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In the title compound, C15H15N7S2, the asymmetric unit consists of two independent mol­ecules which differ from each other in the orientation of the allyl group. In each mol­ecule, there are two very weak intra­molecular C—H...N hydrogen bonds. In the crystal structure, the two independent mol­ecules are arranged alternately through N—H...S hydrogen-bonded rings to form a mol­ecular chain running along the [12\overline{1}] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035495/is2068sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035495/is2068IIsup2.hkl
Contains datablock II

CCDC reference: 624881

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.051
  • wR factor = 0.147
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.15 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT410_ALERT_2_C Short Intra H...H Contact H18A .. H28B .. 1.97 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

3,3'-(Pyridine-2,6-diyl)bis(4-allyl-4,5-dihydro-1H-1,2,4-triazole-5-thione) top
Crystal data top
C15H15N7S2Z = 4
Mr = 357.46F(000) = 744
Triclinic, P1Dx = 1.388 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0527 (7) ÅCell parameters from 20784 reflections
b = 10.7295 (7) Åθ = 2.0–28.1°
c = 16.5864 (12) ŵ = 0.32 mm1
α = 73.027 (5)°T = 296 K
β = 88.204 (6)°Prism, colourless
γ = 89.503 (6)°0.46 × 0.35 × 0.21 mm
V = 1710.3 (2) Å3
Data collection top
Stoe IPDS 2
diffractometer
6725 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus5075 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.038
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.873, Tmax = 0.940l = 2020
25011 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.082P)2 + 0.6577P]
where P = (Fo2 + 2Fc2)/3
6725 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.70 e Å3
437 restraintsΔρmin = 0.49 e Å3
Special details top

Experimental. Melting points were determined in open capillary tubes on a digital Gallenkamp melting point apparatus and are uncorrected. The IR spectra were recorded for KBr disks with a Mattson 1000 F T—IR spectrometer. 1H NMR spectra were recorded on a Varian AS 400 MHz 1H NMR, 100 MHz 13C NMR spectrometer in DMSO-d6 with TMS as an internal standard. 13C NMR (100 MHz, DMSO-d6): δ 169.74, 153.20, 149.60, 135.20, 134.12, 128.10, 118.4, 47.01

