Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102001105/oa1129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102001105/oa1129Isup2.hkl |
CCDC reference: 184492
Data collection: COLLECT (Nonius,1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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).
C17H14N2S | F(000) = 584 |
Mr = 278.37 | Dx = 1.274 Mg m−3 |
Triclinic, P1 | Melting point: 442 K |
a = 9.583 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.740 (2) Å | Cell parameters from 4052 reflections |
c = 15.247 (3) Å | θ = 1.4–14.9° |
α = 106.79 (3)° | µ = 0.21 mm−1 |
β = 90.65 (2)° | T = 293 K |
γ = 104.09 (3)° | Prism, yellow |
V = 1451.5 (5) Å3 | 0.28 × 0.18 × 0.12 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 5053 independent reflections |
Radiation source: fine-focus sealed tube | 2222 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
φ and ω scans | θmax = 25.3°, θmin = 1.4° |
Absorption correction: numerical (maXus; Mackay et al., 1998) | h = −11→11 |
Tmin = 0.942, Tmax = 0.975 | k = −12→12 |
14392 measured reflections | l = −17→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.023P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max < 0.001 |
5053 reflections | Δρmax = 0.17 e Å−3 |
362 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (10) |
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 | ||
S1A | 1.00610 (11) | 0.77438 (10) | 0.58983 (6) | 0.0802 (4) | |
N1A | 0.8105 (3) | 0.5380 (2) | 0.56813 (15) | 0.0460 (7) | |
N2A | 0.7825 (3) | 0.4814 (3) | 0.37996 (16) | 0.0581 (8) | |
C1A | 0.8927 (3) | 0.6294 (3) | 0.5301 (2) | 0.0516 (9) | |
C2A | 0.7106 (3) | 0.4228 (3) | 0.51558 (18) | 0.0420 (8) | |
C3A | 0.6977 (3) | 0.3975 (3) | 0.42236 (18) | 0.0426 (8) | |
C4A | 0.8740 (4) | 0.5896 (3) | 0.4320 (2) | 0.0595 (10) | |
H4A | 0.9318 | 0.6455 | 0.4027 | 0.089* | |
C5A | 0.8328 (4) | 0.5664 (3) | 0.66898 (18) | 0.0668 (11) | |
H5A1 | 0.9340 | 0.5857 | 0.6869 | 0.100* | |
H5A2 | 0.7816 | 0.4893 | 0.6859 | 0.100* | |
H5A3 | 0.7972 | 0.6426 | 0.6995 | 0.100* | |
C6A | 0.6252 (4) | 0.3296 (3) | 0.56205 (18) | 0.0428 (8) | |
C7A | 0.5101 (4) | 0.3606 (4) | 0.6105 (2) | 0.0661 (11) | |
H7A | 0.4889 | 0.4424 | 0.6162 | 0.099* | |
C8A | 0.4268 (5) | 0.2710 (4) | 0.6503 (2) | 0.0791 (13) | |
H8A | 0.3491 | 0.2919 | 0.6819 | 0.119* | |
C9A | 0.4590 (5) | 0.1513 (4) | 0.6431 (2) | 0.0780 (14) | |
