Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035495/is2068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035495/is2068IIsup2.hkl |
CCDC reference: 624881
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).
C15H15N7S2 | Z = 4 |
Mr = 357.46 | F(000) = 744 |
Triclinic, P1 | Dx = 1.388 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0527 (7) Å | Cell parameters from 20784 reflections |
b = 10.7295 (7) Å | θ = 2.0–28.1° |
c = 16.5864 (12) Å | µ = 0.32 mm−1 |
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 |
Stoe IPDS 2 diffractometer | 6725 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 5075 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.038 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.873, Tmax = 0.940 | l = −20→20 |
25011 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-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 parameters | Δρmax = 0.70 e Å−3 |
437 restraints | Δρmin = −0.49 e Å−3 |
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—CH═CH2), 5.08 (dd, Jtrans = 15.60 and 1.60 Hz, 2 1H, N—CH2—CH═CH2), 5.02 (dd, Jcis = 8.20 and 1.60 Hz, 2 1H, N—CH2—CH═CH2), 4.09 (dd, J = 8.08 Hz, 2 2H, NH—CH2—CH═C). 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.83410 (12) | 0.98043 (9) | 0.54281 (6) | 0.0705 (3) | |
S2 | 0.31666 (9) | 0.21111 (7) | 0.89632 (5) | 0.0490 (2) | |
N1 | 0.6262 (3) | 1.0566 (3) | 0.72325 (19) | 0.0603 (7) | |
N2 | 0.7037 (3) | 1.0870 (3) | 0.65137 (19) | 0.0627 (7) | |
H2 | 0.7296 | 1.1650 | 0.6255 | 0.075* | |
N3 | 0.6721 (3) | 0.8826 (2) | 0.68282 (16) | 0.0484 (5) | |
N4 | 0.4928 (3) | 0.7397 (2) | 0.83326 (15) | 0.0420 (5) | |
N5 | 0.3114 (3) | 0.4962 (2) | 0.99662 (15) | 0.0471 (6) | |
N6 | 0.2868 (3) | 0.3727 (2) | 0.99471 (15) | 0.0466 (6) | |
H6 | 0.2470 | 0.3154 | 1.0355 | 0.056* | |
N7 | 0.3875 (2) | 0.4643 (2) | 0.87768 (14) | 0.0395 (5) | |
C1 | 0.6091 (3) | 0.9309 (3) | 0.7419 (2) | 0.0486 (6) | |
C2 | 0.7356 (4) | 0.9842 (3) | 0.6248 (2) | 0.0544 (7) | |
C3 | 0.6833 (4) | 0.7494 (3) | 0.6786 (2) | 0.0557 (7) | |
H3A | 0.6694 | 0.6902 | 0.7349 | 0.067* | |
H3B | 0.7730 | 0.7356 | 0.6596 | 0.067* | |
C4 | 0.5880 (5) | 0.7171 (4) | 0.6219 (3) | 0.0717 (9) | |
H4 | 0.5991 | 0.6370 | 0.6114 | 0.086* | |
