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
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.051
- wR factor = 0.147
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
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
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. |