H9A | 0.4031 | 0.0911 | 0.6702 | 0.117* | |
C10A | 0.5733 (5) | 0.1197 (4) | 0.5962 (2) | 0.0718 (12) | |
H10A | 0.5951 | 0.0384 | 0.5919 | 0.108* | |
C11A | 0.6568 (4) | 0.2091 (3) | 0.55502 (19) | 0.0543 (10) | |
H11A | 0.7337 | 0.1873 | 0.5228 | 0.081* | |
C12A | 0.5925 (4) | 0.2800 (3) | 0.35833 (19) | 0.0457 (9) | |
C13A | 0.4474 (4) | 0.2489 (3) | 0.3709 (2) | 0.0560 (10) | |
H13A | 0.4147 | 0.2989 | 0.4233 | 0.084* | |
C14A | 0.3492 (4) | 0.1446 (4) | 0.3071 (2) | 0.0668 (11) | |
H14A | 0.2514 | 0.1260 | 0.3159 | 0.100* | |
C15A | 0.3983 (5) | 0.0686 (4) | 0.2303 (2) | 0.0740 (12) | |
H15A | 0.3336 | −0.0024 | 0.1876 | 0.111* | |
C16A | 0.5426 (5) | 0.0978 (4) | 0.2171 (2) | 0.0686 (11) | |
H16A | 0.5752 | 0.0462 | 0.1653 | 0.103* | |
C17A | 0.6403 (4) | 0.2033 (3) | 0.28023 (19) | 0.0573 (10) | |
H17A | 0.7377 | 0.2229 | 0.2704 | 0.086* | |
S1B | 0.47642 (10) | 0.22067 (9) | −0.01252 (6) | 0.0666 (3) | |
N1B | 0.6806 (3) | 0.4524 (3) | 0.05934 (14) | 0.0451 (7) | |
N2B | 0.7175 (3) | 0.4966 (3) | −0.10900 (15) | 0.0581 (8) | |
C1B | 0.5976 (3) | 0.3595 (3) | −0.01630 (19) | 0.0482 (9) | |
C2B | 0.7836 (3) | 0.5638 (3) | 0.05241 (17) | 0.0413 (8) | |
C3B | 0.8016 (3) | 0.5839 (3) | −0.03174 (18) | 0.0455 (9) | |
C4B | 0.6230 (4) | 0.3934 (3) | −0.0997 (2) | 0.0576 (10) | |
H4B | 0.5660 | 0.3357 | −0.1524 | 0.086* | |
C5B | 0.6562 (4) | 0.4298 (3) | 0.14960 (18) | 0.0617 (11) | |
H5B1 | 0.5543 | 0.4021 | 0.1547 | 0.093* | |
H5B2 | 0.6982 | 0.5114 | 0.1980 | 0.093* | |
H5B3 | 0.7002 | 0.3605 | 0.1546 | 0.093* | |
C6B | 0.8665 (3) | 0.6614 (3) | 0.13874 (17) | 0.0404 (8) | |
C7B | 0.9819 (4) | 0.6340 (4) | 0.17886 (19) | 0.0601 (10) | |
H7B | 1.0046 | 0.5521 | 0.1543 | 0.090* | |
C8B | 1.0632 (4) | 0.7295 (4) | 0.2558 (2) | 0.0689 (12) | |
H8B | 1.1414 | 0.7122 | 0.2824 | 0.103* | |
C9B | 1.0282 (4) | 0.8488 (4) | 0.2924 (2) | 0.0667 (12) | |
H9B | 1.0825 | 0.9121 | 0.3442 | 0.100* | |
C10B | 0.9137 (4) | 0.8761 (3) | 0.2534 (2) | 0.0636 (11) | |
H10B | 0.8900 | 0.9572 | 0.2789 | 0.095* | |
C11B | 0.8329 (3) | 0.7814 (3) | 0.17538 (18) | 0.0494 (9) | |
H11B | 0.7561 | 0.7999 | 0.1483 | 0.074* | |
C12B | 0.9088 (4) | 0.6992 (3) | −0.04818 (18) | 0.0448 (9) | |
C13B | 1.0527 (4) | 0.7370 (3) | −0.01447 (19) | 0.0552 (10) | |
H13B | 1.0841 | 0.6912 | 0.0219 | 0.083* | |
C14B | 1.1506 (4) | 0.8416 (4) | −0.0340 (2) | 0.0639 (10) | |
H14B | 1.2469 | 0.8655 | −0.0111 | 0.096* | |