C5 | 0.4906 (6) | 0.7888 (6) | 0.5852 (3) | 0.0963 (14) | |
H5A | 0.4754 | 0.8698 | 0.5937 | 0.116* | |
H5B | 0.4358 | 0.7594 | 0.5504 | 0.116* | |
C6 | 0.5315 (3) | 0.8635 (3) | 0.81925 (19) | 0.0445 (6) | |
C7 | 0.4996 (4) | 0.9368 (3) | 0.8738 (2) | 0.0514 (7) | |
H7 | 0.5297 | 1.0221 | 0.8622 | 0.062* | |
C8 | 0.4231 (4) | 0.8817 (3) | 0.9449 (2) | 0.0532 (7) | |
H8 | 0.4008 | 0.9288 | 0.9824 | 0.064* | |
C9 | 0.3798 (3) | 0.7552 (3) | 0.96005 (19) | 0.0484 (6) | |
H9 | 0.3263 | 0.7160 | 1.0073 | 0.058* | |
C10 | 0.4176 (3) | 0.6878 (3) | 0.90352 (18) | 0.0406 (5) | |
C11 | 0.3736 (3) | 0.5506 (3) | 0.92442 (17) | 0.0408 (5) | |
C12 | 0.3302 (3) | 0.3482 (3) | 0.92396 (17) | 0.0416 (6) | |
C13 | 0.4530 (3) | 0.4811 (3) | 0.79494 (18) | 0.0437 (6) | |
H13A | 0.4493 | 0.5720 | 0.7620 | 0.052* | |
H13B | 0.4065 | 0.4303 | 0.7649 | 0.052* | |
C14 | 0.5956 (4) | 0.4379 (3) | 0.8048 (2) | 0.0523 (7) | |
H14 | 0.6521 | 0.4784 | 0.8328 | 0.063* | |
C15 | 0.6434 (5) | 0.3455 (4) | 0.7755 (3) | 0.0736 (10) | |
H15A | 0.5885 | 0.3039 | 0.7473 | 0.088* | |
H15B | 0.7323 | 0.3214 | 0.7828 | 0.088* | |
S3 | 0.19854 (10) | 0.61016 (8) | 0.42074 (5) | 0.0566 (2) | |
S4 | −0.10505 (11) | −0.19925 (8) | 0.85134 (6) | 0.0597 (3) | |
N8 | 0.0764 (3) | 0.6704 (3) | 0.63075 (17) | 0.0579 (6) | |
N9 | 0.1137 (3) | 0.7062 (3) | 0.54762 (17) | 0.0578 (6) | |
H9A | 0.1141 | 0.7858 | 0.5165 | 0.069* | |
N10 | 0.1336 (3) | 0.4999 (2) | 0.58818 (15) | 0.0459 (5) | |
N11 | 0.0236 (3) | 0.3440 (2) | 0.76241 (14) | 0.0407 (5) | |
N12 | −0.1222 (3) | 0.0992 (2) | 0.93899 (17) | 0.0515 (6) | |
N13 | −0.1455 (3) | −0.0268 (2) | 0.94086 (16) | 0.0516 (6) | |
H13 | −0.1873 | −0.0817 | 0.9819 | 0.062* | |
N14 | −0.0411 (3) | 0.0575 (2) | 0.82437 (16) | 0.0489 (5) | |
C16 | 0.0899 (3) | 0.5437 (3) | 0.65450 (19) | 0.0468 (6) | |
C17 | 0.1493 (3) | 0.6072 (3) | 0.51877 (19) | 0.0485 (6) | |
C18 | 0.1668 (4) | 0.3677 (3) | 0.5869 (2) | 0.0588 (7) | |
H18A | 0.1154 | 0.3069 | 0.6315 | 0.071* | |
H18B | 0.1394 | 0.3571 | 0.5338 | 0.071* | |
C19 | 0.3071 (5) | 0.3324 (5) | 0.5973 (3) | 0.0929 (12) | |
H19 | 0.3270 | 0.2446 | 0.6069 | 0.112* | |
C20 | 0.4060 (6) | 0.4077 (7) | 0.5946 (4) | 0.1225 (18) | |
H20A | 0.3924 | 0.4966 | 0.5852 | 0.147* | |