Spectroscopic analysis: IR (ν, cm-1): 3140–3064 (Ar CH), 2980–2878 (Al./Allyl CH), 2945–2762–2560 (SH); 1H NMR (400 MHz, DMSO-d6, δ, p.p.m.): 14.29 (br, 2H, 2 SH), 8.06–8.18 (m, 3H, Pr—CH), 5.79 (dq, J = 9.20 and 1.60 Hz, 2 1H, N—CH2—CHCH2), 5.08 (dd, Jtrans = 15.60 and 1.60 Hz, 2 1H, N—CH2—CHCH2), 5.02 (dd, Jcis = 8.20 and 1.60 Hz, 2 1H, N—CH2—CHCH2), 4.09 (dd, J = 8.08 Hz, 2 2H, NH—CH2—CHC). Analysis, calculated for C15H15N7S2: C 50.40, H 4.23, N 27.43%; found: C 50.38, H 4.22, N 27.45%.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.83410 (12)0.98043 (9)0.54281 (6)0.0705 (3)
S20.31666 (9)0.21111 (7)0.89632 (5)0.0490 (2)
N10.6262 (3)1.0566 (3)0.72325 (19)0.0603 (7)
N20.7037 (3)1.0870 (3)0.65137 (19)0.0627 (7)
H20.72961.16500.62550.075*
N30.6721 (3)0.8826 (2)0.68282 (16)0.0484 (5)
N40.4928 (3)0.7397 (2)0.83326 (15)0.0420 (5)
N50.3114 (3)0.4962 (2)0.99662 (15)0.0471 (6)
N60.2868 (3)0.3727 (2)0.99471 (15)0.0466 (6)
H60.24700.31541.03550.056*
N70.3875 (2)0.4643 (2)0.87768 (14)0.0395 (5)
C10.6091 (3)0.9309 (3)0.7419 (2)0.0486 (6)
C20.7356 (4)0.9842 (3)0.6248 (2)0.0544 (7)
C30.6833 (4)0.7494 (3)0.6786 (2)0.0557 (7)
H3A0.66940.69020.73490.067*
H3B0.77300.73560.65960.067*
C40.5880 (5)0.7171 (4)0.6219 (3)0.0717 (9)
H40.59910.63700.61140.086*
C50.4906 (6)0.7888 (6)0.5852 (3)0.0963 (14)
H5A0.47540.86980.59370.116*
H5B0.43580.75940.55040.116*
C60.5315 (3)0.8635 (3)0.81925 (19)0.0445 (6)
C70.4996 (4)0.9368 (3)0.8738 (2)0.0514 (7)
H70.52971.02210.86220.062*
C80.4231 (4)0.8817 (3)0.9449 (2)0.0532 (7)
H80.40080.92880.98240.064*
C90.3798 (3)0.7552 (3)0.96005 (19)0.0484 (6)
H90.32630.71601.00730.058*
C100.4176 (3)0.6878 (3)0.90352 (18)0.0406 (5)
C110.3736 (3)0.5506 (3)0.92442 (17)0.0408 (5)
C120.3302 (3)0.3482 (3)0.92396 (17)0.0416 (6)
C130.4530 (3)0.4811 (3)0.79494 (18)0.0437 (6)
H13A0.44930.57200.76200.052*
H13B0.40650.43030.76490.052*
C140.5956 (4)0.4379 (3)0.8048 (2)0.0523 (7)
H140.65210.47840.83280.063*
C150.6434 (5)0.3455 (4)0.7755 (3)0.0736 (10)
H15A0.58850.30390.74730.088*
H15B0.73230.32140.78280.088*
S30.19854 (10)0.61016 (8)0.42074 (5)0.0566 (2)
S40.10505 (11)0.19925 (8)0.85134 (6)0.0597 (3)
N80.0764 (3)0.6704 (3)0.63075 (17)0.0579 (6)
N90.1137 (3)0.7062 (3)0.54762 (17)0.0578 (6)
H9A0.11410.78580.51650.069*
N100.1336 (3)0.4999 (2)0.58818 (15)0.0459 (5)
N110.0236 (3)0.3440 (2)0.76241 (14)0.0407 (5)
N120.1222 (3)0.0992 (2)0.93899 (17)0.0515 (6)
N130.1455 (3)0.0268 (2)0.94086 (16)0.0516 (6)
H130.18730.08170.98190.062*
N140.0411 (3)0.0575 (2)0.82437 (16)0.0489 (5)
C160.0899 (3)0.5437 (3)0.65450 (19)0.0468 (6)
C170.1493 (3)0.6072 (3)0.51877 (19)0.0485 (6)
C180.1668 (4)0.3677 (3)0.5869 (2)0.0588 (7)
H18A0.11540.30690.63150.071*
H18B0.13940.35710.53380.071*
C190.3071 (5)0.3324 (5)0.5973 (3)0.0929 (12)
H190.32700.24460.60690.112*