C15B | 1.1049 (4) | 0.9102 (4) | −0.0874 (2) | 0.0656 (11) | |
H15B | 1.1697 | 0.9816 | −0.0999 | 0.098* | |
C16B | 0.9628 (4) | 0.8727 (4) | −0.1222 (2) | 0.0621 (10) | |
H16B | 0.9322 | 0.9179 | −0.1592 | 0.093* | |
C17B | 0.8650 (4) | 0.7682 (3) | −0.10266 (18) | 0.0535 (9) | |
H17B | 0.7691 | 0.7441 | −0.1263 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0757 (8) | 0.0574 (7) | 0.0797 (7) | −0.0073 (6) | 0.0075 (5) | −0.0017 (5) |
N1A | 0.0584 (19) | 0.0399 (18) | 0.0392 (14) | 0.0175 (15) | 0.0046 (12) | 0.0069 (12) |
N2A | 0.073 (2) | 0.0506 (19) | 0.0458 (15) | 0.0046 (16) | 0.0088 (14) | 0.0158 (14) |
C1A | 0.049 (2) | 0.045 (2) | 0.058 (2) | 0.0121 (18) | 0.0109 (16) | 0.0109 (17) |
C2A | 0.047 (2) | 0.036 (2) | 0.0432 (18) | 0.0110 (17) | 0.0060 (15) | 0.0119 (15) |
C3A | 0.050 (2) | 0.041 (2) | 0.0387 (17) | 0.0092 (17) | 0.0073 (15) | 0.0173 (15) |
C4A | 0.065 (3) | 0.055 (3) | 0.056 (2) | 0.008 (2) | 0.0117 (18) | 0.0186 (18) |
C5A | 0.084 (3) | 0.066 (3) | 0.0404 (18) | 0.016 (2) | −0.0036 (17) | 0.0046 (17) |
C6A | 0.058 (2) | 0.036 (2) | 0.0348 (17) | 0.0124 (18) | 0.0033 (15) | 0.0105 (14) |
C7A | 0.088 (3) | 0.053 (2) | 0.067 (2) | 0.024 (2) | 0.033 (2) | 0.0267 (19) |
C8A | 0.106 (4) | 0.065 (3) | 0.068 (2) | 0.014 (3) | 0.035 (2) | 0.029 (2) |
C9A | 0.098 (4) | 0.075 (3) | 0.057 (2) | −0.002 (3) | 0.011 (2) | 0.034 (2) |
C10A | 0.097 (3) | 0.048 (3) | 0.066 (2) | 0.003 (2) | −0.014 (2) | 0.026 (2) |
C11A | 0.071 (3) | 0.044 (2) | 0.0451 (19) | 0.012 (2) | −0.0071 (16) | 0.0106 (16) |
C12A | 0.054 (2) | 0.042 (2) | 0.0434 (18) | 0.0089 (19) | 0.0033 (16) | 0.0194 (16) |
C13A | 0.067 (3) | 0.048 (2) | 0.053 (2) | 0.014 (2) | 0.0001 (18) | 0.0160 (17) |
C14A | 0.063 (3) | 0.065 (3) | 0.073 (2) | 0.010 (2) | −0.001 (2) | 0.026 (2) |
C15A | 0.085 (3) | 0.064 (3) | 0.064 (2) | 0.003 (3) | −0.018 (2) | 0.018 (2) |
C16A | 0.087 (3) | 0.062 (3) | 0.046 (2) | 0.012 (2) | 0.000 (2) | 0.0064 (18) |
C17A | 0.062 (2) | 0.054 (2) | 0.0464 (19) | 0.006 (2) | 0.0045 (17) | 0.0085 (17) |
S1B | 0.0596 (7) | 0.0565 (7) | 0.0689 (6) | −0.0031 (5) | −0.0058 (5) | 0.0115 (5) |
N1B | 0.0530 (18) | 0.0468 (18) | 0.0322 (13) | 0.0108 (15) | 0.0002 (12) | 0.0087 (12) |
N2B | 0.070 (2) | 0.058 (2) | 0.0387 (15) | 0.0068 (17) | −0.0016 (13) | 0.0100 (14) |
C1B | 0.050 (2) | 0.048 (2) | 0.0425 (18) | 0.0125 (18) | −0.0016 (16) | 0.0066 (16) |
