	0.9300
N1—H1	0.8600	C216—C215	1.387 (3)
N3—C2	1.364 (3)	C216—H216	0.9300
N3—C4	1.365 (3)	C215—H215	0.9300
N3—H3	0.8600	C16A—H16A	0.9300
N11A—C16A	1.338 (3)	C13A—H13A	0.9300
N11A—C12A	1.344 (3)	C212—H212	0.9300
N211—C216	1.336 (3)	C22—H22	0.9300
N211—C212	1.336 (3)	C112—C113	1.382 (4)
N21A—C26A	1.339 (3)	C112—H112	0.9300
N21A—C22A	1.343 (3)	C116—C115	1.377 (4)
N21—C26	1.335 (3)	C116—H116	0.9300
N21—C22	1.336 (3)	C113—C114	1.387 (4)
N11—C12	1.336 (3)	C113—H113	0.9300
N11—C16	1.343 (3)	C26A—H26A	0.9300
N111—C112	1.334 (3)	C12—H12	0.9300
N111—C116	1.347 (3)	C114—C115	1.384 (4)
C14A—C15A	1.390 (3)	C115—H115	0.9300
C14A—C13A	1.392 (3)
C14A—S14A—C24A	105.17 (11)	C213—C214—C215	118.8 (2)
C214—S214—S215	104.79 (9)	C213—C214—S214	115.97 (19)
C24—S14—C14	106.27 (12)	C215—C214—S214	125.16 (19)
S214—S215—S115	104.50 (4)	N5—C6—N1	115.62 (19)
C114—S114—S115	104.05 (11)	N5—C6—S6	121.10 (17)
S114—S115—S215	106.05 (4)	N1—C6—S6	123.27 (17)
C6A—N1A—C2A	124.4 (2)	N11—C16—C15	124.1 (2)
C6A—N1A—H1A	117.8	N11—C16—H16	117.9
C2A—N1A—H1A	117.8	C15—C16—H16	117.9
C2A—N3A—C4A	124.77 (19)	C26A—C25A—C24A	119.1 (2)
C2A—N3A—H3A	117.6	C26A—C25A—H25A	120.5
C4A—N3A—H3A	117.6	C24A—C25A—H25A	120.5
C6A—N5A—C4A	124.5 (2)	N21—C26—C25	123.6 (2)
C6A—N5A—H5A	117.7	N21—C26—H26	118.2
C4A—N5A—H5A	117.7	C25—C26—H26	118.2
C4—N5—C6	124.6 (2)	N11A—C12A—C13A	124.4 (2)
C4—N5—H5	117.7	N11A—C12A—H12A	117.8
C6—N5—H5	117.7	C13A—C12A—H12A	117.8
C2—N1—C6	124.2 (2)	C24—C23—C22	118.7 (2)
C2—N1—H1	117.9	C24—C23—H23	120.6
C6—N1—H1	117.9	C22—C23—H23	120.6
C2—N3—C4	124.64 (19)	N21A—C22A—C23A	123.6 (2)
C2—N3—H3	117.7	N21A—C22A—H22A	118.2
C4—N3—H3	117.7	C23A—C22A—H22A	118.2
C16A—N11A—C12A	116.2 (2)	C22A—C23A—C24A	118.7 (2)
C216—N211—C212	117.1 (2)	C22A—C23A—H23A	120.6
C26A—N21A—C22A	117.2 (2)	C24A—C23A—H23A	120.6
C26—N21—C22	117.1 (2)	C12—C13—C14	118.7 (2)
C12—N11—C16	116.5 (2)	C12—C13—H13	120.7
C112—N111—C116	116.5 (2)	C14—C13—H13	120.7
N1A—C6A—N5A	115.80 (19)	N211—C216—C215	123.4 (2)
N1A—C6A—S6A	121.81 (17)	N211—C216—H216	118.3
N5A—C6A—S6A	122.39 (17)	C215—C216—H216	118.3
N3A—C4A—N5A	115.0 (2)	C216—C215—C214	118.4 (2)
N3A—C4A—S4A	123.68 (17)	C216—C215—H215	120.8
N5A—C4A—S4A	121.31 (18)	C214—C215—H215	120.8
C15A—C14A—C13A	117.9 (2)	N11A—C16A—C15A	123.9 (2)
C15A—C14A—S14A	116.30 (17)	N11A—C16A—H16A	118.1
C13A—C14A—S14A	125.68 (19)	C15A—C16A—H16A	118.1
N3—C2—N1	115.6 (2)	C12A—C13A—C14A	118.6 (2)
N3—C2—S2	121.25 (17)	C12A—C13A—H13A	120.7
N1—C2—S2	123.13 (18)	C14A—C13A—H13A	120.7
C15—C14—C13	118.8 (2)	N211—C212—C213	123.9 (2)
C15—C14—S14	123.91 (19)	N211—C212—H212	118.1
C13—C14—S14	117.18 (19)	C213—C212—H212	118.1
N3A—C2A—N1A	115.4 (2)	N21—C22—C23	123.6 (2)
N3A—C2A—S2A	123.57 (17)	N21—C22—H22	118.2
N1A—C2A—S2A	121.07 (18)	C23—C22—H22	118.2
C26—C25—C24	118.3 (2)	N111—C112—C113	124.1 (3)
C26—C25—H25	120.8	N111—C112—H112	117.9
C24—C25—H25	120.8	C113—C112—H112	117.9
C14—C15—C16	118.4 (2)	N111—C116—C115	123.8 (3)
C14—C15—H15	120.8	N111—C116—H116	118.1
C16—C15—H15	120.8	C115—C116—H116	118.1