C200.4060 (6)0.4077 (7)0.5946 (4)0.1225 (18)
H20A0.39240.49660.58520.147*
H20B0.49160.37360.60220.147*
C210.0570 (3)0.4703 (3)0.74263 (18)0.0440 (6)
C220.0558 (4)0.5406 (3)0.8011 (2)0.0521 (7)
H220.08180.62750.78510.063*
C230.0156 (4)0.4790 (3)0.8829 (2)0.0551 (7)
H230.01220.52440.92280.066*
C240.0198 (4)0.3495 (3)0.90512 (19)0.0503 (7)
H240.04690.30570.96010.060*
C250.0137 (3)0.2862 (3)0.84300 (18)0.0427 (6)
C260.0571 (3)0.1487 (3)0.86771 (18)0.0442 (6)
C270.0975 (3)0.0568 (3)0.87327 (19)0.0481 (6)
C280.0205 (4)0.0698 (3)0.7403 (2)0.0626 (8)
H28A0.02780.01520.71370.075*
H28B0.01250.15930.70540.075*
C290.1578 (5)0.0333 (6)0.7439 (3)0.0899 (11)
H290.21460.07300.77200.108*
C300.2090 (6)0.0549 (7)0.7089 (4)0.1122 (17)
H30A0.15450.09620.68040.135*
H30B0.29920.07480.71320.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0907 (7)0.0464 (5)0.0642 (6)0.0038 (4)0.0414 (5)0.0043 (4)
S20.0645 (5)0.0335 (4)0.0497 (4)0.0097 (3)0.0133 (4)0.0144 (3)
N10.0772 (17)0.0358 (11)0.0633 (14)0.0101 (12)0.0303 (12)0.0106 (10)
N20.0803 (17)0.0350 (11)0.0650 (15)0.0103 (12)0.0337 (13)0.0057 (10)
N30.0610 (14)0.0342 (10)0.0461 (11)0.0066 (10)0.0192 (10)0.0075 (9)
N40.0523 (13)0.0314 (10)0.0410 (11)0.0051 (9)0.0127 (10)0.0098 (9)
N50.0630 (14)0.0361 (11)0.0422 (11)0.0118 (10)0.0153 (10)0.0126 (9)
N60.0631 (14)0.0334 (10)0.0415 (11)0.0116 (10)0.0152 (10)0.0095 (9)
N70.0495 (12)0.0315 (9)0.0366 (10)0.0059 (9)0.0103 (9)0.0094 (8)
C10.0612 (15)0.0334 (11)0.0486 (13)0.0075 (11)0.0172 (11)0.0095 (10)
C20.0667 (17)0.0362 (12)0.0536 (14)0.0068 (12)0.0228 (12)0.0049 (11)
C30.0752 (18)0.0359 (12)0.0532 (15)0.0052 (13)0.0233 (13)0.0110 (11)
C40.099 (2)0.0556 (18)0.0616 (18)0.0187 (16)0.0167 (16)0.0205 (15)
C50.105 (3)0.101 (3)0.084 (3)0.018 (2)0.005 (2)0.028 (3)
C60.0543 (14)0.0325 (11)0.0452 (12)0.0065 (10)0.0141 (11)0.0105 (10)
C70.0660 (17)0.0341 (12)0.0547 (14)0.0086 (12)0.0175 (13)0.0155 (11)
C80.0708 (17)0.0382 (13)0.0533 (14)0.0060 (12)0.0194 (13)0.0197 (11)
C90.0616 (16)0.0371 (12)0.0462 (13)0.0062 (12)0.0197 (12)0.0137 (11)
C100.0499 (13)0.0311 (11)0.0402 (12)0.0053 (10)0.0102 (10)0.0103 (9)
C110.0506 (14)0.0323 (10)0.0388 (11)0.0058 (10)0.0108 (10)0.0104 (9)
C120.0517 (14)0.0325 (11)0.0389 (12)0.0069 (11)0.0087 (11)0.0085 (9)
C130.0570 (14)0.0367 (12)0.0369 (12)0.0057 (11)0.0126 (11)0.0113 (10)
C140.0585 (16)0.0495 (15)0.0452 (15)0.0055 (13)0.0132 (13)0.0092 (12)
C150.070 (2)0.081 (3)0.072 (2)0.0180 (19)0.0063 (19)0.026 (2)
S30.0715 (6)0.0486 (5)0.0446 (4)0.0139 (4)0.0147 (4)0.0067 (3)
S40.0844 (7)0.0367 (4)0.0556 (5)0.0120 (4)0.0250 (4)0.0121 (3)