C2B | 0.047 (2) | 0.039 (2) | 0.0352 (17) | 0.0088 (17) | 0.0029 (14) | 0.0079 (14) |
C3B | 0.053 (2) | 0.046 (2) | 0.0314 (16) | 0.0117 (18) | −0.0005 (14) | 0.0047 (14) |
C4B | 0.067 (3) | 0.051 (2) | 0.0424 (19) | 0.009 (2) | −0.0093 (17) | 0.0006 (17) |
C5B | 0.075 (3) | 0.055 (2) | 0.0459 (18) | −0.004 (2) | 0.0003 (17) | 0.0186 (16) |
C6B | 0.043 (2) | 0.041 (2) | 0.0333 (16) | 0.0024 (17) | 0.0003 (14) | 0.0112 (15) |
C7B | 0.069 (3) | 0.063 (3) | 0.0459 (19) | 0.021 (2) | −0.0074 (18) | 0.0111 (17) |
C8B | 0.071 (3) | 0.075 (3) | 0.052 (2) | 0.002 (2) | −0.0173 (19) | 0.021 (2) |
C9B | 0.081 (3) | 0.053 (3) | 0.044 (2) | −0.019 (2) | −0.0094 (19) | 0.0110 (18) |
C10B | 0.083 (3) | 0.046 (2) | 0.046 (2) | −0.003 (2) | 0.0059 (19) | 0.0075 (17) |
C11B | 0.063 (2) | 0.040 (2) | 0.0425 (18) | 0.0046 (19) | 0.0055 (16) | 0.0143 (16) |
C12B | 0.052 (2) | 0.042 (2) | 0.0352 (17) | 0.0098 (18) | 0.0042 (15) | 0.0047 (14) |
C13B | 0.061 (3) | 0.063 (3) | 0.0453 (19) | 0.023 (2) | 0.0086 (17) | 0.0159 (17) |
C14B | 0.049 (2) | 0.065 (3) | 0.074 (2) | 0.006 (2) | 0.0085 (19) | 0.022 (2) |
C15B | 0.072 (3) | 0.063 (3) | 0.059 (2) | 0.008 (2) | 0.019 (2) | 0.0215 (19) |
C16B | 0.072 (3) | 0.068 (3) | 0.051 (2) | 0.019 (2) | 0.0139 (19) | 0.0248 (18) |
C17B | 0.057 (2) | 0.063 (2) | 0.0413 (18) | 0.013 (2) | 0.0062 (16) | 0.0179 (16) |
S1A—C1A | 1.664 (3) | S1B—C1B | 1.668 (3) |
N1A—C1A | 1.372 (3) | N1B—C1B | 1.373 (3) |
N1A—C2A | 1.387 (3) | N1B—C2B | 1.385 (3) |
N1A—C5A | 1.481 (3) | N1B—C5B | 1.476 (3) |
N2A—C4A | 1.305 (4) | N2B—C4B | 1.294 (4) |
N2A—C3A | 1.372 (3) | N2B—C3B | 1.374 (3) |
C1A—C4A | 1.429 (4) | C1B—C4B | 1.428 (4) |
C2A—C3A | 1.366 (3) | C2B—C3B | 1.367 (3) |
C2A—C6A | 1.482 (4) | C2B—C6B | 1.495 (4) |
C3A—C12A | 1.486 (4) | C3B—C12B | 1.489 (4) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—H5A1 | 0.9600 | C5B—H5B1 | 0.9601 |
C5A—H5A2 | 0.9603 | C5B—H5B2 | 0.9601 |
C5A—H5A3 | 0.9599 | C5B—H5B3 | 0.9600 |
C6A—C11A | 1.374 (4) | C6B—C11B | 1.366 (4) |
C6A—C7A | 1.389 (4) | C6B—C7B | 1.390 (4) |
C7A—C8A | 1.380 (4) | C7B—C8B | 1.389 (4) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.367 (5) | C8B—C9B | 1.366 (5) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.374 (5) | C9B—C10B | 1.373 (5) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.394 (4) | C10B—C11B | 1.395 (4) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.378 (4) | C12B—C17B | 1.383 (4) |