H20B | 0.4916 | 0.3736 | 0.6022 | 0.147* | |
C21 | 0.0570 (3) | 0.4703 (3) | 0.74263 (18) | 0.0440 (6) | |
C22 | 0.0558 (4) | 0.5406 (3) | 0.8011 (2) | 0.0521 (7) | |
H22 | 0.0818 | 0.6275 | 0.7851 | 0.063* | |
C23 | 0.0156 (4) | 0.4790 (3) | 0.8829 (2) | 0.0551 (7) | |
H23 | 0.0122 | 0.5244 | 0.9228 | 0.066* | |
C24 | −0.0198 (4) | 0.3495 (3) | 0.90512 (19) | 0.0503 (7) | |
H24 | −0.0469 | 0.3057 | 0.9601 | 0.060* | |
C25 | −0.0137 (3) | 0.2862 (3) | 0.84300 (18) | 0.0427 (6) | |
C26 | −0.0571 (3) | 0.1487 (3) | 0.86771 (18) | 0.0442 (6) | |
C27 | −0.0975 (3) | −0.0568 (3) | 0.87327 (19) | 0.0481 (6) | |
C28 | 0.0205 (4) | 0.0698 (3) | 0.7403 (2) | 0.0626 (8) | |
H28A | −0.0278 | 0.0152 | 0.7137 | 0.075* | |
H28B | 0.0125 | 0.1593 | 0.7054 | 0.075* | |
C29 | 0.1578 (5) | 0.0333 (6) | 0.7439 (3) | 0.0899 (11) | |
H29 | 0.2146 | 0.0730 | 0.7720 | 0.108* | |
C30 | 0.2090 (6) | −0.0549 (7) | 0.7089 (4) | 0.1122 (17) | |
H30A | 0.1545 | −0.0962 | 0.6804 | 0.135* | |
H30B | 0.2992 | −0.0748 | 0.7132 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0907 (7) | 0.0464 (5) | 0.0642 (6) | −0.0038 (4) | 0.0414 (5) | −0.0043 (4) |
S2 | 0.0645 (5) | 0.0335 (4) | 0.0497 (4) | −0.0097 (3) | 0.0133 (4) | −0.0144 (3) |
N1 | 0.0772 (17) | 0.0358 (11) | 0.0633 (14) | −0.0101 (12) | 0.0303 (12) | −0.0106 (10) |
N2 | 0.0803 (17) | 0.0350 (11) | 0.0650 (15) | −0.0103 (12) | 0.0337 (13) | −0.0057 (10) |
N3 | 0.0610 (14) | 0.0342 (10) | 0.0461 (11) | −0.0066 (10) | 0.0192 (10) | −0.0075 (9) |
N4 | 0.0523 (13) | 0.0314 (10) | 0.0410 (11) | −0.0051 (9) | 0.0127 (10) | −0.0098 (9) |
N5 | 0.0630 (14) | 0.0361 (11) | 0.0422 (11) | −0.0118 (10) | 0.0153 (10) | −0.0126 (9) |
N6 | 0.0631 (14) | 0.0334 (10) | 0.0415 (11) | −0.0116 (10) | 0.0152 (10) | −0.0095 (9) |
N7 | 0.0495 (12) | 0.0315 (9) | 0.0366 (10) | −0.0059 (9) | 0.0103 (9) | −0.0094 (8) |
C1 | 0.0612 (15) | 0.0334 (11) | 0.0486 (13) | −0.0075 (11) | 0.0172 (11) | −0.0095 (10) |
C2 | 0.0667 (17) | 0.0362 (12) | 0.0536 (14) | −0.0068 (12) | 0.0228 (12) | −0.0049 (11) |
C3 | 0.0752 (18) | 0.0359 (12) | 0.0532 (15) | −0.0052 (13) | 0.0233 (13) | −0.0110 (11) |
C4 | 0.099 (2) | 0.0556 (18) | 0.0616 (18) | −0.0187 (16) | 0.0167 (16) | −0.0205 (15) |
