The title compound, C
9H
8N
6OS, crystallizes with two molecules in the asymmetric unit. In the crystal structure, intermolecular N—H
N hydrogen bonds form a three-dimensional network.
Supporting information
CCDC reference: 274660
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.087
- wR factor = 0.284
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 2.283
Test value = 1.600
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 2.28 e/A 3
PLAT230_ALERT_2_B Hirshfeld Test Diff for S1A - C6A .. 8.59 su
Alert level C
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.284
PLAT084_ALERT_2_C High R2 Value .................................. 0.28
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.21
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7B - C8B .. 5.03 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1A
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7A
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6A - C7A ... 1.55 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C4A .. 3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. N3B .. 2.64 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA; data reduction: X-AREA; 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).
3-(2-Thienylmethyl)-4,4'-bi-1
H-1,2,4-triazol-5(4
H)-one
top
Crystal data top
C9H8N6OS | F(000) = 1024 |
Mr = 248.27 | Dx = 1.506 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4150 reflections |
a = 15.8942 (13) Å | θ = 1.5–28.3° |
b = 6.9666 (3) Å | µ = 0.29 mm−1 |
c = 20.2673 (17) Å | T = 293 K |
β = 102.634 (6)° | Prism, colorless |
V = 2189.8 (3) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 8 | |
Data collection top
Stoe IPDS-2 diffractometer | 5396 independent reflections |
Radiation source: fine-focus sealed tube | 2911 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.3°, θmin = 1.5° |
φ scans | h = −35→35 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −5→5 |
Tmin = 0.804, Tmax = 0.935 | l = −22→22 |
13819 measured reflections | |
Refinement top
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)] = 0.087 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.284 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1827P)2] where P = (Fo2 + 2Fc2)/3 |
5396 reflections | (Δ/σ)max < 0.001 |
304 parameters | Δρmax = 2.28 e Å−3 |