C12A—C17A | 1.391 (4) | C12B—C13B | 1.386 (4) |
C13A—C14A | 1.387 (4) | C13B—C14B | 1.384 (4) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.379 (5) | C14B—C15B | 1.376 (5) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.372 (5) | C15B—C16B | 1.375 (4) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.385 (4) | C16B—C17B | 1.383 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C1A—N1A—C2A | 122.3 (2) | C1B—N1B—C2B | 121.9 (2) |
C1A—N1A—C5A | 117.2 (2) | C1B—N1B—C5B | 117.5 (3) |
C2A—N1A—C5A | 120.4 (2) | C2B—N1B—C5B | 120.5 (2) |
C4A—N2A—C3A | 117.8 (3) | C4B—N2B—C3B | 117.8 (3) |
N1A—C1A—C4A | 113.9 (3) | N1B—C1B—C4B | 113.6 (3) |
N1A—C1A—S1A | 124.7 (2) | N1B—C1B—S1B | 123.9 (2) |
C4A—C1A—S1A | 121.3 (3) | C4B—C1B—S1B | 122.4 (2) |
C3A—C2A—N1A | 118.6 (3) | C3B—C2B—N1B | 119.3 (2) |
C3A—C2A—C6A | 122.4 (3) | C3B—C2B—C6B | 122.4 (3) |
N1A—C2A—C6A | 119.0 (2) | N1B—C2B—C6B | 118.2 (2) |
C2A—C3A—N2A | 121.7 (3) | C2B—C3B—N2B | 121.0 (3) |
C2A—C3A—C12A | 124.1 (3) | C2B—C3B—C12B | 124.4 (3) |
N2A—C3A—C12A | 114.2 (2) | N2B—C3B—C12B | 114.6 (3) |
N2A—C4A—C1A | 125.5 (3) | N2B—C4B—C1B | 126.3 (3) |
N2A—C4A—H4A | 117.3 | N2B—C4B—H4B | 116.9 |
C1A—C4A—H4A | 117.3 | C1B—C4B—H4B | 116.9 |
N1A—C5A—H5A1 | 109.5 | N1B—C5B—H5B1 | 109.5 |
N1A—C5A—H5A2 | 109.4 | N1B—C5B—H5B2 | 109.9 |
H5A1—C5A—H5A2 | 109.5 | H5B1—C5B—H5B2 | 109.5 |
N1A—C5A—H5A3 | 109.5 | N1B—C5B—H5B3 | 109.1 |
H5A1—C5A—H5A3 | 109.5 | H5B1—C5B—H5B3 | 109.4 |
H5A2—C5A—H5A3 | 109.5 | H5B2—C5B—H5B3 | 109.5 |
C11A—C6A—C7A | 119.3 (3) | C11B—C6B—C7B | 120.0 (3) |
C11A—C6A—C2A | 120.0 (3) | C11B—C6B—C2B | 119.4 (3) |
C7A—C6A—C2A | 120.7 (3) | C7B—C6B—C2B | 120.5 (3) |
C8A—C7A—C6A | 120.6 (4) | C6B—C7B—C8B | 119.6 (3) |
C8A—C7A—H7A | 119.7 | C6B—C7B—H7B | 120.2 |
C6A—C7A—H7A | 119.7 | C8B—C7B—H7B | 120.2 |
C9A—C8A—C7A | 119.8 (4) | C9B—C8B—C7B | 120.0 (4) |
C9A—C8A—H8A | 120.1 | C9B—C8B—H8B | 120.0 |
C7A—C8A—H8A | 120.1 | C7B—C8B—H8B | 120.0 |
C8A—C9A—C10A | 120.3 (4) | C8B—C9B—C10B | 120.6 (3) |
C8A—C9A—H9A | 119.8 | C8B—C9B—H9B | 119.7 |
C10A—C9A—H9A | 119.8 | C10B—C9B—H9B | 119.7 |
C9A—C10A—C11A | 120.1 (4) | C9B—C10B—C11B | 119.7 (4) |
C9A—C10A—H10A | 120.0 | C9B—C10B—H10B | 120.2 |
C11A—C10A—H10A | 120.0 | C11B—C10B—H10B | 120.2 |
C6A—C11A—C10A | 119.9 (4) | C6B—C11B—C10B | 120.1 (3) |
C6A—C11A—H11A | 120.0 | C6B—C11B—H11B | 120.0 |