C5 | 0.105 (3) | 0.101 (3) | 0.084 (3) | −0.018 (2) | −0.005 (2) | −0.028 (3) |
C6 | 0.0543 (14) | 0.0325 (11) | 0.0452 (12) | −0.0065 (10) | 0.0141 (11) | −0.0105 (10) |
C7 | 0.0660 (17) | 0.0341 (12) | 0.0547 (14) | −0.0086 (12) | 0.0175 (13) | −0.0155 (11) |
C8 | 0.0708 (17) | 0.0382 (13) | 0.0533 (14) | −0.0060 (12) | 0.0194 (13) | −0.0197 (11) |
C9 | 0.0616 (16) | 0.0371 (12) | 0.0462 (13) | −0.0062 (12) | 0.0197 (12) | −0.0137 (11) |
C10 | 0.0499 (13) | 0.0311 (11) | 0.0402 (12) | −0.0053 (10) | 0.0102 (10) | −0.0103 (9) |
C11 | 0.0506 (14) | 0.0323 (10) | 0.0388 (11) | −0.0058 (10) | 0.0108 (10) | −0.0104 (9) |
C12 | 0.0517 (14) | 0.0325 (11) | 0.0389 (12) | −0.0069 (11) | 0.0087 (11) | −0.0085 (9) |
C13 | 0.0570 (14) | 0.0367 (12) | 0.0369 (12) | −0.0057 (11) | 0.0126 (11) | −0.0113 (10) |
C14 | 0.0585 (16) | 0.0495 (15) | 0.0452 (15) | −0.0055 (13) | 0.0132 (13) | −0.0092 (12) |
C15 | 0.070 (2) | 0.081 (3) | 0.072 (2) | 0.0180 (19) | 0.0063 (19) | −0.026 (2) |
S3 | 0.0715 (6) | 0.0486 (5) | 0.0446 (4) | −0.0139 (4) | 0.0147 (4) | −0.0067 (3) |
S4 | 0.0844 (7) | 0.0367 (4) | 0.0556 (5) | −0.0120 (4) | 0.0250 (4) | −0.0121 (3) |
N8 | 0.0843 (17) | 0.0374 (11) | 0.0466 (12) | −0.0039 (12) | 0.0121 (12) | −0.0052 (10) |
N9 | 0.0828 (17) | 0.0368 (11) | 0.0462 (12) | −0.0061 (12) | 0.0124 (12) | −0.0017 (9) |
N10 | 0.0556 (13) | 0.0347 (10) | 0.0426 (10) | −0.0081 (9) | 0.0103 (10) | −0.0050 (9) |
N11 | 0.0463 (12) | 0.0331 (10) | 0.0396 (10) | −0.0018 (9) | 0.0057 (9) | −0.0062 (8) |
N12 | 0.0667 (15) | 0.0367 (11) | 0.0473 (12) | −0.0053 (11) | 0.0172 (11) | −0.0083 (9) |
N13 | 0.0677 (15) | 0.0356 (11) | 0.0465 (12) | −0.0070 (11) | 0.0201 (11) | −0.0063 (9) |
N14 | 0.0645 (14) | 0.0355 (10) | 0.0433 (11) | −0.0066 (10) | 0.0157 (10) | −0.0076 (9) |
C16 | 0.0583 (15) | 0.0347 (11) | 0.0433 (11) | −0.0051 (11) | 0.0082 (11) | −0.0058 (9) |
C17 | 0.0584 (16) | 0.0381 (12) | 0.0437 (12) | −0.0104 (12) | 0.0072 (12) | −0.0040 (10) |
C18 | 0.0764 (17) | 0.0410 (13) | 0.0552 (16) | 0.0005 (13) | 0.0172 (14) | −0.0099 (12) |
C19 | 0.094 (2) | 0.083 (2) | 0.096 (2) | 0.0215 (18) | 0.005 (2) | −0.017 (2) |
C20 | 0.091 (3) | 0.158 (5) | 0.110 (4) | 0.003 (3) | −0.006 (3) | −0.027 (4) |
