The title compound, C17H14N2S, crystallizes in a triclinic unit cell, with two crystallographically independent molecules in the asymmetric unit. The two independent molecules pack in the same sense and form segregated layers along the c axis. The crystal is light-stable and no dimers are formed under irradiation. The intermolecular distances between the potential reactive centers (the C-3 and C-5 ring positions) are 4.093 (4) and 5.643 (4) Å for molecule A, and 4.081 (4) and 5.614 (4) Å for molecule B.
Supporting information
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).
1-Methyl-5,6-diphenyl-2(1
H)-pyrazinethione
top
Crystal data top
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 | |
Data collection top
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 top
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) |
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 | |
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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Comparison of bond lengths (Å) and angles (°) in pyrazinones. top | (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). |