3 restraints | Δρmin = −1.04 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
S1B | 0.81262 (9) | 0.1074 (2) | 0.75390 (7) | 0.0738 (4) | |
N1B | 0.85667 (17) | −0.1609 (4) | 0.92768 (15) | 0.0365 (7) | |
O1B | 0.70305 (17) | −0.3701 (4) | 0.93585 (15) | 0.0491 (7) | |
C3B | 0.7032 (2) | −0.2016 (5) | 0.91989 (18) | 0.0374 (8) | |
N6B | 0.63872 (18) | −0.0732 (5) | 0.90399 (17) | 0.0451 (8) | |
H6B | 0.5859 | −0.0998 | 0.9041 | 0.054* | |
N5B | 0.6658 (2) | 0.1064 (5) | 0.88744 (18) | 0.0449 (8) | |
N4B | 0.77350 (17) | −0.0932 (4) | 0.91147 (15) | 0.0364 (7) | |
C4B | 0.7477 (2) | 0.0916 (5) | 0.89323 (18) | 0.0378 (8) | |
C1B | 0.9117 (2) | −0.1531 (6) | 0.9887 (2) | 0.0429 (8) | |
H1B | 0.9004 | −0.0929 | 1.0268 | 0.051* | |
N2B | 0.9737 (2) | −0.3088 (6) | 0.92022 (19) | 0.0514 (9) | |
N3B | 0.9829 (2) | −0.2425 (5) | 0.98625 (19) | 0.0518 (9) | |
C6B | 0.8569 (2) | 0.2070 (6) | 0.83012 (19) | 0.0421 (8) | |
C2B | 0.8983 (2) | −0.2607 (6) | 0.8871 (2) | 0.0477 (9) | |
H2B | 0.8756 | −0.2900 | 0.8419 | 0.057* | |
C7B | 0.9459 (2) | 0.2461 (6) | 0.8341 (2) | 0.0483 (9) | |
H7B | 0.9823 | 0.3064 | 0.8704 | 0.058* | |
C5B | 0.8073 (3) | 0.2479 (6) | 0.8837 (2) | 0.0441 (9) | |
H5B1 | 0.8479 | 0.2704 | 0.9263 | 0.053* | |
H5B2 | 0.7743 | 0.3647 | 0.8718 | 0.053* | |
C8B | 0.9710 (4) | 0.1814 (10) | 0.7760 (3) | 0.0811 (17) | |
H8B | 1.0276 | 0.1884 | 0.7707 | 0.097* | |
C9B | 0.9085 (5) | 0.1106 (10) | 0.7299 (3) | 0.088 (2) | |
H9B | 0.9157 | 0.0663 | 0.6881 | 0.106* | |
S1A | 0.42971 (11) | 0.1755 (3) | 0.81980 (9) | 0.0919 (6) | |
N1A | 0.36088 (17) | 0.6437 (4) | 0.94220 (15) | 0.0347 (6) | |
N6A | 0.14367 (18) | 0.5558 (5) | 0.92329 (17) | 0.0446 (8) | |
H6A | 0.0911 | 0.5826 | 0.9242 | 0.053* | |
N4A | 0.27759 (16) | 0.5751 (4) | 0.92949 (15) | 0.0352 (6) | |
C4A | 0.2516 (2) | 0.3887 (5) | 0.91262 (18) | 0.0363 (7) | |
O1A | 0.20865 (17) | 0.8529 (4) | 0.95267 (15) | 0.0472 (7) | |
N5A | 0.17031 (19) | 0.3745 (5) | 0.90714 (17) | 0.0437 (8) | |
C7A | 0.2835 (2) | 0.3654 (5) | 0.77073 (18) | 0.0382 (2) | |
H7A | 0.2295 | 0.4224 | 0.7651 | 0.046* | |
C1A | 0.4155 (2) | 0.6657 (6) | 1.0034 (2) | 0.0415 (8) | |
H1A | 0.4040 | 0.6288 | 1.0447 | 0.050* | |
C3A | 0.2082 (2) | 0.6852 (5) | 0.93736 (17) | 0.0361 (7) | |
C2A | 0.4027 (3) | 0.7181 (6) | 0.8960 (2) | 0.0483 (9) | |