C21 | 0.0523 (14) | 0.0348 (11) | 0.0418 (11) | −0.0026 (11) | 0.0062 (11) | −0.0071 (9) |
C22 | 0.0709 (17) | 0.0346 (12) | 0.0496 (13) | −0.0046 (12) | 0.0072 (13) | −0.0112 (10) |
C23 | 0.0777 (18) | 0.0413 (13) | 0.0472 (13) | −0.0017 (13) | 0.0079 (14) | −0.0154 (11) |
C24 | 0.0664 (17) | 0.0407 (13) | 0.0408 (13) | −0.0005 (12) | 0.0087 (12) | −0.0085 (10) |
C25 | 0.0499 (14) | 0.0350 (11) | 0.0400 (11) | −0.0002 (10) | 0.0066 (11) | −0.0065 (9) |
C26 | 0.0545 (14) | 0.0343 (11) | 0.0400 (12) | −0.0028 (11) | 0.0094 (11) | −0.0060 (9) |
C27 | 0.0618 (16) | 0.0349 (11) | 0.0434 (13) | −0.0049 (12) | 0.0137 (12) | −0.0063 (10) |
C28 | 0.0836 (18) | 0.0492 (16) | 0.0546 (15) | −0.0152 (14) | 0.0258 (15) | −0.0168 (13) |
C29 | 0.078 (2) | 0.126 (3) | 0.076 (2) | −0.019 (2) | 0.0218 (18) | −0.048 (2) |
C30 | 0.083 (3) | 0.161 (4) | 0.107 (3) | 0.017 (3) | 0.017 (3) | −0.064 (3) |
S1—C2 | 1.667 (3) | C15—H15A | 0.9300 |
S2—C12 | 1.671 (3) | C15—H15B | 0.9300 |
S3—C17 | 1.676 (3) | N8—C16 | 1.307 (4) |
S4—C27 | 1.674 (3) | N8—N9 | 1.360 (4) |
N1—C1 | 1.305 (4) | N9—C17 | 1.328 (4) |
N1—N2 | 1.361 (4) | N9—H9A | 0.8600 |
N2—C2 | 1.335 (4) | N10—C16 | 1.376 (4) |
N2—H2 | 0.8600 | N10—C17 | 1.376 (4) |
N3—C2 | 1.372 (4) | N10—C18 | 1.461 (4) |
N3—C1 | 1.373 (4) | N11—C21 | 1.341 (4) |
N3—C3 | 1.454 (4) | N11—C25 | 1.342 (4) |
N4—C6 | 1.340 (4) | N12—C26 | 1.303 (4) |
N4—C10 | 1.346 (4) | N12—N13 | 1.366 (4) |
N5—C11 | 1.310 (4) | N13—C27 | 1.329 (4) |
N5—N6 | 1.360 (3) | N13—H13 | 0.8600 |
N6—C12 | 1.335 (4) | N14—C27 | 1.374 (4) |
N6—H6 | 0.8600 | N14—C26 | 1.379 (4) |
N7—C11 | 1.374 (3) | N14—C28 | 1.478 (4) |
N7—C12 | 1.378 (3) | C16—C21 | 1.473 (4) |
N7—C13 | 1.467 (3) | C18—C19 | 1.459 (7) |
C1—C6 | 1.477 (4) | C18—H18A | 0.9700 |
C3—C4 | 1.475 (6) | C18—H18B | 0.9700 |
C3—H3A | 0.9700 | C19—C20 | 1.278 (6) |
C3—H3B | 0.9700 | C19—H19 | 0.9300 |
C4—C5 | 1.293 (7) | C20—H20A | 0.9300 |
C4—H4 | 0.9300 | C20—H20B | 0.9300 |
C5—H5A | 0.9300 | C21—C22 | 1.391 (4) |
C5—H5B | 0.9300 | C22—C23 | 1.374 (4) |
C6—C7 | 1.390 (4) | C22—H22 | 0.9300 |
C7—C8 | 1.369 (4) | C23—C24 | 1.375 (4) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C8—C9 | 1.378 (4) | C24—C25 | 1.389 (4) |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C9—C10 | 1.384 (4) | C25—C26 | 1.477 (4) |