N80.0843 (17)0.0374 (11)0.0466 (12)0.0039 (12)0.0121 (12)0.0052 (10)
N90.0828 (17)0.0368 (11)0.0462 (12)0.0061 (12)0.0124 (12)0.0017 (9)
N100.0556 (13)0.0347 (10)0.0426 (10)0.0081 (9)0.0103 (10)0.0050 (9)
N110.0463 (12)0.0331 (10)0.0396 (10)0.0018 (9)0.0057 (9)0.0062 (8)
N120.0667 (15)0.0367 (11)0.0473 (12)0.0053 (11)0.0172 (11)0.0083 (9)
N130.0677 (15)0.0356 (11)0.0465 (12)0.0070 (11)0.0201 (11)0.0063 (9)
N140.0645 (14)0.0355 (10)0.0433 (11)0.0066 (10)0.0157 (10)0.0076 (9)
C160.0583 (15)0.0347 (11)0.0433 (11)0.0051 (11)0.0082 (11)0.0058 (9)
C170.0584 (16)0.0381 (12)0.0437 (12)0.0104 (12)0.0072 (12)0.0040 (10)
C180.0764 (17)0.0410 (13)0.0552 (16)0.0005 (13)0.0172 (14)0.0099 (12)
C190.094 (2)0.083 (2)0.096 (2)0.0215 (18)0.005 (2)0.017 (2)
C200.091 (3)0.158 (5)0.110 (4)0.003 (3)0.006 (3)0.027 (4)
C210.0523 (14)0.0348 (11)0.0418 (11)0.0026 (11)0.0062 (11)0.0071 (9)
C220.0709 (17)0.0346 (12)0.0496 (13)0.0046 (12)0.0072 (13)0.0112 (10)
C230.0777 (18)0.0413 (13)0.0472 (13)0.0017 (13)0.0079 (14)0.0154 (11)
C240.0664 (17)0.0407 (13)0.0408 (13)0.0005 (12)0.0087 (12)0.0085 (10)
C250.0499 (14)0.0350 (11)0.0400 (11)0.0002 (10)0.0066 (11)0.0065 (9)
C260.0545 (14)0.0343 (11)0.0400 (12)0.0028 (11)0.0094 (11)0.0060 (9)
C270.0618 (16)0.0349 (11)0.0434 (13)0.0049 (12)0.0137 (12)0.0063 (10)
C280.0836 (18)0.0492 (16)0.0546 (15)0.0152 (14)0.0258 (15)0.0168 (13)
C290.078 (2)0.126 (3)0.076 (2)0.019 (2)0.0218 (18)0.048 (2)
C300.083 (3)0.161 (4)0.107 (3)0.017 (3)0.017 (3)0.064 (3)
Geometric parameters (Å, º) top
S1—C21.667 (3)C15—H15A0.9300
S2—C121.671 (3)C15—H15B0.9300
S3—C171.676 (3)N8—C161.307 (4)
S4—C271.674 (3)N8—N91.360 (4)
N1—C11.305 (4)N9—C171.328 (4)
N1—N21.361 (4)N9—H9A0.8600
N2—C21.335 (4)N10—C161.376 (4)
N2—H20.8600N10—C171.376 (4)
N3—C21.372 (4)N10—C181.461 (4)
N3—C11.373 (4)N11—C211.341 (4)
N3—C31.454 (4)N11—C251.342 (4)
N4—C61.340 (4)N12—C261.303 (4)
N4—C101.346 (4)N12—N131.366 (4)
N5—C111.310 (4)N13—C271.329 (4)
N5—N61.360 (3)N13—H130.8600
N6—C121.335 (4)N14—C271.374 (4)
N6—H60.8600N14—C261.379 (4)
N7—C111.374 (3)N14—C281.478 (4)
N7—C121.378 (3)C16—C211.473 (4)
N7—C131.467 (3)C18—C191.459 (7)
C1—C61.477 (4)C18—H18A0.9700
C3—C41.475 (6)C18—H18B0.9700
C3—H3A0.9700C19—C201.278 (6)
C3—H3B0.9700C19—H190.9300
C4—C51.293 (7)C20—H20A0.9300
C4—H40.9300C20—H20B0.9300
C5—H5A0.9300C21—C221.391 (4)
C5—H5B0.9300C22—C231.374 (4)
C6—C71.390 (4)C22—H220.9300
C7—C81.369 (4)C23—C241.375 (4)
C7—H70.9300C23—H230.9300
C8—C91.378 (4)C24—C251.389 (4)
C8—H80.9300C24—H240.9300
C9—C101.384 (4)C25—C261.477 (4)
C9—H90.9300C28—C291.430 (6)
C10—C111.478 (4)C28—H28A0.9700