H2A | 0.3805 | 0.7233 | 0.8496 | 0.058* | |
N2A | 0.4863 (2) | 0.7462 (5) | 0.99543 (19) | 0.0491 (8) | |
C6A | 0.3372 (3) | 0.2612 (6) | 0.83368 (19) | 0.0430 (8) | |
C5A | 0.3103 (2) | 0.2350 (6) | 0.90032 (19) | 0.0409 (8) | |
H5A1 | 0.2817 | 0.1119 | 0.9003 | 0.049* | |
H5A2 | 0.3613 | 0.2341 | 0.9368 | 0.049* | |
N3A | 0.4778 (2) | 0.7801 (6) | 0.92629 (19) | 0.0524 (9) | |
C8A | 0.3392 (5) | 0.3513 (9) | 0.7225 (3) | 0.0791 (16) | |
H8A | 0.3238 | 0.4055 | 0.6797 | 0.095* | |
C9A | 0.4116 (5) | 0.2589 (10) | 0.7425 (3) | 0.0875 (19) | |
H9A | 0.4504 | 0.2415 | 0.7146 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1B | 0.0666 (8) | 0.0912 (11) | 0.0592 (7) | 0.0053 (7) | 0.0047 (6) | −0.0103 (7) |
N1B | 0.0243 (13) | 0.0402 (16) | 0.0479 (16) | 0.0044 (11) | 0.0139 (12) | 0.0026 (13) |
O1B | 0.0427 (15) | 0.0458 (16) | 0.0615 (17) | −0.0040 (12) | 0.0172 (12) | 0.0094 (13) |
C3B | 0.0325 (17) | 0.041 (2) | 0.0414 (18) | −0.0008 (14) | 0.0139 (14) | 0.0017 (15) |
N6B | 0.0224 (13) | 0.0517 (19) | 0.064 (2) | 0.0002 (13) | 0.0156 (13) | 0.0025 (16) |
N5B | 0.0339 (15) | 0.0433 (18) | 0.060 (2) | 0.0068 (13) | 0.0153 (14) | 0.0052 (15) |
N4B | 0.0226 (13) | 0.0379 (16) | 0.0505 (17) | 0.0014 (11) | 0.0121 (11) | 0.0037 (13) |
C4B | 0.0294 (16) | 0.0396 (19) | 0.0468 (19) | 0.0045 (14) | 0.0133 (14) | 0.0027 (15) |
C1B | 0.0303 (17) | 0.046 (2) | 0.053 (2) | 0.0014 (15) | 0.0091 (15) | −0.0017 (17) |
N2B | 0.0302 (16) | 0.057 (2) | 0.069 (2) | 0.0074 (14) | 0.0150 (15) | −0.0058 (17) |
N3B | 0.0322 (17) | 0.057 (2) | 0.065 (2) | 0.0014 (15) | 0.0089 (15) | −0.0067 (17) |
C6B | 0.0420 (19) | 0.038 (2) | 0.047 (2) | −0.0013 (15) | 0.0123 (16) | 0.0045 (15) |
C2B | 0.0350 (18) | 0.053 (2) | 0.057 (2) | 0.0070 (17) | 0.0160 (17) | −0.0067 (19) |
C7B | 0.0354 (19) | 0.059 (2) | 0.052 (2) | −0.0031 (17) | 0.0126 (16) | −0.0140 (19) |
C5B | 0.043 (2) | 0.0371 (19) | 0.055 (2) | −0.0006 (16) | 0.0187 (17) | −0.0004 (16) |
C8B | 0.072 (4) | 0.094 (4) | 0.093 (4) | −0.002 (3) | 0.050 (3) | 0.001 (3) |
C9B | 0.120 (5) | 0.103 (5) | 0.051 (3) | 0.035 (4) | 0.039 (3) | 0.010 (3) |
S1A | 0.0761 (10) | 0.1115 (13) | 0.0969 (12) | 0.0161 (9) | 0.0377 (9) | 0.0173 (10) |
N1A | 0.0231 (12) | 0.0399 (16) | 0.0427 (15) | −0.0068 (11) | 0.0107 (11) | −0.0015 (12) |