C9—H9 | 0.9300 | C28—C29 | 1.430 (6) |
C10—C11 | 1.478 (4) | C28—H28A | 0.9700 |
C13—C14 | 1.502 (5) | C28—H28B | 0.9700 |
C13—H13A | 0.9700 | C29—C30 | 1.337 (7) |
C13—H13B | 0.9700 | C29—H29 | 0.9300 |
C14—C15 | 1.306 (5) | C30—H30A | 0.9300 |
C14—H14 | 0.9300 | C30—H30B | 0.9300 |
C1—N1—N2 | 104.3 (3) | C16—N8—N9 | 103.9 (3) |
C2—N2—N1 | 113.6 (3) | C17—N9—N8 | 114.1 (3) |
C2—N2—H2 | 123.2 | C17—N9—H9A | 123.0 |
N1—N2—H2 | 123.2 | N8—N9—H9A | 123.0 |
C2—N3—C1 | 108.0 (2) | C16—N10—C17 | 107.4 (3) |
C2—N3—C3 | 121.8 (3) | C16—N10—C18 | 129.5 (3) |
C1—N3—C3 | 130.2 (2) | C17—N10—C18 | 123.1 (3) |
C6—N4—C10 | 116.5 (2) | C21—N11—C25 | 116.6 (2) |
C11—N5—N6 | 104.1 (2) | C26—N12—N13 | 104.2 (2) |
C12—N6—N5 | 114.0 (2) | C27—N13—N12 | 113.7 (2) |
C12—N6—H6 | 123.0 | C27—N13—H13 | 123.1 |
N5—N6—H6 | 123.0 | N12—N13—H13 | 123.1 |
C11—N7—C12 | 107.6 (2) | C27—N14—C26 | 107.6 (2) |
C11—N7—C13 | 129.9 (2) | C27—N14—C28 | 122.1 (3) |
C12—N7—C13 | 122.5 (2) | C26—N14—C28 | 130.3 (3) |
N1—C1—N3 | 110.6 (3) | N8—C16—N10 | 110.9 (3) |
N1—C1—C6 | 118.9 (3) | N8—C16—C21 | 119.1 (3) |
N3—C1—C6 | 130.5 (3) | N10—C16—C21 | 129.9 (3) |
N2—C2—N3 | 103.5 (3) | N9—C17—N10 | 103.7 (3) |
N2—C2—S1 | 127.9 (2) | N9—C17—S3 | 128.7 (2) |
N3—C2—S1 | 128.6 (2) | N10—C17—S3 | 127.6 (2) |
N3—C3—C4 | 113.7 (3) | C19—C18—N10 | 115.5 (4) |
N3—C3—H3A | 108.8 | C19—C18—H18A | 108.4 |
C4—C3—H3A | 108.8 | N10—C18—H18A | 108.4 |
N3—C3—H3B | 108.8 | C19—C18—H18B | 108.4 |
C4—C3—H3B | 108.8 | N10—C18—H18B | 108.4 |
H3A—C3—H3B | 107.7 | H18A—C18—H18B | 107.5 |
C5—C4—C3 | 126.6 (4) | C20—C19—C18 | 127.9 (5) |
C5—C4—H4 | 116.7 | C20—C19—H19 | 116.1 |
C3—C4—H4 | 116.7 | C18—C19—H19 | 116.1 |
C4—C5—H5A | 120.0 | C19—C20—H20A | 120.0 |
C4—C5—H5B | 120.0 | C19—C20—H20B | 120.0 |
H5A—C5—H5B | 120.0 | H20A—C20—H20B | 120.0 |
N4—C6—C7 | 123.2 (3) | N11—C21—C22 | 123.3 (3) |
N4—C6—C1 | 120.5 (3) | N11—C21—C16 | 120.1 (3) |
C7—C6—C1 | 116.2 (3) | C22—C21—C16 | 116.5 (3) |
C8—C7—C6 | 119.1 (3) | C23—C22—C21 | 118.7 (3) |
C8—C7—H7 | 120.5 | C23—C22—H22 | 120.6 |
C6—C7—H7 | 120.5 | C21—C22—H22 | 120.6 |
C7—C8—C9 | 118.9 (3) | C22—C23—C24 | 119.4 (3) |
C7—C8—H8 | 120.5 | C22—C23—H23 | 120.3 |