C13—C141.502 (5)C28—H28B0.9700
C13—H13A0.9700C29—C301.337 (7)
C13—H13B0.9700C29—H290.9300
C14—C151.306 (5)C30—H30A0.9300
C14—H140.9300C30—H30B0.9300
C1—N1—N2104.3 (3)C16—N8—N9103.9 (3)
C2—N2—N1113.6 (3)C17—N9—N8114.1 (3)
C2—N2—H2123.2C17—N9—H9A123.0
N1—N2—H2123.2N8—N9—H9A123.0
C2—N3—C1108.0 (2)C16—N10—C17107.4 (3)
C2—N3—C3121.8 (3)C16—N10—C18129.5 (3)
C1—N3—C3130.2 (2)C17—N10—C18123.1 (3)
C6—N4—C10116.5 (2)C21—N11—C25116.6 (2)
C11—N5—N6104.1 (2)C26—N12—N13104.2 (2)
C12—N6—N5114.0 (2)C27—N13—N12113.7 (2)
C12—N6—H6123.0C27—N13—H13123.1
N5—N6—H6123.0N12—N13—H13123.1
C11—N7—C12107.6 (2)C27—N14—C26107.6 (2)
C11—N7—C13129.9 (2)C27—N14—C28122.1 (3)
C12—N7—C13122.5 (2)C26—N14—C28130.3 (3)
N1—C1—N3110.6 (3)N8—C16—N10110.9 (3)
N1—C1—C6118.9 (3)N8—C16—C21119.1 (3)
N3—C1—C6130.5 (3)N10—C16—C21129.9 (3)
N2—C2—N3103.5 (3)N9—C17—N10103.7 (3)
N2—C2—S1127.9 (2)N9—C17—S3128.7 (2)
N3—C2—S1128.6 (2)N10—C17—S3127.6 (2)
N3—C3—C4113.7 (3)C19—C18—N10115.5 (4)
N3—C3—H3A108.8C19—C18—H18A108.4
C4—C3—H3A108.8N10—C18—H18A108.4
N3—C3—H3B108.8C19—C18—H18B108.4
C4—C3—H3B108.8N10—C18—H18B108.4
H3A—C3—H3B107.7H18A—C18—H18B107.5
C5—C4—C3126.6 (4)C20—C19—C18127.9 (5)
C5—C4—H4116.7C20—C19—H19116.1
C3—C4—H4116.7C18—C19—H19116.1
C4—C5—H5A120.0C19—C20—H20A120.0
C4—C5—H5B120.0C19—C20—H20B120.0
H5A—C5—H5B120.0H20A—C20—H20B120.0
N4—C6—C7123.2 (3)N11—C21—C22123.3 (3)
N4—C6—C1120.5 (3)N11—C21—C16120.1 (3)
C7—C6—C1116.2 (3)C22—C21—C16116.5 (3)
C8—C7—C6119.1 (3)C23—C22—C21118.7 (3)
C8—C7—H7120.5C23—C22—H22120.6
C6—C7—H7120.5C21—C22—H22120.6
C7—C8—C9118.9 (3)C22—C23—C24119.4 (3)
C7—C8—H8120.5C22—C23—H23120.3
C9—C8—H8120.5C24—C23—H23120.3
C8—C9—C10118.6 (3)C23—C24—C25118.1 (3)
C8—C9—H9120.7C23—C24—H24121.0
C10—C9—H9120.7C25—C24—H24121.0
N4—C10—C9123.6 (3)N11—C25—C24123.9 (3)
N4—C10—C11119.8 (2)N11—C25—C26119.0 (3)
C9—C10—C11116.6 (2)C24—C25—C26117.0 (3)
N5—C11—N7110.9 (2)N12—C26—N14110.7 (3)
N5—C11—C10119.9 (2)N12—C26—C25120.1 (3)
N7—C11—C10129.3 (2)N14—C26—C25129.1 (3)
N6—C12—N7103.5 (2)N13—C27—N14103.8 (3)
N6—C12—S2128.8 (2)N13—C27—S4128.6 (2)
N7—C12—S2127.7 (2)N14—C27—S4127.6 (2)
N7—C13—C14110.5 (3)C29—C28—N14112.9 (3)
N7—C13—H13A109.5C29—C28—H28A109.0
C14—C13—H13A109.5N14—C28—H28A109.0
N7—C13—H13B109.5C29—C28—H28B109.0
C14—C13—H13B109.5N14—C28—H28B109.0
H13A—C13—H13B108.1H28A—C28—H28B107.8
C15—C14—C13122.5 (4)C30—C29—C28123.7 (5)
C15—C14—H14118.8C30—C29—H29118.2
C13—C14—H14118.8C28—C29—H29118.2
C14—C15—H15A120.0C29—C30—H30A120.0
C14—C15—H15B120.0C29—C30—H30B120.0
H15A—C15—H15B120.0H30A—C30—H30B120.0
C1—N1—N2—C20.2 (5)C16—N8—N9—C170.1 (4)