N6A | 0.0246 (14) | 0.0495 (19) | 0.062 (2) | −0.0010 (13) | 0.0148 (13) | −0.0054 (15) |
N4A | 0.0212 (12) | 0.0401 (16) | 0.0460 (16) | −0.0023 (11) | 0.0110 (11) | −0.0008 (12) |
C4A | 0.0290 (16) | 0.0384 (18) | 0.0430 (18) | −0.0026 (14) | 0.0110 (13) | 0.0002 (14) |
O1A | 0.0425 (14) | 0.0440 (16) | 0.0593 (17) | 0.0030 (12) | 0.0204 (12) | −0.0061 (12) |
N5A | 0.0277 (14) | 0.0455 (18) | 0.060 (2) | −0.0045 (13) | 0.0137 (13) | −0.0025 (15) |
C7A | 0.042 | 0.033 | 0.039 | 0.0036 (14) | 0.0071 (13) | −0.0072 (14) |
C1A | 0.0328 (17) | 0.044 (2) | 0.048 (2) | −0.0026 (15) | 0.0100 (15) | 0.0003 (16) |
C3A | 0.0317 (16) | 0.043 (2) | 0.0366 (17) | 0.0006 (14) | 0.0129 (13) | −0.0008 (14) |
C2A | 0.0372 (19) | 0.061 (3) | 0.050 (2) | −0.0124 (18) | 0.0163 (16) | 0.0040 (19) |
N2A | 0.0307 (16) | 0.052 (2) | 0.063 (2) | −0.0066 (14) | 0.0068 (14) | −0.0031 (17) |
C6A | 0.046 (2) | 0.0367 (19) | 0.047 (2) | −0.0015 (15) | 0.0128 (16) | −0.0048 (15) |
C5A | 0.0372 (18) | 0.0383 (19) | 0.048 (2) | 0.0013 (15) | 0.0121 (15) | 0.0000 (16) |
N3A | 0.0319 (16) | 0.059 (2) | 0.069 (2) | −0.0099 (15) | 0.0168 (15) | 0.0052 (18) |
C8A | 0.118 (5) | 0.067 (3) | 0.052 (3) | 0.006 (3) | 0.017 (3) | 0.003 (2) |
C9A | 0.098 (4) | 0.093 (5) | 0.090 (4) | −0.006 (4) | 0.061 (4) | −0.007 (3) |
Geometric parameters (Å, º) top
S1B—C9B | 1.699 (7) | S1A—C9A | 1.637 (7) |
S1B—C6B | 1.699 (4) | S1A—C6A | 1.667 (4) |
N1B—C1B | 1.351 (5) | N1A—C1A | 1.358 (5) |
N1B—C2B | 1.355 (5) | N1A—C2A | 1.364 (5) |
N1B—N4B | 1.374 (4) | N1A—N4A | 1.377 (4) |
O1B—C3B | 1.218 (5) | N6A—C3A | 1.348 (5) |
C3B—N6B | 1.346 (5) | N6A—N5A | 1.394 (5) |
C3B—N4B | 1.389 (4) | N6A—H6A | 0.8600 |
N6B—N5B | 1.388 (5) | N4A—C3A | 1.381 (4) |
N6B—H6B | 0.8600 | N4A—C4A | 1.383 (5) |
N5B—C4B | 1.285 (4) | C4A—N5A | 1.277 (4) |
N4B—C4B | 1.377 (5) | C4A—C5A | 1.476 (5) |
C4B—C5B | 1.484 (5) | O1A—C3A | 1.209 (5) |
C1B—N3B | 1.302 (5) | C7A—C8A | 1.458 (7) |
C1B—H1B | 0.9300 | C7A—C6A | 1.551 (5) |
N2B—C2B | 1.284 (5) | C7A—H7A | 0.9300 |
N2B—N3B | 1.393 (5) | C1A—N2A | 1.299 (5) |
C6B—C7B | 1.425 (5) | C1A—H1A | 0.9300 |
C6B—C5B | 1.502 (5) | C2A—N3A | 1.291 (5) |
C2B—H2B | 0.9300 | C2A—H2A | 0.9300 |
C7B—C8B | 1.399 (7) | N2A—N3A | 1.398 (5) |
C7B—H7B | 0.9300 | C6A—C5A | 1.514 (5) |
C5B—H5B1 | 0.9700 | C5A—H5A1 | 0.9700 |