C9—C8—H8 | 120.5 | C24—C23—H23 | 120.3 |
C8—C9—C10 | 118.6 (3) | C23—C24—C25 | 118.1 (3) |
C8—C9—H9 | 120.7 | C23—C24—H24 | 121.0 |
C10—C9—H9 | 120.7 | C25—C24—H24 | 121.0 |
N4—C10—C9 | 123.6 (3) | N11—C25—C24 | 123.9 (3) |
N4—C10—C11 | 119.8 (2) | N11—C25—C26 | 119.0 (3) |
C9—C10—C11 | 116.6 (2) | C24—C25—C26 | 117.0 (3) |
N5—C11—N7 | 110.9 (2) | N12—C26—N14 | 110.7 (3) |
N5—C11—C10 | 119.9 (2) | N12—C26—C25 | 120.1 (3) |
N7—C11—C10 | 129.3 (2) | N14—C26—C25 | 129.1 (3) |
N6—C12—N7 | 103.5 (2) | N13—C27—N14 | 103.8 (3) |
N6—C12—S2 | 128.8 (2) | N13—C27—S4 | 128.6 (2) |
N7—C12—S2 | 127.7 (2) | N14—C27—S4 | 127.6 (2) |
N7—C13—C14 | 110.5 (3) | C29—C28—N14 | 112.9 (3) |
N7—C13—H13A | 109.5 | C29—C28—H28A | 109.0 |
C14—C13—H13A | 109.5 | N14—C28—H28A | 109.0 |
N7—C13—H13B | 109.5 | C29—C28—H28B | 109.0 |
C14—C13—H13B | 109.5 | N14—C28—H28B | 109.0 |
H13A—C13—H13B | 108.1 | H28A—C28—H28B | 107.8 |
C15—C14—C13 | 122.5 (4) | C30—C29—C28 | 123.7 (5) |
C15—C14—H14 | 118.8 | C30—C29—H29 | 118.2 |
C13—C14—H14 | 118.8 | C28—C29—H29 | 118.2 |
C14—C15—H15A | 120.0 | C29—C30—H30A | 120.0 |
C14—C15—H15B | 120.0 | C29—C30—H30B | 120.0 |
H15A—C15—H15B | 120.0 | H30A—C30—H30B | 120.0 |
C1—N1—N2—C2 | −0.2 (5) | C16—N8—N9—C17 | 0.1 (4) |
C11—N5—N6—C12 | −0.5 (4) | C26—N12—N13—C27 | −0.2 (4) |
N2—N1—C1—N3 | −0.9 (4) | N9—N8—C16—N10 | −0.4 (4) |
N2—N1—C1—C6 | 178.2 (3) | N9—N8—C16—C21 | −179.7 (3) |
C2—N3—C1—N1 | 1.7 (4) | C17—N10—C16—N8 | 0.5 (4) |
C3—N3—C1—N1 | 178.2 (3) | C18—N10—C16—N8 | 177.3 (3) |
C2—N3—C1—C6 | −177.3 (4) | C17—N10—C16—C21 | 179.7 (3) |
C3—N3—C1—C6 | −0.8 (6) | C18—N10—C16—C21 | −3.5 (6) |
N1—N2—C2—N3 | 1.2 (4) | N8—N9—C17—N10 | 0.1 (4) |
N1—N2—C2—S1 | −176.7 (3) | N8—N9—C17—S3 | 178.9 (3) |
C1—N3—C2—N2 | −1.7 (4) | C16—N10—C17—N9 | −0.4 (4) |
C3—N3—C2—N2 | −178.5 (3) | C18—N10—C17—N9 | −177.4 (3) |
C1—N3—C2—S1 | 176.2 (3) | C16—N10—C17—S3 | −179.1 (3) |
C3—N3—C2—S1 | −0.7 (6) | C18—N10—C17—S3 | 3.8 (5) |
C2—N3—C3—C4 | −84.8 (4) | C16—N10—C18—C19 | −94.3 (4) |
C1—N3—C3—C4 | 99.1 (4) | C17—N10—C18—C19 | 82.1 (4) |
N3—C3—C4—C5 | −8.2 (6) | N10—C18—C19—C20 | −11.4 (8) |
C10—N4—C6—C7 | 1.1 (5) | C25—N11—C21—C22 | 0.8 (5) |
C10—N4—C6—C1 | −177.2 (3) | C25—N11—C21—C16 | −175.6 (3) |