C10A—C11A—H11A | 120.0 | C10B—C11B—H11B | 120.0 |
C13A—C12A—C17A | 118.7 (3) | C17B—C12B—C13B | 118.3 (3) |
C13A—C12A—C3A | 122.1 (3) | C17B—C12B—C3B | 118.9 (3) |
C17A—C12A—C3A | 119.1 (3) | C13B—C12B—C3B | 122.8 (3) |
C12A—C13A—C14A | 121.3 (3) | C14B—C13B—C12B | 121.2 (3) |
C12A—C13A—H13A | 119.3 | C14B—C13B—H13B | 119.4 |
C14A—C13A—H13A | 119.3 | C12B—C13B—H13B | 119.4 |
C15A—C14A—C13A | 119.3 (4) | C15B—C14B—C13B | 119.7 (3) |
C15A—C14A—H14A | 120.4 | C15B—C14B—H14B | 120.1 |
C13A—C14A—H14A | 120.4 | C13B—C14B—H14B | 120.1 |
C16A—C15A—C14A | 120.0 (3) | C16B—C15B—C14B | 119.6 (3) |
C16A—C15A—H15A | 120.0 | C16B—C15B—H15B | 120.2 |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 120.2 |
C15A—C16A—C17A | 120.6 (4) | C15B—C16B—C17B | 120.6 (3) |
C15A—C16A—H16A | 119.7 | C15B—C16B—H16B | 119.7 |
C17A—C16A—H16A | 119.7 | C17B—C16B—H16B | 119.7 |
C16A—C17A—C12A | 120.0 (3) | C16B—C17B—C12B | 120.5 (3) |
C16A—C17A—H17A | 120.0 | C16B—C17B—H17B | 119.7 |
C12A—C17A—H17A | 120.0 | C12B—C17B—H17B | 119.7 |
C2A—N1A—C1A—C4A | −4.6 (4) | C2B—N1B—C1B—C4B | −3.2 (4) |
C5A—N1A—C1A—C4A | 175.0 (3) | C5B—N1B—C1B—C4B | 176.7 (3) |
C2A—N1A—C1A—S1A | 175.6 (2) | C2B—N1B—C1B—S1B | 177.7 (2) |
C5A—N1A—C1A—S1A | −4.7 (4) | C5B—N1B—C1B—S1B | −2.5 (4) |
C1A—N1A—C2A—C3A | 2.4 (5) | C1B—N1B—C2B—C3B | 1.4 (5) |
C5A—N1A—C2A—C3A | −177.3 (3) | C5B—N1B—C2B—C3B | −178.5 (3) |
C1A—N1A—C2A—C6A | −179.6 (3) | C1B—N1B—C2B—C6B | 178.6 (3) |
C5A—N1A—C2A—C6A | 0.8 (4) | C5B—N1B—C2B—C6B | −1.3 (4) |
N1A—C2A—C3A—N2A | 1.2 (5) | N1B—C2B—C3B—N2B | 1.1 (5) |
C6A—C2A—C3A—N2A | −176.7 (3) | C6B—C2B—C3B—N2B | −176.0 (3) |
N1A—C2A—C3A—C12A | −178.3 (3) | N1B—C2B—C3B—C12B | −179.7 (3) |
C6A—C2A—C3A—C12A | 3.8 (5) | C6B—C2B—C3B—C12B | 3.2 (5) |
C4A—N2A—C3A—C2A | −2.1 (5) | C4B—N2B—C3B—C2B | −1.4 (5) |
C4A—N2A—C3A—C12A | 177.5 (3) | C4B—N2B—C3B—C12B | 179.4 (3) |
C3A—N2A—C4A—C1A | −0.6 (5) | C3B—N2B—C4B—C1B | −0.7 (5) |
N1A—C1A—C4A—N2A | 3.9 (5) | N1B—C1B—C4B—N2B | 3.0 (5) |
S1A—C1A—C4A—N2A | −176.3 (3) | S1B—C1B—C4B—N2B | −177.8 (3) |
C3A—C2A—C6A—C11A | 72.3 (4) | C3B—C2B—C6B—C11B | 73.2 (4) |
N1A—C2A—C6A—C11A | −105.6 (3) | N1B—C2B—C6B—C11B | −103.9 (3) |
C3A—C2A—C6A—C7A | −105.6 (4) | C3B—C2B—C6B—C7B | −103.4 (4) |
N1A—C2A—C6A—C7A | 76.4 (4) | N1B—C2B—C6B—C7B | 79.5 (4) |
C11A—C6A—C7A—C8A | −0.8 (5) | C11B—C6B—C7B—C8B | −0.5 (4) |
C2A—C6A—C7A—C8A | 177.1 (3) | C2B—C6B—C7B—C8B | 176.0 (3) |