C5B—H5B2 | 0.9700 | C5A—H5A2 | 0.9700 |
C8B—C9B | 1.303 (9) | C8A—C9A | 1.303 (9) |
C8B—H8B | 0.9300 | C8A—H8A | 0.9300 |
C9B—H9B | 0.9300 | C9A—H9A | 0.9300 |
| | | |
C9B—S1B—C6B | 92.1 (3) | C9A—S1A—C6A | 93.3 (3) |
C1B—N1B—C2B | 105.8 (3) | C1A—N1A—C2A | 105.9 (3) |
C1B—N1B—N4B | 127.0 (3) | C1A—N1A—N4A | 127.3 (3) |
C2B—N1B—N4B | 127.1 (3) | C2A—N1A—N4A | 126.6 (3) |
O1B—C3B—N6B | 131.2 (3) | C3A—N6A—N5A | 113.5 (3) |
O1B—C3B—N4B | 127.2 (3) | C3A—N6A—H6A | 123.2 |
N6B—C3B—N4B | 101.6 (3) | N5A—N6A—H6A | 123.2 |
C3B—N6B—N5B | 113.3 (3) | N1A—N4A—C3A | 123.0 (3) |
C3B—N6B—H6B | 123.3 | N1A—N4A—C4A | 126.5 (3) |
N5B—N6B—H6B | 123.3 | C3A—N4A—C4A | 110.3 (3) |
C4B—N5B—N6B | 105.5 (3) | N5A—C4A—N4A | 109.6 (3) |
N1B—N4B—C4B | 126.8 (3) | N5A—C4A—C5A | 126.4 (3) |
N1B—N4B—C3B | 122.8 (3) | N4A—C4A—C5A | 123.9 (3) |
C4B—N4B—C3B | 109.9 (3) | C4A—N5A—N6A | 105.2 (3) |
N5B—C4B—N4B | 109.6 (3) | C8A—C7A—C6A | 102.4 (4) |
N5B—C4B—C5B | 126.3 (3) | C8A—C7A—H7A | 128.8 |
N4B—C4B—C5B | 124.1 (3) | C6A—C7A—H7A | 128.8 |
N3B—C1B—N1B | 109.9 (4) | N2A—C1A—N1A | 109.4 (3) |
N3B—C1B—H1B | 125.1 | N2A—C1A—H1A | 125.3 |
N1B—C1B—H1B | 125.1 | N1A—C1A—H1A | 125.3 |
C2B—N2B—N3B | 107.8 (3) | O1A—C3A—N6A | 131.4 (3) |
C1B—N3B—N2B | 106.6 (3) | O1A—C3A—N4A | 127.3 (3) |
C7B—C6B—C5B | 126.5 (4) | N6A—C3A—N4A | 101.2 (3) |
C7B—C6B—S1B | 109.8 (3) | N3A—C2A—N1A | 109.8 (4) |
C5B—C6B—S1B | 123.8 (3) | N3A—C2A—H2A | 125.1 |
N2B—C2B—N1B | 109.9 (4) | N1A—C2A—H2A | 125.1 |
N2B—C2B—H2B | 125.1 | C1A—N2A—N3A | 107.5 (3) |
N1B—C2B—H2B | 125.1 | C5A—C6A—C7A | 125.3 (3) |
C8B—C7B—C6B | 110.7 (4) | C5A—C6A—S1A | 122.6 (3) |
C8B—C7B—H7B | 124.7 | C7A—C6A—S1A | 112.0 (3) |
C6B—C7B—H7B | 124.7 | C4A—C5A—C6A | 112.0 (3) |
C4B—C5B—C6B | 114.0 (3) | C4A—C5A—H5A1 | 109.2 |
C4B—C5B—H5B1 | 108.8 | C6A—C5A—H5A1 | 109.2 |
C6B—C5B—H5B1 | 108.8 | C4A—C5A—H5A2 | 109.2 |
C4B—C5B—H5B2 | 108.8 | C6A—C5A—H5A2 | 109.2 |
C6B—C5B—H5B2 | 108.8 | H5A1—C5A—H5A2 | 107.9 |
H5B1—C5B—H5B2 | 107.7 | C2A—N3A—N2A | 107.3 (3) |
C9B—C8B—C7B | 114.4 (5) | C9A—C8A—C7A | 116.7 (5) |
C9B—C8B—H8B | 122.8 | C9A—C8A—H8A | 121.6 |
C7B—C8B—H8B | 122.8 | C7A—C8A—H8A | 121.6 |
C8B—C9B—S1B | 113.0 (4) | C8A—C9A—S1A | 115.5 (4) |
C8B—C9B—H9B | 123.5 | C8A—C9A—H9A | 122.3 |
S1B—C9B—H9B | 123.5 | S1A—C9A—H9A | 122.3 |
| | | |