C23—C24—C25	118.6 (2)	C112—C113—C114	118.2 (3)
C23—C24—S14	114.68 (19)	C112—C113—H113	120.9
C25—C24—S14	126.56 (19)	C114—C113—H113	120.9
N5—C4—N3	115.3 (2)	N21A—C26A—C25A	123.1 (2)
N5—C4—S4	122.52 (18)	N21A—C26A—H26A	118.4
N3—C4—S4	122.21 (17)	C25A—C26A—H26A	118.4
C212—C213—C214	118.3 (2)	N11—C12—C13	123.4 (2)
C212—C213—H213	120.8	N11—C12—H12	118.3
C214—C213—H213	120.8	C13—C12—H12	118.3
C16A—C15A—C14A	119.0 (2)	C115—C114—C113	119.0 (2)
C16A—C15A—H15A	120.5	C115—C114—S114	117.0 (2)
C14A—C15A—H15A	120.5	C113—C114—S114	124.0 (2)
C25A—C24A—C23A	118.3 (2)	C116—C115—C114	118.4 (3)
C25A—C24A—S14A	117.88 (18)	C116—C115—H115	120.8
C23A—C24A—S14A	123.76 (19)	C114—C115—H115	120.8
C2A—N1A—C6A—N5A	−2.1 (3)	C12—N11—C16—C15	0.2 (4)
C2A—N1A—C6A—S6A	177.26 (18)	C14—C15—C16—N11	2.9 (4)
C4A—N5A—C6A—N1A	1.8 (3)	C23A—C24A—C25A—C26A	0.5 (4)
C4A—N5A—C6A—S6A	−177.59 (18)	S14A—C24A—C25A—C26A	177.2 (2)
C2A—N3A—C4A—N5A	−3.3 (3)	C22—N21—C26—C25	0.4 (4)
C2A—N3A—C4A—S4A	177.41 (19)	C24—C25—C26—N21	0.7 (4)
C6A—N5A—C4A—N3A	0.7 (3)	C16A—N11A—C12A—C13A	−0.4 (4)
C6A—N5A—C4A—S4A	−179.95 (18)	C25—C24—C23—C22	0.5 (4)
C24A—S14A—C14A—C15A	168.76 (19)	S14—C24—C23—C22	176.3 (2)
C24A—S14A—C14A—C13A	−14.5 (2)	C26A—N21A—C22A—C23A	0.5 (4)
C4—N3—C2—N1	−1.8 (3)	N21A—C22A—C23A—C24A	1.5 (4)
C4—N3—C2—S2	177.81 (18)	C25A—C24A—C23A—C22A	−1.9 (4)
C6—N1—C2—N3	0.2 (3)	S14A—C24A—C23A—C22A	−178.4 (2)
C6—N1—C2—S2	−179.34 (18)	C15—C14—C13—C12	0.9 (4)
C24—S14—C14—C15	−43.2 (2)	S14—C14—C13—C12	176.62 (19)
C24—S14—C14—C13	141.4 (2)	C212—N211—C216—C215	0.4 (4)
C4A—N3A—C2A—N1A	3.0 (3)	N211—C216—C215—C214	0.3 (4)
C4A—N3A—C2A—S2A	−177.64 (19)	C213—C214—C215—C216	−0.9 (4)
C6A—N1A—C2A—N3A	−0.1 (3)	S214—C214—C215—C216	176.1 (2)
C6A—N1A—C2A—S2A	−179.48 (18)	C12A—N11A—C16A—C15A	−0.9 (4)
C13—C14—C15—C16	−3.4 (4)	C14A—C15A—C16A—N11A	1.4 (4)
S14—C14—C15—C16	−178.76 (19)	N11A—C12A—C13A—C14A	1.1 (4)
C26—C25—C24—C23	−1.1 (4)	C15A—C14A—C13A—C12A	−0.6 (4)
C26—C25—C24—S14	−176.49 (19)	S14A—C14A—C13A—C12A	−177.24 (19)
C14—S14—C24—C23	168.46 (19)	C216—N211—C212—C213	−0.6 (4)
C14—S14—C24—C25	−16.0 (3)	C214—C213—C212—N211	0.0 (4)
C6—N5—C4—N3	0.4 (3)	C26—N21—C22—C23	−1.2 (4)
C6—N5—C4—S4	179.35 (18)	C24—C23—C22—N21	0.7 (4)
C2—N3—C4—N5	1.5 (3)	C116—N111—C112—C113	−0.2 (4)
C2—N3—C4—S4	−177.47 (19)	C112—N111—C116—C115	1.0 (4)
C13A—C14A—C15A—C16A	−0.6 (4)	N111—C112—C113—C114	−1.0 (4)
S14A—C14A—C15A—C16A	176.39 (19)	C22A—N21A—C26A—C25A	−2.0 (4)
C14A—S14A—C24A—C25A	135.2 (2)	C24A—C25A—C26A—N21A	1.6 (4)
C14A—S14A—C24A—C23A	−48.3 (2)	C16—N11—C12—C13	−2.9 (4)
C212—C213—C214—C215	0.8 (4)	C14—C13—C12—N11	2.4 (4)
C212—C213—C214—S214	−176.4 (2)	C112—C113—C114—C115	1.5 (4)
S215—S214—C214—C213	−170.77 (18)	C112—C113—C114—S114	−179.4 (2)
S215—S214—C214—C215	12.2 (2)	S115—S114—C114—C115	−157.90 (19)
C4—N5—C6—N1	−1.8 (3)	S115—S114—C114—C113	23.0 (2)
C4—N5—C6—S6	179.10 (18)	N111—C116—C115—C114	−0.5 (4)
C2—N1—C6—N5	1.4 (3)	C113—C114—C115—C116	−0.8 (4)
C2—N1—C6—S6	−179.48 (19)	S114—C114—C115—C116	−180.0 (2)