C6A—C7A—C8A—C9A | 0.9 (5) | C6B—C7B—C8B—C9B | 1.0 (5) |
C7A—C8A—C9A—C10A | −0.3 (6) | C7B—C8B—C9B—C10B | −0.5 (5) |
C8A—C9A—C10A—C11A | −0.4 (5) | C8B—C9B—C10B—C11B | −0.4 (5) |
C7A—C6A—C11A—C10A | 0.1 (4) | C7B—C6B—C11B—C10B | −0.4 (4) |
C2A—C6A—C11A—C10A | −177.9 (3) | C2B—C6B—C11B—C10B | −177.0 (3) |
C9A—C10A—C11A—C6A | 0.5 (5) | C9B—C10B—C11B—C6B | 0.9 (5) |
C2A—C3A—C12A—C13A | 51.7 (5) | C2B—C3B—C12B—C17B | −134.0 (3) |
N2A—C3A—C12A—C13A | −127.9 (3) | N2B—C3B—C12B—C17B | 45.2 (4) |
C2A—C3A—C12A—C17A | −132.1 (3) | C2B—C3B—C12B—C13B | 48.9 (5) |
N2A—C3A—C12A—C17A | 48.3 (4) | N2B—C3B—C12B—C13B | −131.9 (3) |
C17A—C12A—C13A—C14A | −0.8 (5) | C17B—C12B—C13B—C14B | 0.5 (5) |
C3A—C12A—C13A—C14A | 175.4 (3) | C3B—C12B—C13B—C14B | 177.6 (3) |
C12A—C13A—C14A—C15A | 1.4 (5) | C12B—C13B—C14B—C15B | 0.3 (5) |
C13A—C14A—C15A—C16A | −0.9 (6) | C13B—C14B—C15B—C16B | −1.1 (5) |
C14A—C15A—C16A—C17A | −0.1 (6) | C14B—C15B—C16B—C17B | 1.1 (5) |
C15A—C16A—C17A—C12A | 0.7 (5) | C15B—C16B—C17B—C12B | −0.4 (5) |
C13A—C12A—C17A—C16A | −0.2 (5) | C13B—C12B—C17B—C16B | −0.4 (5) |
C3A—C12A—C17A—C16A | −176.6 (3) | C3B—C12B—C17B—C16B | −177.6 (3) |
(Ib)a | (Ib) | (Ia)b | (Ia) | (Ic)c | |
Molecule A | Molecule B | Molecule A | Molecule B | ||
N1—C1 | 1.372 (3) | 1.372 (3) | 1.393 (4) | 1.389 (4) | 1.385 (4) |
N1—C2 | 1.387 (3) | 1.385 (3) | 1.391 (4) | 1.391 (3) | 1.378 (3) |
N2—C4 | 1.305 (3) | 1.294 (3) | 1.291 (4) | 1.297 (4) | 1.299 (4) |
N2—C3 | 1.372 (3) | 1.374 (3) | 1.361 (3) | 1.362 (4) | 1.372 (4) |
C1—C4 | 1.424 (4) | 1.428 (4) | 1.437 (4) | 1.440 (4) | 1.437 (4) |
C2—C3 | 1.366 (3) | 1.367 (3) | 1.361 (3) | 1.362 (4) | 1.372 (4) |
C1—N1—C2 | 122.3 (2) | 121.9 (2) | 121.2 (3) | 121.9 (3) | 121.9 (2) |
C4—N2—C3 | 117.8 (3) | 117.8 (3) | 117.6 (3) | 118.3 (3) | 118.0 (2) |
S1/O1—C1—N1 | 124.7 (2) | 123.9 (2) | 121.8 (3) | 122.2 (3) | 121.4 (3) |
S1/O1—C1—C(4) | 121.3 (3) | 122.4 (2) | 124.5 (3) | 124.1 (3) | 124.6 (3) |
N1—C1—C4 | 113.9 (3) | 113.6 (3) | 113.7 (3) | 113.8(30 | 114.0 (2) |
C3—C2—N1 | 118.6 (3) | 119.3 (2) | 119.4 (2) | 118.8 (2) | 119.2 (2) |
C2—C3—N2 | 121.7 (3) | 121.0 (3) | 121.7 (2) | 121.7 (3) | 121.4 (2) |
N2—C4—C1 | 125.5 (3) | 126.3 (3) | 126.2 (2) | 125.3 (2) | 125.4 (3) |
Notes: (a) (Ib) is the title compound; (b) (Ia) is 1-methyl-5,6-diphenylpyrazin-2(1H)-one; (c) (Ic) is the light-stable modification of (Ia). |
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