C11—N5—N6—C120.5 (4)C26—N12—N13—C270.2 (4)
N2—N1—C1—N30.9 (4)N9—N8—C16—N100.4 (4)
N2—N1—C1—C6178.2 (3)N9—N8—C16—C21179.7 (3)
C2—N3—C1—N11.7 (4)C17—N10—C16—N80.5 (4)
C3—N3—C1—N1178.2 (3)C18—N10—C16—N8177.3 (3)
C2—N3—C1—C6177.3 (4)C17—N10—C16—C21179.7 (3)
C3—N3—C1—C60.8 (6)C18—N10—C16—C213.5 (6)
N1—N2—C2—N31.2 (4)N8—N9—C17—N100.1 (4)
N1—N2—C2—S1176.7 (3)N8—N9—C17—S3178.9 (3)
C1—N3—C2—N21.7 (4)C16—N10—C17—N90.4 (4)
C3—N3—C2—N2178.5 (3)C18—N10—C17—N9177.4 (3)
C1—N3—C2—S1176.2 (3)C16—N10—C17—S3179.1 (3)
C3—N3—C2—S10.7 (6)C18—N10—C17—S33.8 (5)
C2—N3—C3—C484.8 (4)C16—N10—C18—C1994.3 (4)
C1—N3—C3—C499.1 (4)C17—N10—C18—C1982.1 (4)
N3—C3—C4—C58.2 (6)N10—C18—C19—C2011.4 (8)
C10—N4—C6—C71.1 (5)C25—N11—C21—C220.8 (5)
C10—N4—C6—C1177.2 (3)C25—N11—C21—C16175.6 (3)
N1—C1—C6—N4168.7 (3)N8—C16—C21—N11156.2 (3)
N3—C1—C6—N412.3 (6)N10—C16—C21—N1122.9 (5)
N1—C1—C6—C79.7 (5)N8—C16—C21—C2220.5 (5)
N3—C1—C6—C7169.2 (4)N10—C16—C21—C22160.4 (3)
N4—C6—C7—C81.1 (6)N11—C21—C22—C231.7 (5)
C1—C6—C7—C8177.4 (3)C16—C21—C22—C23174.9 (3)
C6—C7—C8—C90.2 (6)C21—C22—C23—C241.3 (6)
C7—C8—C9—C101.3 (5)C22—C23—C24—C250.3 (6)
C6—N4—C10—C90.0 (5)C21—N11—C25—C240.3 (5)
C6—N4—C10—C11178.5 (3)C21—N11—C25—C26177.4 (3)
C8—C9—C10—N41.2 (5)C23—C24—C25—N110.5 (5)
C8—C9—C10—C11177.4 (3)C23—C24—C25—C26177.7 (3)
N6—N5—C11—N70.3 (4)N13—N12—C26—N141.0 (4)
N6—N5—C11—C10179.8 (3)N13—N12—C26—C25180.0 (3)
C12—N7—C11—N50.1 (4)C27—N14—C26—N121.5 (4)
C13—N7—C11—N5178.1 (3)C28—N14—C26—N12177.2 (4)
C12—N7—C11—C10179.9 (3)C27—N14—C26—C25179.7 (3)
C13—N7—C11—C102.1 (5)C28—N14—C26—C251.7 (6)
N4—C10—C11—N5173.5 (3)N11—C25—C26—N12164.0 (3)
C9—C10—C11—N55.2 (5)C24—C25—C26—N1213.3 (5)
N4—C10—C11—N76.7 (5)N11—C25—C26—N1414.7 (5)
C9—C10—C11—N7174.6 (3)C24—C25—C26—N14168.0 (3)
N5—N6—C12—N70.5 (4)N12—N13—C27—N140.7 (4)
N5—N6—C12—S2178.5 (3)N12—N13—C27—S4180.0 (3)
C11—N7—C12—N60.3 (3)C26—N14—C27—N131.2 (4)
C13—N7—C12—N6178.0 (3)C28—N14—C27—N13177.5 (3)
C11—N7—C12—S2178.8 (3)C26—N14—C27—S4179.5 (3)
C13—N7—C12—S23.0 (5)C28—N14—C27—S41.8 (5)
C11—N7—C13—C1492.1 (4)C27—N14—C28—C2987.8 (4)
C12—N7—C13—C1485.8 (3)C26—N14—C28—C2993.7 (5)
N7—C13—C14—C15121.0 (4)N14—C28—C29—C30126.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···N40.972.533.131 (4)120
C13—H13A···N40.972.473.054 (4)118
C18—H18A···N110.972.473.150 (4)127
C28—H28B···N110.972.443.071 (4)123
N2—H2···S3i0.862.423.266 (3)169
N6—H6···S4ii0.862.373.212 (2)167
N9—H9A···S1i0.862.473.297 (3)163
N13—H13···S2ii0.862.433.288 (3)172
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y, z+2.
 

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