O1B—C3B—N6B—N5B | −179.0 (4) | C1A—N1A—N4A—C3A | 78.6 (5) |
N4B—C3B—N6B—N5B | −0.8 (4) | C2A—N1A—N4A—C3A | −95.5 (5) |
C3B—N6B—N5B—C4B | −0.3 (4) | C1A—N1A—N4A—C4A | −96.1 (5) |
C1B—N1B—N4B—C4B | 84.9 (5) | C2A—N1A—N4A—C4A | 89.7 (5) |
C2B—N1B—N4B—C4B | −100.0 (5) | N1A—N4A—C4A—N5A | 177.4 (3) |
C1B—N1B—N4B—C3B | −86.7 (5) | C3A—N4A—C4A—N5A | 2.0 (4) |
C2B—N1B—N4B—C3B | 88.5 (5) | N1A—N4A—C4A—C5A | −5.0 (6) |
O1B—C3B—N4B—N1B | −7.3 (6) | C3A—N4A—C4A—C5A | 179.7 (3) |
N6B—C3B—N4B—N1B | 174.4 (3) | N4A—C4A—N5A—N6A | −2.1 (4) |
O1B—C3B—N4B—C4B | 180.0 (4) | C5A—C4A—N5A—N6A | −179.6 (3) |
N6B—C3B—N4B—C4B | 1.6 (4) | C3A—N6A—N5A—C4A | 1.5 (4) |
N6B—N5B—C4B—N4B | 1.4 (4) | C2A—N1A—C1A—N2A | −0.6 (4) |
N6B—N5B—C4B—C5B | −177.3 (4) | N4A—N1A—C1A—N2A | −175.7 (3) |
N1B—N4B—C4B—N5B | −174.4 (3) | N5A—N6A—C3A—O1A | 179.5 (4) |
C3B—N4B—C4B—N5B | −2.0 (4) | N5A—N6A—C3A—N4A | −0.3 (4) |
N1B—N4B—C4B—C5B | 4.2 (6) | N1A—N4A—C3A—O1A | 3.7 (6) |
C3B—N4B—C4B—C5B | 176.7 (3) | C4A—N4A—C3A—O1A | 179.2 (4) |
C2B—N1B—C1B—N3B | −0.1 (5) | N1A—N4A—C3A—N6A | −176.5 (3) |
N4B—N1B—C1B—N3B | 175.8 (3) | C4A—N4A—C3A—N6A | −1.0 (4) |
N1B—C1B—N3B—N2B | 0.9 (5) | C1A—N1A—C2A—N3A | 0.4 (5) |
C2B—N2B—N3B—C1B | −1.3 (5) | N4A—N1A—C2A—N3A | 175.6 (3) |
C9B—S1B—C6B—C7B | 1.8 (4) | N1A—C1A—N2A—N3A | 0.5 (4) |
C9B—S1B—C6B—C5B | −178.9 (4) | C8A—C7A—C6A—C5A | 179.2 (4) |
N3B—N2B—C2B—N1B | 1.3 (5) | C8A—C7A—C6A—S1A | −1.6 (4) |
C1B—N1B—C2B—N2B | −0.8 (5) | C9A—S1A—C6A—C5A | −179.7 (4) |
N4B—N1B—C2B—N2B | −176.7 (3) | C9A—S1A—C6A—C7A | 1.1 (4) |
C5B—C6B—C7B—C8B | 177.5 (5) | N5A—C4A—C5A—C6A | 104.5 (4) |
S1B—C6B—C7B—C8B | −3.3 (5) | N4A—C4A—C5A—C6A | −72.7 (5) |
N5B—C4B—C5B—C6B | −122.0 (4) | C7A—C6A—C5A—C4A | −27.4 (5) |
N4B—C4B—C5B—C6B | 59.6 (5) | S1A—C6A—C5A—C4A | 153.5 (3) |
C7B—C6B—C5B—C4B | −137.9 (4) | N1A—C2A—N3A—N2A | −0.1 (5) |
S1B—C6B—C5B—C4B | 42.9 (5) | C1A—N2A—N3A—C2A | −0.2 (5) |
C6B—C7B—C8B—C9B | 3.6 (8) | C6A—C7A—C8A—C9A | 1.7 (7) |
C7B—C8B—C9B—S1B | −2.2 (8) | C7A—C8A—C9A—S1A | −1.1 (8) |
C6B—S1B—C9B—C8B | 0.2 (6) | C6A—S1A—C9A—C8A | −0.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6B—H6B···N3Ai | 0.86 | 2.05 | 2.881 (4) | 163 |
N6A—H6A···N2Bii | 0.86 | 2.00 | 2.849 (4) | 170 |
N6A—H6A···N3Bii | 0.86 | 2.64 | 3.400 (5) | 148 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z. |