N1—C1—C6—N4 | 168.7 (3) | N8—C16—C21—N11 | 156.2 (3) |
N3—C1—C6—N4 | −12.3 (6) | N10—C16—C21—N11 | −22.9 (5) |
N1—C1—C6—C7 | −9.7 (5) | N8—C16—C21—C22 | −20.5 (5) |
N3—C1—C6—C7 | 169.2 (4) | N10—C16—C21—C22 | 160.4 (3) |
N4—C6—C7—C8 | −1.1 (6) | N11—C21—C22—C23 | −1.7 (5) |
C1—C6—C7—C8 | 177.4 (3) | C16—C21—C22—C23 | 174.9 (3) |
C6—C7—C8—C9 | −0.2 (6) | C21—C22—C23—C24 | 1.3 (6) |
C7—C8—C9—C10 | 1.3 (5) | C22—C23—C24—C25 | −0.3 (6) |
C6—N4—C10—C9 | 0.0 (5) | C21—N11—C25—C24 | 0.3 (5) |
C6—N4—C10—C11 | −178.5 (3) | C21—N11—C25—C26 | 177.4 (3) |
C8—C9—C10—N4 | −1.2 (5) | C23—C24—C25—N11 | −0.5 (5) |
C8—C9—C10—C11 | 177.4 (3) | C23—C24—C25—C26 | −177.7 (3) |
N6—N5—C11—N7 | 0.3 (4) | N13—N12—C26—N14 | 1.0 (4) |
N6—N5—C11—C10 | −179.8 (3) | N13—N12—C26—C25 | 180.0 (3) |
C12—N7—C11—N5 | −0.1 (4) | C27—N14—C26—N12 | −1.5 (4) |
C13—N7—C11—N5 | −178.1 (3) | C28—N14—C26—N12 | 177.2 (4) |
C12—N7—C11—C10 | −179.9 (3) | C27—N14—C26—C25 | 179.7 (3) |
C13—N7—C11—C10 | 2.1 (5) | C28—N14—C26—C25 | −1.7 (6) |
N4—C10—C11—N5 | 173.5 (3) | N11—C25—C26—N12 | −164.0 (3) |
C9—C10—C11—N5 | −5.2 (5) | C24—C25—C26—N12 | 13.3 (5) |
N4—C10—C11—N7 | −6.7 (5) | N11—C25—C26—N14 | 14.7 (5) |
C9—C10—C11—N7 | 174.6 (3) | C24—C25—C26—N14 | −168.0 (3) |
N5—N6—C12—N7 | 0.5 (4) | N12—N13—C27—N14 | −0.7 (4) |
N5—N6—C12—S2 | −178.5 (3) | N12—N13—C27—S4 | −180.0 (3) |
C11—N7—C12—N6 | −0.3 (3) | C26—N14—C27—N13 | 1.2 (4) |
C13—N7—C12—N6 | 178.0 (3) | C28—N14—C27—N13 | −177.5 (3) |
C11—N7—C12—S2 | 178.8 (3) | C26—N14—C27—S4 | −179.5 (3) |
C13—N7—C12—S2 | −3.0 (5) | C28—N14—C27—S4 | 1.8 (5) |
C11—N7—C13—C14 | 92.1 (4) | C27—N14—C28—C29 | −87.8 (4) |
C12—N7—C13—C14 | −85.8 (3) | C26—N14—C28—C29 | 93.7 (5) |
N7—C13—C14—C15 | 121.0 (4) | N14—C28—C29—C30 | 126.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···N4 | 0.97 | 2.53 | 3.131 (4) | 120 |
C13—H13A···N4 | 0.97 | 2.47 | 3.054 (4) | 118 |
C18—H18A···N11 | 0.97 | 2.47 | 3.150 (4) | 127 |
C28—H28B···N11 | 0.97 | 2.44 | 3.071 (4) | 123 |
N2—H2···S3i | 0.86 | 2.42 | 3.266 (3) | 169 |
N6—H6···S4ii | 0.86 | 2.37 | 3.212 (2) | 167 |
N9—H9A···S1i | 0.86 | 2.47 | 3.297 (3) | 163 |
N13—H13···S2ii | 0.86 | 2.43 | 3.288 (3) | 172 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y, −z+2. |